Nonbenzamidine acylsulfonamide tissue factor-factor VIIa inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 18, 2013, Pages 5244-5248

  Glunz, Peter W ^a   Zhang, Xiaojun ^a   Zou, Yan ^a   Delucca, Indawati ^a   Nirschl, Alexandra H ^a   Cheng, Xuhong ^a   Weigelt, Carolyn A ^a   Cheney, Daniel L ^a   Wei, Anzhi ^a   Anumula, Rushith ^a   Luettgen, Joseph M ^a   Rendina, Alan R ^a   Harpel, Mark ^a   Luo, Gang ^a   Knabb, Robert ^a   Wong, Pancras C ^a   Wexler, Ruth R ^a   Priestley, E Scott ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Factor VIIa; Serine protease inhibitors; Structure based design; TF FVIIa inhibitor; Tissue factor

Indexed keywords

AMINOISOQUINOLINE; BENZAMIDINE DERIVATIVE; BLOOD CLOTTING FACTOR 7A INHIBITOR; ISOQUINOLINE DERIVATIVE; NONBENZAMIDINE ACYLSULFONAMIDE TISSUE FACTOR; THROMBIN; TRYPSIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG BIOAVAILABILITY; MOLECULAR MODEL; X RAY CRYSTALLOGRAPHY;

FACTOR VIIA; SERINE PROTEASE INHIBITORS; STRUCTURE-BASED DESIGN; TF-FVIIA INHIBITOR; TISSUE FACTOR;

BENZAMIDINES; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; FACTOR VIIA; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SERINE PROTEINASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84882586245     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.06.027     Document Type: Article

References (42)

1. Global Status Report on Noncommunicable Diseases 2010; WHO Press: Geneva, 2011.
2. R.J. Peters, S.R. Mehta, K.A. Fox, F. Zhao, B.S. Lewis, S.L. Kopecky, R. Diaz, P.J. Commerford, V. Valentin, and S. Yusuf Circulation 108 2003 1682
3. The CURRENT-OASIS 7 Investigators New Eng. J. Med. 363 2010 930
4. L. Wallentin, R.G. Wilcox, W.D. Weaver, H. Emanuelsson, A. Goodvin, P. Nystrom, and A. Bylock Lancet 362 2003 789
5. J.L. Mega, E. Braunwald, S.D. Wiviott, J.-P. Bassand, D.L. Bhatt, C. Bode, P. Burton, M. Cohen, N. Cook-Bruns, K.A.A. Fox, S. Goto, S.A. Murphy, A.N. Plotnikov, D. Schneider, X. Sun, F.W.A. Verheugt, and C.M. Gibson New Eng. J. Med. 366 2012 9
6. P. Tricoci, Z. Huang, C. Held, D.J. Moliterno, P.W. Armstrong, F. Van de Werf, H.D. White, P.E. Aylward, L. Wallentin, E. Chen, Y. Lokhnygina, J. Pei, S. Leonardi, T.L. Rorick, A.M. Kilian, L.H.K. Jennings, G. Ambrosio, C. Bode, A. Cequier, J.H. Cornel, R. Diaz, A. Erkan, K. Huber, M.P. Hudson, L. Jiang, J.W. Jukema, B.S. Lewis, A.M. Lincoff, G. Montalescot, J.C. Nicolau, H. Ogawa, M. Pfisterer, J.C. Prieto, W. Ruzyllo, P.R. Sinnaeve, R.F. Storey, M. Valgimigli, D.J. Whellan, P. Widimsky, J. Strony, and R.A. Harrington New Eng. J. Med. 366 2012 20
7. J.H. Alexander, R.D. Lopes, S. James, R. Kilaru, Y. He, P. Mohan, D.L. Bhatt, S. Goodman, F.W. Verheugt, M. Flather, K. Huber, D. Liaw, S.E. Husted, J. Lopez-Sendon, R. De Caterina, P. Jansky, H. Darius, D. Vinereanu, J.H. Cornel, F. Cools, D. Atar, J.L. Leiva-Pons, M. Keltai, H. Ogawa, P. Pais, A. Parkhomenko, W. Ruzyllo, R. Diaz, H. White, M. Ruda, M. Geraldes, J. Lawrence, R.A. Harrington, and L. Wallentin New Eng. J. Med. 365 2011 699
8. A.G. Olivero, C. Eigenbrot, R. Goldsmith, K. Robarge, D.R. Artis, J. Flygare, T. Rawson, D.P. Sutherlin, S. Kadkhodayan, M. Beresini, L.O. Elliott, G.G. DeGuzman, D.W. Banner, M. Ultsch, U. Marzec, S.R. Hanson, C. Refino, S. Bunting, and D. Kirchhofer J. Biol. Chem. 280 2005 9160
9. O.D. Suleymanov, J.A. Szalony, A.K. Salyers, R.M. Lachance, J.J. Parlow, M.S. South, R.S. Wood, and N.S. Nicholson J. Pharmacol. Exp. Ther. 306 2003 1115
10. J.A. Szalony, O.D. Suleymanov, A.K. Salyers, S.G. Panzer-Knodle, J.D. Blom, R.M. LaChance, B.L. Case, J.J. Parlow, M.S. South, R.S. Wood, and N.S. Nicholson Thromb. Res. 112 2003 167
11. J.A. Szalony, B.B. Taite, T.J. Girard, N.S. Nicholson, and R.M. LaChance J. Thromb. Thrombolysis 14 2002 113
12. A.K. Salyers, J.A. Szalony, O.D. Suleymanov, J.J. Parlow, R.S. Wood, M.S. South, and N.S. Nicholson Pharmacology 70 2004 100
13. P. Wong, E. Crain, C. Watson, A. Staus, J. Luettgen, A. Rendina, L. Abell, R. Knabb, X. Baomin, J. Zhou, I. DeLucca, and E.S. Priestley J. Thromb. Haemost. 3 Suppl. 1 2005 P0162
14. R.A. Shirk, and G.P. Vlasuk Arterioscler. Thromb. Vasc. Biol. 27 2007 1895
15. M. Miura, N. Seki, T. Koike, T. Ishihara, T. Niimi, F. Hirayama, T. Shigenaga, Y. Sakai-Moritani, A. Tagawa, T. Kawasaki, S. Sakamoto, M. Okada, M. Ohta, and S. Tsukamoto Bioorg. Med. Chem. 15 2007 160
16. R. Rai, A. Kolesnikov, P.A. Sprengeler, S. Torkelson, T. Ton, B.A. Katz, C. Yu, J. Hendrix, W.D. Shrader, R. Stephens, R. Cabuslay, E. Sanford, and W.B. Young Bioorg. Med. Chem. Lett. 16 2006 2270
17. J.R. Riggs, H. Hu, A. Kolesnikov, E.M. Leahy, K.E. Wesson, W.D. Shrader, D. Vijaykumar, T.A. Wahl, Z. Tong, P.A. Sprengeler, M.J. Green, C. Yu, B.A. Katz, E. Sanford, M. Nguyen, R. Cabuslay, and W.B. Young Bioorg. Med. Chem. Lett. 16 2006 3197
18. H. Hu, A. Kolesnikov, J.R. Riggs, K.E. Wesson, R. Stephens, E.M. Leahy, W.D. Shrader, P.A. Sprengeler, M.J. Green, E. Sanford, M. Nguyen, E. Gjerstad, R. Cabuslay, and W.B. Young Bioorg. Med. Chem. Lett. 16 2006 4567
19. J.I. Trujillo, H.C. Huang, W.L. Neumann, M.W. Mahoney, S. Long, W. Huang, D.J. Garland, C. Kusturin, Z. Abbas, M.S. South, and D.B. Reitz Bioorg. Med. Chem. Lett. 17 2007 4568
20. J.J. Parlow, B.L. Case, T.A. Dice, R.L. Fenton, M.J. Hayes, D.E. Jones, W.L. Neumann, R.S. Wood, R.M. Lachance, T.J. Girard, N.S. Nicholson, M. Clare, R.A. Stegeman, A.M. Stevens, W.C. Stallings, R.G. Kurumbail, and M.S. South J. Med. Chem. 46 2003 4050
21. M.S. South, B.L. Case, R.S. Wood, D.E. Jones, M.J. Hayes, T.J. Girard, R.M. Lachance, N.S. Nicholson, M. Clare, A.M. Stevens, R.A. Stegeman, W.C. Stallings, R.G. Kurumbail, and J.J. Parlow Bioorg. Med. Chem. Lett. 13 2003 2319
22. X. Zhang, P.W. Glunz, W. Jiang, A. Schmitt, M. Newman, F.A. Barbera, J.M. Bozarth, A.R. Rendina, A. Wei, X. Wen, K.A. Rossi, J.M. Luettgen, P.C. Wong, R.M. Knabb, R.R. Wexler, and E.S. Priestley Bioorg. Med. Chem. Lett. 23 2013 1604
23. E.S. Priestley, I. DeLucca, J. Zhou, J. Zhou, E. Saiah, R. Stanton, L. Robinson, J.M. Luettgen, A. Wei, X. Wen, R.M. Knabb, P.C. Wong, and R.R. Wexler Bioorg. Med. Chem. Lett. 23 2013 2432
24. Examples of prodrugs of Factor VIIa inhibitors: K.G. Zbinden, U. Obst-Sander, K. Hilpert, H. Kuehne, D.W. Banner, H.-J. Boehm, M. Stahl, J. Ackermann, L. Alig, L. Weber, H.P. Wessel, M.A. Riederer, T.B. Tschopp, and T. Lave Bioorg. Med. Chem. Lett. 15 2005 5344
25. J.R. Riggs, A. Kolesnikov, J. Hendrix, W.B. Young, W.D. Shrader, D. Vijaykumar, R. Stephens, L. Liu, L. Pan, J. Mordenti, M.J. Green, and J. Sukbuntherng Bioorg. Med. Chem. Lett. 16 2006 2224
26. D. Vijaykumar, R. Rai, M. Shaghafi, T. Ton, S. Torkelson, E.M. Leahy, J.R. Riggs, H. Hu, P.A. Sprengeler, W.D. Shrader, C. O'Bryan, R. Cabuslay, E. Sanford, E. Gjerstadt, L. Liu, J. Sukbuntherng, and W.B. Young Bioorg. Med. Chem. Lett. 16 2006 3829
27. L.P. Masic Curr. Med. Chem. 13 2006 3627
28. Aliagas-Martin, I.; Artis, D. R.; Dina, M. S.; Flygare, J. A.; Goldsmith, R. A.; Munroe, R. A.; Olivero, A. G.; Pastor, R.; Rawson, T. E.; Robarge, K. D.; Sutherlin, D. P.; Weese, K. J.; Zhou, Z.; Zhu, Y. (Genentech, Inc., USA). Chemical synthesis of serine protease inhibitors and their use to treat clotting disorders. U.S. Patent WO2,000,041,531, July 20, 2000.
29. 2, AcOH).
30. J. Sakaki, T. Murata, Y. Yuumoto, I. Nakamura, T. Frueh, T. Pitterna, G. Iwasaki, K. Oda, T. Yamamura, and K. Hayakawa Bioorg. Med. Chem. Lett. 8 1998 2241
31. A.K. Roy J. Am. Chem. Soc. 115 1993 2598
32. Glunz, P. W.; Bisacchi, G. S.; Morton, G. C.; Holubec, A. A.; Priestley, E. S.; Zhang, X.; Treuner, U. D. (Bristol-Myers Squibb, USA). Phenylglycine derivatives useful as serine protease inhibitors. U.S. Patent 7,122,559, October 17, 2006.
33. M.H. Ali, and S.L. Buchwald J. Org. Chem. 66 2001 2560
34. Lam, P. Y.; Clark, C. G.; Dominguez, C.; Fevig, J. M.; Han, Q.; Li, R.; Pinto, D. J. -P.; Pruitt, J. R.; Quan, M. L. (DuPont Pharmaceuticals Company, USA). Guanidine mimics as factor Xa inhibitors. U.S. Patent 6,339,099, January 15, 2002.
35. J.B.M. Rewinkel, H. Lucas, P.J.M. Van Galen, A.B.J. Noach, T.G. Van Dinther, A.M.M. Rood, A.J.S.M. Jenneboer, and C.A.A. Van Boeckel Bioorg. Med. Chem. Lett. 9 1999 685
36. S.A. Bolton, J.C. Sutton, R. Anumula, G.S. Bisacchi, B. Jacobson, W.A. Slusarchyk, U.D. Treuner, S.C. Wu, G. Zhao, Z. Pi, S. Sheriff, R.A. Smirk, S. Bisaha, D.L. Cheney, A. Wei, W.A. Schumacher, K.S. Hartl, E. Liu, R. Zahler, and S.M. Seiler Bioorg. Med. Chem. Lett. 23 2013 5239
37. Y. Song, L. Clizbe, C. Bhakta, W. Teng, W. Li, P. Wong, B. Huang, U. Sinha, G. Park, A. Reed, R.M. Scarborough, and B.-Y. Zhu Bioorg. Med. Chem. Lett. 12 2002 2043
38. M.L. Quan, Q. Han, J.M. Fevig, P.Y.S. Lam, S. Bai, R.M. Knabb, J.M. Luettgen, P.C. Wong, and R.R. Wexler Bioorg. Med. Chem. Lett. 16 2006 1795
39. M.L. Quan, P.Y.S. Lam, Q. Han, D.J.P. Pinto, M.Y. He, R. Li, C.D. Ellis, C.G. Clark, C.A. Teleha, J.-H. Sun, R.S. Alexander, S. Bai, J.M. Luettgen, R.M. Knabb, P.C. Wong, and R.R. Wexler J. Med. Chem. 48 2005 1729
40. P.Y.S. Lam, C.G. Clark, R. Li, D.J.P. Pinto, M.J. Orwat, R.A. Galemmo, J.M. Fevig, C.A. Teleha, R.S. Alexander, A.M. Smallwood, K.A. Rossi, M.R. Wright, S.A. Bai, K. He, J.M. Luettgen, P.C. Wong, R.M. Knabb, and R.R. Wexler J. Med. Chem. 46 2003 4405
41. S. Krishnaswamy J. Thromb. Haemost. 3 2005 54
42. P.C. Wong, J.M. Luettgen, A.R. Rendina, C.A. Kettner, B. Xin, R.M. Knabb, R. Wexler, and E.S. Priestley Thromb. Haemost. 104 2010 261