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US 9,364,481 B2Granted
Substituted bicyclic aromatic compounds as S-nitrosoglutathione reductase inhibitors
AssigneeNivalis Therapeutics, Inc.
InventorsXicheng Sun, Jian Qiu, Adam Stout
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Abstract
The present invention is directed to novel substituted bicyclic aromatic compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.
Claims22
A method of inhibiting the activity of the enzyme S-nitrosoglutathione reductase (GSNOR) comprising the step of contacting said enzyme with a compound of Formula I:
- wherein
- Z1 is selected from the group consisting of CR2a and N;
- Z2 is selected from the group consisting of CR2b and N;
- Z3 is selected from the group consisting of CR2c and N;
- with the proviso that at least 1 of Z1, Z2, or Z3 must be N;
- m is selected from the group consisting of 0, 1, 2, or 3;
- R1 is independently selected from the group consisting of chloro, fluoro, and bromo;
- R2a, R2b, and R2c, are independently selected from the group consisting of hydrogen, halogen,
- C1-C3 alkyl, fluorinated C1-C3 alkyl, cyano, C1-C3 alkoxy, and N(CH3)2;
- X is selected from the group consisting of
- n is selected from 0, 1, and 2;
- R3 is independently selected from the group consisting of halogen, C1-C3 alkyl, fluorinated C1-C3 alkyl, cyano, C1-C3 alkoxy, and NR4R4′ where R4 and R4′ are independently selected from the group consisting of C1-C3 alkyl, or R4 when taken together with R4′ form a ring with 3 to 6 members;
- A is selected from the group consisting of
- or a pharmaceutically acceptable salt, stereoisomer, or N-oxide thereof.
11 more elements
The method of claim I wherein the compound is a compound of Formula X:
- wherein
- m is selected from the group consisting of 0, 1, 2, or 3;
- R1 is independently selected from the group consisting of chloro, fluoro, and bromo;
- R2a is selected from the group consisting of hydrogen, halogen, C1-C3 alkyl, fluorinated C1-C3 alkyl, cyano, C1-C3 alkoxy, and N(CH3)2;
- X is selected from the group consisting of
- n is selected from 0, 1, and 2;
- R3 is independently selected from the group consisting of halogen, C1-C3 alkyl, fluorinated C1-C3 alkyl, cyano, C1-C3 alkoxy, and NR4R4′ where R4 and R4′ are independently selected from the group consisting of C1-C3 alkyl, or R4 when taken together with R4′ form a ring with 3 to 6 members;
- A is selected from the group consisting of
- or a pharmaceutically acceptable salt, stereoisomer, or N-oxide thereof.
6 more elements
Dependencies are inferred from the claim text.