Abstract: This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of vincamine and other related compounds possessing interesting psychopharmacologic properties.A N-benzyl-tetrahydro-.gamma.-carboline compound (III) is halogenated with t-butyl hypochlorite to obtain a haloindolenine compound which is directly treated with a metal dialkyl malonate such as thallium dialkyl malonate to provide a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5,5-dicarboxylate compound, said latter compound being hydrogenated to provide a dialkyl 1,2,3,4,5,6 hexahydroazepino (4,5-b) indole-5,5-dicarboxylate, said latter compound being condensed with a functionalized aldehyde, typically a haloaldehyde, to provide vincadifformine or a related derivative by passing through an intermediate compound being a salt of a dialkyl 3,3-(alkenyl)-1,2,3,4,5,6-hexahydroazepino(4,5-b) indolinium-(5,5)-dicarboxylate.

Abstract: The invention relates to new indole derivatives, their preparation and use as drugs.Said compounds may be represented by the general formula ##STR1## in which R represents a hydrogen atom or an alkyl or benzyl group and Z represents a hydrogen atom or a halogen atom or an alkyl, hydroxy, acyloxy, carbamate or methoxy group.They are prepared by reacting tryptamine derivatives with synthons of the formula ##STR2## in which X and Y each represent an oxygen or sulphur atom, and R.sub.1 and R.sub.2 each represent an alkyl or phenyl radical or form together an alkylidene chain.They may be used as intermediate compounds for chemical syntheses and also as drug for treating cerebro-vascular and cardio-circulatory insufficiencies.

Abstract: N-disubstituted aminoethyl esters of 11-methoxy-raubasinic acid of the formula : ##STR1## in which R is an alkyl group containing up to 4 carbon atoms or the two R groups, together with the nitrogen atom to which they are attached, form a morpholinyl, piperidinyl, piperazinyl or pyrrolidinyl group, and their physiologically acceptable acid addition salts. The process for the preparation of an N-disubstituted aminoethyl ester of 11-methoxy-raubasinic acid of the formula specified hereinabove, which comprises esterifying 11-methoxy-raubasinic acid with a substituted aminoethyl halide of the formula: ##STR2## in which X is a halogen atom and R has the meaning specified in claim 1.

Abstract: As novel compounds: N-disubstituted amino-ethyl esters of raubasine of the general formula: ##STR1## in which: R.sub.1 and R.sub.2 are alkyl radicals or form together with the nitrogen atom to which they are attached a heterocyclic ring of the morpholinyl, piperidinyl, piperazinyl or pyrrolidinyl type.Preparation of the compounds by reacting raubasinic acid with a halide of a substituted amino-ethane of the formula ##STR2## R.sub.1 and R.sub.2 have the same significance and X is a halogen in an organic solvent in the presence of an alkali carbonate insoluble in the reaction medium.

Abstract: In the preparation of vincadifformine and derivatives thereof, such as 3-oxo-1,2-dehydroaspidospermidine and 1,2-dehydro-aspidospermidine, 2-hydroxy-tryptamine or a derivative thereof substituted in the benzene ring is condensed with dimethyl 4-ethyl-4-formyl-pimelate to form an oxindolic lactam-ester as the first step of the process. By means of this process, vincadifformine and its derivatives can be obtained in a smaller number of steps than in known processes.