Novel tetrahydro-isoquinoline derivatives and a process for the manufacture thereof

摘要

Tye invention comprises tetrahydro-isoquinoline derivatives of the formula wherein S1 denotes substitution in up to three positions with the substituents alkoxy, aralkoxy, hydroxy and alkylenedioxy and S2 denotes substitution in up to three positions with the substituents alkyl, alkoxy, nitro and halo, and wherein the broken line denotes that the S2 substitution is optional, and esters and acid-addition salts thereof. The compounds are prepared by reducing a ketone of the formula or a salt thereof, preferably using an alkali-metal earth-metal hydride, e.g. lithium aluminium hydride or sodium or potassium borohydride, and, if desired, in the case where the reduction product is a base, converting the base into an acid-addition salt, or, if desired, esterifying the reduction product and, if desired, when the resulting ester is a base, converting the ester into a salt. Ketones of Formula II may be prepared by condensing in the presence of a basic condensing agent a dihydroisoquinilium salt of the formula where A- represents a monovalent anion, with an acetophenone of the formula: Pharmaceutical compositions, having analgesic spasmolytic and antitussive activity, for enteral or parenteral administration, comprise a compound of the invention in admixture with a compatible pharmaceutical carrier. The compositions may be formulated as tablets, dragees, suppositories, capsules, solutions, suspensions or, emulsions.