A new 4-(2-methylquinolin-4-ylmethyl)phenyl P1′ group for the β-amino hydroxamic acid derived TACE inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 7, 2007, Pages 1865-1870

  Chen, Xiao Tao ^a   Ghavimi, Bahman ^a   Corbett, Ronald L ^a   Xue, Chu Biao ^a   Liu, Rui Qin ^a   Covington, Maryanne B ^a   Qian, Mingxin ^a   Vaddi, Krishna G ^a   Christ, David D ^a   Hartman, Karl D ^a   Ribadeneira, Maria D ^a   Trzaskos, James M ^a   Newton, Robert C ^a   Decicco, Carl P ^a   Duan, James J W ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Amino hydroxamic acid; Anti inflammatory agent; Matrix metalloproteinase inhibitor; TACE inhibitor

Indexed keywords

HYDROXAMIC ACID DERIVATIVE; QUINOLINE DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA CONVERTING ENZYME INHIBITOR;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ADAM PROTEINS; ANIMALS; CHEMISTRY, PHARMACEUTICAL; DOGS; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; HYDROXAMIC ACIDS; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; MOLECULAR CONFORMATION; OXYGEN; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE;

SUS;

EID: 33847636782     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.01.041     Document Type: Article

References (37)

1. Vassalli P. Annu. Rev. Immunol. 10 (1992) 411
2. Szatmary Z. Neoplasma 46 (1999) 257
3. William R.O., Feldmann M., and Maini R.N. Proc. Natl. Acad. Sci. U.S.A. 89 (1992) 9784
4. Murch S.H., and Braeger C.P. Gut 34 (1993) 1705
5. Ettehadi P., Greaves M.W., Wallach D., Aderka D., and Camp R.D. Clin. Exp. Immunol. 96 (1994) 146
6. Dinarello C.A. J. Infect. Dis. 163 (1991) 1177
7. Cannon J.G., Tompkins R.G., Gelfand J.A., Michie H.R., Stanford G.G., van der Meer J.W., Endres S., Lonnemann G., Corsetti J., and Chernow B. J. Infect. Dis. 161 (1990) 79
8. Moreland L.W., Baumgartner S.W., Schiff M.H., Tindall E.A., Fleischmann R.M., Weaver A.L., Ettlinger R.E., Cohen S., Koopman W.J., Mohler K., Widmer M.B., and Blosch C.M. N. Engl. J. Med. 337 (1997) 141
9. Lipsky P.E., van der Heijde D.M., St. Clair E.W., Furst D.E., Breedveld F.C., Kalden J.R., Smolen J.S., Weisman M., Emery P., Feldmann M., Harriman G.R., and Maini R.N. N. Engl. J. Med. 343 (2000) 1594
10. Leonardi C.L., Powers J.L., Matheson R.T., Goffe B.S., Zitnik R., Wang A., and Gottlieb A.B. N. Engl. J. Med. 349 (2003) 2014
11. Black R.A., Rauch C.T., Kozlosky C.J., Peschon J.J., Slack J.L., Wolfson M.F., Castner B.J., Stocking K.L., Reddy P., Srinivasan S., Nelson N., Boiani N., Schooley K.A., Gerhart M., Davis R., Fitzner J.N., Johnson R.S., Paxton R.J., March C.J., and Cerretti D.P. Nature 385 (1997) 729
12. Moss M.L., Jin C.S.-L., Milla M.E., Burkhart W., Carter H.L., Chen W.-J., Clay W.C., Didsbury J.R., Hassler D., Hoffman C.R., Kost T.A., Lambert M.H., Leesnitzer M.A., McCauley P., McGeehan G., Mitchell J., Moyer M., Pahel G., Rocque W., Overton L.K., Schoenen F., Seaton T., Su J.-L., Warner J., Willard D., and Becherer J.D. Nature 385 (1997) 733
13. Wasserman Z.R., Duan J.J., Voss M.E., Xue C.-B., Cherney R.J., Nelson D.J., Hardman K.D., and Decicco C.P. Chem. Biol. 10 (2003) 215 and references cited therein
14. Mohler K.M., Sleath P.R., Fitzner J.N., Cerretti D.P., Alderson M., Kerwar S.S., Torrance D.S., Otten-Evans C., Greenstreet T., Weerawarna K., Kronheim S.R., Petersen M., Gerhart M., Kozlosky C.J., March C.J., and Black R.A. Nature 370 (1994) 218
15. Xue C.-B., He X., Corbett R.L., Roderick J., Wasserman Z., Liu R.-Q., Jaffee B.D., Covington M.B., Qian M., Trzaskos J.M., Newton R.C., Magolda R.L., Wexler R.R., and Decicco C.P. J. Med. Chem. 44 (2001) 3351
16. Rabinowitz M.H., Andrews R.C., Becherer J.D., Bickett D.M., Bubacz D.G., Conway J.G., Cowan D.J., Gaul M., Glennon K., Lambert M.H., Leesnitzer M.A., McDougald D.L., Moss M.L., Musso D.L., and Rizzolio M.C. J. Med. Chem. 44 (2001) 4252
17. Holms J., Mast K., Marcotte P., Elmore I., Li J., Pease L., Glaser K., Morgan D., Michaelides M., and Davidsen S. Bioorg. Med. Chem. Lett. 11 (2001) 2907
18. Chen J.M., Jin G., Sung A., and Levin J.I. Bioorg. Med. Chem. Lett. 12 (2002) 1195
19. Cherney R.J., Duan J.J.-W., Voss M.E., Chen L., Wang L., Meyer D.T., Wasserman Z.R., Hardman K.D., Liu R.-Q., Covington M.B., Qian M., Mandlekar S., Christ D.D., Trzaskos J.M., Newton R.C., Magolda R.L., Wexler R.R., and Decicco C.P. J. Med. Chem. 46 (2003) 1811
20. Wojtowicz-Praga S., Torri J., Johnson M., Steen V., Marshall J., Ness E., Dickson R., Sale M., Rasmussen H.S., Chiodo T.A., and Hawkins M.J. J. Clin. Oncol. 16 (1998) 2150
21. Levitt N.C., Eskens F.A., O'Byrne K.J., Propper D.J., Denis L.J., Owen S.J., Choi L., Foekens J.A., Wilner S., Wood J.M., Nakajima M., Talbot D.C., Steward W.P., Harris A.L., and Verweij. J. Clin. Cancer Res. 7 (2001) 1912
22. Xue C.-B., He X., Roderick J., Corbett R.L., Duan J.J.-W., Liu R.-Q., Covington M.B., Qian M., Ribadeneira M.D., Vaddi K., Christ D.D., Newton R.C., Trzaskos J.M., Magolda R.L., Wexler R.R., and Decicco C.P. Bioorg. Med. Chem. Lett. 13 (2003) 4299
23. Xue C.-B., He X., Roderick J., Corbett R.L., Duan J.J.-W., Liu R.-Q., Covington M.B., Newton R.C., Trzaskos J.M., Magolda R.L., Wexler R.R., and Decicco C.P. Bioorg. Med. Chem. Lett. 13 (2003) 4293
24. Levin J.I., Chen J.M., Du M.T., Nelson F.C., Killar L.M., Skala S., Sung A., Jin G., Cowling R., Barone D., March C.J., Mohler K.H., Black R.A., and Skotnicki J.S. Bioorg. Med. Chem. Lett. 12 (2002) 1199
25. Letavic M.A., Axt M.Z., Barberia J.T., Carty T.J., Danley D.E., Geoghegan K.F., Halim N.S., Hoth L.R., Kamath A.V., Laird E.R., Lopresti-Morrow L.L., McClure K.F., Mitchell P.G., Natarajan V., Noe M.C., Pandit J., Reeves L., Schulte G.K., Snow S.L., Sweeney F.J., Tan D.H., and Yu C.H. Bioorg. Med. Chem. Lett. 12 (2002) 1387
26. Duan J.J.W., Chen L., Wasserman Z.R., Lu Z., Liu R.-Q., Covington M.B., Qian M., Hardman K.D., Magolda R.L., Newton R.C., Christ D.D., Wexler R.R., and Decicco C.P. J. Med. Chem. 45 (2002) 4954
27. Duan J.J.-W., Lu Z., Xue C.-B., He X., Seng J.L., Roderick J.J., Wasserman Z.R., Liu R.-Q., Covington M.B., Magolda R.L., Newton R.C., Trzaskos J.M., and Decicco C.P. Bioorg. Med. Chem. Lett. 13 (2003) 2035
28. Duan, J. J.-W.; Ott, G. R.; King, B.W.; Maduskuie, T. P.; Xue, C.-B.; Chen, L.; Lu, Z.; Gilmore, J. L.; Asakawa, N.; Mercer, S. E.; Xu, M.; Harris, C. M.; Wasserman, Z. R.; Liu, R.-Q.; Covington, M. B.; Qian, M.; Vaddi, K. G.; Christ, D. D.; Hardman, K. D.; Ribadeneira, M. D.; Newton, R. C.; Trzaskos, J. M.; Decicco, C. P. Abstracts of papers, 226th ACS National Meeting, New York, NY, USA, 2003, September 7-11, MEDI-201.
29. Ott, G. R.; Lu, Z.; Asakawa, N.; Covington, M. B.; Qian, M.; Liu, R.-Q.; Newton, R. C.; Christ, D. D.; Decicco, C. P.; Duan, J. J.-W. Abstracts of Papers, 228th ACS National Meeting, Philadelphia, PA, USA, 2004, August 22-26, MEDI-324.
30. Gilmore J.L., King B.W., Harris C., Maduskuie T.P., Mercer S.E., Liu R.-Q., Covington M.B., Qian M., Ribadeneria M.D., Vaddi K.G., Trzaskos J.M., Newton R.C., Decicco C.P., and Duan J.J.-W. Bioorg. Med. Chem. Lett. 16 (2006) 2699
31. Ott, G. R.; Asakawa, N.; Lu, Z.; Anand, R.; Liu, R.; Covington, M.; Vaddi, K.; Qian, M.; Duan, J. J.-W. Abstracts of Papers, 230th ACS National Meeting, Washington, DC, USA, 2005, August 28-September 1, MEDI-289.
32. Lu, Z.; Anand, R.; Liu, R.; Covington, M.; Vaddi, K.; Qian, M.; Duan, J. J.-W.; Ott, G. R. Abstracts of Papers, 230th ACS National Meeting, Washington, DC, USA, 2005, August 28-September 1, MEDI-288.
33. Xue C.-B., He X., Roderick J., Degrado W.F., Cherney R.J., Hardman K.D., Nelson D.J., Copeland R.A., Jaffee B.D., and Decicco C.P. J. Med. Chem. 41 (1998) 1745 and references cited therein
34. Liang L., Chi C., Wright M., Timby D., and Unger S. Am. Biotech. Lab. 17 (1999) 8
35. Shiota T., and Yamamori T. J. Org. Chem. 64 (1999) 453
36. Reynolds G.A., and Hauser C.R. Org. Syn. 29 (1949) 70 and references cited therein
37. Ott, G.; Chen, X.-T.; Duan, J.; Lu, Z. PCT Int. Appl. WO 2003024899A2, 2003.