Granted Patent B2

US 12,378,242 · App. 17/669,112 · Granted Aug 5, 2025

Inventors: Shawn E. R. Schiller (Haverhill, MA); Torsten Herbertz (Stow, MA); Hongbin Li (Madison, CT); Bradford Graves (Nutley, NJ); Steven Mischke (Waltham, MA); Angela West (Franklin, MA); Jennifer R. Downing (Clinton, MA); Anna Ericsson (Shrewsbury, MA)

Assignee: FORMA Therapeutics, Inc.

C07D471/04

Abstract

Claims (29)

1. A compound according to the following formula:

or a pharmaceutically acceptable salt or enantiomer thereof, wherein:

R 1 is —OR 5 ;

R 5 is —C 1 -C 6 alkyl, —C 3 -C 8 cycloalkyl, heterocyclyl, aryl, or heteroaryl;

R 6 is —C 3 -C 8 cycloalkyl, —C 4 -C 8 cycloalkenyl, heterocyclyl, heteroaryl, aryl, wherein each cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, or aryl is optionally substituted with one or more —R 10 ;

R 6′ is —C 1 -C 6 alkyl-C 1 -C 2 alkyl;

R 7 is —H at one occurrence, and —C(O) OH or —C(O)OC 1 -C 6 alkyl at the other occurrence;

R 10 is independently, at each occurrence, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 6 cycloalkyl, —C 4 -C 8 cycloalkenyl, heterocyclyl, heteroaryl, aryl, —OH, halogen, oxo, —NO 2 , —CN, —NH 2 , —OC 1 -C 6 alkyl, —OC 3 -C 6 cycloalkyl, -Oaryl, -Oheteroaryl, —NHC 1 -C 6 alkyl, —N(C 1 -C 6 alkyl) 2 , —S(O) 2 NH(C 1 -C 6 alkyl), —S(O) 2 N(C 1 -C 6 alkyl) 2 , —S(O) 2 C 1 -C 6 alkyl, —C(O)C 1 -C 6 alkyl, —C(O)NH 2 , —C(O)NH(C 1 -C 6 alkyl), —NHC(O)C 1 -C 6 alkyl, —C(O)N(C 1 -C 6 alkyl) 2 , —C(O)OC 1 -C 6 alkyl, —N(C 1 -C 6 alkyl) SO 2 C 1 -C 6 alkyl, —S(O) (C 1 -C 6 alkyl), —S(O)N(C 1 -C 6 alkyl) 2 , or —N(C 1 -C 6 alkyl)S(O)(C 1 -C 6 alkyl), wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, or aryl is optionally substituted with one or more —R 12 ; and

R 12 is independently, at each occurrence, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 8 cycloalkyl, —C 4 -C 8 cycloalkenyl, heterocyclyl, heteroaryl, aryl, —OH, halogen, oxo, —NO 2 , —CN, —NH 2 , —OC 1 -C 6 alkyl, —NHC 1 -C 6 alkyl, —N(C 1 -C 6 alkyl) 2 , —S(O) 2 NH(C 1 -C 6 alkyl), —S(O) 2 N(C 1 -C 6 alkyl) 2 , —S(O) 2 C 1 -C 6 alkyl, —C(O)C 1 -C 6 alkyl, —C(O)NH 2 , —C(O)NH(C 1 -C 6 alkyl), —C(O)N(C 1 -C 6 alkyl) 2 , —C(O)OC 1 -C 6 alkyl, —N(C 1 -C 6 alkyl) SO 2 C 1 -C 6 alkyl, —S(O) (C 1 -C 6 alkyl), —S(O)N(C 1 -C 6 alkyl) 2 , or —N(C 1 -C 6 alkyl)S(O)(C 1 -C 6 alkyl).

2. The compound of claim 1 , wherein R 5 is —C 1 -C 6 alkyl.

3. The compound of claim 1 , wherein R 5 is methyl.

4. The compound of claim 1 , wherein q is 1.

5. The compound of claim 1 , wherein R 7 is —H at one occurrence and —C(O)OH at the other occurrence.

6. The compound of claim 1 , wherein m is 3, q is 1, and R 7 is —C(O) OH.

7. The compound of claim 1 , wherein R 6′ is —C 1 -C 3 alkyl.

8. The compound of any one of claim 1 , wherein R 6′ is selected from methyl and ethyl.

9. The compound of claim 1 , wherein R 6 is selected from aryl and heteroaryl, and each aryl or heteroaryl is optionally substituted with one or more —R 10 .

10. The compound of claim 1 , wherein each R 10 is independently selected from halogen and —OC 1 -C 6 alkyl.

11. The compound of claim 1 , wherein each R 10 is independently selected from F and —OCH 3 .

12. The compound of claim 1 , selected from the group consisting of:

13. A compound selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

14. A compound selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

15. The compound of claim 14 , wherein the compound is:

16. The compound of claim 14 , wherein the compound is:

17. The compound of claim 14 , wherein the compound is:

18. The compound of claim 14 , wherein the compound is:

19. A pharmaceutical composition comprising the compound of claim 14 , or a pharmaceutically acceptable salt thereof.

Assignments (1)

Continuity (5)

References Cited (121)