EP0428268A2 — Pharmaceutical phenylpyridone derivatives

USPTO Abstract

Compounds of the formula (1) : and pharmaceutically acceptable salts are described, wherein X is O or S; R¹ is C₁₋₆alkyl, C₂₋₆alkenyl, C₃₋₅cycloalkylC₁₋₄alkyl, or C₁₋₄alkyl substituted by 1 to 3 fluoro groups; R² is hydrogen, -CN, -CONR⁵R⁶, -CO₂R⁷, 5-tetrazolyl, -NO₂, -NH₂ or -NHCOR⁸ wherein R⁵ to R⁸ are independently hydrogen or C₁₋₄alkyl; R³ is hydrogen or C₁₋₄alkyl; R⁴ is hydrogen or C₁₋₄alkyl; and R is halo, C₁₋₄alkyl, C₁₋₄alkoxy, cyano, -CONR⁹R¹⁰, -CO₂R¹¹, -S(0) n C₁₋₄alkyl, -NO₂, -NH₂, -NHCOR¹², or -SO₂NR¹³R¹⁴ wherein n is 0, 1 or 2 and R⁹ to R¹⁴ are independently hydrogen or C₁₋₄alkyl; with the proviso that R¹ is not methyl when R² is -CO₂H, -CO₂CH₂CH₃ or -CN, X is 0, R³ is hydrogen, R⁴ is hydrogen or methyl and R is 6-methoxy. These compounds have bronchodilator, anti-allergic, vasodilator and anti-inflammatory activities. Pharmaceutical compositions are described as are methods of use. Processes for the preparation of the compounds of the formula (1) are described.