5,6-di-substituted oxadiazolopyrazines and thiadiazolopyrazines as CXC-chemokine receptor ligands
View Patent ↗Disclosed are compounds of the formula and the pharmaceutically acceptable salts thereof. The compounds are useful for the treatment of chemokine-mediated diseases such as COPD.
1. A compound of the formula:
and the pharmaceutically acceptable salts thereof, wherein:
X is O;
A is:
A is A8 wherein said A group is substituted with 1 to 6 independently selected alkyl groups;
B is:
R 2 is OH;
R 3 is —C(O)NR 13 R 14 wherein R 13 and R 14 are the same or different alkyl group;
R 4 , R 5 , and R 6 are H; and
R 7 is H; and
R 8 is alkyl.
2. The compound of claim 1 wherein R 13 and R 14 are methyl.
3. The compound of claim 1 wherein A is A8 wherein the furan ring is substituted.
4. The compound of claim 1 wherein A is selected from the group consisting of:
5. The compound of claim 1 wherein said compound is a calcium salt.
6. The compound of claim 1 wherein said compound is a sodium salt.
7. The compound of claim 1 selected from the group consisting of
8. The compound of claim 1 selected from the group consisting of
9. The compound of claim 1 selected from the group consisting of
10. The compound of claim 7 wherein said compound is a calcium or sodium salt.
11. A pharmaceutical composition comprising an effective amount of at least one compound of claim 1 , or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.
12. A pharmaceutical composition comprising an effective amount of at least one compound of claim 7 , or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.