Patent IE-41611-B1 (IE)
Title: Salicylanilide derivatives
IPC: C07C315/04
Filed: 1975-08-28
Abstract: 1493375 Salicylanilides IMPERIAL CHEMICAL INDUSTRIES Ltd 19 Aug 1975 [20 Sept 1974] 41053/74 Heading C2C The invention comprises salicylanilides of the formula wherein R1 is H or C 1-4 alkanoyl; R2 is CN or C 1-4 alkanoyl or a phenylazo, phenylthio, phenylsulphinyl or phenylsulphonyl radical in which the phenyl radical optionally bears from 1 to 3 substituents selected from halogen atoms, cyano, nitro, trifluoromethyl C 1-4 alkyl and C 1-4 alkoxy radicals; X is a secondary or tertiary C 3-6 alkyl radical; Y is H or methyl; and ring B bears from 1 to 3 substituents selected from halogen atoms, cyano, nitro, trifluoromethyl, C 1-4 alkyl radicals and phenoxy, phenylthio, phenylthio, phenylsulphonyl and benzoyl radicals each optionally bearing 1 or 2 substituents selected from halogen atoms and cyano and nitro radicals and for those compounds wherein R1 is a hydrogen atom salts thereof. The compounds are prepared by (a) reacting the appropriate acids or reactive esters or mixed anhydrides thereof with the corresponding anilines; (b) for those compounds in which R2 is CN and/or ring B bears a cyano radical, reacting compounds of Formula I wherein R2 is a halogen atom and/or ring B bears a halogen atom with cuprous cyanide; (c) for those compounds in which R2 is a formyl radical, formylating the corresponding compounds of Formula I wherein R2 is H; (d) for those compounds in which R2 is an optionally substituted phenylazo radical, reacting the corresponding compounds of Formula I in which R2 is H with the appropriate benzenediazonium salts; (e) for those compounds in which R2 is an optionally substituted phenylsulphinyl or phenylsulphonyl radical and/or ring B bears an optionally substituted phenylsulphinyl or phenylsulphonyl radical, oxidizing the corresponding compounds of Formula I in which R2 is an optionally substituted phenylthio and/or ring B bears an optionally substituted phenylthio; and (f) for those compounds in which R1 is C 1-4 alkanoyl, acylating the corresponding compounds of Formula I in which R1 is H. The following intermediates are also prepared; 5-bromo-6-methyl-3-t-butylsalicylic acid and its methyl ester; salicylic acids of the Formula II wherein R1 is H; X is t-butyl, Y is methyl and R2 is as defined above; methyl 5-cyano-6- methyl-3-t-butylsalicylate; p-nitrobenzenesulphenyl chloride; 2-acetoxy-5-acetyl-6-methyl-3- t-butyl-salicylic acid; salicylanilides of Formula I above in which R2 is H, X is t-butyl, Y is CH 3 , R1 is H and ring B is 3,5-bistrifluoromethylphenyl 2,4-dichlorophenyl, 4-(4-nitrophenylthio) phenyl; 4-nitro-2-trifluoromethylphenyl, 2-methyl-4-nitrolphenyl, 2-chloro-4-nitrophenyl, 4-nitrophenyl and 4-cyanophenyl; 5-(4-nitrophenylthio) -3-isopropyl-6-methyl-salicylic acid; 5-(4-nitrophenylthio) -3-(-butylsalicylic acid; 5 - (4 - nitrophenylsulphonyl) - 3 - isopropyl - 6- methyl-salicylic acid; 5-(4-nitrophenylsulphonyl)-3-t-butyl-salicylic acid; 5-(4-chlorophenylsulphonyl)-3-isopropyl-6-methylsalicylic acid and 5-bromo-41-iodo-6-methyl-3-(-butylsalicylanilide. Anthelmintic compositions, suitable for oral, parenteral or topical administration, contain the above salicylanilides or salts thereof and diluents or carriers therefor.