IP Library Granted Patent US 8,486,939
Granted Patent B2
US 8,486,939 · App. 12/831,128 · Granted Jul 16, 2013

Pyrimidinyl and 1,3,5-triazinyl benzimidazoles and their use in cancer therapy

Inventors: Gordon William Rewcastle (Auckland, NZ); Kit Yee Tsang (Auckland, NZ); Swarnalatha Akuratiya Gamage (Auckland, NZ); Anna Claire Giddens (Auckland, NZ)
Assignee: Pathway Therapeutics Inc.
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Quick Facts
Patent No.
US 8,486,939
App. No.
12/831,128
Granted
Jul 16, 2013
Kind
B2
Abstract

Provided herein are pyrimidinyl and 1,3,5-triazinyl benzimidazoles of Formula I, and their pharmaceutical compositions, preparation, and use as agents or drugs for cancer therapy, either alone or in combination with radiation and/or other anticancer drugs.

Claims (346)

1. A compound of Formula I, IA, or IB:

or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof; or a pharmaceutically acceptable salt or prodrug thereof;

wherein:

each R 1 is independently hydrogen, C 1-6 alkyl, —S—C 1-6 alkyl, —S(O)—C 1-6 alkyl, or —SO 2 —C 1-6 alkyl;

each R 2 and R 3 is independently (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; or (c) —C(O)R 1a , —C(O)OR 1b , —C(O)NR 1b R 1c , —C(NR a )NR 1b R 1c , —OR 1a , —OC(O)R 1a , —OC(O)OR 1a , —OC(O)NR 1b R 1c , —OC(═NR 1a )NR 1b R 1c , —OS(O)R 1a , —OS(O) 2 R 1a , —OS(O)NR 1b R 1c , —OS(O) 2 NR 1b R 1c , —NR 1b R 1c , —NR 1a C(O)R 1d , —NR 1a C(O)OR 1d , —NR 1a C(O)NR 1b R 1c , —NR 1a C(═NR 1d )NR 1b R 1c , —NR 1a S(O)R 1d , —NR 1a S(O) 2 R 1d , —NR 1a S(O)NR 1b R 1c , —NR 1a S(O) 2 NR 1b R 1c , —SR 1a , —S(O)R 1a , —S(O) 2 R 1a , —S(O)NR 1b R 1c , or —S(O) 2 NR 1b R 1c ;

each R 4 and R 5 is independently hydrogen or C 1-6 alkyl; or R 4 and R 5 are linked together to form a bond, C 1-6 alkylene, C 1-6 heteroalkylene, C 2-6 alkenylene, or C 2-6 heteroalkenylene;

each R 6 is independently C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heteroaryl-C 1-6 alkyl;

each U is independently —C(O)—, —C(O)O—, —C(O)NR 1a —, —O—, —OC(O)O—, —OC(O)NR 1a —, —NR 1a —, —NR 1a C(O)NR 1d —, —NR 1a S(O)—, —NR 1a S(O) 2 —, —NR 1a S(O)NR 1d —, —NR 1a S(O) 2 NR 1d —, —S—, —S(O)—, or —S(O) 2 —;

each X, Y, and Z is N;

each A, B, D, and E is independently a bond, C, O, N, S, NR 9 , CR 9 , or CR 9 R 10 , where each R 9 and R 10 is independently hydrogen, halo, C 1-6 alkyl, C 2-6 alkenyl, or C 2-6 alkynyl; wherein the bonds between A, B, D, and E may be saturated or unsaturated; with the proviso that no more than one of A, B, D, and E are a bond; and

each R 1a , R 1b , R 1c , and R 1d is independently (i) hydrogen; or (ii) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl;

wherein each alkyl, alkylene, heteroalkylene, alkenyl, alkenylene, heteroalkenylene, alkynyl, cycloalkyl, aryl, aralkyl, heteroaryl, and heterocyclyl R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 10 , R 1a , R 1b , R 1c , or R 1d is optionally substituted with one or more groups, each independently selected from (a) cyano, halo, and nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, and heterocyclyl, each of which is further optionally substituted with one or more substituents Q; and (c) —C(O)R a , —C(O)OR a , —C(O)NR b R c , —C(NR a )NR b R c , —OR a , —OC(O)R a , —OC(O)OR a , —OC(O)NR b R c , —OC(═NR a )NR b R c , —OS(O)R a , —OS(O) 2 R a , —OS(O)NR b R c , —OS(O) 2 NR b R c , —NR b R c , —NR a C(O)R d , —NR a C(O)OR d , —NR a C(O)NR b R c , —NR a C(═NR d )NR b R c , —NR a S(O)R d , —NR a S(O)NR b R c , —SR a , —S(O)R a , and —S(O)NR b R c , wherein each R a , R b , R c , and R d is independently (i) hydrogen; (ii) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl, each optionally substituted with one or more substituents Q; or (iii) R b and R c together with the N atom to which they are attached form heterocyclyl, optionally substituted with one or more substituents Q;

wherein each Q is independently selected from the group consisting of (a) cyano, halo, and nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, and heterocyclyl; and (c) —C(O)R e , —C(O)OR e , —C(O)NR f R g , —C(NR e )NR f R g , —OR e , —OC(O)R e , —OC(O)OR e , —OC(O)NR f R g , —OC(═NR e )NR f R g , —OS(O)R e , —OS(O) 2 R e , —OS(O)NR f R g , —OS(O) 2 NR f R g , —NR f R g , —NR e C(O)R h , —NR e C(O)OR h , —NR e C(O)NR f R g , —NR e C(═NR h )NR f R g , —NR e S(O)R h , —NR e S(O)NR f R g , —SR e , —S(O)R e , and —S(O)NR f R g , wherein each R e , R f , R g , and R h is independently (i) hydrogen; (ii) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; or (iii) R f and R g together with the N atom to which they are attached form heterocyclyl.

2. The compound of claim 1 having the structure of Formula II, Ia, or Ib:

or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof; or a pharmaceutically acceptable salt or prodrug thereof.

3. The compound of claim 1 having the structure of Formula VIII:

or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof; or a pharmaceutically acceptable salt or prodrug thereof.

4. The compound of claim 1 having the structure of Formula IX

or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof; or a pharmaceutically acceptable salt prodrug thereof.

5. The compound of claim 1 , wherein A is N.

6. The compound of claim 1 , wherein B is N.

7. The compound of claim 1 , wherein B is CH or CH 2 .

8. The compound of claim 1 , wherein D is N.

9. The compound of claim 1 , wherein D is CH or CH 2 .

10. The compound of claim 1 , wherein R 6 is C 6-14 aryl, optionally substituted with one or more substituents Q.

11. The compound of claim 10 , wherein R 6 is phenyl, optionally substituted with one or more substituents, each independently selected from the group consisting of halo, cyano, nitro, amino, hydroxyl, and methoxy.

12. The compound of claim 10 , wherein R 6 is phenyl, aminophenyl, nitrophenyl, or methoxyphenyl.

13. The compound of claim 1 , wherein R 6 is C 7-15 aralkyl, optionally substituted with one or more substituents Q.

14. The compound of claim 13 , wherein R 6 is —(CR A R B ) m —C 6-14 aryl, and each R A and R B is independently (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; and m is an integer of 1, 2, or 3; and where each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heteroaryl, and heterocyclyl is optionally substituted with one or more substituents Q.

15. The compound of claim 13 , wherein R 6 is benzyl, optionally substituted with one or more substituents Q.

16. The compound of claim 13 , wherein R 6 is benzyl or phenyl-ethyl, each optionally substituted with one or more substituents Q.

17. The compound of claim 1 , wherein R 6 is heteroaryl, optionally substituted with one or more substituents Q.

18. The compound of claim 17 , wherein R 6 is pyrazolyl, imidazolyl, thiazolyl, 1,2,3-triazolyl, tetrazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, or quinolinyl, each optionally substituted with one or more substituents Q.

19. The compound of claim 17 , wherein each substituent is independently -L-(CR C R D ) n —R E , where R C and R D are each independently (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; each optionally substituted with one or more substituents Q; R E is hydrogen, —NR F R G , or heterocyclyl; L is a bond, —O—, or —N(R H )—; R F , R G , and R H are each independently hydrogen or C 1-6 alkyl; and n is an integer of 0, 1, 2, or 3; and where each alkyl and heterocyclyl is independently, optionally substituted with one or more substituents Q.

20. The compound of claim 19 , wherein L is a bond, —O—, —NH—, or —N(CH 3 )—.

21. The compound of claim 19 , wherein R C and R D are hydrogen.

22. The compound of claim 19 , wherein R E is hydrogen, methylamino, dimethylamino, pyrrolidinyl, piperidinyl, or morpholinyl, wherein the pyrrolidinyl, piperidinyl, and morpholinyl are independently, optionally substituted with methyl.

23. The compound of claim 17 , wherein each substituent is independently selected from the group consisting of amino, fluoro, chloro, methyl, (dimethylamino)methyl, (dimethylamino)ethyl, (dimethylamino)propyl, morpholinylmethyl, (morpholinyl)ethyl, (morpholinyl)propyl, methoxy, (dimethylamino)ethoxy, (dimethylamino)propoxy, (morpholinyl)ethoxy, (morpholinyl)propoxy, (methyl-piperidinyl)oxy, (methyl-pyrrolidinyl)-oxy, methylamino, dimethylamino, (dimethylamino)ethylamino, (dimethylaminoethyl)-(methyl)amino, (dimethylamino)propylamino, ((dimethylamino)propyl)(methyl)amino, (morpholinyl)ethylamino, ((morpholinyl)ethyl)(methyl)amino, (morpholinyl)propylamino, ((morpholinyl)propyl)(methyl)amino, methyl-piperidinylamino, (methyl-piperidinyl)-(methyl)amino, methyl-piperazinyl, and (dimethylamino)-piperidinyl.

24. The compound of claim 18 , wherein R 6 is pyridinyl.

25. The compound of claim 24 , wherein R 6 is 3-pyridinyl.

26. The compound of claim 1 having the structure of Formula III:

or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof; or a pharmaceutically acceptable salt or prodrug thereof;

wherein:

U is —C(O)—, —C(O)O—, —C(O)NR 1a —, —O—, —OC(O)O—, —OC(O)NR 1a —, —NR 1a —, —NR 1a C(O)NR 1d —, —NR 1a S(O)—, —NR 1a S(O) 2 —, —NR 1a S(O)NR 1d —, —NR 1a S(O) 2 NR 1d —, —S—, —S(O)—, or —S(O) 2 —; and

R 8 is (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; each optionally substituted with one or more substituents Q; or (c) —C(O)R 1a , —C(O)OR 1b , —C(O)NR 1b R 1c , —C(NR a )NR 1b R 1c , —OR 1a , —OC(O)R 1a , —OC(O)OR 1a , —OC(O)NR 1b R 1c , —OC(═NR 1a )NR 1b R 1c , —OS(O)R 1a , —OS(O) 2 R 1a , —OS(O)NR 1b R 1c , —OS(O) 2 NR 1b R 1c , —NR 1b R 1c , —NR 1a C(O)R 1d , —NR 1a C(O)OR 1d , —NR 1a C(O)NR 1b R 1c , —NR 1a C(═NR 1d )NR 1b R 1c , —NR 1a S(O)R 1d , —NR 1a S(O) 2 R 1d , —NR 1a S(O)NR 1b R 1c , —NR 1a S(O) 2 NR 1b R 1c , —SR 1a , —S(O)R 1a , —S(O) 2 R 1a —S(O)NR 1b R 1c , or —S(O) 2 NR 1b R 1c .

27. The compound of claim 1 having the structure of Formula IV:

or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof; or a pharmaceutically acceptable salt or prodrug thereof;

wherein:

R 8 is (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; each optionally substituted with one or more substituents Q; or (c) —C(O)R 1a , —C(O)OR 1b , —C(O)NR 1b R 1c , —C(NR a )NR 1b R 1c , —OR 1a , —OC(O)R 1a , —OC(O)OR 1a , —OC(O)NR 1b R 1c , —OC(═NR 1a )NR 1b R 1c , —OS(O)R 1a , —OS(O) 2 R 1a , —OS(O)NR 1b R 1c , —OS(O) 2 NR 1b R 1c , —NR 1b R 1c , —NR 1a C(O)R 1d , —NR 1a C(O)OR 1d , —NR 1a C(O)NR 1b R 1c , —NR 1a C(═NR 1d )NR 1b R 1c , —NR 1a S(O)R 1d , —NR 1a S(O) 2 R 1d , —NR 1a S(O)NR 1b R 1c , —NR 1a S(O) 2 NR 1b R 1c , —SR 1a , —S(O)R 1a , —S(O) 2 R 1a , —S(O)NR 1b R 1c , or —S(O) 2 NR 1b R 1c ;

each R A and R B is independently (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; each optionally substituted with one or more substituents Q; and

m is an integer of 1, 2, or 3.

28. The compound of claim 26 , wherein R 8 is hydrogen, hydroxyl, or methoxy.

29. The compound of claim 1 having the structure of Formula V:

or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof; or a pharmaceutically acceptable salt or prodrug thereof;

wherein:

A 2 , A 3 , and A 4 are each independently C, N, or CR 8 ; with the proviso that no more than one of A 2 , A 3 , and A 4 is N;

each R A and R B are each independently (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; each optionally substituted with one or more substituents Q;

each R 8 is independently (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; each optionally substituted with one or more substituents Q; or (c) —C(O)R 1a , —C(O)OR 1b , —C(O)NR 1b R 1c , —C(NR a )NR 1b R 1c , —OR 1a , —OC(O)R 1a , —OC(O)OR 1a , —OC(O)NR 1b R 1c , —OC(═NR 1a )NR 1b R 1c , —OS(O)R 1a , —OS(O) 2 R 1a , —OS(O)NR 1b R 1c , —OS(O) 2 NR 1b R 1c , —NR 1b R 1c , —NR 1a C(O)R 1d , —NR 1a C(O)OR 1d , —NR 1a C(O)NR 1b R 1c , —NR 1a C(═NR 1d )NR 1b R 1c , —NR 1a S(O)R 1d , —NR 1a S(O) 2 R 1d , —NR 1a S(O)NR 1b R 1c , —NR 1a S(O) 2 NR 1b R 1c , —SR 1a , —S(O)R 1a , —S(O) 2 R 1a , —S(O)NR 1b R 1c , or —S(O) 2 NR 1b R 1c ; and

p is an integer of 0, 1, 2, or 3.

30. The compound of claim 29 , wherein A 2 , A 3 , and A 4 are independently CR 8 .

31. The compound of claim 29 , wherein A 2 is N, and A 3 and A 4 are independently CR 8 .

32. The compound of claim 29 , wherein A 2 and A 4 are independently CR 8 , and A 3 is N.

33. The compound of claim 29 , wherein A 2 and A 3 are independently CR 8 , and A 4 is N.

34. The compound of claim 29 having the structure of Formula VI:

or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof; or a pharmaceutically acceptable salt or prodrug thereof.

35. The compound of claim 1 having the structure of Formula VII:

or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof; or a pharmaceutically acceptable salt or prodrug thereof;

wherein:

E 2 , E 3 , and E 4 are each independently C, N, O, S, CR 8 , or NR 8 ;

each R A and R B is independently (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; each optionally substituted with one or more substituents Q;

each R 8 is independently (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; each optionally substituted with one or more substituents Q; or (c) —C(O)R 1a , —C(O)OR 1b , —C(O)NR 1b R 1c , —C(NR a )NR 1b R 1c , —OR 1a , —OC(O)R 1a , —OC(O)OR 1a , —OC(O)NR 1b R 1c , —OC(═NR 1a )NR 1b R 1c , —OS(O)R 1a , —OS(O) 2 R 1a , —OS(O)NR 1b R 1c , —OS(O) 2 NR 1b R 1c , —NR 1b R 1c , —NR 1a C(O)R 1d , —NR 1a C(O)OR 1d , —NR 1a C(O)NR 1b R 1c , —NR 1a C(═NR 1d )NR 1b R 1c , —NR 1a S(O)R 1d , —NR 1a S(O) 2 R 1d , —NR 1a S(O)NR 1b R 1c , —NR 1a S(O) 2 NR 1b R 1c , —SR 1a , —S(O)R 1a , —S(O) 2 R 1a , —S(O)NR 1b R 1c , or —S(O) 2 NR 1b R 1c ; and

p is an integer of 0, 1, 2, or 3.

36. The compound of claim 35 , wherein E 2 , E 3 , and E 4 are CR 8 .

37. The compound of claim 35 , wherein E 2 and E 4 are CR 8 , and E 3 is NR 8 , O, or S.

38. The compound of claim 35 , wherein E 2 and E 3 are N, and E 4 is CR 8 .

39. The compound of claim 35 , wherein E 2 , E 3 , and E 4 are N.

40. The compound of claim 29 , wherein R 8 is hydrogen.

41. The compound of claim 29 , wherein R 8 is -L-(CR C R D ) n —R E , where R C and R D are each independently (a) hydrogen, cyano, halo, or nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; R E is hydrogen, —NR F R G , or heterocyclyl; L is a bond, —O—, or —N(R H )—; R F , R G , and R H are each independently hydrogen or C 1-6 alkyl; and n is an integer of 0, 1, 2, or 3.

42. The compound of claim 41 , wherein L is a bond, —O—, —NH—, or —N(CH 3 )—.

43. The compound of claim 41 , wherein R C and R D are hydrogen.

44. The compound of claim 41 , wherein R E is hydrogen, methylamino, dimethylamino, pyrrolidinyl, piperidinyl, or morpholinyl, wherein the pyrrolidinyl, piperidinyl, and morpholinyl are independently, optionally substituted with methyl.

45. The compound of claim 41 , wherein R 8 is independently selected from the group consisting of amino, fluoro, chloro, methyl, (dimethylamino)methyl, (dimethylamino)ethyl, (dimethylamino)propyl, morpholinylmethyl, (morpholinyl)ethyl, (morpholinyl)propyl, methoxy, (dimethylamino)ethoxy, (dimethylamino)propoxy, (morpholinyl)ethoxy, (morpholinyl)propoxy, (methyl-piperidinyl)oxy, (methyl-pyrrolidinyl)oxy, methylamino, dimethylamino, (dimethylamino)ethylamino, (dimethylaminoethyl)(methyl)amino, (dimethylamino)propylamino, ((dimethylamino)propyl)(methyl)amino, (morpholinyl)ethylamino, ((morpholinyl)ethyl)(methyl)amino, (morpholinyl)propylamino, ((morpholinyl)propyl)(methyl)amino, methyl-piperidinylamino, (methyl-piperidinyl)(methyl)amino, methyl-piperazinyl, and (dimethylamino)-piperidinyl.

46. The compound of claim 27 , wherein R A and R B are hydrogen.

47. The compound of claim 1 , wherein R 1 is C 1-6 alkyl, —S—C 1-6 alkyl or —SO 2 —C 1-6 alkyl, where each alkyl is independently, optionally substituted with one to three halo.

48. The compound of claim 47 , wherein R 1 is methyl, fluoromethyl, difluoromethyl, trifluoromethyl, methanesulfanyl, or methanesulfonyl.

49. The compound of claim 47 , wherein R 1 is difluoromethyl.

50. The compound of claim 47 , wherein R 1 is methanesulfanyl.

51. The compound of claim 47 , wherein R 1 is methanesulfonyl.

52. The compound of claim 1 , wherein R 2 is hydrogen, C 1-6 alkyl, or —O—C 1-6 alkyl, where each alkyl is optionally substituted with one or more substituents Q.

53. The compound of claim 52 , wherein R 2 is hydrogen.

54. The compound of claim 52 , wherein R 2 is methoxy.

55. The compound of claim 1 , wherein R 3 is hydrogen, amino, or C 1-6 alkyl, optionally substituted with one or more substituents Q.

56. The compound of claim 55 , wherein R 3 is hydrogen.

57. The compound of claim 55 , wherein R 3 is amino.

58. The compound of claim 1 , wherein R 4 is hydrogen or C 1-6 alkyl, optionally substituted with one or more substituents Q.

59. The compound of claim 58 , wherein R 4 is hydrogen.

60. The compound of claim 1 , wherein R 5 is hydrogen or C 1-6 alkyl, optionally substituted with one or more substituents Q.

61. The compound of claim 60 , wherein R 5 is hydrogen.

62. The compound of claim 1 , wherein R 4 and R 5 are linked together to form a bond or C 1-6 alkylene.

63. The compound of claim 62 , wherein R 4 and R 5 are linked together to form a bond, methylene, or ethylene.

64. The compound of claim 1 , wherein U is —O—, —NR 1a —, —S—, —S(O)—, or —S(O) 2 —, where R 1a is C 1-6 alkyl, optionally substituted with one or more substituents Q.

65. The compound of claim 64 , wherein U is —O—, —NH—, —NCH 3 —, —S—, —S(O)—, or —S(O) 2 —.

66. The compound of claim 64 , wherein U is —NH—.

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

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine;

4-[2-(methylsulfanyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine;

4-[2-(methylsulfonyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-phenyl-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-phenyl-1,3,5-triazin-2-amine;

N-benzyl-4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

N-benzyl-4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-phenoxy-1,3,5-triazin-2-yl]-1H-benzimidazole;

2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(phenylsulfanyl)-1,3,5-triazin-2-yl]-1H-benzimidazole;

2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(phenylsulfonyl)-1,3,5-triazin-2-yl]-1H-benzimidazole;

N-(2-chloro-5-pyrimidinyl)-4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(5-pyrimidinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(5-pyrimidinyl)-1,3,5-triazin-2-amine;

and enantiomers, mixtures of enantiomers, or mixtures of two or more diastereomers thereof; and pharmaceutically acceptable salts and prodrugs thereof.

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

N-[4-[6-amino-2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N-(3-pyridinyl)amine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(dimethylamino)propyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(dimethylamino)propyl]-N 2 -methyl-2,5-pyridinediamine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(6-methoxy-3-pyridinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{6-[3-(dimethylamino)propoxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(5-pyrimidinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridazinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-imidazol-5-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine; and

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-pyrazol-5-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine; and enantiomers, mixtures of enantiomers, or mixtures of two or more diastereomers thereof; and pharmaceutically acceptable salts and prodrugs thereof.

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

4-[4-methoxy-2-(methylsulfonyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(2-pyridinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(2-pyridinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(4-pyridinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(4-pyridinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(4-pyrimidinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(4-pyrimidinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(5-pyrimidinyl)-1,3,5-triazin-2-amine;

2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(3-pyridinyloxy)-1,3,5-triazin-2-yl]-1H-benzimidazole;

2-(difluoromethyl)-4-methoxy-1-[4-(4-morpholinyl)-6-(3-pyridinyloxy)-1,3,5-triazin-2-yl]-1H-benzimidazole;

2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(5-pyrimidinyloxy)-1,3,5-triazin-2-yl]-1H-benzimidazole;

2-(difluoromethyl)-4-methoxy-1-[4-(4-morpholinyl)-6-(5-pyrimidinyloxy)-1,3,5-triazin-2-yl]-1H-benzimidazole;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(1-methyl-1H-pyrazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-pyrazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(2-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(2-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(4-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(4-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(2-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(2-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(3-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(3-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(4-pyridinylmethyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(4-pyridinylmethyl)-1,3,5-triazin-2-amine;

2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(2-pyridinylmethoxy)-1,3,5-triazin-2-yl]-1H-benzimidazole;

2-(difluoromethyl)-4-methoxy-1-[4-(4-morpholinyl)-6-(2-pyridinylmethoxy)-1,3,5-triazin-2-yl]-1H-benzimidazole;

2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(3-pyridinylmethoxy)-1,3,5-triazin-2-yl]-1H-benzimidazole;

2-(difluoromethyl)-4-methoxy-1-[4-(4-morpholinyl)-6-(3-pyridinylmethoxy)-1,3,5-triazin-2-yl]-1H-benzimidazole;

2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(4-pyridinylmethoxy)-1,3,5-triazin-2-yl]-1H-benzimidazole;

2-(difluoromethyl)-4-methoxy-1-[4-(4-morpholinyl)-6-(4-pyridinylmethoxy)-1,3,5-triazin-2-yl]-1H-benzimidazole;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-[2-(2-pyridinyl)ethyl]-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-[2-(2-pyridinyl)ethyl]-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-[2-(3-pyridinyl)ethyl]-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-[2-(3-pyridinyl)ethyl]-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-[2-(4-pyridinyl)ethyl]-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-[2-(4-pyridinyl)ethyl]-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-[2-(1H-imidazol-4-yl)ethyl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-[2-(1H-imidazol-4-yl)ethyl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

N-[4-[6-amino-2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N-(3-pyridinyl)amine;

N-[4-[2-(difluoromethyl)-6-(methylamino)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N-(3-pyridinyl)amine;

N-[4-[2-(difluoromethyl)-4-methoxy-6-(methylamino)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N-(3-pyridinyl)amine;

N-[4-[2-(difluoromethyl)-6-(dimethylamino)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N-(3-pyridinyl)amine;

N-[4-[2-(difluoromethyl)-6-(dimethylamino)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N-(3-pyridinyl)amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(6-methoxy-3-pyridinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(2-methoxy-4-pyridinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-4-pyridinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{6-[2-(dimethylamino)ethoxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{6-[2-(dimethylamino)ethoxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{6-[2-(4-morpholinyl)ethoxy]-3-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{6-[2-(4-morpholinyl)ethoxy]-3-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{6-[3-(dimethylamino)propoxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{6-[3-(4-morpholinyl)propoxy]-3-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{6-[3-(4-morpholinyl)propoxy]-3-pyridinyl}-1,3,5-triazin-2-amine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 ,N 2 -dimethyl-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 ,N 2 -dimethyl-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(dimethylamino)ethyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(dimethylamino)ethyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(4-morpholinyl)ethyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(4-morpholinyl)ethyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(dimethylamino)ethyl]-N 2 -methyl-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(dimethylamino)ethyl]-N 2 -methyl-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -[2-(4-morpholinyl)ethyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -[2-(4-morpholinyl)ethyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(dimethylamino)propyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(dimethylamino)propyl]-N 2 -methyl-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(4-morpholinyl)propyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(4-morpholinyl)propyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -[3-(4-morpholinyl)propyl]-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -[3-(4-morpholinyl)propyl]-2,5-pyridinediamine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{6-[2-(dimethylamino)ethyl]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{6-[2-(dimethylamino)ethyl]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{6-[2-(4-morpholinyl)ethyl]-3-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{6-[2-(4-morpholinyl)ethyl]-3-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{2-[2-(dimethylamino)ethyl]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{2-[2-(dimethylamino)ethyl]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{2-[2-(4-morpholinyl)ethyl]-5-pyrimidinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{2-[2-(4-morpholinyl)ethyl]-5-pyrimidinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{5-[2-(dimethylamino)ethoxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{5-[2-(dimethylamino)ethoxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{5-[2-(4-morpholinyl)ethoxy]-3-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{5-[2-(4-morpholinyl)ethoxy]-3-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{5-[3-(dimethylamino)propoxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{5-[3-(dimethylamino)propoxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{5-[3-(4-morpholinyl)propoxy]-3-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{5-[3-(4-morpholinyl)propoxy]-3-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{2-[2-(dimethylamino)ethoxy]-4-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{2-[2-(dimethylamino)ethoxy]-4-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{2-[2-(4-morpholinyl)ethoxy]-4-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{2-[2-(4-morpholinyl)ethoxy]-4-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{2-[3-(dimethylamino)propoxy]-4-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{2-[3-(dimethylamino)propoxy]-4-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{2-[3-(4-morpholinyl)propoxy]-4-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{2-[3-(4-morpholinyl)propoxy]-4-pyridinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{2-[2-(dimethylamino)ethoxy]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{2-[2-(dimethylamino)ethoxy]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{2-[3-(dimethylamino)propoxy]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{2-[3-(dimethylamino)propoxy]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{2-[2-(4-morpholinyl)ethoxy]-5-pyrimidinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{2-[2-(4-morpholinyl)ethoxy]-5-pyrimidinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{2-[3-(4-morpholinyl)propoxy]-5-pyrimidinyl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{2-[3-(4-morpholinyl)propoxy]-5-pyrimidinyl}-1,3,5-triazin-2-amine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(dimethylamino)ethyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(dimethylamino)ethyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(dimethylamino)ethyl]-N 2 -methyl-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(dimethylamino)ethyl]-N 2 -methyl-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(dimethylamino)propyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(dimethylamino)propyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(dimethylamino)propyl]-N 2 -methyl-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(dimethylamino)propyl]-N 2 -methyl-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(4-morpholinyl)ethyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[2-(4-morpholinyl)ethyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -[2-(4-morpholinyl)ethyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -[2-(4-morpholinyl)ethyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(4-morpholinyl)propyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -[3-(4-morpholinyl)propyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -[3-(4-morpholinyl)propyl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -[3-(4-morpholinyl)propyl]-2,5-pyrimidinediamine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-[6-(4-methyl-1-piperazinyl)-3-pyridinyl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-[6-(4-methyl-1-piperazinyl)-3-pyridinyl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-[2-(4-methyl-1-piperazinyl)-5-pyrimidinyl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-[2-(4-methyl-1-piperazinyl)-5-pyrimidinyl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{6-[4-(dimethylamino)-1-piperidinyl]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{6-[4-(dimethylamino)-1-piperidinyl]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{2-[4-(dimethylamino)-1-piperidinyl]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{2-[4-(dimethylamino)-1-piperidinyl]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -(1-methyl-4-piperidinyl)-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -(1-methyl-4-piperidinyl)-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -(1-methyl-4-piperidinyl)-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -(1-methyl-4-piperidinyl)-2,5-pyridinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -(1-methyl-4-piperidinyl)-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -(1-methyl-4-piperidinyl)-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -(1-methyl-4-piperidinyl)-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N 2 -methyl-N 2 -(1-methyl-4-piperidinyl)-2,5-pyrimidinediamine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{6-[(1-methyl-4-piperidinyl)oxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{6-[(1-methyl-4-piperidinyl)oxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{2-[(1-methyl-4-piperidinyl)oxy]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{2-[(1-methyl-4-piperidinyl)oxy]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{6-[(1-methyl-3-pyrrolidinyl)oxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{6-[(1-methyl-3-pyrrolidinyl)oxy]-3-pyridinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{2-[(1-methyl-3-pyrrolidinyl)oxy]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{2-[(1-methyl-3-pyrrolidinyl)oxy]-5-pyrimidinyl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{1-[3-(dimethylamino)propyl]-1H-pyrazol-4-yl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{1-[3-(dimethylamino)propyl]-1H-pyrazol-4-yl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{1-[3-(4-morpholinyl)propyl]-1H-pyrazol-4-yl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-{1-[3-(4-morpholinyl)propyl]-1H-pyrazol-4-yl}-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(1,3-thiazol-5-yl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(1,3-thiazol-5-yl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-{2-[(dimethylamino)methyl]-1,3-thiazol-5-yl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-{2[(dimethylamino)methyl]-1,3-thiazol-5-yl}-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-[2-(4-morpholinylmethyl)-1,3-thiazol-5-yl]-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-[2-(4-morpholinylmethyl)-1,3-thiazol-5-yl]-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(1-methyl-1H-imidazol-5-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-1,2,3-triazol-5-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(1-methyl-1H-1,2,3-triazol-5-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(2-methyl-2H-1,2,3-triazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methyl-2H-1,2,3-triazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-1,2,3-triazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(1-methyl-1H-1,2,3-triazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(2-methyl-2H-tetrazol-5-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methyl-2H-tetrazol-5-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-tetrazol-5-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(1-methyl-1H-tetrazol-5-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

N 5 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2,5-pyrimidinediamine;

N 5 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2,5-pyrimidinediamine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(2-pyrazinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl) -N-(2-pyrazinyl)-1,3,5-triazin-2-amine;

N 2 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-pyrazinediamine;

N 2 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-pyrazinediamine;

N 2 -[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2,6-pyrazinediamine;

N 2 -[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl) -1,3,5-triazin-2-yl]-2,6-pyrazinediamine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(6-methoxy-2-pyrazinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(6-methoxy-2-pyrazinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine; and

N-[4-[6-amino-2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N-(3-pyridinyl)amine;

and enantiomers, mixtures of enantiomers, or mixtures of two or more diastereomers thereof; and pharmaceutically acceptable salts and prodrugs thereof.

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

N-[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-3-quinolinamine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(2-pyrimidinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(4-pyrimidinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(5-pyrimidinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(4-methoxy-3-pyridinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(6-fluoro-3-pyridinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

N-(6-chloro-3-pyridinyl)-4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

4-(2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl)-N-(6-methoxypyrimidin-4-yl)-6-morpholino-1,3,5-triazin-2-amine;

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridazinyl)-1,3,5-triazin-2-amine; and

4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(6-methoxy-3-pyridazinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine;

and enantiomers, mixtures of enantiomers, or mixtures of two or more diastereomers thereof; and pharmaceutically acceptable salts and prodrugs thereof.

71. A pharmaceutical composition comprising the compound of claim 1 , or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof; or a pharmaceutically acceptable salt or prodrug thereof; and one or more pharmaceutically acceptable carriers.

72. The pharmaceutical composition of claim 71 , further comprising a second therapeutic agent.

73. The pharmaceutical composition of claim 71 , wherein the composition is formulated for single dose administration.

74. The pharmaceutical composition of claim 71 , wherein the composition is formulated as oral, parenteral, or intravenous dosage form.

75. The pharmaceutical composition of claim 74 , wherein the oral dosage form is a tablet or capsule.

76. The compound of claim 14 , wherein m is 2.

77. The compound of claim 76 , wherein each R A is independently hydrogen or C 1-6 alkyl optionally substituted with one or more substituents Q.

78. The compound of claim 76 , wherein each R A is independently hydrogen or methyl.

79. The compound of claim 76 , wherein each R B is independently hydrogen or C 1-6 alkyl optionally substituted with one or more substituents Q.

80. The compound of claim 76 , wherein each R B is independently hydrogen or methyl.

81. The compound of claim 76 , wherein each R A and R B is independently hydrogen or methyl.

82. The compound of claim 27 , wherein m is 2.

83. The compound of claim 82 , wherein each R A is independently hydrogen or C 1-6 alkyl optionally substituted with one or more substituents Q.

84. The compound of claim 82 , wherein each R A is independently hydrogen or methyl.

85. The compound of claim 82 , wherein each R B is independently hydrogen or C 1-6 alkyl optionally substituted with one or more substituents Q.

86. The compound of claim 82 , wherein each R B is independently hydrogen or methyl.

87. The compound of claim 82 , wherein each R A and R B is independently hydrogen or methyl.

Assignments (5)
CHANGE OF NAME Recorded May 7, 2026
From: MEI PHARMA, INC.
To: LITE STRATEGY, INC.
Reel/Frame 075780/0968 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2013
From: PATHWAY THERAPEUTICS, INC.
To: MEI PHARMA, INC.
Reel/Frame 031215/0779 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2010
From: PATHWAY THERAPEUTICS LIMITED
To: PATHWAY THERAPEUTICS INC.
Reel/Frame 025375/0721 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2010
From: AUCKLAND UNISERVICES LIMITED
To: PATHWAY THERAPEUTICS LIMITED
Reel/Frame 024996/0891 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2010
From: REWCASTLE, GORDON WILLIAM; GAMAGE, SWARNALATHA AKURATIYA; TSANG, KIT YEE; GIDDENS, ANNA CLAIRE
To: AUCKLAND UNISERVICES LIMITED
Reel/Frame 024842/0743 →
Continuity (4)
Provisional Application 61223684 · Jul 7, 2009
Provisional Application 61247448 · Sep 30, 2009
Provisional Application 61318195 · Mar 26, 2010
Related Publication 20110009405A1 · Jan 13, 2011