# US 10,370,342 B2 · Toll like receptor modulator compounds

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- Number: US 10,370,342 B2
- Document ID: US10370342B2
- Status: Granted
- Kind: B2
- Application number: 15/692,093
- Filed: 2017-08-31
- Published: 2018-03-08
- Granted: 2019-08-06
- Earliest claimed: 2016-09-02
- Assignees: Gilead Sciences, Inc.
- Applicants: Gilead Sciences, Inc.
- Inventors: Gregory Chin; Richard L. Mackman; Michael R. Mish; Jeff Zablocki
- Web page: https://patentgrep.com/patent/US10370342B2

## CPC

- C07D 239/95: with hetero atoms directly attached in positions 2 and 4
- A61K 31/517: ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 31/18: for HIV
- A61P 35/00: Antineoplastic agents
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This application relates generally to toll like receptor modulator compounds and pharmaceutical compositions which, among other things, modulate toll-like receptors (e.g. TLR8), and methods of making and using them.

## Claims

### Claim 1

A compound of Formula I
or a pharmaceutically acceptable salt thereof,
wherein:
R1 is —H, C1-4 alkyl, or C1-4 haloalkyl;
R2 is C1-6 alkyl or C1-6 haloalkyl;
Q is CR4;
R3 and R4 are taken together to form phenyl
optionally substituted with 1 to 3 R5;
each R5 is independently halogen, —OH, —NH2, —CN, C1-4 alkyl optionally substituted with 1 to 3 RZ, C1-4 haloalkyl, C1-4 alkoxy, —C(O)OH, —C(O)C1-4 alkyl, —C(O)OC1-4 alkyl, —C(O)NH2, —C(O)NH(C1-4 alkyl), —C(O)N(C1-4 alkyl)2, —N(H)C(O)C1-4 alkyl, —S(O)2C1-4 alkyl, or 5 to 6 membered heteroaryl having 1 to 3 heteroatoms selected from oxygen, nitrogen, and sulfur optionally substituted with 1 to 3 RZ; and
each RZ is independently —NH2, C1-4 alkyl, halogen, —CN, —OC1-4 alkyl, C1-4 haloalkyl, or —C(O)NH2.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 is —H or C1-4 alkyl.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R1 is methyl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R2 is C3-6 alkyl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R3 and R4 are taken together to form phenyl optionally substituted with 1 to 3 chloro, fluoro, bromo, —CN, C1-2 alkyl optionally substituted with —OH, C1-2 alkoxy, —C(O)C1-2 alkyl, —C(O)OC1-2 alkyl, pyrazolyl optionally substituted with 1 to 3 C1-2 alkyl; or imidazolyl optionally substituted with 1 to 3 C1-2 alkyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein:
R1 is —H or C1-4 alkyl;
R2 is C3-6 alkyl;
R3 and R4 are taken together to form phenyl optionally substituted with 1 to 3 halogen.

### Claim 7 (depends on 1)

The compound of claim 1, wherein Formula I is represented by Formula II

### Claim 8 (depends on 1)

The compound of claim 1, wherein Formula I is represented by Formula III

### Claim 9 (depends on 6)

The compound of claim 6, wherein R3 and R4 are taken together to form phenyl optionally substituted with 1 to 3 fluoro.

### Claim 10 (depends on 1)

The compound of claim 1, selected from
or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

### Claim 12 (depends on 11)

The pharmaceutical composition of claim 11, further comprising one or more additional therapeutic agents.

### Claim 13 (depends on 1)

A kit comprising a compound of claim 1, or a pharmaceutically acceptable salt thereof.