# US 4,396,623 A · Carbocyclic analogs of uracil nucleosides as antiviral agents

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- Number: US 4,396,623 A
- Document ID: US4396623A
- Status: Granted
- Kind: A
- Application number: 06/296,507
- Filed: 1981-08-26
- Granted: 1983-08-02
- Earliest claimed: 1981-08-26
- Assignees: Southern Research Institute
- Inventors: Y. Fulmer Shealy; C. Allen O'Dell; William M. Shannon
- Web page: https://patentgrep.com/patent/US4396623A

## CPC

- C07D 239/54: as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D 239/545: with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D 239/553: with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

There is provided a method for the treatment of viral infections by treating a host animal with a pharmaceutically effective amount of a carbocyclic analog of a nucleoside represented by Formula I: ##STR1## wherein X is chlorine, bromine, iodine, a lower alkyl group or an amino group of the formula --NHR.sup.2 wherein R.sup.2 is a lower alkyl group; and R and R' can be the same or different members selected from the group consisting of hydrogen, an alkanoyl group or an aroyl group.

## Claims

### Claim 1

A process for the treatment of a host animal having a herpes virus infection which comprises administering to said host animal a therapeutically effective amount of a compound represented by the following formula: ##STR4## wherein X is bromine, iodine, methyl or an amino group of the formula --NHR.sup.2 wherein R.sup.2 is a C.sub.1-4 lower alkyl group; and R and R.sup.1 can be the same or different members selected from the group consisting of hydrogen or a C.sub.1-6 alkanoyl group.

### Claim 2 (depends on 1)

A process as defined in claim 1 wherein said virus infection is a herpes simplex virus infection.

### Claim 3 (depends on 2)

A process as defined in claim 2 wherein X is Br.

### Claim 4 (depends on 3)

A process as defined in claim 3 wherein each of R and R.sup.1 is CH.sub.3 CO--.

### Claim 5 (depends on 3)

A process as defined in claim 3 wherein each of R and R.sup.1 is hydrogen.

### Claim 6 (depends on 2)

A process as defined in claim 2 wherein X is I.

### Claim 7 (depends on 6)

A process as defined in claim 6 wherein each of R and R.sup.1 is hydrogen.

### Claim 8 (depends on 6)

A process as defined in claim 6 wherein each of R and R.sup.1 is CH.sub.3 CO--.

### Claim 9 (depends on 2)

A process as defined in claim 2 wherein X is --NHCH.sub.3 and each of R and R.sup.1 is hydrogen.

### Claim 10 (depends on 2)

A process as defined in claim 2 wherein X is --NHC.sub.4 H.sub.9 and each of R and R.sup.1 is hydrogen.

### Claim 11 (depends on 2)

A process as defined in claim 2 wherein X is --CH.sub.3 and each of R and R.sup.1 is hydrogen.

### Claim 12

A compound having the formula: ##STR5## wherein R.sup.2 is a C.sub.1-4 lower alkyl group, and R and R.sup.1 can be the same or different members selected from the group consisting of hydrogen or a C.sub.1-6 alkanoyl group.

### Claim 13 (depends on 12)

A compound as defined in claim 12 wherein X is --NHCH.sub.3 and each of R and R.sup.1 is hydrogen.

### Claim 14 (depends on 12)

A compound as defined in claim 12 wherein X is --NHC.sub.4 H.sub.9 and each of R and R.sup.1 is hydrogen.

### Claim 15

(.+-.)-5-Bromo-1-[(1.alpha.,3.b eta.,4.alpha.)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]-2,4(1H,3H)-pyrimidin edione diacetate.

### Claim 16

(.+-.)-1-[(1. alpha.,3.beta.,4.alpha.)-3-Hydroxy-4-(hydroxymethyl)cyclopentyl]-5-iodo-2,4 (1H,3H)-pyrimidinedione diacetate.