1-(2,3,4,5,6-penta'ACH'benzyl)piperazine Substances (323) Details by Asch

Query Query

Results

Date

323 substances in Reaxys

2016-05-20 14h:58m:12s (EST)

ACH ACH N

1. Query

NH ACH

ACH ACH

Search as: As drawn

1/337

2016-05-20 15:00:44

Reaxys ID 141624 View in Reaxys

1/323 CAS Registry Number: 2759-28-6 Chemical Name: 1-phenylmethylpiperazine; 1 -benzylpiperazine Linear Structure Formula: NH(CH2)4NCH2C6H5 Molecular Formula: C11H16N2 Molecular Weight: 176.261 Type of Substance: heterocyclic InChI Key: IQXXEPZFOOTTBA-UHFFFAOYSA-N Note:

NH N

Substance Label (127) Label References 3a

Ferte, Jacques; Kuehnel, Jean-Marc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 - 489, View in Reaxys; Congiu, Cenzo; Onnis, Valentina; Deplano, Alessandro; Balboni, Gianfranco; Ceruso, Mariangela; Supuran, Claudiu T.; Bioorganic and Medicinal Chemistry; vol. 23; nb. 17; (2015); p. 5619 - 5625, View in Reaxys; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 9; (2016); p. 2380 - 2382, View in Reaxys

He, Feng-Qi; Liu, Xing-Hai; Wang, Bao-Lei; Li, Zheng-Ming; Journal of Chemical Research; nb. 12; (2006); p. 809 - 811, View in Reaxys; Wang, Bao-Lei; Zhan, Yi-Zhou; Zhang, Li-Yuan; Zhang, Yan; Zhang, Xiao; Li, Zheng-Ming; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; nb. 1; (2016); p. 48 - 54, View in Reaxys

Umamahesh, Balijapalli; Mandlimath, Triveni Rajashekhar; Sathiyanarayanan, Kulathu I.; RSC Advances; vol. 5; nb. 9; (2015); p. 6578 - 6587, View in Reaxys; Zhang, Li-Yuan; Wang, Bao-Lei; Zhan, Yi-Zhou; Hua, Xue-Wen; Liu, Ming; Zhang, Xiao; Song, Hai-Bin; Li, Zheng-Ming; Letters in Drug Design and Discovery; vol. 13; nb. 4; (2016); p. 343 - 351, View in Reaxys

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

Gianatassio, Ryan; Lopchuk, Justin M.; Wang, Jie; Pan, Chung-Mao; Malins, Lara R.; Prieto, Liher; Brandt, Thomas A.; Collins, Michael R.; Gallego, Gary M.; Sach, Neal W.; Spangler, Jillian E.; Zhu, Huichin; Zhu, Jinjiang; Baran, Phil S.; Science; vol. 351; nb. 6270; (2016); p. 241 - 246, View in Reaxys

Periasamy, Mariappan; Reddy, Polimera Obula; Satyanarayana, Iddum; Mohan, Lakavathu; Edukondalu, Athukuri; Journal of Organic Chemistry; vol. 81; nb. 3; (2016); p. 987 - 999, View in Reaxys

Atlan; Bienayme; El Kaim; Majee; Chemical Communications; nb. 17; (2000); p. 1585 - 1586, View in Reaxys; Wang, She-Feng; Yin, Yong; Wu, Xun; Qiao, Fang; Sha, Shao; Lv, Peng-Cheng; Zhao, Jing; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 22; nb. 21; (2014); p. 5727 - 5737, View in Reaxys; Congiu, Cenzo; Onnis, Valentina; Deplano, Alessandro; Balboni, Gianfranco; Dedeoglu, Nurcan; Supuran, Claudiu T.; Bioorganic and Medicinal Chemistry Letters; vol. 25; nb. 18; (2015); p. 3850 - 3853; Art.No: 22949, View in Reaxys; See, Yi Yang; Dang, Tuan Thanh; Chen, Anqi; Seayad, Abdul Majeed; European Journal of Organic Chemistry; vol. 2014; nb. 33; (2014); p. 7405 - 7412, View in Reaxys

Zhou, An; Wu, Hongfei; Pan, Jian; Wang, Xuncui; Li, Jiaming; Wu, Zeyu; Hui, Ailing; Molecules; vol. 20; nb. 1; (2015); p. 1304 - 1318, View in Reaxys

14E

Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Yuan, Wen; Liu, Qiang; Shi, Yikun; Ang, Wei; Luo, Youfu; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 348 - 366, View in Reaxys

Kadam, Kishorkumar S.; Gandhi, Thirumanavelan; Reddy, M. Maheshkumar; Gupte, Amol; Sharma, Rajiv; Journal of Heterocyclic Chemistry; vol. 52; nb. 3; (2015); p. 802 - 814, View in Reaxys

Ashok, Penta; Lu, Cui-Lin; Chander, Subhash; Zheng, Yong-Tang; Murugesan, Sankarnarayanan; Chemical Biology and Drug Design; vol. 85; nb. 6; (2015); p. 722 - 728, View in Reaxys

Schinin, Barbara; Martorana, Andrea; Colabufo, Nicola Antonio; Contino, Marialessandra; Niso, Mauro; Perrone, Maria Grazia; De Guidi, Guido; Catalfo, Alfio; Rappazzo, Giancarlo; Zuccarello, Elisa; Prezzavento, Orazio; Amata, Emanuele; Rescifina, Antonio; Marrazzo, Agostino; RSC Advances; vol. 5; nb. 58; (2015); p. 47108 - 47113, View in Reaxys

Maslivetc, Vladimir A.; Rubina, Marina; Rubin, Michael; Organic and Biomolecular Chemistry; vol. 13; nb. 34; (2015); p. 8993 - 8995, View in Reaxys

D15

Eleftheriadis, Nikolaos; Neochoritis, Constantinos G.; Leus, Niek G. J.; Van Der Wouden, Petra E.; Dömling, Alexander; Dekker, Frank J.; Journal of Medicinal Chemistry; vol. 58; nb. 19; (2015); p. 7850 7862, View in Reaxys

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Wang, Baolei; Shi, Yanxia; Zhan, Yizhou; Zhang, Liyuan; Zhang, Yan; Wang, Lizhong; Zhang, Xiao; Li, Yonghong; Li, Zhengming; Li, Baoju; Chinese Journal of Chemistry; vol. 33; nb. 10; (2015); p. 1124 - 1134, View in Reaxys

Plas, Aurlie; Martin, Camille; Joubert, Nicolas; Viaud-Massuard, Marie-Claude; Organic Letters; vol. 17; nb. 19; (2015); p. 4710 - 4713, View in Reaxys

Li, Wanfang; Wu, Xiao-Feng; Chemistry - A European Journal; vol. 21; nb. 42; (2015); p. 14943 - 14948, View in Reaxys

Aicher, Thomas D.; Anderson, Robert C.; Bebernitz, Gregory R.; Coppola, Gary M.; Jewell, Charles F.; Knorr, Douglas C.; Liu, Charles; Sperbeck, Donald M.; Brand, Leonard J.; Strohschein, Robert J.; Gao, Jiaping; Vinluan, Christine C.; Shetty, Suraj S.; Dragland, Carol; Kaplan, Emma L.; DelGrande, Dominick; Islam, Amin; Liu, Xilin; Lozito, Robert J.; Maniara, Wieslawa M.; Walter, R. Erik; Mann, William R.; Journal of Medicinal Chemistry; vol. 42; nb. 15; (1999); p. 2741 - 2746, View in Reaxys; Perrio-Huard, Cecile; Aubert, Catherine; Lasne, Marie-Claire; Journal of the Chemical Society, Perkin Transactions 1; nb. 3; (2000); p. 311 - 316, View in Reaxys; Lemoucheux, Laurent; Rouden, Jacques; Ibazizene, Meziane; Sobrio, Franck; Lasne, Marie-Claire; Journal of Organic Chemistry; vol. 68; nb. 19; (2003); p. 7289 - 7297, View in Reaxys; Wang, Jin; Li, Shuo; Hu, Xiao; Yang, Jian; Organic Preparations and Procedures International; vol. 46; nb. 5; (2014); p. 469 - 474, View in Reaxys

Kumar, Kamal; Michalik, Dirk; Castro, Ivette Garcia; Tillack, Annegret; Zapf, Alexander; Arlt, Michael; Heinrich, Timo; Boettcher, Henning; Beller, Matthias; Chemistry - A European Journal; vol. 10; nb. 3; (2004); p. 746 - 757, View in Reaxys; Bahadur, Vijay; Mastronicola, Daniela; Tiwari, Hemandra K.; Kumar, Yogesh; Falabella, Micol; Pucillo, Leopoldo P.; Sarti, Paolo; Giuffre, Alessandro; Singh, Brajendra K.; Antimicrobial Agents and Chemotherapy; vol. 58; nb. 1; (2014); p. 543 - 549, View in Reaxys

Bergbreiter, David E.; Osburn, Philip L.; Li, Chunmei; Organic Letters; vol. 4; nb. 5; (2002); p. 737 - 740, View in Reaxys; Murty; Jyothirmai; Krishna, Palakodety Radha; Yadav; Synthetic Communications; vol. 33; nb. 14; (2003); p. 2483 - 2486, View in Reaxys; Bailliez, Vincent; El Kaim, Laurent; Michaut, Valerie; Synthetic Communications; vol. 34; nb. 1; (2004); p. 109 - 118, View in Reaxys; Xu, Zian; Ge, Jingying; Wang, Tianchi; Luo, Ting; Liu, Hongwei; Yu, Xinhong; Synlett; vol. 25; nb. 20; (2014); p. 2913 - 2917, View in Reaxys

xxx; Journal of Organic Chemistry; vol. 66; nb. 3; (2001); p. 1035 - 1037, View in Reaxys; Salvatore; Seung Il Shin; Nagle; Kyung Woon Jung; Journal of Organic Chemistry; vol. 66; nb. 3; (2001); p. 1035 - 1037, View in Reaxys; Tangallapally, Rajendra P.; Sun, Dianqing; Rakesh; Budha, Nageshwar; Lee, Robin E.B.; Lenaerts, Anne J.M.; Meibohm, Bernd; Lee, Richard E.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 23; (2007); p. 6638 - 6642, View in Reaxys; Yin, Kai-Hao; Hsieh, Yi-Han; Sulake, Rohidas S.; Wang, Su-Pei; Chao, Jui-I.; Chen, Chinpiao; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 22; (2014); p. 5247 - 5250, View in Reaxys

Tyagi, Vipin; Gupta, Ashok Kumar; Synthetic Communications; vol. 44; nb. 4; (2014); p. 493 - 499, View in Reaxys

Ghosh, Subhash Chandra; Li, Cheng Chao; Zeng, Hua Chun; Ngiam, Joyce S. Y.; Seayad, Abdul M.; Chen, Anqi; Advanced Synthesis and Catalysis; vol. 356; nb. 2-3; (2014); p. 475 - 484, View in Reaxys

15a

Biannic, Berenger; Bozell, Joseph J.; Elder, Thomas; Green Chemistry; vol. 16; nb. 7; (2014); p. 3635 3642, View in Reaxys

10g

Manda, Bhaskar Reddy; Alla, Manjula; Ganji, Roopa Jones; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 39 - 47, View in Reaxys

Brossard, Dominique; Lechevrel, Mathilde; El Kihel, Laila; Quesnelle, Celine; Khalid, Mohamed; Moslemi, Safa; Reimund, Jean-Marie; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 279 - 290, View in Reaxys

Xiao, Jun-An; Liu, Qi; Ren, Ji-Wei; Liu, Jian; Carter, Rich G.; Chen, Xiao-Qing; Yang, Hua; European Journal of Organic Chemistry; vol. 2014; nb. 26; (2014); p. 5700 - 5704, View in Reaxys

Jallapally, Anvesh; Addla, Dinesh; Yogeeswari, Perumal; Sriram, Dharmarajan; Kantevari, Srinivas; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 23; (2014); p. 5520 - 5524, View in Reaxys

Djigou, Guy B.; Maltais, Ren; Poirier, Donald; Combinatorial Chemistry and High Throughput Screening; vol. 17; nb. 9; (2014); p. 734 - 744, View in Reaxys

Kotsuki, Hiyoshizo; Sakai, Hiromitsu; Shinohara, Toshio; Synlett; nb. 1; (2000); p. 116 - 118, View in Reaxys; Wagh, Yogesh S.; Tiwari, Neelam J.; Bhanage, Bhalchandra M.; Tetrahedron Letters; vol. 54; nb. 10; (2013); p. 1290 - 1293, View in Reaxys

Cuppoletti, Andrea; Dagostin, Claudio; Florea, Cristina; Galli, Carlo; Gentili, Patrizia; Lanzalunga, Osvaldo; Petride, Aurica; Petride, Horia; Chemistry - A European Journal; vol. 5; nb. 10; (1999); p. 2993 2999, View in Reaxys; Modica, Maria; Santagati, Maria; Guccione, Salvatore; Russo, Filippo; Cagnotto, Alfredo; Goegan, Mara; Mennini, Tiziana; European Journal of Medicinal Chemistry; vol. 35; nb. 12; (2000); p. 1065 - 1079, View in Reaxys; Modica, Maria; Santagati, Maria; Guccione, Salvatore; Russo,

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Filippo; Cagnotto, Alfredo; Goegan, Mara; Mennini, Tiziana; European Journal of Medicinal Chemistry; vol. 36; nb. 3; (2001); p. 287 - 301, View in Reaxys; Patent; The University of Tokyo; Nagano, Tetsuo; Kojima, Hirotatsu; Kiyose, Kazuki; US8507677; (2013); (B2) English, View in Reaxys e

Erker, Thomas; Schreder, Maria E.; Studenik, Christian; Archiv der Pharmazie; vol. 333; nb. 2-3; (2000); p. 58 - 62, View in Reaxys; Tabuchi, Yukako; Kakumoto, Yusa; Uchimoto, Hitomi; Kawasaki, Ikuo; Ohishi, Yoshitaka; Nishide, Kiyoharu; Heterocycles; vol. 87; nb. 1; (2013); p. 177 - 191, View in Reaxys

BZP

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys; Patent; Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2631231; (2013); (A1) English, View in Reaxys

Caproiu, Miron; Florea, Cristina; Galli, Carlo; Petride, Aurica; Petride, Horia; European Journal of Organic Chemistry; nb. 6; (2000); p. 1037 - 1043, View in Reaxys; Patent; Kovach, John S.; Johnson, Francis; US2009/36309; (2009); (A1) English, View in Reaxys; Prezzavento; Arena; Parenti; Pasquinucci; Arico; Scoto; Grancara; Toninello; Ronsisvalle; Journal of Medicinal Chemistry; vol. 56; nb. 6; (2013); p. 2447 - 2455, View in Reaxys

Patel, Divyesh; Patel, Rahul; Kumari, Premlata; Patel, Navin; Acta Poloniae Pharmaceutica - Drug Research; vol. 69; nb. 5; (2012); p. 879 - 891, View in Reaxys; Sadeghzadeh, Masoud; Sheibani, Shahab; Ghandi, Mehdi; Daha, Fariba Johari; Amanlou, Massoud; Arjmand, Mohammad; Hasani Bozcheloie, Abolfazl; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 488 - 497, View in Reaxys

45a

Stoessel, Anne; Schlenk, Miriam; Hinz, Sonja; Kueppers, Petra; Heer, Jag; Guetschow, Michael; Mueller, Christa E.; Journal of Medicinal Chemistry; vol. 56; nb. 11; (2013); p. 4580 - 4596, View in Reaxys

Gadge, Sandip T.; Bhanage, Bhalchandra M.; Journal of Organic Chemistry; vol. 78; nb. 13; (2013); p. 6793 - 6797, View in Reaxys

for 8

Rajaram, Singanaboina; Ramulu, Udugu; Ramesh, Dasari; Srikanth, Dudem; Bhattacharya, Papri; Prabhakar, Peddikotla; Kalivendi, Shasi V.; Babu, Katragadda Suresh; Venkateswarlu, Yenamandra; Navath, Suryakiran; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 23; (2013); p. 6234 - 6238, View in Reaxys

13c

Koch, Pierre; Akkari, Rhalid; Brunschweiger, Andreas; Borrmann, Thomas; Schlenk, Miriam; Kueppers, Petra; Koese, Meryem; Radjainia, Hamid; Hockemeyer, Joerg; Drabczynska, Anna; Kiec-Kononowicz, Katarzyna; Mueller, Christa E.; Bioorganic and Medicinal Chemistry; vol. 21; nb. 23; (2013); p. 7435 - 7452, View in Reaxys

Patel, Rahul V.; Patel, Amit B.; Kumari, Premlata; Chikhalia, Kishor H.; Medicinal Chemistry Research; vol. 21; nb. 10; (2012); p. 3119 - 3132, View in Reaxys

Hayashi, Shigeo; Ohashi, Katsuyo; Nakata, Eriko; Emoto, Chie; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 228 - 242, View in Reaxys

Zhu, Mingwen; Fujita, Ken-Ichi; Yamaguchi, Ryohei; Journal of Organic Chemistry; vol. 77; nb. 20; (2012); p. 9102 - 9109,8, View in Reaxys

Loison, Stephanie; Cottet, Martin; Orcel, Helene; Adihou, Helene; Rahmeh, Rita; Lamarque, Laurent; Trinquet, Eric; Kellenberger, Esther; Hibert, Marcel; Durroux, Thierry; Mouillac, Bernard; Bonnet, Dominique; Journal of Medicinal Chemistry; vol. 55; nb. 20; (2012); p. 8588 - 8602, View in Reaxys

Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/71286; (2011); (A1) English, View in Reaxys

run5/c

Bhor, Malhari D.; Bhanushali, Mayur J.; Nandurkar, Nitin S.; Bhanage, Bhalchandra M.; Tetrahedron Letters; vol. 49; nb. 6; (2008); p. 965 - 969, View in Reaxys

substrate, T/E 25,26

Kamal, Ahmed; Reddy, J. Surendranadha; Bharathi, E. Vijaya; Dastagiri; Tetrahedron Letters; vol. 49; nb. 2; (2008); p. 348 - 353, View in Reaxys

Kumar Parai, Maloy; Panda, Gautam; Srivastava, Kumkum; Kumar Puri, Sunil; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 2; (2008); p. 776 - 781, View in Reaxys

1 (Ar&1% = C6H5CH2)

Yoon, Juhee; Yoo, Eun A; Kim, Ji-Yeon; Pae, Ae Nim; Rhim, Hyewhon; Park, Woo-Kyu; Kong, Jae Yang; Park Choo, Hea-Young; Bioorganic and Medicinal Chemistry; vol. 16; nb. 10; (2008); p. 5405 - 5412, View in Reaxys

piperazine, f

Yang, Yinghua; Sun, Lianli; Dong, Shengyi; Wang, Xiaoyu; Yang, Leixiang; Wu, Xiumei; Bai, Hua; Zhao, Yu; Mendeleev Communications; vol. 18; nb. 4; (2008); p. 186 - 187, View in Reaxys

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amine, entry 20

Shrikhande, Janhavi J.; Gawande, Manoj B.; Jayaram, Radha V.; Tetrahedron Letters; vol. 49; nb. 32; (2008); p. 4799 - 4803, View in Reaxys

Flipo, Marion; Beghyn, Terence; Charton, Julie; Leroux, Virginie A.; Deprez, Benoit P.; Deprez-Poulain, Rebecca F.; Bioorganic and Medicinal Chemistry; vol. 15; nb. 1; (2007); p. 63 - 76, View in Reaxys

Tab 1, amine, entry 12

Lemiegre, Loic; Tanaka, Takatsugu; Nanao, Takeshi; Isobe, Hiroyuki; Nakamura, Eiichi; Chemistry Letters; vol. 36; nb. 1; (2007); p. 20 - 21, View in Reaxys

Guo, Li-Na; Duan, Xin-Hua; Bi, Hai-Peng; Liu, Xue-Yuan; Liang, Yong-Min; Journal of Organic Chemistry; vol. 72; nb. 4; (2007); p. 1538 - 1540, View in Reaxys

Flipo, Marion; Beghyn, Terence; Leroux, Virginie; Florent, Isabelle; Deprez, Benoit P.; Deprez-Poulain, Rebecca F.; Journal of Medicinal Chemistry; vol. 50; nb. 6; (2007); p. 1322 - 1334, View in Reaxys

educt to 4d

Pratap, Ramendra; Ram, Vishnu Ji; Tetrahedron Letters; vol. 48; nb. 15; (2007); p. 2755 - 2759, View in Reaxys

amine, tab 2/6

Schwarz, Nicolle; Tillack, Annegret; Alex, Karolin; Sayyed, Iliyas Ali; Jackstell, Ralf; Beller, Matthias; Tetrahedron Letters; vol. 48; nb. 16; (2007); p. 2897 - 2900, View in Reaxys

amine educt of 4f

Pratap, Ramendra; Ram, Vishnu Ji; Tetrahedron Letters; vol. 48; nb. 10; (2007); p. 1715 - 1719, View in Reaxys

Chaudhary, Preeti; Kumar, Rupesh; Verma, Akhilesh K.; Singh, Devender; Yadav, Vibha; Chhillar, Anil K.; Sharma; Chandra, Ramesh; Bioorganic and Medicinal Chemistry; vol. 14; nb. 6; (2006); p. 1819 - 1826, View in Reaxys; Chaudhary, Preeti; Nimesh, Surendra; Yadav, Veena; Verma, Akhilesh Kr.; Kumar, Rupesh; European Journal of Medicinal Chemistry; vol. 42; nb. 4; (2007); p. 471 - 476, View in Reaxys

Tab. 4, Ent. 6, amine

Ramu, Enugala; Varala, Ravi; Sreelatha, Nuvula; Adapa, Srinivas R.; Tetrahedron Letters; vol. 48; nb. 40; (2007); p. 7184 - 7190, View in Reaxys

14, R2=benzyl

Anandan, Sampath-Kumar; Ward, John S.; Brokx, Richard D.; Denny, Trisha; Bray, Mark R.; Patel, Dinesh V.; Xiao, Xiao-Yi; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 21; (2007); p. 5995 - 5999, View in Reaxys

amine for 20

Petricci, Elena; Mann, Andre; Salvadori, Jessica; Taddei, Maurizio; Tetrahedron Letters; vol. 48; nb. 48; (2007); p. 8501 - 8504, View in Reaxys

Perrone, Roberto; Berardi, Francesco; Colabufo, Nicola A.; Leopoldo, Marcello; Lograno, Marcello D.; Tortorella, Vincenzo; Medicinal Chemistry Research; vol. 7; nb. 2; (1997); p. 76 - 86, View in Reaxys; Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 60; nb. 12; (2007); p. 928 - 933, View in Reaxys

Piras, Sandra; Loriga, Mario; Carta, Antonio; Paglietti, Giuseppe; Costi, M. Paola; Ferrari, Stefania; Journal of Heterocyclic Chemistry; vol. 43; nb. 3; (2006); p. 541 - 548, View in Reaxys

Landwehr, Jens; George, Sven; Karg, Eva-Maria; Poeckel, Daniel; Steinhilber, Dieter; Troschuetz, Reinhard; Werz, Oliver; Journal of Medicinal Chemistry; vol. 49; nb. 14; (2006); p. 4327 - 4332, View in Reaxys

Kuklish, Steven L.; Backer, Ryan T.; Briner, Karin; Doecke, Christopher W.; Husain, Saba; Mullaney, Jeffrey T.; Ornstein, Paul L.; Zgombick, John M.; O'Brien, Thomas P.; Fisher, Matthew J.; Bioorganic and Medicinal Chemistry Letters; vol. 16; nb. 14; (2006); p. 3843 - 3846, View in Reaxys

Moehrle; Azodi; Pharmazie; vol. 61; nb. 10; (2006); p. 815 - 822, View in Reaxys

Takahashi, Toshiyuki; Sakuraba, Aya; Hirohashi, Tomoko; Shibata, Takunobu; Hirose, Masaaki; Haga, Yuji; Nonoshita, Katsumasa; Kanno, Tetsuya; Ito, Junko; Iwaasa, Hisashi; Kanatani, Akio; Fukami, Takehiro; Sato, Nagaaki; Bioorganic and Medicinal Chemistry; vol. 14; nb. 22; (2006); p. 7501 - 7511, View in Reaxys

Petride, Horia; Corbu, Andreea; Florea, Cristina; Petride, Aurica; Udrea, Silvia; Revue Roumaine de Chimie; vol. 51; nb. 7-8; (2006); p. 635 - 642, View in Reaxys

amine, Tab.2, entry 4

Varala, Ravi; Sreelatha, Nuvula; Adapa, Srinivas R.; Synlett; nb. 10; (2006); p. 1549 - 1553, View in Reaxys

Moehrle, Hans; Azodi, Katja; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 8; (2006); p. 1021 - 1034, View in Reaxys

Ruchelman, Alexander L.; Houghton, Peter J.; Zhou, Nai; Liu, Angela; Liu, Leroy F.; LaVoie, Edmond J.; Journal of Medicinal Chemistry; vol. 48; nb. 3; (2005); p. 792 - 804, View in Reaxys

Bohnert, Juergen A.; Kern, Winfried V.; Antimicrobial Agents and Chemotherapy; vol. 49; nb. 2; (2005); p. 849 - 852, View in Reaxys

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6, X=CH2C6H5

Agarwal, Anu; Srivastava, Kumkum; Puri; Chauhan, Prem M.S.; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 12; (2005); p. 3130 - 3132, View in Reaxys

1, Table 1, Entry 5 Verma, Akhilesh K.; Kumar, Rupesh; Chaudhary, Preeti; Saxena, Amit; Shankar, Ravi; Mozumdar, Subho; Chandra, Ramesh; Tetrahedron Letters; vol. 46; nb. 31; (2005); p. 5229 - 5232, View in Reaxys 12d

Yuecel, Baris; Arve, Lars; De Meijere, Armin; Tetrahedron; vol. 61; nb. 48; (2005); p. 11355 - 11373, View in Reaxys

Gomez, Ana M.; Moreno, Eduardo; Uriel, Clara; Jarosz, Slawomir; Valverde, Serafin; Lopez, J. Cristobal; Tetrahedron Asymmetry; vol. 16; nb. 14; (2005); p. 2401 - 2407, View in Reaxys

Angrish, Chetna; Kumar, Anil; Chauhan; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 44; nb. 7; (2005); p. 1515 - 1518, View in Reaxys

educt of IVb

Goekce, Mehtap; Bakir, Goekcen; Sahin, Mustafa Fethi; Kuepeli, Esra; Yesilada, Erdem; ArzneimittelForschung/Drug Research; vol. 55; nb. 6; (2005); p. 318 - 325, View in Reaxys

amine, 3

Becker, Irwin; Journal of Heterocyclic Chemistry; vol. 42; nb. 7; (2005); p. 1289 - 1295, View in Reaxys

290

Patent; SEQUELLA, INC.; WO2005/34857; (2005); (A2) English, View in Reaxys

14b

Patent; Anandan, Sampath K.; Xiao, Ziao-Yi; Patel, Dinesh V.; Ward, John S.; US2005/234033; (2005); (A1) English, View in Reaxys

5, t.2, entry 1

Kumar, Kamal; Zapf, Alexander; Michalik, Dirk; Tillack, Annegret; Heinrich, Timo; Boettcher, Henning; Arlt, Michael; Beller, Matthias; Organic Letters; vol. 6; nb. 1; (2004); p. 7 - 10, View in Reaxys

educt to 3m

Zapol'skii, Viktor A.; Namyslo, Jan C.; Adam, Arnold E. W.; Kaufmann, Dieter E.; Heterocycles; vol. 63; nb. 6; (2004); p. 1281 - 1298, View in Reaxys

35g

Hussenether, Thomas; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and Medicinal Chemistry; vol. 12; nb. 10; (2004); p. 2625 - 2637, View in Reaxys

amine, Tab.1, entry 6

Varala, Ravi; Ramu; Alam, M. Mujahid; Adapa, Srinivas R.; Synlett; nb. 10; (2004); p. 1747 - 1750, View in Reaxys

Lee, Jeewoo; Kang, Sang-Uk; Lim, Ju-Ok; Choi, Hyun-Kyung; Jin, Mi-Kyung; Toth, Attila; Pearce, Larry V.; Tran, Richard; Wang, Yun; Szabo, Tamas; Blumberg, Peter M.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 2; (2004); p. 371 - 385, View in Reaxys

Mahesh, Radhakrishnan; Venkatesha Perumal, Ramachandran; Vijaya Pandi, Pandi; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 20; (2004); p. 5179 - 5181, View in Reaxys

Fedi, Valentina; Altamura, Maria; Balacco, Giuseppe; Canfarini, Franca; Criscuoli, Marco; Giannotti, Danilo; Giolitti, Alessandro; Giuliani, Sandro; Guidi, Antonio; Harmat, Nicholas J. S.; Nannicini, Rossano; Pasqui, Franco; Patacchini, Riccardo; Perrotta, Enzo; Tramontana, Manuela; Triolo, Antonio; Maggi, Carlo Alberto; Journal of Medicinal Chemistry; vol. 47; nb. 27; (2004); p. 6935 - 6947, View in Reaxys

amine, Tab. 3, en- Rataboul, Franck; Zapf, Alexander; Jackstell, Ralf; Harkal, Surendra; Riermeier, Thomas; Monsees, try 16 Axel; Dingerdissen, Uwe; Beller, Matthias; Chemistry - A European Journal; vol. 10; nb. 12; (2004); p. 2983 - 2990, View in Reaxys amine to 5g

El-Emam, Ali A.; Al-Deeb, Omar A.; Al-Omar, Mohamed; Lehmann, Jochen; Bioorganic and Medicinal Chemistry; vol. 12; nb. 19; (2004); p. 5107 - 5113, View in Reaxys

substrate to 7b, 8b

Voronkov, Michael V.; Gontcharov, Alexander V.; Wang, Zhi-Min; Richardson, Paul F.; Kolb, Hartmuth C.; Tetrahedron; vol. 60; nb. 41; (2004); p. 9043 - 9048, View in Reaxys

secondary amine

Lal, Bansi; Gund, Vitthal Genbhau; Bhise, Nandu Baban; Gangopadhyay, Ashok Kumar; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1751 - 1768, View in Reaxys

Starting, Tab. 1/2

Michalik, Dirk; Kumar, Kamal; Zapf, Alexander; Tillack, Annegret; Arlt, Michael; Heinrich, Timo; Beller, Matthias; Tetrahedron Letters; vol. 45; nb. 10; (2004); p. 2057 - 2061, View in Reaxys

educt to 9

Tewari, Amit; Hein, Martin; Zapf, Alexander; Beller, Matthias; Tetrahedron Letters; vol. 45; nb. 41; (2004); p. 7703 - 7707, View in Reaxys

educt to 7, entry 15

Menichincheri, Maria; Bassini, Domenico Fusar; Gude, Markus; Angiolini, Mauro; Tetrahedron Letters; vol. 44; nb. 3; (2003); p. 519 - 522, View in Reaxys

Suzuki, Yuichi; Yamamoto, Noboru; Iimura, Yoichi; Kawano, Koki; Kimura, Teiji; Nagato, Satoshi; Ito, Koichi; Komatsu, Makoto; Norimine, Yoshihiko; Kimura, Manami; Teramoto, Tetsuyuki; Kaneda, Yoshihisa; Hamano, Takeshi; Niidome, Tetsuhiro; Yonaga, Masahiro; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 5; (2003); p. 919 - 922, View in Reaxys

6/337

2016-05-20 15:00:44

2, run j,m

Yadav; Reddy; Basak; Venkat Narsaiah; Tetrahedron Letters; vol. 44; nb. 10; (2003); p. 2217 - 2220, View in Reaxys

7g(tab.1)

Cabon, Gaelle; Gaucher, Berangere; Gegout, Aline; Heulle, Sophie; Masquelin, Thierry; Chimia; vol. 57; nb. 5; (2003); p. 248 - 254, View in Reaxys

Limbeck, Marcus; Guendisch, Daniela; Journal of Heterocyclic Chemistry; vol. 40; nb. 5; (2003); p. 895 900, View in Reaxys

Yadav; Reddy; Basak; Narsaiah; Chemistry Letters; vol. 32; nb. 11; (2003); p. 988 - 989, View in Reaxys

2, X = BnN

Ji, Jianguo; Li, Tao; Bunnelle, William H.; Organic Letters; vol. 5; nb. 24; (2003); p. 4611 - 4614, View in Reaxys

Blanchard, Stephanie; Guillaumet, Gerald; Caubere, Paul; Tetrahedron Letters; vol. 42; nb. 40; (2001); p. 7037 - 7039, View in Reaxys; Guisado, Olga; Martinez, Sonia; Pastor, Joaquin; Tetrahedron Letters; vol. 43; nb. 39; (2002); p. 7105 - 7109, View in Reaxys

Salvatore, Ralph N; Chu, Feixia; Nagle, Advait S; Kapxhiu, Elona A; Cross, Richard M; Jung, Kyung Woon; Tetrahedron; vol. 58; nb. 17; (2002); p. 3329 - 3347, View in Reaxys

19d

Naito, Hiroyuki; Ohsuki, Satoru; Sugimori, Masamichi; Atsumi, Ryo; Minami, Megumi; Nakamura, Yoshihide; Ishii, Mineko; Hirotani, Kenji; Kumazawa, Eiji; Ejima, Akio; Chemical and pharmaceutical bulletin; vol. 50; nb. 4; (2002); p. 453 - 462, View in Reaxys

Holland, Richard; Spencer, John; Deadman, John J.; Synthesis; nb. 16; (2002); p. 2379 - 2382, View in Reaxys

13f

Gomez, Ana M.; Moreno, Eduardo; Valverde, Serafin; Lopez; Tetrahedron Letters; vol. 43; nb. 44; (2002); p. 7863 - 7866, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Chu-Moyer, Margaret Y.; Ballinger, William E.; Beebe, David A.; Berger, Richard; Coutcher, James B.; Day, Wesley W.; Li, Jiancheng; Mylari, Banavara L.; Oates, Peter J.; Weekly, R. Matthew; Journal of Medicinal Chemistry; vol. 45; nb. 2; (2002); p. 511 - 528, View in Reaxys

Am2

Liegeois, Jean-Francois; Eyrolles, Laurence; Ellenbroek, Bart A.; Lejeune, Christel; Carato, Pascal; Bruhwyler, Jacques; Geczy, Joseph; Damas, Jacques; Delarge, Jacques; Journal of Medicinal Chemistry; vol. 45; nb. 23; (2002); p. 5136 - 5149, View in Reaxys

Petasis, Nicos A.; Boral, Sougato; Tetrahedron Letters; vol. 42; nb. 4; (2001); p. 539 - 542, View in Reaxys

Salvatore, Ralph N.; Sahab, Suma; Jung, Kyung Woon; Tetrahedron Letters; vol. 42; nb. 11; (2001); p. 2055 - 2058, View in Reaxys

substrate to A2, B2

Kang, Kyung Ho; Pae, Ae Nim; Choi, Kyung Il; Cho, Yong Seo; Chung, Bong Young; Lee, Jee Eun; Jung, Sun Ho; Koh, Hun Yeong; Lee, Hee-Yoon; Tetrahedron Letters; vol. 42; nb. 6; (2001); p. 1057 1060, View in Reaxys

Onkol; Ito; Yildirim; Erol; Sahin; Archiv der Pharmazie; vol. 334; nb. 1; (2001); p. 17 - 20, View in Reaxys

HN(CH2CH2)2NCH2C6H5

Kossakowski, Jerzy; Jarocka, Monika; Farmaco; vol. 56; nb. 10; (2001); p. 785 - 789, View in Reaxys

amine f

Volovenko; Volovnenko; Tverdokhlebov; Chemistry of Heterocyclic Compounds; vol. 37; nb. 8; (2001); p. 1011 - 1020, View in Reaxys

4; R1=CH2C6H5

Ram; Srivastava; Agarwal; Sharon; Maulik; Journal of the Chemical Society. Perkin Transactions 1; nb. 16; (2001); p. 1953 - 1959, View in Reaxys

15c

Leroy, Vincent; Lee, George E.; Lin, Jiang; Herman, Sandra H.; Lee, Thomas B.; Organic Process Research and Development; vol. 5; nb. 2; (2001); p. 179 - 183, View in Reaxys

starting to 3u (R=Bn)

De Blas, Jesus; Dominguez, Esteban; Ezquerra, Jesus; Tetrahedron Letters; vol. 41; nb. 23; (2000); p. 4567 - 4571, View in Reaxys

amine to 1e

Golebiowski, Adam; Klopfenstein, Sean R.; Chen, Jack J.; Shao, Xia; Tetrahedron Letters; vol. 41; nb. 25; (2000); p. 4841 - 4844, View in Reaxys

(CH2)2N(CH2Ph) (CH2)2

Mikhura; Formanovskii; Russian Journal of Organic Chemistry; vol. 36; nb. 1; (2000); p. 64 - 68, View in Reaxys

Olsson; Hansen; Andersson; Tetrahedron Letters; vol. 41; nb. 41; (2000); p. 7947 - 7950, View in Reaxys

Oenkol; Dogruer; Ito; Sahin; Archiv der Pharmazie; vol. 333; nb. 10; (2000); p. 337 - 340, View in Reaxys

7/337

2016-05-20 15:00:44

Ablordeppey, Seth Y.; Fischer, James B.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 8; nb. 8; (2000); p. 2105 - 2111, View in Reaxys

product 9

Sabitha, Gowravaram; Subba Reddy; Abraham, Sunny; Yadav; Tetrahedron Letters; vol. 40; nb. 8; (1999); p. 1569 - 1570, View in Reaxys

Sabitha, Gowravaram; Abraham, Sunny; Reddy, B. V. Subba; Yadav; Synlett; nb. 11; (1999); p. 1745 1746, View in Reaxys

13a

Walczynski, Krzysztof; Guryn, Roman; Zuiderveld, Obbe P.; Timmerman, Henk; Farmaco; vol. 54; nb. 10; (1999); p. 684 - 694, View in Reaxys

Patent-Specific Data (24) Prophetic ComLocation in Patent References pound Page/Page column

Patent; SK CHEMICALS CO. LTD.; Kim, Seon Mi; Lee, Min Hee; Kim, Jae Sun; Jung, Hoe Chul; Lee, So Young; Lee, Soo Min; Kim, Eun Jeong; Park, Eui Sun; Park, Sung Hoon; Lee, Bong Yong; Um, Key An; US2013/137661; (2013); (A1) English, View in Reaxys; Patent; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; US2013/137688; (2013); (A1) English, View in Reaxys; Patent; Huazhong University of Science and Technology; Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd.; JIANG, Fengchao; ZHOU, Ping; CHEN, Jianguo; WANG, Yue; CAO, Baoshuai; YAN, Jia; EP2682390; (2014); (A1) English, View in Reaxys; Patent; Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd.; Huazhong University of Science and Technology; JIANG, Fengchao; ZHOU, Ping; CHEN, Jianguo; WANG, Yue; CAO, Baoshuai; YAN, Jia; US2014/4155; (2014); (A1) English, View in Reaxys; Patent; Genentech, Inc.; Babu, Srinivasan; Cheng, Zhigang; Gosselin, Francis; Hidber, Pirmin; Hoffmann, Ursula; Humphries, Theresa; Reents, Reinhard; Tian, Qingping; Yajima, Herbert; US2014/100366; (2014); (A1) English, View in Reaxys; Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; WANG, Kai; EP2725024; (2014); (A1) English, View in Reaxys; Patent; Shen, Jianhua; Wang, Yiping; Wang, Kai; US2014/171431; (2014); (A1) English, View in Reaxys; Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Kaufman, Michael D.; Patt, William C.; Ahn, YuMi; US2014/275016; (2014); (A1) English, View in Reaxys; Patent; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); (A1) English, View in Reaxys; Patent; National Defense Medical Center; Huang, Hsu-Shan; Chen, Tsung-Chih; Chen, Shiang-Jiun; Chen, Chun-Liang; Lee, Chia-Chung; US2015/197492; (2015); (A1) English, View in Reaxys Patent; SANOFI; US2012/10208; (2012); (A1) English, View in Reaxys Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CORMINBOEUF, Olivier; HEIDMANN, Bibia; SIEGRIST, Romain; WO2011/83413; (2011); (A1) English, View in Reaxys Patent; SANOFI-AVENTIS; US2010/152157; (2010); (A1) English, View in Reaxys Patent; SANOFI-AVENTIS; US2010/179154; (2010); (A1) English, View in Reaxys Patent; FOREST LABORATORIES HOLDINGS LIMITED; US2009/239848; (2009); (A1) English, View in Reaxys Patent; CHOI, Kyung Il; Nam, Ghilsoo; Kim, Hye Ran; Rhim, Hyewhon; Seo, Seon Hee; Kim, Yoon Jee; Shin, Hee Sup; Kim, Dong Jin; Pae, Ae Nim; Chung, Hye Jin; Cho, Yong Seo; Choo, Hyunah; Roh, Eun Joo; Kang, Soon Bang; Shin, Kye Jung; Hahn, Hoh Gyu; Shin, Dong Yun; Cheong, Chan Seong; Nam, Kee Dal; Kang, Yong Koo; Lee, Jae Kyun; Park, Woong Seo; Kim, Youngsoo; Kim, Eunice Eun-Kyeong; Kim, Key-Sun; Chung, Hesson; Keum, Gyo Chang; Lee, Cheolju; Choi, Kee Hyun; US2009/325979; (2009); (A1) English, View in Reaxys Patent; JANSSEN PHARMACEUTICA NV; WO2008/90200; (2008); (A2) English, View in Reaxys Patent; SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A.; WO2007/96251; (2007); (A1) English, View in Reaxys Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/67401; (2006); (A1) English, View in Reaxys Patent; JANSSEN PHARMACEUTICA N.V.; WO2004/56805; (2004); (A1) English, View in Reaxys

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Patent; ACTELION PHARMACEUTICALS LTD; WO2004/99179; (2004); (A1) English, View in Reaxys Patent; Zhao, Matthew M.; Yin, Jingjun; US2004/23979; (2004); (A1) English, View in Reaxys Patent; Nicolai, Eric; Curtet, Sophie; Sicsic, James; Lezoualc'h, Frank; Fischemeister, Rodolphe; Langlois, Michel; Maillet, Magali; Launay, Michele; US2004/58933; (2004); (A1) English, View in Reaxys prophetic product

Patent; Takasago International Corporation; US6365776; (2002); (B1) English, View in Reaxys; Patent; A. H. Robins Company, Incorporated; US4826866; (1989); (A1) English, View in Reaxys; Patent; Zambon Group S.p.A.; US4983606; (1991); (A1) English, View in Reaxys; Patent; Lion Bioscience AG; US6515122; (2003); (B1) English, View in Reaxys; Patent; DROPIC, Societe Civile de gestion de droits de Propriete Industrielle; US4760062; (1988); (A1) English, View in Reaxys; Patent; ELI LILLY AND COMPANY; EP825164; (1998); (A2) English, View in Reaxys Patent; Scios, Inc.; US6340685; (2002); (B1) English, View in Reaxys Patent; Shiseido Co, Ltd.; US6339154; (2002); (B1) English, View in Reaxys Patent; Bristol-Myers Squibb Company; US6344450; (2002); (B1) English, View in Reaxys Patent; Solvay Pharmaceuticals GmbH; EP1176144; (2002); (A1) German, View in Reaxys Patent; Takeda Chemical Industries, Ltd.; EP1180513; (2002); (A1) English, View in Reaxys Patent; The Jordanian Pharmaceutical Manufacturing and Medical Equipment Co.Ltd.; EP1219614; (2002); (A1) English, View in Reaxys Patent; Sankyo Company Limited; EP1243589; (2002); (A1) English, View in Reaxys Patent; Bayer Aktiengesellschaft; EP1174431; (2002); (A2) German, View in Reaxys Patent; Kyorin Pharmaceutical Co., Ltd.; US6348461; (2002); (B1) English, View in Reaxys

Derivative (7) Comment (Derivative)

References

Hydrochlorid: F: 251grad

Menaux et al.; Ingenieur Chimiste (Brussels); vol. 54; (1973); p. 54, View in Reaxys

N-Benzyl-piperazin*I2 C11H16N2*I2: Zers.-P.: 62-64grad; zitronengelb; IR

Okishi et al.; Journal of Inorganic and Nuclear Chemistry; vol. 35; (1973); p. 101,102,103, View in Reaxys

Dihydrochlorid: F: 252-253grad (unkorr); aus A.

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

Dihydrochlorid: B.: 1-Benzyl-4ethoxycarbonylpiperazin, 1. Ethylmagnesiumbromid (Bzl., 4h, Raumt.; dann 4h, Kochen), 2. W.

Dimmock et al.; Canadian Journal of Chemistry; vol. 47; nb. 13; (1969); p. 2413, View in Reaxys

Dihydrochlorid: B.; F: 259grad (Zers.)

Zikolova et al.; Farmatsiya (Sofia, Bulgaria); vol. 18; nb. 3; (1968); p. 17,18-24; Chem.Abstr.; vol. 71; nb. 38905c; (1969), View in Reaxys

Pikrat: P

Masuzawa et al.; Bulletin of the Chemical Society of Japan; vol. 40; (1967); p. 244, View in Reaxys

Dihydrochlorid: F: 252-255grad (Zers.; unkorr.)

Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys

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2016-05-20 15:00:44

Melting Point (1) 1 of 1

Melting Point [°C]

230

Patent; BASF Aktiengesellschaft; US5849743; (1998); (A1) English, View in Reaxys Boiling Point (18) Boiling Point [°C] Pressure (Boiling Point) [Torr] 131 - 134

References Wang, Bao-Lei; Zhan, Yi-Zhou; Zhang, Li-Yuan; Zhang, Yan; Zhang, Xiao; Li, ZhengMing; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; nb. 1; (2016); p. 48 - 54, View in Reaxys

131 - 134

Wang, Bao-Lei; Liu, Xing-Hai; Zhang, Xiu-Lan; Zhang, Ji-Feng; Song, Hai-Bin; Li, Zheng-Ming; Chemical Biology and Drug Design; vol. 78; nb. 1; (2011); p. 42 - 49, View in Reaxys

120 - 123

Caproiu, Miron; Florea, Cristina; Galli, Carlo; Petride, Aurica; Petride, Horia; European Journal of Organic Chemistry; nb. 6; (2000); p. 1037 - 1043, View in Reaxys

120

89 - 90

0.1

Zlatoidsky; Maliar; European Journal of Medicinal Chemistry; vol. 31; nb. 9; (1996); p. 669 - 673, View in Reaxys

145 - 147

Baltzly et al.; Journal of the American Chemical Society; vol. 66; (1944); p. 263,265, View in Reaxys; Menaux et al.; Ingenieur Chimiste (Brussels); vol. 54; (1973); p. 54, View in Reaxys

152 - 160

23 - 26

Rylski et al.; Acta Poloniae Pharmaceutica; vol. 28; (1971); p. 267,268, View in Reaxys

137 - 145

Rylski et al.; Acta Poloniae Pharmaceutica; vol. 27; (1970); p. 357,359, View in Reaxys

110 - 113

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

153 - 154

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

119 - 120

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 20; nb. 4; (1967); p. 289,290-295; Chem.Abstr.; vol. 68; nb. 29674n; (1968), View in Reaxys

140 - 155

Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys

76 - 80

Craig; Journal of the Chemical Society; (1959); p. 3634, View in Reaxys

89 - 96

0.2

Horrom et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 753, View in Reaxys

154 - 160

Baltzly et al.; Journal of the American Chemical Society; vol. 66; (1944); p. 263,265, View in Reaxys

127 - 130

Baltzly et al.; Journal of the American Chemical Society; vol. 66; (1944); p. 263,265, View in Reaxys

122 - 124

2.5

Craig; Young; Org. Synth. Coll. Vol. V; <1973> 88, View in Reaxys

Refractive Index (6) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.545

Menaux et al.; Ingenieur Chimiste (Brussels); vol. 54; (1973); p. 54, View in Reaxys

1.548

589

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

1.5455

589

Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys

10/337

2016-05-20 15:00:44

1.5485

589

Craig; Journal of the Chemical Society; (1959); p. 3634, View in Reaxys

1.544

589

Craig; Journal of the Chemical Society; (1959); p. 3634, View in Reaxys

1.543

589

Horrom et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 753, View in Reaxys

Density (1) 1 of 1

Density [g·cm-3]

1.0348

Measurement Temperature [°C]

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys Association (MCS) (1) 1 of 1

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

phosphate buffer; water-d2; water; dimethylsulfoxide-d6

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

Bcl-xL protein

Barelier, Sarah; Pons, Julien; Marcillat, Olivier; Lancelin, Jean-Marc; Krimm, Isabelle; Journal of Medicinal Chemistry; vol. 53; nb. 6; (2010); p. 2577 - 2588, View in Reaxys Chromatographic Data (1) Chromatographic References data LC (Liquid chromatography)

Jeong, Eun Sook; Kim, So-Hee; Cha, Eun-Ju; Lee, Kang Mi; Kim, Ho Jun; Lee, Sang-Won; Kwon, OhSeung; Lee, Jaeick; Rapid Communications in Mass Spectrometry; vol. 29; nb. 4; (2015); p. 367 - 384, View in Reaxys; Jeong, Eun Sook; Kim, So-Hee; Cha, Eun-Ju; Lee, Kang Mi; Kim, Ho Jun; Lee, SangWon; Kwon, Oh-Seung; Lee, Jaeick; Rapid Communications in Mass Spectrometry; vol. 29; nb. 4; (2015); p. 367 - 384, View in Reaxys

Crystal Property Description (6) Colour & Other Location Properties yellow

supporting information

colourless

References Tyagi, Vipin; Gupta, Ashok Kumar; Synthetic Communications; vol. 44; nb. 4; (2014); p. 493 - 499, View in Reaxys; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 9; (2016); p. 2380 - 2382, View in Reaxys Wang, Jin; Li, Shuo; Hu, Xiao; Yang, Jian; Organic Preparations and Procedures International; vol. 46; nb. 5; (2014); p. 469 - 474, View in Reaxys; Wang, Baolei; Shi, Yanxia; Zhan, Yizhou; Zhang, Liyuan; Zhang, Yan; Wang, Lizhong; Zhang, Xiao; Li, Yonghong; Li, Zhengming; Li, Baoju; Chinese Journal of Chemistry; vol. 33; nb. 10; (2015); p. 1124 - 1134, View in Reaxys

supporting information

Biannic, Berenger; Bozell, Joseph J.; Organic Letters; vol. 15; nb. 11; (2013); p. 2730 2733, View in Reaxys; Biannic, Berenger; Bozell, Joseph J.; Elder, Thomas; Green Chemistry; vol. 16; nb. 7; (2014); p. 3635 - 3642, View in Reaxys

yellow

colourless

Myochin, Takuya; Kiyose, Kazuki; Hanaoka, Kenjiro; Kojima, Hirotatsu; Terai, Takuya; Nagano, Tetsuo; Journal of the American Chemical Society; vol. 133; nb. 10; (2011); p. 3401 - 3409, View in Reaxys; Wang, Bao-Lei; Liu, Xing-Hai; Zhang, Xiu-Lan; Zhang, Ji-Feng; Song, Hai-Bin; Li, Zheng-Ming; Chemical Biology and Drug Design; vol. 78; nb. 1; (2011); p. 42 - 49, View in Reaxys

white

supporting information

Davies, Stephen G.; Mortimer, Duncan A. B.; Mulvaney, Andrew W.; Russell, Angela J.; Skarphedinsson, Hjalmar; Smith, Andrew D.; Vickers, Richard J.; Organic and Biomolecular Chemistry; vol. 6; nb. 9; (2008); p. 1625 - 1634, View in Reaxys

11/337

2016-05-20 15:00:44

Dissociation Exponent (1) 1 of 1

Type (Dissociation Exponent)

Iozep, A. A.; Il'ina, T. Yu.; Passet, B. V.; Russian Journal of Applied Chemistry; vol. 68; nb. 1part2; (1995); p. 92 95; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 68; nb. 1; (1995); p. 106 - 109, View in Reaxys Electrochemical Behaviour (1) Description (Elec- References trochemical Behaviour) Proton affinity

Iozep, A. A.; Il'ina, T. Yu.; Passet, B. V.; Russian Journal of Applied Chemistry; vol. 68; nb. 1part2; (1995); p. 92 - 95; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 68; nb. 1; (1995); p. 106 109, View in Reaxys

Further Information (4) Description (Fur- References ther Information) Further information

Okishi et al.; Journal of Inorganic and Nuclear Chemistry; vol. 35; (1973); p. 101,102,103, View in Reaxys

Further information

Dimmock et al.; Canadian Journal of Chemistry; vol. 47; nb. 13; (1969); p. 2413, View in Reaxys

Further information

Zikolova et al.; Farmatsiya (Sofia, Bulgaria); vol. 18; nb. 3; (1968); p. 17,18-24; Chem.Abstr.; vol. 71; nb. 38905c; (1969), View in Reaxys

Further information

Masuzawa et al.; Bulletin of the Chemical Society of Japan; vol. 40; (1967); p. 244, View in Reaxys

NMR Spectroscopy (18) 1 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 9; (2016); p. 2380 - 2382, View in Reaxys 2 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

600

Zhou, An; Wu, Hongfei; Pan, Jian; Wang, Xuncui; Li, Jiaming; Wu, Zeyu; Hui, Ailing; Molecules; vol. 20; nb. 1; (2015); p. 1304 - 1318, View in Reaxys 3 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

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Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Wang, Jin; Li, Shuo; Hu, Xiao; Yang, Jian; Organic Preparations and Procedures International; vol. 46; nb. 5; (2014); p. 469 - 474, View in Reaxys 4 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Myochin, Takuya; Kiyose, Kazuki; Hanaoka, Kenjiro; Kojima, Hirotatsu; Terai, Takuya; Nagano, Tetsuo; Journal of the American Chemical Society; vol. 133; nb. 10; (2011); p. 3401 - 3409, View in Reaxys; Stojanovska, Natasha; Kelly, Tamsin; Tahtouh, Mark; Beavis, Alison; Fu, Shanlin; Rapid Communications in Mass Spectrometry; vol. 28; nb. 7; (2014); p. 731 - 740, View in Reaxys 5 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Stojanovska, Natasha; Kelly, Tamsin; Tahtouh, Mark; Beavis, Alison; Fu, Shanlin; Rapid Communications in Mass Spectrometry; vol. 28; nb. 7; (2014); p. 731 - 740, View in Reaxys 6 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Tyagi, Vipin; Gupta, Ashok Kumar; Synthetic Communications; vol. 44; nb. 4; (2014); p. 493 - 499, View in Reaxys 7 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Tyagi, Vipin; Gupta, Ashok Kumar; Synthetic Communications; vol. 44; nb. 4; (2014); p. 493 - 499, View in Reaxys 8 of 18

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy)

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Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Lorentz-Petersen, Linda L. R.; Nordstrom, Lars Ulrik; Madsen, Robert; European Journal of Organic Chemistry; nb. 34; (2012); p. 6752 - 6759, View in Reaxys 9 of 18

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Lorentz-Petersen, Linda L. R.; Nordstrom, Lars Ulrik; Madsen, Robert; European Journal of Organic Chemistry; nb. 34; (2012); p. 6752 - 6759, View in Reaxys 10 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125.8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

200

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

14/337

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Cuppoletti, Andrea; Dagostin, Claudio; Florea, Cristina; Galli, Carlo; Gentili, Patrizia; Lanzalunga, Osvaldo; Petride, Aurica; Petride, Horia; Chemistry - A European Journal; vol. 5; nb. 10; (1999); p. 2993 - 2999, View in Reaxys; Bergbreiter, David E.; Osburn, Philip L.; Li, Chunmei; Organic Letters; vol. 4; nb. 5; (2002); p. 737 - 740, View in Reaxys 14 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Bergbreiter, David E.; Osburn, Philip L.; Li, Chunmei; Organic Letters; vol. 4; nb. 5; (2002); p. 737 - 740, View in Reaxys 15 of 18

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.432

Bergbreiter, David E.; Osburn, Philip L.; Li, Chunmei; Organic Letters; vol. 4; nb. 5; (2002); p. 737 - 740, View in Reaxys 16 of 18

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

299.959

Bergbreiter, David E.; Osburn, Philip L.; Li, Chunmei; Organic Letters; vol. 4; nb. 5; (2002); p. 737 - 740, View in Reaxys 17 of 18

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Caproiu, Miron; Florea, Cristina; Galli, Carlo; Petride, Aurica; Petride, Horia; European Journal of Organic Chemistry; nb. 6; (2000); p. 1037 - 1043, View in Reaxys 18 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy)

15/337

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Protiva; Dlabac; Valchar; et al.; Collection of Czechoslovak Chemical Communications; vol. 51; nb. 1; (1986); p. 156 - 166, View in Reaxys; Caproiu, Miron; Florea, Cristina; Galli, Carlo; Petride, Aurica; Petride, Horia; European Journal of Organic Chemistry; nb. 6; (2000); p. 1037 - 1043, View in Reaxys IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Bands

Location

supporting information

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Stojanovska, Natasha; Kelly, Tamsin; Tahtouh, Mark; Beavis, Alison; Fu, Shanlin; Rapid Communications in Mass Spectrometry; vol. 28; nb. 7; (2014); p. 731 - 740, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

CH-Valenzschwingungsbanden.

Wright; Journal of Organic Chemistry; vol. 24; (1959); p. 1362, View in Reaxys Mass Spectrometry (10) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

electrospray ionisation (ESI); spectrum

Stojanovska, Natasha; Kelly, Tamsin; Tahtouh, Mark; Beavis, Alison; Fu, Shanlin; Rapid Communications in Mass Spectrometry; vol. 28; nb. 7; (2014); p. 731 - 740, View in Reaxys; Jeong, Eun Sook; Kim, So-Hee; Cha, Eun-Ju; Lee, Kang Mi; Kim, Ho Jun; Lee, Sang-Won; Kwon, Oh-Seung; Lee, Jaeick; Rapid Communications in Mass Spectrometry; vol. 29; nb. 4; (2015); p. 367 - 384, View in Reaxys; Wang, Jin; Li, Shuo; Hu, Xiao; Yang, Jian; Organic Preparations and Procedures International; vol. 46; nb. 5; (2014); p. 469 - 474, View in Reaxys

liquid chromatography mass spectrometry (LCMS); electrospray ionisation (ESI); spectrum

Jeong, Eun Sook; Kim, So-Hee; Cha, Eun-Ju; Lee, Kang Mi; Kim, Ho Jun; Lee, Sang-Won; Kwon, Oh-Seung; Lee, Jaeick; Rapid Communications in Mass Spectrometry; vol. 29; nb. 4; (2015); p. 367 - 384, View in Reaxys

tandem mass spectrometry; fragmentation pattern; spectrum

Stojanovska, Natasha; Kelly, Tamsin; Tahtouh, Mark; Beavis, Alison; Fu, Shanlin; Rapid Communications in Mass Spectrometry; vol. 28; nb. 7; (2014); p. 731 - 740, View in Reaxys

EI (Electron impact); GCMS (Gas chromatography mass spectrometry); Spectrum

Msimanga, Huggins Z.; Everhart, Gregory P.; Spectroscopy Letters; vol. 45; nb. 3; (2012); p. 161 - 166, View in Reaxys

gas chromatography mass spectrometry (GCMS); spectrum

Lorentz-Petersen, Linda L. R.; Nordstrom, Lars Ulrik; Madsen, Robert; European Journal of Organic Chemistry; nb. 34; (2012); p. 6752 - 6759, View in Reaxys

LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation); Spectrum

Myochin, Takuya; Kiyose, Kazuki; Hanaoka, Kenjiro; Kojima, Hirotatsu; Terai, Takuya; Nagano, Tetsuo; Journal of the American Chemical Society; vol. 133; nb. 10; (2011); p. 3401 - 3409, View in Reaxys

CID (collision-induced dissociation); ESI (Elec-

Chai, Yunfeng; Sun, Hezhi; Pan, Yuanjiang; Sun, Cuirong; Journal of the American Society for Mass Spectrometry; vol. 22; nb. 9; (2011); p. 1526 - 1533, View in Reaxys

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trospray ionisation); IT (ion trap); Spectrum ESI (Electrospray ionisation); CID (collision-induced dissociation); Spectrum

Chai, Yunfeng; Jiang, Kezhi; Pan, Yuanjiang; Journal of Mass Spectrometry; vol. 45; nb. 5; (2010); p. 496 - 503, View in Reaxys

HRMS (High resolution mass spectrometry); TOFMS (Time of flight mass spectrum); ESI (Electrospray ionisation); LCMS (Liquid chromatography mass spectrometry); Spectrum

Vonaparti; Lyris; Angelis; Panderi; Koupparis; Tsantili-Kakoulidou; Peters; Nielen; Georgakopoulos; Rapid Communications in Mass Spectrometry; vol. 24; nb. 11; (2010); p. 1595 - 1609, View in Reaxys

LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation); Tandem mass spectrometry; Spectrum

mol peak

Thoerngren, John-Olof; Oestervall, Fredrik; Garle, Mats; Journal of Mass Spectrometry; vol. 43; nb. 7; (2008); p. 980 - 992, View in Reaxys

Pharmacological Data (25) 1 of 25

Comment (Pharmacological Data)

Bioactivities present

Patent; Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.); US6339091; (2002); (B1) English, View in Reaxys; Patent; Scios, Inc.; US6340685; (2002); (B1) English, View in Reaxys; Patent; Takasago International Corporation; US6365776; (2002); (B1) English, View in Reaxys; Patent; Aventis Pharma Deutschland GmbH; US6369088; (2002); (B2) English, View in Reaxys; Patent; Dr. Karl Thomae GmbH; US6344/449; (2002); (B1) English, View in Reaxys; Patent; THE UPJOHN COMPANY; EP263213; (1988); (A1) English, View in Reaxys; Patent; THE WELLCOME FOUNDATION LIMITED; EP459819; (1991); (A2) English, View in Reaxys; Patent; MARION MERRELL DOW INC.; EP486734; (1992); (A1) English, View in Reaxys; Aschwanden; Kyburz; Schoenholzer; Helvetica Chimica Acta; vol. 59; nb. 4; (1976); p. 1245 - 1252, View in Reaxys; Seidlova,V. et al.; Collection of Czechoslovak Chemical Communications; vol. 34; nb. 8; (1969); p. 2258 - 2277, View in Reaxys; Patent; F. HOFFMANN-LA ROCHE AG; EP748800; (1996); (A3) English, View in Reaxys; Patent; SUMITOMO PHARMACEUTICALS COMPANY, LIMITED; EP947515; (1999); (A1) English, View in Reaxys; Sauter,F. et al.; Monatshefte fuer Chemie; vol. 98; nb. 5; (1967); p. 2089 - 2096, View in Reaxys; Patent; Parke, Davis and Company; US3951982; (1976); (A1) English, View in Reaxys; Patent; Parke, Davis and Company; US3954734; (1976); (A1) English, View in Reaxys; Patent; Tokyo Tanabe Company, Ltd.; US3957790; (1976); (A1) English, View in Reaxys; Uno; Kurokawa; Natsuka; et al.; Chemical and Pharmaceutical Bulletin; vol. 24; nb. 4; (1976); p. 632 - 643, View in Reaxys; Patent; University of Illinois Foundation; US3987035; (1976); (A1) English, View in Reaxys; Patent; Hoechst Aktiengesellschaft; US4115569; (1978); (A1) English, View in Reaxys; Patent; Hoechst Aktiengesellschaft; US4128643; (1978); (A1) English, View in Reaxys; Patent; Boehringer Ingelheim GmbH; US4213985; (1980); (A1) English, View in Reaxys; Patent; Hoechst Aktiengesellschaft; US4221793; (1980); (A1) English, View in Reaxys; Patent; Pfizer Inc.; US4337250; (1982); (A1) English, View in Reaxys; Patent; American Cyanamid Company; US4421753; (1983); (A1) English, View in Reaxys; Patent; ICI Americas Inc.; US4247549; (1981); (A1) English, View in Reaxys; Patent; Pfizer Inc.; US4255426; (1981); (A1) English, View in Reaxys; Patent; Laboratorie Roger Bellon; Dainippon Pharmaceutical; US4292317; (1981); (A1) English, View in Reaxys; Patent; Sterling Drug Inc.; US4308382; (1981); (A1) English, View in Reaxys; Patent; Otsuka Pharmaceutical Co., Ltd.; US4454130; (1984); (A1) English, View in Reaxys; Patent; Otsuka Pharmaceutical Co., Ltd.; US4455422; (1984); (A1) English, View in Reaxys; Patent; Merck and Co., Inc.; US4456604; (1984); (A1) English, View in Reaxys; Patent; Bjork; Anders K.; Abramo; Aina L.; Christensson; Erik G.; US4492698; (1985); (A1) English, View in Reaxys; Patent; Rhone-Poulenc Sante; US4529728; (1985); (A1) English, View in Reaxys; Patent; American Cyanamid Company; US4562189; (1985); (A1) English, View in Reaxys; Patent; American Cyanamid Company; US4576943; (1986); (A1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US4590189; (1986); (A1) English, View in Reaxys; Patent; Mitsubishi Yuka Pharmaceutical Co., Ltd.; US4607034; (1986); (A1) English, View in Reaxys; Patent; Boehringer Mannheim GmbH; US4616086; (1986); (A1) English, View in Reaxys; Patent; Bjork; Anders K.; Christensson; Erik G.; US4624953; (1986); (A1) English, View in Reaxys; Patent; Eisai Co., Ltd.; EP1099692; (2001); (A1) English, View in Reaxys; Patent; G. D. Searle and Co.; US5298514; (1994); (A1) English, View in Reaxys; Patent; Mitsui Toatsu Chemicals, Incorporated; US5308848; (1994); (A1) English, View in Reaxys; Patent; Pfizer Inc.; US4656174; (1987); (A1) English,

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View in Reaxys; Patent; Hoechst-Roussel Pharmaceuticals Inc.; US4663453; (1987); (A1) English, View in Reaxys; Steiner,G.; Justus Liebigs Annalen der Chemie; (1978); p. 643 - 657, View in Reaxys; Patent; American Cyanamid Company; US4692449; (1987); (A1) English, View in Reaxys; Patent; WELFIDE CORPORATION; EP1308439; (2003); (A1) English, View in Reaxys; DeGraw; Brown; Skinner; Journal of medicinal chemistry; vol. 9; nb. 1; (1966); p. 140 - 142, View in Reaxys; Patent; Ciba-Geigy Corporation; US4804661; (1989); (A1) English, View in Reaxys; Patent; A. H. Robins Company, Incorporated; US4826866; (1989); (A1) English, View in Reaxys; Patent; Sociedad Espanola De Especialidades Terepeuticas, S.A.; US4835156; (1989); (A1) English, View in Reaxys; Herrin; Pauvlik; Schuber; Geiszler; Journal of Medicinal Chemistry; vol. 18; nb. 12; (1975); p. 1216 - 1223, View in Reaxys; Uno,H. et al.; Journal of Medicinal Chemistry; vol. 22; (1979); p. 180 - 183, View in Reaxys; Patent; Ortho Pharmaceutical Corporation; US4876257; (1989); (A1) English, View in Reaxys; Patent; Ortho Pharmaceutical Corporation; US4885300; (1989); (A1) English, View in Reaxys; Patent; Karl Thomae GmbH; US4724236; (1988); (A1) English, View in Reaxys; Patent; Boehringer Ingelheim Ltd.; US4725597; (1988); (A1) English, View in Reaxys; Patent; Otsuka Pharmaceutical Co., Ltd.; US4734416; (1988); (A1) English, View in Reaxys; Patent; Mitsui Petrochemical Industries, Ltd.; US4734418; (1988); (A1) English, View in Reaxys; Patent; Nippon Shoji Kabushiki Kaisha; US5716950; (1998); (A1) English, View in Reaxys; Patent; Zeneca Limited; US5753659; (1998); (A1) English, View in Reaxys; Patent; BASF Aktiengesellschaft; US5773439; (1998); (A1) English, View in Reaxys; Patent; Boehringer Mannheim GmbH; US5786371; (1998); (A1) English, View in Reaxys; Patent; Sumitomo Pharmaceuticals Company, Ltd.; US5843957; (1998); (A1) English, View in Reaxys; Patent; Missbach, Martin; US2001/16207; (2001); (A1) English, View in Reaxys; Patent; Rudolf, Klaus; Eberlein, Wolfgang; Engel, Wolfhard; Pieper, Helmut; Doods, Henri; Hallermayer, Gerhard; Entzeroth, Michael; Wienen, Wolfgang; US2001/36946; (2001); (A1) English, View in Reaxys; Patent; Ikeda, Takafumi; Kawamura, Mitsuhiro; Murase, Noriaki; Nukui, Seiji; Shishido, Yuji; Kawai, Makato; Okumura, Yoshiyuki; US2001/46993; (2001); (A1) English, View in Reaxys; Patent; Schering A.G.; US4906634; (1990); (A1) English, View in Reaxys; Patent; American Cyanamid Company; US4916137; (1990); (A1) English, View in Reaxys; Patent; Ravizza S.p.a.; US4940793; (1990); (A1) English, View in Reaxys; Patent; Ciba-Geigy Corporation; US4945092; (1990); (A1) English, View in Reaxys; Patent; Janssen Pharmaceutica N.V.; US4946843; (1990); (A1) English, View in Reaxys; Patent; Heumann Pharma GmbH and Co.; US4954501; (1990); (A1) English, View in Reaxys; Patent; G. 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Searle and Co.; US4959364; (1990); (A1) English, View in Reaxys; Patent; ADIR Et Cie; US4960778; (1990); (A1) English, View in Reaxys; Patent; American Cyanamid Company; US4963552; (1990); (A1) English, View in Reaxys; Patent; American Cyanamid Co.; US4963553; (1990); (A1) English, View in Reaxys; Patent; Zambon Group S.p.A.; US4983606; (1991); (A1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US4990511; (1991); (A1) English, View in Reaxys; Patent; Janssen Pharmaceutica N.V.; US4992433; (1991); (A1) English, View in Reaxys; Patent; Marion Laboratories, Inc.; US5001160; (1991); (A1) English, View in Reaxys; Patent; Karl Thomae GmbH; US5006522; (1991); (A1) English, View in Reaxys; Robba,M. et al.; Bulletin de la Societe Chimique de France; (1967); p. 4220 - 4235, View in Reaxys; Patent; Schering AG; US5051423; (1991); (A1) English, View in Reaxys; Patent; Pierre Fabre Medicament; US6191130; (2001); (B1) English, View in Reaxys; Patent; Tularik Inc.; US6200977; (2001); (B1) English, View in Reaxys; Patent; Cell Pathways, Inc.; US6200980; (2001); (B1) English, View in Reaxys; Patent; Molecular Geriatrics Corporation; US6214994; (2001); (B1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US6235731; (2001); (B1) English, View in Reaxys; Patent; Recordati S.A., Chemical and Pharmaceutical Company; US6271234; (2001); (B1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US6310107; (2001); (B1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US6319916; (2001); (B1) English, View in Reaxys; Patent; Boehringer Ingelheim Pharma KG; US6323207; (2001); (B1) English, View in Reaxys; Patent; Merck Sharpe and Dohme Ltd.; US5432177; (1995); (A1) English, View in Reaxys; Patent; Merck and Co., Inc.; US5434158; (1995); (A1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US5466689; (1995); (A1) English, View in Reaxys; Patent; Adir et Compagnie; US5512569; (1996); (A1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US5527800; (1996); (A1) English, View in Reaxys; Patent; Pfizer Inc.; US5538984; (1996); (A1) English, View in Reaxys; Patent; Aktiebolaget Astra; US5585378; (1996); (A1) English, View in Reaxys; Patent; Virginia Commonwealth University; US6057371; (2000); (A1) English, View in Reaxys; Das,P.C. et al.; Indian Journal of Chemistry; vol. 6; (1968); p. 691 - 693, View in Reaxys; Patent; Zeneca Limited; US6090813; (2000); (A1) English, View in Reaxys; Patent; Zeneca Limited; US6093718; (2000); (A1) English, View in Reaxys; Patent; Astra Aktiebolag; US6124283; (2000); (A1) English, View in Reaxys; Patent; John Wyeth and Brother, Ltd.; US6127357; (2000); (A1) English, View in Reaxys; Patent; Kowa Co., Ltd.; US6127360; (2000); (A1) English, View in Reaxys; Patent; Pfizer Inc.; US6131226; (2000); (A1) English, View in Reaxys; Patent; UCB, S.A.; US6140501; (2000); (A1) English, View in Reaxys; Patent; Bristol-Myers Squibb Company; US6153611; (2000); (A1) English, View in Reaxys; Patent; Pfizer Inc; US6156752; (2000); (A1) English, View in Reaxys; Patent; Syntex (U.S.A.) 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4713, View in Reaxys; Li, Wanfang; Wu, Xiao-Feng; Chemistry - A European Journal; vol. 21; nb. 42; (2015); p. 14943 - 14948, View in Reaxys; Rehman, Muneeb-Ur; Imran, Muhammad; Zia-Ur-Rehman; Hassan, Abbas; Badshah, Amin; Shah, Afzal; Tahir, Muhammad Nawaz; Shah, Ghani; Journal of Coordination Chemistry; vol. 68; nb. 2; (2015); p. 295 - 307, View in Reaxys; Eleftheriadis, Nikolaos; Neochoritis, Constantinos G.; Leus, Niek G. 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Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 9; (2016); p. 2380 - 2382, View in Reaxys 2 of 25

Comment (Pharmacological Data)

physiological behaviour discussed

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; Randox Laboratories Limited; Benchikh, Elouard; McConnell, Ivan; Lowry, Philip; Fitzgerald, Peter; US2013/224882; (2013); (A1) English, View in Reaxys 4 of 25

Location

Paragraph

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2631231; (2013); (A1) English, View in Reaxys 5 of 25

Effect (Pharmacological Data)

reinstate response to amphetamine self-administration; induction of

Species or Test-System (Pharmacological Data)

Macaca mulatta, rhesus monkey

Sex

male and female

Route of Application

intravenous

Concentration (Pharmacological Data)

0.3 - 0.1 mg/kg

Further Details (Pharmacological Data)

peak response rates induced by an amphetamine prime = 0.51 responses/s; mass of species: 8 - 15 kg

Type (Pharmacological Data)

peak response rate

Value of Type (Pharmacological Data)

69 percent

McClung, Jessica; Fantegrossi, William; Howell, Leonard L.; Psychopharmacology; vol. 210; nb. 1; (2010); p. 75 - 83, View in Reaxys 6 of 25

Effect (Pharmacological Data)

reinstate response to amphetamine self-administration; attenuation of

Species or Test-System (Pharmacological Data)

Macaca mulatta, rhesus monkey

Sex

male and female

Route of Application

intravenous

Concentration (Pharmacological Data)

0.3 - 0.1 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. administered after pre-treatment with fluoxetine (3 mg/kg)

Further Details (Pharmacological Data)

mass of species: 8 - 15 kg

Type (Pharmacological Data)

reduction rate

Value of Type (Pharmacological Data)

43 percent

McClung, Jessica; Fantegrossi, William; Howell, Leonard L.; Psychopharmacology; vol. 210; nb. 1; (2010); p. 75 - 83, View in Reaxys 7 of 25

Effect (Pharmacological Data)

procaspase-3; activation of

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Species or Test-System (Pharmacological Data)

procaspase-3

Method (Pharmacological Data)

[0056] Figure 1. A) In vitro activation of procaspase-3 and active caspase-3 by PAC-1. PAC-1 activates procaspase-3 with an EC50 = 0.22 μM. Error bars represent standard deviations from the mean. B) Cleavage of procaspase-3 to active caspase-3 as induced by PAC-1. Procaspase-3 was recombinantly expressed in E. coli with an N-terminal His-6 tag and purified, lmmunoblotting was performed with an anti-His-6 antibody. In the absence of PAC-1 , no maturation of procaspase-3 is observed. In the presence of 100 μM PAC-1 , cleavage to generate the p19 fragment is observed within 1 hour, and >50percent cleavage is observed after 4 hours.; [00123] Of the compounds evaluated, four induced a significant increase over background in the hydrolysis of the peptidic caspase-3 substrate. Of those four, one showed a strong dose-dependent effect on in vitro procaspase-3 activation. As shown in Figure 1A, this first procaspase activating compound (PAC-1 ) gives half- maximal activation of procaspase-3 at a concentration of 0.22 μM. This compound is not simply increasing the activity of caspase-3 itself, as it has no effect on the catalytic activity of the fully processed caspase-3 enzyme (Figure 1A).; Of those four, one showed a strong dose dependent effect on in vitro procaspase-3 activation. As shown in Figure 1A, this first procaspase-activating compound (PAC-1 ) gives half-maximal activation of procaspase-3 at a concentration of 0.22 μM. This compound is not simply increasing the activity of caspase-3 itself, as it has no effect on the catalytic activity of the fully processed caspase-3 enzyme (Figure 1A).; Figures 1 and 2. The structure of PAC-1 is shown elsewhere in the specification. Fig. 1A) In vitro activation of procaspase-3 and active caspase-3 by PAC-1. PAC-1 activates procaspase-3 with an EC5O = 0.22 μM.; [00193] Table 3. PAC-1 and de-allyl PAC-1 activate procaspase-3 in vitro and induce death in cancer cells in cell culture, but other structural analogues have no procaspase-3 activating effect in vitro and give no induction of death in cell culture.

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

> 50 μmol/l

Location

Page/Page column 55; 60

Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; WO2008/134474; (2008); (A2) English, View in Reaxys 8 of 25

Effect (Pharmacological Data)

cell death; induction of

Species or Test-System (Pharmacological Data)

leukemia HL-60 cells

Method (Pharmacological Data)

Type (Pharmacological Data)

IC50

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Value of Type (Pharmacological Data)

> 100 μmol/l

Location

Page/Page column 55; 60-61

Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; WO2008/134474; (2008); (A2) English, View in Reaxys 9 of 25

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.0percent

Method (Pharmacological Data)

synaptosomes pre-loaded with <3H>norepinephrine added to plate containing title comp.; 30 min at 25 deg C; scintillation counted

Further Details (Pharmacological Data)

non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 1.1E-8 M); cocaine: no effect

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

6.8E-8 mol/l

Results

title comp. strongly stimulated release of norepinephrine

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 10 of 25

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.0percent

Method (Pharmacological Data)

synaptosomes pre-loaded with <3H>5-HT added to plate containing title comp.; 30 min at 25 deg C; scintillation counted

Further Details (Pharmacological Data)

non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 7.9E-7 M); cocaine: no effect; 5-HT: serotonin

Comment (Pharmacological Data)

No effect

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 11 of 25

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

brain crude striatum synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.0percent

Method (Pharmacological Data)

synaptosomes pre-loaded with <3H>dopamine added to plate containing title comp.; 5 min at 25 deg C; scintillation counted

Further Details (Pharmacological Data)

non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 2.80E-8 M); cocaine: no effect

Type (Pharmacological Data)

EC50

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Value of Type (Pharmacological Data)

6.0E-7 mol/l

Results

title comp. strongly stimulated release of dopamine

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 12 of 25

Effect (Pharmacological Data)

monoamine re-uptake; inhibition of

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.0percent

Method (Pharmacological Data)

synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>norepinephrine addition; 5 min at 37 deg C; scintillation counted

Further Details (Pharmacological Data)

non-specific uptake obtained at 0 deg C; positive control: cocaine (IC50 = 3.4E-7 M) and methamphetamine (IC50 = 2.0E-7 M)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

6.2E-7 mol/l

Results

title comp. strongly inhibited norepinephrine re-uptake

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 13 of 25

Effect (Pharmacological Data)

monoamine re-uptake; inhibition of

Species or Test-System (Pharmacological Data)

brain crude striatum synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.0percent

Method (Pharmacological Data)

synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>dopamine addition; 5 min at 37 deg C; scintillation counted

Further Details (Pharmacological Data)

non-specific uptake obtained in the presence of GBR12909; positive control: cocaine (IC50 = 8.5E-7 M) and methamphetamine (IC50 = 3.7E-7 M)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

1.9E-6 mol/l

Results

title comp. strongly inhibited dopamine re-uptake

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 14 of 25

Effect (Pharmacological Data)

monoamine re-uptake; inhibition of

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.0percent

Method (Pharmacological Data)

synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>5-HT addition; 5 min at 37 deg C; scintillation counted

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Further Details (Pharmacological Data)

non-specific uptake obtained in the presence of citalopram; positive control: cocaine (IC50 = 2.1E-6 M) and methamphetamine (IC50 = 4.0E-6 M); 5-HT: serotonin

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

2.0E-5 mol/l

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 15 of 25

Effect (Pharmacological Data)

monoamine transporter; interaction with

Species or Test-System (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction incubated with title comp. and 2 nmol/l <3H>DHTBZ for 4 h at 25 deg C; rapid filtration; liquid scintillation counting

Further Details (Pharmacological Data)

DHTBZ: dihydrotetrabenazine; VMAT2: vesicular monoamine transporter type 2; IC50 for title comp. inhibition of <3H>DHTBZ binding

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.; Journal of Pharmacology and Experimental Therapeutics; vol. 319; nb. 1; (2006); p. 237 - 246, View in Reaxys 16 of 25

Effect (Pharmacological Data)

monoamine transporter; interaction with

Species or Test-System (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction incubated with title comp. and 60 nmol/l <3H>dopamine for 5 min at 25 deg C; rapid filtration; liquid scintillation counting

Further Details (Pharmacological Data)

DHTBZ: dihydrotetrabenazine; VMAT2: vesicular monoamine transporter type 2; IC50 for title comp. inhibition of <3H>dopamine uptake

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction preloaded with 60 nmol/l <3H>tyramine for 20 min at 25 deg C, incubated with title comp. for 2 min at 25 deg C; rapid filtration; liquid scintillation counting; <3H>tyramine release evaluated

Further Details (Pharmacological Data)

EC50 for title comp. inhibition of <3H>tyramine release

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

> 100 μmol/l

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18 of 25

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction preloaded with 60 nmol/l <3H>dopamine for 20 min at 25 deg C, incubated with title comp. for 10 min at 25 deg C; rapid filtration; liquid scintillation counting; <3H>dopamine release evaluated

Further Details (Pharmacological Data)

EC50 for title comp. inhibition of <3H>dopamine release

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Effect (Pharmacological Data)

procaspase-3; activation of

Species or Test-System (Pharmacological Data)

procaspase-3 of Homo sapiens, human

Method (Pharmacological Data)

EXAMPLE 3. Analogs of PAC-1.[00126] Analog compounds of PAC-1 were prepared and assessed for the capability to directly activate purified procaspase-3 in vitro. EPO Table 2. Activity of PAC-1 and analog compounds.; [00152] Several derivatives of PAC-1 were synthesized and evaluated for both their procaspase-3 activating properties and their effects on cancer cells in cell culture (Table 3). The PAC-1 derivative that lacks the ally. group (de-allyl PAC-1) is able to induce procaspase-3 activation and cell death at levels similar to PAC-1. However, all other derivatives showed no activity in either assay. Thus, while it appears the allyl group is dispensable for biological activity, the phenolic hydroxyl and aromatic rings are all critical for PAC-1 activity. This data is also consistent with the proposed mechanism of action of PAC-1; compounds that do not activate procaspase-3 in vitro have no proapoptotic effect on cancer cells in culture.; [00163] Table 3. PAC-1 and de-allyl PAC-1 activate procaspase-3 in vitro and induce death in cancer cells in cell culture, but other structural analogues have no procaspase-3 activating effect in vitro and give no induction of death in cell culture.

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 50 μmol/l

Location

Page/Page column 34

Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; WO2006/128173; (2006); (A2) English, View in Reaxys 20 of 25

Effect (Pharmacological Data)

cell death; induction of

Species or Test-System (Pharmacological Data)

leukemia (HL-60) cells of human

Method (Pharmacological Data)

[00152] Several derivatives of PAC-1 were synthesized and evaluated for both their procaspase-3 activating properties and their effects on cancer cells in cell culture (Table 3). The PAC-1 derivative that lacks the ally. group (de-allyl PAC-1) is able to induce procaspase-3 activation and cell death at levels similar to PAC-1. However, all other derivatives showed no activity in either assay. Thus, while it appears the allyl group is dispensable for biological activity, the phenolic hydroxyl and aromatic rings are all critical for PAC-1 activity. This data is also consistent with the proposed mechanism of action of PAC-1; compounds that do not activate procaspase-3 in vitro have no proapoptotic effect on cancer cells in culture.; [00163] Table 3. PAC-1 and de-allyl PAC-1 activate procaspase-3 in vitro and induce death in cancer cells in cell culture, but other structural analogues have no procaspase-3 activating effect in vitro and give no induction of death in cell culture.

Type (Pharmacological Data)

IC50

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Value of Type (Pharmacological Data)

> 100 μmol/l

Location

Page/Page column 43; 48-49

Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; WO2006/128173; (2006); (A2) English, View in Reaxys 21 of 25

Effect (Pharmacological Data)

bacterial resistance; inhibition of

Species or Test-System (Pharmacological Data)

Escherichia coli 3-AG100MKX

Method (Pharmacological Data)

cells incubated with levofloxacin in presence of title comp.; levofloxacin MIC determined by spectrofotometric assay

Further Details (Pharmacological Data)

3-AG100MKX: AcrAB-overexpressing gyrA mutant derived from AG100MKX (AG100 marA::Kmr); AcrAB: efflux pump; reference comp.: Phe-Arg-β-naphtylamide

Results

title comp. conc. to reduce levofloxacin MIC by 4-fold was 250 μg/ml

Bohnert, Juergen A.; Kern, Winfried V.; Antimicrobial Agents and Chemotherapy; vol. 49; nb. 2; (2005); p. 849 852, View in Reaxys 22 of 25

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human acetylcholinesterase

Concentration (Pharmacological Data)

<= 100 μmol/l

Method (Pharmacological Data)

AChE treated with title comp.; pH 7.4; acetylcholine used as substrate; AChE activity determined at 15-s intervals for 2 min

Further Details (Pharmacological Data)

AChE: acetylcholinesterase

Comment (Pharmacological Data)

No effect

Harel, Michal; Hyatt, Janice L.; Brumshtein, Boris; Morton, Christopher L.; Yoon, Kyoung Jin P.; Wadkins, Randy M.; Silman, Israel; Sussman, Joel L.; Potter, Philip M.; Molecular Pharmacology; vol. 67; nb. 6; (2005); p. 1874 - 1881, View in Reaxys 23 of 25

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

guinea pig brain membranes

Method (Pharmacological Data)

σ1-radioligand binding assay; (+)-<3H>pentazocine as the radioligand; pH 8.0; incubated for 4 h at 37 deg C; quenched; filtered; radioactivity on filter determined by scintillation spectrometer

Further Details (Pharmacological Data)

nonspecific binding was determined in the presence of 10 μmol/l haloperidol; Ki value was determined from three to five separate determinations

Results

Ki > 10 000 nmol/l

Ablordeppey, Seth Y.; Fischer, James B.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 8; nb. 8; (2000); p. 2105 - 2111, View in Reaxys 24 of 25

Comment (Pharmacological Data)

5-HT2 and 5-HT1C receptors binding affinity (frontal cortical regions of male rats)

Herndon, Jeff L.; Ismaiel, Abd; Ingher, Stacy P.; Teitler, M.; Glennon, Richard A.; Journal of Medicinal Chemistry; vol. 35; nb. 26; (1992); p. 4903 - 4910, View in Reaxys 25 of 25

Comment (Pharmacological Data)

affinity to σ receptors (guinea pig brain)

Glennon; Yousif; Ismaiel; El-Ashmawy; Herndon; Fischer; Server; Howie; Journal of Medicinal Chemistry; vol. 34; nb. 12; (1991); p. 3360 - 3365, View in Reaxys

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Reaxys ID 155493 View in Reaxys

2/323 CAS Registry Number: 23145-88-2 Chemical Name: 1-[(4-chlorophenyl)methyl]piperazine; 1-(4chlorobenzyl)piperazine Linear Structure Formula: C11H15N2Cl Molecular Formula: C11H15ClN2 Molecular Weight: 210.706 Type of Substance: heterocyclic InChI Key: GSJXJZOWHSTWOX-UHFFFAOYSA-N Note:

NH N

Substance Label (22) Label References 3b

Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 9; (2016); p. 2380 - 2382, View in Reaxys

Ferte, Jacques; Kuehnel, Jean-Marc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 - 489, View in Reaxys; Congiu, Cenzo; Onnis, Valentina; Deplano, Alessandro; Balboni, Gianfranco; Dedeoglu, Nurcan; Supuran, Claudiu T.; Bioorganic and Medicinal Chemistry Letters; vol. 25; nb. 18; (2015); p. 3850 - 3853; Art.No: 22949, View in Reaxys

Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 2086, View in Reaxys; Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

Zhou, An; Wu, Hongfei; Pan, Jian; Wang, Xuncui; Li, Jiaming; Wu, Zeyu; Hui, Ailing; Molecules; vol. 20; nb. 1; (2015); p. 1304 - 1318, View in Reaxys

Flanagan, Jack U.; Atwell, Graham J.; Heinrich, Daniel M.; Brooke, Darby G.; Silva, Shevan; Rigoreau, Laurent J.M.; Trivier, Elisabeth; Turnbull, Andrew P.; Raynham, Tony; Jamieson, Stephen M.F.; Denny, William A.; Bioorganic and Medicinal Chemistry; vol. 22; nb. 3; (2014); p. 967 - 977, View in Reaxys

Jallapally, Anvesh; Addla, Dinesh; Yogeeswari, Perumal; Sriram, Dharmarajan; Kantevari, Srinivas; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 23; (2014); p. 5520 - 5524, View in Reaxys

Bali, Alka; Reddy, A. C. Dinesh Kumar; Medicinal Chemistry Research; vol. 22; nb. 1; (2013); p. 382 - 391, View in Reaxys

45d

13d

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

25e

Bavetsias, Vassilios; Crumpler, Simon; Sun, Chongbo; Avery, Sian; Atrash, Butrus; Faisal, Amir; Moore, Andrew S.; Brown, Nathan; Sheldrake, Peter W.; Bush, Katherine; Henley, Alan; Box, Gary; Valenti, Melanie; De Haven Brandon, Alexis; Raynaud, Florence I.; Workman, Paul; Eccles, Suzanne A.; Linardopoulos, Spiros; Blagg, Julian; Kosmopoulou, Magda; Bayliss, Richard; Journal of Medicinal Chemistry; vol. 55; nb. 20; (2012); p. 8721 - 8734,14, View in Reaxys; Bavetsias, Vassilios; Crumpler, Simon; Sun, Chongbo; Avery, Sian; Atrash, Butrus; Faisal, Amir; Moore, Andrew S.; Kosmopoulou, Magda; Brown, Nathan; Sheldrake, Peter W.; Bush, Katherine; Henley, Alan; Box, Gary; Valenti, Melanie; De Haven Brandon, Alexis; Raynaud, Florence I.; Workman, Paul; Eccles, Suzanne A.; Bayliss, Richard; Linardopoulos, Spiros; Blagg, Julian; Journal of Medicinal Chemistry; vol. 55; nb. 20; (2012); p. 8721 - 8734, View in Reaxys

Moehrle; Azodi; Pharmazie; vol. 61; nb. 10; (2006); p. 815 - 822, View in Reaxys

He, Feng-Qi; Liu, Xing-Hai; Wang, Bao-Lei; Li, Zheng-Ming; Journal of Chemical Research; nb. 12; (2006); p. 809 - 811, View in Reaxys

Moehrle, Hans; Azodi, Katja; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 8; (2006); p. 1021 - 1034, View in Reaxys

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2016-05-20 15:00:44

pCBP

Bohnert, Juergen A.; Kern, Winfried V.; Antimicrobial Agents and Chemotherapy; vol. 49; nb. 2; (2005); p. 849 - 852, View in Reaxys

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 4331, View in Reaxys

Zhao, He; Zhang, Xiaoyan; Hodgetts, Kevin; Thurkauf, Andrew; Hammer, Jack; Chandrasekhar, Jayaraman; Kieltyka, Andrzej; Brodbeck, Robbin; Rachwal, Stanislaw; Primus, Renee; Manly, Charles; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 4; (2003); p. 701 - 704, View in Reaxys

11, R&3%=4-Cl

Zhao, He; Thurkauf, Andrew; He, Xiaoshu; Hodgetts, Kevin; Zhang, Xiaoyan; Rachwal, Stanislaw; Kover, Renata X.; Hutchison, Alan; Peterson, John; Kieltyka, Andrzej; Brodbeck, Robbin; Primus, Renee; Wasley, Jan W.F.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 21; (2002); p. 3105 - 3109, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Zhao, He; He, Xiaoshu; Thurkauf, Andrew; Hoffman, Diane; Kieltyka, Andrzej; Brodbeck, Robbin; Primus, Renee; Wasley, Jan W.F.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 21; (2002); p. 3111 - 3115, View in Reaxys

10, 18 R1=Cl

Zhao, He; Thurkauf, Andrew; Braun, Julia; Brodbeck, Robin; Kieltyka, Andrzej; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 18; (2000); p. 2119 - 2122, View in Reaxys

Patent-Specific Data (6) Prophetic ComLocation in Patent References pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys Patent; Scios, Inc.; US6340685; (2002); (B1) English, View in Reaxys Patent; Schering Aktiengesellschaft; EP1254899; (2002); (A2) English, View in Reaxys Patent; Neurogen Corporation; US6355644; (2002); (B1) English, View in Reaxys Claim

Patent; Neurogen Corporation; US5859246; (1999); (A1) English, View in Reaxys

Derivative (3) Comment (Derivative)

References

Methansulfonat: F: 181-182grad

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys

Dihydrochlorid: F: 293.5-295.5grad (unkorr., aus A.)

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

*2HCl: F: 240-243grad

Patent; U.S. Vit. Pharm.; BE617599; (1962); Chem.Abstr.; vol. 59; nb. 646; (1963), View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

150

Solvent (Melting Point)

methanol

Bali, Alka; Reddy, A. C. Dinesh Kumar; Medicinal Chemistry Research; vol. 22; nb. 1; (2013); p. 382 - 391, View in Reaxys 2 of 3

Melting Point [°C]

150

Melting Point [°C]

93 - 97

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys Boiling Point (10) Boiling Point [°C] Pressure (Boiling Point) [Torr]

References

58/337

2016-05-20 15:00:44

138 - 141

Wang, Bao-Lei; Liu, Xing-Hai; Zhang, Xiu-Lan; Zhang, Ji-Feng; Song, Hai-Bin; Li, Zheng-Ming; Chemical Biology and Drug Design; vol. 78; nb. 1; (2011); p. 42 - 49, View in Reaxys

114 - 116

0.2

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

104 - 106

0.1

Buckle, Derek R.; Outred, D. James; Smith, Harry; Spicer, Barbara A.; Journal of Medicinal Chemistry; vol. 27; nb. 11; (1984); p. 1452 - 1457, View in Reaxys

124 - 126

0.6

Pesson et al.; European Journal of Medicinal Chemistry; vol. 10; (1975); p. 567,570, View in Reaxys

160 - 162

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys

132 - 135

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

122 - 126

0.8

Patent; U.S. Vit. Pharm.; BE617599; (1962); Chem.Abstr.; vol. 59; nb. 646; (1963), View in Reaxys

132 - 134

1.4

Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys

140 - 142

2.5

Baltzly et al.; Journal of the American Chemical Society; vol. 66; (1944); p. 263,265, View in Reaxys

Crystal Property Description (3) Colour & Other References Properties colourless

yellow

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys

colourless

Wang, Bao-Lei; Liu, Xing-Hai; Zhang, Xiu-Lan; Zhang, Ji-Feng; Song, Hai-Bin; Li, Zheng-Ming; Chemical Biology and Drug Design; vol. 78; nb. 1; (2011); p. 42 - 49, View in Reaxys

NMR Spectroscopy (11) 1 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

600

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Zhou, An; Wu, Hongfei; Pan, Jian; Wang, Xuncui; Li, Jiaming; Wu, Zeyu; Hui, Ailing; Molecules; vol. 20; nb. 1; (2015); p. 1304 - 1318, View in Reaxys 3 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Bali, Alka; Sharma, Komal; Bhalla, Abhishek; Bala, Suman; Reddy, Dinesh; Singh, Anant; Kumar, Anil; European Journal of Medicinal Chemistry; vol. 45; nb. 6; (2010); p. 2656 - 2662, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Bali, Alka; Reddy, A. C. Dinesh Kumar; Medicinal Chemistry Research; vol. 22; nb. 1; (2013); p. 382 - 391, View in Reaxys 4 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Chai, Yunfeng; Wang, Lin; Sun, Hezhi; Guo, Cheng; Pan, Yuanjiang; Journal of the American Society for Mass Spectrometry; vol. 23; nb. 5; (2012); p. 823 - 833, View in Reaxys 5 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Chai, Yunfeng; Wang, Lin; Sun, Hezhi; Guo, Cheng; Pan, Yuanjiang; Journal of the American Society for Mass Spectrometry; vol. 23; nb. 5; (2012); p. 823 - 833, View in Reaxys 6 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy)

60/337

2016-05-20 15:00:44

Bourrain, Sylvie; Collins, Ian; Neduvelil, Joseph G.; Rowley, Michael; Leeson, Paul D.; Patel, Smita; Patel, Shil; Emms, Frances; Marwood, Rosemarie; Chapman, Kerry L.; Fletcher, Alan E.; Showell, Graham A.; Bioorganic and Medicinal Chemistry; vol. 6; nb. 10; (1998); p. 1731 - 1743, View in Reaxys; Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys 8 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 9 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 10 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys 11 of 11

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Bali, Alka; Sharma, Komal; Bhalla, Abhishek; Bala, Suman; Reddy, Dinesh; Singh, Anant; Kumar, Anil; European Journal of Medicinal Chemistry; vol. 45; nb. 6; (2010); p. 2656 - 2662, View in Reaxys; Bali, Alka; Reddy, A. C. Dinesh Kumar; Medicinal Chemistry Research; vol. 22; nb. 1; (2013); p. 382 - 391, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

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Solvent (IR Spectroscopy)

KBr

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys Mass Spectrometry (4) Description (Mass Location Spectrometry)

References

electron impact (EI); spectrum

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CID (collision-induced dissociation); ESI (Electrospray ionisation); IT (ion trap); Spectrum

Chai, Yunfeng; Wang, Lin; Sun, Hezhi; Guo, Cheng; Pan, Yuanjiang; Journal of the American Society for Mass Spectrometry; vol. 23; nb. 5; (2012); p. 823 - 833, View in Reaxys

CID (collision-insupporting inforduced dissociamation tion); IT (ion trap); ESI (Electrospray ionisation); Spectrum

Chai, Yunfeng; Jiang, Kezhi; Sun, Cuirong; Pan, Yuanjiang; Chemistry - A European Journal; vol. 17; nb. 39; (2011); p. 10820 - 10824, View in Reaxys

EI (Electron impact); Spectrum

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Pharmacological Data (4) 1 of 4

Comment (Pharmacological Data)

Bioactivities present

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wari, Perumal; Sriram, Dharmarajan; Kantevari, Srinivas; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 23; (2014); p. 5520 - 5524, View in Reaxys; Zhou, An; Wu, Hongfei; Pan, Jian; Wang, Xuncui; Li, Jiaming; Wu, Zeyu; Hui, Ailing; Molecules; vol. 20; nb. 1; (2015); p. 1304 - 1318, View in Reaxys; Han, Sheng Hua; Chen, Jian Xin; Liu, Hong Yan; Zhang, Hai Rong; Ma, Peng Fei; Asian Journal of Chemistry; vol. 27; nb. 4; (2015); p. 1299 - 1303, View in Reaxys; Gurdal, Enise Ece; Durmaz, Irem; Cetin-Atalay, Rengul; Yarim, Mine; Journal of Enzyme Inhibition and Medicinal Chemistry; vol. 30; nb. 4; (2015); p. 649 - 654, View in Reaxys; Raundal, Hemant N.; Jadhav, Rahul P.; Patil, Amar A.; Bobade, Vivek D.; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 54B; nb. 8; (2015); p. 979 - 987, View in Reaxys; Congiu, Cenzo; Onnis, Valentina; Deplano, Alessandro; Balboni, Gianfranco; Dedeoglu, Nurcan; Supuran, Claudiu T.; Bioorganic and Medicinal Chemistry Letters; vol. 25; nb. 18; (2015); p. 3850 - 3853; Art.No: 22949, View in Reaxys; Wang, Baolei; Shi, Yanxia; Zhan, Yizhou; Zhang, Liyuan; Zhang, Yan; Wang, Lizhong; Zhang, Xiao; Li, Yonghong; Li, Zhengming; Li, Baoju; Chinese Journal of Chemistry; vol. 33; nb. 10; (2015); p. 1124 - 1134, View in Reaxys; Patent; REMYND NV; GRIFFIOEN, Gerard; DE TAEYE, Bart; PRINCEN, Katrien; DE WITTE, Koen; BLANCHE, Emilie; RATNI, Hasane; NETTEKOVEN, Matthias; ROGERS-EVANS, Mark; WO2015/140130; (2015); (A1) English, View in Reaxys; Akgun, Hulya; Yilmaz, Demet Us; Atalay, Rengul Cetin; Gozen, Damla; Letters in Drug Design and Discovery; vol. 13; nb. 1; (2016); p. 64 - 76, View in Reaxys; Akgun, Hulya; Yilmaz, Demet Us; Atalay, Rengul Cetin; Gozen, Damla; Letters in Drug Design and Discovery; vol. 13; nb. 1; (2016); p. 64 - 76, View in Reaxys; Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 9; (2016); p. 2380 - 2382, View in Reaxys 2 of 4

Comment (Pharmacological Data)

physiological behaviour discussed

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys 3 of 4

Comment (Pharmacological Data)

physiological behaviour discussed

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys 4 of 4

Effect (Pharmacological Data)

bacterial resistance; inhibition of

Species or Test-System (Pharmacological Data)

Escherichia coli 3-AG100MKX

Method (Pharmacological Data)

cells incubated with levofloxacin in presence of title comp.; levofloxacin MIC determined by spectrofotometric assay

Further Details (Pharmacological Data)

3-AG100MKX: AcrAB-overexpressing gyrA mutant derived from AG100MKX (AG100 marA::Kmr); AcrAB: efflux pump; reference comp.: Phe-Arg-β-naphtylamide

Results

title comp. conc. to reduce levofloxacin MIC by 4-fold was 100 μg/ml

Bohnert, Juergen A.; Kern, Winfried V.; Antimicrobial Agents and Chemotherapy; vol. 49; nb. 2; (2005); p. 849 852, View in Reaxys

Reaxys ID 4182292 View in Reaxys

3/323 CAS Registry Number: 70931-28-1 Chemical Name: 1-(4-fluorophenylmethyl)piperazine; 1-(4-fluoro-benzyl)-piperazine; 1-(p-fluorobenzyl)piperazine; 4-(4-fluorobenzyl)piperazine; N-(4-fluorobenzyl)piperazine; 4-Fluorobenzylpiperazine; 1-(4-fluorobenzyl)-piperazine Linear Structure Formula: C11H15FN2 Molecular Formula: C11H15FN2 Molecular Weight: 194.252 Type of Substance: heterocyclic InChI Key: OOSZCNKVJAVHJI-UHFFFAOYSA-N Note:

NH N

Substance Label (10) Label References

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Singh, Anil K.; Rathi, Brijesh; Medviediev, Volodymyr V.; Shishkin, Oleg V.; Bahadur, Vijay; Singh, Taruna; Singh, Brajendra K.; Vijayan; Balachandran; Gorobets, Nikolay Yu; Journal of Chemical Sciences; vol. 128; nb. 2; (2016); p. 297 - 309, View in Reaxys

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

Jallapally, Anvesh; Addla, Dinesh; Yogeeswari, Perumal; Sriram, Dharmarajan; Kantevari, Srinivas; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 23; (2014); p. 5520 - 5524, View in Reaxys

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

H-B4

Revesz, Laszlo; Bollbuck, Birgit; Buhl, Thomas; Eder, Joerg; Esser, Ronald; Feifel, Roland; Heng, Richard; Hiestand, Peter; Jachez-Demange, Benedicte; Loetscher, Pius; Sparrer, Helmut; Schlapbach, Achim; Waelchli, Rudolf; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 23; (2005); p. 5160 5164, View in Reaxys

4-2

Oh, Seung-Jun; Lee, Kyo Chul; Lee, Sang-Yoon; Ryu, Eun Kyoung; Saji, Hideo; Choe, Yearn Seong; Chi, Dae Yoon; Kim, Sang Eun; Lee, Jeewoo; Kim, Byung-Tae; Bioorganic and Medicinal Chemistry; vol. 12; nb. 21; (2004); p. 5505 - 5513, View in Reaxys

11, R&3%=4-F

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

16c

Tapia, Ines; Alonso-Cires, Luisa; Lopez-Tudanca, Pedro Luis; Mosquera, Ramon; Labeaga, Luis; Innerarity, Ana; Orjales, Aurelio; Journal of Medicinal Chemistry; vol. 42; nb. 15; (1999); p. 2870 - 2880, View in Reaxys

Patent-Specific Data (3) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys Patent; PIERRE FABRE MEDICAMENT; WO2007/147824; (2007); (A1) English, View in Reaxys Patent; Solvay Pharmaceuticals GmbH; EP1176144; (2002); (A1) German, View in Reaxys

Derivative (1) Derivative

References

1-(4-fluorobenBartl; Dlabac; Protiva; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 11; (1980); p. zyl)piperazine 3182 - 3189, View in Reaxys bis(hydrogen maleate); 1-(4-fluorobenzyl)piperazine dimethanesulfonate Melting Point (1) 1 of 1

Melting Point [°C]

64 - 65

Solvent (Melting Point)

light petroleum

Bartl; Dlabac; Protiva; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 11; (1980); p. 3182 3189, View in Reaxys Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

80 - 84

0.2

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

108

2.3

Bartl; Dlabac; Protiva; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 11; (1980); p. 3182 - 3189, View in Reaxys

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Crystal Property Description (1) Colour & Other References Properties yellow

Perez, Michel; Lamothe, Marie; Maraval, Catherine; Mirabel, Etienne; Loubat, Chantal; Planty, Bruno; Horn, Clemens; Michaux, Julien; Marrot, Sebastien; Letienne, Robert; Pignier, Christophe; Bocquet, Arnaud; Nadal-Wollbold, Florence; Cussac, Didier; De Vries, Luc; Le Grand, Bruno; Journal of Medicinal Chemistry; vol. 52; nb. 19; (2009); p. 5826 - 5836, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys

NMR Spectroscopy (13) 1 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR

Location

Page/Page column 22

Comment (NMR Spectroscopy)

Signals given

(400 MHz, DMSO-d6) δ (ppm): 7.33-7.10 (m, 4 Ar H), 3.4 (s, 2H), 2.70 (t, J=4.8 Hz, 4H), 2.30 (t, J=1.6 Hz, 4 H).

Patent; KHAMRAI, Uttam; Ronsheim, Matthew; Karak, Sumit Kumar; US2010/152160; (2010); (A1) English, View in Reaxys 4 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

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dal-Wollbold, Florence; Cussac, Didier; De Vries, Luc; Le Grand, Bruno; Journal of Medicinal Chemistry; vol. 52; nb. 19; (2009); p. 5826 - 5836, View in Reaxys 5 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3; tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3; tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]

200

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3; tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]

200

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 9 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

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10 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 11 of 13

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 12 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

Solvents (NMR Spectro- CDCl3 scopy) Tapia, Ines; Alonso-Cires, Luisa; Lopez-Tudanca, Pedro Luis; Mosquera, Ramon; Labeaga, Luis; Innerarity, Ana; Orjales, Aurelio; Journal of Medicinal Chemistry; vol. 42; nb. 15; (1999); p. 2870 - 2880, View in Reaxys Mass Spectrometry (4) Description (Mass Location Spectrometry) LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)

Page/Page column 74

References Patent; PAMLICO PHARMACEUTICAL INC.; ATKINSON, Robert N.; OMMEN, Andy J.; VEAL, James M.; HUANG, Kenneth H.; SMITH, Emilie, D.; WO2012/88411; (2012); (A1) English, View in Reaxys

CID (collision-insupporting inforduced dissociamation tion); IT (ion trap); ESI (Electrospray ionisation); Spectrum

Chai, Yunfeng; Jiang, Kezhi; Sun, Cuirong; Pan, Yuanjiang; Chemistry - A European Journal; vol. 17; nb. 39; (2011); p. 10820 - 10824, View in Reaxys

CID (collision-insupporting inforduced dissociamation tion); IT (ion trap); ESI (Electrospray ionisation); Tandem mass spec-

Chai, Yunfeng; Jiang, Kezhi; Sun, Cuirong; Pan, Yuanjiang; Chemistry - A European Journal; vol. 17; nb. 39; (2011); p. 10820 - 10824, View in Reaxys

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trometry; Spectrum LCMS (Liquid chromatography mass spectrometry)

Page/Page column 22

Patent; KHAMRAI, Uttam; Ronsheim, Matthew; Karak, Sumit Kumar; US2010/152160; (2010); (A1) English, View in Reaxys

Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

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Comment (Pharmacological Data)

physiological behaviour discussed

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys 3 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Reaxys ID 616695 View in Reaxys

4/323

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CAS Registry Number: 5011-34-7 Chemical Name: 1-(2,3,4-trimethoxybenzyl)piperazine; Trimetazidine Linear Structure Formula: C14H22N2O3 Molecular Formula: C14H22N2O3 Molecular Weight: 266.34 Type of Substance: heterocyclic InChI Key: UHWVSEOVJBQKBE-UHFFFAOYSA-N Note:

O O

N NH

Substance Label (9) Label References 5

Chhatriwala, Nirmal M.; Patel, Amit B.; Patel, Rahul V.; Kumari, Premlata; Journal of Chemical Research; vol. 38; nb. 10; (2014); p. 611 - 616, View in Reaxys

Patel, Rahul V.; Patel, Jigar K.; Kumari, Premlata; Chikhalia, Kishor H.; Letters in Organic Chemistry; vol. 9; nb. 7; (2012); p. 478 - 486, View in Reaxys; Patel, Rahul V.; Patel, Jigar K.; Nile, Shivraj H.; Park, Se Won; Letters in Drug Design and Discovery; vol. 10; nb. 5; (2013); p. 462 - 470, View in Reaxys

Patel, Divyesh; Patel, Rahul; Kumari, Premlata; Patel, Navin; Acta Poloniae Pharmaceutica - Drug Research; vol. 69; nb. 5; (2012); p. 879 - 891, View in Reaxys

Patel, Rahul V.; Patel, Amit B.; Kumari, Premlata; Chikhalia, Kishor H.; Medicinal Chemistry Research; vol. 21; nb. 10; (2012); p. 3119 - 3132, View in Reaxys

TMZ

Reymond, Frederic; Carrupt, Pierre-Alain; Testa, Bernard; Girault, Hubert H.; Chemistry - A European Journal; vol. 5; nb. 1; (1999); p. 39 - 47, View in Reaxys; Salducci; Chauvet-Monges; Tillement; Albengres; Testa; Carrupt; Crevat; Journal of Pharmacology and Experimental Therapeutics; vol. 277; nb. 1; (1996); p. 417 - 422, View in Reaxys; Stary; Kohin; Samaja; Howlett; Hogan; Experimental Physiology; vol. 88; nb. 3; (2003); p. 415 - 421, View in Reaxys; Chander, Vikas; Singh, Devinder; Chopra, Kanwaljit; Pharmacology; vol. 67; nb. 1; (2003); p. 41 - 48, View in Reaxys; Baumert, Herve; Faure, Jean-Pierre; Zhang, Keqiang; Petit, Isabelle; Goujon, Jean Michel; Dutheil, Delphine; Favreau, Frederic; Barriere, Michel; Tillement, Jean Paul; Mauco, Gerard; Papadopoulos, Vassilios; Hauet, Thierry; Pharmacology; vol. 71; nb. 1; (2004); p. 25 - 37, View in Reaxys; Saeedi, Ramesh; Grist, Mark; Wambolt, Richard B.; Bescond-Jacquet, Anne; Lucien, Arnaud; Allard, Michael F.; Journal of Pharmacology and Experimental Therapeutics; vol. 314; nb. 1; (2005); p. 446 - 454, View in Reaxys; D'Hahan, Nathalie; Taouil, Karima; Dassouli, Abdelilah; Jean-Emile Morel; European Journal of Pharmacology; vol. 328; nb. 2-3; (1997); p. 163 - 174, View in Reaxys; Domanski, Leszek; Sulikowski, Tadeusz; Safranow, Krzysztof; Pawlik, Andrzej; Olszewska, Maria; Chlubek, Dariusz; Urasinska, Elzbieta; Ciechanowski, Kazimierz; European Journal of Pharmaceutical Sciences; vol. 27; nb. 4; (2006); p. 320 - 327, View in Reaxys; Kutala, Vijay Kumar; Khan, Mahmood; Mandal, Rajarsi; Ganesan, Latha P.; Tridandapani, Susheela; Kalai, Tamas; Hideg, Kalman; Kuppusamy, Periannan; Journal of Pharmacology and Experimental Therapeutics; vol. 317; nb. 3; (2006); p. 921 - 928, View in Reaxys; Thrainsdottir, Inga S.; Von Bibra, Helene; Malmberg, Klas; Ryden, Lars; Journal of Cardiovascular Pharmacology; vol. 44; nb. 1; (2004); p. 101 - 108, View in Reaxys; Faure, Jean-Pierre; Baumert, Herve; Han, Zeqiu; Goujon, Jean Michel; Favreau, Frederic; Dutheil, Delphine; Petit, Isabelle; Barriere, Michel; Tallineau, Claude; Tillement, Jean Paul; Carretier, Michel; Mauco, Gerard; Papadopoulos, Vassilios; Hauet, Thierry; Biochemical Pharmacology; vol. 66; nb. 11; (2003); p. 2241 - 2250, View in Reaxys

Plemper Van Balen, Georgette; Carrupt, Pierre-Alain; Morin, Didier; Tillement, Jean-Paul; Le Ridant, Alain; Testa, Bernard; Biochemical Pharmacology; vol. 63; nb. 9; (2002); p. 1691 - 1697, View in Reaxys; Kalai, Tamas; Khan, Mahmood; Balog, Maria; Kutala, Vijay Kumar; Kuppusamy, Periannan; Hideg, Kalman; Bioorganic and Medicinal Chemistry; vol. 14; nb. 16; (2006); p. 5510 - 5516, View in Reaxys

Thiery; Coudert; Bizot-Espiard; Pfeiffer; Renard; Lindenbaum; Guillaumet; Journal of Medicinal Chemistry; vol. 44; nb. 23; (2001); p. 3904 - 3914, View in Reaxys

TMZ; Merck 9835

Hauet, Thierry; Baumert, Herve; Amor, Imed Ben; Gibelin, Helene; Tallineau, Claude; Eugene, Michel; Tillement, Jean Paul; Carretier, Michel; Journal of Pharmacology and Experimental Therapeutics; vol. 292; nb. 1; (2000); p. 254 - 260, View in Reaxys

Ferte, Jacques; Kuehnel, Jean-Marc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 - 489, View in Reaxys

Patent-Specific Data (3) Prophetic ComLocation in Patent References pound Page/Page column

prophetic product

Patent; ZAKRYTOE AKTSIONERNOE OBSCHSHESTVO "VERTEX"; Veselkina, Olga Sergejevna; Viktorov, Nikolay Borisovich; Petrishchev, Nikolay Nikolaevich; Poplavskaya, Yuliya Vyacheslavovna; US2013/267707; (2013); (A1) English, View in Reaxys Patent; Gorczynski, Richard J.; US2007/293552; (2007); (A1) English, View in Reaxys

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Patent; SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A.; WO2007/96251; (2007); (A1) English, View in Reaxys Derivative (3) Comment (Derivative)

References

Dipikrat, F: 234grad

Patent; Sci. Union et Cie Soc. Franc. de Rech. Med.; FR1302958; (1961); Chem.Abstr.; vol. 58; nb. 6844d; (1963), View in Reaxys

Dihydrochlorid, F: 235-238grad

Patent; Sci. Union et Cie Soc. Franc. de Rech. Med.; FR1302958; (1961); Chem.Abstr.; vol. 58; nb. 6844d; (1963), View in Reaxys

Dihydrochlorid, F: 225-228grad

Patent; Biofarma SA; FRM805; (1961); Chem.Abstr.; vol. 58; nb. 3442g; (1963), View in Reaxys

Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

200 - 205

Patent; Sci. Union et Cie Soc. Franc. de Rech. Med.; FR1302958; (1961); Chem.Abstr.; vol. 58; nb. 6844d; (1963), View in Reaxys

200 - 205

Patent; Biofarma SA; FRM805; (1961); Chem.Abstr.; vol. 58; nb. 3442g; (1963), View in Reaxys

Crystal Property Description (1) Colour & Other References Properties brown - yellow

Mao, Dan; Xu, Yungen; Hu, Xiaoping; Zhang, Guomin; Dong, Jin; Gong, Guoqing; Chemistry and Biodiversity; vol. 6; nb. 10; (2009); p. 1727 - 1736, View in Reaxys

Dissociation Exponent (2) 1 of 2

Dissociation Exponent (pK)

-0.961421

Solvent (Dissociation Exponent)

H2O

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a1/apparent

Dissociation Exponent (pK)

-0.655138

Solvent (Dissociation Exponent)

H2O

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a2/apparent

Plemper Van Balen, Georgette; Carrupt, Pierre-Alain; Morin, Didier; Tillement, Jean-Paul; Le Ridant, Alain; Testa, Bernard; Biochemical Pharmacology; vol. 63; nb. 9; (2002); p. 1691 - 1697, View in Reaxys Electrochemical Behaviour (1) Description (Elec- References trochemical Behaviour) Electrolytic dissociation / protonation equilibrium

Reymond, Frederic; Carrupt, Pierre-Alain; Testa, Bernard; Girault, Hubert H.; Chemistry - A European Journal; vol. 5; nb. 1; (1999); p. 39 - 47, View in Reaxys

Liquid/Liquid Systems (MCS) (2) 1 of 2

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

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Comment (Liquid/Liquid Systems (MCS))

pH dependence

Partner (Liquid/Liquid Systems (MCS))

1,2-DICHLOROETHANE

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Comment (Liquid/Liquid Systems (MCS))

pH dependence

Partner (Liquid/Liquid Systems (MCS))

1-Octanol

Plemper Van Balen, Georgette; Carrupt, Pierre-Alain; Morin, Didier; Tillement, Jean-Paul; Le Ridant, Alain; Testa, Bernard; Biochemical Pharmacology; vol. 63; nb. 9; (2002); p. 1691 - 1697, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray mol peak ionisation); CID (collision-induced dissociation); Tandem mass spectrometry; LCMS (Liquid chromatography mass spectrometry); Spectrum

References Zou, Jianjun; Dai, Li; Guang, Ji Wang; Zhu, Yubing; Fan, Hongwei; Xiao, Da Wei; Arzneimittel-Forschung/Drug Research; vol. 58; nb. 9; (2008); p. 429 - 434, View in Reaxys

Pharmacological Data (94) 1 of 94

Comment (Pharmacological Data)

Bioactivities present

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Location

Page/Page column

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; CHANGZHOU HI-TECH DISTRICT MULTIPLE DIMENSION INDUSTRY TECHNOLOGY INSTITUTE CO., LTD; XIE, Hebing; LI, Qingyi; GU, Shuhua; LV, Weihong; (17 pag.); US2016/81966; (2016); (A1) English, View in Reaxys 3 of 94

Comment (Pharmacological Data)

physiological behaviour discussed

Quartararo, Christine E.; Reznik, Eduard; DeCarvalho, Ana C.; Mikkelsen, Tom; Stockwell, Brent R.; ACS Medicinal Chemistry Letters; vol. 6; nb. 8; (2015); p. 948 - 952, View in Reaxys 4 of 94

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; LES LABORATOIRES SERVIER; GENTY, Patrick; HERMELIN, Christophe; PEAN, Jean-Manuel; US2013/202710; (2013); (A1) English, View in Reaxys 5 of 94

Effect (Pharmacological Data)

transporter; inhibition of

Species or Test-System (Pharmacological Data)

HEK293-Flp-In cells; genetically modified/infected with: human OCT2

Concentration (Pharmacological Data)

20 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

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Further Details (Pharmacological Data)

OCT2: organic cation transporter 2 (solute carrier 22A2); HEK: human embryonic kidney; fluorescent probe substrate: 4-(4-(dimethylamino)styryl)-N-methyl-pyridinium (ASP+) (5 μmol/l); high-throughput assay; fluorimetry; inhibition rate related to: OCT2

Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

28.5 percent

Location

supporting information

Kido, Yasuto; Matsson, Paer; Giacomini, Kathleen M.; Journal of Medicinal Chemistry; vol. 54; nb. 13; (2011); p. 4548 - 4558, View in Reaxys 6 of 94

Effect (Pharmacological Data)

transporter; inhibition of

Species or Test-System (Pharmacological Data)

HEK293-Flp-In cells; genetically modified/infected with: human OCT2

Concentration (Pharmacological Data)

20 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

Results

molecular target: human OCT2

Location

supporting information

Kido, Yasuto; Matsson, Paer; Giacomini, Kathleen M.; Journal of Medicinal Chemistry; vol. 54; nb. 13; (2011); p. 4548 - 4558, View in Reaxys 7 of 94

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

20 mg

Kind of Dosing (Pharmacological Data)

used as hydrochloride, purity 99.9percent; tablet given with 250 ml of water after overnight fasting

Further Details (Pharmacological Data)

halflife time (elimination) (t1/2); t1/2 related to: plasma

Type (Pharmacological Data)

t1/2

Value of Type (Pharmacological Data)

8.4 h

Zou, Jianjun; Dai, Li; Guang, Ji Wang; Zhu, Yubing; Fan, Hongwei; Xiao, Da Wei; Arzneimittel-Forschung/Drug Research; vol. 58; nb. 9; (2008); p. 429 - 434, View in Reaxys 8 of 94

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

20 mg

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2016-05-20 15:00:44

Kind of Dosing (Pharmacological Data)

used as hydrochloride, purity 99.9percent; tablet given with 250 ml of water after overnight fasting

Further Details (Pharmacological Data)

maximum plasma concentration (Cmax); Cmax related to: plasma

Type (Pharmacological Data)

Cmax

Value of Type (Pharmacological Data)

75.2 ng/ml

Zou, Jianjun; Dai, Li; Guang, Ji Wang; Zhu, Yubing; Fan, Hongwei; Xiao, Da Wei; Arzneimittel-Forschung/Drug Research; vol. 58; nb. 9; (2008); p. 429 - 434, View in Reaxys 9 of 94

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

20 mg

Kind of Dosing (Pharmacological Data)

used as hydrochloride, purity 99.9percent; tablet given with 250 ml of water after overnight fasting

Further Details (Pharmacological Data)

time to Cmax (tmax); tmax related to: plasma

Type (Pharmacological Data)

tmax

Value of Type (Pharmacological Data)

1.3 h

Zou, Jianjun; Dai, Li; Guang, Ji Wang; Zhu, Yubing; Fan, Hongwei; Xiao, Da Wei; Arzneimittel-Forschung/Drug Research; vol. 58; nb. 9; (2008); p. 429 - 434, View in Reaxys 10 of 94

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

20 mg

Kind of Dosing (Pharmacological Data)

used as hydrochloride, purity 99.9percent; tablet given with 250 ml of water after overnight fasting

Further Details (Pharmacological Data)

area under the curve: 0-36 h (AUC0-36); AUC0-36 related to: plasma

Type (Pharmacological Data)

AUC0-36

Value of Type (Pharmacological Data)

743.0 ng*h/ml

Zou, Jianjun; Dai, Li; Guang, Ji Wang; Zhu, Yubing; Fan, Hongwei; Xiao, Da Wei; Arzneimittel-Forschung/Drug Research; vol. 58; nb. 9; (2008); p. 429 - 434, View in Reaxys 11 of 94

Effect (Pharmacological Data)

antiparasitic

Species or Test-System (Pharmacological Data)

human erythrocytes

Method (Pharmacological Data)

<3H>hypoxanthine incorporation assay using Plasmodium falciparum D6-infected cells

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Further Details (Pharmacological Data)

chloroquine used as reference comp. (IC50: 0.18 μmol/l); IC50: conc. causing 50 percent of growth inhibition

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

100 μmol/l

Auffret, Gwenola; Labaied, Mehdi; Frappier, Francois; Rasoanaivo, Philippe; Grellier, Philippe; Lewin, Guy; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 4; (2007); p. 959 - 963, View in Reaxys 12 of 94

Effect (Pharmacological Data)

fibromyalgia syndrome (FMS); effect on

Species or Test-System (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Method (Pharmacological Data)

Example 1 Treatment Of Human Subject Diagnosed With Fibromyalgia With TrimetazidineA 40 year old male presented with long-standing complaints (15 years) of widespread pain - headaches, upper and lower back pain, neck pain, elbow and knee pain bilaterally, calf pain bilaterally and jaw pain. General non-specific symptoms were fatigue, symptoms of irritable bowel syndrome (constipation- type), insomnia, cognitive and memory impairment, morning stiffness, dizziness, irritability and depression.Physical Examination: A physical examination revealed tender points located at:(i) the sub-occipital muscle insertions bilaterally, at the occiput(ii) the lateral epicondyle at the right elbow(iii) the medial fat pads of the knees, just proximal to the joint lines, bilaterally(iv) the trapezius muscles, at the midpoint of the upper border of the muscles, bilaterally(v) the supraspinatus muscles, at the origins, above the spine of the scapula near the medial border, bilaterally.Laboratory Tests: The following laboratory investigations were conducted: CBC, ESR, CRP, Rheumatoid Factor, Thyroid Function Tests, ANA. These tests yielded no positive results. X-Rays were also taken and resulted in no positive findings.Patient History of Prior Treatment: A patient history was taken. Prior treatments targeting pain relief were as follows. OTC analgesics such as paracetamol (also known as acetaminophen), NSAIDs and low dose codeine provided no pain relief whatsoever. Prescription analgesics such as high dose codeine, tramadol and meperidine provided, at best, mild to moderate and very temporary relief and were frequently accompanied by unpleasant side effects. Trigger point injections with lidocaine or lidocaine mixed with triamcinolone (a corticosteroid) provided the best localized pain relief. However, these injections often had to be repeated at 2 to 4 week intervals, and were usually extremely painful procedures.-27- Prior treatments targeting other symptoms included the following. The subject had taken tegaserod for irritable bowel syndrome. Additional prior therapies included sertraline for depression, and Zolpidem for insomnia. The subject has also taken proclorperazine for dizziness.All of the above therapies were either minimally effective or completely ineffective.Diagnosis: The subject was diagnosed with fibromyalgia syndrome.Relevant Additional Medical History: The subject also has cardiac tachyarrhythmia (likely supraventricular tachycardia) with paroxysmal episodes of chest pains and syncope - currently in the process of being investigated.Treatment Regime: The subject was administered trimetazidine (modified release formulation, Vastarel.(R). MR), 35 mg orally, twice daily, originally for treatment of his cardiac condition.Results: Within 72 hours of starting treatment, there was a surprising and completely unexpected and vast improvement in all symptoms and signs of fibromyalgia. The benefits were first noticed within 24 hours of commencing therapy and further improved gradually thereafter. Positive results were as follows. The subject reported a "90percent reduction" in the widespread pain, with minimal residual pain reported at the left medial knee. The subject additionally reported very significantly increased energy levels, very significantly improved sleep patterns (described as "uninterrupted and very restful"), markedly improved regularity of bowel habits, markedly increased clarity of thoughts and improvement in short and long term memory, and very improved mood and markedly reduced level of irritability.Follow-up. After six (6) months of continuous use of trimetazidine (modified release) 35 mg, orally, twice daily, the patient has reported that he continues to experience the same marked improvement in the quality of his life, with infrequent episodes of pain at his trigger points, which usually occurs in reaction to stressful episodes or concurrent bacterial or viral infections and usually reduces once again to negligible

Results

within 72 hours of starting treatment with 35 mg (twice daily) of title compound, there was a vast improvement in all symptoms and signs of fibromyalgia; the subject reported a 90percent reduction in widespread pain; significant increase in energy levels and clarity of thoughts, improvement in sleep patterns, regularity of bowel habits, mood and short and long term memory, and reduction in level of irritability were among the positive results

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Location

Page/Page column 27-28

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys 13 of 94

Effect (Pharmacological Data)

fibromyalgia syndrome (FMS); effect on

Species or Test-System (Pharmacological Data)

human

Sex

female

Route of Application

peroral

Method (Pharmacological Data)

Example 2Treatment Of Human Subject Diagnosed With Fibromyalgia With TrimetazidineA 35 year old female presented with long-standing complaints (10 years) of widespread pain - headaches, upper and lower back pain, neck pain, hip pain bilaterally, knee pain bilaterally and jaw pain.-28- General non-specific symptoms were fatigue, symptoms of irritable bowel syndrome (constipation-type), insomnia, cognitive and memory impairment, morning stiffness, and depression.Physical Examination: A physical examination revealed tender points located at:(i) the sub-occipital muscle insertions bilaterally, at the occiput(ii) the medial fat pads of the knees, just proximal to the joint lines, bilaterally(iii) the trapezius muscles, at the midpoint of the upper border of the muscles, bilaterally(iv) greater trochanter: bilateral, posterior to the trochanteric prominence(v) the supraspinatus muscles, at the origins, above the spine of the scapula near the medial border, bilaterally.Laboratory Tests: The following laboratory investigations were conducted: CBC, ESR, CRP, Rheumatoid Factor, Thyroid Function Tests, ANA. These tests yielded no positive results. X-Rays were also taken and resulted in no positive findings.Patient History of Prior Treatment: A patient history was taken. Prior treatments targeting pain relief were as follows. OTC analgesics such as paracetamol (also known as acetaminophen), NSAIDs and low dose codeine provided no pain relief whatsoever. Prescription analgesics such as high dose codeine, tramadol and meperidine provided, at best, mild to moderate and very temporary relief and were frequently accompanied by unpleasant side effects. Trigger point injections with lidocaine or lidocaine mixed with triamcinolone (a corticosteroid) provided the best localized pain relief. However, these injections often had to be repeated at 2 to 4 week intervals, and were usually extremely painful procedures.Prior treatments targeting other symptoms included the following. The subject had taken tegaserod for irritable bowel syndrome. Additional prior therapies included sertraline for depression, and Zolpidem for insomnia.All of the above therapies were either minimally effective or completely ineffective.Diagnosis: The subject was diagnosed with fibromyalgia syndrome.-29- Treatment Regime: The subject was administered trimetazidine (modified release formulation, Vastarel.(R). MR), 35 mg orally, twice daily.Results: Within 24 hours of starting treatment, there was vast improvement in all symptoms and signs of fibromyalgia. Positive results were as follows. The subject reported a "95percent reduction" in the widespread pain, with minimal residual pain reported at the left hip. The subject additionally reported very significantly increased energy levels, very significantly improved sleep patterns (described as "uninterrupted and very restful"), markedly improved regularity of bowel habits, markedly increased clarity of thoughts and improvement in short and long term memory, and very improved mood.Follow-up. After four (4) months of continuous use of trimetazidine (modified release) 35 mg, orally, twice daily, the patient has reported that she continues to experience the same marked improvement in the quality of her life. She has had no relapse of symptoms to date.Example 3Treatment Of Human Subject Diagnosed With Fibromyalgia With TrimetazidineA 32 year old female presented with a 5 year history of complaints of widespread pain - headaches, upper and lower back pain, neck pain, hip pain bilaterally and knee pain bilaterally. General non-specific symptoms were fatigue, symptoms of irritable bowel syndrome (constipation-type), insomnia, morning stiffness and emotional liability.Physical Examination: A physical examination revealed tender points located at:(i) the sub-occipital muscle insertions bilaterally, at the occiput(ii) the medial fat pads of the knees, just proximal to the joint lines, bilaterally(iii) the trapezius muscles, at

Results

within 24 hours of starting treatment with 35 mg (twice daily) of title compound, there was a vast improvement in all symptoms and signs of fibromyalgia; subjects reported a 95percent reduction in widespread pain; significant increase in energy levels and clarity of thoughts, improvement in sleep patterns, and regularity of bowel habits, mood and short and long term memory were among the positive results; four months of continuous treatment further improved subjects' quality of life

Location

Page/Page column 29-31

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys 14 of 94

Effect (Pharmacological Data)

fibromyalgia syndrome (FMS); effect on

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Species or Test-System (Pharmacological Data)

human

Sex

male and female

Route of Application

peroral

Method (Pharmacological Data)

Example 4Treatment Of Eight (8) Human Subjects Diagnosed With Fibromyalgia With TrimetazidineThe following is a synopsis of the clinical response of each of eight (8) patients diagnosed with FMS, each of whom received treatment with trimetazidine MR (Vastarel. (R). MR), 35 mg orally, twice daily, for a period of at least four (4) weeks-32- Table 1. Summary of Treatment of 8 FMS Patients With Trimetazidine

Results

within 72 hours of starting treatment with 35 mg (twice daily) of title compound, there was a vast improvement in all symptoms and signs of fibromyalgia; subjects reported a 90percent reduction in widespread pain; improved mood and concentration, infrequent dizziness, consistent restful sleep, energetic feeling, absence of nausea, clarity of thinking, 90percent reduction of feeling of generalized tightness and stiffness of muscles, reduced symptoms of irritable bowel syndrome, absence of chest pain

Location

Page/Page column 32-40

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys 15 of 94

Effect (Pharmacological Data)

nucleotide level; effect on

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

peroral

Kind of Dosing (Pharmacological Data)

title comp. administered twice daily for 30 days in dose 10 mg/kg/day before surgery

Method (Pharmacological Data)

effect of title comp. on nucleotide profile in kidney after ischemia-reperfusion studied; conc. of adenosine and guanosine and their mono-, di- and triphosphates (Ado, Guo, AMP, ADP, ATP, GMP, GDP, GTP), NAD, NADP determined by HPLC

Further Details (Pharmacological Data)

left kidney artery clamped whereas right kidney artery non-clamped; NAD (NADP): nicotinamide adenine dinucleotide (phosphate); total adenine nucleotide conc. (TAN) and adenylate energy charge (AEC) calculated; placebo control

Results

title comp. increased conc. of Ado, ATP, ADP, AMP, TAN, GTP, GDP, NAD and AEC but decreased conc. of Guo, GMP and NADP; conc. of ATP, ADP, AMP, GDP, GMP, NADP, Guo were less in clamped kidney than those in non-clamped kidney (table)

Domanski, Leszek; Sulikowski, Tadeusz; Safranow, Krzysztof; Pawlik, Andrzej; Olszewska, Maria; Chlubek, Dariusz; Urasinska, Elzbieta; Ciechanowski, Kazimierz; European Journal of Pharmaceutical Sciences; vol. 27; nb. 4; (2006); p. 320 - 327, View in Reaxys 16 of 94

Effect (Pharmacological Data)

nucleotide level; effect on

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

peroral

Kind of Dosing (Pharmacological Data)

title comp. administered twice daily for 30 days in dose 10 mg/kg/day before surgery

Method (Pharmacological Data)

effect of title comp. on nucleotide profile in kidney after ischemia-reperfusion studied; conc. of inosine monophosphate (IMP), inosine (Ino), hypoxanthine (Hyp), xanthine (Xan), uric acid (UA), uridine (Urd) determined by HPLC

Further Details (Pharmacological Data)

left kidney artery clamped whereas right kidney artery non-clamped; placebo control

Results

title comp. decreased conc. of Ino, Urd, Hyp, Xan, UA (table)

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17 of 94

Effect (Pharmacological Data)

nephroprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

peroral

Kind of Dosing (Pharmacological Data)

title comp. administered twice daily for 30 days in dose 10 mg/kg/day before surgery

Method (Pharmacological Data)

effect of title comp. on acute tubular necrosis (ATN) in kidney after ischemia-reperfusion studied; kidney evaluated histologically

Further Details (Pharmacological Data)

left kidney artery clamped whereas right kidney artery non-clamped; placebo control

Results

title comp. protected against ischemic damage (prevalence of mild ATN was observed and severe ATN was not detected); intensity of ATN did not differ sign. between clamped and non-clamped kidneys (table, figure)

Effect (Pharmacological Data)

cellular calcium homeostasis improver

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

daily for 7 days

Method (Pharmacological Data)

treatment started 1 d before ISO injection (5 mg/kg/d; s.c.; for 2 d); after treatment myocytes from left ventricle loaded with fura-2 AM; cytosolic Ca(2+) level/caffeine (perfusion of 10 mmol/l for 20 s)-induced Ca(2+) transients assayed by fluorometry

Further Details (Pharmacological Data)

ISO: isoprenaline; amplitude of Ca(2+) peak induced by caffeine used as an index of sarcoplasmic reticulum (SR) Ca(2+) content

Results

title comp. prevented rise of cytosolic Ca(2+) level, depression of caffeine-induced Ca(2+) transients and decrease of SR Ca(2+) content caused by ISO administration

Meng, Dan; Feng, Lin; Chen, Xiang-Jian; Yang, Di; Zhang, Ji-Nan; Experimental Physiology; vol. 91; nb. 3; (2006); p. 591 - 601, View in Reaxys 19 of 94

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

daily for 7 days

Method (Pharmacological Data)

treatment started 1 d before ISO injection (5 mg/kg/d; s.c.; for 2 d); after treatment left ventricular tissues isolated; SERCA2a protein content determined by immunoblot assay; Ca(2+)-ATPase activity in sarcoplasmic reticulum (SR) fraction measured

Further Details (Pharmacological Data)

ISO: isoprenaline; SERCA2a: sarcoplasmic reticulum Ca(2+)-ATPase

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Results

title comp. prevented decrease of SR Ca(2+)-ATPase activity caused by ISO administration without affecting cardiac SERCA2a protein expression

Meng, Dan; Feng, Lin; Chen, Xiang-Jian; Yang, Di; Zhang, Ji-Nan; Experimental Physiology; vol. 91; nb. 3; (2006); p. 591 - 601, View in Reaxys 20 of 94

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

daily for 7 days

Method (Pharmacological Data)

treatment started 1 d before ISO injection (5 mg/kg/d; s.c.; for 2 d); slices of heart apex prepared and stained with haematoxylin/eosin for histopathological evaluation; left ventricular tissue supernatants assayed for ATP level (HPLC) and MDA content

Further Details (Pharmacological Data)

ISO: isoprenaline; ATP: adenosine triphosphate; MDA: maleic dialdehyde

Results

title comp. completely prevented myocardial damage induced by ISO, abolished ISOmediated decrease of energy metabolism (ATP level) and markedly reduced increase of lipid peroxidation (MDA content) caused by ISO administration

Meng, Dan; Feng, Lin; Chen, Xiang-Jian; Yang, Di; Zhang, Ji-Nan; Experimental Physiology; vol. 91; nb. 3; (2006); p. 591 - 601, View in Reaxys 21 of 94

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

daily for 7 days

Method (Pharmacological Data)

treatment started 1 d before ISO injection; after treatment ventricular myocytes isolated; whole-cell standard gigaseal patch clamp technique; ICa,L evoked by depolarization from holding potential of -50 mV to +40 mV (frequency of 2 kHz)

Further Details (Pharmacological Data)

ISO: isoprenaline (5 mg/kg/day; s.c.; for 2 days); ICa,L: L-type Ca(2+) current

Results

title comp. prevented ISO-induced reduction of ICa,L density, had little effect on time constant of ICa,L inactivation in heart cells

Meng, Dan; Feng, Lin; Chen, Xiang-Jian; Yang, Di; Zhang, Ji-Nan; Experimental Physiology; vol. 91; nb. 3; (2006); p. 591 - 601, View in Reaxys 22 of 94

Effect (Pharmacological Data)

hemodynamics; effect on

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

hearts infused with title comp. for 1 min; CF, LVSP, HR, LVDP and RPP continuously monitored

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Further Details (Pharmacological Data)

CF: coronary flow; LVSP: left ventricular systolic pressure; HR: heart rate; LVDP: left ventricular developed pressure; RPP: rate pressure product

Comment (Pharmacological Data)

No effect

Kutala, Vijay Kumar; Khan, Mahmood; Mandal, Rajarsi; Ganesan, Latha P.; Tridandapani, Susheela; Kalai, Tamas; Hideg, Kalman; Kuppusamy, Periannan; Journal of Pharmacology and Experimental Therapeutics; vol. 317; nb. 3; (2006); p. 921 - 928, View in Reaxys 23 of 94

Effect (Pharmacological Data)

hemodynamics; effect on

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

hearts subjected to 30 min of global ischemia followed by reperfusion for up to 45 min; title comp. infused for 1 min before ischemia; CF, LVSP, HR, LVDP and RPP continuously monitored

Further Details (Pharmacological Data)

CF: coronary flow; LVSP: left ventricular systolic pressure; HR: heart rate; LVDP: left ventricular developed pressure; RPP: rate pressure product

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

hearts subjected to 30 min of global ischemia followed by reperfusion for up to 45 min; title comp. infused for 1 min before ischemia; coronary effluent collected for up to 30 min of reperfusion; LDH and CK activities determined using spectrophotometer

Further Details (Pharmacological Data)

LDH: lactate dehydrogenase; CK: creatine kinase

Results

title comp. sign. decreased ischemia/reperfusion-induced LDH and CK activities in heart effluents

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

hearts subjected to 30 min of global ischemia followed by reperfusion for up to 120 min; title comp. infused for 1 min before ischemia; hearts sectioned, stained with triphenyltetrazolium chloride and examined microscopically for infarct size evaluation

Results

percentage infarct size in title comp.-treated group (36 percent) was sign. less compared with control (43 percent)

Effect (Pharmacological Data)

antioxidant

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Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

hearts subjected to 30 min of global ischemia followed by reperfusion for up to 15 min; title comp. infused for 1 min before ischemia; heart sections incubated with dihydroethidium for 30 min and then measured by fluorescence microscopy

Results

title comp. sign. attenuated generation of superoxide compared with control

Effect (Pharmacological Data)

enzyme; examination of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

hearts subjected to 30 min of global ischemia followed by reperfusion for 10 min; title comp. infused for 1 min before ischemia; heart tissue homogenized; phosphorylation of Akt, ERK1/2, and p38 MAPK determined by Western blotting

Further Details (Pharmacological Data)

ERK1/2: extracellular signal-regulated kinase 1/2; MAPK: mitogen-activated protein kinase

Results

Akt and ERK1/2 phosphorylation, but not p38 MAPK during ischemia was sign. decreased in hearts treated with title comp.; during reperfusion title comp. had no sign. effect

Effect (Pharmacological Data)

anti-ischemic

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Concentration (Pharmacological Data)

50 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt; title comp. solution in Krebs buffer infused through side arm at rate of 1 ml/min for 1 min

Method (Pharmacological Data)

test heart perfused with 95 percent O2/5 percent CO2 at 37 deg C for 15 min; title comp. infused; heart subjected to 30-min of ischemia, followed by 45-min of reperfusion; functional recovery of CF, LVDP and RPP expressed as percent of pre-ischemic baseline value

Further Details (Pharmacological Data)

CF: coronary flow; LVDP: left ventricular developed pressure; RPP: rate pressure product defined as product of heart rate and LVDP

Results

title comp. had no influence on CF; title comp. had influence on RPP and LVDP, but their effect was not significant compared to control

Kalai, Tamas; Khan, Mahmood; Balog, Maria; Kutala, Vijay Kumar; Kuppusamy, Periannan; Hideg, Kalman; Bioorganic and Medicinal Chemistry; vol. 14; nb. 16; (2006); p. 5510 - 5516, View in Reaxys 29 of 94

Effect (Pharmacological Data)

neutrophil activation; inhibition of

Species or Test-System (Pharmacological Data)

human neutrophils

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in saline

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Method (Pharmacological Data)

cells incubated with title comp. for 3 min; activated with fLMP; neutrophil activation evaluated by measuring neutrophil aggregation, lysosomal enzyme release, oxidant production by light transmission, β-glucuronidase assay, chemiluminescence, resp.

Further Details (Pharmacological Data)

6E6/ml neutrophils; computerized aggregometer-luminometer, 37 deg C, in presence of cytochalasin B (5 μg/ml); vehicle control; fLMP: formyl-methionyl-leucyl-peptide (1E-5 mol/l)

Results

title comp. at 1E-6 mol/l significantly inhibited fMLP-induced neutrophil aggregation, β-glucuronidase release, oxidant production indicating inhibition of neutrophil activation; higher conc. of title comp. did not further affect neutrophil activation

Tritto, Isabella; Wang, Penghai; Kuppusamy, Periannan; Giraldez, Roberto; Zweier, Jay L.; Ambrosio, Giuseppe; Journal of Cardiovascular Pharmacology; vol. 46; nb. 1; (2005); p. 89 - 98, View in Reaxys 30 of 94

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

human neutrophils

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

dissolved in saline

Method (Pharmacological Data)

cells incubated with purine and xanthine oxidase in presence of luminol; title comp. added; amount of luminescence generated by purine/xanthine oxidase system recorded for 15 min, quantified by integrating area under chemiluminescence curve

Further Details (Pharmacological Data)

6E6/ml neutrophils; aggregometer-luminometer, 37 deg C, in presence of cytochalasin (5 μg/ml); luminol: 3.2 μmol/l; purine: 2.3 mmol/l; xantine: 100 mU/ml; vehicle control

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

cytochrome c

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Method (Pharmacological Data)

0.2 mmol/l xanthine, 100 mU/ml xanthine oxidase incubated with title comp. in buffer; flux of superoxide radicals measured as optical density changes during first 60 s of reaction using double-beam spectrophotometer

Further Details (Pharmacological Data)

oxygen-equilibrated Krebs-Ringer-bicarbonate buffer with glucose, pH 7.4, 37 deg C; vehicle control; reference comp.: specific scavenger superoxide dismutase; to prevent H2O2, hydroxyl radical interferences 500 mU/ml catalase, 1 mmol/l deferoxamine used

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

deoxyribose

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Method (Pharmacological Data)

1 mmol/l deoxyribose incubated with title comp. in buffer; enzyme oxidation measured spectrophotometrically from formation of aldehyde detected after reaction with thiobarbituric acid by changes in absorbance at 532 nm

Further Details (Pharmacological Data)

oxygenated Krebs-Ringer-bicarbonate buffer, 37 deg C, in presence of FeCl3; vehicle control; reference comp.: specific scavenger dimethylthiourea

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Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

female

Route of Application

subcutaneous

Concentration (Pharmacological Data)

3 mg/kg

Kind of Dosing (Pharmacological Data)

daily, for 1 week

Method (Pharmacological Data)

after pretreatment with title comp., hearts subjected to ischemia (I); at 1-st 5 min of reflow (R), HN and 5 percent rat plasma infused; hemodynamics, coronary blood flow recorded by balloon in LV, via flow transducer, resp., before I and for last 40 min of R

Further Details (Pharmacological Data)

isolated perfused hearts; 20-min I; Krebs buffer R for last 40 min; HN: human neutrophils (300000/ml); hemodynamic parameters: left ventricular, end-diastolic, systolic pressure, heart rate (HR); LV developed pressure, HR x pressure product calculated

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Sex

female

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

title comp. infused to hearts 5 min before 20-min ischemia (I), for up to 1-st 15 min of reflow (R); HN, 5 percent rat plasma infused at 1-st 5 min of R; hemodynamics recorded before I, for 40 min after HN infusion by balloon in LV connected to transducer

Further Details (Pharmacological Data)

HN: human neutrophils; LV: left ventricle; hemodynamics: LV, end-diastolic and systolic pressure, heart rate (HR); LV developed pressure, HR x pressure product calculated; further invest. with pretreatment with title comp. (3 mg/kg/d, s.c., for 1 wk)

Results

title comp. infusion significantly ameliorated postischemic recovery of rate x pressure product, end-diastolic and LV pressure; combined pretreatment plus acute infusion of title comp. was as effective as infusion alone (figures)

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Sex

female

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

title comp. infused to hearts 5 min prior to 20-min ischemia (I), for up to 1-st 15 min of reflow (R); HN and 5 percent rat plasma infused at 1-st 5 min of R; coronary flow monitored via flow transducer before I and for 40 min after end of HN infusion

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Further Details (Pharmacological Data)

HN: human neutrophils (300000/ml); perfusion continued with standard Krebs buffer for remaining 3o min; further invest. of title comp. infusion in combination with pretreatment with title comp. (3 mg/kg, s.c., daily, for 1 wk)

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Sex

female

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

title comp. infused to isolated heart 5 min prior to ischemia, for up to 1-st 15 min of reperfusion; hemodynamics recorded using balloon inserted in LV connected to transducer, coronary flow recorded by flow transducer before, for last 40 min of reflow

Further Details (Pharmacological Data)

20-min ischemia at 37 deg C; perfusion with standard Krebs buffer for remaining 30 min of reperfusion; hemodynamic parameters: left ventricular, end-diastolic and systolic pressure, heart rate; developed pressure, rate x pressure product calculated

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Sex

female

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

title comp. infused to hearts for 5 min before ischemia (I), for up to first 15 min of reflow (R); HN and 5 percent rat plasma infused for 1-st 5 min of R; coronary effluent sampled before I, during R; oxygen radical conc. measured with EPR spectroscopy

Further Details (Pharmacological Data)

isolated perfused hearts; ischemia for 20 min, at 37 deg C; HN: human neutrophils (300000/ml); perfusion continued with Krebs buffer for next 30 min of R; ERP: electron paramagnetic resonance; 5,5'-dimethyl-1-pyrroline-N-oxide used as spin trap for ERP

Results

title comp. infusion significantly reduced oxygen radical generation to values averaging less than 30 percent of those observed in control hearts (figure)

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Sex

female

Concentration (Pharmacological Data)

1 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. was dissolved in saline

Method (Pharmacological Data)

title comp. infused to heart 5 min prior ischemia, during ischemia (20 min) and first 15 min of reflow; human neutrophils and rat plasma infused; oxygen radical production measured with EPR spectroscopy of coronary effluent samples with 40 mmol/l DMPO

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Further Details (Pharmacological Data)

samples collected at baseline, every 20 s throughout first 3 min of reflow, and at 4 - 45 min of postischemic reperfusion; ERP: electron paramagnetic resonance; DMPO: 5,5'-dimethyl-1-pyrroline-N-oxide

Results

title comp. infusion significantly reduced oxygen radical generation to values averaging less than 30 percent of those observed in control hearts (figure)

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Sex

male

Concentration (Pharmacological Data)

1 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in Krebs-Henseleit solution at 37 deg C

Method (Pharmacological Data)

heart subjected to 20-min global non-flow ischemia and perfused with title comp. and <9,10-3H>palmitate or <U-14C> lactate (for corresponding oxidation assay) for 30 min before and 40 min after ischemia; parameters of substrate oxidation determined

Further Details (Pharmacological Data)

parameters of substrate oxidation: rates of lactate and palmitate oxidation estimated by production <14C>CO2 and <3H>H2O, resp.; corresponding ATP production calculated

Results

title comp. had no effect on palmitate and lactate oxidation rates, but tended to reduce the contribution of fatty acids to ATP production

Saeedi, Ramesh; Grist, Mark; Wambolt, Richard B.; Bescond-Jacquet, Anne; Lucien, Arnaud; Allard, Michael F.; Journal of Pharmacology and Experimental Therapeutics; vol. 314; nb. 1; (2005); p. 446 - 454, View in Reaxys 40 of 94

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Sex

male

Concentration (Pharmacological Data)

1 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in Krebs-Henseleit solution at 37 deg C

Method (Pharmacological Data)

heart subjected to 20-min global non-flow ischemia and perfused with title comp. and <5-3H> or <U-14C> glucose (for glycolysis and glucose oxidation assay, resp.) for 30 min before and 40 after ischemia; parameters of glucose catabolism calculated

Further Details (Pharmacological Data)

glucose oxidation and glycolysis measured by <14C>CO2 and <3H>H2O production, resp.; percentage of oxidized and catabolized to lactate glucose, H(1+), and ATP production calculated

Results

title comp. had no effect on rates of glycolysis, it's role in ATP production, H(1+) production and nonoxidative glycolysis; title comp. increased oxidized glucose before and after ischemia and rates of glucose oxidation only after ischemia

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Sex

male

Concentration (Pharmacological Data)

1 μmol/l

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Kind of Dosing (Pharmacological Data)

title comp. dissolved in Krebs-Henseleit solution at 37 deg C

Method (Pharmacological Data)

heart subjected to 20-min global non-flow ischemia and perfused with title comp. for 30 min before and for 40 min after ischemia; cardiovascular parameters estimated

Further Details (Pharmacological Data)

estimated cardiovascular parameters: heart rate, peak systolic pressure, cardiac output, coronary flow, hydraulic power, rate pressure product

Results

title comp. increased hydraulic power either before or after ischemia and increased peak systolic pressure and cardiac output only after ischemia

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Sex

male

Concentration (Pharmacological Data)

1 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in Krebs-Henseleit solution at 37 deg C

Method (Pharmacological Data)

hearts from rats with cardiac hypertrophy; heart subjected to 20-min global non-flow ischemia and perfused with title comp. for 30 min before and for 40 min after ischemia; cardiovascular parameters estimated

Further Details (Pharmacological Data)

cardiac hypertrophy (25 to 30 percent increased heart weight) produced by constriction of suprarenal abdominal aorta; estimated cardiovascular parameters: heart rate, peak systolic pressure, cardiac output, coronary flow, hydraulic power, rate pressure product

Results

title comp. increased cardiac output and hydraulic power either before or after ischemia and increased peak systolic pressure, coronary flow, and rate pressure product only after ischemia

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

Sex

male

Concentration (Pharmacological Data)

1 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in Krebs-Henseleit solution at 37 deg C

Method (Pharmacological Data)

hypertrophied heart subjected to 20-min global non-flow ischemia and perfused with title comp. and <5-3H> or <U-14C> glucose (for glycolysis and glucose assay, resp.) for 30 min before and 40 after ischemia; parameters of glucose catabolism calculated

Further Details (Pharmacological Data)

hypertrophy produced by constriction of suprarenal abdominal aorta for 8 wk; glucose oxidation and glycolysis measured by <14C>CO2 and <3H>H2O production; percentage of oxidized and catabolized to lactate glucose, H(1+), and ATP production calculated

Results

title comp. reduced rates of glycolysis, it's role in ATP production, H(1+) production before and after ischemia, and nonoxidative glycolysis after it, but increased oxidized glucose before and after ischemia and rates of glucose oxidation only after it

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat heart

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Sex

male

Concentration (Pharmacological Data)

1 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in Krebs-Henseleit solution at 37 deg C

Method (Pharmacological Data)

hypertrophied heart subjected to 20-min global non-flow ischemia and perfused with title comp. and <9,10-3H>palmitate or <U-14C> lactate (for corresponding oxidation assay) for 30 min before and 40 after ischemia; oxidation parameters determined

Further Details (Pharmacological Data)

hypertrophy produced by constriction of suprarenal abdominal aorta for 8 wk; parameters of substrate oxidation: rates of lactate and palmitate oxidation estimated by production <14C>CO2 and <3H>H2O, resp.; corresponding ATP production calculated

Results

title comp. had no effect on palmitate and lactate oxidation rates, but tended to reduce contribution of fatty acids to ATP production

Effect (Pharmacological Data)

anti-inflammatory

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1.8 - 7.2 mg/kg

Method (Pharmacological Data)

treatment with title comp.; after 30 min subplantar injection of 100 μl of 1 percent carrageenan into right hind paw; carrageenan-induced paw oedema was assessed for 1-4 h; paw volume was measured

Further Details (Pharmacological Data)

saline control; reference comp.: indomethacin; further investigations using rofecoxib, dexamethasone or indomethacin

Results

title comp. at 3.6-7.2 mg/kg significantly inhibited carrageenan-induced paw oedema at 2-3 h; reference comp. significantly inhibited paw oedema response at 1-4 h; rofecoxib, dexamethasone or indomethacin increased effect of title comp. (figure)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 46 of 94

Effect (Pharmacological Data)

antinociceptive

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1.8 - 7.2 mg/kg

Method (Pharmacological Data)

treatment with title comp.; after 30 min hot-plate test (52 deg C, cut-off time 30 s) was performed; latency to lick hind paw or jump out of apparatus was recorded at 0.5-2 h posttreatment

Further Details (Pharmacological Data)

saline control; reference comp.: indomethacin

Results

title comp. significantly delayed hot-plate latency at 1-2 h post-treatment; reference comp. had similar effect (figure)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 47 of 94

Effect (Pharmacological Data)

antinociceptive

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3.6 - 7.2 mg/kg

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Method (Pharmacological Data)

treatment with title comp.; tail electric stimulation test; minimum current required to elicit vocalization upon electric stimulation of tail was determined at 1-2 h

Further Details (Pharmacological Data)

saline control; reference comp.: indomethacin

Results

title comp. dose-dependently increased threshold for vocalization during 2 h; reference comp. had similar effect (table)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 48 of 94

Effect (Pharmacological Data)

antinociceptive

Species or Test-System (Pharmacological Data)

Swiss albino mouse

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3.6 - 7.2 mg/kg

Method (Pharmacological Data)

treatment with title comp.; after 30 min injection of capsaicin (1.6 μg/paw) under dorsal surface of right hind paw; duration of licking response was assessed for 5 min

Further Details (Pharmacological Data)

saline control

Results

title comp. significantly inhibited duration of paw licking following capsaicin injection (figure)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 49 of 94

Effect (Pharmacological Data)

antinociceptive

Species or Test-System (Pharmacological Data)

Swiss albino mouse

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3.6 - 7.2 mg/kg

Method (Pharmacological Data)

treatment with title comp.; injection of 20 μl of 2.5 percent formalin solution s.c. into plantar surface of left paw; formalin-induced nociceptive responses; number of flinch behaviours was counted from 0 to 60 min

Further Details (Pharmacological Data)

saline control

Results

title comp. dose-dependently inhibited formalin-evoked nociceptive behaviour (figure)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 50 of 94

Effect (Pharmacological Data)

antinociceptive

Species or Test-System (Pharmacological Data)

Swiss albino mouse

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1.8 - 7.2 mg/kg

Method (Pharmacological Data)

treatment with title comp.; then acetic acid (0.6 percent, i.p.) was administered; acetic acid-induced writhing was assessed

Further Details (Pharmacological Data)

saline control; further invest. using α2-adrenoceptor antagonist yohimbine, non-selective adenosine receptor antagonists theophylline and caffeine, dopamine D2-receptor antagonist sulpiride, dopamine D2-receptor agonist bromocryptine or indomethacin

Results

title comp. at 3.6-7.2 mg/kg dose-dependently reduced acetic acid-induced writhing; yohimbine, theophylline, sulpiride reduced effect of title comp.; bromocryptine and indomethacin increased effect of title comp.; caffeine had no effect (figure)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys

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51 of 94

Effect (Pharmacological Data)

antinociceptive

Species or Test-System (Pharmacological Data)

Swiss albino mouse

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1.8 - 7.2 mg/kg

Method (Pharmacological Data)

treatment with title comp.; then acetic acid (0.6 percent, i.p.) was administrated; acetic acid-induced writhing was assessed

Further Details (Pharmacological Data)

further invest. using α1-adrenoceptor antagonist prazosin, adrenergic blocker guanethidine, non-selective β-adrenoceptor antagonist propranolol, muscarinic acetylcholine receptor antagonist atropine, non-selective opioid receptor antagonist naloxone

Results

title comp. at 3.6-7.2 mg/kg dose-dependently reduced acetic acid-induced writhing; naloxone, prazosin, propranolol, atropine, guanethidine had no effect (figure)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 52 of 94

Effect (Pharmacological Data)

antinociceptive

Species or Test-System (Pharmacological Data)

Swiss albino mouse

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1.8 - 7.2 mg/kg

Method (Pharmacological Data)

treatment with title comp.; then acetic acid (0.6 percent, i.p.) was administrated; acetic acid-induced writhing was assessed

Further Details (Pharmacological Data)

further investigations using potassium chnnel blocker glibenclamide, dopamine D2-receptor antagonists haloperidol and domperidone, dopamine D1-receptor antagonist clozapine

Results

title comp. at 3.6-7.2 mg/kg dose-dependently reduced acetic acid-induced writhing; glibenclamine, haloperidol, domperidone, clozapine had no effect (figure)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 53 of 94

Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

Swiss albino mouse

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3.6 - 7.2 mg/kg

Method (Pharmacological Data)

treatment with title comp.; after 0.5-2 h rotarod testing (acceleration 4-40 rpm over 5 min); motor performance was measured

Further Details (Pharmacological Data)

saline control

Comment (Pharmacological Data)

No effect

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 54 of 94

Effect (Pharmacological Data)

antidepressant

Species or Test-System (Pharmacological Data)

Swiss albino mouse

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3.6 - 7.2 mg/kg

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Method (Pharmacological Data)

treatment with title comp.; then Porsolt's forsed-swimming test was performed; mouse was forced to swim for 6 min; duration of immobility was measured

Further Details (Pharmacological Data)

saline control; reference comp.: tricyclic antidepressant imipramine

Results

title comp. significantly reduced duration of immobility; reference comp. had similar effect (figure)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 55 of 94

Effect (Pharmacological Data)

gastroprotective

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1.8 - 7.2 mg/kg

Method (Pharmacological Data)

treatment with title comp.; administration of indomethacin (20 mg/kg, i.p.); after 24 h number and severity of gastric mucosal lesions was assessed

Further Details (Pharmacological Data)

saline control

Results

title comp. dose-dependently inhibited indomethacin-induced gastric mucosal lesions (figure)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 56 of 94

Effect (Pharmacological Data)

secretion stimulant

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3.6 - 7.2 mg/kg

Method (Pharmacological Data)

anaesthetized rats (urethane 1.25 g/kg, i.p.); stomach was distended by filling with 2 ml of saline; treatment with title comp.; after 2 h gastric acid output was determined by titration to pH 7.0 with 0.01 N NaOH

Further Details (Pharmacological Data)

rats deprived of food for 18 h before experiment

Results

title comp. dose-dependently increased gastric acid secretion induced by distention (figure)

Abdel-Salam, Omar M.E.; El-Batran, Siham; Pharmacology; vol. 75; nb. 3; (2005); p. 122 - 132, View in Reaxys 57 of 94

Effect (Pharmacological Data)

antihypoxic

Species or Test-System (Pharmacological Data)

Wistar rat heart

Sex

female

Concentration (Pharmacological Data)

25 μmol/l

Method (Pharmacological Data)

heart perfused with Krebs modified solution (KMS) for 60 min in Langendorff perfusion apparatus; title comp. added; heart submitted to 120-min ischemia; heart mitochondrial fraction prepared; mitochondrial function assessed by laboratory methods

Further Details (Pharmacological Data)

glutamate/malate used as energy substrate; ischemia: KMS without glucose and carbogen

Results

title comp. significantly protected heart mitochondria from deleterious effects of ischemia on respiratory control rate decreasing O2 consumption after ADP phosphorylation (from 16.73 to 10.21 nmol O2/min)

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Monteiro, Pedro; Duarte, Ana I.; Goncalves, Lino M.; Moreno, Antonio; Providncia, Luis A.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 123 - 128, View in Reaxys 58 of 94

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Wistar rat heart

Sex

female

Concentration (Pharmacological Data)

25 μmol/l

Method (Pharmacological Data)

heart perfused with Krebs modified solution (KMS) for 60 min in Langendorff perfusion apparatus; title comp. added; heart submitted to 120-min ishemia; heart mitochondrial fraction prepared; electrical potential assessed by laboratory methods

Further Details (Pharmacological Data)

glutamate/malate (G/M), succinate (S), or ascorbate/TMPD (N,N,N',N',-tetramethyl-P-phenylenodiamine) used as energy substrates; ischemia: KMS without glucose and carbogen

Results

title comp. increased electrical potential 186.66 (ischemia) to 199.49 mV decreased when G/M used as energy substrate; similar results obtained when S (197.41 vs 187.23 mV) and ascorbate/TMPD (199.77 vs 189.24 mV) used as energy substrates

Monteiro, Pedro; Duarte, Ana I.; Goncalves, Lino M.; Moreno, Antonio; Providncia, Luis A.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 123 - 128, View in Reaxys 59 of 94

Effect (Pharmacological Data)

antihypoxic

Species or Test-System (Pharmacological Data)

Wistar rat heart

Sex

female

Concentration (Pharmacological Data)

25 μmol/l

Method (Pharmacological Data)

heart perfused with Krebs modified solution (KMS) for 60 min in Langendorff perfusion apparatus; title comp. added; heart submitted to 120-min ischemia; heart mitochondrial fraction prepared; time needed to phosphorylate of 250 nmol ADP evaluated

Further Details (Pharmacological Data)

glutamate/malate, succinate, or ascorbate/N,N,N',N',-tetramethyl-P-phenylenodiamine used as energy substrates; ischemia: KMS without glucose and carbogen

Comment (Pharmacological Data)

No effect

Monteiro, Pedro; Duarte, Ana I.; Goncalves, Lino M.; Moreno, Antonio; Providncia, Luis A.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 123 - 128, View in Reaxys 60 of 94

Effect (Pharmacological Data)

antihypoxic

Species or Test-System (Pharmacological Data)

Wistar rat heart

Sex

female

Concentration (Pharmacological Data)

25 μmol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

glutamate/malate, succinate, or ascorbate/N,N,N',N',-tetramethyl-P-phenylenodiamine used as energy substrates; ischemia: KMS without glucose and carbogen

Comment (Pharmacological Data)

No effect

Monteiro, Pedro; Duarte, Ana I.; Goncalves, Lino M.; Moreno, Antonio; Providncia, Luis A.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 123 - 128, View in Reaxys 61 of 94

Effect (Pharmacological Data)

antihypoxic

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Species or Test-System (Pharmacological Data)

Wistar rat heart

Sex

female

Concentration (Pharmacological Data)

25 μmol/l

Method (Pharmacological Data)

heart perfused with Krebs modified solution (KMS) for 60 min in LPA; title comp. added; heart submitted to 120-min ischemia; heart mitochondrial fraction prepared; enzyme activity of complexes I, II-III, IV, and ATP synthase evaluated

Further Details (Pharmacological Data)

glutamate/malate, succinate, or ascorbate/N,N,N',N',-tetramethyl-P-phenylenodiamine used as energy substrates; LPA: Langendorff perfusion apparatus; ischemia: KMS without glucose and carbogen

Results

title comp. increased complex I enzyme activity

Monteiro, Pedro; Duarte, Ana I.; Goncalves, Lino M.; Moreno, Antonio; Providncia, Luis A.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 123 - 128, View in Reaxys 62 of 94

Effect (Pharmacological Data)

nephroprotective

Species or Test-System (Pharmacological Data)

pig kidney

Concentration (Pharmacological Data)

1e-06 mol/l

Method (Pharmacological Data)

test system cold-flushed and preserved at 4 deg C in each preservative soln. for 24-72 h in presence/absence of title comp.; autotransplanted; urine sample collected after 24 h; GFR, FENa and FEMg measured on d 1 to d 14 using automatic analyzer

Further Details (Pharmacological Data)

preservatives: University of Wisconsin soln., Hopital Edouard-Herriot soln. (HEH), Celsior soln.; GFR: glomerular filtration rate; FENa: fractional excretion of sodium; FEMg: fractional excretion of magnesium; uninephrectomized animals also assessed

Results

title comp. protected test system against ischemia-reperfusion injury in all preserved groups by improving renal and tubular function, particularly in combination with HEH; diagram

Baumert, Herve; Faure, Jean-Pierre; Zhang, Keqiang; Petit, Isabelle; Goujon, Jean Michel; Dutheil, Delphine; Favreau, Frederic; Barriere, Michel; Tillement, Jean Paul; Mauco, Gerard; Papadopoulos, Vassilios; Hauet, Thierry; Pharmacology; vol. 71; nb. 1; (2004); p. 25 - 37, View in Reaxys 63 of 94

Effect (Pharmacological Data)

nephroprotective

Species or Test-System (Pharmacological Data)

pig kidney

Concentration (Pharmacological Data)

1e-06 mol/l

Method (Pharmacological Data)

test system cold-flushed and preserved at 4 deg C in each preservative soln. for 24-72 h in presence/absence of title comp.; autotransplanted; kidney fragments fixed and stained; mitochondrial injury evaluated from early (30 min to 1 h), d 7 and d 14

Further Details (Pharmacological Data)

preservatives: University of Wisconsin soln., Hopital Edouard-Herriot soln. (HEH), Celsior soln.; stained with hematoxylin and eosin; uninephrectomized animals also assessed; further study done on proximal tubule cell lesions

Results

title comp. improved mitochondrial integrity after cold ischemia and ischemia-reperfusion injury in all preserved groups, particularly in combination with HEH; also reduced tubular cell lesions after 48 or 72 h of preservation; tables, picture

Effect (Pharmacological Data)

cardiovascular

Species or Test-System (Pharmacological Data)

human

Sex

male and female

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Concentration (Pharmacological Data)

60 mg

Kind of Dosing (Pharmacological Data)

title comp. (20 mg three times daily)/matching placebo was admin. during initial period of 4 weeks, followed by 2-wk washout period, then switched to opposite treatment for 4 weeks

Method (Pharmacological Data)

diabetic patients with IHF (mean age 66 years; NYHA class II-III) were randomized to title comp./placebo in double-blind crossover design; exercise tolerance, 2-dimensional echocardiograms, and TDI (rest, exercise) studied before and during treatment

Further Details (Pharmacological Data)

ET: exercise tolerance; EF: ejection fraction; IHF: ischemic heart failure; TDI: tissue Doppler imaging; parameters: peak systolic velocity, peak early diastolic, late diastolic velocity; NYHA: New York heart association classification of heart failure

Results

changes in ET did not differ in two groups; EF at rest and moderate exercise only improved significantly with title comp. when analyzed for first treatment period; TDI velocities unchanged; no signif. differences in other parameters; tables, diagrams

Thrainsdottir, Inga S.; Von Bibra, Helene; Malmberg, Klas; Ryden, Lars; Journal of Cardiovascular Pharmacology; vol. 44; nb. 1; (2004); p. 101 - 108, View in Reaxys 65 of 94

Effect (Pharmacological Data)

nephroprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3 mg/kg

Method (Pharmacological Data)

animals deprived water for 24 h and injected with glycerol for ARF; title comp. administered 30 min before and 12 h after glycerol; 24 h later kidneys isolated, fixed, cut and stained with haematoxylin and eosin; histopathological changes evaluated

Further Details (Pharmacological Data)

control: saline; ARF: acute renal failure

Results

title comp. partially reverted morphological changes produced by glycerol (table, figure)

Chander, Vikas; Singh, Devinder; Chopra, Kanwaljit; Pharmacology; vol. 67; nb. 1; (2003); p. 41 - 48, View in Reaxys 66 of 94

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3 mg/kg

Method (Pharmacological Data)

animals deprived water for 24 h and injected with glycerol for ARF; title comp. administered 30 min before and 12 h after glycerol; 24 h later kidneys isolated and PMS obtained; lipid peroxidation estimated by measurement of malondialdehyde content

Further Details (Pharmacological Data)

control: saline; ARF: acute renal failure; PMS: postmitochondrial supernatant, obtained from whole-kidney homogenate

Results

title comp. produced significant decrease in lipid peroxidation elevated by glycerol (figure)

Chander, Vikas; Singh, Devinder; Chopra, Kanwaljit; Pharmacology; vol. 67; nb. 1; (2003); p. 41 - 48, View in Reaxys 67 of 94

Effect (Pharmacological Data)

enzyme; induction of

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

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Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3 mg/kg

Method (Pharmacological Data)

animals deprived water for 24 h, injected with glycerol for ARF; title comp. administered 30 min before and 12 h after glycerol; 24 h later kidneys isolated; reduced glutathione conc. and enzyme activities were measured in PMS photometrically

Further Details (Pharmacological Data)

control: saline; ARF: acute renal failure; PMS: postmitochondrial supernatant from wholekidney homogenate; enzymes (used as measure of oxidative stress): catalase, glutathione reductase, and superoxide dismutase

Results

title comp. significantly improved glycerol-induced reductions in reduced glutathione conc. and in activities of catalase, glutathione reductase, and superoxide dismutase (figure)

Chander, Vikas; Singh, Devinder; Chopra, Kanwaljit; Pharmacology; vol. 67; nb. 1; (2003); p. 41 - 48, View in Reaxys 68 of 94

Effect (Pharmacological Data)

nephroprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3 mg/kg

Method (Pharmacological Data)

animals (150 - 200 g) deprived water for 24 h and injected with hypertonic glycerol for ARF; title comp. administered 30 min before and 12 h after glycerol; 24 h later urine output measured

Further Details (Pharmacological Data)

control: saline; ARF: acute renal failure

Results

title comp. significantly decreased glycerol-induced fall in urine output (table)

Chander, Vikas; Singh, Devinder; Chopra, Kanwaljit; Pharmacology; vol. 67; nb. 1; (2003); p. 41 - 48, View in Reaxys 69 of 94

Effect (Pharmacological Data)

water intake; stimulation of

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3 mg/kg

Method (Pharmacological Data)

animals (150 - 200 g) deprived water for 24 h and injected with hypertonic glycerol for ARF; title comp. administered 30 min before and 12 h after glycerol; 24 h later water intake measured

Further Details (Pharmacological Data)

control: saline; ARF: acute renal failure

Results

title comp. significantly decreased glycerol-induced fall in water intake (table)

Chander, Vikas; Singh, Devinder; Chopra, Kanwaljit; Pharmacology; vol. 67; nb. 1; (2003); p. 41 - 48, View in Reaxys 70 of 94

Effect (Pharmacological Data)

metabolic

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

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Concentration (Pharmacological Data)

3 mg/kg

Method (Pharmacological Data)

animals deprived water for 24 h and injected with glycerol for ARF; title comp. administered 30 min before and 12 h after glycerol; 24 h later blood collected; BUN and creatinine levels and urea and creatinine clearances assayed by standard kits

Further Details (Pharmacological Data)

control: saline; ARF: acute renal failure; BUN: blood urea nitrogen

Results

title comp. produced significant decrease in BUN and plasma creatinine concentrations elevated by glycerol and significantly improved glycerol-reduced creatinine and urea clearances (figure)

Chander, Vikas; Singh, Devinder; Chopra, Kanwaljit; Pharmacology; vol. 67; nb. 1; (2003); p. 41 - 48, View in Reaxys 71 of 94

Effect (Pharmacological Data)

kidney protectant

Species or Test-System (Pharmacological Data)

pig kidney

Concentration (Pharmacological Data)

1e-06 mol/l

Kind of Dosing (Pharmacological Data)

in UW, HEH or CEL solutions

Method (Pharmacological Data)

following nephrectomy, kidneys cold-flushed and preserved at 4 deg C for 24, 48 and 72 h in title comp.-containing solution, then organs autotransplanted; ureteneocystostomy and contralateral nephrectomy performed; blood and urine measured with AA

Further Details (Pharmacological Data)

UW: University of Wisconsin solution; HEH: Hopital Edouard Herriot solution; CEL: Celsior solution; AA: automatic analyser; IRI: ischemia-reperfusion injury

Results

title comp. in CEL and HEH reduced chronic injury; in all experiments fibrosis dramatically reduced by title comp. and correlated with improved preservation of nephronic mass even after 72 h; CD4+-cells infiltration modulated, IRI reduced

Faure, Jean-Pierre; Baumert, Herve; Han, Zeqiu; Goujon, Jean Michel; Favreau, Frederic; Dutheil, Delphine; Petit, Isabelle; Barriere, Michel; Tallineau, Claude; Tillement, Jean Paul; Carretier, Michel; Mauco, Gerard; Papadopoulos, Vassilios; Hauet, Thierry; Biochemical Pharmacology; vol. 66; nb. 11; (2003); p. 2241 - 2250, View in Reaxys 72 of 94

Effect (Pharmacological Data)

renoprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3 mg/kg

Method (Pharmacological Data)

rats (150-200 g) treated with title comp. 30 min prior to i.p. injection of Fe-NTA (8 mg iron per kg body wt); 1 h after Fe-NTA injection rats killed; kidneys isolated for histopathological examination

Further Details (Pharmacological Data)

Fe-NTA: ferric nitrilotriacetate; 3 groups: control (saline only), Fe-NTA, title comp. plus FeNTA

Results

treatment with title comp. preserved normal morphology of kidney, showed normal glomeruli, no cast formation and slight oedema of tubular cells; table, photo

Singh, Devinder; Chander, Vikas; Chopra, Kanwaljit; Toxicology; vol. 191; nb. 2-3; (2003); p. 143 - 151, View in Reaxys 73 of 94

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

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Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3 mg/kg

Method (Pharmacological Data)

rats (150-200 g) treated with title comp. 30 min prior to i.p. injection of Fe-NTA (8 mg iron per kg body wt); 1 h after Fe-NTA injection rats killed; kidneys isolated, homogenized, PMS prepared; lipid peroxidation analyzed by TBARS assay

Further Details (Pharmacological Data)

Fe-NTA: ferric nitrilotriacetate; PMS: post mitochondrial supernatant; TBARS: thiobarbituric acid reactive substances; 3 groups: control (saline only), Fe-NTA, title comp. plus FeNTA

Results

title comp. inhibited Fe-NTA-induced lipid peroxidation; diagram

Singh, Devinder; Chander, Vikas; Chopra, Kanwaljit; Toxicology; vol. 191; nb. 2-3; (2003); p. 143 - 151, View in Reaxys 74 of 94

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3 mg/kg

Method (Pharmacological Data)

Further Details (Pharmacological Data)

Fe-NTA: ferric nitrilotriacetate; PMS: post mitochondrial supernatant; GSH: reduced glutathione; GR: glutathione reductase; CAT: catalase; SOD: superoxide dismutase; 3 groups: control (saline only), Fe-NTA, title comp. plus Fe-NTA

Results

title comp. prevented severe depletion of renal antioxidant enzyme pool induced by FeNTA; diagrams

Singh, Devinder; Chander, Vikas; Chopra, Kanwaljit; Toxicology; vol. 191; nb. 2-3; (2003); p. 143 - 151, View in Reaxys 75 of 94

Effect (Pharmacological Data)

renoprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

3 mg/kg

Method (Pharmacological Data)

rats (150-200 g) treated with title comp. 30 min prior to i.p. injection of Fe-NTA (8 mg iron per kg body wt); 1 h after Fe-NTA injection rats killed; blood collected; plasma samples assayed for BUN and serum creatinine by using standard diagnostic kits

Further Details (Pharmacological Data)

Fe-NTA: ferric nitrilotriacetate; BUN: blood urea nitrogen; 3 groups: control (saline only), Fe-NTA, title comp. plus Fe-NTA

Results

title comp. blocked Fe-NTA-induced renal dysfunction; levels of BUN and serum creatinine similiar to those in control; diagrams

Singh, Devinder; Chander, Vikas; Chopra, Kanwaljit; Toxicology; vol. 191; nb. 2-3; (2003); p. 143 - 151, View in Reaxys 76 of 94

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

human red blood cells

Sex

male

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Concentration (Pharmacological Data)

1 - 5 μmol/l

Method (Pharmacological Data)

6 healthy volunteers RBC suspension (hematocrit 20 percent) incubated with PMS in presence of title comp. for 120 min; 37 deg C; PBS; after centrifugation RBC filterability (flows through filter with 5-μm pores) measured

Further Details (Pharmacological Data)

PMS: phenazine methosulfate; RBC: red blood cells; PBS: phosphate-buffered saline; RCTT: red blood cells transit time

Results

title comp. prevented RCTT increase induced by PMS (harden RBC because of free radical generation) at 5 μmol/l (12.9 percent prevention) (table)

Marton, Zsolt; Halmosi, Robert; Horvath, Beata; Alexy, Tamas; Kesmarky, Gabor; Vekasi, Judit; Battyany, Istvan; Hideg, Kalman; Toth, Kalman; Journal of Cardiovascular Pharmacology; vol. 38; nb. 5; (2001); p. 745 - 753, View in Reaxys 77 of 94

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

human red blood cells

Sex

male

Concentration (Pharmacological Data)

1 - 5 μmol/l

Method (Pharmacological Data)

6 healthy volunteers RBC suspension (hematocrit 20 percent) incubated with PMS in presence of title comp. for 120 min; 37 deg C; PBS; after centrifugation potassium conc. in supernatant measured using flame photometer; lithium base solution used

Further Details (Pharmacological Data)

PMS: phenazine methosulfate; RBC: red blood cells; PBS: phosphate-buffered saline

Results

title comp. prevented potassium leaking evelation induced by PMS due to free radical generation at 5 μmol/l (14.3 percent prevention) (table)

Effect (Pharmacological Data)

cytoprotective

Species or Test-System (Pharmacological Data)

pig kidney

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

kidneys from 45 kg white male pigs excised; preserved in Euro-Collins or University of Wisconsin sol. with title comp. (48 h; 4 deg C), then autotransplanted (TR); pigs contralaterally nephrectomized

Further Details (Pharmacological Data)

renal function (plasma, urinary creatinine, Na(+)) assessed, glomerular filtration rate <GFR>, fractional Na(+) clearance calculated; osmolality of urine, plasma measured by osmometer; osmolyte molecules detected by NMR

Results

renal medullary damage significantly reduced (decreased excretion of trimethylamine-Noxide, dimethylamine, dimethylglycine, acetate in urine) urinary concentrating ability improved (graph)

Effect (Pharmacological Data)

hepatoprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intramuscular

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Concentration (Pharmacological Data)

5 - 20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in saline; daily administration

Method (Pharmacological Data)

rats were treated with title comp. for 7 d; 120-min normothermic liver ischemia followed by 30-min reperfusion; macroscopic observation of liver

Further Details (Pharmacological Data)

vehicle control

Results

title comp. dose-dependently prevented ischemia-reperfusion-induced pathological liver changes

Elimadi, Aziz; Settaf, Abdellatif; Morin, Didier; Sapena, Rosa; Lamchouri, Fatima; Cherrah, Yahia; Tillement, Jean-Paul; Journal of Pharmacology and Experimental Therapeutics; vol. 286; nb. 1; (1998); p. 23 - 28, View in Reaxys 80 of 94

Effect (Pharmacological Data)

hepatoprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intramuscular

Concentration (Pharmacological Data)

5 - 20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in saline; daily administration

Method (Pharmacological Data)

rats were treated with title comp. for 7 d; 120-min normothermic liver ischemia followed by 30-min reperfusion; blood samples; ischemia-induced increase in plasma ASAT and ALAT levels was assessed; Boehringer-Mannheim kit

Further Details (Pharmacological Data)

vehicle control; ASAT: aspartate aminotransferase; ALAT: alanine aminotransferase

Results

title comp. at 10 - 20 mg/kg reduced ischemia-induced increase in plasma ASAT and ALAT levels (figure)

Effect (Pharmacological Data)

hepatoprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intramuscular

Concentration (Pharmacological Data)

5 - 20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in saline; daily administration

Method (Pharmacological Data)

rats were treated with title comp. for 7 d; 120-min normothermic liver ischemia followed by 30-min reperfusion; decrease in hepatic ATP content caused by ischemia was determined; enzymatic assay

Further Details (Pharmacological Data)

vehicle control

Results

title comp. significantly improved ischemia-induced decrease in ATP content (figure)

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Effect (Pharmacological Data)

hepatoprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intramuscular

Concentration (Pharmacological Data)

5 - 20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in saline; daily administration

Method (Pharmacological Data)

rats were treated with title comp. for 7 d; 120-min normothermic liver ischemia followed by 30-min reperfusion; cannulation of common bile duct; ischemia-induced decrease in bile flow was determined

Further Details (Pharmacological Data)

vehicle control

Results

title comp. prevented ischemia-induced decrease in bile flow (figure)

Effect (Pharmacological Data)

hepatoprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intramuscular

Concentration (Pharmacological Data)

5 - 20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in saline; daily administration

Method (Pharmacological Data)

rats were treated with title comp. for 7 d; 120-min normothermic liver ischemia followed by 30-min reperfusion; isolated liver mitochondria in PB at 25 deg C; ischemia-induced decrease of mitochondrial coupling and ATP synthesis was assessed

Further Details (Pharmacological Data)

polarography; vehicle control; PB: phosphate buffer; mitochondrial coupling and ATP synthesis was demonstrated by decrease in RCR (respiratory control ratio) and P/O, respectively

Results

title comp. at 10 - 20 mg/kg protected mitochondria from ischemia-induced decrease in mitochondrial coupling and ATP synthesis (figure)

Effect (Pharmacological Data)

hepatoprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intramuscular

Concentration (Pharmacological Data)

5 - 20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in saline; daily administration

Method (Pharmacological Data)

rats were treated with title comp. for 7 d; 120-min normothermic liver ischemia followed by 30-min reperfusion; isolated liver mitochondria in PB at 25 deg C; ischemia-induced dissipation of membrane potential was determined using rhodamine 123

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Further Details (Pharmacological Data)

vehicle control; fluorescence spectrometry; PB: phosphate buffer

Results

title comp. prevented ischemia-induced decrease in mitochondrial membrane potential (figure, table)

Effect (Pharmacological Data)

hepatoprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intramuscular

Concentration (Pharmacological Data)

5 - 20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in saline; daily administration

Method (Pharmacological Data)

Further Details (Pharmacological Data)

vehicle control; PB: phosphate buffer; NAD(P)H: pyridine nucleotides

Results

title comp. at 10 - 20 mg/kg prevented ischemia-induced decrease in NAD(P)H level (figure, table)

Effect (Pharmacological Data)

cytoprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intramuscular

Concentration (Pharmacological Data)

5 - 20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in saline; daily administration

Method (Pharmacological Data)

rats were treated with title comp. for 7 d; 120-min normothermic liver ischemia followed by 30-min reperfusion; isolated liver mitochondria in PB at 25 deg C; ischemia-induced enhancement of swelling rate was assessed; spectrophotometry

Further Details (Pharmacological Data)

vehicle control; PB: phosphate buffer; swelling was initiated either by energizing mitochondria with succinate or by adding t-butylhydroperoxide and Ca(2+) to deenergized mitochondria

Results

title comp. at 10 - 20 mg/kg completely prevented ischemia-induced enhancement of swelling rate (figure)

Effect (Pharmacological Data)

protective

Species or Test-System (Pharmacological Data)

Syrian hamster BIO 14:6

Sex

male

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Route of Application

peroral

Concentration (Pharmacological Data)

18 mg/kg

Kind of Dosing (Pharmacological Data)

the dose was 12 mg/kg (0.12 g in 1 l of drinking water); after 80 days dose increase by 50 percent and became 18 mg/kg (0.18 g in 1 l of drinking water)

Method (Pharmacological Data)

cardiomyopathic hamsters treated with title comp. for 350 days; weight measured weekly until death; survival rate studied

Further Details (Pharmacological Data)

verapamil used as reference comp. (7 of 10 animals died before 350 days); vehicle (distilled water) used as control

Results

survival was longer (560 days) in comparison with control (360 days) by about 57 percent; 1 of 20 animals died by 350 days

D'Hahan, Nathalie; Taouil, Karima; Dassouli, Abdelilah; Jean-Emile Morel; European Journal of Pharmacology; vol. 328; nb. 2-3; (1997); p. 163 - 174, View in Reaxys 88 of 94

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

Syrian hamster BIO 14:6

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

18 mg/kg

Kind of Dosing (Pharmacological Data)

0.18 g of title comp. added to 1 l of drinking water

Method (Pharmacological Data)

cardiomyopathic hamsters (180-220 days old) treated with title comp.; concentration of title comp. in plasma measured after 8, 18, 32 days after treatment

Further Details (Pharmacological Data)

verapamil used as reference comp.; vehicle (distilled water) used as control

Results

plasma levels of title comp. and reference comp. were constant after 8-32 days of title comp. treatment (16.9 ng/ml) and after 30 days of reference comp. treatment (29.6 ng/ml)

D'Hahan, Nathalie; Taouil, Karima; Dassouli, Abdelilah; Jean-Emile Morel; European Journal of Pharmacology; vol. 328; nb. 2-3; (1997); p. 163 - 174, View in Reaxys 89 of 94

Effect (Pharmacological Data)

protective

Species or Test-System (Pharmacological Data)

Syrian hamster BIO 14:6

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

18 mg/kg

Kind of Dosing (Pharmacological Data)

0.18 g of title comp. administered in 1 l of drinking water per day from age of 30 days to 220 days or from age of 30 days to 350 days

Method (Pharmacological Data)

cardiomyopathic hamsters treated with title comp. for 350 days; body, heart, liver and lung weight measured after 30, 65, 140, 220 and 350 days

Further Details (Pharmacological Data)

verapamil used as reference comp. (reduced ventricular hypertrophy at 350 days by 22 percent, liver hypertrophy at 220 and 350 days by 25 percent and 18 percent, resp.); vehicle (distilled water) used as control

Results

title comp. reduced ventricular hypertrophy at 220 and 350 days by 12 percent and 14 percent, resp., liver hypertrophy at 220 and 350 days by 28 percent and 29 percent, resp.; no effect on body weight

D'Hahan, Nathalie; Taouil, Karima; Dassouli, Abdelilah; Jean-Emile Morel; European Journal of Pharmacology; vol. 328; nb. 2-3; (1997); p. 163 - 174, View in Reaxys

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Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Syrian hamster F1B

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

18 mg/kg

Kind of Dosing (Pharmacological Data)

0.18 g of title comp. administered in 1 l of drinking water per day from age of 30 days to 220 days or from age of 30 days to 350 days

Method (Pharmacological Data)

hamsters treated with title comp. for 350 days; body, heart, liver and lung weight measured after 30, 65, 140, 220 and 350 days

Further Details (Pharmacological Data)

verapamil used as reference comp.; vehicle (distilled water) used as control

Results

title comp. reduced ventricular to body weight ratio; no effect on body weight

D'Hahan, Nathalie; Taouil, Karima; Dassouli, Abdelilah; Jean-Emile Morel; European Journal of Pharmacology; vol. 328; nb. 2-3; (1997); p. 163 - 174, View in Reaxys 91 of 94

Effect (Pharmacological Data)

intracellular calcium level; decrease of

Species or Test-System (Pharmacological Data)

Syrian hamster BIO 14:6

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

18 mg/kg

Kind of Dosing (Pharmacological Data)

0.18 g of title comp. administered in 1 l of drinking water per day from age of 30 days to 220 days

Method (Pharmacological Data)

cardiomyopathic hamsters treated with title comp. from 30 to 220 days; total calcium content measured on 220 days; cytosolic calcium concentration determined by spectrofluorometry; intracellular calcium levels studied by laser scanning cytometry

Further Details (Pharmacological Data)

verapamil used as reference comp. (reduced cytosolic calcium concentration by 39 percent); vehicle (distilled water) used as control

Results

title comp. reduced total calcium concentration and decreased cytosolic calcium concentration by 54 percent (figures)

D'Hahan, Nathalie; Taouil, Karima; Dassouli, Abdelilah; Jean-Emile Morel; European Journal of Pharmacology; vol. 328; nb. 2-3; (1997); p. 163 - 174, View in Reaxys 92 of 94

Effect (Pharmacological Data)

restoration of oxidative phosphorylation

Species or Test-System (Pharmacological Data)

Wistar rat liver mitochondria

Sex

male

Concentration (Pharmacological Data)

0.025 - 2 μmol/l

Method (Pharmacological Data)

weight 170-220 g; decapitated; liver tissues excised; mitochondria prepared; impairment of oxidative phosphorylation experimentally induced by simultaneous addition of CsA (1 μM) and Ca++ (30 nmol/mg protein); measured V3 and P/O

Further Details (Pharmacological Data)

CsA=cyclosporin A; V3=oxygen consumption rate during state 3, corresponding to ATP synthesis; P/O ratio corresponds to number of ADP molecules added in the medium per oxygen atom consumed during phosphorylation, represents the yield of ATP synthesis

Type (Pharmacological Data)

EC50

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Value of Type (Pharmacological Data)

0.14 - 0.21 μmol/l

Results

CsA and Ca++ induced significant decrease in V3 and P/O; title comp. according to doses had two opposite effects: 0.025-0.800 μM restored V3 and P/O to initial values, >= 1 μM decreased them; EC50 0.14 and 0.21 μM for V3 and P/O, resp.

Salducci; Chauvet-Monges; Tillement; Albengres; Testa; Carrupt; Crevat; Journal of Pharmacology and Experimental Therapeutics; vol. 277; nb. 1; (1996); p. 417 - 422, View in Reaxys 93 of 94

Effect (Pharmacological Data)

reversion of Ca++ accumulation

Species or Test-System (Pharmacological Data)

Wistar rat liver mitochondria

Sex

male

Concentration (Pharmacological Data)

0.25 - 20 μmol/l

Method (Pharmacological Data)

weight 170-220 g; decapitated; liver tissues excised; mitochondria prepared; SSD study performed in presence of Ca++ and CsA; specific Ca++ electrode used to record Ca++ movements in extramitochondrial medium

Further Details (Pharmacological Data)

CsA = cyclosporin A; SSD = steady state duration; RR = ruthenium red

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.55 μmol/l

Results

after Ca++ addition rapid uptake observed which was prolonged by CsA; title comp. dosedependently antagonized this effect; title comp. itself (without CsA) induced Ca++ efflux from mitochondria; promoted Ca++ efflux after RR addition

Salducci; Chauvet-Monges; Tillement; Albengres; Testa; Carrupt; Crevat; Journal of Pharmacology and Experimental Therapeutics; vol. 277; nb. 1; (1996); p. 417 - 422, View in Reaxys 94 of 94

Effect (Pharmacological Data)

reversion of Ca++ accumulation

Species or Test-System (Pharmacological Data)

Wistar rat liver mitochondria

Sex

male

Concentration (Pharmacological Data)

0.25 - 10 μmol/l

Method (Pharmacological Data)

weight 170-220 g; decapitated; liver tissues excised; mitochondria prepared; SSD study performed in presence of Ca++ 100 nmol/mg protein and ADP (100 μM); specific Ca++ electrode used to record Ca++ movements in extramitochondrial medium

Further Details (Pharmacological Data)

SSD = steady state duration

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.46 μmol/l

Results

after Ca++ addition rapid uptake observed which was prolonged by ADP; title comp. antagonized the ADP-increased SSD in dose-dependent manner

Salducci; Chauvet-Monges; Tillement; Albengres; Testa; Carrupt; Crevat; Journal of Pharmacology and Experimental Therapeutics; vol. 277; nb. 1; (1996); p. 417 - 422, View in Reaxys Ecotoxicology (2) 1 of 2

Effect (Ecotoxicology)

intracellular Ca(2+) level; reduction of

Species or Test-System (Ecotoxicology)

Xenopus laevis skeletal muscle fibre

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Sex

female

Concentration (Ecotoxicology)

100 μmol/l

Method (Ecotoxicology)

fibres injected with fura 2 and incubated in RS + title comp.; fibres electrically stimulated for induction of TC and perfused 3 min at high PO2 (159 mmHg) and 15 min at hypoxia (3 5 mm Hg) following 3-min reoxygenation; <Ca(2+)>c measured by FS

Further Details (Ecotoxi- RS: Ringer solution; TC: tetanic contractions; <Ca(2+)>c: relative free cytosolic Ca(2+) cology) concentration; FS: fluorescence spectroscopy in inverted microscope; vehicle (RS) control Results

title comp. decreased basal (resting) <Ca(2+)>c at the end of hypoxic period and after reoxygenation (to 126 and 123 percent of resting values before stimulation, resp., vs 197 and 169 percent in control); relative peak <Ca(2+)>c was unaffected by title comp.

Stary; Kohin; Samaja; Howlett; Hogan; Experimental Physiology; vol. 88; nb. 3; (2003); p. 415 - 421, View in Reaxys 2 of 2

Effect (Ecotoxicology)

muscle relaxant

Species or Test-System (Ecotoxicology)

Xenopus laevis skeletal muscle fibre

Sex

female

Concentration (Ecotoxicology)

100 μmol/l

Method (Ecotoxicology)

fibres incubated in RS containing title comp.; fibres electrically stimulated for induction of TC every 5 s and perfused 3 min at high PO2 (159 mmHg) and 15 min at hypoxia (3 - 5 mm Hg) following 3-min reoxygenation; muscle force measured with FTS

Further Details (Ecotoxi- RS: Ringer solution; TC: tetanic contractions; FTS: force transducer system; vehicle (RS) cology) control Comment (Ecotoxicology)

No effect

Stary; Kohin; Samaja; Howlett; Hogan; Experimental Physiology; vol. 88; nb. 3; (2003); p. 415 - 421, View in Reaxys Use (53) Use Pattern

Location

References

Pharmaceuticals

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angina pectoris

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Patent; LES LABORATOIRES SERVIER; GENTY, Patrick; HERMELIN, Christophe; PEAN, Jean-Manuel; US2013/202710; (2013); (A1) English, View in Reaxys

chorioretinal disorders

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Patent; LES LABORATOIRES SERVIER; GENTY, Patrick; HERMELIN, Christophe; PEAN, Jean-Manuel; US2013/202710; (2013); (A1) English, View in Reaxys

vertigo of vascular origin

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Fibromyalgia syndrome (FMS)

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Chronic fatigue syndrome (CFS)

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Myofascial pain syndrome (MPS)

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Gulf War syndrome (GWS)

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Rheumatic condition

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Trigger point pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Trigger point tenderness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Depression

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Dizziness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Impaired concentration

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Irritable bowel syndrome

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Headache

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Fatigue

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Sleep disturbance

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Chronic headaches

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Sleep disorder

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Jaw pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Cognitive impairment

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Memory impairment

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Post-exertional malaise

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Muscle pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Morning stiffness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Menstrual cramping

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Numbness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Tingling sensations

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Skin sensitivities

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Chemical sensitivities

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Balance problems

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Stiffness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Fluid retention

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

weight loss

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

110/337

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Skin rashes

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Chronic fevers

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Peripheral numbness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Joint pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Coronary heart disease

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Stable angina

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

a partial fatty acid oxidation (pFox) inhibitor

Patent; Kaesemeyer, Wayne; US2006/205727; (2006); (A1) English, View in Reaxys

acute coronary syndrome (ACS) , especially in type II diabetics

Patent; Kaesemeyer, Wayne; US2006/205727; (2006); (A1) English, View in Reaxys

chronic angina, especially in type II diabetics

Patent; Kaesemeyer, Wayne; US2006/205727; (2006); (A1) English, View in Reaxys

chronic heart failure (CHF)

Patent; Kaesemeyer, Wayne; US2006/205727; (2006); (A1) English, View in Reaxys

peripheral arterial disease (PAD)

Patent; Kaesemeyer, Wayne; US2006/205727; (2006); (A1) English, View in Reaxys

endothelial dysfunction

Patent; Kaesemeyer, Wayne; US2006/205727; (2006); (A1) English, View in Reaxys

control of glucose levels

Patent; Kaesemeyer, Wayne; US2006/205727; (2006); (A1) English, View in Reaxys

bioactive agent for polymeric composition

Patent; Life Medical Sciences, Inc.; US6870012; (2005); (B2) English, View in Reaxys

adenosine enhancing function or a phospholipase inhibiting function

Patent; Kowa Co., Ltd.; Nissan Chemical Industries, Ltd.; EP1488808; (2004); (A1) English, View in Reaxys

glomerular disease

Patent; Kowa Co., Ltd.; Nissan Chemical Industries, Ltd.; EP1488808; (2004); (A1) English, View in Reaxys

anti-thrombocytic agent

Patent; Kowa Co., Ltd.; Nissan Chemical Industries, Ltd.; EP1488808; (2004); (A1) English, View in Reaxys

Reaxys ID 172796 View in Reaxys

5/323 CAS Registry Number: 21867-69-6 Chemical Name: 1-(4-methoxybenzyl)piperazine; 1-[(4-Methoxyphenyl)methyl]piperazine; 1-(4-methoxybenzyl)-piperazine; p-methoxybenzylpiperazine; 1-N-para-methoxybenzylpiperazine; 1-(4-methoxybenzyl) piperazine; 1-(4-Methoxybenzyl)piperazine Linear Structure Formula: HN(CH2CH2)2NCH2C6H4OCH3 Molecular Formula: C12H18N2O Molecular Weight: 206.288 Type of Substance: heterocyclic InChI Key: MGLUVVBFISROAH-UHFFFAOYSA-N

NH N

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Note: Substance Label (14) Label References 16

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 9; (2016); p. 2380 - 2382, View in Reaxys

Dib, Josef; Schlörer, Nils; Schänzer, Wilhelm; Thevis, Mario; Journal of Mass Spectrometry; vol. 50; nb. 2; (2015); p. 407 - 417, View in Reaxys

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

13f

Sadeghzadeh, Masoud; Sheibani, Shahab; Ghandi, Mehdi; Daha, Fariba Johari; Amanlou, Massoud; Arjmand, Mohammad; Hasani Bozcheloie, Abolfazl; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 488 - 497, View in Reaxys

Ed. to 12a

Wolf, Janine; Gonzalez Tanarro, Camino M.; Guetschow, Michael; Sieler, Joachim; Schulze, Baerbel; Helvetica Chimica Acta; vol. 91; nb. 1; (2008); p. 35 - 45, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 60; nb. 12; (2007); p. 928 - 933, View in Reaxys

Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 2086, View in Reaxys

Patent; THE UNIVERSITY OF MARYLAND, BALTIMORE; WO2006/105237; (2006); (A2) English, View in Reaxys; Hancock, Chad N.; Macias, Alba; Lee, Eun Kyoung; Yu, Su Yeon; MacKerell Jr., Alexander D.; Shapiro, Paul; Journal of Medicinal Chemistry; vol. 48; nb. 14; (2005); p. 4586 - 4595, View in Reaxys

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 4331, View in Reaxys

11, R&3%=4OMe

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

13c

Walczynski, Krzysztof; Guryn, Roman; Zuiderveld, Obbe P.; Timmerman, Henk; Farmaco; vol. 54; nb. 10; (1999); p. 684 - 694, View in Reaxys

Patent-Specific Data (4) Location in Patent References Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/91531; (2015); (A1) English, View in Reaxys Page/Page column

Patent; Korea Research Institute of Chemical Technology; Katholieke Universiteit Leuven, K.U. Leuven RandD; JUNG, Young Sik; LEE, Chong Kgo; KIM, Hae Soo; JEONG, Hee Chun; KIM, Pil Ho; HAN, Soo Bong; NEYTS, Johan; THIBAUT, Hendrik Jan; SHIN, Jin Soo; EP2722042; (2014); (A2) English, View in Reaxys

Page/Page column

Patent; KATHOLIEKE UNIVERSITEIT LEUVEN K.U. LEUVEN R and D; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Jung, Young Sik; Lee, Chong Kgo; Kim, Hae Soo; Jeong, Hee Chun; Kim, Pil Ho; Han, Soo Bong; Shin, Jin Soo; Neyts, Johan; Thibaut, Hendrik Jan; US2014/114068; (2014); (A1) English, View in Reaxys Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys

Derivative (2) Comment (Derivative)

References

112/337

2016-05-20 15:00:44

Dihydrochlorid: F: 261-263.5grad <unkorr.; Zers.; aus A.>

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

Dipikrat: F: 245-248grad

Patent; US Vit. Pharm.; BE617599; (1962); Chem.Abstr.; vol. 59; nb. 646; (1963), View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

99 - 101

Solvent (Melting Point)

petroleum ether

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys 2 of 3

Melting Point [°C]

28 - 31

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys 3 of 3

Melting Point [°C]

105 - 107

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys Boiling Point (9) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

122 - 124

0.7

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

132 - 133

1.5

Pesson et al.; European Journal of Medicinal Chemistry; vol. 10; (1975); p. 567,570, View in Reaxys

180 - 182

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys

137 - 138

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

158 - 160

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

147 - 148

Patent; US Vit. Pharm.; BE617599; (1962); Chem.Abstr.; vol. 59; nb. 646; (1963), View in Reaxys

130 - 136

1.5

Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys

128 - 130

1.5

Morren et al.; Bulletin des Societes Chimiques Belges; vol. 60; (1951); p. 282,288, View in Reaxys

150

2.5

Baltzly et al.; Journal of the American Chemical Society; vol. 66; (1944); p. 263,265, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5511

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

589

Density (1) 1 of 1

Density [g·cm-3]

1.0629

Measurement Temperature [°C]

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys Crystal Property Description (2) Colour & Other Location Properties

References

113/337

2016-05-20 15:00:44

yellow

Peterson, Quinn P.; Hsu, Danny C.; Goode, David R.; Novotny, Chris J.; Totten, Ryan K.; Hergenrother, Paul J.; Journal of Medicinal Chemistry; vol. 52; nb. 18; (2009); p. 5721 - 5731, View in Reaxys

NMR Spectroscopy (12) 1 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Peterson, Quinn P.; Hsu, Danny C.; Goode, David R.; Novotny, Chris J.; Totten, Ryan K.; Hergenrother, Paul J.; Journal of Medicinal Chemistry; vol. 52; nb. 18; (2009); p. 5721 - 5731, View in Reaxys

114/337

2016-05-20 15:00:44

5 of 12

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

101

Location

supporting information

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys 7 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys 8 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 9 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 10 of 12

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy)

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2016-05-20 15:00:44

Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 11 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys 12 of 12

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

neat liquid

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum

supporting information

References Peterson, Quinn P.; Hsu, Danny C.; Goode, David R.; Novotny, Chris J.; Totten, Ryan K.; Hergenrother, Paul J.; Journal of Medicinal Chemistry; vol. 52; nb. 18; (2009); p. 5721 - 5731, View in Reaxys

Pharmacological Data (6) 1 of 6

Comment (Pharmacological Data)

Bioactivities present

Patent; Laboratoire Roger Bellon; US3950338; (1976); (A1) English, View in Reaxys; Patent; American Cyanamid Company; US4562189; (1985); (A1) English, View in Reaxys; Patent; Boehringer Mannheim GmbH; US4616086; (1986); (A1) English, View in Reaxys; Patent; Boehringer Ingelheim Ltd.; US4725597; (1988); (A1) English, View in Reaxys; Patent; Massachusetts College of Pharmacy; US2002/115655; (2002); (A1) English, View in Reaxys; Patent; ZAMBON GROUP S.p.A.; EP781126; (2001); (B1) English, View in Reaxys; Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys; Patent; THE UNIVERSITY OF MARYLAND, BALTIMORE; WO2006/105237; (2006); (A2) English, View in Reaxys; Patent;

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2016-05-20 15:00:44

Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys; Baltzly et al.; Journal of the American Chemical Society; vol. 66; (1944); p. 263,265, View in Reaxys; Horrom et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 753, View in Reaxys; Morren et al.; Bulletin des Societes Chimiques Belges; vol. 60; (1951); p. 282,288, View in Reaxys; Pesson et al.; European Journal of Medicinal Chemistry; vol. 10; (1975); p. 567,570, View in Reaxys; Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys; Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys; Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys; Patent; US Vit. 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vol. 12; nb. 21; (2002); p. 3105 - 3109, View in Reaxys; Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys; Zhao, He; He, Xiaoshu; Thurkauf, Andrew; Hoffman, Diane; Kieltyka, Andrzej; Brodbeck, Robbin; Primus, Renee; Wasley, Jan W.F.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 21; (2002); p. 3111 - 3115, View in Reaxys; Feng, Song; Xia, Yu; Han, Dongmei; Zheng, Chunyan; He, Xuchang; Tang, Xican; Bai, Donglu; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 3; (2005); p. 523 - 526, View in Reaxys; Hancock, Chad N.; Macias, Alba; Lee, Eun Kyoung; Yu, Su Yeon; MacKerell Jr., Alexander D.; Shapiro, Paul; Journal of Medicinal Chemistry; vol. 48; nb. 14; (2005); p. 4586 - 4595, View in Reaxys; Omran, Ziad; Cailly, Thomas; Lescot, Elodie; Santos, Jana Sopkova-De Oliveira; Agondanou, Jean-Hugues; Lisowski, Vincent; Fabis, Frederic; Godard, Anne-Marie; Stiebing, Silvia; Le Flem, Guillaume; Boulouard, Michel; Dauphin, Francois; Dallemagne, Patrick; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 40; nb. 12; (2005); p. 1222 - 1245, View in Reaxys; Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys; Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 - 2086, View in Reaxys; Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 60; nb. 12; (2007); p. 928 - 933, View in Reaxys; Wolf, Janine; Gonzalez Tanarro, Camino M.; Guetschow, Michael; Sieler, Joachim; Schulze, Baerbel; Helvetica Chimica Acta; vol. 91; nb. 1; (2008); p. 35 - 45, View in Reaxys; Patent; Ebdrup, Soren; de Jong, Johannes Cornelis; Jacobsen, Poul; Hansen, Holger Claus; Vedso, Per; US2003/166644; (2003); (A1) English, View in Reaxys; Patent; Zambon Group; US5674909; (1997); (A1) English, View in Reaxys; Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; 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Hoon; Xia, Yan; Kim, Eun Kyung; Jin, Yinglan; Kaur, Navneet; Kim, Eun Seon; Kim, Dae Kyong; Jung, Hwa Young; Choi, Yongseok; Park, Mi-Kyung; Min, Yong Ki; Lee, Kiho; Lee, Kyeong; Bioorganic and Medicinal Chemistry Letters; vol. 19; nb. 18; (2009); p. 5376 - 5379, View in Reaxys; Oezkay, Yusuf; Isikdag, Ilhan; Incesu, Zerrin; Akalin, Guelsen; European Journal of Medicinal Chemistry; vol. 45; nb. 8; (2010); p. 3320 - 3328, View in Reaxys; Long, Jonathan Z.; Jin, Xin; Adibekian, Alexander; Li, Weiwei; Cravatt, Benjamin F.; Journal of Medicinal Chemistry; vol. 53; nb. 4; (2010); p. 1830 - 1842, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Ding, Huaiwei; Chen, Zhe; Zhang, Cunlong; Xin, Tian; Wang, Yini; Song, Hongrui; Jiang, Yuyang; Chen, Yuzong; Xu, Yongnan; Tan, Chunyan; Molecules; vol. 17; nb. 4; (2012); p. 4703 - 4716, View in Reaxys; Wu, Yan; Ma, Long-Xu; Niu, TianWei; Cui, Xun; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 13; (2012); p. 4229 - 4232, View in Reaxys; Cacchi, Sandro; Fabrizi, Giancarlo; Filisti, Eleonora; Goggiamani, Antonella; Iazzetti, Antonia; Maurone, Loredana; Organic and Biomolecular Chemistry; vol. 10; nb. 24; (2012); p. 4699 - 4703, View in Reaxys; Song, Jiho; Kim, Young Jin; Min, Kyung Hoon; Lee, Hyun-E; Kim, Su Yeon; Kim, Dong-Seok; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 22; (2012); p. 6943 - 6946,4, View in Reaxys; Grob, Jonathan E.; Dechantsreiter, Michael A.; Tichkule, Ritesh B.; Connolly, Michael K.; Honda, Ayako; Tomlinson, Ronald C.; Hamann, Lawrence G.; Organic Letters; vol. 14; nb. 21; (2012); p. 5578 - 5581,4, View in Reaxys; Oezkay, Uemide Demir; Can, Oezgur Devrim; Ozkay, Yusuf; Oztuerk, Yusuf; Pharmacological Reports; vol. 64; nb. 4; (2012); p. 834 - 847, View in Reaxys; Wu, Yan; Ma, Long-Xu; Sun, Liang-Peng; Song, Ming-Xia; Cui, Xun; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 3; (2013); p. 757 - 760, View in Reaxys; Wu, Yan; Sun, Liang-Peng; Ma, Long-Xu; Che, Jian; Song, Ming-Xia; Cui, Xun; Piao, Hu-Ri; Chemical Biology and Drug Design; vol. 81; nb. 5; (2013); p. 591 - 599, View in Reaxys; Sadeghzadeh, Masoud; Sheibani, Shahab; Ghandi, Mehdi; Daha, Fariba Johari; Amanlou, Massoud; Arjmand, Mohammad; Hasani Bozcheloie, Abolfazl; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 488 - 497, View in Reaxys; Koch, Pierre; Akkari, Rhalid; Brunschweiger, Andreas; Borrmann, Thomas; Schlenk, Miriam; Kueppers, Petra; Koese, Meryem; Radjainia, Hamid; Hockemeyer, Joerg; Drabczynska, Anna; Kiec-Kononowicz, Katarzyna; Mueller, Christa E.; Bioorganic and Medicinal Chemistry; vol. 21; nb. 23; (2013); p. 7435 - 7452, View in Reaxys; Patent; KATHOLIEKE UNIVERSITEIT LEUVEN K.U. 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Mackerell JR.; US2007/66616; (A1); (2007), View in Reaxys; Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOIKE, Tatsuki; YOSHIKAWA, Masato; ANDO, Haruhi; FARNABY, William John; IKEDA, Shuhei; KAJITA, Yuichi; NISHI, Toshiya; (71 pag.); US2016/24049; (2016); (A1) English, View in Reaxys; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 9; (2016); p. 2380 - 2382, View in Reaxys 2 of 6

Comment (Pharmacological Data)

physiological behaviour discussed

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys 3 of 6

Effect (Pharmacological Data)

ERK-mediated phosphorylation of RSK-1; inhibition of

Species or Test-System (Pharmacological Data)

cervical carcinoma HeLa cells of human

Method (Pharmacological Data)

All obtained compounds were subjected to assays of ERK specific phosphorylation of Rsk-1 and/or EIk-I as examined by immunoblot analysis using phosphorylation specific

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antibodies. In Figure 4A HeLa cells were cultured in 24 well EPO plates and pretreated for 20-30 minutes with 0-100 mM of the selected test compounds. The cells were then stimulated with epidermal growth factor (EGF5 50 ng/ml) for 5 minutes to activate the ERK pathway. Cell lysates were collected and immunoblotted for ERK- mediated phosphorylation of Rsk-1 on Thr573. As shown, EGF treatment alone caused a robust increase in Thr573 phosphorylation on Rsk-1 in the absence of test compounds. A typical immunoblot for Rsk-1 phosphorylation in the presence of 15 test compounds is shown in Figure 4A. The presence of test compounds had varying inhibitory effects on ERK-mediated Rsk-1 phosphorylation. In these samples, densitometry quantification of the inimunoblots showed that two compounds caused greater than 50percent inhibition of Rsk-1 phosphorylation. Four additional compounds (17, 36, 79 and 80) inhibited ERK-mediated Rsk-1 phosphorylation by 20-25percent out of the 80 compounds tested (data not shown).The ERK-specific phosphorylation of the transcription factor EIk-I on Ser383 was also tested with the compounds that showed the highest inhibition of Rsk-1 phosphorylation in Figure 4A, i.e. compound 76. As shown, increasing doses of compound 76 inhibited ERK-mediated EIk-I phosphorylation in response to EGF stimulation (Fig. 4B). As a protein loading control, the expression of a -tubulin was unchanged. Importantly, ERKl/2 phosphorylation on its activating sites was largely unaffected by the test compound. This finding support the specificity of this test compound for inhibiting ERK phosphorylation of downstream substrates, but has little effect on ERK protein phosphorylation by its upstream activator MEKl / 2.Compounds that were identified using the 3D structure of phosphorylated ERK2 also were tested. In Figure 4C four (89, 92, 93, and 95) of the ten compounds tested showed evidence for inhibiting ERK-mediated ELK-I phosphorylation. It should be noted that in vitro experiments using purified active ERK2 and a non-specific peptide substrate demonstrated that the test compounds did not affect ERK2 catalytic activity (data not shown). Therefore, these data suggest that CADD can identify compounds that will disrupt interactions with substrate proteins using either the unphosphorylated or phosphorylated ERK2 structures. EPO Figures 5A-5B show the chemical structures for some of the compounds that have been tested for their ability to inhibit ERK-mediated substrate phosphorylation. These include compounds 17, 36, 67, 68, 76, 79, 80, and 81, which were developed against the CD and ED domain (Sl site) using unphosphorylated ERK2 and compounds 86-98, which were developed against the Sl site using the phosphorylated (active) ERK2 protein structure. All compounds except compounds 36 and 68 showed some inhibition of ERK- mediated phosphorylation of RSK-I. Compound 36 was used as control as it had little effect on ERK substrate phosphorylation. The structure of compound 68 was included because it appeared to enhance ERK phosphorylation of RSK-I. As shown, the compounds have diverse chemical structures, although some similarities are evident. For example, 17, 79, 80 and 81 have amide moieties directly adjacent to aromatic rings with many of compounds including piperazine groups. The advantage of having chemically diverse structures as this stage of the project is, during future lead optimization efforts, to maximize the potential that one or more of the compounds will have the desired bioavailability properties as well as specifically targeting ERK-substrate interactions. Results

showed some inhibition of the effect

Location

Page/Page column 33-35

Patent; THE UNIVERSITY OF MARYLAND, BALTIMORE; WO2006/105237; (2006); (A2) English, View in Reaxys 4 of 6

Effect (Pharmacological Data)

cell proliferation; inhibition of

Species or Test-System (Pharmacological Data)

cervical carcinoma HeLa cells of human

Method (Pharmacological Data)

Effects of active compounds on cell proliferationThe effects of the active compounds on cell proliferation and survival were tested using a colony formation assay. A screen of five test compounds showed that two compounds (76 and 81) completely inhibited cell proliferation, as evident by decreased number of cell colonies (Fig. 8A). Other compounds, including 36, 67, and 68, had little effect on colony formation (Fig. 8A).Dose response assays demonstrated that compounds 76 and 81 similarly inhibited HeLa cell colony formation with an IC50 of approximately 15-20 μM (Fig. 8B). In A549 lung carcinoma cells the IC50 for compounds 76 and 81 was approximately 25 and 15 EPO μM, respectively (Fig. 8C). Moreover, inhibition of cell proliferation following incubation with compounds 76 and 81 was observed in the SUM- 159 estrogen-receptor negative breast cancer cell line (Fig. 8D) and HTl 080 fibrosarcoma cells (data not shown). Compounds 17, 79, and 80 also inhibited HeLa, A549, HT1080, and MDA-MB-468 cell proliferation with IC50 values similar to 76 and 81. Thus, several test compounds that show maximal inhibition of ERK substrates are also effective inhibitors of proliferation in cultured cancer cell lines.Compounds 86-98 also were tested in the colony formation assay. Colony formation inhibition is shown for compounds 92 and 94-95. AU compounds showed some degree of colony formation inhibition (Fig. 8E), although compound 94 (Fig. 8E) and 93 were the most effective inhibi-

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tors of colony formation, their effect may be non-specific as these compounds interactions with ERK2 were inconclusive as determined by fluorescence titrations (Fig. 6B). However, 92 and 95 inhibited in the 10-100 mM range, consistent with the binding in the fluorescence quenching experiment (Fig. 6B), indicating their function to be associated with direct binding to ERK. The differences in effects of active compounds on cell proliferation may be due to differences in how the active compounds affect ERK substrate phosphorylation. For example, active compounds that show stronger inhibition of cell proliferation may target a broader range of ERK substrates. Table 3 provides the IC50 concentrations (micromolar) for compounds 86-9 Results

had little effect on colony formation

Location

Page/Page column 38-39

Patent; THE UNIVERSITY OF MARYLAND, BALTIMORE; WO2006/105237; (2006); (A2) English, View in Reaxys 5 of 6

Effect (Pharmacological Data)

antiproliferative

Species or Test-System (Pharmacological Data)

human cervical carcinoma HeLa cells

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

colony formation assay; cells incubated with title comp. in DMEM with 10 percent FBS for 10 d; cells stained with crystal violet and colonies counted

Results

title comp. had little effect on cell proliferation

Hancock, Chad N.; Macias, Alba; Lee, Eun Kyoung; Yu, Su Yeon; MacKerell Jr., Alexander D.; Shapiro, Paul; Journal of Medicinal Chemistry; vol. 48; nb. 14; (2005); p. 4586 - 4595, View in Reaxys 6 of 6

Effect (Pharmacological Data)

protein binding

Species or Test-System (Pharmacological Data)

extracellular signal-regulated ERK2 kinase

Method (Pharmacological Data)

fluorescence titration assay; Tris-HCl, pH 7.5

Results

title comp. did not show fluorescence quenching at concentrations tested

Hancock, Chad N.; Macias, Alba; Lee, Eun Kyoung; Yu, Su Yeon; MacKerell Jr., Alexander D.; Shapiro, Paul; Journal of Medicinal Chemistry; vol. 48; nb. 14; (2005); p. 4586 - 4595, View in Reaxys

Reaxys ID 146857 View in Reaxys

6/323 CAS Registry Number: 23173-57-1 Chemical Name: 1-(4-methylbenzyl)piperazine; 1-(4-methylphenylmethyl)piperazine; 1-(4-methylbenzyl)-piperazine; 4-(4methylbenzyl)piperazine; N-(4-methylbenzyl)piperazine; 1-(4Methylbenzyl)piperazine; 1-(4-methyl-benzyl)-piperazine Linear Structure Formula: C12H18N2 Molecular Formula: C12H18N2 Molecular Weight: 190.288 Type of Substance: heterocyclic InChI Key: RNAXUUAJNMDESG-UHFFFAOYSA-N Note:

NH N

Substance Label (10) Label References 2b

Zhou, An; Wu, Hongfei; Pan, Jian; Wang, Xuncui; Li, Jiaming; Wu, Zeyu; Hui, Ailing; Molecules; vol. 20; nb. 1; (2015); p. 1304 - 1318, View in Reaxys

5{13}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

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Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 2086, View in Reaxys

He, Feng-Qi; Liu, Xing-Hai; Wang, Bao-Lei; Li, Zheng-Ming; Journal of Chemical Research; nb. 12; (2006); p. 809 - 811, View in Reaxys

11, R&3%=4-Me

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

18 R1=Me

Zhao, He; Thurkauf, Andrew; Braun, Julia; Brodbeck, Robin; Kieltyka, Andrzej; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 18; (2000); p. 2119 - 2122, View in Reaxys

13b

Walczynski, Krzysztof; Guryn, Roman; Zuiderveld, Obbe P.; Timmerman, Henk; Farmaco; vol. 54; nb. 10; (1999); p. 684 - 694, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Derivative (1) Comment (Derivative)

References

Dimaleat: F: 174-176grad; Pharmakolog. Eigensch.

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

35 - 36.5

Solvent (Melting Point)

petroleum ether

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys 2 of 2

Melting Point [°C]

36 - 37

Steck,E.A.; Journal of Organic Chemistry; vol. 27; (1962); p. 306 - 308, View in Reaxys Boiling Point (5) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

97 - 98

0.3

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

156 - 158

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

118 - 120

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

78 - 83

0.1

Steck,E.A.; Journal of Organic Chemistry; vol. 27; (1962); p. 306 - 308, View in Reaxys

121 - 122

Morren et al.; Bulletin des Societes Chimiques Belges; vol. 60; (1951); p. 282,288, View in Reaxys

Chromatographic Data (1) Chromatographic References data GC (Gas chroma- Drinkel, Emma E.; Campedelli, Roberta R.; Manfredi, Alex M.; Fiedler, Haidi D.; Nome, Faruk; Journal of tography) Organic Chemistry; vol. 79; nb. 6; (2014); p. 2574 - 2579, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties

References

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white

Paragraph 0130

yellow

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys

NMR Spectroscopy (9) 1 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

600

Zhou, An; Wu, Hongfei; Pan, Jian; Wang, Xuncui; Li, Jiaming; Wu, Zeyu; Hui, Ailing; Molecules; vol. 20; nb. 1; (2015); p. 1304 - 1318, View in Reaxys 2 of 9

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Location

supporting information

Drinkel, Emma E.; Campedelli, Roberta R.; Manfredi, Alex M.; Fiedler, Haidi D.; Nome, Faruk; Journal of Organic Chemistry; vol. 79; nb. 6; (2014); p. 2574 - 2579, View in Reaxys 3 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Original Text (NMR Spectroscopy)

1H-NMR (500 MHz, CDCl ): δ 7.18 (d, 2H, J=8.0 Hz), 7.09 (d, 2H, J=7.5 Hz), 3.42 (s, 2H), 3 2.84 (t, 4H, J=5.0 Hz), 2.37 (br s, 4H), 2.31 (s, 3H), 1.54 (br s, 1H)

Location

Paragraph 0130

Signals [ppm]

7.18; 7.09; 3.42; 2.84; 2.37; 2.31; 1.54

Kind of signal

d, 2H, J=8.0 Hz; d, 2H, J=7.5 Hz; s, 2H; t, 4H, J=5.0 Hz; br s, 4H; s, 3H; br s, 1H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 4 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Original Text (NMR Spectroscopy)

13C-NMR

(125 MHz, CDCl3): δ 136.3, 134.7, 129.0, 128.6, 63.2, 54.3, 45.9, 20.9

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2016-05-20 15:00:44

Location

Paragraph 0130

Signals [ppm]

136.3; 134.7; 129; 128.6; 63.2; 54.3; 45.9; 20.9

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 5 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 8 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 9 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

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Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

gas chromatogra- supporting inforphy mass specmation trometry (GCMS); spectrum

Drinkel, Emma E.; Campedelli, Roberta R.; Manfredi, Alex M.; Fiedler, Haidi D.; Nome, Faruk; Journal of Organic Chemistry; vol. 79; nb. 6; (2014); p. 2574 - 2579, View in Reaxys

CID (collision-induced dissociation); ESI (Electrospray ionisation); IT (ion trap); Spectrum

Chai, Yunfeng; Sun, Hezhi; Pan, Yuanjiang; Sun, Cuirong; Journal of the American Society for Mass Spectrometry; vol. 22; nb. 9; (2011); p. 1526 - 1533, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys; Patent; Beecham Group Limited; US4405620; (1983); (A1) English, View in Reaxys; Patent; American Cyanamid Company; US4421753; (1983); (A1) English, View in Reaxys; Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US4692448; (1987); (A1) English, View in Reaxys; Patent; Boehringer Ingelheim Ltd.; US4725597; (1988); (A1) English, View in Reaxys; Steck,E.A.; Journal of Organic Chemistry; vol. 27; (1962); p. 306 - 308, View in Reaxys; Morren et al.; Bulletin des Societes Chimiques Belges; vol. 60; (1951); p. 282,288, View in Reaxys; Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys; Ohtaka; Yoshida; Suzuki; Shimohara; Tajima; Ito; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 12; (1988); p. 4825 - 4833, View in Reaxys; Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys; Buckle, Derek R.; Rockell, Caroline J. M.; Smith, Harry; Spicer, Barbara A.; Journal of Medicinal Chemistry; vol. 29; nb. 11; (1986); p. 2262 - 2267, View in Reaxys; Baziard-Mouysset, Genevieve; Younes, Salouma; Labssita, Youssef; Payard, Marc; Caignard, Daniel-Henri; Rettori, Marie-Claire; Renard, Pierre; Pfeiffer, Bruno; Guardiola-Lemaitre, Beatrice; European Journal of Medicinal Chemistry; vol. 33; nb. 5; (1998); p. 339 - 347, View in Reaxys; Zhao, He; Thurkauf, Andrew; Braun, Julia; Brodbeck, Robin; Kieltyka, Andrzej; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 18; (2000); p. 2119 2122, View in Reaxys; Walczynski, Krzysztof; Guryn, Roman; Zuiderveld, Obbe P.; Timmerman, Henk; Farmaco; vol. 54; nb. 10; (1999); p. 684 - 694, View in Reaxys; Zhao, He; Thurkauf, Andrew; He, Xiaoshu; Hodgetts, Kevin; Zhang, Xiaoyan; Rachwal, Stanislaw; Kover, Renata X.; Hutchison, Alan; Peterson, John; Kieltyka, Andrzej; Brodbeck, Robbin; Primus, Renee; Wasley, Jan W.F.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 21; (2002); p. 3105 - 3109, View in Reaxys; Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys; Zhao, He; He, Xiaoshu; Thurkauf, Andrew; Hoffman, Diane; Kieltyka, Andrzej; Brodbeck, Robbin; Primus, Renee; Wasley, Jan W.F.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 21; (2002); p. 3111 - 3115, View in Reaxys; Zhao, He; Zhang, Xiaoyan; Hodgetts, Kevin; Thurkauf, Andrew; Hammer, Jack; Chandrasekhar, Jayaraman; Kieltyka, Andrzej; Brodbeck, Robbin; Rachwal, Stanislaw; Primus, Renee; Manly, Charles; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 4; (2003); p. 701 - 704, View in Reaxys; Omran, Ziad; Cailly, Thomas; Lescot, Elodie; Santos, Jana Sopkova-De Oliveira; Agondanou, Jean-Hugues; Lisowski, Vincent; Fabis, Frederic; Godard, Anne-Marie; Stiebing, Silvia; Le Flem, Guillaume; Boulouard, Michel; Dauphin, Francois; Dallemagne, Patrick; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 40; nb. 12; (2005); p. 1222 - 1245, View in Reaxys; Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 - 2086, View in Reaxys; He, Feng-Qi; Liu, Xing-Hai; Wang, Bao-Lei; Li, Zheng-Ming; Journal of Chemical Research; nb. 12; (2006); p. 809 - 811, View in Reaxys; Romagnoli, Romeo; Baraldi, Pier Giovanni; Carrion, Maria Dora; Cara, Carlota Lopez; Preti, Delia; Cruz-Lopez, Olga; Tabrizi, Mojgan Aghazadeh; Moorman, Allan R.; Gessi, Stefania; Fogli, Eleonora; Sacchetto, Valeria; Borea, Pier Andrea; Journal of Medicinal Chemistry; vol. 50; nb. 15; (2007); p. 3706 - 3715, View in Reaxys; Patent; Rhone-Poulenc Sante; US4769366; (1988); (A1) English, View in Reaxys; Patent; Rhone-Poulenc Sante; US4831034; (1989); (A1) English, View in Reaxys; Patent; Rhone-Poulenc Sante; US4977166; (1990); (A1) English, View in Reaxys; Patent; Ebdrup, Soren; de Jong, Johannes Cornelis; Jacobsen, Poul; Hansen, Holger Claus; Vedso, Per; US2003/166644; (2003); (A1) English, View in Reaxys; Patent; Merck, Sharp and Dohme, Ltd.; US5684006; (1997); (A1) English, View in Reaxys; Liu, Xue-Kun; Cui, Xun; Hong, Lan; Sun, Liang-Peng; Quan, Zhe-Shan; Piao, Hu-Ri; European Journal of Medicinal Chemistry; vol. 44; nb. 7; (2009); p. 3027 - 3031, View in Reaxys; Cacchi, Sandro; Fabrizi, Giancarlo; Filisti, Eleonora; Synlett; nb. 11; (2009); p. 1817 - 1821, View in Reaxys; Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Prastaro, Alessandro; Tetrahedron; vol. 65; nb. 44; (2009); p. 8916 - 8929, View in Reaxys; Borrmann, Thomas; Hinz, Sonja; Bertarelli, Daniela C. G.; Li, Wenjin; Florin, Nicole C.; Scheiff, Anja B.; Mueller, Christa E.; Journal of Medicinal Chemistry; vol. 52; nb. 13; (2009); p. 3994 - 4006, View in Reaxys; Patent; Dainippon Sumitomo Pharma Co., Ltd.; AstraZeneca AB; EP2138497; (2009); (A1) English, View in Reaxys; Gitto, Rosaria; De Luca, Laura; Ferro, Stefania; De Grazia, Sara; Di Giorgio, Rosa Maria; Festa, Filomena; De Luca, Grazia; Journal of Heterocyclic Chemistry; vol. 47; nb. 1; (2010); p. 54 - 62, View in Reaxys; Oezkay, Yusuf; Isikdag, Ilhan; Incesu, Zerrin; Akalin, Guelsen; European Journal of Medicinal Chemistry; vol. 45; nb. 8; (2010); p. 3320 - 3328,

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View in Reaxys; Patent; Takeda Pharmaceutical Company Limited; EP1661898; (2006); (A1) English, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Patent; ARGUSINA INC.; LIAO, Jiayu; HONG, Yufeng; WANG, Yong; VON GELDERN, Thomas W.; ZHANG, Kanyin E.; WO2011/94890; (2011); (A1) English, View in Reaxys; Patent; ARGUSINA INC.; US2012/4198; (2012); (A1) English, View in Reaxys; Hsu, Danny C.; Roth, Howard S.; West, Diana C.; Botham, Rachel C.; Novotny, Chris J.; Schmid, Steven C.; Hergenrother, Paul J.; ACS Combinatorial Science; vol. 14; nb. 1; (2012); p. 44 - 50, View in Reaxys; Chai, Yunfeng; Sun, Hezhi; Pan, Yuanjiang; Sun, Cuirong; Journal of the American Society for Mass Spectrometry; vol. 22; nb. 9; (2011); p. 1526 - 1533, View in Reaxys; Baytas, Sultan; Turan Dural, Niludie Nermin; Oezkan, Yesim; Simsek, Hasan Bolkan; Guersel, Tuerkiz; Uenlue, Serdar; Turkish Journal of Chemistry; vol. 36; nb. 3; (2012); p. 367 - 382, View in Reaxys; Wu, Yan; Ma, LongXu; Niu, Tian-Wei; Cui, Xun; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 13; (2012); p. 4229 - 4232, View in Reaxys; Cacchi, Sandro; Fabrizi, Giancarlo; Filisti, Eleonora; Goggiamani, Antonella; Iazzetti, Antonia; Maurone, Loredana; Organic and Biomolecular Chemistry; vol. 10; nb. 24; (2012); p. 4699 - 4703, View in Reaxys; Oezkay, Uemide Demir; Can, Oezgur Devrim; Ozkay, Yusuf; Oztuerk, Yusuf; Pharmacological Reports; vol. 64; nb. 4; (2012); p. 834 - 847, View in Reaxys; Wu, Yan; Ma, Long-Xu; Sun, Liang-Peng; Song, Ming-Xia; Cui, Xun; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 3; (2013); p. 757 - 760, View in Reaxys; Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys; Wu, Yan; Sun, Liang-Peng; Ma, Long-Xu; Che, Jian; Song, Ming-Xia; Cui, Xun; Piao, Hu-Ri; Chemical Biology and Drug Design; vol. 81; nb. 5; (2013); p. 591 - 599, View in Reaxys; Peddibhotla, Satyamaheshwar; Hedrick, Michael P.; Hershberger, Paul; Maloney, Patrick R.; Li, Yujie; Milewski, Monika; Gosalia, Palak; Gray, Wilson; Mehta, Alka; Sugarman, Eliot; Hood, Becky; Suyama, Eigo; Nguyen, Kevin; Heynen-Genel, Susanne; Vasile, Stefan; Salaniwal, Sumeet; Stonich, Derek; Su, Ying; Mangravita-Novo, Arianna; Vicchiarelli, Michael; Roth, Gregory P.; Smith, Layton H.; Chung, Thomas D. Y.; Hanson, Glen R.; Thomas, James B.; Caron, Marc G.; Barak, Lawrence S.; Pinkerton, Anthony B.; ACS Medicinal Chemistry Letters; vol. 4; nb. 9; (2013); p. 846 - 851, View in Reaxys; Kim, Beom-Cheol; Lee, SeungHwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys; Drinkel, Emma E.; Campedelli, Roberta R.; Manfredi, Alex M.; Fiedler, Haidi D.; Nome, Faruk; Journal of Organic Chemistry; vol. 79; nb. 6; (2014); p. 2574 - 2579, View in Reaxys; Zhou, An; Wu, Hongfei; Pan, Jian; Wang, Xuncui; Li, Jiaming; Wu, Zeyu; Hui, Ailing; Molecules; vol. 20; nb. 1; (2015); p. 1304 - 1318, View in Reaxys; Han, Sheng Hua; Chen, Jian Xin; Liu, Hong Yan; Zhang, Hai Rong; Ma, Peng Fei; Asian Journal of Chemistry; vol. 27; nb. 4; (2015); p. 1299 - 1303, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Reaxys ID 611152 View in Reaxys

7/323 CAS Registry Number: 23145-91-7 Chemical Name: 1-(3-chlorobenzyl)piperazine; N-(3-chlorobenzyl)piperazine; 1-(3-chloro-benzyl)-piperazine; 4-(3-chlorophenyl)methylpiperazine; 1-(3-chlorobenzyl)-piperazine; 3-chlorobenzylpiperazine Linear Structure Formula: C11H15ClN2 Molecular Formula: C11H15ClN2 Molecular Weight: 210.706 Type of Substance: heterocyclic InChI Key: JTEQMTYOCBFLNH-UHFFFAOYSA-N Note:

H N

Substance Label (9) Label References 3e

Zhang, Li-Yuan; Wang, Bao-Lei; Zhan, Yi-Zhou; Hua, Xue-Wen; Liu, Ming; Zhang, Xiao; Song, Hai-Bin; Li, Zheng-Ming; Letters in Drug Design and Discovery; vol. 13; nb. 4; (2016); p. 343 - 351, View in Reaxys

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

Luo, Renshi; Xie, Ling; Liao, Jianhua; Xin, Hu; Chan, Albert S.C.; Tetrahedron Asymmetry; vol. 25; nb. 9; (2014); p. 709 - 717, View in Reaxys

5{8}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

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Zeng, Xiaoyun; Zheng, Jinhong; Fu, Chenglai; Su, Hang; Sun, Xiaoli; Zhang, Xuesi; Hou, Yingjian; Zhu, Yi; Molecular Pharmacology; vol. 83; nb. 5; (2013); p. 1099 - 1108, View in Reaxys

45c

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Salvatore, Ralph N.; Sahab, Suma; Jung, Kyung Woon; Tetrahedron Letters; vol. 42; nb. 11; (2001); p. 2055 - 2058, View in Reaxys

Patent-Specific Data (2) Prophetic ComLocation in Patent References pound Page/Page column prophetic product

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Derivative (3) Comment (Derivative)

References

Di-HCl: F: 227-230grad

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Maleat: F: 125-126grad; pharmakolog. Eigensch.

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Dihydrochlorid: F: 275-278.5grad (Zers.; unkorr.; aus A.)

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

Boiling Point (3) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

115 - 120

0.05

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

123 - 127

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

120 - 123

1.5

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

Crystal Property Description (2) Colour & Other Location Properties yellow

Paragraph 0100

yellow

References Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys

NMR Spectroscopy (6) 1 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy)

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2016-05-20 15:00:44

Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR (400 MHz, CDCl ): δ 7.28 (br s, 1H) 7.19-7.12 (m, 3H), 3.39 (s, 2H), 2.82 (t, 4H, 3 J=5.6 Hz), 2.34 (br s, 4H), 1.54 (br s, 1H)

Location

Paragraph 0100

Signals [ppm]

7.28; 7.12 - 7.19; 3.39; 2.82; 2.34; 1.54

Kind of signal

br s, 1H; m, 3H; s, 2H; t, 4H, J=5.6 Hz; br s, 4H; br s, 1H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Original Text (NMR Spectroscopy)

13C-NMR

Location

Paragraph 0100

Signals [ppm]

140.2; 133.9; 129.2; 128.8; 127; 126.9; 62.8; 54.3; 45.9

(100 MHz, CDCl3): δ 140.2, 133.9, 129.2, 128.8, 127.0, 126.9, 62.8, 54.3, 45.9

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 3 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy)

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Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 6 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

CID (collision-insupporting inforduced dissociamation tion); IT (ion trap); ESI (Electrospray ionisation); Spectrum

Chai, Yunfeng; Jiang, Kezhi; Sun, Cuirong; Pan, Yuanjiang; Chemistry - A European Journal; vol. 17; nb. 39; (2011); p. 10820 - 10824, View in Reaxys

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

physiological behaviour discussed

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

Reaxys ID 6392108 View in Reaxys

8/323 CAS Registry Number: 89292-78-4 Chemical Name: 1-(o-fluorobenzyl)piperazine; 4-(2-fluorobenzyl)piperazine; 2-fluorobenzylpiperazine; 1-(2-Fluorobenzyl)piperazine; 1-(2-fluoro-benzyl)-piperazine; 1 -(2-fluorobenzyl)piperazine; 1-(2-fluorobenzyl)piperazine Linear Structure Formula: C11H15FN2 Molecular Formula: C11H15FN2 Molecular Weight: 194.252 Type of Substance: heterocyclic InChI Key: IGVNZJBYRPULAI-UHFFFAOYSA-N Note:

F N NH

Substance Label (5) Label References 5e

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 2086, View in Reaxys

He, Feng-Qi; Liu, Xing-Hai; Wang, Bao-Lei; Li, Zheng-Ming; Journal of Chemical Research; nb. 12; (2006); p. 809 - 811, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Patent-Specific Data (1)

128/337

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Prophetic Compound

References

prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Boiling Point (1) Boiling Point [°C] 93 - 96

Pressure (Boiling Point) [Torr]

References

0.2

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 4 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy)

129/337

2016-05-20 15:00:44

Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 5 of 5

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; American Cyanamid Co.; US4963553; (1990); (A1) English, View in Reaxys; Patent; Molecular Geriatrics Corporation; US6214994; (2001); (B1) English, View in Reaxys; Patent; ASTRAZENECA AB; WO2006/91160; (2006); (A1) English, View in Reaxys; Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys; Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys; Zhao, He; He, Xiaoshu; Thurkauf, Andrew; Hoffman, Diane; Kieltyka, Andrzej; Brodbeck, Robbin; Primus, Renee; Wasley, Jan W.F.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 21; (2002); p. 3111 - 3115, View in Reaxys; Omran, Ziad; Cailly, Thomas; Lescot, Elodie; Santos, Jana Sopkova-De Oliveira; Agondanou, Jean-Hugues; Lisowski, Vincent; Fabis, Frederic; Godard, Anne-Marie; Stiebing, Silvia; Le Flem, Guillaume; Boulouard, Michel; Dauphin, Francois; Dallemagne, Patrick; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 40; nb. 12; (2005); p. 1222 - 1245, View in Reaxys; Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 - 2086, View in Reaxys; Lee, Chang-Sun; Liu, Weili; Sprengeler, Paul A.; Somoza, John R.; Janc, James W.; Sperandio, David; Spencer, Jeffrey R.; Green, Michael J.; McGrath, Mary E.; Bioorganic and Medicinal Chemistry Letters; vol. 16; nb. 15; (2006); p. 4036 - 4040, View in Reaxys; He, Feng-Qi; Liu, Xing-Hai; Wang, Bao-Lei; Li, Zheng-Ming; Journal of Chemical Research; nb. 12; (2006); p. 809 - 811, View in Reaxys; Patent; Molecular Geriatrics Corporation; US5658909; (1997); (A1) English, View in Reaxys; Patent; Molecular Geriatrics Corporation; US5693804; (1997); (A1) English, View in Reaxys; Patent; PIRAMAL LIFE SCIENCES LIMITED; WO2009/16565; (2009); (A1) English, View in Reaxys; Lee, Hyung Kook; Lee, Yun Suk; Roh, Eun Joo; Rhim, Hyewhon; Lee, Jae Yeol; Shin, Kye Jung; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 15; (2008); p. 4424 - 4427, View in Reaxys; Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys; Liu, Xue-Kun; Cui, Xun; Hong, Lan; Sun, Liang-Peng; Quan, Zhe-Shan; Piao, Hu-Ri; European Journal of Medicinal Chemistry; vol. 44; nb. 7; (2009); p. 3027 - 3031, View in Reaxys; Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Prastaro, Alessandro; Tetrahedron; vol. 65; nb. 44; (2009); p. 8916 - 8929, View in Reaxys; Gitto, Rosaria; De Luca, Laura; Ferro, Stefania; De Grazia, Sara; Di Giorgio, Rosa Maria; Festa, Filomena; De Luca, Grazia; Journal of Heterocyclic Chemistry; vol. 47; nb. 1; (2010); p. 54 - 62, View in Reaxys; De Jonghe, Steven; Marchand, Arnaud; Gao, Ling-Jie; Calleja, Agnes; Cuveliers, Eva; Sienaert, Ilse; Herman, Jean; Clydesdale, Gavin; Sefrioui, Hassane; Lin, Yuan; Pfleiderer, Wolfgang; Waer, Mark; Herdewijn, Piet; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 1; (2011); p. 145 - 149, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Rolfe, Alan; Painter, Thomas O.; Asad, Naeem; Hur, Moon Young; Jeon, Kyu Ok; Brzozowski, Marek; Klimberg, Sarra V.; Porubsky, Patrick; Neuenswander, Benjamin; Lushington, Gerald H.; Santini, Conrad; Hanson, Paul R.; ACS Combinatorial Science; vol. 13; nb. 5; (2011); p. 511 - 517, View in Reaxys; Rolfe, Alan; Ullah, Farman; Samarakoon, Thiwanka B.; Kurtz, Ryan D.; Porubsky, Patrick; Neuenswander, Benjamin; Lushington, Gerald H.; Santini, Conrad; Organ, Michael G.; Hanson, Paul R.; ACS Combinatorial Science; vol. 13; nb. 6; (2011); p. 653 - 658, View in Reaxys; Wu, Yan; Ma, Long-Xu; Niu, Tian-Wei; Cui, Xun; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 13; (2012); p. 4229 4232, View in Reaxys; Ismail, Mohamed M.; Kamel, Mona M.; Mohamed, Lamia W.; Faggal, Samar I.; Molecules; vol. 17; nb. 5; (2012); p. 4811 - 4823, View in Reaxys; Saghyan, Ashot S.; Simonyan, Hayarpi M.; Stepanyan, Lala A.; Ghazaryan, Samvel G.; Geolchanyan, Arpine V.; Manasyan, Luiza L.; Ghochikyan, Vahe T.; Ghochikyan, Tariel V.; Hovhannisyan, Nelli A.; Gevorgyan, Ashot; Iaroshenko, Viktor O.; Langer, Peter; Tetrahedron Asymmetry; vol. 23; nb. 11-12; (2012); p. 891 - 897, View in Reaxys; Ismail, Mohamed M.; Kamel, Mona M.; Mohamed, Lamia W.; Faggal, Samar I.; Galal, Mai A.; Molecules; vol. 17; nb. 6; (2012); p. 7217 - 7231, View in Reaxys; Wu, Yan; Ma, Long-Xu; Sun, Liang-Peng; Song, Ming-Xia; Cui, Xun; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 3; (2013); p. 757 - 760, View in Reaxys; Park, Jung-Eun; Ji, Wan Keun; Jang, Jae Wan; Pae, Ae Nim; Choi, Keehyun; Choi, Ki Hang; Kang, Jahyo; Roh, Eun Joo; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 6; (2013); p. 1887 - 1890, View in Reaxys; Wu, Yan; Sun, LiangPeng; Ma, Long-Xu; Che, Jian; Song, Ming-Xia; Cui, Xun; Piao, Hu-Ri; Chemical Biology and Drug Design; vol. 81; nb. 5; (2013); p. 591 - 599, View in Reaxys; Genest, David; Rochais, Christophe; Lecoutey, Cedric; Oliveira

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Santos, Jana Sopkova-De; Ballandonne, Celine; Butt-Gueulle, Sabrina; Legay, Remi; Since, Marc; Dallemagne, Patrick; MedChemComm; vol. 4; nb. 6; (2013); p. 925 - 931, View in Reaxys; Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys; Ojeda-Gomez, Claudia; Pessoa-Mahana, Hernan; Iturriaga-Vasquez, Patricio; Pessoa-Mahana, Carlos David; Recabarren-Gajardo, Gonzalo; Mendez-Rojas, Claudio; Archiv der Pharmazie; vol. 347; nb. 3; (2014); p. 174 - 184, View in Reaxys; Han, Sheng Hua; Chen, Jian Xin; Liu, Hong Yan; Zhang, Hai Rong; Ma, Peng Fei; Asian Journal of Chemistry; vol. 27; nb. 4; (2015); p. 1299 - 1303, View in Reaxys; Britton, Joshua; Chalker, Justin M.; Raston, Colin L.; Chemistry - A European Journal; vol. 21; nb. 30; (2015); p. 10660 - 10665, View in Reaxys; Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 2260, View in Reaxys; Zhang, Li-Yuan; Wang, Bao-Lei; Zhan, Yi-Zhou; Zhang, Yan; Zhang, Xiao; Li, ZhengMing; Chinese Chemical Letters; vol. 27; nb. 1; (2016); p. 163 - 167, View in Reaxys 2 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys 3 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Reaxys ID 147512 View in Reaxys

9/323 CAS Registry Number: 17532-19-3 Chemical Name: 1-(2-chloro-benzyl)-piperazine; 1-(2-chlorobenzyl)-piperazine; (2-chlorobenzyl)piperazine; 1-(2-chlorobenzyl)piperazine; N-(2-chlorobenzyl)piperazine; 1-(2-Chlor-benzyl)-piperazin; 4-<2-Chlor-benzyl>-piperazin Linear Structure Formula: C11H15ClN2 Molecular Formula: C11H15ClN2 Molecular Weight: 210.706 Type of Substance: heterocyclic InChI Key: JOWPEBYCPPLVNX-UHFFFAOYSA-N Note:

Cl N NH

Substance Label (10) Label References 5d

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

Bali, Alka; Reddy, A. C. Dinesh Kumar; Medicinal Chemistry Research; vol. 22; nb. 1; (2013); p. 382 - 391, View in Reaxys

45b

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Ferte, Jacques; Kuehnel, Jean-Marc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 - 489, View in Reaxys

4, Ar=2-ClPh

Buckle, Derek R.; Rockell, Caroline J. M.; Smith, Harry; Spicer, Barbara A.; Journal of Medicinal Chemistry; vol. 29; nb. 11; (1986); p. 2262 - 2267, View in Reaxys

XIII b

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

I-9

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

IIIb

Masuzawa et al.; Bulletin of the Chemical Society of Japan; vol. 40; (1967); p. 244, View in Reaxys

Patent; Kyorin Pharm. Co., Ltd.; JP6829142; (1966); Chem.Abstr.; vol. 70; nb. 87853x; (1969), View in Reaxys; Patent; Kyorin Pharm. Co., Ltd.; JP1783067; (1965); Chem.Abstr.; vol. 68; nb. 114642v; (1968), View in Reaxys

131/337

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Patent-Specific Data (2) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys Patent; Scios, Inc.; US6340685; (2002); (B1) English, View in Reaxys

Derivative (3) Comment (Derivative)

References

Maleat: F: 181-182grad; pharmakolog. Eigensch.

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Dihydrochlorid: F: 218-219.5grad (unkorr.; aus A.)

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

Pikrat:P

Masuzawa et al.; Bulletin of the Chemical Society of Japan; vol. 40; (1967); p. 244, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

157

Solvent (Melting Point)

methanol

Bali, Alka; Reddy, A. C. Dinesh Kumar; Medicinal Chemistry Research; vol. 22; nb. 1; (2013); p. 382 - 391, View in Reaxys 2 of 2

Melting Point [°C]

157

Pressure (Boiling Point) [Torr]

References

108 - 110

0.9

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

122 - 124

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

220

Patent; Kyorin Pharm. Co., Ltd.; JP6829142; (1966); Chem.Abstr.; vol. 70; nb. 87853x; (1969), View in Reaxys; Patent; Kerin Seijaku Kabusihi Kaisja; JP29142; (1968); Ref. Zh., Khim.; vol. 8; nb. N420; (1970), View in Reaxys; Patent; Kyorin Pharm. Co., Ltd.; JP1783067; (1965); Chem.Abstr.; vol. 68; nb. 114642v; (1968), View in Reaxys

92 - 98

0.1

Patent; U.S. Vit. Pharm.; BE617599; (1962); Chem.Abstr.; vol. 59; nb. 646; (1963), View in Reaxys

121 - 123

Baltzly et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 4809, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

Further Information (2) Description (Fur- References ther Information) Further information

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Further information

Masuzawa et al.; Bulletin of the Chemical Society of Japan; vol. 40; (1967); p. 244, View in Reaxys

NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts troscopy)

132/337

2016-05-20 15:00:44

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 4 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 5 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys IR Spectroscopy (1)

133/337

2016-05-20 15:00:44

1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Bali, Alka; Sharma, Komal; Bhalla, Abhishek; Bala, Suman; Reddy, Dinesh; Singh, Anant; Kumar, Anil; European Journal of Medicinal Chemistry; vol. 45; nb. 6; (2010); p. 2656 - 2662, View in Reaxys; Bali, Alka; Reddy, A. C. Dinesh Kumar; Medicinal Chemistry Research; vol. 22; nb. 1; (2013); p. 382 - 391, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry)

References

electron impact (EI); spectrum

Bali, Alka; Reddy, A. C. Dinesh Kumar; Medicinal Chemistry Research; vol. 22; nb. 1; (2013); p. 382 - 391, View in Reaxys

CID (collision-insupporting inforduced dissociamation tion); IT (ion trap); ESI (Electrospray ionisation); Spectrum

Chai, Yunfeng; Jiang, Kezhi; Sun, Cuirong; Pan, Yuanjiang; Chemistry - A European Journal; vol. 17; nb. 39; (2011); p. 10820 - 10824, View in Reaxys

EI (Electron impact); Spectrum

Bali, Alka; Sharma, Komal; Bhalla, Abhishek; Bala, Suman; Reddy, Dinesh; Singh, Anant; Kumar, Anil; European Journal of Medicinal Chemistry; vol. 45; nb. 6; (2010); p. 2656 - 2662, View in Reaxys

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

physiological behaviour discussed

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

Reaxys ID 184285 View in Reaxys

10/323 CAS Registry Number: 55513-17-2 Chemical Name: 1-(3,4-chlorobenzyl)piperazine; 1-(3,4-dichloro-benzyl)-piperazine; 1-(3,4-dichlorobenzyl)piperazine; 1(3,4-dichlorobenzyl) piperazine; 3,4-dichlorobenzylpiperazine Linear Structure Formula: C11H14N2Cl2 Molecular Formula: C11H14Cl2N2 Molecular Weight: 245.152 Type of Substance: heterocyclic InChI Key: PNDSYXGJCWKNFG-UHFFFAOYSA-N Note:

H N

Cl Cl

Substance Label (2) Label References 5c

18b

Patent; Gong, Leyi; Wilhelm, Robert Stephen; US2005/90504; (2005); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product Boiling Point (1) Boiling Point [°C] 124 - 128

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys Pressure (Boiling Point) [Torr]

References

0.02

Patent; U.S. Vit. Pharm.; BE617599; (1962); Chem.Abstr.; vol. 59; nb. 646; (1963), View in Reaxys

Pharmacological Data (1)

134/337

2016-05-20 15:00:44

1 of 1

Comment (Pharmacological Data)

physiological behaviour discussed

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

Reaxys ID 156352 View in Reaxys

11/323 CAS Registry Number: 91345-62-9 Chemical Name: 1-(4-bromobenzyl)piperazine; N-(4-bromobenzyl)piperazine; 1-(4-bromo-benzyl)-piperazine Linear Structure Formula: C11H15BrN2 Molecular Formula: C11H15BrN2 Molecular Weight: 255.157 Type of Substance: heterocyclic InChI Key: MAHWBNAOEVAPJF-UHFFFAOYSA-N Note:

NH N

Substance Label (7) Label References 2a

Roberts, Maxine P.; Nguyen, Vu; Ashford, Mark E.; Berghofer, Paula; Wyatt, Naomi A.; Krause-Heuer, Anwen M.; Pham, Tien Q.; Taylor, Stephen R.; Hogan, Leena; Jiang, Cathy D.; Fraser, Benjamin H.; Lengkeek, Nigel A.; Matesic, Lidia; Gregoire, Marie-Claude; Denoyer, Delphine; Hicks, Rodney J.; Katsifis, Andrew; Greguric, Ivan; Journal of Medicinal Chemistry; vol. 58; nb. 15; (2015); p. 6214 - 6224, View in Reaxys

5{9}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

A-2

Patent; PROZYMEX A/S; PEDERSEN, John; LAURITZEN, Conni; WO2012/119941; (2012); (A1) English, View in Reaxys

Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 2086, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Patent-Specific Data (2) Prophetic ComLocation in Patent References pound Page/Page column prophetic product Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

122 - 124

0.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

112 - 116

0.3

Patent; U.S. Vit. Pharm.; BE617599; (1962); Chem.Abstr.; vol. 59; nb. 646; (1963), View in Reaxys

Crystal Property Description (2) Colour & Other Location Properties white

Paragraph 0106

References Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

135/337

2016-05-20 15:00:44

light-yellow

Page/Page column 133

Patent; PROZYMEX A/S; PEDERSEN, John; LAURITZEN, Conni; WO2012/119941; (2012); (A1) English, View in Reaxys

NMR Spectroscopy (6) 1 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR

(400 MHz, CDCl3): δ 7.42 (d, 2H, J=8.4 Hz) 7.19 (d, 2H, J=8.4 Hz), 3.42 (s, 2H) 2.87 (t, 4H, J=4.8 Hz), 2.38 (br s, 4H), 2.07 (br s, 1H)

Location

Paragraph 0106

Signals [ppm]

7.42; 7.19; 3.42; 2.87; 2.38; 2.07

Kind of signal

d, 2H, J=8.4 Hz; d, 2H, J=8.4 Hz; s, 2H; t, 4H, J=4.8 Hz; br s, 4H; br s, 1H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Original Text (NMR Spectroscopy)

13C-NMR

Location

Paragraph 0106

Signals [ppm]

137.1; 131.3; 130.9; 120.8; 62.8; 54.2; 45.9

(100 MHz, CDCl3): δ 137.1, 131.3, 130.9, 120.8, 62.8, 54.2, 45.9

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 3 of 6

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

Location

Page/Page column 133

Comment (NMR Spectroscopy)

Signals given

NMR (300Hz, CDCI3) δ = 7.41 (d, J = 8.4 Hz, 2H), 7.20 (d, J = 8.4 Hz, 2H), 3.42 (s, 2H), 2.89 (t, J = 4.8 Hz, 4H), 2.40 (br, 4H)

Patent; PROZYMEX A/S; PEDERSEN, John; LAURITZEN, Conni; WO2012/119941; (2012); (A1) English, View in Reaxys 4 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy)

136/337

2016-05-20 15:00:44

Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 5 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 6 of 6

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

References

CID (collision-insupporting inforduced dissociamation tion); IT (ion trap); ESI (Electrospray ionisation); Spectrum

Chai, Yunfeng; Jiang, Kezhi; Sun, Cuirong; Pan, Yuanjiang; Chemistry - A European Journal; vol. 17; nb. 39; (2011); p. 10820 - 10824, View in Reaxys

Reaxys ID 147016 View in Reaxys

12/323 CAS Registry Number: 5321-48-2 Chemical Name: 1-(3-methylbenzyl)piperazine; 1-(3-methylbenzyl)-piperazine; 1-(3-Methyl-benzyl)-piperazin Linear Structure Formula: C12H18N2 Molecular Formula: C12H18N2 Molecular Weight: 190.288 Type of Substance: heterocyclic InChI Key: VTEOTZPEMDQENX-UHFFFAOYSA-N Note:

H N

Substance Label (3) Label References 5

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Patent-Specific Data (2)

137/337

2016-05-20 15:00:44

Prophetic Compound

References

prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys Patent; Solvay Pharmaceuticals GmbH; EP1176144; (2002); (A1) German, View in Reaxys

Derivative (2) Comment (Derivative)

References

Methansulfonat: F: 125-126grad; Pharmakolog. Eigensch.

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Dihydrochlorid: F: 268-270grad (unkorr., Zers.)

Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys

Boiling Point (7) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

Comment (Boiling References Point)

108 - 110

0.2

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

148 - 152

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

150 - 165

Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys

123 - 125

1.5

Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys

130 - 132

1.4

Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys

103 - 105

0.2

118 - 121

verschiedene Praeparate.

Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys Morren; Strubbe; J. Pharm. Belg. <NS>; vol. 10; (1955); p. 239,242, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.545

Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys

589

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

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2 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 4 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 5 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys; Morren et al.; Industrie Chimique Belge; vol. 22; (1957); p. 409,416, View in Reaxys; Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys; Morren; Strubbe; J. Pharm. Belg. <NS>; vol. 10; (1955); p. 239,244, View in Reaxys; Morren et al.; Industrie Chimique Belge; vol. 19; (1954); p. 1176,1181, View in Reaxys; Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys; Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys; Youngman, Mark A.; Dax, Scott L.; Tetrahedron Letters; vol. 38; nb. 36; (1997); p. 6347 - 6350, View in Reaxys; Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys; Omran, Ziad; Cailly, Thomas; Lescot, Elodie; Santos, Jana Sopkova-De Oliveira; Agondanou, Jean-Hugues; Lisowski, Vincent; Fabis, Frederic; Godard, Anne-Marie; Stiebing, Silvia; Le Flem, Guillaume; Boulouard, Michel; Dauphin, Francois; Dallemagne, Patrick; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 40; nb. 12; (2005); p. 1222 - 1245, View in Reaxys; Lee, Hyung Kook; Lee, Yun Suk; Roh, Eun Joo; Rhim, Hyewhon; Lee, Jae Yeol; Shin, Kye Jung; Bioorganic and Medicinal Chemistry

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Letters; vol. 18; nb. 15; (2008); p. 4424 - 4427, View in Reaxys; Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys; Ye, Yangliang; Zhou, Zhou; Zou, Han-jun; Shen, Yu; Xu, Ti-fei; Tang, Jing; Yin, Hua-zhong; Chen, Min-li; Leng, Ying; Shen, Jian-hua; Bioorganic and Medicinal Chemistry; vol. 17; nb. 15; (2009); p. 5722 - 5732, View in Reaxys; Patent; Solvay Pharmaceuticals GmbH; EP1176144; (2002); (A1) German, View in Reaxys; Perez, Michel; Lamothe, Marie; Maraval, Catherine; Mirabel, Etienne; Loubat, Chantal; Planty, Bruno; Horn, Clemens; Michaux, Julien; Marrot, Sebastien; Letienne, Robert; Pignier, Christophe; Bocquet, Arnaud; Nadal-Wollbold, Florence; Cussac, Didier; De Vries, Luc; Le Grand, Bruno; Journal of Medicinal Chemistry; vol. 52; nb. 19; (2009); p. 5826 5836, View in Reaxys; Gitto, Rosaria; De Luca, Laura; Ferro, Stefania; De Grazia, Sara; Di Giorgio, Rosa Maria; Festa, Filomena; De Luca, Grazia; Journal of Heterocyclic Chemistry; vol. 47; nb. 1; (2010); p. 54 - 62, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Rolfe, Alan; Painter, Thomas O.; Asad, Naeem; Hur, Moon Young; Jeon, Kyu Ok; Brzozowski, Marek; Klimberg, Sarra V.; Porubsky, Patrick; Neuenswander, Benjamin; Lushington, Gerald H.; Santini, Conrad; Hanson, Paul R.; ACS Combinatorial Science; vol. 13; nb. 5; (2011); p. 511 - 517, View in Reaxys; Patent; ST. MARY'S UNIVERSITY; VAUGHAN, Keith; WO2013/23273; (2013); (A1) English, View in Reaxys; Karakaya, Guelsah; Aytemir, Mutlu Dilsiz; Oezcelik, Berrin; Calis, Uensal; Journal of Enzyme Inhibition and Medicinal Chemistry; vol. 28; nb. 3; (2013); p. 627 - 638, View in Reaxys; Aytemir, Mutlu Dilsiz; Oezcelik, Berrin; Karakaya, Guelsah; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 12; (2013); p. 3646 3649, View in Reaxys; Sadeghzadeh, Masoud; Sheibani, Shahab; Ghandi, Mehdi; Daha, Fariba Johari; Amanlou, Massoud; Arjmand, Mohammad; Hasani Bozcheloie, Abolfazl; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 488 - 497, View in Reaxys; Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys; Patent; ENVOY THERAPEUTICS, INC.; HITCHCOCK, Stephen; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; KIKUCHI, Shota; MACKLIN, Todd; HOPKINS, Maria; WO2014/28479; (2014); (A1) English, View in Reaxys; Morren; Strubbe; J. Pharm. Belg. <NS>; vol. 10; (1955); p. 239,242, View in Reaxys; Shah, Dhruvin R.; Lakum, Harshad P.; Chikhalia, Kishor H.; Heterocyclic Communications; vol. 20; nb. 5; (2014); p. 305 312, View in Reaxys; Han, Sheng Hua; Chen, Jian Xin; Liu, Hong Yan; Zhang, Hai Rong; Ma, Peng Fei; Asian Journal of Chemistry; vol. 27; nb. 4; (2015); p. 1299 - 1303, View in Reaxys; Shah, Dhruvin R.; Lakum, Harshad P.; Chikhalia, Kishor H.; Letters in Organic Chemistry; vol. 12; nb. 4; (2015); p. 237 - 250, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Reaxys ID 159543 View in Reaxys

13/323 CAS Registry Number: 956-61-6 Chemical Name: 1-(4-tert-butylbenzyl)piperazine; 1-(4-(tert-butyl)benzyl)piperazine; 1-(4-tert-Butylbenzyl)piperazin; 1-(4-t-butylbenzyl)piperazine; 1-(4-tert-butyl-benzyl)-piperazine; 1-(4tert-Butyl-benzyl)-piperazin; 1-p-tert-Butylbenzyl-piperazin Linear Structure Formula: C15H24N2 Molecular Formula: C15H24N2 Molecular Weight: 232.369 Type of Substance: heterocyclic InChI Key: UQLCETYSARZZSR-UHFFFAOYSA-N Note:

N NH

Substance Label (6) Label References 2d

5{20}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys; Patent; HERGENROTHER, Paul J.; ROTH, Howard Steven; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; WO2014/22858; (2014); (A1) English, View in Reaxys

Moehrle; Azodi; Pharmazie; vol. 61; nb. 10; (2006); p. 815 - 822, View in Reaxys; Moehrle, Hans; Azodi, Katja; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 8; (2006); p. 1021 - 1034, View in Reaxys

11, R&3%=4-tertBu

Zhao, He; Thurkauf, Andrew; He, Xiaoshu; Hodgetts, Kevin; Zhang, Xiaoyan; Rachwal, Stanislaw; Kover, Renata X.; Hutchison, Alan; Peterson, John; Kieltyka, Andrzej; Brodbeck, Robbin; Primus, Renee;

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Wasley, Jan W.F.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 21; (2002); p. 3105 - 3109, View in Reaxys 13d

Walczynski, Krzysztof; Guryn, Roman; Zuiderveld, Obbe P.; Timmerman, Henk; Farmaco; vol. 54; nb. 10; (1999); p. 684 - 694, View in Reaxys

III

Lui et al.; Yaoxue Xuebao; vol. 11; nb. 8; (1964); p. 317,318-320; Chem.Abstr.; vol. 62; nb. 2776b; (1965), View in Reaxys

Patent-Specific Data (2) Prophetic ComLocation in Patent References pound Page/Page column prophetic product

Melting Point (1) 1 of 1

Melting Point [°C]

50 - 54

Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

122 - 124

0.5

Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys

128 - 130

0.1

Morren; Strubbe; J. Pharm. Belg. <NS>; vol. 10; (1955); p. 239,242, View in Reaxys

Crystal Property Description (3) Colour & Other Location Properties

References

beige

Page/Page column 36

Patent; HERGENROTHER, Paul J.; ROTH, Howard Steven; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; WO2014/22858; (2014); (A1) English, View in Reaxys

beige

Paragraph 0172

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

white

supporting information

Nalluri, Siva Krishna Mohan; Ravoo, Bart Jan; Angewandte Chemie - International Edition; vol. 49; nb. 31; (2010); p. 5371 - 5374, View in Reaxys

NMR Spectroscopy (6) 1 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Original Text (NMR Spectroscopy)

1H-NMR (500 MHz, CDCl3): δ 7.30 (d, 2H, J = 8.5 Hz), 7.22 (d, 2H, J= 8.5 Hz), 3.44 (s, 2H), 2.85 (t, 4H, J = 5.0 Hz), 2.38 (br s, 4H), 1.54 (br s, 1H), 1.29 (s, 9H).13C-NMR (125 MHz, CDCb): 8 149.6, 134.7, 128.7, 124.8, 63.1, 54.3, 45.9, 34.2, 31.2.

Location

Page/Page column 36

Patent; HERGENROTHER, Paul J.; ROTH, Howard Steven; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; WO2014/22858; (2014); (A1) English, View in Reaxys 2 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

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Original Text (NMR Spectroscopy)

13C-NMR (125 MHz, CDCl3): δ 149.6, 134.7, 128.7, 124.8, 63.1, 54.3, 45.9, 34.2, 31.2.

Location

Page/Page column 36

Patent; HERGENROTHER, Paul J.; ROTH, Howard Steven; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; WO2014/22858; (2014); (A1) English, View in Reaxys 3 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Original Text (NMR Spectroscopy)

1H-NMR (500 MHz, CDCl ): δ 7.30 (d, 2H, J=8.5 Hz), 7.22 (d, 2H, J=8.5 Hz), 3.44 (s, 2H), 3 2.85 (t, 4H, J=5.0 Hz), 2.38 (br s, 4H), 1.54 (br s, 1H), 1.29 (s, 9H)

Location

Paragraph 0172

Signals [ppm]

7.3; 7.22; 3.44; 2.85; 2.38; 1.54; 1.29

Kind of signal

d, 2H, J=8.5 Hz; d, 2H, J=8.5 Hz; s, 2H; t, 4H, J=5.0 Hz; br s, 4H; br s, 1H; s, 9H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 4 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Original Text (NMR Spectroscopy)

13C-NMR

Location

Paragraph 0172

Signals [ppm]

149.6; 134.7; 128.7; 124.8; 63.1; 54.3; 45.9; 34.2; 31.2

(125 MHz, CDCl3): δ 149.6, 134.7, 128.7, 124.8, 63.1, 54.3, 45.9, 34.2, 31.2

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 5 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Nalluri, Siva Krishna Mohan; Ravoo, Bart Jan; Angewandte Chemie - International Edition; vol. 49; nb. 31; (2010); p. 5371 - 5374, View in Reaxys 6 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy)

142/337

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Nalluri, Siva Krishna Mohan; Ravoo, Bart Jan; Angewandte Chemie - International Edition; vol. 49; nb. 31; (2010); p. 5371 - 5374, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum

References

supporting information

Nalluri, Siva Krishna Mohan; Ravoo, Bart Jan; Angewandte Chemie - International Edition; vol. 49; nb. 31; (2010); p. 5371 - 5374, View in Reaxys

Reaxys ID 5948511 View in Reaxys

14/323 CAS Registry Number: 107890-32-4 Chemical Name: 1-(4-trifluoromethylbenzyl)piperazine; 1-(4(trifluoromethyl)benzyl)piperazine; 1-[4-(trifluoromethyl)benzyl]piperazine; N-(4-trifluoromethylbenzyl)piperazine Linear Structure Formula: C12H15F3N2 Molecular Formula: C12H15F3N2 Molecular Weight: 244.26 Type of Substance: heterocyclic InChI Key: FAFAFWFQFVLXGF-UHFFFAOYSA-N Note:

N F

F F

Substance Label (6) Label References 23

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

5{15}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

13e

11, R&3%=4-CF3

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column Boiling Point (1) Boiling Point [°C] 98 - 100

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys Pressure (Boiling Point) [Torr]

References

0.05

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties yellow

Paragraph 0142

References Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

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NMR Spectroscopy (9) 1 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR (400 MHz, CDCl ): δ 7.52 (d, 2H, J=8.0 Hz), 7.40 (d, 2H, J=8.0 Hz), 3.48 (s, 2H), 3 2.84 (t, 4H, J=4.8 Hz), 2.36 (br s, 4H), 1.55 (br s, 1H)

Location

Paragraph 0142

Signals [ppm]

7.52; 7.4; 3.48; 2.84; 2.36; 1.55

Kind of signal

d, 2H, J=8.0 Hz; d, 2H, J=8.0 Hz; s, 2H; t, 4H, J=4.8 Hz; br s, 4H; br s, 1H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Original Text (NMR Spectroscopy)

13C-NMR

(100 MHz, CDCl3): δ 142.4, 129.1 (q, JC-F=32.1 Jz) 129.1 (br), 125.0 (br), 124.1 (q, JC-F=338.0 Hz), 62.9, 54.4, 45.9

Location

Paragraph 0142

Signals [ppm]

142.4; 129.1; 129.1; 125; 124.1; 62.9; 54.4; 45.9

Kind of signal

q, J&C-F%=32.1 Jz; br; br; q, J&C-F%=338.0 Hz

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 3 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

375

Original Text (NMR Spectroscopy)

19F-NMR

Location

Paragraph 0142

(375 MHz, CDCl3): δ-62.5

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 4 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy)

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Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 5 of 9

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 6 of 9

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 7 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 8 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Baziard-Mouysset, Genevieve; Younes, Salouma; Labssita, Youssef; Payard, Marc; Caignard, Daniel-Henri; Rettori, Marie-Claire; Renard, Pierre; Pfeiffer, Bruno; Guardiola-Lemaitre, Beatrice; European Journal of Medicinal Chemistry; vol. 33; nb. 5; (1998); p. 339 - 347, View in Reaxys 9 of 9

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Description (IR Spectroscopy)

Bands

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Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3391 - 1616 cm**(-1)

Baziard-Mouysset, Genevieve; Younes, Salouma; Labssita, Youssef; Payard, Marc; Caignard, Daniel-Henri; Rettori, Marie-Claire; Renard, Pierre; Pfeiffer, Bruno; Guardiola-Lemaitre, Beatrice; European Journal of Medicinal Chemistry; vol. 33; nb. 5; (1998); p. 339 - 347, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) CID (collision-inChai, Yunfeng; Sun, Hezhi; Pan, Yuanjiang; Sun, Cuirong; Journal of the American Society for Mass duced dissociaSpectrometry; vol. 22; nb. 9; (2011); p. 1526 - 1533, View in Reaxys tion); ESI (Electrospray ionisation); IT (ion trap); Spectrum

Reaxys ID 137457 View in Reaxys

15/323 CAS Registry Number: 5321-47-1 Chemical Name: 1-(2-methylbenzyl)piperazine; 2-methylbenzylpiperazine; 1-(2-methyl-benzyl)-piperazine; 1-(2-Methyl-benzyl)-piperazin Linear Structure Formula: C12H18N2 Molecular Formula: C12H18N2 Molecular Weight: 190.288 Type of Substance: heterocyclic InChI Key: GRVNOUKHAZXMJK-UHFFFAOYSA-N Note:

N NH

Substance Label (3) Label References 4

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Kurosu, Michio; Dey, Sevendu Sekhar; Crick, Dean C.; Tetrahedron Letters; vol. 47; nb. 28; (2006); p. 4871 - 4875, View in Reaxys

11, R&3%=2-Me

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product Derivative (2) Comment (Derivative)

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys References

Maleat: F: 163-164grad, Pharmakolog. Eigensch.

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Dihydrochlorid: F: 228-230grad (unkorr., Zers.)

Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys

Boiling Point (6) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

146/337

2016-05-20 15:00:44

150 - 153

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

145 - 160

Patent; Inst. Farm.; PL50668; (1966); Chem.Abstr.; vol. 66; nb. 76035, View in Reaxys

140 - 160

Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys

77 - 80

0.1

Steck,E.A.; Journal of Organic Chemistry; vol. 27; (1962); p. 306 - 308, View in Reaxys

0.1

Morren et al.; Industrie Chimique Belge; vol. 22; (1957); p. 409,416, View in Reaxys; Patent; Morren; BE549420; Chem.Abstr.; nb. 12169; (1960), View in Reaxys

104 - 106

0.05

Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys

Refractive Index (2) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5415

589

Patent; Inst. Farm.; PL50668; (1966); Chem.Abstr.; vol. 66; nb. 76035, View in Reaxys

1.5425

589

Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Comment (Pharmacological Data)

Bioactivities present

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys; Patent; Ciba-Geigy Corporation; US5286728; (1994); (A1) English, View in Reaxys; Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US4692448; (1987); (A1) English, View in Reaxys; Steck,E.A.; Journal of Organic Chemistry; vol. 27; (1962); p. 306 - 308, View in Reaxys; Morren et al.; Industrie Chimique Belge; vol. 22; (1957); p. 409,416, View in Reaxys; Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys; Toldy et al.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 53; (1967); p. 279, View in Reaxys; Patent; Morren; BE549420; Chem.Abstr.; nb. 12169; (1960), View in Reaxys; Sacha; Acta Poloniae Pharmaceutica; vol. 21; (1964); p. 369,373,376, View in Reaxys; Patent; Inst. Farm.; PL50668; (1966);

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Chem.Abstr.; vol. 66; nb. 76035, View in Reaxys; Hideg; Hankovszky; Acta Chimica Academiae Scientiarum Hungaricae; vol. 53; (1967); p. 271; Chem.Abstr.; vol. 69; nb. 59156h; (1968), View in Reaxys; Toldy et al.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 52; (1967); p. 283, View in Reaxys; Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys; Bourrain, Sylvie; Collins, Ian; Neduvelil, Joseph G.; Rowley, Michael; Leeson, Paul D.; Patel, Smita; Patel, Shil; Emms, Frances; Marwood, Rosemarie; Chapman, Kerry L.; Fletcher, Alan E.; Showell, Graham A.; Bioorganic and Medicinal Chemistry; vol. 6; nb. 10; (1998); p. 1731 - 1743, View in Reaxys; Zhao, He; Thurkauf, Andrew; He, Xiaoshu; Hodgetts, Kevin; Zhang, Xiaoyan; Rachwal, Stanislaw; Kover, Renata X.; Hutchison, Alan; Peterson, John; Kieltyka, Andrzej; Brodbeck, Robbin; Primus, Renee; Wasley, Jan W.F.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 21; (2002); p. 3105 - 3109, View in Reaxys; Omran, Ziad; Cailly, Thomas; Lescot, Elodie; Santos, Jana Sopkova-De Oliveira; Agondanou, Jean-Hugues; Lisowski, Vincent; Fabis, Frederic; Godard, Anne-Marie; Stiebing, Silvia; Le Flem, Guillaume; Boulouard, Michel; Dauphin, Francois; Dallemagne, Patrick; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 40; nb. 12; (2005); p. 1222 - 1245, View in Reaxys; Kurosu, Michio; Dey, Sevendu Sekhar; Crick, Dean C.; Tetrahedron Letters; vol. 47; nb. 28; (2006); p. 4871 - 4875, View in Reaxys; Patent; Rhone-Poulenc Sante; US4769366; (1988); (A1) English, View in Reaxys; Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Karakaya, Guelsah; Aytemir, Mutlu Dilsiz; Oezcelik, Berrin; Calis, Uensal; Journal of Enzyme Inhibition and Medicinal Chemistry; vol. 28; nb. 3; (2013); p. 627 - 638, View in Reaxys; Aytemir, Mutlu Dilsiz; Oezcelik, Berrin; Karakaya, Guelsah; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 12; (2013); p. 3646 - 3649, View in Reaxys; Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys; Moukha-Chafiq, Omar; Reynolds, Robert C.; ACS Combinatorial Science; vol. 16; nb. 5; (2014); p. 232 - 237, View in Reaxys; Han, Sheng Hua; Chen, Jian Xin; Liu, Hong Yan; Zhang, Hai Rong; Ma, Peng Fei; Asian Journal of Chemistry; vol. 27; nb. 4; (2015); p. 1299 - 1303, View in Reaxys; Moukha-Chafiq, Omar; Reynolds, Robert C.; Nucleosides, Nucleotides and Nucleic Acids; vol. 33; nb. 11; (2014); p. 709 - 729, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Reaxys ID 4251296 View in Reaxys

16/323 CAS Registry Number: 58198-49-5 Chemical Name: 1-(4-nitrobenzyl)piperazine; N-(4-nitrobenzyl)piperazine; 4-Nitrobenzylpiperazine Linear Structure Formula: C11H15N3O2 Molecular Formula: C11H15N3O2 Molecular Weight: 221.259 Type of Substance: heterocyclic InChI Key: VDHHZWTYFFZYBM-UHFFFAOYSA-N Note:

O O

NH N

Substance Label (5) Label References 11

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

Zhou, An; Wu, Hongfei; Pan, Jian; Wang, Xuncui; Li, Jiaming; Wu, Zeyu; Hui, Ailing; Molecules; vol. 20; nb. 1; (2015); p. 1304 - 1318, View in Reaxys

Zhao, Yan-Fang; Liu, Zi-Jian; Zhai, Xin; Ge, Dan-Dan; Huang, Qiang; Gong, Ping; Chinese Chemical Letters; vol. 24; nb. 5; (2013); p. 386 - 388, View in Reaxys

Palimkar, Sanjay S.; More, Vijaykumar S.; Kumar, P. Harish; Srinivasan, Kumar V.; Tetrahedron; vol. 63; nb. 51; (2007); p. 12786 - 12790, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

250 - 255

Solvent (Melting Point)

CH2Cl2; hexane

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Comment (Melting Point)

Decomposition

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 2 of 2

Melting Point [°C]

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys Crystal Property Description (2) Colour & Other References Properties light-yellow

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

yellow

Dannhardt, Gerd; Gruchalla, Markus V.; Kohl, Beate K.; Parsons; Archiv der Pharmazie; vol. 333; nb. 8; (2000); p. 267 - 274, View in Reaxys; Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys

NMR Spectroscopy (6) 1 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

600

Zhou, An; Wu, Hongfei; Pan, Jian; Wang, Xuncui; Li, Jiaming; Wu, Zeyu; Hui, Ailing; Molecules; vol. 20; nb. 1; (2015); p. 1304 - 1318, View in Reaxys 2 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 3 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 4 of 6

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

149/337

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Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 5 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys 6 of 6

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) CID (collision-inChai, Yunfeng; Sun, Hezhi; Pan, Yuanjiang; Sun, Cuirong; Journal of the American Society for Mass duced dissociaSpectrometry; vol. 22; nb. 9; (2011); p. 1526 - 1533, View in Reaxys tion); ESI (Electrospray ionisation); IT (ion trap); Spectrum

Reaxys ID 520481 View in Reaxys

17/323 CAS Registry Number: 51619-56-8 Chemical Name: 1-(2,4-dichlorobenzyl)piperazine; 1-(2,4-dichloro-benzyl)-piperazine; 1-(2,4-dichlorobenzyl)-piperazine Linear Structure Formula: C11H14Cl2N2 Molecular Formula: C11H14Cl2N2 Molecular Weight: 245.152 Type of Substance: heterocyclic InChI Key: VYKXBWXIOSLDQR-UHFFFAOYSA-N Note:

Cl N Cl

Substance Label (5) Label References 1b

Wang, Bao-Lei; Zhan, Yi-Zhou; Zhang, Li-Yuan; Zhang, Yan; Zhang, Xiao; Li, Zheng-Ming; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; nb. 1; (2016); p. 48 - 54, View in Reaxys

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

He, Feng-Qi; Liu, Xing-Hai; Wang, Bao-Lei; Li, Zheng-Ming; Journal of Chemical Research; nb. 12; (2006); p. 809 - 811, View in Reaxys

150/337

2016-05-20 15:00:44

Patent-Specific Data (1) References Patent; ABBOTT GMBH and CO. KG; WO2006/66885; (2006); (A1) German, View in Reaxys Boiling Point (4) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

147 - 150

Wang, Bao-Lei; Liu, Xing-Hai; Zhang, Xiu-Lan; Zhang, Ji-Feng; Song, Hai-Bin; Li, Zheng-Ming; Chemical Biology and Drug Design; vol. 78; nb. 1; (2011); p. 42 - 49, View in Reaxys

106 - 108

0.05

Patent; U.S. Vit. Pharm.; BE617599; (1962); Chem.Abstr.; vol. 59; nb. 646; (1963), View in Reaxys

Crystal Property Description (3) Colour & Other References Properties colourless

yellow

colourless

Wang, Bao-Lei; Liu, Xing-Hai; Zhang, Xiu-Lan; Zhang, Ji-Feng; Song, Hai-Bin; Li, Zheng-Ming; Chemical Biology and Drug Design; vol. 78; nb. 1; (2011); p. 42 - 49, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Comment (Pharmacological Data)

Bioactivities present

Patent; ABBOTT GMBH and CO. KG; WO2006/66885; (2006); (A1) German, View in Reaxys; Patent; U.S. Vit. Pharm.; BE617599; (1962); Chem.Abstr.; vol. 59; nb. 646; (1963), View in Reaxys; Rault, Sylvain; Lancelot, Jean-

151/337

2016-05-20 15:00:44

Charles; Prunier, Herve; Robba, Max; Renard, Pierre; Delagrange, Philippe; Pfeiffer, Bruno; Caignard, DanielHenri; Guardiola-Lemaitre, Beatrice; Hamon, Michel; Journal of Medicinal Chemistry; vol. 39; nb. 10; (1996); p. 2068 - 2080, View in Reaxys; Prunier, Herve; Rault, Sylvain; Lancelot, Jean-Charles; Robba, Max; Renard, Pierre; Delagrange, Philippe; Pfeiffer, Bruno; Caignard, Daniel-Henri; Misslin, Rene; Guardiola-Lemaitre, Beatrice; Hamon, Michel; Journal of Medicinal Chemistry; vol. 40; nb. 12; (1997); p. 1808 - 1819, View in Reaxys; Baziard-Mouysset, Genevieve; Younes, Salouma; Labssita, Youssef; Payard, Marc; Caignard, Daniel-Henri; Rettori, Marie-Claire; Renard, Pierre; Pfeiffer, Bruno; Guardiola-Lemaitre, Beatrice; European Journal of Medicinal Chemistry; vol. 33; nb. 5; (1998); p. 339 - 347, View in Reaxys; Mouithys-Mickalad, Ange; Poupaert, Jacques H.; Spampinato, Santi; Lesieur, Daniel; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 8; (2002); p. 1149 - 1152, View in Reaxys; Omran, Ziad; Cailly, Thomas; Lescot, Elodie; Santos, Jana Sopkova-De Oliveira; Agondanou, Jean-Hugues; Lisowski, Vincent; Fabis, Frederic; Godard, Anne-Marie; Stiebing, Silvia; Le Flem, Guillaume; Boulouard, Michel; Dauphin, Francois; Dallemagne, Patrick; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 40; nb. 12; (2005); p. 1222 - 1245, View in Reaxys; He, Feng-Qi; Liu, Xing-Hai; Wang, Bao-Lei; Li, Zheng-Ming; Journal of Chemical Research; nb. 12; (2006); p. 809 - 811, View in Reaxys; Patent; ABBOTT LABORATORIES; BHATIA, Pramila, A.; DOHERTY, George, A.; DRIZIN, Irene; MACK, Helmut; PERNER, Richard, J.; STEWART, Andrew, O.; ZHANG, Qing Wei; WO2010/39947; (2010); (A1) English, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Cai, Mingyi; Li, Zhong; Fan, Feng; Huang, Qingchun; Shao, Xusheng; Song, Gonghua; Journal of Agricultural and Food Chemistry; vol. 58; nb. 5; (2010); p. 2624 - 2629, View in Reaxys; Doherty, George A.; Bhatia, Pramila; Vortherms, Timothy A.; Marsh, Kennan C.; Wetter, Jill M.; MacK, Helmut; Scott, Victoria E.; Jarvis, Michael F.; Stewart, Andrew O.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 4; (2012); p. 1716 - 1718, View in Reaxys; Wang, Bao-Lei; Liu, Xing-Hai; Zhang, Xiu-Lan; Zhang, Ji-Feng; Song, Hai-Bin; Li, Zheng-Ming; Chemical Biology and Drug Design; vol. 78; nb. 1; (2011); p. 42 - 49, View in Reaxys; Wu, Yan; Ma, Long-Xu; Sun, Liang-Peng; Song, Ming-Xia; Cui, Xun; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 3; (2013); p. 757 - 760, View in Reaxys; Karakaya, Guelsah; Aytemir, Mutlu Dilsiz; Oezcelik, Berrin; Calis, Uensal; Journal of Enzyme Inhibition and Medicinal Chemistry; vol. 28; nb. 3; (2013); p. 627 - 638, View in Reaxys; Wu, Yan; Sun, Liang-Peng; Ma, Long-Xu; Che, Jian; Song, Ming-Xia; Cui, Xun; Piao, Hu-Ri; Chemical Biology and Drug Design; vol. 81; nb. 5; (2013); p. 591 - 599, View in Reaxys; Aytemir, Mutlu Dilsiz; Oezcelik, Berrin; Karakaya, Guelsah; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 12; (2013); p. 3646 - 3649, View in Reaxys; Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys; Wang, Baolei; Shi, Yanxia; Zhan, Yizhou; Zhang, Liyuan; Zhang, Yan; Wang, Lizhong; Zhang, Xiao; Li, Yonghong; Li, Zhengming; Li, Baoju; Chinese Journal of Chemistry; vol. 33; nb. 10; (2015); p. 1124 - 1134, View in Reaxys; Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys; Zhang, Li-Yuan; Wang, Bao-Lei; Zhan, Yi-Zhou; Zhang, Yan; Zhang, Xiao; Li, Zheng-Ming; Chinese Chemical Letters; vol. 27; nb. 1; (2016); p. 163 - 167, View in Reaxys; Wang, Bao-Lei; Zhan, Yi-Zhou; Zhang, Li-Yuan; Zhang, Yan; Zhang, Xiao; Li, Zheng-Ming; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; nb. 1; (2016); p. 48 - 54, View in Reaxys 2 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys 3 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Reaxys ID 5666411 View in Reaxys

18/323 CAS Registry Number: 13171-25-0; 127881-54-3 Chemical Name: trimetazidine dihydrochloride; 1-(2,3,4-trimethoxybenzyl)piperazine dihydrochloride; Trimetazidine dihydrochloride; 2,3,4-trimethoxybenzylpiperazine dihydrochloride; trimetazidine; 1-(2,3,4-trimethoxybenzyl)-piperazine dihydrochloride; 1-(2,3,4-trimethyloxybenzyl)piperazine dihydrochloride Linear Structure Formula: C14H22N2O3*2HCl Molecular Formula: C14H22N2O3*2ClH Molecular Weight: 339.262 Type of Substance: heterocyclic InChI Key: QHWBCHACIJBSFV-UHFFFAOYSA-N Note:

O O

Cl 2 H NH

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Substance Label (4) Label References TMZ

Vedrinne, Catherine; Sebbag, Laurent; Arvieux, Charles; Cannet, Emmanuelle; Forrat, Remi; Hadour, Guylaine; Ferrera, Rene; Guidollet, Jeannine; Lehot, Jean-Jacques; De Lorgeril, Michel; Journal of Cardiovascular Pharmacology; vol. 28; nb. 4; (1996); p. 500 - 506, View in Reaxys; Tabbi-Anneni, Imene; Helies-Toussaint, Cecile; Morin, Didier; Bescond-Jacquet, Anne; Lucien, Arnaud; Grynberg, Alain; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 3; (2003); p. 1003 - 1009, View in Reaxys; Napoli, Pericle Di; Giovanni, Paolo Di; Gaeta, Marta Assunta; Taccardi, Alfonso A.; Barsotti, Antonio; Journal of Cardiovascular Pharmacology; vol. 50; nb. 5; (2007); p. 585 - 589, View in Reaxys; Dayanithi, Govindan; Desmadryl, Gilles; Travo, Cecile; Chabbert, Christian; Sans, Alain; European Journal of Pharmacology; vol. 574; nb. 1; (2007); p. 8 - 14, View in Reaxys

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys

Ohtaka; Miyake; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2774 - 2781, View in Reaxys; Jackson; Brownsill; Taylor; Resplandy; Walther; Schwietert; Xenobiotica; vol. 26; nb. 2; (1996); p. 221 - 228, View in Reaxys

TMZ, Merck 9835

Lagadic-Gossmann, Dominique; Le Prigent, Karine; Feuvray, Danielle; British Journal of Pharmacology; vol. 117; nb. 5; (1996); p. 831 - 838, View in Reaxys

Patent-Specific Data (2) Location in Patent References Page/Page column

Claim

Patent; Science Union Et Cie; US4407801; (1983); (A1) English, View in Reaxys; Patent; Bayer Classics; EP1104673; (2001); (A1) English, View in Reaxys; Patent; USV Ltd.; EP1195160; (2002); (A1) English, View in Reaxys

Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Wang; Sun; Rong; Tang; He, Zhonggui G.; Pharmazie; vol. 62; nb. 1; (2007); p. 27 - 30, View in Reaxys

Pharmacological Data (28) 1 of 28

Comment (Pharmacological Data)

Bioactivities present

Patent; Science Union Et Cie; US4407801; (1983); (A1) English, View in Reaxys; Patent; Bayer Classics; EP1104673; (2001); (A1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US4880809; (1989); (A1) English, View in Reaxys; Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys; Ohtaka; Yoshida; Suzuki; Shimohara; Tajima; Ito; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 3948 - 3954, View in Reaxys; Ohtaka; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 8; (1987); p. 3270 - 3275, View in Reaxys; Ohtaka; Miyake; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2774 - 2781, View in Reaxys; Jackson; Brownsill; Taylor; Resplandy; Walther; Schwietert; Xenobiotica; vol. 26; nb. 2; (1996); p. 221 - 228, View in Reaxys; Lagadic-Gossmann, Dominique; Le Prigent, Karine; Feuvray, Danielle; British Journal of Pharmacology; vol. 117; nb. 5; (1996); p. 831 - 838, View in Reaxys; Vedrinne, Catherine; Sebbag, Laurent; Arvieux, Charles; Cannet, Emmanuelle; Forrat, Remi; Hadour, Guylaine; Ferrera, Rene; Guidollet, Jeannine; Lehot, Jean-Jacques; De Lorgeril, Michel; Journal of Cardiovascular Pharmacology; vol. 28; nb. 4; (1996); p. 500 - 506, View in Reaxys; Tabbi-Anneni, Imene; Helies-Toussaint, Cecile; Morin, Didier; Bescond-Jacquet, Anne; Lucien, Arnaud; Grynberg, Alain; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 3; (2003); p. 1003 - 1009, View in Reaxys; Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys; D'hahan; Taouil; Janmot; Morel; British journal of pharmacology; vol. 123; nb. 4; (1998); p. 611 - 616, View in Reaxys; Wang; Sun; Rong; Tang; He, Zhonggui G.; Pharmazie; vol. 62; nb. 1; (2007); p. 27 - 30, View in Reaxys; Napoli, Pericle Di; Giovanni, Paolo Di; Gaeta, Marta Assunta; Taccardi, Alfonso A.; Barsotti, Antonio; Journal of Cardiovascular Pharmacology; vol. 50; nb. 5; (2007); p. 585 - 589, View in Reaxys; Dayanithi, Govindan; Desmadryl, Gilles; Travo, Cecile; Chabbert, Christian; Sans, Alain; European Journal of Pharmacology; vol. 574; nb. 1; (2007); p. 8 - 14, View in Reaxys; Patent; Kanebo, Ltd.; US4797400; (1989); (A1) English, View in Reaxys; Patent; USV Ltd.; EP1195160; (2002); (A1) English, View in Reaxys; Patent; SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A.; WO2007/96251; (2007); (A1) English, View in Reaxys; Jin, Lu; Jiang, Xiang-Min; Du, Ping; Xu, Jing; Gong, Guo-Qing; Wang, Qiu-Juan; Xu, Yun-Gen; European Journal of Medicinal Chemistry; vol. 46; nb. 9; (2011); p. 4107 - 4116, View in Reaxys; Lagadic-Gossmann; Le Prigent; Feuvray; British Journal of Pharmacology; vol. 117; nb. 5; (1996); p. 831 - 838, View in Reaxys; Patent; ZAKRYTOE AKTSIONERNOE OBSCHSHESTVO "VERTEX"; Veselkina, Olga Sergejevna; Viktorov, Nikolay Borisovich; Petrishchev, Nikolay Nikolaevich; Poplavskaya, Yuliya Vyacheslavovna; US2013/267707; (2013); (A1) English, View in Reaxys

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Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

20 mg

Kind of Dosing (Pharmacological Data)

title comp. administered as single tablet purchased from Chinese (test) and French (reference) suppliers

Method (Pharmacological Data)

serial blood samples collected 0.25, 0.5, 0.75, 1.0, 1.5, 2.0, 2.5, 3.0, 4.0, 6.0, 8.0, 12.0, 24.0 and 30.0 h after administration; plasma separated; concn. of title comp. measured (LCI-ESI-MS); pharmacokinetic parameters Cmax, tmax, AUC calculated

Further Details (Pharmacological Data)

20 healthy volunteers (mean age 22 years, mean wt 60 kg) used for test; Cmax = maximum blood concn., tmax = time to reach Cmax, AUC = area under time-concn. curve; LCI-ESIMS: liquid chromatography-electrospray ionization mass spectrometry

Results

test and reference tablets are bioequivalent; no differences in pharmacokinetics; test: Cmax = 60.5 ng/ml, tmax = 1.9 h; reference: Cmax = 61.3 ng/ml, tmax = 1.9 h; diagram

Wang; Sun; Rong; Tang; He, Zhonggui G.; Pharmazie; vol. 62; nb. 1; (2007); p. 27 - 30, View in Reaxys 3 of 28

Effect (Pharmacological Data)

toxicity

Species or Test-System (Pharmacological Data)

human

Concentration (Pharmacological Data)

20 mg

Kind of Dosing (Pharmacological Data)

title comp. admin. thrice daily

Method (Pharmacological Data)

single center, open-label, randomized trial study; chronic heart failure subjects treated with title comp.; all-cause mortality studied at baseline and 6-48 months

Further Details (Pharmacological Data)

control: without title comp.

Results

title comp. signif. reduced all-cause mortality (17percent versus 39percent control) after 48 months; mean survival time was 42 months in title comp.-treated group and 29 months in control group; table, fig.

Napoli, Pericle Di; Giovanni, Paolo Di; Gaeta, Marta Assunta; Taccardi, Alfonso A.; Barsotti, Antonio; Journal of Cardiovascular Pharmacology; vol. 50; nb. 5; (2007); p. 585 - 589, View in Reaxys 4 of 28

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

human

Concentration (Pharmacological Data)

20 mg

Kind of Dosing (Pharmacological Data)

title comp. admin. thrice daily

Method (Pharmacological Data)

single center, open-label, randomized trial study; chronic heart failure subjects treated with title comp.; heart failure hospitalization determined at baseline and 6-48 months

Further Details (Pharmacological Data)

control: without title comp.

Results

mean survival time from hospitalization was 20.5 months in title comp.-treated group; title comp. increased dosages of diuretics, angiotensin-converting enzyme and beta-blockers while it did not lead to any modification or discontinuation; table, fig.

Napoli, Pericle Di; Giovanni, Paolo Di; Gaeta, Marta Assunta; Taccardi, Alfonso A.; Barsotti, Antonio; Journal of Cardiovascular Pharmacology; vol. 50; nb. 5; (2007); p. 585 - 589, View in Reaxys

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Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

human

Concentration (Pharmacological Data)

20 mg

Kind of Dosing (Pharmacological Data)

title comp. admin. thrice daily

Method (Pharmacological Data)

single center, open-label, randomized trial study; chronic heart failure subjects treated with title comp.; functional status and 6-min walk test performed at baseline and 6-48 months

Further Details (Pharmacological Data)

control: without title comp.

Results

significant functional improvement was noted in title comp.-treated groups starting at the 12-month; distance walked in title comp.-treated group from 362 m at baseline to 425 m at the end of follow-up; fig., table

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

human

Concentration (Pharmacological Data)

20 mg

Kind of Dosing (Pharmacological Data)

title comp. admin. thrice daily

Method (Pharmacological Data)

single center, open-label, randomized trial study; chronic heart failure subjects treated with title comp.; echocardiography performed at baseline and 6-48 months

Further Details (Pharmacological Data)

control: without title comp.; ES: end-systolic; ED: end-diastolic; LVEF: left ventricle ejection fraction

Results

increase of LVEF was noted starting 6 months, maintained after 48 months in title comp.treated groups while it signif. reduced left ventricle ES/ED volumes; prevalence and severity of mitral insufficiency were stable in title comp.-treated group; fig.

Effect (Pharmacological Data)

protein levels; effect on

Species or Test-System (Pharmacological Data)

human

Concentration (Pharmacological Data)

20 mg

Kind of Dosing (Pharmacological Data)

title comp. admin. thrice daily

Method (Pharmacological Data)

single center, open-label, randomized trial study; chronic heart failure subjects treated with title comp.; C-reactive protein plasma levels determined

Further Details (Pharmacological Data)

control: without title comp.

Results

C-reactive protein plasma levels remained stable in title comp.-treated groups; fig.

Effect (Pharmacological Data)

adverse effect

Species or Test-System (Pharmacological Data)

human

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Concentration (Pharmacological Data)

20 mg

Kind of Dosing (Pharmacological Data)

title comp. admin. thrice daily

Method (Pharmacological Data)

single center, open-label, randomized trial study; chronic heart failure subjects treated with title comp.; adverse effects monitored at 6-48 months

Further Details (Pharmacological Data)

control: without title comp.

Results

title comp. was well tolerated in patients with ischemic dilated cardiomyopathy up to 48 months; no significant changes in blood determination of renal and hepatic function or serum electrolytes were related to title comp.-treatment

Effect (Pharmacological Data)

Ca2+ entry; inhibition of

Species or Test-System (Pharmacological Data)

vestibular ganglion neurons of Wistar rat

Concentration (Pharmacological Data)

1 - 100 μmol/l

Method (Pharmacological Data)

neurons loaded with Fura-2/AM and stimulated with 100 μM kainate at 37 deg C; fluorescence read

Further Details (Pharmacological Data)

neurons obtained from 3-day-old rats

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

7 μmol/l

Results

title comp. dose-dependently inhibited kainate-induced Ca2+ responses; fig.

Dayanithi, Govindan; Desmadryl, Gilles; Travo, Cecile; Chabbert, Christian; Sans, Alain; European Journal of Pharmacology; vol. 574; nb. 1; (2007); p. 8 - 14, View in Reaxys 10 of 28

Effect (Pharmacological Data)

Ca2+ entry; inhibition of

Species or Test-System (Pharmacological Data)

vestibular ganglion neurons of Wistar rat

Concentration (Pharmacological Data)

20 μmol/l

Method (Pharmacological Data)

neurons loaded with Fura-2/AM, pretreated with title comp. for 3 min and stimulated with 100 μM AMPA at 37 deg C; fluorescence read

Further Details (Pharmacological Data)

neurons obtained from 3-day-old rats

Results

title comp. reduced (by ca. 60percent) AMPA-induced Ca2+ responses, effect reversible after wash-out; fig.

Dayanithi, Govindan; Desmadryl, Gilles; Travo, Cecile; Chabbert, Christian; Sans, Alain; European Journal of Pharmacology; vol. 574; nb. 1; (2007); p. 8 - 14, View in Reaxys 11 of 28

Effect (Pharmacological Data)

neuroregulatoric

Species or Test-System (Pharmacological Data)

vestibular ganglion neurons of Wistar rat

Concentration (Pharmacological Data)

Ca. 0.01 - 1000 μmol/l

Method (Pharmacological Data)

currents induced by 1 mM glutamate, measured using whole-cell (voltage-clamp configuration) from holding potential of -70 mV

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Further Details (Pharmacological Data)

neurons obtained from 3-day-old rats

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

10 μmol/l

Results

title comp. dose-dependently inhibited glutamate-induced currents with maximum inhibition of 90percent at ca. 1 mM; fig.

Dayanithi, Govindan; Desmadryl, Gilles; Travo, Cecile; Chabbert, Christian; Sans, Alain; European Journal of Pharmacology; vol. 574; nb. 1; (2007); p. 8 - 14, View in Reaxys 12 of 28

Effect (Pharmacological Data)

neuroregulatoric

Species or Test-System (Pharmacological Data)

vestibular ganglion neurons of Wistar rat

Concentration (Pharmacological Data)

Ca. 0.01 - 10000 μmol/l

Method (Pharmacological Data)

currents induced by 100 μM AMPA, measured using whole-cell (voltage-clamp configuration) from holding potential of -70 mV

Further Details (Pharmacological Data)

neurons obtained from 3-day-old rats

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

25 μmol/l

Results

title comp. dose-dependently inhibited AMPA-induced currents with maximum inhibition of 100percent at ca. 10 mM; fig.

Dayanithi, Govindan; Desmadryl, Gilles; Travo, Cecile; Chabbert, Christian; Sans, Alain; European Journal of Pharmacology; vol. 574; nb. 1; (2007); p. 8 - 14, View in Reaxys 13 of 28

Effect (Pharmacological Data)

cardiotonic

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intravenous

Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. injected as bolus

Method (Pharmacological Data)

left anterior descending coronary artery occlusion (ligation); title comp. administered 20 min before 30-min occlusion, 10 min before preconditioning ischemia or carbachol infusion; arterial blood pressure and heart rate evaluated; ECG recorded

Further Details (Pharmacological Data)

preconditioning 5-min ischemia or preconditioning carbachol infusion (i.v., 4 μg/kg/min) 5 min before 30-min ischemia; blood pressure measured in left carotid artery; ECG: electrocardiogram

Comment (Pharmacological Data)

No effect

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys 14 of 28

Effect (Pharmacological Data)

cardiotonic

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

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Route of Application

intravenous

Kind of Dosing (Pharmacological Data)

infusion 2 mg/kg/min for 5 min

Method (Pharmacological Data)

left anterior descending coronary artery occlusion (ligation); title comp. administered 5 min before 30-min occlusion; arterial blood pressure and heart rate evaluated; ECG recorded

Further Details (Pharmacological Data)

blood pressure measured in left carotid artery; ECG: electrocardiogram

Comment (Pharmacological Data)

No effect

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys 15 of 28

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intravenous

Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. injected as bolus

Method (Pharmacological Data)

Further Details (Pharmacological Data)

preconditioning 5-min ischemia or preconditioning carbachol infusion (i.v., 4 μg/kg/min) 5 min before 30-min ischemia

Comment (Pharmacological Data)

No effect

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys 16 of 28

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intravenous

Kind of Dosing (Pharmacological Data)

infusion 2 mg/kg/min for 5 min

Method (Pharmacological Data)

left anterior descending coronary artery occlusion (ligation); title comp. administered 5 min before 30-min occlusion; plasma creatine kinase-MB activity determined

Comment (Pharmacological Data)

No effect

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys 17 of 28

Effect (Pharmacological Data)

metabolic

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intravenous

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Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. injected as bolus

Method (Pharmacological Data)

left anterior descending coronary artery occlusion (ligation); title comp. administered 20 min before 30-min occlusion, 10 min before preconditioning ischemia or carbachol infusion; plasma lactate, cardiac troponin C, malondialdehyde (MDA) determined

Further Details (Pharmacological Data)

preconditioning 5-min ischemia or preconditioning carbachol infusion (i.v., 4 μg/kg/min) 5 min before 30-min ischemia; troponin T determined by immunoassay; MDA determined by spectrophotometry (assay of thiobarbituric acid-reactive substances)

Comment (Pharmacological Data)

No effect

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys 18 of 28

Effect (Pharmacological Data)

metabolic

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intravenous

Kind of Dosing (Pharmacological Data)

infusion 2 mg/kg/min for 5 min

Method (Pharmacological Data)

left anterior descending coronary artery occlusion (ligation); title comp. administered 5 min before 30-min occlusion; plasma lactate, cardiac troponin C, malondialdehyde (MDA) determined

Further Details (Pharmacological Data)

troponin T determined by immunoassay; MDA determined by spectrophotometry (assay of thiobarbituric acid-reactive substances)

Comment (Pharmacological Data)

No effect

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys 19 of 28

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intravenous

Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. injected as bolus

Method (Pharmacological Data)

left anterior descending coronary artery occlusion (ligation); title comp. administered 20 min before 30-min occlusion, 10 min before preconditioning ischemia or carbachol infusion; area at risk (Evans blue dye) and infarct size (with TTC) determined

Further Details (Pharmacological Data)

preconditioning 5-min ischemia or preconditioning carbachol infusion (i.v., 4 μg/kg/min) 5 min before 30-min ischemia; TTC: 2,3,5-triphenyltetrazolium chloride

Results

title comp. potentiated protective effect of preconditioning on infarct size

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys 20 of 28

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Wistar rat

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Sex

male

Route of Application

intravenous

Kind of Dosing (Pharmacological Data)

infusion 2 mg/kg/min for 5 min

Method (Pharmacological Data)

left anterior descending coronary artery occlusion (ligation); title comp. administered 5 min before 30-min occlusion; area at risk (with Evans blue dye) and infarct size (with TTC) determined

Further Details (Pharmacological Data)

TTC: 2,3,5-triphenyltetrazolium chloride

Results

title comp. decreased infarct size

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys 21 of 28

Effect (Pharmacological Data)

antiarrhythmic

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intravenous

Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. injected as bolus

Method (Pharmacological Data)

left anterior descending coronary artery occlusion (ligation); title comp. administered 20 min before 30-min occlusion, 10 min before preconditioning ischemia or carbachol infusion; arrhythmia onset and duration registered during occlusion by ECG

Further Details (Pharmacological Data)

preconditioning 5-min ischemia or preconditioning carbachol infusion (i.v., 4 μg/kg/min) 5 min before 30-min ischemia; ventricular arrythmias (tachycardia, fibrillation, ectopic beat) recorded; ECG: electrocardiogram

Results

title comp. potentiated ischemic preconditioning-induced reduction of arrhythmia and preserved carbohol preconditioning; title comp. markedly delayed occurrence of first arrhythmia after preconditioning

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys 22 of 28

Effect (Pharmacological Data)

antiarrhythmic

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intravenous

Kind of Dosing (Pharmacological Data)

infusion 2 mg/kg/min for 5 min

Method (Pharmacological Data)

left anterior descending coronary artery occlusion (ligation); title comp. administered 5 min before 30-min occlusion; arrhythmia onset and duration registered during occlusion by ECG

Further Details (Pharmacological Data)

ventricular arrythmias (tachycardia, fibrillation, ectopic beat) recorded; ECG: electrocardiogram

Results

title comp. infusion suppressed numbers of ectopic beats (177 vs 622 in control), decreased incidence of ventricular tachycardia (to 30 percent), abolished incidence of fibrillation, and delayed occurrence of first arrhythmia

Kara, Ali F.; Demiryuerek, Seniz; Celik, Ahmet; Tarakcioglu, Mehmet; Demiryuerek, Abdullah T.; European Journal of Pharmacology; vol. 503; nb. 1-3; (2004); p. 135 - 145, View in Reaxys 23 of 28

Effect (Pharmacological Data)

cardioprotective

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Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

peroral

Kind of Dosing (Pharmacological Data)

7.5 mg/d in jellied diet for 8 or 12 weeks

Method (Pharmacological Data)

aortic stenosis induced via left incision by banding ascending aorta with hemoclip, title comp. treatment started 3-4 days later; plasma BNP levels measured by RIA; heart weight to body weight ratio determined; macroscopic necropsy

Further Details (Pharmacological Data)

further studies on myocardial α- and β-adrenoceptor (AR) density by using radioligands; BNP: brain natriuretic protein, marker of heart failure severity

Results

title comp. treatment significantly reduced severity of cardiac hypertrophy (mainly affecting left ventricle), reduced increased BNP plasma level and prevented down-regulation of αand β-ARs induced by ascending aorta banding

Tabbi-Anneni, Imene; Helies-Toussaint, Cecile; Morin, Didier; Bescond-Jacquet, Anne; Lucien, Arnaud; Grynberg, Alain; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 3; (2003); p. 1003 - 1009, View in Reaxys 24 of 28

Effect (Pharmacological Data)

cardioprotective

Species or Test-System (Pharmacological Data)

Syrian cardiomyopathic BIO 14:6 hamster

Concentration (Pharmacological Data)

18 mg/kg

Kind of Dosing (Pharmacological Data)

daily in drinking water from age 30 days to up to 350 days

Method (Pharmacological Data)

myosin isoenzyme distribution studied at prenecrotic stage (30 days), necrotic stage (65 days), hypertrophic stage (220 days) and final stage (350 days) by PGE, followed by CB staining and scanning densitometry at 600 nm; ATPase activity also determined

Further Details (Pharmacological Data)

PGE: pyrophosphate polyacrylamide gel electrophoresis, at 2 deg C for 22 h; CB: Coomassie brilliant blue

Results

within 65 days, title comp. reduced V1 to low level (53 percent)

D'hahan; Taouil; Janmot; Morel; British journal of pharmacology; vol. 123; nb. 4; (1998); p. 611 - 616, View in Reaxys 25 of 28

Effect (Pharmacological Data)

metabolic

Species or Test-System (Pharmacological Data)

human

Sex

male and female

Route of Application

peroral

Concentration (Pharmacological Data)

80 mg/day

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

four healthy Caucasian volunteers, two female (20-23 years old, weight 78-66 kg) and two male (19-22 years old, weight 67-69 kg); urine were collected between 0 and 12 h after dosing; plasma was collected 6-82 h after the first dose

Results

unchanged title comp. was the major compound observed in urine and plasma; 10 metabolites in urine (0.01 percent to 1.4 percent dose); metabolic profile; pathway

Jackson; Brownsill; Taylor; Resplandy; Walther; Schwietert; Xenobiotica; vol. 26; nb. 2; (1996); p. 221 - 228, View in Reaxys 26 of 28

Effect (Pharmacological Data)

pharmacokinetics

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Species or Test-System (Pharmacological Data)

human

Sex

male and female

Route of Application

peroral

Concentration (Pharmacological Data)

80 mg/day

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

four healthy Caucasian volunteers, two female (20-23 years old, weight 78-66 kg) and two male (19-22 years old, weight 67-69 kg); plasma was collected 6-82 h after the first dose

Results

conc. in plasma: 51.1-125.8 ng/ml after 6 h, 65.2-92.2 ng/ml after 10 h, 65.9-129.3 ng/ml after 78 h, 68.4-103.9 ng/ml after 82 h

Jackson; Brownsill; Taylor; Resplandy; Walther; Schwietert; Xenobiotica; vol. 26; nb. 2; (1996); p. 221 - 228, View in Reaxys 27 of 28

Effect (Pharmacological Data)

intracellular pH regulator

Species or Test-System (Pharmacological Data)

ventricular myocytes of Wistar rat

Sex

male

Concentration (Pharmacological Data)

0.3 - 1 mmol/l

Method (Pharmacological Data)

weight 250-300 g; procedures by Ministere de l'Agriculture et de la Foret, France; to myocytes from hearts applied for 15 min, 2, 3, 5.5 h prior to induction of acid-load twice by NH4(1+) prepulse method in absence and presence of title comp.

Further Details (Pharmacological Data)

intracellular pH (pHi) monitored ratiometrically by use of pH-sensitive carboxy-seminaphthorhodafluor; intracellular intrinsic buffering power (βi); Student's t test

Results

rates of pHi recovery was given in table; time-, dose-dependent; slowing by ca. 64 percent for 2-3 h treatment with 1 mM; βi increased roughly linearly with decrease in pHi; acid efflux decreased only by treatment with 1 mM for 2-3 h

Lagadic-Gossmann, Dominique; Le Prigent, Karine; Feuvray, Danielle; British Journal of Pharmacology; vol. 117; nb. 5; (1996); p. 831 - 838, View in Reaxys 28 of 28

Effect (Pharmacological Data)

cardiotonic

Species or Test-System (Pharmacological Data)

anglonormand dogs

Sex

male and female

Kind of Dosing (Pharmacological Data)

oral treatment: 1 mg/kg/day title comp. for 3 days before experim. day, 15 min after instrumentation a bolus of 0.5 mg/kg title comp. followed by infusion of 0.5 mg/h for 4 h

Method (Pharmacological Data)

in vivo; 30 dogs pretreated with title comp.; anesthesia, tracheal intubation, thoracotomy performed, heart exposed and suspended in a pericardial cradle, left anterior descending coronary artery (LAD) occluded with silk snare for 15 min and reperfused

Further Details (Pharmacological Data)

effect of title comp. on postischemic regional myocardial stunning; LAD occluded 15 min after beginning of infusion; control: placebo, saline; after 125 min of reperfusion, 10 μg/kg/min dobutamine infused for 15 min; blood sampling, hemodynamic measur.

Results

despite lower heart rate and reduction of lipid peroxidation in treated dogs, myocardial stunning and recruitment of contractile reserve by dobutamine infusion in the postischemic myocardium were not modified by title comp. (tables, diagram)

References

inhibits long fatty acid oxidation;

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

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stimulates glucose oxidation Fibromyalgia syn- Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, drome (FMS) View in Reaxys Chronic fatigue syndrome (CFS)

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Myofascial pain syndrome (MPS)

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Gulf War syndrome (GWS)

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Rheumatic condition

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Trigger point pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Trigger point tenderness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Depression

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Dizziness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Impaired concentration

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Irritable bowel syndrome

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Headache

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Fatigue

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Sleep disturbance Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys Chronic headaches

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Sleep disorder

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Jaw pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Cognitive impairment

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Memory impairment

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Post-exertional malaise

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Muscle pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Morning stiffness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Menstrual cramping

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Numbness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Tingling sensations

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

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Skin sensitivities

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Chemical sensitivities

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Balance problems Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys Stiffness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Fluid retention

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

weight loss

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Skin rashes

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Chronic fevers

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Peripheral numbness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Joint pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Coronary heart disease

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Stable angina

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Reaxys ID 5747566 View in Reaxys

19/323 CAS Registry Number: 55513-16-1 Chemical Name: N-[3-(trifluoromethyl)benzyl]piperazine; 1-[3(trifluoromethyl)-benzyl]piperazine; 1-[3-(trifluoromethyl)benzyl]piperazine; 1-(3-(trifluoromethyl)benzyl)piperazine; 1-(3-trifluoromethylbenzyl)piperazine; 1-(3-Trifluoromethyl-benzyl) piperazine; 1-[3-(trifluoromethyl)benzyl]piperazine Linear Structure Formula: C12H15F3N2 Molecular Formula: C12H15F3N2 Molecular Weight: 244.26 Type of Substance: heterocyclic InChI Key: IUMQPHHEFKTLOZ-UHFFFAOYSA-N Note:

N NH

Substance Label (3) Label References mTFMBP

Bohnert, Juergen A.; Kern, Winfried V.; Antimicrobial Agents and Chemotherapy; vol. 49; nb. 2; (2005); p. 849 - 852, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Scotto di Tella; Dessaigne; Boyer; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 2; (1984); p. 131 - 135, View in Reaxys

Patent-Specific Data (2) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys Patent; Brinkman, John A.; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Guertin, Kevin Richard; Marcopulos, Nicholas; Qi, Lida; Racha, Jagdish Kumar; Sarabu, Ramakanth; Tan, Jenny; Tilley, Jefferson Wright; US2007/270433; (2007); (A1) English, View in Reaxys

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Derivative (1) Derivative

References

1-(3-TrifluoroScotto di Tella; Dessaigne; Boyer; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 2; (1984); methyl-benzyl)-pi- p. 131 - 135, View in Reaxys perazine; hydrochloride Boiling Point (1) Boiling Point [°C] 100 - 104

Pressure (Boiling Point) [Torr]

References

0.09

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (6) 1 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 4 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy)

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Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 5 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 6 of 6

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Pharmacological Data (4) 1 of 4

Comment (Pharmacological Data)

Bioactivities present

Patent; American Home Products Corporation; US4837325; (1989); (A1) English, View in Reaxys; Patent; American Cyanamid Co.; US4963553; (1990); (A1) English, View in Reaxys; Patent; Wu, Chengde; Anderson, C. Eric; Bui, Huong; Dupre, Brian; Gao, Daxin; Holland, George W.; Kassir, Jamal; Li, Wen; Wang, Junmei; US2005/54850; (2005); (A1) English, View in Reaxys; Patent; Brinkman, John A.; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Guertin, Kevin Richard; Marcopulos, Nicholas; Qi, Lida; Racha, Jagdish Kumar; Sarabu, Ramakanth; Tan, Jenny; Tilley, Jefferson Wright; US2007/270433; (2007); (A1) English, View in Reaxys; Scotto di Tella; Dessaigne; Boyer; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 2; (1984); p. 131 - 135, View in Reaxys; Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 597, View in Reaxys; Kuwahara; Kato; Sugawara; Miyake; Chemical and Pharmaceutical Bulletin; vol. 43; nb. 9; (1995); p. 1511 - 1515, View in Reaxys; Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys; Bohnert, Juergen A.; Kern, Winfried V.; Antimicrobial Agents and Chemotherapy; vol. 49; nb. 2; (2005); p. 849 - 852, View in Reaxys; Omran, Ziad; Cailly, Thomas; Lescot, Elodie; Santos, Jana Sopkova-De Oliveira; Agondanou, Jean-Hugues; Lisowski, Vincent; Fabis, Frederic; Godard, Anne-Marie; Stiebing, Silvia; Le Flem, Guillaume; Boulouard, Michel; Dauphin, Francois; Dallemagne, Patrick; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 40; nb. 12; (2005); p. 1222 - 1245, View in Reaxys; Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys; Ye, Yang-liang; Zhou, Zhou; Zou, Hanjun; Shen, Yu; Xu, Ti-fei; Tang, Jing; Yin, Hua-zhong; Chen, Min-li; Leng, Ying; Shen, Jian-hua; Bioorganic and Medicinal Chemistry; vol. 17; nb. 15; (2009); p. 5722 - 5732, View in Reaxys; Borrmann, Thomas; Hinz, Sonja; Bertarelli, Daniela C. G.; Li, Wenjin; Florin, Nicole C.; Scheiff, Anja B.; Mueller, Christa E.; Journal of Medicinal Chemistry; vol. 52; nb. 13; (2009); p. 3994 - 4006, View in Reaxys; Patent; ABBOTT LABORATORIES; BHATIA, Pramila, A.; DOHERTY, George, A.; DRIZIN, Irene; MACK, Helmut; PERNER, Richard, J.; STEWART, Andrew, O.; ZHANG, Qing Wei; WO2010/39947; (2010); (A1) English, View in Reaxys; Gitto, Rosaria; De Luca, Laura; Ferro, Stefania; De Grazia, Sara; Di Giorgio, Rosa Maria; Festa, Filomena; De Luca, Grazia; Journal of Heterocyclic Chemistry; vol. 47; nb. 1; (2010); p. 54 - 62, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Sun, Aiming; Moore, Terry W.; Gunther, Jillian R.; Kim, Mi-Sun; Rhoden, Eric; Du, Yuhong; Fu, Haian; Snyder, James P.; Katzenellenbogen, John A.; ChemMedChem; vol. 6; nb. 4; (2011); p. 654 - 666, View in Reaxys; Doherty, George A.; Bhatia, Pramila; Vortherms, Timothy A.; Marsh, Kennan C.; Wetter, Jill M.; MacK, Helmut; Scott, Victoria E.; Jarvis, Michael F.; Stewart, Andrew O.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 4; (2012); p. 1716 - 1718, View in Reaxys; Agai-Csongor, Eva; Domany, Gyoergy; Nogradi, Katalin; Galambos, Janos; Vago, Istvan; Keser, Gyoergy Miklos; Greiner, Istvan; Laszlovszky, Istvan; Gere, Aniko; Schmidt, Eva; Kiss, Bela; Vastag, Monika; Tihanyi, Karoly; Saghy, Katalin; Laszy, Judit; Gyertyan, Istvan; Zajer-Balazs, Maria; Gemesi, Larisza; Kapas, Margit; Szombathelyi, Zsolt; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 10; (2012); p. 3437 -

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3440, View in Reaxys; Karakaya, Guelsah; Aytemir, Mutlu Dilsiz; Oezcelik, Berrin; Calis, Uensal; Journal of Enzyme Inhibition and Medicinal Chemistry; vol. 28; nb. 3; (2013); p. 627 - 638, View in Reaxys; Aytemir, Mutlu Dilsiz; Oezcelik, Berrin; Karakaya, Guelsah; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 12; (2013); p. 3646 - 3649, View in Reaxys; Foley, Timothy L.; Rai, Ganesha; Yasgar, Adam; Daniel, Thomas; Baker, Heather L.; Attene-Ramos, Matias; Kosa, Nicolas M.; Leister, William; Burkart, Michael D.; Jadhav, Ajit; Simeonov, Anton; Maloney, David J.; Journal of Medicinal Chemistry; vol. 57; nb. 3; (2014); p. 1063 - 1078, View in Reaxys 2 of 4

Effect (Pharmacological Data)

bacterial resistance; inhibition of

Species or Test-System (Pharmacological Data)

Escherichia coli 3-AG100MKX

Method (Pharmacological Data)

cells incubated with levofloxacin in presence of title comp.; levofloxacin MIC determined by spectrofotometric assay

Further Details (Pharmacological Data)

3-AG100MKX: AcrAB-overexpressing gyrA mutant derived from AG100MKX (AG100 marA::Kmr); AcrAB: efflux pump; reference comp.: Phe-Arg-β-naphtylamide

Results

title comp. conc. to reduce levofloxacin MIC by 4-fold was 200 μg/ml

Bohnert, Juergen A.; Kern, Winfried V.; Antimicrobial Agents and Chemotherapy; vol. 49; nb. 2; (2005); p. 849 852, View in Reaxys 3 of 4

Effect (Pharmacological Data)

drug accumulation; effect on

Species or Test-System (Pharmacological Data)

Escherichia coli 3-AG100MKX

Concentration (Pharmacological Data)

100 mg/l

Method (Pharmacological Data)

after 10 min incubation with 10 μg/ml of levofloxacin in (pH 7.0) at 37 deg C cells cultivated in presence or title comp. up to 20 min; 1 ml samples removed periodically; released levofloxacin measured by spectrofluorometric assay at 496 nm

Further Details (Pharmacological Data)

3-AG100MKX: acrAB-overexpressing gyrA mutant derived from AG100MKX (AG100 marA::Kmr)

Comment (Pharmacological Data)

No effect

Bohnert, Juergen A.; Kern, Winfried V.; Antimicrobial Agents and Chemotherapy; vol. 49; nb. 2; (2005); p. 849 852, View in Reaxys 4 of 4

Comment (Pharmacological Data)

antidysrythmicactivity on rats

Scotto di Tella; Dessaigne; Boyer; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 2; (1984); p. 131 135, View in Reaxys

Reaxys ID 4249340 View in Reaxys

20/323 CAS Registry Number: 55513-19-4 Chemical Name: 1-(3-fluoro-benzyl)-piperazine; 1-(3-fluorobenzyl)piperazine; 1-(3fluoro-benzyl)-piperazine Linear Structure Formula: C11H15FN2 Molecular Formula: C11H15FN2 Molecular Weight: 194.252 Type of Substance: heterocyclic InChI Key: ITHBJSRWFNLKIH-UHFFFAOYSA-N Note:

H N

Substance Label (5) Label References 5g

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

167/337

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piperazine, b

Yang, Yinghua; Sun, Lianli; Dong, Shengyi; Wang, Xiaoyu; Yang, Leixiang; Wu, Xiumei; Bai, Hua; Zhao, Yu; Mendeleev Communications; vol. 18; nb. 4; (2008); p. 186 - 187, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Boiling Point (1) Boiling Point [°C] 110 - 115

Pressure (Boiling Point) [Torr]

References

0.25

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 4 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

168/337

2016-05-20 15:00:44

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 5 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Kurokawa, Mikio; Sato, Fuminori; Hatano, Naonobu; Honda, Yayoi; Uno, Hitoshi; Journal of Medicinal Chemistry; vol. 34; nb. 2; (1991); p. 593 - 599, View in Reaxys; Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys; Zhao, He; He, Xiaoshu; Thurkauf, Andrew; Hoffman, Diane; Kieltyka, Andrzej; Brodbeck, Robbin; Primus, Renee; Wasley, Jan W.F.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 21; (2002); p. 3111 - 3115, View in Reaxys; Omran, Ziad; Cailly, Thomas; Lescot, Elodie; Santos, Jana Sopkova-De Oliveira; Agondanou, Jean-Hugues; Lisowski, Vincent; Fabis, Frederic; Godard, Anne-Marie; Stiebing, Silvia; Le Flem, Guillaume; Boulouard, Michel; Dauphin, Francois; Dallemagne, Patrick; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 40; nb. 12; (2005); p. 1222 - 1245, View in Reaxys; Patent; Applied Research Systems ARS Holding N.V.; EP1094063; (2001); (A1) English, View in Reaxys; Patent; Ebdrup, Soren; de Jong, Johannes Cornelis; Jacobsen, Poul; Hansen, Holger Claus; Vedso, Per; US2003/166644; (2003); (A1) English, View in Reaxys; Esteve, Cristina; Nueda, Arsenio; Diaz, Jose Luis; Beleta, Jorge; Cardenas, Alvaro; Lozoya, Estrella; Cadavid, Maria Isabel; Loza, Maria Isabel; Ryder, Hamish; Vidal, Bernat; Bioorganic and Medicinal Chemistry Letters; vol. 16; nb. 14; (2006); p. 3642 - 3645, View in Reaxys; Yang, Yinghua; Sun, Lianli; Dong, Shengyi; Wang, Xiaoyu; Yang, Leixiang; Wu, Xiumei; Bai, Hua; Zhao, Yu; Mendeleev Communications; vol. 18; nb. 4; (2008); p. 186 - 187, View in Reaxys; Lee, Hyung Kook; Lee, Yun Suk; Roh, Eun Joo; Rhim, Hyewhon; Lee, Jae Yeol; Shin, Kye Jung; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 15; (2008); p. 4424 - 4427, View in Reaxys; Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys; Borrmann, Thomas; Hinz, Sonja; Bertarelli, Daniela C. G.; Li, Wenjin; Florin, Nicole C.; Scheiff, Anja B.; Mueller, Christa E.; Journal of Medicinal Chemistry; vol. 52; nb. 13; (2009); p. 3994 4006, View in Reaxys; Gitto, Rosaria; De Luca, Laura; Ferro, Stefania; De Grazia, Sara; Di Giorgio, Rosa Maria; Festa, Filomena; De Luca, Grazia; Journal of Heterocyclic Chemistry; vol. 47; nb. 1; (2010); p. 54 - 62, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Wu, Yan; Ma, Long-Xu; Niu, Tian-Wei; Cui, Xun; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 13; (2012); p. 4229 - 4232, View in Reaxys; Wu, Yan; Ma, Long-Xu; Sun, Liang-Peng; Song, Ming-Xia; Cui, Xun; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 3; (2013); p. 757 - 760, View in Reaxys; Wu, Yan; Sun, Liang-Peng; Ma, Long-Xu; Che, Jian; Song, Ming-Xia; Cui, Xun; Piao, Hu-Ri; Chemical Biology and Drug Design; vol. 81; nb. 5; (2013); p. 591 - 599, View in Reaxys; Sadeghzadeh, Masoud; Sheibani, Shahab; Ghandi, Mehdi; Daha, Fariba Johari; Amanlou, Massoud; Arjmand, Mohammad; Hasani Bozcheloie, Abolfazl; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 488 - 497, View in Reaxys; Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys; Han, Sheng Hua; Chen, Jian Xin; Liu, Hong Yan; Zhang, Hai Rong; Ma, Peng Fei; Asian Journal of Chemistry; vol. 27; nb. 4; (2015); p. 1299 1303, View in Reaxys; Pau, Amedeo; Catto, Marco; Pinna, Giovanni; Frau, Simona; Murineddu, Gabriele; Asproni, Battistina; Curzu, Maria M.; Pisani, Leonardo; Leonetti, Francesco; Loza, Maria Isabel; Brea, Jos; Pinna, Grard A.; Carotti, Angelo; ChemMedChem; vol. 10; nb. 6; (2015); p. 1054 - 1070, View in Reaxys; Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys 2 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260, View in Reaxys

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3 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Reaxys ID 618159 View in Reaxys

21/323 CAS Registry Number: 52146-35-7 Chemical Name: 4-(3,4,5-trimethoxyphenylmethyl)piperazine; N-(3,4,5-trimethoxybenzyl)-piperazine; 1-(3,4,5-trimethoxybenzyl)piperazine; 1-(2,3,4-trimethoxybenzyl)piperazine; N-(3,4,5trimethoxybenzyl)piperazine; N-3,4,5-Trimethoxybenzylpiperazine; 3,4,5-trimethoxybenzylpiperazine Linear Structure Formula: C14H22N2O3 Molecular Formula: C14H22N2O3 Molecular Weight: 266.34 Type of Substance: heterocyclic InChI Key: OVEVYSWOILUFMF-UHFFFAOYSA-N Note:

N NH

O O

Substance Label (3) Label References 5{16}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Ferte, Jacques; Kuehnel, Jean-Marc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 - 489, View in Reaxys

Patent-Specific Data (2) Location in Patent References Page/Page column

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys Patent; Scios, Inc.; US6340685; (2002); (B1) English, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

66 - 67

Solvent (Melting Point)

hexane; ethyl acetate

Zlatoidsky; Maliar; European Journal of Medicinal Chemistry; vol. 31; nb. 11; (1996); p. 895 - 899, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties white

Paragraph 0148

yellow

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

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Original Text (NMR Spectroscopy)

1H-NMR (500 MHz, CDCl ): δ 6.46 (s, 2H), 3.75 (s, 6H), 3.72 (s, 3H), 3.30 (s, 2H), 2.78 (t, 3 4H, J=5.0 Hz), 2.29 (br s, 4H), 1.55 (br s, 1H)

Location

Paragraph 0148

Signals [ppm]

6.46; 3.75; 3.72; 3.3; 2.78; 2.29; 1.55

Kind of signal

s, 2H; s, 6H; s, 3H; s, 2H; t, 4H, J=5.0 Hz; br s, 4H; br s, 1H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Original Text (NMR Spectroscopy)

13C-NMR

Location

Paragraph 0148

Signals [ppm]

152.7; 136.4; 133.7; 105.4; 63.6; 60.5; 55.7; 54.2; 45.8

(125 MHz, CDCl3): δ 152.7, 136.4, 133.7, 105.4, 63.6, 60.5, 55.7, 54.2, 45.8

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Comment (Pharmacological Data)

Bioactivities present

Patent; Scios, Inc.; US6340685; (2002); (B1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US4880809; (1989); (A1) English, View in Reaxys; Patent; Hoechst Aktiengesellschaft; US4882329; (1989); (A1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US4937246; (1990); (A1) English, View in Reaxys; Patent; Nippon Chemiphar Co., Ltd.; US5070089; (1991); (A1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; US6166006; (2000); (A1) English, View in Reaxys; Patent; Sankyo Company, Limited; US5192766; (1993); (A1) English, View in Reaxys; Patent; Takeda Chemical Industries, Ltd.; EP318235; (1991); (A3) English, View in Reaxys; Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys; Fukushi; Mabuchi; Itoh; Terashita; Nishikawa; Sugihara; Chemical and

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Pharmaceutical Bulletin; vol. 42; nb. 3; (1994); p. 541 - 550, View in Reaxys; Zlatoidsky; Maliar; European Journal of Medicinal Chemistry; vol. 31; nb. 11; (1996); p. 895 - 899, View in Reaxys; Ferte, Jacques; Kuehnel, JeanMarc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 - 489, View in Reaxys; Patent; Chugai Seiyaku, Kabushiki Kaisha; EP903346; (1999); (A1) English, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Hsu, Danny C.; Roth, Howard S.; West, Diana C.; Botham, Rachel C.; Novotny, Chris J.; Schmid, Steven C.; Hergenrother, Paul J.; ACS Combinatorial Science; vol. 14; nb. 1; (2012); p. 44 - 50, View in Reaxys; Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys; Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys; Ding, Xiao; Li, Yan; Lv, Li; Zhou, Mi; Han, Li; Zhang, Zhengxi; Ba, Qian; Li, Jingquan; Wang, Hui; Liu, Hong; Wang, Renxiao; ChemMedChem; vol. 8; nb. 12; (2013); p. 1986 - 2014, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Kim, Beom-Cheol; Lee, Seung-Hwan; Jang, Mi; Shon, Min Young; Park, Jeong Ho; Bulletin of the Korean Chemical Society; vol. 34; nb. 11; (2013); p. 3322 - 3326, View in Reaxys

Reaxys ID 3713237 View in Reaxys

NH N

22/323 CAS Registry Number: 5321-63-1; 72878-35-4; 110475-31-5 Chemical Name: dihydrochloride salt of 1-benzylpiperazine; 1benzylpiperazine dihydrochloride; N-benzylpiperazine hydrochloride; 1-benzyl-piperazine; dihydrochloride; 1-Benzyl-piperazin; Dihydrochlorid; -4-benzylpiperazine dihydrochloride; N-benzyl-piperazine dihydrochloride Linear Structure Formula: NHC4H8N(CH2C6H5)*2HCl Molecular Formula: C11H16N2*2ClH Molecular Weight: 249.183 Type of Substance: heterocyclic InChI Key: HRSFWIYFGGDGQO-UHFFFAOYSA-N Note:

Cl 2 H

Patent-Specific Data (2) Location in Patent References Page/Page column

Patent; Genentech, Inc.; Babu, Srinivasan; Cheng, Zhigang; Gosselin, Francis; Hidber, Pirmin; Hoffmann, Ursula; Humphries, Theresa; Reents, Reinhard; Tian, Qingping; Yajima, Herbert; US2014/100366; (2014); (A1) English, View in Reaxys Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

247 - 249

Comment (Melting Point)

Decomposition

Valenta, Vladimir; Bartosova, Marie; Protiva, Miroslav; Collection of Czechoslovak Chemical Communications; vol. 46; nb. 5; (1981); p. 1280 - 1287, View in Reaxys 2 of 3

Melting Point [°C]

279 - 280

Comment (Melting Point)

Decomp.nach Sintern bei 253-254grad.

Craig; Young; Org. Synth. Coll. Vol. V; <1973> 88, View in Reaxys; Craig; Journal of the Chemical Society; (1959); p. 3634, View in Reaxys 3 of 3

Melting Point [°C]

253

Solvent (Melting Point)

ethanol

Baltzly et al.; Journal of the American Chemical Society; vol. 66; (1944); p. 263,265, View in Reaxys

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Reaxys ID 785024 View in Reaxys

23/323 CAS Registry Number: 55212-32-3 Chemical Name: 1-(3-methoxy-benzyl)-piperazine; 4-(3-methoxybenzyl)piperazine; 3-methoxy-benzyl-piperazine; 1-(3-methoxybenzyl)piperazine; 1-(3-Methoxybenzyl)piperazine; (3-methoxybenzyl)-piperazine; 3-methoxybenzyl piperazine Linear Structure Formula: C4H8N2HCH2C6H4OCH3 Molecular Formula: C12H18N2O Molecular Weight: 206.288 Type of Substance: heterocyclic InChI Key: BYWNAISVQHRFEE-UHFFFAOYSA-N Note:

H N

Substance Label (2) Label References 8c

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 60; nb. 12; (2007); p. 928 - 933, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Derivative (1) Comment (Derivative) Maleat: F: 122-124grad; Pharmakolog. Eigenschaften Boiling Point (1) Boiling Point [°C] 125 - 130

References Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Pressure (Boiling Point) [Torr]

References

0.5

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Crystal Property Description (2) Colour & Other References Properties yellow

white

Patent; Eisai Co., Ltd.; EP1382603; (2004); (A1) English, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

NMR Spectroscopy (6) 1 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125.8

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

1H-NMR (CDCl3) δ: 2.68 (m, 4H), 3.15(m, 4H), 3.81(s, 3H), 4.20(s, 2H), 6.80-6.90s(m, 3H), 7.24(t, J=8.0Hz, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; Eisai Co., Ltd.; EP1382603; (2004); (A1) English, View in Reaxys 4 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 5 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 6 of 6

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Reaxys ID 6401275 View in Reaxys

24/323 CAS Registry Number: 89292-70-6 Chemical Name: N-(4-cyanobenzyl)piperazine; α-(1-piperazinyl)-p-tolunitrile; 4-(piperazin-1-ylmethyl)benzonitrile; 1-(4-cyano-

N NH N

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benzyl)-piperazine; 1-(4-cyanobenzyl)piperazine; 4-cyanobenzylpiperazine Linear Structure Formula: C12H15N3 Molecular Formula: C12H15N3 Molecular Weight: 201.271 Type of Substance: heterocyclic InChI Key: RPOOHOJBILYQET-UHFFFAOYSA-N Note: Substance Label (1) Label References 20

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys Boiling Point (1) Boiling Point [°C]

References

207 - 209

Patent; American Cyanamid Company; US4421753; (1983); (A1) English, View in Reaxys

Crystal Property Description (2) Colour & Other Location Properties yellow

Page/Page column 110

yellow

References Patent; Teijin Intellectual Property Center Limited; Combichem, Inc.; US6686353; (2004); (B1) English, View in Reaxys Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys

Reaxys ID 523016 View in Reaxys

25/323 CAS Registry Number: 102292-50-2 Chemical Name: 1-(2,6-Dichlorobenzyl)piperazine; 1-(2,6-dichloro-benzyl)-piperazine; 1-(2,6-dichlorobenzyl)piperazine; 2,6-dichlorobenzylpiperazine Linear Structure Formula: C11H14Cl2N2 Molecular Formula: C11H14Cl2N2 Molecular Weight: 245.152

Cl N Cl

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Type of Substance: heterocyclic InChI Key: WQTPGHSKQDVCQQ-UHFFFAOYSA-N Note: Substance Label (2) Label References 5

Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; STOCKWELL, Brent R.; WELSCH, Matthew; WO2015/184349; (2015); (A2) English, View in Reaxys

Patent; Rhone-Poulenc; FRM104; (1960); Chem.Abstr.; vol. 58; nb. 10211g; (1963), View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

Patent; Rhone-Poulenc; FRM104; (1960); Chem.Abstr.; vol. 58; nb. 10211g; (1963), View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1 H NMR (400 MHz, Methanol-d ) δ 7.62 -7.30 (m, 2H), 7.23 (dd, J = 8.7, 7.4 Hz, 1 H), 4 3.74 (s, 2H), 2.92-2.69 (m, 4H), 2.56 (t, J = 4.9 Hz, 4H).

Location

Paragraph 0221

Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; STOCKWELL, Brent R.; WELSCH, Matthew; WO2015/184349; (2015); (A2) English, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

101

Original Text (NMR Spectroscopy)

13C

Location

Paragraph 0221

NMR (101 MHz, MeOD) 136.76, 133.67, 129.18, 128.24, 56.55, 53.41 , 44.95.

Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; STOCKWELL, Brent R.; WELSCH, Matthew; WO2015/184349; (2015); (A2) English, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

high resolution Paragraph 0221 mass spectrometry (HRMS); spectrum

Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; STOCKWELL, Brent R.; WELSCH, Matthew; WO2015/184349; (2015); (A2) English, View in Reaxys

Reaxys ID 10347921 View in Reaxys

26/323 Chemical Name: 1-(2-chloro-6-fluorobenzyl)piperazine Linear Structure Formula: C11H14N2ClF Molecular Formula: C11H14ClFN2 Molecular Weight: 228.697 Type of Substance: heterocyclic InChI Key: PBJVZHBDDDMHIT-UHFFFAOYSA-N Note:

Cl N F

Substance Label (2) Label References 5{7}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 2086, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Crystal Property Description (2) Colour & Other Location Properties white

Paragraph 0094

yellow

NMR Spectroscopy (4)

177/337

2016-05-20 15:00:44

1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR (400 MHz, CDCl ): δ 7.14-7.08 (m, 2H), 6.94-6.86 (m, 1H), 3.62 (d, 2H, J=2.0 3 Hz), 2.78 (t, 4H, J=4.8 Hz), 2.44 (br s, 4H), 1.40 (br s, 1H)

Location

Paragraph 0094

Signals [ppm]

7.08 - 7.14; 6.86 - 6.94; 3.62; 2.78; 2.44; 1.4

Kind of signal

m, 2H; m, 1H; d, 2H, J=2.0 Hz; t, 4H, J=4.8 Hz; br s, 4H; br s, 1H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Original Text (NMR Spectroscopy)

13C-NMR (100 MHz, CDCl ): δ 161.8 (d, J 3 C-F=247.5 Hz), 136.4 (d, JC-F=6.0 Hz), 128.8 (d, JC-F=9.6 Hz), 125.2, 123.6 (d, JC-F=18.0 Hz), 113.7 (d, JC-F=23.3 Hz), 54.0, 52.8, 45.9

Location

Paragraph 0094

Signals [ppm]

161.8; 136.4; 128.8; 125.2; 123.6; 113.7; 54; 52.8; 45.9

Kind of signal

d, J&C-F%=247.5 Hz; d, J&C-F%=6.0 Hz; d, J&C-F%=9.6 Hz; d, J&C-F%=18.0 Hz; d, J&C-F%=23.3 Hz

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

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Comment (Pharmacological Data)

Bioactivities present

Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 - 2086, View in Reaxys; Park, Jung Hwan; Choi, Jin Kyu; Lee, Eunjung; Lee, Jae Kyun; Rhim, Hyewhon; Seo, Seon Hee; Kim, Yoonjee; Doddareddy, Munikumar Reddy; Pae, Ae Nim; Kang, Jahyo; Roh, Eun Joo; Bioorganic and Medicinal Chemistry; vol. 15; nb. 3; (2007); p. 1409 - 1419, View in Reaxys; Patent; Ebdrup, Soren; de Jong, Johannes Cornelis; Jacobsen, Poul; Hansen, Holger Claus; Vedso, Per; US2003/166644; (2003); (A1) English, View in Reaxys; Patent; PIRAMAL LIFE SCIENCES LIMITED; WO2009/16565; (2009); (A1) English, View in Reaxys; Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); (A1) English, View in Reaxys; Jhansi Lakshmi; Suneel Kumar; Nayana, Ravi Shasi; Srinivas Mohan; Bolligarla, Ramababu; Das, Samar K.; Uday Bhanu; Kondapi, Anand K.; Ravikumar, Muttineni; Bioorganic and Medicinal Chemistry; vol. 17; nb. 16; (2009); p. 6040 - 6047, View in Reaxys; Gitto, Rosaria; De Luca, Laura; Ferro, Stefania; De Grazia, Sara; Di Giorgio, Rosa Maria; Festa, Filomena; De Luca, Grazia; Journal of Heterocyclic Chemistry; vol. 47; nb. 1; (2010); p. 54 - 62, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Cai, Mingyi; Li, Zhong; Fan, Feng; Huang, Qingchun; Shao, Xusheng; Song, Gonghua; Journal of Agricultural and Food Chemistry; vol. 58; nb. 5; (2010); p. 2624 - 2629, View in Reaxys; Van Goethem, Sebastiaan; Matheeussen, Veerle; Joossens, Jurgen; Lambeir, Anne-Marie; Chen, Xin; De Meester, Ingrid; Haemers, Achiel; Augustyns, Koen; Van Der Veken, Pieter; Journal of Medicinal Chemistry; vol. 54; nb. 16; (2011); p. 5737 - 5746, View in Reaxys; Hsu, Danny C.; Roth, Howard S.; West, Diana C.; Botham, Rachel C.; Novotny, Chris J.; Schmid, Steven C.; Hergenrother, Paul J.; ACS Combinatorial Science; vol. 14; nb. 1; (2012); p. 44 - 50, View in Reaxys; Jordan, John B.; Poppe, Leszek; Xia, Xiaoyang; Cheng, Alan C.; Sun, Yax; Michelsen, Klaus; Eastwood, Heather; Schnier, Paul D.; Nixey, Thomas; Zhong, Wenge; Journal of Medicinal Chemistry; vol. 55; nb. 2; (2012); p. 678 - 687, View in Reaxys; Park, Jung-Eun; Ji, Wan Keun; Jang, Jae Wan; Pae, Ae Nim; Choi, Keehyun; Choi, Ki Hang; Kang, Jahyo; Roh, Eun Joo; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 6; (2013); p. 1887 - 1890, View in Reaxys; Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 4

Effect (Pharmacological Data)

protein binding affinity

Species or Test-System (Pharmacological Data)

β-site APP cleaving enzyme 1

Kind of Dosing (Pharmacological Data)

title comp. dissolved in non-deuterated DMSO

Further Details (Pharmacological Data)

19F

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

> 1000 μmol/l

nuclear magnetic resonance spectroscopy; dissociation constant (Kd)

Jordan, John B.; Poppe, Leszek; Xia, Xiaoyang; Cheng, Alan C.; Sun, Yax; Michelsen, Klaus; Eastwood, Heather; Schnier, Paul D.; Nixey, Thomas; Zhong, Wenge; Journal of Medicinal Chemistry; vol. 55; nb. 2; (2012); p. 678 - 687, View in Reaxys 3 of 4

Effect (Pharmacological Data)

protein binding affinity

Species or Test-System (Pharmacological Data)

immobilized β-site APP cleaving enzyme 1

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

surface plasmon resonance spectroscopy

Results

molecular target: immobilized β-site APP cleaving enzyme 1

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4 of 4

Effect (Pharmacological Data)

protein binding affinity

Species or Test-System (Pharmacological Data)

immobilized β-site APP cleaving enzyme 1

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

surface plasmon resonance spectroscopy; dissociation constant (Kd)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

> 2000 μmol/l

Reaxys ID 518652 View in Reaxys

27/323 CAS Registry Number: 41717-26-4 Chemical Name: 1-(2,4,6-trimethylbenzyl)-piperazine; N-(2,4,6trimethylbenzyl)-piperazine; 2,4,6-trimethylbenzylpiperazine; 1(2,4,6-trimethylbenzyl)piperazine; N-(2,4,6-trimethylbenzyl)piperazine; 1-(2,4,6-trimethyl-benzyl)-piperazine; 1-(2,4,6-trimethylbenzyl)-piperazin Linear Structure Formula: C14H22N2 Molecular Formula: C14H22N2 Molecular Weight: 218.342 Type of Substance: heterocyclic InChI Key: FOERNUXLFALRDN-UHFFFAOYSA-N Note:

N NH

Substance Label (3) Label References 5n

Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 2086, View in Reaxys

Traxler, Peter; Kump, Wilhelm; Mueller, Klaus; Tosch, Werner; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 552 - 560, View in Reaxys

Protiva et al.; Collection of Czechoslovak Chemical Communications; vol. 41; (1976); p. 1034,1037, 1040, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

122 - 125

Traxler, Peter; Kump, Wilhelm; Mueller, Klaus; Tosch, Werner; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 552 - 560, View in Reaxys 2 of 2

Melting Point [°C]

99 - 100

Solvent (Melting Point)

ethanol

Protiva et al.; Collection of Czechoslovak Chemical Communications; vol. 41; (1976); p. 1034,1037, 1040, View in Reaxys Crystal Property Description (1) Colour & Other References Properties

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yellow

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

Protiva et al.; Collection of Czechoslovak Chemical Communications; vol. 41; (1976); p. 1034,1037, 1040, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; Hoechst Aktiengesellschaft; US4115569; (1978); (A1) English, View in Reaxys; Protiva et al.; Collection of Czechoslovak Chemical Communications; vol. 41; (1976); p. 1034,1037, 1040, View in Reaxys; Traxler, Peter; Kump, Wilhelm; Mueller, Klaus; Tosch, Werner; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 552 560, View in Reaxys; Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys; Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Organic Letters; vol. 8; nb. 10; (2006); p. 2083 - 2086, View in Reaxys; Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys; Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Prastaro, Alessandro; Tetrahedron; vol. 65; nb. 44; (2009); p. 8916 - 8929, View in Reaxys; Gitto, Rosaria; De Luca, Laura; Ferro, Stefania; De Grazia, Sara; Di Giorgio, Rosa Maria; Festa, Filomena; De Luca, Grazia; Journal of Heterocyclic Chemistry; vol. 47; nb. 1; (2010); p. 54 - 62, View in Reaxys; Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414, View in Reaxys; Devegowda, Vani Nelamane; Seo, Seon Hee; Pae, Ae Nim; Nam, Ghilsoo; Choi, Kyung Il; Bulletin of the Korean Chemical Society; vol. 33; nb. 2; (2012); p. 647 - 650, View in Reaxys; Traxler; Kump; Mueller; Tosch; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 552 - 560, View in Reaxys; Pathak, Ashish K.; Pathak, Vibha; Reynolds, Robert C.; ACS Combinatorial Science; vol. 16; nb. 9; (2014); p. 485 - 493, View in Reaxys; Cacchi, Sandro; Fabrizi, Giancarlo; Iazzetti, Antonia; Molinaro, Carmela; Verdiglione, Rosanna; Goggiamani, Antonella; Advanced Synthesis and Catalysis; vol. 357; nb. 5; (2015); p. 1053 - 1059, View in Reaxys 2 of 2

Comment (Pharmacological Data)

hypolipidemic activity, antibacterial activity

Traxler, Peter; Kump, Wilhelm; Mueller, Klaus; Tosch, Werner; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 552 - 560, View in Reaxys

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Reaxys ID 3713234 View in Reaxys

NH N

28/323

CAS Registry Number: 110475-31-5 Chemical Name: N-benzyl-piperazine hydrochloride; 1-benzylpiperazine hydrochloride; N-benzylpiperazine hydrochloride; 4benzylpiperazinium chloride; N-benzylpiperazinium chloride; 1benzyl-piperazine; monohydrochloride; 1-Benzyl-piperazin; Monohydrochlorid Linear Structure Formula: NH(CH2CH2)2NHCH2C6H5 (1+)*Cl(1-) Molecular Formula: C11H17N2*Cl Molecular Weight: 212.722 Type of Substance: heterocyclic InChI Key: HRSFWIYFGGDGQO-UHFFFAOYSA-N Note:

Substance Label (2) Label References 3

Okamura, Naoe; Habay, Stephen A.; Zeng, Joanne; Chamberlin, A. Richard; Reinscheid, Rainer K.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 3; (2008); p. 893 - 901, View in Reaxys

Cao, Sheng-Li; Feng, Yu-Ping; Jiang, Yu-Yang; Liu, Shi-Ying; Ding, Guo-Yu; Li, Run-Tao; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 7; (2005); p. 1915 - 1917, View in Reaxys

Patent-Specific Data (1) References Patent; INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF MEDICAL SCIENCES; EP1783115; (2007); (A1) English, View in Reaxys Melting Point (2) 1 of 2

Melting Point [°C]

167 - 168

Solvent (Melting Point)

ethanol

Craig; Young; Org. Synth. Coll. Vol. V; <1973> 88, View in Reaxys; Craig; Journal of the Chemical Society; (1959); p. 3634, View in Reaxys 2 of 2

Melting Point [°C]

167.5 - 168

Stone et al.; Journal of the Chemical Society; (1958); p. 52, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Original Text (NMR Spectroscopy)

1H-NMR

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

3.05 - 3.67; 4.38; 7.35 - 7.7; 9.61

Kind of signal

9H,m; 2H,br; 5H,m; 1H,br

(DMSO-d6) δ: 3.05-3.67(9H,m), 4.38(2H,br), 7.35-7.70(5H,m), 9.61(1H,br)

Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1104754; (2001); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) electron impact (EI); spectrum

Stojanovska, Natasha; Kelly, Tamsin; Tahtouh, Mark; Beavis, Alison; Fu, Shanlin; Rapid Communications in Mass Spectrometry; vol. 28; nb. 7; (2014); p. 731 - 740, View in Reaxys

Reaxys ID 615075 View in Reaxys

29/323

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CAS Registry Number: 32231-07-5 Chemical Name: 1-(3,4-dimethoxy-benzyl)-piperazine; 1-(3,4dimethoxybenzyl)piperazine; N-3,4-dimethoxybenzylpiperazine Linear Structure Formula: C13H20N2O2 Molecular Formula: C13H20N2O2 Molecular Weight: 236.314 Type of Substance: heterocyclic InChI Key: ONIFCGFFEZDWSC-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 3e

Ferte, Jacques; Kuehnel, Jean-Marc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 - 489, View in Reaxys

Derivative (2) Comment (Derivative)

Derivative

References

1-(3,4-dimethoxybenzyl)-piperazine; hydrochloride

Ferte, Jacques; Kuehnel, Jean-Marc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 489, View in Reaxys

Hydrochlorid: F: 222 - 226 grad

Patent; Servier; FR1191668; (1958); Chem.Abstr.; vol. 56; nb. 1463; (1962), View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

Pesson et al.; European Journal of Medicinal Chemistry; vol. 10; (1975); p. 567,570, View in Reaxys; Boissier et al.; Journal of Medicinal Chemistry; vol. 6; (1963); p. 541,542, View in Reaxys Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

148

Pesson et al.; European Journal of Medicinal Chemistry; vol. 10; (1975); p. 567,570, View in Reaxys

135 - 140

0.5

Boissier et al.; Journal of Medicinal Chemistry; vol. 6; (1963); p. 541,542, View in Reaxys

Reaxys ID 881435 View in Reaxys

30/323 CAS Registry Number: 55037-81-5 Chemical Name: 1-(2-methoxybenzyl)piperazine; 1-(2-methoxy-benzyl)-piperazine; 1-(2-methoxybenzyl)-piperazine; N(2-methoxybenzyl)piperazine Linear Structure Formula: C12H18N2O Molecular Formula: C12H18N2O Molecular Weight: 206.288 Type of Substance: heterocyclic InChI Key: ODXQCAXQWUZKSB-UHFFFAOYSA-N Note:

O N NH

Substance Label (2) Label References 11, R&3%=2OMe

Derivative (1) Comment (Derivative)

References

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Maleat: F: 137-139grad Boiling Point (3) Boiling Point [°C]

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys Pressure (Boiling Point) [Torr]

References

162 - 168

0.01

Patent; Boehringer Mannheim G.m.b.H.; FR2334361; (1977); DE2555290; Chem.Abstr.; vol. 85; nb. 102383, View in Reaxys

134 - 136

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys

124 - 126

1.8

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys

Reaxys ID 5783379 View in Reaxys

31/323 CAS Registry Number: 107049-57-0 Chemical Name: 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride; N-(3,4,5-trimethoxybenzyl)piperazine hydrochloride; 1(3,4,5-trimethoxybenzyl)piperazine Linear Structure Formula: C14H22N2O3*2ClH Molecular Formula: C14H22N2O3*2ClH Molecular Weight: 339.262 Type of Substance: heterocyclic InChI Key: KQVXQLNBEHFJNR-UHFFFAOYSA-N Note:

N NH

Cl 2 H

Substance Label (3) Label References 8a*2HCl

Fukushi; Mabuchi; Itoh; Terashita; Nishikawa; Sugihara; Chemical and Pharmaceutical Bulletin; vol. 42; nb. 3; (1994); p. 541 - 550, View in Reaxys

2, X=3,4,5(OMe)3

Ohtaka; Yoshida; Suzuki; Shimohara; Tajima; Ito; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 12; (1988); p. 4825 - 4833, View in Reaxys

5h (3,4,5-(OMe)3, Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; m=2) nb. 7; (1987); p. 2782 - 2791, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

210 - 211

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Decomposition. Crystallization with 2 Mol(s) HCl

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Reaxys ID 6601415 View in Reaxys

32/323 Chemical Name: 1-[2-(trifluoromethyl)-benzyl]piperazine; 1-(2trifluoromethyl-benzyl)-piperazine; 1-[2-(trifluoromethyl)benzyl]piperazine; 2-trifluoromethylbenzyl piperazine Linear Structure Formula: C12H15F3N2 Molecular Formula: C12H15F3N2 Molecular Weight: 244.26 Type of Substance: heterocyclic InChI Key: MJBOPIADUICXHW-UHFFFAOYSA-N Note:

F F

F N NH

Substance Label (3) Label References

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Patent; PIERRE FABRE MEDICAMENT; LEROY, Isabelle; DUPONT-PASSELAIGUE, Elisabeth; VALEILLE, Karine; RIVAL, Yves; JUNQUERO, Didier; WO2010/6962; (2010); (A1) English, View in Reaxys

amine to 5h

El-Emam, Ali A.; Al-Deeb, Omar A.; Al-Omar, Mohamed; Lehmann, Jochen; Bioorganic and Medicinal Chemistry; vol. 12; nb. 19; (2004); p. 5107 - 5113, View in Reaxys

substrate to A1, B1

Patent-Specific Data (1) References Patent; PIERRE FABRE MEDICAMENT; LEROY, Isabelle; DUPONT-PASSELAIGUE, Elisabeth; VALEILLE, Karine; RIVAL, Yves; JUNQUERO, Didier; WO2010/6962; (2010); (A1) English, View in Reaxys

Reaxys ID 9203010 View in Reaxys

33/323 CAS Registry Number: 340759-27-5 Chemical Name: 1-(4-(trifluoromethoxy)benzyl)piperazine; 1[4-(trifluoromethoxy)benzyl]piperazine; 1-(4-trifluoromethoxybenzyl)piperazine; N-(4-trifluoromethoxy)benzylpiperazine; 1(4-trifluoromethoxy-benzyl)-piperazine Linear Structure Formula: C12H15F3N2O Molecular Formula: C12H15F3N2O Molecular Weight: 260.259 Type of Substance: heterocyclic InChI Key: YYHAJSIKVDIQNW-UHFFFAOYSA-N Note:

N NH

O F

F F

Substance Label (5) Label References 170c

Palmer, Brian D.; Sutherland, Hamish S.; Blaser, Adrian; Kmentova, Iveta; Franzblau, Scott G.; Wan, Baojie; Wang, Yuehong; Ma, Zhenkun; Denny, William A.; Thompson, Andrew M.; Journal of Medicinal Chemistry; vol. 58; nb. 7; (2015); p. 3036 - 3059, View in Reaxys

I-6q

Patent; Shanghai Sun-Sail Pharmaceutical Science and Technology Co., Ltd; WANG, Tiancai; XIN, Ting; FAN, Houxing; CHEN, Yilang; EP2573090; (2013); (A1) English, View in Reaxys; Patent; Wang, Tiancai; Xin, Ting; Fan, Houxing; Chen, Yilang; US2013/143864; (2013); (A1) English, View in Reaxys

5{17}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

11, R&3%=4OCF3

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Patent-Specific Data (2) Location in Patent References Page/Page column

Patent; Shanghai Sun-Sail Pharmaceutical Science and Technology Co., Ltd; WANG, Tiancai; XIN, Ting; FAN, Houxing; CHEN, Yilang; EP2573090; (2013); (A1) English, View in Reaxys; Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Page/Page column

Patent; Wang, Tiancai; Xin, Ting; Fan, Houxing; Chen, Yilang; US2013/143864; (2013); (A1) English, View in Reaxys

Boiling Point (1) Boiling Point [°C] 100 - 105

Pressure (Boiling Point) [Torr]

References

0.05

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties

References

185/337

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yellow

Paragraph 0154

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

NMR Spectroscopy (9) 1 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

NMR (400 MHz, CDCl3): δ 2.39 (s, 4H), 2.78-2.91 (m, 5H), 3.45 (s, 2H), 7.12 (d, J = 8.5 Hz, 2H), 7.31 (d, J = 8.7 Hz, 2H)

Location

Paragraph 0071

Patent; Shanghai Sun-Sail Pharmaceutical Science and Technology Co., Ltd; WANG, Tiancai; XIN, Ting; FAN, Houxing; CHEN, Yilang; EP2573090; (2013); (A1) English, View in Reaxys 2 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Original Text (NMR Spectroscopy)

1H-NMR (500 MHz, CDCl ): 6 7.28 (d, 2H, J=8.0 Hz), 7.08 (d, 2H, J=8.0 Hz), 3.40 (s, 2H), 3 2.81 (t, 4H, J=5.0 Hz), 2.33 (br s, 4H), 1.51 (br s, 1H)

Location

Paragraph 0154

Signals [ppm]

7.08; 3.4; 2.81; 2.33; 1.51

Kind of signal

d, 2H, J=8.0 Hz; s, 2H; t, 4H, J=5.0 Hz; br s, 4H; br s, 1H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 3 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Original Text (NMR Spectroscopy)

13C-NMR

Location

Paragraph 0154

Signals [ppm]

148; 136.9; 130.1; 120.5; 120.3; 62.6; 54.3; 45.9

Kind of signal

q, J&C-F%=255.5 Hz

(125 MHz, CDCl3): δ 148.0, 136.9, 130.1, 120.5, 120.3 (q, JC-F=255.5 Hz), 62.6, 54.3, 45.9

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 4 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

375

Original Text (NMR Spectroscopy)

19F-NMR

Location

Paragraph 0154

Signals [ppm]

-58.4

(375 MHz, CDCl3): -58.4

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 5 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

NMR (400 MHz, CDCl3): δ2.39 (s, 4H), 2.78-2.91 (m, 5H), 3.45 (s, 2H), 7.12 (d, J=8.5 Hz, 2H), 7.31 (d, J=8.7 Hz, 2H)

Location

Paragraph 0129

Patent; Wang, Tiancai; Xin, Ting; Fan, Houxing; Chen, Yilang; US2013/143864; (2013); (A1) English, View in Reaxys 6 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 7 of 9

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 8 of 9

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

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9 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Reaxys ID 9260189 View in Reaxys

34/323 CAS Registry Number: 298705-59-6 Chemical Name: 1-(2-bromo-benzyl)-piperazine; 1-(2-bromobenzyl)piperazine; 1-(2-Bromobenzyl)piperazine Linear Structure Formula: C11H15BrN2 Molecular Formula: C11H15BrN2 Molecular Weight: 255.157 Type of Substance: heterocyclic InChI Key: XVHSZKUVDNZYDF-UHFFFAOYSA-N Note:

Br N NH

Substance Label (2) Label References 23

Bolognesi, Maria Laura; Cavalli, Andrea; Andrisano, Vincenza; Bartolini, Manuela; Banzi, Rita; Antonello, Alessandra; Rosini, Michela; Melchiorre, Carlo; Farmaco; vol. 58; nb. 9; (2003); p. 917 - 928, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product Boiling Point (1) Boiling Point [°C] 108 - 112

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys Pressure (Boiling Point) [Torr]

References

0.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Bolognesi, Maria Laura; Cavalli, Andrea; Andrisano, Vincenza; Bartolini, Manuela; Banzi, Rita; Antonello, Alessandra; Rosini, Michela; Melchiorre, Carlo; Farmaco; vol. 58; nb. 9; (2003); p. 917 - 928, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy)

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Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 4 of 4

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Reaxys ID 4217341 View in Reaxys

35/323 CAS Registry Number: 127881-54-3 Chemical Name: trimetazidine; TMZ HCl; 1-(2,3,4-trimethoxybenzyl)piperazine dihydrochloride; 1-(2,3,4-trimethoxybenzyl)piperazine hydrochloride; (2,3,4-trimethoxybenzyl)piperazine hydrochloride; 1-(2,3,4-trimethyloxybenzyl)piperazine hydrochloride; trimetazidine hydrochloride Linear Structure Formula: C14H22N2O3*ClH Molecular Formula: C14H22N2O3*ClH Molecular Weight: 302.801 Type of Substance: heterocyclic InChI Key: QHWBCHACIJBSFV-UHFFFAOYSA-N Note:

O O

Substance Label (2) Label References TMZ

Girgin, Ferhan; Karaoglu, Oender; Erkus, Muhan; Tuezuen, Sevgi; Oezuetemiz, Oemer; Dincer, Cigdem; Batur, Yuecel; Tanyalcin, Tijen; Journal of Toxicology and Environmental Health - Part A; vol. 59; nb. 8; (2000); p. 641 - 652, View in Reaxys

Yoshino, Kohichiro; Goto, Katsumi; Yoshiizumi, Kazuya; Morita, Tominori; Tsukamoto, Goro; Journal of Medicinal Chemistry; vol. 33; nb. 8; (1990); p. 2192 - 2196, View in Reaxys

Patent-Specific Data (1) Location in Patent References Claim

Patent; SRCHEM Incorporated; US5288503; (1994); (A1) English, View in Reaxys; Patent; Nippon Shinyaju Co., Ltd.; US5811547; (1998); (A1) English, View in Reaxys

Density (4) 1 of 4

Density [g·cm-3]

0.992232

Measurement Temperature [°C]

39.99

Gen, Lütfi; Journal of Molecular Liquids; vol. 208; (2015); p. 165 - 169, View in Reaxys

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2 of 4

Density [g·cm-3]

0.99406

Measurement Temperature [°C]

34.99

Gen, Lütfi; Journal of Molecular Liquids; vol. 208; (2015); p. 165 - 169, View in Reaxys 3 of 4

Density [g·cm-3]

0.99567

Measurement Temperature [°C]

29.99

Gen, Lütfi; Journal of Molecular Liquids; vol. 208; (2015); p. 165 - 169, View in Reaxys 4 of 4

Density [g·cm-3]

0.997068

Measurement Temperature [°C]

24.99

Gen, Lütfi; Journal of Molecular Liquids; vol. 208; (2015); p. 165 - 169, View in Reaxys Mechanical Properties (1) Description (MeReferences chanical Properties) Compressibility

Gen, Lütfi; Journal of Molecular Liquids; vol. 208; (2015); p. 165 - 169, View in Reaxys

Pharmacological Data (13) 1 of 13

Comment (Pharmacological Data)

Bioactivities present

Patent; SRCHEM Incorporated; US5288503; (1994); (A1) English, View in Reaxys; Patent; Nippon Shinyaju Co., Ltd.; US5811547; (1998); (A1) English, View in Reaxys; Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys; Yoshino, Kohichiro; Goto, Katsumi; Yoshiizumi, Kazuya; Morita, Tominori; Tsukamoto, Goro; Journal of Medicinal Chemistry; vol. 33; nb. 8; (1990); p. 2192 - 2196, View in Reaxys; Aritomi; Ueda; Nishimura; Chemical and Pharmaceutical Bulletin; vol. 28; nb. 11; (1980); p. 3163 - 3171, View in Reaxys; Girgin, Ferhan; Karaoglu, Oender; Erkus, Muhan; Tuezuen, Sevgi; Oezuetemiz, Oemer; Dincer, Cigdem; Batur, Yuecel; Tanyalcin, Tijen; Journal of Toxicology and Environmental Health - Part A; vol. 59; nb. 8; (2000); p. 641 - 652, View in Reaxys; Patent; Gu, Shuhua; Mei, Changlin; Su, Dingfeng; Du, Juan; Fan, Rong; US2009/12096; (2009); (A1) English, View in Reaxys; Gen, Lütfi; Journal of Molecular Liquids; vol. 208; (2015); p. 165 - 169, View in Reaxys 2 of 13

Effect (Pharmacological Data)

antioxidant

Endpoint of Effect (Pharmacological Data)

GSH status, macroscopic and microscopic score in colon

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

rectal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dosing 1 h before TNBS, then once daily for 7 d

Method (Pharmacological Data)

rats weighing 180-220 g, n=10; TNBS-induced chronic colitis; title comp. adm. for 7 d; rats killed on day 8; colonic segments isol.; estim. of title comp. effect on TNBS-induced GSH status and histopathologic damages in rat colon; 0.9 percent saline as control

Further Details (Pharmacological Data)

trinitrobenzenesulfonic acid (TNBS, 30/mg/kg, in 0.25 ml of 50 percent EtOH, intrarectally, single adm.); control: 0.9 percent saline, 1 ml/rat, intrarectally, once a day for 7 d; GSH status: total GSH (tGSH), reduced GSH (GSH), oxidized GSH (GSSG) and GSH/GSSG ratio

Comment (Pharmacological Data)

No effect

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3 of 13

Effect (Pharmacological Data)

antioxidant

Endpoint of Effect (Pharmacological Data)

GSH status, macroscopic and microscopic score in colon

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dosing 1 h before TNBS, then once daily for 7 d

Method (Pharmacological Data)

Further Details (Pharmacological Data)

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

antioxidant

Endpoint of Effect (Pharmacological Data)

GSH status, microscopic and macroscopic damages in colon

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

rectal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dosing 1 h before saline, then once daily for 7 d

Method (Pharmacological Data)

rats weighing 180-220 g, n=10; treated with saline intrarectally; title comp. adm. for 7 d; rats killed on day 8; colonic segments isolated; estim. of title comp. effect on GSH status and histopathological alterations in rat colon

Further Details (Pharmacological Data)

saline-induced colitis: 0.9 percent saline, 1 ml/rat, intrarectally, single adm.; GSH status: total GSH (tGSH), reduced GSH (GSH), oxidized GSH (GSSG) and GSH/GSSG ratio

Results

sign. increase in tGSH, GSH, and GSH/GSSG ratio and decrease in GSSG; no effect on macro- and microscopic colonic status compared to control rats (saline only)

Effect (Pharmacological Data)

antioxidant

Endpoint of Effect (Pharmacological Data)

GSH status, microscopic and macroscopic damages in colon

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

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Route of Application

intraperitoneal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dosing 1 h before saline, then once daily for 7 d

Method (Pharmacological Data)

Further Details (Pharmacological Data)

saline-induced colitis: 0.9 percent saline, 1 ml/rat, intrarectally, single adm.; GSH status: total GSH (tGSH), reduced GSH (GSH), oxidized GSH (GSSG) and GSH/GSSG ratio

Results

sign. increase in tGSH, GSH, and GSH/GSSG ratio and decrease in GSSG; no effect on macro- and microscopic colonic status compared to control rats (saline only)

Effect (Pharmacological Data)

enzyme; examination of

Endpoint of Effect (Pharmacological Data)

MPO level in colon mucosa

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

rectal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dosing 1 h before TNBS + ethanol and then once daily for 7 d

Method (Pharmacological Data)

rats weighing 180-220 g, n=10; TNBS-induced chronic colitis (30 mg/kg, intrarectally, in 0.25 ml of 50 percent EtOH, single adm.); title comp. adm. for 7 d; rats killed on day 8; colonic segments isolated; MPO level meas.

Further Details (Pharmacological Data)

MPO: myeloperoxidase; TNBS - 2,4,6-trinitrosulfonic acid; title comp. effect on TNBS-induced MPO level estim.

Results

diagram representation

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

enzyme; examination of

Endpoint of Effect (Pharmacological Data)

MPO level in colon mucosa

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dosing 1 h before TNBS + ethanol and then once daily for 7 d

Method (Pharmacological Data)

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Further Details (Pharmacological Data)

MPO: myeloperoxidase; TNBS - 2,4,6-trinitrosulfonic acid; title comp. effect on TNBS-induced MPO level estim.

Results

diagram representation

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

enzyme; examination of

Endpoint of Effect (Pharmacological Data)

MPO level in colon mucosa

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dosing 1 h before saline adm. and then once daily for 7 d

Method (Pharmacological Data)

rats weighing 180-220 g, n=10; saline adm. (0.9 percent, 1 ml/rat, for 7 d, intrarectally); title comp. adm. for 7 d; rats killed on day 8; colonic segments isolated; MPO level meas.

Further Details (Pharmacological Data)

MPO: myeloperoxidase; effect of title comp. on colonic MPO level

Results

sign. decrease in MPO level compared to control rats (saline only); diagram representation

Effect (Pharmacological Data)

enzyme; examination of

Endpoint of Effect (Pharmacological Data)

MPO level in colon mucosa

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

rectal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dosing 1 h before saline adm. and then once daily for 7 d

Method (Pharmacological Data)

rats weighing 180-220 g, n=10; saline adm. (0.9 percent, 1 ml/rat, for 7 d, intrarectally); title comp. adm. for 7 d; rats killed on day 8; colonic segments isolated; MPO level meas.

Further Details (Pharmacological Data)

MPO: myeloperoxidase; effect of title comp. on colonic MPO level

Results

sign. decrease in MPO level compared to control rats (saline only); diagram representation

Effect (Pharmacological Data)

antioxidant

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Endpoint of Effect (Pharmacological Data)

malondialdehyde level in colonic tissue

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dose 1 h before TNBS, then once daily for 7 d

Method (Pharmacological Data)

rats weighing 180-220 g, n=10; TNBS-induced chronic colitis; title comp. adm. for 7 d; rats killed on day 8; colonic segments isolated; MDA level meas. spectrophotometrically as thiobarbituric acid reactive substances

Further Details (Pharmacological Data)

MDA: malonedialdehyde; TNBS: trinitrobenzenesulfonic acid (30/mg/kg, in 0.25 ml of 50 percent EtOH, intrarectally, single adm.); title comp. effect on TNBS-altered MDA level

Results

marked decrease in TNBS-induced MDA level; diagram representation

Effect (Pharmacological Data)

colonic irritation

Endpoint of Effect (Pharmacological Data)

malondialdehyde level in colonic tissue

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

rectal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dose 1 h before TNBS, then once daily for 7 d

Method (Pharmacological Data)

Further Details (Pharmacological Data)

MDA: malonedialdehyde; TNBS: trinitrobenzenesulfonic acid (30/mg/kg, in 0.25 ml of 50 percent EtOH, intrarectally, single adm.); title comp. effect on TNBS-altered MDA level

Results

sign. increase in MDA level compared with control (saline) and TNBS alone; diagram representation

Effect (Pharmacological Data)

colonic irritation

Endpoint of Effect (Pharmacological Data)

MDA level in colonic tissue

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

rectal

Concentration (Pharmacological Data)

5 mg/kg

194/337

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Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dosing 1 h before saline adm. and then once daily for 7 d

Method (Pharmacological Data)

rats weighing 180-220 g, n=10; saline adm. (0.9 percent, 1 ml/rat, for 7 d, intrarectally); title comp. adm. for 7 d; rats killed on day 8; colonic segments isolated; MDA level meas. spectrophotometrically as thiobarbituric acid reactive substances

Further Details (Pharmacological Data)

MDA: malonedialdehyde; effect of title comp. on colonic MDA level

Results

sign. increase in MDA level compared to control rats (saline only); diagram representation

Effect (Pharmacological Data)

colonic irritation

Endpoint of Effect (Pharmacological Data)

MDA level in colonic tissue

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

5 mg/kg/day, first dosing 1 h before saline adm. and then once daily for 7 d

Method (Pharmacological Data)

Further Details (Pharmacological Data)

MDA: malonedialdehyde; effect of title comp. on colonic MDA level

Results

sign. increase in MDA level compared to control rats (saline only); diagram representation

References Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Fibromyalgia syn- Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, drome (FMS) View in Reaxys Chronic fatigue syndrome (CFS)

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Myofascial pain syndrome (MPS)

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Gulf War syndrome (GWS)

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Rheumatic condition

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Trigger point pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Trigger point tenderness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Depression

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

195/337

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Dizziness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Impaired concentration

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Irritable bowel syndrome

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Headache

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Fatigue

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Sleep disturbance Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys Chronic headaches

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Sleep disorder

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Jaw pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Cognitive impairment

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Memory impairment

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Post-exertional malaise

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Muscle pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Morning stiffness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Menstrual cramping

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Numbness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Tingling sensations

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Skin sensitivities

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Chemical sensitivities

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Balance problems Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys Stiffness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Fluid retention

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

weight loss

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Skin rashes

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Chronic fevers

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Peripheral numbness

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

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Joint pain

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Coronary heart disease

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Stable angina

Patent; GENERICS [UK] LIMITED; MINTAILS LIMITED; WO2007/116074; (2007); (A1) English, View in Reaxys

Reaxys ID 13676403 View in Reaxys

36/323 Chemical Name: 4-(2,5-difluorobenzyl)piperazine; 2,5-Difluorobenzylpiperazine; 1-(2,5-difluorobenzyl)piperazine Linear Structure Formula: C11H14F2N2 Molecular Formula: C11H14F2N2 Molecular Weight: 212.242 InChI Key: VTKXPESKKMTHJP-UHFFFAOYSA-N Note:

F N NH F

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H NMR (300 MHz, CDCl ) δ7.36-7.22 (m, 1H), 7.10-6.90 (m, 3H), 3.55 (s, 2H), 3.30-3.10 3 9m, 4H), 2.85-2.65 (m, 4H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

7.22 - 7.36; 6.9 - 7.1; 3.55; 3.1 - 3.3; 9; 4

Kind of signal

m, 1H; m, 3H; s, 2H

Patent; Molecular Geriatrics Corporation; US6214994; (2001); (B1) English, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

7.22 - 7.36; 6.9 - 7.1; 3.55; 3.1 - 3.3; 9; 4

Kind of signal

m, 1 H; m, 3 H; s, 2 H

H NMR (300 MHz, CDCl3) δ 7.36-7.22 (m, 1 H), 7.10-6.90 (m, 3 H), 3.55 (s, 2 H), 3.30-3.10 9m, 4 H), 2.85-2.65 (m, 4 H)

Patent; Molecular Geriatrics Corporation; US5658909; (1997); (A1) English, View in Reaxys 3 of 3

Solvents (NMR Spectro- CDCl3 scopy)

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Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

NMR (300 MHz, CDCl3) δ 7.36-7.22 (m, 1 H), 7.10-6.90 (m, 3 H), 3.55 (s, 2 H), 3.30-3.10 9m, 4 H), 2.85-2.65 (m, 4 H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

7.22 - 7.36; 6.9 - 7.1; 3.55; 3.1 - 3.3; 9; 4

Kind of signal

m, 1 H; m, 3 H; s, 2 H

Patent; Molecular Geriatrics Corporation; US5693804; (1997); (A1) English, View in Reaxys

Reaxys ID 9259790 View in Reaxys

37/323 CAS Registry Number: 423154-81-8 Chemical Name: 1-(3-bromobenzyl)piperazine Linear Structure Formula: C11H15BrN2 Molecular Formula: C11H15BrN2 Molecular Weight: 255.157 Type of Substance: heterocyclic InChI Key: TUKZQYYLUARXKM-UHFFFAOYSA-N Note:

H N

Substance Label (2) Label References 15

Patent; GLAXO GROUP LIMITED; WO2005/87236; (2005); (A1) English, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product Boiling Point (1) Boiling Point [°C] 110 - 115

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys Pressure (Boiling Point) [Torr]

References

0.04

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties light-brown

Patent; GLAXO GROUP LIMITED; WO2005/87236; (2005); (A1) English, View in Reaxys

NMR Spectroscopy (4) 1 of 4

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

;'H NMR, 5 (CDCI3) 1.84 (br s), 2.41 and 2.89 (each 4H, m) 3.45 (2H, s) 7.10-7. 49 (4H, m).

Comment (NMR Spectroscopy)

Signals given

Patent; GLAXO GROUP LIMITED; WO2005/87236; (2005); (A1) English, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 4 of 4

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

References

ESI (Electrospray ionisation)

Patent; GLAXO GROUP LIMITED; WO2005/87236; (2005); (A1) English, View in Reaxys

Molecular peak

Reaxys ID 9263322 View in Reaxys

38/323 CAS Registry Number: 194233-47-1 Chemical Name: 1-(2,5-dichlorobenzyl)-piperazine; 1-(2,5-dichlorobenzyl)piperazine Linear Structure Formula: C11H14Cl2N2 Molecular Formula: C11H14Cl2N2 Molecular Weight: 245.152 Type of Substance: heterocyclic InChI Key: OCDKHNIROLGDKR-UHFFFAOYSA-N Note:

Cl N NH Cl

Patent-Specific Data (1) References Patent; RECORDATI S.A.; RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA S.p.a.; EP1000047; (2003); (B1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

1H-NMR (CDCl3, δ): 7.50 (d, 1H, aromatic H6), 7.26 (d, 1H, aromatic H3), 7.14 (dd, 1H, aromatic H4), 3.55 (s, 2H, benzyl CH2), 3.00-2.85 (m, 4H, piperazine protons), 2.55-2.48 (m, 4H, piperazine protons), 1.76 (s, 1H, NH)

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Comment (NMR Spectroscopy)

Signals given

Patent; RECORDATI S.A.; RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA S.p.a.; EP1000047; (2003); (B1) English, View in Reaxys

Reaxys ID 10163311 View in Reaxys

39/323 Chemical Name: 1-(3-nitrobenzyl)piperazine; 1-(3-Nitrobenzyl)piperazine; CB-29 Linear Structure Formula: C11H15N3O2 Molecular Formula: C11H15N3O2 Molecular Weight: 221.259 Type of Substance: heterocyclic InChI Key: NPEYPFYIBGIHQW-UHFFFAOYSA-N Note:

O O

N NH

Substance Label (2) Label References 18

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

Compound 83; Compound ID 5881261

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties yellow

supporting information

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Description (IR Spectroscopy)

Bands

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Location

supporting information

Comment (IR Spectroscopy)

neat liquid

Peterson, Quinn P.; Hsu, Danny C.; Goode, David R.; Novotny, Chris J.; Totten, Ryan K.; Hergenrother, Paul J.; Journal of Medicinal Chemistry; vol. 52; nb. 18; (2009); p. 5721 - 5731, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry) CID (collision-induced dissociation); ESI (Electrospray ionisation); IT (ion trap); Spectrum HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum

References Chai, Yunfeng; Sun, Hezhi; Pan, Yuanjiang; Sun, Cuirong; Journal of the American Society for Mass Spectrometry; vol. 22; nb. 9; (2011); p. 1526 - 1533, View in Reaxys

supporting information

Peterson, Quinn P.; Hsu, Danny C.; Goode, David R.; Novotny, Chris J.; Totten, Ryan K.; Hergenrother, Paul J.; Journal of Medicinal Chemistry; vol. 52; nb. 18; (2009); p. 5721 - 5731, View in Reaxys

Pharmacological Data (4) 1 of 4

Comment (Pharmacological Data)

Bioactivities present

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys; Omran, Ziad; Cailly, Thomas; Lescot, Elodie; Santos, Jana Sopkova-De Oliveira; Agondanou, Jean-Hugues; Lisowski, Vincent; Fabis, Frederic; Godard, Anne-Marie; Stiebing, Silvia; Le Flem, Guillaume; Boulouard, Michel; Dauphin, Francois; Dallemagne, Patrick; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 40; nb. 12; (2005); p. 1222 - 1245, View in Reaxys; Peterson, Quinn P.; Hsu, Danny C.; Goode, David R.; Novotny, Chris J.; Totten, Ryan K.; Hergenrother, Paul J.; Journal of Medicinal Chemistry; vol. 52; nb. 18; (2009); p. 5721 5731, View in Reaxys; Chai, Yunfeng; Sun, Hezhi; Pan, Yuanjiang; Sun, Cuirong; Journal of the American Society for Mass Spectrometry; vol. 22; nb. 9; (2011); p. 1526 - 1533, View in Reaxys; Patent; JANSSEN PHARMACEUTICA NV; DIELS, Gaston, Stanislas, Marcella; SCHOENTJES, Bruno; VERSELE, Matthias, Luc, Aimé; BERTHELOT, Didier, Jean-Claude; WILLEMS, Marc; VIELLEVOYE, Marcel; EMBRECHTS, Werner, Constant, Johan; WROBLOWSKI, Berthold; MEERPOEL, Lieven; WO2015/150555; (2015); (A1) English, View in Reaxys; Patent; JANSSEN PHARMACEUTICA NV; DIELS, Gaston, Stanislas, Marcella; SCHOENTJES, Bruno; VERSELE, Matthias, Luc, Aimé; BERTHELOT, Didier, Jean-Claude; WILLEMS, Marc; VIELLEVOYE, Marcel; SOMMEN, François, Maria; WROBLOWSKI, Berthold; MEERPOEL, Lieven; WO2015/150557; (2015); (A1) English, View in Reaxys; Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys 2 of 4

Effect (Pharmacological Data)

anti-microbial

Species or Test-System (Pharmacological Data)

Pseudomonas aeruginosa PA01

Method (Pharmacological Data)

[93 ] Bacterial strains, plasmids and media.[94] Pseudomonas aeruginosa MPAOl was obtained from the University of Washington, Genome Center, Seattle, WA. The pa-ΗO and nm-HO genes cloned into pET21a were transformed into E. coli strain BL21 (DE3) pLysS [F" ompT hsdS^ (ΓE 'ΓUB ") gal dcm (DE3)] for protein expression as previously described 25' 53. Luria Bertani (LB) broth was used for growth and maintenance of E. coli strains in the presence of ampicillin, 100 μg/ml. MinA minimal medium plates were used for growth and maintenance of the MPAOl strain. Succinate minimal (SM) media (pH 7.0) was used for all growth studies oP. aeruginosa. [95] General methods.[96] A stock solution of hemoglobin was prepared in SM media (pH 7.0). Pyoverdine was purified as described by Dr. Jean-Marie Meyer, Department de Genetique Moleculaire, Denomique et Micorbiologie, Strasbourg, France. A single colony of MPAOl was grown in 10 ml LB-media for 16 hrs. The culture was pelleted by centrifugation (4,000 rpm for 10 min at 40C) and re-suspended in 1 ml of SM media. A 1 : 1000 dilution was made into 1 L of SM and grown for 24 hrs. Subsequently, the culture was harvested by centrifugation in a Beckman JA-10 rotor (10,000 rpm for 15 min) at 40C and the resulting supernatant was acidified to pH 6.0. The acidified supernatant was applied to an Amberlite XAD-4 (Sigma) column (2.5 x 10 cm) previously washed with 50percent methanol (MeOH) and extensively equilibrated with double distilled water. The column was washed with 3 volumes of water, and the pigment was eluted in 50percent MeOH. The eluate was evaporated to dryness under vacuum and re-suspended in 5 ml of water. The concentration of iron-free pyoverdine (1 : 1000) was

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determined in 0.5 M acetic acid-sodium acetate buffer, pH 5.0 from the extinction coefficient at 340 nm of εmax = 16,500 M"1 cm"1 m.[97] A stock solution of FeCl3 (4.5 mM) was prepared in 0.5 M sodium citrate for reconstitution of the holo-pyoverdine. A 2.5 μM stock solution of apo-pyoverdine was reconstituted with FeCl3 at a 1 : 1 ratio to yield the resulting holo-pyoverdine. All inhibitors were prepared by solubilization in dimethyl sulfoxide (DMSO) and added directly to the cultures or purified protein in the concentrations stated. MPAOl growth inhibition assays were carried out in SM media with a range of inhibitor concentrations from 250-1500 μM. Location

Page/Page column 21; 86-87; 115

Comment (Pharmacological Data)

No effect

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys 3 of 4

Effect (Pharmacological Data)

neisseria meningitidis heme oxygenase (Nm-HO); binding affinity to

Species or Test-System (Pharmacological Data)

Neisseria meningitidis heme oxygenase (Nm-HO) of Neisseria meningitidis

Method (Pharmacological Data)

Measurement of the binding affinities (KD) of the selected compounds. [101] The binding of the compounds to apo-"w-HO and apo-pα-HO were obtained by fluorescence titrations. Measurements were made on an ISS PC-I spectrofluorimeter configured in the L format. Full excitation/emission spectra were recorded for each compound to determine the intrinsic fluorescence properties of the selected inhibitors. All experiments with either apo-"wHO or apo-pα-HO were carried out in 20 mM Tris-HCl (pH 7.5). The titrations were performed by addition of increasing concentrations of the selected compound (0.05-500 μM) while maintaining the apo-"w-HO and apo-pα-HO protein concentrations at 1 μM. The optimal excitation wavelength for the apo-proteins was 295 nm and the fluorescence emission was monitored from 300 to 500 nm. The dissociation constants (K) were calculated from reciprocal plots of 1/ΔA vs 1/[I] where the decrease in fluorescence,. ΔA, at the maximum emission (330 nm), represents the fraction of occupied binding sites, and [I] the concentration of the inhibitor. The slope of the curve equals the KD as described by the equilibrium equation (1):[P] + [ I ] ^=^ [PI] (1)KD = [PI][P] + [ I ]The binding affinities (KD) of each compound for both nm-HO and pa-HO were measured and calculated based on an average of three separate experiments.

Results

title compound treatment showed binding affinity to pseudomonas aeruginosa heme oxygenase (pa-HO)

Location

Page/Page column 21-22; 88-89

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys 4 of 4

Effect (Pharmacological Data)

pseudomonas aeruginosa heme oxygenase (pa-HO); binding affinity to

Species or Test-System (Pharmacological Data)

Pseudomonas aeruginosa heme oxygenase (pa-HO) of Pseudomonas aeruginosa

Method (Pharmacological Data)

Results

title compound treatment showed binding affinity to pseudomonas aeruginosa heme oxygenase (pa-HO)

Location

Page/Page column 88-89; 115

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Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys Use (19) Use Pattern microbial heme oxygenase inhibitor; heme utilization inhibitor

References Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Microbial infection Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys Bioremediation

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Infectious disease Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys Ameliorate the Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys adverse impact of an undesired organism requiring heme oxygenase (HO) Conditions asso- Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys ciated with inflammation Inflammation in the central nervous system (CNS)

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Cancers that have a microbial origin

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Mycobacterium infection

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Mycobacterium tuberculosis (tuberculosis)

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

sepsis

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Methicillin-resistant Staphylococcus aureus (MRSA)

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Nosocomial infec- Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys tions Malaria

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Cystic fibrosis

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Fungal infection

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

viral infection

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Protist infection

Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Bacterial infection Patent; UNIVERSITY OF MARYLAND, BALTIMORE; WO2008/14266; (2008); (A2) English, View in Reaxys

Reaxys ID 13415048 View in Reaxys

40/323 CAS Registry Number: 220213-15-0 Chemical Name: 4-Piperazin-1-ylmethyl-benzoic acid Linear Structure Formula: C12H16N2O2 Molecular Formula: C12H16N2O2 Molecular Weight: 220.271 InChI Key: PNRGRAZXFRLSJE-UHFFFAOYSA-N

N HO

NH O

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Note:

Reaxys ID 15884212 View in Reaxys

41/323 CAS Registry Number: 204013-06-9 Chemical Name: 1-(2,4-difluorobenzyl)piperazine Linear Structure Formula: C11H14F2N2 Molecular Formula: C11H14F2N2 Molecular Weight: 212.242 InChI Key: GGARUFCQRZCXHK-UHFFFAOYSA-N Note:

F N NH

Patent-Specific Data (2) Prophetic ComLocation in Patent References pound Page/Page column

Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Brown, Jason; Hitchcock, Steve; Hopkins, Maria; Kikuchi, Shota; Monenschein, Holger; Reichard, Holly; Schleicher, Kristin; Sun, Huikai; Macklin, Todd; US2015/175602; (2015); (A1) English, View in Reaxys

prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Mass Spectrometry (3) Description (Mass Location Spectrometry)

References

electrospray ionisation (ESI); spectrum

Paragraph 0163

electrospray ionisation (ESI); spectrum

Paragraph 0142

Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; HITCHCOCK, Stephen; HOPKINS, Maria; KIKUCHI, Shota; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; MACKLIN, Todd; WO2015/123505; (2015); (A1) English, View in Reaxys

electrospray ionisation (ESI); spectrum

Paragraph 0145

Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; ADAMS, Mark E.; BROWN, Jason W.; HITCHCOCK, Stephen; HOPKINS, Maria; KIKUCHI, Shota; LAM, Betty; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; WO2015/123533; (2015); (A1) English, View in Reaxys

Reaxys ID 152125 View in Reaxys

42/323 CAS Registry Number: 23145-95-1 Chemical Name: 1-(4-isopropylbenzyl)piperazine; 1-(p-Isopropylbenzyl)piperazine; 1-(4-isopropyl-benzyl)-piperazine; 1-(4Isopropyl-benzyl)-piperazin Linear Structure Formula: C14H22N2 Molecular Formula: C14H22N2 Molecular Weight: 218.342 Type of Substance: heterocyclic InChI Key: HOBCRUDGINOFNV-UHFFFAOYSA-N Note:

NH N

Substance Label (3) Label References 5{19}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

11, R&3%=4isoPr

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Carpino, Louis A.; Mansour, E. M. E.; Knapczyk, Jerome; Journal of Organic Chemistry; vol. 48; nb. 5; (1983); p. 666 - 669, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Derivative (1) Derivative

References

1-(p-Isopropylbenzyl)piperazine hydrochloride Boiling Point (2) Boiling Point [°C]

Carpino, Louis A.; Mansour, E. M. E.; Knapczyk, Jerome; Journal of Organic Chemistry; vol. 48; nb. 5; (1983); p. 666 - 669, View in Reaxys

Pressure (Boiling Point) [Torr]

References

146 - 148

2.8

Carpino, Louis A.; Mansour, E. M. E.; Knapczyk, Jerome; Journal of Organic Chemistry; vol. 48; nb. 5; (1983); p. 666 - 669, View in Reaxys

155 - 157

8-9

Patent; Monsanto Chem. Co.; US2451645; (1947), View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties white

Paragraph 0166

References Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Original Text (NMR Spectroscopy)

1H-NMR (500 MHz, CDCl ): δ 7.21 (d, 2H, J=8.0 Hz), 7.14 (d, 2H, J=8.0 Hz), 4.15 (q, 2H, 3 J=7.0 Hz), 3.43 (s, 2H), 2.89-2.84 (m, 5H), 2.39 (br s, 4H), 2.25 (br s, 1H), 1.22 (d, 6H, J=6.5 Hz)

Location

Paragraph 0166

Signals [ppm]

7.21; 7.14; 4.15; 3.43; 2.84 - 2.89; 2.39; 2.25; 1.22

Kind of signal

d, 2H, J=8.0 Hz; d, 2H, J=8.0 Hz; q, 2H, J=7.0 Hz; s, 2H; m, 5H; br s, 4H; br s, 1H; d, 6H, J=6.5 Hz

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Original Text (NMR Spectroscopy)

13C-NMR

Location

Paragraph 0166

Signals [ppm]

147.3; 135; 128.9; 125.9; 63.2; 54.1; 45.7; 33.5; 23.8

(125 MHz, CDCl3): δ 147.3, 135.0, 128.9, 125.9, 63.2, 54.1, 45.7, 33.5, 23.8

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Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Carpino, Louis A.; Mansour, E. M. E.; Knapczyk, Jerome; Journal of Organic Chemistry; vol. 48; nb. 5; (1983); p. 666 - 669, View in Reaxys

Reaxys ID 889025 View in Reaxys

43/323 CAS Registry Number: 13790-75-5 Chemical Name: N-(3,5-di-tert-butyl-4-hydroxybenzyl)piperazine; 2,6-di-tert-butyl-4-piperazin-1-ylmethyl-phenol; 1-(3,5bis(1,1-dimethylethyl)-4-hydroxyphenyl)methylpiperazine Linear Structure Formula: C19H32N2O Molecular Formula: C19H32N2O Molecular Weight: 304.476 Type of Substance: heterocyclic InChI Key: NSHPHKYHPUUZGS-UHFFFAOYSA-N Note:

H N

Melting Point (1) 1 of 1

Melting Point [°C]

197 - 199

Patent; Ethyl Corp.; US3218322; (1962); Chem.Abstr.; vol. 64; nb. 6666; (1966), View in Reaxys; Patent; Ethyl Corp.; US3186993; (1965); Chem.Abstr.; vol. 63; nb. 16368e; (1965), View in Reaxys NMR Spectroscopy (1) 1 of 1

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

NMR (CDCl3, 300 MHz) δ7.07 (s, 2H); 5.2 (br s, 1H); 3.42 (s, 2H); 2.91-2.86 (m, 4H); 2.43 (br s, 4H); 2.2 (br, 1H); 1.43 (s, 18H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

7.07; 5.2; 3.42; 2.86 - 2.91; 2.43; 2.2; 1.43

Kind of signal

s, 2H; br s, 1H; s, 2H; m, 4H; br s, 4H; br, 1H; s, 18H

Patent; Monash University; US6232314; (2001); (B1) English, View in Reaxys Use (1) Laboratory Use and Handling

References

effective stabilizer Zagidullin, R. N.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 26; nb. 10; during the distilla- (1990); p. 1140 - 1142; Khimiya Geterotsiklicheskikh Soedinenii; nb. 10; (1990); p. 1367 - 1369, tion or storage of View in Reaxys unsaturated hydrocarbons and their chloro derivatives

Reaxys ID 9766444 View in Reaxys

44/323

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CAS Registry Number: 523980-99-6 Chemical Name: 1-(2-iodobenzyl)piperazine Linear Structure Formula: C11H15IN2 Molecular Formula: C11H15IN2 Molecular Weight: 302.158 Type of Substance: heterocyclic InChI Key: SFIMCLLRGYXWSF-UHFFFAOYSA-N Note:

I N NH

Substance Label (2) Label References 5{27}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

11, Y=N, Z=2-I

Boy, Kenneth M.; Dee, Michael; Yevich, Joseph; Torrente, John; Gao, Qi; Iben, Lawrence; Stark, Arlene; Mattson, Ronald J.; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 17; (2004); p. 4467 4470, View in Reaxys

Patent-Specific Data (2) Prophetic ComLocation in Patent References pound Page/Page column prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties yellow

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Paragraph 0214

References Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR

(400 MHz, CDCl3): 6 7.80 (dd, 1H, J=1.2, 8.0 Hz) 7.39 (dd, 1H, J=1.2, 7.6 Hz), 7.30-7.26 (m, 1H), 6.91 (dt, 1H, J=1.2, 7.2 Hz), 3.47 (s, 2H), 2.86 (t, 4H, J=4.8 Hz), 2.46 (br s, 4H), 1.76 (br s, 1H)

Location

Paragraph 0214

Signals [ppm]

7.39; 7.26 - 7.3; 6.91; 3.47; 2.86; 2.46; 1.76

Kind of signal

dd, 1H, J=1.2, 7.6 Hz; m, 1H; dt, 1H, J=1.2, 7.2 Hz; s, 2H; t, 4H, J=4.8 Hz; br s, 4H; br s, 1H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Original Text (NMR Spectroscopy)

13C-NMR

(100 MHz, CDCl3): 6 140.4, 139.3, 130.2, 128.6, 127.8, 100.6, 66.9, 54.3, 46.0

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Location

Paragraph 0214

Signals [ppm]

139.3; 130.2; 128.6; 127.8; 100.6; 66.9; 54.3; 46

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Reaxys ID 10162478 View in Reaxys

45/323 Chemical Name: 1-(2,3-dichlorobenzyl)piperazine; dichlorobenzylpiperazine Linear Structure Formula: C11H14Cl2N2 Molecular Formula: C11H14Cl2N2 Molecular Weight: 245.152 Type of Substance: heterocyclic InChI Key: LFMDJDXSAUVJHV-UHFFFAOYSA-N Note:

Cl Cl

N NH

Substance Label (1) Label References piperazine, j

Yang, Yinghua; Sun, Lianli; Dong, Shengyi; Wang, Xiaoyu; Yang, Leixiang; Wu, Xiumei; Bai, Hua; Zhao, Yu; Mendeleev Communications; vol. 18; nb. 4; (2008); p. 186 - 187, View in Reaxys

Reaxys ID 10253660 View in Reaxys

46/323 Chemical Name: 1-(4-vinylbenzyl)piperazine; N-(4-vinylbenzyl)piperazine; 4-vinylbenzylpiperazine Linear Structure Formula: C13H18N2 Molecular Formula: C13H18N2 Molecular Weight: 202.299 Type of Substance: heterocyclic InChI Key: ADHMJVLPJMDBLH-UHFFFAOYSA-N Note:

NH N

Substance Label (1) Label References 8

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties white

Paragraph 0220

References Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

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Original Text (NMR Spectroscopy)

1H-NMR (500 MHz, CDCl ): δ 7.32 (d, 2H, J=8.0 Hz), 7.24 (d, 2H, J=8.0 Hz), 6.66 (dd, 1H, 3 J=11.0, 18.0 Hz), 5.69 (dd, 1H, J=0.5, 18.0 Hz), 5.18 (dd, 1H, J=0.5, 11.0 Hz), 3.43 (s, 2H), 2.84 (t, 4H, J=5.0 Hz), 2.63 (br s, 1H), 2.37 (br s, 4H)

Location

Paragraph 0220

Signals [ppm]

7.32; 7.24; 6.66; 5.69; 5.18; 3.43; 2.84; 2.63; 2.37

Kind of signal

d, 2H, J=8.0 Hz; d, 2H, J=8.0 Hz; dd, 1H, J=11.0, 18.0 Hz; dd, 1H, J=0.5, 18.0 Hz; dd, 1H, J=0.5, 11.0 Hz; s, 2H; t, 4H, J=5.0 Hz; br s, 1H; br s, 4H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Original Text (NMR Spectroscopy)

13C-NMR

Location

Paragraph 0220

Signals [ppm]

137.5; 136.4; 136.2; 129.1; 125.8; 113.3; 63.1; 54; 45.7

(125 MHz, CDCl3): δ 137.5, 136.4, 136.2, 129.1, 125.8, 113.3, 63.1, 54.0, 45.7

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Reaxys ID 5032494 View in Reaxys

47/323 CAS Registry Number: 118778-74-8 Chemical Name: 1-(3,5-dimethoxybenzyl)piperazine; 3,5-dimethoxybenzylpiperazine Linear Structure Formula: C13H20N2O2 Molecular Formula: C13H20N2O2 Molecular Weight: 236.314 Type of Substance: heterocyclic InChI Key: QBONNKXMYASOKV-UHFFFAOYSA-N Note:

H N

N O

Substance Label (1) Label References 5c

Masaguer, Christian F.; Ravina, Enrique; Tetrahedron Letters; vol. 37; nb. 29; (1996); p. 5171 - 5174, View in Reaxys

Derivative (1) Derivative

References

1-(3,5-Dimethoxy- Masaguer, Christian F.; Ravina, Enrique; Tetrahedron Letters; vol. 37; nb. 29; (1996); p. 5171 - 5174, benzyl)-piperaView in Reaxys zine; hydrochloride Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy)

209/337

2016-05-20 15:00:44

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Reaxys ID 7920040 View in Reaxys

48/323 Chemical Name: 1-(3-aminobenzyl)piperazine Linear Structure Formula: C11H17N3 Molecular Formula: C11H17N3 Molecular Weight: 191.276 Type of Substance: heterocyclic InChI Key: WQJUXLSPLDPDDF-UHFFFAOYSA-N Note:

H N

NH 2

Substance Label (1) Label References 13

Borzenko, Andrey; Rotta-Loria, Nicolas L.; Macqueen, Preston M.; Lavoie, Christopher M.; McDonald, Robert; Stradiotto, Mark; Angewandte Chemie - International Edition; vol. 54; nb. 12; (2015); p. 3773 3777; Angew. Chem.; vol. 127; nb. 12; (2015); p. 3844 - 3848,5, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties yellow

supporting information

References Borzenko, Andrey; Rotta-Loria, Nicolas L.; Macqueen, Preston M.; Lavoie, Christopher M.; McDonald, Robert; Stradiotto, Mark; Angewandte Chemie - International Edition; vol. 54; nb. 12; (2015); p. 3773 - 3777; Angew. Chem.; vol. 127; nb. 12; (2015); p. 3844 - 3848,5, View in Reaxys

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

210/337

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Borzenko, Andrey; Rotta-Loria, Nicolas L.; Macqueen, Preston M.; Lavoie, Christopher M.; McDonald, Robert; Stradiotto, Mark; Angewandte Chemie - International Edition; vol. 54; nb. 12; (2015); p. 3773 - 3777; Angew. Chem.; vol. 127; nb. 12; (2015); p. 3844 - 3848,5, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

75.4

Location

supporting information

Borzenko, Andrey; Rotta-Loria, Nicolas L.; Macqueen, Preston M.; Lavoie, Christopher M.; McDonald, Robert; Stradiotto, Mark; Angewandte Chemie - International Edition; vol. 54; nb. 12; (2015); p. 3773 - 3777; Angew. Chem.; vol. 127; nb. 12; (2015); p. 3844 - 3848,5, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

500.1

Location

supporting information

Lundgren, Rylan J.; Peters, Brendan D.; Alsabeh, Pamela G.; Stradiotto, Mark; Angewandte Chemie - International Edition; vol. 49; nb. 24; (2010); p. 4071 - 4074, View in Reaxys 4 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

125.8

Location

supporting information

Lundgren, Rylan J.; Peters, Brendan D.; Alsabeh, Pamela G.; Stradiotto, Mark; Angewandte Chemie - International Edition; vol. 49; nb. 24; (2010); p. 4071 - 4074, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); IT (ion trap); spectrum

supporting information

Borzenko, Andrey; Rotta-Loria, Nicolas L.; Macqueen, Preston M.; Lavoie, Christopher M.; McDonald, Robert; Stradiotto, Mark; Angewandte Chemie - International Edition; vol. 54; nb. 12; (2015); p. 3773 - 3777; Angew. Chem.; vol. 127; nb. 12; (2015); p. 3844 - 3848,5, View in Reaxys

HRMS (High resolution mass spectrometry);

supporting information

Lundgren, Rylan J.; Peters, Brendan D.; Alsabeh, Pamela G.; Stradiotto, Mark; Angewandte Chemie - International Edition; vol. 49; nb. 24; (2010); p. 4071 - 4074, View in Reaxys

211/337

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ESI (Electrospray ionisation); Spectrum

Reaxys ID 10090259 View in Reaxys

49/323 CAS Registry Number: 919109-49-2 Chemical Name: 5-(tert-butyl)-2-hydroxy-3-(piperazin-1-ylmethyl)benzaldehyde; 5-tert-butyl-2-hydroxy-3-(piperazin-1-ylmethyl)benzaldehyde; 5-tert-butyl-2-hydroxy-3-(piperazinomethyl)benzaldehyde; 5-t-butyl-2-hydroxy-3-(piperazinomethyl)benzaldehyde Linear Structure Formula: C16H24O2N2 Molecular Formula: C16H24N2O2 Molecular Weight: 276.379 Type of Substance: heterocyclic InChI Key: FTWVZAOQPDWNEC-UHFFFAOYSA-N Note:

H N

OH O

Substance Label (4) Label References 9.3a

Biannic, Berenger; Bozell, Joseph J.; Organic Letters; vol. 15; nb. 11; (2013); p. 2730 - 2733, View in Reaxys

Galbraith, Stuart G.; Wang, Qiang; Li, Li; Blake, Alexanders; Wilson, Claire; Collinson, Simon R.; Lindoy, Leonard F.; Plieger, Paul G.; Schroeder, Martin; Tasker, Peter A.; Chemistry - A European Journal; vol. 13; nb. 21; (2007); p. 6090 - 6107, View in Reaxys

Wang, Qiang; Wilson, Claire; Blake, Alexander J.; Collinson, Simon R.; Tasker, Peter A.; Schroeder, Martin; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8983 - 8987, View in Reaxys

12f

Fennie, Michael W.; DiMauro, Erin F.; O'Brien, Erin M.; Annamalai, Venkatachalam; Kozlowski, Marisa C.; Tetrahedron; vol. 61; nb. 26; (2005); p. 6249 - 6265, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

220 - 225

Comment (Melting Point)

Decomposition; Crystallization with 0.15 Mol(s) CH2Cl2

Wang, Qiang; Wilson, Claire; Blake, Alexander J.; Collinson, Simon R.; Tasker, Peter A.; Schroeder, Martin; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8983 - 8987, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties yellow

supporting information

yellow

References Biannic, Berenger; Bozell, Joseph J.; Organic Letters; vol. 15; nb. 11; (2013); p. 2730 2733, View in Reaxys Wang, Qiang; Wilson, Claire; Blake, Alexander J.; Collinson, Simon R.; Tasker, Peter A.; Schroeder, Martin; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8983 - 8987, View in Reaxys; Galbraith, Stuart G.; Wang, Qiang; Li, Li; Blake, Alexanders; Wilson, Claire; Collinson, Simon R.; Lindoy, Leonard F.; Plieger, Paul G.; Schroeder, Martin; Tasker, Peter A.; Chemistry - A European Journal; vol. 13; nb. 21; (2007); p. 6090 6107, View in Reaxys

NMR Spectroscopy (8) 1 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

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Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

67.93

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300.13

Wang, Qiang; Wilson, Claire; Blake, Alexander J.; Collinson, Simon R.; Tasker, Peter A.; Schroeder, Martin; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8983 - 8987, View in Reaxys 4 of 8

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300.13

Wang, Qiang; Wilson, Claire; Blake, Alexander J.; Collinson, Simon R.; Tasker, Peter A.; Schroeder, Martin; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8983 - 8987, View in Reaxys 5 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.42

Wang, Qiang; Wilson, Claire; Blake, Alexander J.; Collinson, Simon R.; Tasker, Peter A.; Schroeder, Martin; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8983 - 8987, View in Reaxys 6 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Fennie, Michael W.; DiMauro, Erin F.; O'Brien, Erin M.; Annamalai, Venkatachalam; Kozlowski, Marisa C.; Tetrahedron; vol. 61; nb. 26; (2005); p. 6249 - 6265, View in Reaxys

213/337

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7 of 8

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Fennie, Michael W.; DiMauro, Erin F.; O'Brien, Erin M.; Annamalai, Venkatachalam; Kozlowski, Marisa C.; Tetrahedron; vol. 61; nb. 26; (2005); p. 6249 - 6265, View in Reaxys 8 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Fennie, Michael W.; DiMauro, Erin F.; O'Brien, Erin M.; Annamalai, Venkatachalam; Kozlowski, Marisa C.; Tetrahedron; vol. 61; nb. 26; (2005); p. 6249 - 6265, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Wang, Qiang; Wilson, Claire; Blake, Alexander J.; Collinson, Simon R.; Tasker, Peter A.; Schroeder, Martin; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8983 - 8987, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Fennie, Michael W.; DiMauro, Erin F.; O'Brien, Erin M.; Annamalai, Venkatachalam; Kozlowski, Marisa C.; Tetrahedron; vol. 61; nb. 26; (2005); p. 6249 - 6265, View in Reaxys

Reaxys ID 10159900 View in Reaxys

50/323 CAS Registry Number: 203047-38-5 Chemical Name: 3-(piperazin-1-ylmethyl)benzonitrile; 1-(3-cyanobenzyl)piperazine Linear Structure Formula: C12H15N3 Molecular Formula: C12H15N3 Molecular Weight: 201.271 Type of Substance: heterocyclic InChI Key: XDYXEYUQBGLAOZ-UHFFFAOYSA-N Note:

H N

Patent-Specific Data (2) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys Patent; Gruenenthal GmbH; US2008/153843; (2008); (A1) English, View in Reaxys

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Reaxys ID 13414987 View in Reaxys

51/323 CAS Registry Number: 86620-81-7 Chemical Name: methyl 4-(piperazin-1-ylmethyl)benzoate; 4piperazin-1-ylmethylbenzoic acid methyl ester; methyl 4-(piperazin-1-ylmethyl)-benzoate Linear Structure Formula: C13H18N2O2 Molecular Formula: C13H18N2O2 Molecular Weight: 234.298 InChI Key: XJIVYTXCTMWGLR-UHFFFAOYSA-N Note:

N O

NH O

Substance Label (1) Label References 19

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties colourless

Page/Page column 64

References Patent; UNIVERSITA' DEGLI STUDI DI MILANO - BICOCCA; UNIVERSITÉ DE GENÈVE; UNIVERSITÉ CLAUDE BERNARD LYON 1; GAMBACORTI-PASSERINI, Carlo; MOLOGNI, Luca; SCAPOZZA, Leonardo; BISSON, William; GOEKJIAN, Peter; BENOIT, Joseph; WO2015/1024; (2015); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

VH MN (300MHz, CDC ) δ 7.95 (d, J = 8.3 Hz, 2H, Har), 7.37 (d, J = 8.3 Hz, 2H, Har), 3.87 (s, 3H, CH3), 3.50 (s,2H, CH2), 2.86 (t, J = 5.0 Hz, 4H, 2xCH2), 2.38 (t, J = 5.0 Hz, 4H, 2xCH2), 1.89 (s, 1H, NH).

Location

Page/Page column 64

Patent; UNIVERSITA' DEGLI STUDI DI MILANO - BICOCCA; UNIVERSITÉ DE GENÈVE; UNIVERSITÉ CLAUDE BERNARD LYON 1; GAMBACORTI-PASSERINI, Carlo; MOLOGNI, Luca; SCAPOZZA, Leonardo; BISSON, William; GOEKJIAN, Peter; BENOIT, Joseph; WO2015/1024; (2015); (A1) English, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Original Text (NMR Spectroscopy)

13C

Location

Page/Page column 64

RMN (75 MHz, CDCb) δ 167.3 (C), 144.0 (2xC), 129.8 (2xCH), 129.2 (2xCH), 63.5 (CH2), 54.7 (2xCH2), 52.3 (CH3), 46.3 (2xCH2).

Reaxys ID 13676577 View in Reaxys

52/323

215/337

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Chemical Name: 1-(2,3-difluoro-benzyl)-piperazine; 2,3-Difluorobenzylpiperazine Linear Structure Formula: C11H14F2N2 Molecular Formula: C11H14F2N2 Molecular Weight: 212.242 InChI Key: GBODJTRKPPKFDZ-UHFFFAOYSA-N Note:

F F

N NH

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H NMR (300 MHz, CDCl ) δ7.20-6.97 (m, 2H), 3.60 (s, 2H), 2.90 (t, 4H), 2.55-2.35 (brs, 3 4H), 1.67 (s, 1H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

6.97 - 7.2; 3.6; 2.9; 2.35 - 2.55; 1.67

Kind of signal

m, 2H; s, 2H; t, 4H; brs, 4H; s, 1H

Patent; Molecular Geriatrics Corporation; US6214994; (2001); (B1) English, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

6.97 - 7.2; 3.6; 2.9; 2.35 - 2.55; 1.67

Kind of signal

m, 2 H; s, 2 H; t, 4 H; brs, 4 H; s, 1 H

H NMR (300 MHz, CDCl3) δ 7.20-6.97 (m, 2 H), 3.60 (s, 2 H), 2.90 (t, 4 H), 2.55-2.35 (brs, 4 H), 1.67 (s, 1 H)

Patent; Molecular Geriatrics Corporation; US5658909; (1997); (A1) English, View in Reaxys 3 of 3

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

NMR (300 MHz, CDCl3) δ 7.20-6.97 (m, 2 H), 3.60 (s, 2 H), 2.90 (t, 4 H), 2.55-2.35 (brs, 4 H), 1.67 (s, 1 H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

6.97 - 7.2; 3.6; 2.9; 2.35 - 2.55; 1.67

Kind of signal

m, 2 H; s, 2 H; t, 4 H; brs, 4 H; s, 1 H

Patent; Molecular Geriatrics Corporation; US5693804; (1997); (A1) English, View in Reaxys

216/337

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Reaxys ID 14352744 View in Reaxys

53/323 Chemical Name: 5-(piperazin-1-ylmethyl)benzene-1,3-diol dihydrochloride; 5-(piperazin-1-ylmethyl)benzene-1,3-diol; 5-piperazin-1-ylmethyl-benzene-1,3-diol dihydrochloride Linear Structure Formula: C11H16N2O2*2ClH Molecular Formula: C11H16N2O2*2ClH Molecular Weight: 281.182 InChI Key: AFWIQBGEAAKKSY-UHFFFAOYSA-N Note:

2 HCl

N NH OH

Substance Label (2) Label References 15a

Jorgensen, William T.; Gulliver, Damien W.; Werry, Eryn L.; Reekie, Tristan; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 730 - 740, View in Reaxys

Reekie, Tristan A.; McGregor, Iain S.; Kassiou, Michael; Tetrahedron Letters; vol. 55; nb. 33; (2014); p. 4568 - 4571, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

278 - 280

Melting Point [°C]

278 - 280

Location

supporting information

Reekie, Tristan A.; McGregor, Iain S.; Kassiou, Michael; Tetrahedron Letters; vol. 55; nb. 33; (2014); p. 4568 4571, View in Reaxys Chromatographic Data (2) Chromatographic Location data TLC (Thin layer chromatography) TLC (Thin layer chromatography)

Crystal Property Description (3) Colour & Other Location Properties white

white

References

Reekie, Tristan A.; McGregor, Iain S.; Kassiou, Michael; Tetrahedron Letters; vol. 55; nb. 33; (2014); p. 4568 - 4571, View in Reaxys References Jorgensen, William T.; Gulliver, Damien W.; Werry, Eryn L.; Reekie, Tristan; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 730 - 740, View in Reaxys

supporting information

white

Reekie, Tristan A.; McGregor, Iain S.; Kassiou, Michael; Tetrahedron Letters; vol. 55; nb. 33; (2014); p. 4568 - 4571, View in Reaxys Patent; Ferring B.V.; EP1512687; (2005); (A1) English, View in Reaxys

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy)

217/337

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Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Reekie, Tristan A.; McGregor, Iain S.; Kassiou, Michael; Tetrahedron Letters; vol. 55; nb. 33; (2014); p. 4568 4571, View in Reaxys 4 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Reekie, Tristan A.; McGregor, Iain S.; Kassiou, Michael; Tetrahedron Letters; vol. 55; nb. 33; (2014); p. 4568 4571, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Description (IR Spectroscopy)

Bands

Location

supporting information

Reekie, Tristan A.; McGregor, Iain S.; Kassiou, Michael; Tetrahedron Letters; vol. 55; nb. 33; (2014); p. 4568 4571, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry) electrospray ionisation (ESI); liquid chromatography mass spectrometry (LCMS); IT (ion trap); spectrum

References Jorgensen, William T.; Gulliver, Damien W.; Werry, Eryn L.; Reekie, Tristan; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 730 - 740, View in Reaxys

218/337

2016-05-20 15:00:44

electrospray ionisation (ESI); spectrum

supporting information

Reekie, Tristan A.; McGregor, Iain S.; Kassiou, Michael; Tetrahedron Letters; vol. 55; nb. 33; (2014); p. 4568 - 4571, View in Reaxys

Reaxys ID 19151757 View in Reaxys

54/323 CAS Registry Number: 523981-01-3 Chemical Name: 1-(4-iodobenzyl)piperazine; 1-(4-iodobenzyl)piperazine Linear Structure Formula: C11H15IN2 Molecular Formula: C11H15IN2 Molecular Weight: 302.158 InChI Key: HWHUEYHTSBKINK-UHFFFAOYSA-N Note:

NH N

Substance Label (1) Label References 6

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

CID (collision-insupporting inforduced dissociamation tion); IT (ion trap); ESI (Electrospray ionisation); Spectrum

Chai, Yunfeng; Jiang, Kezhi; Sun, Cuirong; Pan, Yuanjiang; Chemistry - A European Journal; vol. 17; nb. 39; (2011); p. 10820 - 10824, View in Reaxys

Reaxys ID 884136 View in Reaxys

55/323 CAS Registry Number: 92033-66-4 Chemical Name: 2-hydroxy-5-piperazin-1-ylmethyl-benzoic acid methyl ester; 1-<3'-Carbomethoxy-4'-hydroxy-benzyl>-piperazin; 2-Hydroxy-5-piperidinomethyl-benzoesaeure-methylester Linear Structure Formula: C13H18N2O3 Molecular Formula: C13H18N2O3 Molecular Weight: 250.298 Type of Substance: heterocyclic InChI Key: YOFPFEGWEAYKSI-UHFFFAOYSA-N Note:

O O

N HO

Substance Label (2) Label References 1, A

Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys

S.13 Z.18 Ex.2

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Derivative (3) Comment (Derivative)

References

219/337

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Dihydrochlorid Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys C13H18N2O3*2H Cl*1.5 H2O: F: 174-182grad (Zers.) Dihydrochlorid*1 H2O: F: 180-185grad <Zers.>

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Dihydrochlorid*0.5 H2O: F: 165-171grad <Zers.>

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

165 - 171

Patent; Science Union and Cie.; BE630639; (1963); Chem.Abstr.; vol. 61; nb. 668; (1964), View in Reaxys 2 of 2

Melting Point [°C]

180 - 185

Patent; Science Union and Cie.; BE630639; (1963); Chem.Abstr.; vol. 61; nb. 668; (1964), View in Reaxys

Reaxys ID 884856 View in Reaxys

56/323 Chemical Name: 2-hydroxy-5-piperazin-1-ylmethyl-benzoic acid; 2-Hydroxy-5-piperidinomethyl-benzoesaeure Linear Structure Formula: C12H16N2O3 Molecular Formula: C12H16N2O3 Molecular Weight: 236.271 Type of Substance: heterocyclic InChI Key: WWPBUUCFFKUGJA-UHFFFAOYSA-N Note:

OH O

N HO

Substance Label (2) Label References Verb. 7 F

Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys

S.14 Z.25

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Derivative (3) Comment (Derivative)

References

Dihydrochlorid Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys C12H16N2O3*2H Cl: F: 204-209grad (Kofler) Dihydrochlorid: F: 205-210grad

Patent; Science Union and Cie.; BE630639; (1963); Chem.Abstr.; vol. 61; nb. 668; (1964), View in Reaxys

Dihydrochlorid: F: 205-210grad (Zers.)

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Reaxys ID 885343 View in Reaxys

57/323

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Chemical Name: 2-hydroxy-3-piperazin-1-ylmethyl-benzoic acid methyl ester; 1-<3'-Carbomethoxy-2'-hydroxy-benzyl>-piperazin; 2-Hydroxy-3-piperidinomethyl-benzoesaeure-methylester Linear Structure Formula: C13H18N2O3 Molecular Formula: C13H18N2O3 Molecular Weight: 250.298 Type of Substance: heterocyclic InChI Key: JYCSWSWGZTXJCP-UHFFFAOYSA-N Note:

N NH

Substance Label (2) Label References 5B

Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys

S.15 Z.5

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Derivative (3) Comment (Derivative)

References

Dihydrochlorid Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys C13H18N2O3*2H Cl : F: 173-183grad (Kofler, Zers.) Dihydrochlorid: F: 173-183grad

Patent; Science Union and Cie.; BE630639; (1963); Chem.Abstr.; vol. 61; nb. 668; (1964), View in Reaxys

Dihydrochlorid: F: 173-183grad (Zers.)

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Patent; Science Union and Cie.; BE630639; (1963); Chem.Abstr.; vol. 61; nb. 668; (1964), View in Reaxys

Reaxys ID 885825 View in Reaxys

58/323 Chemical Name: 2-ethoxy-5-piperazin-1-ylmethyl-benzoic acid methyl ester; <4-Aethoxy-3-methoxycarbonyl-benzyl>-piperazinzin Linear Structure Formula: C15H22N2O3 Molecular Formula: C15H22N2O3 Molecular Weight: 278.351 Type of Substance: heterocyclic InChI Key: TVTKWQSVXOKXSP-UHFFFAOYSA-N Note:

O O

N O

Substance Label (2) Label References 4

Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys

S.15 Z.15

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Derivative (3) Comment (Derivative)

References

Dihydrochlorid Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys C15H22N2O3*2H Cl*0.5H2O: F: 180-192grad (Kofler)

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Dihydrochlorid: F: 180-192grad

Patent; Science Union and Cie.; BE630639; (1963); Chem.Abstr.; vol. 61; nb. 668; (1964), View in Reaxys

Dihydrochlorid: F: 180-192grad (Zers.)

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Reaxys ID 887139 View in Reaxys

59/323 Chemical Name: 2-hydroxy-5-piperazin-1-ylmethyl-benzoic acid butyl ester; 2-Hydroxy-5-piperidinomethyl-benzoesaeurebutylester Linear Structure Formula: C16H24N2O3 Molecular Formula: C16H24N2O3 Molecular Weight: 292.378 Type of Substance: heterocyclic InChI Key: MADBQEMBJPXVNO-UHFFFAOYSA-N Note:

O O

N NH

Substance Label (2) Label References 3, G

Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys

S.14 Z.21

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Derivative (3) Comment (Derivative)

References

Dihydrochlorid Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys C16H24N2O3*2H Cl : F: 160-166grad (Kofler) Dihydrochlorid: F: 160-166grad

Patent; Science Union and Cie.; BE630639; (1963); Chem.Abstr.; vol. 61; nb. 668; (1964), View in Reaxys

Dihydrochlorid: F: 160-166grad (Zers.)

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Reaxys ID 887446 View in Reaxys

60/323 CAS Registry Number: 10207-40-6 Chemical Name: 2,4,6-triiodo-3-piperazin-1-ylmethyl-aniline Linear Structure Formula: C11H14I3N3 Molecular Formula: C11H14I3N3 Molecular Weight: 568.966 Type of Substance: heterocyclic InChI Key: KBHCAABCGDLYOU-UHFFFAOYSA-N Note:

I H 2N

N I

Substance Label (3) Label References XIX, X=NH2, NR %1&R%2&= piperazin

Hebky,J. et al.; Collection of Czechoslovak Chemical Communications; vol. 35; (1970); p. 867 - 881, View in Reaxys

II; N-subst. BenPatent; SPOFA United Pharmaceutical Works; NL6516674; (1964); Chem.Abstr.; vol. 65; nb. 15270c; zylamin (II) (R=Pi- (1966), View in Reaxys perazino; R%

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I (X=Piperazino, Y=NH2) Derivative (1) Comment (Derivative) Hydrochlorid: F: 190-200grad (Zers.)

Patent; Hebky et al.; CS121655; (1964); Chem.Abstr.; vol. 68; nb. 2696j; (1968), View in Reaxys

References Hebky,J. et al.; Collection of Czechoslovak Chemical Communications; vol. 35; (1970); p. 867 - 881, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

153 - 155

Hebky,J. et al.; Collection of Czechoslovak Chemical Communications; vol. 35; (1970); p. 867 - 881, View in Reaxys; Patent; SPOFA United Pharmaceutical Works; NL6516674; (1964); Chem.Abstr.; vol. 65; nb. 15270c; (1966), View in Reaxys; Patent; Hebky et al.; CS121655; (1964); Chem.Abstr.; vol. 68; nb. 2696j; (1968), View in Reaxys

Reaxys ID 891725 View in Reaxys

61/323 Chemical Name: 2-acetoxy-5-piperazin-1-ylmethyl-benzoic acid methyl ester; 1-<4-Acetoxy-3-methoxycarbonyl-benzyl>-piperazin; 1-<3'-Carbomethoxy-4'-acetoxy-benzyl>-piperazin Linear Structure Formula: C15H20N2O4 Molecular Formula: C15H20N2O4 Molecular Weight: 292.335 Type of Substance: heterocyclic InChI Key: LMXRBJQYACVRQS-UHFFFAOYSA-N Note:

O O

N NH

O O

Substance Label (2) Label References 2C

Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys

S.15 Z.20

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Derivative (2) Comment (Derivative)

References

Dihydrochlorid Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys C15H20N2O4*2H Cl : F: 212grad (Kofler) Dihydrochlorid: F: 212grad

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys; Patent; Science Union and Cie.; BE630639; (1963); Chem.Abstr.; vol. 61; nb. 668; (1964), View in Reaxys

Reaxys ID 3723464 View in Reaxys

62/323

NH N

CAS Registry Number: 23145-89-3 Chemical Name: 1-(4-chloro-benzyl)-piperazine; dihydrochloride; 1-(4-Chlor-benzyl)-piperazin; Dihydrochlorid; N-(4-chlorobenzyl)-piperazine dihydrochloride; N-(4-chlorobenzyl)piperazine dihydrochloride Linear Structure Formula: C11H15ClN2*2ClH Molecular Formula: C11H15ClN2*2ClH Molecular Weight: 283.628 Type of Substance: heterocyclic InChI Key: ZKQKYKNSUWSKAN-UHFFFAOYSA-N Note:

Cl 2 H

Patent-Specific Data (1)

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References Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys Melting Point (2) 1 of 2

Melting Point [°C]

278 - 280

Solvent (Melting Point)

ethanol

Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys 2 of 2

Melting Point [°C]

296

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Decomp.

Baltzly et al.; Journal of the American Chemical Society; vol. 66; (1944); p. 263,265, View in Reaxys

Reaxys ID 3726990 View in Reaxys

63/323

CAS Registry Number: 21868-01-9; 109188-09-2 Chemical Name: 1-(4-methoxy-benzyl)-piperazine; dihydrochloride; 1-(4-Methoxy-benzyl)-piperazin; Dihydrochlorid; N-(4methoxybenzyl)-piperazine dihydrochloride; N-(4-methoxybenzyl)piperazine dihydrochloride Linear Structure Formula: C12H18N2O*2ClH Molecular Formula: C12H18N2O*2ClH Molecular Weight: 279.21 Type of Substance: heterocyclic InChI Key: ZABGCTWCNIKLHR-UHFFFAOYSA-N Note:

Cl 2 H

Patent-Specific Data (1) References Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys Melting Point (3) 1 of 3

Melting Point [°C]

250 - 252

Solvent (Melting Point)

ethanol

Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys 2 of 3

Melting Point [°C]

260

Comment (Melting Point)

Decomp.

Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys 3 of 3

Melting Point [°C]

263

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Decomp.

Baltzly et al.; Journal of the American Chemical Society; vol. 66; (1944); p. 263,265, View in Reaxys

Reaxys ID 5865498 View in Reaxys H 2N

64/323 Chemical Name: 4-(p-aminobenzyl)piperazine Linear Structure Formula: C11H17N3 Molecular Formula: C11H17N3 Molecular Weight: 191.276 Type of Substance: heterocyclic

NH N

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InChI Key: YTUKQWQYHKOYCO-UHFFFAOYSA-N Note:

Reaxys ID 6392674 View in Reaxys

65/323 CAS Registry Number: 104481-67-6 Chemical Name: 1-(2,5-dimethyl-benzyl)-piperazine Linear Structure Formula: C13H20N2 Molecular Formula: C13H20N2 Molecular Weight: 204.315 Type of Substance: heterocyclic InChI Key: CFQKZODRQRHNLP-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 11, R&3%=2,5diMe

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 6398891 View in Reaxys

66/323 CAS Registry Number: 89292-72-8 Chemical Name: 1-(p-n-Butylbenzyl)-piperazine Linear Structure Formula: C15H24N2 Molecular Formula: C15H24N2 Molecular Weight: 232.369 Type of Substance: heterocyclic InChI Key: MWYUBLMUYQPQSC-UHFFFAOYSA-N Note:

NH N

Boiling Point (1) Boiling Point [°C]

References

127 - 130

Patent; American Cyanamid Company; US4421753; (1983); (A1) English, View in Reaxys

Reaxys ID 6404466 View in Reaxys O

67/323 Linear Structure Formula: C11H15N3O2 Molecular Formula: C11H15N3O2 Molecular Weight: 221.259 Type of Substance: heterocyclic InChI Key: AMMRJTDWARUWQZ-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 21

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

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Reaxys ID 7920162 View in Reaxys

68/323

H N

Chemical Name: 1-(3,4-dimethylbenzyl)piperazine Linear Structure Formula: C13H20N2 Molecular Formula: C13H20N2 Molecular Weight: 204.315 Type of Substance: heterocyclic InChI Key: PXHRDWNRXRGHDR-UHFFFAOYSA-N Note:

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 9196194 View in Reaxys

69/323 CAS Registry Number: 340759-26-4 Chemical Name: 1-(4-ethyl-benzyl)-piperazine Linear Structure Formula: C13H20N2 Molecular Formula: C13H20N2 Molecular Weight: 204.315 Type of Substance: heterocyclic InChI Key: FUHWWXRPMBXPNY-UHFFFAOYSA-N Note:

NH N

Substance Label (1) Label References 11, R&3%=4-Et

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 9329852 View in Reaxys

70/323 CAS Registry Number: 150019-64-0 Chemical Name: 4-(2-fluoro-5-methoxybenzyl)piperazine; 4-(2Fluoro-5-methoxybenzyl)piperazine Linear Structure Formula: C12H17FN2O Molecular Formula: C12H17FN2O Molecular Weight: 224.278 Type of Substance: heterocyclic InChI Key: IKJSKPQZMPWISO-UHFFFAOYSA-N Note:

F N NH O

Crystal Property Description (1) Colour & Other References Properties light-yellow

Mattson, Ronald J.; Catt, John D.; Keavy, Daniel; Sloan, Charles P.; Epperson, James; Gao, Qi; Hodges, Donald B.; Iben, Lawrence; Mahle, Cathy D.; Ryan, Elaine; Yocca, Frank D.; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 6; (2003); p. 1199 - 1202, View in Reaxys

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

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Patent; Briston-Myers Squibb; US5387593; (1995); (A1) English, View in Reaxys; Mattson, Ronald J.; Catt, John D.; Keavy, Daniel; Sloan, Charles P.; Epperson, James; Gao, Qi; Hodges, Donald B.; Iben, Lawrence; Mahle, Cathy D.; Ryan, Elaine; Yocca, Frank D.; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 6; (2003); p. 1199 - 1202, View in Reaxys; Patent; John D. Catt; Ronald J. Mattson; US5478828; (A); (1995), View in Reaxys

Reaxys ID 10313445 View in Reaxys

71/323 CAS Registry Number: 656233-41-9 Chemical Name: 1-[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzylpiperazine Linear Structure Formula: C33H47N3O Molecular Formula: C33H47N3O Molecular Weight: 501.756 Type of Substance: heterocyclic InChI Key: KCTHBJPUZWMTMW-KUBAVDMBSA-N Note:

N NH HN O

Z Z

Substance Label (1) Label References 6

Patent; Wang, Yuqiang; US2004/34033; (2004); (A1) English, View in Reaxys; Wang, Yuqiang; Li, Lianfa; Jiang, Wei; Larrick, James W.; Bioorganic and Medicinal Chemistry; vol. 13; nb. 19; (2005); p. 5592 - 5599, View in Reaxys

Reaxys ID 10380669 View in Reaxys

72/323

Chemical Name: 1-(4-methoxybenzyl)piperazine monohydrochloride; 4-methoxybenzylpiperazine hydrochloride Linear Structure Formula: C12H18N2O*ClH Molecular Formula: C12H18N2O*ClH Molecular Weight: 242.749 Type of Substance: heterocyclic InChI Key: ZABGCTWCNIKLHR-UHFFFAOYSA-N Note:

Substance Label (1) Label References 5, HCl salt

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 4331, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2679241; (2014); (A1) English, View in Reaxys; Patent; BENCHIKH, Elouard; McCONNELL, Ivan; LOWRY, Philip; FITZGERALD, Peter; US2014/4623; (2014); (A1) English, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

154 - 157

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys

Reaxys ID 11657177 View in Reaxys

73/323

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Chemical Name: 4-piperazinomethyl-nitrobenzene-dihydrochloride; N-(4-nitrobenzyl)-piperazine dihydrochloride; N-(4-nitrobenzyl)piperazine dihydrochloride Linear Structure Formula: C11H15N3O2*2ClH Molecular Formula: C11H15N3O2*2ClH Molecular Weight: 294.181 InChI Key: RKOLZKKLAVRQBJ-UHFFFAOYSA-N Note:

N O

H 2 Cl

Patent-Specific Data (1) References Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

242 - 244

Solvent (Melting Point)

ethanol

Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys

Reaxys ID 14400146 View in Reaxys

74/323 CAS Registry Number: 1268716-82-0 Chemical Name: (E)-3-(4-piperazin-1-ylmethyl-phenyl)-acrylic acid methyl ester; (E)-3-(4-piperazin-1-ylmethylphenyl)acrylic acid methyl ester; 3-(4-piperazin-1-ylmethyl-phenyl)-acrylic acid methyl ester Linear Structure Formula: C15H20N2O2 Molecular Formula: C15H20N2O2 Molecular Weight: 260.336 InChI Key: VADVIINJOGMHQO-VOTSOKGWSA-N Note:

N O

E O

Crystal Property Description (2) Colour & Other Location Properties

References

white

Page/Page column 56

Patent; NOVARTIS AG; CHO, Young Shin; JIANG, Lei; SHULTZ, Michael; CHEN, Christine Hiu-Tung; LIU, Gang; LI, Jianke; WO2012/25155; (2012); (A1) English, View in Reaxys

white

Page/Page column 30

Patent; Novartis AG; US2011/53925; (2011); (A1) English, View in Reaxys

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray Molecular peak ionisation); LCMS (Liquid chromatography mass spectrometry)

References Patent; S*BIO PTE LTD; WO2005/40101; (2005); (A1) English, View in Reaxys

Reaxys ID 14520306 View in Reaxys

75/323 CAS Registry Number: 774525-10-9 Chemical Name: 1-(3,5-di-tert-butylbenzyl)piperazine; {[3,5bis(t-butyl)phenyl]methyl}piperazine Linear Structure Formula: C19H32N2 Molecular Formula: C19H32N2 Molecular Weight: 288.476 InChI Key: IWBWLNZXWAFZHQ-UHFFFAOYSA-N Note:

H N

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Substance Label (1) Label References 5{22}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties white

Paragraph 0184

References Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Original Text (NMR Spectroscopy)

1H-NMR (500 MHz, CDCl ): δ 7.31 (t, 1H, J=2.0 Hz), 7.15 (d, 2H, J=2.0 Hz), 3.51 (s, 2H), 3 2.89 (t, 4H, J=5.0 Hz), 2.42 (br s, 4H), 1.73 (br s, 1H), 1.33 (s, 18H)

Location

Paragraph 0184

Signals [ppm]

7.31; 7.15; 3.51; 2.89; 2.42; 1.73; 1.33

Kind of signal

t, 1H, J=2.0 Hz; d, 2H, J=2.0 Hz; s, 2H; t, 4H, J=5.0 Hz; br s, 4H; br s, 1H; s, 18H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Original Text (NMR Spectroscopy)

13C-NMR

Location

Paragraph 0184

Signals [ppm]

150.3; 136.8; 123.3; 120.7; 64.1; 54.3; 46.1; 34.7; 31.5

(125 MHz, CDCl3): δ 150.3, 136.8, 123.3, 120.7, 64.1, 54.3, 46.1, 34.7, 31.5

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Reaxys ID 18797098 View in Reaxys

76/323 CAS Registry Number: 523981-00-2 Chemical Name: 1-(3-iodo-benzyl)-piperazine; 1-(3-iodobenzyl)piperazine Linear Structure Formula: C11H15IN2 Molecular Formula: C11H15IN2 Molecular Weight: 302.158

N NH I

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InChI Key: FWDJFONFIPVXSF-UHFFFAOYSA-N Note: Substance Label (1) Label References 4e

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/153752; (2008); (A2) English, View in Reaxys

Molecular peak

Reaxys ID 19151760 View in Reaxys

77/323 CAS Registry Number: 203860-01-9 Chemical Name: 1 -(3,4-difluorobenzyl)piperazine Linear Structure Formula: C11H14F2N2 Molecular Formula: C11H14F2N2 Molecular Weight: 212.242 InChI Key: BZUZZARHVURUSK-UHFFFAOYSA-N Note:

NH N

Substance Label (1) Label References 14

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 19413560 View in Reaxys

78/323 CAS Registry Number: 763120-63-4 Chemical Name: 4-(piperazin-1-ylmethyl)phenylboronic acid Linear Structure Formula: C11H17BN2O2 Molecular Formula: C11H17BN2O2 Molecular Weight: 220.079 InChI Key: MXWIZZUTFZHLIB-UHFFFAOYSA-N Note:

N HO

Substance Label (1) Label References Intermediate B16

Patent; NOVARTIS AG; WO2009/87212; (2009); (A2) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Page/page column 144

Patent; NOVARTIS AG; WO2009/87212; (2009); (A2) English, View in Reaxys

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Reaxys ID 22261011 View in Reaxys

79/323 CAS Registry Number: 1082399-22-1 Chemical Name: 1-(4-(methylsulfonyl)benzyl)piperazine Linear Structure Formula: C12H18N2O2S Molecular Formula: C12H18N2O2S Molecular Weight: 254.353 InChI Key: IFRXZQUNPUNQLC-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References 22

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties white

Page/Page column 42

References Patent; CHEMIZON, A DIVISION OF OPTOMAGIC CO., LTD.; US2012/53180; (2012); (A1) English, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR

(400 MHz, CDCl3) δ 2.42 (4H, m), 2.89 (4H, m), 3.05 (3H, s), 3.57 (2H, s), 7.55 (2H, d, J=8.4 Hz), 7.88 (2H, d, J=8.4 Hz)

Location

Page/Page column 42

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

2.42; 2.89; 3.05; 3.57; 7.55; 7.88

Kind of signal

4H, m; 4H, m; 3H, s; 2H, s; 2H, d, J=8.4 Hz; 2H, d, J=8.4 Hz

Patent; CHEMIZON, A DIVISION OF OPTOMAGIC CO., LTD.; US2012/53180; (2012); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)

Page/Page column 42

Comment (Mass Spectrometry)

Peak

References

Molecular peak

255.05 m/z

Patent; CHEMIZON, A DIVISION OF OPTOMAGIC CO., LTD.; US2012/53180; (2012); (A1) English, View in Reaxys

Reaxys ID 780143 View in Reaxys

80/323 CAS Registry Number: 60261-51-0 Chemical Name: 2-piperazin-1-ylmethyl-aniline; N-Hydro-N4(2-aminobenzyl)piperazin Linear Structure Formula: C11H17N3 Molecular Formula: C11H17N3 Molecular Weight: 191.276 Type of Substance: heterocyclic InChI Key: VFCGUUIXGRFYJI-UHFFFAOYSA-N Note:

NH 2 N NH

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Substance Label (1) Label References Seite 11

Patent; Takeda Chem. Ind.; FR2291757; (1976); DE2551355; (1976); Chem.Abstr.; vol. 85; nb. 94405, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

127 - 128

Patent; Takeda Chem. Ind.; FR2291757; (1976); DE2551355; (1976); Chem.Abstr.; vol. 85; nb. 94405, View in Reaxys

Reaxys ID 785640 View in Reaxys

81/323

CAS Registry Number: 55212-35-6 Chemical Name: 1-(4-methylsulfanyl-benzyl)-piperazine; 1-(4methylthio)-benzylpiperazine Linear Structure Formula: C12H18N2S Molecular Formula: C12H18N2S Molecular Weight: 222.354 Type of Substance: heterocyclic InChI Key: QLOKJRIVRGCVIM-UHFFFAOYSA-N Note:

NH N

Substance Label (1) Label References XXIb

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Patent-Specific Data (1) References Patent; Scios, Inc.; US6340685; (2002); (B1) English, View in Reaxys Derivative (1) Comment (Derivative) Methansulfonat: F:160-162grad; Pharmakolog. Eigenschaften Boiling Point (1) Boiling Point [°C] 135 - 138

References Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Pressure (Boiling Point) [Torr]

References

1.5

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Reaxys ID 789922 View in Reaxys

82/323

CAS Registry Number: 21867-72-1 Chemical Name: 1-(4-isopropoxy-benzyl)-piperazine Linear Structure Formula: C14H22N2O Molecular Formula: C14H22N2O Molecular Weight: 234.341 Type of Substance: heterocyclic InChI Key: CZFKNKGWFGWBSD-UHFFFAOYSA-N Note:

NH N

Boiling Point (1) Boiling Point [°C] 172 - 174

Pressure (Boiling Point) [Torr]

References

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

232/337

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Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5331

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

589

Density (1) 1 of 1

Density [g·cm-3]

1.0294

Measurement Temperature [°C]

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Reaxys ID 884137 View in Reaxys

83/323 Chemical Name: 2-hydroxy-4-piperazin-1-ylmethyl-benzoic acid methyl ester; 1-<3-Hydroxy-4-methoxycarbonyl-benzyl>-piperazin Linear Structure Formula: C13H18N2O3 Molecular Formula: C13H18N2O3 Molecular Weight: 250.298 Type of Substance: heterocyclic InChI Key: UXANVFVUSJWLOW-UHFFFAOYSA-N Note:

O O

NH N

Substance Label (2) Label References 6

Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys

S.15 Z.10

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Derivative (2) Comment (Derivative)

References

Dihydrochlorid Regnier et al.; Bulletin de la Societe Chimique de France; (1966); p. 2821,2825, View in Reaxys C13H18N2O3*2H Cl: F: 180-185grad (Kofler) Dihydrochlorid: F: 180-185grad (Zers.)

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Reaxys ID 888080 View in Reaxys

84/323 Chemical Name: 2,5-dihydroxy-3-piperazin-1-ylmethyl-benzoic acid; <3-Carboxy-2,5-dihydroxy-benzyl>-piperazin Linear Structure Formula: C12H16N2O4 Molecular Formula: C12H16N2O4 Molecular Weight: 252.27 Type of Substance: heterocyclic InChI Key: PGIGXNXAOYLTNI-UHFFFAOYSA-N Note:

N NH OH

Substance Label (1) Label References

233/337

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S.19, Z. 9

Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; (1964), View in Reaxys

Derivative (1) Comment (Derivative)

References

Dihydrochlorid: Patent; Sci.-Un. et Cie.-Soc. Franc. Rech. Med.; BE630639; (1962); Chem.Abstr.; vol. 61; nb. 9509f; F= (1964), View in Reaxys; Patent; Science Union and Cie.; BE630639; (1963); Chem.Abstr.; vol. 61; nb. 668; 225-235grad(Zers (1964), View in Reaxys .)

Reaxys ID 3720389 View in Reaxys

85/323 Chemical Name: 1-(2-chloro-benzyl)-piperazine; hydrochloride; 1-(2-Chlor-benzyl)-piperazin; Hydrochlorid; 1-(2-chloro-benzyl)piperazine hydrochloride Linear Structure Formula: C11H15ClN2*ClH Molecular Formula: C11H15ClN2*ClH Molecular Weight: 247.167 Type of Substance: heterocyclic InChI Key: OVVARYZAMVDNDQ-UHFFFAOYSA-N Note:

Cl N

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

220

Baltzly et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 4809, View in Reaxys

Reaxys ID 6398037 View in Reaxys

86/323 CAS Registry Number: 118630-33-4 Chemical Name: 1-(2-Chloro-4-fluorobenzyl)piperazine; 1-(2chloro-4-fluoro-benzyl)-piperazine Linear Structure Formula: C11H14ClFN2 Molecular Formula: C11H14ClFN2 Molecular Weight: 228.697 Type of Substance: heterocyclic InChI Key: WWHXLQXVHUCVRZ-UHFFFAOYSA-N Note:

Cl N F

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product Boiling Point (1) Boiling Point [°C] 125 - 130

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys Pressure (Boiling Point) [Torr]

References

0.05

Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy)

234/337

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys

Reaxys ID 8987722 View in Reaxys

87/323 CAS Registry Number: 362054-66-8 Chemical Name: N-(4-diethylaminobenzyl)piperazine Linear Structure Formula: C15H25N3 Molecular Formula: C15H25N3 Molecular Weight: 247.384 Type of Substance: heterocyclic InChI Key: VHOBJZNOFDFYFB-UHFFFAOYSA-N Note:

N NH

Patent-Specific Data (1) References Patent; Scios, Inc.; US6340685; (2002); (B1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Delarue; Girault; Maes; Debreu-Fontaine; Labaeid; Grellier; Sergheraert; Journal of Medicinal Chemistry; vol. 44; nb. 17; (2001); p. 2827 - 2833, View in Reaxys

Reaxys ID 9198177 View in Reaxys

88/323

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Linear Structure Formula: C11H14Cl2N2 Molecular Formula: C11H14Cl2N2 Molecular Weight: 245.152 Type of Substance: heterocyclic InChI Key: CRJIMSPOLFYOPJ-UHFFFAOYSA-N Note:

H N

N Cl

Substance Label (1) Label References 11, R&3%=3,5diCl

Reaxys ID 9200352 View in Reaxys

89/323 CAS Registry Number: 868054-29-9 Chemical Name: 1 -(3,5-difluorobenzyl)piperazine Linear Structure Formula: C11H14F2N2 Molecular Formula: C11H14F2N2 Molecular Weight: 212.242 Type of Substance: heterocyclic InChI Key: KIUFJPFAJJKTOP-UHFFFAOYSA-N Note:

H N

N F

Substance Label (1) Label References 11, R&3%=3,5diF

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 9202985 View in Reaxys

F F

O F

90/323 Chemical Name: 1-(3-trifluoromethoxy-benzyl)-piperazine Linear Structure Formula: C12H15F3N2O Molecular Formula: C12H15F3N2O Molecular Weight: 260.259 Type of Substance: heterocyclic InChI Key: GOLWWZWJWXGGPC-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 11, R&3%=3OCF3

Reaxys ID 9263360 View in Reaxys

91/323

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Linear Structure Formula: C12H17ClN2O Molecular Formula: C12H17ClN2O Molecular Weight: 240.733 Type of Substance: heterocyclic InChI Key: DWELHCAXFIUDQR-UHFFFAOYSA-N Note:

O N NH Cl

Reaxys ID 9264102 View in Reaxys

92/323 CAS Registry Number: 356085-57-9 Linear Structure Formula: C13H20N2O2 Molecular Formula: C13H20N2O2 Molecular Weight: 236.314 Type of Substance: heterocyclic InChI Key: KITIJFNTLBMYQD-UHFFFAOYSA-N Note:

O N NH O

Reaxys ID 9281716 View in Reaxys

93/323 Chemical Name: 1-(2,3,4,5,6-pentafluorobenzyl)piperazine; 1((perfluorophenyl)methyl)piperazine Linear Structure Formula: C11H11F5N2 Molecular Formula: C11H11F5N2 Molecular Weight: 266.214 Type of Substance: heterocyclic InChI Key: FEEJBVIIKCDHIT-UHFFFAOYSA-N Note:

F F

Substance Label (2) Label References 4b

Frank, Dominik J.; Franzke, Axel; Pfaltz, Andreas; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2405 - 2415, View in Reaxys

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

68 - 69

Location

supporting information

Frank, Dominik J.; Franzke, Axel; Pfaltz, Andreas; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2405 - 2415, View in Reaxys 2 of 2

Melting Point [°C]

216 - 217

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Boiling Point (1) Boiling Point [°C] 75 - 80

Pressure (Boiling Point) [Torr]

References

0.35

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Frank, Dominik J.; Franzke, Axel; Pfaltz, Andreas; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2405 - 2415, View in Reaxys

NMR Spectroscopy (6)

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1 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

400.1

Location

supporting information

Frank, Dominik J.; Franzke, Axel; Pfaltz, Andreas; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2405 - 2415, View in Reaxys 2 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

100.6

Location

supporting information

Frank, Dominik J.; Franzke, Axel; Pfaltz, Andreas; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2405 - 2415, View in Reaxys 3 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

376.5

Location

supporting information

Frank, Dominik J.; Franzke, Axel; Pfaltz, Andreas; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2405 - 2415, View in Reaxys 4 of 6

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 5 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

238/337

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 6 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Frank, Dominik J.; Franzke, Axel; Pfaltz, Andreas; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2405 - 2415, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

electron impact (EI); spectrum

Frank, Dominik J.; Franzke, Axel; Pfaltz, Andreas; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2405 - 2415, View in Reaxys

supporting information

Reaxys ID 9956611 View in Reaxys

94/323 Linear Structure Formula: C11H17N3O*ClH Molecular Formula: C11H17N3O*ClH Molecular Weight: 243.736 Type of Substance: heterocyclic InChI Key: JIAMPUHGXQCUMR-UHFFFAOYSA-N Note:

OH N NH

NH 2

Substance Label (2) Label References 3d

Venkatesha Perumal, Ramachandran; Mahesh, Radhakrishnan; Bioorganic and Medicinal Chemistry Letters; vol. 16; nb. 10; (2006); p. 2769 - 2772, View in Reaxys

Mahesh, Radhakrishnan; Perumal, Ramachandran Venkatesha; Pandi, Pandi Vijaya; Biological and Pharmaceutical Bulletin; vol. 27; nb. 9; (2004); p. 1403 - 1405, View in Reaxys

Reaxys ID 10380682 View in Reaxys F

NH N

95/323

Chemical Name: 1-(4-fluorobenzyl)piperazine monohydrochloride; 1-(4-fluorobenzyl) piperazine hydrochloride; 1-(4-fluorobenzyl)-piperazine hydrochloride Linear Structure Formula: C11H15FN2*ClH Molecular Formula: C11H15FN2*ClH

239/337

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Molecular Weight: 230.713 Type of Substance: heterocyclic InChI Key: NARSRVMPDQTUDE-UHFFFAOYSA-N Note: Substance Label (1) Label References 8

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 4331, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

164 - 167

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys

Reaxys ID 10382942 View in Reaxys

96/323 Chemical Name: 1-(4-nitrobenzyl)piperazine monohydrochloride; 1-(4-Nitrobenzyl)piperazine hydrochloride Linear Structure Formula: C11H15N3O2*ClH Molecular Formula: C11H15N3O2*ClH Molecular Weight: 257.72 Type of Substance: heterocyclic InChI Key: RKOLZKKLAVRQBJ-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 6

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 4331, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

209 - 212

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy)

240/337

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Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Mehanna, Ahmed S.; Jin, Yung Kim; Bioorganic and Medicinal Chemistry; vol. 13; nb. 13; (2005); p. 4323 - 4331, View in Reaxys

Reaxys ID 11702413 View in Reaxys

97/323 Chemical Name: 1-(4-fluoro-benzyl)-piperazine dihydrochloride; N-(4-fluorobenzyl)-piperazine dihydrochloride; N-(4-fluorobenzyl)piperazine dihydrochloride Linear Structure Formula: C11H15FN2*2ClH Molecular Formula: C11H15FN2*2ClH Molecular Weight: 267.174 InChI Key: NARSRVMPDQTUDE-UHFFFAOYSA-N Note:

2 HCl

NH N

Substance Label (1) Label References 13

Patent; CHEMOCENTRYX, INC.; WO2007/22257; (2007); (A2) English, View in Reaxys

Patent-Specific Data (1) References Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

282 - 284

Solvent (Melting Point)

ethanol

Patent; Shanghai Institute of Pharmaceutical Industry; US2005/267121; (2005); (A1) English, View in Reaxys

Reaxys ID 16746019 View in Reaxys 2

98/323 Chemical Name: bis(N-benzylpiperazinium) tetrachlorocuprate bis(hydrochloride); (NbzpipzH2Cl)2CuCl4 Linear Structure Formula: 2C6H5CH2C4H11N2 (2+)*2Cl(1-)*CuCl (2-)={(C H CH C H N )Cl}2CuCl 4 6 5 2 4 11 2 4 Molecular Formula: 2C11H16N2*2ClH*Cl4Cu*2H Molecular Weight: 632.819 Type of Substance: Coordination compound InChI Key: UVUQCPSGEXQFNS-UHFFFAOYSA-K Note:

HCl

H+ Cl

N NH

Cu 2Cl ClCl

(v4)

Melting Point (1) 1 of 1

Melting Point [°C]

202 - 206

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Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys Density (2) 1 of 2

Density [g·cm-3]

1.488

Measurement Temperature [°C]

Type (Density)

crystallographic

Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys 2 of 2

Density [g·cm-3]

1.48

Comment (Density)

Solid

Bray, Kevin L.; Drickamer, Harry G.; Journal of Physical Chemistry; vol. 94; (1990); p. 2154 - 2159, View in Reaxys; Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys

Crystal Phase (2) Description (Crys- References tal Phase) Crystal growth

Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys

Single Crystal Xray Diffraction

Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys

Crystal Property Description (1) Colour & Other References Properties green

Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys

Crystal System (1) Crystal System References Monoclinic

Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys

Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles

Single Crystal Xray Diffraction

Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys

Magnetic Data (1) Description (Mag- Moment (Magnet- References netic Data) ic Data) [Acm2] Magnetic moment 1.77135E-19

Space Group (1) Space Group 7

Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys

Comment (Space Group)

References

a = 21.954 Angstroem, b = 7.0889 Angstroem, c = 9.1391 Angstroem, β =

Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys

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97.054; Z = 2; T = 20 Deg C; atomic positions available UV/VIS Spectroscopy (2) 1 of 2

Description (UV/VIS Spectroscopy)

Spectrum; Band assignment

Solvent (UV/VIS Spectroscopy)

solid

Comment (UV/VIS Spectroscopy)

500 nm - 2000 nm

Bray, Kevin L.; Drickamer, Harry G.; Journal of Physical Chemistry; vol. 94; (1990); p. 2154 - 2159 ; (from Gmelin), View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

Band assignment

Solvent (UV/VIS Spectroscopy)

neat (no solvent, solid phase)

Comment (UV/VIS Spectroscopy)

692.042 nm - 949.668 nm

Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Inorganica Chimica Acta; vol. 58; (1982); p. 193 - 200 ; (from Gmelin), View in Reaxys

Reaxys ID 18136888 View in Reaxys

99/323

N NH

Chemical Name: 1-benzylpiperazine hydrobromide; N-benzylpiperazinium bromide Linear Structure Formula: NH(CH2CH2)2NHCH2C6H5 (1+)*Br(1-) Molecular Formula: BrH*C11H16N2 Molecular Weight: 257.173 InChI Key: BZUJANDHJUQJNG-UHFFFAOYSA-N Note:

HBr

Reaxys ID 18987612 View in Reaxys

100/323 CAS Registry Number: 1124212-41-4 Chemical Name: N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide Linear Structure Formula: C16H25N3O Molecular Formula: C16H25N3O Molecular Weight: 275.394 InChI Key: ALFLGLAENVMJMG-UHFFFAOYSA-N Note:

O N H

N NH

Crystal Property Description (1) Colour & Other References Properties white

Patent; N.V. ORGANON; WO2009/24550; (2009); (A1) English, View in Reaxys; Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); (A1) English, View in Reaxys

Mass Spectrometry (2) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray ionisation)

Peak

Molecular peak

References Patent; N.V. ORGANON; WO2009/24550; (2009); (A1) English, View in Reaxys

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ESI (Electrospray ionisation)

Molecular peak

276.3 m/z

Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); (A1) English, View in Reaxys

Reaxys ID 18987614 View in Reaxys

101/323 CAS Registry Number: 1124216-71-2 Chemical Name: (R)-N-sec-butyl-3-(piperazin-1-ylmethyl)benzamide Linear Structure Formula: C16H25N3O Molecular Formula: C16H25N3O Molecular Weight: 275.394 InChI Key: ULYIGRGLEUFHNX-CYBMUJFWSA-N Note:

O N H

N NH

Mass Spectrometry (2) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray ionisation)

Molecular peak

ESI (Electrospray ionisation)

Molecular peak

Peak

References Patent; N.V. ORGANON; WO2009/24550; (2009); (A1) English, View in Reaxys

276.3 m/z

Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); (A1) English, View in Reaxys

Reaxys ID 18987617 View in Reaxys

102/323 CAS Registry Number: 1124215-67-3 Chemical Name: N-tert-butyl-2-fluoro-3-(piperazin-1-ylmethyl)benzamide Linear Structure Formula: C16H24FN3O Molecular Formula: C16H24FN3O Molecular Weight: 293.384 InChI Key: LTLMCEBLFZBLPL-UHFFFAOYSA-N Note:

N H

N NH

Mass Spectrometry (2) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray ionisation)

Molecular peak

ESI (Electrospray ionisation)

Molecular peak

Peak

References Patent; N.V. ORGANON; WO2009/24550; (2009); (A1) English, View in Reaxys

294.4 m/z

Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); (A1) English, View in Reaxys

Reaxys ID 18987621 View in Reaxys

103/323 CAS Registry Number: 1124216-41-6 Chemical Name: 3-(piperazin-1-ylmethyl)-N-(1,1,1-trifluoro-2methylpropan-2-yl)benzamide Linear Structure Formula: C16H22F3N3O Molecular Formula: C16H22F3N3O Molecular Weight: 329.365 InChI Key: KIJQPWJJJXMOBQ-UHFFFAOYSA-N Note:

O F F

N H

Mass Spectrometry (2) Description (Mass Comment (Mass Spectrometry) Spectrometry)

N NH

Peak

References

244/337

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ESI (Electrospray ionisation)

Molecular peak

ESI (Electrospray ionisation)

Molecular peak

Patent; N.V. ORGANON; WO2009/24550; (2009); (A1) English, View in Reaxys 330.3 m/z

Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); (A1) English, View in Reaxys

Reaxys ID 18987658 View in Reaxys

104/323 2

O N H

N NH

Mass Spectrometry (2) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray ionisation)

Chemical Name: N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide dihydrochloride Linear Structure Formula: C16H25N3O*2ClH Molecular Formula: C16H25N3O*2ClH Molecular Weight: 348.316 InChI Key: XUWUEJMHMYGBAR-UHFFFAOYSA-N Note:

HCl

References

Molecular peak

Patent; N.V. ORGANON; WO2009/24550; (2009); (A1) English, View in Reaxys

ESI (Electrospray ionisation)

Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); (A1) English, View in Reaxys

Reaxys ID 18987686 View in Reaxys

105/323

O O

Chemical Name: methyl 3-(piperazin-1-ylmethyl)benzoate bis(2,2,2-trifluoroacetate) Linear Structure Formula: 2C2HF3O2*C13H18N2O2 Molecular Formula: 2C2HF3O2*C13H18N2O2 Molecular Weight: 462.346 InChI Key: DEUJCNYFRNPCAX-UHFFFAOYSA-N Note:

O 2 HO

N NH

Mass Spectrometry (2) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray ionisation)

Molecular peak

ESI (Electrospray ionisation)

Molecular peak

F F

Peak

References Patent; N.V. ORGANON; WO2009/24550; (2009); (A1) English, View in Reaxys

235.1 m/z

Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); (A1) English, View in Reaxys

Reaxys ID 19085583 View in Reaxys

106/323 Chemical Name: 1-benzyl piperazine dihydrobromide; 1-benzylpiperazinium bromide Linear Structure Formula: NH2NH(CH2)4CH2C6H5 (2+)*2Br(1-)=NH NH(CH )4CH C H (Br)2 2 2 2 6 5 Molecular Formula: 2BrH*C11H16N2 Molecular Weight: 338.085 InChI Key: BZUJANDHJUQJNG-UHFFFAOYSA-N Note:

2 HBr N NH

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Reaxys ID 22229995 View in Reaxys

107/323 CAS Registry Number: 1345843-97-1 Chemical Name: 1-(2,3,4,5,6-pentamethylbenzyl)piperazine Linear Structure Formula: C16H26N2 Molecular Formula: C16H26N2 Molecular Weight: 246.396 InChI Key: XOFXXWUUDISUGE-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 5{14}

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties white

Paragraph 0136

References Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR

(400 MHz, CDCl3): δ 3.52 (s, 2H), 2.80 (t, 4H, J=4.8 Hz), 2.45 (br s, 4H), 2.32 (s, 6H), 2.25 (s, 3H), 2.23 (s, 6H), 1.63 (br s, 1H)

Location

Paragraph 0136

Signals [ppm]

3.52; 2.8; 2.45; 2.32; 2.25; 2.23; 1.63

Kind of signal

s, 2H; t, 4H, J=4.8 Hz; br s, 4H; s, 6H; s, 3H; s, 6H; br s, 1H

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Original Text (NMR Spectroscopy)

13C-NMR

Location

Paragraph 0136

Signals [ppm]

133.9; 133.7; 132.3; 131.9; 57.2; 54.1; 46.5; 17; 16.8; 16.6

(125 MHz, CDCl3): δ 133.9, 133.7, 132.3, 131.9, 57.2, 54.1, 46.5, 17.0, 16.8,

16.6

Patent; The Board of Trustees of the University lllinois; HERGENROTHER, Paul J.; US2013/96133; (2013); (A1) English, View in Reaxys

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Reaxys ID 22743245 View in Reaxys

108/323 CAS Registry Number: 1177491-31-4 Chemical Name: 2-piperazin-1-ylmethyl-phenol Linear Structure Formula: C11H16N2O Molecular Formula: C11H16N2O Molecular Weight: 192.261 InChI Key: GQRQDGSWNXOCNK-UHFFFAOYSA-N Note:

OH N NH

Reaxys ID 23604756 View in Reaxys

109/323

CAS Registry Number: 1158547-02-4 Linear Structure Formula: ClH*C11H15ClN2 Molecular Formula: C11H15ClN2*ClH Molecular Weight: 247.167 InChI Key: PHHFZSZJEUSYDV-UHFFFAOYSA-N Note:

HCl

Substance Label (1) Label References a

Zeng, Xiaoyun; Zheng, Jinhong; Fu, Chenglai; Su, Hang; Sun, Xiaoli; Zhang, Xuesi; Hou, Yingjian; Zhu, Yi; Molecular Pharmacology; vol. 83; nb. 5; (2013); p. 1099 - 1108, View in Reaxys

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Radl, Stanislav; Hezky, Petr; Proska, Jan; Hejnova, Lucie; Krejci, Ivan; Archiv der Pharmazie; vol. 333; nb. 5; (2000); p. 107 - 112, View in Reaxys; Zeng, Xiaoyun; Zheng, Jinhong; Fu, Chenglai; Su, Hang; Sun, Xiaoli; Zhang, Xuesi; Hou, Yingjian; Zhu, Yi; Molecular Pharmacology; vol. 83; nb. 5; (2013); p. 1099 - 1108, View in Reaxys

Reaxys ID 24007267 View in Reaxys

110/323 Chemical Name: 4-(1-piperazinylmethyl)benzamide dihydrochloride Linear Structure Formula: 2ClH*C12H17N3O Molecular Formula: C12H17N3O*2ClH Molecular Weight: 292.208 InChI Key: IRWDGSABEUUHJZ-UHFFFAOYSA-N Note:

2 HCl N O

NH NH 2

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); (A1) English, View in Reaxys

Reaxys ID 24667271 View in Reaxys

111/323 Chemical Name: 4-hydroxybenzylpiperazine dihydrobromide Linear Structure Formula: 2BrH*C11H16N2O Molecular Formula: 2BrH*C11H16N2O Molecular Weight: 354.085 InChI Key: JOWCZTOKPOEUBC-UHFFFAOYSA-N Note:

2 HBr

NH N

Patent-Specific Data (1) Location in Patent References

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Page/Page column

Reaxys ID 26611655 View in Reaxys

112/323 Chemical Name: 1-(2,4-difluorobenzyl)piperazine hydrochloride Linear Structure Formula: ClH*C11H14F2N2 Molecular Formula: C11H14F2N2*ClH Molecular Weight: 248.703 Note:

F N

HCl NH

Reaxys ID 176236 View in Reaxys

113/323 CAS Registry Number: 100800-14-4 Chemical Name: 1-(4-methoxymethyl-benzyl)-piperazine; 1-(4Methoxymethyl-benzyl)-piperazin Linear Structure Formula: C13H20N2O Molecular Formula: C13H20N2O Molecular Weight: 220.315 Type of Substance: heterocyclic InChI Key: FMQNTZPKIRKYDG-UHFFFAOYSA-N Note:

O NH N

Boiling Point (1) Boiling Point [°C] 147 - 149

Pressure (Boiling Point) [Torr]

References

Patent; Miles Labor. Inc.; US2792398; (1954), View in Reaxys

Reaxys ID 518868 View in Reaxys

114/323 Chemical Name: 1-p-Isopropyl-benzyl-piperazin Linear Structure Formula: C14H22N2 Molecular Formula: C14H22N2 Molecular Weight: 218.342 Type of Substance: heterocyclic InChI Key: IADLEPYOAVUBSQ-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References I-8 Derivative (1) Comment (Derivative) Dihydrochlorid C14H22N2*2HCl: F: 278-281.5grad (Zers., unkorr., aus A.) Boiling Point (1) Boiling Point [°C]

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys References Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

Pressure (Boiling Point) [Torr]

References

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140 - 143

Ikeda; Yakugaku Zasshi; vol. 89; (1969); p. 677,685; Chem.Abstr.; vol. 71; nb. 61339; (1969), View in Reaxys

Reaxys ID 530461 View in Reaxys

115/323 CAS Registry Number: 35340-70-6 Chemical Name: 2,6-dimethoxy-3-piperazin-1-ylmethyl-phenol Linear Structure Formula: C13H20N2O3 Molecular Formula: C13H20N2O3 Molecular Weight: 252.313 Type of Substance: heterocyclic InChI Key: MQRLYFVZRNUVOO-UHFFFAOYSA-N Note:

O HO

N NH

Derivative (1) Comment (Derivative)

References

Dihydrochlorid Naito; Osumi; Kitao; Tetsuo; Kitaura; Fujita; Journal of pharmaceutical sciences; vol. 60; nb. 8; (1971); p. C13H20N2O3*2H 1257 - 1259, View in Reaxys Cl, F: 240-245grad, Zers.; NMR;

Reaxys ID 541339 View in Reaxys

116/323 Chemical Name: 2-Chlor-4-nitrobenzylpiperazin Linear Structure Formula: C11H14ClN3O2 Molecular Formula: C11H14ClN3O2 Molecular Weight: 255.704 Type of Substance: heterocyclic InChI Key: YCSSVPGXQBOTCU-UHFFFAOYSA-N Note:

Cl N O

N O

Substance Label (1) Label References V

Patent; Rhone-Poulenc S.A.; FRM23; (1960); Chem.Abstr.; vol. 58; nb. 3444e; (1963), View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

Patent; Rhone-Poulenc S.A.; FRM23; (1960); Chem.Abstr.; vol. 58; nb. 3444e; (1963), View in Reaxys

Reaxys ID 782363 View in Reaxys

117/323 Chemical Name: 2-methyl-6-piperazin-1-ylmethyl-phenol; 6-Piperazinomethyl-2-methylphenol Linear Structure Formula: C12H18N2O Molecular Formula: C12H18N2O Molecular Weight: 206.288 Type of Substance: heterocyclic InChI Key: NNLRLFCECBRPIT-UHFFFAOYSA-N Note:

OH N NH

Substance Label (1) Label References IV

Muehlenbruch; Roth; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 304; (1971); p. 819,822, View in Reaxys

Derivative (1)

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Comment (Derivative)

References

Dihydrochlorid: aus II, Ra-Ni/ N2H4*H2O; F: 257grad, IR

Muehlenbruch; Roth; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 304; (1971); p. 819,822, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Muehlenbruch; Roth; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 304; (1971); p. 819,822, View in Reaxys

Reaxys ID 782364 View in Reaxys

118/323 CAS Registry Number: 55212-33-4 Chemical Name: 1-(2-methylsulfanyl-benzyl)-piperazine Linear Structure Formula: C12H18N2S Molecular Formula: C12H18N2S Molecular Weight: 222.354 Type of Substance: heterocyclic InChI Key: VMELBBDZRYZILQ-UHFFFAOYSA-N Note:

S N NH

Substance Label (1) Label References XIXb

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Derivative (1) Comment (Derivative) Maleat: F: 138-139grad; Pharmakolog. Eigenschaften

References Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

96 - 97

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- NMR troscopy) Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Reaxys ID 785027 View in Reaxys

119/323 CAS Registry Number: 55212-34-5 Chemical Name: 1-(3-methylsulfanyl-benzyl)-piperazine Linear Structure Formula: C12H18N2S Molecular Formula: C12H18N2S Molecular Weight: 222.354 Type of Substance: heterocyclic InChI Key: SXSKFCQMDACWEI-UHFFFAOYSA-N Note:

H N

Substance Label (1) Label References

250/337

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XXb

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Derivative (1) Comment (Derivative) Maleat: F: 109-110grad; Pharmakolog. Eigenschaften Boiling Point (1) Boiling Point [°C] 125 - 128

References Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Pressure (Boiling Point) [Torr]

References

Protiva; Rajsner; Trcka; et al.; Collection of Czechoslovak Chemical Communications; vol. 40; nb. 12; (1975); p. 3904 - 3923, View in Reaxys

Reaxys ID 786410 View in Reaxys

120/323

CAS Registry Number: 21867-70-9 Chemical Name: 1-(4-ethoxy-benzyl)-piperazine; N-(4-Ethoxybenzyl)piperazin Linear Structure Formula: C13H20N2O Molecular Formula: C13H20N2O Molecular Weight: 220.315 Type of Substance: heterocyclic InChI Key: UBALQHBNQQCDGM-UHFFFAOYSA-N Note:

NH N

Substance Label (1) Label References IIi

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Boiling Point (1) Boiling Point [°C] 162 - 163

Pressure (Boiling Point) [Torr]

References

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5406

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

589

Density (1) 1 of 1

Density [g·cm-3]

1.0346

Measurement Temperature [°C]

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Reaxys ID 790224 View in Reaxys

121/323

251/337

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CAS Registry Number: 21867-71-0 Chemical Name: 1-(4-propoxy-benzyl)-piperazine; N-(4-n-Propoxybenzyl)piperazin Linear Structure Formula: C14H22N2O Molecular Formula: C14H22N2O Molecular Weight: 234.341 Type of Substance: heterocyclic InChI Key: JNRDBTWOUHUGSM-UHFFFAOYSA-N Note:

NH N

Substance Label (1) Label References IIj

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Boiling Point (1) Boiling Point [°C] 168 - 169

Pressure (Boiling Point) [Torr]

References

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5331

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

589

Density (1) 1 of 1

Density [g·cm-3]

1.0294

Measurement Temperature [°C]

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Reaxys ID 790254 View in Reaxys

122/323 Chemical Name: 2,4-dibromo-6-piperazin-1-ylmethyl-aniline Linear Structure Formula: C11H15Br2N3 Molecular Formula: C11H15Br2N3 Molecular Weight: 349.068 Type of Substance: heterocyclic InChI Key: YJJQMOFOBJQWNT-UHFFFAOYSA-N Note:

NH 2 Br

N NH Br

Substance Label (1) Label References Seite 14

Patent; Takeda Chem. Ind.; FR2291757; (1976); DE2551355; (1976); Chem.Abstr.; vol. 85; nb. 94405, View in Reaxys

Derivative (1) Comment (Derivative)

References

Hydrochlorid: F: 194-196grad

Patent; Takeda Chem. Ind.; FR2291757; (1976); DE2551355; (1976); Chem.Abstr.; vol. 85; nb. 94405, View in Reaxys

Reaxys ID 790976 View in Reaxys

123/323

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CAS Registry Number: 21867-74-3 Chemical Name: 1-(4-isobutoxy-benzyl)-piperazine; N-(4-Isobutoxybenzyl)piperazin Linear Structure Formula: C15H24N2O Molecular Formula: C15H24N2O Molecular Weight: 248.368 Type of Substance: heterocyclic InChI Key: WGTBQMZUCWMPOH-UHFFFAOYSA-N Note:

NH N

Substance Label (1) Label References IIm

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

95 - 96

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys Boiling Point (1) Boiling Point [°C] 161 - 163

Pressure (Boiling Point) [Torr]

References

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Reaxys ID 790998 View in Reaxys

124/323

CAS Registry Number: 21867-73-2 Chemical Name: 1-(4-butoxy-benzyl)-piperazine; N-(4-n-Butoxybenzyl)piperazin Linear Structure Formula: C15H24N2O Molecular Formula: C15H24N2O Molecular Weight: 248.368 Type of Substance: heterocyclic InChI Key: DLEWDSSLJATWIV-UHFFFAOYSA-N Note:

NH N

Substance Label (1) Label References II l

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

81 - 83

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys Boiling Point (1) Boiling Point [°C] 189 - 190

Pressure (Boiling Point) [Torr]

References

Mndzhoyan et al.; Armyanskii Khimicheskii Zhurnal; vol. 21; nb. 7; (1968); p. 603,604-614; Chem.Abstr.; vol. 70; nb. 96754t; (1969), View in Reaxys

Reaxys ID 794622 View in Reaxys HO O

125/323 Chemical Name: 2-hydroxy-4-piperazin-1-ylmethyl-benzoic acid Linear Structure Formula: C12H16N2O3 Molecular Formula: C12H16N2O3 Molecular Weight: 236.271

N NH

253/337

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Type of Substance: heterocyclic InChI Key: SMMZIYPUMSHXLY-UHFFFAOYSA-N Note: Derivative (1) Comment (Derivative) Dihydrochlorid: F: 180-185grad

References Patent; Science Union and Cie.; BE630639; (1963); Chem.Abstr.; vol. 61; nb. 668; (1964), View in Reaxys

Reaxys ID 3719147 View in Reaxys

126/323 CAS Registry Number: 131591-42-9 Chemical Name: 1-(4-tert-butyl-benzyl)-piperazine; dihydrochloride; 1-(4-tert-Butyl-benzyl)-piperazin; Dihydrochlorid Linear Structure Formula: C15H24N2*2ClH Molecular Formula: C15H24N2*2ClH Molecular Weight: 305.291 Type of Substance: heterocyclic InChI Key: FGKHHGRUCMOIED-UHFFFAOYSA-N Note:

N Cl 2 H

Melting Point (1) 1 of 1

Melting Point [°C]

319 - 320

Solvent (Melting Point)

ethanol

Comment (Melting Point)

with:0.5 Mol.H2O (solvent).Decomp.

Patent; Brit. Drug Houses Ltd.; GB840358; (1957), View in Reaxys

Reaxys ID 3723449 View in Reaxys

127/323

NH N

Chemical Name: 1-(4-bromo-benzyl)-piperazine; dihydrochloride; 1-(4-Brom-benzyl)-piperazin; Dihydrochlorid Linear Structure Formula: C11H15BrN2*2ClH Molecular Formula: C11H15BrN2*2ClH Molecular Weight: 328.079 Type of Substance: heterocyclic InChI Key: GBFYODBHQSMYIV-UHFFFAOYSA-N Note:

Cl 2 H

Melting Point (1) 1 of 1

Solvent (Melting Point)

H2O

Comment (Melting Point)

Kristalle, die unterhalb 290grad nicht schmelzen..

Baltzly et al.; Journal of the American Chemical Society; vol. 76; (1954); p. 1165, View in Reaxys

Reaxys ID 3735983 View in Reaxys

128/323 Chemical Name: 1-(3,4-dichloro-benzyl)-piperazine; dihydrochloride; 1-(3,4-Dichlor-benzyl)-piperazin; Dihydrochlorid Linear Structure Formula: C11H14Cl2N2*2ClH Molecular Formula: C11H14Cl2N2*2ClH Molecular Weight: 318.073 Type of Substance: heterocyclic InChI Key: HSWQXYKCUISMQO-UHFFFAOYSA-N

H N

N Cl 2 H

Cl Cl

254/337

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Note: Melting Point (1) 1 of 1

Melting Point [°C]

257

Solvent (Melting Point)

ethanol; ethyl acetate

Comment (Melting Point)

Decomp.

Baltzly et al.; Journal of the American Chemical Society; vol. 76; (1954); p. 1165, View in Reaxys

Reaxys ID 3845781 View in Reaxys

129/323

CAS Registry Number: 122678-61-9 Chemical Name: 4-benzyl-piperazine-1-carboxylic acid ; 4-benzyl-piperazine salt; 4-Benzyl-piperazin-1-carbonsaeure; 4-Benzyl-piperazin-Salz Linear Structure Formula: C12H16N2O2*C11H16N2 Molecular Formula: C11H16N2*C12H16N2O2 Molecular Weight: 396.533 Type of Substance: heterocyclic InChI Key: UEJJNSGMZXLGAV-UHFFFAOYSA-N Note:

N NH N HO

Melting Point (1) 1 of 1

Melting Point [°C]

99 - 100

Comment (Melting Point)

with:1 Mol.H2O (solvent).Decomp.bei schnellem Erhitzen..

Craig; Journal of the Chemical Society; (1959); p. 3634, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

3390 - 1000 cm**(-1)

Craig; Journal of the Chemical Society; (1959); p. 3634, View in Reaxys

Reaxys ID 4064080 View in Reaxys

130/323

NH N

CAS Registry Number: 55037-86-0 Chemical Name: 1-(p-Chlorbenzyl)piperazin-Methansulfonat Linear Structure Formula: C11H15ClN2*CH4O3S Molecular Formula: CH4O3S*C11H15ClN2 Molecular Weight: 306.813 Type of Substance: heterocyclic InChI Key: NDKDITJSMPVJSL-UHFFFAOYSA-N Note:

S HO

Substance Label (1) Label References XXI

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

181 - 182

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys

255/337

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Reaxys ID 4069036 View in Reaxys

131/323

HO N

Z O

CAS Registry Number: 61014-84-4 Chemical Name: 1-(2,4,6-Trimethylbenzyl)-piperazin-maleat Linear Structure Formula: C14H22N2*C4H4O4 Molecular Formula: C4H4O4*C14H22N2 Molecular Weight: 334.415 Type of Substance: heterocyclic InChI Key: HFRZTGINFJAHMZ-BTJKTKAUSA-N Note:

Substance Label (1) Label References V-M

Protiva et al.; Collection of Czechoslovak Chemical Communications; vol. 41; (1976); p. 1034,1037, 1040, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

176 - 178

Solvent (Melting Point)

aq. ethanol

Protiva et al.; Collection of Czechoslovak Chemical Communications; vol. 41; (1976); p. 1034,1037, 1040, View in Reaxys

Reaxys ID 4092848 View in Reaxys

132/323

CAS Registry Number: 29140-82-7 Linear Structure Formula: C12H16N2S2*C11H16N2 Molecular Formula: C11H16N2*C12H16N2S2 Molecular Weight: 428.666 Type of Substance: heterocyclic InChI Key: RCLXDLIBOHDVRH-UHFFFAOYSA-N Note:

N NH N HS

Substance Label (1) Label References 32

Florvall; Corrodi; Acta Pharmaceutica Suecica; vol. 7; (1970); p. 7,15, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

168 - 170

Florvall; Corrodi; Acta Pharmaceutica Suecica; vol. 7; (1970); p. 7,15, View in Reaxys

Reaxys ID 4116586 View in Reaxys

133/323

CAS Registry Number: 6792-69-4; 10510-56-2 Chemical Name: N-Benzyl-piperazin-tartrat Linear Structure Formula: C11H16N2*C4H6O6 Molecular Formula: C4H6O6*C11H16N2 Molecular Weight: 326.349 Type of Substance: heterocyclic InChI Key: RMTLWEKQURMMKH-UHFFFAOYSA-N Note:

NH HO OH

Melting Point (1) 1 of 1

Melting Point [°C]

152

Patent; Wellcome Found.; NL6507758; (1965); Chem.Abstr.; vol. 65; nb. 7196d; (1966), View in Reaxys

256/337

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Reaxys ID 4116587 View in Reaxys

134/323

N NH

CAS Registry Number: 6792-69-4; 10510-56-2 Chemical Name: 1-Benzylpiperazin-Tartrat Linear Structure Formula: C11H16N2*C4H6O6 Molecular Formula: C4H6O6*C11H16N2 Molecular Weight: 326.349 Type of Substance: heterocyclic InChI Key: RMTLWEKQURMMKH-YKWZRPGSSA-N Note:

Substance Label (1) Label References XX

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

155.5 - 156.5

Vejdelek et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2276,2277,2280, View in Reaxys

Reaxys ID 4249268 View in Reaxys

135/323 CAS Registry Number: 75341-33-2 Linear Structure Formula: C11H16N2O Molecular Formula: C11H16N2O Molecular Weight: 192.261 Type of Substance: heterocyclic InChI Key: CNRXJITXJZQWPJ-UHFFFAOYSA-N Note:

NH N

Reaxys ID 4584656 View in Reaxys

136/323

CAS Registry Number: 84418-45-1 Chemical Name: 1-(p-Isopropylbenzyl)piperazine hydrochloride Linear Structure Formula: C14H22N2*ClH Molecular Formula: C14H22N2*ClH Molecular Weight: 254.803 Type of Substance: heterocyclic InChI Key: WJDNKELXXNAINH-UHFFFAOYSA-N Note:

Melting Point (1) 1 of 1

Melting Point [°C]

268 - 274

Carpino, Louis A.; Mansour, E. M. E.; Knapczyk, Jerome; Journal of Organic Chemistry; vol. 48; nb. 5; (1983); p. 666 - 669, View in Reaxys

Reaxys ID 4620549 View in Reaxys

137/323 CAS Registry Number: 107165-54-8 Chemical Name: 1-benzylpiperazine dimethanesulfonate Linear Structure Formula: C11H16N2*2CH4O3S Molecular Formula: 2CH4O3S*C11H16N2 Molecular Weight: 368.475 Type of Substance: heterocyclic InChI Key: CQPUARMVMSCOTG-UHFFFAOYSA-N

2 HO

NH N

257/337

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Note: Melting Point (1) 1 of 1

Melting Point [°C]

204 - 206

Solvent (Melting Point)

ethanol

Protiva; Dlabac; Valchar; et al.; Collection of Czechoslovak Chemical Communications; vol. 51; nb. 1; (1986); p. 156 - 166, View in Reaxys

Reaxys ID 4623758 View in Reaxys

138/323

S HO

CAS Registry Number: 77602-91-6 Chemical Name: 1-(4-fluorobenzyl)piperazine dimethanesulfonate Linear Structure Formula: C11H15FN2*2CH4O3S Molecular Formula: 2CH4O3S*C11H15FN2 Molecular Weight: 386.466 Type of Substance: heterocyclic InChI Key: JBNVBMZDXLROMK-UHFFFAOYSA-N Note:

NH N

Melting Point (1) 1 of 1

Melting Point [°C]

202 - 204

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Crystallization with 1 Mol(s) H2O

Bartl; Dlabac; Protiva; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 11; (1980); p. 3182 3189, View in Reaxys

Reaxys ID 4626757 View in Reaxys

139/323

CAS Registry Number: 77602-90-5 Chemical Name: 1-(4-fluorobenzyl)piperazine bis(hydrogen maleate) Linear Structure Formula: C11H15FN2*2C4H4O4 Molecular Formula: 2C4H4O4*C11H15FN2 Molecular Weight: 426.399 Type of Substance: heterocyclic InChI Key: WMVOLHQERIBVNV-BTJKTKAUSA-N Note:

Melting Point (1) 1 of 1

Melting Point [°C]

167 - 168

Solvent (Melting Point)

H2O

Bartl; Dlabac; Protiva; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 11; (1980); p. 3182 3189, View in Reaxys

Reaxys ID 4831489 View in Reaxys

140/323

Linear Structure Formula: C11H16N2*C2H4O2 Molecular Formula: C2H4O2*C11H16N2 Molecular Weight: 236.314 Type of Substance: heterocyclic InChI Key: DLJQSRXRDKNYHY-UHFFFAOYSA-N Note:

258/337

2016-05-20 15:00:44

Substance Label (1) Label References 2n

Cliffe; Ifill; Mansell; Todd; White; Tetrahedron Letters; vol. 32; nb. 46; (1991); p. 6789 - 6792, View in Reaxys

Reaxys ID 5664239 View in Reaxys

141/323 CAS Registry Number: 90754-98-6 Linear Structure Formula: C12H15F3N2*2ClH Molecular Formula: C12H15F3N2*2ClH Molecular Weight: 317.182 Type of Substance: heterocyclic InChI Key: GVOKACNFIJZZFQ-UHFFFAOYSA-N Note:

F Cl 2 H

Substance Label (1) Label References 15*2HCl

Scotto di Tella; Dessaigne; Boyer; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 2; (1984); p. 131 - 135, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

162

Solvent (Melting Point)

acetone; propan-1-ol

Scotto di Tella; Dessaigne; Boyer; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 2; (1984); p. 131 135, View in Reaxys

Reaxys ID 5946476 View in Reaxys

142/323 CAS Registry Number: 158776-75-1 Linear Structure Formula: C13H20N2O2 Molecular Formula: C13H20N2O2 Molecular Weight: 236.314 Type of Substance: heterocyclic InChI Key: RHKQXCFGQFIGNO-UHFFFAOYSA-N Note:

O O

N NH

Substance Label (1) Label References 3d

Ferte, Jacques; Kuehnel, Jean-Marc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 - 489, View in Reaxys

Reaxys ID 6010737 View in Reaxys

143/323 CAS Registry Number: 113698-78-5 Linear Structure Formula: C12H18N2O*2ClH Molecular Formula: C12H18N2O*2ClH Molecular Weight: 279.21 Type of Substance: heterocyclic InChI Key: JOFJCFSMTNJALX-UHFFFAOYSA-N Note:

O Cl 2 H

N NH

Substance Label (1) Label References 5a ( 2-OMe, m=2 )

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Melting Point (1)

259/337

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1 of 1

Melting Point [°C]

207 - 209

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Crystallization with 2 Mol(s) HCl

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Reaxys ID 6013503 View in Reaxys

144/323 CAS Registry Number: 113698-79-6 Linear Structure Formula: C12H18N2O*2ClH Molecular Formula: C12H18N2O*2ClH Molecular Weight: 279.21 Type of Substance: heterocyclic InChI Key: RJBBLLPOVJBNMC-UHFFFAOYSA-N Note:

H N

N Cl 2 H

Substance Label (1) Label References 5b ( 3-OMe, m=2 )

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

216 - 218

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Crystallization with 2 Mol(s) HCl

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Reaxys ID 6017651 View in Reaxys

145/323 CAS Registry Number: 113698-80-9 Linear Structure Formula: C13H20N2O2*2ClH Molecular Formula: C13H20N2O2*2ClH Molecular Weight: 309.236 Type of Substance: heterocyclic InChI Key: RQPHTJYIUSJXSD-UHFFFAOYSA-N Note:

O O

Cl 2 H

N NH

Substance Label (1) Label References 5d ( 2,3-(OMe)2, m=2 )

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

215 - 218

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Decomposition. Crystallization with 2 Mol(s) HCl

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

260/337

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Reaxys ID 6023113 View in Reaxys

146/323 CAS Registry Number: 113698-83-2 Chemical Name: 1-(2,4,6-trimethoxybenzyl)piperazine Linear Structure Formula: C14H22N2O3*2ClH Molecular Formula: C14H22N2O3*2ClH Molecular Weight: 339.262 Type of Substance: heterocyclic InChI Key: QLMVKYRPRVCCRK-UHFFFAOYSA-N Note:

O N O

Cl 2 H NH

Substance Label (1) Label References 5i (2,4,6-(OMe)3, m=2)

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

218 - 224

Solvent (Melting Point)

methanol; diethyl ether

Comment (Melting Point)

Decomposition. Crystallization with 2 Mol(s) HCl

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Reaxys ID 6028009 View in Reaxys

NH N

147/323

Linear Structure Formula: C12H18N2O*2ClH*H2O Molecular Formula: C12H18N2O*2ClH*H2O Molecular Weight: 297.225 Type of Substance: heterocyclic InChI Key: ZRXJIQNDZGUQMH-UHFFFAOYSA-N Note:

Cl 2 H

Substance Label (1) Label References 5c ( 4-OMe, m=2 )

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

253 - 255

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Decomposition. Crystallization with 2 Mol(s) HCl

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Reaxys ID 6030401 View in Reaxys

Linear Structure Formula: 4C13H20N2O2*8ClH*H2O Molecular Formula: 4C13H20N2O2*8ClH*H2O Molecular Weight: 1254.96 Type of Substance: heterocyclic InChI Key: PHWMCDDNPTYJCA-UHFFFAOYSA-N Note:

Cl 8 H

O N

148/323

H NH

Substance Label (1) Label References

261/337

2016-05-20 15:00:44

5e ( 2,4-(OMe)2, m=2 )

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

187 - 188

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Decomposition. Crystallization with 2 Mol(s) HCl

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Reaxys ID 6031031 View in Reaxys

149/323 Linear Structure Formula: 4C13H20N2O2*8ClH*H2O Molecular Formula: 4C13H20N2O2*8ClH*H2O Molecular Weight: 1254.96 Type of Substance: heterocyclic InChI Key: UIZQNKVTBAFNQR-UHFFFAOYSA-N Note:

Cl 8 H O

H NH

Substance Label (1) Label References 5f ( 3,4-(OMe)2, m=2 )

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

228 - 229

Solvent (Melting Point)

methanol; diethyl ether

Comment (Melting Point)

Decomposition. Crystallization with 2 Mol(s) HCl

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Reaxys ID 6031067 View in Reaxys

150/323 Linear Structure Formula: 4C13H20N2O2*8ClH*H2O Molecular Formula: 4C13H20N2O2*8ClH*H2O Molecular Weight: 1254.96 Type of Substance: heterocyclic InChI Key: TWUUPQWQZVKPRV-UHFFFAOYSA-N Note:

H N

N 4

Cl 8 H H

Substance Label (1) Label References 5g ( 3,5-(OMe)2, m=2 )

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

220 - 221

Solvent (Melting Point)

ethanol; diethyl ether

Comment (Melting Point)

Decomposition. Crystallization with 2 Mol(s) HCl

Ohtaka; Fujimoto; Yoshida; Kanazawa; Ito; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2782 - 2791, View in Reaxys

262/337

2016-05-20 15:00:44

Reaxys ID 6396703 View in Reaxys

151/323

Linear Structure Formula: C13H21N3 Molecular Formula: C13H21N3 Molecular Weight: 219.33 Type of Substance: heterocyclic InChI Key: WBSHKPALUOHZAK-UHFFFAOYSA-N Note:

NH N

Reaxys ID 6401187 View in Reaxys

152/323

N NH

Boiling Point (1) Boiling Point [°C] 164 - 167

CAS Registry Number: 118630-31-2 Chemical Name: 1-<3-Bromo-4-(dimethylamino)benzyl>piperazine; 1-[3-Bromo-4-(dimethylamino)benzyl]piperazine Linear Structure Formula: C13H20BrN3 Molecular Formula: C13H20BrN3 Molecular Weight: 298.226 Type of Substance: heterocyclic InChI Key: YEWPDTJGYQWHBW-UHFFFAOYSA-N Note:

Pressure (Boiling Point) [Torr]

References

0.05

Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys

Reaxys ID 6402553 View in Reaxys

153/323 CAS Registry Number: 118630-32-3 Chemical Name: 1-<2-Chloro-4-(dimethylamino)benzyl>piperazine; 1-[2-Chloro-4-(dimethylamino)benzyl]piperazine Linear Structure Formula: C13H20ClN3 Molecular Formula: C13H20ClN3 Molecular Weight: 253.775 Type of Substance: heterocyclic InChI Key: MLLZAMOGCGMHBY-UHFFFAOYSA-N Note:

Cl N N

Melting Point (1) 1 of 1

Melting Point [°C]

54 - 56

Meyer; Tomcufcik; Chan; Haug; Journal of Medicinal Chemistry; vol. 32; nb. 3; (1989); p. 593 - 597, View in Reaxys

Reaxys ID 6887686 View in Reaxys

154/323

263/337

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Chemical Name: 1-benzylpiperazine Linear Structure Formula: C11H16N2*2C6H3N3O7 Molecular Formula: 2C6H3N3O7*C11H16N2 Molecular Weight: 634.473 Type of Substance: heterocyclic InChI Key: JNGVWOMLEOFRJV-UHFFFAOYSA-N Note:

O O

N O

N NH

2HO

N O

Substance Label (1) Label References 5c*dipicrate

Kawaguchi, Mamoru; Hayashi, Osamu; Kanamoto, Masahiro; Hamada, Masayuki; Yamamoto, Yukio; Oda, Jun'ichi; Agricultural and Biological Chemistry; vol. 51; nb. 2; (1987); p. 435 - 440, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

257 - 258

Kawaguchi, Mamoru; Hayashi, Osamu; Kanamoto, Masahiro; Hamada, Masayuki; Yamamoto, Yukio; Oda, Jun'ichi; Agricultural and Biological Chemistry; vol. 51; nb. 2; (1987); p. 435 - 440, View in Reaxys

Reaxys ID 7669851 View in Reaxys

155/323 Linear Structure Formula: C13H20N2O2*ClH Molecular Formula: C13H20N2O2*ClH Molecular Weight: 272.775 Type of Substance: heterocyclic InChI Key: JLZYALQSEPFDRB-UHFFFAOYSA-N Note:

H N

N O

Melting Point (1) 1 of 1

Melting Point [°C]

151 - 152

Masaguer, Christian F.; Ravina, Enrique; Tetrahedron Letters; vol. 37; nb. 29; (1996); p. 5171 - 5174, View in Reaxys

Reaxys ID 8287924 View in Reaxys

156/323

Linear Structure Formula: C13H20N2O2*ClH Molecular Formula: C13H20N2O2*ClH Molecular Weight: 272.775 Type of Substance: heterocyclic InChI Key: MFRIQPBHLRTPKG-UHFFFAOYSA-N Note:

Substance Label (1) Label References 3e*HCl

Ferte, Jacques; Kuehnel, Jean-Marc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 - 489, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

220 - 223

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

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Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Ferte, Jacques; Kuehnel, Jean-Marc; Chapuis, Genevieve; Rolland, Yves; Lewin, Guy; Schwaller, Marc A.; Journal of Medicinal Chemistry; vol. 42; nb. 3; (1999); p. 478 - 489, View in Reaxys

Reaxys ID 8337862 View in Reaxys

157/323 Linear Structure Formula: C16H23N3O2 Molecular Formula: C16H23N3O2 Molecular Weight: 289.378 Type of Substance: heterocyclic InChI Key: ALTOTQSMFUEFGV-UHFFFAOYSA-N Note:

O O

N H

N NH

Substance Label (1) Label References M8

Wu; McKown; Takacs; Jones; Reitz; Xenobiotica; vol. 29; nb. 5; (1999); p. 453 - 466, View in Reaxys

Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI); chemical ionization (CI)

Wu; McKown; Takacs; Jones; Reitz; Xenobiotica; vol. 29; nb. 5; (1999); p. 453 - 466, View in Reaxys

Reaxys ID 8343427 View in Reaxys

158/323 Linear Structure Formula: C16H25N3O2 Molecular Formula: C16H25N3O2 Molecular Weight: 291.393 Type of Substance: heterocyclic InChI Key: OAMODADBLOSMCD-UHFFFAOYSA-N Note:

O HO

N H

N NH

Substance Label (1) Label References M9

Wu; McKown; Takacs; Jones; Reitz; Xenobiotica; vol. 29; nb. 5; (1999); p. 453 - 466, View in Reaxys

Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI); chemical ionization (CI)

Wu; McKown; Takacs; Jones; Reitz; Xenobiotica; vol. 29; nb. 5; (1999); p. 453 - 466, View in Reaxys

Reaxys ID 8353608 View in Reaxys

159/323

N F

Chemical Name: 1-(4-fluorophenylmethyl)piperazine hydrobromide Linear Structure Formula: C11H15FN2*BrH Molecular Formula: BrH*C11H15FN2 Molecular Weight: 275.164 Type of Substance: heterocyclic InChI Key: GKYLWUHXXVVMOG-UHFFFAOYSA-N Note:

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Substance Label (1) Label References 16c*HBr

Reaxys ID 8509213 View in Reaxys

160/323

H N

Chemical Name: 4-Benzylpiperazine*borane complex Linear Structure Formula: C11H16N2*BH3 Molecular Formula: BH3*C11H16N2 Molecular Weight: 190.096 Type of Substance: heterocyclic InChI Key: SDFVPFGLKGZMDX-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 17

Perrio-Huard, Cecile; Aubert, Catherine; Lasne, Marie-Claire; Journal of the Chemical Society, Perkin Transactions 1; nb. 3; (2000); p. 311 - 316, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

125

Perrio-Huard, Cecile; Aubert, Catherine; Lasne, Marie-Claire; Journal of the Chemical Society, Perkin Transactions 1; nb. 3; (2000); p. 311 - 316, View in Reaxys NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Perrio-Huard, Cecile; Aubert, Catherine; Lasne, Marie-Claire; Journal of the Chemical Society, Perkin Transactions 1; nb. 3; (2000); p. 311 - 316, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Perrio-Huard, Cecile; Aubert, Catherine; Lasne, Marie-Claire; Journal of the Chemical Society, Perkin Transactions 1; nb. 3; (2000); p. 311 - 316, View in Reaxys 3 of 4

Nucleus (NMR Spectroscopy)

11B

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

128

Perrio-Huard, Cecile; Aubert, Catherine; Lasne, Marie-Claire; Journal of the Chemical Society, Perkin Transactions 1; nb. 3; (2000); p. 311 - 316, View in Reaxys

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4 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

11B

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

128

Perrio-Huard, Cecile; Aubert, Catherine; Lasne, Marie-Claire; Journal of the Chemical Society, Perkin Transactions 1; nb. 3; (2000); p. 311 - 316, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Perrio-Huard, Cecile; Aubert, Catherine; Lasne, Marie-Claire; Journal of the Chemical Society, Perkin Transactions 1; nb. 3; (2000); p. 311 - 316, View in Reaxys

Reaxys ID 8581788 View in Reaxys H N

161/323 2

Chemical Name: 1-(3-chlorobenzyl)piperazine dihydrochloride Linear Structure Formula: C11H15ClN2*2ClH Molecular Formula: C11H15ClN2*2ClH Molecular Weight: 283.628 Type of Substance: heterocyclic InChI Key: PHHFZSZJEUSYDV-UHFFFAOYSA-N Note:

HCl

Substance Label (1) Label References 5d*2HCl

Radl, Stanislav; Hezky, Petr; Proska, Jan; Hejnova, Lucie; Krejci, Ivan; Archiv der Pharmazie; vol. 333; nb. 5; (2000); p. 107 - 112, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

214 - 217

Solvent (Melting Point)

ethanol

Radl, Stanislav; Hezky, Petr; Proska, Jan; Hejnova, Lucie; Krejci, Ivan; Archiv der Pharmazie; vol. 333; nb. 5; (2000); p. 107 - 112, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Radl, Stanislav; Hezky, Petr; Proska, Jan; Hejnova, Lucie; Krejci, Ivan; Archiv der Pharmazie; vol. 333; nb. 5; (2000); p. 107 - 112, View in Reaxys Pharmacological Data (5) 1 of 5

Comment (Pharmacological Data)

Bioactivities present

Radl, Stanislav; Hezky, Petr; Proska, Jan; Hejnova, Lucie; Krejci, Ivan; Archiv der Pharmazie; vol. 333; nb. 5; (2000); p. 107 - 112, View in Reaxys 2 of 5

Effect (Pharmacological Data)

analgesic, other

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Species or Test-System (Pharmacological Data)

NMRI mouse

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

30 mg/kg

Kind of Dosing (Pharmacological Data)

30 min prior to HOAc injection

Method (Pharmacological Data)

writhings induced by 0.7 percent HOAc i.p.; counted for 20 min

Results

7 percent decrease of the stretching movements

Radl, Stanislav; Hezky, Petr; Proska, Jan; Hejnova, Lucie; Krejci, Ivan; Archiv der Pharmazie; vol. 333; nb. 5; (2000); p. 107 - 112, View in Reaxys 3 of 5

Effect (Pharmacological Data)

analgesic, other

Species or Test-System (Pharmacological Data)

NMRI mouse

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

30 mg/kg

Method (Pharmacological Data)

hot plate test; mice placed into a glass cylinder; plate temp. maintained at 54 deg C; time necessary to induce the licking reflex of the forepaws or jumping recorded 30 and 60 min after title comp. application

Results

38 percent prolongation of the licking latencies

Radl, Stanislav; Hezky, Petr; Proska, Jan; Hejnova, Lucie; Krejci, Ivan; Archiv der Pharmazie; vol. 333; nb. 5; (2000); p. 107 - 112, View in Reaxys 4 of 5

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

adult rat striatal membrane

Sex

male

Kind of Dosing (Pharmacological Data)

used in 1E-6 M concentrations

Method (Pharmacological Data)

displacement of 2.00 nM <3H>-5-HT; termination by filtration; filter retained radioactivity measured by liq. scintillation spectrometry

Further Details (Pharmacological Data)

binding affinity for the 5-HT1B receptor evaluated

Results

85 percent of radioligand retained bound after displacement period

Radl, Stanislav; Hezky, Petr; Proska, Jan; Hejnova, Lucie; Krejci, Ivan; Archiv der Pharmazie; vol. 333; nb. 5; (2000); p. 107 - 112, View in Reaxys 5 of 5

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

adult rat hippocampal membrane

Sex

male

Kind of Dosing (Pharmacological Data)

used in 1E-6 M concentrations

Method (Pharmacological Data)

displacement of 0.25 nM <3H>-8-OH-DPAT; termination by filtration; filter retained radioactivity measured by liq. scintillation spectrometry

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Further Details (Pharmacological Data)

binding affinity for the 5-HT1A receptor evaluated

Results

88 percent of radioligand retained bound after displacement period

Radl, Stanislav; Hezky, Petr; Proska, Jan; Hejnova, Lucie; Krejci, Ivan; Archiv der Pharmazie; vol. 333; nb. 5; (2000); p. 107 - 112, View in Reaxys

Reaxys ID 9261468 View in Reaxys

162/323 CAS Registry Number: 118220-96-5 Linear Structure Formula: C11H12D4N2 Molecular Formula: C11H16N2 Molecular Weight: 180.23 Type of Substance: heterocyclic InChI Key: IQXXEPZFOOTTBA-KXGHAPEVSA-N Note:

2H 2H

N NH 2H

Reaxys ID 9263815 View in Reaxys

163/323 Linear Structure Formula: C12H17ClN2O Molecular Formula: C12H17ClN2O Molecular Weight: 240.733 Type of Substance: heterocyclic InChI Key: USKLTPRRCHGTQO-UHFFFAOYSA-N Note:

O N NH

Reaxys ID 9263869 View in Reaxys

164/323 Linear Structure Formula: C12H17FN2 Molecular Formula: C12H17FN2 Molecular Weight: 208.279 Type of Substance: heterocyclic InChI Key: FKWZSNVKYGCYED-UHFFFAOYSA-N Note:

H N

Reaxys ID 9267660 View in Reaxys

165/323 Linear Structure Formula: C13H19ClN2O Molecular Formula: C13H19ClN2O Molecular Weight: 254.76 Type of Substance: heterocyclic InChI Key: AGBMRTWKONJJMH-UHFFFAOYSA-N Note:

O N NH Cl

Reaxys ID 9268224 View in Reaxys

166/323

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Linear Structure Formula: C14H21ClN2O Molecular Formula: C14H21ClN2O Molecular Weight: 268.787 Type of Substance: heterocyclic InChI Key: GQWZYEWMSVDCMW-UHFFFAOYSA-N Note:

O N NH Cl

Reaxys ID 9270094 View in Reaxys

167/323 Linear Structure Formula: C11H13ClF2N2 Molecular Formula: C11H13ClF2N2 Molecular Weight: 246.687 Type of Substance: heterocyclic InChI Key: VKMGWJMJIZPTNJ-UHFFFAOYSA-N Note:

F N NH

Cl F

Reaxys ID 9270095 View in Reaxys

168/323 Linear Structure Formula: C11H13ClF2N2 Molecular Formula: C11H13ClF2N2 Molecular Weight: 246.687 Type of Substance: heterocyclic InChI Key: TWYPUCMNAXJDRL-UHFFFAOYSA-N Note:

Cl F

N NH

Reaxys ID 9330167 View in Reaxys

169/323 Linear Structure Formula: C13H20N2O Molecular Formula: C13H20N2O Molecular Weight: 220.315 Type of Substance: heterocyclic InChI Key: GOATYXBTKLSVSU-UHFFFAOYSA-N Note:

O N NH

Reaxys ID 9330168 View in Reaxys

170/323 Linear Structure Formula: C13H20N2O Molecular Formula: C13H20N2O Molecular Weight: 220.315 Type of Substance: heterocyclic InChI Key: VPVBTJQMHXERRH-UHFFFAOYSA-N Note:

O N NH

Reaxys ID 9397122 View in Reaxys

171/323 Linear Structure Formula: C12H18N2O Molecular Formula: C12H18N2O Molecular Weight: 206.288 Type of Substance: heterocyclic InChI Key: VBWCHVVSZCVMPN-UHFFFAOYSA-N

OH N NH

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Note: Substance Label (1) Label References prod., reaction 4

Page, Philip C. Bulman; Heaney, Harry; McGrath, Matthew J.; Sampler, Edward P.; Wilkins, Robert F.; Tetrahedron Letters; vol. 44; nb. 14; (2003); p. 2965 - 2970, View in Reaxys

Reaxys ID 9914973 View in Reaxys

172/323 Linear Structure Formula: C11H17N3O Molecular Formula: C11H17N3O Molecular Weight: 207.275 Type of Substance: heterocyclic InChI Key: WAIZCIMILZIFNO-UHFFFAOYSA-N Note:

H N

NH 2

Reaxys ID 10324370 View in Reaxys

173/323 Chemical Name: trimetazidinium tetraphenylborate Linear Structure Formula: 2C24H20B(1-)*C14H22N2O3*2H(1+) Molecular Formula: C14H22N2O3*2C24H20B*2H Molecular Weight: 906.824 Type of Substance: heterocyclic InChI Key: DOEQEOUBXBZMQA-UHFFFAOYSA-O Note:

O O

H+

B–

Substance Label (1) Label References Trim-TPB

Issa, Yousry M.; Abdel-Ghani, Nour T.; Ahmed, Howayda M.; Scientia Pharmaceutica; vol. 73; nb. 4; (2005); p. 173 - 193, View in Reaxys

Solubility (MCS) (1) 1 of 1

Solubility [g·l-1]

0.001904

Saturation

in pure solvent

Temperature (Solubility (MCS)) [°C]

Solvent (Solubility (MCS))

H2O

Issa, Yousry M.; Abdel-Ghani, Nour T.; Ahmed, Howayda M.; Scientia Pharmaceutica; vol. 73; nb. 4; (2005); p. 173 - 193, View in Reaxys

Reaxys ID 11139101 View in Reaxys

174/323 Chemical Name: 4-(2-trifluoromethylbenzyl)piperazine hydrochloride Linear Structure Formula: C12H15F3N2*HCl Molecular Formula: C12H15F3N2*ClH Molecular Weight: 280.721 InChI Key: JLYPTMOIWITOPH-UHFFFAOYSA-N Note:

F HCl

N NH

Substance Label (1) Label References

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Liu, Gang; Lynch, John K.; Freeman, Jennifer; Liu, Bo; Xin, Zhili; Zhao, Hongyu; Serby, Michael D.; Kym, Philip R.; Suhar, Tom S.; Smith, Harriet T.; Cao, Ning; Yang, Ruojing; Janis, Rich S.; Krauser, Joel A.; Cepa, Steven P.; Beno, David W. A.; Sham, Hing L.; Collins, Christine A.; Surowy, Teresa K.; Camp, Heidi S.; Journal of Medicinal Chemistry; vol. 50; nb. 13; (2007); p. 3086 - 3100, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Reaxys ID 11250314 View in Reaxys

175/323 Linear Structure Formula: HN(C2H4)2NCH2C6H4OC2H5 Molecular Formula: C13H20N2O Molecular Weight: 220.315 InChI Key: BQEOHXXGJIUXQE-UHFFFAOYSA-N Note:

O N NH

Substance Label (1) Label References 11

Jung, Ji Young; Ho Jung, Sun; Koh, Hun Yeong; European Journal of Medicinal Chemistry; vol. 42; nb. 7; (2007); p. 1044 - 1048, View in Reaxys

Reaxys ID 11348699 View in Reaxys

176/323 Type of Substance: mixture (composition partially given) Composition: Comp. Name: 1-(2,3,4-trimethoxybenzyl)piperazine; HAP; water Composition: Comp. Conc.: 1.0 percent; 0.1 percent Note:

No Structure

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; KABUSHIKI KAISHA SANGI; EP1797900; (2007); (A1) English, View in Reaxys 2 of 2

Effect (Pharmacological Data)

skin permeability; effect on

Species or Test-System (Pharmacological Data)

abdominal skin of hairless rat

Method (Pharmacological Data)

[Example 14: Skin permeability study of various drugs] Table 9 shows compositions used in the skin permeability study of various drugs (Examples 14-1 to 14-16). Compositions that do not contain HAP were prepared as controls (Comparative examples 4-1 to 4-16). [Study 6: Comparative study of skin permeability for various drugs] The skin permeability study was conducted using the abdominal skin of hairless rats. 16 ml of isotonic phosphate buffer (pH 7.1) was incubated at 37°C in the receptor phase (dermis side) while being stirred with a stirrer. The samples (1 g each) in Examples 14-1 to 14-16 and Comparative examples 4-1 to 4-16 were added (applied area, 3.14 cm2) to the donor phase (horny layer side). The top was sealed with laboratory film (Studies 6-1 to 6-16, and Controlled

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studies 6-1 to 6-16). The solutions were sampled from the receptor phase 24 hours after the start of study. The concentrations of drugs in the solutions were quantified by high performance liquid chromatography to determine the amounts of drugs permeated through the skin. The result is shown in Table 10; the values represent skin permeability (μg/cm2). Results

skin permeability of 309.0 μg/cm2 was observed after title compound treatment

Location

Page/Page column 18-20

Patent; KABUSHIKI KAISHA SANGI; EP1797900; (2007); (A1) English, View in Reaxys

Reaxys ID 12324765 View in Reaxys O

177/323 Linear Structure Formula: C15H24N2O2 Molecular Formula: C15H24N2O2 Molecular Weight: 264.368 InChI Key: BIWVAEQIPMKGRG-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 69

Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Reaxys ID 12324876 View in Reaxys O

178/323 Linear Structure Formula: C18H30N2O2 Molecular Formula: C18H30N2O2 Molecular Weight: 306.448 InChI Key: BSERROPIDNBQLH-UHFFFAOYSA-N Note:

Substance Label (1) Label References 37

Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Reaxys ID 12324967 View in Reaxys

179/323

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Linear Structure Formula: C20H34N2O2 Molecular Formula: C20H34N2O2 Molecular Weight: 334.502 InChI Key: NVGYZVOBOADMIR-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 53

Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Reaxys ID 12325112 View in Reaxys

180/323 Linear Structure Formula: C23H40N2O Molecular Formula: C23H40N2O Molecular Weight: 360.583 InChI Key: NBFZXWBIMGJUAN-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 85

Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Reaxys ID 12325136 View in Reaxys

181/323 Linear Structure Formula: C23H40N2O2 Molecular Formula: C23H40N2O2 Molecular Weight: 376.583 InChI Key: AQWMMMNHYDJCNS-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 101

Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

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Reaxys ID 12325170 View in Reaxys

182/323 Linear Structure Formula: C24H42N2O2 Molecular Formula: C24H42N2O2 Molecular Weight: 390.61 InChI Key: OHJLAPUUTHGDPC-UHFFFAOYSA-N Note:

H N

O O

Substance Label (1) Label References 21

Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; Haap, Wolfgang; Holzl, Werner; Petzold, Karin; US2004/6061; (2004); (A1) English, View in Reaxys

Reaxys ID 13516590 View in Reaxys

183/323 Chemical Name: 1-(3,4,5-trimethoxybenzyl)piperazine hydrochloride Linear Structure Formula: C14H22N2O3*ClH Molecular Formula: C14H22N2O3*ClH Molecular Weight: 302.801 InChI Key: KQVXQLNBEHFJNR-UHFFFAOYSA-N Note:

HCl O

N NH

O O

Reaxys ID 13771842 View in Reaxys

184/323 Chemical Name: N-(2-hydroxy-3,4-dimethoxybenzyl)-piperazine Linear Structure Formula: C13H20N2O3 Molecular Formula: C13H20N2O3 Molecular Weight: 252.313 InChI Key: YTTUZRPTSWBBDZ-UHFFFAOYSA-N Note:

OH O

N NH

Melting Point (1) 1 of 1

Melting Point [°C]

190

Patent; Adir et Compagnie; US5492913; (1996); (A1) English, View in Reaxys

Reaxys ID 14007986 View in Reaxys

185/323 CAS Registry Number: 194233-50-6 Chemical Name: 1-(2-bromo-5-methoxybenzyl)piperazine Linear Structure Formula: C12H17BrN2O Molecular Formula: C12H17BrN2O Molecular Weight: 285.184 InChI Key: HNUDCOJENMOJPE-UHFFFAOYSA-N Note:

Br N NH O

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Reaxys ID 14009513 View in Reaxys

186/323 CAS Registry Number: 223514-09-8 Chemical Name: N-(4-((piperazin-1-yl)methyl)phenylmethyl)acetamide Linear Structure Formula: C14H21N3O Molecular Formula: C14H21N3O Molecular Weight: 247.34 InChI Key: BYXIAOXSRKGTPN-UHFFFAOYSA-N Note:

O NH NH N

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Original Text (NMR Spectroscopy)

1H-NMR(CDCl )δ: 2.01(3H, s), 2.35-2.40(4H, m), 2.84-2.87(4H, m), 3.46(2H, s), 4.40(2H, 3 d, J=5.30 Hz), 5.91(1H, brs), 7.20-7.30(4H, m)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

2.01; 2.35 - 2.4; 2.84 - 2.87; 3.46; 4.4; 5.91; 7.2 - 7.3

Kind of signal

3H, s; 4H, m; 4H, m; 2H, s; 2H, d, J=5.30 Hz; 1H, brs; 4H, m

Patent; Mitsubishi Pharma Corporation; US6455528; (2002); (B1) English, View in Reaxys Mass Spectrometry (1) Comment (Mass Peak Spectrometry) Molecular peak

References

247 m/z

Patent; Mitsubishi Pharma Corporation; US6455528; (2002); (B1) English, View in Reaxys

Reaxys ID 14170674 View in Reaxys HO

187/323 CAS Registry Number: 486450-90-2 Chemical Name: 4-{6-[(piperazin-1-yl)methyl]-2,3-dimethoxyphenoxy}butyric acid Linear Structure Formula: C17H26N2O5 Molecular Formula: C17H26N2O5 Molecular Weight: 338.404 InChI Key: DQYOVIHTBXQBPM-UHFFFAOYSA-N Note:

O O

N NH

Patent-Specific Data (1) Location in Patent References Claim

Patent; Labidalle, Serge; Tillement, Jean-Paul; Testa, Bernard; Cecchelli, Romeo; Ridant, Alain Le; Harpey, Catherine; Spedding, Michael; Schenker, Esther; US2003/158207; (2003); (A1) English, View in Reaxys

Reaxys ID 14185244 View in Reaxys HO

188/323 2 HCl

Chemical Name: 4-{6-[(Piperazin-1-yl)methyl]-2,3-dimethoxyphenoxy}butyric Acid Dihydrochloride Linear Structure Formula: C17H26N2O5*2ClH Molecular Formula: C17H26N2O5*2ClH Molecular Weight: 411.326 InChI Key: DILPXVCGRFSMOM-UHFFFAOYSA-N Note:

O O

N NH

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Melting Point (1) 1 of 1

Melting Point [°C]

141

Reaxys ID 14185747 View in Reaxys

189/323 2 HCl

Chemical Name: ethyl 4-{6-[(piperazin-1-yl)methyl]-2,3-dimethoxyphenoxy}-butyrate Dihydrochloride Linear Structure Formula: C19H30N2O5*2ClH Molecular Formula: C19H30N2O5*2ClH Molecular Weight: 439.379 InChI Key: FRADTPFNKWZCCR-UHFFFAOYSA-N Note:

O O

N NH

Reaxys ID 14186950 View in Reaxys

190/323 2

Chemical Name: 7-{6-[(Piperazin-1-yl)methyl]-2,3-dimethoxyphenoxy}heptanoic Acid Dihydrochloride Linear Structure Formula: C20H32N2O5*2ClH Molecular Formula: C20H32N2O5*2ClH Molecular Weight: 453.406 InChI Key: DJFLRAQRVJGYMY-UHFFFAOYSA-N Note:

HCl

H N

Melting Point (1) 1 of 1

Melting Point [°C]

160

Reaxys ID 14187119 View in Reaxys

191/323 2 HCl

Chemical Name: ethyl 7-{6-[(piperazin-1-yl)methyl]-2,3-dimethoxyphenoxy}heptanoate Dihydrochloride Linear Structure Formula: C22H36N2O5*2ClH Molecular Formula: C22H36N2O5*2ClH Molecular Weight: 481.46 InChI Key: FAZYVYYSTBCTNC-UHFFFAOYSA-N Note:

O O

N NH

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Reaxys ID 14199053 View in Reaxys (v1)

Pol

192/323 Chemical Name: piperazine-1-yl methyl resin Linear Structure Formula: C11H15N2Pol Molecular Formula: C11H15N2Pol InChI Key: JLMCZYHDYDEZHW-UHFFFAOYSA-N Note:

NH N

Reaxys ID 14210146 View in Reaxys H N

193/323 Chemical Name: N-(2,3-dichlorophenylmethyl)piperazine dihydrochloride Linear Structure Formula: C11H14Cl2N2*2ClH Molecular Formula: C11H14Cl2N2*2ClH Molecular Weight: 318.073 InChI Key: IGRCCKVCHQEDMT-UHFFFAOYSA-N Note:

2 HCl

Substance Label (1) Label References Intermediate (4)

Patent; Poindexter, Graham S.; Luo, Guanglin; Chen, Ling; US2003/232807; (2003); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties white

Patent; Poindexter, Graham S.; Luo, Guanglin; Chen, Ling; US2003/232807; (2003); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Original Text (NMR Spectroscopy)

1H NMR (DMSO-d6) δ9.81 (br, 2H), 7.87 (d, J=7.5 Hz, 1H), 7.75 (d, J=8.0 Hz), 7.47 (t, J=7.9 Hz), 4.45 (s, 2H), 3.40 (s, 4H), 3.16 (s, 1H);

Comment (NMR Spectroscopy)

Signals given

Patent; Poindexter, Graham S.; Luo, Guanglin; Chen, Ling; US2003/232807; (2003); (A1) English, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Original Text (NMR Spectroscopy)

13C NMR (DMSO-d6) δ133.0, 132.6, 132.5, 131.9, 128.7, 56.9, 48.2, 40.6;

Comment (NMR Spectroscopy)

Signals given

Patent; Poindexter, Graham S.; Luo, Guanglin; Chen, Ling; US2003/232807; (2003); (A1) English, View in Reaxys Mass Spectrometry (1) Comment (Mass References Spectrometry) Molecular peak

Patent; Poindexter, Graham S.; Luo, Guanglin; Chen, Ling; US2003/232807; (2003); (A1) English, View in Reaxys

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Reaxys ID 14305256 View in Reaxys 2

194/323 Chemical Name: 1-(3-hydroxybenzyl)piperazine dihydrochloride Linear Structure Formula: C11H16N2O*2ClH Molecular Formula: C11H16N2O*2ClH Molecular Weight: 265.183 InChI Key: GURMYICYIOZTJQ-UHFFFAOYSA-N Note:

HCl

NH N

Crystal Property Description (1) Colour & Other References Properties white

Patent; Ferring B.V.; EP1449844; (2004); (A1) English, View in Reaxys

Reaxys ID 14305260 View in Reaxys

195/323 Chemical Name: 1-(3-(hydroxymethyl)benzyl)piperazine dihydrochloride Linear Structure Formula: C12H18N2O*2ClH Molecular Formula: C12H18N2O*2ClH Molecular Weight: 279.21 InChI Key: MBOQVIIFWAKLSK-UHFFFAOYSA-N Note:

2 HCl

NH HO

Crystal Property Description (1) Colour & Other References Properties white

Patent; Ferring B.V.; EP1449844; (2004); (A1) English, View in Reaxys

Reaxys ID 14352745 View in Reaxys

196/323 2

S N

Chemical Name: N,N-dimethyl-3-piperazin-1-ylmethyl-thiobenzamide dihydrochloride Linear Structure Formula: C14H21N3S*2ClH Molecular Formula: C14H21N3S*2ClH Molecular Weight: 336.329 InChI Key: LPRIQAODKRGZHO-UHFFFAOYSA-N Note:

HCl

N NH

Reaxys ID 14352746 View in Reaxys

197/323 2

O N

Chemical Name: N,N-Dimethyl-3-piperazin-1-ylmethyl-benzamide dihydrochloride Linear Structure Formula: C14H21N3O*2ClH Molecular Formula: C14H21N3O*2ClH Molecular Weight: 320.262 InChI Key: DRFKRTQVXDYTDU-UHFFFAOYSA-N Note:

HCl

N NH

Reaxys ID 14400356 View in Reaxys

198/323

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N NH 2 O

Chemical Name: 4-piperazin-1-ylmethyl-benzoic acid methyl ester ditrifluoroacetic acid Linear Structure Formula: 2C2HF3O2*C13H18N2O2 Molecular Formula: 2C2HF3O2*C13H18N2O2 Molecular Weight: 462.346 InChI Key: MJMYNYKEFHPBNS-UHFFFAOYSA-N Note:

F F

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

'H NMR (CD30D) 8 8. 01 (d, 2H, J=8.3 Hz), 7.58 (d, 2H, J = 8. 3 Hz), 4.39 (s, 2H), 3. 84 (s, 3H, OCH3), 3.52-3. 47 (m, 8H) ; 13C NMR (CD30D) 6 167.7, 135.3, 132.4, 131.2, 61.1, 52.9, 49.5, 42.2.

Comment (NMR Spectroscopy)

Signals given

Patent; S*BIO PTE LTD; WO2005/40101; (2005); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray Molecular peak ionisation); LCMS (Liquid chromatography mass spectrometry)

References Patent; S*BIO PTE LTD; WO2005/40101; (2005); (A1) English, View in Reaxys

Reaxys ID 14478898 View in Reaxys

199/323 Linear Structure Formula: 2C2HF3O2*C11H15BrN2 Molecular Formula: 2C2HF3O2*C11H15BrN2 Molecular Weight: 483.205 InChI Key: CJYUPBCWTIQSDP-UHFFFAOYSA-N Note:

NH 2 HO F

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Original Text (NMR Spectroscopy)

;'H NMR, 5 (CD30D) 3.05 (4H, m), 3.37 (4H, m), 3.95 (2H, s), 7.35 (2H, m), 7.54 (1H, dd, J 1.5 and 6.2 Hz), 7.64 (1 H, d, J 1.5 Hz).

Comment (NMR Spectroscopy)

Signals given

Patent; GLAXO GROUP LIMITED; WO2005/87236; (2005); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; GLAXO GROUP LIMITED; WO2005/87236; (2005); (A1) English, View in Reaxys

Molecular peak

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Reaxys ID 14531025 View in Reaxys

200/323 Chemical Name: {[3,5-bis(t-butyl)phenyl]methyl}piperazine dihydrochloride Linear Structure Formula: C19H32N2*2ClH Molecular Formula: C19H32N2*2ClH Molecular Weight: 361.398 InChI Key: IFDNRWYGSRMJCE-UHFFFAOYSA-N Note:

2 HCl N NH

Crystal Property Description (1) Colour & Other References Properties white

Patent; Chugai Seiyaku Kabushiki Kaisha; US6645951; (2003); (B1) English, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H-NMR(300 MHz, CD OD) δ: 1.38(s, 18H), 3.56-3.64(m, 8H), 4.45(s, 2H), 7.50(s, 2H), 3 7.61(s, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; Chugai Seiyaku Kabushiki Kaisha; US6645951; (2003); (B1) English, View in Reaxys

Reaxys ID 14564520 View in Reaxys

201/323 CAS Registry Number: 523980-75-8 Chemical Name: 1-[(5-fluoro-2-methoxyphenyl)methyl]-piperazine Linear Structure Formula: C12H17FN2O Molecular Formula: C12H17FN2O Molecular Weight: 224.278 InChI Key: WSVHAGDWEZZIGZ-UHFFFAOYSA-N Note:

O N NH F

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

CI (Chemical ioni- Molecular peak zation)

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/56752; (2006); (A1) English, View in Reaxys

Reaxys ID 14564535 View in Reaxys

202/323 CAS Registry Number: 523980-87-2 Chemical Name: 1-[[2-methoxy-5-(1-methylethyl)phenyl]methyl]-piperazine Linear Structure Formula: C15H24N2O Molecular Formula: C15H24N2O Molecular Weight: 248.368 InChI Key: MEWPGWMHPNZGFI-UHFFFAOYSA-N Note:

O N NH

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

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CI (Chemical ioni- Molecular peak zation)

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/56752; (2006); (A1) English, View in Reaxys

Reaxys ID 14564573 View in Reaxys

203/323 CAS Registry Number: 888973-22-6 Chemical Name: [4-chloro-2-(1-piperazinylmethyl)phenoxy]acetic acid ethyl ester Linear Structure Formula: C15H21ClN2O3 Molecular Formula: C15H21ClN2O3 Molecular Weight: 312.796 InChI Key: LMJFJMPKGYZPNN-UHFFFAOYSA-N Note:

O N NH Cl

Reaxys ID 14564586 View in Reaxys O

204/323 CAS Registry Number: 888972-26-7 Chemical Name: [4-chloro-2-(1-piperazinylmethyl)phenoxy]acetic acid, 1,1-dimethylethyl ester Linear Structure Formula: C17H25ClN2O3 Molecular Formula: C17H25ClN2O3 Molecular Weight: 340.85 InChI Key: UMMNNZYYIUAROS-UHFFFAOYSA-N Note:

O N NH Cl

Reaxys ID 14564602 View in Reaxys

205/323 Chemical Name: [2-(1-piperazinylmethyl)-4-(trifluoromethyl)phenoxy]-acetic acid Linear Structure Formula: C14H17F3N2O3 Molecular Formula: C14H17F3N2O3 Molecular Weight: 318.296 InChI Key: UOEFOQWGBUBUOD-UHFFFAOYSA-N Note:

H N

F F O OH O

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (CDCl3): δ 7.68 (IH, s); 7.44 (IH, dd); 6.76 (IH, d), 4.57(2H, s), 3.64(2H,s), 2.94 (2H, s), 2.52 (4H, t), 1.48 (9H, s).

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/56752; (2006); (A1) English, View in Reaxys

Reaxys ID 14564623 View in Reaxys

206/323

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CAS Registry Number: 888972-23-4 Chemical Name: [2-(1-piperazinylmethyl)-4-(trifluoromethyl)phenoxy]-acetic acid 1,1-dimethylethyl ester Linear Structure Formula: C18H25F3N2O3 Molecular Formula: C18H25F3N2O3 Molecular Weight: 374.403 InChI Key: UMJDRQYOBDOUPR-UHFFFAOYSA-N Note:

O N NH F

F F

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (CDCl3):: δ 7.68 (IH, s); 7.47 (IH, d); 6.76 (IH, d), 4.57(2H, s), 3.65(2H,s), 3.45 (4H,t), 2.46 (4H,s), 1.48 (9H,s), 1.45 (9H,s).

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/56752; (2006); (A1) English, View in Reaxys

Reaxys ID 14572424 View in Reaxys

207/323 CAS Registry Number: 523981-23-9 Chemical Name: 1-(3,4-dibromo-benzyl)-piperazine Linear Structure Formula: C11H14Br2N2 Molecular Formula: C11H14Br2N2 Molecular Weight: 334.054 InChI Key: YOIVYWFLFQIMFP-UHFFFAOYSA-N Note:

N NH

Crystal Property Description (1) Colour & Other References Properties colorless

Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/74025; (2006); (A1) English, View in Reaxys

Reaxys ID 14572866 View in Reaxys

208/323

Chemical Name: 1-(3,4-dibromo-benzyl)-piperazine hydrochloride Linear Structure Formula: C11H14Br2N2*ClH Molecular Formula: C11H14Br2N2*ClH Molecular Weight: 370.514 InChI Key: WJGODYRNLSYSIQ-UHFFFAOYSA-N Note:

HCl

Crystal Property Description (1) Colour & Other References Properties white

Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/74025; (2006); (A1) English, View in Reaxys

Reaxys ID 14834570 View in Reaxys

209/323

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Chemical Name: 1-Benzylpiperazine N-carbamoylglycine amide Linear Structure Formula: C3H7N3O2*C11H16N2 Molecular Formula: C3H7N3O2*C11H16N2 Molecular Weight: 293.369 InChI Key: MLMFXAIUSRCDDV-UHFFFAOYSA-N Note:

NH 2

N NH 2

N H

Reaxys ID 15001104 View in Reaxys

210/323 CAS Registry Number: 174609-74-6 Chemical Name: o-cyanobenzyl piperazine Linear Structure Formula: C12H15N3 Molecular Formula: C12H15N3 Molecular Weight: 201.271 InChI Key: DVUNFWADPIWIAY-UHFFFAOYSA-N Note:

N NH

Reaxys ID 15007963 View in Reaxys

211/323 Chemical Name: N-(2-tert-Butylcarbonyloxy-3,4-dimethoxy)benzylpiperazine dihydrochloride Linear Structure Formula: C18H28N2O4*2ClH Molecular Formula: C18H28N2O4*2ClH Molecular Weight: 409.353 InChI Key: WTSMEUBKNUKBPF-UHFFFAOYSA-N Note:

O H 2 Cl

N NH

Melting Point (1) 1 of 1

Melting Point [°C]

230

Patent; ADIR et Compagnie; US5849745; (1998); (A1) English, View in Reaxys

Reaxys ID 15052227 View in Reaxys

212/323 Chemical Name: 1-(3,4-dimethoxyphenylmethyl)piperazine dihydrochloride Linear Structure Formula: C13H20N2O2*2ClH Molecular Formula: C13H20N2O2*2ClH Molecular Weight: 309.236 InChI Key: MFRIQPBHLRTPKG-UHFFFAOYSA-N Note:

H 2 Cl O

N NH

Reaxys ID 15137302 View in Reaxys

213/323 CAS Registry Number: 1177490-59-3 Chemical Name: (4-ethoxycarbonylbenzyl)piperazine Linear Structure Formula: C14H20N2O2 Molecular Formula: C14H20N2O2 Molecular Weight: 248.325 InChI Key: DFNLBHGWXMPXOS-UHFFFAOYSA-N Note:

N O

NH O

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Reaxys ID 15401205 View in Reaxys

214/323 CAS Registry Number: 199468-12-7 Chemical Name: 1-(3-(1,1-dimethylethyl)-4-hydroxy-5-methylphenyl)methylpiperazine Linear Structure Formula: C16H26N2O Molecular Formula: C16H26N2O Molecular Weight: 262.395 InChI Key: OSKZAKXJPOTOJD-UHFFFAOYSA-N Note:

N NH

Melting Point (1) 1 of 1

Melting Point [°C]

155 - 160

Patent; Monash University; US6232314; (2001); (B1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

7.02; 6.94; 3.4; 2.93; 2.45; 2.23; 1.41

Kind of signal

d, J=2.0 Hz, 1H; d, J=1.5 Hz, 1H; s, 2H; t, J=4.9 Hz, 4H; bs, 4H; s, 3H; s, 9H

NMR (CDCl3) δ7.02 (d, J=2.0 Hz, 1H); 6.94 (d, J=1.5 Hz, 1H); 3.40 (s, 2H); 2.93 (t, J=4.9 Hz, 4H); 2.45 (bs, 4H); 2.23 (s, 3H); 1.41 (s, 9H)

Patent; Monash University; US6232314; (2001); (B1) English, View in Reaxys

Reaxys ID 15508759 View in Reaxys

215/323 Linear Structure Formula: C12H14FN3 Molecular Formula: C12H14FN3 Molecular Weight: 219.262 InChI Key: VJXHMAYQCZAJOM-UHFFFAOYSA-N Note:

N N NH

Reaxys ID 15575788 View in Reaxys

216/323 Chemical Name: -4-(trifluoromethyl-benzyl)piperazine dihydrochloride Linear Structure Formula: C12H15F3N2*2ClH Molecular Formula: C12H15F3N2*2ClH Molecular Weight: 317.182 InChI Key: JLYPTMOIWITOPH-UHFFFAOYSA-N Note:

F F

F H 2 Cl

N NH

Melting Point (1) 1 of 1

Melting Point [°C]

209 - 211

Patent; EGIS GYOGYSZERGYAR; US2004/186170; (2004); (A1) English, View in Reaxys

Reaxys ID 15929468 View in Reaxys

217/323

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CAS Registry Number: 81567-09-1 Chemical Name: bis(N-benzylpiperazinium) tetrachlorocuprate(II) bis(hydrochloride) Linear Structure Formula: 2C11H17N2 (1+)*CuCl4 (2-)*2HCl=(C H N )2CuCl *2HCl 11 17 2 4 Molecular Formula: 2C11H16N2*2ClH*Cl4Cu*2H Molecular Weight: 632.819 Type of Substance: Coordination compound InChI Key: UVUQCPSGEXQFNS-UHFFFAOYSA-K Note:

Cl 2 H

2 H+

N 2

Cl CuCl2Cl SP-4 Cl (v4) N H

Conformation (1) Object of Investi- References gation Conformation

McDonald, Robbie G.; Riley, Mark J.; Hitchman, Michael A.; Inorganic Chemistry; vol. 27; (1988); p. 894 900 ; (from Gmelin), View in Reaxys

Crystal Property Description (1) Colour & Other References Properties green

McDonald, Robbie G.; Riley, Mark J.; Hitchman, Michael A.; Inorganic Chemistry; vol. 27; (1988); p. 894 900 ; (from Gmelin), View in Reaxys

Crystal System (1) Crystal System References Monoclinic

McDonald, Robbie G.; Riley, Mark J.; Hitchman, Michael A.; Inorganic Chemistry; vol. 27; (1988); p. 894 900 ; (from Gmelin), View in Reaxys

Interatomic Distances and Angles (1) Description References Interatomic distances and angles Space Group (1) Comment (Space Group) Z=2

McDonald, Robbie G.; Riley, Mark J.; Hitchman, Michael A.; Inorganic Chemistry; vol. 27; (1988); p. 894 900 ; (from Gmelin), View in Reaxys

References McDonald, Robbie G.; Riley, Mark J.; Hitchman, Michael A.; Inorganic Chemistry; vol. 27; (1988); p. 894 900 ; (from Gmelin), View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Spectrum; Band assignment

Solvent (UV/VIS Spectroscopy)

neat (no solvent)

Comment (UV/VIS Spectroscopy)

526.316 nm - 1428.6 nm

McDonald, Robbie G.; Riley, Mark J.; Hitchman, Michael A.; Inorganic Chemistry; vol. 27; (1988); p. 894 - 900 ; (from Gmelin), View in Reaxys Quantum Chemical Calculations (1) Calculated Prop- Method (Quantum References erties Chemical Calculations) UV/VIS wave lengths

further quantum chemical calcns.

McDonald, Robbie G.; Riley, Mark J.; Hitchman, Michael A.; Inorganic Chemistry; vol. 27; (1988); p. 894 - 900 ; (from Gmelin), View in Reaxys

Reaxys ID 16129449 View in Reaxys

218/323

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NH +

(v1)

CAS Registry Number: 77932-60-6 Chemical Name: N-benzylpiperazinium pentachloroantimonate(III) Linear Structure Formula: C6H5CH2NHC4H8NH2 (2+)*SbCl5 (2-)=(C H CH NHC H NH )SbCl 6 5 2 4 8 2 5 Molecular Formula: C11H18N2*Cl5Sb Molecular Weight: 477.292 InChI Key: KKWZPMOENDRRER-UHFFFAOYSA-K Note:

(v1)– Cl – (v1) –(v5) 3+ Cl Cl Sb Cl – (v1) –

(v1)

N+ H2

Use (1) Laboratory Use and Handling stable in air

References Caritati, Franco; Panzanelli, Angelo; Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Marcotrigiano, Giuseppe; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1981); p. 909 - 913 ; (from Gmelin), View in Reaxys

Reaxys ID 16132845 View in Reaxys

NH +

(v1)

219/323 CAS Registry Number: 77932-61-7 Chemical Name: N-benzylpiperazinium pentabromoantimonate(III) Linear Structure Formula: C6H5CH2NHC4H8NH2 (2+)*SbBr5 (2-)=(C H CH NHC H NH )SbBr 6 5 2 4 8 2 5 Molecular Formula: Br5Sb*C11H18N2 Molecular Weight: 699.547 InChI Key: CHIIBXMYKGMTKN-UHFFFAOYSA-K Note:

(v1)– Br (v5) – (v1) –BrSb 3+ Br Br– (v1) –

(v1)

N+ H2

Use (1) Laboratory Use and Handling stable in air

Reaxys ID 16132846 View in Reaxys

NH +

(v1)

220/323 CAS Registry Number: 77932-62-8 Chemical Name: N-benzylpiperazinium pentachlorobismuthate(III) Linear Structure Formula: C6H5CH2NHC4H8NH2 (2+)*BiCl5 (2-)=(C H CH NHC H NH )BiCl 6 5 2 4 8 2 5 Molecular Formula: BiCl5*C11H18N2 Molecular Weight: 564.523 InChI Key: CVPJOZAXMDVUTG-UHFFFAOYSA-K Note:

(v1) Cl – –(v5) Cl 3+–– (v1) Cl BiCl (v1) –

(v1)

N+ H2

Use (1) Laboratory Use and Handling stable in air

Reaxys ID 16132847 View in Reaxys

221/323

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NH +

(v1)

CAS Registry Number: 77932-63-9 Chemical Name: N-benzylpiperazinium pentabromobismuthate(III) Linear Structure Formula: C6H5CH2NHC4H8NH2 (2+)*BiBr5 (2-)=(C H CH NHC H NH )BiBr 6 5 2 4 8 2 5 Molecular Formula: BiBr5*C11H18N2 Molecular Weight: 786.778 InChI Key: KQPUVJGRTUYCLD-UHFFFAOYSA-K Note:

(v1) Br– –(v5) 3+– (v1) Br BiBr Br– (v1) –

(v1)

N+ H2

Use (1) Laboratory Use and Handling stable in air

Reaxys ID 16897086 View in Reaxys

222/323 Chemical Name: N-benzylpiperazinium tetrabromocuprate(II) hydrate Linear Structure Formula: {C11H18N2}(2+)*{CuBr4}(2-)*H2O Molecular Formula: Br4Cu*C11H16N2*2H*H2O Molecular Weight: 579.455 Type of Substance: Coordination compound InChI Key: JQUXGTDXQPVSME-UHFFFAOYSA-K Note:

Br Br

Cu 2BrBr

(v4)

H 2 H+

Density (1) 1 of 1

Density [g·cm-3]

2.18

Measurement Temperature [°C]

Type (Density)

crystallographic

Place, Helen; Willett, Roger D.; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 44; (1988); p. 34 - 38 ; (from Gmelin), View in Reaxys Crystal Phase (3) Description (Crys- References tal Phase) plates

Place, Helen; Willett, Roger D.; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 44; (1988); p. 34 - 38 ; (from Gmelin), View in Reaxys

Structure of the solid

Place, Helen; Willett, Roger D.; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 44; (1988); p. 34 - 38 ; (from Gmelin), View in Reaxys

Single Crystal Xray Diffraction

Place, Helen; Willett, Roger D.; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 44; (1988); p. 34 - 38 ; (from Gmelin), View in Reaxys

Crystal Property Description (1) Colour & Other References Properties black

Place, Helen; Willett, Roger D.; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 44; (1988); p. 34 - 38 ; (from Gmelin), View in Reaxys

Crystal System (1) Crystal System References Triclinic

Place, Helen; Willett, Roger D.; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 44; (1988); p. 34 - 38 ; (from Gmelin), View in Reaxys

Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles)

288/337

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Interatomic distances and angles Space Group (1) Space Group 14

Single Crystal Xray Diffraction

Place, Helen; Willett, Roger D.; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 44; (1988); p. 34 - 38 ; (from Gmelin), View in Reaxys

Comment (Space Group)

References

a = 7.413 AngPlace, Helen; Willett, Roger D.; Acta Crystallographica, Section C: Crystal Structure stroem, b = Communications; vol. 44; (1988); p. 34 - 38 ; (from Gmelin), View in Reaxys 16.459 Angstroem, c = 14.961 Angstroem, β = 104.78; Z = 4; T = 20 Deg C; atomic positions available

Reaxys ID 17027657 View in Reaxys

223/323 I

Cd 2I I

H+

Linear Structure Formula: C11H18N2 (2+)*CdI4 (2-)*H O=(C H N )CdI *H O 2 11 18 2 4 2 Molecular Formula: C11H16N2*CdI4*2H*H2O Molecular Weight: 816.321 Type of Substance: Coordination compound InChI Key: NCQAHHQHBIUTGC-UHFFFAOYSA-K Note:

(v4)

H O

IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

polyethylene

Comment (IR Spectroscopy)

50 cm**-1 - 500 cm**-1

Bruni, Silvia; Cariati, Franco; Pozzi, Andrea; Battaglia, Luigi Pietro; Corradi, Anna Bonamartini; Inorganica Chimica Acta; vol. 183; (1991); p. 221 - 228 ; (from Gmelin), View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

polyethylene

Comment (IR Spectroscopy)

50 cm**-1 - 500 cm**-1

Bruni, Silvia; Cariati, Franco; Pozzi, Andrea; Battaglia, Luigi Pietro; Corradi, Anna Bonamartini; Inorganica Chimica Acta; vol. 183; (1991); p. 221 - 228 ; (from Gmelin), View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

not given

Comment (IR Spectroscopy)

500 cm**-1 - 4000 cm**-1

Bruni, Silvia; Cariati, Franco; Pozzi, Andrea; Battaglia, Luigi Pietro; Corradi, Anna Bonamartini; Inorganica Chimica Acta; vol. 183; (1991); p. 221 - 228 ; (from Gmelin), View in Reaxys Raman Spectroscopy (1) Description (Ram- References an Spectroscopy)

289/337

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Raman

Bruni, Silvia; Cariati, Franco; Pozzi, Andrea; Battaglia, Luigi Pietro; Corradi, Anna Bonamartini; Inorganica Chimica Acta; vol. 183; (1991); p. 221 - 228 ; (from Gmelin), View in Reaxys

Reaxys ID 17029633 View in Reaxys

224/323 Br

Linear Structure Formula: C11H18N2 (2+)*CdBr4 2O=(C11H18N2)CdBr4*H2O Molecular Formula: Br4Cd*C11H16N2*2H*H2O Molecular Weight: 628.319 Type of Substance: Coordination compound InChI Key: RVYHXNVLCSGYSY-UHFFFAOYSA-K Note:

(v4)

Cd 2BrBr

(2-)*H

2 H+

IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

polyethylene

Comment (IR Spectroscopy)

50 cm**-1 - 500 cm**-1

Bruni, Silvia; Cariati, Franco; Pozzi, Andrea; Battaglia, Luigi Pietro; Corradi, Anna Bonamartini; Inorganica Chimica Acta; vol. 183; (1991); p. 221 - 228 ; (from Gmelin), View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

polyethylene

Comment (IR Spectroscopy)

50 cm**-1 - 500 cm**-1

Bruni, Silvia; Cariati, Franco; Pozzi, Andrea; Battaglia, Luigi Pietro; Corradi, Anna Bonamartini; Inorganica Chimica Acta; vol. 183; (1991); p. 221 - 228 ; (from Gmelin), View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

not given

Comment (IR Spectroscopy)

500 cm**-1 - 4000 cm**-1

Bruni, Silvia; Cariati, Franco; Pozzi, Andrea; Battaglia, Luigi Pietro; Corradi, Anna Bonamartini; Inorganica Chimica Acta; vol. 183; (1991); p. 221 - 228 ; (from Gmelin), View in Reaxys

Reaxys ID 17030141 View in Reaxys

225/323

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Linear Structure Formula: C11H18N2 (2+)*CdBr4 11H18N2)CdBr4 Molecular Formula: Br4Cd*C11H16N2*2H Molecular Weight: 610.303 Type of Substance: Coordination compound InChI Key: GVSMSIYGTMKOFZ-UHFFFAOYSA-K Note:

Br Br

Cd 2BrBr

(v4)

(2-)=(C

2 H+

Reaxys ID 17030975 View in Reaxys

226/323 Linear Structure Formula: C11H18N2 (2+)*CdCl4 (2-)=(C H N )CdCl 11 18 2 4 Molecular Formula: C11H16N2*CdCl4*2H Molecular Weight: 432.499 Type of Substance: Coordination compound InChI Key: ZEXZUWYOQWGUIH-UHFFFAOYSA-K Note:

Cl Cl

Cd 2Cl Cl

(v4)

2 H+

Reaxys ID 17032343 View in Reaxys

227/323 Cl

(2+)*CdCl

Linear Structure Formula: C11H18N2 4 2O=(C11H18N2)CdCl4*H2O Molecular Formula: C11H16N2*CdCl4*2H*H2O Molecular Weight: 450.515 Type of Substance: Coordination compound InChI Key: ZRULVUFNUWBNTQ-UHFFFAOYSA-K Note:

(v4)

Cd 2Cl Cl

H+

(2-)*H

H O

IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

polyethylene

Comment (IR Spectroscopy)

50 cm**-1 - 500 cm**-1

Bruni, Silvia; Cariati, Franco; Pozzi, Andrea; Battaglia, Luigi Pietro; Corradi, Anna Bonamartini; Inorganica Chimica Acta; vol. 183; (1991); p. 221 - 228 ; (from Gmelin), View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

polyethylene

Comment (IR Spectroscopy)

50 cm**-1 - 500 cm**-1

Bruni, Silvia; Cariati, Franco; Pozzi, Andrea; Battaglia, Luigi Pietro; Corradi, Anna Bonamartini; Inorganica Chimica Acta; vol. 183; (1991); p. 221 - 228 ; (from Gmelin), View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

not given

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Comment (IR Spectroscopy)

500 cm**-1 - 4000 cm**-1

Bruni, Silvia; Cariati, Franco; Pozzi, Andrea; Battaglia, Luigi Pietro; Corradi, Anna Bonamartini; Inorganica Chimica Acta; vol. 183; (1991); p. 221 - 228 ; (from Gmelin), View in Reaxys

Reaxys ID 17032498 View in Reaxys

228/323 (2+)*CdI

I I

Cd 2I I

Linear Structure Formula: C11H18N2 4 (2-)=(C H N )CdI 11 18 2 4 Molecular Formula: C11H16N2*CdI4*2H Molecular Weight: 798.305 Type of Substance: Coordination compound InChI Key: URXCCSHFGOMZDA-UHFFFAOYSA-K Note:

(v4)

2 H+

Reaxys ID 17432013 View in Reaxys

NH +

229/323

0.5 H (v1)– ClO

Chemical Name: [bzpipzn][CuCl4]*0.5H2O Linear Structure Formula: NH2CH2CH2NHCH2C6H5CH2CH2 (2+)*CuCl (2-)*0.5H O=CuCl NH C H NHCH C H *0.5H O 4 2 4 2 4 8 2 6 5 2 Molecular Formula: C11H18N2*Cl4Cu*0H2O Molecular Weight: 392.643 Type of Substance: Coordination compound InChI Key: YKUGUYMXZCUTQH-UHFFFAOYSA-L Note:

H (v4)

(v1)

–Cl

Cu 2+ – – ClCl

(v1) (v1)

Density (2) 1 of 2

Density [g·cm-3]

1.599

Type (Density)

crystallographic

Antolini, Luciano; Menabue, Ledi; Pellacani, Gian Carlo; Saladini, Monica; Marcotrigiano, Giuseppe; Porzio, William; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1981); p. 1753 1759 ; (from Gmelin), View in Reaxys 2 of 2

Density [g·cm-3]

1.59

Type (Density)

crystallographic

Crystal Phase (1) Description (Crys- References tal Phase)

292/337

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Single Crystal Xray Diffraction

Crystal Property Description (1) Colour & Other References Properties yellow

Crystal System (1) Crystal System References Monoclinic

Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles

Single Crystal Xray Diffraction

Magnetic Data (1) Description (Mag- Moment (Magnet- References netic Data) ic Data) [Acm2] Magnetic moment 1.72498E-19

Space Group (1) Space Group 14

Comment (Space Group)

References

a = 17.015 Angstroem, b = 16.977 Angstroem, c = 11.377 Angstroem, β = 97.156; Z = 8; atomic positions available

IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

Comment (IR Spectroscopy)

264 cm**-1 - 310 cm**-1

293/337

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1 of 1

Description (UV/VIS Spectroscopy)

Band assignment

Solvent (UV/VIS Spectroscopy)

not given

Comment (UV/VIS Spectroscopy)

1064.96 nm - 1574.8 nm

Reaxys ID 17448226 View in Reaxys

NH +

230/323 CAS Registry Number: 79503-34-7 Chemical Name: [bzpipzn][CuCl4] Linear Structure Formula: NH2CH2CH2NHCH2C6H5CH2CH2 (2+)*CuCl (2-)=CuCl NH C H NHCH C H 4 4 2 4 8 2 6 5 Molecular Formula: C11H18N2*Cl4Cu Molecular Weight: 383.635 Type of Substance: Coordination compound InChI Key: ITPVEMWHYNPSMI-UHFFFAOYSA-L Note:

(v1)– Cl (v4)

(v1)

–Cl

Cu 2+ – – ClCl

(v1) (v1)

Density (2) 1 of 2

Density [g·cm-3]

1.584

Type (Density)

crystallographic

Density [g·cm-3]

1.59

Type (Density)

crystallographic

Crystal Phase (1) Description (Crys- References tal Phase) Single Crystal Xray Diffraction

Crystal Property Description (1) Colour & Other References Properties green

Crystal System (1) Crystal System References Monoclinic

294/337

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Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles

Single Crystal Xray Diffraction

Magnetic Data (1) Description (Mag- Moment (Magnet- References netic Data) ic Data) [Acm2] Magnetic moment 1.72498E-19

Space Group (1) Space Group 4

Comment (Space Group)

References

a = 12.075 Angstroem, b = 28.479 Angstroem, c = 9.925 Angstroem, β = 109.54; Z = 8; atomic positions available

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

Signals [cm-1]

300

Reaxys ID 17529822 View in Reaxys

231/323 2

H O

Chemical Name: (N-benzylpiperazinium)3[Pb2Br10]*2H2O Linear Structure Formula: 3C6H5CH2NH(C2H4)2NH2 (2+)*[Pb Br ] 2 10 (6-)*2H O=(C H CH NH(C H )2NH )3[Pb Br ]*2H O 2 6 5 2 2 4 2 2 10 2 Molecular Formula: 3C11H16N2*6H*2H2O*Br10Pb2 Molecular Weight: 1784.3 Type of Substance: Coordination compound InChI Key: VGEFZNMMQXVEQO-UHFFFAOYSA-O Note:

H+

3 N

Br10Pb2( 6-)

Density (2) 1 of 2

Density [g·cm-3]

2.32

Measurement Temperature [°C]

Type (Density)

crystallographic

Bonamartini Corradi; Ferrari; Righi; Sgarabotto; Inorganic Chemistry; vol. 40; nb. 2; (2001); p. 218 - 223 ; (from Gmelin), View in Reaxys 2 of 2

Density [g·cm-3]

2.31

Type (Density)

crystallographic

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Bonamartini Corradi; Ferrari; Righi; Sgarabotto; Inorganic Chemistry; vol. 40; nb. 2; (2001); p. 218 - 223 ; (from Gmelin), View in Reaxys Crystal Phase (2) Description (Crys- References tal Phase) Structure of the solid

Bonamartini Corradi; Ferrari; Righi; Sgarabotto; Inorganic Chemistry; vol. 40; nb. 2; (2001); p. 218 - 223 ; (from Gmelin), View in Reaxys

Single Crystal Xray Diffraction

Bonamartini Corradi; Ferrari; Righi; Sgarabotto; Inorganic Chemistry; vol. 40; nb. 2; (2001); p. 218 - 223 ; (from Gmelin), View in Reaxys

Crystal Property Description (1) Colour & Other References Properties white

Bonamartini Corradi; Ferrari; Righi; Sgarabotto; Inorganic Chemistry; vol. 40; nb. 2; (2001); p. 218 - 223 ; (from Gmelin), View in Reaxys

Crystal System (1) Crystal System References Monoclinic

Bonamartini Corradi; Ferrari; Righi; Sgarabotto; Inorganic Chemistry; vol. 40; nb. 2; (2001); p. 218 - 223 ; (from Gmelin), View in Reaxys

Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles Space Group (1) Space Group 14

Single Crystal Xray Diffraction

Bonamartini Corradi; Ferrari; Righi; Sgarabotto; Inorganic Chemistry; vol. 40; nb. 2; (2001); p. 218 - 223 ; (from Gmelin), View in Reaxys

Comment (Space Group)

References

a = 22.380 Angstroem, b = 9.304 Angstroem, c = 24.577 Angstroem, β = 94.28; Z = 4; T = 20 Deg C

Bonamartini Corradi; Ferrari; Righi; Sgarabotto; Inorganic Chemistry; vol. 40; nb. 2; (2001); p. 218 - 223 ; (from Gmelin), View in Reaxys

Reaxys ID 18074893 View in Reaxys

232/323 Chemical Name: N-benzylpiperaziniumpentachlorodimercury(II) Linear Structure Formula: C6H5CH2NHC4H8NH(1+)*2Hg(2+)*5Cl(1-)=(C6H5CH2NHC4H8NH)H g2Cl5 Molecular Formula: C11H17N2*5Cl*2Hg Molecular Weight: 755.714 Type of Substance: Coordination compound InChI Key: DZKMLEKVIAYIQB-UHFFFAOYSA-N Note:

5 Cl – 2 Hg 2+ H N+ NH

Density (2) 1 of 2

Density [g·cm-3]

2.728

Type (Density)

crystallographic

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys 2 of 2

Density [g·cm-3]

2.73 - 2.75

Type (Density)

crystallographic

296/337

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Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys Conformation (1) Object of Investi- References gation Conformation

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys

Crystal Phase (3) Description (Crys- References tal Phase) prisms

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys

Structure of the solid

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys

Single Crystal Xray Diffraction

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys

Crystal Property Description (2) Colour & Other References Properties colorless

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys

white

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys

Crystal System (1) Crystal System References Triclinic

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys

Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles Space Group (1) Space Group 2

Single Crystal Xray Diffraction

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys

Comment (Space Group)

References

a = 14.747 AngAlbinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. stroem, b = 8.839 C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), Angstroem, c = View in Reaxys 7.501 Angstroem, α = 95.64, β = 98.57, γ = 72.32; Z = 2; atomic positions available

IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

150 cm**-1 - 400 cm**-1

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

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Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

150 cm**-1 - 400 cm**-1

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Comment (IR Spectroscopy)

2730 cm**-1 - 3215 cm**-1

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys Raman Spectroscopy (1) Description (Ram- References an Spectroscopy) Raman

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys

Reaxys ID 18137097 View in Reaxys

233/323 Linear Structure Formula: C6H5CH2NHC4H8NH(1+)*2Hg(2+)*5Br(1-)=(C6H5CH2NHC4H8NH)H g2Br5 Molecular Formula: 5Br*C11H17N2*2Hg Molecular Weight: 977.969 Type of Substance: Coordination compound InChI Key: QBMSJCOLXIWFFW-UHFFFAOYSA-N Note:

5 Br–

H N+

Hg 2+

IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

150 cm**-1 - 400 cm**-1

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

150 cm**-1 - 400 cm**-1

Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Comment (IR Spectroscopy)

2730 cm**-1 - 3215 cm**-1

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Albinati, A.; Meille, S. V.; Cariati, F.; Marcotrigiano, G.; Menabue, L.; Pellacani, G. C.; Inorganica Chimica Acta; vol. 38; (1980); p. 221 - 226 ; (from Gmelin), View in Reaxys

Reaxys ID 18468208 View in Reaxys

234/323 2

Chemical Name: 1-(2,4-difluorobenzyl)piperazine dihydrochloride; 4-(2,4-difluorobenzyl)piperazine dihydrochloride Linear Structure Formula: C11H14F2N2*2ClH Molecular Formula: C11H14F2N2*2ClH Molecular Weight: 285.164 InChI Key: FUTZACFTEYEBBK-UHFFFAOYSA-N Note:

HCl

N F

Melting Point (1) 1 of 1

Melting Point [°C]

237

Patent; Moorman, Allan R.; US2008/242672; (2008); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Patent; Moorman, Allan R.; US2008/242672; (2008); (A1) English, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

3.44; 4.39; 7.25; 7.43; 7.84; 9.84

Kind of signal

m, 8H; s, 2H; dt, 1H, J=8.4 Hz and 1.6 Hz; dt, 1H, J=9.2 Hz and 2.0 Hz; dd, 1H, J=15.2 Hz and 8.4 Hz; br s, NH

NMR (DMSO-d6, 400 MHz) δ 3.44 (m, 8H), 4.39 (s, 2H), 7.25 (dt, 1H, J=8.4 Hz and 1.6 Hz), 7.43 (dt, 1H, J=9.2 Hz and 2.0 Hz), 7.84 (dd, 1H, J=15.2 Hz and 8.4 Hz), 9.84 (br s, NH)

Patent; Moorman, Allan R.; US2008/242672; (2008); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) LCMS (Liquid chromatography mass spectrometry)

Molecular peak

References Patent; Moorman, Allan R.; US2008/242672; (2008); (A1) English, View in Reaxys

Reaxys ID 18590470 View in Reaxys

235/323

299/337

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CAS Registry Number: 1043508-54-8 Chemical Name: N-[(4-((dimethylamino)methyl)phenyl)methyl]piperazine Linear Structure Formula: C14H23N3 Molecular Formula: C14H23N3 Molecular Weight: 233.357 InChI Key: UJRLPOICELDLRH-UHFFFAOYSA-N Note:

N N

Substance Label (1) Label References 6d

Fouchet, Marie-Helene; Donche, Frederic; Martin, Christelle; Bouillot, Anne; Junot, Christophe; Boullay, Anne-Benedicte; Potvain, Florent; Magny, Sylvie Demaria; Coste, Herve; Walker, Max; Issandou, Marc; Dodic, Nerina; Bioorganic and Medicinal Chemistry; vol. 16; nb. 11; (2008); p. 6218 - 6232, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties light-yellow

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

ambient temperature

Reaxys ID 18657759 View in Reaxys

Chemical Name: 1-[(2,3,5-trifluorophenyl)methyl]piperazine dihydrochloride Linear Structure Formula: C11H13F3N2*2ClH Molecular Formula: C11H13F3N2*2ClH Molecular Weight: 303.155 InChI Key: CFSJSMKATUWFNL-UHFFFAOYSA-N Note:

2 HCl

F F

236/323

N NH F

Substance Label (1) Label References 2

Patent; PANACOS PHARMACEUTICALS, INC.; NITZ, Theodore, J.; SALZWEDEL, Karl; FINNEGAN, Catherine; WILD, Carl; BRUNTON, Shirley; FLANAGAN, Stuart; MONTALBETTI, Christian; COULTER, Thomas, Stephen; KIMBER, Marc; MAGARACI, Filippo; JOHNSTON, David; WO2008/134035; (2008); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties light-yellow

Mass Spectrometry (1)

300/337

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Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray Molecular peak ionisation); LCMS (Liquid chromatography mass spectrometry)

Reaxys ID 18741166 View in Reaxys

–C

237/323 Chemical Name: (CuCN)3(N-benzylpiperazine)2; (CuCN)3(BzPip)2 Linear Structure Formula: 3Cu(1+)*3CN(1-)*2(CH2)4(NCH2C6H5)NH=(CuCN)3((CH2)4(NCH 2C6H5)NH)2 Molecular Formula: 3CN*2C11H16N2*3Cu Molecular Weight: 621.214 Type of Substance: Coordination compound InChI Key: SNZODUUSTQBMFN-UHFFFAOYSA-N Note:

3 N

3 Cu +

Density (1) 1 of 1

Density [g·cm-3]

1.519

Measurement Temperature [°C]

-73.16

Type (Density)

crystallographic

Mi, Jung Lim; Murray, Courtney A.; Tronic, Tristan A.; Dekrafft, Kathryn E.; Ley, Amanda N.; DeButts, Jordan C.; Pike, Robert D.; Lu, Haiyan; Patterson, Howard H.; Inorganic Chemistry; vol. 47; nb. 15; (2008); p. 6931 6947 ; (from Gmelin), View in Reaxys Conformation (1) Object of Investi- References gation Conformation

Crystal Phase (3) Description (Crys- References tal Phase) plates

Structure of the solid

Single Crystal Xray Diffraction

Crystal Property Description (2) Colour & Other References Properties pale yellow

colorless

Crystal System (1) Crystal System References

301/337

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Monoclinic

Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles Space Group (1) Space Group 4

Single Crystal Xray Diffraction

Comment (Space Group)

References

a = 19.3691 Angstroem, b = 6.82790 Angstroem, c = 21.6030 Angstroem, β = 108.035; Z = 2; T = 200 K; atomic positions available

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Comment (IR Spectroscopy)

701 cm**-1 - 3285 cm**-1

Reaxys ID 18741168 View in Reaxys

–C

238/323 Chemical Name: (CuCN)7(N-benzylpiperazine)2; (CuCN)7(BzPip)2 Linear Structure Formula: 7Cu(1+)*7CN(1-)*2(CH2)4(NCH2C6H5)NH=(CuCN)7((CH2)4(NCH 2C6H5)NH)2 Molecular Formula: 7CN*2C11H16N2*7Cu Molecular Weight: 979.469 Type of Substance: Coordination compound InChI Key: SNZODUUSTQBMFN-UHFFFAOYSA-N Note:

7 N

7 Cu +

Crystal Property Description (1) Colour & Other References Properties white

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

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Comment (IR Spectroscopy)

700 cm**-1 - 3246 cm**-1

Reaxys ID 18741169 View in Reaxys

–C

239/323

Chemical Name: (CuCN)5(N-benzylpiperazine)2; (CuCN)5(BzPip)2 Linear Structure Formula: 5Cu(1+)*5CN(1-)*2(CH2)4(NCH2C6H5)NH=(CuCN)5((CH2)4(NCH 2C6H5)NH)2 Molecular Formula: 5CN*2C11H16N2*5Cu Molecular Weight: 800.341 Type of Substance: Coordination compound InChI Key: SNZODUUSTQBMFN-UHFFFAOYSA-N Note:

5 N

5 Cu +

Crystal Property Description (1) Colour & Other References Properties cream

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Comment (IR Spectroscopy)

702 cm**-1 - 3282 cm**-1

Reaxys ID 18741170 View in Reaxys

–C

N NH

240/323 Chemical Name: (CuCN)4(N-benzylpiperazine); (CuCN)4(BzPip) Linear Structure Formula: 4Cu(1+)*4CN(1-)*(CH2)4(NCH2C6H5)NH=(CuCN)4((CH2)4(NCH2 C6H5)NH) Molecular Formula: 4CN*C11H16N2*4Cu Molecular Weight: 534.516 Type of Substance: Coordination compound InChI Key: SNZODUUSTQBMFN-UHFFFAOYSA-N Note:

4 N

4 Cu +

Density (1) 1 of 1

Density [g·cm-3]

1.858

Measurement Temperature [°C]

-173.16

Type (Density)

crystallographic

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Crystal Phase (2) Description (Crys- References tal Phase) Structure of the solid

Single Crystal Xray Diffraction

Crystal Property Description (2) Colour & Other References Properties white

colorless

Crystal System (1) Crystal System References Rhombic

Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles Space Group (1) Space Group 62

Single Crystal Xray Diffraction

Comment (Space Group)

References

a = 18.8238 Angstroem, b = 9.2760 Angstroem, c = 10.9423 Angstroem; Z = 4; T = 100 K; atomic positions available

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Comment (IR Spectroscopy)

702 cm**-1 - 3026 cm**-1

304/337

2016-05-20 15:00:44

Reaxys ID 18975170 View in Reaxys

241/323 CAS Registry Number: 523981-50-2 Chemical Name: 1-(2,6-dimethylbenzyl)piperazine Linear Structure Formula: C13H20N2 Molecular Formula: C13H20N2 Molecular Weight: 204.315 InChI Key: AHMHWLYAQFAVIW-UHFFFAOYSA-N Note:

H N

Reaxys ID 18975171 View in Reaxys

242/323 CAS Registry Number: 1109275-88-8 Chemical Name: 1-(3,5-dimethoxy-2-methylbenzyl)piperazine Linear Structure Formula: C14H22N2O2 Molecular Formula: C14H22N2O2 Molecular Weight: 250.341 InChI Key: PIQFMUCTFKTDCG-UHFFFAOYSA-N Note:

H N

N O

Reaxys ID 18975172 View in Reaxys

243/323 CAS Registry Number: 1109276-04-1 Chemical Name: 2,4-dimethoxy-6-(piperazin-1-ylmethyl)benzaldehyde Linear Structure Formula: C14H20N2O3 Molecular Formula: C14H20N2O3 Molecular Weight: 264.324 InChI Key: WOJHPPNLHUWJRZ-UHFFFAOYSA-N Note:

O O

N NH O

Reaxys ID 18975173 View in Reaxys

244/323 CAS Registry Number: 1109275-95-7 Chemical Name: 1-(2-fluoro-6-(trifluoromethyl)benzyl)piperazine Linear Structure Formula: C12H14F4N2 Molecular Formula: C12H14F4N2 Molecular Weight: 262.25 InChI Key: BRBBZTVFKGLHKL-UHFFFAOYSA-N Note:

F F

F N F

Reaxys ID 18975174 View in Reaxys

245/323

305/337

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CAS Registry Number: 1109275-99-1 Chemical Name: (2,4-dimethoxy-6-(piperazin-1-ylmethyl)phenyl)methanol Linear Structure Formula: C14H22N2O3 Molecular Formula: C14H22N2O3 Molecular Weight: 266.34 InChI Key: WWCTXDWNCBMMIJ-UHFFFAOYSA-N Note:

OH O

N NH O

Reaxys ID 18975175 View in Reaxys N O

246/323 CAS Registry Number: 1109276-02-9 Chemical Name: 2,4-dimethoxy-6-(piperazin-1-ylmethyl)benzaldehyde oxime Linear Structure Formula: C14H21N3O3 Molecular Formula: C14H21N3O3 Molecular Weight: 279.339 InChI Key: MCVYLDFLRRYOEI-UHFFFAOYSA-N Note:

OH N NH

Reaxys ID 18975176 View in Reaxys

247/323 CAS Registry Number: 1109275-90-2 Chemical Name: (4,6-dimethoxy-3-methyl-2-(piperazin-1-ylmethyl)phenyl)methanol Linear Structure Formula: C15H24N2O3 Molecular Formula: C15H24N2O3 Molecular Weight: 280.367 InChI Key: SLDLGOCOBISODJ-UHFFFAOYSA-N Note:

HO O

N NH O

Reaxys ID 18987831 View in Reaxys

248/323 CAS Registry Number: 203047-39-6 Chemical Name: methyl 3-(piperazin-1-ylmethyl)benzoate Linear Structure Formula: C13H18N2O2 Molecular Formula: C13H18N2O2 Molecular Weight: 234.298 InChI Key: SLMZNHRCTAWNQK-UHFFFAOYSA-N Note:

O O

N NH

Mass Spectrometry (1) Description (Mass References Spectrometry) ESI (Electrospray ionisation)

Patent; N.V. ORGANON; WO2009/138438; (2009); (A1) English, View in Reaxys

Reaxys ID 19009202 View in Reaxys

249/323

306/337

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Linear Structure Formula: C16H27N3O Molecular Formula: C16H27N3O Molecular Weight: 277.41 InChI Key: NEGYOXOFDLGATB-UHFFFAOYSA-N Note:

O N

Reaxys ID 19012060 View in Reaxys 2H 2H

250/323 CAS Registry Number: 1141922-46-4 Chemical Name: 1-benzyl-d7-piperazine dihydrochloride Linear Structure Formula: C11H9 (2)H7N2 Molecular Formula: C11H16N2 Molecular Weight: 183.206 InChI Key: IQXXEPZFOOTTBA-DMCBOUTMSA-N Note:

Melting Point (1) 1 of 1

Melting Point [°C]

277 - 280

You, Zong-Yi; Chen, Yi-Jing; Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 55; nb. 3; (2008); p. 663 - 667, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

300

You, Zong-Yi; Chen, Yi-Jing; Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 55; nb. 3; (2008); p. 663 - 667, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

You, Zong-Yi; Chen, Yi-Jing; Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 55; nb. 3; (2008); p. 663 - 667, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Mid IR (MIR); Bands

Comment (IR Spectroscopy)

film

You, Zong-Yi; Chen, Yi-Jing; Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 55; nb. 3; (2008); p. 663 - 667, View in Reaxys Mass Spectrometry (2) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

EI (Electron impact); Spectrum

You, Zong-Yi; Chen, Yi-Jing; Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 55; nb. 3; (2008); p. 663 - 667, View in Reaxys

mol peak

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HRMS (High resolution mass spectrometry); EI (Electron impact)

mol peak

You, Zong-Yi; Chen, Yi-Jing; Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 55; nb. 3; (2008); p. 663 - 667, View in Reaxys

Reaxys ID 19085593 View in Reaxys

NH + +H

251/323

Br–

CAS Registry Number: 1138319-44-4 Chemical Name: [1-benzylpiperazinium][TlBr4]Br Linear Structure Formula: NH2NH(CH2)4CH2C6H5 (2+)*TlBr4 (1-)*Br(1-)=NH NH(CH )4CH C H (TlBr )Br 2 2 2 6 5 4 Molecular Formula: Br*Br4Tl*C11H18N2 Molecular Weight: 782.18 Type of Substance: Coordination compound InChI Key: HJFCCXQGOKOTMG-UHFFFAOYSA-K Note:

(v1)– Br (v4)

(v1)

–Br

Tl3+– – BrBr

(v1) (v1)

Melting Point (1) 1 of 1

Melting Point [°C]

240

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 71 ; (from Gmelin), View in Reaxys Density (1) 1 of 1

Density [g·cm-3]

2.735

Measurement Temperature [°C]

-113.16

Type (Density)

crystallographic

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 71 ; (from Gmelin), View in Reaxys Conformation (1) Object of Investi- References gation Conformation

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 - 71 ; (from Gmelin), View in Reaxys

Crystal Phase (4) Description (Crys- References tal Phase) plates

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 - 71 ; (from Gmelin), View in Reaxys

Crystal growth forms

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 - 71 ; (from Gmelin), View in Reaxys

Structure of the solid

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 - 71 ; (from Gmelin), View in Reaxys

Single Crystal Xray Diffraction

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 - 71 ; (from Gmelin), View in Reaxys

Crystal Property Description (1) Colour & Other References Properties orange

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 - 71 ; (from Gmelin), View in Reaxys

Crystal System (1) Crystal System References Monoclinic

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 - 71 ; (from Gmelin), View in Reaxys

Interatomic Distances and Angles (1)

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Description

Comment (Interatomic Distances and Angles)

References

Interatomic distances and angles

Single Crystal Xray Diffraction

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 - 71 ; (from Gmelin), View in Reaxys

Comment (Space Group)

References

a = 7.1573 Angstroem, b = 14.8364 Angstroem, c = 17.8889 Angstroem, β = 90.5038; Z = 4; T = 160 K

Linden, Anthony; Petridis, Alexander; James, Bruce D.; Helvetica Chimica Acta; vol. 92; nb. 1; (2009); p. 29 - 71 ; (from Gmelin), View in Reaxys

Space Group (1) Space Group 14

Reaxys ID 19151814 View in Reaxys

252/323 CAS Registry Number: 435345-16-7 Chemical Name: 1-(2-methyl-benzyl)-piperazine hydrochloride Linear Structure Formula: C12H18N2*ClH Molecular Formula: C12H18N2*ClH Molecular Weight: 226.749 InChI Key: ITRVJMRBZMXNQV-UHFFFAOYSA-N Note:

H N

HCl

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 19151816 View in Reaxys

253/323

NH N

CAS Registry Number: 435342-11-3 Chemical Name: 1-(4-chloro-benzyl)-piperazine hydrochloride Linear Structure Formula: C11H15ClN2*ClH Molecular Formula: C11H15ClN2*ClH Molecular Weight: 247.167 InChI Key: ZKQKYKNSUWSKAN-UHFFFAOYSA-N Note:

HCl

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 19151817 View in Reaxys

254/323

NH N

CAS Registry Number: 435345-17-8 Chemical Name: 1-(4-methyl-benzyl)-piperazine hydrochloride Linear Structure Formula: C12H18N2*ClH Molecular Formula: C12H18N2*ClH Molecular Weight: 226.749

HCl

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InChI Key: IBQZMJDYEZMXKW-UHFFFAOYSA-N Note: Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 19151818 View in Reaxys

255/323 CAS Registry Number: 1048648-80-1 Chemical Name: 1-(3-fluoro-benzyl)-piperazine hydrochloride Linear Structure Formula: C11H15FN2*ClH Molecular Formula: C11H15FN2*ClH Molecular Weight: 230.713 InChI Key: OFWHWGFADDKKHZ-UHFFFAOYSA-N Note:

N NH HCl F

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 19151819 View in Reaxys

256/323 Chemical Name: 1-(3-methyl-benzyl)-piperazine dihydrochloride Linear Structure Formula: C12H18N2*2ClH Molecular Formula: C12H18N2*2ClH Molecular Weight: 263.21 InChI Key: LRIBNLURQXBORF-UHFFFAOYSA-N Note:

2 HCl N NH

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 19151822 View in Reaxys

257/323 CAS Registry Number: 435341-97-2 Chemical Name: 1-(4-ethyl-benzyl)-piperazine hydrochloride Linear Structure Formula: C13H20N2*ClH Molecular Formula: C13H20N2*ClH Molecular Weight: 240.776 InChI Key: LNACVROTABIGQP-UHFFFAOYSA-N Note:

NH HCl N

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

310/337

2016-05-20 15:00:44

Reaxys ID 19151823 View in Reaxys

258/323 2

O N

Chemical Name: 1-(3-nitrobenzyl)piperazine dihydrochloride Linear Structure Formula: C11H15N3O2*2ClH Molecular Formula: C11H15N3O2*2ClH Molecular Weight: 294.181 InChI Key: OVVDYGYSNSCOEN-UHFFFAOYSA-N Note:

HCl

N NH

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 19151824 View in Reaxys O

259/323 Chemical Name: 1 -(2-nitrobenzyl)piperazine dihydrochloride Linear Structure Formula: C11H15N3O2*2ClH Molecular Formula: C11H15N3O2*2ClH Molecular Weight: 294.181 InChI Key: RQCUMEZZBVRDIF-UHFFFAOYSA-N Note:

HCl

N NH

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English, View in Reaxys

Reaxys ID 19471274 View in Reaxys

260/323 CAS Registry Number: 1187890-59-0 Chemical Name: 1-(3,4,5-trifluoro-benzyl)-piperazine hydrochloride Linear Structure Formula: C11H13F3N2*ClH Molecular Formula: C11H13F3N2*ClH Molecular Weight: 266.694 InChI Key: OEKIOSHPCNHHFJ-UHFFFAOYSA-N Note:

F F

NH HCl N

Reaxys ID 19558863 View in Reaxys O HO

261/323 CAS Registry Number: 1000517-09-8 Linear Structure Formula: C13H18N2O2 Molecular Formula: C13H18N2O2 Molecular Weight: 234.298 InChI Key: UMNKYAHZIYWRKK-UHFFFAOYSA-N Note:

H N

Substance Label (1) Label References Cap-45

Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/102318; (2009); (A1) English, View in Reaxys

Mass Spectrometry (1) Description (Mass References Spectrometry)

311/337

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LCMS (Liquid chromatography mass spectrometry)

Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/102318; (2009); (A1) English, View in Reaxys

Reaxys ID 19757379 View in Reaxys

262/323 CAS Registry Number: 1196693-61-4 Chemical Name: 1,1,1,3,3,3-hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol Linear Structure Formula: C14H16F6N2O Molecular Formula: C14H16F6N2O Molecular Weight: 342.284 InChI Key: XTBJONBTIAHHGH-UHFFFAOYSA-N Note:

N NH

F HO F

F F

Mass Spectrometry (1) Description (Mass References Spectrometry) ESI (Electrospray ionisation)

Patent; N.V. ORGANON; WO2009/138438; (2009); (A1) English, View in Reaxys

Reaxys ID 19889767 View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties yellow

supporting information

263/323 CAS Registry Number: 1187960-09-3 Chemical Name: 1-(3-(azidomethyl)benzyl)piperazine Linear Structure Formula: C12H17N5 Molecular Formula: C12H17N5 Molecular Weight: 231.3 InChI Key: JLTFGLGHWXBAFQ-UHFFFAOYSA-N Note:

N NH

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy)

312/337

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Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Peterson, Quinn P.; Hsu, Danny C.; Goode, David R.; Novotny, Chris J.; Totten, Ryan K.; Hergenrother, Paul J.; Journal of Medicinal Chemistry; vol. 52; nb. 18; (2009); p. 5721 - 5731, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum

References

supporting information

Peterson, Quinn P.; Hsu, Danny C.; Goode, David R.; Novotny, Chris J.; Totten, Ryan K.; Hergenrother, Paul J.; Journal of Medicinal Chemistry; vol. 52; nb. 18; (2009); p. 5721 - 5731, View in Reaxys

Reaxys ID 19981851 View in Reaxys

NH N

264/323

O S

Linear Structure Formula: CH4O3S*C11H16N2 Molecular Formula: CH4O3S*C11H16N2 Molecular Weight: 272.368 InChI Key: CQPUARMVMSCOTG-UHFFFAOYSA-N Note:

Reaxys ID 20049640 View in Reaxys

265/323 CAS Registry Number: 1206515-95-8 Chemical Name: 1-(4-fluoro-2-trifluoromethyl-benzyl)-piperazine Linear Structure Formula: C12H14F4N2 Molecular Formula: C12H14F4N2 Molecular Weight: 262.25 InChI Key: JOFNQKGOVZPLSU-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 7b

Patent; PIERRE FABRE MEDICAMENT; LEROY, Isabelle; DUPONT-PASSELAIGUE, Elisabeth; VALEILLE, Karine; RIVAL, Yves; JUNQUERO, Didier; WO2010/6962; (2010); (A1) English, View in Reaxys

Reaxys ID 20170472 View in Reaxys

266/323 Chemical Name: 1-[4-fluoro-3-(trifluoromethyl)benzyl]piperazine hydrochloride Linear Structure Formula: C12H14F4N2*ClH Molecular Formula: C12H14F4N2*ClH Molecular Weight: 298.711 InChI Key: RQZUCGBERARWOD-UHFFFAOYSA-N Note:

F F N

F F

HCl NH

Mass Spectrometry (1)

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Description (Mass Location Spectrometry)

References

DCI (Desorption chemical ionization)

Patent; ABBOTT LABORATORIES; BHATIA, Pramila, A.; DOHERTY, George, A.; DRIZIN, Irene; MACK, Helmut; PERNER, Richard, J.; STEWART, Andrew, O.; ZHANG, Qing Wei; WO2010/39947; (2010); (A1) English, View in Reaxys

Page/Page column 151

Reaxys ID 20493627 View in Reaxys

267/323 CAS Registry Number: 1400541-81-2 Linear Structure Formula: C11H15BrN2O Molecular Formula: C11H15BrN2O Molecular Weight: 271.157 InChI Key: OZZSNFLVYHBCOL-UHFFFAOYSA-N Note:

OH N NH Br

Reaxys ID 20561337 View in Reaxys

268/323 CAS Registry Number: 1082474-73-4 Chemical Name: 4-(piperazin-1-ylmethyl)benzenesulfonamide Linear Structure Formula: C11H17N3O2S Molecular Formula: C11H17N3O2S Molecular Weight: 255.341 InChI Key: WRXKVWZWTQMQSA-UHFFFAOYSA-N Note:

N O H 2N

S O

Substance Label (1) Label References 6

Crystal Property Description (1) Colour & Other Location Properties light-yellow

Page/Page column 71

References Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; HERGENROTHER, Paul Joseph; PETERSON, Quinn Patrick; HSU, Danny Chung; WEST, Diana C.; FAN, Timothy M.; NOVOTNY, Chris J.; WO2010/91382; (2010); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- water-d2; hexadeuterioacetone scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H NMR (400 MHz, D O/(CD ) CO): δ 7.84 (d, J = 8.4Hz, 2H), 7.51 (d, J = 8.4Hz, 2H), 2 3 2 3.69 (s, 2H), 3.42 (s, 2H), 3.22 (m, 4H), 2.74 (m, 4H), 1.87 (apparent s, 1 H).

Location

Page/Page column 71

Comment (NMR Spectroscopy)

Signals given

Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

126

Original Text (NMR Spectroscopy)

13C

Location

Page/Page column 71

Comment (NMR Spectroscopy)

Signals given

NMR (126 MHz, CDCI3): δ 140.93, 140.87, 131.0, 126.3, 61.1 , 49.0, 43.13.

Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; HERGENROTHER, Paul Joseph; PETERSON, Quinn Patrick; HSU, Danny Chung; WEST, Diana C.; FAN, Timothy M.; NOVOTNY, Chris J.; WO2010/91382; (2010); (A1) English, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Neat (no solvent)

Original Text (IR Spectroscopy)

IR (neat): 3142, 1158 cm-1.

Location

Page/Page column 71

References

Page/Page column 71

Reaxys ID 20688004 View in Reaxys

269/323 CAS Registry Number: 1032620-20-4 Linear Structure Formula: C11H17BN2O2 Molecular Formula: C11H17BN2O2 Molecular Weight: 220.079 InChI Key: FJQOCSNNOVOYQI-UHFFFAOYSA-N Note:

OH HO

N NH

Reaxys ID 21308112 View in Reaxys F

270/323 CAS Registry Number: 1163144-92-0 Linear Structure Formula: C13H15F3N2O2 Molecular Formula: C13H15F3N2O2 Molecular Weight: 288.27 InChI Key: VUDYVDUAMXOANH-UHFFFAOYSA-N Note:

N O

NH OH

Mass Spectrometry (1) Description (Mass References Spectrometry) IT (ion trap); ESI Gong, Aishen; Chen, Xiaoyan; Deng, Pan; Zhong, Dafang; Drug Metabolism and Disposition; vol. 38; nb. (Electrospray ioni- 8; (2010); p. 1328 - 1340, View in Reaxys sation); TOFMS (Time of flight

315/337

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mass spectrum); LCMS (Liquid chromatography mass spectrometry); Spectrum

Reaxys ID 21379789 View in Reaxys

271/323 Chemical Name: N1-benzylpiperazine hydrochloride Linear Structure Formula: C11H16N2*(x)ClH Molecular Formula: C11H16N2*(x)ClH InChI Key: HRSFWIYFGGDGQO-UHFFFAOYSA-N Note:

-1 HCl N NH

Reaxys ID 21563479 View in Reaxys

272/323 CAS Registry Number: 874774-61-5 Linear Structure Formula: C11H14F2N2 Molecular Formula: C11H14F2N2 Molecular Weight: 212.242 InChI Key: DCUMZROHXKMGAR-UHFFFAOYSA-N Note:

H N

Reaxys ID 21860152 View in Reaxys

273/323 CAS Registry Number: 84884-91-3 Linear Structure Formula: C13H19N3O2 Molecular Formula: C13H19N3O2 Molecular Weight: 249.313 InChI Key: WIRHJGQOGIGNCE-UHFFFAOYSA-N Note:

H N

HN O

Reaxys ID 22424831 View in Reaxys

274/323 CAS Registry Number: 1370010-59-5 Linear Structure Formula: C12H15ClN2O Molecular Formula: C12H15ClN2O Molecular Weight: 238.717 InChI Key: DHVVXTHTHMCJON-UHFFFAOYSA-N Note:

Cl O

NH N

Reaxys ID 22424836 View in Reaxys

275/323

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CAS Registry Number: 1370010-58-4 Linear Structure Formula: C12H15ClN2O Molecular Formula: C12H15ClN2O Molecular Weight: 238.717 InChI Key: VAUGDRCHWZKVFZ-UHFFFAOYSA-N Note:

O Cl

N NH

Reaxys ID 22424896 View in Reaxys H N

NH 2

276/323 Linear Structure Formula: C13H19N5OS Molecular Formula: C13H19N5OS Molecular Weight: 293.393 InChI Key: SVXOGQPUQXDXRZ-UHFFFAOYSA-N Note:

O N H

N NH

Reaxys ID 22424897 View in Reaxys S

277/323

NH 2 HN

Linear Structure Formula: C13H19N5OS Molecular Formula: C13H19N5OS Molecular Weight: 293.393 InChI Key: RHDNQZRJKXOAPH-UHFFFAOYSA-N Note:

NH N

Reaxys ID 22637135 View in Reaxys

278/323 CAS Registry Number: 1369294-76-7 Linear Structure Formula: C20H34N2O Molecular Formula: C20H34N2O Molecular Weight: 318.503 InChI Key: DEXFQRFNPMDOSH-UHFFFAOYSA-N Note:

H N

Reaxys ID 22688167 View in Reaxys

279/323 CAS Registry Number: 1384448-26-3 Linear Structure Formula: C11H12 (2)H2F2N2*ClH Molecular Formula: C11H14F2N2*ClH Molecular Weight: 250.687 InChI Key: BWTIPGSURKWXJM-PTYOUXKQSA-N Note:

HCl 2H 2H

N NH F

Reaxys ID 22750546 View in Reaxys

280/323

317/337

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N H 13 2 C

CAS Registry Number: 1384626-59-8 Chemical Name: (13)C4-1-benzylpiperazine Linear Structure Formula: C7 (13)C4H16N2 Molecular Formula: C11H16N2 Molecular Weight: 180.217 InChI Key: IQXXEPZFOOTTBA-NNZQUYKOSA-N Note:

H 13C 2

13CH

13C

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Lake, Fredrik; Linde, Christian; Tetrahedron Letters; vol. 53; nb. 30; (2012); p. 3927 - 3929, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

ESI (Electrospray supporting inforionisation); LCMS mation (Liquid chromatography mass spectrometry); Spectrum

Lake, Fredrik; Linde, Christian; Tetrahedron Letters; vol. 53; nb. 30; (2012); p. 3927 3929, View in Reaxys

Reaxys ID 22835058 View in Reaxys

281/323 CAS Registry Number: 523980-91-8 Linear Structure Formula: C13H20N2 Molecular Formula: C13H20N2 Molecular Weight: 204.315 InChI Key: YPZULLYQDCUEFL-UHFFFAOYSA-N Note:

N NH

Reaxys ID 23161013 View in Reaxys

282/323 CAS Registry Number: 1429900-27-5 Linear Structure Formula: C11H15 (18)FN2 Molecular Formula: C11H15FN2 Molecular Weight: 193.253 InChI Key: OOSZCNKVJAVHJI-DWSYCVKZSA-N Note:

N 18

Substance Label (1) Label References 5

Dahl, Kenneth; Schou, Magnus; Halldin, Christer; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 55; nb. 13; (2012); p. 455 - 459, View in Reaxys

Reaxys ID 23711519 View in Reaxys

283/323

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CAS Registry Number: 1443057-88-2 Chemical Name: 1-(2-(3-methoxypropoxy)benzyl)piperazine Linear Structure Formula: C15H24N2O2 Molecular Formula: C15H24N2O2 Molecular Weight: 264.368 InChI Key: UFJXBAHHXNDYRZ-UHFFFAOYSA-N Note:

O N NH

Substance Label (1) Label References Amine 5

Patent; CADILA HEALTHCARE LIMITED; THOMBARE, Pravin, S.; DESAI, Jigar, N.; WO2013/84241; (2013); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties white

References

Page/Page column 20

Patent; CADILA HEALTHCARE LIMITED; THOMBARE, Pravin, S.; DESAI, Jigar, N.; WO2013/84241; (2013); (A1) English, View in Reaxys

Reaxys ID 23711523 View in Reaxys

284/323 CAS Registry Number: 1443057-89-3 Chemical Name: 1-(3-(3-methoxypropoxy)benzyl)piperazine Linear Structure Formula: C15H24N2O2 Molecular Formula: C15H24N2O2 Molecular Weight: 264.368 InChI Key: PIPMKMWGTBMJDP-UHFFFAOYSA-N Note:

NH O

Substance Label (1) Label References Amine 6

Patent; CADILA HEALTHCARE LIMITED; THOMBARE, Pravin, S.; DESAI, Jigar, N.; WO2013/84241; (2013); (A1) English, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties white

References

Page/Page column 21

Patent; CADILA HEALTHCARE LIMITED; THOMBARE, Pravin, S.; DESAI, Jigar, N.; WO2013/84241; (2013); (A1) English, View in Reaxys

Reaxys ID 23961720 View in Reaxys

285/323 2

Chemical Name: N-(2,3,4-triethoxybenzyl)piperazine dihydrochloride Linear Structure Formula: C17H28N2O3*2ClH Molecular Formula: C17H28N2O3*2ClH Molecular Weight: 381.343 InChI Key: HVODZLDLSZZTOE-UHFFFAOYSA-N Note:

HCl

O O

Patent-Specific Data (1) Location in Patent References Page/Page column

Reaxys ID 23961730 View in Reaxys

286/323

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Chemical Name: N-(3,5-dimethoxy-4-ethoxybenzyl)piperazine dihydrochloride Linear Structure Formula: C15H24N2O3*2ClH Molecular Formula: C15H24N2O3*2ClH Molecular Weight: 353.289 InChI Key: NHROYCUNJOSSQM-UHFFFAOYSA-N Note:

2 HCl

N NH

O O

Patent-Specific Data (1) Location in Patent References Page/Page column

Reaxys ID 23961736 View in Reaxys

287/323 Chemical Name: N-(4-(2-methylpropyloxy)-3-methoxybenzyl)piperazine dihydrochloride Linear Structure Formula: C16H26N2O2*2ClH Molecular Formula: C16H26N2O2*2ClH Molecular Weight: 351.317 InChI Key: KLOIOLZWVHFDAW-UHFFFAOYSA-N Note:

2 HCl

N NH

Patent-Specific Data (1) Location in Patent References Page/Page column

Reaxys ID 24005879 View in Reaxys

288/323 Chemical Name: (3-tert-butyl-4-methoxybenzyl)-piperazine dihydrochloride Linear Structure Formula: C16H26N2O*2ClH Molecular Formula: C16H26N2O*2ClH Molecular Weight: 335.317 InChI Key: PLFSOCPBTUVDHU-UHFFFAOYSA-N Note:

2 HCl N NH

Patent-Specific Data (1) Location in Patent References Page/Page column

Reaxys ID 24622700 View in Reaxys

289/323 Chemical Name: trimetazidine; 1-(2,3,4-trimethoxybenzyl)piperazine hydrochloride Linear Structure Formula: C14H22N2O3*xClH Molecular Formula: C14H22N2O3*(x)ClH InChI Key: QHWBCHACIJBSFV-UHFFFAOYSA-N Note:

-1 HCl O O

N NH

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Spectrum

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Solvent (UV/VIS Spectroscopy)

water

Li, Jiao; Quan, Jie; Du, Jianxiu; Liu, Mei; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 114; (2013); p. 33 - 37, View in Reaxys

Reaxys ID 25076508 View in Reaxys O

290/323 Linear Structure Formula: C12H16N2O3 Molecular Formula: C12H16N2O3 Molecular Weight: 236.271 InChI Key: ITCOFNVMLHDHMD-UHFFFAOYSA-N Note:

OH N NH

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Chipeleme, Alex; Gut, Jiri; Rosenthal, Philip J.; Chibale, Kelly; Bioorganic and Medicinal Chemistry; vol. 15; nb. 1; (2007); p. 273 - 282, View in Reaxys

Reaxys ID 25076514 View in Reaxys

291/323

H N

Linear Structure Formula: C13H19N5O2S Molecular Formula: C13H19N5O2S Molecular Weight: 309.392 InChI Key: OXUPCPBXBIEUTQ-FRKPEAEDSA-N Note:

OH E

NH 2 S

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Chipeleme, Alex; Gut, Jiri; Rosenthal, Philip J.; Chibale, Kelly; Bioorganic and Medicinal Chemistry; vol. 15; nb. 1; (2007); p. 273 - 282, View in Reaxys

Reaxys ID 25459936 View in Reaxys

292/323 Linear Structure Formula: C11H13ClF2N2 Molecular Formula: C11H13ClF2N2 Molecular Weight: 246.687 InChI Key: KUGCUPZFTNHCGU-UHFFFAOYSA-N Note:

H N

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

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Reaxys ID 26521657 View in Reaxys

293/323

N 2H 2H

CAS Registry Number: 1477749-92-0 Chemical Name: (2,3-dimethoxybenzyl)piperazine-D8 Linear Structure Formula: C13H12 (2)H8N2O2 Molecular Formula: C13H20N2O2 Molecular Weight: 244.25 InChI Key: RHKQXCFGQFIGNO-COMRDEPKSA-N Note:

NH 2H

Chromatographic Data (1) Chromatographic References data GC (Gas chroma- Abdel-Hay, Karim M.; Deruiter, Jack; Clark, C. Randall; Rapid Communications in Mass Spectrometry; tography) vol. 27; nb. 22; (2013); p. 2551 - 2558, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) gas chromatogra- Abdel-Hay, Karim M.; Deruiter, Jack; Clark, C. Randall; Rapid Communications in Mass Spectrometry; phy mass specvol. 27; nb. 22; (2013); p. 2551 - 2558, View in Reaxys trometry (GCMS); electron impact (EI); spectrum

Reaxys ID 26532489 View in Reaxys

294/323 Linear Structure Formula: C12H16N2O2*2ClH Molecular Formula: C12H16N2O2*2ClH Molecular Weight: 293.193 Note:

2 HCl N O

NH OH

Substance Label (1) Label References 9d

Peng, Zhenghong; Maxwell, David S.; Sun, Duoli; Bhanu Prasad, Basvoju A.; Pal, Ashutosh; Wang, Shimei; Balatoni, Julius; Ghosh, Pradip; Lim, Seok T.; Volgin, Andrei; Shavrin, Aleksander; Alauddin, Mian M.; Gelovani, Juri G.; Bornmann, William G.; Bioorganic and Medicinal Chemistry; vol. 22; nb. 1; (2014); p. 623 - 632, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

1H; 19F

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

600.1

Reaxys ID 26611649 View in Reaxys

295/323

322/337

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CAS Registry Number: 1261232-17-0 Chemical Name: 1-(2,5-dichlorobenzyl)piperazine hydrochloride Linear Structure Formula: C11H14Cl2N2*ClH Molecular Formula: C11H14Cl2N2*ClH Molecular Weight: 281.613 Note:

H N

N HCl

Reaxys ID 26835964 View in Reaxys

296/323 CAS Registry Number: 1609658-60-7 Chemical Name: 2-dipropylaminomethyl-4-piperazin-1-ylmethylphenol hydrochloride Linear Structure Formula: ClH*C18H31N3O Molecular Formula: C18H31N3O*ClH Molecular Weight: 341.925 InChI Key: VXZMFYWEGJSXEJ-UHFFFAOYSA-N Note:

N NH HCl

Chromatographic Data (1) Chromatographic Original string data

Location

References

LC (Liquid chromatography)

Page/Page column 61

Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CIANA, Claire-Lise; SIEGRIST, Romain; WO2014/72903; (2014); (A1) English, View in Reaxys

RT (min) 0.34

Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

liquid chromatog- Page/Page colraphy mass spec- umn 61 trometry (LCMS); spectrum

Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CIANA, Claire-Lise; SIEGRIST, Romain; WO2014/72903; (2014); (A1) English, View in Reaxys

Reaxys ID 26876676 View in Reaxys

297/323 CAS Registry Number: 859027-31-9 Chemical Name: 1-(4-nitro-2-trifluoromethyl-benzyl)-piperazine Linear Structure Formula: C12H14F3N3O2 Molecular Formula: C12H14F3N3O2 Molecular Weight: 289.257 InChI Key: SQBMNLHHBDQRAK-UHFFFAOYSA-N Note:

F F

F N

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

600

Original Text (NMR Spectroscopy)

1H NMR (600 MHz, DMSO-d6) δ ppm 2.35 (br. s., 4 H) 2.73 (t, J=4.67 Hz, 5 H) 3.69 (s, 2 H) 8.11 (d, J=8.43 Hz, 1 H)8.41 (d, J=2.20 Hz, 1 H) 8.51 (dd, J=8.70, 2.11 Hz, 1 H).

Location

Page/Page column 40

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Patent; NERVIANO MEDICAL SCIENCES S.R.L.; MENICHINCHERI, Maria; ANGIOLINI, Mauro; BERTRAND, Jay Aaron; CARUSO, Michele; POLUCCI, Paolo; QUARTIERI, Francesca; SALOM, Barbara; SALSA, Matteo; ZUCCOTTO, Fabio; WO2014/72220; (2014); (A1) English, View in Reaxys

Reaxys ID 27386267 View in Reaxys

298/323 Chemical Name: (E)-ethyl 3-(4-((piperazin-1-yl)methyl)phenyl)prop-2-enoate Linear Structure Formula: C16H22N2O2 Molecular Formula: C16H22N2O2 Molecular Weight: 274.363 InChI Key: FKOCLCSABYLKEX-BQYQJAHWSA-N Note:

N NH E O O

Substance Label (1) Label References R-09c

Patent; FUNDACIÓN PARA LA INVESTIGACIÓN MÉDICA APLICADA; CUADRADO TEJEDOR, María Del Mar; FRANCO FERNÁNDEZ, Rafael; GARCÍA OSTA, Ana María; OYARZABAL SANTAMARINA, Julen; RABAL GRACIA, Maria Obdulia; WO2014/131855; (2014); (A1) English, View in Reaxys

Mass Spectrometry (1) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

References

Page/Page column 68

Reaxys ID 27791031 View in Reaxys

299/323 Linear Structure Formula: C11H14BrFN2 Molecular Formula: C11H14BrFN2 Molecular Weight: 273.148 InChI Key: NRCBEINBLSTDHM-UHFFFAOYSA-N Note:

H N

Reaxys ID 27866702 View in Reaxys H 2N O

300/323 Chemical Name: 2-amino-5-chloro-4-piperazin-1-ylmethylbenzoic acid ethyl ester Linear Structure Formula: C14H20ClN3O2 Molecular Formula: C14H20ClN3O2 Molecular Weight: 297.785 InChI Key: JQOFOGILEUDJPN-UHFFFAOYSA-N Note:

N Cl

Substance Label (1) Label References d2

Patent; Chugai Seiyaku Kabushiki Kaisha; MURATA, Takeshi; KAWADA, Hatsuo; NIIZUMA, Satoshi; HARA, Sousuke; HADA, Kihito; SHIMADA, Hideaki; TANAKA, Hiroshi; MIO, Toshiyuki; EP2842946; (2015); (A1) English, View in Reaxys

Patent-Specific Data (1) Location in Patent References

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Page/Page column

Reaxys ID 27866716 View in Reaxys

301/323 Chemical Name: 2-amino-5-chloro-3-piperazin-1-ylmethylbenzoic acid ethyl ester Linear Structure Formula: C14H20ClN3O2 Molecular Formula: C14H20ClN3O2 Molecular Weight: 297.785 InChI Key: XUEXILPFVKDDFX-UHFFFAOYSA-N Note:

H N

N Cl

NH 2 O

Substance Label (1) Label References d17

Patent-Specific Data (1) Location in Patent References Page/Page column

Reaxys ID 27866826 View in Reaxys

302/323 Chemical Name: 2-amino-3,5-dichloro-4-piperazin-1-ylmethylbenzoic acid ethyl ester Linear Structure Formula: C14H19Cl2N3O2 Molecular Formula: C14H19Cl2N3O2 Molecular Weight: 332.23 InChI Key: ORMNXDAMIAPWRE-UHFFFAOYSA-N Note:

H N

Cl O

NH 2

Substance Label (1) Label References i5

Patent-Specific Data (1) Location in Patent References Page/Page column

Reaxys ID 27965961 View in Reaxys 2H 2H

303/323 (2)H

Linear Structure Formula: C12H10 8N2O Molecular Formula: C12H18N2O Molecular Weight: 214.224 InChI Key: MGLUVVBFISROAH-COMRDEPKSA-N Note:

H 2H

N O

2H 2H

NH 2

H 2H

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Reaxys ID 28130421 View in Reaxys

304/323 Chemical Name: 5-allyl-3-(piperazin-1-ylmethyl)benzene-1,2diol Linear Structure Formula: C14H20N2O2 Molecular Formula: C14H20N2O2 Molecular Weight: 248.325 InChI Key: STUXPWGMBLSNKZ-UHFFFAOYSA-N Note:

H N

Substance Label (1) Label References 10

Kumar, Sunil; Pathania, Anoop S.; Satti, Naresh K.; Dutt, Parbhu; Sharma, Neha; Mallik, Fayaz A.; Ali, Asif; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 236 - 245, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

190 - 191

Kumar, Sunil; Pathania, Anoop S.; Satti, Naresh K.; Dutt, Parbhu; Sharma, Neha; Mallik, Fayaz A.; Ali, Asif; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 236 - 245, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400.1

Original Text (NMR Spectroscopy)

1H NMR (400 MHz, CDCl ) δ: 6.70 (s, 1H), 6.36 (s, 1H), 5.91 (ddt, J = 16.8, 9.9, 6.7 Hz, 3 1H), 5.16-4.99 (m, 2H), 3.70 (s, 2H), 3.24 (d, J = 6.7 Hz, 2H) 2.94 (d, J = 10.9 Hz, 2H), 2.09 (t, J = 11.2 Hz, 2H), 1.67 (ds t, 2H), 1.35-1.23 (m, 2H)

Location

supporting information

Signals [ppm]

6.7; 6.36; 5.91; 4.99 - 5.16; 3.7; 3.24; 2.94; 2.09; 1.67; 1.23 - 1.35

Kind of signal

s, 1H; s, 1H; ddt, J = 16.8, 9.9, 6.7 Hz, 1H; m, 2H; s, 2H; d, J = 6.7 Hz, 2H; d, J = 10.9 Hz, 2H; t, J = 11.2 Hz, 2H; ds t, 2H; m, 2H

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Original Text (NMR Spectroscopy)

13C

Location

supporting information

Signals [ppm]

145.82; 144.1; 139.16; 132.78; 122.33; 121.14; 116.54; 116.37; 62.09; 53.68; 49.45; 40.84

Kind of signal

symmetric, 2*CH&2%; symmetric, 2*CH&2%

NMR (101 MHz, CD3OD) δ: 145.82, 144.10, 139.16, 132.78, 122.33, 121.14, 116.54, 116.37, 62.09, 53.68 (symmetric, 2*CH2), 49.45 (symmetric, 2*CH2), 40.84

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Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Location

supporting information

Kumar, Sunil; Pathania, Anoop S.; Satti, Naresh K.; Dutt, Parbhu; Sharma, Neha; Mallik, Fayaz A.; Ali, Asif; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 236 - 245, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution supporting informass spectrome- mation try (HRMS); timeof-flight mass spectra (TOFMS); electrospray ionisation (ESI); spectrum

Peak

References

249.1619 m/z

Kumar, Sunil; Pathania, Anoop S.; Satti, Naresh K.; Dutt, Parbhu; Sharma, Neha; Mallik, Fayaz A.; Ali, Asif; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 236 - 245, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Comment (Pharmacological Data)

physiological behaviour discussed

Kumar, Sunil; Pathania, Anoop S.; Satti, Naresh K.; Dutt, Parbhu; Sharma, Neha; Mallik, Fayaz A.; Ali, Asif; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 236 - 245, View in Reaxys

Reaxys ID 28290789 View in Reaxys

305/323

OH O -1

O N

Chemical Name: 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'tetraacetic acid N,N'-di[(2-octyloxy)ethyl ester] 1-(2,3,4-trimethoxybenzyl)piperazinium Linear Structure Formula: C42H64N2O12*xC14H22N2O3 Molecular Formula: (x)C14H22N2O3*C42H64N2O12 InChI Key: RWPOCNOCJKNGRS-UHFFFAOYSA-N Note:

N O

OH O

Reaxys ID 28334277 View in Reaxys

306/323 Chemical Name: 1-(3,5-dichlorobenzyl)piperazine dihydrochloride Linear Structure Formula: C11H14Cl2N2*2ClH Molecular Formula: C11H14Cl2N2*2ClH Molecular Weight: 318.073 InChI Key: YNNBYZCZMNQIEM-UHFFFAOYSA-N Note:

2 HCl

N NH Cl

Crystal Property Description (1)

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Colour & Other Properties

Location

References

colourless

Page/Page column 615

Patent; GENENTECH, INC.; XENON PHARMACEUTICALS INC.; ANDREZ, JeanChristophe; BICHLER, Paul Robert; CHEN, Chien-An; CHOWDHURY, Sultan; DECKER, Shannon Marie; DEHNHARDT, Christoph Martin; FOCKEN, Thilo; GRIMWOOD, Michael Edward; HEMEON, Ivan William; JIA, Qi; LI, Jun; LIU, Zhiguo; ORTWINE, Daniel F.; SAFINA, Brian; SUTHERLIN, Daniel; SHENG, Tao; SUN, Shaoyi; WHITE, Andrew D.; WILSON, Michael Scott; ZENOVA, Alla Yurevna; ZHU, Jiuxiang; WO2015/78374; (2015); (A1) English, View in Reaxys

Mass Spectrometry (1) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

References

Page/Page column 615

Reaxys ID 28371754 View in Reaxys

307/323 Chemical Name: N,N-dimethyl-2-(4-(piperazin-1-ylmethyl)phenoxy)ethanamine hydrochloride Linear Structure Formula: C15H25N3O*xClH Molecular Formula: C15H25N3O*(x)ClH InChI Key: AKMFOZYBFYGBHK-UHFFFAOYSA-N Note:

-1 HCl N N

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H-NMR

Location

Page/Page column 52

δ (300 MHz, CD3OD): 3.0 (s, 6H), 3.6 (s, 10H), 4.3 - 4.5 (m, 4H), 7.2 (d, 2H), 7.6

(d, 2H).

Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/91531; (2015); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) spectrum

Page/Page column 52

References Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/91531; (2015); (A1) English, View in Reaxys

Reaxys ID 28444826 View in Reaxys

308/323

328/337

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Chemical Name: tert-butyl (2-(4-(piperazin-1-ylmethyl)phenoxy)ethyl)carbamate Linear Structure Formula: C18H29N3O3 Molecular Formula: C18H29N3O3 Molecular Weight: 335.447 InChI Key: WNGADVKBFVODDI-UHFFFAOYSA-N Note:

H N

NH O

Mass Spectrometry (1) Description (Mass Location Spectrometry) spectrum

References

Page/Page column 98

Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); (A1) English, View in Reaxys

Reaxys ID 28444838 View in Reaxys

309/323 Chemical Name: tert-butyl methyl{2-[4-(piperazin-1-ylmethyl)phenoxy]ethyl}carbamate Linear Structure Formula: C19H31N3O3 Molecular Formula: C19H31N3O3 Molecular Weight: 349.473 InChI Key: XKSFYQAFIGVQJJ-UHFFFAOYSA-N Note:

N O

Mass Spectrometry (1) Description (Mass Location Spectrometry) spectrum

References

Page/Page column 100

Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); (A1) English, View in Reaxys

Reaxys ID 28444981 View in Reaxys

310/323

N N

Chemical Name: N,N-dimethyl-2-(4-(piperazin-1-ylmethyl)phenoxy)ethanamine hydrochloride Linear Structure Formula: C15H25N3O*ClH Molecular Formula: C15H25N3O*ClH Molecular Weight: 299.844 InChI Key: AKMFOZYBFYGBHK-UHFFFAOYSA-N Note:

HCl

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H-NMR (300 MHz, CD3OD): 3.0 (s, 6H), 3.6 (s, 1OH), 4.3 - 4.5 (m, 4H), 7.2 (d, 2H), 7.6 (d, 2H).

Location

Page/Page column 65

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Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) spectrum

References

Page/Page column 65

Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); (A1) English, View in Reaxys

Reaxys ID 28444985 View in Reaxys

311/323

H N

Chemical Name: N,N-dimethyl-2-[3-(piperazin-1-ylmethyl)phenoxy]ethanamine Linear Structure Formula: C15H25N3O Molecular Formula: C15H25N3O Molecular Weight: 263.383 InChI Key: XAIWMGQPSOZYNQ-UHFFFAOYSA-N Note:

Crystal Property Description (1) Colour & Other Location Properties colourless

Page/Page column 67

Mass Spectrometry (1) Description (Mass Location Spectrometry) spectrum

Page/Page column 67

References Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); (A1) English, View in Reaxys References Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); (A1) English, View in Reaxys

Reaxys ID 28444986 View in Reaxys

312/323 Chemical Name: N,N-dimethyl-3-(4-(piperazin-1-ylmethyl)phenoxy)propan-1-amine hydrochloride Linear Structure Formula: C16H27N3O*ClH Molecular Formula: C16H27N3O*ClH Molecular Weight: 313.871 InChI Key: SEZBGEJWGPDJFS-UHFFFAOYSA-N Note:

N N

NH HCl

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR (400 MHz, D20): 2.26 (m, 2H), 2.96 (s, 6H), 3.94 (t, 2H), 3.61 (bs,8H), 4.22 (m, 2H), 4.44 (s, 2H), 7.11 -7.13 (d, 2H), 7.49 -7.51 (d, 2H).

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Location

Page/Page column 68

References

Page/Page column 68

Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); (A1) English, View in Reaxys

Reaxys ID 28444995 View in Reaxys

313/323 Chemical Name: {2-[2,6-dimethyl-4-(piperazin-1-ylmethyl)phenoxy]ethyl}dimethylamine hydrochloride Linear Structure Formula: C17H29N3O*ClH Molecular Formula: C17H29N3O*ClH Molecular Weight: 327.898 InChI Key: YBNVEXUNHIEMBK-UHFFFAOYSA-N Note:

H N

HCl O

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR (400 MHz, D20): 2.35 (s, 6H), 3.09 (s, 6H), 3.53 - 3.65 (m, 8H), 3.66 -3.71 (m, 2H), 4.17-4.28 (m, 2H), 4.38 (s, 2H), 7.26 (s, 2H).

Location

Page/Page column 71

Reaxys ID 28444998 View in Reaxys

314/323 Chemical Name: {2-[3,5-dimethyl-4-(piperazin-1-ylmethyl)phenoxy]ethyl}dimethylamine Linear Structure Formula: C17H29N3O Molecular Formula: C17H29N3O Molecular Weight: 291.437 InChI Key: PWWVGUSZGRITPN-UHFFFAOYSA-N Note:

N N

NMR Spectroscopy (1)

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1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR (400 MHz, D20): 2.32 (s, 6H), 2.84 (s, 6H), 3.43 - 3.52 (m, 8H), 3.53 -3.62 (m, 2H), 4.23 - 4.28 (m, 2H), 4.41 (s, 2H), 6.74 (s, 2H).

Location

Page/Page column 71

References

Page/Page column 71

Patent; ALMIRALL, S.A.; BACH TAÑA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); (A1) English, View in Reaxys

Reaxys ID 28532146 View in Reaxys

315/323 Chemical Name: 1-(2-fluoro-4-methoxybenzyl)piperazine trifluoroacetate Linear Structure Formula: C12H17FN2O*xC2HF3O2 Molecular Formula: (x)C2HF3O2*C12H17FN2O InChI Key: JZSFIQBZKMRRJQ-UHFFFAOYSA-N Note:

F OH N

-1 O NH

F F

Reaxys ID 28532151 View in Reaxys H N

316/323 Chemical Name: 1-(4-(difluoromethoxy)-2-fluorobenzyl)piperazine hydrochloride Linear Structure Formula: C12H15F3N2O*xClH Molecular Formula: C12H15F3N2O*(x)ClH InChI Key: MDMFAQHVTSIGMF-UHFFFAOYSA-N Note:

-1 HCl

N F F

Crystal Property Description (1) Colour & Other Location Properties white

Paragraph 0151

References Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; HITCHCOCK, Stephen; HOPKINS, Maria; KIKUCHI, Shota; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; MACKLIN, Todd; WO2015/123505; (2015); (A1) English, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

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Original Text (NMR Spectroscopy)

1H NMR (400 MHz, DMSO-d6) ö ppm 2.78 - 3.56 (m, 8 H), 4.29 (br, 2 H), 7.15 (d, J =7.8 Hz, 1 H), 7.21 - 7.59 (m, 2 H), 7.76 (br, 1 H), 9.46 (br, 2 H)

Location

Paragraph 0151

References

electrospray ionisation (ESI); spectrum

Paragraph 0151

Reaxys ID 28532163 View in Reaxys

317/323 Chemical Name: 1-(2-fluoro-4-methoxybenzyl)piperazine Linear Structure Formula: C12H17FN2O Molecular Formula: C12H17FN2O Molecular Weight: 224.278 InChI Key: BVGBSIYYAKUSLR-UHFFFAOYSA-N Note:

F N NH

Reaxys ID 28532169 View in Reaxys

318/323 Chemical Name: 1-(2,4-difluorobenzyl)piperazine hydrochloride Linear Structure Formula: C11H14F2N2*xClH Molecular Formula: C11H14F2N2*(x)ClH InChI Key: FUTZACFTEYEBBK-UHFFFAOYSA-N Note:

-1 HCl

F N

Reaxys ID 28715626 View in Reaxys

319/323 Chemical Name: 1-[4-(difluoromethyl)benzyl]piperazine Linear Structure Formula: C12H16F2N2 Molecular Formula: C12H16F2N2 Molecular Weight: 226.269 InChI Key: YHDFEGSRUIVYSN-UHFFFAOYSA-N Note:

F F

NH N

Mass Spectrometry (1) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

Paragraph 0238

References Patent; ASTELLAS PHARMA INC.; Ohnuki, Kei; Azami, Hidenori; Sawada, Yuki; Shin, Takashi; Kuramoto, Kazuyuki; Kikuchi, Shigetoshi; Saito, Tomoyuki; Hamaguchi, Hisao; Nagashima, Takeyuki; US2015/266869; (2015); (A1) English, View in Reaxys

Reaxys ID 28811733 View in Reaxys

320/323

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Linear Structure Formula: C12H14F4N2*ClH Molecular Formula: C12H14F4N2*ClH Molecular Weight: 298.711 InChI Key: FLABRAWBMSQRNL-UHFFFAOYSA-N Note:

F N F F

HCl NH

Mass Spectrometry (1) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

References

Paragraph 0238

Patent; ASTELLAS PHARMA INC.; Ohnuki, Kei; Azami, Hidenori; Sawada, Yuki; Shin, Takashi; Kuramoto, Kazuyuki; Kikuchi, Shigetoshi; Saito, Tomoyuki; Hamaguchi, Hisao; Nagashima, Takeyuki; US2015/266869; (2015); (A1) English, View in Reaxys

Reaxys ID 28959394 View in Reaxys

321/323 Chemical Name: 1-(3,5-dimethoxybenzyl)piperazine dihydrochloride Linear Structure Formula: C13H20N2O2*2ClH Molecular Formula: C13H20N2O2*2ClH Molecular Weight: 309.236 InChI Key: JLZYALQSEPFDRB-UHFFFAOYSA-N Note:

2 HCl O

N NH O

Substance Label (1) Label References 15b

Jorgensen, William T.; Gulliver, Damien W.; Werry, Eryn L.; Reekie, Tristan; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 730 - 740, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

239 - 240

Jorgensen, William T.; Gulliver, Damien W.; Werry, Eryn L.; Reekie, Tristan; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 730 - 740, View in Reaxys Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)

Jorgensen, William T.; Gulliver, Damien W.; Werry, Eryn L.; Reekie, Tristan; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 730 - 740, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties white

Jorgensen, William T.; Gulliver, Damien W.; Werry, Eryn L.; Reekie, Tristan; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 730 - 740, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Jorgensen, William T.; Gulliver, Damien W.; Werry, Eryn L.; Reekie, Tristan; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 730 - 740, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) electrospray ionisation (ESI); liquid chromatography mass spectrometry (LCMS); IT (ion trap); spectrum

Jorgensen, William T.; Gulliver, Damien W.; Werry, Eryn L.; Reekie, Tristan; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 730 - 740, View in Reaxys

Reaxys ID 28969853 View in Reaxys

322/323 Chemical Name: 1-[4-(trifluoromethylsulfanyl)benzyl]piperazine Linear Structure Formula: C12H15F3N2S Molecular Formula: C12H15F3N2S Molecular Weight: 276.326 InChI Key: DNDIZWDLNDUDKM-UHFFFAOYSA-N Note:

N S

Substance Label (1) Label References 24

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties yellow

supporting information

References Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 133, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

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Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electron impact (EI); spectrum

References

supporting information

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 133, View in Reaxys

Reaxys ID 28969856 View in Reaxys

Chemical Name: 1-{4-[(trifluoromethyl)sulfonyl]benzyl}piperazine Linear Structure Formula: C12H15F3N2O2S Molecular Formula: C12H15F3N2O2S Molecular Weight: 308.325 InChI Key: ODPVMFKTAPDGHM-UHFFFAOYSA-N Note:

N NH

S O

323/323

Substance Label (1) Label References 25

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties yellow

supporting information

References Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 133, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy)

336/337

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Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 - 133, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

References Obreque-Balboa, Jos Esteban; Sun, Qiu; Bernhardt, Günther; König, Burkhard; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 124 133, View in Reaxys

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