Identification of pyridazin-3-one derivatives as potent, selective histamine H 3 receptor inverse agonists with robust wake activity

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 18, 2011, Pages 5493-5497

  Hudkins, Robert L ^a   Aimone, Lisa D ^a   Bailey, Thomas R ^a   Bendesky, Robert J ^a   Dandu, Reddeppa Reddy ^a   Dunn, Derek ^a   Gruner, John A ^a   Josef, Kurt A ^a   Lin, Yin Guo ^a   Lyons, Jacquelyn ^a   Marcy, Val R ^a   Mathiasen, Joanne R ^a   Sundar, Babu G ^a   Tao, Ming ^a   Zulli, Allison L ^a   Raddatz, Rita ^a   Bacon, Edward R ^a  

^a CEPHALON INC   (United States)

Author keywords

CEP 26401; H 3 inverse agonist; Histamine H 3; Pyridazin 3 one; Sleep wake

Indexed keywords

PYRIDAZIN 3 ONE DERIVATIVE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; DRUG IDENTIFICATION; DRUG STRUCTURE; MALE; NONHUMAN; RAT; WAKEFULNESS;

ANIMALS; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRINKING; HISTAMINE AGONISTS; HUMANS; MALE; MOLECULAR STRUCTURE; PYRIDAZINES; RATS; RECEPTORS, HISTAMINE H3; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; WAKEFULNESS;

RATTUS;

EID: 80051933140     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.06.108     Document Type: Article

References (32)

1. For reviews see: M. Berlin, C.W. Boyce, and M. de Lera Ruiz J. Med. Chem. 54 2011 26
2. R.E. Brown, D.R. Stevens, and H.L. Haas Prog. Neurobiol. 63 2001 637
3. R. Leurs, R.A. Bakker, H. Timmerman, and I.J. de Esch Nat. Rev. Drug Discovery 4 2005 107
4. M. Wijtmans, R. Leurs, and I. de Esch Expert Opin. Investig. Drugs 16 2007 967
5. T.A. Esbenshade, G.B. Fox, and M.D. Cowart Mol. Interv. 6 2006 77
6. T.A. Esbenshade, K.E. Browman, R.S. Bitner, M. Strakhova, M.D. Cowart, and J.D. Brioni Br. J. Pharmacol. 154 2008 1166
7. R.L. Hudkins, and R. Raddatz Ann. Rep. Med. Chem. 42 2007 49
8. R. Raddatz, M. Tao, and R.L. Hudkins Curr. Top. Med. Chem. 10 2010 153
9. J.D. Brioni, T.A. Esbenshade, T.R. Garrison, S.R. Bitner, and M.D. Cowart J. Pharmacol. Exp. Ther. 336 2011 38
10. A.D. Medhurst, A.R. Atkins, I.J. Beresford, K. Brackenborough, M.A. Briggs, A.R. Calver, J. Cilia, J.E. Cluderay, B. Crook, J.B. Davis, R.K. Davis, R.P. Davis, L.A. Dawson, A.G. Foley, J. Gartlon, M.I. Gonzalez, T. Heslop, W.D. Hirst, C. Jennings, D.N. Jones, L.P. Lacroix, A. Martyn, S. Ociepka, A. Ray, C.M. Regan, J.C. Roberts, J. Schogger, E. Southam, T.O. Stean, B.K. Trail, N. Upton, G. Wadsworth, J.A. Wald, T. White, J. Witherington, M.L. Woolley, A. Worby, and D.M. Wilson J.Pharmacol. Exp. Ther. 321 2007 1032
11. T. Nagase, T. Mizutani, S. Ishikawa, E. Sekino, T. Sasaki, T. Fujimura, S. Ito, Y. Mitobe, Y. Miyamoto, R. Yoshimoto, T. Tanaka, A. Ishihara, N. Takenaga, S. Tokita, T. Fukami, and N. Sato J. Med. Chem. 51 2008 4780
12. Thompson Reuters Integrity, Bavisant, entry 470497, 2011.
13. Thompson Reuters Integrity, MK-0249, entry 433171, 2011.
14. R. Leurs, P.L. Chazot, F.C. Shenton, H.D. Lim, and I.J. de Esch Br. J. Pharmacol. 157 2009 14
15. E. Zampeli, and E. Tiligada Br. J. Pharmacol. 157 2009 24
16. H.G. Bhatt, Y.K. Agrawal, H.G. Raval, K. Manna, and P.R. Desai Mini Rev. Med. Chem. 10 2010 1293
17. Bacon, E. R.; Bailey, T. R.; Becknell, N. C.; Chatterjee, S.; Dunn, D.; Hostetler, G. A.; Hudkins, R. L.; Josef, K. A.; Knutsen, L.; Tao, M.; Zulli, A. L.; US2010273779, 2010.
18. R.L. Hudkins, R. Raddatz, M. Tao, J.R. Mathiasen, L.D. Aimone, N.C. Becknell, C.P. Prouty, L. Knutsen, M. Yazdanian, G. Moachon, M.A. Ator, J.P. Mallamo, M.J. Marino, E.R. Bacon, and M. Williams J. Med. Chem. 54 2011 4781
19. W.V. Curran, and A. Ross J. Med. Chem. 17 1974 273
20. E. Sotelo, and E. Ravina Syn. Comm. 30 2000 1
21. C.G. Wermuth, G. Schlewer, J.J. Bourguignon, G. Maghioros, M.J. Bouchet, C. Moire, J.P. Kan, P. Worms, and K. Biziere J. Med. Chem. 32 1989 528
22. W.J. Coates, and A. McKillop Synthesis 1993 334
23. A.L. Hopkins, C.R. Groom, and A. Alex Drug Discovery Today 9 2004 430
24. P.D. Lesson, and B. Springthorpe Nat. Rev. Drug Discovery 6 2007 881
25. E. Perola J. Med. Chem. 53 2010 2986
26. J.P. Ploemen, J. Kelder, T. Hafmans, H. van de Sandt, J.A. van Burgsteden, P.J. Saleminki, and E. van Esch Exp. Toxicol. Pathol. 55 2004 347
27. M.J. Reasor, K.L. Hastings, and R.G. Ulrich Expert Opin. Drug Saf. 5 2006 567
28. J. Clapham, and G.J. Kilpatrick Eur. J. Pharmacol. 232 1993 99
29. J.S. Lin, O.A. Sergeeva, and H.L. Haas J. Pharmacol. Exp. Ther. 336 2011 17
30. S. Le, J.A. Gruner, J.R. Mathiasen, M.J. Marino, and H. Schaffhauser J. Pharmacol. Exp. Ther. 325 2008 902
31. D.M. Edgar, and W.F. Seidel J. Pharmacol. Exp. Ther. 283 1997 757
32. M.R. Opp, and J.M. Krueger Brain Res. 639 1994 57