Morphinan derivatives

Abstract

Abstract Compounds of formula I <IMAGE> wherein X and Y each denotes hydrogen or together denote -0-, R1 denotes allyl optionally substituted by 1 to 3 alkyl groups, the substituent or substituents having in total a maximum of 3 carbon atoms, cyclopropyl-methyl or 3-furylmethyl, R2 denotes hydrogen, alkyl with 1 to 10 C-atoms, cycloalkyl with 5 or 6 carbon atoms, optionally substituted phenyl or optionally substituted phenyl-alkyl with 7 to 12 C-atoms, R3 denotes hydrogen, alkyl with 1 to 10 C-atoms or phenyl, R4 denotes hydrogen, OH, NR6R7, NHCOR, NHSO2R' or NHCOOR'', R6 and R7, independently of one another, denote hydrogen or alkyl with 1 to 3 C-atoms, R denotes alkyl with 1 to 6 C-atoms, phenyl or -A-COOR'', A denotes alkylene or alkenylene each with 2 to 4 C-atoms, R' denotes alkyl with 1 to 6 C-atoms or phenyl, R'' denotes methyl or ethyl and wherein either R3 is in the alpha -position and R4 is in the beta -position, or R3 is in the beta position and R4 is in the alpha -position, or R3 and R4 together are =O, or =CH2, and R5 denotes hydrogen or methyl, with the provisos that when X and Y denotes -O-, R2 denotes hydrogen, R4 denotes a alpha OH group and R3 and R5 denote hydrogen, then R1 is other than cyclopropylmethyl of allyl, and that when R2, R3, R4 and R5 are each hydrogen, R1 is other than cyclopropymethyl, in free base from or in acid addition salt form, as well as the physiologically hydrolyzable, pharmaceutically acceptable esters of such compounds, which contain a free OH group, in free base form or in acid addition salt form. The compounds according to the invention are opiate agonists/antagonists and LH secretion stimulators.

Inventors

• 👤 Laszlo Revesz

Bibliographic Details