ES453838A1 - 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 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, SO2-R4 and NR4R5, where R4 represents phenyl optionally substituted by Hal OH, NH2, alcohol- or dialcoylamino, alcohol or alkoxy of 1 to 4 carbon atoms, or straight-chain or branched alcohol of 1 to 4 carbon atoms, and R5 means hydrogen, being able to signify the group NR4R5 also a saturated 5- to 6-membered heterocyclic ring, which is eventually interrupted by O, N or S atoms; A stands for an optionally unsaturated alcoholic chain of 2 to 3 carbon atoms, which can be interrupted by O or S atoms, or can be substituted with halogen atoms and/or with possibly branched lower alcohol radicals or aryl, or A represents a ortho-phenylene radical or grouping **(See formula)** where Y means a single bond or an alcohol 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 sulfamyl benzoic acid derivatives of the general formula V or Va are cyclized **(See formula)** where B means a protecting group of the general formula **(See formula)** wherein R8, R9 and R10 signify the same or different lower alcohol groups, R8 may also mean hydrogen, and/or in each case two of the substituents R8, R9 or R10 may also be cyclically linked to each other, and the radicals R1 up to R3, A and X have the meanings indicated above and L represents an "active surplus group", possibly by treatment with acids or bases; 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 esters of carboxylic acids of the formula are transformed General I, by hydrolysis or by elimination reactions, in the carboxylic acids R3 = H) and/or by removal of a protecting group, hydroxy, amino or mercapto groups are released, mercapto or sulfinyl groups are oxidized or amino groups are alcoholized, 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)