OA12305A - Novel beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing the same. - Google Patents

Novel beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing the same. Download PDF

Info

Publication number: OA12305A
Authority: OA; OAPI
Prior art keywords: formula; compound; crystalline form; pharmaceutical composition; solution
Prior art date: 2000-07-06

Application number

OA1200200398A

Other languages

English (en)

Inventor

Stephane Beilles

Gerard Coquerel

Yves-Michel Ginot

Bruno Pfeiffer

Original Assignee

Servier Lab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-07-06

Filing date

2001-07-06

Publication date

2003-12-29

2001-07-06 Application filed by Servier Lab filed Critical Servier Lab

2003-12-29 Publication of OA12305A publication Critical patent/OA12305A/en

Links

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 10
238000002360 preparation method Methods 0.000 title abstract 2
238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 6
238000000034 method Methods 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
238000001914 filtration Methods 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 4
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 3
239000010949 copper Substances 0.000 claims description 3
238000010586 diagram 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
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 claims description 2
108090000882 Peptidyl-Dipeptidase A Proteins 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
239000002934 diuretic Substances 0.000 claims 2
230000001882 diuretic effect Effects 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
229940125758 compound 15 Drugs 0.000 claims 1
239000003112 inhibitor Substances 0.000 claims 1
229960002582 perindopril Drugs 0.000 abstract description 8
-1 perindopril tertiary butylamine salt Chemical class 0.000 abstract description 3
230000000694 effects Effects 0.000 abstract description 2
239000000203 mixture Substances 0.000 abstract description 2
239000005541 ACE inhibitor Substances 0.000 abstract 1
229940086440 Angiotensin I converting enzyme inhibitor Drugs 0.000 abstract 1
230000010534 mechanism of action Effects 0.000 abstract 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 6
239000007787 solid Substances 0.000 description 4
238000005259 measurement Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
101800000734 Angiotensin-1 Proteins 0.000 description 1
102400000344 Angiotensin-1 Human genes 0.000 description 1
108010064733 Angiotensins Proteins 0.000 description 1
102000015427 Angiotensins Human genes 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
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
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 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
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
238000006243 chemical reaction Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000008101 lactose Substances 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
150000003839 salts Chemical class 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
229940100445 wheat starch Drugs 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)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Epidemiology (AREA)
Hematology (AREA)
Diabetes (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

OA1200200398A 2000-07-06 2001-07-06 Novel beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing the same. OA12305A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
OA12305A true OA12305A (en)	2003-12-29

Family

ID=8852171

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200398A OA12305A (en)	2000-07-06	2001-07-06	Novel beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing the same.

Country Status (36)

Country	Link
US (2)	US20040029813A1 (xx)
EP (2)	EP1294689B1 (xx)
JP (2)	JP3592297B2 (xx)
KR (1)	KR100513571B1 (xx)
CN (1)	CN1328260C (xx)
AP (1)	AP1407A (xx)
AR (1)	AR029571A1 (xx)
AT (1)	ATE324367T1 (xx)
AU (2)	AU7641901A (xx)
BG (1)	BG66131B1 (xx)
BR (1)	BR0112244A (xx)
CA (1)	CA2415442C (xx)
CZ (1)	CZ301765B6 (xx)
DE (1)	DE60119107T2 (xx)
DK (1)	DK1294689T3 (xx)
EA (1)	EA004874B1 (xx)
EE (1)	EE05285B1 (xx)
ES (1)	ES2262666T3 (xx)
FR (1)	FR2811319B1 (xx)
GE (1)	GEP20043360B (xx)
HK (1)	HK1058200A1 (xx)
HR (2)	HRP20030079B8 (xx)
HU (1)	HU227673B1 (xx)
ME (1)	ME00440B (xx)
MX (1)	MXPA02012921A (xx)
NO (1)	NO323446B1 (xx)
NZ (1)	NZ523234A (xx)
OA (1)	OA12305A (xx)
PL (1)	PL348493A1 (xx)
PT (1)	PT1294689E (xx)
RS (1)	RS51717B (xx)
SI (1)	SI1294689T1 (xx)
SK (1)	SK286918B6 (xx)
UA (1)	UA57189C2 (xx)
WO (1)	WO2001087836A1 (xx)
ZA (1)	ZA200300024B (xx)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
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
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
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
PL1636185T3 (pl)	2003-06-24	2012-12-31	Servier Lab	Nowe formy krystaliczne peryndoprylu erbuminy
WO2005037788A1 (en)	2003-10-21	2005-04-28	Lupin Ltd.	Novel method for preparation of crystalline perindopril erbumine
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
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
WO2007020009A1 (en) *	2005-08-12	2007-02-22	Sandoz Ag	New crystalline form of perindopril erbumine
MX2008002064A (es) *	2005-08-12	2008-04-17	Lek Pharmaceuticals	Un proceso para la preparacion de perindopril-erbumina.
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
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
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
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)

* Cited by examiner, † Cited by third party
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
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

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 NZ NZ523234A patent/NZ523234A/en not_active IP Right Cessation
- 2001-07-06 AU AU7641901A patent/AU7641901A/xx active Pending
- 2001-07-06 EA EA200300103A patent/EA004874B1/ru not_active IP Right Cessation
- 2001-07-06 WO PCT/FR2001/002168 patent/WO2001087836A1/fr active Application Filing
- 2001-07-06 RS YU100502A patent/RS51717B/sr unknown
- 2001-07-06 EP EP01954059A patent/EP1294689B1/fr not_active Expired - Lifetime
- 2001-07-06 OA OA1200200398A patent/OA12305A/en unknown
- 2001-07-06 DE DE60119107T patent/DE60119107T2/de not_active Expired - Lifetime
- 2001-07-06 ME MEP-2008-669A patent/ME00440B/me unknown
- 2001-07-06 MX MXPA02012921A patent/MXPA02012921A/es active IP Right Grant
- 2001-07-06 DK DK01954059T patent/DK1294689T3/da active
- 2001-07-06 ES ES01954059T patent/ES2262666T3/es not_active Expired - Lifetime
- 2001-07-06 AU AU2001276419A patent/AU2001276419B2/en not_active Ceased
- 2001-07-06 KR KR10-2003-7000116A patent/KR100513571B1/ko not_active IP Right Cessation
- 2001-07-06 SI SI200130535T patent/SI1294689T1/sl unknown
- 2001-07-06 AT AT01954059T patent/ATE324367T1/de active
- 2001-07-06 BR BR0112244-4A patent/BR0112244A/pt not_active Application Discontinuation
- 2001-07-06 JP JP2001584233A patent/JP3592297B2/ja not_active Expired - Fee Related
- 2001-07-06 PL PL01348493A patent/PL348493A1/xx not_active Application Discontinuation
- 2001-07-06 PT PT01954059T patent/PT1294689E/pt unknown
- 2001-07-06 AR ARP010103225A patent/AR029571A1/es unknown
- 2001-07-06 CZ CZ20030356A patent/CZ301765B6/cs not_active IP Right Cessation
- 2001-07-06 GE GE5076A patent/GEP20043360B/en unknown
- 2001-07-06 EP EP06075789A patent/EP1676839A3/fr not_active Withdrawn
- 2001-07-06 CN CNB018123554A patent/CN1328260C/zh not_active Expired - Fee Related
- 2001-07-06 AP APAP/P/2002/002710A patent/AP1407A/en active
- 2001-07-06 EE EEP200300002A patent/EE05285B1/xx not_active IP Right Cessation
- 2001-07-06 CA CA002415442A patent/CA2415442C/fr not_active Expired - Fee Related
- 2001-07-06 SK SK148-2003A patent/SK286918B6/sk not_active IP Right Cessation
- 2001-07-06 US US10/312,902 patent/US20040029813A1/en not_active Abandoned
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
2006
- 2006-10-20 HR HR20060361A patent/HRP20060361A8/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
SK286918B6 (sk)	2009-07-06
HRP20060361A2 (en)	2008-06-30
EP1676839A2 (fr)	2006-07-05
AP1407A (en)	2005-05-30
NO323446B1 (no)	2007-05-07
HUP0102813A2 (hu)	2002-03-28
GEP20043360B (en)	2004-06-10
AU2001276419B2 (en)	2006-11-16
US20040029813A1 (en)	2004-02-12
YU100502A (sh)	2003-08-29
FR2811319B1 (fr)	2002-08-23
AR029571A1 (es)	2003-07-02
JP2003533508A (ja)	2003-11-11
ES2262666T3 (es)	2006-12-01
CN1440388A (zh)	2003-09-03
NO20030050D0 (no)	2003-01-06
KR100513571B1 (ko)	2005-09-09
NO20030050L (no)	2003-01-06
BG107533A (bg)	2003-11-28
PT1294689E (pt)	2006-07-31
ME00440B (me)	2011-10-10
ZA200300024B (en)	2004-02-05
SI1294689T1 (sl)	2006-08-31
US20050203165A1 (en)	2005-09-15
EA200300103A1 (ru)	2003-06-26
AP2002002710A0 (en)	2002-12-31
JP3592297B2 (ja)	2004-11-24
ATE324367T1 (de)	2006-05-15
US7259181B2 (en)	2007-08-21
BG66131B1 (bg)	2011-06-30
DK1294689T3 (da)	2006-08-28
WO2001087836A1 (fr)	2001-11-22
CN1328260C (zh)	2007-07-25
KR20030016368A (ko)	2003-02-26
RS51717B (sr)	2011-10-31
HRP20030079B1 (en)	2007-12-31
SK1482003A3 (en)	2003-06-03
EE05285B1 (et)	2010-04-15
JP2005002121A (ja)	2005-01-06
DE60119107T2 (de)	2006-12-07
CA2415442C (fr)	2009-01-27
CZ301765B6 (cs)	2010-06-16
CA2415442A1 (fr)	2001-11-22
EE200300002A (et)	2004-08-16
MXPA02012921A (es)	2004-07-30
UA57189C2 (uk)	2003-06-16
HU227673B1 (hu)	2011-11-28
EA004874B1 (ru)	2004-08-26
HUP0102813A3 (en)	2003-12-29
HU0102813D0 (en)	2001-09-28
EP1676839A3 (fr)	2006-11-08
PL348493A1 (en)	2002-01-14
HRP20030079B8 (en)	2008-09-30
EP1294689A1 (fr)	2003-03-26
FR2811319A1 (fr)	2002-01-11
CZ2003356A3 (cs)	2003-05-14
HRP20030079A2 (en)	2003-04-30
AU7641901A (en)	2001-11-26
HRP20060361A8 (en)	2008-07-31
EP1294689B1 (fr)	2006-04-26
DE60119107D1 (de)	2006-06-01
HK1058200A1 (en)	2004-05-07
NZ523234A (en)	2005-01-28
BR0112244A (pt)	2003-06-24

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