PT88528A - Procede de synthese industrielle de l'acide perhydroindole carboxylique-2(2s,3as,7as) application a la synthese de carboxyalkyl dipeptides - Google Patents

Procede de synthese industrielle de l'acide perhydroindole carboxylique-2(2s,3as,7as) application a la synthese de carboxyalkyl dipeptides

Info

Publication number: PT88528A
Authority: PT; Portugal
Prior art keywords: synthese; application; perhydroindole; carboxylique; procede
Prior art date: 1987-09-17

Application number

PT88528A

Other languages

English (en)

Other versions

PT88528B (pt

Inventor

Michel Vincent

Jean Baliarda

Bernard Marchand

Georges Remond

Original Assignee

Adir

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.)

1987-09-17

Filing date

1988-09-16

Publication date

1988-10-01

1988-09-16 Application filed by Adir filed Critical Adir

1988-10-01 Publication of PT88528A publication Critical patent/PT88528A/pt

1992-11-30 Publication of PT88528B publication Critical patent/PT88528B/pt

Links

238000003786 synthesis reaction Methods 0.000 title abstract 4
PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 title 1
108010016626 Dipeptides Proteins 0.000 title 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
230000015572 biosynthetic process Effects 0.000 abstract 2
150000002148 esters Chemical class 0.000 abstract 2
QNRXNRGSOJZINA-QMMMGPOBSA-N (2s)-2,3-dihydro-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2N[C@H](C(=O)O)CC2=C1 QNRXNRGSOJZINA-QMMMGPOBSA-N 0.000 abstract 1
CQYBNXGHMBNGCG-FXQIFTODSA-N (2s,3as,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2[NH2+][C@H](C(=O)[O-])C[C@@H]21 CQYBNXGHMBNGCG-FXQIFTODSA-N 0.000 abstract 1
239000002253 acid Substances 0.000 abstract 1
125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
238000002425 crystallisation Methods 0.000 abstract 1
230000008025 crystallization Effects 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
238000000034 method Methods 0.000 abstract 1
239000000203 mixture Substances 0.000 abstract 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 abstract 1
238000001556 precipitation Methods 0.000 abstract 1
102000004196 processed proteins & peptides Human genes 0.000 abstract 1
108090000765 processed proteins & peptides Proteins 0.000 abstract 1
238000007127 saponification reaction Methods 0.000 abstract 1
238000000926 separation method Methods 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
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Proteomics, Peptides & Aminoacids (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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

PT88528A 1987-09-17 1988-09-16 Processo para a sintese industrial do acido perhidroindol-2(2s,3as,7as)-carboxilico e sua aplicacao para a sintese de carboxialquil-dipeptidos PT88528B (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8712900A FR2620703B1 (fr)	1987-09-17	1987-09-17	Procede de synthese industrielle de l'acide perhydroindole carboxylique - 2(2s, 3as, 7as). application a la synthese de carboxyalkyl dipeptides

Publications (2)

Publication Number	Publication Date
PT88528A true PT88528A (pt)	1988-10-01
PT88528B PT88528B (pt)	1992-11-30

Family

ID=9354992

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PT88528A PT88528B (pt)	1987-09-17	1988-09-16	Processo para a sintese industrial do acido perhidroindol-2(2s,3as,7as)-carboxilico e sua aplicacao para a sintese de carboxialquil-dipeptidos

Country Status (16)

Country	Link
US (2)	US4935525A (pt)
EP (1)	EP0308339B1 (pt)
JP (1)	JPH02191251A (pt)
AT (1)	ATE75735T1 (pt)
AU (1)	AU618752B2 (pt)
DE (1)	DE3870780D1 (pt)
DK (1)	DK514988A (pt)
ES (1)	ES2033450T3 (pt)
FR (1)	FR2620703B1 (pt)
GR (1)	GR3005361T3 (pt)
HK (1)	HK54996A (pt)
IE (1)	IE61009B1 (pt)
NZ (1)	NZ226223A (pt)
OA (1)	OA08954A (pt)
PT (1)	PT88528B (pt)
ZA (1)	ZA886931B (pt)

Families Citing this family (16)

* 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
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
BR0308118A (pt) *	2002-03-01	2005-01-11	Warner Lambert Co	Método para o tratamento de osteoartrite
DE60300166T2 (de) *	2003-04-15	2005-12-01	Les Laboratoires Servier	Verfahren zur Synthese von (2S, 3aS, 7aS)-Perhydroindol-2-carbonsäure und seinen Estern, und Verwendung in der Synthese von Perindopril
DK1354875T3 (da) *	2003-05-19	2005-03-14	Servier Lab	Ny syntesefremgangsmåde for (2S, 3aS, 7aS)-perhydroindol-2-carboxylsyre og estere heraf samt anvendelse ved syntese af perindopril
SI1354876T1 (pt) *	2003-06-13	2005-08-31	Servier Lab
HRP20161602T1 (hr) *	2004-03-29	2016-12-30	Les Laboratoires Servier	Postupak priprave čvrstog farmaceutskog pripravka
SI21800A (sl)	2004-05-14	2005-12-31	Krka, Tovarna Zdravil, D.D., Novo Mesto	Nov postopek sinteze perindoprila
FR2883874A1 (fr) *	2005-04-04	2006-10-06	Substipharm Lab	PROCEDE DE SYNTHESE DE L'ACIDE (2S,3aS, 7aS)-PERHYDROINDOLE- 2 CARBOXYLIQUE ET DE SES ESTHERS
EP1792896A1 (en) *	2005-12-01	2007-06-06	KRKA, tovarna zdravil, d.d., Novo mesto	Process for the preparation of perindopril and salts thereof
FR2985511B1 (fr) *	2012-01-05	2014-01-03	Servier Lab	Forme cristalline delta du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent
CN106631977A (zh) *	2016-11-11	2017-05-10	上海雅本化学有限公司	一种s‑吲哚啉‑2‑羧酸合成的优化方法
CA3183877A1 (en)	2020-06-23	2021-12-30	Jean-Francois Briere	Process for the preparation of ortho-halogenated phenylalanine compounds
CN112375028A (zh) *	2020-12-14	2021-02-19	安徽美诺华药物化学有限公司	合成（2s）-二氢吲哚-甲酸的方法
WO2024224414A1 (en) *	2023-04-25	2024-10-31	Aarti Pharmalabs Limited	Process for preparation of (2s, 3as,7as)-octahydro-1h-indole-2-carboxylic acid

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4303583A (en) *	1979-08-13	1981-12-01	American Home Products Corporation	1H,5H-[1,4]Thiazepino[4,3-a]indole-1,5-diones
FR2487829A2 (fr) *	1979-12-07	1982-02-05	Science Union & Cie	Nouveaux imino acides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme
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
IE52663B1 (en) *	1980-04-02	1988-01-20	Warner Lambert Co	Substituted acyl derivatives of octahydro-1h-indole-2-carboxylic acids
DE3177130D1 (de) *	1980-08-30	1990-01-11	Hoechst Ag	Aminosaeurederivate, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung.
US4479963A (en) *	1981-02-17	1984-10-30	Ciba-Geigy Corporation	1-Carboxyalkanoylindoline-2-carboxylic acids
DE3226768A1 (de) *	1981-11-05	1983-05-26	Hoechst Ag, 6230 Frankfurt	Derivate der cis, endo-2-azabicyclo-(3.3.0)-octan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung
US4520205A (en) *	1982-06-28	1985-05-28	American Home Products Corporation	Chemical resolution of (+)-2,3-dihydroindole-2-carboxylic acid
HU191120B (en) *	1983-01-31	1987-01-28	Hoechts Ag,De	Process for raceme separation of optically active byciclic imino-alpha-carbonic acid esthers
DE3322530A1 (de) *	1983-06-23	1985-01-10	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von mono-, bi- und tricyclischen aminosaeuren
DE3345355A1 (de) *	1983-12-15	1985-06-27	Hoechst Ag, 6230 Frankfurt	Verfahren zur racematspaltung bicyclischer imino-(alpha)-carbonsaeureester
DE3408923A1 (de) *	1984-03-12	1985-09-26	Hoechst Ag, 6230 Frankfurt	Carboxyalkyldipeptidderivate, verfahren zu deren herstellung, diese enthaltende mittel und deren verwendung
JPH0798802B2 (ja) *	1984-07-13	1995-10-25	東レ株式会社	光学活性インドリン―２―カルボン酸の製造法
KR880001848B1 (ko) *	1985-07-04	1988-09-22	재단법인 한국화학연구소	인돌린 유도체의 제조방법

1987
- 1987-09-17 FR FR8712900A patent/FR2620703B1/fr not_active Expired - Lifetime
1988
- 1988-09-15 DK DK514988A patent/DK514988A/da not_active Application Discontinuation
- 1988-09-16 ES ES198888402337T patent/ES2033450T3/es not_active Expired - Lifetime
- 1988-09-16 PT PT88528A patent/PT88528B/pt not_active IP Right Cessation
- 1988-09-16 AU AU22361/88A patent/AU618752B2/en not_active Expired
- 1988-09-16 DE DE8888402337T patent/DE3870780D1/de not_active Expired - Lifetime
- 1988-09-16 NZ NZ226223A patent/NZ226223A/xx unknown
- 1988-09-16 JP JP63232123A patent/JPH02191251A/ja active Pending
- 1988-09-16 ZA ZA886931A patent/ZA886931B/xx unknown
- 1988-09-16 OA OA59434A patent/OA08954A/xx unknown
- 1988-09-16 EP EP88402337A patent/EP0308339B1/fr not_active Expired - Lifetime
- 1988-09-16 IE IE280488A patent/IE61009B1/en not_active IP Right Cessation
- 1988-09-16 US US07/245,352 patent/US4935525A/en not_active Expired - Lifetime
- 1988-09-16 AT AT88402337T patent/ATE75735T1/de not_active IP Right Cessation
1990
- 1990-01-10 US US07/462,797 patent/US4954640A/en not_active Expired - Lifetime
1992
- 1992-08-06 GR GR920401694T patent/GR3005361T3/el unknown
1996
- 1996-03-28 HK HK54996A patent/HK54996A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
OA08954A (fr)	1990-11-30
DE3870780D1 (de)	1992-06-11
FR2620703A1 (fr)	1989-03-24
NZ226223A (en)	1990-09-26
GR3005361T3 (pt)	1993-05-24
AU618752B2 (en)	1992-01-09
EP0308339A1 (fr)	1989-03-22
DK514988A (da)	1989-03-18
ZA886931B (en)	1989-05-30
US4954640A (en)	1990-09-04
ATE75735T1 (de)	1992-05-15
DK514988D0 (da)	1988-09-15
AU2236188A (en)	1989-03-23
FR2620703B1 (fr)	1991-10-04
EP0308339B1 (fr)	1992-05-06
ES2033450T3 (es)	1993-03-16
IE61009B1 (en)	1994-09-07
HK54996A (en)	1996-04-03
PT88528B (pt)	1992-11-30
US4935525A (en)	1990-06-19
JPH02191251A (ja)	1990-07-27
IE882804L (en)	1989-03-17

Legal Events

Date

Code

Title

Description

1992-11-30

FG3A

Patent granted, date of granting

Effective date: 19920505

2002-02-28

PC3A

Transfer or assignment

Free format text: 20011105 LES LABORATOIRES SERVIER FR

2008-09-30

MM4A

Annulment/lapse due to non-payment of fees, searched and examined patent

Free format text: MAXIMUM VALIDITY LIMIT REACHED

Effective date: 20080916

Publication	Publication Date	Title
PT88528A (pt)	1988-10-01	Procede de synthese industrielle de l'acide perhydroindole carboxylique-2(2s,3as,7as) application a la synthese de carboxyalkyl dipeptides
Markland et al.	1967	Subtilisin BPN': VII. ISOLATION OF CYANOGEN BROMIDE PEPTIDES AND THE COMPLETE AMINO ACID SEQUENCE
PT88527A (pt)	1988-10-01	Procede de synthese industrielle du perindopril et des principaux intermediaires de synthese
FR2603581B1 (fr)	1993-08-13	Procede pour isoler et purifier des aminoacides par chromatographie
BG103694A (bg)	2000-07-31	Метод за получаване и пречистване на n- алкилирано аспарагиново производно
FR2625690B1 (fr)	1993-04-23	Procede de separation des constituants d'un melange en phase gazeuse au moyen d'une membrane composite
BR9808785A (pt)	2000-08-08	Processos para produzir ésteres de citrato
FR2827860B1 (fr)	2004-12-10	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
BE851080A (fr)	1977-08-04	Procede de purification d'eaux contenant des produits organiques par extraction desdits produits organiques au moyen d'un solvant immobilise
DE59705670D1 (de)	2002-01-17	Chromatographisches verfahren zur gewinnung von hochgereinigtem cyclosporin a und verwandten cyclosporinen
BE899254A (fr)	1984-07-16	Procede ameliore pour la purification de la tylosine.
DE69411492D1 (de)	1998-08-13	Verfahren zur Reinigung von mittleren Olefinen
BE862990A (fr)	1978-05-16	Procede pour l'epuration d'eaux residuaires contenant du phenol par voie d'adsorption, ainsi que pour la valorisation des produits d'adsorption
IT1231751B (it)	1991-12-21	Procedimento per la produzione di r(+) amminocarnitina e s(-) amminocarnitina
FR2455602A1 (fr)	1980-11-28	Derives d'acide folique marques au radio-iode, leur procede de production et leur application a l'analyse medicale
WO1999009004A3 (en)	1999-06-03	Process for preparing and/or purifying amido acid phenyl ester sulfonates
ATE125874T1 (de)	1995-08-15	Verfahren zur herstellung von fester lactulose.
PT74766A (fr)	1982-05-01	Procede de preparation de nouveaux derives de l'acide cyclopropane carboxylique
BE866756A (fr)	1978-11-06	Procede de preparation de produits racemiques ou optiquement actifs pentacycliques du groupe de l'acide apovincaminique
FR2753703B1 (fr)	1998-12-04	Procede de synthese de l'acide mercapto-3-propionique
FR2411158A1 (fr)	1979-07-06	Procede de purification du chlorure de potassium cristallin
FR2609978B1 (fr)	1989-03-31	Procede de synthese de l'arsine par reduction de l'anhydride arsenieux
IT1163772B (it)	1987-04-08	Oligosaccaridi eterogenei complessabili ed alfa-idosani ad attivita' terapeutica, procedimento per la loro preparazione e relative composizioni farmaceutiche
FR2441612A1 (fr)	1980-06-13	Procede de purification du tryptophane et de derives du triptophane
FR2611743B1 (fr)	1994-06-10	Procede pour la production de l-aminoacides ou d'acide 5'-inosinique par fermentation