DK514988A - Fremgangsmaade til industriel syntese af (2s,3as,7as)-2-carboxyperhydroindol - Google Patents

Fremgangsmaade til industriel syntese af (2s,3as,7as)-2-carboxyperhydroindol

Info

Publication number: DK514988A
Authority: DK; Denmark
Prior art keywords: carboxyper; hydroindol; procedure; industrial synthesis; synthesis
Prior art date: 1987-09-17

Application number

DK514988A

Other languages

English (en)

Other versions

DK514988D0 (da

Inventor

Michel Vincent

Jean Baliarda

Bernard Marchand

Georges Remond

Original Assignee

Aidr Et Compagnie

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

1988-09-15

Publication date

1989-03-18

1988-09-15 Application filed by Aidr Et Compagnie filed Critical Aidr Et Compagnie

1988-09-15 Publication of DK514988D0 publication Critical patent/DK514988D0/da

1989-03-18 Publication of DK514988A publication Critical patent/DK514988A/da

Links

230000015572 biosynthetic process Effects 0.000 title abstract 3
238000003786 synthesis reaction Methods 0.000 title abstract 3
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 title abstract 2
238000000034 method Methods 0.000 title abstract 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 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
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
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)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Life Sciences & Earth Sciences (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)

DK514988A 1987-09-17 1988-09-15 Fremgangsmaade til industriel syntese af (2s,3as,7as)-2-carboxyperhydroindol DK514988A (da)

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
DK514988D0 DK514988D0 (da)	1988-09-15
DK514988A true DK514988A (da)	1989-03-18

Family

ID=9354992

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK514988A DK514988A (da)	1987-09-17	1988-09-15	Fremgangsmaade til industriel syntese af (2s,3as,7as)-2-carboxyperhydroindol

Country Status (16)

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

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
AU2003248584A1 (en) *	2002-03-01	2003-09-16	Warner-Lambert Company Llc	Method of treating osteoarthritis
EP1354874B1 (fr) *	2003-04-15	2004-11-24	Les Laboratoires Servier	Nouveau procédé de synthèse de l'acide (2s, 3aS, 7aS)-perhydroindole-2-carboxylique et de ses esters, et application a la synthèse du perindopril
SI1354875T1 (en) *	2003-05-19	2005-02-28	Les Laboratoires Servier	Method for synthesis of (2S,3aS,7aS)-perhydroindole-2-carboxylic acid and esters thereof; and use in the synthesis of perindopril
ATE294161T1 (de) *	2003-06-13	2005-05-15	Servier Lab	Verfahren zur synthese von (2s,3as,7as)- perhydroindol-2-carbonsäure und seiner estern, und verwendung in der synthese von perindopril
JP4948392B2 (ja) *	2004-03-29	2012-06-06	レラボラトアセルビエ	固形薬学的組成物を調製するためのプロセス
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
US20230250049A1 (en)	2020-06-23	2023-08-10	Cnrs	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 NZ NZ226223A patent/NZ226223A/xx unknown
- 1988-09-16 PT PT88528A patent/PT88528B/pt not_active IP Right Cessation
- 1988-09-16 JP JP63232123A patent/JPH02191251A/ja active Pending
- 1988-09-16 AU AU22361/88A patent/AU618752B2/en not_active Expired
- 1988-09-16 AT AT88402337T patent/ATE75735T1/de not_active IP Right Cessation
- 1988-09-16 OA OA59434A patent/OA08954A/xx unknown
- 1988-09-16 DE DE8888402337T patent/DE3870780D1/de not_active Expired - Lifetime
- 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 ZA ZA886931A patent/ZA886931B/xx unknown
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
JPH02191251A (ja)	1990-07-27
ATE75735T1 (de)	1992-05-15
AU618752B2 (en)	1992-01-09
ES2033450T3 (es)	1993-03-16
AU2236188A (en)	1989-03-23
FR2620703A1 (fr)	1989-03-24
PT88528A (pt)	1988-10-01
IE61009B1 (en)	1994-09-07
OA08954A (fr)	1990-11-30
US4954640A (en)	1990-09-04
GR3005361T3 (da)	1993-05-24
PT88528B (pt)	1992-11-30
DE3870780D1 (de)	1992-06-11
US4935525A (en)	1990-06-19
FR2620703B1 (fr)	1991-10-04
DK514988D0 (da)	1988-09-15
ZA886931B (en)	1989-05-30
HK54996A (en)	1996-04-03
NZ226223A (en)	1990-09-26
IE882804L (en)	1989-03-17
EP0308339A1 (fr)	1989-03-22
EP0308339B1 (fr)	1992-05-06

Legal Events

Date	Code	Title	Description
1995-07-03	AHS	Application shelved for other reasons than non-payment

Publication	Publication Date	Title
DK514988D0 (da)	1988-09-15	Fremgangsmaade til industriel syntese af (2s,3as,7as)-2-carboxyperhydroindol
DK481889D0 (da)	1989-09-29	Fremgangsmaade til adskillelse af stereoisomere i flerfase- og ekstraktive membranreaktorer
NO302366B1 (no)	1998-02-23	4-merkaptoacetylamino-£2\|benzazepinon(3)-derivater, og farmasöytisk preparat
DK162233C (da)	1992-03-16	Fremgangsmaade til isolering af faktor viii fra blodplasma og pharmaceutisk praeparat indeholdende den saaledes isolerede fator viii
DK163819C (da)	1992-09-07	Fremgangsmaade til adskillelse af racemiske blandinger af bicycliske imino-alfa-carboxylsyreestere
NO920193D0 (no)	1992-01-15	Fremgangsmaate for fremstilling av aspartam fra et diketopiperazin og nye mellomprodukter og derivater derfor
DE69411492D1 (de)	1998-08-13	Verfahren zur Reinigung von mittleren Olefinen
IT1231751B (it)	1991-12-21	Procedimento per la produzione di r(+) amminocarnitina e s(-) amminocarnitina
DK0640095T3 (da)	1999-04-12	Fremgangsmåde til fremstilling af vancomycin
ATE57907T1 (de)	1990-11-15	Kontinuierliches verfahren zur herstellung von 1,2-diolen.
PT78036B (de)	1986-05-30	Verfahren zur racemattrennung optisch aktiver bicyclischer imino-alpha-carbonsaeureester und verwendung der so erhaeltlichen verbindungen zur synthese von carboxyalkyldipeptiden
BG98888A (en)	1995-05-31	Method for the preparation of 3-acylestratrienes and acylbezenes
ATE88188T1 (de)	1993-04-15	Verfahren zur herstellung von antihaemophilem faktor (faktor viii), der eine hohe reinheit aufweist.
DK123089A (da)	1989-09-15	Fremgangsmaade til adskillese af alpha-l-asparagyl-l-phenylalaninmethylester fra en oploesning
DK632187D0 (da)	1987-12-02	Ny forbedret fremgangsmaade til fremstilling af penicillansyrederivater
ATE38668T1 (de)	1988-12-15	Verfahren zur verwertung von phthalsaeureanhydrid- und/oder maleinsaeureanhydrid- destillationsrueckstaenden.
NO793794L (no)	1980-06-17	7,8,9,10-tetrahydrotieno/3,2-e/pyrido/4,3-b/-indoler, fremgangsmaate til deres fremstilling og deres anvendelse som legemiddel
KR880005114A (ko)	1988-06-28	광학적활성 2-메틸-1-(4-트리플루오로메틸페닐)-3-피롤리디노-1-프로파논 및 그 제조방법
JPS5777623A (en)	1982-05-15	Method for preparing blood preparation using activated earth
JPS528007A (en)	1977-01-21	Fractionation of oil and fat
JPS5463107A (en)	1979-05-21	Production of detergent
JPS6183159A (ja)	1986-04-26	Ｎ−アセチルインドリン−２−カルボン酸のラセミ化方法
JPS5242863A (en)	1977-04-04	Process for preparation of n -naphthalenesulfonylarginine esters or am ides or their acid salts
JPS6490137A (en)	1989-04-06	Production of alkene
JPS5216499A (en)	1977-02-07	Method for separation and purification of boron compounds.