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Generated: July 21, 2017

DrugPatentWatch Database Preview

Details for Patent: 6,069,252

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Details for Patent: 6,069,252

Title: Method of resolution and antiviral activity of 1,3-oxathiolane nucleoside enantiomers
Abstract:A process for the resolution of a racemic mixture of nucleoside enantiomers that includes the step of exposing the racemic mixture to an enzyme that preferentially catalyzes a reaction in one of the enantiomers. The nucleoside enantiomer (-)-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner.
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:08/474,406
Claims:1. A (+)-.beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane compound at least 95% free of the corresponding (-)-.beta.-enantiomer of the formula: ##STR1## 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 a physiologically acceptable salt thereof.

2. The 5'-phosphate ester of the compound of claim 1.

3. The 5'-monophosphate ester of the compound of claim 1.

4. The 5'-diphosphate ester of the compound of claim 1.

5. The 5'-triphosphate ester of the compound of claim 1.

6. The compound of claim 1 wherein R.sub.1 is acetyl and R.sub.2 is hydrogen.

7. (+)-.beta.-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, or a physiologically acceptable salt thereof, substantially in the absence of its corresponding (-)-.beta.-L-enantiomer.

8. A (+)-.beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane compound substantially in the absence of its corresponding (-)-.beta.-L-enantiomer of the formula: ##STR2## 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 a physiologically acceptable salt thereof.

9. (+)-.beta.-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, or a physiologically acceptable salt thereof, at least 95% free of the corresponding (-)-.beta.-enantiomer.
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Farmers Insurance
Baxter
Cantor Fitzgerald
McKinsey
Harvard Business School
Healthtrust
Novartis
Julphar
Mallinckrodt
Queensland Health

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