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With triethylamine In dichloromethane; acetonitrile
17 (E)-4-(2-(2-(N-Morpholinoacetyl-N-(4-methoxybenzenesulfonyl)amino)phenyl)ethenyl)pyridine 1-oxide hydrochloride
EXAMPLE 17 (ANOTHER METHOD FOR PREPARATION) (E)-4-(2-(2-(N-Morpholinoacetyl-N-(4-methoxybenzenesulfonyl)amino)phenyl)ethenyl)pyridine 1-oxide hydrochloride Morpholinoacetic acid (5.18 g) prepared in the same manner as Reference Example 1 was dissolved in methylene chloride (230 ml), and triethylamine (4.86 g) was added thereto. To the mixture was added dropwise ethyl chlorocarbonate (5.21 g) under ice-cooling, and the mixture was stirred for thirty minutes at room temperature. To the mixture was added (E)-4-(2-(2-(N-(4-methoxybenzenesulfonyl)amino)phenyl)ethenyl)pyridine 1-oxide (7.65 g) and the mixture was further stirred for three hours at room temperature. The reaction solution was washed with water, dried over magnesium sulfate and concentrated. The resultant residue was dissolved in acetonitrile. To the solutuion was added hydrochloric acid-methanol and the mixture was stirred over night at room temperature. The precipitated crystals were filtered off, washed with acetonitrile and further with ether and the crude crystals were obtained. The recrystallizaion from methanol yielded the objective compound (8.16 g).
20 (E)-4-[2-[2-[[(p-Methoxyphenyl)sulfonyl]amino]phenyl]ethenyl]pyridine 1-oxide
EXAMPLE 20 (E)-4-[2-[2-[[(p-Methoxyphenyl)sulfonyl]amino]phenyl]ethenyl]pyridine 1-oxide In 10 ml of acetic acid was dissolved 1.83 g of the compound obtained in Example 3. Then, 2.80 g of 30% aqueous hydrogen peroxide solution was added and the mixture was stirred at 70 ° C. overnight. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by extraction with chloroform. The chloroform layer was dehydrated over anhydrous magnesium sulfate and the solvent was evaporated off. The residue was purified by silica gel column chromatography (chloroform-methanol=9:1). The crystal crop was recrystallized from ethanol to provide 0.48 g of the title compound (white needles). m.p. 224-226° C. (decomp.)
Examples of the compounds of the present invention may include compounds of the formula [1]. ... (E)-4-[2-{2-[N-acetyl-N-(4-methoxybenzenesulfonyl)amino]pheny 1}ethenyl]pyridine, (E)-4-[2-{2-[N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl ]pyridine 1-oxide, (E)-4-[2-{2-[N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl ]pyridine, (E)-4-[2-{2-[N-(2-hydroxyethyl)-N-(4-methoxybenzenesulfonyl)a mino]phenyl)ethenyl]pyridine 1-oxide, ...
The remedy for chronic rheumatoid arthritis according to claim 1, wherein the compound represented by the formula [I] is a compound selected from the group consisting of (E)-4-[2-{2-[N-acetyl-N-(4-methoxybenzenesulfonyl)amino]pheny 1}ethenyl]pyridine 1-oxide, (E)-4-[2-{2-[N-acetyl-N-(4-methoxybenzenesulfonyl)amino]pheny 1}ethenyl]pyridine, (E)-4-[2-{2-[N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl ]pyridine 1-oxide, (E)-4-[2-{2-[N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl ]pyridine, (E)-4-[2-{2-[N-(2-hydroxyethyl)-N-(4-methoxybenzenesulfonyl)a mino]phenyl}ethenyl]pyridine 1-oxide, ...