Abstract: The present invention is directed to compounds having formula (1), wherein n is from 0 to 8; R1 is CH2OH, CH(OH)R5, CH2OR5, CO2R5, C(O)NH2, C(I)NHR5, C(O)NR5R6, C(O)NHNH2, C(O)NHNHR5, C(O)NHNR5R6, C(O)NR5NH2, C(O)NR5NHR6, C(O)NR5NR6R7, C(O)NHNH(C(O)R5), C(O)NHNR5(C(O)R6) C(O)NR5NH(C(O)R6), C(O)NR5NR6(C(O)R7), CN, or C(O)R5; R2 is H, unsubstituted or substituted alkyl, YH, YR8, YC(O)R8, C(O)YR8, C(O)NH2, C(O)NHR8, C(O)NR8R9, NH2, NHR8, NR8R9, NHC(O)R8, or NR8C(O)R9; R3 and R4 are the same or different and are selected from the group consisting of H, halogens, unsubstituted or substituted alkyl, OH, OR10, NH2, NHR10, NR10R11, NHC(O)R10, or NR10C(O)R11; R5, R6, R7, R8, R9, R10, and R11 are the same or different and are selected from the group consisting of unsubstituted alkyl and substituted alkyl and substituted alkyl; R12 is selected from the group consisting of J, unsubstituted alkyl, and substituted alkyl; and Y is O or S; provided that when n is O, R2 is selected from the group consisting of H, substituted

Abstract: Sensitizing tumoral cells to anticancerous drugs and/or inhibiting the tumoral cells resistance to antitumoral drugs employing as a modulator agent a vinca alkaloid dimer, analog to vinblastine or vincristine, with a low cytotoxicity or devoid of cytotoxicity, comprising at least one stereoisomerism different from that of vinblastine or vincristine in the C-14', C-16' or C-20' position. Notably, the modulator agent may have the R absolute configuration in the C-16' position.

Abstract: This invention relates to novel tetrahydroazepinoindoles used in the preparation of novel alkyl pyrrolo(2,3-d)carbazole-6-carboxylates and to addition salts thereof; and to preparation of the same by a synthesis sequence starting from a tryptamine and a 3-halopyruvate and involving a rearrangement of the reaction mixture, said rearrangement being effected by heating the reaction mixture in the presence of a base. The pyrrolo(2,3-d)carbazole final products have both antianoxic and psychotropic activities.

Abstract: This invention relates to alkyl pyrrolo(2,3-d) carbazole-6-carboxylates having antianoxic, psychotropic and hemodynamic properties and to addition salts thereof; and to preparation of the same by a synthesis sequence starting from a tryptamine and a 3-halopyruvate and involving a rearrangement of an addition compound with an aldehyde, said rearrangement being effected by Nb-alkylation of the aforementioned addition compound; and to pharmaceutical compositions containing the same; and to tetrahydroazepinoindoles used in the preparation of the same.

Abstract: This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of among other alkaloids vincamine and other similar compounds possessing interesting psychopharmacologic properties.A tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide a 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (III). Then compound (III) is reduced to give a 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into a chloroindolenine derivative (V) which is immediately treated with a metal dialkylmalonate such as thallium t-butyl methyl malonate to give a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into a alkyl 3-benzyl-1,2,3,4,5,6-hexahydro-(4,5-b) indole-5-carboxylate (VII).

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 preparation of vincadifformine and some derivatives thereof for use as a starting material for synthesis of the corresponding vincamine derivatives or for synthesis of bisindole alkaloids having clinically important antitumor properties.

Abstract: The invention relates to the preparation of vincadifformine.Tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-[3,4b]-indole (III). Then compound (III) is reduced to give 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4b]-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into chloroindolenine derivative (V) which is immediately treated with thallium t-butyl methyl malonate to give t-butyl methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (VII). Compound (VII) is hydrogenated to give methyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (IX). In an alternative embodiment, compound (VI) can be hydrogenated to methyl t-butyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VIII) which is then decarboxylated into compound (IX).