Alkyl substituted piperidine derivatives and their use as monoamine neurotransmitter re-uptake inhibitors
This invention relates to novel alkyl substituted piperidine derivatives useful as monoamine neurotransmitter re-up-take 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 piperidine derivative of the Formula I:
any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof,
wherein
R a represents hydrogen or alkyl;
X represents —O—;
R b represents a phenyl group, which phenyl group is substituted with one or more substituents independently selected from the group consisting of: halo, trifluoromethyl, trifluoromethoxy, cyano and alkoxy;
each of R 2 , R 2′ , R 6 and R 6′ represents alkyl; and
each of R 3 , R 3′ , R 5 and R 5′ represents hydrogen.
2. The chemical compound of claim 1 , wherein R b represents a phenyl group, which phenyl group is optionally substituted twice with halo.
3. The chemical compound of claim 1 , wherein each of R 2 , R 2′ , R 6 and R 6′ represents methyl.
4. The chemical compound of claim 1 , which is
4-(3,4-Dichloro-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(4-Chloro-3-trifluoromethyl-phenoxy)-1,2,2,6,6-pentamethyl-piperidine;
4-(4-Chloro-3-fluoro-phenoxy)-1,2,2,6,6-pentamethyl-piperidine;
4-(4-Bromo-3-chlorophenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(3,4-Dichloro-phenoxy)-1,2,2,6,6-pentamethyl-piperidine;
4-(3-Chloro-4-fluoro-phenoxy)-1,2,2,6,6-pentamethyl-piperidine;
4-(3-Chloro-4-fluoro-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(2-Chloro-5-fluoro-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(4-Trifluoromethyl-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(4-Chloro-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(2,4-Dichloro-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(2,5-Dichloro-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(2,4,5-Trichloro-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(3-Bromo-4-chloro-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(2,3,4-Trichloro-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(4-Chloro-3-trifluoromethyl-phenoxy)-2,2,6,6-tetramethyl-piperidine;
or a pharmaceutically acceptable salt thereof.
5. A pharmaceutical composition, comprising a therapeutically effective amount of a compound of claim 1 , or the compound:
4-(4-hydroxy-phenoxy)-2,2,6,6-tetramethyl-piperidine;
4-(4-methoxy-phenoxy)-2,2,6,6-tetramethyl-piperidine;
[4-(3,4-Dichloro-phenoxy)-2,2,6,6-tetramethyl-piperidin-1-yl]-acetonitrile; or a pharmaceutically acceptable salt thereof, together with at least one pharmaceutically acceptable carrier, excipient or diluent.
6. The chemical compound of claim 1 , wherein R b represents a tri-halo-phenyl group.