New azole antagonists with high affinity for the P2Y1 receptor

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 12, 2013, Pages 3519-3522

  Ruel, Réjean ^a,b   L'Heureux, Alexandre ^a,c   Thibeault, Carl ^a,d   Daris, Jean Paul ^a   Martel, Alain ^a,b   Price, Laura A ^a   Wu, Qimin ^a   Hua, Ji ^a   Wexler, Ruth R ^a   Rehfuss, Robert ^a   Lam, Patrick Y S ^a,e  

^a BRISTOL MYERS SQUIBB   (United States)

^b INSTITUTE FOR RESEARCH IN IMMUNOLOGY AND CANCER   (Canada)

^c OmegaChem   (Canada)

^d BOEHRINGER INGELHEIM CANADA LTD   (Canada)

^e Lam Drug Discovery Consulting LLC   (United States)

Author keywords

Five membered ring heterocyclic urea mimics; P2Y1 antagonists; Platelet aggregation; Purinergic receptor; Thiadiazoles

Indexed keywords

ANTITHROMBOCYTIC AGENT; PURINERGIC P2Y RECEPTOR ANTAGONIST; PURINERGIC P2Y1 RECEPTOR; PYRROLE DERIVATIVE; THIADIAZOLE DERIVATIVE;

ARTICLE; DRUG POTENCY; DRUG STRUCTURE; RECEPTOR BLOCKING; STRUCTURE ACTIVITY RELATION;

BIOMIMETIC MATERIALS; HUMANS; KINETICS; PROTEIN BINDING; PURINERGIC P2Y RECEPTOR ANTAGONISTS; RECEPTORS, PURINERGIC P2Y1; STRUCTURE-ACTIVITY RELATIONSHIP; THIADIAZOLES; UREA;

EID: 84878114275     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.04.041     Document Type: Article

References (27)

1. M. Cattaneo Drug News Perspect. 19 2006 253
2. S. Murugappan, and S.P. Kunapuli Front. Biosci. 11 2006 1977
3. J.M. Herbert Expert Opin. Investig. Drugs 13 2004 457
4. B.N. Kahner Front. Biosci. 13 2008 433
5. B.N. Kahner, H. Shankar, S. Murugappan, G.L. Prasad, and S.P. Kunapuli J. Thromb. Haemost. 4 2006 2317
6. P. Illes, and J.A. Ribeiro Eur. J. Pharmacol. 483 2004 5
7. M. Cattaneo A.D. Michelson, Platelets 2006 Academic Press San Diego
8. J.E. Fabre, M. Nguyen, A. Latour, J.A. Keifer, L.P. Audoly, T.M. Coffman, and B.H. Koller Nat. Med. 5 1999 1199
9. C. Leon, B. Hechler, M. Freund, A. Eckly, C. Vial, P. Ohlmann, A. Dierich, M. LeMeur, J.-P. Cazenave, and C. Gachet J. Clin. Invest. 104 1999 1731
10. C.J. Foster, D.M. Prosser, J.M. Agans, Y. Zhai, M.D. Smith, J.E. Lachowicz, F.L. Zhang, E. Gustafson, F.J. Monsma, M.T. Wiekowski, S.J. Abbondanzo, D.N. Cook, M.L. Bayne, S.A. Lira, and M.S. Chintala J. Clin. Invest. 107 2001 1591
11. For a recent review see: M.A. Giorgi, H.C. Arazi, C.D. Gonzalez, and G. Di Girolamo Expert Opin. Pharmacother. 12 2011 1285 and references cited therein
12. M. Chhatriwala, R.G. Ravi, R.I. Patel, J.L. Boyer, K.A. Jacobson, and T.K. Harden J. Pharmacol. Exp. Ther. 311 2004 1038 and references cited therein
13. A. Norambuena, M.I. Poblete, M.V. Donoso, C.S. Espinoza, A. Gonzalez, and J.P. Huidobro-Toro Mol. Pharmacol. 74 2008 1666
14. B. Hechler, C. Nonne, E.J. Roh, M. Cattaneo, J.-P. Cazenave, F. Lanza, K.A. Jacobson, and C. Gachet J. Pharmacol. Exp. Ther. 316 2006 556 and references cited therein
15. J.A. Pfefferkorn, C. Choi, T. Winters, R. Kennedy, L. Chi, L.A. Perrin, G. Lu, Y.-W. Ping, T. McClanahan, R. Schroeder, M.T. Leininger, A. Geyer, S. Schefzick, and J. Atherton Bioorg. Med. Chem. Lett. 18 2008 3338
16. A.I. Morales-Ramos, J.S. Mecom, T.J. Kiesow, T.L. Graybill, G.D. Brown, N.V. Aiyar, E.A. Davenport, L.A. Kallal, B.A. Knapp-Reed, P. Li, A.T. Londregan, D.M. Morrow, S. Senadhi, R.K. Thalji, S. Zhao, C.L. Burns-Kurtis, and J.P. Marino Bioorg. Med. Chem. Lett. 18 2008 6222
17. D. Houston, S. Costanzi, K.A. Jacobson, and T.K. Harden Comb. Chem. High Through Screen. 11 2008 410
18. R.K. Thalji, N. Aiyar, E.A. Davenport, J.A. Erhardt, L.A. Kallal, D.M. Morrow, S. Senadhi, C.L. BurnsKurtis, and J.P. Marino Jr. Bioorg. Med. Chem. Lett. 20 2010 4104
19. J.E. Bird, X. Wang, P.L. Smith, F. Barbera, C. Huang, and W.A. Schumacher J. Thromb. Thrombolysis 34 2012 199
20. P.C. Wong, E.J. Crain, X. Jiang, J.S. Bostwick, C. Thibault, R. Ruel, R. Rehfuss, W.A. Schumacher, and M.L. Ogletree Circulation 2006 114 II-248, abstract 1310
21. W.A. Schumacher, J.S. Bostwick, M.L. Ogletree, A. Stewart, T.E. Steinbacher, J. Hua, L.A. Price, P.C. Wong, and R. Rhefuss J. Pharmacol. Exp. Ther. 322 2007 1
22. H. Chao, H. Turdi, T.F. Herpin, J.Y. Roberge, Y. Liu, D. Schnur, M.A. Poss, R. Rehfuss, J. Hua, Q. Wu, L.A. Price, L.M. Abell, W.A. Schumacher, J.S. Bostwick, Steinbacher, A.B. Stewart, E. T, M.R. Ogletree, C.S. Huang, M. Chang, A.M. Cacace, M.J. Arcuri, D. Celani, R.R. Wexler, and R.M. Lawrence J. Med. Chem. 56 2013 1704
23. The compounds reported herein were disclosed in: Sutton, J.; Pi, Z.; Ruel, R.; L'Heureux, A.; Thibeault, C.; Lam, P. Y. S. U.S. 2006/0173002A1.
24. 1. These included phenyl and pyridine analogs. Unpublished results.
25. Pi, Z.; Sutton, J.; Lloyd, J.; Hua, J.; Price, L.; Wu, Q.; Chang, M.; Zheng, J.; Rehfuss, R.; Huang, C. S.; Wexler, R. R.; Lam, P. Y. S. Bioorg. Med. Chem. Lett. submitted for publication.
26. T.G.M. Dhar, C. Liu, W.J. Pitts, J. Guo, S.H. Watterson, H. Gu, C.A. Fleener, K. Rouleau, N.Z. Sherbina, J.C. Barrish, D. Hollenbaugh, and E.J. Iwanowicz Bioorg. Med. Chem. Lett. 12 2002 3125
27. C.A. James, B. Poirier, C. Grisé, A. Martel, and E.H. Ruediger Tetrahedron Lett. 47 2006 511