US20040029813A1 - Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same - Google Patents

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

Info

Publication number: US20040029813A1
Authority: US; United States
Prior art keywords: compound; formula; crystalline form; preparation; pharmaceutical composition
Prior art date: 2000-07-06
Legal status (The legal status 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 status listed.): Abandoned

Application number

US10/312,902

Other languages

English (en)

Inventor

Bruno Pfeiffer

Yves-Michel Ginot

Gerard Coquerel

Stephane Beilles

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Laboratoires Servier SAS

Original Assignee

Laboratoires Servier SAS

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

2004-02-12

2001-07-06 Application filed by Laboratoires Servier SAS filed Critical Laboratoires Servier SAS

2003-09-22 Assigned to LES LABORATOIRES SERVIER reassignment LES LABORATOIRES SERVIER ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BEILLES, STEPHANE, COQUEREL, GERARD, GINOT, YVES-MICHEL, PFEIFFER, BRUNO

2004-02-12 Publication of US20040029813A1 publication Critical patent/US20040029813A1/en

2005-02-04 Priority to US11/052,489 priority Critical patent/US7259181B2/en

Status Abandoned legal-status Critical Current

Links

238000002360 preparation method Methods 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
239000008194 pharmaceutical composition Substances 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 17
238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 6
238000010586 diagram Methods 0.000 claims abstract description 4
239000003814 drug Substances 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
238000001914 filtration Methods 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 claims description 3
108090000882 Peptidyl-Dipeptidase A Proteins 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
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
238000004519 manufacturing process Methods 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 6
229960002582 perindopril Drugs 0.000 description 6
XVEVFLNZMLBCJQ-MXLIJYGISA-N C.C.[H][C@@]12CCCC[C@]1([H])N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(=O)O)C2 Chemical compound C.C.[H][C@@]12CCCC[C@]1([H])N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(=O)O)C2 XVEVFLNZMLBCJQ-MXLIJYGISA-N 0.000 description 3
238000005259 measurement Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
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
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
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-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
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 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
238000006731 degradation reaction Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 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
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000203 mixture 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
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
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

Definitions

the present invention relates to a new ⁇ crystalline form of perindopril tert-butylamine salt of formula (I:
the present invention relates to the ⁇ crystalline form of the compound of formula (I), characterised by the following powder X-ray diffraction diagram, measured using a Siemens D5005 diffractometer (copper anticathode) and expressed in terms of inter-planar distance d, Bragg's angle 2 theta, intensity and relative intensity (expressed as a percentage of the most intense ray): Angle 2 theta Inter-planar Relative intensity (°) distance d ( ⁇ ) Intensity (%) 5.169 17.08 523 16.5 8.379 10.54 1001 31.5 9.350 9.45 3175 100 14.746 6.00 236 7.4 15.411 5.74 753 23.7 15.931 5.56 279 8.8 16.711 5.30 113 3.6 18.161 4.88 122 3.8 20.564 4.32 1198 37.7 21.285 4.17 330 10.4 21.781 4.08 317 10 22.632 3.93 190 6 23.308 3.81 133 4.2 23.797 3.74 427 13.
the invention relates also to a process for the preparation of the ⁇ crystalline form of the compound of formula (I), which process is characterised in that:
a solution of perindoprtil tert-butylamine salt in ethyl acetate is heated at reflux and is then rapidly cooled to 5° C. and the solid obtained is collected by filtration.
the concentration of the compound of formula (I) in the dichloromethane is preferably from 100 to 200 g/litre.
the concentration of the compound of formula (I) in the ethyl acetate is preferably from 70 to 90 g/litre.
the invention relates also to pharmaceutical compositions comprising as active ingredient the ⁇ crystalline form of the compound of formula (1) together with one or more appropriate, inert, non-toxic excipients.
pharmaceutical compositions according to the invention there may be mentioned more especially those that are suitable for oral, parenteral (intravenous or subcutaneous) or nasal administration, tablets or drages, sublingual tablets, gelatin capsules, lozenges, suppositories, creams, ointments, dermal gels, injectable preparations, drinkable suspensions etc.
the useful dosage can be varied according to the nature and severity of the disorder, the administration route and the age and weight of the patient. It varies from 1 to 500 mg per day in one or more administrations.
compositions according to the invention may also comprise a diuretic such as indapamide.
variable slits v6
Preparation formula for 1000 tablets each containing 4 mg of active ingredient Preparation formula for 1000 tablets each containing 4 mg of active ingredient: Compound of Example 1 4 g Hydroxypropylcellulose 2 g Wheat starch 10 g Lactose 100 g Magnesium stearate 3 g Talc 3 g

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Epidemiology (AREA)
Hospice & Palliative Care (AREA)
Hematology (AREA)
Diabetes (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

US10/312,902 2000-07-06 2001-07-06 Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same Abandoned US20040029813A1 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
US11/052,489 US7259181B2 (en)	2000-07-06	2005-02-04	β crystalline form of perindopril tert-butylamine salt

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR0008792		2000-07-06
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

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
US11/052,489 Continuation US7259181B2 (en)	2000-07-06	2005-02-04	β crystalline form of perindopril tert-butylamine salt

Publications (1)

Publication Number	Publication Date
US20040029813A1 true US20040029813A1 (en)	2004-02-12

Family

ID=8852171

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
US10/312,902 Abandoned US20040029813A1 (en)	2000-07-06	2001-07-06	Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same
US11/052,489 Expired - Fee Related US7259181B2 (en)	2000-07-06	2005-02-04	β crystalline form of perindopril tert-butylamine salt

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
US11/052,489 Expired - Fee Related US7259181B2 (en)	2000-07-06	2005-02-04	β crystalline form of perindopril tert-butylamine salt

Country Status (35)

Country	Link
US (2)	US20040029813A1 (fr)
EP (2)	EP1676839A3 (fr)
JP (2)	JP3592297B2 (fr)
KR (1)	KR100513571B1 (fr)
CN (1)	CN1328260C (fr)
AP (1)	AP1407A (fr)
AR (1)	AR029571A1 (fr)
AT (1)	ATE324367T1 (fr)
AU (2)	AU2001276419B2 (fr)
BG (1)	BG66131B1 (fr)
BR (1)	BR0112244A (fr)
CA (1)	CA2415442C (fr)
CZ (1)	CZ301765B6 (fr)
DE (1)	DE60119107T2 (fr)
DK (1)	DK1294689T3 (fr)
EA (1)	EA004874B1 (fr)
EE (1)	EE05285B1 (fr)
ES (1)	ES2262666T3 (fr)
FR (1)	FR2811319B1 (fr)
GE (1)	GEP20043360B (fr)
HR (2)	HRP20060361A8 (fr)
HU (1)	HU227673B1 (fr)
ME (1)	ME00440B (fr)
MX (1)	MXPA02012921A (fr)
NO (1)	NO323446B1 (fr)
NZ (1)	NZ523234A (fr)
OA (1)	OA12305A (fr)
PL (1)	PL348493A1 (fr)
PT (1)	PT1294689E (fr)
RS (1)	RS51717B (fr)
SI (1)	SI1294689T1 (fr)
SK (1)	SK286918B6 (fr)
UA (1)	UA57189C2 (fr)
WO (1)	WO2001087836A1 (fr)
ZA (1)	ZA200300024B (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20040248817A1 (en) *	2000-07-06	2004-12-09	Bruno Pfeiffer	Gamma crystalline form of perindopril tert-butylamine salt
US20050059609A1 (en) *	2000-07-06	2005-03-17	Bruno Pfeiffer	New alpha crystalline form of perindopril tert-butylamine salt
US20070135512A1 (en) *	2003-06-24	2007-06-14	Christoph Strassler	Novel crystalline forms of perindopril erbumine
US20070172524A1 (en) *	2004-03-29	2007-07-26	Krka, Tovarna Zdravil, D.D., Novo Mesto	Process for preparing a solid pharmaceutical composition
US20080051584A1 (en) *	2004-05-14	2008-02-28	Les Laboratoires Servier	Process For The Preparation Of Perindopril And Salts Thereof
WO2007092758A3 (fr) *	2006-02-03	2008-06-19	Reddys Lab Ltd Dr	Formes cristallines de périndopril erbumine
US20100016614A1 (en) *	2005-08-12	2010-01-21	Lek Pharmaceuticals D.D	Process for the preparation of perindopril erbumine
AU2007220434B2 (en) *	2006-02-28	2010-10-14	Les Laboratoires Servier	Beta-crystalline form of perindopril arginine salt, method for making same, and pharmaceutical compositions containing same
AU2007220435B2 (en) *	2006-02-28	2010-11-04	Les Laboratoires Servier	Alpha crystalline form of the arginine salt of perindopril, process for preparing it, and pharmaceutical compositions comprising it
US8470869B2 (en)	2007-06-27	2013-06-25	Krka, Tovarna Zdravil D.D. Novo Mesto	Salts of perindopril

Families Citing this family (17)

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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
ES2336554T3 (es)	2003-10-21	2010-04-14	Les Laboratoires Servier	Nuevo metodo para la preparacion de perindopril erbumina cristalina.
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
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 (fr) *	2005-05-05	2007-02-15	Arch Pharmalabs Limited	Preparation d'une nouvelle forme cristalline $g(h)(eta) de perindopril erbumine
JP2009505970A (ja) *	2005-08-12	2009-02-12	サンド・アクチエンゲゼルシヤフト	ペリンドプリルエルブミンの新規結晶形
EP1815857A1 (fr)	2006-02-02	2007-08-08	LEK Pharmaceuticals D.D.	Composition pharmaceutique comprenant du perindopril
WO2008050185A2 (fr) *	2006-10-26	2008-05-02	Glenmark Pharmaceuticals Limited	Nouveaux polymorphes de la périndopril erbumine
WO2008120241A2 (fr) *	2007-03-29	2008-10-09	Ipca Laboratories Limited	Nouveaux solvates alcooliques de périndopril erbumine
PL2318365T3 (pl) *	2008-06-24	2016-02-29	Mylan Laboratories Ltd	Nowe odmiany polimorficzne (L) argininianu peryndoprylu i sposoby ich wytwarzania
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 (fr)	2019-12-23	2021-06-30	KRKA, d.d., Novo mesto	Composition pour la préparation de granulés de périndopril arginine, procédé pour leur préparation et composition pharmaceutique comprenant les granulés

Citations (1)

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- 2001-07-06 US US10/312,902 patent/US20040029813A1/en not_active Abandoned
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- 2001-07-06 CA CA002415442A patent/CA2415442C/fr not_active Expired - Fee Related
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- 2001-07-06 HR HR20060361A patent/HRP20060361A8/xx not_active Application Discontinuation
- 2001-07-06 WO PCT/FR2001/002168 patent/WO2001087836A1/fr active Application Filing
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Cited By (16)

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Publication number	Priority date	Publication date	Assignee	Title
US20050059609A1 (en) *	2000-07-06	2005-03-17	Bruno Pfeiffer	New alpha crystalline form of perindopril tert-butylamine salt
US20040248817A1 (en) *	2000-07-06	2004-12-09	Bruno Pfeiffer	Gamma crystalline form of perindopril tert-butylamine salt
US20100160404A1 (en) *	2003-06-24	2010-06-24	Christoph Strassler	New crystalline forms of perindopril erbumine
US20070135512A1 (en) *	2003-06-24	2007-06-14	Christoph Strassler	Novel crystalline forms of perindopril erbumine
US7981921B2 (en)	2003-06-24	2011-07-19	Les Laboratoires Servier	Crystalline forms of perindopril erbumine
US7705046B2 (en)	2003-06-24	2010-04-27	Les Laboratoires Servier	Crystalline forms of perindopril erbumine
US20070172524A1 (en) *	2004-03-29	2007-07-26	Krka, Tovarna Zdravil, D.D., Novo Mesto	Process for preparing a solid pharmaceutical composition
EP1729739B1 (fr)	2004-03-29	2016-09-28	Les Laboratoires Servier	Procede de preparation d'une composition pharmaceutique solide
US20100172995A1 (en) *	2004-03-29	2010-07-08	Les Laboratoires Servier	Process For Preparing A Solid Pharmaceutical Composition
US20080051584A1 (en) *	2004-05-14	2008-02-28	Les Laboratoires Servier	Process For The Preparation Of Perindopril And Salts Thereof
US7674814B2 (en)	2004-05-14	2010-03-09	Les Laboratoires Servier	Process for the preparation of perindopril and salts thereof
US20100016614A1 (en) *	2005-08-12	2010-01-21	Lek Pharmaceuticals D.D	Process for the preparation of perindopril erbumine
WO2007092758A3 (fr) *	2006-02-03	2008-06-19	Reddys Lab Ltd Dr	Formes cristallines de périndopril erbumine
AU2007220434B2 (en) *	2006-02-28	2010-10-14	Les Laboratoires Servier	Beta-crystalline form of perindopril arginine salt, method for making same, and pharmaceutical compositions containing same
AU2007220435B2 (en) *	2006-02-28	2010-11-04	Les Laboratoires Servier	Alpha crystalline form of the arginine salt of perindopril, process for preparing it, and pharmaceutical compositions comprising it
US8470869B2 (en)	2007-06-27	2013-06-25	Krka, Tovarna Zdravil D.D. Novo Mesto	Salts of perindopril

Also Published As

Publication number	Publication date
BG66131B1 (bg)	2011-06-30
SI1294689T1 (sl)	2006-08-31
CN1328260C (zh)	2007-07-25
ES2262666T3 (es)	2006-12-01
JP2003533508A (ja)	2003-11-11
AP2002002710A0 (en)	2002-12-31
OA12305A (en)	2003-12-29
JP2005002121A (ja)	2005-01-06
BR0112244A (pt)	2003-06-24
AP1407A (en)	2005-05-30
ATE324367T1 (de)	2006-05-15
EP1676839A2 (fr)	2006-07-05
EA200300103A1 (ru)	2003-06-26
US20050203165A1 (en)	2005-09-15
NO20030050D0 (no)	2003-01-06
MXPA02012921A (es)	2004-07-30
FR2811319B1 (fr)	2002-08-23
AU2001276419B2 (en)	2006-11-16
NO323446B1 (no)	2007-05-07
HRP20030079B8 (hr)	2008-09-30
CZ2003356A3 (cs)	2003-05-14
HK1058200A1 (en)	2004-05-07
CA2415442A1 (fr)	2001-11-22
GEP20043360B (en)	2004-06-10
ZA200300024B (en)	2004-02-05
US7259181B2 (en)	2007-08-21
SK286918B6 (sk)	2009-07-06
PL348493A1 (en)	2002-01-14
ME00440B (fr)	2011-10-10
HUP0102813A3 (en)	2003-12-29
HRP20060361A2 (hr)	2008-06-30
HRP20030079A2 (en)	2003-04-30
AR029571A1 (es)	2003-07-02
YU100502A (sh)	2003-08-29
PT1294689E (pt)	2006-07-31
HRP20030079B1 (hr)	2007-12-31
AU7641901A (en)	2001-11-26
EE05285B1 (et)	2010-04-15
DE60119107T2 (de)	2006-12-07
NZ523234A (en)	2005-01-28
HRP20060361A8 (hr)	2008-07-31
HU227673B1 (hu)	2011-11-28
EP1294689B1 (fr)	2006-04-26
NO20030050L (no)	2003-01-06
CA2415442C (fr)	2009-01-27
RS51717B (sr)	2011-10-31
SK1482003A3 (en)	2003-06-03
EA004874B1 (ru)	2004-08-26
CZ301765B6 (cs)	2010-06-16
UA57189C2 (uk)	2003-06-16
KR100513571B1 (ko)	2005-09-09
EE200300002A (et)	2004-08-16
WO2001087836A1 (fr)	2001-11-22
EP1676839A3 (fr)	2006-11-08
JP3592297B2 (ja)	2004-11-24
HUP0102813A2 (hu)	2002-03-28
HU0102813D0 (en)	2001-09-28
CN1440388A (zh)	2003-09-03
BG107533A (bg)	2003-11-28
EP1294689A1 (fr)	2003-03-26
DE60119107D1 (de)	2006-06-01
KR20030016368A (ko)	2003-02-26
DK1294689T3 (da)	2006-08-28
FR2811319A1 (fr)	2002-01-11

Publication	Publication Date	Title
US20040029813A1 (en)	2004-02-12	Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same
US20030186896A1 (en)	2003-10-02	Crystalline form of perindopril tert-butylamine salt
US20030158121A1 (en)	2003-08-21	Novel $G(y)crystalline form of perindopril tert- butylamine salt, preparation method, and pharmaceutical compositions containing same
US7923569B2 (en)	2011-04-12	β Crystalline form of the arginine salt of perindopril, a process for its preparation and pharmaceutical compositions containing it
US20090203758A1 (en)	2009-08-13	Alpha Crystalline form of the Arginine salt of Perindopril, a Process for its Preparation and Pharmceutical Compositions Containing it.
AU2006235841A1 (en)	2006-11-23	Novel beta crystalline form of perindopril tert-butylamine salt, a process for its preparation and pharmaceutical compositions containing it
HK1058199B (en)	2007-12-14	Novel $g(y) crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same
HK1058200B (en)	2007-12-14	Novel $g(b) crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same
HK1055425B (en)	2007-12-07	A crystalline form of perindopril tert-butylamine salt

Legal Events

Date	Code	Title	Description
2003-09-22	AS	Assignment	Owner name: LES LABORATOIRES SERVIER, FRANCE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:PFEIFFER, BRUNO;GINOT, YVES-MICHEL;COQUEREL, GERARD;AND OTHERS;REEL/FRAME:014514/0172 Effective date: 20021210
2005-03-18	STCB	Information on status: application discontinuation	Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION

Date

Code

Title

Description

2003-09-22

Assignment

Owner name: LES LABORATOIRES SERVIER, FRANCE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:PFEIFFER, BRUNO;GINOT, YVES-MICHEL;COQUEREL, GERARD;AND OTHERS;REEL/FRAME:014514/0172

Effective date: 20021210

2005-03-18

STCB

Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION