FIELD: organic chemistry, chemical technology, medicine, pharmacy. SUBSTANCE: invention relates to novel derivatives of azolidinedione of the formula (1) where one of X, Y and Z means c=O or C=S and one of remaining X, Y and Z means group C= and others mean C= C; R1, R2, R3 are substituted either by X, Y and Z or by nitrogen atom and they can be similar or different and mean hydrogen, halogen atom, hydroxy-group, nitro-group and others; group -(CH2)n-O can be linked through nitrogen atom or X, Y, Z; n = 1-4; Ar means phenylene or naphthylene; R4 means hydrogen atom or forms a bond with the group A; A means nitrogen atom or CR5 where R5 means hydrogen, halogen atom or forms a bond with R4; B means O or S atom when A means CR5; B means O atom when A means N atom; its tautomeric forms, stereoisomers, polymorphic forms, pharmaceutically acceptable salts and solvates. Invention relates also to method of synthesis of compound of the formula (1) by interaction of compound of the formula (VIII)
with compound of the formula (XII)
and so on. Invention relates also to pharmaceutical composition eliciting antidiabetic activity and containing compound of the formula (1) and pharmaceutically acceptable carrier, vehicle, filling agent or solvate. Invention relates also to method of prophylaxis or treatment of diseases where insulin non-susceptibility confers the base of pathophysiological mechanism involving administration of compound of the formula (1) in patient needing with its. Invention relates also to method of reduction of blood glucose, plasma triglycerides or free fatty acids involving administration of compound of the formula (1) in patient needing with its. Invention relates to intermediate compound of the formula (III)
where G means -CHO, -NH2, - CH=NOH and so on; J means hydroxy-group, halogen atom; R means hydrogen atom, lower alkyl; one of X, Y and Z means C=O or C=S and one of remaining X, Y and Z means group C= and others mean group C=C; R1, R2, R3 are substituted by either X, Y and Z or by nitrogen atom and they can be similar or different and mean hydrogen, halogen atom, hydroxy-group, nitro-group and so on; or any two of R1, R2, R3 in common with adjacent atoms to which they are bound can form substituted or unsubstituted 4-7- membered cycle with one or more double bonds and so on; group (CH2)n-O- can be linked through nitrogen atom or X, Y, Z; n = 1-4; Ar means phenylene or naphthylene; R4 means hydrogen atom or forms a bond with group A; A means nitrogen atom or CR5 where R5 means hydrogen, nitrogen atom or forms a bond with R4; B means O or S atom when A means CR5; B means O atom when A means N atom. Invention provides synthesis of novel derivatives of azolidinedione. EFFECT: improved method of synthesis, valuable medicinal properties of compounds. 24 cl, 3 tbl, 43 ex
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Authors
Dates
2003-03-10—Published
1997-06-30—Filed