Synthesis and structure-activity relationship of the isoindolinyl benzisoxazolpiperidines as potent, selective, and orally active human dopamine D4 receptor antagonists

ChemBioChem

Volumn 3, Issue 10, 2002, Pages 999-1009

  Hendrix, James A ^a   Shimshock, Stephen J ^a   Shutske, Gregory M ^a   Tomer IV, John D ^b   Kapples, Kevin J ^a   Palermo, Mark G ^c   Corbett, Thomas J ^f   Vargas, Hugo M ^d   Kafka, Sharon ^a   Brooks, Karen M ^a   Laws Ricker, Lynn ^a   Lee, David K H ^e   De Lannoy, Inez ^e   Bordeleau, Michel ^e   Rizkalla, Geihan ^e   Owolabi, Joshua ^e   Kamboj, Rajender K ^e  

^a SANOFI   (France)

^b ELI LILLY AND COMPANY   (United States)

^c NOVARTIS PHARMA AG   (Switzerland)

^d MERCK RESEARCH LABORATORIES   (United States)

^e NPS Allelix Corp   (Canada)

^f NONE

Author keywords

Alcohols; Chirality; Dopamines; G protein coupled receptors; Isoindolines; Schizophrenia

Indexed keywords

2 PHENYL 4 [4 (2 PYRIMIDINYL) 1 PIPERAZINYLMETHYL]IMIDAZOLE; 3 (2,3 DIHYDRO 1H ISOINDOL 2 YL) 2 [4 (6 FLUOROBENZO[D]ISOXAZOL 3 YL)PIPERIDIN 1 YL]PROPAN 1 OL DIMALEATE; 3 (2,3 DIHYDRO 5 FLUORO 1H ISOINDOL 2 YL) 2 [4 (6 FLUOROBENZO[D]ISOXAZOL 3 YL)PIPERIDIN 1 YL]PROPAN 1 OL DIMALEATE; 3 (2,3 DIHYDRO 5 METHOXY 1H ISOINDOL 2 YL) 2 [4 (6 FLUOROBENZO[D]ISOXAZOL 3 YL)PIPERIDIN 1 YL]PROPAN 1 OL DIMALEATE; 3 [[4 (4 CHLOROPHENYL) 1 PIPERAZINYL]METHYL] 1H PYRROLO[2,3 B]PYRIDINE; ALPHA 1 ADRENERGIC RECEPTOR; BALAPERIDONE; BELAPERIDONE; CLOZAPINE; DOPAMINE 2 RECEPTOR; DOPAMINE 4 RECEPTOR; DOPAMINE RECEPTOR BLOCKING AGENT; HALOPERIDOL; ISOINDOLINYLBENZISOXAZOLPIPERIDINE DERIVATIVE; SONEPIPRAZOLE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENANTIOMER; HUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANIMALS; APOMORPHINE; BENZYL COMPOUNDS; DIZOCILPINE MALEATE; INDOLES; INFUSIONS, PARENTERAL; ISOXAZOLES; PIPERIDINES; PRAZOSIN; RATS; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D4; SERINE; SPIPERONE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 18644386045     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/1439-7633(20021004)3:10<999::AID-CBIC999>3.0.CO;2-A     Document Type: Article

References (30)

1. G. P. Reynolds, Trends Pharmacol. Sci. 1992, 13, 116-121.
2. (a) R. J. Baldessarini, F. I. Tarazi, Harv. Rev. Psychiatry 1996, 3, 301-325;
3. (b) K. A. Neve, R. L. Neve, The Dopamine Receptors, Humana Press, Totowa, 1997.
4. R. J. Baldessarini, D. Tarsey, Annu. Rev. Neurosci. 1980, 3, 23-41.
5. P. Krupp, P. Barnes, Br. J. Psychiatry 1992, 160 (Suppl. 17), 38-41.
6. H. H. M. Van Tol, J. R. Bunzow, H.-C. Guan, R. K. Sunahara, P. Seeman, H. B. Niznik, O. Civelli, Nature 1991, 350, 610-614.
7. L. Mrzljak, C. Bergson, M. Pappy, R. Huff, R. Levenson, P. S. Goldman-Rakic, Nature 1996, 381, 245-248.
8. (a) P. Seeman, Neuropsychopharmacology 1992, 7, 261-284;
9. (b) R. A. Lahti, D. L. Evans, N. C. Stratman, L. M. Figur, Eur. J. Pharmacology 1993, 236, 483-486.
10. A. Thurkauf, J. Yuan, X. Chen, X. S. He, J. W. F. Wasley, A. Hutchison, K. H. Woodruff, R. Meade, D. C. Hoffman, H. Donovan, D. K. Jones-Hertzog, J. Med. Chem. 1997, 40, 1-3.
11. L. J. Bristow, M. S. Kramer, J. Kulagowski, S. Patel, C. I. Ragan, S. R. Seabrook, Trends Pharmacol. Sci. 1997, 18, 186-188.
12. R. E. TenBrink, C. L. Bergh, J. N. Duncan, D. W. Harris, R. M. Huff, R. A. Lahti, C. F. Lawson, B. S. Lutzke, I. J. Martin, S. A. Rees, S. K. Schlachter, J. C. Sih, M. W. Smith, J. Med. Chem. 1996, 39, 2435-2437.
13. th American Chemical Society National Meeting, San Francisco, 1997, Abstract MEDI 186.
14. 4, see: N. J. Hrib, Drugs Future 2000, 25, 587-611. For a recent reviews on current approaches to the treatment of schizophrenia, see: a) M. Rowley, L. J. Bristow, P. H. Hutson, J. Med. Chem. 2001, 44, 477-501; b) R. Armer, D. J. Miller, Current Opinion Investigational Drugs (PharmaPress Ltd.) 2000, 1, 481-493.
15. 4, see: N. J. Hrib, Drugs Future 2000, 25, 587-611. For a recent reviews on current approaches to the treatment of schizophrenia, see: a) M. Rowley, L. J. Bristow, P. H. Hutson, J. Med. Chem. 2001, 44, 477-501; b) R. Armer, D. J. Miller, Current Opinion Investigational Drugs (PharmaPress Ltd.) 2000, 1, 481-493.
16. 4, see: N. J. Hrib, Drugs Future 2000, 25, 587-611. For a recent reviews on current approaches to the treatment of schizophrenia, see: a) M. Rowley, L. J. Bristow, P. H. Hutson, J. Med. Chem. 2001, 44, 477-501; (b) R. Armer, D. J. Miller, Current Opinion Investigational Drugs (PharmaPress Ltd.) 2000, 1, 481-493.
17. S.J. Peroutka, D.C. U'Prichard, D.A. Greenberg, S.H. Snyder, Neuropharmacology 1977, 16, 549-556.
18. P. De Witt, D. Misiti, G. Zappia, Tetrahedron Lett. 1989, 30, 5505.
19. For the preparation of 30, see: J. T. Strupczewski; R. C. Allen, B. A. Gardner, B. L. Schmid, U. Stache, E. J. Glamkowski, M. C. Jones, D. B. Ellis, F. P. Huger, R. W. Dunn J. Med. Chem. 1985, 28, 761-769.
20. F. Effenberger, U. Burkard, J. Willfahrt, Liebigs Ann. Chem. 1986, 314-333.
21. J. A. Kaydos, T. A. Spencer, J. Org. Chem. 1991, 56, 425-428.
22. J. Bornstein, J. E. Shields, A. P. Biosselle, Organic Synthesis, Collect. Vol. V, Wiley, New York, 1973, pp. 406-408.
23. P. Pigeon, B. Decroix, J. Heterocyclic Chem. 1996, 33, 129-135.
24. R. Corbett, F. Camacho, A. T. Woods, L. L. Kerman, R. J. Fishkin, K. Brooks, R. W. Dunn, Psychopharmacology 1995, 120, 67-74.
25. J. T. Strupczewski, E. J. Glamkowski, Y. Chiang, K. J. Bordeau, P. A. Nemoto, J. J. Tegeler, US 5591745, 1997.
26. E. J. Glamkowski, Y. Chiang, J. T. Strupczewski, P. A. Nemoto, J. J. Tegeler, US 5977140, 1999.
27. E. J. Glamkowski, Y. Chiang, US 5580886, 1996.
28. E. J. Glamkowski, Y. Chiang, J. T. Strupczewski, K. J. Bordeau, P. A. Nemoto, J. J. Tegeler, US 5607945, 1997.
29. P. Power, S. Rakhit, WO9618630, 1996.
30. J. W. Hubbard, S. T. Nordstrom, C. P. Smith, K. M. Brooks, L. Laws-Ricker, L. Zhou, H. M. Vargas, J. Pharmacol. Exp. Ther. 1997, 281, 337-346.