GB1382586A - 5,11-dihydrodibenzoxa -or thia- zepine derivatives - Google Patents

Abstract

1382586 5,11 - Dihydrodibenzoxazepines and -thiazepines E R SQUIBB & SONS Inc 23 Nov 1971 [24 Nov 1970 (2)] 54465/71 Heading C2C 5,11 - Dihydrodibenzoxazepines and - thiazepines of the general formula wherein A is O, S, SO or SO 2 , each of R and R 1 is a halogen atom or a trifluoromethyl, C 1-8 alkyl, cycloalkyl, C 1-8 alkylthio, C 1-8 alkoxy, cyano or di-C 1-8 alkyl-sulphamoyl group, each of n and n 1 is 0, 1 or 2, X is an alkylene group having 1-6 C atoms in the linking chain, Y is an alkylene group having 1-4 C atoms in the linking chain, m is 0 or 1, each of R 2 and R 3 is a hydrogen atom or a C 1-8 alkyl, C 1-8 hydroxyalkyl, monocyclic cycloalkyl, monocyclic cycloalkyl-C 1-8 alkyl, monocyclic aryl, monocyclic aryl-C 1-8 alkyl or monocyclic heterocyclic-alkyl or, when m is 0, optionally substituted aminoalkyl group or NR 2 R 3 is an optionally substituted heterocyclic radical, and acid addition salts and quaternary ammonium salts thereof are prepared by reaction of a carboxylic acid of the general formula or an acid halide, ester or salt thereof with a compound of the general formula B-NR 2 R 3 , wherein B is a hydrogen atom or a -Y-OH group, followed optionally by salification of the product. Acid halides of carboxylic acids of the second general formula above are prepared by reaction of the said acid or an ester or salt thereof with a phosphorus pentahalide in the absence of oxygen. Carboxylic acids of the second general formula above are prepared (a) when A is SO or SO 2 , by oxidation of the corresponding compound in which A is S; and (b) by reaction of the corresponding nitrile with an alcoholic hydrogen halide and saponification of the resulting ester with an alkali metal hydroxide. The nitriles used in (b) above are prepared (i) when X is -CH 2 CHR 4 - (R 4 is H or alkyl), by reaction of a 5,11-dihydrodibenzoxazepine or -thiazepine of the general formula with a nitrile of the general formula (ii) by reaction of the heterocyclic reactant of (i) above with a nitrile of the general formula Z-X-CN, wherein Z is a halogen atom; and (iii) by treatment of a corresponding halide with an alkali metal cyanide. Pharmaceutical compositions having hypotensive and anti-inflammatory activity and disinfectant compositions comprise, as active ingredient, a 5,11-dihydrodibenzoxazepine or -thiazepine of the first general formula above or an acid addition salt or quaternary ammonium salt thereof, together with a suitable carrier.