GB968395A - Dibenzodiazepinone derivatives - Google Patents

Abstract

The invention comprises compounds of formula: <FORM:0968395/C1/1> where R is H, CH3 or C2H5, R1 is halogen trifluoromethyl, CH3 or C2H5, R2 is H, CH3 or C2H5, and R3 is CH3 or C2H5 and N1-oxides and acid addition salts of such compounds. The compounds are prepared by reacting an alkali metal salt of a dibenzodiazepinone of formula: <FORM:0968395/C1/2> with a compound of formula Z-CH2CH2-halogen where Z i <FORM:0968395/C1/3> or a substituent convertible to <FORM:0968395/C1/4> The alkali metal salt of the dibenzodiazepinone is prepared by reacting the dibenzo-diazepinone with an alkali metal amide, or by reacting the corresponding N-(2-amino-5-R1-substituted phenyl) anthranilic acid ester with an alkali metal amide. The compounds where R2 is hydrogen may be obtained by reacting a benzalkylaminoethyl halide with the alkali metal salt of the dibenzodiazepinone and subsequently removing the N-benzyl group by hydrogenolysis. The dibenzodiazepinones may be obtained by heating the corresponding N-(2-amino-5-R1-substituted phenyl) anthranilic acid, and the latter may be prepared by reacting anthranilic acid or N-alkylated derivative thereof with a 2-bromo-4-R1 substituted nitrobenzene, and reducing the N-(2-nitro-5-R1-substituted phenyl) anthranilic acid so obtained to the N-(2-amino-5-R1-substituted phenyl) anthranilic acid. Alternatively potassium o-bromobenzoate may be reacted with 2-amino-4-R1-substituted nitrobenzene or N-alkyl derivative thereof and the N-(2-nitro-5-R1-substituted phenyl) anthranilic acid or N-alkyl derivative thereof so obtained reduced to the amino compound. Esters may be obtained by reacting the N-(2-amino-5-R1-substituted phenyl) anthranilic acid with an aliphatic alcohol. Examples are given.