GB824875A - Improvements in or relating to ethers - Google Patents

Abstract

The invention comprises ethers of the general formula <FORM:0824875/IV (b)/1> (wherein R is hydrogen, methyl or an alkyl or alkenyl group of 2 to 8 carbon atoms, R1 is a diphenylmethyl group which may be substituted in one or both phenyl radicals by one or more halogen atoms and/or alkoxy groups of 1 3 to carbon atoms, and n is 2, 3 or 4, except that it is not 2 when R is methyl) and acid-addition salts thereof; and their preparation by reacting a halide R1X (X being a halogen atom) with the appropriate alcohol, advantageously at an elevated temperature in an inert, anhydrous organic solvent containing a tertiary amine. In examples, products having the following values for n, R and R1 are prepared:- .n.R.R1 .2.ethyl.diphenylmethyl .2.ethyl.p-methoxy-diphenylmethyl .2.ethyl.p-chloro-diphenylmethyl .2.n-propyl.diphenylmethyl .2.iso-propyl.diphenylmethyl .2.n-butyl.diphenylmethyl .2.n-amyl.diphenylmethyl .2.n-hexyl.diphenylmethyl .2.n-heptyl.diphenylmethyl .2.n-octyl.diphenylmethyl .2.n-allyl.diphenylmethyl .2.benzyl.diphenylmethyl .3.ethyl.diphenylmethyl .3.n-propyl.diphenylmethyl .3.n-propyl.p-dichloro-diphenylmethyl .3.iso-propyl.diphenylmethyl .3.n-butyl.diphenylmethyl .3.n-amyl.diphenylmethyl .4.n-propyl.diphenylmethyl .3.n-methyl.diphenylmethyl .2.iso-butyl.diphenylmethyl .2.iso-propyl.p-methoxy-diphenylmethyl .2.n-propyl.p:p1-dibromo-diphenylmethyl .2.iso-amyl.diphenylmethyl .2.iso-amyl.p-methoxy-diphenylmethyl .2.hydrogen.diphenylmethyl .2.hydrogen.p-methoxy-diphenylmethyl .2.hydrogen.p-chloro-diphenylmethyl .3.hydrogen.diphenylmethyl as either hydrochlorides, methanesulphonates or hydrobromides Alcohols of the general formula <FORM:0824875/IV (b)/2> are prepared by the Robinson synthesis from dialdehydes, acetone dicarboxylic acid and ammonia or primary amines, with subsequent N-alkylation if required, when ammonia is used. Reference has been directed by the Comptroller to Specification 804,837.ALSO:Pharmaceutical compositions comprise ethers of the formula <FORM:0824875/VI/1> (wherein R is hydrogen, methyl or an alkyl or alkenyl group of 2 to 8 carbon atoms, R1 is a diphenylmethyl group which may be substituted in one or both phenyl radicals by one or more halogen atoms and/or alkoxy groups of 1 to 3 carbon atoms, and n is 2, 3 or 4 except that it is not 2 when R is methyl) or acid-addition salts thereof in admixture with or in solution in a carrier or diluent. Examples describe ampoules containing N-isopropyl-nortropine-benzhydryl ether methane sulphonate and water; a jelly containing this active ingredient, sodium benzoate, sorbite, hydroxyethylmethyl cellulose and water; and tablets containing the corresponding hydrobromide, potato starch, carbowax, "Aerosil" (Registered Trade Mark) and lactose. Reference has been directed by the Comptroller to Specification 804,837, [Group IV (b)].