Richter Gedeon Vegyeszeti Gyar Rt

Ferenc Drexler

Csaba Szantay

Lajos Szabo

Gyorgy Kalaus

Tibor Keve

Lajos Dancsi

Bela Stefko

Janos Kreidl

Katalin Nogradi

Maria Farkas Nee Kirjak

Gyorgy Visky

Ida Deutsch Nee Juhasz

Maria Stiller

Zsuzsanna Aracs Nee Tischler

Bela Benke

Krisztina Mihalyfi

Judit Meszaros Nee Brill, Deceased

The present invention relates to racemic or optically active cis octahydro-indolo [2,3-a] quinolizine diester derivatives.

Process for preparing the octahydro-indolo[2,3-a] quinolizine diester

The invention concerns a new process for the preparation of apovincaminic acid ester derivatives of the general formula (I) ##STR1## wherein R.sup.1 and R.sup.2 independently represent an alkyl group having 1 to 6 carbon atoms,

Process for the preparation of apovincaminic acid ester derivatives

The invention relates to new halovincamone derivatives of the general formula (I), ##STR1## wherein R is a C.sub.1-6 alkyl group and X is halogen, and pharmaceutically acceptable acid addition salts and optically active isomers thereof. These compounds possess valuable vasodilating effect, and can be applied to advantage in the therapy. The new compounds defined above are prepared according to the invention so that a single epimer or an epimeric mixture of a racemic or optically active halogenated 14-oxo-15-hydroxy-E-homoeburnane derivative of the general formula (II), ##STR2## wherein R and X are as defined above, or an acid addition salt thereof is treated with an oxidizing agent, and, if desired, the resulting compound of the general formula (I) is converted into its pharmaceutically acceptable acid addition salt and/or resolved.

Process for the preparation of halovincamone derivatives

The invention relates to new, racemic or optically active, halogenated 15-hydroxy-E-homoeburnane derivatives of the formulae (Ia) and/or (Ib), ##STR1## wherein R is a C.sub.1-6 alkyl group and X is halogen, and acid addition salts thereof. These compounds are biologically active, furthermore they can be applied as intermediates in the synthesis of other pharmaceutically active substances.

Halogenated 15-hydroxy-E-homoeburane derivatives

A process for the preparation of 15-hydroxyimino-E-homoeburnane derivatives of the formula (I), ##STR1## wherein X.sup.1 stands for hydrogen or halogen and

Process for the preparation of 15-hydroxyimino-E-homoeburnane and

The invention relates to new 10-halo-E-homoeburnane derivatives of the general formula (I), ##STR1## wherein R.sup.2 is a C.sub.1-6 alkyl group and X is halogen, and epimers, optically active derivatives and pharmaceutically acceptable acid addition salts thereof. These substances exert vasodilating effects and can be applied to advantage in the therapy. The new compounds are prepared so that a racemic or optically active 9-halo-octahydroindoloquinolisine derivative of the general formula (II), ##STR2## wherein R.sup.2 and X are as defined above and R.sup.1 is a C.sub.1-6 alkyl group, or an acid addition salt thereof is treated with a strong base, and, if desired, the 15-epimers of the resulting compound having the general formula (I) are separated from each other, and/or, if desired, the resulting substance is converted into its pharmaceutically acceptable acid addition salt and/or resolved.

10-halo-E-homoeburnane derivatives, a process for the preparation

The invention relates to new, racemic or optically active, halogenated 15-hydroxy-E-homoeburnane derivatives of the general formula (Ia) and/or (Ib), ##STR1## wherin R is a C.sub.1-6 alkyl group and X is halogen, and acid addition salts thereof. These compounds are biologically active, furthermore they can be applied as intermediates in the synthesis of other pharmaceutically active substances. The compounds of the general formulae (Ia) and (Ib) are prepared by halogenating the respective racemic or optically active 15-hydroxy-E-homoeburnane derivative of the general formula (II), wherein R is as defined above. ##STR2##

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Ferenc Drexler