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Generated: July 27, 2017

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Title:5HT.sub.2c receptor modulators
Abstract: The present invention relates to novel compounds of Formula (I): ##STR00001## which act as 5HT.sub.2C receptor modulators. These compounds are useful in pharmaceutical compositions whose use includes the treatment of obesity.
Inventor(s): Smith; Brian (San Diego, CA), Smith; Jeffrey (San Diego, CA)
Assignee: Arena Pharmaceuticals, Inc. (San Diego, CA)
Application Number:10/917,979
Patent Claims: 1. A method of decreasing food intake, inducing satiety, or controlling weight gain; or of treatment of a disorder selected from schizophrenia, anxiety, and obesity; in a patient in need thereof, comprising administering to said patient a pharmaceutically effective amount of a compound of Formula (I): ##STR00061## wherein: R.sub.1 is H or C.sub.1-8 alkyl; R.sub.2 is C.sub.1-8 alkyl, --CH.sub.2--O--C.sub.1-8 alkyl, --C(.dbd.O)--O--C.sub.1-8 alkyl, --C(.dbd.O)--NH--C.sub.1-8 alkyl, OH, or CH.sub.2OH; R.sub.2a is H; or R.sub.2 and R.sub.2a together form --CH.sub.2--CH.sub.2--; R.sub.3 and R.sub.4 are each independently H, halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, OH, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom; each R.sub.5 is independently C.sub.1-8 alkyl, C.sub.1-8 alkenyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl or perhaloalkyl, or allyl; and R.sub.6 is H or C.sub.1-8 alkyl; or a pharmaceutically acceptable salt, solvate or hydrate thereof; provided that: (A) if R.sub.2 is methyl and R.sub.1 and R.sub.3 are both H, then R.sub.4 is not thiazole, substituted thiazole or a thiazole derivative: (B) if R.sub.6 is other than H, then neither R.sub.3 nor R.sub.4 can be H; (C) if R.sub.1 and R.sub.2 are methyl, and R.sub.4 is H, then R.sub.3 cannot be NHR.sub.5 or N(R.sub.5).sub.2; (D) if R.sub.1 and R.sub.2 are methyl, and R.sub.4 is H, then R.sub.3 cannot be imidazole, substituted imidazole, or an imidazole derivative; and (E) if R.sub.3 is OH, and R.sub.1 is methyl then R.sub.2 cannot be cyclopentyl, --CH.sub.2-cyclohexyl, cyclopropylmethyl, or cyclohexyl.

2. The method according to claim 1 wherein: R.sub.3 is H, halogen, perhaloalkyl, CN, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; R.sub.4 is H, halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, OH, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom.

3. The method according to claim 1 wherein: R.sub.3 is halogen, perhaloalkyl, CN, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; and R.sub.4 is H, halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, OH, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom.

4. The method according to claim 1 wherein: R.sub.3 is H, halogen, perhaloalkyl, CN, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; and R.sub.4 is halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, OH, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom.

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

6. The method according to claim 1 wherein R.sub.2 is C.sub.1-8 alkyl.

7. The method according to claim 1 wherein R.sub.2 is methyl.

8. The method according to claim 1 wherein R.sub.3 is halogen.

9. The method according to claim 1 wherein R.sub.3 is chlorine.

10. The method according to claim 1 wherein R.sub.4 is H.

11. The method according to claim 1 wherein R.sub.6 is H.

12. The method according to claim 1 wherein said compound is 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, or pharmaceutically acceptable salt, solvate or hydrate thereof.

13. The method according to claim 1 wherein said compound is (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, or pharmaceutically acceptable salt, solvate or hydrate thereof.

14. The method according to claim 13 wherein said disorder is obesity.

15. The method according to claim 13 wherein said disorder is anxiety.

16. The method according to claim 13 wherein said disorder is schizophrenia.

17. The method according to claim 13 wherein said method is a method of decreasing food intake in a patient in need thereof.

18. The method according to claim 13 wherein said method is a method of inducing satiety in a patient in need thereof.

19. The method according to claim 13 wherein said method is a method of controlling weight gain in a patient in need thereof.

20. The method according to claim 1 wherein said disorder is obesity.

21. The method according to claim 1 wherein said disorder is anxiety.

22. The method according to claim 1 wherein said disorder is schizophrenia.

23. The method according to claim 1 wherein said method is a method of decreasing food intake in a patient in need thereof.

24. The method according to claim 1 wherein said method is a method of inducing satiety in a patient in need thereof.

25. The method according to claim 1 wherein said method is a method of controlling weight gain in a patient in need thereof.

26. A method of decreasing food intake or controlling weight gain; or of treatment of obesity; in a patient in need thereof, comprising administering to said patient a pharmaceutically effective amount of a compound of Formula (I): ##STR00062## wherein: R.sub.1 is H or C.sub.1-8 alkyl; R.sub.2 is C.sub.1-8 alkyl, --CH.sub.2--O--C.sub.1-8 alkyl, --C(.dbd.O)--O--C.sub.1-8 alkyl, --C(.dbd.O)--NH--C.sub.1-8 alkyl, or CH.sub.2OH; R.sub.2a is H; or R.sub.2 and R.sub.2a together form --CH.sub.2--CH.sub.2--; R.sub.3 and R.sub.4 are each independently H, halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom; each R.sub.5 is independently C.sub.1-8 alkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, perhaloalkyl, or allyl; and R.sub.6 is H or C.sub.1-8 alkyl; or a pharmaceutically acceptable salt or solvate thereof; provided that: (A) if R.sub.2 is methyl and R.sub.1 and R.sub.3 are both H, then R.sub.4 is not thiazole, substituted thiazole or a thiazole derivative; (B) if R.sub.6 is other than H, then neither R.sub.3 nor R.sub.4 can be H; (C) if R.sub.1 and R.sub.2 are methyl, and R.sub.4 is H, then R.sub.3 cannot be NHR.sub.5 or N(R.sub.5).sub.2; (D) if R.sub.1 and R.sub.2 are methyl, and R.sub.4 is H, then R.sub.3 cannot be imidazole, substituted imidazole, or an imidazole derivative; and (E) if R.sub.4 is OR.sub.5, then R.sub.2 cannot be cyclopentyl, --CH.sub.2-cyclohexyl, 3,3-dimethyl-2-allyl, 3,3-dimethyl-2-methyl-allyl, 2-methylallyl, 2-butenyl, cyclopropylmethyl, cyclohexyl or allyl.

27. A method of treatment of depression in a patient in need thereof, comprising administering to said patient a pharmaceutically effective amount of a compound of Formula (I): ##STR00063## wherein: R.sub.1 is H or C.sub.1-8 alkyl; R.sub.2 is C.sub.1-8 alkyl, --CH.sub.2--O--C.sub.1-8 alkyl, --C(.dbd.O)--O--C.sub.1-8 alkyl, --C(.dbd.O)--NH--C.sub.1-8 alkyl, OH, or CH.sub.2OH; R.sub.2a is H; or R.sub.2 and R.sub.2a together form --CH.sub.2--CH.sub.2--; R.sub.3 is H, halogen, perhaloalkyl, CN, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; R.sub.4 is H, halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, OH, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom; each R.sub.5 is independently C.sub.1-8 alkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, perhaloalkyl, or allyl; and R.sub.6 is H or C.sub.1-8 alkyl; or a pharmaceutically acceptable salt, solvate or hydrate thereof; provided that: (A) if R.sub.2 is methyl and R.sub.1 and R.sub.3 are both H, then R.sub.4 is not thiazole, substituted thiazole or a thiazole derivative; (B) if R.sub.6 is other than H, then neither R.sub.3 nor R.sub.4 can be H; (C) if R.sub.1 and R.sub.2 are methyl, and R.sub.4 is H, then R.sub.3 cannot be NHR.sub.5 or N(R.sub.5).sub.2; and (D) if R.sub.1 and R.sub.2 are methyl, and R.sub.4 is H, then R.sub.3 cannot be imidazole, substituted imidazole, or an imidazole derivative.

28. The method according to claim 27 wherein: R.sub.3 is halogen, perhaloalkyl, CN, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; and R.sub.4 is H, halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, OH, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhalo alkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom.

29. The method according to claim 27 wherein: R.sub.3 is H, halogen, perhaloalkyl, CN, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; and R.sub.4 is halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, OH, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom.

30. The method according to claim 27 wherein R.sub.1 is H.

31. The method according to claim 27 wherein R.sub.2 is C.sub.1-8 alkyl.

32. The method according to claim 27 wherein R.sub.2 is methyl.

33. The method according to claim 27 wherein R.sub.3 is halogen.

34. The method according to claim 27 wherein R.sub.3 is chlorine.

35. The method according to claim 27 wherein R.sub.4 is H.

36. The method according to claim 27 wherein R.sub.6 is H.

37. The method according to claim 27 wherein said compound is 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, or pharmaceutically acceptable salt, solvate or hydrate thereof.

38. The method according to claim 27 wherein said compound is (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, or pharmaceutically acceptable salt, solvate or hydrate thereof.

39. A method of treatment of a disorder selected from psychoses and alcohol addiction in a patient in need thereof, comprising administering to said patient a pharmaceutically effective amount of a compound of Formula (I): ##STR00064## wherein: R.sub.1 is H or C.sub.1-8 alkyl; R.sub.2 is C.sub.1-8 alkyl, --CH.sub.2--O--C.sub.1-8 alkyl, --C(.dbd.O)--O--C.sub.1-8 alkyl, --C(.dbd.O)--NH--C.sub.1-8 alkyl, OH, or CH.sub.2OH; R.sub.2a is H; or R.sub.2 and R.sub.2a together form --CH.sub.2--CH.sub.2--; R.sub.3 is H, halogen, perhaloalkyl, CN, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; R.sub.4 is halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, OH, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom; each R.sub.5 is independently C.sub.1-8 alkyl, C.sub.1-8 alkenyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, perhaloalkyl, or allyl; and R.sub.6 is H or C.sub.1-8 alkyl; or a pharmaceutically acceptable salt, solvate or hydrate thereof; provided that: (A) if R.sub.2 is methyl and R.sub.1 and R.sub.3 are both H, then R.sub.4 is not thiazole, substituted thiazole or a thiazole derivative: (B) if R.sub.6 is other than H, then neither R.sub.3 nor R.sub.4 can be H; (C) if R.sub.1 and R.sub.2 are methyl, and R.sub.4 is H, then R.sub.3 cannot be NHR.sub.5 or N(R.sub.5).sub.2; and (D) if R.sub.1 and R.sub.2 are methyl, and R.sub.4 is H, then R.sub.3 cannot be imidazole, substituted imidazole, or an imidazole derivative.

40. The method according to claim 39 wherein: R.sub.3 is H, halogen, perhaloalkyl, CN, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; and R.sub.4 is halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, OH, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhalo alkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom.

41. The method according to claim 39 wherein: R.sub.3 is H, halogen, perhaloalkyl, CN, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; and R.sub.4 is halogen, perhaloalkyl, CN, OR.sub.5, SR.sub.5, NHR.sub.5, N(R.sub.5).sub.2, OH, aryl, or heteroaryl, wherein said aryl can be optionally substituted with up to two substituents selected from C.sub.1-8 alkyl, halogen, perhaloalkyl, and alkoxy, and said heteroaryl can be optionally substituted with up to two substituents selected from halogen and C.sub.1-8 alkyl; or R.sub.3 and R.sub.4 together with the atoms to which they are attached can form a 5- or 6-member heterocyclic ring having one O atom.

42. The method according to claim 39 wherein R.sub.1 is H.

43. The method according to claim 39 wherein R.sub.2 is C.sub.1-8 alkyl.

44. The method according to claim 39 wherein R.sub.2 is methyl.

45. The method according to claim 39 wherein R.sub.3 is halogen.

46. The method according to claim 39 wherein R.sub.3 is chlorine.

47. The method according to claim 39 wherein R.sub.4 is H.

48. The method according to claim 39 wherein R.sub.6 is H.

49. The method according to claim 39 wherein said compound is 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, or pharmaceutically acceptable salt, solvate or hydrate thereof.

50. The method according to claim 39 wherein said compound is (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, or pharmaceutically acceptable salt, solvate or hydrate thereof.

51. The method according to claim 50 wherein said disorder is psychoses.

52. The method according to claim 50 wherein said disorder is alcohol addiction.

53. The method according to claim 39 wherein said disorder is psychoses.

54. The method according to claim 39 wherein said disorder is alcohol addiction.
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