Quinoline derivatives and their use as 5-HT6 ligands
Disclosed are quinoline compounds having affinity for the 5-HT 6 receptor and having the formula: where R 1 , R 2 , R 3 , R 4 , R 5 , n, m, p and A are defined herein, and salts thereof, compositions containing these compounds and salts and processes for making and using the same.
1. A method of treating a patient suffering from a disorder selected from anxiety and depression, which method comprises administering a therapeutically effective amount of a compound of formula (I):
wherein:
R 1 represents hydrogen, methyl, ethyl, isopropyl, isobutyl or 2,2-dimethylpropyl;
R 2 represents hydrogen or methyl or is linked to R 1 to form a group (CH 2 ) 3 ;
R 3 represents hydrogen, methyl or halogen;
R 4 and R 5 independently represent hydrogen, or methyl;
m represents 1 or 2, or m is 2 and both R 2 groups are linked to form a CH 2 group linking C-2 and C-5 of the piperazine ring;
n represents 1;
p represents 1 or 2;
A represents a group —Ar 1 wherein Ar 1 represents unsubstituted phenyl or phenyl substituted by halogen, cyano, C 1-6 alkyl, C 1-6 alkoxy, trifluoromethyl or trifluoromethoxy,
or a pharmaceutically acceptable salt thereof,
to a patient in need thereof.
2. The method according to claim 1 , wherein the disorder is anxiety.
3. The method according to claim 1 , wherein the disorder is depression.
4. The method according to claim 1 , wherein:
R 1 represents hydrogen or methyl;
R 2 represents hydrogen or methyl;
R 3 represents hydrogen or halogen;
m represents 1;
n represents 1;
p represents 1;
A represents a group —Ar 1 wherein Ar 1 represents unsubstituted phenyl or phenyl substituted by halogen, cyano, trifluoromethyl or trifluoromethoxy.
5. The method according to claim 1 , wherein the compound is 3-phenylsulfonyl-8-piperazin-1-yl-quinoline or a pharmaceutically acceptable salt thereof.
6. The method according to claim 1 , wherein the compound is the free base of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline.
7. The method according to claim 2 , wherein the compound is 3-phenylsulfonyl-8-piperazin-1-yl-quinoline or a pharmaceutically acceptable salt thereof.
8. The method according to claim 2 , wherein the compound is the free base of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline.
9. The method according to claim 3 , wherein the compound is 3-phenylsulfonyl-8-piperazin-1-yl-quinoline or a pharmaceutically acceptable salt thereof.
10. The method according to claim 3 , wherein the compound is the free base of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline.