Development of amino-pyrimidine inhibitors of c-Jun N-terminal kinase (JNK): Kinase profiling guided optimization of a 1,2,3-benzotriazole lead

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 5, 2013, Pages 1486-1492

  Palmer, Wylie S ^a,b   Alam, Muzaffar ^a   Arzeno, Humberto B ^a   Chang, Kung Ching ^a   Dunn, James P ^a   Goldstein, David M ^a   Gong, Leyi ^a   Goyal, Bindu ^a   Hermann, Johannes C ^a   Hogg, J Heather ^a   Hsieh, Gary ^a   Jahangir, Alam ^a   Janson, Cheryl ^b   Jin, Sue ^a   Ursula Kammlott, R ^b   Kuglstatter, Andreas ^a   Lukacs, Christine ^b   Michoud, Christophe ^b   Niu, Linghao ^a   Reuter, Deborah C ^a   Shao, Ada ^a   Silva, Tania ^a   Trejo Martin, Teresa A ^a   Stein, Karin ^a   Tan, Yun Chou ^a   Tivitmahaisoon, Parcharee ^a   Tran, Patricia ^a   Wagner, Paul ^a   Weller, Paul ^a   Wu, Shao Yong ^a   more..

^a ROCHE BIOSCIENCE   (United States)

^b HOFFMANN LA ROCHE INC   (United States)

Author keywords

c Jun N terminal kinase (JNK); CDK; Kinase inhibitor; Kinase selectivity

Indexed keywords

BENZOTRIAZOLE DERIVATIVE; MITOGEN ACTIVATED PROTEIN KINASE 6; STRESS ACTIVATED PROTEIN KINASE 1; STRESS ACTIVATED PROTEIN KINASE INHIBITOR;

ALKYLATION; ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; IN VIVO STUDY; MALE; MAXIMUM PLASMA CONCENTRATION; MOLECULAR WEIGHT; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HUMANS; JNK MITOGEN-ACTIVATED PROTEIN KINASES; MODELS, MOLECULAR; PROTEIN KINASE INHIBITORS; PYRIMIDINES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

RATTUS;

EID: 84873709116     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.12.047     Document Type: Article

References (24)

1. G.L. Johnson, and R. Lapadat Science 2002 1911 298
2. B. Dérijard, M. Hibi, I.-H. Wu, T. Barrett, B. Su, T. Deng, M. Karin, and R.J. Davis Cell 1025 1994 76
3. B.J. Pulverer, J.M. Kyriakis, J. Avruch, E. Nikolakaki, and J.R. Woodgett Nature 353 1991 670
4. S. Gupta, T. Barrett, A.J. Whitmarsh, J. Cavanagh, H.K. Sluss, B. Dérijard, and R.J. Davis EMBO J. 15 1996 2760
5. T. Kallunki, B. Su, I. Tsigelny, H.K. Sluss, B. Derijard, G. Moore, R. Davis, and M. Karin Genes Dev. 8 1994 2996
6. J.H. Martin, A.A. Mohit, and C.A. Miller Mol. Brain Res. 35 1996 47
7. R.J. Davis Cell 103 2000 239
8. M.A. Bogoyevitch, K.R.W. Ngoei, T.T. Zhao, Y.Y.C. Yeap, and D.C.H. Ng Biochim. Biophys. Acta 1804 2010 463
9. M.A. Siddiqui, and P.A. Reddy J. Med. Chem. 53 2010 3005
10. J.A. Christopher, F.L. Atkinson, B.D. Bax, M.J.B. Brown, A.C. Champigny, T.T. Chuang, E.J. Jones, J.E. Mosley, and J.R. Musgrave Bioorg. Med. Chem. Lett. 19 2009 2230
11. M. Alam, R.E. Beevers, T. Ceska, R.J. Davenport, K.M. Dickson, M. Fortunato, L. Gowers, A.F. Haughan, L.A. James, M.W. Jones, N. Kinsella, C. Lowe, J.W.G. Meissner, A.-L. Nicolas, B.G. Perry, D.J. Phillips, W.R. Pitt, A. Platt, A.J. Ratcliffe, A. Sharpe, and L.J. Tait Bioorg. Med. Chem. Lett. 17 2007 3463
12. M.J. Stocks, S. Barber, R. Ford, F. Leroux, S. St-Gallay, S. Teague, and Y. Xue Bioorg. Med. Chem. Lett. 15 2005 3459
13. S.K. De, V. Chen, J.L. Stebbins, L.-H. Chen, J.F. Cellitti, T. Machleidt, E. Barile, M. Riel-Mehan, R. Dahl, L. Yang, A. Emdadi, R. Murphy, and M. Pellecchia Bioorg. Med. Chem. 18 2010 590
14. T. Kamenecka, R. Jiang, X. Song, D. Duckett, W. Chen, Y.Y. Ling, J. Habel, J.D. Laughlin, J. Chambers, M. Figuera-Losada, M.D. Cameron, L. Lin, C.H. Ruiz, and P.V. LoGrasso J. Med. Chem. 53 2010 419
15. L. Gong, Y.-C. Tan, G. Boice, S. Abbot, K. McCaleb, P. Iyer, F. Zuo, J.D. Porto, B. Wong, S. Jin, A. Chang, P. Tran, G. Hsieh, L. Niu, A. Shao, D. Reuter, C.M. Lukacs, R. Ursula Kammlott, A. Kuglstatter, and D. Goldstein Bioorg. Med. Chem. Lett. 22 2012 7381
16. A.M. Manning, and R.J. Davis Nat. Rev. Drug Disc. 2 2003 554
17. Z. Han, L. Chang, Y. Yamanishi, M. Karin, and G.S. Firestein Arthritis Rheum. 46 2002 818
18. K.F. Byth, J.D. Culshaw, S. Green, S.E. Oakes, and A.P. Thomas Bioorg. Med. Chem. Lett. 14 2004 2245
19. M.A. Fabian, W.H. Biggs, D.K. Treiber, C.E. Atteridge, M.D. Azimioara, M.G. Benedetti, T.A. Carter, P. Ciceri, P.T. Edeen, M. Floyd, J.M. Ford, M. Galvin, J.L. Gerlach, R.M. Grotzfeld, S. Herrgard, D.E. Insko, M.A. Insko, A.G. Lai, J.-M. Lelias, S.A. Mehta, Z.V. Milanov, A.M. Velasco, L.M. Wodicka, H.K. Patel, P.P. Zarrinkar, and D.J. Lockhart Nat. Biotechnol. 23 2005 329
20. M.W. Karaman, S. Herrgard, D.K. Treiber, P. Gallant, C.E. Atteridge, B.T. Campbell, K.W. Chan, P. Ciceri, M.I. Davis, P.T. Edeen, R. Faraoni, M. Floyd, J.P. Hunt, D.J. Lockhart, Z.V. Milanov, M.J. Morrison, G. Pallares, H.K. Patel, S. Pritchard, L.M. Wodicka, and P.P. Zarrinkar Nat. Biotechnol. 26 2008 127 The selectivity score calculation is also described at: http://www.discoverx.com/ tools-resources/leadhunter-study-reports-data-analysis
21. P.R. Ortiz de Montellano, and J.M. Mathews Biochem. J. 195 1981 761
22. WO2010097335 F. Hoffmann-La Roche, Switzerland.
23. Alternative binding modes have been reported for an imidazopyridine analogue similar to compound 10, see: G.M. Buckley, T.A. Ceska, J.L. Fraser, L. Gowers, C.R. Groom, A.P. Higueruelo, K. Jenkins, S.R. Mack, T. Morgan, D.M. Parry, W.R. Pitt, O. Rausch, M.D. Richard, and V. Sabin Bioorg. Med. Chem. Lett. 18 2008 3291
24. U.S. Patent 8183,254, May 22, 2012.