1-azabicyclo[2.2.2]octan-8-ol (3-Quinuclidinol; Quinuclidin-3-ol) [CAS 1619-34-7; InChIKey IV by Asch

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39 substances in Reaxys

2016-04-25 15h:26m:09s (EST)

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Reaxys ID 80124 View in Reaxys

1/39 CAS Registry Number: 1619-34-7 Chemical Name: 3-quinuclidinol; Quinuclidin-3-ol Linear Structure Formula: C7H13NO Molecular Formula: C7H13NO Molecular Weight: 127.186 Type of Substance: heterocyclic InChI Key: IVLICPVPXWEGCA-UHFFFAOYSA-N Note:

Substance Label (21) Label References 26

Kennedy, Nicole; Cohen, Theodore; Journal of Organic Chemistry; vol. 80; nb. 16; (2015); p. 8134 - 8141, View in Reaxys

Arias-Perez; Cosme; Galvez; Sanz-Aparicio; Fonseca; Bellanato; Journal of Molecular Structure; vol. 644; nb. 1-3; (2003); p. 171 - 179, View in Reaxys; Bhadani, Avinash; Endo, Takeshi; Koura, Setsuko; Sakai, Kenichi; Abe, Masahiko; Sakai, Hideki; Langmuir; vol. 30; nb. 30; (2014); p. 9036 - 9044, View in Reaxys; Trinadhachari, Ganala Naga; Kamat, Anand Gopalkrishna; Venkata Balaji, Boddu; Prabahar, Koilpillai Joseph; Naidu, Kolukuluru Mohan; Babu, Korupolu Raghu; Sanasi, Paul Douglas; Organic Process Research and Development; vol. 18; nb. 8; (2014); p. 934 - 940, View in Reaxys

Sasano, Yusuke; Nagasawa, Shota; Yamazaki, Mai; Shibuya, Masatoshi; Park, Jaiwook; Iwabuchi, Yoshiharu; Angewandte Chemie - International Edition; vol. 53; nb. 12; (2014); p. 3236 - 3240; Angew. Chem.; vol. 126; nb. 12; (2014); p. 3300 - 3304,5, View in Reaxys

Kim, Hong-Yong; Shieh, Wen-Chung; Prashad, Mahavir; Tetrahedron Letters; vol. 55; nb. 36; (2014); p. 5055 - 5057, View in Reaxys

Heikkinen, Sami; Mesilaakso, Markku; Rahkamaa, Erkki; Magnetic Resonance in Chemistry; vol. 36; nb. 9; (1998); p. 627 - 634, View in Reaxys; Dolle, F.; Hinnen, F.; Valette, H.; Demphel, S.; Coulon, C.; Ottaviani, M.; Bottlaender, M.; Crouzel, C.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 44; (2001); p. S7 - S8, View in Reaxys; Dolle, Freanddeandric; Valette, Heandic; Hinnen, Francoise; Vaufrey, Francoise; Demphel, Steandphane; Coulon, Christine; Ottaviani, Micheandle; Bottlaender, Michel; Crouzel, Christian; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 44; nb. 11; (2001); p. 785 - 795, View in Reaxys; Kim, Young Seub; Jung, Sun Hwa; Park, Beoung-Geon; Ko, Min Kyung; Jang, Hyun-Seo; Choi, Kihang; Baik, Ja-Hyun; Lee, Jiyoun; Lee, Jae Kyun; Pae, Ae Nim; Cho, Yong Seo; Min, Sun-Joon; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 71 - 83, View in Reaxys

O'Neil, Ian A.; Wynn, Duncan; Lai, Justine Y. Q.; Tetrahedron Letters; vol. 41; nb. 2; (2000); p. 271 - 274, View in Reaxys; Chavakula, Ramadas; Rao, Mutyala Narayana; Rao, Chennupati Srinivasa; Journal of the Indian Chemical Society; vol. 90; nb. 2; (2013); p. 261 - 262, View in Reaxys

Patent; Ji, Jianguo; Li, Tao; US2005/137203; (2005); (A1) English, View in Reaxys; Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys

Patent; AUROBINDO PHARMA LIMITED; KAMAT, Anand, Gopalkrishna; KOILPILLAI, Joseph, Prabahar; GANALA, Naga, Trinadhachari; UPPUTURI, Venkata, Lakshmi; BODDU, Venkata, Balaji; MEENAKSHISUNDERAM, Sivakumaran; WO2012/1481; (2012); (A1) English, View in Reaxys

tab1, alcohol, entry12

Kondaiah; Reddy, L. Amarnath; Babu, K. Srihari; Gurav; Huge; Bandichhor; Reddy, P. Pratap; Bhattacharya; Anand, R. Vijaya; Tetrahedron Letters; vol. 49; nb. 1; (2008); p. 106 - 109, View in Reaxys

Castro, Enrique A.; Aliaga, Margarita; Campodonico, Paola R.; Leis, J. Ramon; Garcia-Rio, Luis; Santos, Jose G.; Journal of Physical Organic Chemistry; vol. 21; nb. 2; (2008); p. 102 - 107, View in Reaxys

Witty, David R.; Bateson, John; Hervieu, Guillaume J.; Al-Barazanji, Kamal; Jeffrey, Phillip; Hamprecht, Dieter; Haynes, Andrea; Johnson, Christopher N.; Muir, Alison I.; O'Hanlon, Peter J.; Stemp, Geoffrey; Stevens, Alex J.; Thewlis, Kevin; Winborn, Kim Y.; Bioorganic and Medicinal Chemistry Letters; vol. 16; nb. 18; (2006); p. 4872 - 4878, View in Reaxys

Tab. 1., Ent. 2., amine

Castro, Enrique A.; Aliaga, Margarita; Campodonico, Paola R.; Leis, J. Ramon; Garcia-Rio, Luis; Santos, Jose G.; Journal of Physical Organic Chemistry; vol. 19; nb. 10; (2006); p. 683 - 688, View in Reaxys

(+/-)-3

Ishihara, Tsukasa; Kakuta, Hirotoshi; Moritani, Hiroshi; Ugawa, Tohru; Yanagisawa, Isao; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 10; (2004); p. 1204 - 1209, View in Reaxys; Han, Xiang-Yu; Liu, He; Liu, Chun-He; Wu, Bo; Chen, Lan-Fu; Zhong, Bo-Hua; Liu, Ke-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 8; (2005); p. 1979 - 1982, View in Reaxys

Tatsumi, Ryo; Seio, Kohji; Fujio, Masakazu; Katayama, Jiro; Horikawa, Takashi; Hashimoto, Kenji; Tanaka, Hiroshi; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 14; (2004); p. 3781 - 3784, View in Reaxys

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Guendisch, Daniela; Andrae, Matthias; Munoz, Lenka; Cristina Tilotta, Maria; Bioorganic and Medicinal Chemistry; vol. 12; nb. 18; (2004); p. 4953 - 4962, View in Reaxys

(+/-)-1

Nomoto, Fumiki; Hirayama, Yoshihiko; Ikunaka, Masaya; Inoue, Toru; Otsuka, Koutaro; Tetrahedron Asymmetry; vol. 14; nb. 13; (2003); p. 1871 - 1877, View in Reaxys

3-OHQD

Aggarwal, Varinder K.; Emme, Ingo; Fulford, Sarah Y.; Journal of Organic Chemistry; vol. 68; nb. 3; (2003); p. 692 - 700, View in Reaxys

3-QNu

11a

Brown, George R.; Hollinshead, David M.; Stokes, Elaine S. E.; Clarke, David S.; Eakin, M. Allan; Foubister, Alan J.; Glossop, Steven C.; Griffiths, David; Johnson, Michael C.; McTaggart, Fergus; Mirrlees, Donald J.; Smith, Graham J.; Wood, Robin; Journal of Medicinal Chemistry; vol. 42; nb. 7; (1999); p. 1306 - 1311, View in Reaxys

3-Q

Ferri, Davide; Burgi, Thomas; Baiker, Alfons; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 7; (1999); p. 1305 - 1312, View in Reaxys

3-QB

Krylov; Kosarev; Dezhinova; Mikhaleva; Pharmaceutical Chemistry Journal; vol. 31; nb. 4; (1997); p. 168 169, View in Reaxys

Patent-Specific Data (3) Location in Patent References Page/Page column

Patent; EXXONMOBIL RESEARCH AND ENGINEERING COMPANY; WESTON, SIMON C.; STROHMAIER, KARL G.; VROMAN, HILDA B.; US2013/115163; (2013); (A1) English, View in Reaxys; Patent; Kamat, Anand Gopalkrishna; Koilpillai, Joseph Prabahar; Ganala, Naga Trinadhachari; Upputuri, Venkata Lakshmi; Boddu, Venkata Balalji; Meenakshisunderam, Sivakumaran; US2013/123502; (2013); (A1) English, View in Reaxys; Patent; KOTOBUKI PHARMACEUTICAL CO., LTD.; Astellas Pharma Inc.; Kameda, Minoru; Kuriwaki, Ikumi; Iikubo, Kazuhiko; Hisamichi, Hiroyuki; Kawamoto, Yuichiro; Moritomo, Hiroyuki; Suzuki, Tomoyuki; Futami, Takashi; Suzuki, Atsushi; Tsunoyama, Kazuhisa; Asaumi, Makoto; Tomiyama, Hiroshi; Noda, Atsushi; Iwai, Yoshinori; Tokuzaki, Kazuo; Okada, Haruki; Miyasaka, Kozo; US2014/142084; (2014); (A1) English, View in Reaxys; Patent; ExxonMobil Research and Engineering Company; Weston, Simon C.; Strohmaier, Karl G.; Vroman, Hilda B.; US2015/87841; (2015); (A1) English, View in Reaxys Patent; Astellas Pharma Inc.; EP2119716; (2009); (A1) English, View in Reaxys Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/22556; (2004); (A1) English, View in Reaxys

Derivative (2) Comment (Derivative)

Derivative

References

3-quinuclidinol-H+

Castro, Enrique A.; Andujar, Monica; Toro, Alejandra; Santos, Jose G.; Journal of Organic Chemistry; vol. 68; nb. 9; (2003); p. 3608 - 3613, View in Reaxys

Semiperchlorat: IR-Studien

Grech; Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques; vol. 26; (1978); p. 621, View in Reaxys

Melting Point (10) 1 of 10

Melting Point [°C]

215 - 217

Patent; Sokolovsky et al.; US3997543; (1976); Chem.Abstr.; vol. 87; nb. 23087, View in Reaxys 2 of 10

Melting Point [°C]

219 - 220

Kemp; Cassey; Journal of the American Chemical Society; vol. 95; (1973); p. 6670,6673,6675, View in Reaxys 3 of 10

Melting Point [°C]

224 - 226

Palecek; Collection of Czechoslovak Chemical Communications; vol. 36; (1971); p. 2070, View in Reaxys 4 of 10

Melting Point [°C]

225 - 227

Kostyanovsky et al.; Organic Mass Spectrometry; vol. 3; (1970); p. 1023,1026, View in Reaxys 5 of 10

Melting Point [°C]

205 - 210

Patent; United States Dept. of the Army; US3464997; (1969); Chem.Abstr.; vol. 72; nb. 43495u; (1970), View in Reaxys 6 of 10

Melting Point [°C]

218 - 220

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Micklina,E.E.; Rubtsov,M.V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; (1960); p. 163 - 171,174 - 181, View in Reaxys; Levine; Diassi; Journal of Organic Chemistry; vol. 30; (1965); p. 1325, View in Reaxys 7 of 10

Melting Point [°C]

223 - 224

Solvent (Melting Point)

petroleum ether

Grob; Zergenyi; Helvetica Chimica Acta; vol. 46; (1963); p. 2658,2663, View in Reaxys 8 of 10

Melting Point [°C]

225 - 227

Solvent (Melting Point)

acetone

Comment (Melting Point)

Sublimation.

Grob et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 2170,2176, View in Reaxys 9 of 10

Melting Point [°C]

221 - 223

Solvent (Melting Point)

benzene

Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys 10 of 10

Melting Point [°C]

221 - 223

Solvent (Melting Point)

acetone

Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys Sublimation (2) Sublimation [°C]

120

Pressure (Sublimation) [Torr]

Comment (Sublimation)

References

90-100grad/0.5

Vorobeva et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 6; (1970); p. 964; Khimiya Geterotsiklicheskikh Soedinenii; vol. 6; (1970); p. 1037, View in Reaxys

Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys

Association (MCS) (8) 1 of 8

Description (Association IR spectrum of the complex (MCS)) Solvent (Association (MCS))

CH2Cl2

Partner (Association (MCS))

acetic acid

Ferri, Davide; Burgi, Thomas; Baiker, Alfons; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 7; (1999); p. 1305 - 1312, View in Reaxys 2 of 8

Description (Association NMR spectrum of the complex (MCS)) Solvent (Association (MCS))

benzene-d6

Partner (Association (MCS))

1,1'-binaphthyl-2,2'-diyl hydrogenphosphate

Shapiro, M. J.; Archinal, A. E.; Jarema, M. A.; Journal of Organic Chemistry; vol. 54; nb. 24; (1989); p. 5826 5828, View in Reaxys 3 of 8

Description (Association Spectrum of the complex (MCS)) Solvent (Association (MCS))

ethyl acetate; cyclohexane

Temperature (Association (MCS)) [°C]

Comment (Association (MCS))

UV spectrum; Ratio of solvents: 1:1

Partner (Association (MCS))

p-benzoquinone

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Campbell, Michel J. M.; Demetriou, Basil; Jones, Ronald; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 917 - 922, View in Reaxys 4 of 8

Description (Association Spectrum of the complex (MCS)) Solvent (Association (MCS))

ethyl acetate; cyclohexane

Temperature (Association (MCS)) [°C]

Comment (Association (MCS))

UV spectrum; Ratio of solvents: 1:1

Partner (Association (MCS))

Duroquinone

Campbell, Michel J. M.; Demetriou, Basil; Jones, Ronald; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 917 - 922, View in Reaxys 5 of 8

Description (Association Spectrum of the complex (MCS)) Solvent (Association (MCS))

ethyl acetate; cyclohexane

Temperature (Association (MCS)) [°C]

Comment (Association (MCS))

UV spectrum; Ratio of solvents: 1:1

Partner (Association (MCS))

2,3,5,6-tetrafluoro-1,4-benzoquinone

Campbell, Michel J. M.; Demetriou, Basil; Jones, Ronald; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 917 - 922, View in Reaxys 6 of 8

Description (Association Spectrum of the complex (MCS)) Solvent (Association (MCS))

ethyl acetate; cyclohexane

Temperature (Association (MCS)) [°C]

Comment (Association (MCS))

UV spectrum; Ratio of solvents: 1:1

Partner (Association (MCS))

chloranil

Campbell, Michel J. M.; Demetriou, Basil; Jones, Ronald; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 917 - 922, View in Reaxys 7 of 8

Description (Association Spectrum of the complex (MCS)) Solvent (Association (MCS))

ethyl acetate; cyclohexane

Temperature (Association (MCS)) [°C]

Comment (Association (MCS))

UV spectrum; Ratio of solvents: 1:1

Partner (Association (MCS))

tetrabromo-p-benzoquinone

Campbell, Michel J. M.; Demetriou, Basil; Jones, Ronald; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 917 - 922, View in Reaxys 8 of 8

Description (Association Spectrum of the complex (MCS))

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Solvent (Association (MCS))

ethyl acetate; cyclohexane

Temperature (Association (MCS)) [°C]

Comment (Association (MCS))

UV spectrum; Ratio of solvents: 1:1

Partner (Association (MCS))

2,3-Dichloro-1,4-naphthoquinone

Campbell, Michel J. M.; Demetriou, Basil; Jones, Ronald; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 917 - 922, View in Reaxys Chromatographic Data (2) Chromatographic Location data

References

GC (Gas chromatography)

Zhang; He; Xue; Chu; Mu; RSC Advances; vol. 6; nb. 16; (2016); p. 12850 - 12861, View in Reaxys

HPLC (High performance liquid chromatography)

supporting information

Trinadhachari, Ganala Naga; Kamat, Anand Gopalkrishna; Venkata Balaji, Boddu; Prabahar, Koilpillai Joseph; Naidu, Kolukuluru Mohan; Babu, Korupolu Raghu; Sanasi, Paul Douglas; Organic Process Research and Development; vol. 18; nb. 8; (2014); p. 934 - 940, View in Reaxys

Conformation (1) Object of Investi- References gation The author investigated the; Conformation

Heikkinen, Sami; Mesilaakso, Markku; Rahkamaa, Erkki; Magnetic Resonance in Chemistry; vol. 36; nb. 9; (1998); p. 627 - 634, View in Reaxys

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

Kennedy, Nicole; Cohen, Theodore; Journal of Organic Chemistry; vol. 80; nb. 16; (2015); p. 8134 - 8141, View in Reaxys

Dissociation Exponent (16) 1 of 16

Dissociation Exponent (pK)

-0.991

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Type (Dissociation Exponent)

a1/apparent

Dissociation Exponent (pK)

9.8

Dissociation Group

N(+)-H

Temperature (Dissociation Exponent) [°C]

Method (Dissociation Exponent)

kinetics

Type (Dissociation Exponent)

a1/apparent

Castro, Enrique A.; Campodonico, Paola R.; Contreras; Fuentealba; Santos, Jose G.; Leis, J. Ramon; GarciaRio, Luis; Saez, Jose A.; Domingo, Luis R.; Tetrahedron; vol. 62; nb. 11; (2006); p. 2555 - 2562, View in Reaxys 3 of 16

Dissociation Exponent (pK)

9.8

Dissociation Group

N(+)-H

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Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Type (Dissociation Exponent)

a1/apparent

Castro, Enrique A.; Aliaga, Margarita; Santos, Jose G.; Journal of Organic Chemistry; vol. 70; nb. 7; (2005); p. 2679 - 2685, View in Reaxys 4 of 16

Dissociation Exponent (pK)

9.8

Temperature (Dissociation Exponent) [°C]

Method (Dissociation Exponent)

spectrophotometric

Type (Dissociation Exponent)

a1/apparent

Castro, Enrique A.; Munoz, Patricio; Santos, Jose G.; Journal of Organic Chemistry; vol. 64; nb. 22; (1999); p. 8298 - 8301, View in Reaxys 5 of 16

Dissociation Exponent (pK)

-1.03

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

D2O

Type (Dissociation Exponent)

a1/apparent

Amyes, Tina L.; Richard, John P.; Journal of the American Chemical Society; vol. 118; nb. 13; (1996); p. 3129 3141, View in Reaxys 6 of 16

Dissociation Exponent (pK)

10.02

Dissociation Group

N(1+)-H

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O; acetonitrile

Type (Dissociation Exponent)

a1/apparent

Suh, Junghun; Koh, Dongsoo; Min, Changhee; Journal of Organic Chemistry; vol. 53; nb. 6; (1988); p. 1147 1153, View in Reaxys 7 of 16

Dissociation Exponent (pK)

9.48

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Type (Dissociation Exponent)

a1/apparent

Hine, Jack; Chen, Yao-Jung; Journal of Organic Chemistry; vol. 52; nb. 10; (1987); p. 2091 - 2094, View in Reaxys 8 of 16

Dissociation Exponent (pK)

9.91

Temperature (Dissociation Exponent) [°C]

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Solvent (Dissociation Exponent)

H2O

Type (Dissociation Exponent)

a1/apparent

Grob, Cyril A.; Helvetica Chimica Acta; vol. 68; (1985); p. 882 - 886, View in Reaxys 9 of 16

Dissociation Exponent (pK)

10.04

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a1/apparent

Bruice, Paula Yurkanis; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 5959 - 5964, View in Reaxys 10 of 16

Dissociation Exponent (pK)

9.54

Dissociation Group

NH(+)

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a1/thermodynamic

Beltrame, Paolo; Gelli, Gioanna; Loi, Aldo; Gazzetta Chimica Italiana; vol. 110; nb. 9/10; (1980); p. 491 - 494, View in Reaxys 11 of 16

Dissociation Exponent (pK)

18.7

Dissociation Group

NH(+)

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

acetonitrile

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a1/thermodynamic

Beltrame, Paolo; Gelli, Gioanna; Loi, Aldo; Gazzetta Chimica Italiana; vol. 110; nb. 9/10; (1980); p. 491 - 494, View in Reaxys 12 of 16

Comment (Dissociation Exponent)

(pk')pK(a)

Bruice,P.Y. et al.; Journal of the American Chemical Society; vol. 98; (1976); p. 2973 - 2981, View in Reaxys; Bruice; Bruice; Journal of the American Chemical Society; vol. 100; (1978); p. 4793,4796, 4797, View in Reaxys 13 of 16

Comment (Dissociation Exponent)

(pk')pK-Wert

Gresser,M.J.; Jencks,W.P.; Journal of the American Chemical Society; vol. 99; nb. 21; (1977); p. 6963 - 6970, View in Reaxys

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14 of 16

Comment (Dissociation Exponent)

(pk')

Abrams,W.R.; Kallen,R.G.; Journal of the American Chemical Society; vol. 98; (1976); p. 7777 - 7789, View in Reaxys 15 of 16

Comment (Dissociation Exponent)

(pk')pK(a); 'kinetic pK(a)'; δpK(a) (Tab.I)

Kemp; Cassey; Journal of the American Chemical Society; vol. 95; (1973); p. 6670,6673,6675, View in Reaxys 16 of 16

Comment (Dissociation Exponent)

(pk')pK(A)

Page; Jencks; Journal of the American Chemical Society; vol. 94; (1972); p. 8818,8820,8822, View in Reaxys Electrochemical Behaviour (2) Description (Elec- References trochemical Behaviour) Electrolytic dissociation / protonation equilibrium

Beltrame, Paolo; Gelli, Gioanna; Loi, Aldo; Gazzetta Chimica Italiana; vol. 110; nb. 9/10; (1980); p. 491 494, View in Reaxys; Amyes, Tina L.; Richard, John P.; Journal of the American Chemical Society; vol. 118; nb. 13; (1996); p. 3129 - 3141, View in Reaxys; Castro, Enrique A.; Andujar, Monica; Toro, Alejandra; Santos, Jose G.; Journal of Organic Chemistry; vol. 68; nb. 9; (2003); p. 3608 - 3613, View in Reaxys

Electrochemical properties

Smith; Masheder; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1977); p. 1732,1733, View in Reaxys

Further Information (3) Description (Fur- References ther Information) Further information

Grech; Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques; vol. 26; (1978); p. 621, View in Reaxys

Further information

Ermakov et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 11; (1975); p. 1174,1177; Khimiya Geterotsiklicheskikh Soedinenii; vol. 11; (1975); p. 1376, View in Reaxys

Further information

Werber; Shalitin; Bioorganic Chemistry; vol. 2; (1973); p. 202,209, View in Reaxys

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

Description (Liquid/ Activity coefficients of the components in the mixture Vapour Systems (MCS)) Solvent (Liquid/Vapour Systems (MCS))

acetonitrile

Temperature (Liquid/ 25 Vapour Systems (MCS)) [°C] Partner (Liquid/Vapour Systems (MCS))

0.7M HClO4

Beltrame, Paolo; Gelli, Gioanna; Loi, Aldo; Gazzetta Chimica Italiana; vol. 110; nb. 9/10; (1980); p. 491 - 494, View in Reaxys 2 of 2

Description (Liquid/ Activity coefficients of the components in the mixture Vapour Systems (MCS)) Solvent (Liquid/Vapour Systems (MCS))

H2O

Temperature (Liquid/ 25 Vapour Systems (MCS)) [°C] Partner (Liquid/Vapour Systems (MCS))

0.7M HClO4

Beltrame, Paolo; Gelli, Gioanna; Loi, Aldo; Gazzetta Chimica Italiana; vol. 110; nb. 9/10; (1980); p. 491 - 494, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

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Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Patent; Sokolovsky et al.; US3997543; (1976); Chem.Abstr.; vol. 87; nb. 23087, View in Reaxys NMR Spectroscopy (14) 1 of 14

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

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Kennedy, Nicole; Cohen, Theodore; Journal of Organic Chemistry; vol. 80; nb. 16; (2015); p. 8134 - 8141, View in Reaxys 2 of 14

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

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

400

Kennedy, Nicole; Cohen, Theodore; Journal of Organic Chemistry; vol. 80; nb. 16; (2015); p. 8134 - 8141, View in Reaxys 3 of 14

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

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

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

24.85

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Arias-Perez; Cosme; Galvez; Sanz-Aparicio; Fonseca; Bellanato; Journal of Molecular Structure; vol. 644; nb. 1-3; (2003); p. 171 - 179, View in Reaxys 5 of 14

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

24.85

Arias-Perez; Cosme; Galvez; Sanz-Aparicio; Fonseca; Bellanato; Journal of Molecular Structure; vol. 644; nb. 1-3; (2003); p. 171 - 179, View in Reaxys 6 of 14

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

24.85

Arias-Perez; Cosme; Galvez; Sanz-Aparicio; Fonseca; Bellanato; Journal of Molecular Structure; vol. 644; nb. 1-3; (2003); p. 171 - 179, View in Reaxys 7 of 14

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

Solvents (NMR Spectro- dimethylsulfoxide scopy) Temperature (NMR Spectroscopy) [°C]

Comment (NMR Spectroscopy)

acidity dependence

Aggarwal, Varinder K.; Emme, Ingo; Fulford, Sarah Y.; Journal of Organic Chemistry; vol. 68; nb. 3; (2003); p. 692 - 700, View in Reaxys 8 of 14

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

Solvents (NMR Spectro- dimethylsulfoxide scopy) Temperature (NMR Spectroscopy) [°C]

Comment (NMR Spectroscopy)

acidity dependence. Object(s) of Study: diagram

Aggarwal, Varinder K.; Emme, Ingo; Fulford, Sarah Y.; Journal of Organic Chemistry; vol. 68; nb. 3; (2003); p. 692 - 700, View in Reaxys 9 of 14

Description (NMR Spec- Linewidth of NMR absorption troscopy) Nucleus (NMR Spectroscopy)

14N

Heikkinen, Sami; Mesilaakso, Markku; Rahkamaa, Erkki; Magnetic Resonance in Chemistry; vol. 36; nb. 9; (1998); p. 627 - 634, View in Reaxys 10 of 14

Description (NMR Spec- Spectrum troscopy)

11/60

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]

29.85

Frequency (NMR Spectroscopy) [MHz]

400

Heikkinen, Sami; Mesilaakso, Markku; Rahkamaa, Erkki; Magnetic Resonance in Chemistry; vol. 36; nb. 9; (1998); p. 627 - 634, View in Reaxys 11 of 14

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

Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]

29.85

Frequency (NMR Spectroscopy) [MHz]

400

Heikkinen, Sami; Mesilaakso, Markku; Rahkamaa, Erkki; Magnetic Resonance in Chemistry; vol. 36; nb. 9; (1998); p. 627 - 634, View in Reaxys 12 of 14

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]

29.85

Frequency (NMR Spectroscopy) [MHz]

400

Heikkinen, Sami; Mesilaakso, Markku; Rahkamaa, Erkki; Magnetic Resonance in Chemistry; vol. 36; nb. 9; (1998); p. 627 - 634, View in Reaxys 13 of 14

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

13C

Solvents (NMR Spectro- acetone-d6 scopy) Heikkinen, Sami; Mesilaakso, Markku; Rahkamaa, Erkki; Magnetic Resonance in Chemistry; vol. 36; nb. 9; (1998); p. 627 - 634, View in Reaxys 14 of 14

Description (NMR Spec- NMR troscopy) Jachontow et al.; Voprosy Stereokhimii; vol. 1; (1971); p. 117; Chem.Abstr.; vol. 77; nb. 100598; (1972), View in Reaxys; Turchin et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 7; (1971); p. 916,918; Khimiya Geterotsiklicheskikh Soedinenii; vol. 7; (1971); p. 981, View in Reaxys

IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

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Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CH2Cl2

Ferri, Davide; Burgi, Thomas; Baiker, Alfons; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 7; (1999); p. 1305 - 1312, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); timeof-flight mass spectra (TOFMS); spectrum

spectrum; fragmentation pattern; collision-induced dissociation

Bednar, Petr; Lemr, Karel; Bartaak, Petr; Sevcik, Juraj; Hlavac, Jan; Styskala, Jakub; Wiedermannova, Iveta; Stransky, Zdenek; Journal of Mass Spectrometry; vol. 37; nb. 12; (2002); p. 1213 - 1218, View in Reaxys Kostyanovsky et al.; Organic Mass Spectrometry; vol. 3; (1970); p. 1023,1026, View in Reaxys; Ermakov et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 11; (1975); p. 1174,1177; Khimiya Geterotsiklicheskikh Soedinenii; vol. 11; (1975); p. 1376, View in Reaxys

Pharmacological Data (7) 1 of 7

Comment (Pharmacological Data)

Bioactivities present

Patent; MERCK and CO. INC.; EP431972; (1991); (A2) English, View in Reaxys; Patent; MERCK and CO. INC.; EP518675; (1992); (A2) English, View in Reaxys; Patent; ELI LILLY AND COMPANY; EP773027; (1997); (A1) English, View in Reaxys; Patent; ELI LILLY AND COMPANY; EP774256; (1997); (A1) English, View in Reaxys; Patent; The United States of America as represented by the Secretary of the Army; US3956365; (1976); (A1) English, View in Reaxys; Bruice,P.Y. et al.; Journal of the American Chemical Society; vol. 98; (1976); p. 2973 - 2981, View in Reaxys; Abrams,W.R.; Kallen,R.G.; Journal of the American Chemical Society; vol. 98; (1976); p. 7777 7789, View in Reaxys; Gresser,M.J.; Jencks,W.P.; Journal of the American Chemical Society; vol. 99; nb. 21; (1977); p. 6963 - 6970, View in Reaxys; Granoth; Kalir; Pelah; Bergmann; Tetrahedron; vol. 25; nb. 17; (1969); p. 3919 - 3924, View in Reaxys; Patent; Bracco International B.V.; US5387409; (1995); (A1) English, View in Reaxys; Patent; Eli Lilly and Company; US5852037; (1998); (A1) English, View in Reaxys; Patent; John Wyeth and Brother, Limited; US4921860; (1990); (A1) English, View in Reaxys; Patent; The United States of America represented by the Secretary Department of Health and Human Services; US5569447; (1996); (A1) English, View in Reaxys; Patent; Yamanouchi Pharmaceutical Co., Ltd.; US6017927; (2000); (A1) English, View in Reaxys; Patent; Eli Lilly and Company; US6040442; (2000); (A1) English, View in Reaxys; Patent; RhonePoulenc Rorer Pharmaceuticals Inc.; US6057369; (2000); (A1) English, View in Reaxys; Patent; Lonza AG; US6075145; (2000); (A1) English, View in Reaxys; Patent; Pharmacia and Upjohn AB; US6124354; (2000); (A1) English, View in Reaxys; Patent; Hoechst Marion Roussel Inc.; US5880121; (1999); (A1) English, View in Reaxys; Patent; Eli Lilly and Company; US5998404; (1999); (A1) English, View in Reaxys; Patent; Rhone-Poulenc Sante; US5086051; (1992); (A1) English, View in Reaxys; Patent; Degussa AG; US2002/22726; (2002); (A1) English, View in Reaxys; Patent; Asahi Kasei Kogyo Kabushiki Kaisha; US5200415; (1993); (A1) English, View in Reaxys; Patent; Eli Lilly and Company; US5605908; (1997); (A1) English, View in Reaxys; Patent; Fernandez Forner, Dolors; Prat Quinones, Maria; Buil Albero, Maria Antonia; US2003/55080; (2003); (A1) English, View in Reaxys; Patent; H. Lundbeck A/S; US2003/138376; (2003); (A1) English, View in Reaxys; Patent; Syngenta Limited; EP674635; (2001); (B1) English, View in Reaxys; Patent; NEUROSEARCH A/S; WO2004/16608; (2004); (A1) English, View in Reaxys; Granoth,I. et al.; Israel Journal of Chemistry; vol. 6; (1968); p. 651 - 657, View in Reaxys; Micklina,E.E.; Rubtsov,M.V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; (1960); p. 163 - 171,174 - 181, View in Reaxys; Smith,J.R.L.; Mead,L.A.V.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1976); p. 1172 - 1176, View in Reaxys; Patent; NeuroSearch A/S; WO2005/75479; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/245531; (2005); (A1) English, View in Reaxys; Patent; NeuroSearch A/S; WO2006/40352; (2006); (A1) English, View in Reaxys; Grob et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 2170,2176, View in Reaxys; Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys; Sternbach; Kaiser; Journal of the American Chemical Society; vol. 75; (1953); p. 6068, View in Reaxys; Patent; Hoffmann-La Roche; DE931653; (1953), View in Reaxys; Patent; Hoffmann-La Roche; US2658067; (1952), View in Reaxys; Vorobeva et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 6; (1970); p. 964; Khimiya Geterotsiklicheskikh Soedi-

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nenii; vol. 6; (1970); p. 1037, View in Reaxys; Palecek; Collection of Czechoslovak Chemical Communications; vol. 36; (1971); p. 2070, View in Reaxys; Jachontow et al.; Voprosy Stereokhimii; vol. 1; (1971); p. 117; Chem.Abstr.; vol. 77; nb. 100598; (1972), View in Reaxys; Turchin et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 7; (1971); p. 916,918; Khimiya Geterotsiklicheskikh Soedinenii; vol. 7; (1971); p. 981, View in Reaxys; Grech; Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques; vol. 26; (1978); p. 621, View in Reaxys; Smith; Masheder; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1977); p. 1732,1733, View in Reaxys; Dennis et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 3783, View in Reaxys; Ritchie; Journal of the American Chemical Society; vol. 97; (1975); p. 1170, View in Reaxys; Werber; Shalitin; Bioorganic Chemistry; vol. 2; (1973); p. 202,209, View in Reaxys; Michlina; Rubzow; J. 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Jung; WO2012/102580; (2012); (A1) English, View in Reaxys; Patent; SK BIOPHARMACEUTICALS CO., LTD.; MAENG, Cheol Young; JANG, Young Koo; CHA, Su Bong; SHIN, Hye Won; JOUNG, Chan Mi; YI, Eun Jung; WO2012/102583; (2012); (A1) English, View in Reaxys; Patent; TAKASAGO INTERNATIONAL CORPORATION; TOUGE, Taichiro; AOKI, Kunie; NARA, Hideki; KURIYAMA, Wataru; WO2012/144650; (2012); (A1) English, View in Reaxys; Patent; EXXONMOBIL RESEARCH AND ENGINEERING COMPANY; WESTON, SIMON C.; STROHMAIER, KARL G.; VROMAN, HILDA B.; US2013/115163; (2013); (A1) English, View in Reaxys; Kim, Young Seub; Jung, Sun Hwa; Park, Beoung-Geon; Ko, Min Kyung; Jang, Hyun-Seo; Choi, Kihang; Baik, JaHyun; Lee, Jiyoun; Lee, Jae Kyun; Pae, Ae Nim; Cho, Yong Seo; Min, Sun-Joon; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 71 - 83, View in Reaxys; Patent; Kamat, Anand Gopalkrishna; Koilpillai, Joseph Prabahar; Ganala, Naga Trinadhachari; Upputuri, Venkata Lakshmi; Boddu, Venkata Balalji; Meenakshisunderam, Sivakumaran; US2013/123502; (2013); (A1) English, View in Reaxys; Chavakula, Ramadas; Rao, Mutyala Narayana; Rao, Chennupati Srinivasa; Journal of the Indian Chemical Society; vol. 90; nb. 2; (2013); p. 261 262, View in Reaxys; Nogrady; Algieri; Journal of medicinal chemistry; vol. 11; nb. 2; (1968); p. 212 - 213, View in Reaxys; Bolanos; Schechter; Miquel; Emerit; Rumigny; Hamon; Gozlan; Biochemical pharmacology; vol. 40; nb. 7; (1990); p. 1541 - 1550, View in Reaxys; Steves, Janelle E.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 135; nb. 42; (2013); p. 15742 - 15745, View in Reaxys; Saba, Shahrokh; Hernandez, Renee; Choy, Christine Chin; Carta, Kristine; Bennett, Yaasmin; Bondi, Steven; Kolaj, Sebastian; Bennett, Caitlin; Journal of Fluorine Chemistry; vol. 153; (2013); p. 168 - 171, View in Reaxys; Lauber, Markus B.; Stahl, Shannon S.; ACS Catalysis; vol. 3; nb. 11; (2013); p. 2612 - 2616, View in Reaxys; Patent; SK BIOPHARMACEUTICALS CO., LTD.; Maeng, Cheol Young; Jang, Young Koo; Cha, Su Bong; Shin, Hye Won; Joung, Chan Mi; Cha, Hwa Ryun; Yi, Eun Jung; US2013/317059; (2013); (A1) English, View in Reaxys; Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys; D'Agostino, Simone; Grepioni, Fabrizia; Braga, Dario; Moreschi, Daniele; Fattori, Valeria; Delchiaro, Francesca; Di Motta, Simone; Negri, Fabrizia; CrystEngComm; vol. 15; nb. 48; (2013); p. 10470 - 10480, View in Reaxys; Sasano, Yusuke; Nagasawa, Shota; Yamazaki, Mai; Shibuya, Masatoshi; Park, Jaiwook; Iwabuchi, Yoshiharu; Angewandte Chemie - International Edition; vol. 53; nb. 12; (2014); p. 3236 - 3240; Angew. 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Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

Fischer-344 rat

Sex

male

Route of Application

intraarterial

Concentration (Pharmacological Data)

250 μmol/l

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Kind of Dosing (Pharmacological Data)

co-administered with <3H>choline

Method (Pharmacological Data)

affinity at active binding site of the blood-brain barrier choline transporter evaluated by measuring brain <3H>choline uptake using in situ brain perfusion method; anesthetized rats (220-230 g)

Further Details (Pharmacological Data)

infused for 60 s with perfusion fluid containing 1 μCi/ml <3H>choline (spec. act.: 79.2 Ci/ mmol); rats sacrificed and cerebral samples obtained; radioactivity of perfusate and brain samples assessed by dual-label liquid scintillation counting

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

200 μmol/l

Geldenhuys, Werner J.; Lockman, Paul R.; McAfee, James H.; Fitzpatrick, Kevin T.; Van Der Schyf, Cornelis J.; Allen, David D.; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 12; (2004); p. 3085 - 3092, View in Reaxys 3 of 7

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

pig adrenals

Kind of Dosing (Pharmacological Data)

dissolved in HEPES salt solution (pH 7.4)

Method (Pharmacological Data)

receptor binding assays were used to evaluate the title comp. abilities to compete <3H>epibatidine bindig for α3β4* subtype of nicotinic acetylcholine receptor (nAChR)

Further Details (Pharmacological Data)

compared to (-)-epibatidine (Ki = 0.05 nmol/l) and (-)-nicotine (Ki = 73.4 nmol/l)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

14604 nmol/l

Guendisch, Daniela; Andrae, Matthias; Munoz, Lenka; Cristina Tilotta, Maria; Bioorganic and Medicinal Chemistry; vol. 12; nb. 18; (2004); p. 4953 - 4962, View in Reaxys 4 of 7

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

rat forebrain

Kind of Dosing (Pharmacological Data)

dissolved in HEPES salt solution (pH 7.4)

Method (Pharmacological Data)

receptor binding assays were used to evaluate the title comp. abilities to compete <3H>epibatidine bindig for α4β2* subtype of nicotinic acetylcholine receptor (nAChR)

Further Details (Pharmacological Data)

compared to (-)-epibatidine (Ki = 0.008 nmol/l) and (-)-nicotine (Ki = 0.84 nmol/l)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

5924 nmol/l

Guendisch, Daniela; Andrae, Matthias; Munoz, Lenka; Cristina Tilotta, Maria; Bioorganic and Medicinal Chemistry; vol. 12; nb. 18; (2004); p. 4953 - 4962, View in Reaxys 5 of 7

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

rat forebrain

Kind of Dosing (Pharmacological Data)

dissolved in HEPES salt solution (pH 7.4)

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Method (Pharmacological Data)

receptor binding assays were used to evaluate the title comp. abilities to compete <3H>methyllycaconitine bindig for α7* subtype of nicotinic acetylcholine receptor (nAChR)

Further Details (Pharmacological Data)

compared to (-)-epibatidine (Ki = 4 nmol/l) and (-)-nicotine (Ki = 130 nmol/l)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

7761 nmol/l

Guendisch, Daniela; Andrae, Matthias; Munoz, Lenka; Cristina Tilotta, Maria; Bioorganic and Medicinal Chemistry; vol. 12; nb. 18; (2004); p. 4953 - 4962, View in Reaxys 6 of 7

Effect (Pharmacological Data)

mydriatic

Species or Test-System (Pharmacological Data)

white mongrel mice

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

0.5 mg/kg

Kind of Dosing (Pharmacological Data)

test comp. inject. in physiol. solution or normal rabbit serum

Method (Pharmacological Data)

mice weigh. ca. 20 g; intact and immun. with 3-QB3-BSA-30 and 3-QB5-BSA-32; pupil diam. meas. by the number of marks on scale of eyepiece of the microscope (50 marks/mm)

Results

weakly pronounc. antimydriatic effect

Krylov; Kosarev; Dezhinova; Mikhaleva; Pharmaceutical Chemistry Journal; vol. 31; nb. 4; (1997); p. 168 - 169, View in Reaxys 7 of 7

Effect (Pharmacological Data)

motor activity

Species or Test-System (Pharmacological Data)

rat

Sex

not specified

Concentration (Pharmacological Data)

1 - 10 mg/kg

Exposure Period (Pharmacological Data)

60 min

Method (Pharmacological Data)

active immunization with conjugates of 3-QB3-BSA-30 and QB5-BSA-32 types; "open field" test

Results

signif. motor activ.

Krylov; Kosarev; Dezhinova; Mikhaleva; Pharmaceutical Chemistry Journal; vol. 31; nb. 4; (1997); p. 168 - 169, View in Reaxys

Reaxys ID 80123 View in Reaxys

2/39 CAS Registry Number: 25333-42-0 Chemical Name: (R)-quinuclidin-3-ol Linear Structure Formula: C7H13NO Molecular Formula: C7H13NO Molecular Weight: 127.186 Type of Substance: heterocyclic InChI Key: IVLICPVPXWEGCA-ZETCQYMHSA-N Note:

Substance Label (19) Label References

19/60

2016-04-25 15:32:22

Formula V

Patent; DR. REDDY'S LABORATORIES LTD.; DR. REDDY'S LABORATORIES, INC.; WO2008/11462; (2008); (A2) English, View in Reaxys; Patent; GLENMARK PHARMACEUTICALS LIMITED; GLENMARK GENERICS LIMITED; BHIRUD, Shekhar Bhaskar; NAIK, Samir Jaivant; MISHRA, Sushanta Kumar; YADAV, Premkumar Ramraj; KAJALE, Yogesh Baburao; MARATHE, Lalit Vasant; WO2015/71824; (2015); (A1) English, View in Reaxys

III

Patent; Dipharma Francis S.r.l.; US2009/203915; (2009); (A1) English, View in Reaxys; Patent; Dipharma Francis S.r.l.; EP2088148; (2009); (A2) English, View in Reaxys; Patent; ZENTIVA, K.S.; CERNA, Igor; HAJICEK Josef; WO2015/62560; (2015); (A1) English, View in Reaxys

formula II

Patent; PHARMATHEN S.A.; KOFTIS, Theocharis, V.; SONI, Rohit, Ravikant; BODA, Bharat, Becharbhai; GHOTIKAR, Ravindra, Charudatta; PATEL, Vimal, Sudhirbhai; WO2014/5601; (2014); (A1) English, View in Reaxys

Babu, R. Anji; Reddy, N. Siva Senkar; Reddy, B. V. Subba; Reddy, B. Jagan Mohan; Synthesis; vol. 46; nb. 20; (2014); p. 2794 - 2798; Art.No: SS-2014-N0306-OP, View in Reaxys

Patent; Ji, Jianguo; Li, Tao; US2005/137203; (2005); (A1) English, View in Reaxys; Chavakula, Ramadas; Rao, Mutyala Narayana; Rao, Chennupati Srinivasa; Journal of the Indian Chemical Society; vol. 90; nb. 2; (2013); p. 261 - 262, View in Reaxys

Patent; KYUNG DONG PHARM. CO., LTD.; LEE, Byoung Suk; SHIN, Sang Hoon; LEE, Ki Young; WO2013/147458; (2013); (A1) English, View in Reaxys

Patent; BUCK INSTITUTE FOR RESEARCH ON AGING; JOHN, Varghese; BREDESEN, Dale E.; WO2013/19901; (2013); (A2) English, View in Reaxys

Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys

Patent; Corporacion Medichem, S.L.; US2010/29944; (2010); (A1) English, View in Reaxys

3-R; IIIa

Patent; National University Corporation Hokkaido University; Nippon Soda Co., Ltd.; EP2186812; (2010); (A1) English, View in Reaxys

Formula I

Patent; Jirman, Josef; Junek, Richard; Lustig, Petr; Richter, Jindrich; Placek, Lukas; US2009/203914; (2009); (A1) English, View in Reaxys; Patent; Jirman, Josef; Junek, Richard; US2010/145055; (2010); (A1) English, View in Reaxys

Patent; Medichem, S.A.; US2008/242697; (2008); (A1) English, View in Reaxys; Patent; MEGAFINE PHARMA(P) LTD.; MATHAD, Vijayvitthal, Thippannachar; NIPHADE, Navnath, Chintaman; MALI, Anil, Chaturlal; JAGTAP, Kunal, Madhav; PANDIT, Bhushan, Sudhakar; KUMAR, P., Raghvendra; LANDGE, Shashikant, Baburao; WO2010/103529; (2010); (A1) English, View in Reaxys

Formula-2

Patent; MSN LABORATORIES LIMITED; WO2009/139002; (2009); (A2) English, View in Reaxys

S-9

Patent; ZAKLADY FARMACEUTYCZNE POLPHARMA SA; WO2009/142522; (2009); (A1) English, View in Reaxys

(R)-3

Han, Xiang-Yu; Liu, He; Liu, Chun-He; Wu, Bo; Chen, Lan-Fu; Zhong, Bo-Hua; Liu, Ke-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 8; (2005); p. 1979 - 1982, View in Reaxys

(R)-34

Naito, Ryo; Yonetoku, Yasuhiro; Okamoto, Yoshinori; Toyoshima, Akira; Ikeda, Ken; Takeuchi, Makoto; Journal of Medicinal Chemistry; vol. 48; nb. 21; (2005); p. 6597 - 6606, View in Reaxys

(-)-3

Ishihara, Tsukasa; Kakuta, Hirotoshi; Moritani, Hiroshi; Ugawa, Tohru; Yanagisawa, Isao; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 10; (2004); p. 1204 - 1209, View in Reaxys

(R)-1

Nomoto, Fumiki; Hirayama, Yoshihiko; Ikunaka, Masaya; Inoue, Toru; Otsuka, Koutaro; Tetrahedron Asymmetry; vol. 14; nb. 13; (2003); p. 1871 - 1877, View in Reaxys

(R)-(-)-1

Ringdahl, Bjorn; Ohnsorge, F. W.; Craig, J. Cymerman; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1981); p. 697 - 698, View in Reaxys

Patent-Specific Data (13) Location in Patent References Page/Page column

Patent; CHIESI FARMACEUTICI S.p.A.; Armani, Elisabetta; Amari, Gabriele; Riccaboni, Mauro; BakerGlenn, Charles; US2014/155373; (2014); (A1) English, View in Reaxys; Patent; CHIESI FARMACEUTICI S.p.A; ARMANI, Elisabetta; Amari, Gabriele; Riccaboni, Mauro; Baker-Glenn, Charles; US2014/155428; (2014); (A1) English, View in Reaxys; Patent; CHIESI FARMACEUTICI S.p.A.; Armani, Elisabetta; Amari, Gabriele; Riccaboni, Mauro; Rizzi, Andrea; Baker-Glenn, Charles; Blackaby, Wesley; Van de Poel, Herve'; Whittaker, Ben; US2014/155427; (2014); (A1) English, View in Reaxys; Patent; ISOCHEM; Bessa Bellunt, Jordi; Corbella Morato, Marina; US2014/228575; (2014); (A1) English, View in Reaxys; Patent; Kyung Dong Pharm. Co., Ltd.; Lee, Byoung Suk; Shin, Sang Hoon; Lee, Ki Young; US2015/112072; (2015); (A1) English, View in Reaxys; Patent; CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; ARMANI, Elisabetta; GHIDINI, Eleonora; BAKER-GLENN, Charles; VAN DE POËL, Hervé; WHITTAKER, Ben;

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US2015/158858; (2015); (A1) English, View in Reaxys; Patent; CHIESI FARMACEUTICI S.p.A.; AMARI, Gabriele; Armani, Elisabetta; Capaldi, Carmelida; De Fanti, Renato; Riccaboni, Mauro; Baker-Glenn, Charles; Van De Poël, Hervé; US2015/158857; (2015); (A1) English, View in Reaxys Patent; CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; PESENTI, Cristina; BOSSOLO, Stefano; WO2013/98145; (2013); (A1) English, View in Reaxys Page/Page column

Patent; Chiesi Farmaceutici S.p.A.; AMARI, Gabriele; Pesenti, Cristina; Bossolo, Stefano; US2013/172302; (2013); (A1) English, View in Reaxys Patent; CHIESI FARMACEUTICI S.p.A.; US2012/134934; (2012); (A1) English, View in Reaxys Patent; CHIESI FARMACEUTICI S.p.A.; AMARI, Gabriele; RICCABONI, Mauro; CALIGIURI, Antonio; WO2011/160918; (2011); (A1) English, View in Reaxys Patent; National University Corporation Hokkaido University; Nippon Soda Co., Ltd.; EP2186812; (2010); (A1) English, View in Reaxys Patent; Astellas Pharma Inc.; EP2119716; (2009); (A1) English, View in Reaxys Patent; Astellas Pharma Inc.; EP1714965; (2006); (A1) English, View in Reaxys Patent; ALMIRALL PRODESFARMA, SA; WO2006/10452; (2006); (A1) English, View in Reaxys Patent; ALMIRALL PRODESFARMA, SA; WO2005/90342; (2005); (A1) English, View in Reaxys Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/22556; (2004); (A1) English, View in Reaxys Patent; ALMIRALL PRODESFARMA S.A.; WO2004/840; (2003); (A2) English, View in Reaxys

Claim

Patent; Daicel Chemical Industries, Ltd.; EP1318200; (2003); (A2) English, View in Reaxys; Patent; Daicel Chemical Industries, Ltd.; US5888804; (1999); (A1) English, View in Reaxys

Related Structure (2) Related Structure References Ringdahl; Resul; Dahlbom; Acta Pharmaceutica Suecica; vol. 16; nb. 4 suppl; (1979); p. 281 - 283, View in Reaxys Die Konfiguration folgt aus der genetischen Beziehung zu (-) (#R!)-3-Acetoxy-1-methyl-chinuclidinium-jodid s..

Baker; Pauling; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1972); p. 2340, View in Reaxys; Belleau; Pauling; Journal of Medicinal Chemistry; vol. 13; (1970); p. 737, View in Reaxys; Robinson; Belleau; Cox; Journal of medicinal chemistry; vol. 12; nb. 5; (1969); p. 848 - 851, View in Reaxys

Melting Point (4) 1 of 4

Melting Point [°C]

221 - 224

Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys 2 of 4

Melting Point [°C]

223 - 224

Zhao, Ning; Kumar, Narendra; Neuenschwander, Kent; Nakanishi, Koji; Berova, Nina; Journal of the American Chemical Society; vol. 117; nb. 29; (1995); p. 7844 - 7845, View in Reaxys 3 of 4

Melting Point [°C]

223.5 - 224.5

Ringdahl; Resul; Dahlbom; Acta Pharmaceutica Suecica; vol. 16; nb. 4 suppl; (1979); p. 281 - 283, View in Reaxys 4 of 4

Melting Point [°C]

220 - 222

Solvent (Melting Point)

acetone

Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys Chromatographic Data (4) Chromatographic Original string data

Location

References

GC (Gas chroma- Rt = 7.5 min tography)

Page/Page column 17

Patent; ZENTIVA, K.S.; CERNA, Igor; HAJICEK Josef; WO2015/62560; (2015); (A1) English, View in Reaxys

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GC (Gas chromatography)

Wang, Yu; Li, Jianjiong; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 88; (2013); p. 14 - 19, View in Reaxys

HPLC (High performance liquid chromatography)

Wang, Yu; Li, Jianjiong; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 88; (2013); p. 14 - 19, View in Reaxys

GC (Gas chromatography)

supporting information

Circular Dichroism (1) Solvent (Circular Comment (CircuDichroism) lar Dichroism)

References

ethanol; H2O

1360 nm

Crystal Property Description (4) Colour & Other Location Properties white

Zhang, Wen-Xia; Xu, Guo-Chao; Huang, Lei; Pan, Jiang; Yu, HuiLei; Xu, Jian-He; Organic Letters; vol. 15; nb. 19; (2013); p. 4917 4919, View in Reaxys

Ringdahl, Bjorn; Ohnsorge, F. W.; Craig, J. Cymerman; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1981); p. 697 698, View in Reaxys References Wang, Yu; Li, Jianjiong; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 88; (2013); p. 14 - 19, View in Reaxys; Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys

colourless

supporting information

Arai, Noriyoshi; Akashi, Masaya; Sugizaki, Satoshi; Ooka, Hirohito; Inoue, Tsutomu; Ohkuma, Takeshi; Organic Letters; vol. 12; nb. 15; (2010); p. 3380 - 3383, View in Reaxys

white

Page/Page column 52; 64

Patent; ABBOTT LABORATORIES; WO2006/65233; (2006); (A1) English, View in Reaxys

white

Patent; Ji, Jianguo; Li, Tao; US2005/137184; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137203; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137204; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137226; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137398; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/159597; (2005); (A1) English, View in Reaxys; Patent; Schrimpf, Michael R.; Sippy, Kevin B.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Briggs, Clark A.; US2005/171079; (2005); (A1) English, View in Reaxys

Optical Rotatory Power (12) 1 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2 g/100ml

Solvent (Optical Rotatory Power)

hydrochlorid acid

Optical Rotatory Power [deg]

-45

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Zhang, Wen-Xia; Xu, Guo-Chao; Huang, Lei; Pan, Jiang; Yu, Hui-Lei; Xu, Jian-He; Organic Letters; vol. 15; nb. 19; (2013); p. 4917 - 4919, View in Reaxys 2 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3 g/100ml

Solvent (Optical Rotatory Power)

hydrochlorid acid

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2016-04-25 15:32:22

Optical Rotatory Power [deg]

-43.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys 3 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.06 g/100ml

Enantiomeric excess [%ee]

Solvent (Optical Rotatory Power)

acidic aq. solution

Optical Rotatory Power [deg]

-42.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Arai, Noriyoshi; Akashi, Masaya; Sugizaki, Satoshi; Ooka, Hirohito; Inoue, Tsutomu; Ohkuma, Takeshi; Organic Letters; vol. 12; nb. 15; (2010); p. 3380 - 3383, View in Reaxys 4 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/100ml

Solvent (Optical Rotatory Power)

HCl; H2O

Optical Rotatory Power [deg]

-44.9

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Comment (Optical Rota- Ratio of solvents: 1 M HCl tory Power) Nomoto, Fumiki; Hirayama, Yoshihiko; Ikunaka, Masaya; Inoue, Toru; Otsuka, Koutaro; Tetrahedron Asymmetry; vol. 14; nb. 13; (2003); p. 1871 - 1877, View in Reaxys 5 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

45.1

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

23/60

2016-04-25 15:32:22

Zhao, Ning; Kumar, Narendra; Neuenschwander, Kent; Nakanishi, Koji; Berova, Nina; Journal of the American Chemical Society; vol. 117; nb. 29; (1995); p. 7844 - 7845, View in Reaxys 6 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

-44.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Langlois; Meyer; Soulier; Synthetic Communications; vol. 22; nb. 13; (1992); p. 1895 - 1911, View in Reaxys 7 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

-37

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Saunders; Showell; Baker; Freedman; Hill; McKnight; Newberry; Salamone; Hirshfield; Springer; Journal of Medicinal Chemistry; vol. 30; nb. 6; (1987); p. 969 - 975, View in Reaxys 8 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

-45

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Rzeszotarski; Eckelman; Francis; Simms; Gibson; Jagoda; Grissom; Eng; Conklin; Reba; Journal of Medicinal Chemistry; vol. 27; nb. 2; (1984); p. 156 - 160, View in Reaxys 9 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.9 g/100ml

Solvent (Optical Rotatory Power)

ethanol; H2O

Optical Rotatory Power [deg]

-1.7

Wavelength (Optical Ro- 589 tatory Power) [nm]

24/60

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Temperature (Optical Rotatory Power) [°C]

Ringdahl, Bjorn; Ohnsorge, F. W.; Craig, J. Cymerman; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1981); p. 697 - 698, View in Reaxys 10 of 12

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

-45.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Ringdahl; Resul; Dahlbom; Acta Pharmaceutica Suecica; vol. 16; nb. 4 suppl; (1979); p. 281 - 283, View in Reaxys 11 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

c=7

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys 12 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

c=3

Solvent (Optical Rotatory Power)

aq. HCl (1n)

Optical Rotatory Power [deg]

-43.8

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys NMR Spectroscopy (20) 1 of 20

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

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

500

Location

supporting information

25/60

2016-04-25 15:32:22

Guo-Chao; Huang, Lei; Pan, Jiang; Yu, Hui-Lei; Xu, Jian-He; Organic Letters; vol. 15; nb. 19; (2013); p. 4917 4919, View in Reaxys 2 of 20

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

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

600

Wang, Yu; Li, Jianjiong; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 88; (2013); p. 14 - 19, View in Reaxys 3 of 20

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

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Location

supporting information

Zhang, Wen-Xia; Xu, Guo-Chao; Huang, Lei; Pan, Jiang; Yu, Hui-Lei; Xu, Jian-He; Organic Letters; vol. 15; nb. 19; (2013); p. 4917 - 4919, View in Reaxys 4 of 20

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

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

400

Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys 5 of 20

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

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

400

Location

supporting information

26/60

2016-04-25 15:32:22

Arai, Noriyoshi; Akashi, Masaya; Sugizaki, Satoshi; Ooka, Hirohito; Inoue, Tsutomu; Ohkuma, Takeshi; Organic Letters; vol. 12; nb. 15; (2010); p. 3380 - 3383, View in Reaxys 7 of 20

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

13C

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

100

Location

supporting information

Arai, Noriyoshi; Akashi, Masaya; Sugizaki, Satoshi; Ooka, Hirohito; Inoue, Tsutomu; Ohkuma, Takeshi; Organic Letters; vol. 12; nb. 15; (2010); p. 3380 - 3383, View in Reaxys 8 of 20

Nucleus (NMR Spectroscopy)

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

300

Original Text (NMR Spectroscopy)

Location

Page/Page column 52

Comment (NMR Spectroscopy)

Signals given

NMR (300 MHz, CD3OD) δ 1.36-1.50 (m, 1 H), 1.52-1.60 (m, 1 H), 1 .76-1.85 (m, 2H), 1.90-2.05 (m, 1 H), 2.50- 2.95(m, 5H), 3.10 (ddd, J=14.2, 8.4, 2.3 Hz, 1 H), 3.82-3.88 (m, 1 H) ppm.

Patent; ABBOTT LABORATORIES; WO2006/65233; (2006); (A1) English, View in Reaxys 9 of 20

Nucleus (NMR Spectroscopy)

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

300

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

1.36 - 1.5; 1.52 - 1.6; 1.76 - 1.85; 1.9 - 2.05; 2.5 - 2.95; 3.1; 3.82 - 3.88

Kind of signal

m, 1H; m, 1H; m, 2H; m, 1H; m, 5H; ddd, J=14.2, 8.4, 2.3 Hz, 1H; m, 1H

NMR (300 MHz, CD3OD) δ 1.36-1.50 (m, 1H), 1.52-1.60 (m, 1H), 1.76-1.85 (m, 2H), 1.90-2.05 (m, 1H), 2.50-2.95(m, 5H), 3.10 (ddd, J=14.2, 8.4, 2.3 Hz, 1H), 3.82-3.88 (m, 1H) ppm

Patent; Ji, Jianguo; Li, Tao; US2005/137184; (2005); (A1) English, View in Reaxys 10 of 20

Nucleus (NMR Spectroscopy)

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

300

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (300 MHz, MeOH-d4) δ 1.36-1.50 (m, 1H), 1.52-1.60 (m, 1H), 1.76-1.85 (m, 2H), 1.90-2.05 (m, 1H), 2.50-2.95 (m, 5H), 3.10 (ddd, J=14.2, 8.4, 2.3 Hz, 1H), 3.82-3.88 (m, 1H) ppm.

Patent; Ji, Jianguo; Li, Tao; US2005/137203; (2005); (A1) English, View in Reaxys

27/60

2016-04-25 15:32:22

11 of 20

Nucleus (NMR Spectroscopy)

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

300

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

1.36 - 1.5; 1.52 - 1.6; 1.76 - 1.85; 1.9 - 2.05; 2.5 - 2.95; 3.1; 3.82 - 3.88

Kind of signal

m, 1H; m, 1H; m, 2H; m, 1H; m, 5H; ddd, J=14.2, 8.4, 2.3 Hz, 1H; m, 1H

NMR (300 MHz, CD3OD) δ 1.36-1.50 (m, 1H), 1.52-1.60 (m, 1H), 1.76-1.85 (m, 2H), 1.90-2.05 (m, 1H), 2.50-2.95(m, 5H), 3.10 (ddd, J=14.2, 8.4, 2.3 Hz, 1H), 3.82-3.88 (m, 1H) ppm.

Patent; Abbott Laboratories; US2005/137204; (2005); (A1) English, View in Reaxys 12 of 20

Nucleus (NMR Spectroscopy)

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

300

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

1.36 - 1.5; 1.52 - 1.6; 1.76 - 1.85; 1.9 - 2.05; 2.5 - 2.95; 3.1; 3.82 - 3.88

Kind of signal

m, 1H; m, 1H; m, 2H; m, 1H; m, 5H; ddd, J=14.2, 8.4, 2.3 Hz, 1H; m, 1H

NMR (300 MHz, MeOH-d4) δ 1.36-1.50 (m, 1H), 1.52-1.60 (m, 1H), 1.76-1.85 (m, 2H), 1.90-2.05 (m, 1H), 2.50-2.95(m, 5H), 3.10 (ddd, J=14.2, 8.4, 2.3 Hz, 1H), 3.82-3.88 (m, 1H) ppm

Patent; Abbott Laboratories; US2005/137226; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137398; (2005); (A1) English, View in Reaxys 13 of 20

Nucleus (NMR Spectroscopy)

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

300

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

1.36 - 1.5; 1.52 - 1.6; 1.76 - 1.85; 1.9 - 2.05; 2.5 - 2.95; 3.1; 3.82 - 3.88

Kind of signal

m, 1H; m, 1H; m, 2H; m, 1H; m, 5H; ddd, J=14.2, 8.4, 2.3 Hz, 1H; m, 1H

NMR (300 MHz, MeOH-d4) δ 1.36-1.50 (m, 1H), 1.52-1.60 (m, 1H), 1.76-1.85 (m, 2H), 1.90-2.05 (m, 1H), 2.50-2.95 (m, 5H), 3.10 (ddd, J=14.2, 8.4, 2.3 Hz, 1H), 3.82-3.88 (m, 1H) ppm

Patent; Abbott Laboratories; US2005/159597; (2005); (A1) English, View in Reaxys 14 of 20

Nucleus (NMR Spectroscopy)

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

300

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Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

3.82 - 3.88; 3.1; 2.5 - 2.95; 1.9 - 2.05; 1.851; 1.52 - 1.6; 1.36 - 1.5

Kind of signal

1H, m; 1H, ddd, J=14, 8, 2 Hz; 5H, m; 1H, m; 2H, m; 1H, m; 1H, m

NMR (300 MHz, methanol-d4) δ 3.88-3.82 (1H, m), 3.10 (1H, ddd, J=14, 8, 2 Hz), 2.95-2.50 (5H, m), 2.05-1.90 (1H, m), 1.851.76 (2H, m), 1.60-1.52 (1H, m), 1.50-1.36 (1H, m)

Patent; Schrimpf, Michael R.; Sippy, Kevin B.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Briggs, Clark A.; US2005/171079; (2005); (A1) English, View in Reaxys 15 of 20

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

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

400

Nomoto, Fumiki; Hirayama, Yoshihiko; Ikunaka, Masaya; Inoue, Toru; Otsuka, Koutaro; Tetrahedron Asymmetry; vol. 14; nb. 13; (2003); p. 1871 - 1877, View in Reaxys 16 of 20

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

Solvents (NMR Spectro- CDCl3 scopy) Knight, David W.; Lewis, Neil; Share, Andrew C.; Haigh, David; Journal of the Chemical Society - Perkin Transactions 1; nb. 22; (1998); p. 3673 - 3683, View in Reaxys 17 of 20

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

13C

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Knight, David W.; Lewis, Neil; Share, Andrew C.; Haigh, David; Journal of the Chemical Society - Perkin Transactions 1; nb. 22; (1998); p. 3673 - 3683, View in Reaxys 19 of 20

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

Solvents (NMR Spectro- D2O scopy) Langlois; Meyer; Soulier; Synthetic Communications; vol. 22; nb. 13; (1992); p. 1895 - 1911, View in Reaxys 20 of 20

Description (NMR Spec- Spin-spin coupling constants troscopy)

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Solvents (NMR Spectro- D2O scopy) Comment (NMR Spectroscopy)

1H-1H

Langlois; Meyer; Soulier; Synthetic Communications; vol. 22; nb. 13; (1992); p. 1895 - 1911, View in Reaxys IR Spectroscopy (4) 1 of 4

Description (IR Spectroscopy)

Bands

Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Arai, Noriyoshi; Akashi, Masaya; Sugizaki, Satoshi; Ooka, Hirohito; Inoue, Tsutomu; Ohkuma, Takeshi; Organic Letters; vol. 12; nb. 15; (2010); p. 3380 - 3383, View in Reaxys; Matsumura, Kazuhiko; Arai, Noriyoshi; Hori, Kiyoto; Saito, Takao; Sayo, Noboru; Ohkuma, Takeshi; Journal of the American Chemical Society; vol. 133; nb. 28; (2011); p. 10696 - 10699, View in Reaxys 3 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Nomoto, Fumiki; Hirayama, Yoshihiko; Ikunaka, Masaya; Inoue, Toru; Otsuka, Koutaro; Tetrahedron Asymmetry; vol. 14; nb. 13; (2003); p. 1871 - 1877, View in Reaxys 4 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3450 cm**(-1)

Knight, David W.; Lewis, Neil; Share, Andrew C.; Haigh, David; Journal of the Chemical Society - Perkin Transactions 1; nb. 22; (1998); p. 3673 - 3683, View in Reaxys Mass Spectrometry (7) Description (Mass Location Spectrometry)

Comment (Mass Spectrometry)

Peak

electrospray ionisation (ESI); IT (ion trap); spectrum

References Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys

HRMS (High resolution mass spectrometry); EI (Electron impact); Spectrum

supporting information

Matsumura, Kazuhiko; Arai, Noriyoshi; Hori, Kiyoto; Saito, Takao; Sayo, Noboru; Ohkuma, Takeshi; Journal of the American Chemical Society; vol. 133; nb. 28; (2011); p. 10696 - 10699, View in Reaxys

EI (Electron impact); HRMS (High resolution mass spectrometry); Spectrum

supporting information

Arai, Noriyoshi; Akashi, Masaya; Sugizaki, Satoshi; Ooka, Hirohito; Inoue, Tsutomu; Ohkuma, Takeshi; Organic Letters; vol. 12; nb. 15; (2010); p. 3380 - 3383, View in Reaxys

DCI (Desorption chemical ionization)

Page/Page column 52; 64

CI (Chemical ionization)

Molecular peak

Patent; ABBOTT LABORATORIES; WO2006/65233; (2006); (A1) English, View in Reaxys 128 m/z

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Patent; Ji, Jianguo; Li, Tao; US2005/137398; (2005); (A1) English, View in Reaxys

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DCI (Desorption chemical ionization)

Molecular peak

DCI (Desorption chemical ionization)

Molecular peak

Patent; Ji, Jianguo; Li, Tao; US2005/137398; (2005); (A1) English, View in Reaxys 128 m/z

Patent; Ji, Jianguo; Li, Tao; US2005/137184; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137203; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137204; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137226; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/159597; (2005); (A1) English, View in Reaxys; Patent; Schrimpf, Michael R.; Sippy, Kevin B.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Briggs, Clark A.; US2005/171079; (2005); (A1) English, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

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Janusz; McPherson, Daniel W.; Ferkany, John W.; Kinnier, William J.; Noronha-Blob, Lalita; Kirkien-Rzeszotarski, Alicja; Journal of Medicinal Chemistry; vol. 31; nb. 7; (1988); p. 1463 - 1466, View in Reaxys; Cohen; Gibson; Reba; Journal of Pharmaceutical Sciences; vol. 76; nb. 10; (1987); p. 848 - 850, View in Reaxys; Kiesewetter; Silverton; Eckelman; Journal of Medicinal Chemistry; vol. 38; nb. 10; (1995); p. 1711 - 1719, View in Reaxys; Dei; Bellucci; Gualtieri; Romanelli; Scapecchi; Teodori; Bartolini; Ghelardini; Farmaco; vol. 50; nb. 5; (1995); p. 303 - 309, View in Reaxys; Zhao, Ning; Kumar, Narendra; Neuenschwander, Kent; Nakanishi, Koji; Berova, Nina; Journal of the American Chemical Society; vol. 117; nb. 29; (1995); p. 7844 - 7845, View in Reaxys; Fancelli; Caccia; Fornaretto; McArthur; Severino; Vaghi; Varasi; Bioorganic and Medicinal Chemistry Letters; vol. 6; nb. 3; (1996); p. 263 - 266, View in Reaxys; Visser, Ton J.; Van Waarde, Aren; Jansen, Twan J. H.; Visser, Gerben M.; Van Der Mark, Thom W.; Kraan, Jan; Ensing, Kees; Vaalburg, Willem; Journal of Medicinal Chemistry; vol. 40; nb. 1; (1997); p. 117 - 124, View in Reaxys; Yang, Donglai; Soulier, Jean-Louis; Sicsic, Sames; Mathe-Allainmat, Monique; Bremont, Beatrice; Croci, Tiziano; Cardamone, Rosanna; Aureggi, Giulio; Langlois, Michel; Journal of Medicinal Chemistry; vol. 40; nb. 4; (1997); p. 608 - 621, View in Reaxys; Kaempfer, Ingrid; Heinicke, Jochen; Sorger, Dietlind; Schulze, Klaus; Schliebs, Reinhard; Knapp, Wolfram H.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 38; nb. 11; (1996); p. 1047 - 1052, View in Reaxys; Kiesewetter, Dale O.; Carson, Richard E.; Jagoda, Elaine M.; Endres, Christopher J.; Der, Margaret G.; Herscovitch, Peter; Eckelman, William C.; Bioorganic and Medicinal Chemistry; vol. 5; nb. 8; (1997); p. 1555 - 1567, View in Reaxys; Ward, John S.; Merritt, Leander; Calligaro, Da-

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vid O.; Bymaster, Franklin P.; Shannon, Harlan E.; Mitch, Charles H.; Whitesitt, Celia; Brunsting, David; Sheardown, Malcolm J.; Olesen, Preben H.; Swedberg, Michael D.B.; Jeppesen, Lone; Sauerberg, Per; Journal of Medicinal Chemistry; vol. 41; nb. 3; (1998); p. 379 - 392, View in Reaxys; Knight, David W.; Lewis, Neil; Share, Andrew C.; Haigh, David; Journal of the Chemical Society - Perkin Transactions 1; nb. 22; (1998); p. 3673 3683, View in Reaxys; Naito, Ryo; Takeuchi, Makoto; Morihira, Koichiro; Hayakawa, Masahiko; Ikeda, Ken; Shibanuma, Tadao; Isomura, Yasuo; Chemical and Pharmaceutical Bulletin; vol. 46; nb. 8; (1998); p. 1286 - 1294, View in Reaxys; Primozic, Ines; Hrenar, Tomica; Tomic, Srdanka; Meic, Zlatko; Journal of Physical Organic Chemistry; vol. 15; nb. 8; (2002); p. 608 - 614, View in Reaxys; Nomoto, Fumiki; Hirayama, Yoshihiko; Ikunaka, Masaya; Inoue, Toru; Otsuka, Koutaro; Tetrahedron Asymmetry; vol. 14; nb. 13; (2003); p. 1871 - 1877, View in Reaxys; Ishihara, Tsukasa; Kakuta, Hirotoshi; Moritani, Hiroshi; Ugawa, Tohru; Yanagisawa, Isao; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 10; (2004); p. 1204 - 1209, View in Reaxys; Han, Xiang-Yu; Liu, He; Liu, Chun-He; Wu, Bo; Chen, Lan-Fu; Zhong, Bo-Hua; Liu, Ke-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 8; (2005); p. 1979 - 1982, View in Reaxys; Naito, Ryo; Yonetoku, Yasuhiro; Okamoto, Yoshinori; Toyoshima, Akira; Ikeda, Ken; Takeuchi, Makoto; Journal of Medicinal Chemistry; vol. 48; nb. 21; (2005); p. 6597 - 6606, View in Reaxys; Liu, Yu-Min; Liu, He; Zhong, Bo-Hua; Liu, Ke-Liang; Journal of Chemical Research; nb. 5; (2006); p. 335 - 337, View in Reaxys; Liu, Yu-Min; Liu, He; Zhong, Bo-Hua; Liu, Ke-Liang; Synthetic Communications; vol. 36; nb. 13; (2006); p. 1815 - 1822, View in Reaxys; Patent; Pfizer Inc.; US5292749; (1994); (A1) English, View in Reaxys; Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/22556; (2004); (A1) English, View in Reaxys; Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/48225; (2006); (A1) English, View in Reaxys; Patent; Koltai, Tamas; Nidam, Tamar; Gilboa, Eyal; Perlman, Nurit; Pinhasov, Michael; Abramov, Mili; US2008/114028; (2008); (A1) English, View in Reaxys; Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/59245; (2008); (A1) English, View in Reaxys; Patent; ZENTIVA, A.S.; WO2008/77357; (2008); (A2) English, View in Reaxys; Patent; Medichem, S.A.; US2008/242697; (2008); (A1) English, View in Reaxys; Patent; ARGENTA DISCOVERY LIMITED; WO2008/99186; (2008); (A1) English, View in Reaxys; Patent; DR. REDDY'S LABORATORIES LTD.; DR. REDDY'S LABORATORIES, INC.; WO2008/128028; (2008); (A2) English, View in Reaxys; Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2009/11844; (2009); (A1) English, View in Reaxys; Patent; Laboratorios SALVAT, S.A.; EP2065385; (2009); (A1) English, View in Reaxys; Patent; Jirman, Josef; Junek, Richard; Lustig, Petr; Richter, Jindrich; Placek, Lukas; US2009/203914; (2009); (A1) English, View in Reaxys; Patent; Dipharma Francis S.r.l.; US2009/203915; (2009); (A1) English, View in Reaxys; Patent; CADILA HEALTHCARE LIMITED; WO2009/87664; (2009); (A1) English, View in Reaxys; Patent; Dipharma Francis S.r.l.; EP2088148; (2009); (A2) English, View in Reaxys; Patent; Kanto Kagaku Kabushiki Kaisha; US2009/216019; (2009); (A1) English, View in Reaxys; Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/98453; (2009); (A1) English, View in Reaxys; Patent; Astellas Pharma Inc.; EP2119716; (2009); (A1) English, View in Reaxys; Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); (A1) English, View in Reaxys; Patent; MSN LABORATORIES LIMITED; WO2009/139002; (2009); (A2) English, View in Reaxys; Patent; ASTRAZENECA AB; ARGENTA DISCOVERY Ltd.; FORD, Rhonan; WO2009/139709; (2009); (A1) English, View in Reaxys; Patent; ASTRAZENECA AB; ARGENTA DISCOVERY Ltd.; WO2009/139710; (2009); (A1) English, View in Reaxys; Patent; Ranbaxy Laboratories Limited; EP2130830; (2009); (A1) English, View in Reaxys; Patent; ZAKLADY FARMACEUTYCZNE POLPHARMA SA; WO2009/142522; (2009); (A1) English, View in Reaxys; Patent; ARGENTA DISCOVERY LIMITED; ASTRAZENECA AB; WO2009/153536; (2009); (A1) English, View in Reaxys; Patent; RANBAXY LABORATORIES LIMITED; US2009/326004; (2009); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137184; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137203; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137204; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137226; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137398; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/159597; (2005); (A1) English, View in Reaxys; Patent; ARYX THERAPEUTICS; WO2005/68461; (2005); (A1) English, View in Reaxys; Patent; Schrimpf, Michael R.; Sippy, Kevin B.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Briggs, Clark A.; US2005/171079; (2005); (A1) English, View in Reaxys; Patent; ALMIRALL PRODESFARMA, SA; WO2005/90342; (2005); (A1) English, View in Reaxys; Brossat, Maude; Moody, Thomas S.; Taylor, Stephen J.C.; Wiffen, Jonathan W.; Tetrahedron Asymmetry; vol. 20; nb. 18; (2009); p. 2112 - 2116, View in Reaxys; Prat, Maria; Fernandez, Dolors; Buil, M. 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Comment (Pharmacological Data)

inhibition of antibody binding to the solid phase IC50 = 1.26*10-4M

Burkin; Zoryan; Pharmaceutical Chemistry Journal; vol. 26; nb. 5; (1992); p. 376 - 378, View in Reaxys Use (5) Use Pattern

Location

References

physiologicallyactive compound

Page/Page column title page; 1

Patent; Nagoya Industrial Science Research Institute; Kanto Kagaku Kabushiki Kaisha; EP1867654; (2007); (A1) English, View in Reaxys

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agricultural chem- Page/Page colicals umn title page; 1

Patent; Nagoya Industrial Science Research Institute; Kanto Kagaku Kabushiki Kaisha; EP1867654; (2007); (A1) English, View in Reaxys

liquid-crystal materials

Patent; Nagoya Industrial Science Research Institute; Kanto Kagaku Kabushiki Kaisha; EP1867654; (2007); (A1) English, View in Reaxys

Page/Page column title page; 1

Pharmaceutical intermediate

Patent; Takasago International Corporation; US2006/47122; (2006); (A1) English, View in Reaxys

Agricultural chemical intermediate

Patent; Takasago International Corporation; US2006/47122; (2006); (A1) English, View in Reaxys

Reaxys ID 80122 View in Reaxys

3/39 CAS Registry Number: 3684-26-2; 25333-42-0; 34583-34-1; 1619-34-7 Chemical Name: (S)-quinuclidin-3-ol Linear Structure Formula: C7H13NO Molecular Formula: C7H13NO Molecular Weight: 127.186 Type of Substance: heterocyclic InChI Key: IVLICPVPXWEGCA-SSDOTTSWSA-N Note:

Substance Label (9) Label References 2

Chavakula, Ramadas; Rao, Mutyala Narayana; Rao, Chennupati Srinivasa; Journal of the Indian Chemical Society; vol. 90; nb. 2; (2013); p. 261 - 262, View in Reaxys

Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys

3-S; IIIb

Patent; National University Corporation Hokkaido University; Nippon Soda Co., Ltd.; EP2186812; (2010); (A1) English, View in Reaxys

substrate, tab 3/11

Shibuya, Masatoshi; Tomizawa, Masaki; Suzuki, Iwao; Iwabuchi, Yoshiharu; Journal of the American Chemical Society; vol. 128; nb. 26; (2006); p. 8412 - 8413, View in Reaxys

(S)-3

Han, Xiang-Yu; Liu, He; Liu, Chun-He; Wu, Bo; Chen, Lan-Fu; Zhong, Bo-Hua; Liu, Ke-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 8; (2005); p. 1979 - 1982, View in Reaxys

(S)-34

Naito, Ryo; Yonetoku, Yasuhiro; Okamoto, Yoshinori; Toyoshima, Akira; Ikeda, Ken; Takeuchi, Makoto; Journal of Medicinal Chemistry; vol. 48; nb. 21; (2005); p. 6597 - 6606, View in Reaxys

(+)-3

Ishihara, Tsukasa; Kakuta, Hirotoshi; Moritani, Hiroshi; Ugawa, Tohru; Yanagisawa, Isao; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 10; (2004); p. 1204 - 1209, View in Reaxys

(S)-1

Nomoto, Fumiki; Hirayama, Yoshihiko; Ikunaka, Masaya; Inoue, Toru; Otsuka, Koutaro; Tetrahedron Asymmetry; vol. 14; nb. 13; (2003); p. 1871 - 1877, View in Reaxys

Esikova, I. A.; Serebryakov, E. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 8.2; (1989); p. 1682 - 1690; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 8; (1989); p. 1836 - 1843, View in Reaxys

Patent-Specific Data (2) Location in Patent References Patent; National University Corporation Hokkaido University; Nippon Soda Co., Ltd.; EP2186812; (2010); (A1) English, View in Reaxys Claim

Patent; BEND RESEARCH, INC.; EP577253; (1994); (A2) English, View in Reaxys; Patent; Daicel Chemical Industries, Ltd.; US5888804; (1999); (A1) English, View in Reaxys

Related Structure (1) References Ringdahl; Resul; Dahlbom; Acta Pharmaceutica Suecica; vol. 16; nb. 4 suppl; (1979); p. 281 - 283, View in Reaxys Derivative (1) Derivative

References

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2016-04-25 15:32:22

(S)-quinuclidin-3ol hydrochloride

Melting Point (3) 1 of 3

Melting Point [°C]

215 - 217

Location

supporting information

Melting Point [°C]

221 - 223

Solvent (Melting Point)

acetone

Melting Point [°C]

223.5 - 225

Ringdahl; Resul; Dahlbom; Acta Pharmaceutica Suecica; vol. 16; nb. 4 suppl; (1979); p. 281 - 283, View in Reaxys Chromatographic Data (3) Chromatographic Location data

References

GC (Gas chromatography)

Wang, Yu; Li, Jianjiong; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 88; (2013); p. 14 - 19, View in Reaxys

HPLC (High performance liquid chromatography)

Wang, Yu; Li, Jianjiong; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 88; (2013); p. 14 - 19, View in Reaxys

GC (Gas chroma- supporting infortography) mation

Zhang, Wen-Xia; Xu, Guo-Chao; Huang, Lei; Pan, Jiang; Yu, Hui-Lei; Xu, Jian-He; Organic Letters; vol. 15; nb. 19; (2013); p. 4917 - 4919, View in Reaxys

Crystal Property Description (4) Colour & Other Location Properties

References

white

Wang, Yu; Li, Jianjiong; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 88; (2013); p. 14 - 19, View in Reaxys

colourless

supporting information

Matsumura, Kazuhiko; Arai, Noriyoshi; Hori, Kiyoto; Saito, Takao; Sayo, Noboru; Ohkuma, Takeshi; Journal of the American Chemical Society; vol. 133; nb. 28; (2011); p. 10696 - 10699, View in Reaxys

white

Page/Page column 64

Patent; ABBOTT LABORATORIES; WO2006/65233; (2006); (A1) English, View in Reaxys

white

Patent; Ji, Jianguo; Li, Tao; US2005/137184; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137204; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137226; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137398; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/159597; (2005); (A1) English, View in Reaxys

Optical Rotatory Power (5) 1 of 5

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

45.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

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Langlois; Meyer; Soulier; Synthetic Communications; vol. 22; nb. 13; (1992); p. 1895 - 1911, View in Reaxys 2 of 5

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Esikova, I. A.; Serebryakov, E. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 8.2; (1989); p. 1682 - 1690; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 8; (1989); p. 1836 - 1843, View in Reaxys 3 of 5

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

39.3

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Saunders; Showell; Baker; Freedman; Hill; McKnight; Newberry; Salamone; Hirshfield; Springer; Journal of Medicinal Chemistry; vol. 30; nb. 6; (1987); p. 969 - 975, View in Reaxys 4 of 5

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

45.8

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Rzeszotarski; Eckelman; Francis; Simms; Gibson; Jagoda; Grissom; Eng; Conklin; Reba; Journal of Medicinal Chemistry; vol. 27; nb. 2; (1984); p. 156 - 160, View in Reaxys 5 of 5

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

46.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Ringdahl; Resul; Dahlbom; Acta Pharmaceutica Suecica; vol. 16; nb. 4 suppl; (1979); p. 281 - 283, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy)

37/60

2016-04-25 15:32:22

Nucleus (NMR Spectroscopy)

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

600

Wang, Yu; Li, Jianjiong; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 88; (2013); p. 14 - 19, View in Reaxys 2 of 3

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

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Matsumura, Kazuhiko; Arai, Noriyoshi; Hori, Kiyoto; Saito, Takao; Sayo, Noboru; Ohkuma, Takeshi; Journal of the American Chemical Society; vol. 133; nb. 28; (2011); p. 10696 - 10699, View in Reaxys Mass Spectrometry (4) Description (Mass Location Spectrometry) HRMS (High resolution mass spectrometry); EI (Electron impact); Spectrum

supporting information

DCI (Desorption chemical ionization)

Page/Page column 64

DCI (Desorption chemical ionization)

Comment (Mass Spectrometry)

Peak

References Matsumura, Kazuhiko; Arai, Noriyoshi; Hori, Kiyoto; Saito, Takao; Sayo, Noboru; Ohkuma, Takeshi; Journal of the American Chemical Society; vol. 133; nb. 28; (2011); p. 10696 - 10699, View in Reaxys

Molecular peak

Patent; ABBOTT LABORATORIES; WO2006/65233; (2006); (A1) English, View in Reaxys

Molecular peak

Patent; Ji, Jianguo; Li, Tao; US2005/137184; (2005); (A1) English, View in Reaxys

Molecular peak

128 m/z

38/60

Patent; Ji, Jianguo; Li, Tao; US2005/137203; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137204; (2005);

2016-04-25 15:32:22

(A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137226; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137398; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/159597; (2005); (A1) English, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; BEND RESEARCH, INC.; EP577253; (1994); (A2) English, View in Reaxys; Patent; Lonza AG; US5744606; (1998); (A1) English, View in Reaxys; Patent; Daicel Chemical Industries, Ltd.; US5888804; (1999); (A1) English, View in Reaxys; Patent; Astra AB; US5998429; (1999); (A1) English, View in Reaxys; Patent; Asahi Kasei Kogyo Kabushiki Kaisha; US5200415; (1993); (A1) English, View in Reaxys; Patent; Prat Quinones, Maria; Fernandez Forner, Maria Dolors; Buil Albero, Maria Antonia; US2004/72863; (2004); (A1) English, View in Reaxys; Patent; KAWAKEN FINE CHEMICALS CO., LTD.; WO2004/78686; (2004); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/245531; (2005); (A1) English, View in Reaxys; Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2006/69097; (2006); (A2) English, View in Reaxys; Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys; Ringdahl; Resul; Dahlbom; Acta Pharmaceutica Suecica; vol. 16; nb. 4 suppl; (1979); p. 281 - 283, View in Reaxys; Esikova, I. 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Janusz; McPherson, Daniel W.; Ferkany, John W.; Kinnier, William J.; Noronha-Blob, Lalita; Kirkien-Rzeszotarski, Alicja; Journal of Medicinal Chemistry; vol. 31; nb. 7; (1988); p. 1463 - 1466, View in Reaxys; Cereda; Ezhaya; Bellora; Schiavi; Sagrada; Doods; Donetti; European Journal of Medicinal Chemistry; vol. 29; nb. 6; (1994); p. 411 - 421, View in Reaxys; Kiesewetter; Silverton; Eckelman; Journal of Medicinal Chemistry; vol. 38; nb. 10; (1995); p. 1711 - 1719, View in Reaxys; Fancelli; Caccia; Fornaretto; McArthur; Severino; Vaghi; Varasi; Bioorganic and Medicinal Chemistry Letters; vol. 6; nb. 3; (1996); p. 263 - 266, View in Reaxys; Yang, Donglai; Soulier, Jean-Louis; Sicsic, Sames; Mathe-Allainmat, Monique; Bremont, Beatrice; Croci, Tiziano; Cardamone, Rosanna; Aureggi, Giulio; Langlois, Michel; Journal of Medicinal Chemistry; vol. 40; nb. 4; (1997); p. 608 - 621, View in Reaxys; Ward, John S.; Merritt, Leander; Calligaro, David O.; Bymaster, Franklin P.; Shannon, Harlan E.; Mitch, Charles H.; Whitesitt, Celia; Brunsting, David; Sheardown, Malcolm J.; Olesen, Preben H.; Swedberg, Michael D.B.; Jeppesen, Lone; Sauerberg, Per; Journal of Medicinal Chemistry; vol. 41; nb. 3; (1998); p. 379 - 392, View in Reaxys; Knight, David W.; Lewis, Neil; Share, Andrew C.; Haigh, David; Journal of the Chemical Society - Perkin Transactions 1; nb. 22; (1998); p. 3673 - 3683, View in Reaxys; Naito, Ryo; Takeuchi, Makoto; Morihira, Koichiro; Hayakawa, Masahiko; Ikeda, Ken; Shibanuma, Tadao; Isomura, Yasuo; Chemical and Pharmaceutical Bulletin; vol. 46; nb. 8; (1998); p. 1286 - 1294, View in Reaxys; Primozic, Ines; Hrenar, Tomica; Tomic, Srdanka; Meic, Zlatko; Journal of Physical Organic Chemistry; vol. 15; nb. 8; (2002); p. 608 - 614, View in Reaxys; Nomoto, Fumiki; Hirayama, Yoshihiko; Ikunaka, Masaya; Inoue, Toru; Otsuka, Koutaro; Tetrahedron Asymmetry; vol. 14; nb. 13; (2003); p. 1871 - 1877, View in Reaxys; Ishihara, Tsukasa; Kakuta, Hirotoshi; Moritani, Hiroshi; Ugawa, Tohru; Yanagisawa, Isao; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 10; (2004); p. 1204 - 1209, View in Reaxys; Han, Xiang-Yu; Liu, He; Liu, Chun-He; Wu, Bo; Chen, Lan-Fu; Zhong, Bo-Hua; Liu, Ke-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 8; (2005); p. 1979 - 1982, View in Reaxys; Naito, Ryo; Yonetoku, Yasuhiro; Okamoto, Yoshinori; Toyoshima, Akira; Ikeda, Ken; Takeuchi, Makoto; Journal of Medicinal Chemistry; vol. 48; nb. 21; (2005); p. 6597 - 6606, View in Reaxys; Shibuya, Masatoshi; Tomizawa, Masaki; Suzuki, Iwao; Iwabuchi, Yoshiharu; Journal of the American Chemical Society; vol. 128; nb. 26; (2006); p. 8412 - 8413, View in Reaxys; Liu, Yu-Min; Liu, He; Zhong, Bo-Hua; Liu, Ke-Liang; Journal of Chemical Research; nb. 5; (2006); p. 335 - 337, View in Reaxys; Liu, Yu-Min; Liu, He; Zhong, Bo-Hua; Liu, KeLiang; Synthetic Communications; vol. 36; nb. 13; (2006); p. 1815 - 1822, View in Reaxys; Patent; A. H. Robins Company, Incorporated; US5206246; (1993); (A1) English, View in Reaxys; Patent; Kanto Kagaku Kabushiki Kaisha; US2009/216019; (2009); (A1) English, View in Reaxys; Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137184; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137203; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137204; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137226; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137398; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/159597; (2005); (A1) English, View in Reaxys; Brossat, Maude; Moody, Thomas S.; Taylor, Stephen J.C.; Wiffen, Jonathan W.; Tetrahedron Asymmetry; vol. 20; nb. 18; (2009); p. 2112 - 2116, View in Reaxys; Patent; ARGENTA DISCOVERY LIMITED; ASTRAZENECA AB; NADIN, Alan, John; OSBOURN, Susan, Elizabeth; TISSELLI, Patrizia; RAY, Nicholas, Charles; WO2010/18352; (2010); (A1) English, View in Reaxys; Patent; National University Corporation Hokkaido University; Nippon Soda Co., Ltd.; EP2186812; (2010); (A1) English, View in Reaxys; Patent; CHIESI

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FARMACEUTICI S.P.A.; CALIGIURI, Antonio; RICCABONI, Mauro; AMARI, Gabriele; WO2010/72338; (2010); (A1) English, View in Reaxys; Arai, Noriyoshi; Akashi, Masaya; Sugizaki, Satoshi; Ooka, Hirohito; Inoue, Tsutomu; Ohkuma, Takeshi; Organic Letters; vol. 12; nb. 15; (2010); p. 3380 - 3383, View in Reaxys; Patent; ABBOTT LABORATORIES; WO2006/65233; (2006); (A1) English, View in Reaxys; Clark, George R.; Falshaw, Andrew; Gainsford, Graeme J.; Lensink, Cornelis; Slade, Angela T.; James Wright; Journal of Coordination Chemistry; vol. 63; nb. 3; (2010); p. 373 - 393, View in Reaxys; Patent; NeuroSearch A/S; WO2007/93602; (2007); (A1) English, View in Reaxys; Patent; Nagoya Industrial Science Research Institute; Kanto Kagaku Kabushiki Kaisha; EP1867654; (2007); (A1) English, View in Reaxys; Patent; Bull, Richard James; Skidmore, Elizabeth Anne; Ford, Rhonan Lee; Mather, Andrew Nigel; Mete, Antonio; US2011/172237; (2011); (A1) English, View in Reaxys; Matsumura, Kazuhiko; Arai, Noriyoshi; Hori, Kiyoto; Saito, Takao; Sayo, Noboru; Ohkuma, Takeshi; Journal of the American Chemical Society; vol. 133; nb. 28; (2011); p. 10696 - 10699, View in Reaxys; Patent; TAKASAGO INTERNATIONAL CORPORATION; NARA, Hideki; YOKOZAWA, Tohru; WO2011/135753; (2011); (A1) English, View in Reaxys; Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); (A1) English, View in Reaxys; Hayashi, Masaki; Shibuya, Masatoshi; Iwabuchi, Yoshiharu; Journal of Organic Chemistry; vol. 77; nb. 6; (2012); p. 3005 - 3009, View in Reaxys; Facchetti, Giorgio; Cesarotti, Edoardo; Pellizzoni, Michela; Zerla, Daniele; Rimoldi, Isabella; European Journal of Inorganic Chemistry; nb. 27; (2012); p. 4365 - 4370, View in Reaxys; Chavakula, Ramadas; Rao, Mutyala Narayana; Rao, Chennupati Srinivasa; Journal of the Indian Chemical Society; vol. 90; nb. 2; (2013); p. 261 - 262, View in Reaxys; Wang, Yu; Li, Jianjiong; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 88; (2013); p. 14 - 19, View in Reaxys; Zhang, Wen-Xia; Xu, GuoChao; Huang, Lei; Pan, Jiang; Yu, Hui-Lei; Xu, Jian-He; Organic Letters; vol. 15; nb. 19; (2013); p. 4917 - 4919, View in Reaxys; Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys; Nagashima, Shinya; Matsushima, Yuji; Hamaguchi, Hisao; Nagata, Hiroshi; Kontani, Toru; Moritomo, Ayako; Koshika, Tadatsura; Takeuchi, Makoto; Bioorganic and Medicinal Chemistry; vol. 22; nb. 13; (2014); p. 3478 - 3487, View in Reaxys; Patent; GENZYME CORPORATION; SIEGEL, Craig; GIMI, Rayomand; REARDON, Michael; ZHAO, Jin; WO2014/151291; (2014); (A1) English, View in Reaxys; Patent; GENZYME CORPORATION; SIEGEL, Craig; ZHAO, Jin; WO2014/152215; (2014); (A1) English, View in Reaxys; Zhao, Jin; Gimi, Rayomand; Katti, Sanjeev; Reardon, Michael; Nivorozhkin, Vitaly; Konowicz, Paul; Lee, Edward; Sole, Lynne; Green, Jerome; Siegel, Craig S.; Organic Process Research and Development; vol. 19; nb. 5; (2015); p. 576 - 581, View in Reaxys; Patent; Genzyme Corporation; Bourque, Elyse; Hirth, Bradford; Sklerj, Renato; Makino, Elina; Morshed, Fazeela; Li, Lingyun; Mason, Paul; Leonard, John P.; Lillie, James; Liu, Hanlan; Cromwell, Mary A.; Wang, Bing; O'Shea, Thomas; US9126993; (2015); (B2) English, View in Reaxys 2 of 2

Comment (Pharmacological Data)

inhibition of antibody binding to the solid phase IC50 = 3.98*10-4M

Burkin; Zoryan; Pharmaceutical Chemistry Journal; vol. 26; nb. 5; (1992); p. 376 - 378, View in Reaxys Use (3) Use Pattern

Location

References

physiologicallyactive compound

Page/Page column title page; 1

Patent; Nagoya Industrial Science Research Institute; Kanto Kagaku Kabushiki Kaisha; EP1867654; (2007); (A1) English, View in Reaxys

agricultural chem- Page/Page colicals umn title page; 1

Patent; Nagoya Industrial Science Research Institute; Kanto Kagaku Kabushiki Kaisha; EP1867654; (2007); (A1) English, View in Reaxys

liquid-crystal materials

Patent; Nagoya Industrial Science Research Institute; Kanto Kagaku Kabushiki Kaisha; EP1867654; (2007); (A1) English, View in Reaxys

Page/Page column title page; 1

Reaxys ID 10022607 View in Reaxys

4/39 Chemical Name: (R)-quinuclidin-3-ol hydrochloride; (R)-(-)-3quinuclidinol hydrochloride; (3R)-3-quinuclidinol hydrochloride; (R)-3-Quinuclidinol hydrochloride; (R)-(-)-3-quinuclidinol Linear Structure Formula: C7H13NO*ClH Molecular Formula: C7H13NO*ClH Molecular Weight: 163.647 Type of Substance: heterocyclic InChI Key: OYEJRVVBERZWPD-FJXQXJEOSA-N Note:

HO Cl

Substance Label (1) Label References (R)-QOH

Bosak, Anita; Primozic, Ines; Orsulic, Mislav; Tomic, Srdanka; Simeon-Rudolf, Vera; Croatica Chemica Acta; vol. 78; nb. 1; (2005); p. 121 - 128, View in Reaxys

Patent-Specific Data (1)

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Location in Patent References Claim

Patent; Daicel Chemical Industries, Ltd.; EP1318200; (2003); (A2) English, View in Reaxys

Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; Daicel Chemical Industries, Ltd.; EP1318200; (2003); (A2) English, View in Reaxys; Patent; Mammen, Mathai; Dunham, Sarah; US2005/113417; (2005); (A1) English, View in Reaxys; Patent; ARYX THERAPEUTICS; WO2007/28073; (2007); (A2) English, View in Reaxys; Bosak, Anita; Primozic, Ines; Orsulic, Mislav; Tomic, Srdanka; Simeon-Rudolf, Vera; Croatica Chemica Acta; vol. 78; nb. 1; (2005); p. 121 - 128, View in Reaxys; Patent; CADILA HEALTHCARE LIMITED; WO2009/87664; (2009); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137184; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137203; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137204; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/137226; (2005); (A1) English, View in Reaxys; Patent; Ji, Jianguo; Li, Tao; US2005/137398; (2005); (A1) English, View in Reaxys; Patent; Abbott Laboratories; US2005/159597; (2005); (A1) English, View in Reaxys; Patent; ARYX THERAPEUTICS; WO2005/68461; (2005); (A1) English, View in Reaxys; Patent; Schrimpf, Michael R.; Sippy, Kevin B.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Briggs, Clark A.; US2005/171079; (2005); (A1) English, View in Reaxys; Patent; ABBOTT LABORATORIES; WO2006/65233; (2006); (A1) English, View in Reaxys; Patent; ARYX THERAPEUTICS; WO2007/5951; (2007); (A2) English, View in Reaxys; Patent; Dai, Han; Riera, Thomas V.; Stein, Ross L.; Szczepankiewicz, Bruce; US2013/102009; (2013); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human erythrocytes

Method (Pharmacological Data)

acetylcholinesterase activity tested; acetylcholine used as a substrate; phosphate buffer, pH 7.4; 37 deg C; quantified by Ellman spectrophotometric method using DTNB as thiol reagent; recorded for 3 min starting 30 s after reagent mixing

Further Details (Pharmacological Data)

KSS: dissociation constant of enzyme-substrate complex when 2 molecules of substrate were bound to enzyme

Results

Ki: 8.3 mmol*dm-3; KSS: 2.5 mmol*dm-3; Ka: 2.6 mmol*dm-3; KM: O.31 mmol*dm-3

Bosak, Anita; Primozic, Ines; Orsulic, Mislav; Tomic, Srdanka; Simeon-Rudolf, Vera; Croatica Chemica Acta; vol. 78; nb. 1; (2005); p. 121 - 128, View in Reaxys 3 of 3

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human plasma

Method (Pharmacological Data)

butyrylcholinesterase activity tested; acetylcholine used as a substrate; phosphate buffer, pH 7.4; 37 deg C; quantified by Ellman spectrophotometric method using DTNB as thiol reagent; recorded for 3 min starting 30 s after reagent mixing

Further Details (Pharmacological Data)

KSS: dissociation constant of enzyme-substrate complex when 2 molecules of substrate were bound to enzyme

Results

Ki: 17 mmol*dm-3; KSS: 2.2 mmol*dm-3; Ka: 3.3 mmol*dm-3; KM: O.17 mmol*dm-3

Bosak, Anita; Primozic, Ines; Orsulic, Mislav; Tomic, Srdanka; Simeon-Rudolf, Vera; Croatica Chemica Acta; vol. 78; nb. 1; (2005); p. 121 - 128, View in Reaxys

Reaxys ID 4754592 View in Reaxys

5/39 CAS Registry Number: 6238-13-7 Chemical Name: 3-RS-quinuclidinol hydrochloride; 3-quinuclidinol hydrochloride; (+/-)-1-azabicyclo[2.2.2]octane-3-ol hydrochloride; 3-hydroxyquinuclidine hydrochloride; (+/-)-3-Quinuclidinol; (+-)-quinuclidin-3-ol; hydrochloride; (+-)-Chinuclidin-3-ol; Hydrochlorid Linear Structure Formula: C7H13NO*ClH Molecular Formula: C7H13NO*ClH Molecular Weight: 163.647

HO Cl

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Type of Substance: heterocyclic InChI Key: OYEJRVVBERZWPD-UHFFFAOYSA-N Note: Substance Label (2) Label References 6

Arias-Perez; Cosme; Galvez; Santos; Martinez-Ripoll; Matesanz; Journal of Molecular Structure; vol. 565-566; (2001); p. 353 - 360, View in Reaxys

3-OH-Q*HCl

Berg, Ulf; Jencks, William P.; Journal of the American Chemical Society; vol. 113; nb. 18; (1991); p. 6997 7002, View in Reaxys

Melting Point (1) 1 of 1

Solvent (Melting Point)

methanol; acetone

Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys Electrochemical Behaviour (1) Description (Elec- References trochemical Behaviour) Kinetics of dissociation (electrolytic) / protonation

Berg, Ulf; Jencks, William P.; Journal of the American Chemical Society; vol. 113; nb. 18; (1991); p. 6997 7002, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Arias-Perez; Cosme; Galvez; Santos; Martinez-Ripoll; Matesanz; Journal of Molecular Structure; vol. 565-566; (2001); p. 353 - 360, View in Reaxys 2 of 2

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Arias-Perez; Cosme; Galvez; Santos; Martinez-Ripoll; Matesanz; Journal of Molecular Structure; vol. 565-566; (2001); p. 353 - 360, View in Reaxys

Reaxys ID 6174405 View in Reaxys

6/39 CAS Registry Number: 25333-42-0 Chemical Name: (R)-1-azabicyclo[2.2.2]octan-3-ol; (R)-(-)-3quinuclidinol; (R)-3-quinuclidinol; (R)-quinuclidinol; 3-quinuclidinol; (3R)-(-)-quinuclidin-3-ol; (3R)-1-azabicyclo[2.2.2]octan-3-ol Linear Structure Formula: C7H13NO Molecular Formula: C7H13NO Molecular Weight: 127.186 Type of Substance: heterocyclic InChI Key: IVLICPVPXWEGCA-ZETCQYMHSA-N Note:

Substance Label (2) Label References II

Kolet, Swati P.; Jadhav, Dipesh D.; Priyadarshini, Balaraman; Swarge, Bhagyashree N.; Thulasiram, Hirekodathakallu V.; Tetrahedron Letters; vol. 55; nb. 43; (2014); p. 5911 - 5914, View in Reaxys

Strobl; Von Kruedener; Stockigt; Guengerich; Wolff; Journal of Medicinal Chemistry; vol. 36; nb. 9; (1993); p. 1136 - 1145, View in Reaxys

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Melting Point (2) 1 of 2

Melting Point [°C]

220

Kolet, Swati P.; Jadhav, Dipesh D.; Priyadarshini, Balaraman; Swarge, Bhagyashree N.; Thulasiram, Hirekodathakallu V.; Tetrahedron Letters; vol. 55; nb. 43; (2014); p. 5911 - 5914, View in Reaxys 2 of 2

Melting Point [°C]

223 - 224

Solvent (Melting Point)

ethyl acetate; ethanol

Arai, Noriyoshi; Kurono, Nobuhito; Ohkuma, Takeshi; Tsutsumi, Kunihiko; Katayama, Takeaki; Utsumi, Noriyuki; Murata, Kunihiko; Organic Process Research and Development; vol. 13; nb. 3; (2009); p. 625 - 628, View in Reaxys Chromatographic Data (1) Chromatographic References data GC (Gas chroma- Kolet, Swati P.; Jadhav, Dipesh D.; Priyadarshini, Balaraman; Swarge, Bhagyashree N.; Thulasiram, tography) Hirekodathakallu V.; Tetrahedron Letters; vol. 55; nb. 43; (2014); p. 5911 - 5914, View in Reaxys Crystal Property Description (2) Colour & Other References Properties white

Kolet, Swati P.; Jadhav, Dipesh D.; Priyadarshini, Balaraman; Swarge, Bhagyashree N.; Thulasiram, Hirekodathakallu V.; Tetrahedron Letters; vol. 55; nb. 43; (2014); p. 5911 - 5914, View in Reaxys

white

Patent; Schrimpf, Michael R.; Sippy, Kevin B.; Ji, Jianguo; Li, Tao; Frost, Jennifer M.; Briggs, Clark A.; Bunnelle, William H.; US2005/234031; (2005); (A1) English, View in Reaxys

Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2 g/100ml

Enantiomeric excess [%ee]

Solvent (Optical Rotatory Power)

hydrogenchloride; water

Optical Rotatory Power [deg]

-44.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Kolet, Swati P.; Jadhav, Dipesh D.; Priyadarshini, Balaraman; Swarge, Bhagyashree N.; Thulasiram, Hirekodathakallu V.; Tetrahedron Letters; vol. 55; nb. 43; (2014); p. 5911 - 5914, View in Reaxys 2 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.90 g/100ml

Solvent (Optical Rotatory Power)

acidic aq. solution

Optical Rotatory Power [deg]

-46.1

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

43/60

2016-04-25 15:32:22

1 of 1

Comment (Solubility (MCS))

soluble in water

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

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

500

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

13C

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

125.8

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

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

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

13C

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy)

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Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (300 MHz, methanol-d4) δ 3.88-3.82 (1H, m), 3.10 (1H, ddd, J=14, 8, 2 Hz), 2.95-2.50 (5H, m), 2.05-1.90 (1H, m), 1.85-1.76 (2H, m), 1.60-1.52 (1H, m), 1.50-1.36 (1H, m).

Patent; Schrimpf, Michael R.; Sippy, Kevin B.; Ji, Jianguo; Li, Tao; Frost, Jennifer M.; Briggs, Clark A.; Bunnelle, William H.; US2005/234031; (2005); (A1) English, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

References

electron impact (EI); spectrum

Kolet, Swati P.; Jadhav, Dipesh D.; Priyadarshini, Balaraman; Swarge, Bhagyashree N.; Thulasiram, Hirekodathakallu V.; Tetrahedron Letters; vol. 55; nb. 43; (2014); p. 5911 - 5914, View in Reaxys

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Kolet, Swati P.; Jadhav, Dipesh D.; Priyadarshini, Balaraman; Swarge, Bhagyashree N.; Thulasiram, Hirekodathakallu V.; Tetrahedron Letters; vol. 55; nb. 43; (2014); p. 5911 - 5914, View in Reaxys

DCI (Desorption chemical ionization)

Molecular peak

Patent; Schrimpf, Michael R.; Sippy, Kevin B.; Ji, Jianguo; Li, Tao; Frost, Jennifer M.; Briggs, Clark A.; Bunnelle, William H.; US2005/234031; (2005); (A1) English, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Strobl; Von Kruedener; Stockigt; Guengerich; Wolff; Journal of Medicinal Chemistry; vol. 36; nb. 9; (1993); p. 1136 - 1145, View in Reaxys; Kiesewetter; Tetrahedron Asymmetry; vol. 4; nb. 10; (1993); p. 2183 - 2198, View in Reaxys; Jiang, Xiao-Bin; Lefort, Laurent; Goudriaan, P. Elsbeth; De Vries, Andre H. M.; Van Leeuwen, Piet W. N. M.; De Vries, Johannes G.; Reek, Joost N. H.; Angewandte Chemie - International Edition; vol. 45; nb. 8; (2006); p. 1223 - 1227, View in Reaxys; Patent; Schrimpf, Michael R.; Sippy, Kevin B.; Ji, Jianguo; Li, Tao; Frost, Jennifer M.; Briggs, Clark A.; Bunnelle, William H.; US2005/234031; (2005); (A1) English, View in Reaxys; Arai, Noriyoshi; Kurono, Nobuhito; Ohkuma, Takeshi; Tsutsumi, Kunihiko; Katayama, Takeaki; Utsumi, Noriyuki; Murata, Kunihiko; Organic Process Research and Development; vol. 13; nb. 3; (2009); p. 625 - 628, View in Reaxys; Kolet, Swati P.; Jadhav, Dipesh D.; Priyadarshini, Balaraman; Swarge, Bhagyashree N.; Thulasiram, Hirekodathakallu V.; Tetrahedron Letters; vol. 55; nb. 43; (2014); p. 5911 - 5914, View in Reaxys 2 of 2

Comment (Pharmacological Data)

inhibition of bufuralol 1'-hydroxylation by human liver microsomes

Strobl; Von Kruedener; Stockigt; Guengerich; Wolff; Journal of Medicinal Chemistry; vol. 36; nb. 9; (1993); p. 1136 - 1145, View in Reaxys

Reaxys ID 4654229 View in Reaxys

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CAS Registry Number: 34583-34-1 Chemical Name: 3-quinuclidinol; S-quinuclidinol; (S)-(-)-quinuclidin-3-ol Linear Structure Formula: C7H13NO Molecular Formula: C7H13NO Molecular Weight: 127.186 Type of Substance: heterocyclic InChI Key: IVLICPVPXWEGCA-SSDOTTSWSA-N Note:

Substance Label (2) Label References 3

Dolle, Frederic; Hinnen, Francoise; Vaufrey, Francoise; Demphel, Stephane; Bramoulle, Yann; Fournier, Denis; Ponchant, Michel; Valette, Heric; Crouzel, Christian; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 44; nb. 5; (2001); p. 337 - 345, View in Reaxys

(16)

Fleet; James; Lunn; Tetrahedron Letters; vol. 27; nb. 26; (1986); p. 3053 - 3056, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.23 g/100ml

Solvent (Optical Rotatory Power)

HCl; H2O

Optical Rotatory Power [deg]

35.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Comment (Optical Rota- Ratio of solvents: 1 N tory Power) Fleet; James; Lunn; Tetrahedron Letters; vol. 27; nb. 26; (1986); p. 3053 - 3056, View in Reaxys

Reaxys ID 4958105 View in Reaxys

8/39 Chemical Name: 3-quinuclidinol-H+ Linear Structure Formula: C7H14NO(1+) Molecular Formula: C7H13NO*H Molecular Weight: 128.194 Type of Substance: heterocyclic InChI Key: IVLICPVPXWEGCA-UHFFFAOYSA-O Note:

HO H+ N

Dissociation Exponent (6) 1 of 6

Dissociation Exponent (pK)

9.7

Dissociation Group

N(1+)-H

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O; ethanol

Method (Dissociation Exponent)

spectrophotometric

Type (Dissociation Exponent)

a1/apparent

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Comment (Dissociation Exponent)

Ratio of solvents: 44 wt percent EtOH/H2O

Castro, Enrique A.; Andujar, Monica; Toro, Alejandra; Santos, Jose G.; Journal of Organic Chemistry; vol. 68; nb. 9; (2003); p. 3608 - 3613, View in Reaxys 2 of 6

Dissociation Exponent (pK)

9.8

Dissociation Group

N-H

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Method (Dissociation Exponent)

kinetics

Type (Dissociation Exponent)

a1/apparent

Castro, Enrique A.; Aliaga, Margarita; Campodonico, Paola; Santos, Jose G.; Journal of Organic Chemistry; vol. 67; nb. 25; (2002); p. 8911 - 8916, View in Reaxys 3 of 6

Dissociation Exponent (pK)

10.1

Dissociation Group

N-H

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Type (Dissociation Exponent)

a1/apparent

Antelo, Juan M.; Crugeiras, Juan; Leis, J. Ramon; Rios, Ana; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (2000); p. 2071 - 2076, View in Reaxys 4 of 6

Dissociation Exponent (pK)

10.1

Dissociation Group

N-H

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Type (Dissociation Exponent)

a1/apparent

Antelo, Juan M.; Crugeiras, Juan; Leis, J. Ramon; Rios, Ana; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (2000); p. 2071 - 2076, View in Reaxys 5 of 6

Dissociation Exponent (pK)

10.1

Dissociation Group

N-H

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Type (Dissociation Exponent)

a1/apparent

Antelo, Juan M.; Crugeiras, Juan; Leis, J. Ramon; Rios, Ana; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (2000); p. 2071 - 2076, View in Reaxys 6 of 6

Dissociation Exponent (pK)

10.1

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Dissociation Group

N-H(+)

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Type (Dissociation Exponent)

a1/thermodynamic

Emly, Mark; Leussing, Daniel L.; Journal of the American Chemical Society; vol. 103; nb. 3; (1981); p. 628 - 634, View in Reaxys Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Emly, Mark; Leussing, Daniel L.; Journal of the American Chemical Society; vol. 103; nb. 3; (1981); p. 628 - 634, View in Reaxys; Antelo, Juan M.; Crugeiras, Juan; Leis, J. Ramon; Rios, Ana; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (2000); p. 2071 - 2076, View in Reaxys; Castro, Enrique A.; Aliaga, Margarita; Campodonico, Paola; Santos, Jose G.; Journal of Organic Chemistry; vol. 67; nb. 25; (2002); p. 8911 - 8916, View in Reaxys; Castro, Enrique A.; Andujar, Monica; Toro, Alejandra; Santos, Jose G.; Journal of Organic Chemistry; vol. 68; nb. 9; (2003); p. 3608 - 3613, View in Reaxys; Geldenhuys, Werner J.; Allen, David D.; Lockman, Paul R.; Bioorganic and Medicinal Chemistry Letters; vol. 20; nb. 16; (2010); p. 4870 - 4877, View in Reaxys

Reaxys ID 7444967 View in Reaxys

9/39 Chemical Name: sodium (R)-quinuclidin-3-ol; (R)-3-quinuclidinol sodium salt; sodium (R)-3-quinuclidinol Linear Structure Formula: C7H12NO(1-)*Na(1+) Molecular Formula: C7H12NO*Na Molecular Weight: 149.168 Type of Substance: heterocyclic InChI Key: VERNWZIDFSZOOY-FJXQXJEOSA-N Note:

–O

Na + N

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

Patent; CADILA HEALTHCARE LIMITED; WO2009/87664; (2009); (A1) English, View in Reaxys

Reaxys ID 3619273 View in Reaxys

10/39 CAS Registry Number: 603126-48-3 Chemical Name: (S)-quinuclidin-3-ol hydrochloride; (R)-(-)-3quinuclidinol hydrochloride Linear Structure Formula: C7H13NO*ClH Molecular Formula: C7H13NO*ClH Molecular Weight: 163.647 Type of Substance: heterocyclic InChI Key: OYEJRVVBERZWPD-OGFXRTJISA-N Note:

HO Cl

Substance Label (2) Label References (S)-QOH

Bosak, Anita; Primozic, Ines; Orsulic, Mislav; Tomic, Srdanka; Simeon-Rudolf, Vera; Croatica Chemica Acta; vol. 78; nb. 1; (2005); p. 121 - 128, View in Reaxys

Optical Rotatory Power (1)

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1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3.25 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

47.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Comment (Pharmacological Data)

Bioactivities present

Patent; Mammen, Mathai; Dunham, Sarah; Hughes, Adam; Lee, Tae Weon; Husfeld, Cralg; Stangeland, Eric; US2004/167167; (2004); (A1) English, View in Reaxys; Esikova, I. A.; Serebryakov, E. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 8.2; (1989); p. 1682 1690; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 8; (1989); p. 1836 - 1843, View in Reaxys; Bosak, Anita; Primozic, Ines; Orsulic, Mislav; Tomic, Srdanka; Simeon-Rudolf, Vera; Croatica Chemica Acta; vol. 78; nb. 1; (2005); p. 121 - 128, View in Reaxys 2 of 3

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human erythrocytes

Method (Pharmacological Data)

Further Details (Pharmacological Data)

KSS: dissociation constant of enzyme-substrate complex when 2 molecules of substrate were bound to enzyme

Results

Ki: 8.5 mmol*dm-3; KSS: 4.1 mmol*dm-3; Ka: 4.8 mmol*dm-3; KM: O.69 mmol*dm-3

Bosak, Anita; Primozic, Ines; Orsulic, Mislav; Tomic, Srdanka; Simeon-Rudolf, Vera; Croatica Chemica Acta; vol. 78; nb. 1; (2005); p. 121 - 128, View in Reaxys 3 of 3

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human plasma

Method (Pharmacological Data)

Further Details (Pharmacological Data)

KSS: dissociation constant of enzyme-substrate complex when 2 molecules of substrate were bound to enzyme

Results

Ki: 18 mmol*dm-3; KSS: 1.5 mmol*dm-3; Ka: 2.9 mmol*dm-3; KM: O.11 mmol*dm-3

Bosak, Anita; Primozic, Ines; Orsulic, Mislav; Tomic, Srdanka; Simeon-Rudolf, Vera; Croatica Chemica Acta; vol. 78; nb. 1; (2005); p. 121 - 128, View in Reaxys

Reaxys ID 5470078 View in Reaxys

11/39

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CAS Registry Number: 100611-34-5 Chemical Name: (+-)-quinuclidin-3-ol; picrate; (+-)-Chinuclidin-3-ol; Picrat Linear Structure Formula: C7H13NO*C6H3N3O7 Molecular Formula: C6H3N3O7*C7H13NO Molecular Weight: 356.292 Type of Substance: heterocyclic InChI Key: KKZWJQSSARMOSD-UHFFFAOYSA-N Note:

O O

O HO

N O

Melting Point (2) 1 of 2

Melting Point [°C]

214

Solvent (Melting Point)

ethanol

Grob et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 2170,2176, View in Reaxys 2 of 2

Melting Point [°C]

212 - 214

Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys Crystal Property Description (1) Colour & Other References Properties gelb

Grob et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 2170,2176, View in Reaxys

Reaxys ID 7229109 View in Reaxys

12/39 Linear Structure Formula: C7H12NO(1-)*Li(1+) Molecular Formula: C7H12NO*Li Molecular Weight: 133.119 Type of Substance: heterocyclic InChI Key: SDALWGHOVDXNDQ-UHFFFAOYSA-N Note:

–O

Li+ N

Reaxys ID 10133916 View in Reaxys

13/39 C7H14NO(1+)*BF4 (1-)

Linear Structure Formula: Molecular Formula: BF4*C7H13NO*H Molecular Weight: 214.999 Type of Substance: heterocyclic InChI Key: WIAJXKKPYZGLQQ-UHFFFAOYSA-O Note:

-1 F H + HO

(v4)

B F F

Substance Label (1) Label References 3-OHQD*HBF4

Aggarwal, Varinder K.; Emme, Ingo; Fulford, Sarah Y.; Journal of Organic Chemistry; vol. 68; nb. 3; (2003); p. 692 - 700, View in Reaxys

NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- dimethylsulfoxide scopy) Temperature (NMR Spectroscopy) [°C]

Aggarwal, Varinder K.; Emme, Ingo; Fulford, Sarah Y.; Journal of Organic Chemistry; vol. 68; nb. 3; (2003); p. 692 - 700, View in Reaxys

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Reaxys ID 1446411 View in Reaxys

14/39 CAS Registry Number: 33513-70-1 Chemical Name: 3-Deutero-3-hydroxy-1-azabicyclo<2.2.2>octan; 3-Deutero-3-hydroxy-1-azabicyclo[2.2.2]octan Linear Structure Formula: C7H12DNO Molecular Formula: C7H13NO Molecular Weight: 128.178 Type of Substance: heterocyclic InChI Key: IVLICPVPXWEGCA-WHRKIXHSSA-N Note:

HO 2H

Substance Label (1) Label References VIII

Palecek; Collection of Czechoslovak Chemical Communications; vol. 36; (1971); p. 2070, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

231 - 232

Palecek; Collection of Czechoslovak Chemical Communications; vol. 36; (1971); p. 2070, View in Reaxys

Reaxys ID 1616425 View in Reaxys

15/39 CAS Registry Number: 1619-34-7 Chemical Name: 3-Chinuclidinol Linear Structure Formula: C7H13NO Molecular Formula: C7H13NO Molecular Weight: 127.186 Type of Substance: heterocyclic InChI Key: IVLICPVPXWEGCA-UHFFFAOYSA-N Note:

Dissociation Exponent (1) 1 of 1

Comment (Dissociation Exponent)

(pk')pK

Gresser,M.J.; Jencks,W.P.; Journal of the American Chemical Society; vol. 99; nb. 21; (1977); p. 6963 - 6970, View in Reaxys

Reaxys ID 4735210 View in Reaxys

16/39 CAS Registry Number: 149689-53-2 Chemical Name: 1-aza-bicyclo[2.2.2]octan-3-ol; sodium salt Linear Structure Formula: C7H12NO(1-)*Na(1+) Molecular Formula: C7H12NO*Na Molecular Weight: 149.168 Type of Substance: heterocyclic InChI Key: VERNWZIDFSZOOY-UHFFFAOYSA-N Note:

–

O Na + N

Reaxys ID 5198711 View in Reaxys

17/39 CAS Registry Number: 88341-13-3 Chemical Name: quinuclidin-3-ol*dichlone (1:1) complex Linear Structure Formula: C10H4Cl2O2*C7H13NO Molecular Formula: C7H13NO*C10H4Cl2O2 Molecular Weight: 354.233 Type of Substance: heterocyclic InChI Key: YUZVPDOYVFNDPU-UHFFFAOYSA-N

O HO

N O

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Note:

Reaxys ID 5964884 View in Reaxys

18/39 Chemical Name: 3-Hydroxyquinuclidine hydroiodid Linear Structure Formula: C7H13NO*HI Molecular Formula: C7H13NO*HI Molecular Weight: 255.099 Type of Substance: heterocyclic InChI Key: FCTSVQKVBRUULV-UHFFFAOYSA-N Note:

HO I

Dissociation Exponent (1) 1 of 1

Dissociation Exponent (pK)

-1

Dissociation Group

NH(1+)

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

aq. KOH

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a1/apparent

Lambrecht; Archiv der Pharmazie; vol. 315; nb. 7; (1982); p. 646 - 651, View in Reaxys

Reaxys ID 6122056 View in Reaxys

19/39 CAS Registry Number: 59653-88-2 Chemical Name: (S)-quinuclidin-3-ol; (1S)-2-oxo-bornane-10sulfonate; (S)-Chinuclidin-3-ol; (1S)-2-Oxo-bornan-10-sulfonat Linear Structure Formula: C10H16O4S*C7H13NO Molecular Formula: C7H13NO*C10H16O4S Molecular Weight: 359.487 Type of Substance: heterocyclic InChI Key: RMNDGNWCJSXTAG-QHZLGHJSSA-N Note:

HO O O N

S HO

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

c=7

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys

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Reaxys ID 6122057 View in Reaxys

20/39 CAS Registry Number: 59653-88-2 Chemical Name: (R)-quinuclidin-3-ol; (1S)-2-oxo-bornane-10sulfonate; (R)-Chinuclidin-3-ol; (1S)-2-Oxo-bornan-10-sulfonat Linear Structure Formula: C10H16O4S*C7H13NO Molecular Formula: C7H13NO*C10H16O4S Molecular Weight: 359.487 Type of Substance: heterocyclic InChI Key: RMNDGNWCJSXTAG-VVSVFQIHSA-N Note:

HO O O N

S HO

Melting Point (1) 1 of 1

Melting Point [°C]

260

Solvent (Melting Point)

propan-2-ol; acetone

Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

c=7

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-0.3

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Sternbach; Kaiser; Journal of the American Chemical Society; vol. 74; (1952); p. 2219, View in Reaxys

Reaxys ID 6252550 View in Reaxys

21/39 Linear Structure Formula: C7H12NO(1-)*BH3*Na(1+) Molecular Formula: BH3*C7H12NO*Na Molecular Weight: 163.003 Type of Substance: heterocyclic InChI Key: KAPZNVFLYKTRPZ-XCUBXKJBSA-N Note:

–O

Na +

H N

racemate

Substance Label (1) Label References 3

Stotter, Philip L.; Friedman, Martin D.; Dorsey, Gordon O.; Shiely, Robert W.; Williams, Robert F.; Minter, David E.; Heterocycles; vol. 25; (1987); p. 251 - 258, View in Reaxys

Reaxys ID 7155738 View in Reaxys

22/39

OH OH

2 HO N

Chemical Name: S(+)-3-Quinuclidinol bis-R,R(+)-tartrate Linear Structure Formula: C7H13NO*2C4H6O6 Molecular Formula: 2C4H6O6*C7H13NO Molecular Weight: 427.362 Type of Substance: heterocyclic InChI Key: WFANBEJSDAYBHS-FJXQXJEOSA-N Note:

Density (1)

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1 of 1

Density [g·cm-3]

1.52

Type (Density)

crystallographic

Erman, L. Ya.; Mindrul, V. F.; Mikhaleva, I. L.; Pankov, D. I.; Kurochkin, V. K.; Journal of Structural Chemistry; vol. 35; nb. 3; (1994); p. 418 - 421; Zhurnal Strukturnoi Khimii; vol. 35; nb. 3; (1994); p. 161 - 164, View in Reaxys Crystal Phase (1) Description (Crys- Comment (Crystal References tal Phase) Phase) Crystal structure determination

β=101.2 grad, a=7.46 Angstroem, b=16.04 Angstroem, c=7.76 Angstroem, n=2.; Method of determination: Single Crystal X-ray Diffraction

Crystal System (1) Crystal System References monoclinic

Interatomic Distances and Angles (1) Description References Interatomic distances and angles

Space Group (1) Space Group

References

Reaxys ID 7561586 View in Reaxys

23/39 Chemical Name: 3-hydroxy-azabicyclo[2.2.2]octane pentachlorophenolate monohydrate Linear Structure Formula: C7H13NO*C6HCl5O*H2O Molecular Formula: C6HCl5O*C7H13NO*H2O Molecular Weight: 411.54 Type of Substance: heterocyclic InChI Key: MZRIMQXGVQAZJI-UHFFFAOYSA-N Note:

Cl Cl

Density (1) 1 of 1

Density [g·cm-3]

1.68

Type (Density)

crystallographic

Sawka-Dobrowolska; Malarski; Grech; Polish Journal of Chemistry; vol. 70; nb. 8; (1996); p. 1036 - 1042, View in Reaxys Crystal Phase (1) Description (Crys- Comment (Crystal References tal Phase) Phase) Crystal structure determination

α=68.3 grad, β=72.5 grad, χ=85.4 grad, a=7.71 Angstroem, b=10.69 Angstroem,

Sawka-Dobrowolska; Malarski; Grech; Polish Journal of Chemistry; vol. 70; nb. 8; (1996); p. 1036 - 1042, View in Reaxys

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c=11.18 Angstroem, n=2.; Temperature: 292 K. Method of determination: Single Crystal X-ray Diffraction Crystal System (1) Crystal System References triclinic

Sawka-Dobrowolska; Malarski; Grech; Polish Journal of Chemistry; vol. 70; nb. 8; (1996); p. 1036 - 1042, View in Reaxys

Interatomic Distances and Angles (1) Description References Interatomic distances and angles Space Group (1) Space Group 2

Sawka-Dobrowolska; Malarski; Grech; Polish Journal of Chemistry; vol. 70; nb. 8; (1996); p. 1036 - 1042, View in Reaxys

References Sawka-Dobrowolska; Malarski; Grech; Polish Journal of Chemistry; vol. 70; nb. 8; (1996); p. 1036 - 1042, View in Reaxys

IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

various solvent(s)

Comment (IR Spectroscopy)

4000 - 400 cm**(-1)

Sawka-Dobrowolska; Malarski; Grech; Polish Journal of Chemistry; vol. 70; nb. 8; (1996); p. 1036 - 1042, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

various solvent(s)

Comment (IR Spectroscopy)

3404 - 472 cm**(-1)

Sawka-Dobrowolska; Malarski; Grech; Polish Journal of Chemistry; vol. 70; nb. 8; (1996); p. 1036 - 1042, View in Reaxys

Reaxys ID 8168584 View in Reaxys

24/39 Chemical Name: S-(+)-3-quinuclidinol Linear Structure Formula: C7H12NO(1-)*Na(1+) Molecular Formula: C7H12NO*Na Molecular Weight: 149.168 Type of Substance: heterocyclic InChI Key: VERNWZIDFSZOOY-OGFXRTJISA-N Note:

–O

Na + N

Reaxys ID 8168585 View in Reaxys

25/39

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Chemical Name: R-(-)-3-quinuclidinol Linear Structure Formula: C7H12NO(1-)*Na(1+) Molecular Formula: C7H12NO*Na Molecular Weight: 149.168 Type of Substance: heterocyclic InChI Key: VERNWZIDFSZOOY-FJXQXJEOSA-N Note:

–O

Na + N

Reaxys ID 8261132 View in Reaxys

26/39 Chemical Name: (+)-quinuclidin-3-ol Linear Structure Formula: C7H13NO Molecular Formula: C7H13NO Molecular Weight: 127.186 Type of Substance: heterocyclic InChI Key: IVLICPVPXWEGCA-UHFFFAOYSA-N Note:

N (+)-enantiomer

Substance Label (1) Label References 11b

Reaxys ID 8263124 View in Reaxys

27/39 Chemical Name: (-)-quinuclidin-3-ol Linear Structure Formula: C7H13NO Molecular Formula: C7H13NO Molecular Weight: 127.186 Type of Substance: heterocyclic InChI Key: IVLICPVPXWEGCA-UHFFFAOYSA-N Note:

N (-)-enantiomer

Substance Label (1) Label References 11c

Reaxys ID 9793922 View in Reaxys

H N

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Linear Structure Formula: C7H13NO*BH3 Molecular Formula: BH3*C7H13NO Molecular Weight: 141.021 Type of Substance: heterocyclic InChI Key: NKYGDFFHJHHYDJ-UHFFFAOYSA-N Note:

Substance Label (1) Label References 6

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Reaxys ID 13513267 View in Reaxys

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HO HO

Chemical Name: quinuclidinol methylcarbamate Linear Structure Formula: C2H5NO2*C7H13NO Molecular Formula: C2H5NO2*C7H13NO Molecular Weight: 202.254 InChI Key: SKRLVRNICSZULE-UHFFFAOYSA-N Note:

H N

Reaxys ID 14414158 View in Reaxys

30/39 Chemical Name: (3S)-1-azabicyclo[2.2.2]oct-3-yl benzoate (D)tartrate Linear Structure Formula: C4H6O6*C7H13NO Molecular Formula: C4H6O6*C7H13NO Molecular Weight: 277.274 InChI Key: WFANBEJSDAYBHS-DOIQAPIBSA-N Note:

OH OH

HO N

Reaxys ID 14482325 View in Reaxys

31/39 CAS Registry Number: 1619-34-7 Chemical Name: 3-quinuclidinol Linear Structure Formula: C7H13NO Molecular Formula: C7H13NO Molecular Weight: 127.186 InChI Key: IVLICPVPXWEGCA-UHFFFAOYSA-N Note:

H HO

Reaxys ID 14482326 View in Reaxys

32/39 CAS Registry Number: 42437-96-7 Chemical Name: (R)-3-quinuclidinol hydrochloride Linear Structure Formula: C7H13NO*ClH Molecular Formula: C7H13NO*ClH Molecular Weight: 163.647 InChI Key: OYEJRVVBERZWPD-FJXQXJEOSA-N Note:

H HO HCl N

Reaxys ID 19887020 View in Reaxys

33/39 CAS Registry Number: 1200405-02-2 Chemical Name: (S)-quinuclidin-3-ol butyric acid salt Linear Structure Formula: C4H8O2*C7H13NO Molecular Formula: C4H8O2*C7H13NO Molecular Weight: 215.293 InChI Key: JOOSPPIDADSLCT-OGFXRTJISA-N Note:

O N

Reaxys ID 24055020 View in Reaxys

34/39

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H+

Linear Structure Formula: C7H14NO(1+)*F6P(1-) Molecular Formula: C7H13NO*F6P*H Molecular Weight: 273.158 InChI Key: SCRFFVKAZNLHEN-UHFFFAOYSA-O Note:

P–

F F

Reaxys ID 24570620 View in Reaxys

35/39 Chemical Name: 3-S-quinuclidinol; 1-azabicyclo[2.2.2]octan-3ol Linear Structure Formula: C7H13NO Molecular Formula: C7H13NO Molecular Weight: 127.186 InChI Key: IVLICPVPXWEGCA-SSDOTTSWSA-N Note:

H HO

Substance Label (1) Label References 2

Bjorsvik, Hans-Rene; Liguori, Lucia; Costantino, Francesca; Minisci, Francesco; Organic Process Research and Development; vol. 6; nb. 2; (2002); p. 197 - 200, View in Reaxys

Reaxys ID 25451821 View in Reaxys O HO

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OHO

OH O

O OH

P O

OH P O

O HO

O OHO

Linear Structure Formula: C6H18O24P6*C7H13NO*H(1+) Molecular Formula: C6H18O24P6*C7H13NO*H Molecular Weight: 788.231 InChI Key: LBAHMGJHDGIJHY-UHFFFAOYSA-O Note:

O P

H+

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Vincent, Stephane P; Lehn, Jean-Marie; Lazarte, Jaime; Nicolau, Claude; Bioorganic and medicinal chemistry; vol. 10; nb. 9; (2002); p. 2825 - 2834, View in Reaxys

Reaxys ID 26756784 View in Reaxys

37/39

HO N

Linear Structure Formula: C7H13NO*C18H14O8 Molecular Formula: C7H13NO*C18H14O8 Molecular Weight: 485.491 InChI Key: ULELISQAMBVLDR-WWTMQREUSA-N Note: OH

Melting Point (1)

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1 of 1

Melting Point [°C]

174 - 178

Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Chavakula, Ramadas; Mutyala, Narayana Rao; Chennupati, Srinivasa Rao; Organic Preparations and Procedures International; vol. 45; nb. 6; (2013); p. 507 - 509, View in Reaxys

Reaxys ID 27373799 View in Reaxys

38/39 Linear Structure Formula: C14H9NO4*C7H13NO*1.5H2O Molecular Formula: C7H13NO*C14H9NO4*H2O Molecular Weight: 409.439 InChI Key: XMWABALHVPGGMJ-UHFFFAOYSA-N Note:

HO O

1.5H O 2

N OH O

Substance Label (1) Label References 3

D'Agostino, Simone; Grepioni, Fabrizia; Braga, Dario; Moreschi, Daniele; Fattori, Valeria; Delchiaro, Francesca; Di Motta, Simone; Negri, Fabrizia; CrystEngComm; vol. 15; nb. 48; (2013); p. 10470 - 10480, View in Reaxys

Crystal Phase (3) Description (Crys- References tal Phase) Structure of the solid

Crystal growth

Interplanar spacing

Space Group (1) Comment (Space Group)

References

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Method = Single crystal X-ray diffraction

Reaxys ID 27373805 View in Reaxys

39/39 Linear Structure Formula: C14H9NO4*C7H13NO Molecular Formula: C7H13NO*C14H9NO4 Molecular Weight: 382.416 InChI Key: YSHAGDOSKFVPEH-UHFFFAOYSA-N Note:

O OH

Substance Label (1) Label References 3

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

Fluorescence Spectroscopy (1) Description (Fluo- References rescence Spectroscopy) Maxima; Spectrum; Fluorescence quantum yield

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