The design and synthesis of a potent glucagon receptor antagonist with favorable physicochemical and pharmacokinetic properties as a candidate for the treatment of type 2 diabetes mellitus

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 10, 2013, Pages 3051-3058

  Guzman Perez, Angel ^a   Pfefferkorn, Jeffrey A ^a   Lee, Esther C Y ^a   Stevens, Benjamin D ^a   Aspnes, Gary E ^a   Bian, Jianwei ^a   Didiuk, Mary T ^a   Filipski, Kevin J ^a   Moore, Dianna ^a   Perreault, Christian ^a   Sammons, Matthew F ^a   Tu, Meihua ^a   Brown, Janice ^a   Atkinson, Karen ^a   Litchfield, John ^a   Tan, Beijing ^a   Samas, Brian ^a   Zavadoski, William J ^a   Salatto, Christopher T ^a   Treadway, Judith ^a  

^a PFIZER INC   (United States)

Author keywords

Glucagon receptor antagonist Diabetes mellitus Physicochemical properties

Indexed keywords

3 [4 (1 [3,5 DIMETHYL 4 [4 (TRIFLUOROMETHYL) 1H PYRAZOL 1 YL]PHENOXY]BUTYL]BENZAMIDO]PROPANOIC ACID; ANTIDIABETIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CYTOTOXICITY; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG SAFETY; DRUG SYNTHESIS; IN VIVO STUDY; LIPOPHILICITY; MOLECULAR WEIGHT; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; RAT;

ANIMALS; CHEMISTRY, PHYSICAL; DIABETES MELLITUS, TYPE 2; DOGS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; EPITHELIAL CELLS; HAPLORHINI; HUMANS; LIVER; MICE; MOLECULAR STRUCTURE; PROPIONATES; RATS; RECEPTORS, GLUCAGON; SMALL MOLECULE LIBRARIES; STRUCTURE-ACTIVITY RELATIONSHIP;

CANIS FAMILIARIS; RATTUS;

EID: 84876695331     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.03.014     Document Type: Article

References (28)

1. G. Danaei, M.M. Finucane, Y. Lu, G.M. Singh, M.J. Cowan, C.J. Paciorek, J.K. Lin, F. Farzadfar, Y.-H. Khang, G.A. Stevens, M. Rao, M.K. Ali, L.M. Riley, C.A. Robinson, and M. Ezzati Lancet 378 2011 31
2. A.R. Saltiel Cell 104 2001 517
3. A.J. Krentz, M.B. Patel, and C.J. Bailey Drugs 68 2008 2131
4. B.E. Dunning, and J.E. Gerich Endocr. Rev. 28 2007 253
5. S. Ali, and D.J. Drucker Am. J. Physiol. Endocrinol. Metab. 296 2009 E415
6. S.S. Engel, L. Xu, P.J. Andryuk, M.J. Davies, J. Amatruda, K. Kaufman, and B.J. Goldstein Diabetes 60 2011 A85
7. Parmee, E. R. Abstracts of Papers, 241st National Meeting of the American Chemical Society, Anaheim, CA; American Chemical Society: Washington, DC, 2011; Abstract MEDI-31.
8. Y. Xiong, J. Guo, M.R. Candelore, R. Liang, C. Miller, Q. Dallas-Yang, G. Jiang, P.E. McCann, S.A. Qureshi, X. Tong, S.S. Xu, J. Shang, S.H. Vincent, L.M. Tota, M.J. Wright, X. Yang, B.B. Zhang, J.R. Tata, and E.R. Parmee J. Med. Chem. 55 2012 6137
9. D.-M. Shen, S. Lin, and E.R. Parmee Exp. Opin. Ther. Patents 21 2011 1211
10. R.P. Kelly, P. Garhyan, E.J. Abu-Raddad, H. Fu, C.N. Lim, M.J. Prince, J.A. Pinaire, M.T. Loh, and M.A. Deeg Diabetes 60 2011 A84
11. D.E. DeMong, M.W. Miller, and J.E. Lachowicz Annu. Rep. Med. Chem. 43 2008 119
12. M.P. Edwards, and D.A. Price Annu. Rep. Med. Chem. 45 2010 381
13. P.D. Leeson, and J.R. Empfield Annu. Rep. Med. Chem. 45 2010 393
14. J.D. Hughes, J. Blagg, D.A. Price, S. Bailey, G.A. DeCrescenzo, R.V. Devraj, E. Ellsworth, Y.M. Fobian, M.E. Gibbs, R.W. Gilles, N. Greene, E. Huang, T. Krieger-Burke, J. Loesel, T. Wagner, L. Whiteley, and Y. Zhang Bioorg. Med. Chem. Lett. 18 2008 4872
15. D.A. Price, J. Blagg, L. Jones, N. Greene, and T. Wager Exp. Opin. Drug Metab. Toxicol. 5 2009 921
16. K.J. Filipski, J. Bian, D.C. Ebner, E.C.Y. Lee, J.-C. Li, M.F. Sammons, S.W. Wright, B.D. Stevens, M.T. Didiuk, M. Tu, C. Perreault, J. Brown, K. Atkinson, B. Tan, J. Litchfield, J.A. Pfefferkorn, and A. Guzman-Perez Bioorg. Med. Chem. Lett. 22 2012 415
17. H. Ren, A. Krasovskiy, and P. Knochel Org. Lett. 6 2004 4215
18. J.W. Bae, S.H. Lee, Y.J. Cho, and C.M. Yoon J. Chem. Soc., Perkin Trans. 1 2000 145
19. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, and R. Noyori J. Am. Chem. Soc. 118 1996 2522
20. H. Yamanaka, T. Takekawa, K. Morita, and T. Ishihara Tetrahedron Lett. 1996 1829 37
21. I.W. Davies, J.-F. Marcoux, J. Wu, M. Palucki, E.G. Corley, M.A. Robbins, N. Tsou, R.G. Ball, P. Dormer, R.D. Larson, and P.J. Reider J. Org. Chem. 65 2000 4571
22. K.W. Anderson, T. Ikawa, R.E. Tundel, and S.L. Buchwald J. Am. Chem. Soc. 128 2006 10694
23. K.J. Filipski, J.T. Kohrt, A. Casimiro-Garcia, C.A. Van Huis, D.A. Dudley, W.L. Cody, C.F. Bigge, S. Desiraju, S. Sun, S.N. Maiti, M.R. Jaber, and J.J. Edmunds Tetrahedron Lett. 47 2006 7677
24. P. Li, R. Rogers, D. Smiley, R.D. DiMarchi, and F. Zhang Acta Crystallogr., Sect. F: Struct. Biol. Cryst. Commun. 63 2007 599
25. L. Di, C. Whitney-Pickett, J.P. Umland, H. Zhang, X. Zhang, D.F. Gebhard, Y. Lai, J.J. Federico III, R.E. Davidson, R. Smith, E.L. Reyner, C. Lee, B. Feng, C. Rotter, M.V. Varma, S. Kempshall, K. Fenner, A.F. El-Kattan, T.E. Liston, and M.D. Troutman J. Pharm. Sci. 100 2011 4974
26. R.W.W. Hooft, L.H. Straver, and A.L. Spek J. Appl. Crystallogr. 41 2008 96
27. A.L. Spek J. Appl. Crystallogr. 36 2003 7
28. N. Greene, M.D. Aleo, S. Louise-May, D.A. Price, and Y. Will Bioorg. Med. Chem. Lett. 20 2010 5308