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US 11,548,894 B2Granted
Benzamide or benzamine compounds useful as anticancer agents for the treatment of human cancers
AssigneeBoard of Regents, The University of Texas System
InventorsJef DeBrabander, Luis Parada
Life of this patent
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Abstract
The described invention provides small molecule anti-cancer compounds for treating tumors that respond to cholesterol biosynthesis inhibition. The compounds selectively inhibit the cholesterol biosynthetic pathway in tumor-derived cancer cells, but do not affect normally dividing cells.
Claims4
A pharmaceutical composition comprising a small molecule anti-cancer compound of Formula I-f:
- wherein:
- X1 is selected from the group consisting of H, F, CN, NH2, NO2, N3, and SO2Me;
- n=1, 2, or 3;
- L2 is selected from the group consisting of S, O, NH, CHOH, C═O, —O(CH2)—, —S(CH2)—, —(CH2)O—, and —(CH2)S—;
- R1 is selected from the group consisting of H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxyalkyl, and acyloxyalkyl;
- R1 and R2 may optionally form a ring, such that R1-R2 consists of a three to six subunit chain comprising subunits independently selected from the group consisting of (CR7R8), NR9, O, and S;
- R1 and R3 may optionally form a ring, such that R1-R3 comprises —(CR10R11)m, where m=2, 3, 4 or 5;
- R2 is selected from the group consisting of H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxyalkyl, and acyloxyalkyl;
- R2 and R4 may optionally form a ring, such that R2-R4 consists of a one to four subunit chain comprising subunits independently selected from the group consisting of —(CR12R13);
- R2 may simultaneously form a ring with R1 as described above;
- R3 is selected from the group consisting of H, D, F, Me, and Et;
- R4 is selected from the group consisting of H, Me, CD3, CF3, Et, i-Pr, cyclopropyl, and C2-C6 alkynyl;
- R7 and R8 are independently selected from the group consisting of H, D, F, Me, Et, OR, and NR2;
- wherein R is selected from the group consisting of H, Me, and Et;
- R9 is selected from the group consisting of H, Me, Et, isopropyl, and cyclopropyl;
- R10 and R11 are independently selected from the group consisting of H, D, F, Me, Et, OR, and NR2;
- wherein R is selected from the group consisting of H, Me, and Et;
- R12 and R13 are independently selected from the group consisting of H, D, F, Me, and Et;
- and
- R14 and R15 can be attached at any available position on the aromatic ring and are selected from the group consisting of H, D, F, Cl, Br, CF3, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl, OR, NR2, NO2, N3, CN, CO2R, CO2NR2, SR, alkylacyl and arylacyl;
- wherein R is independently selected from the group consisting of H, Me, Et, isopropyl, cyclopropyl, propargyl, and acyl;
- such that all possible stereoisomers, including optically active isomers, are included whenever stereogenic centers are present;
- or a pharmaceutically acceptable salt, prodrug, active metabolite, or solvate thereof,
- wherein the pharmaceutical composition comprises a therapeutic amount of the compound and a pharmaceutically acceptable carrier.
21 more elements
Dependencies are inferred from the claim text.