WO2008100651A3 - Préparation de darifénacine et ses sels - Google Patents
Préparation de darifénacine et ses sels Download PDFInfo
- Publication number
- WO2008100651A3 WO2008100651A3 PCT/US2008/050388 US2008050388W WO2008100651A3 WO 2008100651 A3 WO2008100651 A3 WO 2008100651A3 US 2008050388 W US2008050388 W US 2008050388W WO 2008100651 A3 WO2008100651 A3 WO 2008100651A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- darifenacin
- salts
- reaction
- salt
- Prior art date
Links
- HXGBXQDTNZMWGS-RUZDIDTESA-N darifenacin Chemical compound C=1C=CC=CC=1C([C@H]1CN(CCC=2C=C3CCOC3=CC=2)CC1)(C(=O)N)C1=CC=CC=C1 HXGBXQDTNZMWGS-RUZDIDTESA-N 0.000 title abstract 4
- 229960002677 darifenacin Drugs 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- RISTUVDQGDQPPP-AREMUKBSSA-N 2-[(3s)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C([C@H]1CN(CCC=2C=C3CCOC3=CC=2)CC1)(C#N)C1=CC=CC=C1 RISTUVDQGDQPPP-AREMUKBSSA-N 0.000 abstract 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical group CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002560 nitrile group Chemical group 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
L'invention concerne plusieurs procédés et composés associés à la darifénacine et/ou à ses sels. L'invention concerne par exemple un procédé de préparation d'une base libre de darifénacine : Formule ou de son sel. Le procédé comprend la mise en réaction de la 3-(S)-(cyanodiphénylméthyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)éthyl] pyrrolidine de formule (IV) ou un de ses sels : Formule (IV) avec une base efficace pour transformer le groupement nitrile du composé de formule (IV) en groupement amide de la darifénacine dans un solvant organique, à condition que le solvant ne soit pas le 2-méthyl-butan-2-ol et que la réaction produise une quantité inférieure à environ 0,5 % du composé de formule (Ic) : Formule (Ic) dans la masse réactionnelle, telle que mesurée par HPLC. L'invention concerne également plusieurs modes de réalisation et plusieurs variantes.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08772573A EP2109601A2 (fr) | 2007-01-05 | 2008-01-07 | Préparation de darifénacine et ses sels |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN34/CHE/2007 | 2007-01-05 | ||
IN34CH2007 | 2007-01-05 | ||
US89471107P | 2007-03-14 | 2007-03-14 | |
US60/894,711 | 2007-03-14 | ||
IN2060CH2007 | 2007-09-13 | ||
IN2060/CHE/2007 | 2007-09-13 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2008100651A2 WO2008100651A2 (fr) | 2008-08-21 |
WO2008100651A3 true WO2008100651A3 (fr) | 2008-11-20 |
Family
ID=39277318
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2008/050388 WO2008100651A2 (fr) | 2007-01-05 | 2008-01-07 | Préparation de darifénacine et ses sels |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP2109601A2 (fr) |
WO (1) | WO2008100651A2 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109641822B (zh) * | 2016-08-12 | 2022-03-11 | 拜耳作物科学股份公司 | 制备取代苯乙烯衍生物的方法 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008126106A2 (fr) * | 2007-04-16 | 2008-10-23 | Manne Satyanarayana Reddy | Procédés nouveaux et perfectionnés pour la préparation d'intermédiaires de darifénacine, de la darifénacine et de ses sels pharmaceutiquement acceptables |
WO2009007853A2 (fr) * | 2007-06-08 | 2009-01-15 | Actavis Group Ptc Ehf | Nouveaux polymorphes de la base libre de darifénacine et son sel d'hydrobromure |
WO2009010846A2 (fr) * | 2007-07-13 | 2009-01-22 | Medichem, S.A. | Forme amorphe du bromhydrate de darifénacine et ses procédés de préparation |
JP2012041277A (ja) * | 2010-08-13 | 2012-03-01 | Kaneka Corp | 1,3位−2置換ピロリジン化合物またはその塩の改良された製造法 |
CN101973971A (zh) * | 2010-09-26 | 2011-02-16 | 山东邹平大展新材料有限公司 | 一种制备5-卤代乙基-2,3-二氢苯并呋喃的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5096890A (en) * | 1989-03-17 | 1992-03-17 | Pfizer Inc. | Pyrrolidine derivatives |
WO2003080599A1 (fr) * | 2002-03-26 | 2003-10-02 | Novartis International Pharmaceutical Ltd. | Hydrate stable d'antagoniste de recepteur muscarinique |
WO2007076158A2 (fr) * | 2005-12-27 | 2007-07-05 | Teva Pharmaceutical Industries Ltd. | Procedes de preparation de bromhydrate de darifenacine |
-
2008
- 2008-01-07 EP EP08772573A patent/EP2109601A2/fr not_active Withdrawn
- 2008-01-07 WO PCT/US2008/050388 patent/WO2008100651A2/fr active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5096890A (en) * | 1989-03-17 | 1992-03-17 | Pfizer Inc. | Pyrrolidine derivatives |
US5096890B1 (en) * | 1989-03-17 | 1995-03-28 | Pfizer | Pyrrolidine derivatives |
WO2003080599A1 (fr) * | 2002-03-26 | 2003-10-02 | Novartis International Pharmaceutical Ltd. | Hydrate stable d'antagoniste de recepteur muscarinique |
US6930188B2 (en) * | 2002-03-26 | 2005-08-16 | Novartis International Pharmaceutical, Ltd. | Stable hydrate of a muscarinic receptor antagonist |
WO2007076158A2 (fr) * | 2005-12-27 | 2007-07-05 | Teva Pharmaceutical Industries Ltd. | Procedes de preparation de bromhydrate de darifenacine |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109641822B (zh) * | 2016-08-12 | 2022-03-11 | 拜耳作物科学股份公司 | 制备取代苯乙烯衍生物的方法 |
Also Published As
Publication number | Publication date |
---|---|
EP2109601A2 (fr) | 2009-10-21 |
WO2008100651A2 (fr) | 2008-08-21 |
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