Property-based design of KDR kinase inhibitors

Current Medicinal Chemistry

Volumn 11, Issue 6, 2004, Pages 709-719

  Fraley, Mark E ^a   Hoffman, William F ^a   Arrington, Kenneth L ^a   Hungate, Randy W ^a   Hartman, George D ^a   McFall, Rosemary C ^a   Coll, Kathleen E ^a   Rickert, Keith ^a   Thomas, Kenneth A ^a   McGaughey, Georgia B ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Angiogenesis; Cellular activity; KDR kinase inhibitors; Oral biovailability; Pharmacokinetics; Property based design; Solubility; Vascular endothelial growth factor (VEGF)

Indexed keywords

2 QUINOLINONE DERIVATIVE; 3 (3 INDOLYL)PYRIDINE DERIVATIVE; 3 (4 BROMO 2,6 DIFLUOROBENZYLOXY) 5 [3 [4 (1 PYRROLIDINYL)BUTYL]UREIDO] 4 ISOTHIAZOLECARBOXAMIDE; BENZIMIDAZOLE DERIVATIVE; CP 547 632; ISOTHIAZOLE DERIVATIVE; N (4 BROMO 2 FLUOROPHENYL) 6 METHOXY 7 [2 (1H 1,2,3 TRIAZOL 1 YL)ETHOXY] 4 QUINAZOLINAMINE; PROTEIN TYROSINE KINASE INHIBITOR; PYRAZOLO[1,5 A]PYRIMIDINE DERIVATIVE; PYRIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; SEMAXANIB; SUNITINIB; UNCLASSIFIED DRUG; VANDETANIB; VASCULOTROPIN RECEPTOR 2; VATALANIB;

CELL MEMBRANE PERMEABILITY; CLINICAL TRIAL; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; LIPOPHILICITY; NONHUMAN; PHYSICAL CHEMISTRY; RAT; REVIEW; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANIMALS; BINDING SITES; BIOLOGICAL AVAILABILITY; CELL MEMBRANE PERMEABILITY; DRUG DESIGN; ENZYME INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR-2;

EID: 12144285906     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867043455729     Document Type: Review

References (31)

1. Adamis, A. P.; Shima, D. T.; Yeo, K. T.; Yeo, T. K.; Brown, L.F.; Berse, B.; D'Amore, P. A.; Folkman, J. Biochem. Biophys. Res. Commun. 1993, 193, 631.
2. Giatromanolaki, A.; Sivridis, E.; Athanassou, N.; Zois, E.; Thorpe, P. E.; Brekken, R. A.; Gatter, K. C.; Harris, A. L.; Koukourakis, I. M.; Koukourakis, M. I. J. Path. 2001, 194, 101.
3. Enomoto, H.; Inoki, I.; Komiya, K.; Shiomi, T.; Ikeda, E.; Obata K.; Matsumoto, H.; Toyama, Y.; Okada, Y. Am. J. Pathol. 2003, 162, 171.
4. Detmar, M. Dermatol. Sci. 2000,24, S78.
5. Carmeliet, P.; Jain, R. K. Nature 2000, 407, 249.
6. Folkman, J. Nature Med. 1995, 1, 27.
7. Zetter, B. R. Ann. Rev. Med. 1998, 49, 407.
8. Hanahan, D.; Folkman, J. Cell 1996, 86, 353.
9. Holmgen, L.; O'Reilly, M. S.; Folkman, J. Nature Med. 1995, 1, 149.
10. Veikkola, T.; Karkkainen, M.; Claesson-Welsh, L.; Alitalo, K. Cancer Res. 2000, 60, 203.
11. Thomas, K. A. J. Biol. Chem. 1996, 271, 603.
12. Kim, K. J.; Li, B.; Winer, J.; Armanini, M.; Gillett, N.; Phillips, H. S.; Ferrara, N. Nature 1993, 362, 841.
13. Witte, L.; Hicklin, D.; Zhu, Z.; Pytowski, B.; Kotanides, H.; Rockwell, P.; Bohlen, P. Cancer Metastasis Rev. 1998, 17, 155.
14. Fong, T. A. T.; Shawver, L. K.; Sun, L.; Tang, C.; App. H.; Powell, T. J.; Kim, Y. H.; Schreck, R.; Wang, X.; Risau, W.; Ullrich, A.; Hirth, K. P.; McMahon, G. Cancer Res. 1999, 59, 99.
15. Drevs, J.; Hofmann, I.; Hugenschmidt, H.; Wittig, C.; Madjar, H.; Müller, M.; Wood, J.; Martiny-Baron, G.; Unger, C.; Marmé, D. Cancer Res. 2000, 60, 4819.
16. Wedge, S. R.; Ogilvie, D. J.; Dukes, M.; Kendrew J.; Chester, R.; Jackson, J. A.; Boffey, S. J.; Valentine, P. J.; Curwen, J. O.; Musgrove, H. L.; Graham, G. A.; Hughes, G. D.; Thomas, A. P.; Stokes, E. S. E.; Curry, B.; Richmond, G. H. P.; Wadsworth, P. F.; Bigley, A. L.; Hennequin, L. F. Cancer Res. 2002, 62, 4645.
17. Connel, R. D. Expert Opin. Ther. Patents 2002, 12, 1763.
18. Bilodeau, M. T.; Fraley, M. E.; Hartman, G. D. Expert Opin. Investig. Drugs 2002, 11, 737.
19. Boyer, S. J. Curr. Top. Med. Chem. 2002, 2, 973-1000.
20. Van de Waterbeemd, H.; Smith, D. A.; Beaumont, K.; Walker, D. A. J. Med. Chem. 2001, 44, 1313.
21. Hennequin, L. F.; Stokes, E. S. E.; Thomas, A. P.; Johnstone, C.; Plé, P. A.; Ogilvie, D. J.; Dukes, M.; Wedge, S. R.; Kendrew, J.; Curwen, J. O. J. Med. Chem. 2002, 45, 1300.
22. Fraley, M. E.; Rubino, R. S.; Hoffman, W. F.; Hambaugh, S. R.; Arrington, K. A.; Hungate, R. W.; Bilodeau, M. T.; Tebben, A. J.; Rutledge, R. Z.; Kendall, R. L.; McFall, R. C.; Huckle, W. R.; Coll, K. E.; Thomas, K. A. Bioorg. Med. Chem. Lett. 2002,12,3537.
23. Kendall, R. L.; Rutledge, R. Z.; Mao, X.; Tebben, A. J.; Hungate, R. W.; Thomas, K. A. J. Biol. Chem. 1999, 274, 6453.
24. Bilodeau, M. T.; Fraley, M. E.; Hungate, R. W.; Kendall, R. L.; Rutledge, R.; Thomas, K. A.; Rubino, R. U.S. Patent 6, 380, 203, 2002.
25. Kerns, E. H. J. Pharm. Sci. 2001, 90, 1838.
26. Hubbard, S. R.; Wei, L.; Ellis, L.; Hendrickson, W. A. Nature 1994, 372, 746.
27. Traxler, P.; Furet, P. Pharmacol. Ther. 1999, 82, 195.
28. Fraley, M. E.; Arrington, K. L.; Hambaugh, S. R.; Hoffman, W. F.; Cunningham, A. M.; Young, M. B.; Hungate, R. W.; Tebben, A. J.; Rutledge, R. Z.; Kendall, R. L.; Huckle, W. R.; McFall, R. C.; Coll, K. E.; Thomas, K. A. Bioorg. Med. Chem. Lett. 2003, 13, 2973.
29. Mendel, D. B.; Laird, A. D.; Smolich, B. D.; Blake, R. A.; Liang, C.; Hannah, A. L.; Shaheen, R. M.; Ellis, L. M.; Weitman, S.; Shawver, L. K.; Cherrington, J. M. Anti-Cancer Drug Design 2000, 15, 15.
30. Marsais, F.; Godard, A.; Queguiner, G. J. Heterocyclic Chem. 1989, 26, 1589.
31. Fraley, M. E.; Arrington, K. L.; Buser, C. A.; Ciecko, P. A.; Coll, K. E.; Fernandes, C.; Hartman, G. D.; Hoffman, W. F.; Lynch, J. J.; McFall, R. C.; Rickert, K.; Singh, R.; Smith, S.; Thomas, K. A.; Wong, B. K. Bioorg. Med. Chem. Lett. 2004, 14, 351.