Purinones and 1H-imidazopyridinones as PKC-theta inhibitors

1. A compound, or salt thereof, represented by Formula I,

wherein:

Q is N;

R 1 is chosen from (i)

wherein

n is an integer from 2 to 6;

R 21 is chosen separately in each occurrence from —H, C 1 -C 4 alkyl and —OH;

R 22 is chosen separately in each occurrence from —H, C 1 -C 4 alkyl and a bond to R 24 ;

R 23 is chosen from —H, C 1 -C 4 alkyl and a bond to R 24 ;

R 24 is chosen from —H, C 1 -C 4 alkyl or together with either of R 22 or R 23 forms a 5-7 membered nitrogen heterocycle optionally substituted with C 1 -C 4 alkyl;

wherein R 9 is chosen from amino(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylamino(C 1 -C 6 )alkyl and di [(C 1 -C 6 )alkyl]amino(C 1 -C 6 )alkyl; and

R 2 is chosen from aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, substituted heteroaryl, hetroarylalkyl, and substituted heteroarylalkyl.

2. A compound, or salt thereof, according to claim 1 , wherein:

R 1 is chosen from

wherein R 9 is chosen from amino(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylamino(C 1 -C 6 )alkyl and di[(C 1 -C 6 )alkyl]amino(C 1 -C 6 )alkyl.

3. A compound, or salt thereof, according to claim 1 , wherein:

R 1 is

4. A compound, or salt thereof, according to claim 3 , wherein:

R 22 is chosen separately in each occurrence from —H and C 1 -C 4 alkyl; and

R 24 together with R 23 forms a 5-7 membered nitrogen heterocycle optionally substituted with C 1 -C 4 alkyl.

5. A compound, or salt thereof, according to claim 3 , wherein:

R 22 is chosen separately in each occurrence from —H and C 1 -C 4 alkyl;

R 23 is chosen from —H, C 1 -C 4 alkyl; and

R 24 is H or C 1 -C 4 alkyl.

6. A compound, or salt thereof, according to claim 3 , wherein:

R 22 is chosen separately in each occurrence from H, C 1 -C 4 alkyl and a bond to R 24 ;

R 23 is chosen from H, C 1 -C 4 alkyl;

R 24 together with one occurrence of R 22 forms a 5-7 membered nitrogen heterocycle optionally substituted with C 1 -C 4 alkyl.

7. A compound, or salt thereof, according to claim 1 , wherein:

R 2 is chosen from

wherein

R 10 , R 11 , and R 12 , are independently chosen from —H, halogen, —OCH 3 , —OCF 3 , —CF 3 , C 1 -C 4 alkyl, and phenyl; and

L is a bond or a C 1 -C 10 alkylene.

8. A compound, or salt thereof, according to claim 7 , wherein:

R 2 is chosen from

wherein

R 10 , R 11 , and R 12 are independently chosen from —H, halogen, —OCH 3 , —OCF 3 , —CF 3 , and C 1 -C 4 alkyl; and

R 15 and R 16 are independently chosen from —H and C 1 -C 4 alkyl.

9. A pharmaceutical composition comprising a compound according to claim 1 , or salt thereof, and a pharmaceutically acceptable carrier.

10. A compound, or salt thereof, represented by Formula I,

wherein:

Q is N;

R 1 is chosen from

wherein

R 4 is chosen from

 and —M—NR 7 R 8 ;

wherein

R 5 , R 6 , and R 9 are independently chosen from —H, C 1 -C 4 alkyl, —OH, —OCH 3 , halogen, and aminoalkyl;

R 7 and R 8 are independently chosen from —H, C 1 -C 4 alkyl, and aminoalkyl;

L 1 is a bond or a C 1 -C 10 alkylene optionally substituted with —OH, with a proviso that —OH cannot be bonded to a carbon atom that is also bonded to N;

M is C 2 -C 10 alkyl optionally substituted with —OH, with a proviso that —OH cannot be bonded to a carbon atom that is also bonded to N;

R 2 is chosen from

wherein

R 10 , R 11 , and R 12 are independently chosen from —H, halogen, —OCH 3 , —OCF 3 , —CF 3 , C 1 -C 4 alkyl, and phenyl; and

L is a bond or a C 1 -C 10 alkylene.

11. A compound, or salt thereof, according to claim 10 , wherein:

R 4 is chosen from

wherein

R 5 , R 6 , and R 9 are independently chosen from —H, C 1 -C 4 alkyl, —OH, —OCH 3 , halogen, and aminoalkyl;

R 7 and R 8 are independently chosen from —H, C 1 -C 4 alkyl, and aminoalkyl; and

R 13 and R 14 are independently chosen from —H, —OH, and C 1 -C 4 alkyl, with a proviso that —OH cannot be bonded to a carbon atom that is also bonded to N.

12. A compound, or salt thereof, according to claim 11 , wherein:

R 5 , R 6 , R 7 , and R 8 are independently chosen from —H and C 1 -C 4 alkyl;

R 9 is —R 17 —NR 7 R 8 ; and

wherein

R 17 is a C 1 -C 4 alkyl.

13. A compound, or salt thereof, according to claim 12 , wherein:

R 4 is chosen from

wherein

R 7 and R 8 are independently chosen from —H and —CH 3 ; and

R 18 is chosen from —H and —OH.

14. A compound, or salt thereof, according to claim 10 , wherein:

R 2 is chosen from

wherein

R 10 , R 11 , and R 12 are independently chosen from —H, halogen, —OCH 3 , —OCF 3 , —CF 3 , and C 1 -C 4 alkyl; and

R 15 and R 16 are independently chosen from —H and C 1 -C 4 alkyl.

15. A pharmaceutical composition comprising a compound according to claim 10 , or salt thereof, and a pharmaceutically acceptable carrier.

16. A compound, or salt thereof, represented by Formula I,

wherein:

Q is N;

R 1 is chosen from

wherein

R 4 is chosen from

wherein

R 5 , R 6 , and R 9 are independently chosen from —H, C 1 -C 4 alkyl, —OH, —OCH 3 , halogen, and aminoalkyl;

R 7 and R 8 are independently chosen from —H, C 1 -C 4 alkyl, and aminoalkyl; and

R 13 and R 14 are independently chosen from —H, —OH, and C 1 -C 4 alkyl, with a proviso that —OH cannot be bonded to a carbon atom that is also bonded to N;

R 2 is chosen from

and

wherein

R 10 , R 11 , and R 12 are independently chosen from —H, halogen, —OCH 3 , —OCF 3 , —CF 3 , and C 1 -C 4 alkyl; and

R 15 and R 16 are independently chosen from —H and C 1 -C 4 alkyl.

17. A compound, or salt thereof, according to claim 16 , wherein:

R 5 , R 6 , R 7 , and R 8 are independently chosen from —H and C 1 -C 4 alkyl;

R 9 is —R 17 —NR 7 R 8 ; and

wherein

R 17 is a C 1 -C 4 alkylene.

18. A compound, or salt thereof, according to claim 17 , wherein:

R 4 is chosen from

wherein

R 7 and R 8 are independently chosen from —H and —CH 3 ; and

R 18 is chosen from —H and —OH.

19. A pharmaceutical composition comprising a compound according to claim 16 , or salt thereof, and a pharmaceutically acceptable carrier.