New organic compounds having opioid properties

摘要

New echiboline derivatives with opioid properties which are 6- hydroxy- 9-methyl-echiboline derivatives having, in the 10-position, a hydrocarbon substituent of up to 4 carbon atoms--preferably a group R.CH. sub.2 -- (wherein R represents a hydrogen atom or a hydrocarbon group of up to 3 carbons) and especially a methyl, cyclopropyl-methyl or allyl group. PPThese are made by dealkylating corresponding 6- alkoxy-9- methyl-10-substituted echibolines, thereby converting the 6- alkoxy group to a 6-hydroxy group, especially using boron tribromide as dealkylating reagent.PPSpecific examples are 6-hydroxy-9, 10-dimethyl- echiboline, 6-hydroxy-9-methyl-10-allyl-echiboline and 6- hydroxy-9-methyl- 10-cyclopropylmethyl-echiboline.PPThe compounds may be in free base or salt form, and be incorporated as active ingredient into pharmaceutical compositions.PPAlso, the corresponding 6- alkoxy-9-methyl-10-substituted echiboline derivatives as useful novel intermediates, which may be made from a 6-alkoxy-9-methyl- echiboline by (A) reaction with a reagent which introduces the desired substituent into 10-position or (B) acylating to introduce the substituent R--CO-- into the 10-position and reducing the acyl group to RCH.sub.2 --.