US 11,680,034 B2
Fluoroalkyl, fluoroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders
Andrew W. Hinman, San Francisco, CA (US); and Steven J. Richards, Brisbane, CA (US)
Assigned to PTC Therapeutics, Inc., South Plainfield, NJ (US)
Filed by PTC THERAPEUTICS, INC., South Plainfield, NJ (US)
Filed on Apr. 12, 2021, as Appl. No. 17/228,648.
Application 17/228,648 is a division of application No. 16/946,786, filed on Jul. 6, 2020, granted, now 10,981,855.
Application 16/946,786 is a division of application No. 16/063,201, granted, now 10,703,701, issued on Jul. 7, 2020, previously published as PCT/US2016/067404, filed on Dec. 17, 2016.
Claims priority of provisional application 62/269,016, filed on Dec. 17, 2015.
Prior Publication US 2021/0238119 A1, Aug. 5, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 50/28 (2006.01); C07C 50/24 (2006.01); C07D 207/06 (2006.01); A61P 39/06 (2006.01); C07C 225/24 (2006.01); C07C 317/04 (2006.01); C07D 213/65 (2006.01); C07D 295/108 (2006.01)
CPC C07C 50/28 (2013.01) [A61P 39/06 (2018.01); C07C 50/24 (2013.01); C07C 225/24 (2013.01); C07C 317/04 (2013.01); C07D 207/06 (2013.01); C07D 213/65 (2013.01); C07D 295/108 (2013.01)] 18 Claims
 
1. A compound of the formula I:

OG Complex Work Unit Chemistry
or the hydroquinone form thereof;
wherein:
R1 and R2 are independently C1-C10 alkyl;
R3 is C1-C6 alkyl or —NHS(O)2CH3;
R4 is C8-C12 n-alkyl and R5 is C1 haloalkyl, —O—C1-C6 alkyl, —O—C1-C6 haloalkyl, —O-phenyl, —O-heteroaryl, or —NR6R7, wherein R5 is attached to R4 at any chemically possible location on the C8-C12 n-alkyl group; or
R4 is C8-C12 alkyl and R5 is C1 haloalkyl, —O—C2-C6 alkyl, —O—C3-C6 haloalkyl, —O-phenyl, —O-heteroaryl, or —NR6R7, wherein R5 is attached to R4 at any chemically possible location on the C8-C12 alkyl group;
R6 and R7 are independently selected from the group consisting of H and C1-C6 alkyl; or R6 and R7 together with the nitrogen atom to which they are attached form a 3-7 membered saturated heterocyclic ring; and
phenyl and heteroaryl are optionally independently substituted with 1-4 substituents each independently selected from the group consisting of C1-C4 alkyl; or a salt, a stereoisomer, or mixture of stereoisomers thereof;
wherein:
when R4 is C8 n-alkyl, then R5 is not CF3;
when R4 is C9 n-alkyl, then R5 is not —CH2Br; and
when R4 is C10 n-alkyl, then R5 is not —OCH3 or —OCH2CF3.