Granted Patent B2

US 12,234,231 · App. 17/822,344 · Granted Feb 25, 2025

Inventor: Christopher L. Vandeusen (Hopkinton, MA)

Assignee: PIC Therapeutics, Inc.

C07D417/14C07D417/12

Abstract

Claims (44)

1. A compound of formula I:

or a pharmaceutically acceptable salt thereof, wherein:

X is CH, CR 4 , or N;

R 1 is H or C 1-6 alkyl optionally substituted 1-6 times by halogen, —OR, —N(R) 2 , or —C(O)—N(R) 2 ;

R 2 is a 3-6 membered monocyclic saturated carbocyclic ring optionally substituted 1-6 times by halogen or —OR′, C 1-6 alkyl optionally substituted 1-6 times by halogen or —OR′, or C 1-6 alkyl optionally substituted 1 time by a 3-6 membered monocyclic saturated carbocyclic ring or a phenyl ring, wherein the 3-6 membered monocyclic saturated carbocyclic ring and phenyl ring are optionally substituted 1-6 times by halogen or —OR′;

R 3 is

each R 4 is independently halogen, —OR 1 , or C 1-6 alkyl optionally substituted 1-6 times by halogen;

each R 5 is independently halogen or C 1-6 alkyl optionally substituted 1-6 times by halogen;

each R is independently H, C 1-6 alkyl optionally substituted 1-6 times by halogen, —OR′, or —N(R′) 2 , or a 3-6 membered monocyclic saturated carbocyclic ring optionally substituted 1-6 times by halogen;

each R′ is independently H or C 1-6 alkyl optionally substituted 1-6 times by halogen;

m is 0 or 1; and

n is 0, 1, or 2.

2. The compound of claim 1 , wherein X is CH or CR 4 .

3. The compound of claim 1 , wherein R 1 is C 1-6 alkyl optionally substituted 1-6 times by halogen, —OR, or —N(R) 2 .

4. The compound of claim 3 , wherein R 1 is unsubstituted C 1-6 alkyl.

5. The compound of claim 1 , wherein R 2 is C 1-6 alkyl optionally substituted 1-6 times by halogen or —OR′.

6. The compound of claim 1 , wherein R 2 is C 1-6 alkyl optionally substituted 1 time by a 3-6 membered monocyclic saturated carbocyclic ring, wherein the 3-6 membered monocyclic saturated carbocyclic ring is optionally substituted 1-6 times by halogen or —OR′.

7. The compound of claim 1 , wherein R 2 is

8. The compound of claim 1 , wherein each R 4 is independently halogen or —OR 1 .

9. The compound of claim 1 , wherein each R 4 is independently selected from —OH, F, Cl,

10. The compound of claim 1 , wherein m is 0.

11. The compound of claim 1 , wherein n is 1.

12. A compound of formula V:

or a pharmaceutically acceptable salt thereof, wherein:

R 11 is H, halogen, C 1-6 alkyl, —O-phenyl, or —O—C 1-6 alkyl, wherein C 1-6 alkyl is optionally substituted by phenyl or —O-phenyl, wherein phenyl is optionally substituted;

X is CH, CR 4 , or N;

R 1 is H or C 1-6 alkyl optionally substituted 1-6 times by halogen, —OR, —N(R) 2 , or —C(O)—N(R) 2 ;

R 2 is a 3-6 membered monocyclic saturated carbocyclic ring optionally substituted 1-6 times by halogen or —OR′, C 1-6 alkyl optionally substituted 1-6 times by halogen or —OR′, or C 1-6 alkyl optionally substituted 1 time by a 3-6 membered monocyclic saturated carbocyclic ring or a phenyl ring, wherein the 3-6 membered monocyclic saturated carbocyclic ring and phenyl ring are optionally substituted 1-6 times by halogen or —OR′;

R 3 is

each R 4 is independently halogen, —OR 1 , or C 1-6 alkyl optionally substituted 1-6 times by halogen;

each R 5 is independently halogen or C 1-6 alkyl optionally substituted 1-6 times by halogen;

each R is independently H, C 1-6 alkyl optionally substituted 1-6 times by halogen, —OR′, or —N(R′) 2 , or a 3-6 membered monocyclic saturated carbocyclic ring optionally substituted 1-6 times by halogen;

each R′ is independently H or —C 1-6 alkyl optionally substituted 1-6 times by halogen;

m is 0 or 1; and

n is 0, 1, or 2.

13. The compound of claim 12 , wherein X is CH or CR 4 .

14. The compound of claim 12 , wherein R 1 is C 1-6 alkyl optionally substituted 1-6 times by halogen, —OR, or —N(R) 2 .

15. The compound of claim 12 , wherein R 2 is C 1-6 alkyl optionally substituted 1-6 times by halogen or —OR′.

16. The compound of claim 12 , wherein each R 4 is independently halogen or —OR 1 .

17. A compound selected from:

pharmaceutically acceptable salt thereof.

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

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

20. A pharmaceutical composition comprising the compound of claim 17 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant, or vehicle.

Assignments (1)

Continuity (2)

References Cited (171)