IP Library › Patent Application 13723422

Patent Application

App. No. 13/723,422

RADIOLABELED 5-HT6 LIGANDS

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Patent No.: US None
App. No.: 13/723,422

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Abstract

Compounds of formula (I) are disclosed Compounds of formula (I) are useful in treating conditions and disorders prevented by or ameliorated by 5-HT 6 receptor ligands. Radiolabeled compounds of formula (I) are also useful as diagnostic tools as 5-HT 6 positron emission tomography ligands. Also disclosed are pharmaceutical compositions comprising compounds of formula (I), methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).

Claims (73)

1 . A compound of formula (I),

or a pharmaceutically acceptable salt, ester, amide, prodrug, or radiolabeled form thereof, wherein

R 1 and R 2 are each independently selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, and C 3 -C 8 cycloalkyl; and

R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from the group consisting of hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, and C 3 -C 8 cycloalkyl.

2 . The compound of claim 1 , wherein said compound comprises a radiolabel.

3 . The compound of claim 1 , wherein R 1 comprises a radiolabel.

4 . The compound of claim 1 , wherein R 1 is hydrogen.

5 . The compound of claim 1 , wherein R 1 is C 1 -C 6 alkyl.

6 . The compound of claim 5 , wherein R 1 is 11 CH 3 .

7 . The compound of claim 5 , wherein R 1 is 11 CH 2 CH 3 .

8 . The compound of claim 5 , wherein R 1 is 11 CH 2 CH 2 CH 3 .

9 . The compound of claim 5 , wherein R 1 is CH 2 CH 2 18 F.

10 . The compound of claim 5 , wherein R 1 is CH 2 CH 2 CH 2 18 F.

11 . The compound of claim 5 , wherein R 1 is C 1 -C 6 hydroxyalkyl.

12 . The compound of claim 5 , wherein R 1 is —CO 2 tBu.

13 . The compound of claim 1 , wherein R 2 is hydrogen.

14 . The compound of claim 1 , where R 2 comprises a radiolabel.

15 . The compound of claim 1 , wherein R 2 is C 1 -C 6 alkyl.

16 . The compound of claim 15 , wherein R 2 is 11 CH 3 .

17 . The compound of claim 15 , wherein R 2 is 11 CH 2 CH 3 .

18 . The compound of claim 15 , wherein R 2 is 11 CH 2 CH 2 CH 3 .

19 . The compound of claim 15 , wherein R 2 is CH 2 CH 2 18 F.

20 . The compound of claim 15 , wherein R 2 is CH 2 CH 2 CH 2 18 F.

21 . The compound of claim 1 , wherein R 7 is 18 F.

22 . The compound of claim 1 , wherein R 9 is 18 F.

23 . The compound of claim 1 , selected from the group consisting of:

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-ethylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-propylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-ethoxyphenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-propoxyphenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-(2-fluoroethyl)piperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-(3-fluoropropyl)piperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-(2-fluoroethoxy)phenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-(3-fluoropropoxy)phenyl)-4-methylpiperazine;

1-(5-(5-(difluoromethoxy)-2-fluorophenylsulfonyl)-2-methoxyphenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)-4-fluorophenylsulfonyl)-2-methoxyphenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)-4-fluorophenylsulfonyl)-2-methoxyphenyl)piperazine;

4-(3-(difluoromethoxy)-4-fluorophenylsulfonyl)-2-(4-methylpiperazin-1-yl)phenol;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-[ 11 C]methylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-[1- 11 C]ethylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-[1- 11 C]propylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-[ 11 C]methoxyphenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-[1- 11 C]ethoxyphenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-[1- 11 C]propoxyphenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-(2-[ 18 F]fluoroethyl)piperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-(3-[ 18 F]fluoropropyl)piperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-(2-[ 18 F]fluoroethoxy)phenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-(3-[ 18 F]fluoropropoxy)phenyl)-4-methylpiperazine;

1-(5-(5-(difluoromethoxy)-2-[ 18 F]fluorophenylsulfonyl)-2-methoxyphenyl)-4-methylpiperazine;

1-(5-(3-(difluoromethoxy)-4-[ 18 F]fluorophenylsulfonyl)-2-methoxyphenyl)-4-methylpiperazine; and

1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-([ 3 H]methyl)-piperazine.

24 . A pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (I) according to claim 1 , or a pharmaceutically acceptable salt, ester, amide, prodrug, or radiolabeled form thereof, in combination with a pharmaceutically acceptable carrier.

25 . Use of a compound of claim 1 as a 5-HT 6 positron emission tomography ligand.

26 . The use of claim 25 , wherein the compound is selected from the group consisting of: