Discovery of a series of acrylic acids and their derivatives as chemical leads for selective EP3 receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 18, 2009, Pages 6567-6582

  Asada, Masaki ^a   Obitsu, Tetsuo ^a   Nagase, Toshihiko ^a   Sugimoto, Isamu ^a   Yamaura, Yoshiyuki ^a   Sato, Kazutoyo ^a   Narita, Masami ^a   Ohuchida, Shuichi ^a   Nakai, Hisao ^a   Toda, Masaaki ^a  

^a ONO PHARMACEUTICAL CO   (Japan)

Author keywords

Antagonist; EP3 receptor; Prostaglandin; Pyrazole

Indexed keywords

3 [2 [2 (2 NAPHTHYL)ETHOXY] 4 (1H PYRAZOL 1 YLMETHYL)PHENYL]ACRYLIC ACID; 3 [2 [2 (2 NAPHTHYL)ETHOXY] 4 (1H PYRAZOL 1 YLMETHYL)PHENYL]PROPANOIC ACID; ACRYLIC ACID DERIVATIVE; PROSTAGLANDIN E RECEPTOR; PROSTAGLANDIN RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DRUG ACTIVITY; DRUG RECEPTOR BINDING; NONHUMAN; RECEPTOR AFFINITY; RECEPTOR BLOCKING;

ACRYLATES; ANIMALS; BINDING, COMPETITIVE; CHO CELLS; CRICETINAE; CRICETULUS; HUMANS; MICE; MICROSOMES, LIVER; MOLECULAR STRUCTURE; PROTEIN BINDING; PYRAZOLES; RATS; RECEPTORS, PROSTAGLANDIN E; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 69249135126     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.08.007     Document Type: Article

References (24)

1. Coleman R.A., Smith W.L., and Narumiya S. Pharmacol. Rev. 46 (1994) 205
2. Minami T., Nakano H., Kobayashi T., Sugimoto Y., Ushikubi F., Ichikawa A., Narumiya S., and Ito S. Br. J. Pharmacol. 133 (2001) 438
3. Ushikubi F., Segi E., Sugimoto Y., Murata T., Matsuoka T., Kobayashi T., Hizaki H., Tuboi K., Katsuyama M., Ichikawa A., Tanaka T., Yoshida N., and Narumiya S. Nature 395 (1998) 281
4. Senior J., Marshall K., Sangha R., Baxter G.S., and Clayton J.K. Br. J. Pharmacol. 102 (1991) 747
5. Goureau O., Tanfin Z., Marc S., and Harbon S. Am. J. Physiol. 263 (1992) C257
6. Chen M.C.Y., Amirian D.A., Toomey M., Sanders M.J., and Soll A.H. Gastroenterology 94 (1988) 1121
7. Ma H., Hara A., Xiao C.Y., Okada Y., Takahata O., Nakaya K., Sugimoto Y., Ichikawa A., Narumiya S., and Ushikubi F. Circulation 104 (2001) 1176
8. Gross S., Tilly P., Hentsch D., Vonesch J.L., and Fabre J.E. J. Exp. Med. 204 (2007) 311
9. Juteau H., Gareau Y., Labelle M., Lamontagne S., Tremblay N., Carriere M.C., Sawyer N., Denis D., and Metters K.M. Bioorg. Med. Chem. Lett. 11 (2001) 747
10. Juteau H., Gareau Y., Labelle M., Sturino C.F., Sawyer N., Tremblay N., Lamontagne S., Carriere M.C., Denis D., and Metters K.M. Bioorg. Med. Chem. 9 (2001) 1977
11. Gallant M., Carriere M.C., Chateauneuf A., Denis D., Gareau Y., Godbout C., Greig G., Juteau H., Lachance N., Lacombe P., Lamontagne S., Metters K.M., Rochette C., Ruel D., Slipetz D., Sawyer N., Tremblay N., and Labelle M. Bioorg. Med. Chem. Lett. 12 (2002) 2583
12. Gallant M., Belley M., Carriere M.C., Chateauneuf A., Denis D., Lachance N., Lamontagne S., Metters K.M., Sawyer N., Slipetz D., Truchon J.F., and Labelle M. Bioorg. Med. Chem. Lett. 13 (2003) 3813
13. Belley M., Gallant M., Roy B., Houde K., Lachance N., Labelle M., Trimble L.A., Chauret N., Li C., Sawyer N., Tremblay N., Lamontagne S., Carriere M.C., Denis D., Greig G.M., Slipetz D., Metters K.M., Gordon R., Chan C.C., and Zamboni R.J. Bioorg. Med. Chem. Lett. 15 (2005) 527
14. Belley M., Chan C.C., Gareau Y., Gallant M., Juteau H., Houde K., Lachance N., Labelle M., Sawyer N., Tremblay N., Lamontagne S., Carriere M.C., Denis D., Greig G.M., Slipetz D., Gordon R., Chauret N., Li C., Zamboni R.J., and Metters K.M. Bioorg. Med. Chem. Lett. 16 (2006) 5639
15. Zhou N., Zeller W., Krohn M., Anderson H., Zhang J., Onua E., Kiselyov A.S., Ramirez J., Halldorsdottir G., Andresson T., Gurney M.E., and Singh J. Bioorg. Med. Chem. Lett. 19 (2009) 123
16. O'Connell M., Zeller W., Burgeson J., Mishra R.K., Ramirez J., Kiselyov A.S., Andresson T., Gurney M.E., and Singh J. Bioorg. Med. Chem. Lett. 19 (2009) 778
17. Zhou N., Zeller W., Zhang J., Onua E., Kiselyov A.S., Ramirez J., Palsdottir G., Halldorsdottir G., Andresson T., Gurney M.E., and Singh J. Bioorg. Med. Chem. Lett. 19 (2009) 1528
18. Zegar S., Tokar C., Enache L.A., Rajagopol V., Zeller W., O'Connell M., Singh J., Muellner F.W., and Zembower D.E. Org. Process Res. Dev. 11 (2007) 747
19. Singh J., Zeller W., Zhou N., Hategen G., Mishra R., Polozov A., Yu P., Onua E., Zhang J., Zembower D., Kiselyov A., Ramirez J.L., Sigthorsson G., Bjornsson J.M., Thorsteinsdottir M., Andresson T., Bjarnadottir M., Magnusson O., Fabre J.E., Stefansson K., and Gurney M.E. ACS Chem. Biol. 4 (2009) 115
20. Ohuchida, S.; Toda, M.; Miyamoto, T. U.S. Patent 5,055,598, 1991.
21. Mendelson W.L., Holmes M., and Dougherty J. Synth. Commun. 26 (1996) 593
22. Sweeney, Z. K. PCT Publication No. WO2008/009613, 2008.
23. Shigeyasu M., Kuwahara M., Sisido M., and Ishikawa T. Chem. Lett. 30 (2001) 634
24. Knochel P., Yeh M.C., Berk S.C., and Talbert J. J. Org. Chem. 53 (1988) 2392