EA011322B1 - Способ получения периндоприла и его солей - Google Patents
Способ получения периндоприла и его солей Download PDFInfo
- Publication number
- EA011322B1 EA011322B1 EA200602117A EA200602117A EA011322B1 EA 011322 B1 EA011322 B1 EA 011322B1 EA 200602117 A EA200602117 A EA 200602117A EA 200602117 A EA200602117 A EA 200602117A EA 011322 B1 EA011322 B1 EA 011322B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- compound
- perindopril
- salt
- chloride
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 31
- 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 claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 229960002582 perindopril Drugs 0.000 title claims description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 229960003767 alanine Drugs 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 238000005755 formation reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000006664 bond formation reaction Methods 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000005541 ACE inhibitor Substances 0.000 abstract 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- CQYBNXGHMBNGCG-FXQIFTODSA-N (2s,3as,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2[NH2+][C@H](C(=O)[O-])C[C@@H]21 CQYBNXGHMBNGCG-FXQIFTODSA-N 0.000 description 4
- CQYBNXGHMBNGCG-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCCC2NC(C(=O)O)CC21 CQYBNXGHMBNGCG-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000012223 aqueous fraction Substances 0.000 description 3
- 239000002037 dichloromethane fraction Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- -1 octahydroindole-2-carboxylic acid benzyl ester Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000005051 trimethylchlorosilane Substances 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
- ZNAYHAPFFQRGES-UHFFFAOYSA-N benzyl 1-[2-[(1-ethoxy-1-oxopentan-2-yl)amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylate Chemical compound CCOC(=O)C(CCC)NC(C)C(=O)N1C2CCCCC2CC1C(=O)OCC1=CC=CC=C1 ZNAYHAPFFQRGES-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 150000001483 arginine derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 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
- C07D209/42—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
- 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
- A61P9/12—Antihypertensives
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)
- Peptides Or Proteins (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI200400143A SI21800A (sl) | 2004-05-14 | 2004-05-14 | Nov postopek sinteze perindoprila |
| SI200400235A SI21852A (sl) | 2004-05-14 | 2004-08-05 | Nov postopek sinteze perindoprila |
| PCT/EP2005/005048 WO2005113500A1 (en) | 2004-05-14 | 2005-05-10 | Process for the preparation of perindopril and salts thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200602117A1 EA200602117A1 (ru) | 2007-04-27 |
| EA011322B1 true EA011322B1 (ru) | 2009-02-27 |
Family
ID=34969318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200602117A EA011322B1 (ru) | 2004-05-14 | 2005-05-10 | Способ получения периндоприла и его солей |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7674814B2 (https=) |
| EP (1) | EP1753720B1 (https=) |
| JP (1) | JP5032983B2 (https=) |
| AU (1) | AU2005245087B2 (https=) |
| CA (1) | CA2566754C (https=) |
| CY (1) | CY1115222T1 (https=) |
| DK (1) | DK1753720T3 (https=) |
| EA (1) | EA011322B1 (https=) |
| ES (1) | ES2466248T3 (https=) |
| HR (1) | HRP20140487T1 (https=) |
| NO (1) | NO337892B1 (https=) |
| PL (1) | PL1753720T3 (https=) |
| PT (1) | PT1753720E (https=) |
| SI (3) | SI21800A (https=) |
| UA (1) | UA83139C2 (https=) |
| WO (1) | WO2005113500A1 (https=) |
| ZA (1) | ZA200609915B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT1729739T (lt) * | 2004-03-29 | 2016-11-10 | Les Laboratoires Servier | Kietos farmacinės kompozicijos gamybos būdas |
| 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 |
| SI22543A (sl) | 2007-06-27 | 2008-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nove soli perindoprila |
| WO2016178591A2 (en) | 2015-05-05 | 2016-11-10 | Gene Predit, Sa | Genetic markers and treatment of male obesity |
| PH12018502155B1 (en) | 2016-04-20 | 2024-03-27 | Servier Lab | Pharmaceutical composition comprising a beta blocker, a converting enzyme inhibitor and an antihypertensive or an nsaid |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19721290A1 (de) * | 1996-05-22 | 1997-12-11 | Krka Tovarna Zdravil D D | Verfahren zur Herstellung von Verbindungen mit ACE-Hemmwirkung |
| WO2004075889A1 (en) * | 2003-02-28 | 2004-09-10 | Lupin Limited | Process for preparation of perindopril and salts thereof |
Family Cites Families (39)
| 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 |
| US4508729A (en) * | 1979-12-07 | 1985-04-02 | Adir | Substituted iminodiacids, their preparation and pharmaceutical compositions containing them |
| US4350704A (en) * | 1980-10-06 | 1982-09-21 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids |
| IE52663B1 (en) | 1980-04-02 | 1988-01-20 | Warner Lambert Co | Substituted acyl derivatives of octahydro-1h-indole-2-carboxylic acids |
| US4425355A (en) * | 1981-02-17 | 1984-01-10 | Warner-Lambert Company | Substituted acyl derivatives of chair form of octahydro-1H-indole-2-carboxylic acids |
| US4743450A (en) | 1987-02-24 | 1988-05-10 | Warner-Lambert Company | Stabilized compositions |
| FR2620700B1 (fr) | 1987-09-17 | 1990-06-01 | Adir | Procede de synthese d'alpha amino acides n alkyles et leurs esters. application a la synthese de carboxyalkyl dipeptides |
| FR2620703B1 (fr) * | 1987-09-17 | 1991-10-04 | Adir | Procede de synthese industrielle de l'acide perhydroindole carboxylique - 2(2s, 3as, 7as). application a la synthese de carboxyalkyl dipeptides |
| 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 |
| US5258525A (en) * | 1991-03-27 | 1993-11-02 | Mcneilab, Inc. | Processes for preparing [2S-(2α,3aβ,7aβ)]octahydro-1H-indole-2-carboxylic acid and esters |
| SI9111842A (sl) * | 1991-11-25 | 1998-04-30 | Krka | Stabilna formulacija soli enalaprila, postopek za njeno pripravo in njena uporaba |
| FR2771010B1 (fr) * | 1997-11-19 | 2003-08-15 | Adir | Utilisation d'une combinaison d'un inhibiteur de l'enzyme de conversion de l'angiotensine et d'un diuretique pour le traitement des desordres microcirculatoires |
| 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 |
| FR2807431B1 (fr) * | 2000-04-06 | 2002-07-19 | Adir | Nouveau procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables |
| 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 |
| FR2811318B1 (fr) | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline gamma du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2811320B1 (fr) * | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline alpha du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2811319B1 (fr) * | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline beta du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| DE10131217A1 (de) * | 2001-06-28 | 2003-01-09 | Solvay Pharm Gmbh | 3-Phenyl-3,7-diazabicyclo 3,3,1 nonan-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| AU2002334939A1 (en) * | 2001-10-12 | 2003-04-22 | Eugene R. Cooper | Compositions having a combination of particles for immediate release and for controlled release |
| EA007981B1 (ru) | 2002-01-15 | 2007-02-27 | Актавис Груп Хф. | Фармацевтический состав, содержащий хинаприл или фармацевтически приемлемую его соль |
| SI1333026T1 (sl) | 2002-01-30 | 2007-10-31 | Servier Lab | Postopek priprave perindoprila visoke äśistoäśe in intermediatov uporabnih v sintezi |
| WO2003075842A2 (en) | 2002-03-08 | 2003-09-18 | Teva Pharmeceuticals Usa, Inc. | Stable formulations of angiotensin converting enzyme (ace) inhibitors |
| FR2838648B1 (fr) | 2002-04-18 | 2004-05-21 | Servier Lab | Nouveau sel de perindopril et les compositions pharmaceutiques qui le contiennent |
| JP4533134B2 (ja) * | 2002-06-10 | 2010-09-01 | エラン ファーマ インターナショナル，リミティド | ナノ粒子ポリコサノール製剤および新規なポリコサノールの組合せ |
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| DK1338591T3 (da) | 2003-02-28 | 2006-01-23 | Servier Lab | Fremgangsmåde til syntese af (2S,3aS,7aS)-perhydroindol-2-carboxylsyre og estere heraf samt anvendelse heraf ved syntese af 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. |
| ES2256689T3 (es) * | 2003-06-30 | 2006-07-16 | Les Laboratoires Servier | Nuevo procedimiento de sintesis del perindopril y de sus sales farmaceuticamente aceptables. |
| US6869963B2 (en) * | 2003-07-11 | 2005-03-22 | Sandoz Ag | Stable pharmaceutical compositions containing an ACE inhibitor |
| GB2404336A (en) | 2003-07-30 | 2005-02-02 | Cipla Ltd | Stabilisation of therapeutic agents using a carbonate salt of an amino acid, preferably in the presence of a saccharide, & pharmaceutical compositions thereof |
| ES2271498T3 (es) * | 2003-07-31 | 2007-04-16 | Les Laboratoires Servier | Nuevo procedimiento de sintesis de perindopril y de sus sales farmaceuticamente aceptables. |
| SI1367062T1 (sl) * | 2003-07-31 | 2006-12-31 | Servier Lab | Nov postopek sinteze perindoprila in njegovih farmacevtsko sprejemljivih soli |
| 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 |
| 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 |
| 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 |
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-
2004
- 2004-05-14 SI SI200400143A patent/SI21800A/sl not_active IP Right Cessation
- 2004-08-05 SI SI200400235A patent/SI21852A/sl not_active IP Right Cessation
-
2005
- 2005-05-10 HR HRP20140487TT patent/HRP20140487T1/hr unknown
- 2005-05-10 SI SI200531867T patent/SI1753720T1/sl unknown
- 2005-05-10 AU AU2005245087A patent/AU2005245087B2/en not_active Ceased
- 2005-05-10 JP JP2007512069A patent/JP5032983B2/ja not_active Expired - Fee Related
- 2005-05-10 DK DK05748048.5T patent/DK1753720T3/da active
- 2005-05-10 EP EP05748048.5A patent/EP1753720B1/en not_active Expired - Lifetime
- 2005-05-10 CA CA2566754A patent/CA2566754C/en not_active Expired - Fee Related
- 2005-05-10 WO PCT/EP2005/005048 patent/WO2005113500A1/en not_active Ceased
- 2005-05-10 US US11/568,908 patent/US7674814B2/en not_active Expired - Fee Related
- 2005-05-10 PL PL05748048T patent/PL1753720T3/pl unknown
- 2005-05-10 PT PT57480485T patent/PT1753720E/pt unknown
- 2005-05-10 ES ES05748048.5T patent/ES2466248T3/es not_active Expired - Lifetime
- 2005-05-10 UA UAA200613250A patent/UA83139C2/uk unknown
- 2005-05-10 EA EA200602117A patent/EA011322B1/ru not_active IP Right Cessation
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2006
- 2006-11-28 ZA ZA200609915A patent/ZA200609915B/en unknown
- 2006-12-11 NO NO20065695A patent/NO337892B1/no not_active IP Right Cessation
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2014
- 2014-07-01 CY CY20141100483T patent/CY1115222T1/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19721290A1 (de) * | 1996-05-22 | 1997-12-11 | Krka Tovarna Zdravil D D | Verfahren zur Herstellung von Verbindungen mit ACE-Hemmwirkung |
| WO2004075889A1 (en) * | 2003-02-28 | 2004-09-10 | Lupin Limited | Process for preparation of perindopril and salts thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| PL1753720T3 (pl) | 2014-09-30 |
| AU2005245087A1 (en) | 2005-12-01 |
| JP5032983B2 (ja) | 2012-09-26 |
| UA83139C2 (uk) | 2008-06-10 |
| EP1753720B1 (en) | 2014-05-07 |
| AU2005245087B2 (en) | 2010-12-16 |
| EA200602117A1 (ru) | 2007-04-27 |
| US7674814B2 (en) | 2010-03-09 |
| ES2466248T3 (es) | 2014-06-09 |
| US20080051584A1 (en) | 2008-02-28 |
| WO2005113500A1 (en) | 2005-12-01 |
| ZA200609915B (en) | 2008-05-28 |
| DK1753720T3 (da) | 2014-06-30 |
| CA2566754C (en) | 2012-09-18 |
| CY1115222T1 (el) | 2017-01-04 |
| NO20065695L (no) | 2006-12-11 |
| EP1753720A1 (en) | 2007-02-21 |
| SI21800A (sl) | 2005-12-31 |
| SI21852A (sl) | 2006-02-28 |
| NO337892B1 (no) | 2016-07-04 |
| JP2007537189A (ja) | 2007-12-20 |
| HRP20140487T1 (hr) | 2014-07-04 |
| CA2566754A1 (en) | 2005-12-01 |
| PT1753720E (pt) | 2014-08-04 |
| SI1753720T1 (sl) | 2014-08-29 |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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