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US 2019/0375737 A1Published application
Quinoline alkenes as cytoprotective agents
OwnerRussell Dahlinventor
Life of this patent
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Abstract
Provided herein are compounds of Formula I, pharmaceutical compositions thereof, and methods of their use for treating, preventing, or ameliorating one or more symptoms of a neurological disease, neurodegenerative disorder, or diabetes.
Claims14
A compound of Formula I:
- or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, or an isotopic variant thereof;
- or a pharmaceutically acceptable salt, solvate, or hydrate thereof;
- wherein:
- R2 is (a) hydrogen or (b) methyl;
- R3, R4, R5, R6, and R7 are each independently (a) hydrogen, cyano, or halo;
- (b) C1-6 alkyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
- or (c) —C(O)R1a, —C(O)OR1a, —C(O)NR1bR1c, —C(NR1a)NR1bR1c,
- —OR1a, —OS(O)NR1bR1c, —OS(O)2NR1bR1c, —NR1bR1c, —NR1aC(O)R1d, —NR1aC(O)OR1d, —NR1aC(O)NR1bR1c, —NR1aS(O)R1d, —NR1aS(O)2R1d;
- each R1a, R1b, R1c, and R1d is independently (i) hydrogen;
- (ii) C1-6 alkyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
- or (iii) R1b and R1c together with the N atom to which they are attached form heterocyclyl;
- and
- R1 is aryl or heteroaryl with the proviso that R1 is not Ph, 4-Me-Ph, 4-OMe-Ph, 4-Br-Ph, 4-OH-Ph, 4-COOMe-Ph, 4-CN-Ph, 4-Ph-Ph, 2-Naphthyl, or 4-NO2-Ph.
10 more elements
A method for treating a neurological or neurodegenerative disorder in a subject comprising administering to the subject an effective amount of a compound of Formula I
- or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, or an isotopic variant thereof, or a pharmaceutically acceptable salt, solvate, or hydrate thereof;
- wherein:
- R2 is (a) hydrogen or (b) methyl;
- R3, R4, R5, R6, and R7 are each independently (a) hydrogen, cyano, or halo;
- (b) C1-6 alkyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
- or (c) —C(O)R1a, —C(O)OR1a, —C(O)NR1bR1c, —C(NR1a)NR1bR1c,
- —OR1a, —OS(O)NR1bR1c, —OS(O)2NR1bR1c, —NR1bR1c, —NR1aC(O)R1d, —NR1aC(O)OR1d, —NR1aC(O)NR1bR1c, —NR1aS(O)R1d, —NR1aS(O)2R1d;
- each R1a, R1b, R1c, and R1d is independently (i) hydrogen;
- (ii) C1-6 alkyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
- or (iii) R1b and R1c together with the N atom to which they are attached form heterocyclyl;
- and
- R1 is aryl or heteroaryl with the proviso that R1 is not Ph, 4-Me-Ph, 4-OMe-Ph, 4-Br-Ph, 4-OH-Ph, 4-COOMe-Ph, 4-CN-Ph, 4-Ph-Ph, 2-Naphthyl, or 4-NO2-Ph.
9 more elements
A method for treating, preventing, or ameliorating one or more symptoms of diabetes in a subject in need thereof comprising administering to the subject an effective amount of the compound Formula I
- or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, or an isotopic variant thereof;
- or a pharmaceutically acceptable salt, solvate, or hydrate thereof;
- wherein:
- R2 is (a) hydrogen or (b) methyl;
- R3, R4, R5, R6, and R7 are each independently (a) hydrogen, cyano, or halo;
- (b) C1-6 alkyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
- or (c) —C(O)R1a, —C(O)OR1a, —C(O)NR1bR1c, —C(NR1a)NR1bR1c,
- —OR1a, —OS(O)NR1bR1c, —OS(O)2NR1bR1c, —NR1bR1c, —NR1aC(O)R1d, —NR1aC(O)OR1d, —NR1aC(O)NR1bR1c, —NR1aS(O)R1d, —NR1aS(O)2R1d;
- each R1a, R1b, R1c, and R1d is independently (i) hydrogen;
- (ii) C1-6 alkyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
- or (iii) R1b and R1c together with the N atom to which they are attached form heterocyclyl;
- and
- R1 is aryl or heteroaryl with the proviso that R1 is not Ph, 4-Me-Ph, 4-OMe-Ph, 4-Br-Ph, 4-OH-Ph, 4-COOMe-Ph, 4-CN-Ph, 4-Ph-Ph, 2-Naphthyl, or 4-NO2-Ph
10 more elements
Dependencies are inferred from the claim text.