IP Library › Granted Patent US 8,969,352
Granted Patent B2
US 8,969,352 · App. 14/206,722 · Granted Mar 3, 2015

Substituted 2-azabicycles and their use as orexin receptor modulators

Inventors: Christine F. Gelin (San Diego, CA); Terry P. Lebold (San Diego, CA); Brock T. Shireman (Poway, CA)
Assignee: Janssen Pharmaceutica NV
C07D413/14C07D401/12C07D401/14C07D403/14C07D471/08C07D487/08C07D519/00
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,969,352
App. No.
14/206,722
Granted
Mar 3, 2015
Kind
B2
Abstract

The present invention is directed to compounds of Formula I: wherein X is N or CR 1 ; Y is N or CR 2 ; R 1 is H, alkoxy, halo, triazolyl, pyrimidinyl, oxazolyl, isoxazole, oxadiazolyl, or pyrazolyl; R 2 is H, alkyl, alkoxy, or halo; Z is NH or O; R 3 is H, alkyl, alkoxy, halo, or triazolyl; R 4 is H or alkyl; or R 3 and R 4 , together with the atoms to which they are attached, form a 6-membered aryl ring or a 5- or 6-membered heteroaryl ring; R 5 is pyridyl, pyrazinyl, or pyrimidinyl, wherein the pyridyl, pyrazinyl, or pyrimidinyl is optionally substituted with halo or alkyl; and n is 1 or 2. Methods of making the compounds of Formula I are also described. The invention also relates to pharmaceutical compositions comprising compounds of Formula I. Methods of using the compounds of the invention are also within the scope of the invention.

Claims (221)

1. A compound of formula I

or an enantiomer or diastereomer thereof;

or a pharmaceutically acceptable salt thereof;

wherein

X is N or CR 1 ;

Y is N or CR 2 ;

R 1 is H, alkoxy, halo, triazolyl, pyrimidinyl, oxazolyl, isoxazolyl, oxadiazolyl, or pyrazolyl;

R 2 is H, alkyl, alkoxy, or halo;

Z is NH or O;

R 3 is H, alkyl, alkoxy, halo, or triazolyl;

R 4 is H or alkyl;

or R 3 and R 4 , together with the atoms to which they are attached, form a 6-membered aryl ring or a 5- or 6-membered heteroaryl ring;

R 5 is pyridyl, pyrazinyl, or pyrimidinyl, wherein the pyridyl, pyrazinyl, or pyrimidinyl is optionally substituted with halo or alkyl; and

n is 1 or 2.

2. The compound of claim 1 , wherein Z is NH.

3. The compound of claim 1 , wherein Z is O.

4. The compound of claim 1 , wherein X is CR 1 and Y is CR 2 .

5. The compound of claim 1 , wherein X is CR 1 and Y is N.

6. The compound of claim 1 , wherein X is N and Y is CR 2 .

7. The compound of claim 1 , wherein R 1 is alkoxy, halo, triazolyl, pyrimidinyl, oxazolyl, isoxaolyl, oxadiazolyl, or pyrazolyl.

8. The compound of claim 7 , wherein R 1 is alkoxy, halo, triazolyl, or pyrimidinyl.

9. The compound of claim 7 , wherein pyrazolyl is methyl-pyrazolyl or dimethyl-pyrazolyl.

10. The compound of claim 7 , wherein oxadiazolyl is methyl-oxadiazolyl.

11. The compound of claim 1 or 6 , wherein R 2 is H.

12. The compound of claim 1 or 6 , wherein R 2 is alkyl.

13. The compound of claim 12 , wherein alkyl is —CH 3 .

14. The compound of claim 1 or 6 , wherein R 2 is alkoxy.

15. The compound of claim 1 or 6 , wherein R 2 is halo.

16. The compound of claim 15 , wherein halo is F.

17. The compound of claim 1 , wherein R 3 is H.

18. The compound of claim 1 , wherein R 3 is alkyl.

19. The compound of claim 1 , wherein R 3 is alkoxy.

20. The compound of claim 1 , wherein R 3 is halo.

21. The compound of claim 1 , wherein R 3 is triazolyl.

22. The compound of claim 1 , wherein R 4 is H.

23. The compound of claim 1 , wherein R 4 is alkyl.

24. The compound of claim 23 , wherein alkyl is —CH 3 .

25. The compound of claim 1 , wherein R 3 and R 4 together with the atoms to which they are attached, form a 6-membered aryl ring.

26. The compound of claim 1 , wherein R 3 and R 4 together with the atoms to which they are attached, form a 6-membered heteroaryl ring containing one N.

27. The compound of claim 1 , wherein R 3 and R 4 together with the atoms to which they are attached, form a 5-membered heteroaryl ring containing one N.

28. The compound of claim 1 , wherein R 5 is pyridyl, optionally substituted with halo or alkyl.

29. The compound of claim 28 , wherein alkyl is trihaloalkyl.

30. The compound of claim 28 , wherein R 5 is pyridyl optionally substituted with trifluoromethyl.

31. The compound of claim 1 , wherein R 5 is pyrazinyl, optionally substituted with halo or alkyl.

32. The compound of claim 31 , wherein alkyl is trihaloalkyl.

33. The compound of claim 31 , wherein R 5 is pyrazinyl optionally substituted with trifluoromethyl.

34. The compound of claim 1 , wherein R 5 is pyrimidinyl, optionally substituted with halo or alkyl.

35. The compound of claim 34 , wherein alkyl is trihaloalkyl.

36. The compound of claim 34 , wherein R 5 is pyrimidinyl optionally substituted with trifluoromethyl.

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

38. The compound of claim 1 , wherein n is 2.

39. A compound selected from the group consisting of

Ex.

No.

Compound

Compound Name

1

(R/S)-(2-(2H-1,2,3-triazol-2- yl)phenyl)(6-((5- (trifluoromethyl)pyrazin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

2

(R/S)-(6-methyl-3-(2H-1,2,3- triazol-2-yl)pyridin-2-yl)(6-((5- (trifluoromethyl)pyrazin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

3

(R/S)-(3-ethoxyisoquinolin-4- yl)((5-(trifluoromethyl)pyrazin-2- yl)oxy)-2-azabicyclo[2.2.1]heptan- 2-yl)methanone

4

(R/S)-5-methyl-3-(2H-1,2,3- triazol-2-yl)pyridin-2-yl)(6-((5- (trifluoromethyl)pyrazin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

7

(R/S)-(2-(2H-1,2,3-triazol-2- yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

8

(R/S)-(3-ethoxyisoquinolin-4- yl)(6-((5-(trifluoromethyl)pyridin- 2-yl)oxy)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

9

(R/S)-(5-methyl-3-(2H-1,2,3- triazol-2-yl)pyridin-2-yl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

10

(R/S)-(7-ethoxyquinolin-8-yl)(6- ((5-(trifluoromethyl)pyridin-2- yl)oxy)-2-azabicyclo[2.2.1]heptan- 2-yl)methanone

11

(R/S)-(3-fluoro-2-(pyrimidin-2- yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

12

(R/S)-(4-methoxy-2-(pyrimidin-2- yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

13

(R/S)-4-methoxy-2-(2H-1,2,3- triazol-2-yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

14

(R/S)-(5-fluoro-2-(2H-1,2,3- triazol-2-yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

15

(R/S)-2-methoxy-6-(2H-1,2,3- triazol-2-yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

16

(R/S)-(3-fluoro-2-(2H-1,2,3- triazol-2-yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

17

(R/S)-(3-methyl-2-(2H-1,2,3- triazol-2-yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

18

(R/S)-(2-fluoro-6-(2H-1,2,3- triazol-2-yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

19

(R/S)-(5-fluoro-2-(pyrimidin-2- yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

20

(R/S)-(4-fluoro-2-(pyrimidin-2- yl)phenyl)(-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

21

(R/S)-(2-(4H-1,2,4-triazol-4- yl)phenyl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

22

(R/S)-(6-methyl-3-(2H-1,2,3- triazol-2-yl)pyridin-2-yl)(6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

23

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1R,4S,6S)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

24

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

25

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

26

(4-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

27

(3-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyrimidin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

28

(5-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

29

(6-methyl-2-(2H-1,2,3-triazol-2- yl)pyridin-3-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

30

(3-(2H-1,2,3-triazol-2-yl)pyridin-2- yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

31

(3-fluoro-2- methoxyphenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

32

(3-methyl-2-(oxazol-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

33

(3-fluoro-2-(1H-1,2,3-triazol-1- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

34

(6-methyl-2-(1H-1,2,3-triazol-1- yl)pyridin-3-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

35

(3-fluoro-2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

36

(2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

37

(3-ethoxy-6-methylpyridin-2- yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

38

(2-fluoro-6-(pyrimidin-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

39

(2-methoxy-6-(1H-pyrazol-5- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

40

(2-methoxy-6-(pyrimidin-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

41

(2-(1,4-dimethyl-1H-pyrazol-5- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

42

(1H-indol-7-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

43

(5-fluoro-2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

44

(4-fluoro-2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

45

(2-bromo-3- fluorophenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

46

(2-fluoro-6-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

47

((1S,4R,6R)-6-((5-bromopyridin-2- yl)oxy)-2-azabicyclo[2.2.1]heptan- 2-yl)(2-fluoro-6-(pyrimidin-2- yl)phenyl)methanone

48

((1S,4R,6R)-6-((5-bromopyridin-2- yl)oxy)-2-azabicyclo[2.2.1]heptan- 2-yl)(3-fluoro-2-(pyrimidin-2- yl)phenyl)methanone

49

(2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4R,6R)-6-((5- bromopyridin-2-yl)oxy)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

50

((1S,4R,6R)-6-((5-bromopyridin-2- yl)oxy)-2-azabicyclo[2.2.1]heptan- 2-yl)(6-methyl-3-(2H-1,2,3-triazol- 2-yl)pyridin-2-yl)methanone

51

(2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4R,6R)-6-((3- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

52

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((3- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

53

(2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

54

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

55

(3-methyl-2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

56

(7-ethoxyquinolin-8- yl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

57

(5-fluoro-2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

58

(5-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

59

(2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyrazin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

60

(2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyrimidin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

61

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyrazin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

62

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyrimidin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

63

(4-methyl-2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

64

(4-methyl-2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyrazin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

65

(4-methyl-2-(2H-1,2,3-triazol-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyrimidin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

66

(3-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

67

(3-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyrazin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

68

(3-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyrimidin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

69

(2-(3-methyl-1,2,4-oxadiazol-5- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

70

(3-fluoro-2-(3-methyl-1,2,4- oxadiazol-5- yl)phenyl)((1S,4S,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.1]heptan-2- yl)methanone

71

(3-fluoro-2-(3-methyl-1,2,4- oxadiazol-5- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

72

(3-fluoro-2-(3-methyl-1,2,4- oxadiazol-5- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.1]heptan-2- yl)methanone

73

(3-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.2]octan-2- yl)methanone

74

(3-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyrazin-2-yl)oxy)- 2-azabicyclo[2.2.2]octan-2- yl)methanone

75

(3-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyrimidin-2- yl)oxy)-2-azabicyclo[2.2.2]octan- 2-yl)methanone

76

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2-yl)oxy)- 2-azabicyclo[2.2.2]octan-2- yl)methanone

77

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyrazin-2-yl)oxy)- 2-azabicyclo[2.2.2]octan-2- yl)methanone

78

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyrimidin-2- yl)oxy)-2-azabicyclo[2.2.2]octan- 2-yl)methanone

79

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyrimidin-2- yl)amino)-2- azabicyclo[2.2.2]octan-2- yl)methanone

80

(3-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyrazin-2- yl)amino)-2- azabicyclo[2.2.2]octan-2- yl)methanone

81

(3-fluoro-2-(pyrimidin-2- yl)phenyl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyrimidin-2- yl)amino)-2- azabicyclo[2.2.2]octan-2- yl)methanone

82

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyridin-2- yl)amino)-2- azabicyclo[2.2.2]octan-2- yl)methanone

83

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyrazin-2- yl)amino)-2- azabicyclo[2.2.2]octan-2- yl)methanone

84

(6-methyl-3-(2H-1,2,3-triazol-2- yl)pyridin-2-yl)((1S,4R,6R)-6-((5- (trifluoromethyl)pyrimidin-2- yl)amino)-2- azabicyclo[2.2.2]octan-2- yl)methanone

40. A pharmaceutical composition comprising a compound according to claim 1 and at least one pharmaceutically acceptable excipient.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2016
From: GELIN, CHRISTINE F.; LEBOLD, TERRY P.; SHIREMAN, BROCK T.
To: JANSSEN PHARMACEUTICA NV
Reel/Frame 040240/0241 →
Continuity (2)
Provisional Application 61780378 · Mar 13, 2013
Related Publication 20140275118A1 · Sep 18, 2014