Roussel Uclaf

Hoechst Marion Roussel

Christian Marie

Francis Brion

Christian Diolez

Alain Mazurie

Didier Pronine

Edmond Toromanoff

Bernadette Chappert

Michel Middendorp

Jean Buendia

Novel tricyclic compounds of formula I as defined in the specification, a process for their preparation and their use for the preparation of optically active or racemic colchicine and thiocolchicine derivatives.

Tricyclic compounds

A process for the asymmetric preparation of a compound of the formula ##STR1## wherein the hydrogen at 3a and 7a are of cis or trans configuration and their non-toxic, pharmaceutically acceptable acid addition salts comprising submitting a compound of the formula ##STR2## to a Hoffman reaction and reacting the resulting product with formaldehyde in the presence of cyanide ions and acid halide of benzoic acid or an aliphatic carboxylic acid of 1 to 5 carbon atoms to obtain a compound of the formula ##STR3## wherein R is acyl of benzoic acid or aliphatic carboxylic acid of 1 to 5 carbon atoms, cyclizing the latter to form a compound of the formula ##STR4## selectively hydrolyzing the latter with a dilute aqueous mineral acid to obtain a compound of the formula ##STR5## subjecting the latter to hydrolysis with a concentrated aqueous mineral acid to form the acid addition salt of a compound of claim 1 and optionally forming the free base.

Process for making perhydroindole-2-carbonxylic acid

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Noisy le Sec, France

Christian Marie