# US 10,865,193 B2 · Pyridone derivatives for the treatment of viral infections and further diseases

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- Number: US 10,865,193 B2
- Document ID: US10865193B2
- Status: Granted
- Kind: B2
- Application number: 16/432,423
- Filed: 2019-06-05
- Published: 2019-12-05
- Granted: 2020-12-15
- Earliest claimed: 2013-05-24
- Assignees: Janssen Sciences Ireland Unlimited Company
- Applicants: Janssen Sciences Ireland Unlimited Company
- Inventors: David Craig McGowan; Pierre Jean-Marie Bernard Raboisson
- Web page: https://patentgrep.com/patent/US10865193B2

## CPC

- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/12: Antivirals
- A61P 37/02: Immunomodulators
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This invention relates to pyridone derivatives, processes for their preparation, pharmaceutical compositions, and their use in therapy.

## Claims

### Claim 1

A compound of formula (I)
or a pharmaceutically acceptable salt, solvate or polymorph thereof, wherein
R1 is C1-6 alkyl, optionally substituted by one or more substituents independently selected from the group consisting of aryl, halogen, OH, NH2, CO2H, CO2C1-3alkyl, C(O)NHC1-3alkyl, C(O)NHSO2C1-3alkyl, C1-3 alkyl, C3-6 cycloalkyl, SO2C1-3alkyl, S(O)C1-3alkyl, SO2NHC1-3alkyl, heterocycle, and CN; and
R2, R3, R4, and R5 are independently selected from hydrogen, halogen, C1-3alkyl, C1-3 alkoxy, C3-6 cycloalkyl, aryl, —CF3 or heterocycle,
provided that
R2 is fused with R3 to form an aryl ring structure,
R3 is fused with R4 to form an aryl ring structure, or
R4 is fused with R5 to form an aryl ring structure.

### Claim 2 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1 or a pharmaceutically acceptable salt, solvate or polymorph thereof together with one or more pharmaceutically acceptable excipients, diluents or carriers.

### Claim 3 (depends on 1)

A method of activating TLR7 and/or TLR8 in a cell, comprising contacting said cell with a therapeutically effective amount of at least one compound of claim 1.

### Claim 4 (depends on 1)

A method of inducing interferon production in a cell, comprising contacting said cell with a therapeutically effective amount of at least one compound of claim 1.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein R1 is C4-6alkyl.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein R2 and R3 form an aryl ring structure.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein R2 and R3 form an aryl ring structure; and R4 and R5 are each hydrogen.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein R1 is C4-6 alkyl; R2 and R3 form an aryl ring structure; and R4 and R5 are each hydrogen.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein R1 is selected from the group consisting of n-butyl, n-pentyl and n-hexyl.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein R1 is n-butyl.

### Claim 11 (depends on 1)

The compound according to claim 1, wherein R1 is n-butyl, and wherein R2 and R3 form an aryl ring structure.

### Claim 12 (depends on 1)

The compound according to claim 1, wherein said compound is

### Claim 13 (depends on 3)

The method of claim 3, wherein the cell is in a human subject.

### Claim 14 (depends on 4)

The method of claim 4, wherein the cell is in a human subject.

### Claim 15

A method of preparing a compound of formula (I), said method comprising reacting a compound of formula A
with a compound of formula A-1
to form the compound of formula B
reducing the compound of formula B to form a compound of formula D
reacting the compound of formula D with a compound of formula D-1
to form a compound of formula (I)
wherein R1 is C1-6 alkyl, optionally substituted by one or more substituents independently selected from the group consisting of aryl, halogen, OH, NH2, CO2H, CO2C1-3alkyl, C(O)NHC1-3alkyl, C(O)NHSO2C1-3alkyl, C1-3alkyl, C3-6 cycloalkyl, SO2C1-3alkyl, S(O)C1-3alkyl, SO2NHC1-3 alkyl, heterocycle, and CN; and
R2, R3, R4, and R5 are each independently selected from the group consisting of hydrogen, halogen, C1-3alkyl, C1-3alkoxy, C3-6cycloalkyl, aryl, —CF3 and heterocyclyl,
provided that
R2 is fused with R3 to form an aryl ring structure,
R3 is fused with R4 to form an aryl ring structure, or
R4 is fused with R5 to form an aryl ring structure.

### Claim 16 (depends on 15)

The method of claim 15, wherein the compound of formula B is reduced to form a compound of formula C
the compound of formula C is reduced to form a compound of formula D