HRP20040781B8 - Process for the preparation of high purity perindopril and intermediates useful in the synthesis - Google Patents

Process for the preparation of high purity perindopril and intermediates useful in the synthesis

Info

Publication number: HRP20040781B8
Authority: HR; Croatia
Prior art keywords: formula; compound; preparation; reacting; alkyl
Prior art date: 2002-01-30

Application number

HR20040781A

Other languages

English (en)

Croatian (hr)

Inventor

Simig Gyula

Mezei Tibor

Porcs-Makkay Marta

Mandi Attila

Original Assignee

Les Laboratoires Servier

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.)

2002-01-30

Filing date

2004-08-27

Publication date

2009-01-31

2004-08-27 Application filed by Les Laboratoires Servier filed Critical Les Laboratoires Servier

2004-12-31 Publication of HRP20040781A2 publication Critical patent/HRP20040781A2/xx

2008-12-31 Publication of HRP20040781B1 publication Critical patent/HRP20040781B1/xx

2009-01-31 Publication of HRP20040781A8 publication Critical patent/HRP20040781A8/xx

2009-01-31 Publication of HRP20040781B8 publication Critical patent/HRP20040781B8/xx

Links

238000000034 method Methods 0.000 title abstract 2
238000002360 preparation method Methods 0.000 title abstract 2
230000015572 biosynthetic process Effects 0.000 title 1
239000000543 intermediate Substances 0.000 title 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 title 1
229960002582 perindopril Drugs 0.000 title 1
238000003786 synthesis reaction Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract 6
125000000217 alkyl group Chemical group 0.000 abstract 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
230000003213 activating effect Effects 0.000 abstract 1
-1 alkyl chloroformate Chemical compound 0.000 abstract 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 abstract 1
125000004432 carbon atom Chemical group C* 0.000 abstract 1
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
239000000356 contaminant Substances 0.000 abstract 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 abstract 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- 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
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Indole Compounds (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

HR20040781A 2002-01-30 2004-08-27 Process for the preparation of high purity perindopril and intermediates useful in the synthesis HRP20040781B8 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP02290206A EP1333026B1 (fr)	2002-01-30	2002-01-30	Procédé de préparation de perindopril de grande pureté et des intermédiaires utiles dans la synthèse
PCT/IB2003/000691 WO2003064388A2 (fr)	2002-01-30	2003-01-29	Procede de preparation de perindopril a purete elevee et produits intermediaires utiles dans la synthese dudit compose

Publications (4)

Publication Number	Publication Date
HRP20040781A2 HRP20040781A2 (en)	2004-12-31
HRP20040781B1 HRP20040781B1 (en)	2008-12-31
HRP20040781A8 HRP20040781A8 (en)	2009-01-31
HRP20040781B8 true HRP20040781B8 (en)	2009-01-31

Family

ID=8185713

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20040781A HRP20040781B8 (en)	2002-01-30	2004-08-27	Process for the preparation of high purity perindopril and intermediates useful in the synthesis

Country Status (36)

Country	Link
US (2)	US7326794B2 (fr)
EP (1)	EP1333026B1 (fr)
JP (1)	JP4171423B2 (fr)
KR (1)	KR100673701B1 (fr)
CN (1)	CN1300111C (fr)
AP (1)	AP1741A (fr)
AR (1)	AR038340A1 (fr)
AT (1)	ATE365714T1 (fr)
AU (1)	AU2003206055B2 (fr)
BG (1)	BG66126B1 (fr)
BR (2)	BR0307293A (fr)
CA (1)	CA2474003C (fr)
CY (1)	CY1106721T1 (fr)
CZ (1)	CZ305892B6 (fr)
DE (1)	DE60220877T2 (fr)
DK (1)	DK1333026T3 (fr)
EA (1)	EA009277B1 (fr)
EE (1)	EE05428B1 (fr)
ES (1)	ES2289060T3 (fr)
GE (1)	GEP20063899B (fr)
HK (1)	HK1076101A1 (fr)
HR (1)	HRP20040781B8 (fr)
HU (1)	HU227591B1 (fr)
ME (1)	ME00444B (fr)
MX (1)	MXPA04007444A (fr)
NO (1)	NO330223B1 (fr)
NZ (1)	NZ534168A (fr)
OA (1)	OA12759A (fr)
PL (1)	PL212354B1 (fr)
PT (1)	PT1333026E (fr)
RS (1)	RS52465B (fr)
SI (1)	SI1333026T1 (fr)
SK (1)	SK287866B6 (fr)
UA (1)	UA77756C2 (fr)
WO (1)	WO2003064388A2 (fr)
ZA (1)	ZA200405548B (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005037788A1 (fr) *	2003-10-21	2005-04-28	Lupin Ltd.	Nouvelle methode de preparation de perindopril erbumine cristalline
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
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
ES2255872B1 (es) *	2004-12-31	2007-08-16	Quimica Sintetica, S.A.	Procedimiento para la preparacion de perindopril erbumina.
EP1679072B9 (fr)	2005-01-06	2009-09-02	IPCA Laboratories Limited	Procédé de synthèse de dérivés de l'acide (2S, 3aS, 7aS)-1-(S)-alanyl-octahydro-1H-indole-2-carboxylique et application à la synthése du perindopril
US7710739B2 (en)	2005-04-28	2010-05-04	Semiconductor Energy Laboratory Co., Ltd.	Semiconductor device and display device
WO2006137082A1 (fr) *	2005-06-23	2006-12-28	Ramesh Babu Potluri	Procédé pour la préparation de périndopril erbumine viable industriellement
US20070032661A1 (en) *	2005-08-03	2007-02-08	Glenmark Pharmaceuticals Limited	Process for the preparation of intermediates of perindopril
UA92613C2 (ru) *	2005-08-12	2010-11-25	Лек Фармасьютиклз Д.Д.	Способ получения кристаллической формы d эрбумина периндоприла
EP1792896A1 (fr) *	2005-12-01	2007-06-06	KRKA, tovarna zdravil, d.d., Novo mesto	Procédé pour la préparation de perindopril et de ses sels
JP5230609B2 (ja) *	2006-05-12	2013-07-10	エギシュヂョヂセルヂャールニルヴァーノサンミケデレースヴェーニタールササーグ	Ａｃｅ阻害薬の合成における新規な医薬中間体及びその使用
WO2016178591A2 (fr)	2015-05-05	2016-11-10	Gene Predit, Sa	Marqueurs génétiques et traitement de l'obésité masculine
FR3050380B1 (fr)	2016-04-20	2020-07-10	Les Laboratoires Servier	Composition pharmaceutique comprenant un betabloquant, un inhibiteur de l'enzyme de conversion et un antihypertenseur ou un ains.

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK144769C (da)	1979-12-06	1982-12-13	Voelund Vaskerimaskiner	Tromlevaskemaskine med varmeveksler
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
US4565819A (en) *	1979-12-07	1986-01-21	Adir	Substituted imino diacids, their preparation and pharmaceutical compositions which contain them
IN156096B (fr)	1981-03-19	1985-05-11	Usv Pharma Corp
FR2620709B1 (fr) *	1987-09-17	1990-09-07	Adir	Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese
SI9600169A (en)	1996-05-22	1997-12-31	Krka Tovarna Zdravil	Process for preparation of compounds with ace inhibitory effect
FR2807431B1 (fr)	2000-04-06	2002-07-19	Adir	Nouveau procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables
AR036187A1 (es)	2001-07-24	2004-08-18	Adir	Un proceso para la preparacion de perindopril, compuestos analogos y sus sales, compuesto intermediario 2,5-dioxo-oxazolidina y proceso para preparar un intermediario
FR2827860B1 (fr)	2001-07-24	2004-12-10	Servier Lab	Nouveau procede de synthese de derives de l'acide (2s, 3as, 7as)-1-[(s)-alanyl]-octahydro-1h-indole-2-carboxyline et application a la synthese du perindopril

2002
- 2002-01-30 DE DE60220877T patent/DE60220877T2/de not_active Expired - Lifetime
- 2002-01-30 SI SI200230586T patent/SI1333026T1/sl unknown
- 2002-01-30 AT AT02290206T patent/ATE365714T1/de active
- 2002-01-30 EP EP02290206A patent/EP1333026B1/fr not_active Expired - Lifetime
- 2002-01-30 DK DK02290206T patent/DK1333026T3/da active
- 2002-01-30 ES ES02290206T patent/ES2289060T3/es not_active Expired - Lifetime
- 2002-01-30 PT PT02290206T patent/PT1333026E/pt unknown
2003
- 2003-01-29 PL PL358514A patent/PL212354B1/pl unknown
- 2003-01-29 WO PCT/IB2003/000691 patent/WO2003064388A2/fr active Application Filing
- 2003-01-29 NZ NZ534168A patent/NZ534168A/en not_active IP Right Cessation
- 2003-01-29 KR KR1020047011731A patent/KR100673701B1/ko not_active IP Right Cessation
- 2003-01-29 BR BR0307293-2A patent/BR0307293A/pt not_active IP Right Cessation
- 2003-01-29 CN CNB038027143A patent/CN1300111C/zh not_active Expired - Fee Related
- 2003-01-29 UA UA20040807143A patent/UA77756C2/uk unknown
- 2003-01-29 MX MXPA04007444A patent/MXPA04007444A/es active IP Right Grant
- 2003-01-29 BR BRPI0307293-2A patent/BRPI0307293B1/pt unknown
- 2003-01-29 EE EEP200400107A patent/EE05428B1/xx not_active IP Right Cessation
- 2003-01-29 SK SK329-2004A patent/SK287866B6/sk not_active IP Right Cessation
- 2003-01-29 HU HU0300231A patent/HU227591B1/hu not_active IP Right Cessation
- 2003-01-29 JP JP2003564011A patent/JP4171423B2/ja not_active Expired - Fee Related
- 2003-01-29 ME MEP-2008-674A patent/ME00444B/fr unknown
- 2003-01-29 EA EA200400929A patent/EA009277B1/ru not_active IP Right Cessation
- 2003-01-29 AU AU2003206055A patent/AU2003206055B2/en not_active Ceased
- 2003-01-29 RS YU66704A patent/RS52465B/en unknown
- 2003-01-29 CZ CZ2004-906A patent/CZ305892B6/cs not_active IP Right Cessation
- 2003-01-29 CA CA002474003A patent/CA2474003C/fr not_active Expired - Fee Related
- 2003-01-29 GE GE5686A patent/GEP20063899B/en unknown
- 2003-01-29 AP APAP/P/2004/003091A patent/AP1741A/en active
- 2003-01-29 US US10/503,272 patent/US7326794B2/en not_active Expired - Fee Related
- 2003-01-29 ZA ZA200405548A patent/ZA200405548B/xx unknown
- 2003-01-29 OA OA1200400196A patent/OA12759A/en unknown
- 2003-01-30 AR ARP030100263A patent/AR038340A1/es not_active Application Discontinuation
2004
- 2004-08-20 NO NO20043472A patent/NO330223B1/no not_active IP Right Cessation
- 2004-08-27 HR HR20040781A patent/HRP20040781B8/xx not_active IP Right Cessation
- 2004-08-27 BG BG108858A patent/BG66126B1/bg unknown
2005
- 2005-09-16 HK HK05108134A patent/HK1076101A1/xx not_active IP Right Cessation
2007
- 2007-04-20 US US11/788,454 patent/US7279595B2/en not_active Expired - Fee Related
- 2007-07-12 CY CY20071100925T patent/CY1106721T1/el unknown

Also Published As

Publication number	Publication date
BG108858A (en)	2005-05-31
ME00444B (fr)	2011-10-10
KR100673701B1 (ko)	2007-01-24
OA12759A (en)	2006-07-04
CY1106721T1 (el)	2012-05-23
HU227591B1 (hu)	2011-09-28
EP1333026B1 (fr)	2007-06-27
DK1333026T3 (da)	2007-10-22
EE200400107A (et)	2004-10-15
US20070197821A1 (en)	2007-08-23
HK1076101A1 (en)	2006-01-06
EE05428B1 (et)	2011-06-15
SI1333026T1 (sl)	2007-10-31
WO2003064388A2 (fr)	2003-08-07
UA77756C2 (uk)	2007-01-15
PL212354B1 (pl)	2012-09-28
NO20043472L (no)	2004-08-20
AU2003206055B2 (en)	2008-07-17
BRPI0307293B1 (pt)	2018-03-06
RS52465B (en)	2013-02-28
HRP20040781A8 (en)	2009-01-31
DE60220877T2 (de)	2008-04-10
KR20040078680A (ko)	2004-09-10
BR0307293A (pt)	2004-12-21
MXPA04007444A (es)	2005-06-17
HUP0300231A3 (en)	2004-04-28
ZA200405548B (en)	2006-09-27
CA2474003A1 (fr)	2003-08-07
GEP20063899B (en)	2006-08-10
HU0300231D0 (en)	2003-03-28
HRP20040781A2 (en)	2004-12-31
WO2003064388A3 (fr)	2004-02-05
HUP0300231A2 (hu)	2003-08-28
NO330223B1 (no)	2011-03-07
NZ534168A (en)	2006-11-30
HRP20040781B1 (en)	2008-12-31
EA009277B1 (ru)	2007-12-28
JP2005521667A (ja)	2005-07-21
AR038340A1 (es)	2005-01-12
CZ2004906A3 (cs)	2004-12-15
EA200400929A1 (ru)	2005-06-30
US20050119492A1 (en)	2005-06-02
RS66704A (en)	2007-02-05
AP2004003091A0 (en)	2004-09-30
PL358514A1 (en)	2003-07-28
CN1300111C (zh)	2007-02-14
JP4171423B2 (ja)	2008-10-22
ES2289060T3 (es)	2008-02-01
CN1622936A (zh)	2005-06-01
SK287866B6 (sk)	2012-02-03
US7279595B2 (en)	2007-10-09
CA2474003C (fr)	2009-06-02
DE60220877D1 (de)	2007-08-09
SK3292004A3 (en)	2004-12-01
ATE365714T1 (de)	2007-07-15
CZ305892B6 (cs)	2016-04-27
PT1333026E (pt)	2007-09-17
US7326794B2 (en)	2008-02-05
EP1333026A1 (fr)	2003-08-06
AP1741A (en)	2007-05-16
BG66126B1 (bg)	2011-06-30

Legal Events

Date	Code	Title	Description
2004-12-31	A1OB	Publication of a patent application
2005-05-17	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2008-12-31	B1PR	Patent granted
2009-01-31	A8IS	Corrected front page of an hr-a document
2009-01-31	B8IS	Corrected front page of an hr-b document
2018-12-28	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20181210 Year of fee payment: 17
2020-08-07	PBON	Lapse due to non-payment of renewal fee	Effective date: 20200129

Publication	Publication Date	Title
HRP20040781B1 (en)	2008-12-31	Process for the preparation of high purity perindopril and intermediates useful in the synthesis
HK1004481A1 (en)	1998-11-27	Depsipeptide derivative, production thereof and use thereof
Qiao et al.	2005	5-Amidinobenzo [b] thiophenes as dual inhibitors of factors IXa and Xa
TNSN05140A1 (en)	2007-05-14	Perindopril
ATE399753T1 (de)	2008-07-15	Amide als pyruvatdehydrogenaseinhibitoren
HUT68056A (en)	1995-05-29	Substituted indoles and azaindoles as angiotensin ii antagonists, pharmaceutical compositions containing same, process for their production and intermediates
HRP20030566B1 (en)	2011-08-31	Improved process for carbapenem synthesis
TW200510299A (en)	2005-03-16	Organic compounds
AU2003242144A1 (en)	2004-01-06	Processes for producing epoxytriazole derivative and intermediate therefor
NO20002589D0 (no)	2000-05-19	Bifenylamidinderivater
DE60335865D1 (de)	2011-03-10	Verfahren zur herstellung von cilostazol
PA8525601A1 (es)	2002-04-25	Profarmacos de (3s,4s)-4-bencil-1-[2-(4-hidroxi-bencenosulfonil)-etil]-piperidin-3-ol
AU714155B2 (en)	1999-12-23	Process for synthesizing carbapenem side chain intermediates
WO2004099138A3 (fr)	2004-12-23	Procede et produit
ATE420067T1 (de)	2009-01-15	Peptid-derivate und ihre pharmazeutisch akzeptablensalze, verfahren zur herstellung von beiden und ihre verwendung
EP1557418A4 (fr)	2008-04-16	Nouveaux derives de quinoxaline
JPH0317051A (ja)	1991-01-25	シクロプロパノイルアミノ酸アミド誘導体
FI944207A0 (fi)	1994-09-12	Cyclohexane derivatives
JPS63238056A (ja)	1988-10-04	ベンズアルドキシム誘導体
MY136639A (en)	2008-11-28	New process for the synthesis of (2s, 3as, 7as)-perhydroindole-2-carboxylic acid and esters thereof, and application in the synthesis of perindopril