2',3'-dideoxy-4'-thioribonucleosides as antiviral agents

Details 2',3'-dideoxy-4'-thioribonucleosides as antiviral agents 2',3'-dideoxy-4'-thioribonucleosides as antiviral agents

1991-01-09

1992-07-07

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

544264, 536 24, 536 26, 536 23, C07H 1900, C07F 1100

Patent

active

051284588

ABSTRACT:
2'3'-dideoxy-4'-thioribonucleosides useful as antiviral agents in the treatment and prevention of AIDS are disclosed. In accordance with one aspect of the invention there are provided compounds of the formula ##STR1## where X=H, N.sub.3 or F, and B is a member selected from the group consisting of pyrimidine, 5-azapyrimidine, 6-azapyrimidine, 3-deazapyrimidine, purine, 3-deazapurine, 7-deazapurine, 8-azapurine, and 2-azapurine bases.
The intermediate 1-O-acetyl-5-O-t-butyldiphenylsilyl-4-thio-2,3-dideoxyribofuranose useful in the production of certain of the 2',3'-dideoxy-4'-thioribonucleosides is also disclosed.

REFERENCES:
Reist, et al, J. Am. Chem. Soc., 86, 5658 (1964).
Miura, et al., Purine and Pyrimidine Metabolism in Man, V, Part B, (Plenum Publishing Corp., 1986) p. 667.
Richie, et al., Can. J. Chem., 56, 794 (1977).
Reist, et al., J. Org. Chem., 33, 189 (1968).
Ototani, et al., J. Med. Chem., 17, 535 (1974).
Fu, et al., J. Org. Chem., 41, 3831 (1976).
Whistler et al., J. Org. Chem., 35, 519 (1970).

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