# US 11,306,071 B2 · Heterocyclic compounds as adenosine antagonists

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- Number: US 11,306,071 B2
- Document ID: US11306071B2
- Status: Granted
- Kind: B2
- Application number: 16/746,763
- Filed: 2020-01-17
- Published: 2020-07-23
- Granted: 2022-04-19
- Earliest claimed: 2019-01-18
- Assignees: Nuvation Bio Inc.
- Applicants: Nuvation Bio Inc.
- Inventors: Son Minh Pham; Jayakanth Kankanala; Pradeep S. Jadhavar; Baban Mohan Mulik; Farha Khan; Sreekanth A. Ramachandran
- Web page: https://patentgrep.com/patent/US11306071B2

## CPC

- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- A61P 35/00: Antineoplastic agents
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/14: containing three or more hetero rings
- C07D 403/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- C07D 417/04: 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

5,6-disubstituted 2-aminopyrazine compounds as modulators of an adenosine receptor are provided. The compounds may find use as therapeutic agents for the treatment of diseases mediated through a G-protein-coupled receptor signaling pathway and may find particular use in oncology.

## Claims

### Claim 1

A compound of the formula (III):
or a tautomer or stereoisomer thereof, or a pharmaceutically acceptable salt of any of the foregoing, wherein:
A is
and
B is a phenyl substituted with 1 to 3 groups which may be the same or different, wherein at least one group is —CN, and wherein each group is halogen, —CF3, —OH, —OCH3, —CN, —C(O)OCH3, —C(O)OC2H5, —NH2, —NHCH3 or C1-C6 alkyl optionally substituted by halogen, —OH or oxo.

### Claim 2 (depends on 1)

The compound of claim 1, or a tautomer or stereoisomer thereof, or a pharmaceutically acceptable salt of any of the foregoing, wherein B is selected from the group consisting of

### Claim 3 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of

### Claim 4 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, or a tautomer or stereoisomer thereof, or a pharmaceutically acceptable salt of any of the foregoing, and a pharmaceutically acceptable carrier.

### Claim 5 (depends on 1)

A method of inhibiting an adenosine receptor of subtype A2A, A2B or A3 in a cell, comprising administering a compound of claim 1, or a tautomer or stereoisomer thereof, or a pharmaceutically acceptable salt of any of the foregoing, to the cell.

### Claim 6 (depends on 5)

The method of claim 5, wherein the adenosine receptor is of subtype A2A.

### Claim 7 (depends on 1)

A kit comprising a compound of claim 1, or a tautomer or stereoisomer thereof, or a pharmaceutically acceptable salt of any of the foregoing.

### Claim 8 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 9 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 10 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 11 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 12 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 13 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 14 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 15 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 16 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 17 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 18 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 19 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 20 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein the compound is