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US 2019/0337899 A1Published application
Quinoline sulfonamides useful to treat disease
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.
Claims13
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) C1-4 alkyl;
- R3, R4, R5, and R7 are each independently (a) hydrogen, cyano, nitro, or halo;
- (b) C1-6 alkyl, C3-6 cycloalkyl, or heteroaryl;
- or (c) —CF3, —O—(C1-C4 alkyl), and —N(C1-C4 alkyl)2;
- R6 is (a) hydrogen, cyano, nitro, or halo;
- (b) C1-6 alkyl, C3-6 cycloalkyl, or heteroaryl;
- or (c) —CF3 and —N(C1-C4 alkyl)2;
- and
- R1 is (a) phenyl, (b) 2-thienyl, (c) 2-benzothienyl, or (d) 2-furyl, wherein R1 is optionally substituted with one to two substituents independently selected from hydrogen, cyano, or halo;
- C1-6 alkyl, C3-6 cycloalkyl, heteroaryl, or heterocyclyl;
- —CF3, —O—(C1-C4 alkyl), and —N(C1-C4 alkyl)2;
- with the proviso that the following compounds are excluded:
- a) Benzenesulfonamide, N-(2-methyl-8-quinolinyl)-
- b) Benzenesulfonamide, 4-methyl-N-(2-methyl-8-quinolinyl)-
- c) Benzenesulfonamide, 4-fluoro-N-(2-methyl-8-quinolinyl)-
- d) Benzenesulfonamide, 4-chloro-N-(2-methyl-8-quinolinyl)-
- e) Benzenesulfonamide, 4-methoxy-N-(2-methyl-8-quinolinyl)-
- f) Benzenesulfonamide, N-(2,4-dimethyl-8-quinolinyl)-4-methyl-
- g) Benzenesulfonamide, 2-bromo-N-(2-methyl-8-quinolinyl)-
- h) Benzenesulfonamide, 2-chloro-N-(2-methyl-8-quinolinyl)-
- i) Benzenesulfonamide, 2-fluoro-N-(2-methyl-8-quinolinyl)-
- j) Benzenesulfonamide, N-(4-chloro-2-methyl-8-quinolinyl)-
- k) Benzenesulfonamide, 3-chloro-N-(2-methyl-8-quinolinyl)-
- l) Benzenesulfonamide, 3-bromo-N-(2-methyl-8-quinolinyl)-
- m) Benzenesulfonamide, 3-fluoro-N-(2-methyl-8-quinolinyl)-
- n) Benzenesulfonamide, N-(4-chloro-2-methyl-8-quinolinyl)-4-methyl-
- o) Benzenesulfonamide, N-(5-methoxy-2-methyl-8-quinolinyl)-4-methyl-
- p) Benzenesulfonamide, 3,5-dichloro-N-(2-methyl-8-quinolinyl)-
- q) Benzenesulfonamide, N-(4-methoxy-2-methyl-8-quinolinyl)-4-methyl-
- r) Benzenesulfonamide, 2,4-dichloro-N-(2-methyl-8-quinolinyl)-
- s) Benzenesulfonamide, N-(5,7-dichloro-2-methyl-8-quinolinyl)-4-methyl-
- t) Benzenesulfonamide, 2-methoxy-5-methyl-N-(2-methyl-8-quinolinyl)-
- u) Benzenesulfonamide, N-(5,7-dichloro-2-methyl-8-quinolinyl)-4-fluoro-
- v) Benzenesulfonamide, N-(5,7-dichloro-2-methyl-8-quinolinyl)-4-methoxy-
- w) 2-Thiophenesulfonamide, 5-methyl-N-(2-methyl-8-quinolinyl)-
- x) 2-Thiophenesulfonamide, 3-methyl-N-(2-methyl-8-quinolinyl)-
- y) 2-Thiophenesulfonamide, 5-chloro-N-(2-methyl-8-quinolinyl)-
- z) 2-Thiophenesulfonamide, 5-bromo-N-(2-methyl-8-quinolinyl)-
- aa) 2-Thiophenesulfonamide, 5-ethyl-N-(2-methyl-8-quinolinyl)-
- bb) 2-Thiophenesulfonamide, 4,5 -dichloro-N-(2-methyl-8-quinolinyl)-
- cc) 2-Thiophenesulfonamide, 4,5-dibromo-N-(2-methyl-8-quinolinyl)-
- dd)2-Thiophenesulfonamide, 4-bromo-5-chloro-N-(2-methyl-8-quinolinyl)-
- ee) 2-Furansulfonamide, N-(2-methyl-8-quinolinyl)-
43 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) C1-4 alkyl;
- R3, R4, R5, and R7 are each independently (a) hydrogen, cyano, nitro, or halo;
- (b) C1-6 alkyl, C3-6 cycloalkyl, or heteroaryl;
- or (c) —CF3, —O—(C1-C4 alkyl), and —N(C1-C4 alkyl)2;
- R6 is (a) hydrogen, cyano, nitro, or halo;
- (b) C1-6 alkyl, C3-6 cycloalkyl, or heteroaryl;
- or (c) —CF3 and —N(C1-C4 alkyl)2;
- and
- R1 is (a) phenyl, (b) 2-thienyl, (c) 2-benzothienyl, or (d) 2-furyl, wherein R1 is optionally substituted with one to two substituents independently selected from hydrogen, cyano, or halo;
- C1-6 alkyl, C3-6 cycloalkyl, heteroaryl, or heterocyclyl;
- —CF3, —O—(C1-C4 alkyl), and —N(C1-C4 alkyl)2.
11 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) C1-4 alkyl;
- R3, R4, R5, and R7 are each independently (a) hydrogen, cyano, nitro, or halo;
- (b) C1-6 alkyl, C3-6 cycloalkyl, or heteroaryl;
- or (c) —CF3, —O—(C1-C4 alkyl), and —N(C1-C4 alkyl)2;
- R6 is (a) hydrogen, cyano, nitro, or halo;
- (b) C1-6 alkyl, C3-6 cycloalkyl, or heteroaryl;
- or (c) —CF3 and —N(C1-C4 alkyl)2;
- and
- R1 is (a) phenyl, (b) 2-thienyl, (c) 2-benzothienyl, or (d) 2-furyl, wherein R1 is optionally substituted with one to two substituents independently selected from hydrogen, cyano, or halo;
- C1-6 alkyl, C3-6 cycloalkyl, heteroaryl, or heterocyclyl;
- —CF3, —O—(C1-C4 alkyl), and —N(C1-C4 alkyl)2.
11 more elements
Dependencies are inferred from the claim text.