Potent non-peptidic dual inhibitors of endothelin-converting enzyme and neutral endopeptidase 24.11

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 8, 1997, Pages 1059-1064

  De Lombaert, Stéphane ^a   Stamford, Lisa B ^a   Blanchard, Louis ^a   Jenny, Tan ^a   Hoyer, Denton ^a   Clive, G ^a   Dongchu, Wei ^a   Wallace, Eli M ^a   Moskal, Michael A ^a   Savage, Paula ^a   Jeng, Arco Y ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 BIPHENYLYL) 1 (1H TETRAZOL 5 YL)ETHYLAMINOMETHYLPHOSPHONIC ACID; CGS 31447; ENDOTHELIN CONVERTING ENZYME; ENZYME INHIBITOR; MEMBRANE METALLOENDOPEPTIDASE; PHOSPHORAMIDON; TETRAZOLE DERIVATIVE; THIORPHAN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY;

EID: 0030934793     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00159-5     Document Type: Article

References (31)

1. Gray, G. A.; Webb, D. J. Pharmacol. Ther. 1996, 72, 109.
2. Patel, T. CNS Drugs 1996, 5, 293.
3. Rabelink, T. J.; Kaasjager, K. A. H.; Stroes, E. S. G.; Koomans, H. A. Kidney Int. 1996, 50, 1827.
4. Hay, D. W. P.; Henry, P. J.; Goldie, R. G. Am. J. Respir. Crit. Care Med. 1996, 154, 1594.
5. Webb, M.; Meek, T. D. Med. Res. Rev. 1997, 17, 17.
6. For a recent review, see: Turner, A. J.; Murphy, L. J. Biochem. Pharmacol. 1995, 51, 91.
7. Yanagisawa, H.; Maika, S. D.; deWit, D.; Emoto, N.; Yanagisawa, M.; Hammer, R. E. 4th Internat. Conf. on Endothelin; April 23-26, London (UK), 1995; P14.
8. Roques, B. P.; Noble, F.; Daugé, V.; Fournié-Zaluski, M.-C.; Beaumont, A. Pharmacol, Rev. 1993, 45, 87.
9. Fukami, T.; Hayama, T.; Amano, Y.; Nakamura, Y.; Arai, Y.; Matsuyama, K.; Yano, M.; Ishikawa, K. Bioorg. Med. Chem. Letters 1994, 4, 1257.
10. Kukkola, P. J.; Bilci, N. A.; Kozak, W. X.; Savage, P.; Jeng, A. Y. Bioorg. Med. Chem. Lett. 1996, 6, 619.
11. Tsurumi, Y.; Ueda, H.; Hayashi, K.; Takase, S.; Nishikawa, M.; Kiyoto, S.; Okuhara, M. J. Antibiotics 1995, 48, 1066.
12. 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.
13. Keller, P. M.; Lee, C.-P.; Fenwick, A. E.; Atkinson, S. T.; Elliott, J. D.; DeWolf, W. E. Biochem. Biophys. Res. Commun. 1996, 223, 372.
14. 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.
15. 50 > 5 μM): Bihovsky, R.; Levinson, B. L.; Loewi, R. C.; Erhardt, P. W.; Polokoff, M. A. J. Med. Chem. 1995, 38, 2119.
16. Bertenshaw, S. R.; Talley, J. T.; Rogers, R. S.; Carter, J. S.; Moore, W. M.; Branson, L. M.; Koboldt, C. M. Bioorg. Med. Chem. Lett. 1993, 3, 1953.
17. De Lombaert, S.; Ghai, R. D.; Jeng, A.; Trapani, A. J.; Webb, R. L. Biochem. Biophys. Res. Commun. 1994, 204, 407.
18. Caner, H. H.; Kwan, A. L.; Arthur, A. A.; Jeng, A. Y.; Lappe, R. W.; Kassell, N. F.; Lee, K. S. J. Neurosurg. 1996, 85, 917.
19. 50 for CGS 26303 was 410 nM, while a value of 1.1 μM had been determined with partially purified porcine ECE (ref 17). In both cases, CGS 26303 was about 3 times more potent than phosphoramidon as an ECE-1 inhibitor. The assessment of NEP inhibition was performed as described previously (ref 23).
20. Trapani, A. J.; Balwierczak, J. L.; Lappe, R. W.; Stanton, J. L.; Graybill, S. C.; Hopkins, M. F.; Savage, P.; Sperbeck, D.; Jeng, A. Y. The Pharmacologist 1992, 34, 159.
21. Kaw, S.; Emoto, N.; Jeng, A.; Yanagisawa, M. 4th Int. Conf. on Endothelin; April 23-25, London (UK), 1995; C6.
22. De Lombaert, S.; Blanchard, L.; Tan, J.; Sakane, Y.; Berry, C.; Ghai, R. D. Bioorg. Med. Chem. Lett. 1995, 5, 145.
23. De Lombaert, S.; Erion, M. D.; Tan, J.; Blanchard, L.; El-Chehabi, L.; Ghai, R.; Sakane, Y.; Berry, C.; Trapani, A. J. J. Med. Chem. 1994, 37, 498.
24. De Lombaert, S.; Blanchard, L.; Tan, J.; Trapani, A. J. Bioorg. Med. Chem. Lett. 1995, 5, 151.
25. Catarzi, D.; Cecchi, L.; Colotta, V.; Filacchioni, G.; Melani, F. J. Heteroc. Chem. 1992, 29, 1161.
26. Borg, S.; Estenne-Bouhtou, G.; Luthman, K.; Csöregh. I.; Hesselink, W.; Hacksell, U. J. Org. Chem. 1996, 60, 3112.
27. Merck & Co., WO 94/09029.
28. Takeda Chem. Ind., EPA 0518299A2.
29. Afarinkia, K.; Rees, C. W.; Cadogan, J. I. G. Tetrahedron 1990, 46, 7175.
30. 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.
31. Deprez, P.; Guillaume, J.; Dumas, J.; Vevert, J.-P. Bioorg. Med. Chem. Lett. 1996, 6, 2317.