Therapeutic compounds

A method of protecting cells from oxidative stress in an animal comprising administering to the animal an effective amount of compound of formula (I);

• or pharmaceutically acceptable salt thereof, wherein:
• R1 is C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl, and wherein the C1-20 alkyl, C2-20 alkenyl and C2-20 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• R2 is C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl, and wherein the C1-20 alkyl, C2-20 alkenyl and C2-20 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• or
• R1 and R2 taken together with the nitrogen to which they are attached form a 3-12 membered heterocycle that is optionally substituted with one or more groups independently selected from
• C1-4 alkyl, C1-4 haloalkyl, —F, —Cl, —Br, —I, —OH, —ORa, —SRa, —NRaRb, —CN, C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl, and wherein the C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl are optionally substituted with one or more groups independently;
• selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• each R3 is independently selected from the group consisting of —F, —Cl, —Br, —I, —OH, —ORa, —SRa, —NRaRb, —CN, C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl, and wherein the C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• each R4 is independently selected from the group consisting of —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl, and wherein the C1-4 alkyl:
• C2-4 alkenyl and C2-4 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• each Ra is independently hydrogen or C1-4 alkyl;
• each Rb is independently hydrogen or C1-4 alkyl;
• the subscript m is 0, 1, 2 or 3;
• and
• the subscnpt n is 0, 1, 2, or 3.

A method of preserving mitochondrial membrane potential and/or augmenting ATP production in an animal comprising administering to the animal an effective amount of compound of formula (I);

• or pharmaceutically acceptable salt thereof, wherein:
• R1 is C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl, and wherein the C1-20 alkyl, C2-20 alkenyl and C2-20 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• R2 is C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl, and wherein the C1-20 alkyl, C2-20 alkenyl and C2-20 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• or
• R1 and R2 taken together with the nitrogen to which they are attached form a 3-12 membered heterocycle that is optionally substituted with one or more groups independently selected from C1-4 alkyl, C1-4 haloalkyl. —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• each R3 is independently selected from the group consisting of —F, —Cl, —Br, —I, —OH, —ORa, —SRa, —NRaRb, —CN, C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl, and wherein the C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• each R4 is independently selected from the group consisting of —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl, and wherein the C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• each Ra is independently hydrogen or C1-4 alkyl;
• each Rb is independently hydrogen or C1-4 alkyl;
• the subscript m is 0, 1, 2 or 3;
• and
• the subscript n is 0, 1, 2, or 3.

A method of preserving mitochondrial membrane potential and/or augmenting ATP production of a cell in vitro comprising contacting the cell with an effective amount of compound of formula (I);

• or pharmaceutically acceptable salt thereof, wherein:
• R1 is C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl, and wherein the C1-20 alkyl, C2-20 alkenyl and C2-20 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• R2 is C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl, and wherein the C1-20 alkyl, C2-20 alkenyl and C2-20 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• or
• R1 and R2 taken together with the nitrogen to which they are attached form a 3-12 membered heterocycle that is optionally substituted with one or more groups independently selected from C1-4 alkyl, C1-4 haloalkyl. —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• each R3 is independently selected from the group consisting of —F, —Cl, —Br, —I, —OH, —ORa, —SRa, —NRaRb, —CN, C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl, and wherein the C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• each R4 is independently selected from the group consisting of —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl, and wherein the C1-4 alkyl, C2-4 alkenyl and C2-4 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —ORa, —SRa, —NRaRb, oxo, —NO2 and —CN;
• each Ra is independently hydrogen or C1-4 alkyl;
• each Rb is independently hydrogen or C1-4 alkyl;
• the subscript m is 0, 1, 2 or 3;
• and
• the subscript n is 0, 1, 2, or 3.