Pyrrole-Type compounds, compositions and methods for treating cancer or viral disease
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 composition comprising 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.
1. A method for treating cervical cancer, prostate cancer, ovarian cancer, lung cancer, breast cancer, colorectal cancer, or melanoma, comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of Formula (V):
or a pharmaceutically acceptable salt thereof, wherein, in the compound of Formula (V):
each R 1 is selected from the group consisting of —H, —CH 3 , —CH 2 CH 3 , —CH 2 C 6 H 5 , —C(O)OC(CH 3 ) 3 , —C(O)OCH 2 C 6 H 5 , and —C(O)CH 3 ;
R 2 is selected from the group consisting of —H, C 1 -C 12 straight chain alkyl, —CH 2 C 6 H 5 , —SiR 10 R 11 R 12 , —C(O)CH 3 , —C(O)C 6 H 5 , -2-tetrahydropyranyl, —OCH 2 OCH 3 , and —C(O)OCH 2 CCl 3 ;
R 7 is selected from the group consisting of —H, C 1 -C 15 straight chain alkyl, —(CH 2 ) 9 CH═CH 2 , —(CH 2 ) 6 F, —(CH 2 ) 5 OC 6 H 5 , —(CH 2 ) 6 OH, —(CH 2 ) 7 CN, —CH 2 CH 2 C 6 H 5 , —(CH 2 ) 4 COOH, —(CH 2 ) 5 COOH, —(CH 2 ) 5 COOMe, —(CH 2 ) 11 COOH, —(CH 2 ) 12 COOH, —(CH 2 ) 12 OH, —(CH 2 ) 13 OH, —(CH 2 ) 11 CN, —(CH 2 ) 11 OC(O)NH 2 , —(CH 2 ) 11 COOEt, —C(O)(CH 2 ) 9 CH 3 , —(CH 2 ) 5 C(O)N(CH 2 CH 2 ) 2 O, C 3 -C 7 cycloalkyl, —C 6 H 5 , 2-pyrrolyl, -3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furanyl, and 3-furanyl, the phenyl being substituted with one or more halo, methyl, methoxyl, hydroxyl, methoxycarbonyl or trifluoromethyl groups;
R 8 is selected from the group consisting of —H, C 1 -C 11 straight chain alkyl, —(CH 2 ) 4 COOEt, and —C 6 H 5 ;
when R 7 is other than 2-pyrrolyl, then R 9 is selected from the group consisting of —H, —CH 3 , —CH 2 CH 3 , and —CH 2 CH 2 CH 3 ;
when R 7 is 2-pyrrolyl, then R 9 is selected from the group consisting of —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , and —OCH 3 ;
R 10 is selected from the group consisting of C 1 -C 4 straight or branched chain alkyl and —C 6 H 5 ;
R 11 and R 12 are independently selected from the group consisting of —CH 3 , —CH 2 CH 3 , and —C 3 H 7 ;
R 16 is selected from the group consisting of —H, —CH 3 , —CH 2 CH 2 CH 3 , and —(CH 2 ) 6 CH 3 ; and
R 17 is selected from the group consisting of —H, —CN, —COOMe, —COOEt, and —COOH.
2. The method of claim 1 , wherein the compound of Formula (V) has the Formula:
or a pharmaceutically acceptable salt thereof.
3. The method of claim 1 , wherein the compound of Formula (V) has the Formula:
or a pharmaceutically acceptable salt thereof.
4. A method for inhibiting the growth of a cervical cancer cell, a prostate cancer cell, an ovarian cancer cell, a lung cancer cell, a breast cancer cell, a colorectal cancer cell, or a melanoma cell, comprising contacting the cell with an effective amount of a compound of Formula (V):
or a pharmaceutically acceptable salt thereof, wherein, in the compound of Formula (V):
each R 1 is selected from the group consisting of—H, —CH 3 , —CH 2 CH 3 , —CH 2 C 6 H 5 , —C(O)OC(CH 3 ) 3 , —C(O)OCH 2 C 6 H 5 , and —C(O)CH 3 ;
R 2 is selected from the group consisting of —H, C 1 -C 12 straight chain alkyl, —CH 2 C 6 H 5 , —SiR 10 R 11 R 12 , —C(O)CH 3 , —C(O)C 6 H 5 , -2-tetrahydropyranyl, —OCH 2 OCH 3 , and —C(O)OCH 2 CCl 3 ;
R 7 is selected from the group consisting of —H, C 1 -C 15 straight chain alkyl, —(CH 2 ) 9 CH═CH 2 , —(CH 2 ) 6 F, —(CH 2 ) 5 OC 6 H 5 , —(CH 2 ) 6 OH, —(CH 2 ) 7 CN, —CH 2 CH 2 C 6 H 5 , —(CH 2 ) 4 COOH, —(CH 2 ) 5 COOH, —(CH 2 ) 5 COOMe, —(CH 2 ) 11 COOH, —(CH 2 ) 12 COOH, —(CH 2 ) 12 OH, —(CH 2 ) 13 OH, —(CH 2 ) 11 CN, —(CH 2 ) 11 OC(O)NH 2 , —(CH 2 ) 11 COOEt, —C(O)(CH 2 ) 9 CH 3 , —(CH 2 ) 5 C(O)N(CH 2 CH 2 ) 2 O, C 3 -C 7 cycloalkyl, —C 6 H 5 , 2-pyrrolyl, -3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furanyl, and 3-furanyl, the phenyl being substituted with one or more halo, methyl, methoxyl, hydroxyl, methoxycarbonyl or trifluoromethyl groups;
R 8 is selected from the group consisting of —H, C 1 -C 11 straight chain alkyl, —(CH 2 ) 4 COOEt, and —C 6 H 5 ;
when R 7 is other than 2-pyrrolyl, then R 9 is selected from the group consisting of —H, —CH 3 , —CH 2 CH 3 , and —CH 2 CH 2 CH 3 ;
when R 7 is 2-pyrrolyl, then R 9 is selected from the group consisting of —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , and —OCH 3 ;
R 10 is selected from the group consisting of C 1 -C 4 straight or branched chain alkyl and —C 6 H 5 ;
R 11 and R 12 are independently selected from the group consisting of—CH 3 , —CH 2 CH 3 , and —C 3 H 7 ;
R 16 is selected from the group consisting of —H, —CH 3 , —CH 2 CH 2 CH 3 , and —(CH 2 ) 6 CH 3 ; and
R 17 is selected from the group consisting of —H, —CN, —COOMe, —COOEt, and —COOH.
5. The method of claim 4 , wherein the compound of Formula (V) has the Formula:
or a pharmaceutically acceptable salt thereof.
6. The method of claim 4 , wherein the compound of Formula (V) has the Formula:
or a pharmaceutically acceptable salt thereof.