NO323445B1 - Ny <gamma>-krystallinsk form av perindopril tert-butylaminsalt, fremgangsmate for dens fremstilling og farmasoytiske sammensetninger inneholdende den - Google Patents
Ny <gamma>-krystallinsk form av perindopril tert-butylaminsalt, fremgangsmate for dens fremstilling og farmasoytiske sammensetninger inneholdende den Download PDFInfo
- Publication number
- NO323445B1 NO323445B1 NO20030051A NO20030051A NO323445B1 NO 323445 B1 NO323445 B1 NO 323445B1 NO 20030051 A NO20030051 A NO 20030051A NO 20030051 A NO20030051 A NO 20030051A NO 323445 B1 NO323445 B1 NO 323445B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- crystalline form
- preparation
- pharmaceutical composition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- IYNMDWMQHSMDDE-MHXJNQAMSA-N perindopril erbumine Chemical class 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 description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 4
- 101800000734 Angiotensin-1 Proteins 0.000 claims description 3
- 102400000344 Angiotensin-1 Human genes 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 239000002934 diuretic Substances 0.000 claims description 3
- 230000001882 diuretic effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- NDDAHWYSQHTHNT-UHFFFAOYSA-N indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 claims description 2
- 229960004569 indapamide Drugs 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000010586 diagram Methods 0.000 abstract description 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 description 6
- 229960002582 perindopril Drugs 0.000 description 6
- 238000009472 formulation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- 102000005862 Angiotensin II Human genes 0.000 description 1
- 101800000733 Angiotensin-2 Proteins 0.000 description 1
- 101800004538 Bradykinin Proteins 0.000 description 1
- 102400000967 Bradykinin Human genes 0.000 description 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 1
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
- 229950006323 angiotensin ii Drugs 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0008791A FR2811318B1 (fr) | 2000-07-06 | 2000-07-06 | Nouvelle forme cristalline gamma du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| PCT/FR2001/002169 WO2001083439A2 (fr) | 2000-07-06 | 2001-07-06 | NOUVELLE FORME CRISTALLINE η DU SEL DE TERT-BUTYLAMINE DU PERINDOPRIL, SON PROCEDE DE PREPARATION, ET LES COMPOSITIONS PHARMACEUTIQUES QUI LA CONTIENNENT |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20030051L NO20030051L (no) | 2003-01-06 |
| NO20030051D0 NO20030051D0 (no) | 2003-01-06 |
| NO323445B1 true NO323445B1 (no) | 2007-05-07 |
Family
ID=8852170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030051A NO323445B1 (no) | 2000-07-06 | 2003-01-06 | Ny <gamma>-krystallinsk form av perindopril tert-butylaminsalt, fremgangsmate for dens fremstilling og farmasoytiske sammensetninger inneholdende den |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US20030158121A1 (et) |
| EP (1) | EP1296948B1 (et) |
| JP (2) | JP3592296B2 (et) |
| KR (1) | KR100513572B1 (et) |
| CN (1) | CN1328258C (et) |
| AP (1) | AP1452A (et) |
| AR (1) | AR029570A1 (et) |
| AT (1) | ATE249435T1 (et) |
| AU (2) | AU7642001A (et) |
| BG (1) | BG66239B1 (et) |
| BR (1) | BR0112211A (et) |
| CA (1) | CA2415447C (et) |
| CZ (1) | CZ302022B6 (et) |
| DE (1) | DE60100761T2 (et) |
| DK (1) | DK1296948T3 (et) |
| EA (1) | EA004275B1 (et) |
| EE (1) | EE05286B1 (et) |
| ES (1) | ES2206423T3 (et) |
| FR (1) | FR2811318B1 (et) |
| GE (1) | GEP20043362B (et) |
| HK (1) | HK1058199A1 (et) |
| HR (1) | HRP20030078B1 (et) |
| HU (1) | HU228115B1 (et) |
| ME (1) | ME01367B (et) |
| MX (1) | MXPA02012904A (et) |
| NO (1) | NO323445B1 (et) |
| NZ (1) | NZ523311A (et) |
| OA (1) | OA12306A (et) |
| PL (1) | PL348491A1 (et) |
| PT (1) | PT1296948E (et) |
| RS (1) | RS51621B (et) |
| SI (1) | SI1296948T1 (et) |
| SK (1) | SK287452B6 (et) |
| UA (1) | UA57187C2 (et) |
| WO (1) | WO2001083439A2 (et) |
| ZA (1) | ZA200300025B (et) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2834893B1 (fr) * | 2002-01-23 | 2004-02-27 | Servier Lab | Composition pharmaceutique orodispersible de 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 |
| CN100395235C (zh) | 2003-06-24 | 2008-06-18 | 瑟维尔实验室 | 培哚普利特丁胺的新晶形 |
| WO2005019173A1 (en) * | 2003-08-21 | 2005-03-03 | Hetero Drugs Limited | Process for pure perindopril tert-butylamine salt |
| DE60330603D1 (de) * | 2003-10-21 | 2010-01-28 | Servier Lab | Verfahren zur herstellung kristallinem perindopril erbumin |
| SI21703A (en) | 2004-01-14 | 2005-08-31 | Lek Farmacevtska Druzba Dd | Inclusion complexes of perindopril, procedure of their preparation, pharmaceutical compositions containing these complexes and their application in treatment of hypertensia |
| SI21704A (en) * | 2004-01-14 | 2005-08-31 | Lek Farmacevtska Druzba Dd | New crystal form of perindopril, procedure of its preparation, pharmaceutical preparations containing this form and their application in treatment of hypertensia |
| WO2005094793A1 (en) * | 2004-03-29 | 2005-10-13 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Process for preparing a solid pharmaceutical composition |
| SI21800A (sl) | 2004-05-14 | 2005-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nov postopek sinteze perindoprila |
| SI21881A (sl) | 2004-10-15 | 2006-04-30 | Diagen, Smartno Pri Ljubljani, D.O.O. | Nove kristalne oblike perindopril erbumin hidratov, postopek za njihovo pripravo in farmacevtske oblike, ki vsebujejo te spojine |
| 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 |
| 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 |
| WO2007017894A2 (en) * | 2005-05-05 | 2007-02-15 | Arch Pharmalabs Limited | PREPARATION OF NOVEL CRYSTALLINE η(ETA) FORM OF PERINDOPRIL ERBUMINE |
| US20090099370A1 (en) * | 2005-08-12 | 2009-04-16 | Sandoz Ag | Crystalline Form of Perindopril Erbumine |
| UA92613C2 (ru) * | 2005-08-12 | 2010-11-25 | Лек Фармасьютиклз Д.Д. | Способ получения кристаллической формы d эрбумина периндоприла |
| EP1815857A1 (en) | 2006-02-02 | 2007-08-08 | LEK Pharmaceuticals D.D. | A pharmaceutical composition comprising perindopril |
| WO2007092758A2 (en) * | 2006-02-03 | 2007-08-16 | Dr. Reddy's Laboratories Ltd. | Crystalline forms of perindopril erbumine |
| FR2897866B1 (fr) * | 2006-02-28 | 2008-04-18 | Servier Lab | Forme cristalline alpha du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2897865B1 (fr) * | 2006-02-28 | 2008-04-18 | Servier Lab | Forme cristalline beta du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| EP2137148A1 (en) * | 2007-03-22 | 2009-12-30 | Aarti Healthcare Limited | Process for the preparation of perindopril erbumine salt and novel polymorph (s) thereof |
| WO2008120241A2 (en) * | 2007-03-29 | 2008-10-09 | Ipca Laboratories Limited | Novel alcohol solvates of perindopril erbumine |
| SI22543A (sl) * | 2007-06-27 | 2008-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nove soli perindoprila |
| WO2009157018A2 (en) * | 2008-06-24 | 2009-12-30 | Matrix Laboratories Ltd | Novel polymorphic forms of perindopril (l)-arginine and process for the preparation thereof |
| KR200453510Y1 (ko) * | 2009-02-09 | 2011-05-11 | 윤유원 | 튀김유 정제기 |
| KR101041878B1 (ko) * | 2009-03-26 | 2011-06-15 | 신준호 | 튀김장치용 찌꺼기 제거장치 |
| SI23149A (sl) | 2009-09-21 | 2011-03-31 | Silverstone Pharma | Nove benzatinske soli ACE inhibitorjev, postopek za njihovo pripravo in njihova uporaba za zdravljenje kardiovaskularnih bolezni |
| 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 |
| EP3842035A1 (en) | 2019-12-23 | 2021-06-30 | KRKA, d.d., Novo mesto | Composition for the preparation of perindopril arginine granules, a method for their preparation and pharmaceutical composition comprising the granules |
Family Cites Families (6)
| 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 |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| 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 |
| 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 |
| 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 |
-
2000
- 2000-07-06 FR FR0008791A patent/FR2811318B1/fr not_active Expired - Fee Related
-
2001
- 2001-06-07 UA UA2003021019A patent/UA57187C2/uk unknown
- 2001-07-05 HU HU0102814A patent/HU228115B1/hu not_active IP Right Cessation
- 2001-07-06 US US10/312,903 patent/US20030158121A1/en not_active Abandoned
- 2001-07-06 SK SK150-2003A patent/SK287452B6/sk not_active IP Right Cessation
- 2001-07-06 EE EEP200300003A patent/EE05286B1/et not_active IP Right Cessation
- 2001-07-06 PT PT01954060T patent/PT1296948E/pt unknown
- 2001-07-06 GE GE5074A patent/GEP20043362B/en unknown
- 2001-07-06 KR KR10-2003-7000117A patent/KR100513572B1/ko not_active IP Right Cessation
- 2001-07-06 AT AT01954060T patent/ATE249435T1/de active
- 2001-07-06 SI SI200130029T patent/SI1296948T1/xx unknown
- 2001-07-06 CZ CZ20030358A patent/CZ302022B6/cs not_active IP Right Cessation
- 2001-07-06 EA EA200300104A patent/EA004275B1/ru not_active IP Right Cessation
- 2001-07-06 OA OA1200200399A patent/OA12306A/en unknown
- 2001-07-06 CA CA002415447A patent/CA2415447C/fr not_active Expired - Fee Related
- 2001-07-06 AR ARP010103224A patent/AR029570A1/es not_active Application Discontinuation
- 2001-07-06 NZ NZ523311A patent/NZ523311A/en not_active IP Right Cessation
- 2001-07-06 PL PL01348491A patent/PL348491A1/xx not_active Application Discontinuation
- 2001-07-06 BR BR0112211-8A patent/BR0112211A/pt not_active Application Discontinuation
- 2001-07-06 RS YU100302A patent/RS51621B/sr unknown
- 2001-07-06 AU AU7642001A patent/AU7642001A/xx active Pending
- 2001-07-06 CN CNB018123538A patent/CN1328258C/zh not_active Expired - Fee Related
- 2001-07-06 AP APAP/P/2002/002709A patent/AP1452A/en active
- 2001-07-06 JP JP2001580868A patent/JP3592296B2/ja not_active Expired - Fee Related
- 2001-07-06 MX MXPA02012904A patent/MXPA02012904A/es active IP Right Grant
- 2001-07-06 ES ES01954060T patent/ES2206423T3/es not_active Expired - Lifetime
- 2001-07-06 DE DE60100761T patent/DE60100761T2/de not_active Expired - Lifetime
- 2001-07-06 DK DK01954060T patent/DK1296948T3/da active
- 2001-07-06 ME MEP-2008-672A patent/ME01367B/me unknown
- 2001-07-06 EP EP01954060A patent/EP1296948B1/fr not_active Expired - Lifetime
- 2001-07-06 WO PCT/FR2001/002169 patent/WO2001083439A2/fr active IP Right Grant
- 2001-07-06 AU AU2001276420A patent/AU2001276420B2/en not_active Ceased
-
2003
- 2003-01-02 ZA ZA200300025A patent/ZA200300025B/en unknown
- 2003-01-06 NO NO20030051A patent/NO323445B1/no not_active IP Right Cessation
- 2003-02-05 BG BG107534A patent/BG66239B1/bg unknown
- 2003-02-06 HR HR20030078A patent/HRP20030078B1/xx not_active IP Right Cessation
-
2004
- 2004-02-12 HK HK04100948A patent/HK1058199A1/xx not_active IP Right Cessation
- 2004-03-29 US US10/811,727 patent/US20040248817A1/en not_active Abandoned
- 2004-07-13 JP JP2004206157A patent/JP5016184B2/ja not_active Expired - Fee Related
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