# US 11,897,878 B2 · Substituted 6-azabenzimidazole compounds

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- Number: US 11,897,878 B2
- Document ID: US11897878B2
- Status: Granted
- Kind: B2
- Application number: 17/522,628
- Filed: 2021-11-09
- Published: 2022-07-07
- Granted: 2024-02-13
- Earliest claimed: 2018-10-31
- Assignees: Gilead Sciences, Inc.
- Applicants: Gilead Sciences, Inc.
- Inventors: Gayatri Balan; Mark J. Bartlett; Jayaraman Chandrasekhar; Julian A. Codelli; John H. Conway; Jennifer L Cosman; Rao V. Kalla; Zachary A. Kasun; Musong Kim; Seung H. Lee; Jennifer R. Lo; Jennifer A. Loyer-Drew; Scott A. Mitchell; Thao D. Perry; Gary B. Phillips; Patrick J. Salvo; Sundaramoorthi Swaminathan; Joshua J. Van Veldhuizen; Suet C Yeung; Jeff Zablocki
- Web page: https://patentgrep.com/patent/US11897878B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 31/18: for HIV
- A61P 31/20: for DNA viruses
- A61P 35/00: Antineoplastic agents
- 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

The present disclosure relates generally to certain 6-azabenzimidazole compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions disclosed herein may be used for the treatment or prevention of diseases, disorders, or infections modifiable by hematopoietic progenitor kinase 1 (HPK1) inhibitors, such as HBV, HIV, cancer, and/or a hyper-proliferative disease.

## Claims

### Claim 1

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 2

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 3

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 4

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 5

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 6

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 7

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 8

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 9

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 10

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 11

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 12

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 13

A compound of Formula:
or a pharmaceutically acceptable salt thereof.

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 2)

A pharmaceutical composition comprising the compound of claim 2, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 16 (depends on 3)

A pharmaceutical composition comprising the compound of claim 3, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 17 (depends on 4)

A pharmaceutical composition comprising the compound of claim 4, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 18 (depends on 5)

A pharmaceutical composition comprising the compound of claim 5, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 19 (depends on 6)

A pharmaceutical composition comprising the compound of claim 6, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 20 (depends on 7)

A pharmaceutical composition comprising the compound of claim 7, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 21 (depends on 8)

A pharmaceutical composition comprising the compound of claim 8, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 22 (depends on 9)

A pharmaceutical composition comprising the compound of claim 9, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 23 (depends on 10)

A pharmaceutical composition comprising the compound of claim 10, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 24 (depends on 11)

A pharmaceutical composition comprising the compound of claim 11, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 25 (depends on 12)

A pharmaceutical composition comprising the compound of claim 12, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 26 (depends on 13)

A pharmaceutical composition comprising the compound of claim 13, or the pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 27 (depends on 1)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 1, or the pharmaceutically acceptable salt thereof.

### Claim 28 (depends on 2)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 2, or the pharmaceutically acceptable salt thereof.

### Claim 29 (depends on 3)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 3, or the pharmaceutically acceptable salt thereof.

### Claim 30 (depends on 4)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 4, or the pharmaceutically acceptable salt thereof.

### Claim 31 (depends on 5)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject the therapeutically effective amount of the compound of claim 5, or a pharmaceutically acceptable salt thereof.

### Claim 32 (depends on 6)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject the therapeutically effective amount of the compound of claim 6, or a pharmaceutically acceptable salt thereof.

### Claim 33 (depends on 7)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject the therapeutically effective amount of the compound of claim 7, or a pharmaceutically acceptable salt thereof.

### Claim 34 (depends on 8)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 8, or a the pharmaceutically acceptable salt thereof.

### Claim 35 (depends on 9)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 9, or the pharmaceutically acceptable salt thereof.

### Claim 36 (depends on 10)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 10, or the pharmaceutically acceptable salt thereof.

### Claim 37 (depends on 11)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 11, or the pharmaceutically acceptable salt thereof.

### Claim 38 (depends on 12)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 12, or the pharmaceutically acceptable salt thereof.

### Claim 39 (depends on 13)

A method of inhibiting hematopoietic progenitor kinase 1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 13, or the pharmaceutically acceptable salt thereof.

### Claim 40 (depends on 1)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 41 (depends on 2)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 2, or the pharmaceutically acceptable salt thereof.

### Claim 42 (depends on 3)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 3, or the pharmaceutically acceptable salt thereof.

### Claim 43 (depends on 4)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 4, or the pharmaceutically acceptable salt thereof.

### Claim 44 (depends on 5)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 5, or the pharmaceutically acceptable salt thereof.

### Claim 45 (depends on 6)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 6, or the pharmaceutically acceptable salt thereof.

### Claim 46 (depends on 7)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 7, or the pharmaceutically acceptable salt thereof.

### Claim 47 (depends on 8)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 8, or the pharmaceutically acceptable salt thereof.

### Claim 48 (depends on 9)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 9, or the pharmaceutically acceptable salt thereof.

### Claim 49 (depends on 10)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 10, or the pharmaceutically acceptable salt thereof.

### Claim 50 (depends on 11)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 11, or the pharmaceutically acceptable salt thereof.

### Claim 51 (depends on 12)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 12, or the pharmaceutically acceptable salt thereof.

### Claim 52 (depends on 13)

A method of increasing T-cell activation in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 13, or the pharmaceutically acceptable salt thereof.

### Claim 53 (depends on 1)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 1, or the pharmaceutically acceptable salt thereof.

### Claim 54 (depends on 2)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 2, or the pharmaceutically acceptable salt thereof.

### Claim 55 (depends on 3)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 3, or the pharmaceutically acceptable salt thereof.

### Claim 56 (depends on 4)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 4, or the pharmaceutically acceptable salt thereof.

### Claim 57 (depends on 5)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 5, or the pharmaceutically acceptable salt thereof.

### Claim 58 (depends on 6)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 6, or the pharmaceutically acceptable salt thereof.

### Claim 59 (depends on 7)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 7, or the pharmaceutically acceptable salt thereof.

### Claim 60 (depends on 8)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 8, or the pharmaceutically acceptable salt thereof.

### Claim 61 (depends on 9)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 9, or the pharmaceutically acceptable salt thereof.

### Claim 62 (depends on 10)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 10, or the pharmaceutically acceptable salt thereof.

### Claim 63 (depends on 11)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 11, or the pharmaceutically acceptable salt thereof.

### Claim 64 (depends on 12)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 12, or the pharmaceutically acceptable salt thereof.

### Claim 65 (depends on 13)

A method of treating a cancer associated with increased HPK1 activity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 13, or the pharmaceutically acceptable salt thereof.