# US 10,501,445 B2 · Quinoxalinones and dihydroquinoxalinones as respiratory syncytial virus antiviral agents

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- Number: US 10,501,445 B2
- Document ID: US10501445B2
- Status: Granted
- Kind: B2
- Application number: 16/140,337
- Filed: 2018-09-24
- Published: 2019-01-24
- Granted: 2019-12-10
- Earliest claimed: 2013-01-28
- Assignees: Janssen Sciences Ireland UC
- Applicants: Janssen Sciences Ireland Uc
- Inventors: Abdellah Tahri; Tim Hugo Maria Jonckers; Pierre Jean-Marie Bernard Raboisson; Samuel Dominique Demin
- Web page: https://patentgrep.com/patent/US10501445B2

## CPC

- C07D 403/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P 31/12: Antivirals
- A61P 31/14: for RNA viruses
- C07D 401/14: containing three or more hetero rings
- C07D 403/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Quinoxalinones and dihydroquinoxalinones having inhibitory activity on RSV replication and having the formula I including addition salts, and stereochemically isomeric forms thereof; compositions containing these compounds as active ingredient and processes for preparing these compounds and compositions.

## Claims

### Claim 1

A compound of formula I
or a stereochemically isomeric or tautomeric form thereof wherein:
Y is N or N—R4;
Z1 is N or C—R6;
Z2 is N or C—R3;
R1 is selected from the group consisting of H, halogen, C1-C6alkyl and C3-C7cycloalkyl;
R2 is —(CR7R8)n—R9;
R3 is selected from the group consisting of H, C1-C6alkyl, C3-C7cycloalkyl, CF3 and halogen;
R4 is selected from the group consisting of H, C1-C6alkyl and C3-C7cycloalkyl;
R6 is selected from the group consisting of H, halogen, aryl and heteroaryl, wherein each of aryl or heteroaryl is optionally substituted with one or more R10;
R7 and R8 are each independently selected from the group consisting of H, C1-C6alkyl and C3-C7cycloalkyl;
n is an integer selected from the range of 1 to 6;
R9 is selected from the group consisting of H, halogen, SO2R7, C1-C6alkyl, CONR7R8, COOR7, OH, CN, F, CFH2, CF2H and CF3;
R10 is selected from the group consisting of H, OH, CN, halogen, CFH2, CF2H, CF3, CONR7R8, COOR7 and C1-C6 alkyl, wherein each of R10 is optionally substituted with one or more substituents selected from the group comprising NR7R8, CF3, CH3, OCH3, OCF3, morpholinyl and halogen;
or an addition salt or solvate thereof.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein R1 is halogen.

### Claim 3 (depends on 1)

A compound according to claim 1, wherein R2 is —(CR7R8)n—R9, R7 and R8 are each independently hydrogen or CH3, n is an integer of 3 or 4, R9 is selected from the group consisting of halogen, CF3 and SO2R7, and R7 is CH3.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein R6 is selected from the group consisting of H, halogen, phenyl, pyridinyl, thiophenyl, pyrimidinyl, pyrazolyl, pyrrolyl, thiazolyl, each R6 is optionally substituted with one or more R10.

### Claim 5 (depends on 1)

A compound according to claim 1, wherein R10 is selected from the group consisting of halogen and C1-C3 alkyl, wherein each R10 is optionally substituted with one or more substituents selected from the group consisting of NR7R8, CF3, morpholinyl and halogen.

### Claim 6 (depends on 1)

A compound according to claim 1, wherein R6 is selected from the group consisting of phenyl, pyridinyl, thiophenyl, pyrimidinyl, pyrazolyl, pyrrolyl, and thiazolyl, each R6 is optionally substituted with halogen.

### Claim 7 (depends on 1)

A compound according to claim 1, wherein R2 is C1-C6 alkyl optionally substituted with one or more of F or SO2-Me.

### Claim 8 (depends on 1)

A compound according to claim 1, wherein R4 is cyclopropyl or H.

### Claim 9 (depends on 1)

A compound of claim 1, wherein the compound is selected from the group consisting of:

### Claim 10 (depends on 1)

A compound according to claim 1, wherein R2 is (CR7R8)n—R9, R7 and R8 are each independently hydrogen or CH3, n is an integer of 3 or 4, R9 is selected from the group consisting of halogen, CF3 and SO2R7, and R7 is H.

### Claim 11 (depends on 1)

A compound according to claim 1, wherein R3 is halogen.

### Claim 12 (depends on 1)

A compound according to claim 1, wherein R6 is H.

### Claim 13 (depends on 1)

A compound according to claim 1, wherein R7 and R8 are H.

### Claim 14 (depends on 1)

A compound according to claim 1, wherein R9 is halogen.

### Claim 15 (depends on 1)

A pharmaceutical composition comprising a pharmaceutically acceptable carrier, and a compound of claim 1.

### Claim 16 (depends on 1)

A process for preparing a pharmaceutical composition, said process comprising mixing a pharmaceutically acceptable carrier with a therapeutically effective amount of a compound of claim 1.

### Claim 17 (depends on 1)

A method of treating an RSV infection in a subject in need thereof, said method comprising administering to the subject a therapeutically effective amount of a compound of claim 1.

### Claim 18 (depends on 1)

A method of inhibiting RSV replication in a subject in need thereof, said method comprising administering to the subject a therapeutically effective amount of a compound of claim 1.