FR2413391A1 - Procede de preparation de la vincadifformine - Google Patents
Procede de preparation de la vincadifformineInfo
- Publication number
- FR2413391A1 FR2413391A1 FR7836935A FR7836935A FR2413391A1 FR 2413391 A1 FR2413391 A1 FR 2413391A1 FR 7836935 A FR7836935 A FR 7836935A FR 7836935 A FR7836935 A FR 7836935A FR 2413391 A1 FR2413391 A1 FR 2413391A1
- Authority
- FR
- France
- Prior art keywords
- vincadifformin
- indole
- hexahydroazepino
- tetrahydro
- synthesis
- 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.)
- Granted
Links
- GIGFIWJRTMBSRP-UHFFFAOYSA-N DL-Vincadifformin Natural products C1C(C(=O)OC)=C2NC3=CC=CC=C3C22CCN3CCCC1(CC)C23 GIGFIWJRTMBSRP-UHFFFAOYSA-N 0.000 title abstract 4
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 abstract 1
- RHJAPLVWPWSYLO-UHFFFAOYSA-N 5-bromo-2-ethylpentanal Chemical compound CCC(C=O)CCCBr RHJAPLVWPWSYLO-UHFFFAOYSA-N 0.000 abstract 1
- -1 T-BUTYL Chemical class 0.000 abstract 1
- 229930013930 alkaloid Natural products 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/313—Compounds having groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/865,657 US4154943A (en) | 1977-12-29 | 1977-12-29 | Preparation of vincadifformine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2413391A1 true FR2413391A1 (fr) | 1979-07-27 |
| FR2413391B1 FR2413391B1 (https=) | 1983-08-05 |
Family
ID=25345973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7836935A Granted FR2413391A1 (fr) | 1977-12-29 | 1978-12-29 | Procede de preparation de la vincadifformine |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4154943A (https=) |
| JP (1) | JPS5498800A (https=) |
| BE (1) | BE873136A (https=) |
| CA (1) | CA1098903A (https=) |
| ES (1) | ES476504A1 (https=) |
| FR (1) | FR2413391A1 (https=) |
| GB (1) | GB2011899B (https=) |
| HU (1) | HU180905B (https=) |
| IT (1) | IT1109011B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2434166A2 (fr) * | 1978-08-24 | 1980-03-21 | Omnium Chimique Sa | Procede de preparation de vincadifformine et derives similaires |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4283536A (en) * | 1977-12-29 | 1981-08-11 | University Of Vermont | Preparation of vincadifformine and related derivatives |
| US4267330A (en) * | 1978-08-24 | 1981-05-12 | Omnium Chimique Societe Anonyme | Process for the synthesis of vincadifformine and related derivatives |
| US4220774A (en) * | 1978-10-26 | 1980-09-02 | Omnium Chimique | Vincadifformine synthesis process |
| US4362739A (en) * | 1981-05-04 | 1982-12-07 | S.A. Omnichem | Pyrrolo(2,3-d)carbazole derivatives, compositions and use |
| US4428880A (en) | 1981-05-04 | 1984-01-31 | S.A. Omnichem | Azepino[4,5-d]indole derivatives and preparation thereof |
| LU85894A1 (fr) * | 1985-05-10 | 1986-12-05 | Omnichem Sa | Derives de 1,2,3,4,5,6-hexahydro-azepino (4,5-b) indole leur preparation,composes intermediaires,et leur application en therapeutique |
| CO5180550A1 (es) | 1999-04-19 | 2002-07-30 | Smithkline Beecham Corp | Inhibidores de fab i |
| CO5370679A1 (es) | 1999-06-01 | 2004-02-27 | Smithkline Beecham Corp | Inhibidores fab 1 |
| US6730684B1 (en) | 1999-10-08 | 2004-05-04 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| US6762201B1 (en) | 1999-10-08 | 2004-07-13 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| ATE285821T1 (de) * | 1999-10-08 | 2005-01-15 | Affinium Pharm Inc | Fab i inhibitoren |
| CA2444597A1 (en) * | 2001-04-06 | 2002-10-06 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| EP1575951B1 (en) * | 2002-12-06 | 2014-06-25 | Debiopharm International SA | Heterocyclic compounds, methods of making them and their use in therapy |
| DE602004016831D1 (de) | 2003-03-17 | 2008-11-13 | Affinium Pharm Inc | Pharmazeutische zusammensetzungen inhibitoren von fab i und weitere antibiotika enthaltend |
| EP2848614A3 (en) * | 2004-06-04 | 2015-07-29 | Debiopharm International SA | Acrylamide derivatives as antibiotic agents |
| EP1973902A2 (en) * | 2005-12-05 | 2008-10-01 | Affinium Pharmaceuticals, Inc. | 3-heterocyclylacrylamide compounds as fabi inhibitors and antibacterial agents |
| EP2687533B1 (en) * | 2006-07-20 | 2017-07-19 | Debiopharm International SA | Acrylamide derivatives as FAB I inhibitors |
| WO2008098374A1 (en) | 2007-02-16 | 2008-08-21 | Affinium Pharmaceuticals, Inc. | Salts, prodrugs and polymorphs of fab i inhibitors |
| US20130178618A1 (en) | 2012-01-10 | 2013-07-11 | William Allen Boulanger | Novel pharmaceutical intermediates and methods for preparing the same |
| SI2861608T1 (sl) | 2012-06-19 | 2019-08-30 | Debiopharm International Sa | Derivati predzdravila (E)-N-metil-N-((3-metilbenzofuran-2-IL)metil)- 3-(7-okso-5,6,7,8-tetrahidro-1 ,8-nafthiridin-3-il)akrilamid |
| BR122023021456A2 (pt) | 2016-02-26 | 2024-02-20 | Debiopharm International S.A. | Uso de di-hidrogeno fosfato de {6- [(e)-3-{metil[(3-metil-1-benfofuran-2- iol)metil]amino)-3- oxopro-1-en-1-il]-2-oxo-3,4-di-hidro-1,8-naftiridin-1(2h)- il}metila para tratamento de osteomielite do pé diabético e composição farmacêutica |
| CN107216328A (zh) * | 2017-07-06 | 2017-09-29 | 贵州医科大学 | 一种α‑卡波林类化合物的合成方法 |
| LT3923914T (lt) | 2019-02-14 | 2023-07-25 | Debiopharm International S.A. | Afabicino kompozicija, jos gamybos būdas |
| CN113939306B (zh) | 2019-06-14 | 2024-07-19 | 德彪药业国际股份公司 | 用于治疗涉及生物膜的细菌感染的药物及其用途 |
| US12116372B1 (en) | 2023-12-14 | 2024-10-15 | William Allen Boulanger | Process for preparing methyl 3-bromo-2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)propanoate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE811614A (en) | 1974-02-27 | 1974-06-17 | (-) Vincadifformine prodn. - by hemisynthesis starting from vindolinine which is obtd. from catharantus roseus |
-
1977
- 1977-12-29 US US05/865,657 patent/US4154943A/en not_active Expired - Lifetime
-
1978
- 1978-12-28 CA CA318,789A patent/CA1098903A/en not_active Expired
- 1978-12-28 HU HU78OI222A patent/HU180905B/hu not_active IP Right Cessation
- 1978-12-28 BE BE192612A patent/BE873136A/xx not_active IP Right Cessation
- 1978-12-29 JP JP16439678A patent/JPS5498800A/ja active Granted
- 1978-12-29 IT IT09692/78A patent/IT1109011B/it active
- 1978-12-29 GB GB7850201A patent/GB2011899B/en not_active Expired
- 1978-12-29 FR FR7836935A patent/FR2413391A1/fr active Granted
- 1978-12-29 ES ES476504A patent/ES476504A1/es not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2434166A2 (fr) * | 1978-08-24 | 1980-03-21 | Omnium Chimique Sa | Procede de preparation de vincadifformine et derives similaires |
| FR2445332A2 (fr) * | 1978-08-24 | 1980-07-25 | Omnium Chimique Sa | Derives de 1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole et leur procede de preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1098903A (en) | 1981-04-07 |
| US4154943A (en) | 1979-05-15 |
| FR2413391B1 (https=) | 1983-08-05 |
| ES476504A1 (es) | 1979-11-16 |
| BE873136A (fr) | 1979-06-28 |
| JPS6215555B2 (https=) | 1987-04-08 |
| GB2011899A (en) | 1979-07-18 |
| HU180905B (en) | 1983-05-30 |
| GB2011899B (en) | 1982-05-26 |
| JPS5498800A (en) | 1979-08-03 |
| IT1109011B (it) | 1985-12-16 |
| IT7809692A0 (it) | 1978-12-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |