ES437053A1 - 3-substituted quinoxaline-2-carboxamide-1,4-dioxides - Google Patents

Abstract

A procedure for preparing quinoxalin-2-carboxamide-1,4-dioxides substituted in position 3 of the formula: wherein X is a substituent at the 6 or 7 position and is hydrogen, halogen, lower alkoxy, trifluomethyl, methyl, lower alkyl sulfide, lower alkyl sulfoxide or lower alkyl sulfone; Y is S, SO or SO2; is lower alkyl substituted with hydroxy, lower alkoxy, amino, mono (lower alkyl) amino, di (lower alkyl) amino, lower alkoxycarbonyl, carbamyl, mono (lower alkyl) carbamyl, di (lower alkyl) carbamyl, halogen, mercapto, sulfo, lower alkyl sulfide, lower alkyl sulfoxide, lower alkyl sulfone, acetoxy, pyrrolidine, piperidine, morpholino, thiomorpholine, piperazine, N- (lower alkyl) piperazine, N-hydroxy (lower alkyl) piperazine, N- (lower alkanoyl) piperazino or N-carbo (lower alkoxy) piperazino; R2, when taken separately, is hydrogen or lower alkyl; R3, when taken separately, is hydrogen, phenyl, lower alkyl or substituted lower alkyl where the substituent is amino, mono (lower alkyl) amino, di (lower alkyl) amino, pyrrolidino, piperidino, morpholino, N- (lower alkyl) piperazino, R-hydroxy (lower-alkyl) piperazino, N- (lower alkanoyl) piperazino, N-carbo (lower alkoxy) piperazino, pyrrolo, piperazino, imicazolidino, hydroxy, lower alkoxy, thio (lower alkyl), carboxy, carbo (lower alkoxy), carbamyl, mono (lower alkyl) carbamyl, di (lower alkyl) carbamyl, lower alkanoyloxy or lower alkanoylamino and R2 and R3, when taken together with the nitrogen atom to which they are attached, form pyrrolo, pyrrolidine groups, piperidino, morpholino, thiomorpholino, piperazino, N- (lower alkyl) piperazino, N-hydroxy (lower alkyl) piperazino, N- (lower alkanoyl) piperazino or N-carbo (lower alkoxy) piperazino; and the pharmaceutically acceptable acid addition salts of those compounds where at least one of R1 and R3 is substituted lower alkyl where the substituent is a basic group; characterized by reacting a compound of the formula where V is C1, Br, N + (CH3) 3C1 or N + (CH3) 3Br- when Z is (see formula) where R2 and R3 are as defined above, or V is Cl or Br when Z is -0-lower alkyl and X is as defined above, with a compound of the formula **(See formula)** wherein R1 is as defined above, in the presence of an aqueous sodium or potassium hydroxide, and in any order and when required, (i) reacting the compound thus formed where Z is -0 -lower alkyl and X and R1 are as defined above, with a compound of the formula **(See formula)** and/or (ii) reacting the compound thus formed with an appropriate oxidizing agent to form a compound of formula I' where I' is -SO- or -SO2 and X, R1, R2 and R3 are as defined in the foregoing, and if desired, to form the pharmaceutically acceptable acid addition salts of those compounds wherein at least one of R1 and R3 is substituted lower alkyl, wherein the substituent is a basic group. (Machine-translation by Google Translate, not legally binding)