SYNTHESES OF CODEINE DERIVATIVES AND OTHER 3-O-ALKYLMORPHINS AND INTERMEDIATE COMPOUNDS USED THEREOF

摘要

THE INVENTION CONCERNS THE SYNTHESIS OF DERIVATIVES OF CODEINE AND OTHER 3-0-ALKYLMORPHINES. A 14-OH GROUP IS INTRODUCED IN A MORPHINANE BY SINGULET OXYGEN REACTION WITH A DIENOL -New ester of an N-SUBSTITUENT-3-O-ALKYLNORMORPHINONE. THE COMPOUND OBTAINED IS ALSO A NEW COMPOUND WHICH CAN BE PROCESSED INTO NOROXYMORPHONE BY SUCCESSIVE CATALYTIC HYDROGENATION OPERATIONS, HYDROLYTIC REMOVAL OF THE NITROGEN ATOM SUBSTITUENT AND HYDROLYSIS AND O-DEALKYLATION. THE INTERMEDIATE DIENOL-ESTER IS PREPARED BY N-DEMETHYLATION OF CODEINE OR ANOTHER 3-O-ALKYLMORPHINE FOLLOWED BY OXIDATION AND ESTERIFICATION OF THE OXIDE PRODUCT USING AN ANHYDRIDE OR ACID HALIDE 14-HYDROXYMORPHINANES ARE POWERFUL ANALGESICS AND ANTAGONISTS OF NARCOTICS. / P