Antiallergy Agents. 1. Substituted 1,8-Naphthyridin-2(1H)-ones as Inhibitors of SRS-a Release

Journal of Medicinal Chemistry

Volumn 31, Issue 11, 1988, Pages 2108-2121

  Sherlock, Margaret H ^a   Kaminski, James J ^a   Tom, Wing C ^a   Lee, Joe F ^a   Wong, Shing Chun ^a   Kreutner, William ^a   Bryant, Robert W ^a   McPhail, Andrew T ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,8 NAPHTHYRIDIN 2(1H) ONE DERIVATIVE; 4 ACETOXY 3 ALLYL 1 PHENYL 1,8 NAPHTHYRIDIN 2(1H) ONE; LEUKOTRIENE D4; SLOW REACTING SUBSTANCE; UNCLASSIFIED DRUG;

ALLERGY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; BRONCHOSPASM; CRYSTALLOGRAPHY; DRUG METABOLISM; DRUG SYNTHESIS; GUINEA PIG; NONHUMAN; ORAL DRUG ADMINISTRATION; STRUCTURE ACTIVITY RELATION;

EID: 0023717299     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00119a010     Document Type: Article

References (52)

1. Herzig, D. J. In New Drug Discovery and Development; Rubin, A. A., Ed.; Marcel Dekker: New York, 1978; p 29.
2. Kellaway, C. H.; Trethwie, E. R. Quat. J. Exp. Physiol. 1940, 30, 121.
3. Orange, R. P.; Austen, K. F. In Advances in Immunology; Dixon, F. J., Kunkel, H. G., Ed.; Academic: New York, 1969, Vol. 10, p 105-144.
4. Goetzl, E. J. N. Engl. J. Med. 1980, 303, 822.
5. Kreutner, W.; Siegel, M. I. In Annual Reports in Medicinal Chemistry; Bailey, D. M., Ed.; Academic: New York, 1984; Vol. 19, pp 241-252.
6. Dahlen, S. E.; Hansson, G.; Hedquist, P.; Bjorck, T.; Granstron, E.; Dahlen, B. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 1712.
7. Dahlen, S. E.; Bjorck, J.; Hedquist, P.; Arfors, K. E.; Hammarstram, S.; Lindgreen, J. A. and Samuelsson, B., Proc. Natl. Acad. Sci. 1981, 78, 3887.
8. Hedquist P.; Dahlen, S. E.; Gustafsson, L.; Hammarstrom, S.; Samuelsson, B. Acta Physiol. Scand. 1980, 110, 331.
9. Holroyde, M. C.; Altouynyan, R. E. C.; Cole, M.; Dixon, M.; Elliott, E. V. Lancet. 1981, 2, 17.
10. Weiss, J. W.; Drazen, J. M.; Cole, N. Science (Washington, D.C.) 1982, 216, 196.
11. Griffin, M.; Weiss, J. W.; Leitch, A. G.; McFadden, E. R.; Corey, E. J.; Austen, K. F.; Drazen, J. N. Engl. J. Med. 1983, 308, 436.
12. Murphy, R. C.; Hammarstron, S.; Samuelson, B. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 4275.
13. Hammarstron, S.; Samuelsson, B.; Clark, D. A.; Goto, G.; Marafat, A.; Miokowski, C.; Corey, E. J. Biochem. Biophys. Res. Commun 1980, 92, 946.
14. Morris, H. R.; Taylor, G. W.; Piper, P. J.; Samhoun, M. N.; Tippins, J. R. Prostaglandins 1980, 19, 185.
15. Morris, H. R.; Taylor, G. W.; Piper, P. J.; Tippins, J. R. Nature (London) 1980, 285, 104.
16. Pong, S. S.; DeHaven, R. N. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 7415.
17. Pong, S. S.; DeHaven, R. N.; Kuehl, F. A., Jr.; Egan, R. W. J. Biol. Chem. 1983, 258, 9616.
18. Bowden, K. J.; Grank, G.; Ross, W. J. J. Chem. Soc. C. 1969, 172.
19. Sliwa, H.; Maitte, P., C. R. Hebol. Seances Acad. Sci. 1964, 259, 2255.
20. Fox, H. H. J. Org. Chem. 1952, 17, 547.
21. Nantka-Namirsky, P.; Piechaczak, J. Pol. 1970, 60, 438;
22. Nantka-Namirsky, P.; Piechaczak, J. Chem. Abstr. 1974, 74, 64214b.
23. Setliff, F. J. Chem. Eng. Data 1970, 15, 590.
24. Godar, E. M.; Mariella, R. P. J. Org. Chem. 1960, 25, 557.
25. Kermack, W. O.; Weatherhead, A. P. J. Chem. Soc. 1942, 726.
26. Nantka-Namirsky, P. Acta. Pol. Pharm. 1967, 24, 111.
27. Bachman, G. B.; Barker, R. S. J. Org. Chem. 1949, 14, 97.
28. Jerchel, D.; Jakob, L. Chem. Ber. 1958, 91, 1266.
29. Dunn, G. E.; Thimm, H. F. Can. J. Chem. 1977, 55, 1342.
30. Bohme, H. Arch. Pharm. 1960, 293, 1011.
31. Sherlock, M. U.S. Pat. 4492702, 1985;
32. Sherlock, M. Chem. Abstr. 1985,102, 132018w.
33. Juby, P. F.; Hudyma, T. W. J. Med. Chem. 1967, 10, 954.
34. Ziegler, E.; Maier, H. Montash. Chem. 1958, 89, 551.
35. Blythin, D. J.; Kaminski, J. J.; Domalski, M. S.; Spitler, J.; Solomon, D. M.; Conn, D. J.; Wong, S. C.; Verbiar, L. L.; Bober, L. A.; Chiu, P. J. S.; Watnick, A. S.; Siegel, M. I.; Hilbert, J. M.; McPhail, A. T. J. Med. Chem. 1986, 29, 1099.
36. Kim, D. H. J. Heterocycl. Chem. 1974, 11, 703.
37. Doering, W. E.; Weil, R. A. N. J. Am. Chem. Soc. 1947, 69, 2461.
38. Solomon, D. M.; Conn, D. J.; Wong, S. C.; Kaminski, J. J. Heterocycles 1986, 24, 2179.
39. Wolfe, S. Acc. Chem. Res. 1972, 5, 102.
40. Anderson, W. H.; O'Donnell, M. O.; Simko, M.; Welton, A. F. Br. J. Pharmacol. 1983, 78, 67.
41. Wong, S. C.; Sasso, S.; Jones, H.; Kaminski, J. J. J. Med. Chem. 1984, 27, 20.
42. Augstein, J.; Farmer, J. B.; Lee, T. B.; Sheard, P.; Tattersall, M. L. Nature (London) 1973, 245, 215.
43. Fromson, J. M.; Pearson, S.; Bramah, S. Xenobiotica 1973, 3, 693.
44. Robertson, D. W.; Katzenellenbogen, J. A.; Long, D. J.; Rurke, E. A.; Katzenellenbogen, B. S. J. Steroid Biochem. 1982, 16, 1.
45. Jordan, V. C.; Bain, R. R.; Brown, R. R.; Gosden, B.; Santos, M. A. Cancer Res. 1983, 43, 1446.
46. Lyman, S. D.; Jordan, R. C. Biochem. Pharmacol. 1985, 34, 2787.
47. Myers, R. F.; Siegel, M. I. Biochem. Biophys. Res. Commun. 1983, 112, 586.
48. Musch, M.; Bryant, R. W.; Cosolluela, C.; Myers, R. F.; Siegel, M. I. Prostaglandins 1985, 29, 405.
49. International Tables for X-Ray Crystallography; Kynoch: Birmingham, England, 1974; Vol. IV.
50. Koopman, W. J.; Orange, R. P.; Austen, K. F. Proc. Soc. Exp. Biol. Med. 1971, 137, 64.
51. Konzett, H.; Rossler, R. Arch. Exp. Pathol. Pharmacol. 1940, 195, 71.
52. Clancy, R. M.; Hugli, T. E. Anal. Biochem. 1983, 133, 30.