# US 8,569,478 B2 · Modified 4′-nucleosides as antiviral agents

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- Number: US 8,569,478 B2
- Document ID: US8569478B2
- Status: Granted
- Kind: B2
- Application number: 12/067,995
- Filed: 2006-09-26
- Published: 2011-01-27
- Granted: 2013-10-29
- Earliest claimed: 2005-09-26
- Assignees: Gilead Pharmasset LLC
- Applicants: Jinfa Du; Phillip Furman; Michael Joseph Sofia
- Inventors: Jinfa Du; Phillip Furman; Michael Joseph Sofia
- Web page: https://patentgrep.com/patent/US8569478B2

## CPC

- C07H 19/06: Pyrimidine radicals
- A61P 31/12: Antivirals
- A61P 31/18: for HIV
- A61P 31/20: for DNA viruses
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07H 19/16: Purine radicals
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds, methods and compositions for treating a host infected with human immunodeficiency virus and hepatitis B virus comprising administering an effective amount of a described 4′-C-substituted β-D- and β-L-nucleoside or a pharmaceutically acceptable salt or prodrug thereof, are provided.

## Claims

### Claim 1

A compound which is a β-D- and β-L-nucleoside or a pharmaceutically acceptable salt thereof, having a structure defined by formula (I) or by formula (II):
wherein:
X is hydrogen, F, Cl, Br, I, NH2, NHR4, NR4R5, NHOH, NHOR4, NHNH2, NR4NH2, NHNHR4, SH, SR4, S(O)bR4, OH, OR4, N3, CN, or CF3;
Y is hydrogen, F, Cl, Br, I, NH2, NHR4, NR4R5, NHOH, NHOR4, NHNH2, NR4NH2, NHNHR4, SH, SR4, S(O)bR4, OH, OR4, N3, CN, CF3, hydroxymethyl, methyl, substituted or unsubstituted ethyl, substituted or unsubstituted vinyl, substituted or unsubstituted 2-bromovinyl, or substituted or unsubstituted ethynyl;
R1 is F or N3;
R2 is OH, OR4, OC(O)R4, —OP(O)(OQ)a(NHR4)b, SH, SR4, S(O)bR4, SC(O)R4, NH2, NHC(O)R4, NHR4, NR4R5, NHOH, NHOR4, NHNH, NR4NH2, or NHNHR4;
R3 is F, cyano, azido, ethynyl, chlorovinyl, fluorovinyl, alkyl (C2-6), one to three halogen substituted alkyl (C1-6), alkenyl or alkynyl (C2-6);
Z is O, S, CH2 or C═CH2;
A is N, CH, or CF; and
R4 and R5 are the same or different and are lower alkyl, lower alkenyl, acyl of carbon 1-17, aryl, or aralkyl;
M is at least one member selected from the group consisting of H+, Na+, and K+;
and
a has a value of 0 or 1, b has a value of 1 or 2, and Q is M or R4.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the nucleoside is a 4′-C-substituted-3′-fluoro-2′,3′-dideoxynucleoside.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the nucleoside is a 4′-C-substituted-3′-azido-2′,3′-dideoxynucleoside.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the nucleoside is a 4′-C-ethynyl-3′-fluoro-2′,3′-dideoxynucleoside.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the nucleoside is a 4′-C-ethynyl-3′-azido-2′,3′-dideoxynucleoside.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the nucleoside is a 4′-C-ethynyl-3′-fluoro-3′-deoxythymidine.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the nucleoside is a 4′-C-ethynyl-3′-azido-3′-deoxythimidine.