ES453837A1 - Procedure for the preparation of derivatives of 5-sulfamilbenzoico acid substituted with heterociclic radicals. (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

Process for the preparation of 5-sulfamyl benzeic acid derivatives substituted with heterocyclic radicals, of the general formula I **(See formula)** wherein the radicals R1 and R2 are the same or different and signify hydrogen or alcohol of 1 to 4 carbon atoms; R3 means hydrogen or straight or branched chain alcohol of 1 to 4 carbon atoms; X stands for halogen, a benzyl optionally substituted in the phenyl nucleus with halogen, hydroxy, amino, lower alcohol or lower alkoxy or one of the groups O-R4, S-R4, SO-R4, SO-R4 and NR4R5, where it represents phenyl optionally substituted with HalOH, NH2, alcohol- or dialcoylamino, alcohol or alkoxy of 1 to 4 carbon atoms, straight-chain or branched alcohol of 1 to 4 carbon atoms, and R5 signifies hydrogen, the group NHR4R5 also meaning a saturated 5- to 6-membered heterocyclic ring, optionally interrupted by 0, N or S atom; A - stands for an optionally unsaturated alcoholic chain of 2 to 3 carbon atoms, which may be interrupted by O or S atoms, or may be substituted with halogen atoms and/or with possibly branched lower alcohol radicals or aryl, or A represents an ortho-phenylene radical or the grouping **(See formula)** where Y signifies a single bond or an alcoholic group of 1 to 4 carbon atoms, and R6 and R7 are the same or different and signify hydrogen or alcohol of 1 to 4 carbon atoms, as well as their pharmaceutically acceptable salts with bases or acids, characterized in that they are transformed with sulfamyl stalls of the general formula IV **(See formula)** in which the radicals R1 and R2, A and X have the indicated meanings and D represents a radical capable of being transformed into a carboxylic acid, by hydrolysis or by mild oxidation reactions, in the 5-sulfamyl benzoic acids substituted in position 3 with heterocyclic radicals, of the formula I (R3 = H); and optionally in compounds of the formula I double bonds are hydrogenated or double bonds are introduced by elimination reactions and/or free carboxylic acids of the formula I are esterified (R3 = H) and/or carboxylic acid esters of the formula are transformed General I, by hydrolysis or by elimination reactions, in carboxylic acids (R3 = H) and/or by separation of a group, protective hydroxy, amino or mercapto groups are released, mercapto or sulfinyl groups are oxidized or alcoholized amino groups, and/or carboxylic acids of the formula I (R3 = H) are transformed, by treatment with bases or with acids, into their pharmaceutically acceptable salts. (Machine-translation by Google Translate, not legally binding)