ES453836A1 - 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 benzoic acid derivatives substituted with heterocyclic radicals, of the general formula I **(See formula)** wherein the radicals and R 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, S0-R4, SO2-R4 and NR4R5, where R4 represents phenyl optionally substituted by Hal, OH, NH2, alcohol- or dialcohilamino, alcohol or alkoxy of 1 to 4 carbon atoms, straight-chain or branched alcohol of 1 to 4 carbon atoms, and signifies hydrogen, being able to signify the group HR4R5 also a saturated 5- to 6-membered heterocyclic ring, which is eventually interrupted by 0, N or S atoms; A stands for an optionally unsaturated alcoholic chain of 2 to 3 carbon atoms, which may be interrupted by atoms of 0 or 3, 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 R5 and R7 are the same or different and signify hydrogen or 1 to 4 carbon atoms alcohol, as well as their pharmaceutically acceptable salts with bases acids, characterized in that derivatives of 5-halogensulfonylbenzoic acids of the general formula III are reacted **(See formula)** in which R3, A and X have the meanings indicated above and Hal represents a halogen atom, with amines of the formula where R1 and R2 have the indicated meanings; 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 the carboxylic acids (R3 = = H) and/or by separation of a protecting group, hydroxy, amino or mercapto groups are released, mercapto or sulfinyl groups are oxidized or alkoxylate amino groups, and/or carboxylic acids of 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)