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Last Updated: March 28, 2024

Details for Patent: 8,404,675


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Title:Benzazepine derivatives and methods of prophylaxis or treatment of 5HT2C receptor associated diseases
Abstract: The present invention relates to certain 1-substituted-2,3,4,5-tetrahydro-3-benzazepine derivatives of Formula (I), that are modulators of the 5HT2C receptor. Accordingly, compounds of the present invention are useful for the prophylaxis or treatment of 5HT2C receptor associated diseases, conditions or disorders, such as, obesity and related disorders.
Inventor(s): Smith; Brian (San Diego, CA), Gilson, III; Charles A. (San Diego, CA), Schultz; Jeffrey (San Diego, CA), Smith; Jeffrey (San Diego, CA)
Assignee: Arena Pharmaceuticals, Inc. (San Diego, CA)
Filing Date:Mar 22, 2010
Application Number:12/729,026
Claims:1. A compound of Formula (I): ##STR00032## wherein: R.sub.1 is H or C.sub.1-8 alkyl; R.sub.2 is C.sub.1-4 alkyl, --CH.sub.2--O--C.sub.1-4 alkyl, C.sub.1-4 haloalkyl or CH.sub.2OH; and R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each independently H, C.sub.1-4 alkyl, amino, cyano, halogen, C.sub.1-4 haloalkyl, nitro or OH; or a pharmaceutically acceptable salt, or hydrate thereof; provided that when R.sub.2 is C.sub.1-4 alkyl, --CH.sub.2--O--C.sub.1-4 alkyl, and CH.sub.2OH then R.sub.3 and R.sub.6 are not both hydrogen.

2. The compound according to claim 1 wherein R.sub.1 is H.

3. The compound according to claim 1 wherein R.sub.1 is C.sub.1-8 alkyl.

4. The compound according to claim 3 wherein R.sub.1 is methyl.

5. The compound according to claim 3 wherein R.sub.1 is ethyl.

6. The compound according to claim 3 wherein R.sub.1 is n-propyl.

7. The compound according to claim 3 wherein R.sub.1 is iso-propyl.

8. The compound according to claim 3 wherein R.sub.1 is n-butyl.

9. The compound according to claim 1 wherein R.sub.2 is C.sub.1-4 alkyl.

10. The compound according to claim 9 wherein R.sub.2 is methyl.

11. The compound according to claim 9 wherein R.sub.2 is ethyl.

12. The compound according to claim 9 wherein R.sub.2 is iso-propyl.

13. The compound according to claim 9 wherein R.sub.2 is n-butyl.

14. The compound according to claim 1 wherein R.sub.2 is C.sub.1-4 haloalkyl.

15. The compound according to claim 14 wherein R.sub.2 is --CF.sub.3.

16. The compound according to claim 1 wherein R.sub.3 is H.

17. The compound according to claim 1 wherein R.sub.3 is C.sub.1-4 alkyl.

18. The compound according to claim 17 wherein R.sub.3 is --CH.sub.3.

19. The compound according to claim 1 wherein R.sub.3 is amino.

20. The compound according to claim 1 wherein R.sub.3 is cyano.

21. The compound according to claim 1 wherein R.sub.3 is halogen.

22. The compound according to claim 21 wherein R.sub.3 is a fluorine atom.

23. The compound according to claim 21 wherein R.sub.3 is a chlorine atom.

24. The compound according to claim 21 wherein R.sub.3 is a bromine atom.

25. The compound according to claim 21 wherein R.sub.3 is an iodine atom.

26. The compound according to claim 1 wherein R.sub.3 is C.sub.1-4 haloalkyl.

27. The compound according to claim 26 wherein R.sub.3 is CF.sub.3.

28. The compound according to claim 1 wherein R.sub.3 is nitro.

29. The compound according to claim 1 wherein R.sub.3 is --OH.

30. The compound according to claim 1 wherein R.sub.4 is H.

31. The compound according to claim 1 wherein R.sub.4 is C.sub.1-4 alkyl.

32. The compound according to claim 31 wherein R.sub.4 is --CH.sub.3.

33. The compound according to claim 1 wherein R.sub.4 is amino.

34. The compound according to claim 1 wherein R.sub.4 is cyano.

35. The compound according to claim 1 wherein R.sub.4 is halogen.

36. The compound according to claim 35 wherein R.sub.4 is a fluorine atom.

37. The compound according to claim 35 wherein R.sub.4 is a chlorine atom.

38. The compound according to claim 35 wherein R.sub.4 is a bromine atom.

39. The compound according to claim 35 wherein R.sub.4 is an iodine atom.

40. The compound according to claim 1 wherein R.sub.4 is C.sub.1-4 haloalkyl.

41. The compound according to claim 40 wherein R.sub.4 is CF.sub.3.

42. The compound according to claim 1 wherein R.sub.4 is nitro.

43. The compound according to claim 1 wherein R.sub.4 is --OH.

44. The compound according to claim 1 wherein R.sub.5 is H.

45. The compound according to claim 1 wherein R.sub.5 is C.sub.1-4 alkyl.

46. The compound according to claim 45 wherein R.sub.5 is --CH.sub.3.

47. The compound according to claim 1 wherein R.sub.5 is amino.

48. The compound according to claim 1 wherein R.sub.5 is cyano.

49. The compound according to claim 1 wherein R.sub.5 is halogen.

50. The compound according to claim 49 wherein R.sub.5 is a fluorine atom.

51. The compound according to claim 49 wherein R.sub.5 is a chlorine atom.

52. The compound according to claim 49 wherein R.sub.5 is a bromine atom.

53. The compound according to claim 49 wherein R.sub.5 is an iodine atom.

54. The compound according to claim 1 wherein R.sub.5 is C.sub.1-4 haloalkyl.

55. The compound according to claim 54 wherein R.sub.5 is CF.sub.3.

56. The compound according to claim 1 wherein R.sub.5 is nitro.

57. The compound according to claim 1 wherein R.sub.5 is --OH.

58. The compound according to claim 1 wherein R.sub.6 is H.

59. The compound according to claim 1 wherein R.sub.6 is C.sub.1-4 alkyl.

60. The compound according to claim 59 wherein R.sub.6 is --CH.sub.3.

61. The compound according to claim 1 wherein R.sub.6 is amino.

62. The compound according to claim 1 wherein R.sub.6 is cyano.

63. The compound according to claim 1 wherein R.sub.6 is halogen.

64. The compound according to claim 63 wherein R.sub.6 is a fluorine atom.

65. The compound according to claim 63 wherein R.sub.6 is a chlorine atom.

66. The compound according to claim 63 wherein R.sub.6 is a bromine atom.

67. The compound according to claim 63 wherein R.sub.6 is an iodine atom.

68. The compound according to claim 1 wherein R.sub.6 is C.sub.1-4 haloalkyl.

69. The compound according to claim 68 wherein R.sub.6 is CF.sub.3.

70. The compound according to claim 1 wherein R.sub.6 is nitro.

71. The compound according to claim 1 wherein R.sub.6 is --OH.

72. The compound of claim 1 selected from: 6,8-Dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine; 6-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine; 8-Chloro-9-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine; and 8,9-Dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine.

73. The compound of claim 1 that is 9-bromo-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine.

74. The compound of claim 1 selected from: N-methyl-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine; and N-methyl-9-bromo-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine.

75. The compound according to claim 1 wherein said compound is an R enantiomer.

76. The compound according to claim 1 wherein said compound is an S enantiomer.

77. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.

78. A method of treatment of obesity comprising administering to an individual in need of such treatment a therapeutically effective amount of a compound according to claim 1.

79. The method according to claim 78 wherein said individual is a mammal.

80. The method according to claim 79 wherein said mammal is a human.

81. A method of decreasing food intake of an individual comprising administering to said individual a therapeutically effective amount of a compound according to claim 1.

82. The method according to claim 81 wherein said individual is a mammal.

83. The method according to claim 82 wherein said mammal is a human.

84. A method of inducing satiety in an individual comprising administering to said individual a therapeutically effective amount of a compound according to claim 1.

85. The method according to claim 84 wherein said individual is a mammal.

86. The method according to claim 85 wherein said mammal is a human.

87. A method of controlling weight gain of an individual comprising administering to said individual suffering from weight control a therapeutically effective amount of a compound according to claim 1.

88. The method according to claim 87 wherein said individual is a mammal.

89. The method according to claim 88 wherein said mammal is a human.

90. The method according to claim 83 wherein the human has a body mass index of about 18.5 to about 45.

91. The method according to claim 83 wherein the human has a body mass index of about 25 to about 45.

92. The method according to claim 83 wherein the human has a body mass index of about 30 to about 45.

93. The method according to claim 83 wherein the human has a body mass index of about 35 to about 45.

94. A method of producing a pharmaceutical composition comprising admixing at least one compound according to claim 1 and at least one pharmaceutically acceptable carrier.

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