AR043411A1 - Procedimiento para la sintesis del acido 2s, 3as ,7as carboxilico y esteresdel mismo, y aplicacion en la sintesis de perindopril - Google Patents
Procedimiento para la sintesis del acido 2s, 3as ,7as carboxilico y esteresdel mismo, y aplicacion en la sintesis de perindoprilInfo
- Publication number
- AR043411A1 AR043411A1 ARP040100611A ARP040100611A AR043411A1 AR 043411 A1 AR043411 A1 AR 043411A1 AR P040100611 A ARP040100611 A AR P040100611A AR P040100611 A ARP040100611 A AR P040100611A AR 043411 A1 AR043411 A1 AR 043411A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- synthesis
- perindopril
- acid
- application
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 4
- 238000003786 synthesis reaction Methods 0.000 title abstract 4
- 239000002253 acid Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 title abstract 2
- 229960002582 perindopril Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical group 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- KTZNVZJECQAMBV-UHFFFAOYSA-N 1-(cyclohexen-1-yl)pyrrolidine Chemical compound C1CCCN1C1=CCCCC1 KTZNVZJECQAMBV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hospice & Palliative Care (AREA)
- Indole Compounds (AREA)
- Peptides Or Proteins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Aplicación en la síntesis de perindopril y sales farmacéuticamente aceptables del mismo. Reivindicación 1: Procedimiento para la síntesis de compuestos de fórmula (19 donde R representa un átomo de H o un grupo protector para la función ácido, caracterizado porque 1-(1-ciclohexen-1-il)-pirrolidina e fórmula (3) se somete a reacción con el compuesto de fórmula (4) donde R es tal como se ha definido para la fórmula (1) y R´ representa un grupo protector para la función amina que es diferente de R, para obtener el compuesto de fórmula (5) donde R y R´ son tal como se han definido anteriormente, la función amina del mismo se desprotege antes de llevar a cabo la ciclización, y luego se efectúa la deshidratación, para obtener el compuesto de fórmula (6) donde R es tal como se ha definido anteriormente, que se somete a hidrogenación catalítica, en presencia de un catalizador como ser platino, paladio, rodio o níquel, bajo una presión que oscila entre 1 y 30 bar, para obtener, después de la desprotección o reprotección opcional de la función ácido, el compuesto de fórmula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03290487A EP1338591B1 (fr) | 2003-02-28 | 2003-02-28 | Nouveau procédé de synthèse de l'acide (2S, 3aS, 7aS)-perhydroindole-2-carboxylique et de ses esters, et application à la synthèse du perindopril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR043411A1 true AR043411A1 (es) | 2005-07-27 |
Family
ID=27635945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040100611A AR043411A1 (es) | 2003-02-28 | 2004-02-27 | Procedimiento para la sintesis del acido 2s, 3as ,7as carboxilico y esteresdel mismo, y aplicacion en la sintesis de perindopril |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7157484B2 (es) |
| EP (1) | EP1338591B1 (es) |
| JP (1) | JP4563371B2 (es) |
| CN (1) | CN100364974C (es) |
| AR (1) | AR043411A1 (es) |
| AT (1) | ATE307801T1 (es) |
| AU (1) | AU2004218200B2 (es) |
| DE (1) | DE60301980T2 (es) |
| DK (1) | DK1338591T3 (es) |
| EA (1) | EA007948B1 (es) |
| ES (1) | ES2250847T3 (es) |
| MY (1) | MY135169A (es) |
| NZ (1) | NZ541422A (es) |
| PL (1) | PL219733B1 (es) |
| SI (1) | SI1338591T1 (es) |
| WO (1) | WO2004078707A2 (es) |
| ZA (1) | ZA200505779B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004099138A2 (en) * | 2003-05-12 | 2004-11-18 | Cipla Limited | Process for the preparation of perindopril |
| HRP20161602T1 (hr) * | 2004-03-29 | 2016-12-30 | Les Laboratoires Servier | Postupak priprave čvrstog farmaceutskog pripravka |
| SI21800A (sl) | 2004-05-14 | 2005-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nov postopek sinteze perindoprila |
| ATE515496T1 (de) * | 2004-12-28 | 2011-07-15 | Dsm Ip Assets Bv | Verfahren zur herstellung von enantiomerenangereicherter indolin-2-carbonsäure |
| CN100391945C (zh) * | 2005-05-31 | 2008-06-04 | 浙江大学 | 一种s-(-)-吲哚啉-2-羧酸的合成方法 |
| CN116120195B (zh) * | 2022-12-29 | 2025-02-25 | 长兴宜生药物科技有限公司 | 一种催化制备培哚普利中间体的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1341296C (en) * | 1981-12-29 | 2001-09-25 | Hansjorg Urbach | 2-azabicycloalkane-3-carboxylic acid derivatives, processes for their preparation, agents containing these compounds and their use |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| NL1008302C2 (nl) * | 1998-02-13 | 1999-08-16 | Dsm Nv | Werkwijze voor de bereiding van een optisch actief indoline-2-carbonzuur of derivaat daarvan. |
| FR2807431B1 (fr) * | 2000-04-06 | 2002-07-19 | Adir | Nouveau procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables |
| FR2827860B1 (fr) * | 2001-07-24 | 2004-12-10 | Servier Lab | Nouveau procede de synthese de derives de l'acide (2s, 3as, 7as)-1-[(s)-alanyl]-octahydro-1h-indole-2-carboxyline et application a la synthese du perindopril |
| DE60301774T2 (de) * | 2003-02-28 | 2006-07-20 | Les Laboratoires Servier | Verfahren zur Synthese von (2S,3aS,7aS)-1-((S)-Alanyl)-octahydro-1H-indol-2-carbonsäurederivaten und Verwendung in der Synthese von Perindopril |
-
2003
- 2003-02-28 SI SI200330107T patent/SI1338591T1/sl unknown
- 2003-02-28 DK DK03290487T patent/DK1338591T3/da active
- 2003-02-28 DE DE60301980T patent/DE60301980T2/de not_active Expired - Lifetime
- 2003-02-28 ES ES03290487T patent/ES2250847T3/es not_active Expired - Lifetime
- 2003-02-28 EP EP03290487A patent/EP1338591B1/fr not_active Expired - Lifetime
- 2003-02-28 AT AT03290487T patent/ATE307801T1/de active
-
2004
- 2004-02-27 NZ NZ541422A patent/NZ541422A/en not_active IP Right Cessation
- 2004-02-27 AR ARP040100611A patent/AR043411A1/es not_active Application Discontinuation
- 2004-02-27 CN CNB2004800054078A patent/CN100364974C/zh not_active Expired - Fee Related
- 2004-02-27 PL PL377232A patent/PL219733B1/pl unknown
- 2004-02-27 ZA ZA200505779A patent/ZA200505779B/xx unknown
- 2004-02-27 MY MYPI20040683A patent/MY135169A/en unknown
- 2004-02-27 JP JP2006500161A patent/JP4563371B2/ja not_active Expired - Fee Related
- 2004-02-27 US US10/546,967 patent/US7157484B2/en not_active Expired - Fee Related
- 2004-02-27 AU AU2004218200A patent/AU2004218200B2/en not_active Ceased
- 2004-02-27 WO PCT/FR2004/000444 patent/WO2004078707A2/fr not_active Ceased
- 2004-02-27 EA EA200501256A patent/EA007948B1/ru not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ541422A (en) | 2008-03-28 |
| SI1338591T1 (sl) | 2006-02-28 |
| US20060167273A1 (en) | 2006-07-27 |
| AU2004218200B2 (en) | 2009-07-30 |
| MY135169A (en) | 2008-02-29 |
| ZA200505779B (en) | 2006-09-27 |
| ES2250847T3 (es) | 2006-04-16 |
| JP4563371B2 (ja) | 2010-10-13 |
| AU2004218200A1 (en) | 2004-09-16 |
| PL219733B1 (pl) | 2015-07-31 |
| CN1753869A (zh) | 2006-03-29 |
| EP1338591B1 (fr) | 2005-10-26 |
| EA200501256A1 (ru) | 2006-04-28 |
| PL377232A1 (pl) | 2006-01-23 |
| DE60301980D1 (de) | 2005-12-01 |
| WO2004078707A3 (fr) | 2004-10-14 |
| WO2004078707A2 (fr) | 2004-09-16 |
| EA007948B1 (ru) | 2007-02-27 |
| JP2006519175A (ja) | 2006-08-24 |
| DK1338591T3 (da) | 2006-01-23 |
| CN100364974C (zh) | 2008-01-30 |
| EP1338591A1 (fr) | 2003-08-27 |
| ATE307801T1 (de) | 2005-11-15 |
| DE60301980T2 (de) | 2006-07-27 |
| HK1086262A1 (en) | 2006-09-15 |
| US7157484B2 (en) | 2007-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure | ||
| FA | Abandonment or withdrawal | ||
| FA | Abandonment or withdrawal |