Aminoindole antidegradant compounds and uses thereof

A composition comprising a compound having Formula (I):

• or a salt or solvate thereof, wherein:
• is a single or a double bond;
• R1 is selected from the group consisting of C1-C12 alkyl, —CHR1aR1b, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• R1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;
• R1b is selected from the group consisting of hydrogen and C1-C9 alkyl;
• R2a, R2b, and R2c are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• or
• R2a and R2b taken together with the two carbon atoms to which they are attached form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4- to 6-membered heterocyclyl, an optionally substituted 4- to 6-membered aryl, or an optionally substituted 4- to 6-membered heteroaryl;
• and
• R3c is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• R3a is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• and
• R3b is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;
• or
• R3a and R3b taken together with the two carbon atoms to which they are attached form an optionally substituted C3-C12 cycloalkyl or an optionally substituted 4- to 6-membered heterocyclyl;
• R4 is selected from the group consisting of hydrogen and C1-C9 alkyl;
• and
• R5 is selected from the group consisting of hydrogen and C1-C9 alkyl;
• and one or more carriers.

A vulcanized elastomeric article comprising a compound having Formula (I):

• or a salt or solvate thereof, wherein:
• is a single or a double bond;
• R1 is selected from the group consisting of C1-C12 alkyl, —CHR1aR1b, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• R1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;
• R1b is selected from the group consisting of hydrogen and C1-C9 alkyl;
• R2a, R2b, and R2c are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• or
• R2a and R2b taken together with the two carbon atoms to which they are attached form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4- to 6-membered heterocyclyl, an optionally substituted 4- to 6-membered aryl, or an optionally substituted 4- to 6-membered heteroaryl;
• and
• R3c is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• R3a is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• and
• R3b is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;
• or
• R3a and R3b taken together with the two carbon atoms to which they are attached form an optionally substituted C3-C12 cycloalkyl or an optionally substituted 4- to 6-membered heterocyclyl;
• R4 is selected from the group consisting of hydrogen and C1-C9 alkyl;
• and
• R5 is selected from the group consisting of hydrogen and C1-C9 alkyl;
• and one or more carriers.

A lubricant composition comprising a lubricant and a compound having Formula (I):

• or a salt or solvate thereof, wherein:
• is a single or a double bond;
• R1 is selected from the group consisting of C1-C12 alkyl, —CHR1aR1b, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• R1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;
• R1b is selected from the group consisting of hydrogen and C1-C9 alkyl;
• R2a, R2b, and R2c are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• or
• R2a and R2b taken together with the two carbon atoms to which they are attached form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4- to 6-membered heterocyclyl, an optionally substituted 4- to 6-membered aryl, or an optionally substituted 4- to 6-membered heteroaryl;
• and
• R3c is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• R3a is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• and
• R3b is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;
• or
• R3a and R3b taken together with the two carbon atoms to which they are attached form an optionally substituted C3-C12 cycloalkyl or an optionally substituted 4- to 6-membered heterocyclyl;
• R4 is selected from the group consisting of hydrogen and C1-C9 alkyl;
• and
• R5 is selected from the group consisting of hydrogen and C1-C9 alkyl.

A combustible fuel composition comprising a combustible fuel and a compound having Formula (I):

• or a salt or solvate thereof, wherein:
• is a single or a double bond;
• R1 is selected from the group consisting of C1-C12 alkyl, —CHR1aR1b, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• R1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;
• R1b is selected from the group consisting of hydrogen and C1-C9 alkyl;
• R2a, R2b, and R2c are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• or
• R2a and R2b taken together with the two carbon atoms to which they are attached form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4- to 6-membered heterocyclyl, an optionally substituted 4- to 6-membered aryl, or an optionally substituted 4- to 6-membered heteroaryl;
• and
• R3c is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• R3a is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• and
• R3b is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;
• or
• R3a and R3b taken together with the two carbon atoms to which they are attached form an optionally substituted C3-C12 cycloalkyl or an optionally substituted 4- to 6-membered heterocyclyl;
• R4 is selected from the group consisting of hydrogen and C1-C9 alkyl;
• and
• R5 is selected from the group consisting of hydrogen and C1-C9 alkyl.

A fuel additive composition comprising a fuel additive and a compound having Formula (I):

• or a salt or solvate thereof, wherein:
• is a single or a double bond;
• R1 is selected from the group consisting of C1-C12 alkyl, —CHR1aR1b, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• R1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;
• R1b is selected from the group consisting of hydrogen and C1-C9 alkyl;
• R2a, R2b, and R2c are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• or
• R2a and R2b taken together with the two carbon atoms to which they are attached form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4- to 6-membered heterocyclyl, an optionally substituted 4- to 6-membered aryl, or an optionally substituted 4- to 6-membered heteroaryl;
• and
• R3c is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• R3a is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
• and
• R3b is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, —OH, C1-C8 alkoxy, —SH, C1-C8 alkylthio, —C(═O)OR4, —OC(═O)R4, —C(═O)NR4R5, —NR4C(═O)R5, —NR4R5, —SC(═O)R4, —SC(═O)SR4, —SC(═O)NR4R5, —NR4C(═O)SR5, —NR4C(═S)SR5, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;
• or
• R3a and R3b taken together with the two carbon atoms to which they are attached form an optionally substituted C3-C12 cycloalkyl or an optionally substituted 4- to 6-membered heterocyclyl;
• R4 is selected from the group consisting of hydrogen and C1-C9 alkyl;
• and
• R5 is selected from the group consisting of hydrogen and C1-C9 alkyl.