ES420241A1 - Phthalazine derivatives and their use in pharmaceutical compo sitions - Google Patents

Abstract

A procedure for preparing phthalazine derivatives of formula I ** (See formula) ** or its enolic or entholic forms of formula Ia ** (See formula) ** where Q is COOH, COOR6, where R6 is an ester forming group or CH2OH; X is oxygen or sulfur; Z is hydrogen or acyl; R is hydrogen or alcohol, and Ar is an unsubstituted phenyl group at the ortho positions and may have one or more substituents, or with which a substituted or unsubstituted mono- or polycyclic ring is fused, which ring or rings may contain one or more heteroatoms, provided that (i) when Q is COOH, COOMe or COOEt, X is oxygen, and R is hydrogen or methyl, then Ar is not phenyl, m or p-chlorophenyl, m or p-nitrophenyl, p - (p-nitrophenylazo) phenyl or p-phenylazophenyl, or (ii) when Q is COOH, X is oxygen and R is hydrogen then Ar is not m or p-aniline or p-acetamidophenyl, or a pharmaceutically acceptable salt with a base inorganic or organic of any compound that is acidic, characterized in that a compound of formula VI ** (See formula) ** wherein Ar1 is Ar or Ar bearing an iodine, bromine, or chlorine substituent in the ortho position, treated with an aqueous or alcoholic acid to hydrolyze the SO3- group to give a hydroxy group; and in the case that Ar1 has an iodine, bromine or chlorine atom in the ortho position, the compound is hydrogenated to remove this halogen group, and if desired a) when Ar1 is meta- or para-nitrophenyl, the nitro group (i) by reductive alcoholization to give an N, N-dialkoxylamino group or (ii) reducing it to an amino group which can itself be further modified later, if desired, by alcoholization to give an N-alcoholic- or N group, N-dialcohilamino; or treatment with a sulfonyl halide to give a sulfonamido group, optionally followed by alkylation to give an N-substituted alcoholic sulfonamido group; either reductive alcoholization or aralkoxylation to give an N-monoalkoxylamino, N, N-dialcohilamino or N-aralcohilo group, or diazotization followed by treatment with an alkanol to give an alkoxy group; either diazotization followed by reduction to give a hydrazino group, or acylation followed by alkylation to give an N-alcoholylacylamino group, or reaction with 2,5-dimethoxytetrahydrofuran to give a 1-pyrrolyl group; b) if desired, a compound obtained is alcoholized to give a compound in which R is alcoholic; c) if desired, a compound obtained is esterified to give a compound in which Q is an ester group; d) if desired, COOH is converted to CH2OH; e) if desired, a compound obtained is sulfided to give a compound in which X is sulfur; f) if desired, a compound obtained is acylated to give a compound in which Z is acyl; and g) if desired, a pharmaceutically acceptable salt is formed with an inorganic or organic base of any compound that is an acid. (Machine-translation by Google Translate, not legally binding)