BR9808740A - Método para fabricação de sertindol - Google Patents
Método para fabricação de sertindolInfo
- Publication number
- BR9808740A BR9808740A BR9808740-1A BR9808740A BR9808740A BR 9808740 A BR9808740 A BR 9808740A BR 9808740 A BR9808740 A BR 9808740A BR 9808740 A BR9808740 A BR 9808740A
- Authority
- BR
- Brazil
- Prior art keywords
- fluorophenyl
- indole
- sertindole
- glycine
- chloro
- Prior art date
Links
- 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 5
- 238000000034 method Methods 0.000 title abstract 4
- 229960000652 sertindole Drugs 0.000 title abstract 4
- -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
- 238000004519 manufacturing process Methods 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
- 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
- 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
- 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 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
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 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 That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Compounds Of Unknown Constitution (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
<B>"MéTODO PARA FABRICAçãO DE SERTINDOL"<D> Um processo para fabricação de sertindol compreendendo a preparação de N-(4-fluorofenil)-N-(2-carbóxi-4-clorofenil)glicina, reagindo-se um sal de metal alcalino de ácido 2,5-diclorobenzóico com um sal de metal alcalino de N-(4-fluorofenil) glicina em um ambiente aquoso e alcalino na presença de um catalisador de cobre; ciclização de N-(4-fluorofenil)-N-(2-carbóxi-4-clorofenil)glicina para o 3-acetóxi-indol correspondente; redução do 3-acetóxi-indol e subsequente eliminação do H~ 2~O, deste modo obtendo-se 5-cloro-1-(4-fluorofenil)indol o qual é reagido com 4-piperidona em uma mistura de um ácido acético e HCI concentrado; redução do 5-cloro-1-(4- fluorofenil)-3-(1,2,3,6-tetrahidropiridin-4-il)indol resultante e reação deste componente com 1-(2-cloroetil)-2-imidazolidinon a fim de obter-se sertindol. Alternativamente, 50-cloro-1-(4-fluorofenil)3-(1,2,3,6-tetrahidropiridin-4-il) indol é primeiramente reagido com 1-(2-cloroetil)-2-imidazolidinon seguido de redução, deste modo obtendo-se sertindol. Este processo utiliza reagentes e solventes que são apropriados e permitindo em manufatura de grande escala. Além disso, bons rendimentos totais são obtidos.
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 (1)
| Publication Number | Publication Date |
|---|---|
| BR9808740A true BR9808740A (pt) | 2000-10-03 |
Family
ID=26064179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR9808740-1A BR9808740A (pt) | 1997-05-09 | 1998-05-07 | Método para fabricação de sertindol |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6335463B1 (pt) |
| EP (2) | EP0983264B1 (pt) |
| JP (1) | JP2002515904A (pt) |
| KR (2) | KR100546477B1 (pt) |
| CN (2) | CN1243001C (pt) |
| AT (2) | ATE286047T1 (pt) |
| AU (1) | AU731835B2 (pt) |
| BG (1) | BG64007B1 (pt) |
| BR (1) | BR9808740A (pt) |
| CA (1) | CA2288334C (pt) |
| CZ (2) | CZ299015B6 (pt) |
| DE (2) | DE69828454T2 (pt) |
| DK (2) | DK1260511T3 (pt) |
| EA (1) | EA003248B1 (pt) |
| ES (2) | ES2234961T3 (pt) |
| HK (1) | HK1029583A1 (pt) |
| HU (1) | HU226858B1 (pt) |
| IL (1) | IL132461A (pt) |
| IS (2) | IS2158B (pt) |
| NO (2) | NO325918B1 (pt) |
| NZ (1) | NZ500700A (pt) |
| PL (1) | PL191174B1 (pt) |
| PT (2) | PT983264E (pt) |
| SI (2) | SI1260511T1 (pt) |
| SK (2) | SK285221B6 (pt) |
| TR (2) | TR200003421T2 (pt) |
| UA (1) | UA61105C2 (pt) |
| WO (1) | WO1998051685A1 (pt) |
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 |
| US20060149076A1 (en) * | 2002-08-02 | 2006-07-06 | Frederick Hicks | Copper catalyzed arylation |
| KR20070026396A (ko) * | 2004-01-30 | 2007-03-08 | 베이징 투올린 메디슨 사이언스 앤드 테크놀로지 컴파니 리미티드 | 마라스미우스 안드로사세우스 Ｌ．ｅｓ Ｆｒ 추출물,피페리돈 유도체 및 항고혈압제로서의 그 용도 |
| 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 |
| 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 |
| 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 |
| 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 BR BR9808740-1A patent/BR9808740A/pt not_active Application Discontinuation
- 1998-05-07 AT AT02018748T patent/ATE286047T1/de active
- 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 PT PT98919090T patent/PT983264E/pt unknown
- 1998-05-07 KR KR1019997010319A patent/KR100546477B1/ko not_active IP Right Cessation
- 1998-05-07 DK DK02018748T patent/DK1260511T3/da active
- 1998-05-07 DE DE69828454T patent/DE69828454T2/de not_active Expired - Lifetime
- 1998-05-07 EP EP98919090A patent/EP0983264B1/en not_active Expired - Lifetime
- 1998-05-07 JP JP54871198A patent/JP2002515904A/ja not_active Ceased
- 1998-05-07 TR TR2000/03421T patent/TR200003421T2/xx unknown
- 1998-05-07 IL IL13246198A patent/IL132461A/xx not_active IP Right Cessation
- 1998-05-07 CZ CZ0396099A patent/CZ298509B6/cs not_active IP Right Cessation
- 1998-05-07 SK SK1527-99A patent/SK285221B6/sk not_active IP Right Cessation
- 1998-05-07 SI SI9830747T patent/SI1260511T1/xx unknown
- 1998-05-07 ES ES02018748T patent/ES2234961T3/es not_active Expired - Lifetime
- 1998-05-07 EP EP02018748A patent/EP1260511B1/en not_active Expired - Lifetime
- 1998-05-07 EA EA199901021A patent/EA003248B1/ru not_active IP Right Cessation
- 1998-05-07 HU HU0003365A patent/HU226858B1/hu not_active IP Right Cessation
- 1998-05-07 SI SI9830608T patent/SI0983264T1/xx unknown
- 1998-05-07 CN CNB988048353A patent/CN1243001C/zh not_active Expired - Fee Related
- 1998-05-07 KR KR1020057015729A patent/KR100627616B1/ko not_active IP Right Cessation
- 1998-05-07 PT PT02018748T patent/PT1260511E/pt unknown
- 1998-05-07 TR TR1999/02759T patent/TR199902759T2/xx unknown
- 1998-05-07 CA CA002288334A patent/CA2288334C/en not_active Expired - Fee Related
- 1998-05-07 ES ES98919090T patent/ES2213897T3/es not_active Expired - Lifetime
- 1998-05-07 DK DK98919090T patent/DK0983264T3/da active
- 1998-05-07 DE DE69821477T patent/DE69821477T2/de not_active Expired - Lifetime
- 1998-05-07 SK SK54-2006A patent/SK285410B6/sk not_active IP Right Cessation
- 1998-05-07 WO PCT/DK1998/000183 patent/WO1998051685A1/en active IP Right Grant
- 1998-05-07 NZ NZ500700A patent/NZ500700A/xx not_active IP Right Cessation
- 1998-05-07 AT AT98919090T patent/ATE258929T1/de active
- 1998-05-07 PL PL336578A patent/PL191174B1/pl not_active IP Right Cessation
- 1998-05-07 US US09/423,096 patent/US6335463B1/en not_active Expired - Fee Related
- 1998-05-07 CN CNB2003101046201A patent/CN1301963C/zh not_active Expired - Fee Related
- 1998-07-05 UA UA99116293A patent/UA61105C2/uk 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
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B09B | Patent application refused [chapter 9.2 patent gazette] |
Free format text: INDEFIRO O PRESENTE PEDIDO, UMA VEZ QUE NAO ATENDE AO REQUISITO DA ATIVIDADE INVENTIVA ( ARTS. 8O E 13 DA LEI NO 9279/96 ) |
|
| B12B | Appeal against refusal [chapter 12.2 patent gazette] |