HRP20020887B1 - Method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine esters and use in synthesis of perindopril - Google Patents
Method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine esters and use in synthesis of perindoprilInfo
- Publication number
- HRP20020887B1 HRP20020887B1 HR20020887A HRP20020887A HRP20020887B1 HR P20020887 B1 HRP20020887 B1 HR P20020887B1 HR 20020887 A HR20020887 A HR 20020887A HR P20020887 A HRP20020887 A HR P20020887A HR P20020887 B1 HRP20020887 B1 HR P20020887B1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- synthesis
- compound
- carboxybutyl
- perindopril
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 3
- 238000003786 synthesis reaction Methods 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 1
- 229960002582 perindopril Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 1
- 235000004279 alanine Nutrition 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 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
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0004610A FR2807430B1 (fr) | 2000-04-11 | 2000-04-11 | Nouveau procede de synthese des esters de la n-[(s)-1- carboxybutyl]-(s)-alanine et application a la synthese du perindopril |
| PCT/FR2001/001088 WO2001056972A1 (fr) | 2000-04-11 | 2001-04-10 | Nouveau procede de synthese des esters de la n-[(s)-1-carboxybutyl]-(s)-alanine et application a la synthese du perindopril |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20020887A2 HRP20020887A2 (en) | 2004-02-29 |
| HRP20020887B1 true HRP20020887B1 (en) | 2011-03-31 |
Family
ID=8849107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020887A HRP20020887B1 (en) | 2000-04-11 | 2002-11-11 | Method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine esters and use in synthesis of perindopril |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US6774259B2 (uk) |
| EP (1) | EP1272454B1 (uk) |
| JP (1) | JP3872344B2 (uk) |
| KR (1) | KR100520700B1 (uk) |
| CN (1) | CN1176903C (uk) |
| AP (1) | AP1417A (uk) |
| AR (1) | AR027782A1 (uk) |
| AT (1) | ATE362913T1 (uk) |
| AU (2) | AU5046701A (uk) |
| BG (1) | BG65833B1 (uk) |
| BR (1) | BR0109963A (uk) |
| CA (1) | CA2405466C (uk) |
| CY (1) | CY1106720T1 (uk) |
| CZ (1) | CZ302603B6 (uk) |
| DE (1) | DE60128554T2 (uk) |
| DK (1) | DK1272454T3 (uk) |
| EA (1) | EA004265B1 (uk) |
| EE (1) | EE05030B1 (uk) |
| ES (1) | ES2287114T3 (uk) |
| FR (1) | FR2807430B1 (uk) |
| GE (1) | GEP20063798B (uk) |
| HK (1) | HK1053300A1 (uk) |
| HR (1) | HRP20020887B1 (uk) |
| HU (1) | HU229189B1 (uk) |
| ME (1) | ME00442B (uk) |
| MX (1) | MXPA02009888A (uk) |
| NO (1) | NO327970B1 (uk) |
| NZ (1) | NZ521846A (uk) |
| OA (1) | OA12246A (uk) |
| PL (1) | PL346553A1 (uk) |
| PT (1) | PT1272454E (uk) |
| RS (1) | RS50240B (uk) |
| SK (1) | SK287067B6 (uk) |
| UA (1) | UA72040C2 (uk) |
| WO (1) | WO2001056972A1 (uk) |
| ZA (1) | ZA200207689B (uk) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2807037B1 (fr) * | 2000-03-31 | 2002-05-10 | Adir | NOUVEAU PROCEDE DE SYNTHESE DES ESTERS DE LA N-[(s)-1- CARBOXYBUTYL]-(S)-ALANINE ET APPLICATION A LA SYNTHESE DU PERINDOPRIL |
| 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 |
| ATE395913T1 (de) | 2003-02-28 | 2008-06-15 | Servier S A Lab | Verfahren zur herstellung von perindopril |
| DK1362845T3 (da) * | 2003-09-01 | 2010-01-18 | Servier Lab | Ny fremgangsmåde til fremstilling af estere af N-((S)-1-carboxybutyl)-(S)-alanin og deres anvendelse ved fremstilling af perindopril |
| EP1403278B1 (fr) * | 2003-09-30 | 2005-06-08 | Les Laboratoires Servier | Procédé de synthèse de la N-((S)-1-carbéthoxybutyl)-(S)-alanine et application à la synthèse du perindopril |
| ES2256693T3 (es) * | 2003-09-30 | 2006-07-16 | Les Laboratoires Servier | Procedimiento de sintesis de n-((s)-1-(etoxicarbonil)butil)-(s)-alanina y su utilizacion en la sintesis de perindopril. |
| EA011712B1 (ru) * | 2004-03-29 | 2009-04-28 | Ле Лаборатуар Сервье | Способ производства твёрдой фармацевтической композиции |
| SI21800A (sl) | 2004-05-14 | 2005-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nov postopek sinteze perindoprila |
| EP1792896A1 (en) | 2005-12-01 | 2007-06-06 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for the preparation of perindopril and salts thereof |
| FI126564B (fi) | 2011-02-28 | 2017-02-15 | Andritz Oy | Menetelmä ja laitteisto meesan polttamiseksi |
| CN107098949B (zh) * | 2017-04-20 | 2021-03-16 | 上药东英（江苏）药业有限公司 | 一种制备培哚普利叔丁胺盐的绿色合成新工艺 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0308340A1 (fr) * | 1987-09-17 | 1989-03-22 | Adir Et Compagnie | Procédé de synthèse d'alpha amino acides N alkyles et de leurs esters. Application à la synthèse de carboxyalkyl dipeptides |
| EP0309324A1 (fr) * | 1987-09-17 | 1989-03-29 | Adir Et Compagnie | Procédé de synthèse d'alpha amino N alkyles et de leurs esters. Application à la synthèse de carboxyalkyl dipeptides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2503155A2 (fr) * | 1980-10-02 | 1982-10-08 | Science Union & Cie | Nouveaux imino diacides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme |
| US4344949A (en) * | 1980-10-03 | 1982-08-17 | Warner-Lambert Company | Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| US4296110A (en) * | 1980-10-28 | 1981-10-20 | E. I. Du Pont De Nemours And Company | Antihypertensive I-substituted cyclic lactam-2-carboxylic acids |
| US4503043A (en) * | 1981-12-07 | 1985-03-05 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-isoindole-1-carboxylic acids |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
-
2000
- 2000-04-11 FR FR0004610A patent/FR2807430B1/fr not_active Expired - Fee Related
-
2001
- 2001-03-20 PL PL01346553A patent/PL346553A1/xx not_active Application Discontinuation
- 2001-03-30 HU HU0101337A patent/HU229189B1/hu not_active IP Right Cessation
- 2001-04-09 AR ARP010101670A patent/AR027782A1/es not_active Application Discontinuation
- 2001-04-10 KR KR10-2002-7013604A patent/KR100520700B1/ko not_active IP Right Cessation
- 2001-04-10 DE DE60128554T patent/DE60128554T2/de not_active Expired - Lifetime
- 2001-04-10 AU AU5046701A patent/AU5046701A/xx active Pending
- 2001-04-10 DK DK01923776T patent/DK1272454T3/da active
- 2001-04-10 GE GEAP20016688A patent/GEP20063798B/en unknown
- 2001-04-10 CZ CZ20023323A patent/CZ302603B6/cs not_active IP Right Cessation
- 2001-04-10 BR BR0109963-9A patent/BR0109963A/pt not_active Application Discontinuation
- 2001-04-10 AU AU2001250467A patent/AU2001250467B2/en not_active Ceased
- 2001-04-10 MX MXPA02009888A patent/MXPA02009888A/es active IP Right Grant
- 2001-04-10 AT AT01923776T patent/ATE362913T1/de active
- 2001-04-10 US US10/257,239 patent/US6774259B2/en not_active Expired - Lifetime
- 2001-04-10 WO PCT/FR2001/001088 patent/WO2001056972A1/fr active IP Right Grant
- 2001-04-10 RS YU76702A patent/RS50240B/sr unknown
- 2001-04-10 SK SK1457-2002A patent/SK287067B6/sk not_active IP Right Cessation
- 2001-04-10 ES ES01923776T patent/ES2287114T3/es not_active Expired - Lifetime
- 2001-04-10 CN CNB018079210A patent/CN1176903C/zh not_active Expired - Fee Related
- 2001-04-10 EP EP01923776A patent/EP1272454B1/fr not_active Expired - Lifetime
- 2001-04-10 CA CA002405466A patent/CA2405466C/fr not_active Expired - Fee Related
- 2001-04-10 NZ NZ521846A patent/NZ521846A/en not_active IP Right Cessation
- 2001-04-10 OA OA1200200313A patent/OA12246A/en unknown
- 2001-04-10 ME MEP-2008-671A patent/ME00442B/me unknown
- 2001-04-10 EE EEP200200586A patent/EE05030B1/xx not_active IP Right Cessation
- 2001-04-10 AP APAP/P/2002/002639A patent/AP1417A/en active
- 2001-04-10 PT PT01923776T patent/PT1272454E/pt unknown
- 2001-04-10 JP JP2001556822A patent/JP3872344B2/ja not_active Expired - Fee Related
- 2001-04-10 EA EA200201049A patent/EA004265B1/ru not_active IP Right Cessation
- 2001-10-04 UA UA2002118916A patent/UA72040C2/uk unknown
-
2002
- 2002-09-25 ZA ZA200207689A patent/ZA200207689B/xx unknown
- 2002-10-04 NO NO20024811A patent/NO327970B1/no not_active IP Right Cessation
- 2002-11-04 BG BG107250A patent/BG65833B1/bg unknown
- 2002-11-11 HR HR20020887A patent/HRP20020887B1/xx not_active IP Right Cessation
-
2003
- 2003-08-01 HK HK03105540A patent/HK1053300A1/xx not_active IP Right Cessation
-
2007
- 2007-07-12 CY CY20071100924T patent/CY1106720T1/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0308340A1 (fr) * | 1987-09-17 | 1989-03-22 | Adir Et Compagnie | Procédé de synthèse d'alpha amino acides N alkyles et de leurs esters. Application à la synthèse de carboxyalkyl dipeptides |
| EP0309324A1 (fr) * | 1987-09-17 | 1989-03-29 | Adir Et Compagnie | Procédé de synthèse d'alpha amino N alkyles et de leurs esters. Application à la synthèse de carboxyalkyl dipeptides |
Also Published As
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Legal Events
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| A1OB | Publication of a patent application | ||
| ARAI | Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application | ||
| B1PR | Patent granted | ||
| ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20180327 Year of fee payment: 18 |
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| PBON | Lapse due to non-payment of renewal fee |
Effective date: 20190410 |