IP Library Granted Patent US 11,306,071
Granted Patent B2
US 11,306,071 · App. 16/746,763 · Granted Apr 19, 2022

Heterocyclic compounds as adenosine antagonists

Inventors: Son Minh Pham (San Francisco, CA); Jayakanth Kankanala (St. Paul, MN); Pradeep S. Jadhavar (Uttar Pradesh, IN); Baban Mohan Mulik (Uttar Pradesh, IN); Farha Khan (Uttar Pradesh, IN); Sreekanth A. Ramachandran (Uttar Pradesh, IN)
Assignee: Nuvation Bio Inc.
C07D403/04A61P35/00C07D401/04C07D401/14C07D403/14C07D405/14C07D413/14C07D417/04
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Quick Facts
Patent No.
US 11,306,071
App. No.
16/746,763
Granted
Apr 19, 2022
Kind
B2
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 (24)

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, —CF 3 , —OH, —OCH 3 , —CN, —C(O)OCH 3 , —C(O)OC 2 H 5 , —NH 2 , —NHCH 3 or C 1 -C 6 alkyl optionally substituted by halogen, —OH or oxo.

2. 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

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

4. 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.

5. A method of inhibiting an adenosine receptor of subtype A 2A , A 2B or A 3 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.

6. The method of claim 5 , wherein the adenosine receptor is of subtype A 2A .

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Assignments (11)
RELEASE OF SECURITY INTEREST Recorded Jul 6, 2026
From: SAGARD HOLDINGS MANAGER LP, AS ADMINISTRATIVE AGENT
To: NUVATION BIO INC.
Reel/Frame 075179/0564 →
SECURITY INTEREST Recorded Mar 4, 2025
From: NUVATION BIO INC.
To: SAGARD HOLDINGS MANAGER LP, AS ADMINISTRATIVE AGENT
Reel/Frame 070400/0200 →
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY NAME TO REMOVE WORDING IN PARENTHESES PREVIOUSLY RECORDED AT REEL: 059136 FRAME: 0865. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Apr 28, 2022
From: GIRAFPHARMA LLC
To: NUVATION BIO OPERATING COMPANY INC.
Reel/Frame 059821/0487 →
CORRECTIVE ASSIGNMENT TO CORRECT THE CONVEYING PARTY NAME PREVIOUSLY RECORDED AT REEL: 059137 FRAME: 0092. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Apr 28, 2022
From: NUVATION BIO OPERATING COMPANY LLC
To: NUVATION BIO INC.
Reel/Frame 059821/0492 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2022
From: GIRAFPHARMA LLC
To: NUVATION BIO OPERATING COMPANY INC. (FORMALLY KNOWN AS NUVATION BIO INC.)
Reel/Frame 059136/0865 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2022
From: NUVATION BIO OPERATING COMPANY LLC (FORMALLY NUVATION BIO OPERATING COMPANY INC., WHICH WAS FORMALLY KNOWN AS NUVATION BIO INC.)
To: NUVATION BIO INC.
Reel/Frame 059137/0092 →
CHANGE OF NAME Recorded Mar 1, 2022
From: NUVATION BIO OPERATING COMPANY INC.
To: NUVATION BIO OPERATING COMPANY LLC
Reel/Frame 059277/0807 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2022
From: JADHAVAR, PRADEEP S.; MULIK, BABAN MOHAN; KHAN, FARHA; RAMACHANDRAN, SREEKANTH A.
To: INTEGRAL BIOSCIENCES PVT. LTD.
Reel/Frame 060299/0009 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2022
From: INTEGRAL BIOSCIENCES PVT. LTD.
To: SPARCBIO LLC
Reel/Frame 059136/0728 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2022
From: PHAM, SON MINH; KANKANALA, JAYAKANTH
To: SPARCBIO LLC
Reel/Frame 059136/0697 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2022
From: SPARCBIO LLC
To: GIRAFPHARMA LLC
Reel/Frame 059136/0802 →
Continuity (3)
Provisional Application 62796046 · Jan 23, 2019
Provisional Application 62794537 · Jan 18, 2019
Related Publication 20200231570A1 · Jul 23, 2020