GB713146A - Anti-cough agents comprising (ú½)-3-hydroxy-n-methyl-morphinane ethers and process for the manufacture thereof - Google Patents

Abstract

The invention comprises ethers of (+)-3-hydroxy-N-methylmorphinane, the ether groups of which are alkyl or alkenyl containing more than one carbon atom, and acid addition salts thereof. The ethers are prepared by treating (+)-3-hydroxy-N-methylmorphinane with an etherifying agent, particularly a compound of general formula <FORM:0713146/IV (b)/1> wherein R1, R2 and R3 represent lower alky or alkenyl radicals of which at least one contains more than one carbon atom, or an alkoxide thereof. An unsaturated morphinane ether may be hydrogenated to the corresponding saturated derivative. In examples: (1) phenyl triethyl ammonium methoxide and (+)-3-hydroxy-N-methylmorphinane are refluxed in toluene, and the product distilled in vacuo to yield (+)-3-ethoxy-N-methylmorphinane, which may be then converted to its acid phosphate; (2) (+)-3-hydroxy-N-methylmorphinane is treated with phenyl allyl dimethyl ammonium hydroxide to yield (+)-3-allyloxy-N-methylmorphinane, and subsequently its hydrobromide; (3) hydrogenation of the 3-allyloxy compound using palladium charcoal produces the corresponding (+)-3-propyloxy ether, which is converted to its tartrate.