3- or 4-Substituted N-alkyl-6-chloro-2 (1H)-pyridones (II) were prepared from the corresponding 6-chloro-2 (1H)-pyridones (I) by alkylation. 4-Substituted N-aryl-6-halo-2 (1H)-pyridones (XII) were prepared by the condensation of N-arylpropiolamide with diethyl malonate followed by the treatment with phosphorous oxychloride and hydrolysis. II and XII were converted to 2 (1H)-pyridone derivatives having amino (III, XVIII), alkoxy (IV, XIX) or alkylthio (V) group at 6-position. Their anti-inflammatory activity and analgesic activity were examined by the inhibition of carrageenin foot edema and acetic acid writhing. Some of them showed strong activities as anti-inflammatory and analgesic agents.