Compounds and methods for promoting smoking cessation

1. A method of treating Tourette's syndrome, comprising administering to a patient in need thereof an effective amount of a compound represented by formula (II):

wherein

A 3 is —R, —N(R) 2 , —C(═NR)N(R) 2 , or —OR;

each Q is, independently, C—X or N, wherein one Q is N and each other Q is C—X;

each X is, independently, H, halogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, with the proviso that at least one X is represented by the formula:

each S is, independently, halogen, alkyl, alkenyl, alkynyl, phenyl, aralkyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, or two S, taken together with the phenyl group to which they are bonded, form a 2-naphthyl group;

c is 1,2,3,4 or 5;

Y is a halogen; and

each R is, independently, H, alkyl, alkenyl, alkynyl, aryl, or aralkyl;

or a pharmaceutically acceptable salt thereof.

2. The method of claim 1 , wherein c is 1.

3. The method of claim 1 , wherein c is 2.

4. The method of claim 1 , wherein c is 3.

5. The method of claim 1 wherein two of said S, taken together with the phenyl group to which they are bonded, form a 2-naphthyl group.

6. The method of claim 1 , wherein c is 1,2,3,4, or 5, and at least one S is halogen, alkyl, alkenyl, alkynyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, wherein R and Y are as defined in claim 1 .

7. The method of claim 1 , wherein c is 1,2,3,4, or 5, and at least one S is halogen, alkyl, or —NO 2 .

8. The method of claim 1 , wherein c is 1,2, or 3, and at least one S is halogen, alkyl, or —NO 2 .

9. The method of claim 1 , wherein c is 1 or 2, and at least one S is halogen, alkyl, or —NO 2 .

10. The method of claim 1 , wherein at least one X is halogen or —NH 2 .

11. The method of claim 1 , wherein at least one X is halogen, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, wherein R is as defined in claim 1 .

12. The method of claim 1 , wherein A 3 is H or alkyl.

13. The method of claim 1 , wherein A 3 is H.

14. The method of claim 1 , wherein one Q is N.

15. The method of claim 1 , wherein each X is independently selected from the group consisting of H, F, Cl, Br, I, CH 3 , OH, NH 2 , (CH 3 ) 2 N, NHAc, CF 3 SO 3 , subject to said proviso.

16. The method of claim 1 , wherein R is H, alkyl or benzyl.

17. The method of claim 1 , wherein said alkyl group in the definition of R is represented by the formula —(CH 2 ) n —Y, wherein Y is a halogen and n is an integer from 1 to 8.

18. The method of claim 1 , wherein the compound is represented by formula (IIa):

wherein

A 3 is as defined in claim 1 ;

X 1 , X 2 , X 3 and X 4 are each, independently, H, halogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, wherein at least one of X 1 , X 2 , X 3 , and X 4 is represented by said formula:

wherein

S and c are as defined in claim 1 ;

Y is as defined in claim 1 ; and

R is as defined in claim 1 .

19. The method of claim 18 , wherein the compound is represented by formula (IIb):

wherein

A 3 is as defined in claim 18 ;

X 1 , X 3 and X 4 are each, independently, H, halogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN;

R is as defined in claim 18 ;

Y is as defined in claim 18 ;

S is as defined in claim 18 ; and

c is as defined in claim 18 .

20. The method of claim 19 , wherein c is 1.

21. The method of claim 19 , wherein c is 2.

22. The method of claim 19 , wherein c is 3.

23. The method of claim 19 , wherein two of said S, taken together with the phenyl group to which they are bonded, form a 2-naphthyl group.

24. The method of claim 19 , wherein c is 1,2,3,4, or 5, and at least one S is halogen, alkyl, alkenyl, alkynyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, wherein R and Y are as defined in claim 19 .

25. The method of claim 19 , wherein c is 1,2,3,4, or 5, and at least one S is halogen, alkyl, or —NO 2 .

26. The method of claim 19 , wherein c is 1,2, or 3, and at least one S is halogen, alkyl, or —NO 2 .

27. The method of claim 19 , wherein c is 1 or 2, and at least one S is halogen, alkyl, or —NO 2 .

28. The method of claim 19 , wherein at least one of X 1 , X 3 , and X 4 is halogen or —NH 2 .

29. The method of claim 19 , wherein at least one of X 1 , X 3 , and X 4 is halogen, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, wherein R is as defined in claim 19 .

30. The method of claim 19 , wherein A 3 is H or alkyl.

31. The method of claim 19 , wherein A 3 is H.

32. The method of claim 19 , wherein X 1 , X 3 , and X 4 are each hydrogen.

33. The method of claim 19 , wherein R is H, alkyl or benzyl.

34. The method of claim 19 , wherein said alkyl group in the definition of R is represented by the formula —(CH 2 ) n —Y, wherein Y is a halogen and n is an integer from 1 to 8.

35. The method of claim 19 , wherein X 1 is fluorine and X 3 and X 4 are hydrogen.

36. The method of claim 35 , wherein c is 1.

37. The method of claim 36 , wherein S is fluorine, chlorine, methoxy, —NO 2 or —NH 2 .

38. The method of claim 37 , wherein A 3 is hydrogen.

39. The method of claim 19 , wherein X 1 is —Cl, —Br, NH 2 or OH and X 3 and X 4 are hydrogen.

40. The method of claim 39 , wherein c is 1.

41. The method of claim 40 , wherein S is —Cl, —Br, —F, —NO 2 , methoxy, —NH 2 or —N(C H 3 ) 3 .

42. The method of claim 41 , wherein A 3 is hydrogen.

43. The method of claim 1 , wherein at least one atom in the compound is a member selected from the group consisting of 3 H, 11 C, 14 C, 35 S, 18 F, 123 I, 125 I, and 131 I.

44. The method of claim 43 , wherein at least one atom in the compound is a member selected from the group consisting of 3 H, 11 C, 18 C, and, 123 I.

45. The method of claim 43 , wherein at least one X is 18 F, 123 I, 125 I, or 131 I.

46. The method of claim 43 , wherein at least one X is a phenyl group substituted with one or more of 18 F, 123 I, or 125 I or 131 I.