ETHERS AND THEIR USE IN THE TREATMENT OF LIVER FLUKE INFECTIONS

摘要

1429852 Amides WELLCOME FOUNDATION Ltd 23 Feb 1973 [25 Feb 1972 28 Feb 1972] 8920/73 Addition to 1380882 Heading C2C [Also in Division A5] The invention comprises amides of the formula wherein L is -Z-A-Z-, where Z is when m is 0 or 1 and X 2 , X 3 and X 4 are H or C 1-3 alkyl; and A is -O.CO.O- or a divalent radical of a dicarboxylic or monocarboxylic acid containing 2 to 14 carbon atoms and having respectively two ester linkages or one ester and one other linkage, to the rest of the molecule, or -CH 2 -, -(CH 2 ) 2 -, or where X and X 1 are H or C 1-3 alkyl ; R and RSP1/SP are H, optionally substituted saturated aliphatic hydrocarbon group having 1 to 7 carbon atoms or an unsaturated aliphatic hydrocarbon group having 2 to 4 carbon atoms; RSP2/SP and RSP3/SP are H, C 1-4 alkyl, RSP5/SPCO, RSP6/SPCO where RSP5/SP and RSP6/SP are H, optionally substituted aliphatic C 1-7 hydrocarbyl, or unsaturated aliphatic C 2-4 hydrocarbyl or together with R and RSP1/SP respectively form C 2-4 alkylene, provided that when L is other than -Z-A-Z- at least one of RSP2/SP and RSP3/SP is, as appropriate, the group RSP5/SPCO or RSP6/SPCO and when one or more of the groups R, RSP1/SP, RSP5/SP and RSP6/SP is a saturated aliphatic C 1-7 hydrocarbyl group substituted by NH 2 , C 1-4 alkylamino or di-(C 1-4 alkyl) amino, acid addition salts thereof. The compounds are obtained by one of the following methods:- (a) reacting in liquid mediums compounds of the Formula III wherein Alk is an alkali metal, D is R or RSP1/SP and E is RSP2/SP or RSP3/SP with compounds of the Formula IV where B is a reactive nucleophilic group or atom; (b) acylating amines of the Formula V wherein at least one of TSP1/SP, TSP2/SP, TSP3/SP and TSP4/SP is H and otherwise TSP1/SP and TSP2/SP are RSP1/SPCO or RCO and TSP3/SP and TSP4/SP are RSP2/SP and RSP3/SP respectively; or (c) reacting in liquid medium compounds of the Formula VII where D is R or RSP1/SP and E is RSP2/SP or RSP3/SP and P is H or an alkali metal with compounds of the Formula VIII wherein G is the moiety of the group A that interconnects the two terminal oxygen atoms thereof. 4SP1/SP-(2-Hydroxyethoxy)acetanilide is made by reacting 4-acetamidophenol with 2-chloroethanol.