New Antiinflammatory Agents. 2. 5-Phenyl-3H-Imidazo[4,5-c][1,8]naphthyridin-4(5H)-ones: A New Class of Nonsteroidal Antiinflammatory Agents with Potent Activity Like Glucocorticoids

Journal of Medicinal Chemistry

Volumn 35, Issue 15, 1992, Pages 2863-2870

  Suzuki, Fumio ^a   Kuroda, Takeshi ^a   Tamura, Tadafumi ^a   Sato, Soichiro ^a   Ohmori, Kenji ^a   Ichikawa, Shunji ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,8 NAPHTHYRIDINE DERIVATIVE; 3 BENZYL 5 PHENYL 3H IMIDAZO[4,5 C][1,8]NAPHTHYRIDIN 4(5H) ONE; 5 PHENYLIMIDAZO[4,5 C][1,8]NAPHTHYRIDIN 4(5H) ONE DERIVATIVE; ARACHIDONATE 5 LIPOXYGENASE; CARRAGEENAN; GLUCOCORTICOID; GUM ARABIC; NONSTEROID ANTIINFLAMMATORY AGENT; PREDNISOLONE; PROSTAGLANDIN SYNTHASE; RABBIT ANTISERUM; UNCLASSIFIED DRUG; ZYMOSAN;

ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION;

EID: 0026635203     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00093a020     Document Type: Article

References (22)

1. Silber, R. H.; Busch, R. D.; Oslaps, R. Practical Procedure for Estimation of Corticosteron or Hydrocortisone. Clin. Chem. 1958, 4, 278-285.
2. Vane, J. R. Inhibition of Prostaglandin Synthesis as a Mechanism of Action for Aspirin Like Drugs. Nature (New Biol.) 1971, 231, 232-235.
3. Flower, R. J. Drugs which Inhibit Prostaglandin. Biosynthesis. Pharmacol. Rev. 1974, 26, 33-71.
4. Moore, G. G. I.; Swingle, K. F. 2,6-Di-tert-butyl-4-(2′-thenoyl) phenol(R-830): A Novel Nonsteroidal Anti-inflammatory Agent with Antioxidant Properties. Agents Actions 1982, 12, 674-683.
5. DiMartino, M. J.; Griswold, D. E.; Berkowitz, B. A. ; Poste, G.; Hanna, N. Pharmacologic Characterization of the Antiinflammatory Properties of a New Dual Inhibitor of Lipoxygenase and Cyclooxygenase. Agents Actions 1987, 20, 113-123.
6. Ikuta, H.; Shirota, H.; Kobayashi, S.; Yamagishi, Y.; Yamada, K.; Yamatsu, I.; Katayama, K. Synthesis and Antiinflammatory Activities of 3-(3,5-Di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones. J. Med. Chem. 1987, 30, 1995-1998.
7. Clemence, F.; Martret, O. L.; Delevallee, F.; Benzoni, J.; Jouanen, A.; Jouquey, S.; Mouren, M.; Deraedt, R. 4-Hydroxy-3-quinolinecarboxamides with Antiarthritic and Analgesic Activities. J. Med. Chem. 1988, 31, 1453-1462.
8. Lazer, E. S.; Wong, H. C.; Possanza, G. J.; Graham, A. G.; Farina, P. R. Antiinflammatory 2,6-Di-ferf-butyl-4-(2-arylethenyllphenols. J. Med. Chem. 1989, 32, 100-104.
9. Mylari, B. L.; Carty, T. J.; Moore, P. F.; Zembrowski, W. J. 1,2-Dihydro-l-oxopyrrolo[3,2,l-kl]phenothiazine-2-carboxamides and Congeners, Dual Cyclooxygenase/5-Lipoxygenase Inhibitors with Antiinflammatory Activity. J. Med. Chem. 1990, 33, 2019-2024.
10. Flynn, D. L.; Capiris, T.; Cetenko, W. J.; Connor, D. T.; Dyer, R. D.; Kostlan, C. R.; Nies, D. E.; Schrier, D. J.; Sircar, J. C. Nonsteroidal Antiinflammatory Drug Hydroxamic Acids. Dual Inhibitors of Cyclooxygenase and 5-Lipoxygenase. J. Med. Chem. 1990, 33, 2070-2072.
11. Burch, R. M.; Weitzberg, M.; Blok, N.; Muhlhauser, R.; Martin, D.; Farmer, S. G.; Bator, J. M.; Connor, J. R.; Ko, C.; Kuhn, W.; McMillian, B. A.; Paynor, M.; Shearer, B. G.; Tiffany, C.; Wilkins, D. E. N-(Fluorenyl-9-methoxycarbonyl)-amino acids, a Class of Antiinflammatory Agents with a Different Mechanism of Action. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 355-359.
12. Gane, K. R.; Galbraith, W.; Roman, R. J.; Haber, S. B.; Kerr, J. S.; Schmidt, W. K.; Smith, C.; Hewes, W. E.; Ackerman, N. R. Anti-inflammatory and Safety Profile of DUP 697, a Novel Orally Effective Prostaglandin Synthesis Inhibitor. J. Pharmacol. Exp. Ther. 1990, 254, 180-187.
13. Brand, L. M.; Skare, K. L.; Loomans., E.; Reller, H. H.; Schwen, R. J.; Lade, D. A.; Bohne, R. L.; Maddin, C. S.; Moorehead, D. P.; Fanelli, R.; Chibrando, C.; Castelli, M. G.; Tai, H. H. Anti-inflammatory Pharmacology and Mechanism of the Orally Active Capsaicin Analogs, NE-19550 and NE-28345. Agents Actions 1990, 31, 329-340.
14. Kuroda, T.; Suzuki, F.; Tamura, T.; Hosoe, H.; Ohmori, K. A Novel Synthesis and Potent Antiinflammatory Activity of 4-Hydroxy-2-oxo-l-phenyl-lH-1,8-naphthyridine-3-carboxamides. J. Med. Chem. 1992, 35, 1130-1136.
15. Moilanen, E.; Alanko, J.; Asmawi, M. Z.; Vapaatalo, H. CP-66,248, a New Anti-inflammatory Agent, is a Potent Inhibitor of Leukotriene B4 and Prostanoid Synthesis in Human Polymorphonuclear Leukocytes in Vitro. Eicosanoids 1988, 1, 35-39.
16. Kuroda, T.; Suzuki, F. A Facile and Novel Synthesis of 5-Phenylimidazo[4,5-c][1,8]naphthyridin-4(5H)-ones. J. Heterocycl. Chem. 1991, 28, 2029-2034.
17. Suzuki, F.; Kuroda, T.; Kitamura, S.; Ohmori, K. Imidazonaphthyridine Derivatives. Eur. Patent 459 505, 1991.
18. Villar, A.; Gaseo, M. A.; Alearaz, M. J. Some Aspects of the Inhibitory Activity of Hypolaetin-8-glucoside in Acute Inflammation. J. Pharm. Pharmacol. 1987, 39, 502-507.
19. Winter, C. A.; Risley, E. A.; Nuss, G. W. Carrageenin-Induced Edema in Hind Paw of the Rat as an Assay for Antiinflammatory Drugs. Proc. Soc. Exp. Biol. Med. 1962, 111, 544-547.
20. Gemmell, D. K.; Cottney, J.; Lewis, A. J. Comparative Effects of Drugs on Four Paw Oedema Models in the Rat. Agents Actions 1979, 9, 107-116.
21. Koda, A.; Nagai, H.; Wada, H. Pharmacological Actions of Baicalin and Baicalein. II. Active Anaphylaxis. Folia Pharmacol. Jpn. 1970, 66, 237-247.
22. Terasawa, M.; Goto, K.; Maruyama, Y. Effect of Traxanox Sodium on Type I-IV Allergic Reactions. Studies on Anti-allergic Agent VII. Folia Pharmacol. Jpn. 1982, 80, 417-427.