Novel prodrug approach to amprenavir-based HIV-1 protease inhibitors via O→N acyloxy migration of P1 moiety

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 15, 2003, Pages 2523-2526

  Kazmierski, Wieslaw M ^a   Bevans, Patricia ^a   Furfine, Eric ^a   Spaltenstein, Andrew ^a   Yang, Hanbiao ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMPRENAVIR; CARBONIC ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; NITRO DERIVATIVE; NITROGEN; OXYGEN; PRODRUG; PROTEINASE INHIBITOR; SULFONAMIDE; WATER;

ANALYTIC METHOD; ARTICLE; ATOM; CHEMISTRY; DRUG EFFECT; DRUG SOLUBILITY; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; KINETICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PHYSICAL CHEMISTRY; RECYCLING; SOLUBILITY; STRUCTURE ACTIVITY RELATION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0038309240     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00463-3     Document Type: Article

References (15)

1. Kim E.E., Baker C.T., Dwyer M.D., Murcko M.A., Rao B.G., Tung R.D., Navia M.A. J. Am. Chem. Soc. 117:1995;1181.
2. Kazmierski W.M., Furfine E., Spaltenstein A., Wright L.L. Bioorg. Med. Chem. Lett. 12:2002;3431.
3. Tung, R., Hale, M., Baker, C., Furfine, E.; Kaldor, I.; Kazmierski, W., Spaltenstein, A. PTC Int. Appl. WO 9933815.
4. Hale, M.; Tung, R.; Baker, C.; Spaltenstein, A.; Furfine. E.; Kaldor, I., Kazmierski, W. PCT Int. Appl. WO 9933795.
5. Hale, M.; Tung, R.; Baker, C.; Spaltenstein, A.; Furfine, E.; Kaldor, I., Kazmierski, W. PCT Int. Appl. WO 9933793.
6. Hale, M.; Tung, R.; Baker, C.; Spaltenstein, A.; Furfine, E.; Kaldor, Kazmierski, W. PCT Int. Appl. WO 9933792.
7. Kazmierski, W. M.; Bevans, P.; Furfine, E.; Porter, D.; Spaltenstein, A.; Yang, H. 223rd ACS National Meeting, Orlando, FL, United States, April 7-11, 2002; MEDI-160.
8. Kiso Y., Matsumoto H., Yamaguchi S., Kimura T. Lett. Pept. Sci. 6:1999;275.
9. Hamada Y., Ohtake J., Sohma Y., Kimura T., Hayashi Y., Kiso Y. Bioorg. Med. Chem. 10:2002;4155.
10. Stieglitz U. Am. Chem. J. 31:1904;501.
11. Ransom A. Am. Chem. J. 23:1900;43.
12. Bernet B., Bishop P.M., Caron M., Kawamata T., Roy B.L., Ruest L., Sauve G., Soucy P., Deslongchamps P. Can. J. Chem. 63:1985;2818.
13. Kato S., Morie T. J. Heterocycl. Chem. 33:1996;1171.
14. 4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/hexane (1:2) to give 75 mg of the desired product 8 (13% yield).
15. The synthesis of 6.