Phosphate prodrugs of PD154075

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 10, 2000, Pages 1121-1124

  Zhu, Zhijian ^a   Chen, Huai Gu ^a   Goel, Om P ^a   Chan, O Helen ^a   Stilgenbauer, Linda A ^a   Stewart, Barbra H ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYMETHYLBENZOYLOXYMETHOXCARBONYL; [2 (1H INDOL 3 YLMETHYL) 1 (1 PHENYLETHYLCARBAMOYL)ETHYL]CARBAMIC ACID BENZOFURAN 2 YLMETHYL ESTER; NEUROKININ 1 RECEPTOR ANTAGONIST; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AQUEOUS SOLUTION; ARTICLE; CROSS LINKING; DRUG SOLUBILITY; DRUG STABILITY; DRUG TRANSFORMATION; MALE; NONHUMAN; PARTIAL DRUG SYNTHESIS; RAT;

ANIMALS; DRUG STABILITY; INDOLES; MALE; PHOSPHATES; PHOSPHORIC ACID ESTERS; PRODRUGS; RATS; RATS, WISTAR; SOLUBILITY; TRYPTOPHAN;

ANIMALIA;

EID: 0034657530     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00183-9     Document Type: Article

References (29)

1. (a) Grunberg, S. M. Support Care Cancer 1997, 5, 9.
2. (b) Herrstedt, J. Support Care Cancer 1996, 4, 416.
3. (c) Tavorath, R.; Hesketh, P. J. Drugs 1996, 52, 639.
4. (a) Rudd, J. A.; Jordan, C. C.; Naylor, R. J. Br. J. Pharmacology 1996, 119, 931.
5. (b) Gardner, C. J.; Twissell, D. J.; Dale, T. J.; Gale, J. D.; Jordan, C. C.; Kilpatrick, G. J.; Bountra, C.; Ward, P. Br. J. Pharmacology 1995, 116, 3158.
6. (a) Gonzalez, M. I.; Field, M. J.; Holloman, E. F.; Hughes, J.; Oles, R. J.; Singh, L. Eur. J. Pharmacol. 1998, 344, 115.
7. (b) Boyle, S.; Guard, S.; Higginbottom, M.; Horwell, D.C.; Howson, W.; McKnight, A. T.; Martin, K.; Pritchard, M. C.; O'Toole, J.; Raphy, J.; Rees, D. C.; Roberts, E.; Watling, K. J.; Woodruff, G. N.; Hughes, J. Bioorg. Med. Chem. 1994, 2, 357.
8. (a) Bundgaard, H. Drug Future 1991, 16, 443.
9. (b) Bundgaard, H.; Rasmussen, G. J. Pharm. Res. 1991, 8, 1238.
10. (c) Bundgaard, H.; Rasmussen, G. J. Pharm. Res. 1991, 8, 313.
11. (d) Buur, A.; Bundgaard, H. Int. J. Pharm. 1988, 46, 159.
12. (e) Klixbull, U.; Bundgaard, H. Int. J. Pharm. 1984, 20, 273.
13. (a) Stewart, B. H.; Taylor, M. D. In Peptide-Based Drug Design: Controlling Transport and Metabolism; Taylor, M. D., Amidon, G. L., Eds.; American Chemical Society: Washington DC, 1994; pp 199-217.
14. (b) Amidon, G. L.; Lee, H. J. Annu. Rev. Pharmacol. Toxicol. 1994, 34, 321.
15. (c) Oliyai, R.; Stella, V. J. Annu. Rev. Pharmacol. Toxicol. 1993, 32, 521.
16. Blade, R. J.; Pang, Y. S.; Selwood, D. L. WO 9532966, 1996; Chem. Abstr. 1996, 124, P232432z.
17. McComb, R. B.; Bowers, G. L. Jr.; Posen, S. Alkaline Phosphatase; Plenum Press: New York, 1979.
18. Murdock K.C., Lee V.J., Citarella R.V., Durr F.E., Nicolau G., Kohlbrenner M. J. Med. Chem. 36:1993;2098.
19. Bundgaard, H. In Design of Prodrugs; Bundgaard, H., Ed.; Elsevier: Amsterdam, 1985; pp 1-92.
20. (a) Remers, W. A. In Heterocyclic Compounds, Indoles, Part 1; Hoalihan, W. J., Ed.; Wiley-Interscience: New York, 1972.
21. (b) Sundberg, R. J. Indoles; Academic: San Diego, 1996; chapter 9.
22. Safadi M., Oliyai R., Stella V.J. Pharm. Res. 10:1993;1350.
23. Bundgaard H., Falch E., Jensen E. J. Med. Chem. 32:1989;2503.
24. (a) Wang, B.; Gangwar, S.; Pauletti, G. M.; Siahaan, T. J.; Borchardt, R. T. J. Org. Chem. 1997, 62, 1363.
25. (b) Nicolaou, M. G.; Yuan, C.-S.; Borchardt, R. T. J. Org. Chem. 1996, 61, 8636.
26. (c) Ueda, Y.; Matiskella, J. D.; Mikkilineni, A. B.; Farina, V.; Knipe, J. O.; Rose, W. C.; Casazza, A. M.; Vyas, D. M. Bioorg. Med. Chem. Lett. 1995, 5, 247.
27. (d) Ueda, Y.; Mikkilineni, A. B.; Knipe, J. O.; Rose, W. C.; Casazza, A. M.; Vyas, D. M. Bioorg. Med. Chem. Lett. 1993, 3, 1761.
28. Kirby, A. J. In Adv. Phys. Org. Chem.; Gold, V. Bethell, D., Eds.; Academic: London, 1980; Vol. 17, pp 241-243.
29. Burton D.J., Koppes W.M. J. Org. Chem. 40:1975;3026.