2',3'-dideoxy-4'-thioribonucleosides and synthetic precursors thereof
AssigneeSouthern Research Institute
InventorsJohn A. Montgomery, John A. Secrist, III
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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.dbd.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 is useful in the production of certain of the 2',3'-dideoxy-4'-thioribonucleosides. Other intermediates include the 4-thio-2,3-dideoxyribofuranose having different hydroxyl protecting groups and leaving groups.
Claims28
A compound having the formula I ##STR20## where X is 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.
A compound having the formula II ##STR21## where X is H, 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.
1-O-acetyl-5-O-t-butyldiphenylsilyl-4-thio-2,3-dideoxyribofuranose.
A compound having the formula 10a ##STR22## wherein R.sup.1 is a protected hydroxy group, and R.sup.2 is selected from the group consisting of lower alkoxy, aryloxy, substituted aryloxy, arylthio, alkyl carboxy, aryl carboxy, alkylsulfonate, arylsulfonate, acyloxy, and halogen.
Dependencies are inferred from the claim text.