Benzoquinone derivatives for treating oxidative stress disorders

US9629815B2 · kind B2 · utility

Assignee

• BIOELECTRON TECHNOLOGY CORPORATION · US

Inventors

• William D. Shrader · Belmont, US
• Andrew W. Hinman · San Francisco, US
• Viktoria Kheifets · Mountain View, US

Key dates

• Filing date: Sep 6, 2013
• Grant date: Apr 25, 2017
• Expiry date: Sep 6, 2033

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C66/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Disclosed herein are 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, or for modulating one or more energy biomarkers, normalizing one or more energy biomarkers, or enhancing one or more energy biomarkers, wherein the compound is a compound of Formula I or Formula II: wherein: R1 and R2 are independently hydrogen, (C1-C6)alkyl or —O(C1-C6)alkyl; or R1 and R2 together represent —CH═CH—CH═CH—; R3 is (C1-C6)alkyl; X is —CH═CH— or —C≡C—; m is 1-10; n is 1-5; k is 1-3, with the proviso that when k is an integer of 2 or 3, n is independently 1-5 in each occurrence of the —X—(CH2)n— group; Y is —OR4, —CN, —C(═O)OR5, —C(═O)R5, or —C(═O)N(R6)2; R4 and R5 are independently selected from the group consisting of hydrogen, —(C1-C6)alkyl, —(C1-C6)haloalkyl, —C(═O)—(C1-C6)alkyl, —C(═O)—(C1-C6)haloalkyl, —C(═O)—NH(C1-C6)alkyl, —C(═O)—N((C1-C6)alkyl)2, —C(═O)—NH2, and phenyl, wherein the phenyl group may optionally be substituted with a substituent selected from the group consisting of —(C1-C6)alkyl, —O—(C1-C6)alkyl, —(C1-C6)…