FR2620703B1 - 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
FR2620703B1
FR2620703B1 FR8712900A FR8712900A FR2620703B1 FR 2620703 B1 FR2620703 B1 FR 2620703B1 FR 8712900 A FR8712900 A FR 8712900A FR 8712900 A FR8712900 A FR 8712900A FR 2620703 B1 FR2620703 B1 FR 2620703B1
Authority
FR
France
Prior art keywords
synthesis
application
carboxylic acid
industrial
carboxyalkyl dipeptides
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
FR8712900A
Other languages
English (en)
French (fr)
Other versions
FR2620703A1 (fr
Inventor
Michel Vincent
Jean Baliarda
Bernard Marchand
Georges Remond
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ADIR SARL
Original Assignee
ADIR SARL
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.)
Filing date
Publication date
Application filed by ADIR SARL filed Critical ADIR SARL
Priority to FR8712900A priority Critical patent/FR2620703B1/fr
Priority to DK514988A priority patent/DK514988A/da
Priority to AU22361/88A priority patent/AU618752B2/en
Priority to ZA886931A priority patent/ZA886931B/xx
Priority to NZ226223A priority patent/NZ226223A/xx
Priority to PT88528A priority patent/PT88528B/pt
Priority to JP63232123A priority patent/JPH02191251A/ja
Priority to IE280488A priority patent/IE61009B1/en
Priority to US07/245,352 priority patent/US4935525A/en
Priority to OA59434A priority patent/OA08954A/xx
Priority to EP88402337A priority patent/EP0308339B1/fr
Priority to ES198888402337T priority patent/ES2033450T3/es
Priority to AT88402337T priority patent/ATE75735T1/de
Priority to DE8888402337T priority patent/DE3870780D1/de
Publication of FR2620703A1 publication Critical patent/FR2620703A1/fr
Priority to US07/462,797 priority patent/US4954640A/en
Application granted granted Critical
Publication of FR2620703B1 publication Critical patent/FR2620703B1/fr
Priority to GR920401694T priority patent/GR3005361T3/el
Priority to HK54996A priority patent/HK54996A/xx
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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)
FR8712900A 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 Expired - Lifetime FR2620703B1 (fr)

Priority Applications (17)

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
DK514988A DK514988A (da) 1987-09-17 1988-09-15 Fremgangsmaade til industriel syntese af (2s,3as,7as)-2-carboxyperhydroindol
ES198888402337T ES2033450T3 (es) 1987-09-17 1988-09-16 Procedimiento de sintesis industrial del acido (2s, 3as, 7as,) 2-perhidroindol carboxilico, aplicacion en la sintesis de carboxialquil dipeptidos
NZ226223A NZ226223A (en) 1987-09-17 1988-09-16 Preparation of (2s,3as,7as)-2-carboxyperhydroindole, and use thereof in the preparation of dipeptides
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
JP63232123A JPH02191251A (ja) 1987-09-17 1988-09-16 （２Ｓ，３↓ａＳ，７↓ａＳ）−２−カルボキシペルヒドロインドールの工業的合成法
IE280488A IE61009B1 (en) 1987-09-17 1988-09-16 Process for the industrial synthesis of (2S, 3aS, 7aS) 2 - carboxy perhydroindole. Application to the industrial synthesis of carboxyalkyl dipeptides
US07/245,352 US4935525A (en) 1987-09-17 1988-09-16 Process for the industrial synthesis of (2S, 3aS, 7aS) 2-carboxy perhydroindole, application to the industrial synthesis of carboxyalkyl dipeptides
AU22361/88A AU618752B2 (en) 1987-09-17 1988-09-16 Process for the industrial synthesis of (2s, 3as, 7as) 2-carboxy perhydroindole. application to the industrial synthesis of carboxyalkyl dipeptides
EP88402337A EP0308339B1 (fr) 1987-09-17 1988-09-16 Procédé de synthèse industrielle de l'acide perhydroindole carboxylique - 2 (2S, 3aS, 7aS). Application à la synthèse de carboxyalkyl dipeptides
ZA886931A ZA886931B (en) 1987-09-17 1988-09-16 Process for the industrial synthesis(2s,3as,7as)2-carboxy perhydroindole and to their application to the industrial synthesis of carboxyalkyl dipeptides
AT88402337T ATE75735T1 (de) 1987-09-17 1988-09-16 Verfahren zur industriellen herstellung von perhydroindol carboxy-2(2s,3as,7as)-saeure, anwendung zur herstellung von carboxyalkyldipeptiden.
DE8888402337T DE3870780D1 (de) 1987-09-17 1988-09-16 Verfahren zur industriellen herstellung von perhydroindol carboxy-2(2s,3as,7as)-saeure, anwendung zur herstellung von carboxyalkyldipeptiden.
OA59434A OA08954A (fr) 1987-09-17 1988-09-16 Procédé de synthése industrielle de l'acide perhydroindole carboxylique - 2(2s 3as 7as)
US07/462,797 US4954640A (en) 1987-09-17 1990-01-10 Alpha-methyl benzyl amine salt of indoline -2- carboxylic acid
GR920401694T GR3005361T3 (enExample) 1987-09-17 1992-08-06
HK54996A HK54996A (en) 1987-09-17 1996-03-28 Process for the industrial preparation of perhydroindole -2(2s,3as,7as)-carboxylic acid, use in the preparation of carboxyalkyl dipeptides

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
FR2620703A1 FR2620703A1 (fr) 1989-03-24
FR2620703B1 true FR2620703B1 (fr) 1991-10-04

Family

ID=9354992

Family Applications (1)

Application Number Title Priority Date Filing Date
FR8712900A Expired - Lifetime 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

Country Status (16)

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

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
MXPA04005557A (es) * 2002-03-01 2005-05-17 Warner Lambert Co Metodo para tratar la osteoartritis.
ES2233913T3 (es) * 2003-04-15 2005-06-16 Les Laboratoires Servier Nuevo procedimiento de sintesis del acido (2s,3as,7as) perhidroindol-2-carboxilico y de sus esteres, y aplicacion as la sintesis de perindopril.
EP1354875B1 (fr) * 2003-05-19 2004-11-24 Les Laboratoires Servier Nouveau procédé de synthèse de l'acide (2S, 3aS, 7aS)-perhydroindole-2-carboxilique et de ses esters, et application à la synthèse du perindopril
DK1354876T3 (da) * 2003-06-13 2005-08-15 Servier Lab Fremgangsmåde til syntese af (2S,3aS,7aS)-perhydroindol-2-carboxylsyre og dennes estere og anvendelse heraf i syntesen af perindopril
PT1729739T (pt) * 2004-03-29 2016-12-01 Servier Lab Processo para a preparação de uma composição farmacêutica sólida
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
CN121219263A (zh) * 2023-04-25 2025-12-26 阿尔蒂制药实验室有限公司 制备(2S,3aS,7aS)-八氢-1H-吲哚-2-羧酸的方法

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
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
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
IE52663B1 (en) * 1980-04-02 1988-01-20 Warner Lambert Co Substituted acyl derivatives of octahydro-1h-indole-2-carboxylic acids
EP0046953B1 (de) * 1980-08-30 1989-12-06 Hoechst Aktiengesellschaft Aminosäurederivate, 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

Also Published As

Publication number Publication date
DE3870780D1 (de) 1992-06-11
ZA886931B (en) 1989-05-30
FR2620703A1 (fr) 1989-03-24
DK514988D0 (da) 1988-09-15
HK54996A (en) 1996-04-03
PT88528B (pt) 1992-11-30
OA08954A (fr) 1990-11-30
JPH02191251A (ja) 1990-07-27
PT88528A (pt) 1988-10-01
DK514988A (da) 1989-03-18
US4954640A (en) 1990-09-04
ATE75735T1 (de) 1992-05-15
AU618752B2 (en) 1992-01-09
US4935525A (en) 1990-06-19
EP0308339B1 (fr) 1992-05-06
ES2033450T3 (es) 1993-03-16
IE882804L (en) 1989-03-17
IE61009B1 (en) 1994-09-07
NZ226223A (en) 1990-09-26
GR3005361T3 (enExample) 1993-05-24
AU2236188A (en) 1989-03-23
EP0308339A1 (fr) 1989-03-22

Similar Documents

Publication Publication Date Title
FR2620703B1 (fr) Procede de synthese industrielle de l'acide perhydroindole carboxylique - 2(2s, 3as, 7as). application a la synthese de carboxyalkyl dipeptides
Markland et al. Subtilisin BPN': VII. ISOLATION OF CYANOGEN BROMIDE PEPTIDES AND THE COMPLETE AMINO ACID SEQUENCE
MY110324A (en) Process for the purification of carboxylic acids and/or their anhydrides
FR2603581B1 (fr) Procede pour isoler et purifier des aminoacides par chromatographie
FR2620709B1 (fr) Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese
BR9808785A (pt) Processos para produzir ésteres de citrato
AU8551091A (en) Process for the production of carboxylic acid anhydrides
RO105609B1 (ro) Procedeu de transvinilare a derivatilor vinilici cu acizi bronsted
DE3479118D1 (en) Process for the racemic separation of bicyclic alpha-imino carboxylic-acid esters
Miller et al. The synthesis of glutamine and asparagine peptides and of glutamine
DE69411492D1 (de) Verfahren zur Reinigung von mittleren Olefinen
FR2669221B1 (fr) Procede de preparation par compression directe de comprimes de derives de l'acide cephalosporanique.
RU95109575A (ru) Способ гидроксикарбонилирования пентеновых кислот, бутадиена и его производных
BE866756A (fr) Procede de preparation de produits racemiques ou optiquement actifs pentacycliques du groupe de l'acide apovincaminique
FR2643059B1 (fr) Procede pour la separation selective d'iode par chromatographie a partir d'une solution aqueuse acide
FR2506759B1 (fr) Procede catalytique de production d'anhydrides d'acides carboxyliques par carbonylation d'une olefine et d'un acide carboxylique
SU567748A1 (ru) Способ получени оксидазы д-аминокислот
US4048197A (en) 2,3,3',4'-Biphenyltetracarboxylic acid dianhydride
RU95121368A (ru) Способ выделения дихлоруксусной кислоты
KR910002745A (ko) 드로프로피진의 광학적 분할방법
ATE20341T1 (de) Verfahren zur trennung von l-leucin und lisoleucin.
FR2367759A1 (fr) Procede de purification d'anhydride phtalique
TW375613B (en) Purification of phthalide
JPS5463107A (en) Production of detergent
FR2540864B1 (fr) Procede de preparation catalytique d'un acide, anhydride ou ester d'acide carboxylique par carbonylation d'une olefine

Legal Events

Date Code Title Description
TP Transmission of property