YU73202A - Novi proces za sintezu n-/(s)-1-karboksibutil/-(s)- alaninskog estra i primena u sintezi perindoprila - Google Patents
Novi proces za sintezu n-/(s)-1-karboksibutil/-(s)- alaninskog estra i primena u sintezi perindoprilaInfo
- Publication number
- YU73202A YU73202A YUP73202A YU73202A YU 73202 A YU73202 A YU 73202A YU P73202 A YUP73202 A YU P73202A YU 73202 A YU73202 A YU 73202A
- Authority
- YU
- Yugoslavia
- Prior art keywords
- synthesis
- perindopril
- carboxybutyl
- novel method
- alanine esters
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 4
- 238000003786 synthesis reaction Methods 0.000 title abstract 4
- 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
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229940117360 ethyl pyruvate Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940054269 sodium pyruvate Drugs 0.000 abstract 1
- 230000000707 stereoselective effect Effects 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
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
Abstract
Pronalazak se odnosi stereoselektivni postupak za industrijsku sintetzu derivata sa formulom (I) gde: R predstavlja linearnu ili razgranatu C1-C6 alkil grupu, iz S-norvalinat etila i natrijum piruvata. Pronalazak je koristan za sintezu perindoprila i njegove farmaceutski prihvatljive soli.[The invention concerns a stereoselective method for industrial synthesis of derivatives of formula (I) wherein: R represents a linear or branched C1-C6 alkyl group, from S-norvalinate ethyl and sodium pyruvate. The invention is useful for the synthesis of perindopril and pharmaceutically acceptable salts thereof.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0004112A FR2807037B1 (fr) | 2000-03-31 | 2000-03-31 | 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 |
|---|---|
| YU73202A true YU73202A (sh) | 2006-03-03 |
| RS50239B RS50239B (sr) | 2009-07-15 |
Family
ID=8848711
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US6818788B2 (sh) |
| EP (1) | EP1268398B1 (sh) |
| JP (1) | JP3930322B2 (sh) |
| KR (1) | KR100498869B1 (sh) |
| CN (1) | CN1171855C (sh) |
| AP (1) | AP1483A (sh) |
| AR (1) | AR027754A1 (sh) |
| AT (1) | ATE297377T1 (sh) |
| AU (2) | AU4843301A (sh) |
| BG (1) | BG65832B1 (sh) |
| BR (1) | BRPI0109609B1 (sh) |
| CA (1) | CA2404700C (sh) |
| CZ (1) | CZ302840B6 (sh) |
| DE (1) | DE60111364T2 (sh) |
| DK (1) | DK1268398T3 (sh) |
| EA (1) | EA004314B1 (sh) |
| EE (1) | EE05079B1 (sh) |
| ES (1) | ES2242743T3 (sh) |
| FR (1) | FR2807037B1 (sh) |
| GE (1) | GEP20063796B (sh) |
| HR (1) | HRP20020860B1 (sh) |
| HU (1) | HU229188B1 (sh) |
| ME (1) | ME00437B (sh) |
| MX (1) | MXPA02009378A (sh) |
| NO (1) | NO328064B1 (sh) |
| NZ (1) | NZ521324A (sh) |
| OA (1) | OA12324A (sh) |
| PL (1) | PL199714B1 (sh) |
| PT (1) | PT1268398E (sh) |
| RS (1) | RS50239B (sh) |
| SI (1) | SI1268398T1 (sh) |
| SK (1) | SK286851B6 (sh) |
| UA (1) | UA73562C2 (sh) |
| WO (1) | WO2001056353A2 (sh) |
| ZA (1) | ZA200207150B (sh) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP1603558B1 (en) | 2003-02-28 | 2008-05-21 | Les Laboratoires Servier S.A. | Process for preparation of perindopril and salts thereof |
| DE60329648D1 (de) * | 2003-09-01 | 2009-11-26 | Servier Lab | Neues Verfahren zur Herstellung von Estern des N-((S)-1-Carboxybutyl)-(S)-alanins und seine Verwendung in der Synthese von Perindopril |
| DK1403278T3 (da) * | 2003-09-30 | 2005-10-03 | Servier Lab | Syntesefremgangsmåde for N-[(S)-1-ethoxycarbonylbutyl]-(S)-alanin og anvendelse heraf ved syntesen af perindopril |
| EP1400531B1 (fr) * | 2003-09-30 | 2006-01-04 | Les Laboratoires Servier | Procédé de synthèse de la N-[(S)-1-carbéthoxybutyl]-(S)-alanine et application à la synthèse du perindopril |
| PT1729739T (pt) * | 2004-03-29 | 2016-12-01 | Servier Lab | Processo para a preparação de uma composição farmacêutica sólida |
| GB2413128A (en) * | 2004-04-13 | 2005-10-19 | Neopharma Ltd | Process for the preparation of perindopril |
| SI21800A (sl) * | 2004-05-14 | 2005-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nov postopek sinteze perindoprila |
| WO2006006183A2 (en) * | 2004-07-12 | 2006-01-19 | Matrix Laboratories Ltd | An improved process for the preparation of n-[(s)-ethoxycarbonyl-l-butyl]-(s)-alanine |
| EP1792896A1 (en) * | 2005-12-01 | 2007-06-06 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for the preparation of perindopril and salts thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4247716A (en) * | 1977-09-02 | 1981-01-27 | Mitsui Toatsu Chemicals, Inc. | Process for producing pyruvic acid |
| FR2620699B1 (fr) * | 1987-09-17 | 1990-06-01 | Adir | Procede de synthese d'alpha amino acides n alkyles et de leurs esters. application a la synthese de carboxyalkyl dipeptides |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| FR2807430B1 (fr) * | 2000-04-11 | 2002-05-17 | Adir | Nouveau procede de synthese des esters de la n-[(s)-1- carboxybutyl]-(s)-alanine et application a la synthese du perindopril |
-
2000
- 2000-03-31 FR FR0004112A patent/FR2807037B1/fr not_active Expired - Fee Related
-
2001
- 2001-03-20 PL PL346554A patent/PL199714B1/pl unknown
- 2001-03-30 AU AU4843301A patent/AU4843301A/xx active Pending
- 2001-03-30 RS YUP73202 patent/RS50239B/sr unknown
- 2001-03-30 UA UA2002108639A patent/UA73562C2/uk unknown
- 2001-03-30 PT PT01921440T patent/PT1268398E/pt unknown
- 2001-03-30 CN CNB018074936A patent/CN1171855C/zh not_active Expired - Fee Related
- 2001-03-30 MX MXPA02009378A patent/MXPA02009378A/es active IP Right Grant
- 2001-03-30 DE DE2001611364 patent/DE60111364T2/de not_active Expired - Lifetime
- 2001-03-30 US US10/221,973 patent/US6818788B2/en not_active Expired - Lifetime
- 2001-03-30 EP EP20010921440 patent/EP1268398B1/fr not_active Expired - Lifetime
- 2001-03-30 DK DK01921440T patent/DK1268398T3/da active
- 2001-03-30 HU HU0101335A patent/HU229188B1/hu not_active IP Right Cessation
- 2001-03-30 WO PCT/FR2001/000959 patent/WO2001056353A2/fr not_active Ceased
- 2001-03-30 ME MEP-2008-664A patent/ME00437B/me unknown
- 2001-03-30 BR BRPI0109609-5A patent/BRPI0109609B1/pt not_active IP Right Cessation
- 2001-03-30 CA CA 2404700 patent/CA2404700C/fr not_active Expired - Fee Related
- 2001-03-30 KR KR10-2002-7012810A patent/KR100498869B1/ko not_active Expired - Fee Related
- 2001-03-30 AR ARP010101537 patent/AR027754A1/es not_active Application Discontinuation
- 2001-03-30 AU AU2001248433A patent/AU2001248433B2/en not_active Ceased
- 2001-03-30 OA OA1200200303A patent/OA12324A/en unknown
- 2001-03-30 JP JP2001556065A patent/JP3930322B2/ja not_active Expired - Fee Related
- 2001-03-30 SK SK1405-2002A patent/SK286851B6/sk not_active IP Right Cessation
- 2001-03-30 AP APAP/P/2002/002628A patent/AP1483A/en active
- 2001-03-30 CZ CZ20023235A patent/CZ302840B6/cs not_active IP Right Cessation
- 2001-03-30 EA EA200201027A patent/EA004314B1/ru not_active IP Right Cessation
- 2001-03-30 GE GEAP20016674A patent/GEP20063796B/en unknown
- 2001-03-30 SI SI200130380T patent/SI1268398T1/xx unknown
- 2001-03-30 EE EEP200200553A patent/EE05079B1/xx unknown
- 2001-03-30 ES ES01921440T patent/ES2242743T3/es not_active Expired - Lifetime
- 2001-03-30 AT AT01921440T patent/ATE297377T1/de active
- 2001-03-30 NZ NZ521324A patent/NZ521324A/en not_active IP Right Cessation
- 2001-03-30 HR HR20020860A patent/HRP20020860B1/xx not_active IP Right Cessation
-
2002
- 2002-09-05 ZA ZA200207150A patent/ZA200207150B/en unknown
- 2002-09-26 NO NO20024616A patent/NO328064B1/no not_active IP Right Cessation
- 2002-10-30 BG BG107234A patent/BG65832B1/bg unknown
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