Vincamine derivatives and process for the preparation of vincamine and derivatives thereof
AssigneeAgence Nationale de Valorisation de la Recherche (ANVAR)
InventorsThierry Sevenet, Claude Thal, Henri Philippe Husson, Pierre Potier
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Abstract
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.
Claims7
20-Deethyl-apovincamine, having the formula:
- ##SPC7##
- under its racemic and optically active forms.
20-Deethyl-eburnamonine, having the formula:
- ##SPC8##
- under its racemic and optically active forms.
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.
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.
A compound having the formula ##SPC15##
- in which R is selected from the group consisting of hydrogen and ethyl.
1,2,3,4,6,7,12,12b-Octahydro-1-ethoxycarbonylmethylindolo[ 2-3a]-quinolizine having the formula:
- ##SPC16##
Dependencies are inferred from the claim text.