Novel 2-(4-methylsulfonylphenyl)pyrimidine derivatives as highly potent and specific COX-2 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 5, 2008, Pages 2183-2199

  Orjales, Aurelio ^a   Mosquera, Ramón ^a   López, Beatriz ^a   Olivera, Roberto ^a   Labeaga, Luis ^a   Núñez, M Teresa ^a  

^a FAES SA   (Spain)

Author keywords

2 (4 Methylsulfonylphenyl)pyrimidines; 2 (4 Sulfamoylphenyl)pyrimidines; COX 2 inhibitors

Indexed keywords

2 (4 METHYLSULFONYLPHENYL)PYRIMIDINE; 2 (4 SULFAMOYLPHENYL)PYRIMIDINE; 4 (4 BENZYLAMINO 6 TRIFLUOROMETHYLPYRIMIDIN 2 YL)BENZENESULFONAMIDE; 4 4 [(PYRIDIN 3 METHYL)AMINO] 6 TRIFLUOROMETHYLPYRIMIDIN 2 YL]BENZENESULFONAMIDE; 4 [4 (CYCLOHEXYLMETHYLAMINO) 6 TRIFLUOROMETHYLPYRIMIDIN 2 YL]BENZENESULFONAMIDE; 4 [4 [(BENZO[B]THIOPHEN 2 YLMETHYL)AMINO] 6 TRIFLUOROMETHYLPYRIMIDIN 2 YL]BENZENESULFONAMIDE; 4 [4 [(BENZO[B]THIOPHEN 3 YLMETHYL [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]AMINE; 4 [4 [(FURAN 2 YLMETHYL)AMINO] 6 TRIFLUOROMETHYLPYRIMIDIN 2 YL]BENZENESULFONAMIDE; 4 [4 [(PYRIDIN 2 YLMETHYL)AMINO] 6 TRIFLUOROMETHYLPYRIMIDIN 2 YL]BENZENESULFONAMIDE; 4 [4 [(THIOPHEN 2 YLMETHYL)AMINO] 6 TRIFLUOROMETHYLPYRIMIDIN 2 YL]BENZENESULFONAMIDE; 4 [4 [(THIOPHEN 3 YLMETHYL)AMINO] 6 TRIFLUOROMETHYLPYRIMIDIN 2 YL]BENZENESULFONAMIDE; 4 [4 [PYRIDIN 4 YLMETHYL)AMINO] 6 TRIFLUOROMETHYLPYRIMIDIN 2 YL]BENZENESULFONAMIDE; [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL] (1 METHYL 1H PYRROL 2 YLMETHYL)AMINE; [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]PYRIDIN 2 YLMETHYLAMINE; [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]PYRIDIN 3 YLMETHYLAMINE; [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]PYRIDIN 4 YLMETHYLAMINE; [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]THIAZOL 2 YLMETHYLAMINE; [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]THIOPHEN 2 YLMETHYLAMINE; [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]THIOPHEN 3 YLMETHYLAMINE; BENZO[B]THIOPHEN 2 YLMETHYL [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]AMINE; BENZYL [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]AMINE; CYCLOHEXYLMETHYL [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]AMINE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; FURAN 2 YLMETHYL [2 (4 METHANESULFONYLPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 4 YL]AMINE; PYRIMIDINE DERIVATIVE; ROFECOXIB; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG INHIBITION; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME PURIFICATION; HUMAN; IC 50; STRUCTURE ACTIVITY RELATION;

CYCLOOXYGENASE 2 INHIBITORS; INHIBITORY CONCENTRATION 50; METHYLATION; MOLECULAR STRUCTURE; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR COMPOUNDS;

EID: 40749135792     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.11.079     Document Type: Article

References (64)

1. Fu J.Y., Masferrer J.L., Seibert K., Raz A., and Needleman P. J. Biol. Chem. 265 (1990) 16737
2. Xie W., Chipman J.G., Robertson D.L., Erikson R.L., and Simmons D.L. Proc. Natl. Acad. Sci. U.S.A. 88 (1991) 2692
3. Hla T., and Neilson K. Proc. Natl. Acad. Sci. U.S.A. 89 (1992) 7382
4. Kujubu D.A., Fletcher B.S., Varnum B.C., Lim R.W., and Herschman H.R. J. Biol. Chem. 266 (1991) 12866
5. Vane J.R. Nature 367 (1994) 215
6. Masferrer J.L., Zweifel B.S., and Manning P.T. Proc. Natl. Acad. Sci. U.S.A. 91 (1994) 3228
7. Vane J.R., Bakhle Y.S., and Botting R.M. Annu. Rev. Pharmacol. Toxicol. 38 (1998) 97
8. Garavito R.M., and De Witt D.L. Biochim. Biophys. Acta 1441 (1999) 278
9. Prasit P., Wang Z., Brideau C.-C., Chan S., 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., Lëger S., Mancini P., O'Neill G.P., Ouellet M., Percival M.D., Perrier H., Riendeau D., Rodger I., Tagari P., Thérien M., Vickers P., Wong E., Xu L.-J., Young R.N., and Zamboni R. Bioorg. Med. Chem. Lett. 9 (1999) 1773
10. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter 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., and Isakson P.C. J. Med. Chem. 40 (1997) 1347
11. 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., and Seibert K. J. Med. Chem. 43 (2000) 775
12. Ormrod D., Wellington K., and Wagstaff A.J. Drugs 62 (2002) 2059
13. Friesen R.W., Brideau C., Chan C.C., Charleson S., Deschênes D., Dubé D., Ethier D., Fortin R., Gauthier J.Y., Girard Y., Gordon R., Greig G.M., Riendeau D., Savoie C., Wang Z., and Wong E. Bioorg. Med. Chem. Lett. 8 (1998) 2777
14. Riendeau D., Percival M.D., Brideau C., Charleson S., Dubé D., Ethier D., Falgueyret J.-P., Friesen R.W., Gordon R., Greig G., Guay J., Mancini J., Ouellet M., Wong E., Xu L., Boyce S., Visco D., Girard Y., Prasit P., Zamboni R., Rodger I.W., Gresser M., Ford-Hutchinson A.W., Young R.N., and Chan C.-C. J. Pharmacol. Exp. Ther. 296 (2001) 558
15. Davies I.W., Marcoux J.-F., Corley E.G., Journet M., Cai D.-W., Palucki M., Wu J., Larsen R.D., Rossen K., Pye P.J., DiMichele L., Dormer P., and Reider P.J. J. Org. Chem. 65 (2000) 8415
16. Merck & Co. Press Release, 30 September 2004. Available from: http://www.merck.com.
17. Mukherjee D., Nissen S.E., and Topol E.J. J. Am. Med. Assoc. 286 (2001) 954
18. Mamdani M., Jurlink D.N., Lee D.S., Rochon P.A., Kopp A., Naglie G., Austin P.C., Laupacis A., and Stukel T.A. The Lancet 363 (2004) 1751
19. Scheen A.J. Rev. Med. Liege 59 (2004) 565
20. Bresalier R.S., Sandier R.S., Quan H., Bolognese J.A., Oxenius B., Horgan K., Lines C., Riddell R., Morton D., Lanas A., Konstam M.A., and Baron J.A. N. Engl. J. Med. 352 (2005) 1092
21. Solomon S.D., McMurray J.J.V., Pfeffer M.A., Wittes J., Fowler R., Finn P., Anderson W.F., Zauber A., Hawk E., and Bertagnolli M. N. Engl. J. Med. 352 (2005) 1071
22. FitzGerald G.A. N. Engl. J. Med. 351 (2004) 1709
23. Lagakos S.W. N. Eng. J. Med. 355 (2006) 113
24. Editorial. Br. Med. J. 2004, 329, 867.
25. Fitzgerald G.A. Nat. Rev. Drug Disc. 2 (2003) 879
26. Davies N.M., and Jamali F. J. Pharm. Pharmaceut. Sci. 7 (2004) 332
27. Chung S., Lim M.L., and Shin S.S. Expert Opin. Ther. Patents 15 (2005) 9
28. Dogné J.-M., Supuran C.T., and Pratico D. J. Med. Chem. 48 (2005) 2251
29. Dogné J.-M., Hanson J., Supuran C., and Pratico D. Curr. Pharm. Des. 12 (2005) 971
30. Grosser T., Fries S., and FitzGerald G.A. J. Clin. Invest. 116 (2006) 4
31. Sohn H.-Y., and Krötz F. Curr. Drug Targets 7 (2006) 1275
32. Maillard M., and Burnier M. Expert Opin. Drug Saf. 5 (2006) 83
33. Hermann M., and Ruschitzka F. Int. Med. J. 36 (2006) 308
34. Oshima M., Dinchuk J.E., Kargman S.L., Oshima H., Hancock B., Kwong E., Trzaskos J.M., Evans J.F., and Taketo M.M. Cell 87 (1996) 803
35. Vainio H. Int. J. Cancer 94 (2001) 613
36. Singh B., and Lucci A. J. Surg. Res. 108 (2002) 173
37. Kim S.I., Kwon S.M., Kim Y.S., and Hong S.J. Urology 60 (2002) 816
38. Fujita H., Koshida K., Keller E.T., Takahashi Y., Yoshimito T., Namiki M., and Mizokami A. Prostate 53 (2002) 232
39. Chu J., Lloyd F.L., Trifan O.C., Knapp B., and Rizzo M.T. Mol. Cancer Ther. 2 (2003) 1
40. Subbaramaiah K., and Dannenberg A.J. Trends Pharmacol. Sci. 24 (2003) 96
41. Pasinetti G.M. J. Neurosci. Res. 54 (1998) 1
42. Xiang Z., Ho L., Yemul S., Zhao Z., Quing W., Pompl P., Kelley K., Dang A., Qing W., Teplow D., and Pasinetti G.M. Gene Expr. 10 (2002) 271
43. Teismann P., Tieu K., Choi D.K., Wu D.C., Naini A., Hunot S., Vola M., Jackson-Lewis V., and Przedborski S. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 5473
44. Talley J.J. Progr. Med. Chem. 36 (1999) 201
45. de Leval X., Delarge J., Somers F., de Tullio P., Henrotin Y., Pirotte B., and Dogné J.-M. Curr. Med. Chem. 7 (2000) 1041
46. Carter J.S. Exp. Opin. Ther. Patents 10 (2000) 1011
47. Dannhardt G., and Kiefer W. Eur. J. Med. Chem. 36 (2001) 109
48. de Leval X., Julémont F., Delarge J., Sanna V., Pirotte B., and Dogné J.-M. Expert Opin. Ther. Patents 12 (2002) 969
49. Sondhi S.M., Singhal N., Johar M., Narayan Reddy B.S., and Lown J.W. Curr. Med. Chem. 9 (2002) 1045
50. Glaxo Group Ltd. Expert Opin. Ther. Patents 2003, 13, 1465.
51. Carter, M. C.; Naylor, A.; Payne, J. J.; Pegg, N. A. WO 03014091, 2003.
52. Weingarten, G.; Bravi, G. WO 2004018452, 2004.
53. Orjales, A.; Mosquera, R.; Labeaga, L.; Berisa, A.; Núñez, M. T.; López, B.; Diéguez, M. C. Poster to the XVIIIth International Symposium on Medicinal Chemistry. August 15-19, 2004. Copenhagen, Denmark and Malmoe, Sweden.
54. Cheng C.C. Org. Prep. Proceed. Int. 22 (1990) 643
55. Futaki N., Takahashi S., Yokoyama M., Arai I., Higuchi S., and Otomo S. Prostaglandins (1994) 55
56. Janusz J. J. Med. Chem. 41 (1998) 1112
57. Patrignani P., Panara M.R., Greco A., Fusco O., Natoli C., Iacobelli S., Cipollone F., Ganci A., Créminon C., Maclouf J., and Patrono C. J. Pharmacol. Exp. Ther. 271 (1994) 1705
58. Brideau C., Kargman S., Liu S., Sallob A.L., Ehrich E.W., Rodger I.W., and Chan C.C. Inflamm. Res. 45 (1996) 68
59. Warner T.D., Giuliano F., Vojnovic I., Bukasa A., Mitchell J.A., and Vane J.R. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 7563
60. Bennett A., and Tavares I. Expert Opin. Pharmacother. 2 (2001) 1859
61. Kurumbail R.G., Stevens A.M., Gierse J.K., McDonald J.J., Stegeman R.A., Pak J.Y., Gildehaus D., Miyashiro J.M., Penning T.D., Seibert K., Isakson P.C., and Stallings W.C. Nature 384 (1996) 644
62. Talley J.J. Prog. Med. Chem. Res. 36 (1999) 201
63. Ouellet M., Falgueyret J.-P., and Percival M.D. Biochem. J. 377 (2004) 675
64. Unpublished results.