PL380409A1 - Proces syntezy perindoprilu i jego farmaceutycznie dopuszczalnych soli - Google Patents

Proces syntezy perindoprilu i jego farmaceutycznie dopuszczalnych soli

Info

Publication number: PL380409A1
Authority: PL; Poland
Prior art keywords: formula; give; reacting; compound; perindopril
Prior art date: 2003-11-19

Application number

PL380409A

Other languages

English (en)

Other versions

PL210769B1 (pl

Inventor

Thierry Dubuffet

Pascal Langlois

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.)

2003-11-19

Filing date

2004-11-18

Publication date

2007-01-22

2004-11-18 Application filed by Les Laboratoires Servier filed Critical Les Laboratoires Servier

2007-01-22 Publication of PL380409A1 publication Critical patent/PL380409A1/pl

2012-02-29 Publication of PL210769B1 publication Critical patent/PL210769B1/pl

Links

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 abstract 4
229960002582 perindopril Drugs 0.000 title abstract 3
150000003839 salts Chemical class 0.000 title abstract 2
230000015572 biosynthetic process Effects 0.000 title 1
238000000034 method Methods 0.000 title 1
238000003786 synthesis reaction Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract 5
JFVLNTLXEZDFHW-QMMMGPOBSA-N (2s)-2-amino-3-(2-bromophenyl)propanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1Br JFVLNTLXEZDFHW-QMMMGPOBSA-N 0.000 abstract 4
-1 (R)-2-substituted propionyl chloride Chemical class 0.000 abstract 3
DPBOUPADTRCCIH-LURJTMIESA-N ethyl (2s)-2-aminopentanoate Chemical compound CCC[C@H](N)C(=O)OCC DPBOUPADTRCCIH-LURJTMIESA-N 0.000 abstract 3
125000001980 alanyl group Chemical class 0.000 abstract 2
238000005859 coupling reaction Methods 0.000 abstract 2
125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 abstract 2
238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
230000008878 coupling Effects 0.000 abstract 1
238000010168 coupling process Methods 0.000 abstract 1
238000010511 deprotection reaction Methods 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

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

PL380409A 2003-11-19 2004-11-18 Sposób otrzymywania perindoprilu i jego farmaceutycznie dopuszczalnych soli oraz związek przejściowy PL210769B1 (pl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP03292864A EP1420028B1 (fr)	2003-11-19	2003-11-19	Pocédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
PCT/FR2004/002936 WO2005054276A1 (fr)	2003-11-19	2004-11-18	Procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables

Publications (2)

Publication Number	Publication Date
PL380409A1 true PL380409A1 (pl)	2007-01-22
PL210769B1 PL210769B1 (pl)	2012-02-29

Family

ID=32116380

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL380409A PL210769B1 (pl)	2003-11-19	2004-11-18	Sposób otrzymywania perindoprilu i jego farmaceutycznie dopuszczalnych soli oraz związek przejściowy

Country Status (28)

Country	Link
US (1)	US7208607B1 (pl)
EP (1)	EP1420028B1 (pl)
JP (1)	JP4377412B2 (pl)
KR (1)	KR100863394B1 (pl)
CN (1)	CN100447152C (pl)
AR (1)	AR047312A1 (pl)
AT (1)	ATE354586T1 (pl)
AU (1)	AU2004295132B2 (pl)
BR (1)	BRPI0416746B1 (pl)
CA (1)	CA2546506C (pl)
CY (1)	CY1106544T1 (pl)
DE (1)	DE60311942T2 (pl)
DK (1)	DK1420028T3 (pl)
EA (1)	EA010102B1 (pl)
EG (1)	EG26629A (pl)
ES (1)	ES2282586T3 (pl)
GE (1)	GEP20084547B (pl)
MA (1)	MA28144A1 (pl)
MX (1)	MXPA06005607A (pl)
MY (1)	MY138550A (pl)
NO (1)	NO336349B1 (pl)
NZ (1)	NZ546931A (pl)
PL (1)	PL210769B1 (pl)
PT (1)	PT1420028E (pl)
SI (1)	SI1420028T1 (pl)
UA (1)	UA83269C2 (pl)
WO (1)	WO2005054276A1 (pl)
ZA (1)	ZA200603675B (pl)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1380591B1 (fr) *	2003-08-29	2005-11-16	Les Laboratoires Servier	Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
NZ548212A (en)	2003-12-29	2010-07-30	Sepracor Inc	Pyrrole and pyrazole DAAO inhibitors
WO2007006003A2 (en)	2005-07-06	2007-01-11	Sepracor Inc.	Combinations of eszopiclone and trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine, and methods of treatment of menopause and mood, anxiety, and cognitive disorders
KR101294014B1 (ko)	2006-01-06	2013-08-09	선오비온 파마슈티컬스 인코포레이티드	모노아민 재흡수 저해제로서의 시클로알킬아민
US8053603B2 (en)	2006-01-06	2011-11-08	Sunovion Pharmaceuticals Inc.	Tetralone-based monoamine reuptake inhibitors
DK2816024T3 (en)	2006-03-31	2017-10-30	Sunovion Pharmaceuticals Inc	CHIRALE AMINER
US7884124B2 (en)	2006-06-30	2011-02-08	Sepracor Inc.	Fluoro-substituted inhibitors of D-amino acid oxidase
US7902252B2 (en)	2007-01-18	2011-03-08	Sepracor, Inc.	Inhibitors of D-amino acid oxidase
MX2009012685A (es)	2007-05-31	2009-12-14	Sepracor Inc	Cicloalquilaminas sustituidas con fenilo como inhibidores de la reabsorcion de monoamina.
WO2016178591A2 (en)	2015-05-05	2016-11-10	Gene Predit, Sa	Genetic markers and treatment of male obesity
PH12018502155B1 (en)	2016-04-20	2024-03-27	Servier Lab	Pharmaceutical composition comprising a beta blocker, a converting enzyme inhibitor and an antihypertensive or an nsaid
CN112047869B (zh) *	2020-08-20	2021-12-21	华南理工大学	一种氮杂5,6-并环化合物的合成方法

Family Cites Families (1)

* 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

2003
- 2003-11-19 PT PT03292864T patent/PT1420028E/pt unknown
- 2003-11-19 AT AT03292864T patent/ATE354586T1/de active
- 2003-11-19 EP EP03292864A patent/EP1420028B1/fr not_active Expired - Lifetime
- 2003-11-19 ES ES03292864T patent/ES2282586T3/es not_active Expired - Lifetime
- 2003-11-19 DE DE60311942T patent/DE60311942T2/de not_active Expired - Lifetime
- 2003-11-19 SI SI200330702T patent/SI1420028T1/sl unknown
- 2003-11-19 DK DK03292864T patent/DK1420028T3/da active
2004
- 2004-11-18 AU AU2004295132A patent/AU2004295132B2/en not_active Ceased
- 2004-11-18 WO PCT/FR2004/002936 patent/WO2005054276A1/fr not_active Ceased
- 2004-11-18 US US10/580,148 patent/US7208607B1/en not_active Expired - Fee Related
- 2004-11-18 KR KR1020067011929A patent/KR100863394B1/ko not_active Expired - Fee Related
- 2004-11-18 UA UAA200606747A patent/UA83269C2/uk unknown
- 2004-11-18 PL PL380409A patent/PL210769B1/pl unknown
- 2004-11-18 AR ARP040104252A patent/AR047312A1/es not_active Application Discontinuation
- 2004-11-18 MX MXPA06005607A patent/MXPA06005607A/es active IP Right Grant
- 2004-11-18 ZA ZA200603675A patent/ZA200603675B/en unknown
- 2004-11-18 GE GEAP20049463A patent/GEP20084547B/en unknown
- 2004-11-18 CN CNB2004800336869A patent/CN100447152C/zh not_active Expired - Fee Related
- 2004-11-18 BR BRPI0416746-5A patent/BRPI0416746B1/pt not_active IP Right Cessation
- 2004-11-18 NZ NZ546931A patent/NZ546931A/en not_active IP Right Cessation
- 2004-11-18 MY MYPI20044785A patent/MY138550A/en unknown
- 2004-11-18 CA CA2546506A patent/CA2546506C/fr not_active Expired - Fee Related
- 2004-11-18 EA EA200600898A patent/EA010102B1/ru not_active IP Right Cessation
- 2004-11-18 JP JP2006540515A patent/JP4377412B2/ja not_active Expired - Fee Related
2006
- 2006-05-02 MA MA28993A patent/MA28144A1/fr unknown
- 2006-05-16 EG EGPCTNA2006000459A patent/EG26629A/en active
- 2006-06-06 NO NO20062599A patent/NO336349B1/no not_active IP Right Cessation
2007
- 2007-04-26 CY CY20071100562T patent/CY1106544T1/el unknown

Also Published As

Publication number	Publication date
NO20062599L (no)	2006-06-06
EA200600898A1 (ru)	2006-10-27
NZ546931A (en)	2010-01-29
MY138550A (en)	2009-06-30
EG26629A (en)	2014-04-13
AU2004295132B2 (en)	2010-07-15
DE60311942T2 (de)	2007-12-06
AR047312A1 (es)	2006-01-18
CA2546506A1 (fr)	2005-06-16
AU2004295132A1 (en)	2005-06-16
CN100447152C (zh)	2008-12-31
US20070083052A1 (en)	2007-04-12
BRPI0416746A (pt)	2007-01-16
SI1420028T1 (sl)	2007-06-30
ES2282586T3 (es)	2007-10-16
UA83269C2 (uk)	2008-06-25
HK1096689A1 (en)	2007-06-08
KR100863394B1 (ko)	2008-10-14
US7208607B1 (en)	2007-04-24
EA010102B1 (ru)	2008-06-30
CN1882607A (zh)	2006-12-20
ZA200603675B (en)	2007-09-26
BRPI0416746B1 (pt)	2018-02-14
CY1106544T1 (el)	2012-01-25
CA2546506C (fr)	2010-04-06
MA28144A1 (fr)	2006-09-01
DK1420028T3 (da)	2007-06-18
EP1420028A2 (fr)	2004-05-19
EP1420028A3 (fr)	2004-05-26
ATE354586T1 (de)	2007-03-15
PT1420028E (pt)	2007-05-31
GEP20084547B (en)	2008-11-25
EP1420028B1 (fr)	2007-02-21
MXPA06005607A (es)	2006-08-17
JP4377412B2 (ja)	2009-12-02
DE60311942D1 (de)	2007-04-05
NO336349B1 (no)	2015-08-03
WO2005054276A1 (fr)	2005-06-16
JP2008502587A (ja)	2008-01-31
PL210769B1 (pl)	2012-02-29
KR20060121202A (ko)	2006-11-28

Publication	Publication Date	Title
CA2073510A1 (en)	1992-06-04	Peptidyl derivatives
MA27130A1 (fr)	2005-01-03	Nouveau procede de synthese de derives de l'acide (2s,3as,7as)-1-[(s)-alanyl]-octahydro- 1h-indole-2-carboxylique et application a la synthese du perindopril
AP1741A (en)	2007-05-16	Process for the preparation of high purity perindopril and intermediates useful in the synthesis
CZ285593B6 (cs)	1999-09-15	Způsob výroby (S)-3-amino-1-substituovaných pyrrolidinů
MA27633A1 (fr)	2005-11-01	Nouveau procede de synthese de l'acide (2s)-indoline -2-carboxylique, et application a la synthese du perindopril.
WO2005054276A1 (fr)	2005-06-16	Procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables
BG65833B1 (bg)	2010-02-26	Метод за синтез на n-[(s)-1-карбоксибутил]-(s)-аланинови естери и използването им в синтеза на периндоприл
US7223872B2 (en)	2007-05-29	Process for the synthesis of perindopril and its pharmaceutically acceptable salts
UA73562C2 (uk)	2005-08-15	Спосіб синтезу n-[(s)-1-карбоксибутил]-(s)-аланінових ефірів і їх застосування у синтезі периндоприлу
WO2009098251A1 (en)	2009-08-13	NOVEL CYCLOALKANONE β-SUBSTITUTED ALANINE DERIVATIVES
US20070043103A1 (en)	2007-02-22	Novel metod for the synthesis of perindopril and the pharmaceutically-acceptable salts thereof
US7534896B2 (en)	2009-05-19	Process for the synthesis of perindopril and its pharmaceutically acceptable salts
JP4368304B2 (ja)	2009-11-18	アミノ−ピロリジン誘導体を製造するための方法
Suzuki et al.	1974	The Synthesis of α-Methylamino Acids
CN1331883C (zh)	2007-08-15	(2S,3aS,7aS)－1－[(S)－丙氨酰]－八氢－1H－吲哚－2－甲酸衍生物的新合成方法及其在合成培哚普利中的应用
WO2004078707A3 (fr)	2004-10-14	Nouveau procede de synthese de lacide (2s, 3as, 7as)-perhydroindole-2-carboxylique et de ses esters et application a la synthese du perindopril
NZ187538A (en)	1982-08-17	2-amino-2-halomethyl-3-phenylpropionic acid derivatives
WO2004082357A3 (fr)	2004-10-28	NOUVEAU PROCEDE DE SYNTHESE DE DERIVES DE L'ACIDE (2S, 3aS, 7aS)-1-[(S)-ALANYL]-OCTAHYDRO-lH-INDOLE-2- CARBOXYLIQUE ET APPLICATION A LA SYNTHESE DU PERINDOPRIL
WO2004099138A3 (en)	2004-12-23	Process for the preparation of perindopril
JP4263743B2 (ja)	2009-05-13	ペリンドプリル及びその薬学的に許容し得る塩の新規な合成方法
US7368580B2 (en)	2008-05-06	Method for the synthesis of perindopril and the pharmaceutically acceptable salts thereof
Ross et al.	1997	Synthesis of 2S-[2-2H]-kynurenine and use in kinetic isotope effect studies with kynureninase
MY136549A (en)	2008-10-31	NEW PROCESS FOR THE SYNTHESIS OF (2S, 3aS, 7aS)-PERHYDROINDOLE-2-CARBOXYLIC ACID AND ESTERS THEREOF, AND APPLICATION IN THE SYNTHESIS OF PERINDOPRIL
JP4608922B2 (ja)	2011-01-12	含窒素複素環化合物の製造方法
MA28223A1 (fr)	2006-10-02	NOUVEAU PROCEDE DE SYNTHESE DE DERIVES DE L'ACIDE (2S,3aS,7aS)-1-[(S)-ALANYL]-OCTAHYDRO-1H-INDOLE-2-CARBOXYLIQUE ET APPLICATION A LA SYNTHESE DU PERINDOPRIL