Design, synthesis, and evaluation of imidazo[1,2-b]pyridazine derivatives having a benzamide unit as novel VEGFR2 kinase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 24, 2012, Pages 7051-7058

  Miyamoto, Naoki ^a   Oguro, Yuya ^a   Takagi, Terufumi ^a   Iwata, Hidehisa ^a   Miki, Hiroshi ^a   Hori, Akira ^a   Imamura, Shinichi ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

Imidazo 1,2 b pyridazine; Kinase inhibitor; VEGF; VEGFR2

Indexed keywords

3 (IMIDAZO[1,2 B]PYRIDAZIN 6 YLOXY) N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 3 (IMIDAZO[1,2 B]PYRIDAZIN 6 YLOXY) N PHENYLBENZAMIDE; BENZAMIDE; IMIDAZO[1,2 B]PYRIDAZINE DERIVATIVE; N [2 (IMIDAZO[1,2 B]PYRIDAZIN 6 YLOXY)PHENYL] N' PHENYLUREA; N [3 (IMIDAZO[1,2 B]PYRIDAZIN 6 YLOXY)PHENYL] 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 (IMIDAZO[1,2 B]PYRIDAZIN 6 YLOXY)PHENYL] N' [3 (TRIFLUOROMETHYL)PHENYL]UREA; N [3 (IMIDAZO[1,2 B]PYRIDAZIN 6 YLOXY)PHENYL] N' [4 (TRIFLUOROMETHYL)PHENYL]UREA; N [3 (IMIDAZO[1,2 B]PYRIDAZIN 6 YLOXY)PHENYL] N' PHENYLUREA; N [3 (IMIDAZO[1,2 B]PYRIDAZIN 6 YLOXY)PHENYL]BENZAMIDE; N [4 (IMIDAZO[1,2 B]PYRIDAZIN 6 YLOXY)PHENYL] N' PHENYLUREA; PHOSPHOTRANSFERASE INHIBITOR; PLATELET DERIVED GROWTH FACTOR BETA RECEPTOR; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG; VASCULOTROPIN RECEPTOR 2;

ARTICLE; DRUG ACTIVITY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZAMIDES; CELL LINE, TUMOR; DRUG DESIGN; HUMANS; IMIDAZOLES; MALE; MICE; MODELS, MOLECULAR; PROSTATIC NEOPLASMS; PROTEIN KINASE INHIBITORS; PYRIDAZINES; STRUCTURE-ACTIVITY RELATIONSHIP; VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR-2; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84870060829     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.10.004     Document Type: Article

References (39)

1. J. Folkman, E. Merler, C. Abernathy, and G. Williams J. Exp. Med. 133 1971 275
2. J. Folkman, and Y. Shing J. Biol. Chem. 267 1992 10931
3. M. Klagsbrun, and M.A. Moses Chem. Biol. 6 1999 R217
4. D.B. Rifkin, and D. Moscatelli J. Cell Biol. 109 1989 1
5. R.F. Nicosia, S.V. Nicosia, and M. Smith Am. J. Pathol. 145 1994 1023
6. C. Suri, J. McClain, G. Thurston, D.M. McDonald, H. Zhou, E.H. Oldmixon, T.N. Sato, and G.D. Yancopoulos Science 282 1998 468
7. M. Shibuya, and L. Claesson-Welsh Exp. Cell Res. 312 2006 549
8. M. Dougher, and B.I. Terman Oncogene 18 1999 1619
9. S.R. Hubbard Prog. Biophys. Mol. Biol. 71 1999 343
10. L.M. Strawn, and L.K. Shawver Expert Opin. Invest. Drugs 7 1998 553
11. D. Shweiki, A. Itin, D. Soffer, and E. Keshet Nature 359 1992 843
12. K. Kawasaki, T. Watabe, H. Sase, M. Hiroshima, H. Koide, Y. Morishita, K. Yuki, T. Sasaoka, T. Suda, M. Katsuki, K. Miyazono, and K. Miyazawa J. Cell Biol. 181 2008 131
13. L. Zhang, D. Yu, M. Hu, S. Xiong, A. Lang, L.M. Ellis, and R.E. Pollock Cancer Res. 60 2000 3655
14. G.D. Guetz, B. Uzzan, P. Nicolas, M. Cucherat, J.F. Morere, R. Benamouzig, J.L. Breau, and G.Y. Perret Br. J. Cancer 94 2006 1823
15. A. Yuan, C.J. Yu, W.J. Chen, F.Y. Lin, S.H. Kuo, K.T. Luh, and P.C. Yang Int. J. Cancer 89 2000 475
16. J. Jacobsen, K. Grankvist, T. Rasmuson, A. Bergh, G. Landberg, and B. Ljungberg Br. J. Urol. Int. 93 2004 297
17. H. Hurwitz, L. Fehrenbacher, W. Novotny, T. Cartwright, J. Hainsworth, W. Heim, J. Berlin, A. Baron, S. Griffing, E. Holmgren, N. Ferrara, G. Fyfe, B. Rogers, R. Ross, and F. Kabbinavar N. Engl. J. Med. 350 2004 2335
18. A. Sandler, R. Gray, M.C. Perry, J. Brahmer, J.H. Schiller, A. Dowlati, R. Lilenbaum, and D.H. Johnson N. Engl. J. Med. 355 2006 2542
19. K. Miller, M. Wang, J. Gralow, M. Dickler, M. Cobleigh, E.A. Perez, T. Shenkier, D. Cella, and N.E. Davidson N. Engl. J. Med. 357 2007 2666
20. D. Strumberg Drugs Today 41 2005 773
21. R.J. Motzer, M.D. Michaelson, B.G. Redman, G.R. Hudes, G. Wilding, R.A. Figlin, M.S. Ginsberg, S.T. Kim, C.M. Baum, S.E. DePrimo, J.Z. Li, C.L. Bello, C.P. Theuer, D.J. George, and B.I. Rini J. Clin. Oncol. 24 2006 16
22. P.A. Harris, A. Boloor, M. Cheung, R. Kumar, R.M. Crosby, R.G. Davis-Ward, A.H. Epperly, K.W. Hinkle, R.N, III Hunter, J.H. Johnson, V.B. Knick, C.P. Laudeman, D.K. Luttrell, R.A. Mook, R.T. Nolte, S.K. Rudolph, J.R. Szewczyk, A.T. Truesdale, J.M. Veal, L. Wang, and J.A. Stafford J. Med. Chem. 51 2008 4632
23. G.J. Roth, A. Heckel, F. Colbatzky, S. Handschuh, J. Kley, T. Lehmann-Lintz, R. Lotz, U. Tontsch-Grunt, R. Walter, and F. Hilberg J. Med. Chem. 52 2009 4466
24. P.A. Renhowe, S. Pecchi, C.M. Shafer, T.D. Machajewski, E.M. Jazan, C. Taylor, W. Antonios-McCrea, C.M. McBride, K. Frazier, M. Wiesmann, G.R. Lapointe, P.H. Feucht, R.L. Warne, C.C. Heise, D. Menezes, K. Aardalen, H. Ye, M. He, V. Le, J. Vora, J.M. Jansen, M.E. Wernette-Hammond, and A.L. Harris J. Med. Chem. 52 2009 278
25. A. Polverino, A. Coxon, C. Starnes, Z. Diaz, T. DeMelfi, L. Wang, J. Bready, J. Estrada, R. Cattley, S. Kaufman, D. Chen, Y. Gan, G. Kumar, J. Meyer, S. Neervannan, G. Alva, J. Talvenheimo, S. Montestruque, A. Tasker, V. Patel, R. Radinsky, and R. Kendall Cancer Res. 66 2006 8715
26. K. Nakamura, E. Taguchi, T. Miura, A. Yamamoto, K. Takahashi, F. Bichat, N. Guilbaud, K. Hasegawa, K. Kubo, Y. Fujiwara, R. Suzuki, K. Kubo, M. Shibuya, and T. Isae Cancer Res. 66 2006 9134
27. D.H. Albert, P. Tapang, T.J. Magoc, L.J. Pease, D.R. Reuter, R.Q. Wei, J. Li, J. Guo, P.F. Bousquet, N.S. Ghoreishi-Haack, B. Wang, G.T. Bukofzer, Y.C. Wang, J.A. Stavropoulos, K. Hartandi, A.L. Niquette, N. Soni, E.F. Johnson, J.O. McCall, J.J. Bouska, Y. Luo, C.K. Donawho, Y. Dai, P.A. Marcotte, K.B. Glaser, M.R. Michaelides, and S.K. Davidsen Mol. Cancer Ther. 5 2006 995
28. Y. Oguro, N. Miyamoto, K. Okada, T. Takagi, H. Iwata, Y. Awazu, H. Miki, A. Hori, K. Kamiyama, and S. Imamura Bioorg. Med. Chem. 18 2010 7260
29. P.W. Manley, G. Bold, J. Brüggen, G. Fendrich, P. Furet, J. Mestan, C. Schnell, B. Stolz, T. Meyer, B. Meyhack, W. Stark, A. Strauss, and J. Wood Biochim. Biophys. Acta 1697 2004 17
30. Y. Miyazaki, S. Matsunaga, J. Tang, Y. Maeda, M. Nakano, R.J. Philippe, M. Shibahara, W. Liu, H. Sato, L. Wang, and R.T. Nolte Bioorg. Med. Chem. Lett. 15 2005 2203
31. M.H. Potashman, J. Bready, A. Coxon, T.M. DeMelfi Jr., L. DiPietro, N. Doerr, D. Elbaum, J. Estrada, P. Gallant, J. Germain, Y. Gu, J.C. Harmange, S.A. Kaufman, R. Kendall, J.L. Kim, G.N. Kumar, A.M. Long, S. Neervannan, V.F. Patel, A. Polverino, P. Rose, S. Plas, D. Whittington, R. Zanon, and H. Zhao J. Med. Chem. 50 2007 4351
32. J.C. Harmange, M.M. Weiss, J. Germain, A.J. Polverino, G. Borg, J. Bready, D. Chen, D. Choquette, A. Coxon, T. DeMelfi, L. DiPietro, N. Doerr, J. Estrada, J. Flynn, R.F. Graceffa, S.P. Harriman, S. Kaufman, D.S. La, A. Long, M.W. Martin, S. Neervannan, V.F. Patel, M. Potashman, K. Regal, P.M. Roveto, M.L. Schrag, C. Starnes, A. Tasker, Y. Teffera, L. Wang, R.D. White, D.A. Whittington, and R. Zanon J. Med. Chem. 51 2008 1649
33. V.J. Cee, A.C. Cheng, K. Romero, S. Bellon, C. Mohr, D.A. Whittington, A. Bak, J. Bready, S. Caenepeel, A. Coxon, H.L. Deak, J. Fretland, Y. Gu, B.L. Hodous, X. Huang, J.L. Kim, J. Lin, A.M. Long, H. Nguyen, P.R. Olivieri, V.F. Patel, L. Wang, Y. Zhou, P. Hughes, and S. Geuns-Meyer Bioorg. Med. Chem. Lett. 19 2009 424
34. K.F. Byth, N. Cooper, J.D. Culshaw, D.W. Heaton, S.E. Oakes, C.A. Minshull, R.A. Norman, R.A. Pauptit, J.A. Tucker, J. Breed, A. Pannifer, S. Rowsell, J.J. Stanway, A.L. Valentine, and A.P. Thomas Bioorg. Med. Chem. Lett. 14 2004 2249
35. E.F. Ullman, H. Kirakossian, S. Singh, Z.P. Wu, B.R. Irvin, J.S. Pease, A.C. Switchenko, J.D. Irvine, A. Dafforn, C.N. Skold, and D.B. Wagner Proc. Natl. Acad. Sci. U.S.A. 91 1994 5426
36. G. Manning, D.B. Whyte, R. Martinez, T. Hunter, and S. Sudarsanam Science 298 2002 1912
37. K. Pietras, T. Sjöblom, K. Rubin, C.H. Heldin, and A. Östman Cancer Cell 3 2003 439
38. A. Abramsson, P. Lindblom, and C. Betsholtz J. Clin. Invest. 112 2003 1142
39. M. Saitoh, J. Kunitomo, E. Kimura, Y. Hayase, H. Kobayashi, N. Uchiyama, T. Kawamoto, T. Tanaka, C.D. Mol, D.R. Dougan, G.S. Textor, G.P. Snell, and F. Itoh Bioorg. Med. Chem. 17 2009 2017