Fluoroalkyl, fluoroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders

A compound of the formula I:

• 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.