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Generated: December 16, 2017

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Claims for Patent: 6,642,245

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Claims for Patent: 6,642,245

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:08/475,339
Patent Claims: 1. A method for treating HIV infection in humans comprising administering an effective amount of (-)-.beta.-L-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, or its physiologically acceptable salt, optionally in a pharmaceutically acceptable carrier.

2. The method of claim 1, wherein the carrier is suitable for oral delivery.

3. The method of claim 1, wherein the carrier comprises a capsule.

4. The method of claim 1, wherein the carrier is in the form of a tablet.

5. The method of claim 1, wherein the administration is parenteral.

6. The method of claim 1, wherein .beta.-L-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is administered in a form that is at least 95% free of its corresponding .beta.-D-enantiomer.

7. The method of claim 1, wherein .beta.-L-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is administered in a form that is at least 95% free of its corresponding .beta.-D-enantiomer.

8. The method of claim 1, wherein .beta.-L-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is administered as an isolated enantiomer.

9. A method for treating HIV infection in humans comprising administering an effective amount of (+)-.beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, or its physiologically acceptable salt, optionally in a pharmaceutically acceptable carrier.

10. The method of claim 9, wherein the carrier is suitable for oral delivery.

11. The method of claim 9, wherein the carrier comprises a capsule.

12. The method of claim 9, wherein the carrier is in the form of a tablet.

13. The method of claim 9, wherein the administration is parenteral.

14. The method of claim 9, wherein .beta.-D-2-hydroxymethyl-5-(5-fluorocytosin- 1-yl)-1,3-oxathiolane is administered in a form that is at least 95% free of its corresponding .beta.-L enantiomer.

15. The method of claim 9, wherein .beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is administered in a form that is at least 95% free of its corresponding .beta.-L-enantiomer.

16. The method of claim 9, wherein .beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is administered as an isolated enantiomer.

17. A method for treating HIV infection in humans comprising administering an effective amount of the monphosphate, diphosphate or triphosphate of .beta.-L-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, or its physiologically acceptable salt, optionally in a pharmaceutically acceptable carrier.

18. The method of claim 17, wherein the phosphate of .beta.-L-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is administered in a form that is at least 95% free of its corresponding .beta.-D-enantiomer.

19. The method of claim 17, wherein the phosphate of .beta.-L-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is administered as an isolated enantiomer.

20. A method for treating HIV infection in humans comprising administering an effective amount of the monophosphate, diphosphate, or triphosphate of .beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, or its physiologically acceptable salt, optionally in a pharmaceutically acceptable carrier.

21. The method of claim 20, wherein the phosphate of .beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is administered in a form that is at least 95% free of its corresponding .beta.-L-enantiomer.

22. The method of claim 20, wherein the phosphate of .beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is administered as an isolated enantiomer.
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