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

Abstract: 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,and pharmaceutically acceptable salts thereof.According to the invention the apovincaminic acid ester derivatives of the general formula (I) are prepared by reacting the corresponding 9- and/or 10- and/or 11-halo-14-oxo-15-hydroxyimino-E-homo-eburnane derivatives with an alkanol of the general formula R.sup.1 --OH, wherein R.sup.1 is as defined above, and with a dehydrating concentrated acid, and subsequently reducing the 9- and/or 10- and/or 11-halo-apovincaminic acid esters obtained, selectively on the aromatic ring. Alternatively, the 9- and/or 10- and/or 11-halo-apovincaminic acid esters can also be used as starting materials.

Abstract: 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.

Abstract: 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.

Abstract: 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 andR is a C.sub.1-6 alkyl group,or acid addition salts and optically active derivatives thereof. These compounds are valuable intermediates of the synthesis of compounds with outstanding biological effects. According to the invention a racemic or optically active 15-hydroxy-E-homoeburnane derivative of the formula (II), ##STR2## is treated, optionally after separating the 15-epimers and/or resolution, with a halogenating agent. The resulting 15-halo-E-homoeburnane derivative of the formula (III), ##STR3## wherein X.sup.2 stands for halogen, is reacted, optionally after separating the 15 epimers and/or resolution, with an alkali nitrite in the presence of an acid, and, if desired, the resulting 15-hydroxyimino-E-homoeburnane derivative of the formula (I) is converted into its acid addition salt and/or resolved.

Abstract: 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.

Abstract: 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.