Granted Patent B2

US 12,351,566 · App. 17/791,755 · Granted Jul 8, 2025

Inventors: Brett Matthew Hall (San Diego, CA); Bart Lieven Decorte (Southampton, PA); Peter John King (San Diego, CA); Ruben Leenders (Cambridge, MA); Anita Wegert (Cambridge, MA); Kevin Fowler (Cambridge, MA); Sarah Kolitz (Cambridge, MA); Robin Doodeman (Cambridge, MA); Jarno Poelakker (Cambridge, MA); Rutger Henk Adriaan Folmer (Cambridge, MA)

Assignee: Immuneering Corporation

C07D311/06A61P35/00C07D405/12C07D407/12C07D409/12

Abstract

Claims (67)

1. A compound of Formula (IIb):

or a pharmaceutically acceptable salt thereof, wherein:

Z is C or N;

R 2 is L;

L is —Z 1 —Z 2 ;

Z 1 is —CH 2 —;

Z 2 is —NR 5 R 5′ ;

each of R 5 and R 5′ are each independently C 1 to C 6 alkyl, and

R 6 is H, deuterium, halogen, or C 1 to C 6 alkyl.

2. The compound of claim 1 , wherein, R 5 and R 5′ are each independently methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, or t-butyl; and R 6 is H.

3. The compound of claim 2 , wherein Z is C.

4. The compound of claim 2 , wherein Z is N.

5. The compound of claim 2 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

6. The compound of claim 2 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

7. The compound of claim 2 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

8. The compound of claim 2 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

9. The compound of claim 2 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

10. The compound of claim 2 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

11. The compound of claim 2 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

12. The compound claim 1 , wherein R 6 is halogen, or a pharmaceutically acceptable salt thereof.

13. The compound of claim 12 , selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

14. A compound of Formula (IIb):

or a pharmaceutically acceptable salt thereof, wherein:

Z is C or N;

R 2 is L;

L is —Z 1 —Z 2 ;

Z 1 is —CH 2 —;

Z 2 is optionally substituted

 and n is 1, 2, 3 or 4; and

R 6 is H, deuterium, halogen, or C 1 to C 6 alkyl.

15. The compound of claim 14 , wherein Z 2 is

16. The compound of claim 14 , wherein R 6 is H.

17. The compound of claim 14 , wherein R 6 is halogen.

18. The compound of claim 14 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

19. A compound of Formula (IIb):

or a pharmaceutically acceptable salt thereof, wherein

Z is C or N;

R 2 is L;

L is —Z 1 —Z 2 ;

Z 1 is —CH 2 —;

Z 2 is optionally substituted

 and

R 6 is H, deuterium, halogen, or C 1 to C 6 alkyl.

20. The compound of claim 19 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

21. A compound having the structure depicted in Formula (IIa):

or a pharmaceutically acceptable salt thereof, wherein:

R 2 is L;

R 3 is the fluoro;

R 6 is H, deuterium, halogen, or C 1 to C 6 alkyl;

R 8 is C 1 to C 6 alkyl;

L is —Z 1 —Z 2 ;

Z 1 is —CH 2 ;

Z 2 is selected from the group consisting of —NR 5 R 5′ , or C 3 to C 8 heterocyclyl;

each R 5 and R 5 are each independently H, deuterium, or C 1 to C 6 alkyl;

X is O;

Y is O; and

Z is C or N.

Assignments (1)

Continuity (2)

References Cited (349)