The reaction of quinolinic anhydride (2) with α-(or ɣ-) picoline yielded 6-(2-pyridinyl) cyclopentylbpyridine-5,7-dione (3) or 6-(4- pyridinyl) analogue 4 Compounds 3 and 4 were changed into the chloro derivatives 5 and 6 respectively by using mixture of phosphorus pentachloride and phosphorus oxychloride. The chloro compounds (5 and 6) underwent nucleophilic substitution condensed with different amines to produce compound 7 and 8 respectively. The hydrazino derivatives 7i and 8i respectively were with different aromatic aldehydes to produce 9 and 10 respectively. Compounds 8g and 10f, which showed a significant antiinflammatory action compared to Indomethacine. Also compounds 8h and 9h were active as anticoagulant as phenindione. Finally, 9f, and 9c. showed antimicrobial activity especially against Staphlococoue aureus and Escherichica coli.