EA199901021A1 - Способ получения сертиндола - Google Patents
Способ получения сертиндолаInfo
- Publication number
- EA199901021A1 EA199901021A1 EA199901021A EA199901021A EA199901021A1 EA 199901021 A1 EA199901021 A1 EA 199901021A1 EA 199901021 A EA199901021 A EA 199901021A EA 199901021 A EA199901021 A EA 199901021A EA 199901021 A1 EA199901021 A1 EA 199901021A1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- fluorophenyl
- indole
- glycine
- chloro
- reduction
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 title abstract 3
- -1 2-carboxy-4-chlorophenyl Chemical group 0.000 abstract 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- YGSFFDHIYYOVHV-UHFFFAOYSA-N 1-(2-chloroethyl)imidazolidin-2-one Chemical compound ClCCN1CCNC1=O YGSFFDHIYYOVHV-UHFFFAOYSA-N 0.000 abstract 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 abstract 2
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 abstract 2
- WLQZFXJVVNNEJU-UHFFFAOYSA-N 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C=2CCNCC=2)=C1 WLQZFXJVVNNEJU-UHFFFAOYSA-N 0.000 abstract 2
- 239000004471 Glycine Substances 0.000 abstract 2
- JBOPQACSHPPKEP-UHFFFAOYSA-N Indoxyl acetate Chemical compound C1=CC=C2C(OC(=O)C)=CNC2=C1 JBOPQACSHPPKEP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 229960000652 sertindole Drugs 0.000 abstract 2
- QVTQYSFCFOGITD-UHFFFAOYSA-N 2,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Cl QVTQYSFCFOGITD-UHFFFAOYSA-N 0.000 abstract 1
- ZFIMCCCQJDZLCT-UHFFFAOYSA-N 2-(4-fluoroanilino)acetic acid Chemical compound OC(=O)CNC1=CC=C(F)C=C1 ZFIMCCCQJDZLCT-UHFFFAOYSA-N 0.000 abstract 1
- JYEKQDWSLSXYTJ-UHFFFAOYSA-N 5-chloro-1-(4-fluorophenyl)indole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C=C1 JYEKQDWSLSXYTJ-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Compounds Of Unknown Constitution (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Способ получения сертиндола, включающий получение N-(4-фторфенил)-N-(2-карбокси-4-хлорфенил)глицина путем взаимодействия соли щелочного металла 2,5-дихлорбензойной кислоты с солью щелочного металла N-(4-фторфенил)глицина в водно-щелочной среде в присутствии медного катализатора; циклизацию N-(4-фторфенил)-N-(2-карбокси-4-хлорфенил)глицина до соответствующего 3-ацетокси-индола; восстановление 3-ацетокси-индола и последующее удаление воды с получением 5-хлор-1-(4-фторфенил)индола, который вводят во взаимодействие с 4-пиперидоном в смеси уксусной кислоты и концентрированной HCl; восстановление полученного 5-хлор-1-(4-фторфенил)-3-(1,2,3,6-тетрагидропиридин-4-ил)индола и взаимодействие этого соединения с 1-(2-хлорэтил)-2-имидазолидиноном с целью получения сертиндола. Альтернативно, 5-хлор-1-(4-фторфенил)-3-(1,2,3,6-тетрагидропиридин-4-ил) индол сначала подвергают взаимодействию с 1-(2-хлорэтил)-2-имидазолидиноном с последующим восстановлением с получением сертиндола. В этом способе используют реагенты и растворители, которые являются подходящими и разрешены для промышленного производства. Кроме того, получают хороший общий выход продукта.Международная заявка была опубликована вместе с отчетом о международном поиске.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4601197P | 1997-05-09 | 1997-05-09 | |
| DK53697 | 1997-05-09 | ||
| PCT/DK1998/000183 WO1998051685A1 (en) | 1997-05-09 | 1998-05-07 | Method of manufacturing sertindole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA199901021A1 true EA199901021A1 (ru) | 2000-06-26 |
| EA003248B1 EA003248B1 (ru) | 2003-02-27 |
Family
ID=26064179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA199901021A EA003248B1 (ru) | 1997-05-09 | 1998-05-07 | Способ получения сертиндола |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6335463B1 (ru) |
| EP (2) | EP1260511B1 (ru) |
| JP (1) | JP2002515904A (ru) |
| KR (2) | KR100627616B1 (ru) |
| CN (2) | CN1301963C (ru) |
| AT (2) | ATE258929T1 (ru) |
| AU (1) | AU731835B2 (ru) |
| BG (1) | BG64007B1 (ru) |
| BR (1) | BR9808740A (ru) |
| CA (1) | CA2288334C (ru) |
| CZ (2) | CZ299015B6 (ru) |
| DE (2) | DE69828454T2 (ru) |
| DK (2) | DK0983264T3 (ru) |
| EA (1) | EA003248B1 (ru) |
| ES (2) | ES2213897T3 (ru) |
| HK (1) | HK1029583A1 (ru) |
| HU (1) | HU226858B1 (ru) |
| IL (1) | IL132461A (ru) |
| IS (2) | IS2158B (ru) |
| NO (2) | NO325918B1 (ru) |
| NZ (1) | NZ500700A (ru) |
| PL (1) | PL191174B1 (ru) |
| PT (2) | PT1260511E (ru) |
| SI (2) | SI0983264T1 (ru) |
| SK (2) | SK285410B6 (ru) |
| TR (2) | TR199902759T2 (ru) |
| UA (1) | UA61105C2 (ru) |
| WO (1) | WO1998051685A1 (ru) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6489341B1 (en) | 1999-06-02 | 2002-12-03 | Sepracor Inc. | Methods for the treatment of neuroleptic and related disorders using sertindole derivatives |
| AR039116A1 (es) * | 2002-03-27 | 2005-02-09 | Lundbeck & Co As H | Metodo para la manufactura de sertindol |
| CN1863752A (zh) * | 2002-08-02 | 2006-11-15 | 罗迪亚药业公司 | 铜催化的芳基化 |
| EP1710235A4 (en) | 2004-01-30 | 2008-12-17 | Beijing Tuolin Medicine Scienc | EXTRACTS OF MARASMINS ANDROSACEUS L.ES, PIPERDINONE DERIVATIVES AND THEIR USE AS BLOOD PRESSURE MEDICINES |
| KR100683274B1 (ko) * | 2004-02-12 | 2007-02-15 | 에스케이케미칼주식회사 | 치환된 벤조피란 화합물의 제조방법 |
| US20070212412A1 (en) * | 2005-09-08 | 2007-09-13 | H. Lundbeck A/S | Stable solid formulation of sertindole |
| TW200821296A (en) * | 2006-06-01 | 2008-05-16 | Lundbeck & Co As H | Use of sertindole for the preventive treatment of suicidal behaviour |
| CN101362704B (zh) * | 2008-09-23 | 2012-04-18 | 上海医药工业研究院 | N-(4-氟苯基)-n-(2-羧基-4-氯苯基)甘氨酸的制备方法 |
| CN101362748B (zh) * | 2008-09-23 | 2012-09-05 | 上海医药工业研究院 | 一种制备舍吲哚的方法 |
| CN101591330B (zh) * | 2009-06-29 | 2013-03-06 | 上海医药工业研究院 | 舍吲哚晶型及其制备方法 |
| CN101899036B (zh) * | 2010-07-22 | 2012-12-19 | 郑州大学 | 以烷基咪唑型离子液体为溶剂制备舍吲哚的方法 |
| CN103214463A (zh) * | 2013-03-30 | 2013-07-24 | 北京德众万全药物技术开发有限公司 | 一种新的舍吲哚制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3131527A1 (de) * | 1981-08-08 | 1983-02-24 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 1-phenyl-2-aminocarbonylindol-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| IE58370B1 (en) * | 1985-04-10 | 1993-09-08 | Lundbeck & Co As H | Indole derivatives |
| IT1271352B (it) * | 1993-04-08 | 1997-05-27 | Boehringer Ingelheim Italia | Derivati dell'indolo utili nel trattamento dei disturbi del sistema nervoso centrale |
| DE19532054A1 (de) * | 1995-08-31 | 1997-03-06 | Hoechst Ag | Verfahren zur Herstellung von N-Carboxymethylen-4-chlor-anthranilsäure, sowie deren Dialkylestern |
-
1998
- 1998-05-07 IL IL13246198A patent/IL132461A/xx not_active IP Right Cessation
- 1998-05-07 SI SI9830608T patent/SI0983264T1/xx unknown
- 1998-05-07 SK SK54-2006A patent/SK285410B6/sk not_active IP Right Cessation
- 1998-05-07 TR TR1999/02759T patent/TR199902759T2/xx unknown
- 1998-05-07 CN CNB2003101046201A patent/CN1301963C/zh not_active Expired - Fee Related
- 1998-05-07 DE DE69828454T patent/DE69828454T2/de not_active Expired - Lifetime
- 1998-05-07 AT AT98919090T patent/ATE258929T1/de active
- 1998-05-07 NZ NZ500700A patent/NZ500700A/xx not_active IP Right Cessation
- 1998-05-07 CN CNB988048353A patent/CN1243001C/zh not_active Expired - Fee Related
- 1998-05-07 HU HU0003365A patent/HU226858B1/hu not_active IP Right Cessation
- 1998-05-07 WO PCT/DK1998/000183 patent/WO1998051685A1/en active IP Right Grant
- 1998-05-07 PL PL336578A patent/PL191174B1/pl not_active IP Right Cessation
- 1998-05-07 DE DE69821477T patent/DE69821477T2/de not_active Expired - Lifetime
- 1998-05-07 CZ CZ20050518A patent/CZ299015B6/cs not_active IP Right Cessation
- 1998-05-07 AU AU72062/98A patent/AU731835B2/en not_active Ceased
- 1998-05-07 EA EA199901021A patent/EA003248B1/ru not_active IP Right Cessation
- 1998-05-07 PT PT02018748T patent/PT1260511E/pt unknown
- 1998-05-07 EP EP02018748A patent/EP1260511B1/en not_active Expired - Lifetime
- 1998-05-07 KR KR1020057015729A patent/KR100627616B1/ko not_active IP Right Cessation
- 1998-05-07 PT PT98919090T patent/PT983264E/pt unknown
- 1998-05-07 CZ CZ0396099A patent/CZ298509B6/cs not_active IP Right Cessation
- 1998-05-07 US US09/423,096 patent/US6335463B1/en not_active Expired - Fee Related
- 1998-05-07 JP JP54871198A patent/JP2002515904A/ja not_active Ceased
- 1998-05-07 SK SK1527-99A patent/SK285221B6/sk not_active IP Right Cessation
- 1998-05-07 EP EP98919090A patent/EP0983264B1/en not_active Expired - Lifetime
- 1998-05-07 ES ES98919090T patent/ES2213897T3/es not_active Expired - Lifetime
- 1998-05-07 KR KR1019997010319A patent/KR100546477B1/ko not_active IP Right Cessation
- 1998-05-07 SI SI9830747T patent/SI1260511T1/xx unknown
- 1998-05-07 DK DK98919090T patent/DK0983264T3/da active
- 1998-05-07 CA CA002288334A patent/CA2288334C/en not_active Expired - Fee Related
- 1998-05-07 AT AT02018748T patent/ATE286047T1/de active
- 1998-05-07 BR BR9808740-1A patent/BR9808740A/pt not_active Application Discontinuation
- 1998-05-07 DK DK02018748T patent/DK1260511T3/da active
- 1998-05-07 ES ES02018748T patent/ES2234961T3/es not_active Expired - Lifetime
- 1998-05-07 TR TR2000/03421T patent/TR200003421T2/xx unknown
- 1998-07-05 UA UA99116293A patent/UA61105C2/ru unknown
-
1999
- 1999-10-19 IS IS5222A patent/IS2158B/is unknown
- 1999-11-04 BG BG103857A patent/BG64007B1/bg unknown
- 1999-11-08 NO NO19995457A patent/NO325918B1/no not_active IP Right Cessation
-
2001
- 2001-01-05 HK HK01100142A patent/HK1029583A1/xx not_active IP Right Cessation
-
2006
- 2006-05-15 IS IS8468A patent/IS2324B/is unknown
-
2007
- 2007-12-03 NO NO20076208A patent/NO331924B1/no not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ KZ KG MD TJ TM |
|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): BY RU |