RS50239B - 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
- RS50239B RS50239B YUP73202A RS50239B RS 50239 B RS50239 B RS 50239B YU P73202 A YUP73202 A YU P73202A RS 50239 B RS50239 B RS 50239B
- Authority
- RS
- Serbia
- 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
- 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
- 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
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229940054269 sodium pyruvate Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (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
Proces za industrijsku sintezu jedinjenja formule I u kojoj R predstavlja lineamu ili razgranatu (C1-6) alkil grupu, naznačen time što se natrijum piruvat formule III kondenzuje sa jedinjenjem formule IV: gde je R kao što je definisano u formuli I, hidrogenacijom koja je katalizovana sa 5% paladijumom na ugljeniku, u vodi, na pritisku od 1 do 20 bar, na temperaturi od 10 do 60 stepeni C, u prisustvu natrijum hidroksida u količini od 0.1 do 0.2 mola po molu korišćenog jedinjenja formule IV da bi se direktnim putem dobilo jedinjenje formule I u optički čistom obliku, zakišeljavanjem reakcione smeše do pH od 2.8 do 4.5 i filtracijom nakon toga.Prijava sadrži još 5 patentnih zahteva.
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 YU73202A (sh) | 2006-03-03 |
| RS50239B true RS50239B (sr) | 2009-07-15 |
Family
ID=8848711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YUP73202 RS50239B (sr) | 2000-03-31 | 2001-03-30 | Novi proces za sintezu n-/(s)-1-karboksibutil/-(s)- alaninskog estra i primena u sintezi perindoprila |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US6818788B2 (sr) |
| EP (1) | EP1268398B1 (sr) |
| JP (1) | JP3930322B2 (sr) |
| KR (1) | KR100498869B1 (sr) |
| CN (1) | CN1171855C (sr) |
| AP (1) | AP1483A (sr) |
| AR (1) | AR027754A1 (sr) |
| AT (1) | ATE297377T1 (sr) |
| AU (2) | AU2001248433B2 (sr) |
| BG (1) | BG65832B1 (sr) |
| BR (1) | BRPI0109609B1 (sr) |
| CA (1) | CA2404700C (sr) |
| CZ (1) | CZ302840B6 (sr) |
| DE (1) | DE60111364T2 (sr) |
| DK (1) | DK1268398T3 (sr) |
| EA (1) | EA004314B1 (sr) |
| EE (1) | EE05079B1 (sr) |
| ES (1) | ES2242743T3 (sr) |
| FR (1) | FR2807037B1 (sr) |
| GE (1) | GEP20063796B (sr) |
| HR (1) | HRP20020860B1 (sr) |
| HU (1) | HU229188B1 (sr) |
| ME (1) | ME00437B (sr) |
| MX (1) | MXPA02009378A (sr) |
| NO (1) | NO328064B1 (sr) |
| NZ (1) | NZ521324A (sr) |
| OA (1) | OA12324A (sr) |
| PL (1) | PL199714B1 (sr) |
| PT (1) | PT1268398E (sr) |
| RS (1) | RS50239B (sr) |
| SI (1) | SI1268398T1 (sr) |
| SK (1) | SK286851B6 (sr) |
| UA (1) | UA73562C2 (sr) |
| WO (1) | WO2001056353A2 (sr) |
| ZA (1) | ZA200207150B (sr) |
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 |
| CA2517205C (en) | 2003-02-28 | 2010-08-24 | Lupin Limited | Process for preparation of perindopril and salts thereof |
| ES2334900T3 (es) * | 2003-09-01 | 2010-03-17 | Les Laboratoires Servier | Nuevo procedimiento de sintesis de esteres de n-((s)-1-carboxibutil)-(s)-alanina y su aplicacion a la sintesis de 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 |
| SI1400531T1 (sl) * | 2003-09-30 | 2006-04-30 | Servier Lab | Postopek za sintezo n-((s)-1-karbetoksibutil)-(s)-alanina in uporaba pri sintezi perindoprila |
| ES2603856T3 (es) * | 2004-03-29 | 2017-03-01 | Les Laboratoires Servier | Procedimiento para preparar una composición farmacéutica 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 SK SK1405-2002A patent/SK286851B6/sk not_active IP Right Cessation
- 2001-03-30 DE DE2001611364 patent/DE60111364T2/de not_active Expired - Lifetime
- 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 AU AU2001248433A patent/AU2001248433B2/en not_active Ceased
- 2001-03-30 ME MEP-2008-664A patent/ME00437B/me unknown
- 2001-03-30 UA UA2002108639A patent/UA73562C2/uk unknown
- 2001-03-30 DK DK01921440T patent/DK1268398T3/da active
- 2001-03-30 US US10/221,973 patent/US6818788B2/en not_active Expired - Lifetime
- 2001-03-30 EE EEP200200553A patent/EE05079B1/xx unknown
- 2001-03-30 JP JP2001556065A patent/JP3930322B2/ja not_active Expired - Fee Related
- 2001-03-30 AP APAP/P/2002/002628A patent/AP1483A/en active
- 2001-03-30 AT AT01921440T patent/ATE297377T1/de active
- 2001-03-30 AU AU4843301A patent/AU4843301A/xx active Pending
- 2001-03-30 PT PT01921440T patent/PT1268398E/pt unknown
- 2001-03-30 RS YUP73202 patent/RS50239B/sr unknown
- 2001-03-30 MX MXPA02009378A patent/MXPA02009378A/es active IP Right Grant
- 2001-03-30 WO PCT/FR2001/000959 patent/WO2001056353A2/fr active IP Right Grant
- 2001-03-30 CZ CZ20023235A patent/CZ302840B6/cs not_active IP Right Cessation
- 2001-03-30 HR HR20020860A patent/HRP20020860B1/xx not_active IP Right Cessation
- 2001-03-30 HU HU0101335A patent/HU229188B1/hu not_active IP Right Cessation
- 2001-03-30 SI SI200130380T patent/SI1268398T1/xx unknown
- 2001-03-30 OA OA1200200303A patent/OA12324A/en unknown
- 2001-03-30 GE GEAP20016674A patent/GEP20063796B/en unknown
- 2001-03-30 NZ NZ521324A patent/NZ521324A/en not_active IP Right Cessation
- 2001-03-30 AR ARP010101537 patent/AR027754A1/es not_active Application Discontinuation
- 2001-03-30 EP EP20010921440 patent/EP1268398B1/fr not_active Expired - Lifetime
- 2001-03-30 BR BRPI0109609-5A patent/BRPI0109609B1/pt not_active IP Right Cessation
- 2001-03-30 CN CNB018074936A patent/CN1171855C/zh not_active Expired - Fee Related
- 2001-03-30 ES ES01921440T patent/ES2242743T3/es not_active Expired - Lifetime
- 2001-03-30 EA EA200201027A patent/EA004314B1/ru 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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