Endoaetheno- oder -aethanomorphid- und -codidderivate

1,223,444. Endoethenonorcodes and normorphides. AMERICAN CYANAMID CO. 26 April, 1968 [27 April, 1967], No. 18457/68. Heading C2C. The invention comprises compounds of the Formula I where R 1 represents hydrogen, C 1-4 alkyl, or C 2-5 alkanoyl, R 2 represents hydrogen, cyano, propargyl, C 1-4 alkyl, phenyl-C 1-4 alkyl, C 2-6 alkenyl or C 4-7 cycloalkylmethyl, such that when R 1 represents C 1-4 alkyl, R 2 represents C 4-7 cycloalkylmethyl, R 3 represents hydrogen, phenyl, or C 1-8 alkyl and Y represents ethano or etheno or non-toxic pharmaceutically acceptable acid addition salts thereof or alkali metal phenolates, where R 1 represents hydrogen and their preparation by treating a compound of the Formula II, where Z represents a group of the Formula IIA, R 4 represents C 1-4 alkyl, R 5 represents hydrogen or C 1-7 alkyl and n is 2 or 3 with dilute aqueous acid at 0-100‹ C. and if desired forming a salt of the product. Ketals of the Formula II may be prepared from appropriate compounds of the Formula I by reaction with an alcohol and a suitable acid. Enol ethers of the Formula II may be obtained by heating compounds of the Formula II where Z represents a group of the formula above its melting point. In compounds of the Formula II, thus produced, the 3-ether group may be converted to the free hydroxy group and the latter etherified to give a R 1 O-group and the N-substituent may be removed, e.g. by reaction with a cyanogen halide, the resulting N-cyano compound hydrolysed to a norcodide (R 2 =H) and the latter alkylated directly or by acylation and reduction of the resulting acylamino compound. Therapeutic compositions having analgesic or anti-nociperceptive properties for oral and parenteral administration comprise the compounds of the invention together with a suitable carrier.