Synthesis and biological evaluation of orally active matrix metaloproteinase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 5, Issue 4, 1997, Pages 765-778

  Hirayama, Ryoichi ^b   Yamamoto, Minoru ^a   Tsukida, Takahiro ^a   Matsuo, Konomi ^a   Obata, Yuji ^b   Sakamoto, Fumio ^a   Ikedaa, Shoji ^a  

^a New Drug Research Laboratories   (Japan)

^b KANEBO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXAMIC ACID DERIVATIVE; METALLOPROTEINASE INHIBITOR;

ADJUVANT ARTHRITIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTHRITIS; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BIOAVAILABILITY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; MALE; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; RAT;

ABSORPTION; ADMINISTRATION, ORAL; ANIMALS; ANTI-INFLAMMATORY AGENTS; ARTHRITIS, EXPERIMENTAL; BIOLOGICAL AVAILABILITY; COLLAGENASES; DISEASE MODELS, ANIMAL; GELATINASES; HINDLIMB; HUMANS; HYDROXAMIC ACIDS; MALE; METALLOENDOPEPTIDASES; MICE; PROTEASE INHIBITORS; RATS; RATS, INBRED LEW; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

ANIMALIA;

EID: 0030987866     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)00028-X     Document Type: Article

References (24)

1. Ann. N.Y. Acad. Sci.; Greenwald, R. A.; Golub, L. M., Eds.;The New York Academy of Sciences, 1994; Vol. 732.
2. Docherty, A. J. P.; Murphy, G. Ann. Rheum. Dis. 1990, 49, 469.
3. Brown, P. D. Curr.Opin. Invest. Drugs 1993, 2, 617.
4. Mohler, K. M; Sleath, P. R.; Fitzzner, J. N.; Cerretti, D. P.; Alderson, M.; Kerwar, S. S.; Torrance, D. S.; Otten-Evans, C.; Greenstreet, T.; Weerawarna, K.; Kronheim, S. R.; Petersen, M.; Gerhart, M.; Kozlosky, C. J.; March, C. J.; Black, R. A. Nature 1994, 370, 218.
5. (a) Johnson, W. H.; Roberts, N. A.; Borkakoti, N. J. Enzyme Inhibition 1987, 2, 1.
6. (b) Henderson, B.; Docherty, A. J. P.; Beeley, N. R. A. Drugs of the Future 1990, 15, 495.
7. (c) Schwartz, M. A.; Van Eart, H. E. Prog. Med. Chem. 1992, 29, 271.
8. (d) Beckett, R. P.: Davidson, A. H.; Drummond, A. H.; Huxley, P.; Whittaker, M. Drug Discovery Today 1996, 1, 16.
9. (a) DiMartino, R. P.; High, W.; Galloway, W. A.;Crimin, M. J. Ann. N.Y. Acad. Sci. 1994, 732, 411.
10. (b) Conway, J. G.; Wakefield, J. A.; Brown, R. H.; Marron, B. E.; Sekut, L.; Stimpson, S. A.; McElroy, A.; Menius, J. A.; Jeffreys, J. J.; Clark, R. L.; McGeehan, G. M.: Connolly, K. M. J. Exp. Med. 1995, 182, 449.
11. Wahl, R. C.; Pulvino, T. A.; Mathiowetz, A. M.; Ghose, A. K.; Johnson, J. S.; Delecki, D., Cook, E. R.; Gainor, J. A.; Gowravaram, M. R.; Tomczuk, B. R. Bioorg. Med. Chem. Lett. 1995, 5, 349.
12. MaCachren, S. S. Arthritis Rheum. 1991, 34, 1085.
13. Japan Kokai 6-145148, 1994 (Kanebo, Ltd).
14. WO 9005716, 1990 (British Bio-technology Ltd).
15. Decicco, C. P.; Nelson, D. J.; Corbett, R. L.; Dreabit, J. C. J. Org. Chem. 1995, 60, 4782.
16. Spurlino, J. C.; Smallwood, A. M.; Carlton, D. D.; Banks, T. M.; Vavra, K. J.; Johnson, J. S.; Cook, E. R.; Falvo, J.; Wahl, R. C.; Pulvino, T. A.; Wendoloski, J. J.; Smith, D. L. Proteins: Struct. Funct. 1994, 19, 98.
17. Clog P values were calculated using 'Daylight PCmodels'.
18. Conradi, R. A.; Hilgers, A.R.; Ho, N. F. H.; Burton, P. S. Pharm. Res. 1992, 9, 435.
19. Inaba, T.; Kozono, I.; Fujita, M.; Ogura, K. Bull. Chem. Soc. Jpn. 1992, 65, 2539.
20. These N-Boc-amino acids were purchased from Synthe-tech, Inc. (OR, U.S.A.).
21. Japan Kokai 3-103178, 1991; 6-86672,1994; 7-75571, 1995 (Kanebo, Ltd).
22. Japan Kokai 3-103178, 1991; 6-86672,1994; 7-75571, 1995 (Kanebo, Ltd).
23. Japan Kokai 3-103178, 1991; 6-86672,1994; 7-75571, 1995 (Kanebo, Ltd).
24. Nagai, N.; Hori, H.; Hattori, S.; Sunada, Y.; Terada, K.; Hashida, R.; Miyamoto, K. Jpn. J. Inflamm. 1984, 4, 123.