Respiratory syncytial virus fusion inhibitors. Part 3: Water-soluble benzimidazol-2-one derivatives with antiviral activity in vivo

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 5, 2006, Pages 1115-1122

  Yu, Kuo Long ^a,c   Wang, Xiangdong Alan ^a   Civiello, Rita L ^a   Trehan, Ashok K ^a   Pearce, Bradley C ^a   Yin, Zhiwei ^a   Combrink, Keith D ^a,d   Gulgeze, H Belgin ^a   Zhang, Yi ^a   Kadow, Kathleen F ^a   Cianci, Christopher W ^a   Clarke, Junius ^a   Genovesi, Eugene V ^a   Medina, Ivette ^a   Lamb, Lucinda ^a   Wyde, Philip R ^b   Krystal, Mark ^a   Meanwell, Nicholas A ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b BAYLOR COLLEGE OF MEDICINE   (United States)

^c ELI LILLY AND COMPANY   (United States)

^d Cumbre Inc   (United States)

Author keywords

Antiviral; Benzimidazol 2 one derivatives; Water soluble respiratory syncytial virus inhibitors

Indexed keywords

ANTIVIRUS AGENT; BENZIMIDAZOL 2 ONE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BMS 433771; PLACEBO; RIBAVIRIN; UNCLASSIFIED DRUG;

ACIDITY; AEROSOL; ALKALINITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIVIRAL ACTIVITY; ARTICLE; CELL CULTURE; CELL STRAIN 3T3; CONTROLLED STUDY; COTTON RAT; CYTOTOXICITY; DOSE RESPONSE; DRUG ACTIVITY; DRUG EFFICACY; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VIVO STUDY; MOUSE; NONHUMAN; PARTICLE SIZE; RAT; RESPIRATORY SYNCYTIAL PNEUMOVIRUS; STRUCTURE ACTIVITY RELATION; VIRUS INFECTION;

AMINES; ANIMALS; ANTIVIRAL AGENTS; BENZIMIDAZOLES; MEMBRANE FUSION; MICE; MOLECULAR STRUCTURE; RATS; RESPIRATORY SYNCYTIAL VIRUSES; SIGMODONTINAE; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

ANIMALIA; RESPIRATORY SYNCYTIAL VIRUS; RICE STRIPE VIRUS; SIGMODON;

EID: 31344453015     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.11.109     Document Type: Article

References (58)

1. For Part 1 of this series see: K.-L. Yu, Y. Zhang, R.L. Civiello, K.F. Kadow, C. Cianci, M. Krystal, and N.A. Meanwell Bioorg. Med. Chem. Lett. 13 2003 2141
2. For Part 2 of this series see: K.-L. Yu, Y. Zhang, R.L. Civiello, A.K. Trehan, B.C. Pearce, Z. Yin, K.D. Combrink, H.B. Gulgeze, X.A. Wang, K.F. Kadow, C.W. Cianci, M. Krystal, and N.A. Meanwell Bioorg. Med. Chem. Lett. 14 2004 1133
3. N.A. Meanwell, and M. Krystal Drug Discovery Today 5 2000 241
4. M.G. Ottolini, and V.G. Hemming Drugs 54 1997 867
5. P.R. Wyde Antiviral Res. 39 1998 63
6. K. Maggon, and S. Barik Rev. Med. Virol. 14 2004 149
7. D.C. Halstead, and S.G. Jenkins South. Med. J. 91 1998 433
8. W.W. Thompson, D.K. Shay, E. Weintraub, L. Brammer, N. Cox, L.J. Anderson, and K. Fukuda JAMA 289 2003 179
9. J. Greensill, P.S. McNamara, W. Dove, B. Flanagan, R.L. Smyth, and C.A. Hart Emerg. Infect. Dis. 9 2003 372
10. T. Heikkinen, and T. Chonmaitree Clin. Microbiol. Rev. 16 2003 230
11. M. Hashem, and C.B. Hall J. Clin. Virol. 27 2003 14
12. A.R. Falsey, P.A. Hennessey, M.A. Formica, C. Cox, and E.E. Walsh N. Engl. J. Med. 352 2005 1749
13. A.R. Falsey, and E.E. Walsh Drugs Aging 22 2005 577
14. M.I. Hertz, J.A. Englund, D. Snover, P.B. Bitterman, and P.B. McGlave Medicine 68 1989 269
15. R.D. Harrington, T.M. Hooton, R.C. Hackman, G.A. Storch, B. Osborne, C.A. Gleaves, A. Benson, and J.D. Meyers J. Infect. Dis. 165 1992 987
16. B.E. Gilbert, and V. Knight Antimicrob. Agents Chemother. 30 1986 201
17. S. Johnson, C. Oliver, G.A. Prince, V.G. Hemming, D.S. Pfarr, S.-C. Wang, M. Dormitzer, J. O'Grady, S. Koenig, J.K. Tamura, R. Woods, G. Bansal, D. Couchenour, E. Tsao, W.C. Hall, and J.F. Young J. Infect. Dis. 176 1997 1215
18. A.B. Russell Hosp. Med. 60 1999 873
19. J. Handforth, M. Sharland, and J.S. Friedland Br. Med. J. 328 2004 1026
20. S. Joffe, G.T. Ray, G.J. Escobar, S.B. Black, and T.A. Lieu Pediatrics 104 1999 419
21. J.H. Lofland, J.P. O'Connor, M.L. Chatterton, E.D. Moxey, L.E. Paddock, D.B. Nash, and S.A. Desai Clin. Ther. 22 2000 1357
22. L.E. Yount, and W.T. Mahle Pediatrics 114 2004 1606
23. G.R. Reyes Curr. Opin. Drug Discov. Devel. 4 2001 651
24. G.A. Prince Expert Opin. Investig. Drugs 10 2001 297
25. G.A. Prince Expert Opin. Ther. Patents 9 1999 753
26. L.R. Krilov Expert Opin. Ther. Patents 12 2002 441
27. R.R. Tidwell, J.D. Geratz, and E.J. DuBovi J. Med. Chem. 26 1983 294
28. W.D. Ding, B. Mitsner, G. Krishnamurthy, A. Aulabaugh, C.D. Hess, J. Zaccardi, M. Cutler, B. Feld, A. Gazumyan, Y. Raifeld, A. Nikitenko, S.A. Lang, Y. Gluzman, B. O'Hara, and G.A. Ellestad J. Med. Chem. 41 1998 2671
29. A.A. Nikitenko, Y.E. Raifeld, and T.Z. Wang Bioorg. Med. Chem. Lett. 11 2001 1041
30. V. Razinkov, A. Gazumyan, A. Nikitenko, G.A. Ellestad, and G. Krishnamurthy Chem. Biol. 8 2001 645
31. V. Razinkov, C. Huntley, G.A. Ellestad, and G. Krishnamurthy Antiviral Res. 55 2002 189
32. C.C. Huntley, W.J. Weiss, A. Gazumyan, A. Buklan, B. Feld, W. Hu, T.R. Jones, T. Murphy, A.A. Nikitenko, B. O'Hara, G. Prince, S. Quartuccio, Y.E. Raifeld, P. Wyde, and J.F. O'Connell Antimicrob. Agents Chemother. 46 2002 841
33. J.L. Douglas, M.L. Panis, E. Ho, K.-Y. Lin, S.H. Krawczyk, D.M. Grant, R. Cai, S. Swaminathan, and T. Cihlar J. Virol. 77 2003 5054
34. K. Andries, M. Moeremans, T. Gevers, R. Willebrords, C. Sommen, J. Lacrampe, F. Janssens, and P.R. Wyde Antiviral Res. 60 2003 209
35. P.R. Wyde, S.N. Chetty, P. Timmerman, B.E. Gilbert, and K. Andries Antiviral Res. 60 2003 221
36. J.L. Douglas, M.L. Panis, E. Ho, K.-Y. Lin, S.H. Krawczyk, D.M. Grant, R. Cai, S. Swaminathan, X. Chen, and T. Cihlar Antimicrob. Agents Chemother. 49 2005 2460
37. M. Liuzzi, S.W. Mason, M. Cartier, C. Lawetz, R.S. McCollum, N. Dansereau, G. Bolger, N. Lapeyre, Y. Gaudette, L. Lagace, M.J. Massariol, F. Do, P. Whitehead, L. Lamarre, E. Scouten, J. Bordeleau, S. Landry, J. Rancourt, G. Fazal, and B. Simoneau J. Virol. 79 2005 13105
38. S.W. Mason, C. Lawetz, Y. Gaudette, F. Do, E. Scouten, L. Lagace, B. Simoneau, and M. Liuzzi Nucleic Acids Res. 32 2004 4758
39. C. Cianci, K.-L. Yu, K. Combrink, N. Sin, B. Pearce, A. Wang, R. Civiello, S. Voss, G. Luo, K. Kadow, E.V. Genovesi, B. Venables, H. Gulgeze, A. Trehan, J. James, L. Lamb, I. Medina, J. Roach, Z. Yang, L. Zadjura, R. Colonno, J. Clark, N. Meanwell, and M. Krystal Antimicrob. Agents Chemother. 48 2004 413
40. C. Cianci, E.V. Genovesi, L. Lamb, I. Medina, Z. Yang, L. Zadjura, H. Yang, C. D'Arienzo, N. Sin, K.-L. Yu, K. Combrink, Z. Li, R. Colonno, N. Meanwell, J. Clark, and M. Krystal Antimicrob. Agents Chemother. 48 2004 2448
41. C. Cianci, D.R. Langley, D.D. Dischino, Y. Sun, K.-L. Yu, A. Stanley, J. Roach, Z. Li, R. Dalterio, R. Colonno, N.A. Meanwell, and M. Krystal Proc. Natl. Acad. Sci. U.S.A. 101 2004 15046
42. L.G. Byrd, and G.A. Prince Clin. Infect. Dis. 25 1997 1363
43. Yu, K.-L.; Civiello, R.; Combrink, K.; Gulgeze, H. B.; Pearce, B. C.; Wang, X.; Meanwell, N. A.; Zhang, Y. W., US Patent 6,506,738, 2003.
44. Chem. Abstr. 136 2002 294826
45. J. Davoll, and D.H. Laney J. Chem. Soc. 1960 308
46. N.A. Meanwell, S.-Y. Sit, J. Gao, H.S. Wong, Q. Gao, D.R. St. Laurent, and N. Balasubramanian J. Org. Chem. 60 1995 1565
47. J.T. Drummond, and G. Johnson Tetrahedron Lett. 1998 1653
48. C.F. Sturino, and M. Labelle Tetrahedron Lett. 39 1998 5891
49. W.G. Finnegan, R.A. Henry, and R. Lofquist J. Org. Chem. 80 1958 3908
50. H. Ulrich, B. Tucker, and R. Richter J. Org. Chem. 43 1978 1544
51. C.E. McKenna, and J. Schmidhauser J. Chem. Soc. Chem. Commun. 1979 739
52. J.R. Herr Bioorg. Med. Chem. 10 2002 3379
53. J.B. Domachowske, C.A. Bonville, and H.F. Rosenberg Pediatr. Infect. Dis. J. 23 2004 S228
54. V. Knight, and B.E. Gilbert Antiviral Chemother. 1 1987 441
55. P.R. Wyde, S.Z. Wilson, R. Petrella, and B.E. Gilbert Antiviral Res. 7 1987 211
56. V. Knight, and B. Gilbert Eur. J. Clin. Microbiol. Infect. Dis. 7 1988 721
57. P.R. Wyde, S. Laquerre, S.N. Chetty, B.E. Gilbert, T.J. Nitz, and D.C. Pevear Antiviral Res. 68 2005 18
58. Yang, Z.; Zadjura, L.; Yeola, S. unpublished results.