# US 10,118,894 B2 · Isoindolinone derivatives useful as antiviral agents

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- Number: US 10,118,894 B2
- Document ID: US10118894B2
- Status: Granted
- Kind: B2
- Application number: 15/326,100
- Filed: 2015-07-20
- Published: 2017-07-20
- Granted: 2018-11-06
- Earliest claimed: 2014-07-22
- Assignees: ViiV Healthcare UK Limited
- Applicants: Viiv Healthcare UK Limited
- Inventors: Brian Alvin Johns; Emile Johann Velthuisen; Jason Gordon Weatherhead
- Web page: https://patentgrep.com/patent/US10118894B2

## CPC

- C07D 209/46: with an oxygen atom in position 1
- A61P 31/12: Antivirals
- A61P 31/14: for RNA viruses
- A61P 31/18: for HIV
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of Formula I are disclosed and methods of treating viral infections with compositions comprising such compounds.

## Claims

### Claim 1

A compound of Formula I:
or a pharmaceutically acceptable salt thereof wherein:
R1 is C1-6 alkyl;
R2 is C5-14aryl, C3-7cycloalkyl, (C3-7)cycloalkenyl, (C2-9)heterocycle, or (C2-9)heteroaryl, each of which is optionally substituted by one to four substituents selected from halo, C1-6 alkyl, C1-6 hetereoalkyl, or C1-6 alkylene or C1-6 hetereoalklylene wherein said C1-6alkylene or C1-6 hetereoalklylene are bonded to adjacent carbon atoms on said C5-14 aryl, C3-7cycloalkyl, (C3-C7)cycloalkenyl, (C2-C9)heterocycle, or (C2-C9)heteroaryl to form a ring, and wherein each heterocycle, heteroaryl, heteroalkyl, and hetereoalkylene contains one to three heteroatoms selected from S, N or O;
L is a bond or C1-3 alkylene: and
R3 is H, C1-6 alkyl, C5-14aryl, C3-7cycloalkyl, (C3-7)cycloalkenyl, (C2-9)heterocycle, or (C2-9)heteroaryl, each of which is optionally substituted by one to four substituents selected from halo, or C1-6 alkyl, and wherein each heterocycle and heteroaryl contains one to three heteroatoms selected from S, N or O.

### Claim 2 (depends on 1)

The compound or salt according to claim 1 wherein R1 is t-butyl.

### Claim 3 (depends on 1)

The compound or salt according to claim 1 wherein R2 is optionally substituted phenyl or optionally substituted cyclohexenyl.

### Claim 4 (depends on 3)

The compound or salt according to claim 3 wherein R2 is phenyl optionally substituted by one to four substituents selected from fluorine, methyl, or —CH2CH2CH2O— or —NHCH2CH2O— wherein said —CH2CH2CH2O— or —NHCH2CH2O— is bonded to adjacent carbon atoms on said phenyl to form a bicyclic ring.

### Claim 5 (depends on 1)

The compound or salt according to claim 1 wherein R3 is phenyl.

### Claim 6 (depends on 1)

The compound or salt according to claim 1 wherein the stereochemistry on the carbon to which OR1 is bound is as depicted below

### Claim 7 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 7)

A method for treating a viral infection in a patient mediated at least in part by a virus in the retrovirus family of viruses, comprising administering to said patient a composition according to claim 7.

### Claim 9 (depends on 8)

The method of claim 8 wherein said viral infection is mediated by HIV virus.