Synthesis and selective cyclooxygenase-2 (COX-2) inhibitory activity of a series of novel bicyclic pyrazoles

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 6, 2004, Pages 1357-1366

  Ranatunge, Ramani R ^a   Garvey, David S ^a   Janero, David R ^a   Letts, L Gordon ^a   Martino, Allison M ^a   Murty, Madhavi G ^a   Richardson, Stewart K ^a   Young, Delano V ^a   Zemetseva, Irina S ^a  

^a NitroMed Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 CYCLOHEXYLIMIDAZOLIDINO[1,2 D]PYRAZOL 3 YL) 4 (METHYLSULFONYL)BENZENE; 1 (6 CYCLOHEXYL 1 METHYLIMIDAZOLIDINO[1,2 D]PYRAZOL 7 YL) 4 (METHYLSULFONYL)BENZENE; 1 [2 CYCLOHEXYL(5H,6H,7H PYRAZOLO[5,1 B] 1,3 OXAZAPERHYDROIN 3 YL)] 4 (METHYLSULFONYL)BENZENE; 1 [5 CYCLOHEXYL(2H,3H PYRAZOLO[5,1 B] 1,3 OXAZOLIDIN 6 YL) 4 (METHYLSULFONYL)]BENZENE; 1 [6 CYCLOHEXYL 2,2 DIMETHYL(3H PYRAZOLO[5,1 B] 1,3 OXAZOLIDIN 7 YL)] 4 (METHYLSULFONYL)BENZENE; 2 [6 CYCLOHEXYL 7 [4 (METHYLSULFONYL)PHENYL]IMIDAZOLIDINO[1,2 D]PYRAZOLYL]ACETIC ACID; 4 (METHYLSULFONYL) 1 [5 BENZYL(2H,3H PYRAZOLO[5,1 B] 1,3 OXAZOLIDIN 6 YL)]BENZENE; 4 (METHYLSULFONYL) 1 [5 BENZYL(2H,3H PYRAZOLO[5,1 B] 1,3 OXAZOLIN 6 YL)]BENZENE; 4 (METHYLSULFONYL) 1 [5 PHENYL(2H,3H PYRAZOLO[5,1 B] 1,3 OXAZOLIDIN 6 YL)]BENZENE; 4 ACETYL 2 CYCLOHEXYL 3 [4 (METHYLSULFONYL)PHENYL]IMIDAZOLIDINO[1,2 D]PYRAZOLE; CELECOXIB; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; PYRAZOLE DERIVATIVE; ROFECOXIB; TERT BUTYL 2 [2 CYCLOHEXYL 3 [4 (METHYLSULFONYL)PHENYL]IMIDAZOLIDINO[1,2 D]PYRAZOL 4 YL]ACETATE; UNCLASSIFIED DRUG;

ARTICLE; BLOOD; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION;

BICYCLO COMPOUNDS, HETEROCYCLIC; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; HUMANS; ISOENZYMES; MEMBRANE PROTEINS; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 1542331641     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.01.012     Document Type: Article

References (33)

1. Skoutakis V.A., Carter C.A., Micklee T.R., Smith V.H., Arkin C.R., Allissantros J., Petty D.A. Drug Intell. Clin. Pharm. 3:1988;850.
2. Lombardino G. Non Steroidal Anti-inflammatory Drugs. 1985;John Wiley & Sons, New York.
3. Dannhardt G., Kiefer W. Eur. J. Med. Chem. 36:2001;109.
4. Carter J.S. Exp. Opin. Ther. Pat. 10:2000;1011.
5. Talley J.J. Prog. Med. Chem. 36:1999;201.
6. Xie W., Chipman J.G., Robertson D.L., Erikson R.L., Simmons D.L. Proc. Natl. Acad. Sci. U.S.A. 88:1991;2692.
7. Kujubu D.A., Fletcher B.S., Varnum B.C., Lim R.W., Herschman H.R. J. Biol. Chem. 266:1991;12866.
8. Chan C.C., Boyce S., Brideau C., Charleson S., Cromlish W., Ethier D., Evans J., Ford-Hutchinson A.W., Forrest M.J., Gauthier J.Y., Gordon R., Gresser M., Guay J., Kargman S., Kennedy B., Leblanc Y., Leger S., Mancini J., O'Neill G.P., Ouellet M., Patrick D., Percival M.D., Perrier H., Prasit P., Rodger I., Tagari P., Therien M., Vickers P., Visco D., Wang Z., Webb J., Wong E., Xu L.J., Young R.N., Zamboni R., Rienddeau D. J. Pharmacol. Exp. Therap. 290:1999;551.
9. Hinz B., Brune K. J. Pharm. Exp. Therap. 300:2002;367.
10. DeWitt D.L. Mol. Pharmacol. 55:1999;625.
11. Mitchell J.A., Akarasereenont P., Thiemermann C., Flower R.J., Vane J.R. Proc. Natl. Acad. Sci. U.S.A. 90:1993;11693.
12. Penning T.D., Tally J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Doctor S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., Isakson P.C. J. Med. Chem. 40:1997;1347.
13. Prasit P., Wang Z., Brideau C., Chan C.-C., Charleson S., Cromlish W., Ethier D., Evans J.F., Ford-Hutchinson A.W., Gauthier J.Y., Gordon R., Guay J., Gresser M., Kargman S., Kennedy B., Leblanc Y., Leger S., Mancini J., O'Neill G.P., Ouellet M., Percival M.D., Perrier H., Riendeau D., Rodger I., Tagari P., Therien M., Vikers P., Wong E., Xu L.-J., Young R.N., Zamboni R., Boyce S., Rupniak N., Forrest M., Visco D., Patrick D. Bioorg. Med. Chem. Lett. 9:1999;1773.
14. Talley J.J., Brown D.L., Carter J.S., Graneto M.J., Koboldt C.M., Masferrer J.L., Perkins W.E., Rogers R.S., Shaffer A.F., Zhang Y.Y., Zweifel B.S., Seibert K. J. Med. Chem. 43:2000;775.
15. Meyer-Kirchrath J., Schror K. Curr. Med. Chem. 7:2000;1121.
16. Catella-Lawson F., Crofford L.J. Am. J. Med. 110:2001;28. S.
17. Mukherjee D., Nissen S.E., Topol E.J. JAMA. 286:2001;954.
18. Wolfe M.M., Lichtenstein D.R., Singh G. N. Engl. J. Med. 340:1999;1888.
19. de Gaetano G., Donati M.B., Cerletti C. Trends Pharm. Sci. 24:2003;245.
20. Beswick, P.; Campbell, I.; Naylor, A. PCT Appl. WO 96/31509, Oct. 10, 1996.
21. Beswick, P.; Campbell, I.; Mathews, N.; Naylor, A. PCT Appl. WO 99/12930, March 18, 1999.
22. Cossy J., Belotti D. Tetrahedron. 55:1999;5145.
23. Laufer S.A., Augustin J., Dannhardt G., Kiefer W. J. Med. Chem. 37:1994;1894.
24. Kirschning A., Ries M., Domann S., Martin W., Albrecht W., Arnold P., Laufer S. Bioorg. Med. Chem. Lett. 7:1997;903.
25. Dannhardt, G.; Steindl, L.; Lehr, M. US Patent 5,260,451, Nov. 9, 1993.
26. Isakson, P. C.; Anderson, G. D.; Gregory, S. A. US Patent 6,136,839, Oct. 24, 2000.
27. Laufer, S.; Striegel, H. G.; Dannhardt, G. US Patent 5,939,415, Aug. 17, 1999.
28. Kolasa, T.; Patel, M. V. US Patent 6,472,416 B1, Oct. 29, 2002.
29. Kolasa, T.; Patel, M. V. PCT Int. Appl., WO 01/016138, March 8, 2001.
30. Gever G. J. Am. Chem. Soc. 76:1954;1283.
31. Potekhin A.A., Barkova T.F. J. Org. Chem. USSR. 1973;1209.
32. Young J.M., Panah S., Satchawatcharaphong C., Cheung P.S. Inflamm. Res. 45:1996;246.
33. Glaser K., Sung M.L., ÓNeill K., Belfast M., Hartman D., Carlson R., Kreft A., Kubrak D., Hsiao C.L., Weichman B. Eur. J. Pharmacol. 281:1995;107.