5-PHENOXYALKYL-2,4-THIAZOLIDINEDIONES, METHODS OF THEIR SYNTHESIS, PHARMACEUTICAL COMPOSITION CONTAINING THEREOF AND INTERMEDIATE COMPOUNDS Russian patent published in 2001 - IPC

FIELD: organic chemistry, pharmacy. SUBSTANCE: invention relates to novel derivatives of 5-phenoxyalkyl-2,4-thiazolidinediones of the general formula (I) where A means linear or branched C₂-C₁₆-alkylene group that is saturated and optionally substituted with hydroxy- -group or phenyl; D means mono- or dicyclic aromatic group that can has one or two oxygen atoms; X means hydrogen atom, C₁-C₆-alkyl, alkoxyalkyl-group, halogen atom, cyano-group, carboxy-group; n = 1-3 under condition that if A means butylene then does not mean 4-chlorophenyl group as free form or pharmacologically acceptable salts. Method of synthesis of 5-phenoxyalkyl-2,4-thiazolidinediones of the general formula (I) involves interaction of compound of the formula (II) with dihalogenalkylene of the formula (III) in the presence of basic agent to yield compound of the formula (IV) which is subjected for reaction with dialkylmalonate of the formula (V) in the presence of alkaline metal alcoholate to yield compound of the formula (VI) which is subjected for halogenation to yield compound of the formula (II) which is heated at boiling with reflux condenser in acid medium to yield α-halogenacid of the formula (VIII) which is subjected for reaction with thiourea to yield 2-imino-4-thiazolidinone of the formula (IX) . Derivatives of dicarboxylic acid of the formula (VII) , derivative of α--halogenacid of the formula (VIII), derivative of 2-imino-4-thiazolidinone of the formula (IX), derivative of 2,4-thiazolidinedione of the formula (XVIII) are formed in the process of synthesis and have values X, D, n, A, Hal, indicated above as intermediate compounds. Invention relates to also pharmaceutical composition showing antidiabetic activity containing compound of the formula (I) and pharmaceutically acceptable nontoxic inert carrier or vehicle. EFFECT: new compounds indicated above, improved method of synthesis, valuable medicinal properties. 18 cl, 2 tbl