HRP20020876B1 - Method for synthesis of perindopril and its pharmaceutically acceotable salts - Google Patents
Method for synthesis of perindopril and its pharmaceutically acceotable saltsInfo
- Publication number
- HRP20020876B1 HRP20020876B1 HR20020876A HRP20020876A HRP20020876B1 HR P20020876 B1 HRP20020876 B1 HR P20020876B1 HR 20020876 A HR20020876 A HR 20020876A HR P20020876 A HRP20020876 A HR P20020876A HR P20020876 B1 HRP20020876 B1 HR P20020876B1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- perindopril
- synthesis
- salts
- Prior art date
Links
- 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 3
- 229960002582 perindopril Drugs 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- -1 benzyl ester Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Peptides Or Proteins (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0004379A FR2807431B1 (fr) | 2000-04-06 | 2000-04-06 | Nouveau procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables |
PCT/FR2001/001026 WO2001058868A1 (fr) | 2000-04-06 | 2001-04-05 | Procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables |
Publications (2)
Publication Number | Publication Date |
---|---|
HRP20020876A2 HRP20020876A2 (en) | 2004-02-29 |
HRP20020876B1 true HRP20020876B1 (en) | 2010-10-31 |
Family
ID=8848925
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20020876A HRP20020876B1 (en) | 2000-04-06 | 2002-11-06 | Method for synthesis of perindopril and its pharmaceutically acceotable salts |
Country Status (35)
Country | Link |
---|---|
US (1) | US6835843B2 (ko) |
EP (1) | EP1268424B1 (ko) |
JP (1) | JP3939553B2 (ko) |
KR (1) | KR100507616B1 (ko) |
CN (1) | CN1296355C (ko) |
AP (1) | AP1385A (ko) |
AT (1) | ATE369338T1 (ko) |
AU (2) | AU4847001A (ko) |
BG (1) | BG65984B1 (ko) |
BR (1) | BRPI0109836B1 (ko) |
CA (1) | CA2405486C (ko) |
CY (1) | CY1108522T1 (ko) |
CZ (1) | CZ302575B6 (ko) |
DE (1) | DE60129800T2 (ko) |
DK (1) | DK1268424T3 (ko) |
EA (1) | EA005079B1 (ko) |
EE (1) | EE05032B1 (ko) |
ES (1) | ES2291307T3 (ko) |
FR (1) | FR2807431B1 (ko) |
GE (1) | GEP20063797B (ko) |
HK (1) | HK1053309A1 (ko) |
HR (1) | HRP20020876B1 (ko) |
HU (1) | HU227674B1 (ko) |
ME (1) | ME00441B (ko) |
MX (1) | MXPA02009706A (ko) |
NO (1) | NO324174B1 (ko) |
NZ (1) | NZ521454A (ko) |
OA (1) | OA12242A (ko) |
PL (1) | PL204471B1 (ko) |
PT (1) | PT1268424E (ko) |
RS (1) | RS50808B (ko) |
SK (1) | SK286921B6 (ko) |
UA (1) | UA75070C2 (ko) |
WO (1) | WO2001058868A1 (ko) |
ZA (1) | ZA200207419B (ko) |
Families Citing this family (32)
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 |
DE60220877T2 (de) | 2002-01-30 | 2008-04-10 | Les Laboratoires Servier | Verfahren zur Herstellung von hochreinem Perindopril und Zwischenverbindungen nützlich in der Synthese |
JP2005256847A (ja) * | 2002-02-28 | 2005-09-22 | Nsk Ltd | 車輪用軸受ユニット |
GB2395195A (en) | 2002-11-18 | 2004-05-19 | Cipla Ltd | Preparation of perindopril from carboxy-protected precursor, & perindopril monohydrates for use as angiotensin converting enzyme (ACE) inhibitors |
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 |
EP1338591B1 (fr) * | 2003-02-28 | 2005-10-26 | Les Laboratoires Servier | Nouveau procédé de synthèse de l'acide (2S, 3aS, 7aS)-perhydroindole-2-carboxylique et de ses esters, et application à la synthèse du perindopril |
SI1603558T1 (sl) | 2003-02-28 | 2008-12-31 | Servier S A Lab | Postopek za pripravo perindoprila in njegovih soli |
ATE307139T1 (de) | 2003-02-28 | 2005-11-15 | Servier Lab | Verfahren für die synthese von perindopril und seiner pharmazeutisch annehmbaren salze |
ES2231759T3 (es) * | 2003-03-12 | 2005-05-16 | Les Laboratoires Servier | Procedimiento para la sintesis de derivados de acido (2s,3as,7as)-1-(s)-alanil)-octahidro-1h-indol-2-carboxilico y su utilizacion en la sintesis de perindopril. |
ES2231760T3 (es) * | 2003-03-12 | 2005-05-16 | Les Laboratoires Servier | Nuevo procedimiento de sintesis del acido(2s, 3as,7as)perhidroindol-2-carboxilico y de sus esteres, y su aplicacion a la sintesis de perindopril. |
EP1321471B1 (fr) * | 2003-03-12 | 2005-05-04 | Les Laboratoires Servier | Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables |
WO2004099138A2 (en) * | 2003-05-12 | 2004-11-18 | Cipla Limited | Process for the preparation of perindopril |
DK1636185T3 (da) | 2003-06-24 | 2012-05-07 | Servier Lab | Nye krystalformer af Perindopril erbumin |
EP1367063B1 (fr) * | 2003-07-31 | 2006-08-23 | Les Laboratoires Servier | Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables |
DK1367062T3 (da) * | 2003-07-31 | 2007-01-02 | Servier Lab | Ny fremgangsmåde til syntese af perindopril og farmaceutisk acceptable salte heraf |
WO2005037788A1 (en) * | 2003-10-21 | 2005-04-28 | Lupin Ltd. | Novel method for preparation of crystalline perindopril erbumine |
EP1420029B9 (fr) * | 2003-12-10 | 2008-11-12 | Les Laboratoires Servier | Procédé de synthèse du perindopril et ses sels pharmaceutiquement acceptables |
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 |
ES2255872B1 (es) * | 2004-12-31 | 2007-08-16 | Quimica Sintetica, S.A. | Procedimiento para la preparacion de perindopril erbumina. |
EP1679072B9 (en) * | 2005-01-06 | 2009-09-02 | IPCA Laboratories Limited | Process for for synthesis of (2S,3aS,7aS)-1-(S)-alanyl-octahydro-1H-indole-2- carboxylic acid derivatives and use in the synthesis of perindopril |
US7291745B2 (en) * | 2005-03-21 | 2007-11-06 | Glenmark Pharmaceuticals Limited | Process for the preparation of perindopril |
JP2006290825A (ja) * | 2005-04-13 | 2006-10-26 | Shiono Chemical Co Ltd | アルファ型ペリンドプリルエルブミンの製造法 |
DE102005058166A1 (de) * | 2005-12-05 | 2007-06-06 | Hexal Ag | Matrixkontrolliertes transdermales System mit Amin-Salzen der ACE-Hemmer-Dicarbonsäuren |
WO2007085933A2 (en) * | 2006-01-25 | 2007-08-02 | Glenmark Pharmaceuticals Limited | Process for the preparation of n-[1-(s)-ethoxycarbonyl-1-butyl]-(s)-alanine-dmt complex and its use in the preparation of perindopril |
WO2008114270A1 (en) * | 2007-03-22 | 2008-09-25 | Aarti Healthcare Limited | Process for the preparation of perindopril erbumine salt and novel polymorph (s) thereof |
FR2961105B1 (fr) * | 2010-06-15 | 2013-02-08 | Servier Lab | Utilisation de l'association d'un inhibiteur du courant if sinusal et d'un inhibiteur de l'enzyme de conversion de l'angiotensine pour le traitement de l'insuffisance cardiaque |
WO2014057404A1 (en) * | 2012-10-10 | 2014-04-17 | Piramal Enterprises Limited | An improved process for preparation of perindopril intermediate |
WO2016178591A2 (en) | 2015-05-05 | 2016-11-10 | Gene Predit, Sa | Genetic markers and treatment of male obesity |
FR3050380B1 (fr) | 2016-04-20 | 2020-07-10 | Les Laboratoires Servier | Composition pharmaceutique comprenant un betabloquant, un inhibiteur de l'enzyme de conversion et un antihypertenseur ou un ains. |
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 (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0049658A1 (fr) * | 1980-10-02 | 1982-04-14 | Adir | Iminodiacides substitués, leur préparation et compositions pharmaceutiques les contenant |
EP0116842A2 (de) * | 1983-01-22 | 1984-08-29 | Boehringer Ingelheim Kg | Aminosäure-Derivate, Verfahren zu ihrer Herstellung und Verwendung |
EP0308341A1 (fr) * | 1987-09-17 | 1989-03-22 | Adir Et Compagnie | Procédé de synthèse industrielle du périndopril et de ses principaux intermédiaires de synthèse |
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 |
-
2000
- 2000-04-06 FR FR0004379A patent/FR2807431B1/fr not_active Expired - Fee Related
-
2001
- 2001-03-20 PL PL346555A patent/PL204471B1/pl unknown
- 2001-03-30 HU HU0101336A patent/HU227674B1/hu not_active IP Right Cessation
- 2001-04-05 CN CNB018073727A patent/CN1296355C/zh not_active Expired - Fee Related
- 2001-04-05 AT AT01921486T patent/ATE369338T1/de active
- 2001-04-05 NZ NZ52145401A patent/NZ521454A/en not_active IP Right Cessation
- 2001-04-05 PT PT01921486T patent/PT1268424E/pt unknown
- 2001-04-05 DE DE60129800T patent/DE60129800T2/de not_active Expired - Lifetime
- 2001-04-05 SK SK1418-2002A patent/SK286921B6/sk not_active IP Right Cessation
- 2001-04-05 GE GEAP20016679A patent/GEP20063797B/en unknown
- 2001-04-05 AU AU4847001A patent/AU4847001A/xx active Pending
- 2001-04-05 WO PCT/FR2001/001026 patent/WO2001058868A1/fr active IP Right Grant
- 2001-04-05 BR BRPI0109836-5A patent/BRPI0109836B1/pt not_active IP Right Cessation
- 2001-04-05 OA OA1200200306A patent/OA12242A/en unknown
- 2001-04-05 MX MXPA02009706A patent/MXPA02009706A/es active IP Right Grant
- 2001-04-05 ES ES01921486T patent/ES2291307T3/es not_active Expired - Lifetime
- 2001-04-05 EP EP01921486A patent/EP1268424B1/fr not_active Expired - Lifetime
- 2001-04-05 CZ CZ20023291A patent/CZ302575B6/cs not_active IP Right Cessation
- 2001-04-05 EA EA200201057A patent/EA005079B1/ru not_active IP Right Cessation
- 2001-04-05 RS YUP-738/02A patent/RS50808B/sr unknown
- 2001-04-05 KR KR10-2002-7013376A patent/KR100507616B1/ko not_active IP Right Cessation
- 2001-04-05 CA CA002405486A patent/CA2405486C/fr not_active Expired - Fee Related
- 2001-04-05 JP JP2001558419A patent/JP3939553B2/ja not_active Expired - Fee Related
- 2001-04-05 ME MEP-2008-670A patent/ME00441B/me unknown
- 2001-04-05 US US10/239,129 patent/US6835843B2/en not_active Expired - Lifetime
- 2001-04-05 AU AU2001248470A patent/AU2001248470B2/en not_active Ceased
- 2001-04-05 DK DK01921486T patent/DK1268424T3/da active
- 2001-04-05 AP APAP/P/2002/002630A patent/AP1385A/en active
- 2001-04-05 EE EEP200200575A patent/EE05032B1/xx not_active IP Right Cessation
- 2001-05-04 UA UA2002118786A patent/UA75070C2/uk unknown
-
2002
- 2002-09-16 ZA ZA200207419A patent/ZA200207419B/en unknown
- 2002-10-04 NO NO20024808A patent/NO324174B1/no not_active IP Right Cessation
- 2002-11-04 BG BG107249A patent/BG65984B1/bg unknown
- 2002-11-06 HR HR20020876A patent/HRP20020876B1/xx not_active IP Right Cessation
-
2003
- 2003-08-01 HK HK03105542A patent/HK1053309A1/xx not_active IP Right Cessation
-
2007
- 2007-10-16 CY CY20071101338T patent/CY1108522T1/el unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0049658A1 (fr) * | 1980-10-02 | 1982-04-14 | Adir | Iminodiacides substitués, leur préparation et compositions pharmaceutiques les contenant |
EP0116842A2 (de) * | 1983-01-22 | 1984-08-29 | Boehringer Ingelheim Kg | Aminosäure-Derivate, Verfahren zu ihrer Herstellung und Verwendung |
EP0308341A1 (fr) * | 1987-09-17 | 1989-03-22 | Adir Et Compagnie | Procédé de synthèse industrielle du périndopril et de ses principaux intermédiaires de synthèse |
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 |
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