FR2192107A1 - Vincamine and apovincamine synthesis - via novel inters - Google Patents

Vincamine and apovincamine synthesis - via novel inters

Info

Publication number
FR2192107A1
FR2192107A1 FR7331032A FR7331032A FR2192107A1 FR 2192107 A1 FR2192107 A1 FR 2192107A1 FR 7331032 A FR7331032 A FR 7331032A FR 7331032 A FR7331032 A FR 7331032A FR 2192107 A1 FR2192107 A1 FR 2192107A1
Authority
FR
France
Prior art keywords
apovincamine
vincamine
resulting
inters
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
Application number
FR7331032A
Other languages
French (fr)
Other versions
FR2192107B1 (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.)
Sandoz AG
Original Assignee
Sandoz AG
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
Priority claimed from CH583372A external-priority patent/CH575415A5/en
Priority claimed from CH731072A external-priority patent/CH576472A5/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of FR2192107A1 publication Critical patent/FR2192107A1/en
Application granted granted Critical
Publication of FR2192107B1 publication Critical patent/FR2192107B1/fr
Granted legal-status Critical Current

Links

Classifications

    • 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
    • C07D471/12—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 three hetero rings
    • C07D471/14—Ortho-condensed systems
    • 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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C07D209/16—Tryptamines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

3-Ethyl-3-formyl-N-(2-(3-indolyl)-ethyl)-2-piperidone is treated with a cpd. of the formula (CH3O)2P(O)-CH(OR)-COOCH3 (where R is lower alkyl) in the presence of a basic condensn. agent, the resulting cpd is subjected to Bischler-Napieralski cyclization and then catalytically reduced, followed by acidic cleavage, the resulting mixture of optically active or racemic vincamine (I) and apovincamine II is sepd. in a conventional manner, and (II) being opt. treated with hydrogen halide at 0 degrees C, the reaction product hydrolysed, and resulting (I) isolated in a conventional manner. (I) has vasodilating, hypotensive and sedative props.
FR7331032A 1972-04-20 1973-08-28 Vincamine and apovincamine synthesis - via novel inters Granted FR2192107A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH583372A CH575415A5 (en) 1972-04-20 1972-04-20 Vincamine and apovincamine synthesis - via novel inters
CH731072A CH576472A5 (en) 1972-05-17 1972-05-17 Vincamine and apovincamine synthesis - via novel inters
CH140873 1973-02-02

Publications (2)

Publication Number Publication Date
FR2192107A1 true FR2192107A1 (en) 1974-02-08
FR2192107B1 FR2192107B1 (en) 1977-02-25

Family

ID=27172953

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7331032A Granted FR2192107A1 (en) 1972-04-20 1973-08-28 Vincamine and apovincamine synthesis - via novel inters

Country Status (1)

Country Link
FR (1) FR2192107A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4173642A (en) * 1976-12-30 1979-11-06 Richter Gedeon Vegyeszeti Gyar Rt Vasodilating 1,1-di-(2-methoxycarbonyl-ethyl)-1,2,3,4,5,6,12,12b-octahydro-indolo[2,3-a]quinolizine

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7206174A (en) * 1971-05-07 1972-11-09

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7206174A (en) * 1971-05-07 1972-11-09

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4173642A (en) * 1976-12-30 1979-11-06 Richter Gedeon Vegyeszeti Gyar Rt Vasodilating 1,1-di-(2-methoxycarbonyl-ethyl)-1,2,3,4,5,6,12,12b-octahydro-indolo[2,3-a]quinolizine
US4278682A (en) * 1976-12-30 1981-07-14 Richter Gedeon Vegyeszeti Gyar Rt. Vasodilating method of treatment using a indolo-quinolizine-monoester, diester or nitrile

Also Published As

Publication number Publication date
FR2192107B1 (en) 1977-02-25

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Legal Events

Date Code Title Description
ST Notification of lapse