Patent GB-1247067-A (GB)
Title: Tricyclic enol ether compounds and the preparation thereof
IPC: C07D405/12
Filed: 1969-02-13
Abstract: 1,247,067. 10-Aminoalkoxy-dibenzo[6,f]oxepins, - dibenzo[6,f]thiepins and - 5H - dibenzo- [6,f]azepines. FUJISAWA PHARMACEUTICAL CO. Ltd. 13 Feb., 1969 [16 Feb., 1968], No. 7990/69. Heading C2C. Novel 10 - aminoalkoxy - dibenzo[6,f]oxepins, - dibenzo[6,f]thiepins and - 5H - dibenzo[6,f]azepines of the general formula wherein X is a hydrogen or halogen atom or a C 1-6  alkyl, C 1-6  alkoxy, C 1-6  alkylthio, di-C 1-6  alkylsulphamoyl, nitro, cyano, amino or trifluoromethyl group, Z is an oxygen or sulphur atom or a C 1-6  alkylimino group, A is a C 1-6  alkylene group and each of R 1  and R 2  is a C 1-6  alkyl group or R 1  and R 2  may be taken together with the adjacent nitrogen atom, with or without an intervening oxygen atom or imino, C 1-6  alkylimino, hydroxy-C 1-6  alkylimino, C 1-6  alkoxy-carbonylimino, formylimino, C 1-6  alkanoyloxy-C 1-6 alkylimino or C 1-6  alkanoylimino group, so that the group of the formula -NR 1 R 2  is a saturated 5-7 membered heterocyclic group, and pharmaceutically acceptable acid addition and quaternary ammonium salts thereof are prepared (a) by reaction of a ketone of the general formula with a compound of the general formula Y-A-NR 1 R 2 , wherein Y is an acid residue; (b) by reaction of a ketone of the second general formula above with a compound of the general formula Y<SP>1</SP>-A-Y, wherein Y<SP>1</SP> is an acid residue which is more reactive than Y, followed by reaction of the resulting 10-(substituted alkoxy) - dibenzo[6,f]oxepin., - dibenzo[6,f]- thiepin or - 5H - dibenzo[6,f]azepine of the general formula with an amine of the general formula HNR 1 R 2 ; (c) when -NR 1 R 2  is a heterocyclic group containing an -NH- group, by heating the corresponding compound in which the -NH- group is replaced by a formylimino or C 1-6  alkoxy-carbonylimino group in an alcoholic solvent in the presence of a base; (d) when a C 1-6  alkylimino, hydroxy-C 1-6 alkylimino, C 1-6  alkoxycarbonylimino, C 1-6 alkanoyloxy - C 1-6  alkylimino or C 1-6  alkanoylimino group is present, by reaction of a compound of the first general formula above wherein -NR 1 R 2  is a heterocyclic group containing an -NH- group with a compound of the general formula Y-R 6 , wherein R 6  is a C 1-6  alkyl, hydroxy- C 1-6  alkyl, C 1-6  alkoxy-carbonyl, C 2-7  alkanoyloxy - C 1-6  alkyl or C 1-6  alkanoyl group; (e) when a hydroxy-C 1-6 -alkylimino group is present, by reaction of a compound of the first general formula above wherein -NR 1 R 2  is a heterocyclic group containing an -NH- group with ethylene oxide or a derivative thereof of the general formula wherein R 7  is a hydrogen atom or a C 1-6  alkyl group; (f) when a C 1-6  alkylimino or hydroxy- C 1-6  alkylimino group is present, by reduction of a compound of the first general formula above wherein -NR 1 R 2  is a heterocyclic group containing a C 1-6  alkanoylimino or C 1-6  alkoxycarbonylimino group or an analogous compound containing an C 1-6  alkoxy-carbonyl-C 1-6 -alkylimino group; or (g) when a C 1-6  alkanoyloxy- C 1-6  alkylimino group is present, by acylation of a compound of the first general formula above wherein -NR 1 R 2  is a heterocyclic group containing a hydroxy-C 1-6  alkylimino group with a carboxylic acid of the general formula R 9 COOH, wherein R 9  is a C 1-6  alkyl group; followed optionally by salification of the product. Pharmaceutical compositions having psychotropic and neurotropic activity comprise, as active ingredient, a 10-aminoalkoxy-dibenzo- [6,f]oxepin, -dibenzo[6,f]thiepin or -5H-dibenzo[6,f]azepine of the first general formula above or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof, in admixture with a pharmacologically acceptable carrier, and may be administered enterally of parenterally.