UA72040C2 - A method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine ethers and use thereof in the synthesis of perindoprile - Google Patents

A method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine ethers and use thereof in the synthesis of perindoprile Download PDF

Info

Publication number: UA72040C2
Authority: UA; Ukraine
Prior art keywords: synthesis; alanine; perindoprile; carboxybutyl; ethers
Prior art date: 2000-04-11

Application number

UA2002118916A

Other languages

English (en)

Ukrainian (uk)

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.)

2000-04-11

Filing date

2001-10-04

Publication date

2005-01-17

2001-10-04 Application filed by Servier Lab filed Critical Servier Lab

2005-01-17 Publication of UA72040C2 publication Critical patent/UA72040C2/uk

Links

230000015572 biosynthetic process Effects 0.000 title abstract description 5
238000000034 method Methods 0.000 title abstract description 3
238000003786 synthesis reaction Methods 0.000 title abstract 4
229960003767 alanine Drugs 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 abstract 1
229960002582 perindopril Drugs 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
230000000707 stereoselective effect Effects 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
YERWBBMSDMSDKT-UHFFFAOYSA-N ethyl 2-oxopentanoate Chemical compound CCCC(=O)C(=O)OCC YERWBBMSDMSDKT-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
- 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
- A61P9/04—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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers

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

UA2002118916A 2000-04-11 2001-10-04 A method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine ethers and use thereof in the synthesis of perindoprile UA72040C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0004610A FR2807430B1 (fr)	2000-04-11	2000-04-11	Nouveau procede de synthese des esters de la n-[(s)-1- carboxybutyl]-(s)-alanine et application a la synthese du perindopril
PCT/FR2001/001088 WO2001056972A1 (fr)	2000-04-11	2001-04-10	Nouveau procede de synthese des esters de la n-[(s)-1-carboxybutyl]-(s)-alanine et application a la synthese du perindopril

Publications (1)

Publication Number	Publication Date
UA72040C2 true UA72040C2 (en)	2005-01-17

Family

ID=8849107

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002118916A UA72040C2 (en)	2000-04-11	2001-10-04	A method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine ethers and use thereof in the synthesis of perindoprile

Country Status (35)

Country	Link
US (1)	US6774259B2 (de)
EP (1)	EP1272454B1 (de)
JP (1)	JP3872344B2 (de)
KR (1)	KR100520700B1 (de)
CN (1)	CN1176903C (de)
AP (1)	AP1417A (de)
AR (1)	AR027782A1 (de)
AT (1)	ATE362913T1 (de)
AU (2)	AU2001250467B2 (de)
BG (1)	BG65833B1 (de)
BR (1)	BR0109963A (de)
CA (1)	CA2405466C (de)
CY (1)	CY1106720T1 (de)
CZ (1)	CZ302603B6 (de)
DE (1)	DE60128554T2 (de)
DK (1)	DK1272454T3 (de)
EA (1)	EA004265B1 (de)
EE (1)	EE05030B1 (de)
ES (1)	ES2287114T3 (de)
FR (1)	FR2807430B1 (de)
GE (1)	GEP20063798B (de)
HR (1)	HRP20020887B1 (de)
HU (1)	HU229189B1 (de)
ME (1)	ME00442B (de)
MX (1)	MXPA02009888A (de)
NO (1)	NO327970B1 (de)
NZ (1)	NZ521846A (de)
OA (1)	OA12246A (de)
PL (1)	PL346553A1 (de)
PT (1)	PT1272454E (de)
RS (1)	RS50240B (de)
SK (1)	SK287067B6 (de)
UA (1)	UA72040C2 (de)
WO (1)	WO2001056972A1 (de)
ZA (1)	ZA200207689B (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2807037B1 (fr) *	2000-03-31	2002-05-10	Adir	NOUVEAU PROCEDE DE SYNTHESE DES ESTERS DE LA N-[(s)-1- CARBOXYBUTYL]-(S)-ALANINE ET APPLICATION A LA SYNTHESE DU PERINDOPRIL
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
US7521566B2 (en)	2003-02-28	2009-04-21	Les Laboratoires Servier	Process for preparation of perindopril and salts thereof
ATE445588T1 (de) *	2003-09-01	2009-10-15	Servier Lab	Neues verfahren zur herstellung von estern des n- ((s)-1-carboxybutyl)-(s)-alanins und seine verwendung in der synthese von perindopril
SI1400531T1 (sl) *	2003-09-30	2006-04-30	Servier Lab	Postopek za sintezo n-((s)-1-karbetoksibutil)-(s)-alanina in uporaba pri sintezi perindoprila
SI1403278T1 (en) *	2003-09-30	2005-10-31	Les Laboratoires Servier	Process for the synthesis of N-((S)-1-(ethoxycarbonyl)butyl)-(S)-alanine and use in the synthese of perindopril
LT1729739T (lt) *	2004-03-29	2016-11-10	Les Laboratoires Servier	Kietos farmacinės kompozicijos gamybos būdas
SI21800A (sl) *	2004-05-14	2005-12-31	Krka, Tovarna Zdravil, D.D., Novo Mesto	Nov postopek sinteze perindoprila
EP1792896A1 (de)	2005-12-01	2007-06-06	KRKA, tovarna zdravil, d.d., Novo mesto	Verfahren zur Herstellung von Perindopril und deren Salze
FI126564B (fi)	2011-02-28	2017-02-15	Andritz Oy	Menetelmä ja laitteisto meesan polttamiseksi
CN107098949B (zh) *	2017-04-20	2021-03-16	上药东英（江苏）药业有限公司	一种制备培哚普利叔丁胺盐的绿色合成新工艺

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
US4344949A (en) *	1980-10-03	1982-08-17	Warner-Lambert Company	Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids
US4296110A (en) *	1980-10-28	1981-10-20	E. I. Du Pont De Nemours And Company	Antihypertensive I-substituted cyclic lactam-2-carboxylic acids
US4503043A (en) *	1981-12-07	1985-03-05	Warner-Lambert Company	Substituted acyl derivatives of octahydro-1H-isoindole-1-carboxylic acids
FR2620699B1 (fr) *	1987-09-17	1990-06-01	Adir	Procede de synthese d'alpha amino acides n alkyles et de leurs esters. application a la synthese de carboxyalkyl dipeptides
FR2620709B1 (fr) *	1987-09-17	1990-09-07	Adir	Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese
FR2620700B1 (fr) *	1987-09-17	1990-06-01	Adir	Procede de synthese d'alpha amino acides n alkyles et leurs esters. application a la synthese de carboxyalkyl dipeptides

2000
- 2000-04-11 FR FR0004610A patent/FR2807430B1/fr not_active Expired - Fee Related
2001
- 2001-03-20 PL PL01346553A patent/PL346553A1/xx not_active Application Discontinuation
- 2001-03-30 HU HU0101337A patent/HU229189B1/hu not_active IP Right Cessation
- 2001-04-09 AR ARP010101670A patent/AR027782A1/es not_active Application Discontinuation
- 2001-04-10 GE GEAP20016688A patent/GEP20063798B/en unknown
- 2001-04-10 KR KR10-2002-7013604A patent/KR100520700B1/ko not_active Expired - Fee Related
- 2001-04-10 BR BR0109963-9A patent/BR0109963A/pt not_active Application Discontinuation
- 2001-04-10 ME MEP-2008-671A patent/ME00442B/me unknown
- 2001-04-10 RS YU76702A patent/RS50240B/sr unknown
- 2001-04-10 EA EA200201049A patent/EA004265B1/ru not_active IP Right Cessation
- 2001-04-10 DE DE60128554T patent/DE60128554T2/de not_active Expired - Lifetime
- 2001-04-10 HR HR20020887A patent/HRP20020887B1/xx not_active IP Right Cessation
- 2001-04-10 WO PCT/FR2001/001088 patent/WO2001056972A1/fr not_active Ceased
- 2001-04-10 ES ES01923776T patent/ES2287114T3/es not_active Expired - Lifetime
- 2001-04-10 SK SK1457-2002A patent/SK287067B6/sk not_active IP Right Cessation
- 2001-04-10 AU AU2001250467A patent/AU2001250467B2/en not_active Ceased
- 2001-04-10 PT PT01923776T patent/PT1272454E/pt unknown
- 2001-04-10 CZ CZ20023323A patent/CZ302603B6/cs not_active IP Right Cessation
- 2001-04-10 JP JP2001556822A patent/JP3872344B2/ja not_active Expired - Fee Related
- 2001-04-10 US US10/257,239 patent/US6774259B2/en not_active Expired - Lifetime
- 2001-04-10 AP APAP/P/2002/002639A patent/AP1417A/en active
- 2001-04-10 CN CNB018079210A patent/CN1176903C/zh not_active Expired - Fee Related
- 2001-04-10 AU AU5046701A patent/AU5046701A/xx active Pending
- 2001-04-10 OA OA1200200313A patent/OA12246A/en unknown
- 2001-04-10 CA CA002405466A patent/CA2405466C/fr not_active Expired - Fee Related
- 2001-04-10 DK DK01923776T patent/DK1272454T3/da active
- 2001-04-10 EP EP01923776A patent/EP1272454B1/de not_active Expired - Lifetime
- 2001-04-10 EE EEP200200586A patent/EE05030B1/xx not_active IP Right Cessation
- 2001-04-10 NZ NZ521846A patent/NZ521846A/en not_active IP Right Cessation
- 2001-04-10 AT AT01923776T patent/ATE362913T1/de active
- 2001-04-10 MX MXPA02009888A patent/MXPA02009888A/es active IP Right Grant
- 2001-10-04 UA UA2002118916A patent/UA72040C2/uk unknown
2002
- 2002-09-25 ZA ZA200207689A patent/ZA200207689B/xx unknown
- 2002-10-04 NO NO20024811A patent/NO327970B1/no not_active IP Right Cessation
- 2002-11-04 BG BG107250A patent/BG65833B1/bg unknown
2007
- 2007-07-12 CY CY20071100924T patent/CY1106720T1/el unknown

Also Published As

Publication number	Publication date
CZ20023323A3 (cs)	2003-01-15
EP1272454A1 (de)	2003-01-08
JP3872344B2 (ja)	2007-01-24
CN1422245A (zh)	2003-06-04
DE60128554D1 (de)	2007-07-05
US20030109743A1 (en)	2003-06-12
NO20024811D0 (no)	2002-10-04
CN1176903C (zh)	2004-11-24
HUP0101337A3 (en)	2002-11-28
EE05030B1 (et)	2008-06-16
CY1106720T1 (el)	2012-05-23
ZA200207689B (en)	2003-09-25
NO20024811L (no)	2002-10-04
BR0109963A (pt)	2003-08-05
BG107250A (bg)	2003-06-30
EE200200586A (et)	2004-04-15
AP1417A (en)	2005-05-24
NO327970B1 (no)	2009-11-02
DE60128554T2 (de)	2008-02-21
ATE362913T1 (de)	2007-06-15
HUP0101337A2 (hu)	2001-11-28
GEP20063798B (en)	2006-04-25
HRP20020887B1 (en)	2011-03-31
PT1272454E (pt)	2007-08-01
CZ302603B6 (cs)	2011-08-03
DK1272454T3 (da)	2007-09-17
HRP20020887A2 (en)	2004-02-29
ME00442B (me)	2011-10-10
RS50240B (sr)	2009-07-15
AP2002002639A0 (en)	2002-09-30
KR20020093902A (ko)	2002-12-16
SK14572002A3 (sk)	2003-02-04
EA004265B1 (ru)	2004-02-26
CA2405466A1 (fr)	2001-08-09
PL346553A1 (en)	2001-09-10
AR027782A1 (es)	2003-04-09
WO2001056972A1 (fr)	2001-08-09
BG65833B1 (bg)	2010-02-26
AU2001250467B2 (en)	2005-02-17
SK287067B6 (sk)	2009-11-05
MXPA02009888A (es)	2004-09-06
HU0101337D0 (en)	2001-06-28
KR100520700B1 (ko)	2005-10-17
AU5046701A (en)	2001-08-14
YU76702A (sh)	2006-05-25
JP2003521530A (ja)	2003-07-15
EA200201049A1 (ru)	2003-02-27
HU229189B1 (hu)	2013-09-30
FR2807430A1 (fr)	2001-10-12
FR2807430B1 (fr)	2002-05-17
ES2287114T3 (es)	2007-12-16
CA2405466C (fr)	2005-02-15
NZ521846A (en)	2004-07-30
US6774259B2 (en)	2004-08-10
HK1053300A1 (en)	2003-10-17
OA12246A (en)	2003-12-08
EP1272454B1 (de)	2007-05-23

Publication	Publication Date	Title
UA72040C2 (en)	2005-01-17	A method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine ethers and use thereof in the synthesis of perindoprile
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Myers et al.	1995	A one-step synthesis of pseudoephedrine glycinamide, a versatile precursor for the synthesis of α-amino acids
JPH10237030A (ja)	1998-09-08	分岐鎖アミノ酸の精製法
UA73562C2 (uk)	2005-08-15	Спосіб синтезу n-[(s)-1-карбоксибутил]-(s)-аланінових ефірів і їх застосування у синтезі периндоприлу
JPWO1999033785A1 (ja)	2002-09-24	β−ハロゲノ−α−アミノカルボン酸並びにフェニルシステイン誘導体及びその中間体の製造方法
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