GB888664A - Improvements in or relating to acylamidophenol derivatives - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:0888664/IV (b)/1> (wherein R1 and R2 are alkyl groups each containing at most 4 carbon atoms and R3 is a hydrogen atom or a saturated aliphatic hydrocarbon group of at most 9 carbon atoms which may be substituted by an aryl or phthalimido group) and their acid-addition salts; and their preparation (1) by reacting a 3-methoxy-4-OR3-aniline with an acid Q-CH2-COOH (Q being the group R1R2N- or a grouping convertible thereto) or a derivative thereof and, when Q is a convertible group, converting it into the group R1R2N-; or (2) by reacting a 1-(Q-CH2CONH) - 3 - methoxy - 4 - OZ - benzene (Z being hydrogen, an alkali metal or one equivalent of an alkaline earth metal) with a halide Hal-R4 (R4 being the group R3 or a group convertible thereto) and, if necessary, converting the groups Q and R4 into the groups R1R2N- and R3, respectively; or (3) by decarboxylating a 1-(Q-CH2CO.O.CO.NH)-3-methoxy-4-OR3-benzene and, when necessary, converting the group Q into the group R1R2N-. Suitable acid derivatives for use in (1) include halides, esters or mixed anhydrides Q-CH2-CO.O.CO.OR5 (R5 being methyl or ethyl), and suitable groups Q are halogen (when the acid is employed as its halide), nitro or quaternary ammonium which are converted by the usual methods to the group R1R2N-. Examples are given and a list of salt-forming acids is provided. 1 - (Q-CH2CONH) - 3 - methoxy - 4 - hydroxy - benzenes are prepared by reacting 3-methoxy-4-hydroxy-aniline with an acid Q-CH2-COOH or a derivative thereof. The preparation of 4-chloroacetamido-2-methoxy-phenol is described. 1 - (4 - chloroacetamido - 2 - methoxyphenoxy) - n-octane is prepared from chloracetyl chloride and 1 - (4 - amino - 2 - methoxyphenoxy - n - octane. n - (4 - Chloracetamido - 2 - methoxyphenoxy) - 5 - phenylpentane and 1 - (4 - chloracetamido - 2 - methoxyphenoxy)-5-phthalimidopentane are prepared similarly. 1 - (Q-CH2CO.O.CO.NH) - 3 - methoxy - 4 - OR3-benzene are prepared by reaction of 3-methoxy - 4-OR3 - phenylisocyanates with acids Q-CH2COOH. 4 - (n - Octyloxy) - 3 - methoxy - phenyliso - cyanate is prepared from 1-(4-amino-2-methoxyphenoxy)-n-octane and phosgene.ALSO:Pharmaceutical compositions having antibilharzial activity comprise one or more compounds of the formula <FORM:0888664/VI/1> (wherein R1 and R2 are alkyl groups, each containing at most 4 carbon atoms, and R3 is a hydrogen atom or a saturated aliphatic hydrocarbon group of at most 9 carbon atoms which may be substituted by an aryl or phthalimido group) or acid-addition salts thereof, and a pharmaceutical carrier. Tablets, powders, pills, granules, capsules, emulsions, solutions, suspensions, syrups and elixirs, which may contain wetting, suspending, dispersing, emulsifying, sweetening, flavouring and preserving agents are referred to. Tablets containing 1 - (4 - diethylaminoacetamido - 2 - methoxyphenoxy)-n-octane are described. A list of salt-forming inorganic and organic acids also is given.