Endothelin converting enzyme inhibitors

Current Pharmaceutical Design

Volumn 3, Issue 6, 1997, Pages 597-614

  Jeng, Arco Y ^a   De Lombaert, Stéphane ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 BIPHENYL 4 YL 1 (1H TETRAZOL 5 YL)ETHYLAMINOMETHYL PHOSPHONIC ACID; DIMERCAPROL; ENDOTHELIN; ENDOTHELIN CONVERTING ENZYME; ENDOTHELIN CONVERTING ENZYME INHIBITOR; ENZYME INHIBITOR; METALLOPROTEINASE INHIBITOR; PHOSPHORAMIDON; SCH 54470; UNCLASSIFIED DRUG;

BRAIN VASOSPASM; DRUG DESIGN; ENZYME INHIBITION; HEART FAILURE; HUMAN; HYPERTENSION; KIDNEY FAILURE; NONHUMAN; PRIORITY JOURNAL; REVIEW; SUBARACHNOID HEMORRHAGE;

EID: 0030731003     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (128)

1. Yanagisawa, M.; Kurihara, H.; Kimura, S.; Tomobe, Y.; Kobayashi, M.; Mitsui, Y.; Yazaki, Y.; Goto, K.; Masaki, T. Nature 1988, 332, 411-415.
2. Inoue, A.; Yanagisawa, M.; Kimura, S., Kasuya, Y.; Miyauchi, T.; Goto, K ; Masaki, T. Proc. Natl. Acad. Sci. USA 1989, 86, 2863-2867.
3. Bloch, K.D.; Friedrich, S.P.; Lee, M.-E.; Eddy, R.L.; Shows, T.B.; Quertermous, T. J. Biol. Chem. 1989, 264, 10851-10857.
4. Bloch, K.D.; Eddy, R L.; Shows, T.B.; Quertermous, T. J. Biol. Chem. 1989, 264, 18156-18161.
5. Bloch, K.D.; Hong, C.C.; Eddy, R.L.; Shows, T.B.; Quertermous, T. Genomics 1991, 10, 236-242.
6. Arinami, T.; Ishikawa, M.; Inoue, A.; Yanagisawa, M.; Masaki, T.; Yoshida, M.C.; Hamaguchi, H. Am. J. Hum. Genet. 1991, 48, 990-996.
7. Arai, H ; Hori, S.; Aramori, I.; Ohkubo, H.; Nakanishi, S. Nature 1990, 348, 730-732.
8. Sakurai, T.; Yanagisawa, M.; Takuwa, Y.; Miyazaki, H.; Kimura, S.; Goto, K.; Masaki, T. Nature 1990, 348, 732-735.
9. Higgins, J.P.; Pelton, J.T.; Miller, R.C. Pharmacol. Thera. 1993, 59, 55-123.
10. Rubanyi, G.M.; Polokoff, M.A. Pharmacol. Rev. 1994, 46, 325-415.
11. Goto, K.; Hama, H.; Kasuya, Y. Jap. J. Pharmacol. 1996, 72, 261-290.
12. Randall, M.D. Pharmacol Thera. 1991, 50, 73-93.
13. Kohan, D.E. Am J Kidney Dis. 1997, 29, 2-26.
14. Patel, T.R CNS Drugs 1996, 5, 293-310.
15. Battistini, B ; D'Orléans-Juste, P.; Sirois, P. Lab. Invest. 1993, 68, 600-628.
16. Warner, T.D. Cardiovasc. Drug Rev 1994, 12, 105-122.
17. Moreland, S. Can. J Physiol. Pharmacol. 1994, 72, 1469-1471.
18. Ferro, C.J , Webb, D.J. Drugs 1996, 51, 12-27.
19. Turner, A.J.; Murphy, L.J. Biochem. Pharmacol. 1996, 51, 91-102.
20. Denault, J.-B ; Claing, A.; D'Orléans-Juste, P.; Sawamura, T.; Kido, T.; Masaki, T., Leduc, R. FEBS Lett. 1995, 362, 276-280.
21. Turner, A.J.; Tanzawa, K. FASEB J. 1997, 11, 355-364
22. Ikegawa, R.; Matsumura, Y.; Tsukahara, Y.; Takaoka, M.; Morimoto, S. Biochem. Biophys. Res. Commun. 1990, 171, 669-675.
23. Sawamura, T.; Kasuya, Y.; Matsushita, Y.; Suzuki, N.; Shinmi, O.; Kishi, N.; Sugita, Y.; Yanagisawa, M.; Goto, K.; Masaki, T.; Kimura, S. Biochem. Biophys. Res. Commun. 1991, 174, 779-784.
24. Ohnaka, K.; Takayanagi, R.; Yamauchi, T.; Umeda, F.; Nawata, H. Biochem. Intern. 1991, 23, 499-506.
25. McMahon, E.G.; Palomo, M A.; Moore, W.M.; McDonald, J.F.; Stern, M.K. Proc. Natl. Acad. Sci. USA 1991, 88, 703-707.
26. Xu, D.; Emoto, N.; Giaid, A.; Slaughter, C.; Kaw, S., deWit, D.; Yanagisawa, M. Cell 1994, 78, 473-485.
27. Schmidt, M.; Kröger, B.; Jacob, E.; Seulberger, H.; Subkowski, T.; Otter, R.; Meyer, T.; Schmalzing, G.; Hillen, H. FEBS Lett. 1994, 356, 238-243.
28. Shimada, K.; Takahashi, M.; Tanzawa, K. J. Biol. Chem. 1994, 269, 18275-18278.
29. Shimada, K.; Takahashi, M.; Ikeda, M.; Tanzawa, K. FEBS Lett. 1995, 371, 140-144.
30. Shimada, K.; Takahashi, M.; Turner, A.J.; Tanzawa, K. Biochem. J. 1996, 315, 863-867.
31. Emoto, N.; Yanagisawa, M. J. Biol. Chem. 1995, 270, 15262-15268.
32. Yanagisawa, M. Intern. Business Communications' Third Intern. Symp. on Endothelin Inhibitors (Philadelphia, PA) 1997.
33. Kimura, S ; Kasuya, Y.; Sawamura, T.; Shinmi, O.; Sugita, Y.; Yanagisawa, M.; Goto, K.; Masaki, T. J. Cardiovasc. Pharmacol. 1989, 13(Suppl. 5), S5-S7.
34. Ashizawa, N.; Okumura, H.; Kobayashi, F.; Aotsuka, T.; Takahashi, M.; Asakura, R.; Arai, K.; Matsuura, A. Biol. Pharm. Bull., 1994, 17, 207-211.
35. Ashizawa, N.; Okumura, H.; Kobayashi, F.; Aotsuka, T.; Asakura, R.; Arai, K.; Ashikawa, N.; Matsuura, A. Biol. Pharm. Bull., 1994, 17, 212-216.
36. Corvol, P.; Williams, T.A.; Soubrier, F. Methods Enzymol. 1995, 248, 283-305.
37. Kagan, H.M.; Reddy, V.B.; Narasimhan, N.; Csiszar, K. CIBA Found. Symp. 1995, 192, 100-121
38. Colombo, G.; Papadopoulos, N.J.; Ash, D.E.; Villafranca, J.J. Arch. Biochem. Biophys. 1987, 252, 71-80.
39. Klee, C.B.; Haiech, J Ann. N. Y. Acad. Sci. 1980, 356, 43-53.
40. Okada, K.; Takada, J ; Arai, Y.; Matsuyama, K ; Yano, M. Biochem. Biophys. Res. Commun. 1991, 180, 1019-1023.
41. Monta, A., Nomizu, M.; Okitsu, M.; Horie, K.; Yokogoshi, H.; Roller, P.P. FEBS Letts. 1994, 353, 84-88.
42. Inagaki, S.; Ikeda, M.; Tomita, T.; Morita, A.; Nomizu, M.; Kumagai, T.; Okitsu, M.; Yokogoshi, H.; Roller, P.P. Jap. J. Pharmacol. 1993, 61(Suppl. 1), 214P.
43. Claing, A.; Neugebauer, W.; Yano, M.; Rae, G.A., D'Orléans-Juste, P. J. Cardiovasc. Pharmacol. 1995, 26(Suppl. 3), S72-S74.
44. Hemsén, A.; Pernow, J.; Lundberg J M. Acta Physiol. Scand. 1991, 141, 325-334.
45. Kobayashi, E.; Ando, K.; Nakano, H.; Iida, T.; Ohno, H.; Morimoto, M.; Tamaoki, T J. Antibiotics 1989, 42, 1470-1474.
46. Iida, T.; Kobayashi, E.; Yoshida, M ; Sano, H J. Antibiotics 1989, 42, 1475-1481.
47. Kojiri, K.; Ihara, M.; Nakajima, S.; Kawamura, K.; Funaishi, K.; Yano, M.; Suda, H. J. Antibiotics 1991, 44, 1342-1347.
48. Nakajima, S.; Niiyama, K.; Ihara, M.; Kojiri, K.; Suda, H. J. Antibiotics 1991, 44, 1348-1356.
49. Ihara, M.; Noguchi, K., Saeki, T.; Fukuroda, T.; Tsuchida, S.; Kimura, S.; Fukami, T.; Ishikawa, K.; Nishikibe, M.; Yano, M. Life Sci. 1992, 50, 247-255.
50. Tsurumi, Y.; Ueda, H.; Hayashi, K.; Takase, S.; Nishikawa, M.; Kiyoto, S.; Okuhara, M. J. Antibiotics 1995, 48, 1066-1072.
51. Yoshimura, S.; Tsurumi, Y.; Takase, S.; Okuhara, M. J. Antibiotics 1995, 48, 1073-1075.
52. Tsurumi, Y.; Ohhata, N.; Iwamoto, T.; Shigematsu, N.; Sakamoto, K ; Nishikawa, M.; Kiyoto, S.; Okuhara, M. J Antibiotics 1994, 47, 619-630.
53. Tsurumi, Y.; Fujie, K.; Nishikawa, M.; Kiyoto, S.; Okuhara, M. J. Antibiotics 1995, 48, 169-174.
54. Matsuura, A.; Okumura, H.; Asakura, R.; Ashizawa, N.; Takahashi, M.; Kobayashi, F.; Ashikawa, N.; Arai, K. Jap. J. Pharmacol. 1993, 63, 187-193.
55. Sato, R.; Iijima, Y.; Matsushita, H.; Negishi, A.; Takamatsu, Y.; Haruyama, H.; Kinoshita, T.; Kodama, K.; Ishii, A. Jap. Patent 1996, JP 8208646.
56. Patil, A.D.; Freyer, A.J ; Eggleston, D.S.; Haltiwanger, R.C.; Tomcowicz, B.; Breen, A.; Johnson, R.K. J. Nat. Prod. 1997, 60, 306-308.
57. Patil, A.D.; Freyer, A.J., Breen, A.; Carte, B.; Johnson, R.K. J. Nat Prod. 1996, 59, 606-608.
58. Schechter, I.; Berger, A. Biochem. Biophys. Res. Commun. 1967, 27, 157-162.
59. Bihovsky, R ; Levinson, B.L.; Loewi, R.C.; Erhardt, P.W.; Polokoff, M A. J. Med. Chem. 1995, 38, 2119-2129.
60. Wakimasu, M.; Mori, M.; Kawada, A. Eur. Patent Appl. 1992, EP 0518299A2.
61. Bertenshaw, S.R.; Rogers, R.S.; Stern, M.K.; Norman, B H.; Moore, W M.; Jerome, G.M.; Branson, L.M.; McDonald, J.F.; McMahon, E.G.; Palomo, M.A. J. Med. Chem. 1993, 36, 173-176.
62. Fukami, T.; Hayama, T.; Amano, Y.; Nakamura, Y.; Arai, Y.; Matsuyama, K.; Yano, M.; Ishikawa, K. Bioorg. Med. Chem. Lett. 1994, 4, 1257-1262.
63. Kukkola, P.J.; Savage, P.; Sakane, Y.; Berry, J.C.; Bilci, N.A.; Ghai, R.D.; Jeng, A.Y J. Cardiovasc. Pharmacol. 1995, 26(Suppl. 3), S65-S68.
64. McKittrick, B.A.; Stamford, A.W.; Weng, X.; Ma, K.; Chackalamannil, S.; Czarniecki, M.; Cleven, R M.; Fawzi, A.B. Bioorg. Med. Chem. Lett. 1996, 6, 1629-1634.
65. Keller, P.M.; Lee, C.-P.; Fenwick, A.E.; Atkinson, S.T.; Elliott, J.D ; DeWolf, W.E., Jr Biochem. Biophys. Res Commun. 1996, 223, 372-378.
66. Balwierczak, J.L.; Kukkola, P.J.; Savage, P.; Jeng, A.Y Biochem. Pharmacol. 1995, 49, 291-296.
67. Pollock, D.M.; Shiosaki, K.; Sullivan, G M.; Opgenorth, T J. Biochem. Biophys. Res. Commun. 1992, 186, 1146-1150.
68. Bigaud, M.; Hauss, B.; Schalk, C.; Jauch, M.F.; D'Orchymont, H. Fundam. Clin. Pharmacol. 1994, 8, 155-161
69. Descombes, J.-J.; Mennecier, P ; Versluys, D., Barou, V , de Nanteuil, G.; Laubie, M.; Verbeuren, T.J. J. Caidiovasc. Pharmacol 1995, 26(Suppl. 3), S61-S64.
70. Norcini, G.; Santangelo, F. Eur. Patent Appl. 1995, EP 0636630A1.
71. McKittrick, B.A.; Czarniecki, M.F.; Chackalamannil, S.; Chung, S.; Defrees, S.; Stamford, A.W. Intern Patent Appl. 1996, WO 96/00732.
72. Chackalamannil, S.; Chung, S.; Stamford, A.W , McKittrick, B A.; Wang, Y.; Tsai, H., Cleven, R.; Fawzi, A.; Czarniecki, M. Bioorg. Med. Chem. Lett. 1996, 6, 1257-1260.
73. Lloyd, J.; Schmidt, J.B.; Hunt, J.T.; Banish, J.C.; Little, D.K.; Tymiak, A.A. Bioorg. Med. Chem. Lett. 1996, 6, 1323-1326.
74. Vemulapalli, S.; Fawzi, A.B.; Chintala, M.; Stamford, A., Sabin, C.; Kurowski, S.; Brown, A.; Chiu, P.; Sybertz, E. The Pharmacologist 1997, 39, 26.
75. Rotmensch, H.H.; Vlasses, P.H.; Swanson, B.N.; Irvin, J.D.; Harris, K.E.; Merrill, D.G.; Ferguson, R.K. Am. J. Cardiol. 1984, 53, 116-119.
76. Karanewsky, D.S.; Badia, M.C ; Cushman, D W.; DeForrest, J M.; Dejneka, T.; Loots, M.J.; Perri, M.G.; Petrillo, E.W., Jr.; Powell, J.R. J. Med Chem. 1988, 31, 204-212.
77. Ikeda, S.; Ashley, J.A.; Wirsching, P.; Janda, K.D. J. Am. Chem. Soc. 1992, 114, 7604-7606.
78. 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, 2833-2836.
79. De Lombaert, S.; Tan, J.; Stamford, L.J.; Sakane, Y.; Berry, C.; Ghai, R.D. Bioorg. Med. Chem. Lett. 1994, 4, 2715-2720.
80. De Lombaert, S.; Erion, M.D.; Tan, J.; Blanchard, L., El-Chehabi, L.; Ghai, R.D.; Sakane, Y.; Berry, C.; Trapani, A.J. J. Med. Chem 1994, 37, 498-511.
81. De Lombaert, S.; Blanchard, L.; Tan, J.; Sakane, Y.; Berry, C., Ghai, R.D Bioorg. Med. Chem. Lett. 1995, 5, 145-150.
82. De Lombaert, S.; Ghai, R.D.; Jeng, A.Y.; Trapani, A.J.; Webb, R.L. Biochem. Biophys. Res. Commun. 1994, 204, 407-412.
83. Caner, H.H.; Kwan, A.-L., Arthur, A.; Jeng, A.Y.; Lappe, R.W.; Kassell, N.F.; Lee, K.S. J. Neurosurg 1996, 85, 917-922.
84. Held, H.-D.; Raschak, M.; Uhlig, S. Naunyn-Schmiedeberg's Arch. Pharmacol. 1997, 355, 619-624.
85. De Lombaert, S ; Blanchard, L.; Berry, C.; Ghai, R.D.; Trapani, A.J Bioorg. Med. Chem. Lett. 1995, 5, 151-154.
86. Trapani, A.J., De Lombaert, S.; Kuzmich, S.; Jeng, A.Y. J. Cardiovasc Pharmacol 1995, 26(Suppl. 3), S69-S71.
87. De Lombaert, S.; Stamford, L.B.; Blanchard, L.; Tan, J ; Hoyer, D.; Diefenbacher, C.G.; Wei, D.; Wallace, E.M.; Moskal, M.A ; Savage, P.; Jeng, A Y. Bioorg. Med Chem. Lett 1997, 7, 1059-1064.
88. Kaw, S.; Emoto, N , Jeng, A Y.; Yanagisawa, M. Fourth Intern. Conf. on Endothelin (London, UK) 1995, Abstract C6.
89. Shetty, S.S.; Savage, P ; DelGrande, D.; De Lombaert, S , Jeng, A Y Fifth Intern. Conf. on Endothelin (Kyoto, Japan) 1997, Abstract, P27.
90. Deprez, P.; Guillaume, J ; Dumas, J., Vevert, J.-P. Bioorg. Med. Chem Lett. 1996, 6, 2317-2322
91. Kukkola, P J.; Bilci, N.A.; Kozak, W.X.; Savage, P.; Jeng, A.Y. Bioorg. Med. Chem Lett. 1996, 6, 619-624.
92. Bertenshaw, S.R.; Talley, J J.; Rogers, R S., Carter, J.S.; Moore, W M , Branson, L.M.; Koboldt, C.M. Bioorg. Med. Chem. Lett. 1993, 3, 1953-1958.
93. Jeng, A.Y , Savage, P.; Balwierczak, J L., Trapani, A J.; Ksander, G.M Fifth Intern. Conf on Endothelin (Kyoto, Japan) 1997, Abstract, P28
94. Norcini, G.; Santangelo, F. Eur. Patent Appl. 1995, EP 0636621A1.
95. Trapani, A J., Balwierczak, J.L.; Lapps, R.W.; Stanton, J.L.; Graybill, S.C.; Hopkins, M.F ; Savage, P.; Sperbeck, D.M.; Jeng, A.Y. Biochem. Mol. Biol. Intern. 1993, 31, 861-867.
96. Levy, D E.; Tang, P.C.; Sweet, K.; Summers, B.; LaPierre, F.; Ezrin, A.M. Med. Chem Res. 1994, 4, 547-553.
97. Doherty, A.M.; Kornberg, B.E.; Nikam, S. Intern. Patent Appl. 1994, WO 94/28012
98. Ueki, M.; Hasato, T.; Saito, H.; Yazawa, S ; Pponda, K. Jap. Patent 1993, JP 05039266A.
99. Fujita, Y.; Satoh, C.; Tsukahara, Y.; Miyawaki, N. Jap. Pharmacol. Soc. 1997, Abstract P-28.
100. Waldeck, H.; Höltje, D.; Messinger, J.; Antel, J.; Wurl, M.; Thormählen, D. Eur Patent Appl. 1996, EP 0733642A1.
101. Ahn, K.; Cheng, X.-M.; Doherty, A.M.; Elslager, E.F., Kornberg, B.; Lee, C.; Leonard, D.; Nikam, S.S ; Werbel, L.M. Intern. Patent Appl. 1996, WO 96/19474.
102. Ahn, K., Sisneros, A M., Pan, S.; Hupe, D ; Nikam, S.; Lee, C ; Doherty, A.; Kaw, S ; Emoto, N.; Yanagisavva, M. FASEB J. 1996, 10, A1404
103. Warner, T.D.; Battistini, B.; Doherty, A.M.; Corder, R. Biochem. Pharmacol. 1994, 48, 625-635.
104. McMahon, E.G.; Palomo, M.A.; Brown, M A.; Bertenshaw, S R.; Carter, J.S. Am. J. Hypertension 1993, 6, 667-673.
105. Vemulapalli, S , Watkins, R.W.; Brown, A., Cook, J.; Bernardino, V.; Chiu, P J.S. Life Sci. 1993, 53, 783-793.
106. Cook, D.A. Pharmacol. Thera. 1995, 66, 259-284.
107. Qureshi, A.I.; Dawson, R.; Frankel, M.R., Stern, B.J. The Neurologist 1996, 2, 53-65.
108. Matsumura, Y ; Ikegawa, R.; Suzuki, Y.; Takaoka, M.; Uchida, T., Kido, H ; Shinyama, H , Hayashi, K., Watanabe, M.; Morimoto, S Life Sci 1991, 49, 841-848.
109. Kwan, A.-L.; Bavbek, M.; Jeng, A Y , Mantara, W ; Toyoda, T ; Lappe, R W., Kassell, N F ; Lee, K S J. Neurosurg. 1997, 87, 281-286.
110. Parmley, W.W. J. Am. Coll. Cardiol. 1989, 13, 771-785.
111. Armstrong, P.W.; Moe, G.W. Circulation 1994, 88, 2941-2952.
112. Love, M.P.; Haynes, W.G.; Gray, G.A.; Webb, D.J.; McMurray, J.J.V. Circulation 1996, 94, 2131-2137.
113. Robbins, S.L. In Pathologic Basis of Disease; W. B. Saunders Co.: Philadelphia, 1974; Chapter 24, pp.1078-1147.
114. Vemulapalli, S.; Chiu, P.J.S ; Chintala, M.; Bernardino, V. Pharmacology 1993, 47, 188-193
115. Bird, J.E ; Webb, M.L., Wasserman, A.J.; Liu, E.C.K.; Giancarli, M.R.; Durham, S.K. Pharmacology 1995, 50, 9-23.
116. Takahashi, K ; Totsune, K.; Mouri, T. Nephron 1994, 66, 373-379
117. Watanabe, T.; Suzuki, N.; Shimamoto, N.; Fujino, M ; Imada, A. Nature 1990, 344, 114.
118. Pernow, J.; Wang, Q.-D. Cardiovasc. Res. 1997, 33, 518-526.
119. Hasdai, D.; Lerman, A. Coronary Artery Dis. 1995, 6, 901-904
120. Douglas, S.A.; Louden, C.; Vickery-Clark, L.M.; Storer, B.L., Hart, T.; Feuerstein, G.Z.; Elliott, J.D.; Ohlstein, E.H Circulation Res. 1994, 75, 190-197.
121. Ferrer, P.; Valentine, M.; Jenkins-West, T.; Weber, H.; Goller, N.L.; Durham, S.K.; Molloy, C.J.; Moreland, S. J. Cardiovasc Pharmacol. 1995, 26, 908-915.
122. Takiguchi, Y.; Sogabe, K. Eur. J. Pharmacol. 1996, 309, 59-62.
123. Hay, D.W.P.; Henry, P.J.; Goldie, R.G. Am. J. Respir. Crit. Care Med. 1996, 154, 1594-1597.
124. Gui, G.; Xu, D.; Emoto, N.; Yanagisawa, M. J. Cardiavasc. Pharmacol. 1993, 22(Suppl. 8), S53-S56.
125. Takahashi, M.; Fukuda, K.; Shimada, K.; Barnes, K.; Turner, A J.; Ikeda, M.; Koike, H.; Yamamoto, Y.; Tanzawa, K. Biochem. J. 1995, 311, 657-665.
126. De Lombaert, S.; Chatelain, R.E., Fink, C.A.; Trapani, A.J. Current Pharmaceutical Design 1996, 2, 443-462.
127. Trifilieff, A ; Da Silva, A.; Gies, J-P. Eur. Respir. J. 1993, 6, 576-587.
128. Skidgel, R.A. J. Cardiovasc. Pharmacol. 1992, 20(Suppl. 9), S4-S9.