Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane
AssigneeEmory University
InventorsDennis C. Liotta, Raymond F. Schinazi, Woo-Baeg Choi
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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 N4 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.
Claims75
A method for treating HIV infection in humans comprising administering an effective amount of (−)-β-L-2-hydroxymethyl-5-(5-fluorocytosine-1-yl)-1,3-oxathiolane, or a compound of the formula:
- wherein R1 and R2 are independently alkyl, acyl or an amino acid;
- and wherein one of R1 and R2 can be H,
- or physiologically acceptable salt, in a gelatin capsule for oral delivery.
A method for treating HIV infection in humans comprising administering an effective amount of (−)-β-L-2-hydroxymethyl-5-(5-fluorocytosine-1-yl)-1,3-oxathiolane, or a compound of the formula:
- wherein R1 and R2 are independently alkyl, acyl or an amino acid;
- and wherein one of R1 and R2 can be H,
- or physiologically acceptable salt, in a pharmaceutically acceptable carrier for oral delivery wherein the carrier comprises cellulose.
A method for treating HIV infection in humans comprising administering an effective amount of (−)-β-L-2-hydroxymethyl-5-(5-fluorocytosine-1-yl)-1,3-oxathiolane, or a compound of the formula:
- wherein R1 and R2 are independently alkyl, acyl or an amino acid;
- and wherein one of R1 and R2 can be H,
- or physiologically acceptable salt, in a pharmaceutically acceptable carrier for oral delivery wherein the carrier comprises magnesium stearate.
A pharmaceutical composition for treating HIV infection in humans comprising an effective amount of (−)-β-L-2-hydroxymethyl-5-(5-fluorocytosine-1-yl)-1,3-oxathiolane, or a compound of the formula:
- wherein R1 and R2 are independently alkyl, acyl or an amino acid;
- and wherein one of R1 and R2 can be H,
- or physiologically acceptable salt, in a gelatin capsule for oral delivery.
A pharmaceutical composition for treating HIV infection in humans comprising an effective amount of (−)-β-L-2-hydroxymethyl-5-(5-fluorocytosine-1-yl)-1,3-oxathiolane, or a compound of the formula:
- wherein R1 and R2 are independently alkyl, acyl or an amino acid;
- and wherein one of R1 and R2 can be H,
- or physiologically acceptable salt, in a pharmaceutically acceptable carrier for oral delivery wherein the carrier comprises cellulose.
A pharmaceutical composition for treating HIV infection in humans comprising an effective amount of (−)-β-L-2-hydroxymethyl-5-(5-fluorocytosine-1-yl)-1,3-oxathiolane, or a compound of the formula:
- wherein R1 and R2 are independently alkyl, acyl or an amino acid;
- and wherein one of R1 and R2 can be H,
- or physiologically acceptable salt, in a pharmaceutically acceptable carrier for oral delivery wherein the carrier compnses magnesium stearate.
Dependencies are inferred from the claim text.