NO323446B1 - Ny <beta>-krystallinsk form av perindopril tert-butylaminsalt, fremgangsmate for dens fremstilling og farmasoytiske sammensetninger inneholdende den - Google Patents
Ny <beta>-krystallinsk form av perindopril tert-butylaminsalt, fremgangsmate for dens fremstilling og farmasoytiske sammensetninger inneholdende den Download PDFInfo
- Publication number
- NO323446B1 NO323446B1 NO20030050A NO20030050A NO323446B1 NO 323446 B1 NO323446 B1 NO 323446B1 NO 20030050 A NO20030050 A NO 20030050A NO 20030050 A NO20030050 A NO 20030050A NO 323446 B1 NO323446 B1 NO 323446B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- preparation
- crystalline form
- pharmaceutical composition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 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 10
- 238000002360 preparation method Methods 0.000 title claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 238000000634 powder X-ray diffraction Methods 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
- 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
- 238000004519 manufacturing process Methods 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
- 239000003814 drug Substances 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 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 7
- 229960002582 perindopril Drugs 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 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
- 238000002441 X-ray diffraction Methods 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
- 235000013312 flour Nutrition 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
- 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
- 239000000725 suspension 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
- 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
- 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)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0008792A FR2811319B1 (fr) | 2000-07-06 | 2000-07-06 | Nouvelle forme cristalline beta du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| PCT/FR2001/002168 WO2001087836A1 (fr) | 2000-07-06 | 2001-07-06 | Nouvelle forme cristalline $g(b) du sel de tert-butylamine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20030050L NO20030050L (no) | 2003-01-06 |
| NO20030050D0 NO20030050D0 (no) | 2003-01-06 |
| NO323446B1 true NO323446B1 (no) | 2007-05-07 |
Family
ID=8852171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030050A NO323446B1 (no) | 2000-07-06 | 2003-01-06 | Ny <beta>-krystallinsk form av perindopril tert-butylaminsalt, fremgangsmate for dens fremstilling og farmasoytiske sammensetninger inneholdende den |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US20040029813A1 (me) |
| EP (2) | EP1676839A3 (me) |
| JP (2) | JP3592297B2 (me) |
| KR (1) | KR100513571B1 (me) |
| CN (1) | CN1328260C (me) |
| AP (1) | AP1407A (me) |
| AR (1) | AR029571A1 (me) |
| AT (1) | ATE324367T1 (me) |
| AU (2) | AU7641901A (me) |
| BG (1) | BG66131B1 (me) |
| BR (1) | BR0112244A (me) |
| CA (1) | CA2415442C (me) |
| CZ (1) | CZ301765B6 (me) |
| DE (1) | DE60119107T2 (me) |
| DK (1) | DK1294689T3 (me) |
| EA (1) | EA004874B1 (me) |
| EE (1) | EE05285B1 (me) |
| ES (1) | ES2262666T3 (me) |
| FR (1) | FR2811319B1 (me) |
| GE (1) | GEP20043360B (me) |
| HK (1) | HK1058200A1 (me) |
| HR (2) | HRP20030079B8 (me) |
| HU (1) | HU227673B1 (me) |
| ME (1) | ME00440B (me) |
| MX (1) | MXPA02012921A (me) |
| NO (1) | NO323446B1 (me) |
| NZ (1) | NZ523234A (me) |
| OA (1) | OA12305A (me) |
| PL (1) | PL348493A1 (me) |
| PT (1) | PT1294689E (me) |
| RS (1) | RS51717B (me) |
| SI (1) | SI1294689T1 (me) |
| SK (1) | SK286918B6 (me) |
| UA (1) | UA57189C2 (me) |
| WO (1) | WO2001087836A1 (me) |
| ZA (1) | ZA200300024B (me) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| ATE540924T1 (de) * | 2003-06-24 | 2012-01-15 | Servier Lab | Neue kristalline formen von perindopril erbumine |
| 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 |
| ES2603856T3 (es) * | 2004-03-29 | 2017-03-01 | Les Laboratoires Servier | Procedimiento para preparar una composición farmacéutica sólida |
| 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 |
| 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 |
| 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 |
| 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 |
| CA2618561C (en) * | 2005-08-12 | 2014-04-29 | Lek Pharmaceuticals D.D. | A process for the preparation of perindopril erbumine |
| 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 |
| WO2008050185A2 (en) * | 2006-10-26 | 2008-05-02 | Glenmark Pharmaceuticals Limited | Novel polymorphs of perindopril erbumine |
| 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 |
| DK2318365T3 (en) * | 2008-06-24 | 2015-11-23 | Mylan Lab Ltd | NOVEL polymorphic forms of perindopril (L) -arginine AND PROCESS FOR PREPARATION THEREOF |
| 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 |
| CN106432042A (zh) * | 2015-08-13 | 2017-02-22 | 南京华威医药科技开发有限公司 | 尼达尼布乙磺酸水合物的药物新晶型 |
| 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 (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| 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 |
| 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 |
-
2000
- 2000-07-06 FR FR0008792A patent/FR2811319B1/fr not_active Expired - Fee Related
-
2001
- 2001-06-07 UA UA2003021021A patent/UA57189C2/uk unknown
- 2001-07-05 HU HU0102813A patent/HU227673B1/hu not_active IP Right Cessation
- 2001-07-06 AU AU7641901A patent/AU7641901A/xx active Pending
- 2001-07-06 DE DE60119107T patent/DE60119107T2/de not_active Expired - Lifetime
- 2001-07-06 CZ CZ20030356A patent/CZ301765B6/cs not_active IP Right Cessation
- 2001-07-06 DK DK01954059T patent/DK1294689T3/da active
- 2001-07-06 GE GE5076A patent/GEP20043360B/en unknown
- 2001-07-06 PL PL01348493A patent/PL348493A1/xx not_active Application Discontinuation
- 2001-07-06 RS YU100502A patent/RS51717B/sr unknown
- 2001-07-06 AR ARP010103225A patent/AR029571A1/es unknown
- 2001-07-06 JP JP2001584233A patent/JP3592297B2/ja not_active Expired - Fee Related
- 2001-07-06 EP EP06075789A patent/EP1676839A3/fr not_active Withdrawn
- 2001-07-06 KR KR10-2003-7000116A patent/KR100513571B1/ko not_active IP Right Cessation
- 2001-07-06 AT AT01954059T patent/ATE324367T1/de active
- 2001-07-06 OA OA1200200398A patent/OA12305A/en unknown
- 2001-07-06 CN CNB018123554A patent/CN1328260C/zh not_active Expired - Fee Related
- 2001-07-06 BR BR0112244-4A patent/BR0112244A/pt not_active Application Discontinuation
- 2001-07-06 PT PT01954059T patent/PT1294689E/pt unknown
- 2001-07-06 MX MXPA02012921A patent/MXPA02012921A/es active IP Right Grant
- 2001-07-06 AU AU2001276419A patent/AU2001276419B2/en not_active Ceased
- 2001-07-06 US US10/312,902 patent/US20040029813A1/en not_active Abandoned
- 2001-07-06 EE EEP200300002A patent/EE05285B1/xx not_active IP Right Cessation
- 2001-07-06 ME MEP-2008-669A patent/ME00440B/me unknown
- 2001-07-06 NZ NZ523234A patent/NZ523234A/en not_active IP Right Cessation
- 2001-07-06 SK SK148-2003A patent/SK286918B6/sk not_active IP Right Cessation
- 2001-07-06 EP EP01954059A patent/EP1294689B1/fr not_active Expired - Lifetime
- 2001-07-06 CA CA002415442A patent/CA2415442C/fr not_active Expired - Fee Related
- 2001-07-06 SI SI200130535T patent/SI1294689T1/sl unknown
- 2001-07-06 EA EA200300103A patent/EA004874B1/ru not_active IP Right Cessation
- 2001-07-06 AP APAP/P/2002/002710A patent/AP1407A/en active
- 2001-07-06 WO PCT/FR2001/002168 patent/WO2001087836A1/fr active Application Filing
- 2001-07-06 ES ES01954059T patent/ES2262666T3/es not_active Expired - Lifetime
-
2003
- 2003-01-02 ZA ZA200300024A patent/ZA200300024B/en unknown
- 2003-01-06 NO NO20030050A patent/NO323446B1/no not_active IP Right Cessation
- 2003-02-05 BG BG107533A patent/BG66131B1/bg unknown
- 2003-02-06 HR HR20030079A patent/HRP20030079B8/xx not_active IP Right Cessation
-
2004
- 2004-02-12 HK HK04100953A patent/HK1058200A1/xx not_active IP Right Cessation
- 2004-07-13 JP JP2004206159A patent/JP2005002121A/ja active Pending
-
2005
- 2005-02-04 US US11/052,489 patent/US7259181B2/en not_active Expired - Fee Related
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2006
- 2006-10-20 HR HR20060361A patent/HRP20060361A8/xx not_active Application Discontinuation
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