Patent EA-003550-B1 (EA)
Title: Novel polyhydroxypyrazine derivatives, preparation and pharmaceutical compositions containing same
Inventor: BOUCHARD HERVE
IPC: A61P3/10
Filed: 2000-01-07
Abstract: 1. A product of general formula in which R1 represents the stereoisomeric forms of the chain -(CHOH)3-CH2-O-COR (II) and either R2 represents a hydrogen atom and R3 represents the stereoisomeric forms of the chain -CH2-(CHOH)2-CH2O-COR (III) or R2 represents the stereoisomeric forms of the chains -(CHOH)3-CH2-O-COR (II) or -CH2-(CHOH)2-CH2-O-COR (III) and R3 represents a hydrogen atom and R represents an -(Alk)i-(Cycloalk) radical, for which: Alk denotes an alkyl, saturated with hydrocarbon radical with normal or branched chain, having from 1 to 6 carbon atoms. Cycloalk denotes a saturated cyclic hydrocarbon radical, having 5 or 6 carbon atoms. i is equal to 0 or 1; or a stereoisomeric forms thereof or salt thereof with mineral or organic acid. 2. The product according to claim 1 of general formula: in which R represents an -(Alk)i-(Cycloalk) radical, for which: Alk denotes an alkyl, saturated with hydrocarbon radical with normal or branched chain, having from 1 to 6 carbon atoms. Cycloalk denotes a saturated cyclic hydrocarbon radical, having 5 or 6 carbon atoms, i is equal to 0 or 1; or a stereoisomeric forms thereof or salt thereof with mineral or organic acid. 3. A product according to the preceding claim of general formula: in which R represents an -(Alk)i-(Cycloalk) radical, for which: Alk denotes an alkyl, saturated with hydrocarbon radical with normal or branched chain, having from 1 to 6 carbon atoms. Cycloalk denotes a saturated cyclic hydrocarbon radical, having 5 or 6 carbon atoms, i is equal to 0 or 1; or a salt thereof with mineral or organic acid. 4. A product according to the preceding claim of general formula: in which R represents an -(Alk)i-(Cycloalk) radical, for which: Alk denotes an alkyl, saturated with hydrocarbon radical with normal or branched chain, having from 1 to 6 carbon atoms. Cycloalk denotes a saturated cyclic hydrocarbon radical, having 5 or 6 carbon atoms, i is equal to 0 or 1; or a salt thereof with mineral or organic acid. 5. A product according to any of claims 1-4 for which R represents an -(Alk)i-(Cycloalk) radical, for which: Alk denotes the methyl saturated with hydrocarbon radical with normal or branched chain, having from 1 to 6 carbon atoms. Cycloalk denotes a cyclohexyl radical, i is equal to 0 or 1; or a stereoisomeric form thereof or salt thereof with mineral or organic acid. 6. A product according to claim 1 selected from the group consisting of: 4,4'-O,O-dicyclohexyloyl-2-[(1R,2S,3R)(1,2,3,4-tetrahydroxylbutyl)]-5-[(2'S,3'R)(2',3',4'-trihydroxybutyl) ]pyrazine, and 4,4'-O,O-di(cyclohexylacetyl)-2-[(1R,2S,3R)-(1,2,3,4-tetrahydroxylbutyl)]-5-[(2'S,3'R)-(2',3',4'-trihydroxybutyl)]pyrazine, r a salt thereof with mineral or organic acid. 7. A compound 4,4'-O,O-Dicyclohexyloyl-2-[(1R,2S,3R)(1,2,3,4-tetrahydroxylbutyl)]-5-[(2'S,3'R)(2',3',4'-trihydroxybutyl)]pyrazine and its salts with an inorganic or organic acid. 8. A process for the preparation of the product according to any of claims 1-7, comprising reacting a product of general formula: in which: Ri1 represents a stereoisomeric form of the chain -(CHOH)3-CH2OH (XI) and Ri2 represents a hydrogen atom and Ri3 represents a stereoisomeric form of the chain -CH2-(CHOH)2-CH2OH (XII) or Ri2 represents the stereoisomeric forms of the chains -(CHOH)3-CH2OH (XI) or -CH2-(CHOH)2-CH2OH (XII) and Ri3 represents a hydrogen atom, with an acyl halide of formula R-COX, in which R is defined as in claim 1 and X represents a halogen atom. 9. The process according to claim 11, wherein the reaction is carried out in the presence of pyridine between 0 and 40 degree C. 10. A medicament comprising as active principle one or more compounds according to any of claims 1-7 and one or more excipients. 11. Use of the product according to any of claims 1-7 in the preparation of a medicament for the prevention or treatment of diabetes or a complication of diabetes.