Isolated hydroxy and N-oxide metabolites and derivatives of O-desmethylvenlafaxine and methods of treatment

Abstract

The present invention provides novel isolated compounds characterized as metabolites or derivatives of desmethylvenlafaxine including hydroxy-DV metabolites, hydroxy-DV-glucuronide metabolites, N-oxide-DV metabolites, and benzyl-hydroxy-DV metabolites. The invention includes pharmaceutical compositions comprising any of the metabolites or derivatives of the invention in combination with a pharmaceutically acceptable carrier or excipient. The invention also includes a method of treating at least one central nervous system disorder in a mammal comprising providing to a mammal in need thereof an effective amount of the compounds of the invention.

Description

Background technique

[0001] This application claims priority to US Provisional Patent Application No. 60 / 854,063, filed October 25, 2006, which is incorporated by reference in its entirety.

[0002] Venlafaxine, chemically known as 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol, has been shown to be a potent monoamine neurotransmitter Inhibitor of mass uptake, a mechanism implicated in clinical antidepressant activity. Due to its novel structure, venlafaxine has an unrelated mechanism of action to other available antidepressants such as the tricyclic antidepressants desipramine, nostriptyline , protriptyline, imipramine, amitriptyline (amitryptyline), trimipramine, and doxepin.

[0003] The mechanism of action of venlafaxine is believed to be related to potent inhibition of the uptake of the monoamine neurotransmitters serotonin and norepinephrine. Venlafaxine also inhibits dopamine reuptake to a lesser extent but has no inhibitory activity on monoamine oxidase....

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