Broad spectrum antiviral compounds and uses thereof
View Patent ↗Disclosed herein, inter alia, are agents having antiviral activity and methods of use thereof.
1. A compound, or a pharmaceutically acceptable salt thereof, having the formula:
wherein
Ring A is an unsubstituted 1,3,4-oxadiazolyl, an unsubstituted 1,2,4-oxadiazolyl, or a substituted or unsubstituted 1,2,3-triazolyl;
Ring B is a phenyl or 6 membered heteroaryl;
R 1 is independently halogen, —CX 1 3 , —CHX 1 2 , —CH 2 X 1 —CN, —OH, —NH 2 , —COOH, —CONH 2 , —NO 2 , —SH, —SO 3 H, —SO 4 H, —SO 2 NH 2 , —NHNH 2 , —ONH 2 , —NHC(O)NHNH 2 , —NHC(O)NH 2 , —NHSO 2 H, —NHC(O)H, —NHC(O)OH, —NHOH, —OCX 1 3 , —OCHX 1 2 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 2 is independently halogen, —CX 2 3 , —CHX 2 2 , —CH 2 X 2 , —CN, —OH, —NH 2 , —COOH, —CONH 2 , —NO 2 , —SH, —SO 3 H, —SO 4 H, —SO 2 NH 2 , —NHNH 2 , —ONH 2 , —NHC(O)NHNH 2 , —NHC(O)NH 2 , —NHSO 2 H, —NHC(O)H, —NHC(O)OH, —NHOH, —OCX 2 3 , —OCHX 2 2 , —OCH 2 X 2 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 3 is independently hydrogen, halogen, —CX 3 3 , —CHX 3 2 , —CH 2 X 3 , —CN, —OH, —NH 2 , —COOH, —CONH 2 , —SH, —SO 3 H, —SO 4 H, —SO 2 NH 2 , —NHNH 2 , —ONH 2 , —NHC(O)NHNH 2 , —NHC(O)NH 2 , —NHSO 2 H, —NHC(O)H, —NHC(O)OH, —NHOH, —OCX 3 3 , —OCHX 3 2 , —OCH 2 X 3 , —N 3 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
Z is —S— or —SO 2 —;
X 1 , X 2 , and X 3 are independently F, —Cl, —Br, or —I;
z1 is an integer from 0 to 5; and
z2 is an integer from 1 to 5.
2. The compound of claim 1 , wherein z2 is 1.
3. The compound of claim 1 , having the formula:
4. The compound of claim 1 , wherein Ring A is
5. The compound of claim 1 , wherein Ring B is a phenyl.
6. A compound, or a pharmaceutically acceptable salt thereof, having the formula:
wherein z1 is an integer from 0 to 4;
Ring A is a substituted or unsubstituted 5 membered heteroaryl;
Ring B is phenyl or a 6 membered heteroaryl;
R 1 is independently halogen, —CX 1 3 , —CHX 1 2 , —CH 2 X 1 —CN, —OH, —NH 2 , —COOH, —CONH 2 , —NO 2 , —SH, —SO 3 H, —SO 4 H, —SO 2 NH 2 , —NHNH 2 , —ONH 2 , —NHC(O)NHNH 2 , —NHC(O)NH 2 , —NHSO 2 H, —NHC(O)H, —NHC(O)OH, —NHOH, —OCX 1 3 , —OCHX 1 2 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 2 is independently halogen, —CX 2 3 , —CHX 2 2 , —CH 2 X 2 , —CN, —OH, —NH 2 , —COOH, —CONH 2 , —NO 2 , —SH, —SO 3 H, —SO 4 H, —SO 2 NH 2 , —NHNH 2 , —ONH 2 , —NHC(O)NHNH 2 , —NHC(O)NH 2 , —NHSO 2 H, —NHC(O)H, —NHC(O)OH, —NHOH, —OCX 2 3 , —OCHX 2 2 , —OCH 2 X 2 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 3 is independently hydrogen, halogen, —CX 3 3 , —CHX 3 2 , —CH 2 X 3 , —CN, —OH, —NH 2 , —COOH, —CONH 2 , —SH, —SO 3 H, —SO 4 H, —SO 2 NH 2 , —NHNH 2 , —ONH 2 , —NHC(O)NHNH 2 , —NHC(O)NH 2 , —NHSO 2 H, —NHC(O)H, —NHC(O)OH, —NHOH, —OCX 3 3 , —OCHX 3 2 , —OCH 2 X 3 , —N 3 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
Z is —S— or —SO 2 —;
X 1 , X 2 , and X 3 are independently —F, —Cl, —Br, or —I; and
z2 is an integer from 1 to 5.
7. The compound of claim 1 , wherein Z is SO 2 —.
8. The compound of claim 1 , wherein R 3 is hydrogen.
9. The compound of claim 1 , wherein R 1 is independently halogen, —CX 1 3 , —CHX 1 2 , —CH 2 X 1 , —OH, —OCH 3 , —SH, —OCX 1 3 , —OCHX 1 2 , —OCH 2 X 1 , substituted or unsubstituted C 1 -C 4 alkyl, or substituted or unsubstituted 2 to 4 membered heteroalkyl.
10. The compound of claim 9 , wherein R 1 is independently —F, —CH 3 , or —OCH 3 .
11. The compound of claim 1 , wherein z1 is 1 or 0.
12. The compound of claim 1 , wherein R 2 is independently halogen, —CX 2 3 , —CHX 2 2 , —CH 2 X 2 , —OH, —NH 2 , —COOH, —CONH 2 , —NO 2 , —SH, —OCX 2 3 , —OCHX 2 2 , —OCH 2 X 2 , substituted or unsubstituted C 1 -C 4 alkyl, or substituted or unsubstituted 2 to 4 membered heteroalkyl.
13. The compound of claim 12 , wherein R 2 is —CF 3 , —NH 2 , —COOH, —COOCH 3 , —NO 2 , —OCH 3 , —OCHX 2 2 , —OCH 2 X 2 , or —COO − (HOCH 2 CH 2 N(CH 3 ) 3 + ).
14. The compound of claim 1 , wherein Ring A is a substituted or unsubstituted 1,2,3-triazolyl.
15. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, having the formula:
wherein z1 is an integer from 0 to 4.
16. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable excipient.