PROCEDIMIENTO PARA PREPARAR DIHIDRO-2-AMINOISOQUINOLINAS.

摘要

1377310 Aminoisoquinolinones GRUPPO LEPETIT SpA 28 Feb 1972 [18 March 1971 28 Dec 1971] 9025/72 Heading C2C Novel aminoisoquinolinones of the general formula wherein X and Y are different and each represents an oxygen atom or two hydrogen atoms and each of R and R 1 is a hydrogen atom or a C 1-4 alkyl, hydroxy-C 1-4 alkyl, amino-C 1-4 alkyl, mono- or di-C 1-4 alkyl-amino-C 1-4 alkyl, carboxy-C 1-4 alkyl, carboalkoxy-C 1-4 alkyl, cycloalkyl, aryl, aralkyl, acyl (derived from an aliphatic, aromatic or heterocyclic carboxylic acid), carbamoyl, thiocarbamoyl, arylcarbamoyl, arylthiocarbamoyl, guanyl, arylsulphonyl alkylsulphonyl or haloalkylsulphonyl group or -NRR 1 is an aralkylidene-, alkylidene-, carboxyalkylidene-, carbalkoxy-alkylidene- or cycloalkylidene-amino group or a heterocyclic group of 5-7 ring atoms, aud pharmaceutically acceptable acid addition salts thereof, are prepared (a) when each of R and R 1 is a hydrogen atom, by reaction of a C 1-4 alkyl 2-(2-haloethyl)- benzoate or 2-halomethyl-phenylacetate with hydrazine in a C 1-4 alkanol; (b) when at least one of R and R 1 is other than a hydrogen atom, by heating a solution of a hydrazide of the general formula wherein either m = n = 1 or m = 0 and n = 2, in an organic solvent in the presence of a strong base ; and (c) by conversion of one value of R and/or R 1 into another by a conventional procedure; followed optionally by salification of the product. Hydrazides of the second general formula above wherein m = 0 and n = 2 are prepared by reaction of a 2-(2-haloethyl)-benzoyl halide with the appropriate hydrazine. 2-(2-Chloroethyl)- benzoyl chloride is prepared by treatment of 1- isochromanone with PCl 5 . N-(2-Chloromethylphenylacetyl) - N1,N1 - dimethylhydrazine is prepared by reaction of 3-isochromanone with N,N-dimethylhydrazine, followed by treatment of the resulting N-(2-hydroxymethyl-phenylacetyl) - N,N1 - dimethylhydrazine with thionyl chloride. Pharmaceutical compositions having antiinflammatory activity comprise, as active ingredient, an aminoisoquinolinone of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier.