A series of non-quinoline cysLT1 receptor antagonists: SAR study on pyridyl analogs of Singulair®

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 5, 1998, Pages 453-458

  Guay, Daniel ^a   Gauthier, J Y ^a   Dufresne, C ^a   Jones, T R ^a   McAuliffe, M ^a   McFarlane, C ^a   Metters, K M ^a   Prasit, P ^a   Rochette, C ^a   Roy, P ^a   Sawyer, N ^a   Zamboni, R ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

L 733321; LEUKOTRIENE RECEPTOR BLOCKING AGENT; MONTELUKAST; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; GUINEA PIG; IN VITRO STUDY; NONHUMAN; SQUIRREL MONKEY; STRUCTURE ACTIVITY RELATION;

ACETATES; ANIMALS; ANTI-ASTHMATIC AGENTS; GUINEA PIGS; HUMANS; LEUKOTRIENE ANTAGONISTS; MEMBRANE PROTEINS; PYRIDINES; QUINOLINES; RATS; RECEPTORS, LEUKOTRIENE; SAIMIRI; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032478258     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00051-1     Document Type: Article

References (26)

1. 1. (a) Drazen, J. M.; Austen, K. F. Am Rev. Respir. Dis. 1987, 136, 985.
2. (b) Parker, C. W. Drug Dev. Res. 1987, 10, 277.
3. (c) Samuelsson, B.; Dahlen, S. E.; Lindgren, J. A.; Rouzer, C.; Serhan, C. N. Science 1987, 237, 1171.
4. 2. Dahlen, S.E.; Hedqvist, P.; Hammarstrom, S.; Samuelsson, B. Nature (London) 1980, 288, 484.
5. 3. (a) Labelle, M.; Prasit, P.; Belley, M.; Blouin, M.; Champion, E.; Charette, L.; DeLuca, J. G.; Dufresne, C.; Frenette, R.; Gauthier, J. Y.; Grimm, E.; Grossman, S. G.; Guay, D.; Herold, E. G.; Jones, T. R.; Lau, C. K.; Leblanc, Y.; Léger, S.; Lord, A.; McAuliffe, M.; McFarlane, C.; Masson, P.; Metters, K. M.; Ouimet, N.; Patrick, D. H.; Perrier, H.; Pickett, C. B.; Piechuta, H.; Roy, P.; Williams, H.; Wang, Z.; Xiang, Y. B.; Zamboni, R. J.; Ford-Hutchinson, A. W.; Young, R. N. Bioorg. Med. Chem. Lett. 1992, 2, 1141.
6. (b) Labelle, M.; Belley, M.; Campion, E.; Gordon, R.; Jones, T. R.; Leblanc, Y.; McAuliffe, M.; McFarlane, C.; Masson, P.; Metters, K. M.; Nicoll-Griffith, D.; Ouimet, N.; Piechuta, H.; Rochette, C.; Sawyer, N.; Xiang, X. B.; Yergey, J.; Ford-Hutchinson, A. W.; Pickett, C. B.; Zamboni, R. J.; Young, R.N. Bioorg. Med. Chem. Lett. 1994, 4, 463.
7. 4. (a) Labelle, M.; Belley, M.; Gareau, Y.; Gauthier, J. Y.; Guay, D.; Gordon, R.; Grossman, S. G.; Jones, T. R.; Leblanc, Y.; McAuliffe, M.; McFarlane, C.; Masson, P.; Metters, K. M.; Ouimet, N.; Patrick, D. H.; Piechuta, H.; Rochette, C.; Sawyer, N.; Xiang, X. B.; Pickett, C. B.; Ford-Hutchinson, A. W.; Zamboni, R. J.; Young, R. N. Bioorg. Med. Chem. Lett. 1995, 5, 283.
8. (b) Jones, T. R.; Labelle, M.; Belley, M.; Campion, E.; Charette, L.; Evans, J.; Ford-Hutchinson, A. W.; Gauthier, J. Y.; Lord, A.; Masson, P.; McAuliffe, M.; McFarlane, C. S.; Metters, K. M.; Pickett, C.; Piechuta, H.; Rochette, C.; Rodger, I. W.; Sawyer, N.; Young, R. N.; Zamboni, R.; Abraham, W. M. Can. J. Phiosiol. Pharmacol. 1995, 73, 191.
9. 5. (a) Bernstein, P. R. Drugs Fut. 1994, 19, 217. Hui, K. P.; Barnes, N. C. Lancet, 1991, 337, 1062.
10. 5. (a) Bernstein, P. R. Drugs Fut. 1994, 19, 217. Hui, K. P.; Barnes, N. C. Lancet, 1991, 337, 1062.
11. (b) Smith, C.; Christie, P. E.; Lee, T. H. J. Allergy Clin. Immunol. 1991, 87, 139. Robuschi, M.; Fuccella, L. M.; Riva, E.; Vida, E.; Barnabe, R.; Rossi, M.; Gambaro, G.; Spagnotto, S.; Bianco, S. Am. Rev. Respir. Dis. 1991, 143, A642.
12. (b) Smith, C.; Christie, P. E.; Lee, T. H. J. Allergy Clin. Immunol. 1991, 87, 139. Robuschi, M.; Fuccella, L. M.; Riva, E.; Vida, E.; Barnabe, R.; Rossi, M.; Gambaro, G.; Spagnotto, S.; Bianco, S. Am. Rev. Respir. Dis. 1991, 143, A642.
13. (c) Nakagawa, T.; Mizushima, Y.; Ishii, A.; Nambu, F.; Motoishi, M.; Yui, Y.; Shida, T.; Miyamoto, T. Adv. Prostaglandin Thromboxane Leukot. Res. 1991, 21a, 465.
14. (d) Wahedna, I.; Wisniewsky, A. F.; Britton, J. R.; Tattersfield, A. E. Am. Rev. Respir. Dis. 1991, 143, A642.
15. 6. Reiss, T. F.; Chervinsky, P.; Noonan, M.; Prenner, B.; Zhang, J.; Hess, J.; Friedman, B.; Kundu, S. Eur. Resp. J. 1995, 8, Suppl 19, P1448.
16. 7. (a) Lau, C. K.; Dufresne, C.; Gareau, Y.; Zamboni, R.; Labelle, M.; Young, R. N.; Metters, K. M.; Rochette, C.; Sawyer, N.; Slipetz, D. M.; Charette, L.; Jones, T.; McAuliffe, M.; McFarlane, C.; Ford-Hutchinson, A. W. Bioorg. Med. Chem. Lett. 1995, 5, 1615.
17. (b) Labelle, M.; Gareau, Y.; Dufresne, C.; Lau, C. K.; Belley, M.; Jones, T. R.; Leblanc, Y.; McAuliffe, M.; McFarlane, C.; Metters, K. M.; Ouimet, N.; Perrier, H.; Rochette, C.; Sawyer, N.; Slipetz, D. M.; Xiang, Y. B.; Wang, Z.; Pickett, C. B.; Ford-Hutchinson, A. W.; Young, R. N.; Zamboni, R. Bioorg. Med. Chem. Lett. 1995, 5, 2551.
18. 8. Pong, S. S.; DeHaven, R. Proc. Natl. Acad. Sci. USA. 1983, 80, 7415.
19. 9. Frey, E. A.; Nicholson, D. W.; Metters, K. M. Eur. J. Pharmacol., Mol. Pharmacol. Sect. 1993, 244, 239.
20. 10. McFarlane, C. S.; Hamel, R.; Ford-Hutchinson, A. W. Agents Actions 1987, 22, 63.
21. 11. For full experimental details see: Zamboni, R.; Guay, D.; Gauthier, J. Y. U.S. Patent 5 506 227, 1996; Chem. Abstr. 199?, 120, 27'0117.
22. 12. Piccolo, O.; Martinengo, T. Synt. Comm. 1981, 11, 497. Kumada, M. Pure Appl. Chem. 1980, 52, 669.
23. 12. Piccolo, O.; Martinengo, T. Synt. Comm. 1981, 11, 497. Kumada, M. Pure Appl. Chem. 1980, 52, 669.
24. 13. Fife, W. K. J. Org. Chem. 1983, 48, 1375.
25. 14. Ciufolini, M. A.; Byrne, N. E. J. Chem. Soc., Chem. Comm. 1988, 1230. Bell, T. W.; Rothenberger, S. D. Tetrahedron Lett. 1987, 28, 4817.
26. 14. Ciufolini, M. A.; Byrne, N. E. J. Chem. Soc., Chem. Comm. 1988, 1230. Bell, T. W.; Rothenberger, S. D. Tetrahedron Lett. 1987, 28, 4817.