Design and synthetic considerations of matrix metalloproteinase inhibitors

Annals of the New York Academy of Sciences

Volumn 878, Issue , 1999, Pages 61-72

  Skotnicki, Jerauld S ^a   Zask, Arie ^a   Nelson, Frances C ^a   Albright, J Donald ^a   Levin, Jeremy I ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 [4,4 (CHLOROPHENYL)PHENYL] 4 OXO (PHENYLTHIOMETHYL)BUTANOIC ACID; 4 [[[4 (4 CHLOROPHENOXY)PHENYL]SULFONYL]METHYL]TETRAHYDRO 2H PYRAN 4 CARBOHYDROXAMIC ACID; CGS 27023A; CHELATING AGENT; CIPEMASTAT; DOXYCYCLINE; HYDROXAMIC ACID; ILOMASTAT; MARIMASTAT; MATRIX METALLOPROTEINASE; MATRIX METALLOPROTEINASE INHIBITOR; N1 (1 CARBAMOYL 2,2 DIMETHYLPROPYL) 2 [3 (4 CHLOROPHENYL)PROPYL] N4 HYDROXYBUTANEDIAMIDE; PRINOMASTAT; UNCLASSIFIED DRUG;

ATHEROSCLEROSIS; CONFERENCE PAPER; CONNECTIVE TISSUE DISEASE; CORNEA ULCER; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME REGULATION; METASTASIS; MULTIPLE SCLEROSIS; OSTEOARTHRITIS; PERIODONTAL DISEASE; RHEUMATOID ARTHRITIS; TUMOR VASCULARIZATION;

EID: 0032803160     PISSN: 00778923     EISSN: None     Source Type: Book Series    
DOI: 10.1111/j.1749-6632.1999.tb07674.x     Document Type: Conference Paper

References (35)

1. 1. Skotnicki, J.S., J.I. Levin, L.M. Killar & A. Zask. 1999. Matrix metalloproteinase inhibitors. In Metalloproteinases as Targets for Anti-inflammatory Drugs. D. Bradshaw, J.S. Nixon & K. Bottomley, Ed. Birkhauser Verlag. Basel. In press.
2. 2. Bottomley, K.M., W.H. Johnson & D.S. Walter. 1998. Matrix metalloproteinase inhibitors in arthritis. J. Enzyme Inhib. 13: 79-101.
3. 3. Whittaker, M. & P. Brown. 1998. Recent advances in matrix metalloproteinase inhibitor research and development. Curr. Opin. Drug Disc. Develop. 1: 157-164.
4. 4. Beckett, R.P. & M. Whittaker. 1998. Matrix metalloproteinase inhibitors 1998. Exp. Opin. Ther. Patents 8: 259-282.
5. 5. Watson, S.A. & G. Tierney. 1998. Matrix metalloproteinase inhibitors. BioDrugs : 325-336.
6. 6. Rothenberg, M.L., A.R. Nelson & K.R. Hande. 1998. New drugs on the horizon: matrix metalloproteinase inhibitors. Oncologist 3: 271-274.
7. 7. Summers J.B. & S.K. Davidsen. 1998. Matrix metalloproteinase inhibitors and cancer. Annu. Rep. Med. Chem. 33: 131-140.
8. 8. Levy, D.E. & A.M. Ezrin. 1997. Matrix metalloproteinase inhibitor drugs. Emerging Drugs 2: 205-230.
9. 9. Denis, L.J. & J. Verweij. 1997. Matrix metalloproteinase inhibitors: present achievements and future prospects. Invest. New Drugs 15: 175-185.
10. 10. White, A.D., T.M.A. Bocan, P.A. Boxer, J.T. Peterson & D. Schrier. 1997. Emerging therapeutic advances for the development of second generation matrix metalloproteinase inhibitors. Curr. Pharm. Design 3: 45-58.
11. 11. Brown, P.D. 1997. Matrix metalloproteinase inhibitors in the treatment of cancer. Medical Oncology 14: 1-10.
12. 12. Zask, A, J.I. Levin, L.M. Killar & J.S. Skotnicki. 1996. Inhibition of matrix metalloproteinases: structure based design. Curr. Pharm. Design 2: 624-661.
13. 13. Hagmann, W.K., M.W. Lark & J.W. Becker. 1996. Inhibition of matrix metalloproteinases. Annu. Rep. Med. Chem. 31: 231-240.
14. 14. Beckett, R.P. 1996. Recent advances in the field of matrix metalloproteinase inhibitors. Exp. Opin. Ther. Patents 6: 1305-1315.
15. 15. Beckett, R.P., A.H. Davidson, A.H. Drummond, P. Huxley & M. Whittaker. 1996. Recent advances in matrix metalloproteinase inhibitor research. Drug Discovery Today 1: 16-26.
16. 16. Cawston, T.E. 1996. Metalloproteinase inhibitors and the prevention of connective tissue breakdown. Pharmacol. Ther. 70: 163-182.
17. 17. Porter, J.R., T.A. Millican & J.R. Morphy. 1995. Recent developments in matrix metalloproteinase inhibitors. Exp. Opin. Ther. Patents 5: 1287-1296.
18. 18. Morphy, J.R., T.A. Millican & J.R. Porter. 1995. Matrix metalloproteinase inhibitors: current status. Curr. Med. Chem. 2: 743-762.
19. 19. Beeley, N.R.A., P.R.J. Ansell & A.J.P. Docherty. 1994. Inhibitors of matrix metalloproteinases (MMPs). Curr. Opin. Ther. Patents 4: 7-16.
20. 20. Schwartz, M.A. & H.E. Van Wart. 1992. Synthetic inhibitors of bacterial and mammalian interstitial collagenases. Prog. Med. Chem. 29: 271-334.
21. 21. Nelson, F.C. & A. Zask. 1999. The therapeutic potential of small molecule TACE inhibitors. Exp. Opin. Invest. Drugs. In press.
22. 22. Lowe, C. 1998. Tumour necrosis factor-α Antagonists and their therapeutic applications. Exp. Opin. Ther. Patents 8: 1309-1322.
23. 23. Shire, M.G. & G.E. Muller. 1988. TNF-α inhibitors and rheumatoid arthritis. Exp. Opin. Ther. Patents 8: 531-544.
24. 24. Black, R.A., T.A. Bird & K.M. Mohler. 1997. Agents that block TNF-α synthesis or activity. Annu. Rep. Med. Chem. 32: 241-250.
25. 25. Davidson, S.K. & J.B. Summers. 1995. Inhibitors of TNF-α Synthesis. Exp. Opin. Ther. Patents 5: 1087-1100.
26. 26. Campbell, D.A., X.-Y. Xiao, D. Harris, S. Ida, R. Mortezaei, K. Ngu, L. Shi, D. Tein, Y. Wang, M. Navre, D.V. Patel, M.A. Scharr, J.F. Dijoseph, L.M. Killar, C.L. Leone, J.I. Levin & J.S. Skotnicki. 1998. Malonyl α-mercaptoketones and α-mercaptoalcohols, a new class of matrix metalloproteinase inhibitors. Bioorg. Med. Chem. Lett. 8: 1157-1162.
27. 27. Levin J.I., J.F. DiJoseph, L.M. Killar, M.A. Sharr, J.S. Skotnicki, D.V. Patel, X.-Y. Xiao, L. Shi, M. Navre & D.A. Campbell. 1998. The asymmetric synthesis and in vitro characterization of succinyl mercaptoalcohol and mercaptoketone inhibitors of matrix metalloproteinases. Bioorg. Med. Chem. Lett. 8: 1163-1168.
28. 28. Baxter, A.D., J. Bird, R. Bhogal, T. Massil, K.J. Minton, J. Montana & D.A. Owen. 1997. A novel synthesis of matrix metalloproteinase inhibitors for the treatment of inflammatory disorders. Bioorg. Med. Chem. Lett. 7: 897-902.
29. 29. Beszant, B., J. Bird, L.M. Gaster, G.P. Harper, I. Hughes, E.H. Karran, R.E. Markwell, A.J. Miles-Williams & S.A. Smith. 1993. Synthesis of novel modified dipeptide inhibitors of human collagenase: β-mercapto carboxylic acid derivatives. J. Med. Chem. 36: 4030-4039.
30. 30. Parker, D.P., L.J. MacPherson, R. Goldstein, M.R. Justice, L.J. Zhu, M. Capparelli, L.W. Whaley, C. Boehm, E.M. O'Byrne, R.L. Goldberg & V.S. Ganu. 1994. CGS 27023A: A novel, potent, and orally active matrix metalloprotease inhibitor. Presented at the Seventh International Conference of the Inflammation Research Association, White Haven, PA.
31. 31. MacPherson, L.J., E.K. Bayhurt, M.P. Capparelli, B.J. Carroll, R. Goldstein, M.R. Justice, L. Zhu, S. Hu, R.A. Melton, L. Fryer, R.L. Goldberg, J.R. Doughty, S. Spirito, V. Blancuzzi, D. Wilson, E.M. O'Byrne, V. Ganu & D.T. Parker. 1997. Discovery of CGS 27023A, A non-peptidic, potent, and orally active stromelysin inhibitor that blocks cartilage degradation in rabbits. J. Med. Chem. 40: 2525-2532.
32. 32. Levin J.I., J.F. Dijoseph, L.M. Killar, A. Sung, T. Walter, M.A. Sharr, C.E. Roth, J.S. Skotnicki & J.D. Albright. 1998. The synthesis and biological activity of a novel series of diazepine MMP inhibitors. Bioorg. Med. Chem. Lett. 8: 2657-2662.
33. 33. DiJoseph, J.F. & M.A. Sharr. 1998. Dialysis tubing implant assay in the rat: a novel in vivo method for identifying inhibitors of matrix metalloproteinases. Drug Develop. Res. 43: 200-205.
34. 34. Health News Daily, 10/2/98; Pink Sheet, 10/5/98; Marketletter 10/12/98.
35. 35. Ryan, M.E., S. Ramamurthy & L.M. Golub. 1996. Matrix metalloproteinases and their inhibition in periodontal treatment. Curr. Opin. Peridontol. 3: 85-96.