IP Library Granted Patent US 9,505,749
Granted Patent B2
US 9,505,749 · App. 14/423,078 · Granted Nov 29, 2016

Quinazolinone compounds and derivatives thereof

Inventors: Howard Bregman (Melrose, MA); John L. Buchanan (Newton, MA); Nagasree Chakka (Lexington, MA); Erin F. Dimauro (Cambridge, MA); Hakan Gunaydin (Somerville, MA); Angel Guzman-Perez (Belmont, MA); Zihao Hua (Andover, MA); Xin Huang (Wellesley, MA)
Assignee: AMGEN INC.
C07D471/02C07D239/90C07D239/95C07D401/12C07D401/14C07D403/12C07D413/12C07D413/14C07D417/12C07D417/14C07D471/04
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Quick Facts
Patent No.
US 9,505,749
App. No.
14/423,078
Granted
Nov 29, 2016
Kind
B2
Abstract

Compounds of Formula I are useful inhibitors of tankyrase. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.

Claims (249)

1. A compound of Formula I:

or a pharmaceutically acceptable salt thereof, a tautomer thereof, a pharmaceutically acceptable salt of the tautomer, a stereoisomer of any of the foregoing, or a mixture thereof, wherein:

R 1 is selected from —H, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —(C 1 -C 6 alkyl)-O—(C 1 -C 6 alkyl), —(C 1 -C 6 alkyl)-S—(C 1 -C 6 alkyl), —(C 1 -C 6 alkyl)-NH—(C 1 -C 6 alkyl), or (C 1 -C 6 alkyl)-NH 2 , or R 1 may additionally be selected from —O—(C 1 -C 6 alkyl), —NH—(C 1 -C 6 alkyl), or —N(C 1 -C 6 alkyl) 2 ;

R 2 is selected from —H, —NH 2 , —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —(C 1 -C 6 alkyl)-O—(C 1 -C 6 alkyl), —(C 1 -C 6 alkyl)-S—(C 1 -C 6 alkyl), —(C 1 -C 6 alkyl)-NH—(C 1 -C 6 alkyl), or —(C 1 -C 6 alkyl)-NH 2 ;

or R 1 and R 2 , together with the atoms to which they are attached, join to form a 6 membered ring comprising 0, 1, or 2 heteroatoms selected from N, O, or S; wherein the 6-membered ring is optionally substituted with one or two substituents selected from —F, —Cl, —Br, —I, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —OH, —O—(C 1 -C 6 alkyl), or —NH 2 ;

V is C;

W is CH or NH;

X is CH 2 , S, or SO 2 ;

Y is CH 2 or S;

one or two of X and Y are CH 2 ;

m is 0, 1, or 2;

Z is a group of formula II or formula III

wherein

R 3 is selected from —O—R 4a , —O—CH 2 —R 4a or —R 4a ;

R 4a is selected from a C 6 -C 10 aryl group, a heteroaryl group with 5 to 10 ring members containing 1, 2, or 3 heteroatoms independently selected from N, O, or S, or a heterocyclyl group with 5 to 10 ring members containing 1, 2, 3, or 4 heteroatoms independently selected from N, O, or S, or a —CH 2 -phenyl group, wherein the C 6 -C 10 aryl group, the heteroaryl group, or the heterocyclyl group are unsubstituted or are substituted with 1, 2, or 3 substituents independently selected from —F, —Cl, —Br, —I, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —OH, —O—(C 1 -C 6 alkyl), —R 4b , —OCH 2 —R 4b , —CH 2 O—R 4b , or —(C 1 -C 4 alkylene)-R 4b , and the heterocyclyl group may be further substituted with 1 oxo substituent;

R 4b is selected from C 6 -C 10 aryl group, a C 3 -C 8 cycloalkyl group, a heteroaryl group with 5 to 10 ring members containing 1, 2, or 3 heteroatoms independently selected from N, O, or S, or a heterocyclyl group with 5 to 10 ring members containing 1, 2, 3, or 4 heteroatoms independently selected from N, O, or S, wherein the C 6 -C 10 aryl group, the C 3 -C 8 cycloalkyl group, the heteroaryl group, and the heterocyclyl group are unsubstituted or are substituted with 1, 2, or 3 substituents independently selected from —F, —Cl, —Br, —I, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —OH, or —O—(C 1 -C 6 alkyl, and the heterocyclyl group or cycloalkyl group may be further substituted with 1 oxo substituent

n is 0, 1, 2, or 3;

p is 1, 2, or 3;

q is 1 or 2;

r is 1, 2, or 3;

A is CH or N;

wherein when Z is a group of formula Ill, R 1 and R 2 , together with the atoms to which they are attached, join to form a 6-membered ring;

wherein the ring that includes the A variable in the group of formula Ill may include 0 or 1 double bond and A is C if the bond between an adjacent ring member and A is a double bond;

U is a heterocyclic or heteroaromatic group selected from

R 5 and R 6a are independently in each instance selected from —F, —Cl, —Br, —I, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —OH, or —O—(C 1 -C 6 alkyl);

R 6b and R 7 are selected from —H and —C 1 -C 6 alkyl;

j is 0, 1, or 2;

k is 0, 1, or 2 and is 1 or 2 if X and Y are both carbon and m is 0; and

Q is selected from Q′ or —CH 2 O-Q′; and

Q′ is selected from C 6 -C 10 aryl group or a heteroaryl group with 5 to 10 ring members containing 1, 2, or 3 heteroatoms independently selected from N, O, or S, wherein the C 6 -C 10 aryl group and the heteroaryl group are unsubstituted or are substituted with 1, 2, or 3 substituents independently selected from —F, —Cl, —Br, —I, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —OH, or —O—(C 1 -C 6 alkyl);

wherein the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

2. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein

R 1 is selected from —H, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —(C 1 -C 6 alkyl)-0-(C 1 -C 6 alkyl), —(C 1 -C 6 alkyl)-S—(C 1 -C 6 alkyl), —(C 1 -C 6 alkyl)-NH—(C 1 -C 6 alkyl), or —(C 1 -C 6 alkyl)-NH 2 , or R 1 may additionally be selected from —O—(C 1 -C 6 alkyl), —NH—(C 1 -C 6 alkyl), or —N(C 1 -C 6 alkyl) 2 ; and

R 2 is selected from —H, —CH 3 , or —NH 2 .

3. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein R 1 is —H.

4. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein the compound of formula I, has the formula IA

5. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein R 1 and R 2 , together with the atoms to which they are attached, join to form a 6 membered ring comprising 0 or 1 heteroatoms selected from N, O, or S; wherein the 6-membered ring is optionally substituted with one or two substituents selected from —F, —Cl, —Br, —I, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —OH, —O—(C 1 -C 6 alkyl), or —NH 2 .

6. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein R 1 and R 2 , together with the atoms to which they are attached, join to form a 6 membered ring comprising 0 heteroatoms, wherein the 6-membered ring is optionally substituted with one or two substituents selected from —F, —Cl, —Br, —I, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —OH, —O—(C 1 -C 6 alkyl), or —NH 2 .

7. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein the compound of formula I, has the formula IB

wherein b is 0, 1, or 2; and

R a is independently selected from —F, —Cl, —Br, —I, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —OH, —O—(C 1 -C 6 alkyl), or —NH 2 .

8. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein the compound of formula I, has the formula IC

wherein b is 0, 1, or 2; and

R a is independently selected from —F, —Cl, —Br, —I, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —OH, —O—(C 1 -C 6 alkyl), or —NH 2 .

9. The compound of claim 7 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein b is 0, or b is 1 and R a is —F.

10. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein W is NH.

11. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein X is S and Y is CH 2 .

12. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein Y is S and X is CH 2 .

13. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein X is CH 2 and Y is CH 2 .

14. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein X is SO 2 and Y is CH 2 .

15. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein m is 0.

16. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein m is 1.

17. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein m is 2.

18. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein Z is a group of formula II.

19. The compound of claim 18 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein Z is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

20. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein Z is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

21. The compound of claim 20 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer or the mixture thereof, wherein Z is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

22. The compound of claim 20 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, or the mixture thereof, wherein Z is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

23. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein R 3 is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

24. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein R 3 is —O—R 4a or —R 4a .

25. The compound of claim 24 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein R 3 is —O—R 4a .

26. The compound of claim 24 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein R 3 is —R 4a .

27. The compound of claim 26 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein —R 4a is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

28. The compound of claim 27 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein R 4b is a C 6 -C 10 aryl group or a heteroaryl group with 5 to 10 ring members containing 1, 2, or 3 heteroatoms independently selected from N, O, or S, and the C 6 -C 10 aryl group and the heteroaryl group are unsubstituted or are substituted with 1, 2, or 3 substituents independently selected from —F, —Cl, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, or —O—(C 1 -C 6 alkyl).

29. The compound of claim 26 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein —R 4a is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

30. The compound of claim 26 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein —R 4a is

and R 4a is unsubstituted or is substituted with 1, 2, or 3 substituents independently selected from —F, —Cl, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, or —O—(C 1 -C 6 alkyl), and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

31. The compound of claim 26 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein —R 4a is selected from a heteroaryl group with 5 to 10 ring members containing 1, 2, or 3 heteroatoms independently selected from N, O, or S, or a heterocyclyl group with 5 to 10 ring members containing 1, 2, 3, or 4 heteroatoms independently selected from N, O, or S, wherein the heteroaryl group or the heterocyclyl group are unsubstituted or are substituted with 1, 2, or 3 substituents independently selected from —F, —CI, —Br, —I, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 perhaloalkyl, —OH, —O—(C 1 -C 6 alkyl), or —R 4b , and the heterocyclyl group may additionally be substituted with 1 oxo substituent.

32. The compound of claim 31 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein —R 4a is a heteroaryl group with 5 ring members comprising 2 or 3 heteroatoms independently selected from N, O, or S, or —R 4a is a heterocyclyl group with 9 ring members comprising 1, 2, or 3 heteroatoms independently selected from N, O, or S, wherein the heteroaryl group or the heterocyclyl group are unsubstituted or are substituted with 1, 2, or 3 substituents independently selected from —F, —Cl, —Br, —I, —CN, —CH 3 , —CF 3 , —OH, —O—CH 3 , or —R 4b and the heterocyclyl group may additionally be substituted with 1 oxo substituent.

33. The compound of claim 31 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein —R 4a is substituted with an R 4b substituent and —R 4b is selected from a phenyl, pyridyl, pyrazinyl, pyrimidinyl, or benzoimidazolonyl group, wherein the phenyl, pyridyl, pyrazinyl, pyrimidinyl, or benzoimidazolonyl group are unsubstituted or are substituted with 1, 2, or 3 substituents independently selected from —F, —Cl, —CN, —CH 3 , —CF 3 , or —O—CH 3 .

34. The compound of claim 18 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein n is 1 or 2.

35. The compound of claim 18 , or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein p is 1 or 2.

36. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein Z is a group of formula III.

37. The compound of claim 36 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein q is 1 or 2.

38. The compound of claim 36 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein r is 1 or 2.

39. The compound of claim 36 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein Z is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

40. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein U is selected from

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

41. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein U is

wherein

R ha is independently selected from —F, —Cl, —CN, —C 1 -C 6 alkyl, —C 1 -C 6 perhaloalkyl, or —O—(C 1 -C 6 alkyl);

k is 1 or 2;

R 6b is —H; and

the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

42. The compound of claim 41 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein R 6a is —F, —Cl, —CN, —CF 3 , —CH 3 , or —O—CH 3 .

43. The compound of claim 42 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein R 6a is —F, —Cl, —CN, —CF 3 , or —O—CH 3 .

44. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof wherein U is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

45. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein U is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

46. The compound of claim 45 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein Q is Q′ and Q′ is a phenyl or a heteroaryl group with 6 ring members containing 1 or 2 N heteroatoms, wherein the phenyl group and the heteroaryl group are unsubstituted or are substituted with 1 or 2 substituents independently selected from —F, —Cl, —CN, —CH 3 , —CF 3 , or —OCH 3 .

47. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein U is

and the symbol , when drawn across a bond, indicates the point of attachment to the rest of the molecule.

48. The compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, wherein the compound is

trans-N-(2-(4-oxo-3,4-dihydro-2-quinazolinypethyl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexanecarboxamide;

3-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

2-(4-(4-(5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-(3-fluorophenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(6-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-methoxy-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(5-phenyl-1,3,4-thiadiazol-2-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

4-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)butanamide;

2-(4-(4-(5-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(5-(2-pyridinyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(5-(3-pyridinyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(5-(2-pyrazinyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-(4-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-((4-chlorophenoxy)methyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-(2-fluorophenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(5-(4-pyridinyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

3-(5-(1-(4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanoyl)-4-piperidinyl)-1,3,4-oxadiazol-2-yl)benzonitrile;

4-(5-(1-(4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanoyl)-4-piperidinyl)-1,3,4-oxadiazol-2-yl)benzonitrile;

2-(4-(4-(5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-(3-chloro-4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-(4-(5-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

N-(trans-4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(5-(3-fluorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

4-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(5-(4-pyridinyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)butanamide;

2-(4-(4-(6-methoxy-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

N-(trans-4-(5-(3-chloro-4-fluorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

3-((4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)thio)-N-((1 r,4r)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

3-((4-oxo-3,4-dihydroquinazolin-2-yl)thio)-N-((1 s,3s)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclobutyl)propanamide;

3-((4-oxo-3,4-dihydroquinazolin-2-yl)thio)-N-((1 r,3r)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclobutyl)propanamide;

2-(4-oxo-4-(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(2-oxo-2,3-dihydro-1H-indol-1-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(2-oxo-1,3-benzoxazol-3(2H)-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-(4-(5-chloro-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-3,6-dihydro-1 (2H)-pyridinyl)butyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-(4-(1H-indazol-3-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(2-oxo-1,3-benzothiazol-3(2H)-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-(4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-oxo-4-(4-(2-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)butyl)-4(3H)-quinazolinone;

2-(4-(4-(6-fluoro-2-oxo-1,3-benzoxazol-3(2H)-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(1H-indazol-3-yl)-1-piperazinyl)-4-oxobutyl)-4(3H)-quinazolinone;

4-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(2-pyridinyloxy)cyclohexyl)butanamide;

N-(trans-4-(2-cyanophenoxy)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(3-cyanophenoxy)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

4-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(3-pyridinyloxy)cyclohexyl)butanamide;

2-(4-(4-(3,3-difluoro-2-oxo-2,3-dihydro-1H-indol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-oxo-1-(1-(4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanoyl)-4-piperidinyl)-2,3-dihydro-1H-benzimidazole-4-carbonitrile;

N-((1R,3R)-3-(benzyloxy)cyclopentyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-((1 S,3S)-3-(benzyloxy)cyclopentyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(4-chloro-3-cyanophenoxy)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(3-chloro-4-cyanophenoxy)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

4-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-((1 S,3S)-3-phenoxycyclopentyl)butanamide;

4-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-((1R,3R)-3-phenoxycyclopentyl)butanamide;

N-(trans-4-(3-chlorophenoxy)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

2-(4-(4-(4-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-oxo-1-(1-(4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanoyl)-4-piperidinyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile;

2-(4-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)-4-oxobutyl)-4(3H)-quinazolinone;

4-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(4-pyridinyloxy)cyclohexyl)butanamide;

2-(4-(4-(1,2-benzisoxazol-3-yl)-1-piperazinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-(5-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

N-(trans-4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(5-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

2-(4-(4-(1H-benzotriazol-1-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-((3S)-6-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

2-(4-(4-((3R)-6-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl)-1-piperidinyl)-4-oxobutyl)-4(3H)-quinazolinone;

N-(trans-4-(4-fluorophenoxy)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(4-cyanophenoxy)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(4-chlorophenoxy)cyclohexyl)-4-(4-oxo-3,4-dihydro-2-quinazolinyl)butanamide;

N-(trans-4-(2-oxo-1,3-benzoxazol-3(2H)-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

3-(4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-2-yl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

2-((3-(4-(5-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl)-3-oxopropyl)sulfanyl)-4(3H)-quinazolinone;

2-((3-oxo-3-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)-1-piperidinyl)propyl)sulfanyl)-4(3H)-quinazolinone;

N-(trans-4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

N-(trans-4-(5-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

N-(trans-4-(6-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

N-(trans-4-(5-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl)-2-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)acetamide;

3-(4-oxo-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidin-2-yl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

2-((2-oxo-2-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)-1-piperidinypethyl)sulfanyl)-4(3H)-quinazolinone;

N-(trans-4-(5-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

3-((4-amino-6-oxo-1,6-dihydro-2-pyrimidinyl)sulfanyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

3-(((4-oxo-3,4-dihydro-2-quinazolinyl)methyl)sulfanyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

2-(((3-(4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-1-piperidinyl)-3-oxopropyl)sulfanyl)methyl)-4(3H)-quinazolinone;

2-((3-(4-(1H-indazol-3-yl)-1-piperazinyl)-3-oxopropyl)sulfanyl)-4(3H)-quinazolinone;

4-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(5-phenyl-1,3-oxazol-2-yl)cyclohexyl)butanamide;

2-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)acetamide;

3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

2-(3-oxo-3-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)-1-piperidinyl)propyl)-4(3H)-quinazolinone;

N-(trans-4-(4-fluorophenoxy)cyclohexyl)-2-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)acetamide;

N-(trans-4-(4-fluorophenoxy)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

3-(6-fluoro-4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

N-(trans-4-(6-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl)-2-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)acetamide;

N-(trans-4-(5-cyano-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl)-2-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)acetamide;

N-(trans-4-(5-cyano-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(4-chlorophenoxy)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(4-cyanophenoxy)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)-N-(trans-4-(2-pyridinyloxy)cyclohexyl)propanamide;

3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)-N-(trans-4-(4-pyridinyloxy)cyclohexyl)propanamide;

N-(trans-4-(3-cyanophenoxy)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

4-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)butanamide;

2-((4-oxo-4-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)-1-piperidinyl)butyl)sulfanyl)-4(3H)-quinazolinone;

N-(trans-4-(3-chlorophenoxy)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(4-chloro-3-cyanophenoxy)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(3-chloro-4-cyanophenoxy)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

3-((4-oxo-3,4,5,6,7,8-hexahydro-2-quinazolinyl)sulfanyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

N-(trans-4-(4-cyanophenoxy)cyclohexyl)-34(4-oxo-3,4,5,6,7,8-hexahydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(5-(3-fluorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(5-(3-chloro-4-fluorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

3-((6-oxo-1,6-dihydro-2-pyrimidinyl)sulfanyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)-N-(trans-4-(5-(4-pyridinyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

N-(trans-4-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)propanamide;

N-(trans-4-(5-(2-fluorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

N-(trans-4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

N-(trans-4-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

N-(trans-4-(5-(3-fluorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

N-(trans-4-(5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

3-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(5-(2-pyridinyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

3-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(5-(4-pyridinyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

3-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(5-(2-pyrimidinyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

N-((1 r,4r)-4-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-(4-oxo-3,4-dihydroquinazolin-2-yl)propanamide;

3-(4-oxo-3,4-dihydroquinazolin-2-yl)-N-((1 r,4r)-4-(5-(tetrahydro-2H-pyran-4-yl)-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

3-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(5-(3-pyridinyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

N-(trans-4-(5-(3-cyanophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

N-(trans-4-(5-cyclohexyl-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

N-(trans-4-(5-benzyl-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

3-(4-oxo-3,4-dihydroquinazolin-2-yl)-N-((1 r,4r)-4-(5-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

N-(trans-4-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)-3-(4-oxo-3,4-dihydro-2-quinazolinyl)propanamide;

3-(4-oxo-3,4-dihydro-2-quinazolinyl)-N-(trans-4-(5-(2-pyrazinyl)-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide;

3-((4-oxo-3,4-dihydro-2-quinazolinyl)sulfinyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide; or

3-((6-fluoro-4-oxo-3,4-dihydro-2-quinazolinyl)sulfanyl)-N-(trans-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)propanamide.

49. A pharmaceutical composition, comprising the compound of claim 1 or the pharmaceutically acceptable salt thereof, the tautomer thereof, the pharmaceutically acceptable salt of the tautomer, the stereoisomer of any of the foregoing, or the mixture thereof, and at least one pharmaceutically acceptable excipient, carrier, or diluent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 13, 2016
From: BREGMAN, HOWARD; BUCHANAN, JOHN L.; CHAKKA, NAGASREE; DIMAURO, ERIN F.; GUNAYDIN, HAKAN; GUZMAN-PEREZ, ANGEL; HUA, ZIHAO; HUANG, XIN
To: AMGEN INC.
Reel/Frame 038272/0497 →
Continuity (2)
Provisional Application 61694560 · Aug 29, 2012
Related Publication 20150225396A1 · Aug 13, 2015