Pyrrole-type compounds, compositions, and methods for treating cancer, treating viral diseases and causing immunosuppression
View Patent ↗The present invention relates to novel Pyrrole-Type compounds, compositions comprising Pyrrole-Type compounds, and methods useful for treating or preventing cancer or a neoplastic disorder comprising administering a Pyrrole-Type compound. The compounds, compositions, and methods of the invention are also useful for inhibiting the growth of a cancer cell or neoplastic cell. The present invention also relates to novel Pyrrole-Type compounds, compositions, and methods useful for treating or preventing a viral infection. The compounds, compositions, and methods of the invention are also useful for inhibiting the replication and/or infectivity of a virus. The present invention also relates to novel Pyrrole-Type compounds, compositions, and methods useful for causing immunosuppression. The present invention also relates to novel Pyrrole-Type compounds, compositions, and methods useful for treating or preventing an autoimmune disease.
1. A compound of general Formula (VIII):
or a pharmaceutically acceptable salt thereof, wherein:
R 2 is a C 1 –C 10 straight chain alkyl or —CH 2 C 6 H 5 ;
R 4 is —H or a C 1 –C 10 straight chain alkyl;
R 5 is —H or a C 1 –C 10 straight chain alkyl; and m is 1 to 4.
2. The compound of claim 1 , wherein:
R 2 is —CH 3 or —CH 2 C 6 H 5 ;
R 4 and R 5 is —H or —CH 3 ; and
m is 2.
3. The compound of claim 2 , wherein:
R 2 and R 5 is —CH 3 ;
R 4 is —H or —CH 3 ; and
m is 2.
4. A compound of general Formula (IX):
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is —H, —CH 3 , —SO 2 -4-methylphenyl, —CH 2 C 6 H 5 , —Si(R 5 R 6 R 7 ), —CH 2 OCH 2 CH 2 SiCH 3 , C(O)OC(CH 3 ) 3 , or —C(O)CH 2 C 6 H 5 ;
R 2 is —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , or —CH 2 C 6 H 5 ;
R 3 is —H or Cl;
R 4 is —H or a C 1 –C 10 straight chain alkyl;
R 5 is a C 1 –C 4 straight or branched chain alkyl or —C 6 H 5 ;
R 6 is a C 1 –C 3 straight or branched chain alkyl;
R 7 is a C 1 –C 3 straight or branched chain alkyl; and
n is 1 to 5.
5. The compound of claim 4 , wherein:
R 1 is —H;
R 2 is —CH 3 or —CH 2 C 6 H 5 ;
R 3 is —H;
R 4 is —H or a C 1 –C 4 straight or branched chain alkyl; and
n is 1 to 3.
6. The compound of claim 5 , wherein:
R 1 is —H;
R 2 is —CH 3 ;
R 3 is —H;
R 4 is —C 4 H 9 ; and
n is 1.
7. The compound of claim 5 , wherein:
R 1 is —H;
R 2 is —CH 3 ;
R 3 is —H;
R 4 is —C 2 H 5 ; and
n is 3.
8. A compound of general Formula (X):
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is —H, —CH 3 , —CH 2 C 6 H 5 , —COCH 3 , —C(O)OC(CH 3 ) 3 , or —C(O)CH 2 C 6 H 5 ;
R 2 is a C 1 –C 10 straight chain alkyl or —CH 2 C 6 H 5 , the —CH 2 C 6 H 5 being unsubstituted or substituted with one or more halo, methoxyl, methyl, methoxycarbonyl, or nitro groups;
R 3 is —H, —CH 3 , —CH 2 C 6 H 5 , or —C(O)OC(CH 3 ) 3 ;
R 4 is —H or —CH 3 ;
R 5 is —H, —CH 3 , —OCH 3 , —F, —Cl, —Br, —I, —CN, —NH 2 ; —NH(C 1 –C 3 straight or branched chain alkyl), —NHCOCH 3 , —NO 2 , —COOH, —COOR 6 , —OH, or —OCH 2 C 6 H 5 ; and
R 6 is a C 1 –C 6 straight chain alkyl.
9. The compound of claim 8 , wherein:
R 1 is —H;
R 2 is —CH 3 or —CH 2 C 6 H 5 ;
R 3 is —H;
R 4 is —H or —CH 3 ;
R 5 is —H, halogen, or —COOR 6 ; and
R 6 is —CH 3 .
10. The compound of claim 9 , wherein:
R 1 is —H;
R 2 is —CH 3 ;
R 3 is —H;
R 4 is —H or —CH 3 ; and
R 5 is —H.
11. A compound of general Formula (XI):
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is —H, —CH 3 , —CH 2 C 6 H 5 , —COCH 3 , —C(O)OC(CH 3 ) 3 , or —C(O)CH 2 C 6 H 5 ;
R 2 is a C 1 –C 10 straight chain alkyl or —CH 2 C 6 H 5 ;
R 3 is —H, —CH 3 , —CH 2 C 6 H 5 , —C(O)OC(CH 3 ) 3 , or —C(O)CH 2 C 6 H 5 ;
R 4 is —H or —CH 3 ;
R 5 is —H, a C 1 –C 10 straight chain alkyl, —OR 6 , —F, —Cl, —Br, —I, —CN, —COOH, —COOR 6 , —NH 2 ; —NHCOR 6 , —NO 2 , —OH, or —OCH 2 C 6 H 5 ; and
R 6 is a C 1 –C 6 straight chain alkyl.
12. The compound of claim 11 , wherein:
R 1 is —H;
R 2 is —CH 3 or —CH 2 C 6 H 5 ;
R 3 is —H;
R 4 is —H or —CH 3 ;
R 5 is —H, —CH 3 , halogen, or COOR 6 ; and
R 6 is —CH 3 .
13. The compound of claim 12 , wherein:
R 1 is —H;
R 2 is —CH 3 ;
R 3 is —H;
R 4 is —CH 3 ; and
R 5 is —H or Cl.
14. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.
15. A pharmaceutical composition comprising the compound of claim 2 and a pharmaceutically acceptable carrier.
16. A pharmaceutical composition comprising the compound of claim 3 and a pharmaceutically acceptable carrier.
17. A pharmaceutical composition comprising the compound of claim 4 and a pharmaceutically acceptable carrier.
18. A pharmaceutical composition comprising the compound of claim 5 and a pharmaceutically acceptable carrier.
19. A pharmaceutical composition comprising the compound of claim 6 and a pharmaceutically acceptable carrier.
20. A pharmaceutical composition comprising the compound of claim 7 and a pharmaceutically acceptable carrier.
21. A pharmaceutical composition comprising the compound of claim 8 and a pharmaceutically acceptable carrier.
22. A pharmaceutical composition comprising the compound of claim 9 and a pharmaceutically acceptable carrier.
23. A pharmaceutical composition comprising the compound of claim 10 and a pharmaceutically acceptable carrier.
24. A pharmaceutical composition comprising the compound of claim 11 and a pharmaceutically acceptable carrier.
25. A pharmaceutical composition comprising the compound of claim 12 and a pharmaceutically acceptable carrier.
26. A pharmaceutical composition comprising the compound of claim 13 and a pharmaceutically acceptable carrier.
27. The compound of claim 11 , having the formula:
or a pharmaceutically acceptable salt thereof.
28. A pharmaceutical composition comprising the compound of claim 27 and a pharmaceutically acceptable carrier.