Compounds for inflammation and immune-related uses
The invention relates to certain compounds or pharmaceutically acceptable salts, solvates, clathrates, or prodrugs thereof, that are useful as immunosuppressive agents and for treating and preventing inflammatory conditions, allergic disorders, and immune disorders.
1. A compound selected from the group consisting of:
Number
Structure
Compound Name
1.
N-(5-(2-chloro-5-( 1 H-pyrazol-4- yl)phenyl)pyrazin-2-yl)-4- methylnicotinamide
2.
N-(5-(2-ethoxy-5-(1-methyl- 1 H- pyrazol-4-yl)phenyl)pyrazin-2-yl)- 4-methylnicotinamide
3.
N-(5-(2-chloro-5-(2-methylthiazol-4- yl)phenyl)pyrazin-2-yl)-4- methylnicotinamide
6.
5-fluoro-N-(5-(2-methoxy-5-(1-methyl- 1 H-pyrazol-4-yl)phenyl)pyrazin- 2-yl)-4-methylnicotinamide
8.
N-(5-(2-ethyl-5-(1-methyl- 1 H- pyrazol-4-yl)phenyl)pyrazin-2-yl)- 4-methylnicotinamide
14.
N-(5-(2-chloro-5-(5-methylthiazol-2- yl)phenyl)pyrazin-2-yl)-4- methylnicotinamide
16.
N-(5-(2-chloro-5-(pyrimidin-2- yloxy)phenyl)pyrazin-2-yl)-4- methylnicotinamide
19.
N-(5-(2-isopropoxy-5-(1-methyl- 1 H-pyrazol-4-yl)phenyl)pyrazin-2- yl)-4-methylnicotinamide
22.
5-fluoro-4-methyl-N-(5-(5-(1-methyl- 1 H-pyrazol-4-yl)-2- (trifluoromethoxy)phenyl)pyrazin- 2-yl)nicotinamide
24.
N-(5-(2-chloro-5-(3-fluoropyridin- 4-yl)phenyl)pyrazin-2-yl)-4- methylnicotinamide
26.
N-(5-(2-chloro-5-(2-methyl-2H- tetrazol-5-yl)phenyl)pyrazin-2-yl)- 5-fluoro-4-methylnicotinamide
27.
N-(5-(2-ethyl-5-(2-methyl-2H- tetrazol-5-yl)phenyl)pyrazin-2-yl)- 5-fluoro-4-methylnicotinamide
34.
N-(5-(2-chloro-5-((6- (trifluoromethyl)pyridin-2- yl)oxy)phenyl)pyrazin-2-yl)-4- methylnicotinamide
36.
N-(5-(5-((3-fluoropyridin-2- yl)oxy)-2-methylphenyl)pyrazin- 2-yl)-4-methylnicotinamide
38.
N-(5-(5-((3-fluoropyridin-2-yl)oxy)-2- (trifluoromethoxy)phenyl)pyrazin- 2-yl)-4-methylnicotinamide
39.
N-(5-(2-cyano-5-(oxetan-3- yloxy)phenyl)pyrazin-2-yl)-4- methylnicotinamide
44.
4-methyl-N-(5-(2-methyl-5-(pyridin- 3-ylethynyl)phenyl)pyrazin-2- yl)nicotinamide
45.
4-methyl-N-(5-(2-methyl-5-(2-methyl- 2H-tetrazol-5-yl)phenyl)pyrazin- 2-yl)nicotinamide
49.
N-(5-(2-chloro-5-(pyridin-2- yloxy)phenyl)pyrazin-2-yl)-4- methylnicotinamide
50.
4-methyl-N-(5-(6- methylbenzo[d][1,3]dioxol-5- yl)pyrazin-2-yl)nicotinamide
51.
4-methyl-N-(5-(5-(pyridin-2-yloxy)-2- (trifluoromethoxy)phenyl)pyrazin- 2-yl)nicotinamide
52.
4-methyl-N-(5-(2-methyl-5-(1-methyl- 1 H-pyrazol-4-yl)phenyl)pyrazin-2- yl)nicotinamide
53.
N-(5-(2-chloro-5-(1-methyl- 1 H- pyrazol-4-yl)phenyl)pyrazin-2-yl)- 4-methylnicotinamide
54.
N-(5-(2-chloro-5-(pyridin-2- yloxy)phenyl)pyrazin-2-yl)-5- fluoro-4-methylnicotinamide
56.
N-(5-(2-ethyl-5-(2-methyl-2H- tetrazol-5-yl)phenyl)pyrazin-2-yl)- 4-methylnicotinamide
57.
N-(5-(2-chloro-5-(2-methyl-2H- tetrazol-5-yl)phenyl)pyrazin-2-yl)- 4-methylnicotinamide
61.
N-(5-(2,5-dimethoxy- 1 H- benzo[d]imidazol-1-yl)pyrazin-2- yl)-4-methylnicotinamide
62.
N-(5-(2-chloro-5- cyclopropoxyphenyl)pyrazin-2- yl)-4-methylnicotinamide
65.
N-(5-(5-methoxy-2-(trifluoromethyl)- 1 H-benzo[d]imidazol-1-yl)pyrazin-2- yl)-4-methylnicotinamide
66.
N-(5-(5-cyclopropoxy-2- methylphenyl)pyrazin-2-yl)-4- methylnicotinamide
68.
4-methyl-3-(5-(4- methylnicotinamido)pyrazin-2- yl)phenyl dimethylsulfamate
69.
4-methyl-3-(5-(4- methylnicotinamido)pyrazin-2- yl)phenyl methanesulfonate
79.
N-(5-(5-cyclopropoxy-2- methylphenyl)pyrazin-2-yl)-5- fluoro-4-methylnicotinamide
80.
N-(5-(2-chloro-5-(1,5-dimethyl- 1 H-pyrazol-4-yl)phenyl)pyrazin-2- yl)-4-methylnicotinamide
81.
5-bromo-N-(5-(2-chloro-5- cyclopropoxyphenyl)pyrazin-2- yl)-4-methylnicotinamide
85.
N-(5-(2-chloro-5-((3-fluoropyridin-2- yl)oxy)phenyl)pyrazin-2-yl)-4- methylnicotinamide
86.
N-(5-(2-cyclopropoxy-5-(1-methyl- 1 H-pyrazol-4-yl)phenyl)pyrazin-2-yl)- 4-methylnicotinamide
87.
N-(5-(2-chloro-5- cyclopropoxyphenyl)pyrazin-2-yl)-4- methylnicotinamide hydrochloride
93.
4-chloro-3-(5-(4- methylnicotinamido)pyrazin-2- yl)phenyl methanesulfonate
101.
4-methyl-N-(5-(2-methyl-5-(1-methyl- 1 H-pyrazol-3-yl)phenyl)pyrazin-2- yl)nicotinamide
110.
N-(5-(2-methoxy-5-(1-methyl- 1 H- pyrazol-4-yl)phenyl)pyrazin-2-yl)- 4-methylnicotinamide
114.
5-chloro-N-(5-(2-chloro-5-(1-methyl- 1 H-pyrazol-4-yl)phenyl)pyrazin-2- yl)-4-methylnicotinamide
121.
5-bromo-N-(5-(2-chloro-5-(1-methyl- 1 H-pyrazol-4-yl)phenyl)pyrazin-2- yl)-4-methylnicotinamide
123.
N-(5-(2-chloro-5-(1-methyl- 1 H- pyrazol-4-yl)phenyl)pyrazin-2-yl)- 5-fluoro-4-methylnicotinamide
124.
4-methyl-N-(5-(2-methyl-5-(2- methylthiazol-4-yl)phenyl)pyrazin-2- yl)nicotinamide
129.
N-(5-(2-chloro-5-(1-methyl- 1 H- pyrazol-4-yl)phenyl)pyrazin-2-yl)- 4,5-dimethylnicotinamide
131.
N-(5-(2-chloro-5-(1-methyl- 1 H- pyrazol-4-yl)phenyl)pyrazin-2-yl)- 5-ethyl-4-methylnicotinamide
132.
N-(5-(2-chloro-5-(1-methyl- 1 H- pyrazol-4-yl)phenyl)pyrazin-2-yl)- 5-cyano-4-methylnicotinamide
137.
N-(5-(2-ethyl-5-((5-methylisoxazol-3- yl)oxy)phenyl)pyrazin-2-yl)-4- methylnicotinamide
142.
N-(5-(2-chloro-5-(1-methyl- 1 H- pyrazol-4-yl)phenyl)pyrazin-2-yl)- 4-methylnicotinamide hydrochloride
143.
5-fluoro-N-(5-(5-((3-fluoropyridin-2- yl)oxy)-2-methylphenyl)pyrazin-2-yl)- 4-methylnicotinamide
144.
N-(5-(2-chloro-5- isopropoxyphenyl)pyrazin-2-yl)-4- methylnicotinamide
196
N-(5-(2-chloro-5- cyclopropoxyphenyl)pyrazin-2-yl)-4- methylnicotinamide hydrochloride
198
N-(5-(2-chloro-5-(oxetan-3- yloxy)phenyl)pyrazin-2-yl)-5- fIuoro-4-methylnicotinamide
200
N-(5-(2-chloro-5- cyclobutoxyphenyl)pyrazin-2-yl)- 5-fluoro-4-methylnicotinamide
201
5-chloro-N-(5-(5-cyclopropoxy-2- methylphenyl)pyrazin-2-yl)-4- methylnicotinamide
202
N-(5-(2-chloro-5- (cyclohexyloxy)phenyl)pyrazin-2- yl)-5-fluoro-4-methylnicotinamide
203
N-(5-(2-cyano-5- cyclopropoxyphenyl)pyrazin-2- yl)-5-fluoro-4-methylnicotinamide
204
N-(5-(2-chloro-5- (cyclopropylmethoxy)phenyl)pyrazin- 2-yl)-4-methylnicotinamide
205
N-(5-(2-cyano-5- cyclopropoxyphenyl)pyrazin-2- yl)-4-methylnicotinamide
206
N-(5-(2-chloro-5- (cyclopentyloxy)phenyl)pyrazin-2- yl)-4-methylnicotinamide
207
N-(5-(2-chloro-5- cyclopropoxyphenyl)pyrazin-2- yl)-5-fluoro-4-methylnicotinamide
208
N-(5-(5-cyclopropoxy-2- ethylphenyl)pyrazin-2-yl)-5- fluoro-4-methylnicotinamide
209
N-(5-(5-cyclopropoxy-2- ethylphenyl)pyrazin-2-yl)-4- methylnicotinamide
212
N-(5-(2-chloro-5- isopropoxyphenyl)pyrazin-2-yl)-4- methylnicotinamide
224
5-fluoro-4-methyl-N-(5-(2-methyl-5-((5- methylthiazol-2-yl)oxy)phenyl)pyrazin- 2-yl)nicotinamide
227
4-methyl-N-(5-(2-methyl-5-((3-methyl- 1,2,4-thiadiazol-5-yl)oxy)phenyl)pyrazin- 2-yl)nicotinamide
228
5-fluoro-4-methyl-N-(5-(2-methyl-5- ((3-methyl-1,2,4-thiadiazol-5- yl)oxy)phenyl)pyrazin-2-yl)nicotinamide
230
N-(5-(2-chloro-5- (trifluoromethoxy)phenyl)pyrazin- 2-yl)-4-methylnicotinamide
231
N-(5-(2-ethyl-5- (trifluoromethoxy)phenyl)pyrazin- 2-yl)-4-methylnicotinamide
240
5-fluoro-4-methyl-N-(5-(2-methyl- 5-(pyrimidin-2-yloxy)phenyl)pyrazin- 2-yl)nicotinamide
And
242
N-(5-(2-chloro-5-(pyrimidin-2- yloxy)phenyl)pyrazin-2-yl)-5- fluoro-4-methylnicotinamide
or a pharmaceutically acceptable salt, or solvate thereof.
2. A pharmaceutical composition comprising the compound of claim 1 or a pharmaceutically acceptable salt or solvate thereof and a pharmaceutically acceptable excipient.
3. The compound of claim 1 of the formula:
or a pharmaceutically acceptable salt, or solvate thereof.
4. The compound of claim 1 of the formula:
or a pharmaceutically acceptable salt, or solvate thereof.
5. The compound of claim 1 of the formula:
or a pharmaceutically acceptable salt, or solvate thereof.
6. The compound of claim 1 of the formula:
or a pharmaceutically acceptable salt, or solvate thereof.
7. The compound of claim 1 of the formula:
or a pharmaceutically acceptable salt, or solvate thereof.
8. The compound of claim 1 of the formula:
or a pharmaceutically acceptable salt, or solvate thereof.
9. The compound of claim 1 of the formula:
or a pharmaceutically acceptable salt, or solvate thereof.