US 6,602,879 B2 · Pyrrole-type compounds, compositions, and methods for treating cancer or viral diseases

Abstract

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.

Claims88

Dependent claims

A method for treating prostate cancer comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of Formula (I):

or a pharmaceutically acceptable salt thereof, wherein, in the compound of Formula (I):
each R1 is independently selected from the group consisting of —H, —CH3, —CH2CH3, —CH2C6H5, C(O)OC(CH3)3, —C(O)OCH2C6H5, and —C(O)CH3;
R2 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH2C6H5, —SiR10R11R12, —C(O)CH3, —C(O)C6H5, -2-tetrahydropyranyl, —OCH2OCH3, and —C(O)OCH2CCl3;
R3 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH(R14)(R15) wherein R14 and R15 are independently C1-C12 straight chain alkyl, —C(O)C1-C9 straight chain alkyl, —CH(OH)C1-C9 straight chain alkyl, —CH(Cl)C1-C9 straight chain alkyl, -(2-pyridyl)methyl, -(3-pyridyl)methyl, -(4-pyridyl)methyl, and —CH2C6H5, the —CH2C6H5 being unsubstituted or substituted on phenyl with one cyano or one or more halo, methoxyl, or trifluoromethyl groups;
R10 is selected from the group consisting of C1-C4 straight or branched chain alkyl and
R11 and R12 are independently C1-C3 straight or branched chain alkyl;
m is an integer ranging from 1 to 5;
and
when m is 3 and R2 is —CH2CH3, then R16 is —H or —CH3 and R17 is —H;
when m is 3 and R2 is —CH3, then R16 is —H or —CH3 and R17 is —H or —COOEt;
and
when m is other than 3 and R2 is other than —CH3 or —CH2CH3, then R16 and R17 are —H only;
with the proviso that the compound of Formula (I) is not metacycloprodigiosin.

10 more elements

A method for treating cervical cancer comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of Formula (I):

or a pharmaceutically acceptable salt thereof, wherein, in the compound of Formula (I):
each R1 is independently selected from the group consisting of —H, —CH3, —CH2CH3, —CH2C6H5, —C(O)OC(CH3)3, —C(O)OCH2C6H5, and —C(O)CH3;
R2 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH2C6H5, —SiR10R11R12, —C(O)CH3, —C(O)C6H5, -2-tetrahydropyranyl, —OCH2OCH3, and —C(O)OCH2CCl3;
R3 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH(R14)(R15) wherein R14 and R15 are independently C1-C12 straight chain alkyl, —C(O)C1-C9 straight chain alkyl, —CH(OH)C1-C9 straight chain alkyl, —CH(Cl)C1-C9 straight chain alkyl, -(2-pyridyl)methyl, -(3-pyridyl)methyl, -(4-pyridyl)methyl, and —CH2C6H5, the —CH2C6H5 being unsubstituted or substituted on phenyl with one cyano or one or more halo, methoxyl, or trifluoromethyl groups;
R10 is selected from the group consisting of C1-C4 straight or branched chain alkyl and —C6H5;
R11 and R12 are independently C1-C3 straight or branched chain alkyl;
m is an integer ranging from 1 to 5;
and
when m is 3 and R2 is —CH2CH3, then R16 is —H or —CH3 and R17 is —H;
when m is 3 and R2 is —CH3, then R16 is —H or —CH3 and R17 is —H or —COOEt;
and
when m is other than 3 and R2 is other than —CH3 or —CH2CH3, then R16 and R17 are —H only;
with the proviso that the compound of Formula (I) is not metacycloprodigiosin.

10 more elements

A method for inhibiting the growth of a prostate cancer cell comprising contacting a said cancer cell with an effective amount of a compound of Formula (I):

or a pharmaceutically acceptable salt thereof, wherein, in the compound of Formula (I):
each R1 is independently selected from the group consisting of —H, —CH3, —CH2CH3, —CH2C6H5, —C(O)OC(CH3)3, —C(O)OCH2C6H5, and —C(O)CH3;
R2 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH2C6H5, —SiR10R11R12, —C(O)CH3, —C(O)C6H5, -2-tetrahydropyranyl, —OCH2OCH3, and —C(O)OCH2CCl3;
R3 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH(R14)(R15) wherein R14 and R15 are independently C1-C12 straight chain alkyl, —C(O)C1-C9 straight chain alkyl, —CH(OH)C1-C9 straight chain alkyl, —CH(Cl)C1-C9 straight chain alkyl, -(2-pyridyl)methyl, -(3-pyridyl)methyl, -(4-pyridyl)methyl, and —CH2C6H5, the —CH2C6H5 being unsubstituted or substituted on phenyl with one cyano or one or more halo, methoxyl, or trifluoromethyl groups;
R10 is selected from the group consisting of C1-C4 straight or branched chain alkyl and —C6H5;
R11 and R12 are independently C1-C3 straight or branched chain alkyl;
m is an integer ranging from 1 to 5;
when m is 3 and R2 is —CH2CH3 then R16 is —H or —CH3 and R17 is —H;
when m is 3 and R2 is —CH3, then R16 is —H or —CH3 and R17 is —H or —COOEt;
and
when m is other than 3 and R2 is other than —CH3 or —CH2CH3, then R16 and R17 are —H only;
with the proviso that the compound of Formula (I) is not metacycloprodigiosin.

9 more elements

A method for inhibiting the growth of a cervical cancer cell comprising contacting a said cancer cell with an effective amount of a compound of Formula (I):

or a pharmaceutically acceptable salt thereof wherein, in the compound of Formula (I):
each R1 is independently selected from the group consisting of —H, —CH3, —CH2CH3, —CH2C6H5, —C(O)OC(CH3)3, —C(O)OCH2C6H5, and —C(O)CH3;
R2 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH2C6H5, —SiR10R11R12, —C(O)CH3, —C(O)C6H5, -2-tetrahydropyranyl, —OCH2OCH3, and —C(O)OCH2CCl3;
R3 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH(R14)(R15) wherein R14 and R15 are independently C1-C12 straight chain alkyl, —C(O)C1-C9 straight chain alkyl, —CH(OH)C1-C9 straight chain alkyl, —CH(Cl)C1-C9 straight chain alkyl, -(2-pyridyl)methyl, -(3-pyridyl)methyl, -(4-pyridyl)methyl, and —CH2C6H5, the —CH2C6H5 being unsubstituted or substituted on phenyl with one cyano or one or more halo, methoxyl, or trifluoromethyl groups;
R10 is selected from the group consisting of C1-C4 straight or branched chain alkyl and —C6H5;
R11 and R12 are independently C1-C3 straight or branched chain alkyl;
m is an integer ranging from 1 to 5;
when m is 3 and R2 is —CH2CH3, then R16 is —H or —CH3 and R17 is —H;
when m is 3 and R2 is —CH3, then R16 is —H or —CH3 and R17 is —H or —COOEt;
and
when m is other than 3 and R2 is other than —CH3 or —CH2CH3, then R16 and R17 are —H only;
with the proviso that the compound of Formula (I) is not metacycloprodigiosin.

9 more elements

A method for treating lung carcinoma comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of Formula (I):

or a pharmaceutically acceptable salt thereof wherein, in the compound of Formula (I):
each R1 is independently selected from the group consisting of —H, —CH3, —CH2CH3, —CH2C6H5, —C(O)OC(CH3)3, —C(O)OCH2C6H5, and —C(O)CH3;
R2 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH2C6H5, —SiR10R11R12, —C(O)CH3, —C(O)C6H5, -2-tetrahydropyranyl, —OCH2OCH3, and —C(O)OCH2CCl3;
R3 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH(R14)(R15) wherein R14 and R15 are independently C1-C12 straight chain alkyl, —C(O)C1-C9 straight chain alkyl, —CH(OH)C1—C9 straight chain alkyl, —CH(Cl)C1—C9 straight chain alkyl, -(2-pyridyl)methyl, -(3-pyridyl)methyl, -(4-pyridyl)methyl, and —CH2C6H5, the —CH2C6H5 being unsubstituted or substituted on phenyl with one cyano or one or more halo, methoxyl, or trifluoromethyl groups;
R10 is selected from the group consisting of C1-C4 straight or branched chain alkyl and —C6H5;
R11 and R12 are independently C1-C3 straight or branched chain alkyl;
m is an integer ranging from 1 to 5;
and
when m is 3 and R2 is —CH2CH3, then R16 is —H or —CH3 and R17 is —H;
when m is 3 and R2 is —CH3, then R16 is —H or —CH3 and R17 is —H or —COOEt;
and
when m is other than 3 and R2 is other than —CH3 or —CH2CH3, then R16 and R17 are —H only;
with the proviso that the compound of Formula (I) is not metacycloprodigiosin.

10 more elements

A method for treating bronchogenic carcinoma comprising

administering to a patient in need of such treatment a therapeutically effective amount of a compound of Formula (I):
or a pharmaceutically acceptable salt thereof, wherein, in the compound of Formula (I):
each R1 is independently selected from the group consisting of —H, —CH3, —CH2CH3, —CH2C6H5, —C(O)OC(CH3)3, —C(O)OCH2C6H5, and —C(O)CH3;
R2 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH2C6H5, —SiR10R11R12, —C(O)CH3, —C(O)C6H5, -2-tetrahydropyranyl, —OCH2OCH3, and —C(O)OCH2CCl3;
R3 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH(R14)(R15) wherein R14 and R15 are independently C1-C12 straight chain alkyl, —C(O)C1-C9 straight chain alkyl, —CH(OH)C1-C9 straight chain alkyl, —CH(Cl)C1-C9 straight chain alkyl, -(2-pyridyl)methyl, -(3-pyridyl)methyl, -(4-pyridyl)methyl, and —CH2C6H5, the —CH2C6H5 being unsubstituted or substituted on phenyl with one cyano or one or more halo, methoxyl, or trifluoromethyl groups;
R10 is selected from the group consisting of C1-C4 straight or branched chain alkyl and —C6H5;
R11 and R12 are independently C1-C3 straight or branched chain alkyl;
m is an integer ranging from 1 to 5;
and
when m is 3 and R2 is —CH2CH3, then R16 is —H or —CH3 and R17 is —H;
when m is 3 and R2 is —CH3, then R16 is —H or —CH3 and R17 is —H or —COOEt;
and
when m is other than 3 and R2 is other than —CH3 or —CH2CH3, then R16 and R17 are —H only;
with the proviso that the compound of Formula (I) is not metacycloprodigiosin.

11 more elements

A method for inhibiting the growth of a lung carcinoma cell comprising contacting a said cancer cell with an effective amount of a compound of Formula (I):

or a pharmaceutically acceptable salt thereof, wherein, in the compound of Formula (I):
each R1 is independently selected from the group consisting of —H, —CH3, —CH2CH3, —CH2C6H5, —C(O)OC(CH3)3, —C(O)OCH2C6H5, and —C(O)CH3;
R2 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH2C6H5, —SiR10R11R12, —C(O)CH3, —C(O)C6H5, -2-tetrahydropyranyl, —OCH2OCH3, and —C(O)OCH2CCl3;
R3 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH(R14)(R15) wherein R14 and R15 are independently C1-C12 straight chain alkyl, —C(O)C1-C9 straight chain alkyl, —CH(OH)C1-C9 straight chain alkyl, —CH(Cl)C1-C9 straight chain alkyl, -(2-pyridyl)methyl, -(3-pyridyl)methyl, -(4-pyridyl)methyl, and —CH2C6H5, the —CH2C6H5 being unsubstituted or substituted on phenyl with one cyano or one or more halo, methoxyl, or trifluoromethyl groups;
R10 is selected from the group consisting of C1-C4 straight or branched chain alkyl and R11 and R12 are independently C1-C3 straight or branched chain alkyl;
m is an integer ranging from 1 to 5;
when m is 3 and R2 is —CH2CH3, then R16 is —H or —CH3 and R17 is —H;
when m is 3 and R2 is —CH3, then R16 is —H or —CH3 and R17 is —H or —COOEt;
and
when m is other than 3 and R2 is other than —CH3 or —CH2CH3, then R16 and R17 are —H only;
with the proviso that the compound of Formula (I) is not metacycloprodigiosin.

8 more elements

A method for inhibiting the growth of a bronchogenic carcinoma cell comprising

contacting a said cancer cell with an effective amount of a compound of Formula (I):
or a pharmaceutically acceptable salt thereof, wherein, in the compound of Formula (I):
each R1 is independently selected from the group consisting of —H, —CH3,—CH2CH3, —CH2C6H5, —C(O)OC(CH3)3, —C(O)OCH2C6H5, and —C(O)CH3;
R2 is selected from the group consisting of —H, C1-C12 straight chain alkyl —CH2C6H5, —SiR10R11R12, —C(O)CH3, —C(O)C6H5, -2-tetrahydropyranyl, —OCH2OCH3, and —C(O)OCH2CCl3;
R3 is selected from the group consisting of —H, C1-C12 straight chain alkyl, —CH(R14)(R15) wherein R14 and R15 are independently C1-C12 straight chain alkyl, —C(O)C1-C9 straight chain alkyl, —CH(OH)C1-C9 straight chain alkyl, —CH(Cl)C1-C9 straight chain alkyl, -(2-pyridyl)methyl, -(3-pyridyl)methyl, -(4-pyridyl)methyl, and —CH2C6H5, the —CH2C6H5 being unsubstituted or substituted on phenyl with one cyano or one or more halo, methoxyl, or trifluoromethyl groups;
R10 is selected from the group consisting of C1-C4 straight or branched chain alkyl and —C6H5;
R11 and R12 are independently C1-C3 straight or branched chain alkyl;
m is an integer ranging from 1 to 5;
when m is 3 and R2 is —CH2CH3, then R16 is —H or —CH3 and R17 is —H;
when m is 3 and R2 is —CH3, then R16 is —H or —CH3 and R17 is —H or —COOEt;
and
when m is other than 3 and R2 is other than —CH3 or —CH2CH3, then R16 and R17 are —H only;
with the proviso that the compound of Formula (I) is not metacycloprodigiosin.

10 more elements

Dependencies are inferred from the claim text.

Pyrrole-type compounds, compositions, and methods for treating cancer or viral diseases

Life of this patent

Pyrrole-type compounds, compositions, and methods for treating cancer or viral diseases

Life of this patent

Abstract

Claims88