4-Piperidin-1-yl-7
View Patent ↗Substituted 4-piperidin-1-yl-7H-pyrrolo[2,3-D]pyrimidine compounds are disclosed, as well as compositions comprising them and methods of their use for the treatment, prevention and management of various diseases and disorders.
1. A compound of the formula:
or a pharmaceutically acceptable salt thereof, wherein:
A 1 and A 2 are each independently optionally substituted aryl or heteroaryl;
X is —CH 2 — or —C(O)—;
Y is —O—, —NR 5 —, —S(O) n NR 5 —, —C(O)NR 5 —, —NR 5 C(O)—, —C(O)—, or —S(O) n —;
n is 1 or 2;
R 1 and R 2 are each independently hydrogen, halo, cyano, hydroxy, —NR 3 R 4 , [thio,] or optionally substituted alkyl, alkoxy, aryl, arylalkyl, heterocycle or heterocycloalkylalkyl; and
R 3 , R 4 , and R 5 are each independently hydrogen or optionally substituted alkyl, aryl, arylalkyl, heterocycle or heterocycloalkylalkyl.
2. The compound of claim 1 , wherein R 2 is hydrogen, cyano, methyl or halo.
3. The compound of claim 1 , wherein R 3 is hydrogen or alkyl.
4. The compound of claim 1 , wherein R 4 is hydrogen or alkyl.
5. The compound of claim 1 , wherein R 5 is hydrogen or lower alkyl.
6. A compound of the formula:
or a pharmaceutically acceptable salt thereof, wherein:
A 1 is optionally substituted aryl or heteroaryl;
X is —CH 2 — or —C(O)—;
Y is —O—, —NR 5 —, —S(O) n NR 5 —, —C(O)NR 5 —, —NR 5 C(O)—, —C(O)—, or —S(O) n —;
n is 1 or 2;
R 1 and R 2 are each independently hydrogen, halo, cyano, hydroxy, —NR 3 R 4 , [thio,] or optionally substituted alkyl, alkoxy, aryl, arylalkyl, heterocycle or heterocycloalkylalkyl;
R 3 , R 4 , and R 5 are each independently hydrogen or optionally substituted alkyl, aryl, arylalkyl, heterocycle or heterocycloalkylalkyl; and
R 6 is hydrogen, halo, cyano, hydroxy, alkoxy, amino or optionally substituted alkyl.
7. The compound of claim 6 , wherein A 1 is thiazolyl or optionally substituted phenyl.
8. The compound of claim 6 , wherein Y is —O—, —C(O)—, —NHC(O)— or —C(O)NH—.
9. The compound of claim 6 , wherein Y is —S(O) n NR 5 — or —S(O) n —, and n is 2.
10. The compound of claim 6 , wherein R 1 is hydrogen.
11. The compound of claim 6 , wherein R 2 is hydrogen, cyano, methyl or halo.
12. A compound of the formula:
or a pharmaceutically acceptable salt thereof, wherein:
A 2 is optionally substituted aryl or heteroaryl;
X is —CH 2 — or —C(O)—;
Y is —O—, —NR 5 —, —S(O) n NR 5 —, —C(O)NR 5 —, —NR 5 C(O)—, —C(O)—, or —S(O) n —;
n is 1 or 2;
R 1 and R 2 are each independently hydrogen, halo, cyano, hydroxy, —NR 3 R 4 , [thio,] or optionally substituted alkyl, alkoxy, aryl, arylalkyl, heterocycle or heterocycloalkylalkyl; and
R 3 , R 4 , and R 5 are each independently hydrogen or optionally substituted alkyl, aryl, arylalkyl, heterocycle or heterocycloalkylalkyl.
13. The compound of claim 12 , wherein A 2 is optionally substituted phenyl, indanyl, indenyl, indolinyl, or pyridyl.
14. The compound of claim 12 , wherein Y is —O—, —C(O)—, —NHC(O)— or —C(O)NH—.
15. The compound of claim 12 , wherein Y is —S(O) n NR 5 — or —S(O) n —, and n is 2.
16. The compound of claim 12 , wherein R 1 is hydrogen.
17. The compound of claim 12 , wherein R 2 is hydrogen, cyano, methyl or halo.
18. A composition comprising a compound of claim 1 and a solvent.