Inhibition of Matrix Metalloproteinases: Structure Based Design

Current Pharmaceutical Design

Volumn 2, Issue 6, 1996, Pages 624-661

  Zask, Arie ^a   Levin, Jeremy I ^a   Killar, Loran M ^a   Skotnicki, Jerauld S ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000647282     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (263)

1. Woessner, J.F., Jr. FASEB J. 1991, 5, 2145.
2. Birkedal-Hansen, H.; Moore, W.G.I.; Bodden, M.K ; Windsor, L.J.; Birkedal-Hanscn, B.; DeCarlo, A.; Engler, J.A. Crit. Rev. Oral Biol. Med. 1993, 4, 197.
3. Cawston, T.E. Pharmacol. Ther. 1996, 70, 163.
4. Powell, W.C., Matrisian, L.M Cur. Top. Microbiol. and Immunol. 1996, 213, 1.
5. Werb, Z.; Alexander, C.M.; Adler, R.R. In Matrix Metalloproteinases and Inhibitors; Birkedal-Hansen, H.; Werb, Z.; Welgus, H.G.; Van Wart, H.E., Eds.; Gustav Fischer: Stuttgart, 1992; Matrix; Spec. Suppl. No.1, P. 337.
6. Werb, Z.; Alexander, C.M.; Adler, R.R. In Matrix Metalloproteinases and Inhibitors; Birkedal-Hansen, H.; Werb, Z.; Welgus, H.G.; Van Wart, H.E., Eds.; Gustav Fischer: Stuttgart, 1992; Matrix; Spec. Suppl. No.1, P. 337.
7. Edwards, D.R. Int. J Obesity, 1996, 20 (Suppl. 3), S121.
8. Moses, M.A.; Marikovsky, M ; Harper, J.W.; Vogt, P.; Eriksson, E : Klagsbrun, M.; Langer, R. J. Cell. Biochem. 1996, 60, 379.
9. Brannstrom, M.; Woessner, J.F., Jr.; Koos, R.D.; Sear, C H.J.; LeMaire, W.J. Endocrinol. 1988, 122, 1715.
10. Tabibzadeh, S. Mol. Hum. Reprod. 1996, 2, 77.
11. Alexander, C.M.; Hansell, E.J ; Behrendtsen, O.; Flannery, M.L.; Kishnani, N.S.; Hawkes, S.P.; Werb, Z. Development, 1996, 122, 1723.
12. Ries, C. ; Petrides, P.E. Biol. Chem. Hoppe-Seyler, 1995, 376, 345.
13. Cornelius, L.A.; Nehring, L.C.; Pierce, R.A. J. Invest. Dermatol., 1996 106, 810.
14. Kennedy, S.H.; Rouda, S.; Qin, H.; Selber, J.; Artlett, C.M.; Varga, J.; Tan, E.M.L. J. Invest. Med. 1996, 44, 276A.
15. Harris, E.J. New. Engl. J. Med. 1990, 322, 1277.
16. Brinckerhoff, C.E.; Auble, D.T. Ann N.Y. Acad. Sci. 1990, 580, 355.
17. Fisher, G.J.; Datta, S.C.; Talwar, H.S.; Wang, Z.Q.; Varani, J.; Kang, S.; Voorhees, J.J. Nature, 1996, 379, 335.
18. Arner, E.C.; Tortorella, M.D. Arthritis Rheum. 1995, 38, 1304.
19. Goetzl, E.J.; Banda, M.J.; Leppert, D. J. Immunol. 1996, 156, 1.
20. Zaoui, P; Barro, C.; Morel, F. Biochim. Biophys. Acts, 1996, 1290, 101.
21. Apte, S.S.; Olsen, B.R., Murphy, G J Biol. Chem. 1995, 270, 14313.
22. Hammani, K.; Henriet, P.; Silbiger, S.M.; DeClerck, Y.A. Gene, 1996, 170, 287.
23. Greene, J.M.; Rosen, C. A. WO Pat. 96/18725
24. Howell, D.S.; Pelletier, J.-P. In Arthritis and Allied Conditions; McCarthy, D.J.; Koopman, W.J., Eds.; Lea and Febiger: Philadelphia, 1993: 12th Edition Vol. 2, P. 1723.
25. Dean, D.D. Sem. Arthritis Rheum. 1991, 20, 2.
26. Crawford, H.C; Matrisian, L.M. Invasion Metast. 1994-95, 14, 234.
27. Ray, J.M.; Stetler-Stevenson, W.O. Exp. Opin. Invest. Drugs, 1996, 5, 323.
28. Dollery, C.M.; McEwan, J.R.; Henney, A.M. Circ. Res. 1995, 77, 863.
29. Zempo, N.; Koyama, N.; Kenagy, R.D.; Lea, H.J.; Clowes, A.W. Artertoscler. Thromb. Vasc. Biol. 1996, 16, 28.
30. Lee, R.T.; Schoen, F.J.; Loree, H.M.; Lark, M.W., Libby, P. Arterioscler. Thromb. Vasc. Biol. 1996, 16, 1070
31. Ciancio, S.B., Ann. N. Y. Acad. Sci. 1994, 732, 132.
32. Gray, R.D.; Paterson, C.A. Ann. N.Y. Acad. Sci. 1994, 732, 206.
33. Vaalamo, M.; Weckroth, M ; Puolakkainen, P.; Kere, J.; Saarinen, P.; Lauharanta, J.; Saarialho-Kere, U.K. Br. J. Dermatol 1996, 135, 52
34. Weckroth, M.; Vaheri, A.; Lauharanta, J.; Sorsa, T.; Knottinen, YT. J. Invest. Dermatol. 1996, 106, 1119.
35. Kubben, FJ G.M.; Heerdmg, M.M.; Sier, C.F.M.; Van Hogezand, R.A.; Wagtmans, M.J.; Lamers, C.B.H.W.; Verspaget, H.W. Gastroenterol. 1996, 110 (Suppl. 4), A943.
36. Matthes, H ; Ulrich, K; Stallmach, A; Herbst, H.; Riecken, E.O. Gastroenterol. 1996, 110 (Suppl. 4), A959.
37. Vadillo-Ortega, F.; Hernandez, A.; Gonzalez-Avila, G.; Bermejo, L.; Iwata, K.; Strauss, J.F., III. Am. J. Obstet. Gynecol. 1996, 174, 1371
38. Steinman, L., Cell, 1996, 85, 299.
39. Moss, M.; Jin, C.; Becherer, D., Bickett, M.; Burkhart, W.; Chen, W.; Didsbury, J.; Hassler, D.; Leesnitzer, T.; McGeehan, G.; McCauley, P.; Moyer, M.; Milla, M.; Rocque, W.; Seaton, T.; Warner, J.; Willard, D. Eur. Cytokine Network, 1996, 7, 181.
40. Black, R.; Rauch, C.; Kozlosky, C.; Wolfson, M.; Castner, B.; Reddy, P.; Davis, R.; Peschon, J.; Slack, J.; Gerhart, M.; Paxton, R.; March, C.; Cerretti, D. Eur. Cytokine Network, 1996, 7, 180.
41. Gearing, A.J.H.; Beckett, P.; Christodoulou, M.; Churchill, M.; Clements, J.; Davidson, A.M.; Drummond, A.H.; Galloway, W.A.; Gilbert, R.; Gordon, J.L. Nature, 1994, 370, 555.
42. McGeehan, G.M.; Becherer, J.D.; Bast, R.C.; Boyer, C.M.; Champion, B.; Connolly, K.M.; Conway, J.G.; Furdon, P.; Karp, S.; Kidao, S. Nature, 1994, 370, 558.
43. Mohler, K.; Sleath, P.R.; Fitzner, J.N.; Cerretti, D.P.; Alderson, M.; Kerwar, S.S.; Torrance, D.S.; Otten-Evans, C.; Greenstreet, T.; Weerawama, K. Nature, 1994, 370, 218.
44. Williams, L.M.; Gibbons, D.L.; Gearing, A.; Maini, R.N.; Feldman, M.; Brennan, M. F. J. Clin. Invest. 1996, 97, 2833.
45. Preece, G.; Murphy, G.; Ager, A. J. Biol. Chem. 1996, 271, 11634.
46. Drummond, A.H., FASEB J. 1996, 10, A1129.
47. Puente, X.S.; Pendas, A.M ; Llano, E.; Velasco, G.; Lopez-Otin, C., Cancer Res. 1996, 56, 944.
48. Galazka, G.; Windsor, L J.; Hansen-Birkedal, H.; Engler, J. A. Biochemistry, 1996, 35, 11221.
49. Murphy, G.; Cockett, M.J., Stephens, P.E.; Smith, B J., Docherty, A.J.P. Biochem J. 1987, 248, 265.
50. Strongin, A.Y.; Collier, I.; Bannikov, G.; Marmer, B.L.; Grant, G.A ; Goldberg, G I. J Biol. Chem. 1995, 270, 5331.
51. Corcoran, M.L.; Hewitt, R.E.; Kleiner, D.E., Jr.; Stetler-Stevenson, W.G. Enzyme Prot. 1996, 49, 7.
52. Pei, D.; Weiss, S.J. J. Biol. Chem 1996, 271, 9135.
53. Imai, K.; Ohuchi, E.; Aoki, T.; Nomura, H.; Fujii, Y.; Sato, H.; Seiki, M.; Okada, Y. Cancer Res. 1996, 56, 2707.
54. Will, H.; Atkinson, S.J.; Butler, G.S.; Smith, B.; Murphy, G. J. Biol. Chem. 1996, 277, 17119.
55. Knauper, V.; Will, H.; Lopez-Otin, C.; Smith, B.; Atkinson, S.J.; Stanton, H.; Hembry, R.M.; Murphy, G. J. Biol. Chem. 1996, 277, 17124.
56. a) Beckett, R.P.; Davidson, A.H.; Drummond, A.H.; Huxley, P ; Whittaker, M. Drug Discovery Today, 1996, 1, 16.
57. b) Morphy, J.R.; Millican, T.A.; Porter, J.R. Current Med. Chem. 1995, 2, 743.
58. c) Porter, J.R , Millican, T.A ; Morphy. J.R. Exp. Opin. Ther Patents, 1995, 5, 1287.
59. d) Beeley, N R.A.; Ansell, P.R.J., Docherty, A.J.P. Curr. Opin. Ther. Patents, 1994, 4, 7.
60. e) Schwanz, M.A., Van Wart, H.E. In Progress in Med. Chem.; Ellis & Luscombe, Ed ; Elsvier Science B.V.; Amsterdam, 1992; Vol 29, P. 271.
61. Crimmin, M.J.; Ayscough, A.P.; Beckett, R.P. WO Pat 94/24140.
62. Beckett, R.P.; Whirtaker, M.; Miller, A.; Martin, F.M. WO Pat. 96/16931.
63. Crimmin, M.J., Beckett, P.R.; Davis, M.H. WO Pat. 94/21625.
64. Miller, A.; Beckett, P R.; Martin, F.; Whittaker, M. WO Pat. 95/32944.
65. Beckett, R P.; Whittaker, M.; Miller, A. WO Pat. 95/19961.
66. Beckett, R.P.; Whittaker, M.; Miller, A.; Martin, F.M. WO Pat. 95/19957
67. Beckett, R.P.; Miller, A.; Whittaker, M. WO Pat. 96/06074.
68. Beckett, R.P.; Whittaker, M.; Miller, A.; Martin, F.M. WO Pat. 95/19956
69. Porter, J.R.; Beeley, N.R.A.; Boyce, B.A.; Mason, B.; Millican, A., Millar, K.; Leonard, J.; Morphy, J.R.; O'Connell, J.P. Bioorg. & Med. Chem. Lett. 1994, 4, 2741.
70. Chander, S.K.; Antoniw, P.; Beeley, N.R.A.; Boyce, B.; Crabbe, T.; Docherty, A.J.P.; Leonard, J.; Mason, B.; Millar, K.; Millican, A.T.; Morphy, R.; Mountain, A.; O'Connel, J.; Porter, J.R.; Willmott, N. J. Pharm. Sci. 1995, 84, 404.
71. a) Morphy, R.J.; Millican, A.T. WO Pat. 94/25434.
72. b) Morphy, R.J.; Millican, A.T. WO Pat. 94/25435.
73. c) Beeley, N.R.A.; Millican, T.A. WO Pat. 95/04033.
74. Morphy, J.R.; Beeley, N.R.A.; Boyce, B.A.; Leonard, J.; Mason, B.; Millican, A.; Millar, K.; O'Connell, J.P.; Porter, J. Bioorg. & Med. Chem. Lett 1994, 4, 2747.
75. Montana, J ; Dickens, J.; Owen, D.A.; Baxter, A.D. WO Pat. 95/13289.
76. a) Montana, J.; Baxter, A.D.; Owen, D.A.; Watson, R.J.; Phillipson, N. WO Pat. 96/11209.
77. b) Exp. Opin. Ther. Patents, 1996, 6(9), 917.
78. Xue, C.-B.; He, X.; Roderick, J.; DeGrado, W.F.; Decicco, C.; Copeland, R.A. Bioorg. & Med. Chem. Lett. 1996, 6, 379.
79. Chapman, K.T.; Kopka, I.E.; Durette, P L.; Esser, C.K.; Lanza, T.J ; Izquierdo-Martin, M ; Niedzwiecki, L.; Chang, B.; Harrison, R.K.; Kuo, D.W.; Lin, T.-Y.; Stein, R.L.; Hagmann, W.K. J. Med Chem. 1993, 36, 4293.
80. Brown, F.K.; Brown, P.J.; Bickett, D.M.; Chambers, C.L.; Davies, H.G.; Deaton, D.N.; Drewry, D.; Foley, M.; McElroy, A B.; Gregson, M.; McGeehan, G.M.; Myers, P.L ; Norton, D.; Salovich, J.M.; Schoenen, F.J.; Ward, P. J. Med. Chem 1994, 37, 674.
81. a) Ogita, T.; Sato, A. et. al. J. Antibiotics, 1992, 45, 1723.
82. b) Tamaki, K.; Kurihara, S.; Oikawa, T.; Tanzawa, K.; Sugimura, Y. J. Antibiotics, 1994, 47, 1481.
83. Kobayashi, T.; Sugimura, Y.; Tamaki, K.; Tanzawa, K. WO Pat. 93/09097
84. Nugiel, D.A.; Jacobs, K.; Decicco, C P.; Nelson, D. J.; Copeland, R. A ;. Hardman, K. D Bioorg. & Med. Chem. Lett. 1995, 5, 3053.
85. Decicco, C.P.; Jacobson, I C.; Magolda, R.L.; Nelson, D.J ; Cheney, R.J. WO Pat 95/29892.
86. Exp. Opin. Ther. Patents, 1996, 6(5), 499.
87. Schwartz, M.A.; Van Wart, H. E. WO Pat 95/09833.
88. Schwartz, M.A.; Van Wart, H. E WO Pat 95/09620.
89. a) McCullagh, K.; Wadsworth, H.; Hann, M. 1984; Eur. Pat. EP 126,974,
90. b) McCullagh, K.; Wadsworth, H.; Hann, M. 1985; Eur. Pat. EP 159,396.
91. Foley, M.A.; Hassman, A.S.; Drewry, D.H.; Greer, D G.; Wagner, C.D.; Feldman, P.L.; Berman, J.; Bickett, D.M.; McGeehan, G.M.; Lambert, M H.; Green, M. Bioorg. & Med. Chem. Lett 1996, 6, 1905.
92. Tippin, T ; St. Claire, R.; Lee, F.W. Faseb J. 1994, 8(4) Part I, 572.
93. 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
94. Conway, J.G.; Wakefield, J.A.; Marron, B.E.; McGeehan, G.M. Proc. Am. Assoc. Cancer Res. 1994, 35, 70.
95. Izquierdo-Martin, M ; Chapman, K.T.; Hagmann, W.K.; Stein, R.L. Biochemistry, 1994, 33, 1356.
96. Sahoo, S.P.; Caldwell, C.G ; Chapman, K.T., Durette, P.L.; Esser, C.K.; Kopka, I.E.; Polo, S.A. ; Sperow, K.M., Niedzwiecki, L.M.; Izquierdo-Martin, M ; Chang, B C.; Harrison, R.K.; Stein, R.L.; MacCoss, M.; Hagmann, W.K. Bioorg. & Med. Chem. Lett. 1995, 5, 2441.
97. Chapman, K.T.; Wales, J.; Sahoo, S.P.; Niedzwiecki, L.M.; Izquierdo-Martin, M.; Chang, B.C.; Harrison, R.K.; Stein, R.L.; Hagmann, W.K. Bioorg. & Med. Chem. Lett., 1996, 6, 329.
98. Chapman, K.T.; Durette, P.L.; Caldwell, C.G.; Sperow, K.M.; Niedzwiecki, L.M.; Harrison, R K., Saphos, C.; Christen, A.J.; Olszewski, J.M ; Moore, V.L.; MacCoss, M.; Hagmann, W.K. Bioorg. & Med. Chem. Lett. 1996, 6, 803.
99. Esser, C.K.; Kopka, I.E.; Durette, P.L.; Harrison, R.K.; Niedzwiecki, L.M., Izquierdo-Martin, M.; Stein, R.L.; Hagmann, W.K. Bioorg. & Med. Chem. Lett. 1995, 5, 539.
100. Goulet, J.L.; Kinneary, J.F.; Durette, P.L.; Stein, R.L.; Harrison, R.K.; Izquierdo-Martin, M.; Kuo, D.W.; Lin, T.-Y.; Hagmann, W.K. Bioorg. & Med. Chem. Lett. 1994, 4, 1221.
101. Caldwell, C.G.; Sahoo, S.P.; Polo, S A..; Eversole, R.R.; Lanza, T.J.; Mills, S.G.; Niedzwiecki, L.M.; Izquierdo-Martin, M.; Chang, B.C.; Harrison, R.K.; Kuo, D.W.; Lin, T.-Y.; Stein, R.L.; Durette, P.L.; Hagmann, W.K. Bioorg. & Med. Chem. Lett. 1996, 6, 323.
102. Hagmann, W.K.; Kopka, I.E. WO Pat. 94/07481.
103. Hagmann, W K.; Caldwell, C.G., Gooley, P.R. 1995; G B 2282598A
104. Robinson, R.P.; Ragan, J.A., Cronin, B.J.; Donahue, K.M.; Lopresti-Morrow, L.L.; Mitchell, P.G.; Reeves, L.M.; Yocum, S.A. Bioorg. & Med Chem. Let: 1996, 6, 1719.
105. Robinson, R.P.; Cronin, B.J.; Donahue, K M.; Jones, B P.; Lopresti-Morrow, L.L.; Mitchell, P.G.; Rizzi, J.P.; Reeves, L.M.; Yocum, S.A. Bioorg. & Med. Chem. Lett. 1996, 6, 1725.
106. Lovejoy, B.; Cleasby, A.; Hassell, A.M.; Longley, K.; Luther, M.A.; Weigl, D., McGeehan, G.; McElroy, A.B.; Drewry, D.; Lambert, M.H.; Jordan, S R. Science, 1994, 263, 375.
107. Yelm, K E. WO Pat. 96/20918.
108. Johnson, W.H. Drug News and Perspectives, 1990, 3, 453.
109. Broadhurst, M J; Handa, B.K.; Johnson, W.H.; Lawton, G.; Machin, P.J. 1987; Eur. Pat. EP 276,436.
110. Handa, B.K.; Johnson, W.H.; Machin, P.J 1988; Eur. Pat. EP 236,872.
111. a) Castelhano, A L.; Billedeau, R.; Dewdney, N.; Donnelly, S.; Home, S ; Kurz, L.J ; Liak, T.J.; Martin, R.; Uppington, R.; Yuan, Z.; Krantz, A. Bioorg. & Med. Chem. Lett. 1995, 5, 1415
112. b) Castelhano, A.L.; Liak, T.J.; Home, S.; Yuan, Z.; Krantz, A. WO Pat 95/04735.
113. a) Lewis, E J.; Bottomley, K.M.K.; Broadhurst, M.J.; Brown, P.A.; Hallam, T.J., Johnson, W.H.; Lawton, G.; Nixon, J.S Joint BCTS and BCR Meeting in Cambridge, UK: "Connective Tissue Matrix Degradation in Health and Disease" Sept. 22-24, 1993.
114. b) Broadhurst, M.J.; Brown, P.A.; Johnson, W.H.; Lawton, G. 1992; Eur. Pat EP 497192.
115. Castelhano, A.L.; Horne, S.; Liak, T.J. WO Pat. 95/12603.
116. Exp. Opin. Ther. Patents, 1995, 5, 1305.
117. Castelhano, A.L.; Bender, S.L.; Deal, J.G.; Horne, S.; Liak, T.J.; Yuan, Z. WO Pat. 96/16027.
118. Chen, J.J.; Zhang, Y.; Hammond, S.; Dewdney, N.; Ho, T.; Lin, X.; Browner, M F.; Castelhano, A.L. Bioorg. & Med. Chem. Lett. 1996, 6, 1601.
119. Frazee, J.S.; Gleason, J.G.; Metcalf, B.W. WO Pat. 95/23790.
120. Broadhurst, M.J.; Brown, P A ; Johnson, W.H. WO Pat 95/33709.
121. Broadhurst, M.J.; Brown, P.A.; Johnson, W.H. 1995; Eur. Pat EP 684,240
122. Broadhurst, M.J.; Brown, P.A ; Johnson, W.H.; Lawton, G. 1993; Eur. Pat. EP 574,758.
123. Lewis, E.J.; Bishop, J.; Bottomley, K.M.; Bradshaw, D.; Brown, P.A ; Broadhurst, M.J.; Budd, J.M.; Elliott, L.; Gibson, V.M.; Greenham, A.K.; Hill, C.H.; Johnson, W.H.; Lawton, G.; Nixon, J.S. P108, BPS Summer Meeting, Bath, U.K. July 9-12, 1996.
124. Sutton, B.; Hoespool, F.; Angus, D.; Bryson, A.; Burden, D.; Harris, S.; Heeps, G.; Hooper, H.; Mitchell, A.; Sharp, S. P234, BPS Summer Meeting, Bath, U.K. July 9-12, 1996.
125. Broadhurst, M.J.; Brown, P.A.; Johnson, W.H. WO Pat. 95/33731.
126. Tamaki, K.; Tanzawa, K., Kurihara, S.; Oikawa, T.; Monma, S.; Shimada, K.; Sugimura, Y. Chem. Pharm. Bull 1995, 43, 1883.
127. Bird, J.; De Mello, R.C.; Harper, G.P.; Hunter, D.J.; Karran, E. H.; Markwell, R.E.; Miles-Williams, A.J.; Rahman, S.S.; Ward, R.W. J. Med. Chem. 1994, 37, 158.
128. Galardy, R.E.; Grobelny, D.; Kortylewicz, Z.P.; Poncz, L. Metalloproteinases Inhib. Proc. Matrix Metalloproteinase Conf., J989, Matrix Suppl n1 1992, 259.
129. Hunter, D.J.; Bird, J.; Cassidy, F.; De Mello, R.C.; Harper, G.P.; Karran, E.H.; Markwell, R.E.; Miles-Williams, A.J ; Ward, R W. Bioorg. & Med. Chem. Lett. 1994, 4, 2833.
130. Brown, P.A.; Borkakoti, N., Bottomley, K.M., Broadhurst, M.J.; D'Arcy, A.; Hallam, T.; Johnson, W.H.; Lawton, G.; Lewis, E.J.; Murray, E J.; Nixon, J.S.; Williams, D.H.; Winkler, F. J. Cell Biochem. Suppl. 18D, 1994, 120
131. Kortylewicz, Z P ; Galardy, R.E. J. Med. Chem. 1990, 33, 263.
132. Darlak, K.; Miller, R.B.; Stack, M.S.; Spatola, A.F.; Gray, R D. J. Biol. Chem. 1990, 265, 5199.
133. Beszant, B.; Bird, J.; Gaster, L.M.; Harper, G.P.; Hughes, I.; Karran, E H.; Markwell, R.E.; Miles-Williams, A.J.; Smith, S.A. J Med. Chem. 1993, 36, 4030.
134. Donald, D.K.; Hann, M.M.; Saunders, J.; Wadsworth, H.J. 1986; U. S. Patent 4,595,700.
135. Schwartz, M.A.; Venkataraman, S.; Ghaffari, M.A.; Libby, A., Mookhtiar, K.A.; Mallya, S.K.; Birkedal-Hansen, H.; Van Wart, H.E. Biochem. Biophys. Res Commun. 1991, 176, 173.
136. Bird, J.; Harper, H.I.; Hunter, D.J.; Karran, E.H.; Markwell, R.E.; Miles-Williams, A.J.; Rahman, S.S.; Ward, R.W. Bioorg. & Med. Chem. Lett. 1995, 5, 2593.
137. Hughes, I., Harper, G.P.; Karran, E.H ; Markwell, R.E.; Miles-Williams, A.J. Bioorg & Med. Chem. Lett. 1995, 5, 3039.
138. Tomczuk, B.E ; Gowravaram, M.R.; Johnson, J S.; Delecki, D.; Cook, E R.; Ghose, A.K.; Mathiowetz, A.M.; Spurlino, J.C.; Rubin, B ; Smith, D.L.; Pulvino, T.; Wahl, R.C. Bioorg. & Med. Chem. Lett. 1995, 5, 343.
139. Gowravaram, M.R.; Tomczuk, B.E.; Johnson, J.S.; Delecki, D.; Cook, E.R.; Ghose, A.K.; Mathiowetz, A.M.; Spurlino, J.C.; Rubin, B ; Smith, D.L.; Pulvino, T.; Wahl, R.C. J. Med. Chem. 1995, 38, 2570.
140. Wahl, R.C.; Pulvino, T.A.; Mathiowetz, A.M.; Chose, A.K.; Johnson, J.S.; Delecki, D.; Cook, E.R.; Gainor, J.A.; Gowravaram, M R ; Tomczuk, B.E. Bioorg. & Med. Chem. Lett. 1995, 5, 349.
141. Singh, J.; Conzentino, P.; Cundy, K.; Gainor, J.A.; Gilliam, C.L.; Gordon, T.D.; Johnson, J.A.; Morgan, B.A.; Schneider, E.D.; Wahl, R.C.; Whipple, D.A. Bioorg. & Med. Chem. Lett. 1995, 5, 337.
142. Isomura, Y.; Akamatsu, S.; Yoden, T.; Kudo, M.; Skira, S. WO Pat. 93/09090.
143. a) Shaw, A.; Wolanin, D.J. 1986, Eur. Pat. EP 231,081
144. b) Seed, M.P.; Ismaiel, S , Cheung, C.Y.; Thompson, T.A.; Gardner, C.R.; Atkins, R.M.; Elson, C.J. Ann. Rheum. Dis. 1993, 52, 37.
145. a) MacPherson, L.J.; Parker, D.T.; Jeng, A.Y. 1996; U.S. Patent 5,506,242.
146. b) MacPherson, L.J.; Parker, D.T. 1995; U.S. Patent 5,455,258.
147. c) MacPherson, L.J.; Parker, D.T.; Jeng, A.Y. WO Pat. 96/00214.
148. d) O'Byrne, E.M.; Parker, D.T.; Roberts, E.D.; Goldberg, R.L ; MacPherson, L.J.; Blancuzzi, V.; Wilson, D.; Singh, H.N.; Ludewig, R.; Ganu, V.S. Inflamm. Res. 1995, 44 (Suppl. 2), S117.
149. e) Parker, D. T.; MacPherson, L. J.; Goldstein, R.; Justice, M. R.; Zu, L. J.; Capparelli, M.; Whaley, L. W.; Boehm, C.; O'Byrne, E. M.; Goldberg, R. L.; Ganu, V. S. P73 7th Int. Conf. Inflammation Res. Assoc., White Haven, PA, Sept. 25-29, 1994.
150. O'Byrne, E.M.; Blancuzzi, V.; Singh, H.N.; Roberts, E.D. Inflamm. Res. 1995, 44 (Suppl. 3), S221.
151. Gonnella, N.C ; Bohacek, R ; Zhang, X ; Kolossvary, I.; Paris, C.G.; Melton, R.; Winter, C.; Hu, S.-I ; Ganu, V. Proc. Natl. Acad. Sci. 1995, 92, 462.
152. a) Miller, A.; Whittaker, M.; Beckett, R. P. WO Pat. 95/35275.
153. b) Miller, A.; Whittaker, M.; Becken, R. P. WO Pat. 95/35276.
154. Kluender, H.C.E.; Benz, G.H.; Brittelli, D.R ; Bullock, W.H.; Combs, K.J.; Dixon, B.R.; Schneider, S.P.E.; Wood, J.; Vanzandt, M.C ; Wolanin, D J.; Wilhelm, S.M. WO Pat. 96/15096.
155. Bols, M.; Binderup, L.; Hansen, J.; Rasmussen, P. J. Med. Chem. 1992, 35, 2768.
156. Liang, C.-M.; Turner, N. A ; Witiak, D. T. WO Pat. 93/23075.
157. Chandler, G.; Collins, M. A.; Fox, F.; Hylands, P.J.; Moore, M.; Weigley, S.K.; Chandler, G.L.; Wngley, S.K.; Collins, M.A.D WO Pat. 92/16517.
158. Harris, G.H.; Hoogsteen, K.; Silverman, K.C.; Raghoobar, S.L.; Bills, G.F.; Lingham, R B.; Smith, J.L.; Dougherty, H.W.; Cascales, C.; Pelaez, F. Tetrahedron, 1993, 49, 2139.
159. Smith, P.W.; Lai, P.W.Q.; Whittington, A.R.; Cox, B.; Houston, J.G. Bioorg. & Med. Chem. Lett. 1994, 4, 2821.
160. Yeh, L-A.; Chen, J.; Baculi, F.; Gingrich, D.E.; Shen, T.Y. Bioorg. & Med Chem. Lett. 1995, 5, 1637.
161. Sun, H H.; Kaplita, P V.; Houck, D.R.; Stawicki, M.B.; McGarry, R.; Wahl, R.C.; Gillum, A.M.; Cooper, R. Phytotherapy Res. 1996, 10, 194.
162. Umino, T.; Yoshizaki, H.; Wakatabe, H. 1996; GB Pat. 2297324A.
163. a) Grams, F.; Reinemer, P.; Powers, J.C.; Kleine, T.; Pieper, M.; Tschesche, H.; Huber, R.; Bode, W. Eur. J. Biochem. 1995, 228, 830.
164. b) Grams, F.; Crimmin, M.; Hinnes, L.; Huxley, P.; Pieper, M.; Tschesche, H.; Bode, W. Biochemistry, 1995, 34, 14012.
165. c) Bode, W.; Reinemer, P.; Huber, R; Kleine, T.; Schnierer, S.; Tschesche, H. EMBO Journal, 1994, 13, 1263.
166. d) Stams, T.; Spurlino, J.C.; Smith, D.L.; Wahl, R.C.; Ho, T.F.; Qoronfleh, M.W.; Banks, T.M.; Rubin B. Structural Biology, 1994, 1, 119.
167. e) Reinemer, P.; Grams, F.; Huber, R.; Kleine, T.; Schnierer, S.; Piper, M.; Tschesche, H., Bode, W. FEBS Letters, 1994, 338, 227-233.
168. f) Stocker, W.; Grams, F.; Baumann, U.; Reinemer, P.; Gomis-Ruth, F.-X.; McKay, D.E.; Bode, W. Protein Science, 1995, 4, 823.
169. a) 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: Structure. Function, and Genetics, 1994, 19, 98.
170. b) Borkakoti, N.; Winkler, F.K.; Williams, D.H.; D'Arcy, A.; Broadhurst, M.J.; Brown, P.A.; Johnson, W.H.; Murray, E.J. Structural Biology, 1994, 1, 106
171. c) Lovejoy, B.; Hassell, A.M.; Luther, M.A.; Weigl, D.; Jordan, S.R. Biochemistry, 1994, 33, 8207.
172. a) Browner, M.F.; Smith, W.W.; Castelhano, A.L. Biochemistry, 1995, 34, 6602.
173. b) Browner, M.F. Perspectives in Drug Discovery and Design, 1994, 2, 343.
174. a) Dhanaraj, V.; Ye, Q.-Z.; Johnson, L.L.; Hupe, D.J.; Ortwine, D.F.; Dunbar, J.B.; Rubin, J.R.; Pavlovsky, A.; Humblet, C.; Blundell, T.L. Structure, 1996, 4, 375.
175. b) Becker, J.W.; Marcy, A.I.; Rokosz, L.L.; Axel, M.G.; Burbaum, J.J.; Fitzgerald, P.M.D.; Cameron, P.M; Esser, C.K.; Hagmann, W.K.; Hermes, J.D.; Springer, J.P. Protein Science, 1995, 4, 1966.
176. a) Van Doren, S.R.; Kurochkin, A.V.; Hu, W.; Ye, Q.-Z.; Johnson, L.L.; Hupe, D.J.; Zuiderweg, E.R.P. Protein Science, 1995, 4, 2487.
177. b) Gooley, P.R ; O'Connell, J.F.; Marcy, A.I.; Cuca, G.G.; Salowe, S.P.; Bush, B.L.; Hermes, J.D ; Esser, C K.; Hagmann, W.K.; Springer, J.P.; Johnson, B.A. Structural Biology, 1994, 1, 111.
178. Welch, A. R.; Holman, C. M.; Huber, M.; Brenner, M. C.; Browner, M. F.; Van Wart, H. E. Biochemistry, 1996, 35(31), 10103.
179. Sapolsky, A.I ; Keiser, H.; Howell, D.S.; Woessner, J.F., Jr.; J. Clin. Invest. 1976, 58, 1030.
180. Pelletier, J.-P.; Martel-Pelletier, J.; Howell, D.S ; Ghandur-Mnaymneh, L.; Enis, J.E.; Woessner, J F., Jr., Arthritis Rheum. 1983, 26, 63.
181. Delaisse, J.; Eechout, Y.; Sear, C.; Galloway, A.; McCullagh, D.; Vaes, G. Biochem. Biohphys, Res. Commun. 1985, 133, 483.
182. DiPasquale, G.; Caccese, R.; Pasternak, R.; Conarty, J.; Hubbs, S.; Perry, K. Proc. Soc. Exp. Biol. Med. 1986, 183, 262.
183. Greenwald, R.A. Ann. N.Y. Acad. Sci. 1994, 752, 181.
184. Smith, G N., Jr.; Brandt, K. D.; Hasty, K.A Ann. N.Y. Acad. Sci. 1994, 732, 436.
185. Yu, L.P. Jr.; Burr, D B ; Brandt, K.D.; O'Connor, B.L.; Rubinow, A.; Albrecht, M. J. Rhematol. 1996, 23, 137.
186. Sewell, K.L.; Breedveld, F.; Furrie, E.; O'Brien, J.; Brinckerhoff, C.; Dynesius-Trentham, R.; Nosaka, Y.; Trentham, D.E. Cell. Immunol. 1996, 167, 195.
187. DiMartino, M.J.; High, W.; Galloway, W.A.; Crimmiti, M.J. Ann. N.Y. Acad. Sci. 1994, 732, 411.
188. Parnham, M.J.; Day, R.O.; van den Berg, W B Agents Actions, 1994, 41, C145.
189. Lewis, E.J.; Bishop, J.; Bottomley, K.M.; Bradshaw, D.; Broadhurst, M.; Brown, P.A.; Greenham, A.K.; Johnson, W.H.; Hallam, T.J.; Lawton, G.; Nixon, J.S. S5, N.Y. Acad. Sci.; Inhibition of Matrix Metalloproteinases, Therapeutic Potential, Tampa, FL. Jan. 19-22, 1994.
190. Scrip, 1996, 2129, 11.
191. Pharmaprojects, 1996, Therapeutic Updates 17 (July), au155-M2Z.
192. Rankin, E.G.; Choy, E.H.; Kassimos, D.; Kingsley, G.H.; Sopwith, A.M.; Isenberg, D.A.; Panayi, G.S. Br. J. Rheumatol. 1995, 34, 334.
193. Pharmaprojects, 1996, Therapeutic Updates 17 (Oct.), au197-M2Z.
194. Gearing, A J.; Beckett, P.; Christodoulou, M.; Churchill, M.; Clements, J.M.; Crimmin, M.; Davidson, A.H.; Drummond, A.H.; Galloway, W A.; Gilbert, R.; Gordon, J.L.; Leber, T.M.; Mangan, M ; Miller, K.; Nayee, P.; Owen, K.; Patel, S.; Thomas, W.; Wells, G.; Wood, L.M.; Woolley, K. J. Leuk. Biol. 1995, 57, 774.
195. Adis R&D Insight (Database), 1995-02-14 Update, GI 155704A.
196. Adis R&D Insight (Database), 1996-07-17 Update, BB 2983.
197. Lohmander, S.L.; Hoerrner, L.A., Lark, M.W. Arthritis Rheum., 1993, 36, 181.
198. Martel-Pelletier, J., McCollum, R.; Fujimoto, N.; Obata, K.; Cloutier, J-M.; Pelletier, J-P. Lab. Invest. 1994, 70, 807.
199. Manicourt, D-H.; Fujimoto, N.; Obata, K.; Thonar, E.J-M.A. Arthritis Rheum. 1994, 37, 1774.
200. Meikle, M C.; Bord, S.; Hembry, R.M.; Reynolds, J.J. Bone, 1995, 17, 225.
201. Dahlberg, L ; Friden, T.; Roos, H.; Lark, M.W.; Lohraander, L.S. Br. J. Rheum. 1994, 33, 1107.
202. Hembry, R.M.; Bagga, M.R.; Reynolds, J.J.; Hamblen, D.L. Ann. Rheum. Dis. 1995, 54, 25.
203. Maeda, S ; Sawai, T.; Uzuki, M.; Takahashi, Y.; Oraoto, H.; Seki, M.; Sakurai, M. Ann. Rheum. Dis. 1995, 54, 970.
204. Cawston, T.E.; Curry, V.; Ramsey, S.; Clark, I.M.; Kyle, V.A.; Adebajo, A.; Silverman, B.;Daymond, T.; Hazleman, B.L. Clin. Exp. Rheum. 1995, 13, 431.
205. Chubinskaya, S.; Much, K.; Mikecz, K.; Cs-Szabo, G.; Hasty, K.A.; Kuettner, K E.; Cole, A.A. Lab. Invest. 1996, 74, 232.
206. Freiji, J M ; Diez-Itza, I., Balbin, M.; Sanchez, L.M.; Blasco, R.; Tolivia, J.; Lopez-Otin, C. J. Biol. Chem. 1994, 209, 16766.
207. Flannery, C.R.; Sandy, J.D. 102-17, 41st Ann. Meet. Orth. Res. Soc Orlando, FL. February 13-16, 1995.
208. Knauper, V.; Lopez-Otin, C.; Smith, B.; Knight, G.; Murphy, G. J. Biol. Chem., 1996, 271, 1544-1550.
209. Mitchell, P.G ; Magna, H.A.; Reeves, L.M ; Lopresti-Morrow, L.L., Yocum, S.A.; Rosner, P.J.; Geoghegan, K.F.; Hambor, J.E. J. Clin. Invest. 1996, 97, 761.
210. Reboul, P.; Pelletier, J-P.; Hambor, J.; Magna, H.; Tardif, G.; Cloutier, J-M.; Martel-Pelletier, J. Arthritis Rheum. 1995, 38 (Suppl. 9), S268.
211. Shlopov, B.V.; Mainardi, C.L.; Hasty, K.A. Arthritis Rheum. 1995, 38 (Suppl. 9), S313.
212. Reboul, P.; Pelletier, J-P.; Tardif, G ; Cloutier, J-M.; Martel-Pelletier, J. J. Clin Invest. 1996, 97, 2011.
213. Dieppe, P.; Brandt, K.D.; Lohmander, S.; Felson, D.T. J. Rheumatol. 1995, 22, 201.
214. Dieppe, P. Acta. Orthop. Scand. 1995, 66, 1.
215. Dougados, M. Cur. Op. Rheumatol. 1995, 7, 87.
216. Rorvik, A.M.; Grondahl, A.M. Vet. Surg. 1995, 24, 255.
217. Sipe, J.D. Sem. Arth. Rheum. 1995, 25, 75.
218. Greenwald, R.; Arthritis Rheum. 1996, 39, 1455.
219. Biswas, C.; Zhang, Y.; Decastro, R.; Guo, H.; Nakamura, T.; Kataoka, H.; Nabeshima, K Cancer Res. 1995, 55, 434.
220. Heppner, K J.; Matrisian, L.M.; Jensen, R.A.; Rodgers, W.H. Am. J. Pathol. 1996, 149, 273.
221. Watanabe, M.; Takahashi, Y.; Ohta, T.; Mai, M; Sasaki, T.; Seiki, M. Cancer, 1996, 77, 1676.
222. Imren, S.; Hohn D.B.; Shimada, H.; Blavier, L. DeClerck, Y.A. Cancer Res. 1996, 56, 2891.
223. Himelstein, B.P., Canete-Soler, R.; Bernhard, E.J., Dilks, D.W.; Muschel, R.J. Invasion Metast. 1994-95, 14, 246.
224. Nuovo, G.J.; MacConnell, P.B.; Simsir, A.; Valea, F.; French, D.L. Cancer Res. 1995, 55, 267.
225. Walther, M.M.; Levy, A.; Hurley, K.; Venzon, D.; Linehen, W.M.; Stetler-Stevenson, W. J Urol. 1995, 153 (Suppl. 4), 403A.
226. Tokuraku, M, Sato, H.; Murakami, S.; Okada, Y.; Watanabe, Y.; Seiki, M. Int. J. Cancer, 1995, 64, 355.
227. Himelstein, B.; Hua, J.; Bernhard, E.; Muschel, R.J. Proc. Am. Assoc. Cancer Res. Ann. Meet. 1996, 37, 632.
228. Ueda, Y.; Imai, K.; Tsuchiya, H.; Fujiraoto, N.; Nakanishi, I.; Katsuda, S.; Seiki, M.; Okada, Y Am. J. Pathol. 1996, 148, 611.
229. Gress, T.M.; Mueller-Pillasch, F.; Lerch, M.M.; Friess, H.; Buechler, M.; Adler, G. Int. J. Cancer, 1995, 62, 407.
230. Kawashima, A.; Nakanishi, I.; Tsuchiya, H.; Roessner, A ; Obata, K.; Okada, Y. Virchows Arch., 1994, 424, 547.
231. Gilles, C.; Polette, M.; Piette, J.; Munaut, C.; Thompson, E.W.; Birembaut, P.; Foidart, J-M. Int. J. Cancer, 1996, 65, 209.
232. Brooks, P.C.; Stromblad, S.; Sanders, L.C.; von Schalscha, T L.; Aimes, R.T.; Stetler-Stevenson, W.G.; Quigley, J.P.; Cheresh, D.A. Cell, 1996, 85, 683.
233. Murray, G.T.; Duncan, ME.; O'Neill, P.; Melvin, W.T.; Fothergill, J.E. Nature Med 1996, 2, 461
234. Imai, K.; Yokohama, Y.; Nakanishi, I.; Ohuchi, E.; Fujii, Y., Nakai, N.; Okada, Y. J. Biol. Chem. 1995, 270, 6691.
235. Rouyer, N.; Wolf, C ; Chenard, M.P.; Rio, M.C.; Chambon, P.; Bellocq, J.P ; Basset, P. Invasion Metast 1994-1995, 14, 269.
236. Noel, A.C.; Lefebvre, O.; Maquoi, E ; Van Hoorde, L.; Chenard, M.P.; Mareel, M; Foidart, J.M.; Basset, P.; Rio, M C. J. Clin. Invest. 1996, 97, 1924.
237. Adts R&D Insight (Database), 1996-01-03 Update, Batimastat.
238. Brown, P.D. Pharmaceut. News, 1995, 2, 29.
239. Giavazzi, R.; Garofalo, A.; Valoti, G.; Valla, R.; Rossi, R.; Bone, E; Lucchini, B. Proc. Am. Assoc. Cancer Res. Ann. Meet. 1996, 37, 90.
240. Eccles, S.; Box, G.M.; Court, W.J.; Bone, E.A.; Thomas, W ; Brown, P.D. Cancer Res. 1996, 56, 2815.
241. Low, J.A.; Johnson, M.D., Bone, E.A.; Dickson, R.B. Clin. Canc. Res. 1996, 2, 1207.
242. Marketletter, 1994, Mar. 21.
243. Scrip, 1995, 2002, 21.
244. Scrip, 1994, 1931, 31.
245. Adis R&D Insight (Database), 1996-07-09 Update, Marimastat.
246. Pajkrt, D.; Stokkers, P.; Koster, F.; Curtis, L.D.; Brown, G.; Van Deventer, S.J.H. Eur. Cytokine Network, 1996, 7, 311.
247. Marketletter, 1996, May 27.
248. Scrip, 1996, 2132, 22.
249. Scrip, 1996, 2133-2134, 22.
250. Gore, M.; A'Hern, R.; Stankiewicz, M.; Slevin, M. Lancet, 1996, 348, 263.
251. Scrip, 1996, 2151, 16.
252. Scrip, 1996, 2141, 21.
253. Adis R&D Insight (Database), 1996-07-12 Update, Ilomastat.
254. Santos, O.; Daniels, R.; McDermott, C.; Appell, K. Proc. Am. Assoc. Cancer Res. Ann. Meet. 1996, 37, 90.
255. Pharmaprojects, 1996, Therapeutic. Main Vol.17 (May), a1525-M2Z
256. Adis R&D Insight (Database), 1996-06-28 Update, AG 3340.
257. An, Z.; Wang, X.; Wilmott, N.; Chander, S.K.; Docherty, A.; Mountain, A.; Millican, A.T.; Morhy, R.; Porter, J.R.; Kubota, T.; Hoffman, R.M. Proc. Am. Assoc. Cancer Res. Ann. Meet. 1996, 37, 89.
258. Anderson, I C ; Shipp, M.A.; Docherty, A.J.P ; Teicher, B.A Cancer Res 1996, 56, 715.
259. Gijbels, K.; Gaiardy, R E.; Steinman, L J. Clin. Invest.. 1994, 94, 2177.
260. Hewson, A K.; Smith, T.; Leonard, J.P.; Cuzner, M.L. Inflamm. Res. 1995, 44, 345
261. Liedtke, W.; Cannella, B.; Gearing, A.; Raine, C.S. Eur. Cytokine Network, 1996, 7, 284.
262. Adis R&D Insight (Database), 1996-05-01 Update, BB 3644.
263. Scrip. 1996, 2140, 17.