1,3-oxathiolane nucleoside analogues and methods for using same

Details 1,3-oxathiolane nucleoside analogues and methods for using same 1,3-oxathiolane nucleoside analogues and methods for using same

1995-06-07

1997-04-08

Wilson, James O.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514 23, 514 24, 514 49, 514 85, 514269, 536 41, 544242, A61K 31505

Patent

active

056188200

ABSTRACT:
The invention relates to 1,3-oxathiolane nucleoside analogues and their use in the treatment of viral infections. More specifically, this invention relates to (-)-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidi n-2-one and pharmaceutically acceptable derivatives and pharmaceutical formulations thereof.

REFERENCES:
patent: 4336381 (1982-06-01), Nagata et al.
patent: 5204466 (1993-04-01), Liotta et al.
patent: 5210085 (1993-05-01), Liotta
S. Doong et al., "Inhibition of the Replication of Hepatitis B Virus in Vitro by 2',3'-Dideoxy-3'-Thiacytidine and Related Analogues", Proc. Natl. Acad. Sci U.S.A., 88, pp. 8495-8499 (1991).
L. Frick et al., "Pharmacokinetics, Oral Bioavilability, and Metabolic Disposition in Rats of (-)-cis-5-Fluoro-1-[2-(Hydroxymethyl)-1,3-Oxathiolan-5-yl] Cytosine, a Nucleoside Analog Active against Human Immunodeficiency Virus and Hepatitis B Virus", Antimicrob. Agents Chemother., 37, pp. 2288-2292 (1993).
P. Furman et al., "The Anti-Hepatitis B Virus Activities, Cytotoxicities, and Anabolic Profiles of the (-) and (+) Enantiomers of cis-5-Fluoro-1-[2-(Hydroxymethyl)-1,3-Oxathiolan-5-yl] Cytosine", Antimicrob. Agents Chemother., 36, pp. 2686-2692 (1992).
L. Jeong et al., "Structure-Activity Relationships of .beta.-D-(25,5R)-and .alpha.-D-(2S, 5S)-1,3-Oxathiolanyl Nucleosides as Potential Anti-HIV Agents", J. Med. Chem., 36, pp. 2627-2638 (1993).
L. Jeong et al., "Asymmetric Synthesis and Biological Evaluation of .beta.-L-(2R,5S)-and .alpha.-L-(2R,5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides as Potential Anti-HIV Agents", J. Med. Chem., 36, pp. 181-195 (1993).

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