3-Indolyl sultams as selective CRTh2 antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 11, 2010, Pages 3287-3290

  Tumey, L Nathan ^a   Robarge, Michael J ^a   Gleason, Elizabeth ^a   Song, Jianping ^a   Murphy, Steven M ^a   Ekema, George ^a   Doucette, Chris ^a   Hanniford, Doug ^a   Palmer, Marc ^a   Pawlowski, Gary ^a   Danzig, Joel ^a   Loftus, Margaret ^a   Hunady, Karen ^a   Sherf, Bruce ^a   Mays, Robert W ^a   Stricker Krongrad, Alain ^a   Brunden, Kurt R ^a   Bennani, Youssef L ^a   Harrington, John J ^a  

^a ATHERSYS INC   (United States)

Author keywords

Antagonist; CRTh2; DP; Indole; Prostaglandin D2; Ramatroban; Sultam

Indexed keywords

3 INDOLYL SULTAM ANTAGONIST; PROSTAGLANDIN D2; RAMATROBAN; SULFONAMIDE; THROMBOXANE A2 RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; EOSINOPHIL; STRUCTURE ACTIVITY RELATION;

ESTERIFICATION; HUMANS; INDOLES; RECEPTORS, IMMUNOLOGIC; RECEPTORS, PROSTAGLANDIN; SULFONAMIDES;

EID: 77953292659     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.04.046     Document Type: Article

References (22)

1. Liu M.C., Bleecker E.R., Lichtenstein L.M., Kagey-Sobotka A., Niv Y., McLemore T.L., Permutt S., Proud D., and Hubbard W.C. Am. Rev. Respir. Dis. 142 (1990) 126
2. Narumiya S., Sugimoto Y., and Ushikubi F. Physiol. Rev. 79 (1999) 1193
3. Cosmi L., Annunziato F., Maggi E., Romagnani S., and Manetti R. Int. Arch. Allergy Immunol. 125 (2001) 273
4. Nagata K., Hirai H., Tanaka K., Ogawa K., Aso T., Sugamura K., Nakamura M., and Takano S. FEBS Lett. 459 (1999) 195
5. Hirai H., Tanaka K., Yoshie O., Ogawa K., Kenmotsu K., Takamori Y., Ichimasa M., Sugamura K., Nakamura M., Takano S., and Nagata K. J. Exp. Med. 193 (2001) 255
6. Tanaka K., Hirai H., Takano S., Nakamura M., and Nagata K. Biochem. Biophys. Res. Commun. 316 (2004) 1009
7. Gervais F.G., Cruz R.P.G., Chateauneuf A., Gale S., Sawyer N., Nantel F., Metters K.M., and O'Neill G.P. J. Allergy Clin. Immunol. 108 (2001) 982
8. Ly T.W., and Bacon K.B. Expert Opin. Invest. Drugs 14 (2005) 769
9. Ulven T., and Kostenis E. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) 6 (2006) 1427
10. Robarge M.J., Bom D.C., Tumey L.N., Varga N., Gleason E., Silver D., Song J., Murphy S.M., Ekema G., Doucette C., Hanniford D., Palmer M., Pawlowski G., Danzig J., Loftus M., Hunady K., Sherf B.A., Mays R.W., Stricker-Krongrad A., Brunden K.R., Harrington J.J., and Bennani Y.L. Bioorg. Med. Chem. Lett. 15 (2005) 1749
11. Birkinshaw T.N., Teague S.J., Beech C., Bonnert R.V., Hill S., Patel A., Reakes S., Sanganee H., Dougall I.G., Phillips T.T., Salter S., Schmidt J., Arrowsmith E.C., Carrillo J.J., Bell F.M., Paine S.W., and Weaver R. Bioorg. Med. Chem. Lett. 16 (2006) 4287
12. Sandham D.A., Adcock C., Bala K., Barker L., Brown Z., Dubois G., Budd D., Cox B., Fairhurst R.A., Furegati M., Leblanc C., Manini J., Profit R., Reilly J., Stringer R., Schmidt A., Turner K.L., Watson S.J., Willis J., Williams G., and Wilson C. Bioorg. Med. Chem. Lett. 19 (2009) 4794
13. Crosignani S., Page P., Missotten M., Colovray V., Cleva C., Arrighi J.-F., Atherall J., Macritchie J., Martin T., Humbert Y., Gaudet M., Pupowicz D., Maio M., Pittet P.-A., Golzio L., Giachetti C., Rocha C., Bernardinelli G., Filinchuk Y., Scheer A., Schwarz M.K., and Chollet A. J. Med. Chem. 51 (2008) 2227
14. Hoegberg T., Ulven T., Receveur J.-M., Grimstrup M., Rist O., Frimurer T.M., Gerlach L.-O., Mathiesen J.M., Kostenis E., and Uller L. J. Med. Chem. 49 (2006) 6638
15. Shichijo M., Arimura A., Hirano Y., Yasui K., Suzuki N., Deguchi M., and Abraham W.M. Clin. Exp. Allergy 39 (2009) 1404
16. Stearns B.A., Baccei C., Bain G., Broadhead A., Clark R.C., Coate H., Evans J.F., Fagan P., Hutchinson J.H., King C., Lee C., Lorrain D.S., Prasit P., Prodanovich P., Santini A., Scott J.M., Stock N.S., and Truong Y.P. Bioorg. Med. Chem. Lett. 19 (2009) 4647
17. Sugimoto H., Shichijo M., Iino T., Manabe Y., Watanabe A., Shimazaki M., Gantner F., and Bacon K.B. J. Pharmacol. Exp. Ther. 305 (2003) 347
18. Iwahashi, M.; Naganawa, A.; Nishiyama, T.; Nagase, T.; Kobayashi, K.; Nambu, F.; (Ono Pharmaceutical Co., Ltd., Japan), WO2004078719, 2004.
19. Davis F.A., Towson J.C., Vashi D.B., ThimmaReddy R., McCauley Jr. J.P., Harakal M.E., and Gosciniak D.J. J. Org. Chem. 55 (1990) 1254
20. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727
21. All compound were made as racemates. Attempts to separate the two enantiomers by chiral HPLC were unsuccessful.
22. McKenniff M.G., Norman P., Cuthbert N.J., and Gardiner P.J. Br. J. Pharmacol. 104 (1991) 585