Carboxylic acid 4-phenylazo-phenyl ester derivatives and their use as monoamine neurotransmitter re-uptake inhibitors
This invention relates to novel carboxylic acid 4-phenylazo-phenyl ester derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.
1. A compound of Formula I:
any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
Q represents a phenyl group;
which phenyl group is optionally substituted with one or more substituents independently selected from the group consisting of:
halo, trifluoromethyl, trifluoromethoxy, cyano and alkoxy;
n is 0 or 1;
R 1 represents hydrogen or alkyl; and
either R 2 and R 3 together form —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 — or —CH 2 —CH 2 —CH 2 —CH 2 —; and R 4 represents hydrogen;
or R 1 and R 4 together form —CH 2 —CH 2 —; and R 3 represents hydrogen;
or R 2 , R 3 and R 4 each represent hydrogen.
2. The compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
n is 1;
R 1 and R 4 together form —CH 2 —CH 2 —; and
R 3 represents hydrogen.
3. The compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
n is 0; and
R 2 and R 3 together form —CH 2 —CH 2 —.
4. The compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
n is 0; and
R 2 and R 3 together form —CH 2 —CH 2 —CH 2 —.
5. The compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
n is 0; and
R 2 and R 3 together form —CH 2 —CH 2 —CH 2 —CH 2 —.
6. The compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
n is 1;
R 2 and R 3 together form —CH 2 —CH 2 —; and
R 4 represents hydrogen.
7. The compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
n is 1;
R 2 and R 3 together form —CH 2 —CH 2 —CH 2 —; and
R 4 represents hydrogen.
8. The compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
n is 0; and
R 2 and R 3 each represent hydrogen.
9. The compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
n is 1; and
R 2 and R 3 each represent hydrogen.
10. The compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
R 1 represents alkyl.
11. The compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein
Q represents phenyl.
12. The compound according to claim 1 , selected from the group consisting of
1,4-Diaza-bicyclo[3.2.2]nonane-4-carboxylic acid 4-phenylazo-phenyl ester;
9-Methyl-3,9-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid 4-phenylazo-phenyl ester;
4-Methyl-piperazine-1-carboxylic acid 4-phenylazo-phenyl ester;
4-Methyl-[1,4]diazepane-1-carboxylic acid 4-phenylazo-phenyl ester;
8-Methyl-3,8-diaza-bicyclo[3.2.1]octane-3-carboxylic acid 4-phenylazo-phenyl ester;
10-Methyl-8,10-diaza-bicyclo[4.3.1]decane-8-carboxylic acid 4-phenylazo-phenyl ester;
10-Methyl-3,10-diaza-bicyclo[4.3.1]decane-3-carboxylic acid 4-phenylazo-phenyl ester;
and
9-Methyl-3,9-diaza-bicyclo[4.2.1]nonane-3-carboxylic acid 4-phenylazo-phenyl ester; or any of its stereoisomers or any mixture of its stereoisomers or a pharmaceutically acceptable salt thereof.
13. A pharmaceutical composition, comprising a therapeutically effective amount of a compound according to claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, together with at least one pharmaceutically acceptable carrier, excipient or diluent.