# US 5,705,492 A · 3'-O-aminoacyl ARA uridines, method of making, and antiviral activity

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,705,492 A
- Document ID: US5705492A
- Status: Granted
- Kind: A
- Application number: 08/677,705
- Filed: 1996-07-10
- Granted: 1998-01-06
- Earliest claimed: 1995-07-13
- Assignees: Hoffmann-La Roche Inc.
- Inventors: Joseph Armstrong Martin; Gareth John Thomas
- Web page: https://patentgrep.com/patent/US5705492A

## CPC

- C07H 19/06: Pyrimidine radicals
- A61P 31/12: Antivirals
- A61P 31/22: for herpes viruses
- 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

Pyrimidine nucleoside derivatives of formula ##STR1## wherein R.sup.1 represents aryl, R.sup.2 represents lower alkyl, R.sup.3 represents an acyl group derived from an amino acid and R.sup.4 represents hydrogen or fluorine and the asterisk denotes that the configuration at the carbon atom indicated thereby is (S) or (R), are disclosed. These compounds, as well as their salts, are useful as antiviral agents.

## Claims

### Claim 1

A compound of the formula ##STR4## wherein R.sup.1 represents aryl,
R.sup.2 represents lower alkyl,
R.sup.3 represents an acyl residue of an amino acid,
R.sup.4 represents hydrogen or fluorine, and the asterisk denotes that the configuration at the carbon atom indicated thereby is (S) or (R),
and pharmaceutically acceptable acid addition salts thereof.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein the configuration at the carbon atom indicated by the asterisk is (S).

### Claim 3 (depends on 1)

A compound according to claim 1, wherein R.sup.1 represents a substituted phenyl group.

### Claim 4 (depends on 3)

A compound according to claim 3, wherein the substituted phenyl group is 2,4-dichioro-5-methoxyphenyl.

### Claim 5 (depends on 1)

A compound according to claim 1, wherein R.sup.2 represents methyl.

### Claim 6 (depends on 1)

A compound according to claim 1, wherein R.sup.3 represents an acyl group derived from a natural .alpha.-amino acid.

### Claim 7 (depends on 6)

A compound according to claim 6, wherein R.sup.3 represents L-valyl.

### Claim 8 (depends on 1)

A compound according to claim 1, wherein R.sup.4 represents fluorine.

### Claim 9 (depends on 3)

A compound according to claim 3, wherein R.sup.2 is methyl, and R.sup.3 represents a natural .alpha.-amino acid.

### Claim 10

The compound 1-›5-›2(S)-(2,4-Dichloro-5-methoxyphenoxy)-propionamido!-2,5-dideoxy-2-flu oro-3-O-L-valyl-.beta.-D-arabinofuranosyl!-5-ethyluracil.

### Claim 11

The compound 1-›5-›2(R)-(2,4-Dichloro-5-methoxyphenoxy)-propionamido!-2,5-dideoxy-2-flu oro-3-O-L-valyl-.beta.-D-arabinofuranosyl!-5-ethyluracil.

### Claim 12 (depends on 1)

A pharmaceutical composition comprising as the therapeutically active ingredient at least one compound of formula I, claim 1, together with a compatible pharmaceutical carrier.

### Claim 13 (depends on 1)

A process for the manufacture of the compounds of formula I, claim 1, which process comprises
a) reacting a compound of the general formula ##STR5## wherein R.sup.1 represents aryl,
R.sup.2 represents lower alkyl,
R.sup.4 represents hydrogen or fluorine, and the asterisk denotes that the configuration at the carbon atom indicated thereby is (S) or (R),
with an N-protected amino acid, and
b) cleaving off the N-protecting group.

### Claim 14 (depends on 1)

A method for the therapy of a viral infection comprising administering to the host a therapeutically effective amount of at least one compound of formula I, claim 1.