NO333128B1 - Fremgangsmate for fremstilling av ¿ krystallinsk form av perindopril erbumin og fremgangsmate for fremstilling av et medikament inneholdende nevnte forbindelse - Google Patents
Fremgangsmate for fremstilling av ¿ krystallinsk form av perindopril erbumin og fremgangsmate for fremstilling av et medikament inneholdende nevnte forbindelse Download PDFInfo
- Publication number
- NO333128B1 NO333128B1 NO20060256A NO20060256A NO333128B1 NO 333128 B1 NO333128 B1 NO 333128B1 NO 20060256 A NO20060256 A NO 20060256A NO 20060256 A NO20060256 A NO 20060256A NO 333128 B1 NO333128 B1 NO 333128B1
- Authority
- NO
- Norway
- Prior art keywords
- crystalline form
- water
- perindopril erbumine
- tert
- methyl ether
- Prior art date
Links
- 229960003929 perindopril erbumine Drugs 0.000 title claims abstract description 34
- IYNMDWMQHSMDDE-MHXJNQAMSA-N perindopril erbumine Chemical compound CC(C)(C)N.C1CCC[C@@H]2N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(O)=O)C[C@@H]21 IYNMDWMQHSMDDE-MHXJNQAMSA-N 0.000 title claims abstract description 34
- 239000003814 drug Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 title 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
- 206010019280 Heart failures Diseases 0.000 claims abstract description 4
- 206010020772 Hypertension Diseases 0.000 claims abstract description 4
- 239000002244 precipitate Substances 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 7
- 238000002441 X-ray diffraction Methods 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 4
- 229910016523 CuKa Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 abstract description 17
- 238000002425 crystallisation Methods 0.000 abstract description 7
- 230000008025 crystallization Effects 0.000 abstract description 7
- 239000013543 active substance Substances 0.000 abstract description 3
- 238000010533 azeotropic distillation Methods 0.000 abstract description 2
- 238000010899 nucleation Methods 0.000 abstract 2
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 239000000725 suspension Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 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 description 5
- 229960002582 perindopril Drugs 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 102100030988 Angiotensin-converting enzyme Human genes 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 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 group 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 1
- 239000005541 ACE inhibitor Substances 0.000 description 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000001131 transforming 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH11092003 | 2003-06-24 | ||
| PCT/CH2004/000374 WO2004113293A1 (fr) | 2003-06-24 | 2004-06-18 | Nouvelles formes cristallines de perindopril erbumine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20060256L NO20060256L (no) | 2006-01-18 |
| NO333128B1 true NO333128B1 (no) | 2013-03-11 |
Family
ID=33520350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20060256A NO333128B1 (no) | 2003-06-24 | 2006-01-18 | Fremgangsmate for fremstilling av ¿ krystallinsk form av perindopril erbumin og fremgangsmate for fremstilling av et medikament inneholdende nevnte forbindelse |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7705046B2 (fr) |
| EP (1) | EP1636185B1 (fr) |
| JP (1) | JP2007507418A (fr) |
| KR (1) | KR20060035636A (fr) |
| CN (2) | CN101333181A (fr) |
| AT (1) | ATE540924T1 (fr) |
| AU (1) | AU2004249345B8 (fr) |
| BR (1) | BRPI0411966A (fr) |
| CA (1) | CA2530550C (fr) |
| CY (1) | CY1112597T1 (fr) |
| DK (1) | DK1636185T3 (fr) |
| EA (1) | EA008603B1 (fr) |
| ES (1) | ES2382171T3 (fr) |
| MX (1) | MXPA05013811A (fr) |
| NO (1) | NO333128B1 (fr) |
| NZ (1) | NZ544160A (fr) |
| PL (1) | PL1636185T3 (fr) |
| PT (1) | PT1636185E (fr) |
| SI (1) | SI1636185T1 (fr) |
| WO (1) | WO2004113293A1 (fr) |
| ZA (1) | ZA200600655B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG125976A1 (en) * | 2005-03-11 | 2006-10-30 | Servier Lab | New gama crystalline form of perindopril tert-butylamine salt, a process for its preparation and pharmaceutical compositions containing it |
| SG125975A1 (en) * | 2005-03-11 | 2006-10-30 | Servier Lab | New alpha crystalline form of perindopril tert-butylamine salt, a process for its preparation and pharmaceutical compositions containing it |
| WO2007017893A2 (fr) * | 2005-05-05 | 2007-02-15 | Arch Pharmalabs Limited | Preparation d'une nouvelle forme cristalline de perindopril erbumine monohydrate |
| WO2007017894A2 (fr) * | 2005-05-05 | 2007-02-15 | Arch Pharmalabs Limited | Preparation d'une nouvelle forme cristalline $g(h)(eta) de perindopril erbumine |
| US20090099370A1 (en) * | 2005-08-12 | 2009-04-16 | Sandoz Ag | Crystalline Form of Perindopril Erbumine |
| EP1943267B1 (fr) * | 2005-08-12 | 2011-03-16 | LEK Pharmaceuticals d.d. | Procede de preparation de perindopril erbumine |
| EP1815857A1 (fr) | 2006-02-02 | 2007-08-08 | LEK Pharmaceuticals D.D. | Composition pharmaceutique comprenant du perindopril |
| WO2007092758A2 (fr) * | 2006-02-03 | 2007-08-16 | Dr. Reddy's Laboratories Ltd. | Formes cristallines de périndopril erbumine |
| EA200600630A1 (ru) * | 2006-04-20 | 2007-02-27 | ИСМАГИЛОВ, Искандар Халиуллович | ζ-ЗЕТА ФОРМА ПЕРИНДОПРИЛ ЭРБУМИНА |
| WO2008050185A2 (fr) * | 2006-10-26 | 2008-05-02 | Glenmark Pharmaceuticals Limited | Nouveaux polymorphes de la périndopril erbumine |
| WO2008114270A1 (fr) * | 2007-03-22 | 2008-09-25 | Aarti Healthcare Limited | Procédé de préparation d'un sel de périndopril erbumine et son ou ses nouveaux polymorphes |
| SI22543A (sl) | 2007-06-27 | 2008-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nove soli perindoprila |
| PT105315B (pt) | 2010-09-29 | 2013-01-16 | Inst Superior Tecnico | Uma nova forma cristalina hidratada de erbumina de perindopril, métodos para a sua preparação e sua utilização em preparações farmacêuticas |
Family Cites Families (11)
| 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 |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| DE69333521T2 (de) * | 1993-01-08 | 2004-09-23 | Kanegafuchi Kagaku Kogyo K.K. | Verfahren zur Kristallisierung von N2-((S)-1-ethoxycarbonyl-3-phenylpropyl)-N6-trifluoroacetyl-L-lysyl-L-prolin |
| FR2807431B1 (fr) | 2000-04-06 | 2002-07-19 | Adir | Nouveau procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| US20070178166A1 (en) * | 2005-12-15 | 2007-08-02 | Acusphere, Inc. | Processes for making particle-based pharmaceutical formulations for pulmonary or nasal administration |
-
2004
- 2004-06-18 CA CA2530550A patent/CA2530550C/fr not_active Expired - Fee Related
- 2004-06-18 KR KR1020057024852A patent/KR20060035636A/ko not_active Ceased
- 2004-06-18 WO PCT/CH2004/000374 patent/WO2004113293A1/fr not_active Ceased
- 2004-06-18 NZ NZ544160A patent/NZ544160A/en not_active IP Right Cessation
- 2004-06-18 BR BRPI0411966-5A patent/BRPI0411966A/pt not_active Application Discontinuation
- 2004-06-18 PT PT04737029T patent/PT1636185E/pt unknown
- 2004-06-18 US US10/560,464 patent/US7705046B2/en not_active Expired - Fee Related
- 2004-06-18 EP EP04737029A patent/EP1636185B1/fr not_active Expired - Lifetime
- 2004-06-18 CN CNA2008100912488A patent/CN101333181A/zh active Pending
- 2004-06-18 AU AU2004249345A patent/AU2004249345B8/en not_active Ceased
- 2004-06-18 MX MXPA05013811A patent/MXPA05013811A/es active IP Right Grant
- 2004-06-18 SI SI200431851T patent/SI1636185T1/sl unknown
- 2004-06-18 EA EA200501859A patent/EA008603B1/ru not_active IP Right Cessation
- 2004-06-18 ES ES04737029T patent/ES2382171T3/es not_active Expired - Lifetime
- 2004-06-18 JP JP2006515624A patent/JP2007507418A/ja active Pending
- 2004-06-18 AT AT04737029T patent/ATE540924T1/de active
- 2004-06-18 DK DK04737029.1T patent/DK1636185T3/da active
- 2004-06-18 CN CNB2004800178672A patent/CN100395235C/zh not_active Expired - Fee Related
- 2004-06-18 PL PL04737029T patent/PL1636185T3/pl unknown
-
2006
- 2006-01-18 NO NO20060256A patent/NO333128B1/no not_active IP Right Cessation
- 2006-01-23 ZA ZA200600655A patent/ZA200600655B/en unknown
-
2010
- 2010-03-09 US US12/720,250 patent/US7981921B2/en not_active Expired - Fee Related
-
2012
- 2012-04-04 CY CY20121100334T patent/CY1112597T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN101333181A (zh) | 2008-12-31 |
| JP2007507418A (ja) | 2007-03-29 |
| WO2004113293A1 (fr) | 2004-12-29 |
| US7981921B2 (en) | 2011-07-19 |
| DK1636185T3 (da) | 2012-05-07 |
| AU2004249345B8 (en) | 2009-06-25 |
| EA200501859A1 (ru) | 2006-06-30 |
| CA2530550C (fr) | 2017-04-04 |
| AU2004249345A1 (en) | 2004-12-29 |
| CY1112597T1 (el) | 2016-02-10 |
| EA008603B1 (ru) | 2007-06-29 |
| EP1636185A1 (fr) | 2006-03-22 |
| MXPA05013811A (es) | 2006-06-27 |
| KR20060035636A (ko) | 2006-04-26 |
| ATE540924T1 (de) | 2012-01-15 |
| NO20060256L (no) | 2006-01-18 |
| PL1636185T3 (pl) | 2012-12-31 |
| CN100395235C (zh) | 2008-06-18 |
| US20100160404A1 (en) | 2010-06-24 |
| PT1636185E (pt) | 2012-04-16 |
| EP1636185B1 (fr) | 2012-01-11 |
| AU2004249345B2 (en) | 2009-02-26 |
| NZ544160A (en) | 2008-07-31 |
| BRPI0411966A (pt) | 2006-08-29 |
| US20070135512A1 (en) | 2007-06-14 |
| HK1093984A1 (zh) | 2007-03-16 |
| ZA200600655B (en) | 2007-05-30 |
| SI1636185T1 (sl) | 2012-06-29 |
| CN1812971A (zh) | 2006-08-02 |
| CA2530550A1 (fr) | 2004-12-08 |
| ES2382171T3 (es) | 2012-06-06 |
| US7705046B2 (en) | 2010-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: LES LABORATOIRES SERVIER Free format text: NEW ADDRESS: 35 RUE DE VERDUN, FR-92284 SURESNES CEDEX, FR |
|
| MM1K | Lapsed by not paying the annual fees |