DE3870780D1 - Verfahren zur industriellen herstellung von perhydroindol carboxy-2(2s,3as,7as)-saeure, anwendung zur herstellung von carboxyalkyldipeptiden. - Google Patents
Verfahren zur industriellen herstellung von perhydroindol carboxy-2(2s,3as,7as)-saeure, anwendung zur herstellung von carboxyalkyldipeptiden.Info
- Publication number
- DE3870780D1 DE3870780D1 DE8888402337T DE3870780T DE3870780D1 DE 3870780 D1 DE3870780 D1 DE 3870780D1 DE 8888402337 T DE8888402337 T DE 8888402337T DE 3870780 T DE3870780 T DE 3870780T DE 3870780 D1 DE3870780 D1 DE 3870780D1
- Authority
- DE
- Germany
- Prior art keywords
- production
- acid
- application
- carboxyalkyldipeptides
- perhydroindol
- 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
Links
- 239000002253 acid Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 title 1
- 238000009776 industrial production Methods 0.000 title 1
- 238000004519 manufacturing process Methods 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
- 238000003786 synthesis reaction Methods 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
- 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)
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 |
|---|---|
| DE3870780D1 true DE3870780D1 (de) | 1992-06-11 |
Family
ID=9354992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8888402337T Expired - Lifetime 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. |
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 |
| BR0308118A (pt) * | 2002-03-01 | 2005-01-11 | Warner Lambert Co | Método para o tratamento de osteoartrite |
| 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 |
| DE60300168T2 (de) * | 2003-05-19 | 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 |
| PT1354876E (pt) * | 2003-06-13 | 2005-06-30 | Servier Lab | Novo processo de sintese do acido (2s,3as,7as)-per-hidroindole-2-carboxilico e dos seus esteres e aplicacao a sintese do perindopril |
| US20070172524A1 (en) * | 2004-03-29 | 2007-07-26 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Process for preparing a solid pharmaceutical composition |
| 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 |
| EP4168387A1 (en) | 2020-06-23 | 2023-04-26 | 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 |
| 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 |
| 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 IE IE280488A patent/IE61009B1/en not_active IP Right Cessation
- 1988-09-16 JP JP63232123A patent/JPH02191251A/ja active Pending
- 1988-09-16 NZ NZ226223A patent/NZ226223A/xx unknown
- 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 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 ZA ZA886931A patent/ZA886931B/xx unknown
- 1988-09-16 US US07/245,352 patent/US4935525A/en not_active Expired - Lifetime
- 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 OA OA59434A patent/OA08954A/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 |
|---|---|
| US4954640A (en) | 1990-09-04 |
| IE61009B1 (en) | 1994-09-07 |
| DK514988A (da) | 1989-03-18 |
| GR3005361T3 (enExample) | 1993-05-24 |
| OA08954A (fr) | 1990-11-30 |
| ES2033450T3 (es) | 1993-03-16 |
| HK54996A (en) | 1996-04-03 |
| ATE75735T1 (de) | 1992-05-15 |
| ZA886931B (en) | 1989-05-30 |
| US4935525A (en) | 1990-06-19 |
| DK514988D0 (da) | 1988-09-15 |
| AU618752B2 (en) | 1992-01-09 |
| EP0308339B1 (fr) | 1992-05-06 |
| IE882804L (en) | 1989-03-17 |
| PT88528B (pt) | 1992-11-30 |
| NZ226223A (en) | 1990-09-26 |
| FR2620703A1 (fr) | 1989-03-24 |
| PT88528A (pt) | 1988-10-01 |
| AU2236188A (en) | 1989-03-23 |
| EP0308339A1 (fr) | 1989-03-22 |
| FR2620703B1 (fr) | 1991-10-04 |
| JPH02191251A (ja) | 1990-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: LES LABORATOIRES SERVIER, NEUILLY SUR SEINE, FR |