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US3755333A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of vincamine

Assignee: Richter Gedeon Vegyeszeti Gyar Nyrt
•
Filing: 1972-05-02
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Granted: 1973-08-28
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Expires: 1992-05-02
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Abstract

Abstract A new process for the preparation of vincamine and of homologues thereof containing acyl groups of 2 to 6 carbon atoms in the 14position, wherein 1-ethyl-2,3,4,6,7,12-hexahydroindolo(2,3a)quinolizine is reacted with an Alpha -acyloxy-acrylic acid derivative of the formula (R C1 5 alkyl) to obtain the corresponding 1-( Beta -acyloxyBeta -R-oxycarbonyl-ethyl)-1-ethyl-1,2,3,4,6,7-hexahydro-12Hindolo(2,3 -a)quinolizine compound, this is converted by deacylation and reduction into the corresponding 1-( Beta hydroxy- Beta -R-oxycarbonyl-ethyl)-1-ethyl-1,2,3,4,6,7,12,12boctahydroindolo(2,3 -a)quinolizine; the latter is treated with an oxidizing agent to yield a mixture of the desired vincamine derivative and the 14-epimer thereof. The latter can be epimerized in a known manner; by using silver carbonate as oxidizing agent, the epimerization occurs simultaneously.

Inventors

  • 👤 C Szantay
  • 👤 V Simonidesz
  • 👤 L Szabo
  • 👤 G Kalaus

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 15:44
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/12; C07D471/14; C07D461/00

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 11 words
A process for the preparation of compounds of the formula I
Claim 2
Dependent Claim 38 words
A process as claimed in claim 1, wherein the compound of the formula VII is oxidized with silver carbonate, whereby the formed epimer of the formula VIII is simultaneously epimerized, to yield a compound of the formula I.
Claim 3
Dependent Claim 38 words
A process as claimed in claim 2, wherein the compound of the formula VII is oxidized with silver carbonate, whereby the formed epimer of the formula VIII is simultaneously epimerized, to yield a compound of the formula I.
Claim 4
Dependent Claim 53 words
A process for the preparation of vincamine, wherein 1-ethyl-2,3,4,6,7,12-hexahydro-12H-indolo(2,3-a)-quinolizine is reacted with Alpha -acetoxy-acrylic acid methyl ester, the obtained 1-( Beta -acetoxy- Beta -methoxycarbonyl-ethyl)-1-ethyl-1,2,3,4,6,7-hexahydro-12H-indolo(2,3 -a)quinolizine or a salt thereof is reduced and deacylated to yield 1-( Beta -hydroxy- Beta -methoxycarbonyl-ethyl)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo(2,3 -a)quinolizin, this product or a salt thereof is treated with an oxidizing agent.
Claim 5
Dependent Claim 24 words
A process as claimed in claim 5, wherein silver carbonate is used as oxidizing agent and toluene or xylene is used as reaction medium.

References Cited (Backward Citations)

US3454583A Cited
US3542796A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1976-08-27 1977-02-26 1977-08-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1980-08-27 1981-02-26 1981-08-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1984-08-27 1985-02-26 1985-08-28 $7700.00 Window Closed / Lapsed

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