IL119400A - Process for the preparation of enantiomerically pure imidazolyl compounds such as cilansetron by optical resolution with pyroglutamic acid - Google Patents
Process for the preparation of enantiomerically pure imidazolyl compounds such as cilansetron by optical resolution with pyroglutamic acidInfo
- Publication number
- IL119400A IL119400A IL11940096A IL11940096A IL119400A IL 119400 A IL119400 A IL 119400A IL 11940096 A IL11940096 A IL 11940096A IL 11940096 A IL11940096 A IL 11940096A IL 119400 A IL119400 A IL 119400A
- Authority
- IL
- Israel
- Prior art keywords
- addition salt
- acid
- mixture
- enantiomer
- compound
- Prior art date
Links
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 title abstract 2
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 title abstract 2
- NCNFDKWULDWJDS-OAHLLOKOSA-N cilansetron Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C=3N4CCCC=3C=CC=2)=C4CC1 NCNFDKWULDWJDS-OAHLLOKOSA-N 0.000 title 1
- 229960002099 cilansetron Drugs 0.000 title 1
- 125000002883 imidazolyl group Chemical group 0.000 title 1
- 230000003287 optical effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000012452 mother liquor Substances 0.000 abstract 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 2
- -1 imidazolyl compound Chemical class 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95202765 | 1995-10-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL119400A0 IL119400A0 (en) | 1997-01-10 |
| IL119400A true IL119400A (en) | 2000-02-29 |
Family
ID=8220714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11940096A IL119400A (en) | 1995-10-13 | 1996-10-10 | Process for the preparation of enantiomerically pure imidazolyl compounds such as cilansetron by optical resolution with pyroglutamic acid |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5663343A (fr) |
| EP (1) | EP0768309B1 (fr) |
| JP (2) | JP4590038B2 (fr) |
| KR (1) | KR100459745B1 (fr) |
| CN (1) | CN1060774C (fr) |
| AT (1) | ATE224896T1 (fr) |
| AU (1) | AU702594B2 (fr) |
| CA (1) | CA2187484C (fr) |
| CZ (1) | CZ288042B6 (fr) |
| DE (1) | DE69623900T2 (fr) |
| DK (1) | DK0768309T3 (fr) |
| DZ (1) | DZ2104A1 (fr) |
| ES (1) | ES2183908T3 (fr) |
| HU (1) | HU226620B1 (fr) |
| IL (1) | IL119400A (fr) |
| NO (1) | NO307257B1 (fr) |
| NZ (1) | NZ299562A (fr) |
| PT (1) | PT768309E (fr) |
| RU (1) | RU2162085C2 (fr) |
| SK (1) | SK283471B6 (fr) |
| TW (1) | TW513423B (fr) |
| UA (1) | UA48947C2 (fr) |
| ZA (1) | ZA968525B (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19813661A1 (de) * | 1997-08-01 | 1999-02-04 | Solvay Pharm Gmbh | Gegen Racemisierung stabilisierte pharmazeutische Zubereitungen von Cilansetron |
| US6372919B1 (en) * | 2001-01-11 | 2002-04-16 | Dov Pharmaceutical, Inc. | (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane, compositions thereof, and uses as an anti-depressant agent |
| RU2213562C2 (ru) * | 2001-03-14 | 2003-10-10 | Научно-исследовательский институт фармакологии РАМН | Лекарственная композиция |
| GB0216027D0 (en) * | 2002-07-10 | 2002-08-21 | Arachnova Therapeutics Ltd | New therapeutic use |
| US20040048874A1 (en) * | 2001-05-22 | 2004-03-11 | Bardsley Hazel Judith | New therapeutic use of 4-(2-fluorophenyl)-6-methyl-2-(1-piperazinyl)thieno[2,3-D]pyrimidine |
| US7015333B2 (en) * | 2002-11-18 | 2006-03-21 | Solvay Pharmaceuticals B.V. | Process for preparation of imidazolyl compounds |
| EP1424337A1 (fr) * | 2002-11-26 | 2004-06-02 | Solvay Pharmaceuticals GmbH | Dérivés 4-hydroxy de 5,6,9,10-tetrahydro-10-((2-méthyl-1h-imidazol-1-yl)méthyl)-4h-pyrido-(3,2,1-jk)-carbazol-11(8h)-one |
| JP2006516977A (ja) * | 2003-01-13 | 2006-07-13 | ダイノゲン ファーマシューティカルズ，インコーポレイテッド | 悪心、嘔吐、レッチング、またはそれらの任意の組み合わせの治療方法 |
| MXPA05007381A (es) * | 2003-01-13 | 2006-02-10 | Dynogen Pharmaceuticals Inc | Metodo para el tratamiento de transtornos funcionales del intestino. |
| JP2006522144A (ja) * | 2003-04-04 | 2006-09-28 | ダイノゲン ファーマシューティカルズ，インコーポレイテッド | 下部尿路障害の治療方法 |
| WO2005047274A1 (fr) * | 2003-11-12 | 2005-05-26 | Dr. Reddy's Laboratories, Inc. | Preparation d'escitaloprame |
| US20070043100A1 (en) | 2005-08-16 | 2007-02-22 | Hagen Eric J | Novel polymorphs of azabicyclohexane |
| US20080045725A1 (en) | 2006-04-28 | 2008-02-21 | Murry Jerry A | Process For The Synthesis of (+) And (-)-1-(3,4-Dichlorophenyl)-3-Azabicyclo[3.1.0]Hexane |
| US7662831B2 (en) | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
| US7601856B2 (en) | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| JP5156222B2 (ja) * | 2006-11-28 | 2013-03-06 | エムキュア ファーマシューティカルズ リミテッド | 制吐作用化合物の新たな製造方法 |
| GB0910373D0 (en) * | 2009-06-16 | 2009-07-29 | Filtrona Int Ltd | Tabacco smoke filter |
| US9806720B1 (en) * | 2016-10-07 | 2017-10-31 | Analog Devices Global | Compound semiconductor based inverter |
| AU2019270163A1 (en) | 2018-05-18 | 2020-12-03 | Kura Oncology, Inc. | Synthesis of tipifarnib |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7413843A (nl) * | 1974-10-23 | 1976-04-27 | Stamicarbon | Optische scheiding van fenylglycine-amide. |
| US4463176A (en) * | 1982-09-13 | 1984-07-31 | Mead Johnson & Company | Process for resolution of optical isomers |
| US4849527A (en) * | 1982-09-13 | 1989-07-18 | Bristol-Myers Company | Process for resolution of optical isomers |
| SE460359B (sv) * | 1984-01-25 | 1989-10-02 | Glaxo Group Ltd | 3-imidazolylmetyltetrahydrokarbazoloner, foerfarande foer framstaellning av dessa och en farmaceutisk komposition |
| DE3885357T2 (de) * | 1987-06-29 | 1994-03-24 | Duphar Int Res | Anellierte Indolderivate. |
| GB8812636D0 (en) * | 1988-05-27 | 1988-06-29 | Glaxo Group Ltd | Chemical compounds |
| EP0350129A1 (fr) * | 1988-07-07 | 1990-01-10 | Duphar International Research B.V | Indole cétones annelées avec un substituant imidazolylalkyle |
| DE4238553A1 (de) * | 1992-11-14 | 1994-05-19 | Kali Chemie Pharma Gmbh | Neue Imidazol-1-yl-Verbindungen enthaltende Arzneimittel |
| RU2041876C1 (ru) * | 1993-12-29 | 1995-08-20 | Научно-производственный центр "Фармзащита" | Способ получения 1,2,3,9- тетрагидро-9-метил-3- [(2-метил-1н- имидазол-1-ил) метил]-4н- карбазол-4-она или его солей, или их гидратов, и промежуточные продукты для их синтеза |
-
1996
- 1996-09-26 AU AU65856/96A patent/AU702594B2/en not_active Ceased
- 1996-10-03 TW TW085112098A patent/TW513423B/zh not_active IP Right Cessation
- 1996-10-08 CZ CZ19962947A patent/CZ288042B6/cs not_active IP Right Cessation
- 1996-10-08 JP JP28461296A patent/JP4590038B2/ja not_active Expired - Fee Related
- 1996-10-08 SK SK1287-96A patent/SK283471B6/sk not_active IP Right Cessation
- 1996-10-09 NO NO964282A patent/NO307257B1/no not_active IP Right Cessation
- 1996-10-09 DZ DZ960148A patent/DZ2104A1/fr active
- 1996-10-09 HU HU9602778A patent/HU226620B1/hu not_active IP Right Cessation
- 1996-10-09 CA CA002187484A patent/CA2187484C/fr not_active Expired - Fee Related
- 1996-10-09 ZA ZA968525A patent/ZA968525B/xx unknown
- 1996-10-09 RU RU96120366/04A patent/RU2162085C2/ru not_active IP Right Cessation
- 1996-10-10 ES ES96202829T patent/ES2183908T3/es not_active Expired - Lifetime
- 1996-10-10 AT AT96202829T patent/ATE224896T1/de active
- 1996-10-10 KR KR1019960044972A patent/KR100459745B1/ko not_active Expired - Fee Related
- 1996-10-10 PT PT96202829T patent/PT768309E/pt unknown
- 1996-10-10 US US08/728,794 patent/US5663343A/en not_active Expired - Lifetime
- 1996-10-10 DE DE69623900T patent/DE69623900T2/de not_active Expired - Lifetime
- 1996-10-10 EP EP96202829A patent/EP0768309B1/fr not_active Expired - Lifetime
- 1996-10-10 UA UA96103876A patent/UA48947C2/uk unknown
- 1996-10-10 CN CN96122637A patent/CN1060774C/zh not_active Expired - Fee Related
- 1996-10-10 IL IL11940096A patent/IL119400A/xx not_active IP Right Cessation
- 1996-10-10 DK DK96202829T patent/DK0768309T3/da active
- 1996-10-11 NZ NZ299562A patent/NZ299562A/en not_active IP Right Cessation
-
2010
- 2010-04-15 JP JP2010094211A patent/JP2010159292A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |