HRP20020860B1 - Novi proces za sintezu n-[(s)-1-karboksibutil]-(s)-alanin estera i primjena u sintezi perindoprila - Google Patents
Novi proces za sintezu n-[(s)-1-karboksibutil]-(s)-alanin estera i primjena u sintezi perindoprilaInfo
- Publication number
- HRP20020860B1 HRP20020860B1 HR20020860A HRP20020860A HRP20020860B1 HR P20020860 B1 HRP20020860 B1 HR P20020860B1 HR 20020860 A HR20020860 A HR 20020860A HR P20020860 A HRP20020860 A HR P20020860A HR P20020860 B1 HRP20020860 B1 HR P20020860B1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- synthesis
- carboxybutyl
- perindopril
- novel method
- 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
- 230000020477 pH reduction Effects 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)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (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 spojeva formule (I) pri čemu R predstavlja ravnu ili razgrananu (C1-C6) alkilnu skupinu, naznačen time, što se natrij piruvat formule (III): kondenzira sa spojem formule (IV): pri čemu je R definiran kao u formuli (I), uz hidrogenaciju kataliziranu 5% paladijem na ugljiku, u vodi, pri tlaku od 1 do 20 bara, na temperaturi od 10 do 60°C, u nazočnosti natrij hidroksida u količini od 0.1 do 0.2 mola po korištenom molu spoja formule (IV), kako bi se izravno dobio spoj formule (I), u optički čistom obliku, nakon zakiseljavanja reakcijske smjese do pH od 2.8 do 4.5 a potom filtriranjem. Patent sadrži još 5 patentnih zahtjeva.
Applications Claiming Priority (2)
| 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 |
| PCT/FR2001/000959 WO2001056353A2 (fr) | 2000-03-31 | 2001-03-30 | Nouveau procede de synthese de esters de la n-[(s)-1-carboxybutyl]-(s)-alanine et application a la synthese du perindopril |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20020860A2 HRP20020860A2 (en) | 2004-02-29 |
| HRP20020860B1 true HRP20020860B1 (hr) | 2011-02-28 |
Family
ID=8848711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020860A HRP20020860B1 (hr) | 2000-03-31 | 2002-10-31 | Novi proces za sintezu n-[(s)-1-karboksibutil]-(s)-alanin estera i primjena u sintezi perindoprila |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US6818788B2 (hr) |
| EP (1) | EP1268398B1 (hr) |
| JP (1) | JP3930322B2 (hr) |
| KR (1) | KR100498869B1 (hr) |
| CN (1) | CN1171855C (hr) |
| AP (1) | AP1483A (hr) |
| AR (1) | AR027754A1 (hr) |
| AT (1) | ATE297377T1 (hr) |
| AU (2) | AU2001248433B2 (hr) |
| BG (1) | BG65832B1 (hr) |
| BR (1) | BRPI0109609B1 (hr) |
| CA (1) | CA2404700C (hr) |
| CZ (1) | CZ302840B6 (hr) |
| DE (1) | DE60111364T2 (hr) |
| DK (1) | DK1268398T3 (hr) |
| EA (1) | EA004314B1 (hr) |
| EE (1) | EE05079B1 (hr) |
| ES (1) | ES2242743T3 (hr) |
| FR (1) | FR2807037B1 (hr) |
| GE (1) | GEP20063796B (hr) |
| HK (1) | HK1053301A1 (hr) |
| HR (1) | HRP20020860B1 (hr) |
| HU (1) | HU229188B1 (hr) |
| ME (1) | ME00437B (hr) |
| MX (1) | MXPA02009378A (hr) |
| NO (1) | NO328064B1 (hr) |
| NZ (1) | NZ521324A (hr) |
| OA (1) | OA12324A (hr) |
| PL (1) | PL199714B1 (hr) |
| PT (1) | PT1268398E (hr) |
| RS (1) | RS50239B (hr) |
| SI (1) | SI1268398T1 (hr) |
| SK (1) | SK286851B6 (hr) |
| UA (1) | UA73562C2 (hr) |
| WO (1) | WO2001056353A2 (hr) |
| ZA (1) | ZA200207150B (hr) |
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 |
| DE60321233D1 (de) | 2003-02-28 | 2008-07-03 | Servier S A Lab | Verfahren zur herstellung von perindopril |
| PT1362845E (pt) * | 2003-09-01 | 2009-11-05 | Servier Lab | Novo processo de síntese dos ésteres da n-((s)-1- carboxibutil)-(s)-alanina e aplicação à síntese do perindopril |
| SI1403278T1 (en) * | 2003-09-30 | 2005-10-31 | Les Laboratoires Servier | Process for the synthesis of N-((S)-1-(ethoxycarbonyl)butyl)-(S)-alanine and use in the synthese of perindopril |
| ATE315046T1 (de) * | 2003-09-30 | 2006-02-15 | Servier Lab | Verfahren zur herstellung von n-((s)-1- (etoxycarbonyl)butyl)-(s)-alanin und verwendung in der synthese von perindopril |
| HUE031058T2 (en) * | 2004-03-29 | 2017-06-28 | Servier Lab | A method of producing a solid pharmaceutical composition |
| 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 CZ CZ20023235A patent/CZ302840B6/cs not_active IP Right Cessation
- 2001-03-30 ES ES01921440T patent/ES2242743T3/es not_active Expired - Lifetime
- 2001-03-30 AR ARP010101537 patent/AR027754A1/es not_active Application Discontinuation
- 2001-03-30 MX MXPA02009378A patent/MXPA02009378A/es active IP Right Grant
- 2001-03-30 SK SK1405-2002A patent/SK286851B6/sk not_active IP Right Cessation
- 2001-03-30 NZ NZ521324A patent/NZ521324A/en not_active IP Right Cessation
- 2001-03-30 SI SI200130380T patent/SI1268398T1/xx unknown
- 2001-03-30 GE GEAP20016674A patent/GEP20063796B/en unknown
- 2001-03-30 EE EEP200200553A patent/EE05079B1/xx unknown
- 2001-03-30 CA CA 2404700 patent/CA2404700C/fr not_active Expired - Fee Related
- 2001-03-30 PT PT01921440T patent/PT1268398E/pt unknown
- 2001-03-30 AT AT01921440T patent/ATE297377T1/de active
- 2001-03-30 US US10/221,973 patent/US6818788B2/en not_active Expired - Lifetime
- 2001-03-30 DE DE2001611364 patent/DE60111364T2/de not_active Expired - Lifetime
- 2001-03-30 CN CNB018074936A patent/CN1171855C/zh not_active Expired - Fee Related
- 2001-03-30 KR KR10-2002-7012810A patent/KR100498869B1/ko not_active IP Right Cessation
- 2001-03-30 DK DK01921440T patent/DK1268398T3/da active
- 2001-03-30 EA EA200201027A patent/EA004314B1/ru not_active IP Right Cessation
- 2001-03-30 OA OA1200200303A patent/OA12324A/en unknown
- 2001-03-30 RS YUP73202 patent/RS50239B/sr unknown
- 2001-03-30 BR BRPI0109609-5A patent/BRPI0109609B1/pt not_active IP Right Cessation
- 2001-03-30 AU AU2001248433A patent/AU2001248433B2/en not_active Ceased
- 2001-03-30 AP APAP/P/2002/002628A patent/AP1483A/en active
- 2001-03-30 ME MEP-2008-664A patent/ME00437B/me unknown
- 2001-03-30 EP EP20010921440 patent/EP1268398B1/fr not_active Expired - Lifetime
- 2001-03-30 HU HU0101335A patent/HU229188B1/hu not_active IP Right Cessation
- 2001-03-30 JP JP2001556065A patent/JP3930322B2/ja not_active Expired - Fee Related
- 2001-03-30 WO PCT/FR2001/000959 patent/WO2001056353A2/fr active IP Right Grant
- 2001-03-30 UA UA2002108639A patent/UA73562C2/uk unknown
- 2001-03-30 AU AU4843301A patent/AU4843301A/xx active Pending
-
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
- 2002-10-31 HR HR20020860A patent/HRP20020860B1/hr not_active IP Right Cessation
-
2003
- 2003-08-01 HK HK03105541A patent/HK1053301A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20020876B1 (hr) | Postupak za sintezu perindoprila i njegovih farmaceutski prihvatljivih soli | |
| HRP20020860B1 (hr) | Novi proces za sintezu n-[(s)-1-karboksibutil]-(s)-alanin estera i primjena u sintezi perindoprila | |
| EA200900817A1 (ru) | Способ получения фторметилзамещённых гетероциклических соединений | |
| HRP20020887B1 (hr) | Postupak za sintezu n-[(s)-1-karboksibutil]-(s)-alanin estera i uporaba u sintezi perindoprila | |
| BR0307376A (pt) | Composições de barra de sabão que compreendem alquil ésteres de ácido graxo alfa sulfonado e álcoois polihidridicos, e processo para a produção das mesmas | |
| NO20025967D0 (no) | Forkortet syntese av 3,3-diarylpropylaminderivater | |
| DE60134472D1 (de) | Oxidationsverfahren zur herstellung des zwischenproduktes 6.alpha.,9.alpha.-difluoro-11.beta.,17.alpone 17.beta.-karbonsäure | |
| MXPA04000634A (es) | Barra de detergente mejorada y un proceso para fabricacion. | |
| HUP0102657A2 (hu) | Eljárás orto-alkilezett benzoesav-származékok, mint intermedierek és hatóanyagok előállítására | |
| IT1297035B1 (it) | Derivati dell'acido 1,4,7,10-tetraazaciclododecan-1,4-diacetico | |
| HRP20040198B1 (hr) | POSTUPAK PROIZVODNJE BERAPROST-a I NJEGOVIH SOLI | |
| ES2132872T3 (es) | Procedimiento de purificacion de diacetilreina. | |
| BR0104188A (pt) | Processo para a preparação fermentativa de l-aminoácidos não proteinogênicos | |
| DE69917282D1 (de) | Verfahren zur herstellung von zofenopril-calciumsalz | |
| GEP20033119B (en) | Novel Octahydro-6, 10-Dioxo-6H-Pyridazino {1,2-a}{1 Carboxylic Acid Derivatives, Method for Preparation and Use Thereof | |
| ATE213781T1 (de) | Mikrobiologisches verfahren zur herstellung von (s,s) äthylendiamin-n,n'-di-bernsteinsäure | |
| DE3360230D1 (en) | Process for the preparation of beta-hydroxy-alpha-amino-carboxylic acids | |
| FI68043B (fi) | N-halogenacylprolinderivat vilka aer mellanprodukter vid framstaellning av terapeutiskt anvaendbara prolinderivat | |
| RU1099558C (ru) | Производные бис-(оксиалкиламиноэфиров) в качестве ингибиторов коррозии стали в кислых средах | |
| DK0777655T3 (da) | Fremgangsmåde til fremstilling af chirale, tetracykliske, dopaminerge forbindelser | |
| DE60020749D1 (de) | Verfahren zur herstellung von alkyl-n-alkylanthranilate | |
| BRPI0411769A (pt) | processo para a produção de melagatran | |
| TH40149A3 (th) | เกลือชนิดใหม่ | |
| NZ337605A (en) | Process for preparing trovafloxacin acid salts | |
| YU41396A (sh) | Novi n-etil-n-1-naftil acilamidi i postupak njihovog dobijanja |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 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: 20180221 Year of fee payment: 18 |
|
| PBON | Lapse due to non-payment of renewal fee |
Effective date: 20190330 |