Novel coumarin quinolone carboxylic acids and processes for...

C - Chemistry – Metallurgy – 07 – D

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C07D 491/052 (2006.01) A61K 31/435 (2006.01) C07D 411/04 (2006.01) C07D 491/14 (2006.01) C07D 491/147 (2006.01)

Patent

CA 2210448

The present invention relates to novel coumarin quinolone carboxylic acids wherein the pyridone system is fused in 3,4-, 6,7- and 7,8-positions of the coumarin system, of the general formula I (see fig. I) wherein R1R2 = -NHCH=C(CO2R6)CO-, R3=NO2 or NH2, R4=R5=H, R6 = H or C2H5; R1R2 = -NHCH=C(CO2R6)CO-, R3 = R4 = H, R5 = F, R6 = H or C2H5; R1R2 = -CO(CO2R6)C=CHNH-, R3 = R4 = R5 = H, R6 = H or C2H5; R1R2 = R3R4 = -NHCH=C(CO2R6)CO-, R5 = H, R6 = H or C2H5; R1 = H or OH, R2 = R5 = H, R3R4 = -NHCH=C(CO2R6)CO-, R6 = H or C2H5; R1 = OH, R2 = R3 = H, R4R5 = -CO(CO2R6)C=CHNH-, R6 = H or C2H5; R1 = R5 = H, R2 = CH3 or CF3, R3R4 = -CO(CO2R6)C=CHNH-, R6 = H or C2H5, as well as pharmaceutically acceptable salts thereof. The object of the invention are also processes for the preparation of novel coumarin quinolone carboxylic acids and the biological action thereof.

La présente invention concerne des nouveaux acides coumarinequinolonecarboxyliques où le système pyridone est lié dans les positions 3,4-, 6,7- et 7,8- du système coumarine, de formule générale I Image où R1R2 = -NHCH=C(CO2R6)CO, R3 = NO2 ou NH2, R4 = R5 = H, R6 = H ou C2H5; R1R2 = -NHCH=C(CO2R6)CO, R3 = R4 = H, R5 = F, R6 = H ou C2H5; R1R2 = -CO(CO2R6)C=CHNH, R3 = R4 = R5 = H, R6 = H ou C2H5; R1R2 = R3R4 = -NHCH=C(CO2R6)CO, R5 = H, R6 = H ou C2H5; R1 = H ou OH, R2 = R5 = H, R3R4 = -NHCH=C(CO2R6)CO, R6 = H ou C2H5; R1 = OH, R2 = R3 = H, R4R5 = -CO(CO2R6)C=CHNH, R6 = H ou C2H5; R1 = R5 = H, R2 = CH3 ou CF3, R3R4 = -CO(CO2R6)C=CHNH, R6 = H ou C2H5, ainsi que des sels pharmaceutiquement acceptables de ces derniers. L'invention porte également sur les procédés de préparation des nouveaux acides coumarinequinolonecarboxyliques et sur l'action biologique de ces derniers.

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