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Volumn 70, Issue 20, 2010, Pages 8036-8044

A novel, selective, and efficacious nanomolar pyridopyrazinone inhibitor of V600EBRAF

Author keywords

[No Author keywords available]

Indexed keywords

1 [3 TERT BUTYL 1 (4 TOLYL) 1H PYRAZOL 5 YL] 3 [2 (METHYLTHIO) 4 (3 OXO 3,4 DIHYDROPYRIDO[2,3 B]PYRAZIN 8 YLOXY)PHENYL]UREA; B RAF KINASE; B RAF KINASE INHIBITOR; CCT 539065; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 78049284316     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-10-1366     Document Type: Article
Times cited : (19)

References (38)
  • 2
    • 18444374405 scopus 로고    scopus 로고
    • Mutations of the BRAF gene in human cancer
    • Davies H, Bignell GR, Cox C, et al. Mutations of the BRAF gene in human cancer. Nature 2002;417:949-54.
    • (2002) Nature , vol.417 , pp. 949-954
    • Davies, H.1    Bignell, G.R.2    Cox, C.3
  • 3
    • 1942506706 scopus 로고    scopus 로고
    • V599EB-RAF is an oncogene in melanocytes
    • Wellbrock C, Ogilvie L, Hedley D, et al. V599EB-RAF is an oncogene in melanocytes. Cancer Res 2004;64:2338-42.
    • (2004) Cancer Res , vol.64 , pp. 2338-2342
    • Wellbrock, C.1    Ogilvie, L.2    Hedley, D.3
  • 4
    • 31544442670 scopus 로고    scopus 로고
    • Oncogenic BRAF is required for tumor growth and maintenance in melanoma models
    • Hoeflich KP, Gray DC, Eby MT, et al. Oncogenic BRAF is required for tumor growth and maintenance in melanoma models. Cancer Res 2006;66:999-1006.
    • (2006) Cancer Res , vol.66 , pp. 999-1006
    • Hoeflich, K.P.1    Gray, D.C.2    Eby, M.T.3
  • 5
    • 4344584872 scopus 로고    scopus 로고
    • B-RAF is a therapeutic target in melanoma
    • Karasarides M, Chiloeches A, Hayward R, et al. B-RAF is a therapeutic target in melanoma. Oncogene 2004;23:6292-8.
    • (2004) Oncogene , vol.23 , pp. 6292-6298
    • Karasarides, M.1    Chiloeches, A.2    Hayward, R.3
  • 6
    • 33748325763 scopus 로고    scopus 로고
    • Sorafenib in advanced melanoma: A phase II randomised discontinuation trial analysis
    • Eisen T, Ahmad T, Flaherty KT, et al. Sorafenib in advanced melanoma: a phase II randomised discontinuation trial analysis. Br J Cancer 2006;95:581-6.
    • (2006) Br J Cancer , vol.95 , pp. 581-586
    • Eisen, T.1    Ahmad, T.2    Flaherty, K.T.3
  • 7
    • 4944249117 scopus 로고    scopus 로고
    • BAY 43-9006 exhibits broad spectrum oral antitumor activity and targets the RAF/MEK/ERK pathway and receptor tyrosine kinases involved in tumor progression and angiogenesis
    • Wilhelm SM, Carter C, Tang L, et al. BAY 43-9006 exhibits broad spectrum oral antitumor activity and targets the RAF/MEK/ERK pathway and receptor tyrosine kinases involved in tumor progression and angiogenesis. Cancer Res 2004;64:7099-109.
    • (2004) Cancer Res , vol.64 , pp. 7099-7109
    • Wilhelm, S.M.1    Carter, C.2    Tang, L.3
  • 8
    • 33744984843 scopus 로고    scopus 로고
    • Phase II placebo-controlled randomized discontinuation trial of sorafenib in patients with metastatic renal cell carcinoma
    • Ratain MJ, Eisen T, Stadler WM, et al. Phase II placebo-controlled randomized discontinuation trial of sorafenib in patients with metastatic renal cell carcinoma. J Clin Oncol 2006;24:2505-12.
    • (2006) J Clin Oncol , vol.24 , pp. 2505-2512
    • Ratain, M.J.1    Eisen, T.2    Stadler, W.M.3
  • 9
    • 61449175950 scopus 로고    scopus 로고
    • Sorafenib for the treatment of unresectable hepatocellular carcinoma
    • Kane RC, Farrell AT, Madabushi R, et al. Sorafenib for the treatment of unresectable hepatocellular carcinoma. Oncologist 2009;14:95-100.
    • (2009) Oncologist , vol.14 , pp. 95-100
    • Kane, R.C.1    Farrell, A.T.2    Madabushi, R.3
  • 10
    • 33846260566 scopus 로고    scopus 로고
    • Sorafenib for the treatment of advanced renal cell carcinoma
    • Kane RC, Farrell AT, Saber H, et al. Sorafenib for the treatment of advanced renal cell carcinoma. Clin Cancer Res 2006;12:7271-8.
    • (2006) Clin Cancer Res , vol.12 , pp. 7271-7278
    • Kane, R.C.1    Farrell, A.T.2    Saber, H.3
  • 11
    • 33845730781 scopus 로고    scopus 로고
    • Demonstration of a genetic therapeutic index for tumors expressing oncogenic BRAF by the kinase inhibitor SB-590885
    • King AJ, Patrick DR, Batorsky RS, et al. Demonstration of a genetic therapeutic index for tumors expressing oncogenic BRAF by the kinase inhibitor SB-590885. Cancer Res 2006;66:11100-5.
    • (2006) Cancer Res , vol.66 , pp. 11100-11105
    • King, A.J.1    Patrick, D.R.2    Batorsky, R.S.3
  • 12
    • 42949149240 scopus 로고    scopus 로고
    • Discovery of a selective inhibitor of oncogenic B-Raf kinase with potent antimelanoma activity
    • Tsai J, Lee JT, Wang W, et al. Discovery of a selective inhibitor of oncogenic B-Raf kinase with potent antimelanoma activity. Proc Natl Acad Sci U S A 2008;105:3041-6.
    • (2008) Proc Natl Acad Sci U S A , vol.105 , pp. 3041-3046
    • Tsai, J.1    Lee, J.T.2    Wang, W.3
  • 13
    • 67651246671 scopus 로고    scopus 로고
    • Phase I study of PLX4032: Proof of concept for V600E BRAF mutation as a therapeutic target in human cancer
    • Meeting Abstracts
    • Flaherty K, Puzanov I, Sosman J, et al. Phase I study of PLX4032: proof of concept for V600E BRAF mutation as a therapeutic target in human cancer. J Clin Oncol (Meeting Abstracts) 2009;27:9000.
    • (2009) J Clin Oncol , vol.27 , pp. 9000
    • Flaherty, K.1    Puzanov, I.2    Sosman, J.3
  • 14
    • 78049299416 scopus 로고    scopus 로고
    • Preparation of pyrido[2,3-b]pyrazine-8-substituted compounds as RAF inhibitors
    • inventors (Cancer Research Technology Limited, UK; Institute of Cancer Research, Royal Cancer Hospital). Assignee. Application: WO patent 2008-GB4208. 2009077766. 2009 20081219
    • Springer CJ, Niculescu-Duvaz D, Niculescu-Duvaz I, Marais R, Suijkerbuijk BMJM, Zambon A, et al., inventors (Cancer Research Technology Limited, UK; Institute of Cancer Research, Royal Cancer Hospital). Assignee. Preparation of pyrido[2,3-b]pyrazine-8-substituted compounds as RAF inhibitors. Application: WO patent 2008-GB4208. 2009077766. 2009 20081219.
    • Springer, C.J.1    Niculescu-Duvaz, D.2    Niculescu-Duvaz, I.3    Marais, R.4    Suijkerbuijk, B.5    Zambon, A.6
  • 15
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones G, Willett P, Glen RC, Leach AR, Taylor R. Development and validation of a genetic algorithm for flexible docking. J Mol Biol 1997;267:727-48.
    • (1997) J Mol Biol , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 16
    • 1642494839 scopus 로고    scopus 로고
    • The cyclin-dependent kinase inhibitor CYC202 (R-roscovitine) inhibits retinoblastoma protein phosphorylation, causes loss of cyclin D1, and activates the mitogen-activated protein kinase pathway
    • Whittaker SR, Walton MI, Garrett MD, Workman P. The cyclin-dependent kinase inhibitor CYC202 (R-roscovitine) inhibits retinoblastoma protein phosphorylation, causes loss of cyclin D1, and activates the mitogen-activated protein kinase pathway. Cancer Res 2004;64:262-72.
    • (2004) Cancer Res , vol.64 , pp. 262-272
    • Whittaker, S.R.1    Walton, M.I.2    Garrett, M.D.3    Workman, P.4
  • 17
    • 30444450278 scopus 로고    scopus 로고
    • Novel inhibitors of B-RAF based on a disubstituted pyrazine scaffold. Generation of a nanomolar lead
    • Niculescu-Duvaz I, Roman E, Whittaker SR, et al. Novel inhibitors of B-RAF based on a disubstituted pyrazine scaffold. Generation of a nanomolar lead. J Med Chem 2006;49:407-16.
    • (2006) J Med Chem , vol.49 , pp. 407-416
    • Niculescu-Duvaz, I.1    Roman, E.2    Whittaker, S.R.3
  • 18
    • 0025775062 scopus 로고
    • Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines
    • Monks A, Scudiero D, Skehan P, et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 1991;83:757-66.
    • (1991) J Natl Cancer Inst , vol.83 , pp. 757-766
    • Monks, A.1    Scudiero, D.2    Skehan, P.3
  • 19
    • 77952812169 scopus 로고    scopus 로고
    • Guidelines for the welfare and use of animals in cancer research
    • Workman P, Aboagye EO, Balkwill F, et al. Guidelines for the welfare and use of animals in cancer research. Br J Cancer 2010;102:1553-4.
    • (2010) Br J Cancer , vol.102 , pp. 1553-1554
    • Workman, P.1    Aboagye, E.O.2    Balkwill, F.3
  • 20
    • 42349084306 scopus 로고    scopus 로고
    • NVP-AUY922: A novel heat shock protein 90 inhibitor active against xenograft tumor growth, angiogenesis, and metastasis
    • Eccles SA, Massey A, Raynaud FI, et al. NVP-AUY922: a novel heat shock protein 90 inhibitor active against xenograft tumor growth, angiogenesis, and metastasis. Cancer Res 2008;68:2850-60.
    • (2008) Cancer Res , vol.68 , pp. 2850-2860
    • Eccles, S.A.1    Massey, A.2    Raynaud, F.I.3
  • 21
    • 27644591251 scopus 로고    scopus 로고
    • In vitro and in vivo pharmacokinetic-pharmacodynamic relationships for the trisubstituted aminopurine cyclin-dependent kinase inhibitors olomoucine, bohemine and CYC202
    • Raynaud FI, Whittaker SR, Fischer PM, et al. In vitro and in vivo pharmacokinetic-pharmacodynamic relationships for the trisubstituted aminopurine cyclin-dependent kinase inhibitors olomoucine, bohemine and CYC202. Clin Cancer Res 2005;11:4875-87.
    • (2005) Clin Cancer Res , vol.11 , pp. 4875-4887
    • Raynaud, F.I.1    Whittaker, S.R.2    Fischer, P.M.3
  • 22
    • 67649992844 scopus 로고    scopus 로고
    • Novel potent BRAF inhibitors: Toward 1 nM compounds through optimization of the central phenyl ring
    • Menard D, Niculescu-Duvaz I, Dijkstra HP, et al. Novel potent BRAF inhibitors: toward 1 nM compounds through optimization of the central phenyl ring. J Med Chem 2009;52:3881-91.
    • (2009) J Med Chem , vol.52 , pp. 3881-3891
    • Menard, D.1    Niculescu-Duvaz, I.2    Dijkstra, H.P.3
  • 23
    • 65249087812 scopus 로고    scopus 로고
    • Pyridoimidazolones as novel potent inhibitors of v-Raf murine sarcoma viral oncogene homologue B1 (BRAF)
    • Niculescu-Duvaz D, Gaulon C, Dijkstra HP, et al. Pyridoimidazolones as novel potent inhibitors of v-Raf murine sarcoma viral oncogene homologue B1 (BRAF). J Med Chem 2009;52:2255-64.
    • (2009) J Med Chem , vol.52 , pp. 2255-2264
    • Niculescu-Duvaz, D.1    Gaulon, C.2    Dijkstra, H.P.3
  • 24
    • 77949401354 scopus 로고    scopus 로고
    • BRAF inhibitors based on an imidazo[4,5]pyridin-2-one scaffold and a meta substituted middle ring
    • Nourry A, Zambon A, Davies L, et al. BRAF inhibitors based on an imidazo[4,5]pyridin-2-one scaffold and a meta substituted middle ring. J Med Chem 2010;53:1964-78.
    • (2010) J Med Chem , vol.53 , pp. 1964-1978
    • Nourry, A.1    Zambon, A.2    Davies, L.3
  • 25
    • 77950559038 scopus 로고    scopus 로고
    • Development of novel, highly potent inhibitors of V-RAF murine sarcoma viral oncogene homologue B1 (BRAF): Increasing cellular potency through optimization of a distal heteroaromatic group
    • Suijkerbuijk BM, Niculescu-Duvaz I, Gaulon C, et al. Development of novel, highly potent inhibitors of V-RAF murine sarcoma viral oncogene homologue B1 (BRAF): increasing cellular potency through optimization of a distal heteroaromatic group. J Med Chem 2010;53:2741-56.
    • (2010) J Med Chem , vol.53 , pp. 2741-2756
    • Suijkerbuijk, B.M.1    Niculescu-Duvaz, I.2    Gaulon, C.3
  • 26
    • 33846899405 scopus 로고    scopus 로고
    • Molecular recognition of protein kinase binding pockets for design of potent and selective kinase inhibitors
    • Liao JJ-L. Molecular recognition of protein kinase binding pockets for design of potent and selective kinase inhibitors. J Med Chem 2007;50:409-24.
    • (2007) J Med Chem , vol.50 , pp. 409-424
    • Liao, J.J.-L.1
  • 27
    • 77955602211 scopus 로고    scopus 로고
    • Gatekeeper mutations mediate resistance to BRAF-targeted therapies
    • Whittaker S, Kirk R, Hayward R, et al. Gatekeeper mutations mediate resistance to BRAF-targeted therapies. Sci Transl Med 2010;2:35ra41.
    • (2010) Sci Transl Med , vol.2
    • Whittaker, S.1    Kirk, R.2    Hayward, R.3
  • 28
    • 0028970609 scopus 로고
    • Transforming p21 mutants and c-Ets-2 activate the cyclin D1 promoter through distinguishable regions
    • Albanese C, Johnson J, Watanabe G, et al. Transforming p21 mutants and c-Ets-2 activate the cyclin D1 promoter through distinguishable regions. J Biol Chem 1995;270:23589-97.
    • (1995) J Biol Chem , vol.270 , pp. 23589-23597
    • Albanese, C.1    Johnson, J.2    Watanabe, G.3
  • 29
    • 77949685981 scopus 로고    scopus 로고
    • RAF inhibitors prime wild-type RAF to activate the MAPK pathway and enhance growth
    • Hatzivassiliou G, Song K, Yen I, et al. RAF inhibitors prime wild-type RAF to activate the MAPK pathway and enhance growth. Nature 2010;464:431-5.
    • (2010) Nature , vol.464 , pp. 431-435
    • Hatzivassiliou, G.1    Song, K.2    Yen, I.3
  • 30
    • 74849109743 scopus 로고    scopus 로고
    • Kinase-dead BRAF, oncogenic RAS cooperate to drive tumor progression through CRAF
    • Heidorn SJ, Milagre C, Whittaker S, et al. Kinase-dead BRAF, oncogenic RAS cooperate to drive tumor progression through CRAF. Cell 2010;140:209-21.
    • (2010) Cell , vol.140 , pp. 209-221
    • Heidorn, S.J.1    Milagre, C.2    Whittaker, S.3
  • 31
    • 33750284658 scopus 로고    scopus 로고
    • In melanoma, RAS mutations are accompanied by switching signaling from BRAF to CRAF and disrupted cyclic AMP signaling
    • Dumaz N, Hayward R, Martin J, et al. In melanoma, RAS mutations are accompanied by switching signaling from BRAF to CRAF and disrupted cyclic AMP signaling. Cancer Res 2006;66:9483-91.
    • (2006) Cancer Res , vol.66 , pp. 9483-9491
    • Dumaz, N.1    Hayward, R.2    Martin, J.3
  • 32
    • 66149126085 scopus 로고    scopus 로고
    • Antitumor efficacy of the novel RAF inhibitor GDC-0879 is predicted by BRAFV600E mutational status and sustained extracellular signal-regulated kinase/mitogen-activated protein kinase pathway suppression
    • Hoeflich KP, Herter S, Tien J, et al. Antitumor efficacy of the novel RAF inhibitor GDC-0879 is predicted by BRAFV600E mutational status and sustained extracellular signal-regulated kinase/mitogen-activated protein kinase pathway suppression. Cancer Res 2009;69:3042-51.
    • (2009) Cancer Res , vol.69 , pp. 3042-3051
    • Hoeflich, K.P.1    Herter, S.2    Tien, J.3
  • 33
    • 0345549402 scopus 로고    scopus 로고
    • Glucuronidation as a mechanism of intrinsic drug resistance in colon cancer cells: Contribution of drug transport proteins
    • Cummings J, Zelcer N, Allen JD, et al. Glucuronidation as a mechanism of intrinsic drug resistance in colon cancer cells: contribution of drug transport proteins. Biochem Pharmacol 2004;67:31-9.
    • (2004) Biochem Pharmacol , vol.67 , pp. 31-39
    • Cummings, J.1    Zelcer, N.2    Allen, J.D.3
  • 34
    • 56749160512 scopus 로고    scopus 로고
    • Design and synthesis of orally bioavailable benzimidazoles as Raf kinase inhibitors
    • Ramurthy S, Subramanian S, Aikawa M, et al. Design and synthesis of orally bioavailable benzimidazoles as Raf kinase inhibitors. J Med Chem 2008;51:7049-52.
    • (2008) J Med Chem , vol.51 , pp. 7049-7052
    • Ramurthy, S.1    Subramanian, S.2    Aikawa, M.3
  • 35
    • 12144289677 scopus 로고    scopus 로고
    • Structural basis for activation of the RAF-ERK signaling pathway by oncogenic mutations of B-RAF
    • Wan PTC, Garnett MJ, Roe SM, et al. Structural basis for activation of the RAF-ERK signaling pathway by oncogenic mutations of B-RAF. Cell 2004;116:855-67.
    • (2004) Cell , vol.116 , pp. 855-867
    • Wan, P.T.C.1    Garnett, M.J.2    Roe, S.M.3
  • 36
    • 0035800507 scopus 로고    scopus 로고
    • Clinical resistance to STI-571 cancer therapy caused by BCR-ABL gene mutation or amplification
    • Gorre ME, Mohammed M, Ellwood K, et al. Clinical resistance to STI-571 cancer therapy caused by BCR-ABL gene mutation or amplification. Science 2001;293:876-80.
    • (2001) Science , vol.293 , pp. 876-880
    • Gorre, M.E.1    Mohammed, M.2    Ellwood, K.3
  • 37
    • 18244371651 scopus 로고    scopus 로고
    • Acquired resistance of lung adenocarcinomas to gefitinib or erlotinib is associated with a second mutation in the EGFR kinase domain
    • Pao W, Miller VA, Politi KA, et al. Acquired resistance of lung adenocarcinomas to gefitinib or erlotinib is associated with a second mutation in the EGFR kinase domain. PLoS Med 2005;2:e73.
    • (2005) PLoS Med , vol.2
    • Pao, W.1    Miller, V.A.2    Politi, K.A.3
  • 38
    • 20844448396 scopus 로고    scopus 로고
    • A new mutation in the KIT ATP pocket causes acquired resistance to imatinib in a gastrointestinal stromal tumor patient
    • Tamborini E, Bonadiman L, Greco A, et al. A new mutation in the KIT ATP pocket causes acquired resistance to imatinib in a gastrointestinal stromal tumor patient. Gastroenterology 2004;127:294-9.
    • (2004) Gastroenterology , vol.127 , pp. 294-299
    • Tamborini, E.1    Bonadiman, L.2    Greco, A.3


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