Imidazole-based compounds, compositions comprising them and methods of their use
View Patent ↗Imidazole-based compounds, compositions comprising them, and methods of their use for the treatment, prevention and management of inflammatory and autoimmune diseases and disorders are disclosed. Particular compounds are of formula I:
1. A compound of the formula:
wherein:
R 1 is hydrogen, alkyl or aryl;
R 3 is OR 3A , NHC(O)R 3A , NHSO 2 R 3A or hydrogen;
each R 3A is independently hydrogen or alkyl, aryl, alkylaryl, arylalkyl, heteroalkyl, heterocycle, alkylheterocycle, or heterocyclealkyl optionally substituted with halo;
R 6 is OR 6A or OC(O)R 6A ;
R 7 is OR 7A or OC(O)R 7A ;
R 8 is OR 8A or OC(O)R 8A ;
R 9 is hydrogen, CH 2 OR 9A or CH 2 OC(O)R 9A ; and
each of R 6A , R 7A , R 8A , and R 9A is independently hydrogen or lower alkyl.
2. The compound of claim 1 , which is of the formula:
3. The compound of claim 1 , which is of the formula:
4. The compound of claim 3 , which is of the formula:
5. The compound of claim 4 , wherein R 1 is lower alkyl.
6. The compound of claim 4 , wherein R 3 is OR 3A .
7. The compound of claim 4 , wherein R 3 is N(R 3A ) 2 or NHC(O)R 3A .
8. The compound of claim 4 , wherein R 3 is NHSO 2 R 3A .
9. The compound of claim 6 , wherein R 3A is hydrogen or lower alkyl.
10. A compound of the formula:
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is lower alkyl;
R 3 is hydrogen, OR 3A , NHC(O)R 3A or NHSO 2 R 3A ;
R 9 is hydrogen or CH 2 OH; and
each R 3A is independently hydrogen or lower alkyl.
11. The compound of claim 10 , which is of the formula:
12. The compound of claim 11 , wherein R 3 is OR 3A .
13. The compound of claim 12 , wherein R 3A is hydrogen.
14. A compound, or a pharmaceutically acceptable salt thereof, wherein the compound is:
(E)-1-(4-((1R,2S ,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime.
15. A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable excipient or diluent.