Diaminocyclobutenediones as potent and orally bioavailable CXCR2 receptor antagonists: SAR in the phenolic amide region

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 15, 2009, Pages 4446-4449

  Aki, Cynthia ^a   Chao, Jianping ^a   Ferreira, Johan A ^a   Dwyer, Michael P ^a   Yu, Younong ^a   Chao, Jianhua ^a   Merritt, Robert J ^b   Lai, Gaifa ^b   Wu, Minglang ^b   Hipkin, R William ^a   Fan, Xuedong ^a   Gonsiorek, Waldemar ^a   Fosseta, James ^a   Rindgen, Diane ^a   Fine, Jay ^a   Lundell, Daniel ^a   Taveras, Arthur G ^a   Biju, Purakkattle ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b PHARMACOPEIA INC   (United States)

Author keywords

Amide modification; CXCR2 receptor antagonist; Diaminocyclobutenediones

Indexed keywords

3,4 DIAMINOCYCLOBUTENEDIONE DERIVATIVE; AMIDE; CHEMOKINE RECEPTOR ANTAGONIST; CHEMOKINE RECEPTOR CXCR1; CHEMOKINE RECEPTOR CXCR1 ANTAGONIST; CHEMOKINE RECEPTOR CXCR2; CHEMOKINE RECEPTOR CXCR2 ANTAGONIST; PHENOL; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; AMIDES; ANIMALS; AREA UNDER CURVE; CHEMISTRY, PHARMACEUTICAL; CYCLOBUTANES; DIAMINES; DRUG DESIGN; HUMANS; INFLAMMATION; KINETICS; MODELS, CHEMICAL; PHENOL; RATS; RECEPTORS, INTERLEUKIN-8A; RECEPTORS, INTERLEUKIN-8B; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67649909861     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.05.049     Document Type: Article

References (37)

1. Leung B.P., Culshaw S., Gracie J.A., Hunter D., Canetti C.A., Campbell C., Cunha F., Liew F.Y., and McInnes I.B. J. Immunol. 167 (2001) 2879
2. Lisig noli G., Toneguzzi S., Pozzi C., Piacentini A., Riccio M., Ferruzzi A., Gualtieri G., and Facchini A. J. Rhe. 26 (1999) 791
3. Laan M., Cui Z.H., Hoshino H., Lotvall J., Sjostrand M., Gruenert D.C., Skoogh B.E., and Linden A. J. Immunol. 162 (1999) 2347
4. Smart S.J., and Casala T.B. Am. J. Physiol. 266 (1994) L238
5. Seino Y., Ikeda U., Sekiguchi H., Morita M., Konishi K., Kasahara T., and Shimada K. Cytokine 7 (1995) 301
6. Adams D.H., and Lioyd A.R. Lancet 349 (1997) 490
7. Saunders J., and Tarby C.M. Drug Discovery Today 4 (1999) 80
8. Gura T. Science 272 (1996) 954
9. Skelton N.J., Quan C., Reilly D., and Lowman H. Structure 7 (1999) 157 and references cited therein
10. Rahman A., Harvey K., and Siddiqui R. Curr. Pharm. Design 5 (1999) 241 and references cited therein
11. Traves S.L., Smith S.J., Barnes P.J., and Donnelly L.E. J. Leukocyte Biol. 76 (2004) 1
12. Luster A.D.N. Eng. J. Med. 338 (1998) 436
13. Barnes P.J., Shapiro S.D., and Pauwels R.A. Eur. Respir. J. 4 (2003) 672
14. Donnely L.E., and Rogers D.F. Drugs 63 (2003) 1973
15. Feldmann M., Brennan F.M., and Maini R.N. Annu. Rev. Immunol. 14 (1996) 397
16. Kucharzik T., Walsh S.V., Chen J., Parkos C.A., and Nusrat A. Am. J. Pathol. 159 (2001) 2001
17. Cummings C.J., Martin T.R., Frevert C.W., Quan J.M., Wong V.A., Mongovin S.M., Hagen T.R., Steinberg K.P., and Goodman R.B. J. Immunol. 162 (1999) 2341
18. Glinski W., and Jablonska S. J. Invest. Dermatol. 82 (1984) 386
19. Keatings V.M., Collins P.D., Scott D.M., and Barnes P.J. Am. J. Respir. Crit. Care Med. 153 (1996) 530
20. Wu L., Ruffing N., Shi X., Newman W., Soler D., Mackay C., and Quin S. J. Biol. Chem. 271 (1996) 31202
21. Jones S.A., Dewald B., Lewis I.C., and Baggiolini M. J. Biol. Chem. 272 (1997) 16166
22. Shibata F., Konishi K., and Nakagawa H. Biol. Pharm. Bull. 25 (2002) 1217
23. Chapman R.W., Phillips J.E., Hipkin R.W., Curran A.K., Lundell D., and Fine J.S. Pharmacol. Ther. 121 (2009) 55
24. Nie H., Widdowson K.L., Palovich M.R., Fu W., Elliot J.D., Bryan D.L., Burman M., Scmidt D.B., Foley J.F., Sarau H.M., and Busch-Petersen J.J. Bioorg. Med. Chem. Lett. 16 (2006) 5513
25. Busch-Petersen, J.; Jin, Q.; McCleland, B. W.; Nie, H.; Palovich, M. R.; Davis, R. S.; Fu, W.; Elliot, J. D.; Burman, M.; Foley, J. J.; Schmidt, D. B.; Podolin, P.; Bolognese, B. J.; Underwood, D. C.; Osborn, R. R.; Dehaas, C. J.; Salmon, M.; Carpenter, D. C.; Kilian, D. J.; Sarau, H. M.; Widdowson, K. L. Abstracts of Papers, 228th National Meeting of the American Chemical Society, Philadelphia, PA, United States, Aug 22-26, 2004; American Chemical Society: Washington, DC, 2004; MEDI-192.
26. Wang Y., Busch-Petersen J., Wang F., Ma L., Fu W., Kerns J.K., Jin J., Palovich M.R., Shen J.-K., Burman M., Foley J.J., Scmidt D.B., Hunsberger G.E., Sarau H.M., and Widdowson K.L. Bioorg. Med. Chem. Lett. 17 (2007) 3864
27. Winters M.P., Crysler C., Subasinghe N., Ryan D., Leong L., Zhao S., Donatelli R., Yurkow E., Mazzulla M., Boczon L., Manthey C.L., Molloy C., Raymond H., Murray L., McAlonan L., and Tomczuk B. Bioorg. Med. Chem. Lett. 18 (2008) 1926
28. Merritt J.R., Rokosz L.L., Nelson K.H., Kaiser B., Wang W., Stauffer T.M., Ozgur L.E., Schilling A., Li G., Baldwin J., Taveras A.G., Dwyer M.P., and Chao J. Bioorg. Med. Chem. Lett. 16 (2006) 4107
29. Dwyer M.P., Yu Y., Chao J.P., Aki C., Chao J.H., Biju P., Girijavallabhan V., Rindgen D., Bond R., Mayer-Ezel R., Jakway J., Hipkin R.W., Fossetta J., Gonsiorek W., Bian H., Fan X., Terminelli C., Fine J., Lundell D., Merritt J.R., Rokosz L.L., Kaiser B., Li G., Wang W., Stauffer T.M., Ozgur L.E., and Taveras A.G. J. Med. Chem. 49 (2006) 7603
30. Chao J.H., Taveras A.G., Chao J.P., Aki C., Dwyer M.P., Yu Y., Biju P., Rindgen D., Jakway J., Hipkin W., Fossetta J., Fan X., Lundell D., Fine J., Minnicozzi M., Phillips J., and Merritt J.R. Bioorg. Med. Chem. Lett. 17 (2007) 3778 and references cited therein
31. Yu Y., Dwyer M.P., Chao J., Aki C., Chao J., Purakkattle B., Rindgen D., Bond R., Mayer-Ezel R., Jakway J., Qiu H., Hipkin R.W., Fossetta J., Gonsiorek W., Bian H., Fan X., Terminelli C., Fine J., Lundell D., Merritt J.R., He Z., Lai G., Wu W., and Taveras A.G.J. Bioorg. Med. Chem. Lett. 18 (2008) 1318
32. Biju P., Taveras A.G., Dwyer M.P., Yu Y., Chao J.R., Hipkin R.W., Rindgen D., Fan X., Fine J., and Lundell D. Bioorg. Med. Chem. Lett. 19 (2009) 1431
33. Biju P., Taveras A., Yu Y., Zheng Z., Chao J., Rindgen D., Jakway J., Hipkin R.W., Fossetta J., Fan X., Fine J., Qiu H., Merritt J.R., and Baldwin J.J. Bioorg. Med. Chem. Lett. 18 (2008) 228
34. Biju P., Taveras A.G., Yu Y., Zheng Z., Hipkin R.W., Fossetta J., Fan X., Fine J., and Lundell D. Bioorg. Med. Chem. Lett. 19 (2009) 1434
35. For the detailed preparation procedures of the left side amines, refer to the patents WO 2002076926, WO 2002076926, WO 2005068460.
36. 50) values and we have seen good correlation with cell based assays. We have not done any competition binding experiments on any of the compounds presented in this paper, except compound 6.
37. Gonsiorek W., Fan X., Hesk D., Fossetta J., Qiu H., Jakway J., Billah M., Dwyer M., Chao J., Deno G., Taveras A., Lundell D.J., and Hipkin R.W. J. Pharmcol. Exp. Ther. 322 (2007) 477