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Vincamine derivatives and process for the preparation of vincamine and derivatives thereof
| Details |
Inventors: Sevenet, Thierry; Thal, Claude; Husson, Henri Philippe; Potier, Pierre;
Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR) (Neuilly-sur-Seine, FR)
Primary Examiner: Todd; G. Thomas
Assistant Examiner:
Attorney, Agent or Firm: Schellin; Eric P.
New compounds having the formula ##SPC1## In which Y represents a hydrogen atom, in which case Z.sub.1 and Z.sub.2 represent simultaneously an oxygen atom, or Z.sub.1 represents a methoxycarbonyl radical and Z.sub.2 a hydroxy radical, or Y and Z.sub.2 form together a carbon-carbon bond and Z.sub.1 is a methoxycarbonyl radical, said compounds being additionally characterized by a cis-fusion of the D/E rings. Said new compounds and vincamine and certain of its derivatives are prepared from an enamine having the formula: ##SPC2## In which R is H or C.sub.2 H.sub.5. |
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DETAILED DESCRIPTION Having now described our invention what we claim as new and desire to secure by Letters Patent is: 1.
20-Deethyl-apovincamine, having the formula: ##SPC7## under its racemic and optically active forms.
2.
20-Deethyl-eburnamonine, having the formula: ##SPC8## under its racemic and optically active forms.
3.
Process for the preparation of compounds having the formula: ##SPC9## in which, taken together, Z.
sub.
1 and Z.
sub.
2 represent an oxygen atom, and, taken separately, represent one a methoxycarbonyl radical and the other a hydroxy radical and R represents a radical selected from the group consisting of hydrogen and the ethyl group, comprising alkylating an enamine having the formula: ##SPC10## in which R has the above-defined meaning, with methyl .
alpha.
-bromomethyl acrylate, reducing the resulting immonium salt, oxydizing the compound produced which cyclizes simultaneously to give the compound in which Z.
sub.
1 is COOCH.
sub.
3 and Z.
sub.
2 is OH, which is converted, if desired, to the compound in which Z.
sub.
1 and Z.
sub.
2 represent together an oxygen atom.
4.
Process as claimed in claim 3, for the preparation of vincamine, comprising alkylating the enamine having the formula: ##SPC11## with methyl .
alpha.
-bromomethylacrylate, reducing the resulting immonium salt having the formula: ##SPC12## with sodium borohydride and then oxidizing the resulting compound ##SPC13## with osmium tetraoxide or potassium permanganate in the presence of periodic acid and, cyclization occurring simultaneously, thus obtaining vincamine.
5.
Process for the preparation of 20-deethyl-eburnamonine, comprising reacting the enamine having the formula ##SPC14## with an ethyl halogeno-acetate, reducing the resulting immonium salt and cyclizing the compound obtained after reduction.
6.
A compound having the formula ##SPC15## in which R is selected from the group consisting of hydrogen and ethyl.
7.
1,2,3,4,6,7,12,12b-Octahydro-1-ethoxycarbonylmethylindolo[ 2-3a]-quinolizine having the formula: ##SPC16##
Description:
This invention relates to new vincamine derivatives and to a novel process for the preparation of vincamine and of vincamine derivatives
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