Synthesis of new 2-arylamino-6-trifluoromethylpyridine-3-carboxylic acid derivatives and investigation of their analgesic activity

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 15, 2004, Pages 4169-4177

  Cocco, Maria T ^a   Congiu, Cenzo ^a   Onnis, Valentina ^a   Morelli, Micaela ^a   Felipo, Vicente ^b   Cauli, Omar ^a,b  

^a UNIVERSITY OF CAGLIARI   (Italy)

^b UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 [(2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBONITRILE; 2 [(2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLIC ACID; 2 [(2,6 DIMETHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBONITRILE; 2 [(2,6 DIMETHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLIC ACID; 2 [(3 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBONITRILE; 2 [(3 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXAMIDE; 2 [(3 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLIC ACID; 2 [(3 TRIFLUOROMETHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBONITRILE; 2 [(3 TRIFLUOROMETHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLIC ACID; 2 [(4 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBONITRILE; 2 [(4 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLIC ACID; 2 [(4 TRIFLUOROMETHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBONITRILE; 2 [(4 TRIFLUOROMETHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLIC ACID; 2 [(5 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBONITRILE; 2 [(5 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXAMIDE; 2 [(5 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLIC ACID; 2 [(6 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBONITRILE; 2 [(6 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLIC ACID; ACETYLSALICYLIC ACID; CARBOXYLIC ACID DERIVATIVE; ETHYL 2 [(5 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLATE; ETHYL 2 [(6 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLATE; FLUFENAMIC ACID; IBUPROFEN; METHYL 2 [(5 CHLORO 2 METHYLPHENYL)AMINO] 6 TRIFLUOROMETHYLPYRIDINE 3 CARBOXYLATE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; IN VIVO STUDY; NONHUMAN; RAT; ULCEROGENESIS; WRITHING TEST;

ANALGESICS; ANIMALS; CARBOXYLIC ACIDS; DRUG EVALUATION, PRECLINICAL; MALE; MOLECULAR STRUCTURE; MOTOR ACTIVITY; NICOTINIC ACIDS; PAIN MEASUREMENT; PYRIDINES; RATS; RATS, SPRAGUE-DAWLEY;

EID: 3042795597     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.05.025     Document Type: Article

References (45)

1. Brooks P.M., Day R.O. N. Engl. J. Med. 324:1991;1716-1725
2. Wallace J.L. Gastroenterology. 112:1997;1000-1016
3. Laine L. Gastroenterology. 120:2001;594-606
4. Vane J.R. Nature. 231:1971;232-235
5. Malmberg A.B., Yaksh T.L. J. Pharmacol. Exp. Ther. 263:1992;136-146
6. Vane J.R., Bakhle Y.S., Botting R.M. Annu. Rev. Pharmacol. Toxicol. 38:1998;97-120
7. Tilley S.L., Coffman T.M., Koller B.H. J. Clin. Invest. 108:2001;15-23
8. Xie W.L., Chipman J.G., Robertson D.L., Erikson R.L., Simmons D.L. Proc. Natl. Acad. Sci. U.S.A. 88:1991;2692-2696
9. Dequeker J., Degner F. Inflamm. Res. 50(Suppl. 1):2001;S3-S4
10. Dubois R.N., Abramson S.B., Crofford L., Gupta R.A., Simon L.S., Van De Putte L.B., Lipsky P.E. FASEB J. 12:1998;1063-1073
11. Jouzeau J.Y., Terlain B., Abid A., Nedelec E., Netter P. Drugs. 53:1997;563-582
12. O'Banion M.K. Crit. Rev. Neurobiol. 13:1999;45-82
13. Siegle I., Klein T., Backman J.T., Saal J.G., Nusing R.M., Fritz P. Arthritis Rheum. 41:1998;122-129
14. Fitzgerald G.A., Patrono C. N. Engl. J. Med. 345:2001;433-442
15. Wallace J.L. Am. J. Med. 107(Suppl 6A):1999;S7-S11
16. Sondhi S.M., Singhal N., Johar M., Reddy B.S.N., Lown J.W. Curr. Med. Chem. 9:2002;1045-1074
17. Effland, R. C.; Klein, J. T. Eur. Pat. Appl. EP 453, 222, 1991
18. Boschelli D.H., Connor D.T., Bornemeier D.A., Dyer R.D., Kennedy J.A., Kuipers P.J., Okonkwo G.C., Schrier D.J., Wright C.D. J. Med. Chem. 36:1993;1802-1810
19. Kumar A., Jaju B.P., Sinha J.N. Ind. J. Pharm. Sci. 1:1990;257-260
20. Goel B., Ram T., Tyagi R., Bansal E., Kumar A., Mukherjee D., Sinha J.N. Eur. J. Med. Chem. 34:1999;265-269
21. Sharma S., Srivastava V.K., Kumar A. Eur. J. Med. Chem. 37:2002;689-697
22. Kermak W.O., Weatherhead A.P. J. Chem. Soc. 1942;726
23. Stampa, A. Ger. Offen. 2, 409, 260; Chem. Abstr. 1975, 82, 156112s
24. Jaouhari R., Quinn P. Heterocycles. 38:1994;2243-2246
25. Sherlock, M. H. US Patent, US 3, 839, 344; Chem. Abstr. 1975, 82, 16705n
26. Nantka-Namirski P., Kaczmarek L. Acta Polym. Pharm. 35:1978;393-402
27. Nantka-Namirski, P.; Kaczmarek, L. Chem. Abstr. 1979, 90, 203821z
28. Nantka-Namirski P., Kaczmarek L. Acta. Polym. Pharm. 35:1978;509-513
29. Nantka-Namirski, P.; Kaczmarek, L. Chem. Abstr. 1979, 91, 123609s
30. Reisch J., Mester I., El-Moghazy Aly S.M. J. Chem. Soc., Perkin. Trans. 1. 1983;219-223
31. Monge A., Narro S., Martinez-Crespo F.J., Lopez de Cerain A., Hamilton E., Barker A.J. Eur. J. Med. Chem. 29:1994;441-445
32. Ting P.C., Kaminski J.J., Sherlock M.H., Tom W.C., Lee J.F., Bryant R.W., Watnick A.S., McPhail A.T. J. Med. Chem. 33:1990;2697-2706
33. Laboratories U.P.S.A., Neth. Appl. 6, 414, 717; Chem. Abstr. 1966, 64, 712h
34. Coppo F.T., Fawzi M.M. J. Heterocycl. Chem. 35:1998;499-501
35. Differding E., Frick W., Lang R.W., Martin P., Schimt C., Veenstra S., Greute H. Bull. Soc. Chim. Belg. 99:1990;647
36. Cocco M.T., Congiu C., Onnis V. J. Heterocycl. Chem. 32:1995;543-545
37. Koster R., Anderson M., De Beer E.J. Fed. Proc. 18:1959;412
38. Collier H.O., Dinneen L.C., Johnson C.A., Schneider C. Br. J. Pharmacol. 32:1968;295-310
39. Ikeda Y., Ueno A., Naraba H., Oh-ishi S. Life Sci. 69:2001;2911-2919
40. McCormack K. Drugs. 47(Suppl 5):1994;28-47
41. Pong S.F., Demuth S.M., Kinney C.M., Deegan P. Arch. Int. Pharmacodyn. Ther. 273:1985;212-220
42. Dubinsky B., Gebre-Mariam S., Capetola R.J., Rosenthale M.E. Agents Actions. 20:1987;50-60
43. Verna M., Sinha J.N., Guijrati V.R. Pharmacol. Res. Commun. 13:1981;967-969
44. Suleyman H., Akcay F., Altinkaynak K. Pharmacol. Res. 45:2002;155-158
45. Cocco M.T., Congiu C., Onnis V., Morelli M., Cauli O. Eur. J. Med. Chem. 38:2003;513-518