SUBSTITUTED DIPHENYL ETHERS

1435755 2 - Phenoxyalkylsulphonanilides RIKER LABORATORIES Inc 2 July 1973 [3 July 1972] 31454/73 Heading C2C Novel compounds of the Formula I wherein R x is C 1-2 alkyl or monohaloalkyl; R is hydrogen, cyano, alkyl, alkylsulphonyl, haloalkylsulphonyl, a cation or -COAR1 where R1 is alkyl and A is oxygen or a bond between the carbonyl carbon and the alkyl group; X is alkoxyl, alkyl, halogen, acetamido, nitro, hydrogen, amino, alkoxycarbamoyl or dialkylamino; Y is nitro, amino, alkoxycarbamoyl, dialkylamino or hydrogen, provided that one of X and Y is nitro, amino, alkoxycarbamoyl, or dialkylamino; Z is halogen, nitro or hydrogen; Z1 is halogen, alkyl, alkoxy, nitro, amino, alkanamido, haloalkyl, hydroxy dialkylamino, alkoxycarbamoyl, alkylthio, alkyl sulphonyl, alkanoyl or alkylsulphinyl and n is 0, 1 or 2 in which aliphatic moieties in R, X, Y and Z1 contain one to four carbon atoms may be prepared (1) where X and Y are not NH 2 , Z1 is not hydroxy or amino and R is hydrogen, by reacting a compound R x SO 2 Q where Q is fluorine or chlorine with a compound of the Formula II (ii) where R is hydrogen, reacting compounds III and IV wherein D is chlorine, bromine or iodine, providing that when D is chlorine X is an activating group and M is an alkali metal or copper provided that if Z or Z1 is halogen, Z or Z1 is a lower atomic weight halogen than D; (iii) reacting a compound I wherein R is hydrogen with a base to introduce a cation; (iv) reacting a product of III where R 1 is a metal cation with an alkyl bromide or iodide dialkylsulphate; (v) reacting a product of (i), (ii) or (iii) with cyanogen halide, alkylsulphonyl or haloalkylsulphonyl halide, alkanoyl halide, or alkyl chloroformic acid to introduce the appropriate group at R; (vi) nitrating a compound I in which Y is hydrogen to introduce an NO 2 group at Y; (vii) modifying the substituents X, Y, Z and Z1 by known methods. Pharmaceutical compositions of the compounds I show anti-inflammatory activity when administered orally, topically, parenterally or rectally with the usual excipients. Selected compounds also show analgesic, antipyretic, antimicrobial and herbicidal activity.