OA08954A - Procédé de synthése industrielle de l'acide perhydroindole carboxylique - 2(2s 3as 7as) - Google Patents
Procédé de synthése industrielle de l'acide perhydroindole carboxylique - 2(2s 3as 7as)Info
- Publication number
- OA08954A OA08954A OA59434A OA59434A OA08954A OA 08954 A OA08954 A OA 08954A OA 59434 A OA59434 A OA 59434A OA 59434 A OA59434 A OA 59434A OA 08954 A OA08954 A OA 08954A
- Authority
- OA
- OAPI
- Prior art keywords
- carboxylic acid
- industrial synthesis
- synthesis
- carboxyindoline
- carboxyperhydroindole
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 3
- 238000003786 synthesis reaction Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- CQYBNXGHMBNGCG-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCCC2NC(C(=O)O)CC21 CQYBNXGHMBNGCG-UHFFFAOYSA-N 0.000 title 1
- 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
- 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
- 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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| OA08954A true OA08954A (fr) | 1990-11-30 |
Family
ID=9354992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA59434A OA08954A (fr) | 1987-09-17 | 1988-09-16 | Procédé de synthése industrielle de l'acide perhydroindole carboxylique - 2(2s 3as 7as) |
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)
| 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)
| 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 |
-
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 EP EP88402337A patent/EP0308339B1/fr not_active Expired - Lifetime
- 1988-09-16 DE DE8888402337T patent/DE3870780D1/de not_active Expired - Lifetime
- 1988-09-16 ES ES198888402337T patent/ES2033450T3/es not_active Expired - Lifetime
- 1988-09-16 AT AT88402337T patent/ATE75735T1/de not_active IP Right Cessation
- 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
- 1988-09-16 OA OA59434A patent/OA08954A/xx unknown
- 1988-09-16 AU AU22361/88A patent/AU618752B2/en not_active Expired
- 1988-09-16 JP JP63232123A patent/JPH02191251A/ja active Pending
- 1988-09-16 PT PT88528A patent/PT88528B/pt not_active IP Right Cessation
- 1988-09-16 NZ NZ226223A patent/NZ226223A/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 |
|---|---|
| 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 |
| 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 |
| FR2620703B1 (fr) | 1991-10-04 |
| AU2236188A (en) | 1989-03-23 |
| EP0308339A1 (fr) | 1989-03-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| OA08954A (fr) | Procédé de synthése industrielle de l'acide perhydroindole carboxylique - 2(2s 3as 7as) | |
| 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 | |
| ATE64958T1 (de) | Kontinuierliches verfahren zur fermentativen herstellung organischer saeuren. | |
| AU8551091A (en) | Process for the production of carboxylic acid anhydrides | |
| BR9808785A (pt) | Processos para produzir ésteres de citrato | |
| DE69411492D1 (de) | Verfahren zur Reinigung von mittleren Olefinen | |
| ATE108174T1 (de) | Verfahren zur herstellung von r(+)-aminocarnitin und s(-)-aminocarnitin. | |
| BE866756A (fr) | Procede de preparation de produits racemiques ou optiquement actifs pentacycliques du groupe de l'acide apovincaminique | |
| PT74766A (fr) | Procede de preparation de nouveaux derives de l'acide cyclopropane carboxylique | |
| IT1222427B (it) | Procedimento per la purificazione di interferone | |
| DE69116879D1 (de) | Verfahren und reinigung von essigsäureanhydrid und essigsäure | |
| US4048197A (en) | 2,3,3',4'-Biphenyltetracarboxylic acid dianhydride | |
| KR910002745A (ko) | 드로프로피진의 광학적 분할방법 | |
| FR2643059B1 (fr) | Procede pour la separation selective d'iode par chromatographie a partir d'une solution aqueuse acide | |
| SU567748A1 (ru) | Способ получени оксидазы д-аминокислот | |
| RU95121368A (ru) | Способ выделения дихлоруксусной кислоты | |
| NO891069L (no) | Fremgangsmaate for rensing av uren alfa-l-aspartyl-l-fenylalaninmethylester (alfa-apm). | |
| FR2367759A1 (fr) | Procede de purification d'anhydride phtalique | |
| Barton et al. | Radical Reactions Based on the Thione Function | |
| ATE38668T1 (de) | Verfahren zur verwertung von phthalsaeureanhydrid- und/oder maleinsaeureanhydrid- destillationsrueckstaenden. | |
| TW375613B (en) | Purification of phthalide | |
| JPS5463107A (en) | Production of detergent | |
| RO95814A2 (ro) | Procedeu de obtinere a acidului piperidin-2-carboxilic | |
| DE59400810D1 (de) | Verfahren zur Herstellung eines Indolderivates |