IP Library › Granted Patent US 7,105,676
Granted Patent B2
US 7,105,676 · App. 10/783,512 · Granted Sep 12, 2006

Tetrahydropyridoethers

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Quick Facts
Patent No.
US 7,105,676
App. No.
10/783,512
Granted
Sep 12, 2006
Kind
B2
Abstract

Compounds of formula (1) in which the substituents have the meanings mentioned in the description, are suitable for the prevention and treatment of gastrointestinal diseases.

Claims (84)

1. A compound of formula 1*

wherein R1 is CH 3 ;

each of R2a and R3b is H; and

each of R2b and R3a is a member selected from the group consisting of OH, OCH 3 , OCH(CH 3 ) 2 , OCH 2 CH 2 CH 3 , and OCH 2 CH 2 CH 2 OCH 3 ;

with the provisos that both R2b and R3a are not concurrently OH, and that, when neither is OH, both are the same.

2. The compound of claim 1 wherein R2b is OH, and R3a is OCH 3 .

3. The compound of claim 1 wherein R2b is OH, and R3a is OCH 2 CH 3 .

4. The compound of claim 1 wherein R2b is OH, and R3a is OCH(CH 3 ) 2 .

5. The compound of claim 1 wherein R2b is OH, and R3a is OCH 2 CH 2 CH 3 .

6. The compound of claim 1 wherein R2b is OH, and R3a is OCH 2 CH 2 CH 2 OCH 3 .

7. The compound of claim 1 wherein R3a is OH, and R2b is OCH 3 .

8. The compound of claim 1 wherein R3a is OH, and R2b is OCH 2 CH 3 .

9. The compound of claim 1 wherein R3a is OH, and R2b is OCH(CH 3 ) 2 .

10. The compound of claim 1 wherein R3a is OH, and R2b is OCH 2 CH 2 CH 3 .

11. The compound of claim 1 wherein R3a is OH, and R2b is OCH 2 CH 2 CH 2 OCH 3 .

12. The compound of claim 1 wherein R2b and R3a is OCH 3 .

13. The compound of claim 1 wherein R2b and R3a is OCH 2 CH 3 .

14. The compound of claim 1 wherein R2b and R3a is OCH(CH 3 ) 2 .

15. The compound of claim 1 wherein R2b and R3a is OCH 2 CH 2 CH 3 .

16. The compound of claim 1 wherein R2b and R3a is OCH 2 CH 2 CH 2 OCH 3 .

17. A compound of claim 1 which is in the form of a pharmaceutically acceptable salt.

18. A compound of formula 1*

wherein R1 is CH 2 OH;

each of R2a and R3b is H; and

each of R2b and R3a is a member selected from the group consisting of OH, OCH 3 , OCH(CH 3 ) 2 , OCH 2 CH 2 CH 3 , and OCH 2 CH 2 CH 2 OCH 3 ;

with the provisos that both R2b and R3a are not concurrently OH, and that, when neither is OH, both are the same.

19. The compound of claim 18 wherein R2b is OH, and R3a is OCH 3 .

20. The compound of claim 18 wherein R2b is OH, and R3a is OCH 2 CH 3 .

21. The compound of claim 18 wherein R2b is OH, and R3a is OCH(CH 3 ) 2 .

22. The compound of claim 18 wherein R2b is OH, and R3a is OCH 2 CH 2 CH 3 .

23. The compound of claim 18 wherein R2b is OH, and R3a is OCH 2 CH 2 CH 2 OCH 3 .

24. The compound of claim 18 wherein R3a is OH, and R2b is OCH 3 .

25. The compound of claim 18 wherein R3a is OH, and R2b is OCH 2 CH 3 .

26. The compound of claim 18 wherein R3a is OH, and R2b is OCH(CH 3 ) 2 .

27. The compound of claim 18 wherein R3a is OH, and R2b is OCH 2 CH 2 CH 3 .

28. The compound of claim 18 wherein R3a is OH, and R2b is OCH 2 CH 2 CH 2 OCH 3 .

29. The compound of claim 18 wherein R2b and R3a is OCH 3 .

30. The compound of claim 18 wherein R2b and R3a is OCH 2 CH 3 .

31. The compound of claim 18 wherein R2b and R3a is OCH(CH 3 ) 2 .

32. The compound of claim 18 wherein R2b and R3a is OCH 2 CH 2 CH 3 .

33. The compound of claim 18 wherein R2b and R3a is OCH 2 CH 2 CH 2 OCH 3 .

34. A compound of claim 18 which is in the form of a pharmaceutically acceptable salt.

35. A compound of formula 1*

wherein R1 is CH 3 ;

each of R2b and R3b is H; and

each of R2a and R3a is a member selected from the group consisting of OH, OCH 3 , OCH(CH 3 ) 2 , OCH 2 CH 2 CH 3 , and OCH 2 CH 2 CH 2 OCH 3 ;

with the provisos that both R2a and R3a are not concurrently OH, and that, when neither is OH, both are the same.

36. The compound of claim 35 wherein R2b is OH, and R3a is OCH 3 .

37. The compound of claim 35 wherein R2b is OH, and R3a is OCH 2 CH 3 .

38. The compound of claim 35 wherein R2b is OH, and R3a is OCH(CH 3 ) 2 .

39. The compound of claim 35 wherein R2b is OH, and R3a is OCH 2 CH 2 CH 3 .

40. The compound of claim 35 wherein R2b is OH, and R3a is OCH 2 CH 2 CH 2 OCH 3 .

41. The compound of claim 35 wherein R3a is OH, and R2b is OCH 3 .

42. The compound of claim 35 wherein R3a is OH, and R2b is OCH 2 CH 3 .

43. The compound of claim 35 wherein R3a is OH, and R2b is OCH(CH 3 ) 2 .

44. The compound of claim 35 wherein R3a is OH, and R2b is OCH 2 CH 2 CH 3 .

45. The compound of claim 35 wherein R3a is OH, and R2b is OCH 2 CH 2 CH 2 OCH 3 .

46. The compound of claim 35 wherein R2b and R3a is OCH 3 .

47. The compound of claim 35 wherein R2b and R3a is OCH 2 CH 3 .

48. The compound of claim 35 wherein R2b and R3a is OCH(CH 3 ) 2 .

49. The compound of claim 35 wherein R2b and R3a is OCH 2 CH 2 CH 3 .

50. The compound of claim 35 wherein R2b and R3a is OCH 2 CH 2 CH 2 OCH 3 .

51. A compound of claim 35 which is in the form of a pharmaceutically acceptable salt.

52. A compound of formula 1*

wherein R1 is CH 2 OH;

each of R2b and R3b is H; and

each of R2a and R3a is a member selected from the group consisting of OH, OCH 3 , OCH(CH 3 ) 2 , OCH 2 CH 2 CH 3 , and OCH 2 CH 2 CH 2 OCH 3 ;

with the provisos that both R2a and R3a are not concurrently OH, and that, when neither is OH, both are the same.

53. The compound of claim 52 wherein R2b is OH, and R3a is OCH 3 .

54. The compound of claim 52 wherein R2b is OH, and R3a is OCH 2 CH 3 .

55. The compound of claim 52 wherein R2b is OH, and R3a is OCH(CH 3 ) 2 .

56. The compound of claim 52 wherein R2b is OH, and R3a is OCH 2 CH 2 CH 3 .

57. The compound of claim 52 wherein R2b is OH, and R3a is OCH 2 CH 2 CH 2 OCH 3 .

58. The compound of claim 52 wherein R3a is OH, and R2b is OCH 3 .

59. The compound of claim 52 wherein R3a is OH, and R2b is OCH 2 CH 3 .

60. The compound of claim 52 wherein R3a is OH, and R2b is OCH(CH 3 ) 2 .

61. The compound of claim 52 wherein R3a is OH, and R2b is OCH 2 CH 2 CH 3 .

62. The compound of claim 52 wherein R3a is OH, and R2b is OCH 2 CH 2 CH 2 OCH 3 .

63. The compound of claim 52 wherein R2b and R3a is OCH 3 .

64. The compound of claim 52 wherein R2b and R3a is OCH 2 CH 3 .

65. The compound of claim 52 wherein R2b and R3a is OCH(CH 3 ) 2 .

66. The compound of claim 52 wherein R2b and R3a is OCH 2 CH 2 CH 3 .

67. The compound of claim 52 wherein R2b and R3a is OCH 2 CH 2 CH 2 OCH 3 .

68. A compound of claim 52 which is in the form of a pharmaceutically acceptable salt.

Assignments (5)
CHANGE OF NAME Recorded Jul 29, 2015
From: NYCOMED GERMANY HOLDING GMBH
To: TAKEDA GMBH
Reel/Frame 036205/0192 →
MERGER Recorded Jul 28, 2015
From: TAKEDA GMBH
To: NYCOMED ASSET MANAGEMENT GMBH
Reel/Frame 036193/0178 →
MERGER Recorded Jul 28, 2015
From: NYCOMED ASSET MANAGEMENT GMBH
To: NYCOMED GERMANY HOLDING GMBH
Reel/Frame 036201/0261 →
CHANGE OF NAME Recorded Mar 21, 2013
From: NYCOMED GMBH
To: TAKEDA GMBH
Reel/Frame 030062/0381 →
CHANGE OF NAME Recorded Oct 5, 2011
From: ALTANA PHARMA AG
To: NYCOMED GMBH
Reel/Frame 027019/0254 →