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ES476504A1 - Un procedimiento para la preparacion de vincadiformina - Google Patents

Un procedimiento para la preparacion de vincadiformina

Info

Publication number
ES476504A1
ES476504A1 ES476504A ES476504A ES476504A1 ES 476504 A1 ES476504 A1 ES 476504A1 ES 476504 A ES476504 A ES 476504A ES 476504 A ES476504 A ES 476504A ES 476504 A1 ES476504 A1 ES 476504A1
Authority
ES
Spain
Prior art keywords
vincadifformine
preparation
relates
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
Application number
ES476504A
Other languages
English (en)
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.)
Omnium Chimique SA
Original Assignee
Omnium Chimique SA
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 Omnium Chimique SA filed Critical Omnium Chimique SA
Publication of ES476504A1 publication Critical patent/ES476504A1/es
Expired legal-status Critical Current

Links

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)

Abstract

Esta invención se refiere a la preparación de vincadiformina. Se hace reaccionar tetrahidro-Beta-carbolina (II) con cloruro de benzoílo para dar 2-benzoil-1,2,3,4-tetrahidro-9H-pirido[3,4b] indol (III). Después se reduce el compuesto (III) para dar 2-bencil-1,2,3,4-tetrahidro-9H-pirido[3,4b] indol (IV). A continuación el compuesto (IV) se transformar con hipoclorito de ter-butilo en un derivado de cloroindolenina (V) que inmediatamente se trata con talio-malonato de ter-butilo y metilo para formar 3-bencil-1,2,3,4,5,6-hexahidroazepino[4,5b]indol-5,5-dicarboxilato de ter-butilo y metilo (VI). El compuesto (VI) se descarboxila después parcialmente para formar 3-bencil-1,2,3,4,5,6-hexahidroazepino[4,5b]indol-5-carboxilato de metilo (VII). El compuesto (VII) se hidrogena para dar 1,2,3,4,5,6-hexahidroazepino [4,5b]indol-5-carboxilato de metilo (IX). En otra realización, el compuesto (VI) puede ser hidrogenado a 1,2,3,4,5,6-hexahidroazepin [4,5b]indol-5,5-dicarboxilato de metilo y ter-butilo (VIII) que después se descarboxila a compuesto (IX). El compuesto (IX) se condensa con 1-bromo-4-formil-hexano para dar vincadiformina (I)
ES476504A 1977-12-29 1978-12-29 Un procedimiento para la preparacion de vincadiformina Expired ES476504A1 (es)

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 (1)

Publication Number Publication Date
ES476504A1 true ES476504A1 (es) 1979-11-16

Family

ID=25345973

Family Applications (1)

Application Number Title Priority Date Filing Date
ES476504A Expired ES476504A1 (es) 1977-12-29 1978-12-29 Un procedimiento para la preparacion de vincadiformina

Country Status (9)

Country Link
US (1) US4154943A (es)
JP (1) JPS5498800A (es)
BE (1) BE873136A (es)
CA (1) CA1098903A (es)
ES (1) ES476504A1 (es)
FR (1) FR2413391A1 (es)
GB (1) GB2011899B (es)
HU (1) HU180905B (es)
IT (1) IT1109011B (es)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
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
FR2434166A2 (fr) * 1978-08-24 1980-03-21 Omnium Chimique Sa Procede de preparation de vincadifformine et derives similaires
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
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
AR024158A1 (es) 1999-06-01 2002-09-04 Smithkline Beecham Corp Compuestos antibacterianos
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
EP1226138B1 (en) * 1999-10-08 2004-12-29 Affinium Pharmaceuticals, Inc. Fab i inhibitors
US7049310B2 (en) * 2001-04-06 2006-05-23 Affinium Pharmaceuticals, Inc. Fab I inhibitors
DK1575951T3 (da) * 2002-12-06 2014-09-15 Debiopharm Int Sa Heterocykliske forbindelser, fremgangsmåder til fremstilling deraf og deres anvendelse i terapi
CA2519429C (en) 2003-03-17 2013-08-06 Affinium Pharmaceuticals, Inc. Pharmaceutical compositions comprising inhibitors of fab i and further antibiotics
DK1828167T3 (da) * 2004-06-04 2014-10-20 Debiopharm Int Sa Acrylamidderivater som antibiotiske midler
JP2009518399A (ja) * 2005-12-05 2009-05-07 アフィニウム ファーマシューティカルズ， インク． Ｆａｂｉ阻害剤および抗菌剤としてのヘテロ環アクリルアミド化合物
EP2687533B1 (en) 2006-07-20 2017-07-19 Debiopharm International SA Acrylamide derivatives as FAB I inhibitors
US8263613B2 (en) * 2007-02-16 2012-09-11 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
EP2861608B8 (en) 2012-06-19 2019-06-19 Debiopharm International SA Prodrug derivatives of (e)-n-methyl-n-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide
MY189221A (en) 2016-02-26 2022-01-31 Debiopharm Int Sa Medicament for treatment of diabetic foot infections
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
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

Also Published As

Publication number Publication date
JPS6215555B2 (es) 1987-04-08
JPS5498800A (en) 1979-08-03
HU180905B (en) 1983-05-30
GB2011899A (en) 1979-07-18
BE873136A (fr) 1979-06-28
FR2413391B1 (es) 1983-08-05
US4154943A (en) 1979-05-15
IT1109011B (it) 1985-12-16
CA1098903A (en) 1981-04-07
IT7809692A0 (it) 1978-12-29
GB2011899B (en) 1982-05-26
FR2413391A1 (fr) 1979-07-27

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