Method for the synthesis, compositions and use of 2'-deoxy-5-fluoro-3'-thiacytidine and related compounds
AssigneeEmory University
InventorsDennis C. Liotta, Raymond F. Schinazi, Woo-Baeg Choi
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Abstract
The present invention relates to a method of preparing the antiviral compounds 2'-deoxy-5-fluoro-3'thiacytidine (FTC) and various prodrug analogues of FTC from inexpensive precursors with the option of introducing functionality as needed; methods of using these compounds, particularly in the prevention and treatment of AIDS; and the compounds themselves. This synthetic route allows the stereoselective preparation of the biologically active isomer of these compounds and related compounds.
Claims21
A method for treating a human having an HIV infection comprising administering to the human an effective HIV-treatment amount of a compound of the formula:
- ##STR9##
A method for treating a human having an HIV infection comprising administering to the human an effective HIV-treatment amount of a .beta.-isomer of a substituted 2'-deoxy-5-fluoro-3'-thiacytidine having the formula:
- ##STR10## wherein Y is independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl and acyl;
- and
- R is selected from the group consisting of H, hydroxyl, oxyacyl, monophosphate, diphosphate, and triphosphate.
A method for treating a human having an HIV infection comprising administering to the human an effective HIV treatment amount of a compound of the formula:
- ##STR11## wherein Y is monophosphate, diphosphate, or triphosphate.
A method for treating a human having an HIV infection comprising administering to the human an effective HIV-treatment amount of a compound of the formula:
- ##STR12## wherein Y is independently selected from the group consisting of H, alkyl, cycloalkyl, and acyl;
- and
- R is selected from the group consisting of H, hydroxyl, oxyacyl, monophosphate, diphosphate, and triphosphate.
A method for treating a human having an HIV infection comprising administering to the human an effective HIV-treatment amount of a pharmaceutically acceptable salt of a compound of the formula:
- ##STR13##
A method for treating a human having an HIV infection comprising administering to the human an effective HIV-treatment amount of the pharmaceutically acceptable salt of .beta.-isomer of a substituted 2'-deoxy-5-fluoro-3'-thiacytidine having the formula:
- ##STR14## wherein Y is independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl and acyl;
- and
- R is selected from the group consisting of H, hydroxy, oxyacyl, monophosphate, diphosphate, and triphosphate.
A method for treating a human having an HIV infection comprising administering to the human an effective HIV-treatment amount of a pharmaceutically acceptable salt of a compound of the formula:
- ##STR15## wherein Y is monophosphate, diphosphate, or triphosphate.
A method for treating a human having an HIV infection comprising administering to the human an effective HIV treatment amount of the pharmaceutically acceptable salt of a compound of the formula:
- ##STR16## wherein Y is independently selected from the group consisting of H, alkyl, cycloalkyl and acyl;
- and
- R is selected from the group consisting of H, hydroxyl, oxyacyl, monophosphate, diphosphate, and triphosphate.
Dependencies are inferred from the claim text.