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US 11,535,596 B2Granted
Analogs of dextromethorphan with balanced receptor activities
AssigneeCenter for Neurologic Study
InventorsRichard Alan Smith, Darryl C. Rideout, Kathleen J. Myers, Andrew Kawasaki
Life of this patent
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Abstract
Substituted analogs of dextromethorphan (DM) are disclosed, which are shown to have substantial binding affinity at both NMDA and sigma-1 receptors, and which are degraded by human liver enzymes more slowly than dextromethorphan. The analogs are useful as alternatives to dextromethorphan, and can provide the same benefits without requiring co-administration of a cytochrome P-450 enzyme inhibitor.
Claims16
A compound of formula I
- wherein R1 is selected from the group consisting of H, CD3, C3-C4 alkenyl, C1-C4 alkyl, C3-C5 cycloalkyl, (C3-C5 cycloalkyl)methyl, and oxetanylmethyl;
- and R2 is one or more substituents selected from the group consisting of halogen, pyridylmethyl, C1-C4 alkyl, and C1-C4 alkoxy;
- with the proviso that at least one of the one or more R2 substituents is C2-C4 alkoxy substituted with one or more fluorine atoms and one or more deuterium atoms.
A pharmaceutical composition comprising one or more pharmaceutically acceptable excipients, and further comprising a compound of formula I
- or a pharmaceutically acceptable salt thereof, wherein R1 is selected from the group consisting of H, CD3, C3-C4 alkenyl, C1-C4 alkyl, C3-C5 cycloalkyl, (C3-C5 cycloalkyl)methyl, and oxetanylmethyl;
- and R2 is one or more selected from the group consisting of halogen, pyridylmethyl, C1-C4 alkyl, and C1-C4 alkoxy, with the proviso that at least one of the one or more R2 is C2-C4 alkoxy substituted with one or more fluorine atoms and one or more deuterium atoms.
Dependencies are inferred from the claim text.