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Generated: August 22, 2017

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Title: Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane
Abstract:A method and composition for the treatment of HIV and HBV infections in humans is disclosed that includes administering an effective amount of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, a pharmaceutically acceptable derivative thereof, including a 5' or N.sup.4 alkylated or acylated derivative, or a pharmaceutically acceptable salt thereof, in a pharmaceutically acceptable carrier. A process for the resolution of a racemic mixture of nucleoside enantiomers is also disclosed that includes the step of exposing the racemic mixture to an enzyme that preferentially catalyzes a reaction in one of the enantiomers.
Inventor(s): Liotta; Dennis C. (Stone Mountain, GA), Schinazi; Raymond F. (Decatur, GA), Choi; Woo-Baeg (North Brunswick, NJ)
Assignee: Emory University (Atlanta, GA)
Application Number:08/488,097
Patent Claims: 1. A derivative of .beta.-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane of the formula:

wherein R.sub.1 is selected from the group consisting of hydrogen, acetyl, propionyl, butyryl, and pentanoyl and R.sub.2 is hydrogen.

2. The mono, di, or trihosphate ester of .beta.-2-Hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane.

3. The compound of claim 1, wherein R.sub.1 is butpryl and R.sub.2 is hydrogen.

4. A physiologically acceptable salt of .beta.-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane.

5. A pharmaceutical composition comprising an effective amount to treat HIV in humans of a physiologically acceptable salt of .beta.-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane.

6. A pharmaceutical composition comprising an effective amount to treat HIV in humans of the mono-, di- or triphosphate ester of .beta.-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane.

7. A pharmaceutical composition comprising an effective amount to treat HIV in humans of the acetyl, propionyl, butyryl, or pentanoyl ester of .beta.-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane.
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Express Scripts
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