6,7-Dihydro-5H-cyclopenta[d]pyrazolo[1,5-a]pyrimidines and their derivatives as novel corticotropin-releasing factor 1 receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 18, 2011, Pages 5432-5445

  Saito, Tetsuji ^a   Obitsu, Tetsuo ^a   Kondo, Takashi ^a   Matsui, Toshiaki ^a   Nagao, Yuuki ^a   Kusumi, Kensuke ^a   Matsumura, Naoya ^a   Ueno, Sonoko ^a   Kishi, Akihiro ^a   Katsumata, Seishi ^a   Kagamiishi, Yoshifumi ^a   Nakai, Hisao ^a   Toda, Masaaki ^a  

^a ONO PHARMACEUTICAL CO   (Japan)

Author keywords

Antagonist; Corticotrophin releasing factor 1 receptor

Indexed keywords

(1 ETHYL PROPYL) [3 (4 METHOXY 2 CHLOROPHENYL) 2 METHYL 6,7 DIHYDRO 5H 1,4,8A TRIAZA S INDACEN 8 YL] AMINE; 2 (2 CHLORO 4 METHYLPHENYL) 3 OXO BUTYRONITRILE; 2 (2 METHYL 4 METHOXYPHENYL) 3 OXO BUTYRONITRILE; 2 (4 METHOXY 2 METHYLPHENYL) 3 OXO PENTANENITRILE; 2 (4 METHOXY 2 METHYLPHENYL) 3 OXO PROPIONITRILE; 3 (4 METHOXY 2 METHYLPHENYL) 2 METHYL 6,7 DIHYDRO 5H 1,4,8A TRIAZA S INDACEN 8 OL; 3 CYLCOBUTYL 2 (4 METHOXY 2 METHYLPHENYL) 3 OXO PROPIONITRILE; 4 (2 METHYL 4 METHYLPHENYL) 3 METHYL 1H PYRAZOL 5 AMINE; 4 (4 CHLORO 2 METHYLPHENYL) 5 METHYL 2H PYRAZOL 3 YLAMINE; 4 (4 METHOXY 2 METHYLPHENYL) 2H PYRAZOL 3 YLAMINE; 4 (4 METHOXY 2 METHYLPHENYL) 5 METHYLSULFANYLMETHYL 2H PYRAZOL 3 YLAMINE; 4 (4 METHOXY 2 METHYLPHENYL) 5 TRIFLUOROMETHYL 2H PYRAZOL 3 YLAMINE; 4,4,4 TRIFLUORO 2 (4 METHOXY 2 METHYLPHENYL) 3 OXO BUTYRONITRILE; 5 CYCLOBUTYL 4 (4 METHOXY 2 METHYLPHENYL) 2H PYRAZOL 3 YLAMINE; 5 ETHYL 4 (4 METHOXY 2 METHYLPHENYL) 2H PYRAZOL 3 YLAMINE; 6,7 DIHYDRO 5H CYCLOPENTAL[D]PYRAZOLO[1,5 A]PYRIMIDINE DERIVATIVE; 7 CHLORO 3 (4 METHOXY 2 METHYLPHENYL) 2,5,6 TRIMETHYL PYRAZIKI[1,5 A]PYRAMIDINE; 8 CHLORO 2 ETHYL 3 (4 METHOXY 2 METHYLPHENYL) 6,7 DIHYDRO 5H 1,4,8A TRIAZA S INDACENE; 8 CHLORO 3 (4 METHOXY 2 METHYLPHENYL) 2 METHYL 5H,7H 6 OXA 1,4,8A TRIAZA S INDACENE; 8 CHLORO 3 (4 METHOXY 2 METHYLPHENYL) 2 METHYL 5H,7H 6 THIA 1,4,8A TRIAZA S INDACENE; 8 CHLORO 3 (4 METHOXY 2 METHYLPHENYL) 2 METHYL 6,7 DIHYDRO 5H 1,4,8A TRIAZA S INDACENE; 8 CHLORO 3 (4 METHOXY 2 METHYLPHENYL) 6,7 DIHYDRO 5H 1,4,8A TRIAZA S INDACENE; 8 CHLORO 5 (4 METHOXY 2 METHYLPHENYL) 6 METHYL 2,3 DIHYDRO 1 OXA 4,7,7A TRIAZA S INDACENE; 8 CHLORO 5 (4 METHOXY 2 METHYLPHENYL) 6 METHYL 2,3 DIHYDRO 1 THIA 4,7,7A TRIAZA S INDACENE; 8 CHLORO 5 (4 METHOXY 2 METHYLPHENYL) 6 METHYL 2,3 DIHYDRO 1H 1,4,7,7A TETRAAZA S INDACENE; CORTICOTROPIN RELEASING FACTOR ANTAGONIST; CORTICOTROPIN RELEASING FACTOR RECEPTOR 1; CORTICOTROPIN RELEASING FACTOR RECEPTOR 1 ANTAGONIST; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG DISTRIBUTION; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; RAT; SINGLE DRUG DOSE;

ANIMALS; CHO CELLS; CRICETINAE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; MALE; MAZE LEARNING; MOLECULAR STRUCTURE; PYRAZOLES; PYRIMIDINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, CORTICOTROPIN-RELEASING HORMONE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE;

EID: 80052600644     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.07.055     Document Type: Article

References (43)

1. F. Holsboer, and M. Ising Eur. J. Pharmacol. 583 2008 350
2. C.F. Hemley, A. McCluskey, and P.A. Keller Curr. Drug Targets 8 2007 105
3. E. Zoumakis, K.C. Rice, P.W. Gold, and G.P. Chrousos Ann. N.Y. Acad. Sci. 1083 2006 239
4. M. Ising, and F. Hosboer Exp. Clin. Psychopharmacol. 15 2007 519
5. W. Vale, J. Speiss, and C. Rivier Science 213 1981 1394
6. J.H. Kehne, and S. De Lombaert Curr. Drug Targets CNS Neurol. Disorders 1 2002 467
7. De Souza, E.;Grigoriadis, D.E., In Neuropsychopharmacology; The Fifth Generation of Williams & Wilkins, Philadelphia; 2002.
8. C.D. Dzierba, R.A. Hartz, and J.J. Bronson Annu. Rep. Med. Chem. 43 2008 3
9. T. Stckler, and F.M. Dautzenberg CNS Neurol. Disord. Drug Targets 5 2006 147
10. P.J. Gilligan, and Y.-W. Li Curr. Opin. Drug Discov Devel. 7 2004 487
11. C. Chen Curr. Med. Chem. 13 2006 1261
12. P.J. Gilligan Expert Opin. Ther. Patents 16 2006 913
13. A.W. Zolbel, T. Nichel, H.E. Kunzel, and N. Ackl J. Psychiatr. Res. 34 2000 171
14. B. Binneman, D. Feltner, S. Kolluri, Y. Shi, R. Qiu, and T. Stiger Am. J. Psychiatry 165 2008 617
15. E.M. Strome, G.H. Wheler, J.D. Higley, D.L. Loriaux, S.J. Soumi, and D.J. Doudet Proc. Natl. Acad. Sci. U.S.A. 99 2002 15749
16. M. Roche, K.G. Commons, A. Peoples, and R.J. Valentino J. Neurosci. 23 2003 970
17. V.P. Bakshi, S. Smith-roe, S.M. Newman, D.E. Grigoriadis, and N.H. Kalin J. Neurosci. 22 2002 2926
18. D.W. Schulz, R.S. Mansbach, J. Sprouse, J.P. Braselton, J. Collins, M. Corman, A. Dunaiskis, S. Faraci, A.W. Schmidt, T. Seeger, P. Seymour, F.D. Tingley III, E.N. Winston, Y.L. Chen, and J. Heym Proc. Natl. Acad. Sci. U.S.A. 93 1996 10477
19. Y.L. Chen, R.S. Mansbach, S.M. Winter, E. Brooks, J. Collins, M.L. Corman, A.R. Dunaiskis, W.S. Faraci, R.J. Gallaschun, A. Schmidt, and D.W. Schulz J. Med. Chem. 40 1997 1749
20. P.J. Gilligan, C. Baldauf, A. Cocuzza, D. Chidester, R. Zaczek, L.W. Fitzgerald, J.F. McElroy, M.A. Smith, H.-S.L. Shen, J.A. Saye, D. Christ, G. Trainor, D.W. Robertson, and P. Hartig Bioorg. Med. Chem. 8 2000 181
21. S. Chaki, A. Nakazato, L. Kennis, M. Nakamura, C. Mackie, M. Sugiura, P. Vinken, D. Ashton, X. Langlois, and T. Steckler Eur. J. Pharmacol. 485 2004 145
22. P.J. Gilligan, B.K. Folmer, R.A. Hartz, S. Koch, K.K. Nanda, S. Andreuski, L. Fitzgerald, K. Miller, and W.J. Marshall Bioorg. Med. Chem. 11 2003 4093
23. B. Dyck, D.E. Grigoriadis, R.S. Gross, Z. Guo, M. Haddach, D. Marinkovic, J.R. McCarthy, M. Moorjani, C.F. Regan, J. Saunders, M.K. Schwaebe, T. Szabo, J.P. Williams, X. Zhang, H. Bozigian, and T.K. Chen J. Med. Chem. 48 2005 4100
24. Z. Guo, J.E. Tellew, R.S. Gross, B. Dyck, J. Grey, M. Haddach, M. Kiankarimi, M. Lanier, B.-F. Li, Z. Luo, J.R. McCarthy, J. Saunders, R. Sullivan, X. Zhang, S. Zamani-Kord, D.E. Grigoriadis, P.D. Crowe, T.K. Chen, and J.P. Williams J. Med. Chem. 48 2005 5104
25. R.S. Gross, Z. Guo, B. Dyck, T. Coon, C.Q. Huang, R.F. Lowe, D. Marinkovic, M. Moorjani, J. Nelson, S. Zamani-Kord, D.E. Grigoriadis, S.R.J. Hoare, P.D. Crowe, J.H. Bu, M. Haddach, J. McCarthy, J. Saunders, R. Sullivan, T. Chen, and J.P. Williams Med. Chem. 48 2005 5780
26. X. Han, S.S. Pin, K. Burris, L.K. Fung, S. Huang, M.T. Taber, J. Zhang, and G.M. Dubowchik Bioorg. Med. Chem. Lett. 15 2005 4029
27. X. Han, R. Civiello, S.S. Pin, K. Burris, L.A. Balanda, J. Knipe, S. Ren, T. Fiedler, K.E. Browman, R. Macci, M.T. Taber, J. Zhang, and G.M. Dubowchik Bioorg. Med. Chem. Lett. 17 2007 2026
28. G. Gentile, R. Di Fabio, F. Pavone, F.M. Sabbatini, Y. St-Denis, M.G. Zampori, G. Vitulli, and A. Worby Bioorg. Med. Chem. Lett. 17 2007 5218
29. Y. St-Denis, R. Di Fabio, G. Bernasconi, E. Castiglioni, S. Conati, E. Fazzolari, G. Gentile, D. Ghirlanda, C. Marchionni, F. Messina, F. Micheli, F. Pavone, A. Pasqarello, F.M. Sabbatini, M.G. Zampori, R. Arban, and G. Vitulli Bioorg. Med. Chem. Lett. 15 2005 3713
30. Nakazato, A.; Okubo, T.; Nozawa, D.; Tamita T.; Kennis, L.E.J., PCT Publication WO 2005/066178.
31. Luo, Z.; Tellew J.E.; Williams, J., PCT Publication WO 2005/063749.
32. Hibi S.; Hoshino Y.; Yoshiuchi T.; Shin K.; Kikuchi K. et al, WO200142247.
33. L. He, P.J. Gilligan, R. Zaczek, L.W. Fitzgerald, J. McElroy, H.-S.L. Shen, J.A. Saye, N.H. Kalin, S. Shelton, D. Christ, G. Trainor, and P. Hartig J. Med. Chem. 43 2000 449
34. T. Matsuda, and M. Yamazaki Chem. Pharm. Bull. 33 1985 937
35. T.G. Miller, and J.W. Thanassi J. Org. Chem. 25 1960 2009
36. G. Battaglia, E.L. Webster, and E.B. De Souza Synapse 1 1987 572
37. J.F. McElroy, K. Ward, K.L. Zeller, K.W. Jones, P.L. Gilligan, L. He, and S. Lelas Psychopharmacology 165 2002 86
38. Y.-W. Li, G. Hill, H. Wong, N. Kelly, K. Ward, M. Pierdomenico, S. Ren, P. Gilligan, S. Grossman, G. Trainor, R. Taub, J. McElroy, and R. Zaczek J. Pharmacol. Exp. Ther. 305 2003 86
39. Y.-W. Li, L. Fitzgerald, H. Wong, S. Lelas, G. Zhang, M.D. Lindner, T. Wallace, McElroy, N.J. Lodge, P.J. Gilligan, and R. Zaczek CNS Drug Rev. 11 2005 21
40. C. Chen, K.M. Wilcoxen, C.Q. Huang, J.R. McCarthy, T. Chen, and D.E. Grigoriadis Bioorg. Med. Chem. Lett. 14 2004 3669
41. R.A. Hartz, K.K. Nanda, C.L. Ingalls, V.T. Ahuja, T.F. Molski, G. Zhang, H. Wong, Y. Peng, M. Kelley, N.J. Lodge, R. Zaczek, P.J. Gilligan, and G.L. Trainor J. Med. Chem. 47 2004 4741
42. P.J. Gilligan, C. Baldauf, A. Cocuzza, D. Chidester, R. Zaczek, L.W. Fitzgerald, J. McElroy, M.A. Smith, H.-S.L. Shen, J.A. Saye, D. Christ, G. Trainor, D.W. Robertson, and P. Hartig Bioorg. Med. Chem. 8 2000 181
43. M.P. Moyer, P.L. Feldman, and H. Rapoport J. Org. Chem. 50 1985 5223