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Generated: September 21, 2017

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Title: Antiviral activity and resolution of 2-hydroxymethyl-5-(5-flurocytosin-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)
Filing Date:Jun 07, 1995
Application Number:08/482,875
Claims:1. A pharmaceutical composition comprising an effective amount to treat HIV infection in humans of (+)-.beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolan or its physiologically acceptable salt, at least 95% free of the corresponding (-)-.beta.-enantiomer in a pharmaceutically acceptable carrier.

2. A pharmaceutical composition comprising in an amount effective to treat HIV infection in humans, a (+)-.beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane at least 95% free of the corresponding (-)-.beta.-enantiomer of the formula: ##STR8## wherein R.sub.1 and R.sub.2 are selected from the group consisting of acetyl, propionyl, butyryl, and pentanoyl or R.sub.1 can be a mono, di or triphosphate ester, and one of R.sub.1 or R.sub.2 can be hydrogen, or its pharmaceutically acceptable salt in a pharmaceutically acceptable carrier.

3. The pharmaceutical composition of claim 2, wherein R.sub.1 is mono, di or triphosphate ester.

4. The pharmaceutical composition of claim 2, wherein R.sub.1 is acetyl and R.sub.2 is hydrogen.

5. A pharmaceutical composition comprising an effective amount to treat HIV infection in humans of (+)-.beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane or its physiologically acceptable salt, substantially in the absence of its corresponding .beta.-L-enantiomer in a pharmaceutically acceptable carrier .
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Cerilliant
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Fish and Richardson
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Cipla
Healthtrust
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