GB834968A - 5-o-alkoxyphenoxymethyl-2-oxazolidones - Google Patents

Abstract

The invention comprises compounds of the general formula <FORM:0834968/IV (b)/1> (wherein X is a lower alkoxy group with 1 to 8 carbon atoms, and R is a hydrogen atom or a hydrocarbon radical, preferably methyl, benzyl and cyclohexyl), and the preparation thereof by: (1) reacting urea with glyceryl guaiacol ether at approximately 170-200 DEG C.; (2) aminating 3 - o - methoxyphenoxy - 1 - halo - 2 - propanols with ammonia or a primary amine to form amino alcohols which are reacted with carbonyl chloride in approximately equimolecular quantities at refluxing temperatures; (3) reacting a 3 - o - lower - alkoxyphenoxy - 1 - halo - 2 - propanol with urea at a temperature not over about 200 DEG C.; (4) reacting a 3-o-lower-alkoxy-1-amino-2-propanol with an approximately equi-molecular quantity of a dialkyl carbonate in the presence of an alkali metal compound. They may also be prepared by reacting 1,2-epoxy - 3 - o - lower - alkoxyphenoxypropanes with urea, sodium cyanate and hydrochloric acid, or ethyl carbamate under alkaline conditions. 3 - o - Methoxyphenoxy - 1 - amino - 2 - propanol, 3 - o - methoxyphenoxy - 1 - methylamino-, 3 - o - methoxyphenoxy - 1 - cyclohexylamino - and 3 - o - methoxyphenoxy - 1 - benzylamino - 2 - propanol are made by reacting 3-o-methoxyphenoxy - 1 - chloro - 2 - propanol with, respectively, ammonia, monomethylamine, cyclohexylamine and benzylamine. 3-o-Methoxyphenoxy - 1 - amino - 2 - propanol is also made by reducing 5-o-methoxyphenoxymethyl-2-oxazolidone with lithium aluminium hydride.ALSO:Compounds of the general formula <FORM:0834968/VI/1> (wherein X is a lower alkoxy group with 1 to 8 carbon atoms, R is a hydrogen atom or a hydrocarbon radical, preferably methyl, benzyl and cyclohexyl) may be embodied in pharmaceutical forms suitable for oral administration, for example, capsules, elixirs, solutions and tablets.