Heterocyclic compounds, compositions comprising them and methods of their use
View Patent ↗Heterocyclic 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:
or a pharmaceutically acceptable salt thereof, wherein:
X is N or NR 9 ;
Y is CR 4 , N, NR 9 , O or S;
Z is CR 4 , CHR 4 , N, NR 9 , O or S;
R 1 is hydrogen or optionally substituted lower alkyl;
each R 4 is independently OR 4A , OC(O)R 4A , hydrogen, halogen, or optionally substituted alkyl, aryl, alkylaryl, arylalkyl, heteroalkyl, heterocycle, alkylheterocycle, or heterocyclealkyl;
R 5 is OR 5A or OC(O)R 5A ;
R 6 is OR 6A or OC(O)R 6A ;
R 7 is OR 7A or OC(O)R 7A ;
R 8 is hydrogen, CH 2 OR 8A or CH 2 OC(O)R 8A ;
each R 9 is independently hydrogen or optionally substituted alkyl, aryl, alkylaryl, arylalkyl, heteroalkyl, heterocycle, alkylheterocycle, or heterocyclealkyl; and
each of R 4A , R 5A , R 6A , R 7A and R 8A is independently hydrogen or lower alkyl.
2. The compound of claim 1 , wherein X is N.
3. The compound of claim 1 , wherein Y is O.
4. The compound of claim 1 , wherein R 4 is hydrogen.
5. The compound of claim 1 , wherein one or more of R 5 , R 6 , R 7 , and R 8 is hydroxyl or acetate.
6. The compound of claim 5 , wherein all of R 5 , R 6 , and R 7 are hydroxyl.
7. A compound of the formula:
or a pharmaceutically acceptable salt thereof, wherein:
X is CR 4 , CHR 4 , N, NR 9 , O or S;
Y is CR 4 , CHR 4 , N, NR 9 , O or S;
Z is CR 4 , CHR 4 , N, NR 9 , O or S;
R 1 is hydrogen or optionally substituted lower alkyl; and
R 3 is optionally substituted alkyl;
each R 4 is independently OR 4A , OC(O)R 4A , hydrogen, halogen, or optionally substituted alkyl, aryl, alkylaryl, arylalkyl, heteroalkyl, heterocycle, alkylheterocycle, or heterocyclealkyl;
R 5 is OR 5A or OC(O)R 5A ;
R 6 is OR 6A or OC(O)R 6A ;
R 7 is OR 7A or OC(O)R 7A ;
R 8 is hydrogen, CH 2 OR 8A or CH 2 OC(O)R 8A ;
each R 9 is independently hydrogen or optionally substituted alkyl, aryl, alkylaryl, arylalkyl, heteroalkyl, heterocycle, alkylheterocycle, or heterocyclealkyl; and
each of R 4A , R 5A , R 6A , R 7A and R 8A is independently hydrogen or lower alkyl.
8. The compound of claim 7 , wherein R 4 is hydrogen.
9. The compound of claim 7 , wherein one or more of R 5 , R 6 , R 7 , and R 8 is hydroxyl or acetate.
10. The compound of claim 9 , wherein all of R 5 , R 6 , and R 7 are hydroxyl.