Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders
AssigneeEdison Pharmaceuticals, Inc.
InventorsAndrew W. HINMAN, Dana Davis, William D. Shrader
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Abstract
Disclosed herein are phenazine-3-one and phenothiazine-3-one derivative compounds and methods of using such compounds for treating or suppressing oxidative stress disorders, including mitochondrial disorders, impaired energy processing disorders, neurodegenerative diseases and diseases of aging.
Claims22
A compound of formula (I):
- wherein:
- R1 and R2 are independently selected from the group consisting of:
- —H, —C1-C4 alkyl, —O—C1-C4 alkyl, and —C1-C4 haloalkyl, and R3 is selected from the group consisting of:
- —H, —C1-C12 alkyl, —O—C1-C12 alkyl, and —C1-C12 haloalkyl;
- or
- R1 and R2 are both —CH3 or R1 and R2 are both —OCH3, and R3 is selected from the group consisting of:
- n is 0, 1, 2, 3, or 4;
- R4, R5, R6, and R7 are independently selected from the group consisting of:
- —H, —C1-C12 alkyl, —C2-C12 alkenyl, —C1-C12 haloalkyl, —O—C1-C12 alkyl, —O—C1-C12 halo alkyl, —C6-C10 aryl, —O—C6-C10 aryl, —C1-C6 alkyl-C6-C10 aryl, —O—C1-C6 alkyl-C6-C10 aryl, —N—(R8)(R9),
- with the proviso that at least two of R4, R5, R6, and R7 are independently selected from the group consisting of:
- —H and —CH3;
- R8 and R9 are independently —H or —C1-C12 alkyl;
- m is 0, 1, 2, or 3;
- and
- R11 is NH or S;
- or a stereoisomer, mixture of stereoisomers, solvate, hydrate, or pharmaceutically acceptable salt thereof;
- with the proviso that the compound is not:
- or a stereoisomer, mixture of stereoisomers, solvate, hydrate, or pharmaceutically acceptable salt thereof.
A method of treating or suppressing an oxidative stress disorder, modulating one or more energy biomarkers, normalizing one or more energy biomarkers, or enhancing one or more energy biomarkers, comprising administering to a subject a therapeutically effective amount or effective amount of a compound of formula (I):
- wherein:
- R1 and R2 are independently selected from the group consisting of:
- —H, —C1-C4 alkyl, —O—C1-C4 alkyl, and —C1-C4 haloalkyl, and R3 is selected from the group consisting of:
- —H, —C1-C12 alkyl, —O—C1-C12 alkyl, and —C1-C12 haloalkyl;
- or
- R1 and R2 are both —CH3 or R1 and R2 are both —OCH3, and R3 is selected from the group consisting of:
- n is 0, 1, 2, 3, or 4;
- R4, R5, R6, and R7 are independently selected from the group consisting of:
- —H, —C1-C12 alkyl, —C2-C12 alkenyl, —C1-C12 haloalkyl, —O—C1-C12 alkyl, —O—C1-C12 haloalkyl, —C6-C10 aryl, —O—C6-C10 aryl, —C1-C6 alkyl-C6-C10 aryl, —O—C1-C6 alkyl-C6-C10 aryl, —N—(R8)(R9),
- with the proviso that at least two of R4, R5, R6, and R7 are independently selected from the group consisting of:
- —H and —CH3;
- R8 and R9 are independently —H or —C1-C12 alkyl;
- m is 0, 1, 2, or 3;
- and
- R11 is S or NH;
- or a stereoisomer, mixture of stereoisomers, solvate, hydrate, or pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.