Benzolactam growth hormone secretagogues: Replacement of the C-3 amide bond in L-692,429

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 24, 1996, Pages 3051-3056

  Ok, Hyun O ^a   Szumiloski, John L ^a   Doldouras, George A ^a   Schoen, William R ^a   Cheng, Kang ^a   Chan, Wanda W S ^a   Butler, Bridget S ^a   Smith, Roy G ^a   Fisher, Michael H ^a   Wyvratt, Matthew J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 HYDROXYPROPYLAMINO) 3 METHYL N [2,3,4,5 TETRAHYDRO 2 OXO 1 [[2' (1H TETRAZOL 5 YL) 1,1' BIPHENYL 4 YL]METHYL] 1H 1 BENZAZEPIN 3 YL]BUTANAMIDE; 3 AMINO 3 METHYL N [2,3,4,5 TETRAHYDRO 2 OXO 1 [[2' (1H TETRAZOL 5 YL) 1,1' BIPHENYL 4 YL]METHYL] 1H 1 BENZAZEPIN 3 YL]BUTANAMIDE; GROWTH HORMONE RELEASING FACTOR DERIVATIVE; L 158432; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL CULTURE; CONTROLLED STUDY; DRUG SYNTHESIS; GROWTH HORMONE RELEASE; HYPOPHYSIS; IN VITRO STUDY; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

EID: 0030591847     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00566-5     Document Type: Article

References (15)

1. 1. Current Address: Institute For Chemistry, Bayer Corp., 400 Morgan Lane B24, West Haven, Ct 06516
2. 2. Strobl, J. S.; Thomas, M. J. Pharmacological Reviews 1994, 46, 1.
3. 3. Thorner, M. O. Acta Paediatr. Suppl. 1993, 388, 2.
4. 4. Schoen, W. R.; Wyvratt, M. J.; Smith, R. G. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed; Academic: San Diego, 1993; Vol. 28, Chapter 19.
5. 5. Low, L. C. K. Neuroendocrinology 1991, 53, 37.
6. 6. Bowers, C. Y. J. Pedatr. Endocrinol. 1993, 6, 21.
7. 7. Smith, R. G.; Cheng, K.; Schoen, W. R.; Pong, S. -S.; Hickey, G.; Jacks, T.; Butler, B.; Chan, W. W.-S.; Chaung, L.-Y. P.; Judith, F.; Taylor, J.; Wyvratt, M. J.; Fisher, M. H. Science 1993, 260, 1640.
8. 8. Gertz, B. J .; Barrett, J. S.; Eisenhandler, R.; Krupa, D. A.; Wittreich, J. M.; Seibold, J. R.; Schneider, S. H. J. Clin. Endocrinol. Metab. 1993, 77, 1393.
9. 9. Schoen, W. R.; Pisano, J. M.; Wyvratt, M. J.; Fisher, M. H.; Prendergast, K.; Cheng, K.; Chan, W. W.-S.; Butler, B.; Smith, R. G.; Ball, R. G. J. Med. Chem. 1994, 37, 897.
10. For a review see: DeVita, R. J.; Wyvratt, M. J. Drugs of the Future, 1996, 21, 273.
11. 10. Ok, D.; Schoen, W. R.; Hodges, P.; DeVita, R. J.; Brown, J. E.; Cheng, K.; Chan W. W. -S.; Butler, B.; Smith, R. G.; Fisher, M. H.; Wyvratt, M. J. Bioorg. Med. Chem. Lett. 1994, 4, 2709.
12. 11. Armstrong, J. D. III; Eng, K. K.; Keller, J. L.; Purick, R. M.; Hartner, F. W., Jr.; Choi, W. B.; Askin, D.; Volante, R. P. Tetrahedron Lett. 1994, 35, 3239.
13. 12. Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937.
14. 13. Compounds 6 and 7 were prepared by the same protocol reported in reference 9 except for using N-3 alkylated benzolactams prepared from 2 by utilizing a reductive amination method with the requisite aldehyde.
15. (equation presented)