GB1088096A - Benzimidazole, benzoxazole and benzothiazole derivatives - Google Patents

Abstract

Novel compounds of formula <FORM:1088096/C2/1> and acid addition salts thereof, in which R is a pyrryl, furyl, thienyl, thiazolyl isothiazolyl or thiadiazolyl radical, A is O, S or NR, where R1 is H, alkanoyl, aroyl or aralkanoyl aralkyl or C1- 5 alkyl, one of R5 and R6 is H and the other is phenyl, naphthyl, halophenyl (C1- 5 alkyl) phenyl (C1- 5 alkoxy) phenyl, (C1- 5 alkylthio) phenyl, (C1- 5 alkyl) aminophenyl or di (C1- 5 alkyl) aminophenyl, are prepared by reacting a compound of formula <FORM:1088096/C2/2> (in which B is H, NO2, NHR1, OH or SH), before or after reduction if B is NO2 and before, after or between nitration and reduction if B is H, with a compound of formula R-D where D is a carboxy carboalkoxy, cyano, carboxamido or acid halide radical, or alternatively, if R5 is phenyl or halophenyl and R6 is H when R is thiazolyl, by reacting a compound in which B is NHR, with a thiazolyl aldehyde and an oxidizing agent; in both cases in a compound where R1 is H it may be substituted to give the other compounds, and/or acid addition salts may be prepared in all cases. Various amidino-, amino- and nitro-biphenyls substituted as in R5 or R6 above are isolated as intermediates in the first process above.ALSO:An anthelmintic composition comprises a compound of formula <FORM:1088096/A5-A6/1> in which Q is a heteroaromatic radical containing from 1 to 3 hetero atoms which may be N, O or S, one of R5 and R6 is H and the other is phenyl, naphthyl, halophenyl, (C1-5 alkyl) phenyl (C1-5 alkoxy) phenyl, (C1-5 alkylthio) phenyl or mono- or di- (C1-5 alkyl)-aminophenyl and A0 is O, S on NR00 where R00 is H, C1-5 alkyl, aralkyl, alkanoyl, aroyl or aralkanoyl, intimately dispersed in or admixed with a solid orally ingestible carrier or in a liquid orally ingestible carrier containing a suspending or wetting agent, either of which may be an animal feedstuff, the composition may be in the form of a capsule, tablet or bolus, optionally having an enteric coating, or a drench. A process for treating animals with the above compositions or the active compound therein is also claimed.