N-(1-Benzylpyrrolidin-3-yl)arylbenzamides as potent and selective human dopamine D 4 antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 19, 2004, Pages 4847-4850

  Egle, Ian ^a   Barriault, Nancy ^a   Bordeleau, Michel ^a   Drage, Jillian ^a   Dube, Laurence ^a   Peragine, Jack ^a   Mazzocco, Lucy ^a   Arora, Jalaj ^a   Jarvie, Keith ^a   Tehim, Ashok ^a  

^a NPS Pharmaceuticals Inc   (Canada)

Author keywords

D 4 antagonists; Dopamine

Indexed keywords

ANTIPARKINSON AGENT; BENZAMIDE DERIVATIVE; DOPAMINE 2 RECEPTOR; DOPAMINE 4 RECEPTOR; DOPAMINE RECEPTOR BLOCKING AGENT; LIGAND;

ADRENERGIC RECEPTOR BLOCKING; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; NONHUMAN; STRUCTURE ACTIVITY RELATION;

BENZAMIDES; DOPAMINE ANTAGONISTS; HUMANS; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D4; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4444252847     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.07.045     Document Type: Article

References (16)

1. H.I. Kaplan, B.J. Saddock, and J.A. Grebb Comprehensive Textbook of Psychiatry 7th ed. 1994 Williams and Wilkins Baltimore
2. M. Beiser, and W.G. Iacono Can. J. Psychiat. 35 1990 657 668
3. A.H.C. Wong, S. Sanyal, M.G.L. Knapp, and H.H.M. Van Tol Expert Opin. Ther. Targets 3 1999 571 586
4. A. Chatterjee, M. Chakos, A. Koreen, S. Geisler, B. Sheitman, M. Woerner, J.M. Kane, J. Alvir, and J.A. Lieberman Am. J. Psychiat. 152 1995 1724 1729
5. A. Breier, R.W. Buchanan, B. Kirkpatrick, O.R. Davis, D. Irish, A. Summerfelt, and W.T. Carpenter Am. J. Psychiat. 151 1994 20 26
6. P. Krupp, and P. Barnes Br. J. Psychiat. 160 1992 38 40
7. M.A. Lee, P.A. Thompson, and H.Y. Meltzer J. Clin. Psychiat. 55 1994 82 87
8. C.A. Tamminga Can. J. Psychiat. 42 1997 265 273
9. J.J. Kulagowski, H.B. Broughton, N.R. Curtis, I.M. Mawer, M.P. Ridgill, R. Baker, F. Emms, S.B. Freedman, R. Marwood, S. Patel, S. Patel, C.I. Ragan, and P.D. Leeson J. Med. Chem. 39 1996 1941 1942
10. K.M. Merchant, G.S. Gill, D.W. Harris, R.M. Huff, M.J. Eaton, K. Lookingland, B.S. Lutzke, R.B. Mccall, M.F. Piercey, P.J. Schreur, V.H. Sethy, M.W. Smith, K.A. Svensson, A.H. Tang, P.F. Vonvoigtlander, and R.E. Tenbrink J. Pharmacol. Exp. Ther. 279 1996 1392 1403
11. M.S. Kramer, B. Last, A. Getson, and S.A. Reines Arch. Gen. Psychiat. 54 1997 567 572
12. F.I. Tarazi, and R.J. Baldessarini Mol. Psychiat. 4 1999 529 538
13. Tehim, A.; Wang, X.; Arora, J.; Treasurywala, A. WO Patent 9837064, 1998
14. J. Ohmori, K. Maeno, K. Hidaka, K. Nakato, M. Matsumoto, S. Tada, H. Hattori, S. Sakamoto, S. Tsukamoto, S. Usada, and T. Mase J. Med. Chem. 39 1996 2764 2772
15. 4), filtered, and concentrated to provide 7b (196 mg, 85%)
16. 3) δ 1.71-1.87 (m, 1H), 2.32-2.48 (m, 2H), 2.67 (dd, 1H), 2.79 (dd, 1H), 2.92-3.03 (m, 1H), 3.69 (s, 2H), 4.64-4.75 (m, 1H), 6.66 (br d, 1H), 7.12 (dd, 1H), 7.25-7.37 (m, 6H), 7.39 (dd, 1H), 7.67 (d, 2H), 7.78 (d, 2H)