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US 2011/0218208 A1Published application
2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases
AssigneeEdison Phamaceuticals, Inc.
InventorsAndrew W. Hinman, Orion D. Jankowski, Kieron E. Wesson
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Abstract
Methods of treating or suppressing oxidative stress disorders including mitochondrial diseases, impaired energy processing disorders, neurodegenerative diseases and diseases of aging are disclosed, as well as compounds useful in the methods of the invention, such as 2-heterocyclylaminoalkyl-(p-quinone) derivatives.
Claims31
A method of treating an oxidative stress disorder, including an oxidative stress disorder affecting normal electron flow in the cells, a disease caused by oxidative stress, a disease aggravated by oxidative stress, a primary oxidative stress disorder, a secondary oxidative stress disorder;
- or 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 one or more compounds of formula I:
- where R is selected from the group consisting of:
- where the * indicates the point of attachment of R to the remainder of the molecule;
- n is 0 or 1;
- R1 and R2 are independently selected from hydrogen, (C1-C6)alkyl, and (C1-C6)alkoxy;
- R3 is (C1-C6)alkyl or (C1-C6)alkoxy;
- R4 is hydrogen, (C1-C6)alkyl, hydroxy, or (C1-C6)alkoxy;
- Het is optionally substituted heterocyclyl;
- M and M′ are independently selected from hydrogen, —C(O)—R10, —C(O)(C2-C6)-alkenyl, —C(O)(C2-C6)-alkynyl, —C(O)-aryl, —C(O)-heterocyclyl, —C(O)O—R10, —C(O)NR10aR10b, —SO2OR10, —SO2—C1-C6-alkyl, —SO2—(C1-C6)-haloalkyl, —SO2-aryl, —SO2—NR10aR10b, and —P(O)(OR10a)(OR10b), and C-linked amino acid or di-peptide, and
- R10, R10a, and R10b are independently hydrogen or (C1-C6)-alkyl optionally substituted with —OH, —NH2, —NH(C1-C4 alkyl), —N(C1-C4 alkyl)2, —C(O)OH, —C(O)O—(C1-C4)-alkyl or halogen;
- or a salt, a solvate, or a hydrate thereof.
8 more elements
A compound of Formula I
- where R is selected from the group consisting of:
- where the * indicates the point of attachment of R to the remainder of the molecule;
- n is 0 or 1;
- R1 and R2 are independently selected from hydrogen, (C1-C6)alkyl, and (C1-C6)alkoxy;
- R3 is (C1-C6)alkyl or (C1-C6)alkoxy;
- R4 is hydrogen, (C1-C6)alkyl, hydroxy, or (C1-C6)alkoxy;
- Het is optionally substituted heterocyclyl;
- M and M′ are independently selected from hydrogen, —C(O)—R10, —C(O)(C2-C6)-alkenyl, —C(O)(C2-C6)-alkynyl, —C(O)-aryl, —C(O)-heterocyclyl, —C(O)O—R10, —C(O)NR10aR10b, —SO2OR10, —SO2—C1-C6-alkyl, —SO2—(C1-C6)-haloalkyl, —SO2-aryl, —SO2—NR10aR10b, and —P(O)(OR10a)(OR10b), and C-linked amino acid or di-peptide, and
- R10, R10a, and R10b are independently hydrogen or (C1-C6)-alkyl optionally substituted with —OH, —NH2, —NH(C1-C4 alkyl), —N(C1-C4 alkyl)2, —C(O)OH, —C(O)O—(C1-C4)-alkyl or halogen;
- with the proviso that the compound of Formula I is not 2-(2-(9-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-ylamino)ethyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione or 2-(2-(9-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-ylamino)ethyl)-3,5,6-trimethoxycyclohexa-2,5-diene-1,4-dione;
- or a salt, a solvate, or a hydrate thereof.
8 more elements
A compound of Formula Ia:
- where:
- n is 0 or 1;
- R1 and R2 are independently selected from hydrogen, (C1-C6)alkyl, and (C1-C6)alkoxy;
- R3 is (C1-C6)alkyl or (C1-C6)alkoxy;
- R4 is hydrogen, (C1-C6)alkyl, hydroxy, or (C1-C6)alkoxy;
- Het is heterocyclyl optionally substituted with (C1-C6)alkyl, (C1-C6)haloalkyl, halogen, nitro, cyano, —C(O)(C1-C4)alkyl, —C(O)(C1-C6)cycloalkyl, —C(O)OH, —C(O)O(C1-C4)-alkyl or oxo;
- or a salt, a solvate, or a hydrate thereof.
4 more elements
A compound of formula Ib
- where:
- n is 0 or 1;
- R1 and R2 are independently selected from hydrogen, (C1-C6)alkyl, and (C1-C6)alkoxy;
- R3 is (C1-C6)alkyl or (C1-C6)alkoxy;
- R4 is hydrogen, (C1-C6)alkyl, hydroxy, or (C1-C6)alkoxy;
- Het is heterocyclyl optionally substituted with (C1-C6)alkyl, (C1-C6)haloalkyl, halogen, nitro, cyano, —C(O)(C1-C4)alkyl, —C(O)(C1-C6)cycloalkyl, —C(O)OH, —C(O)O(C1-C4)-alkyl or oxo;
- M and M′ are independently selected from hydrogen, —C(O)—R10, —C(O)(C2-C6)-alkenyl, —C(O)(C2-C6)-alkynyl, —C(O)-aryl, —C(O)-heterocyclyl, —C(O)O—R10, —C(O)NR10aR10b, —SO2OR10, —SO2—C1-C6-alkyl, —SO2—(C1-C6)-haloalkyl, —SO2-aryl, —SO2—NR10aR10b, and —P(O)(OR10a)(OR10b), and C-linked amino acid or di-peptide, and
- R10, R10a, and R10b are independently hydrogen or (C1-C6)-alkyl optionally substituted with —OH, —NH2, —NH(C1-C4 alkyl), —N(C1-C4 alkyl)2, —C(O)OH, —C(O)O—(C1-C4)-alkyl or halogen;
- or a salt, a solvate, or a hydrate thereof.
6 more elements
Dependencies are inferred from the claim text.