Novel heterocyclic compounds and their pharmaceutical compositions

A compound having the formula:

• or a salt, a prodrug, a diastereomeric mixture, an enantiomer, a tautomer, a racemic mixture thereof, or any combination thereof, wherein:
• R1 is an alkyl, a cycloalkyl, an aryl, an aralkyl, or a heterocyclyl, any of which having up to 12 carbon atoms;
• wherein the heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• R2 is selected from an alkyl, a haloalkyl, a cycloalkyl, or a cycloalkyl-substituted alkyl, any of which having up to 12 carbon atoms, or hydrogen;
• R3 is selected from:
• 1) an alkyl having up to 12 carbon atoms;
• 2) CO2R6, COR8, SO2R8, SO2NR6R7, or CONR6R7;
• 3) a substituted or an unsubstituted aryl, or a substituted or an unsubstituted 5-, 6-, or 7-membered heterocyclyl or heteroaryl, comprising from 1 to 4 heteroatoms or heterogroups, selected independently from >O, >N—, >S, or >NR6, any of which having up to 12 carbon atoms;
• or 4) hydrogen or cyano;
• wherein when R3 is an aryl, a heterocyclyl, or a heteroaryl, R3 is optionally substituted with up to three substituents selected independently from a halide, a hydroxyl, a cyano, an alkoxy having up to 12 carbon atoms, or R11;
• R4, in each occurrence, is selected independently from:
• 1) an alkyl, a cycloalkyl, a haloalkyl, an alkoxy, an aryloxy, a haloalkoxy, an aryl, or a heteroaryl, any of which having up to 12 carbon atoms, wherein any heteroaryl comprises at least one heteroatom or heterogroup selected from >O, >N—, >S, or >NR6;
• or 2) halogen, hydroxy, or cyano;
• m is an integer selected from 0, 1, 2, or 3;
• R5 is selected from:
• 1) an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, or an aryl, any of which having up to 12 carbon atoms;
• 2) CO2R6 or COR8;
• or 3) hydrogen, cyano, or hydroxyl;
• R6 and R7 are independently an alkyl or a haloalkyl, any of which having up to 12 carbon atoms, or hydrogen;
• R8 is an alkyl having up to 12 carbon atoms;
• and
• R10 is selected from:
• 1) an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, or an aryl, any of which having up to 12 carbon atoms;
• 2) CO2R6 or COR8;
• or 3) hydrogen, halogen, or cyano.
• R11 is selected independently from:
• 1) an alkyl, a haloalkyl, a cycloalkyl, or an alkoxycarbonyl, any of which having up to 12 carbon atoms;
• 2) a substituted or an unsubstituted heteroaryl or heterocyclyl, any of which having up to 12 carbon atoms, comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO, wherein any substituted heteroaryl or heterocyclyl is substituted with up to three substituents selected independently from an alkyl having up to 12 carbon atoms or a hydroxyl;
• or
• 3) —CO-Z-R13, —CO—R12, —CO-Z-(CH2)n-CO-Z-R13, —NR15R16, -Z-CO—(CH2)n-Z-R13, -Z-CO—(CH2)n-CO-Z-R13, —O—(CH2)n-CO-Z-R13, —O—(CH2)n-R14, —O—R12—(CH2)n-R13, —O—R14—CO—O—R13, —O—(CH2)n-R12, —O—(CH2)n-NR′R″, —O—(CH2)n-CO2—(CH2)n-R13, —O—(CH2)n-CONR′R″, —O—(CH2)n-SR8, —O—(CH2)n-CO2—R13, —O—(CH2)n-O—(CH2)n-OR13, —O—(CH2)n-CONR′R″, —O—(CH2)n-CONH—(CH2)n-OR13, —O—(CH2)n-SO2R8, —O—(CH2)n-R13, —O—(CH2)n-OR13, —O—(CH2)n-O—(CH2)n-OR13, —S—(CH2)n-CONR′R″, —SO2—(CH2)n-OR13, —SO2—(CH2)n-CONR′R″, —(CH2)n-O—CO—R8, —(CH2)n-R12, —(CH2)n-R13, —(CH2)n-N—(CH2)n-OR13, —(CH2)n-CO-Z-R13, —(CH2)n-Z-R13, or -alkenylene-CO2—(CH2)n-R13;
• n, in each occurrence, is independently 1, 2, or 3;
• R12, in each occurrence, is independently selected from a substituted or an unsubstituted heterocyclyl having up to 12 carbon atoms, comprising at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO, wherein any substituted heterocyclyl is substituted with up to three substituents selected independently from an acyl, an alkyl, or an alkoxycarbonyl, any of which having up to 12 carbon atoms, or —COOH;
• R13, in each occurrence, is independently selected from:
• 1) hydrogen;
• or 2) a cycloalkyl, an aryl, a haloalkyl, a heterocyclyl, or an alkyl group optionally substituted with at least one hydroxyl, any of which having up to 12 carbon atoms, wherein any heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• R14, in each occurrence, is independently selected from a heterocyclyl, a cycloalkyl, or an aryl, any of which having up to 12 carbon atoms, wherein any heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• Z, in each occurrence, is independently >O or >NR6;
• R′ and R″, in each occurrence, are independently selected from hydrogen or an alkyl having up to 12 carbon artoms;
• and
• R15 and R16, in each occurrence, are independently selected from:
• 1) hydrogen;
• 2) an alkyl having up to 12 carbon atoms;
• or 3) —(CH2)n-O—R13, —(CH2)n-R14, —COR13, —(CH2)n-CO-Z-R13, —CO2R13, —CO2—(CH2)n-R13, —CO2—(CH2)n-R12, —CO2—(CH2)n-CO-Z-R13, —CO2—(CH2)n-OR13, —CO—(CH2)n-O—(CH2)n-O—(CH2)n-R13, —CO—(CH2)n-O(CH2)n-OR13, or —CO—NH—(CH2)n-OR13;
• or R15 and R16 together form a substituted or an unsubstituted cyclic moiety comprising up to 12 carbon atoms, further comprising at least one additional, optional heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• wherein any substituted cyclic moiety is substituted with up to three substituents selected independently from:
• 1) hydroxyl;
• 2) an alkyl or a heteroaryl, any of which having up to 12 carbon atoms, wherein any heteroaryl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, or >NR6;
• or 3) COOR13, -Z-(CH2)n-R13, —COR13, —CO2—(CH2)n-R13, —CO(CH2)n-O—R13, —(CH2)n-CO2—R13, —SO2R8, —SO2NR′R″, or —NR′R″;
• wherein the —(CH2)n- linking moiety, in any occurrence, is optionally substituted with at least one group selected independently from hydroxyl, amino, or an alkyl having up to 3 carbon atoms.

A compound having the formula:

• or a salt, a prodrug, a diastereomeric mixture, an enantiomer, a tautomer, a racemic mixture thereof, or any combination thereof, wherein:
• R1 is an alkyl, a cycloalkyl, an aryl, an aralkyl, or a heterocyclyl, any of which having up to 12 carbon atoms;
• wherein the heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• R2 is selected from an alkyl, a haloalkyl, a cycloalkyl, or a cycloalkyl-substituted alkyl, any of which having up to 5 carbon atoms, or hydrogen;
• R3 is selected from:
• 1) an alkyl having up to 12 carbon atoms;
• 2) CO2R6, COR8, SO2R8, SO2NR6R7, or CONR6R7;
• 3) a substituted or an unsubstituted aryl, or a substituted or an unsubstituted 5-, 6-, or 7-membered heterocyclyl or heteroaryl, comprising from 1 to 4 heteroatoms or heterogroups, selected independently from >O, >N—, >S, or >NR6, any of which having up to 12 carbon atoms;
• or 4) hydrogen or cyano;
• wherein when R3 is an aryl, a heterocyclyl, or a heteroaryl, R3 is optionally substituted with up to three substituents selected independently from a halide, a hydroxyl, a cyano, an alkoxy having up to 12 carbon atoms, or R11;
• R4, in each occurrence, is selected independently from:
• 1) an alkyl, a cycloalkyl, a haloalkyl, an alkoxy, an aryloxy, a haloalkoxy, an aryl, or a heteroaryl, any of which having up to 5 carbon atoms, wherein any heteroaryl comprises at least one heteroatom or heterogroup selected from >O, >N—, >S, or >NR6;
• or 2) halogen, hydroxy, or cyano;
• m is an integer selected from 0, 1, 2, or 3;
• R5 is selected from:
• 1) an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, or an aryl, any of which having up to 12 carbon atoms;
• or 2) hydrogen or hydroxyl;
• R6 and R7 are independently an alkyl or a haloalkyl, any of which having up to 12 carbon atoms, or hydrogen;
• R8 is an alkyl having up to 12 carbon atoms;
• and
• R10 is selected from:
• 1) an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, or an aryl, any of which having up to 12 carbon atoms;
• or 2) hydrogen, halogen, or cyano;
• R11 is selected independently from:
• 1) an alkyl, a haloalkyl, a cycloalkyl, or an alkoxycarbonyl, any of which having up to 12 carbon atoms;
• 2) a substituted or an unsubstituted heteroaryl or heterocyclyl, any of which having up to 12 carbon atoms, comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO, wherein any substituted heteroaryl or heterocyclyl is substituted with up to three substituents selected independently from an alkyl having up to 12 carbon atoms or a hydroxyl;
• or
• 3) —CO-Z-R13, —CO—R12, —CO-Z-(CH2)n-CO-Z-R13, —NR15R16, -Z-CO—(CH2)n-Z-R13, -Z-CO—(CH2)n-CO-Z-R13, —O—(CH2)n-CO-Z-R13, —O—(CH2)n-R14, —O—R12—(CH2)n-R13, —O—R14—CO—O—R13, —O—(CH2)n-R12, —O—(CH2)n-NR′R″, —O—(CH2)n-CO2—(CH2)n-R13, —O—(CH2)n-CONR′R″, —O—(CH2)n-SR8, —O—(CH2)n-CO2—R13, —O—(CH2)n-O—(CH2)n-OR13, —O—(CH2)n-CONR′R″, —O—(CH2)n-CONH—(CH2)n-OR13, —O—(CH2)n-SO2R8, —O—(CH2)n-R13, —O—(CH2)n-OR13, —O—(CH2)n-O—(CH2)n-OR13, —S—(CH2)n-CONR′R″, —SO2—(CH2)n-OR13, —SO2—(CH2)n-CONR′R″, —(CH2)n-O—CO—R8, —(CH2)n-R12, —(CH2)n-R13, —(CH2)n-N—(CH2)n-OR13, —(CH2)n-CO-Z-R13, —(CH2)n-Z-R13, or -alkenylene-CO2—(CH2)n-R13;
• n, in each occurrence, is independently 1, 2, or 3;
• R12, in each occurrence, is independently selected from a substituted or an unsubstituted heterocyclyl having up to 12 carbon atoms, comprising at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO, wherein any substituted heterocyclyl is substituted with up to three substituents selected independently from an acyl, an alkyl, or an alkoxycarbonyl, any of which having up to 12 carbon atoms, or —COOH;
• R13, in each occurrence, is independently selected from:
• 1) hydrogen;
• or 2) a cycloalkyl, an aryl, a haloalkyl, a heterocyclyl, or an alkyl group optionally substituted with at least one hydroxyl, any of which having up to 12 carbon atoms, wherein any heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• R14, in each occurrence, is independently selected from a heterocyclyl, a cycloalkyl, or an aryl, any of which having up to 12 carbon atoms, wherein any heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• Z, in each occurrence, is independently >O or >NR6;
• R′ and R″, in each occurrence, are independently selected from hydrogen or an alkyl having up to 12 carbon artoms;
• and
• R15 and R16, in each occurrence, are independently selected from:
• 1) hydrogen;
• 2) an alkyl having up to 12 carbon atoms;
• or 3) —(CH2)n-O—R13, —(CH2)n-R14, —COR13, —(CH2)n-CO-Z-R13, —CO2R13, —CO2—(CH2)n-R13, —CO2—(CH2)n-R12, —CO2—(CH2)n-CO-Z-R13, —CO2—(CH2)n-OR13, —CO—(CH2)n-O—(CH2)n-O—(CH2)n-R13, —CO—(CH2)n-O(CH2)n-OR13, or —CO—NH—(CH2)n-OR13;
• or R15 and R16 together form a substituted or an unsubstituted cyclic moiety comprising up to 12 carbon atoms, further comprising at least one additional, optional heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• wherein any substituted cyclic moiety is substituted with up to three substituents selected independently from:
• 1) hydroxyl;
• 2) an alkyl or a heteroaryl, any of which having up to 12 carbon atoms, wherein any heteroaryl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, or >NR6;
• or 3) COOR13, -Z-(CH2)n-R13, —COR13, —CO2—(CH2)n-R13, —CO(CH2)n-O—R13, —(CH2)n-CO2—R13, —SO2R8, —SO2NR′R″, or —NR′R″;
• wherein the —(CH2)n- linking moiety, in any occurrence, is optionally substituted with at least one group selected independently from hydroxyl, amino, or an alkyl having up to 3 carbon atoms.

A composition comprising a pharmaceutically acceptable carrier and at least one compound having the formula:

• or a salt, a prodrug, a diastereomeric mixture, an enantiomer, a tautomer, a racemic mixture thereof, or any combination thereof, wherein:
• ring A is fused to ring B and is selected from:
• R1 is an alkyl, a cycloalkyl, a haloalkyl, an aryl, an aralkyl, a heteroaryl, or a heterocyclyl, any of which having up to 12 carbon atoms;
• wherein any heteroaryl or heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• R2 and R9 are the same or different, and are selected independently from an alkyl, a haloalkyl, a cycloalkyl, or a cycloalkyl-substituted alkyl, any of which having up to 12 carbon atoms, or hydrogen;
• R3 is selected from:
• 1) an alkyl having up to 12 carbon atoms;
• 2) CO2R6, COR8, SO2R8, SO2NR6R7, or CONR6R7;
• 3) a substituted or an unsubstituted aryl, or a substituted or an unsubstituted 5-, 6-, or 7-membered heterocyclyl or heteroaryl, comprising from 1 to 4 heteroatoms or heterogroups, selected independently from >O, >N—, >S, or >NR6, any of which having up to 12 carbon atoms;
• or 4) hydrogen or cyano;
• wherein when R3 is an aryl, a heterocyclyl, or a heteroaryl, R3 is optionally substituted with up to three substituents selected independently from a halide, a hydroxyl, a cyano, an alkoxy having up to 12 carbon atoms, or R11;
• R4, in each occurrence, is selected independently from:
• 1) an alkyl, a cycloalkyl, a haloalkyl, an alkoxy, an aryloxy, a haloalkoxy, an aryl, or a heteroaryl, any of which having up to 12 carbon atoms, wherein any heteroaryl comprises at least one heteroatom or heterogroup selected from >O, >N—, >S, or >NR6;
• or 2) halogen, hydroxy, or cyano;
• m is an integer selected from 0, 1, 2, or 3;
• R5 is selected from:
• 1) an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, or an aryl, any of which having up to 12 carbon atoms;
• 2) CO2R6 or COR8;
• or 3) hydrogen, cyano, or hydroxyl;
• R6 and R7 are independently an alkyl or a haloalkyl, any of which having up to 12 carbon atoms, or hydrogen;
• R8 is an alkyl having up to 12 carbon atoms;
• and
• R10 is selected from:
• 1) an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, or an aryl, any of which having up to 12 carbon atoms;
• 2) CO2R6 or COR8;
• or 3) hydrogen, halogen, or cyano.
• R11 is selected independently from:
• 1) an alkyl, a haloalkyl, a cycloalkyl, or an alkoxycarbonyl, any of which having up to 12 carbon atoms;
• 2) a substituted or an unsubstituted heteroaryl or heterocyclyl, any of which having up to 12 carbon atoms, comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO, wherein any substituted heteroaryl or heterocyclyl is substituted with up to three substituents selected independently from an alkyl having up to 12 carbon atoms or a hydroxyl;
• or
• 3) —CO-Z-R13, —CO—R12, —CO-Z-(CH2)n-CO-Z-R13, —NR15R16, -Z-CO—(CH2)n-Z-R13, -Z-CO—(CH2)n-CO-Z-R13, —O—(CH2)n-CO-Z-R13, —O—(CH2)n-R14, —O—R12—(CH2)n-R13, —O—R14—CO—O—R13, —O—(CH2)n-R12, —O—(CH2)n-NR′R″, —O—(CH2)n-CO2—(CH2)n-R13, —O—(CH2)n-CONR′R″, —O—(CH2)n-SR8, —O—(CH2)n-CO2—R13, —O—(CH2)n-O—(CH2)n-OR13, —O—(CH2)n-CONR′R″, —O—(CH2)n-CONH—(CH2)n-OR13, —O—(CH2)n-SO2R8, —O—(CH2)n-R13, —O—(CH2)n-OR13, —O—(CH2)n-O—(CH2)n-OR13, —S—(CH2)n-CONR′R″, —SO2—(CH2)n-OR13, —SO2—(CH2)n-CONR′R″, —(CH2)n-O—CO—R8, —(CH2)n-R12, —(CH2)n-R13, —(CH2)n-N—(CH2)n-OR13, —(CH2)n-CO-Z-R13, —(CH2)n-Z-R13, or -alkenylene-CO2—(CH2)n-R13;
• n, in each occurrence, is independently 1, 2, or 3;
• R12, in each occurrence, is independently selected from a substituted or an unsubstituted heterocyclyl having up to 12 carbon atoms, comprising at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO, wherein any substituted heterocyclyl is substituted with up to three substituents selected independently from an acyl, an alkyl, or an alkoxycarbonyl, any of which having up to 12 carbon atoms, or —COOH;
• R13, in each occurrence, is independently selected from:
• 1) hydrogen;
• or 2) a cycloalkyl, an aryl, a haloalkyl, a heterocyclyl, or an alkyl group optionally substituted with at least one hydroxyl, any of which having up to 12 carbon atoms, wherein any heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• R14, in each occurrence, is independently selected from a heterocyclyl, a cycloalkyl, or an aryl, any of which having up to 12 carbon atoms, wherein any heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• Z, in each occurrence, is independently >O or >NR6;
• R′ and R″, in each occurrence, are independently selected from hydrogen or an alkyl having up to 12 carbon artoms;
• and
• R15 and R16, in each occurrence, are independently selected from:
• 1) hydrogen;
• 2) an alkyl having up to 12 carbon atoms;
• or 3) —(CH2)n-O—R13, —(CH2)n-R14, —COR13, —(CH2)n-CO-Z-R13, —CO2R13, —CO2—(CH2)n-R13, —CO2—(CH2)n-R12, —CO2—(CH2)n-CO-Z-R13, —CO2—(CH2)n-OR13, —CO—(CH2)n-O—(CH2)n-O—(CH2)n-R13, —CO—(CH2)n-O(CH2)n-OR13, or —CO—NH—(CH2)n-OR13;
• or R15 and R16 together form a substituted or an unsubstituted cyclic moiety comprising up to 12 carbon atoms, further comprising at least one additional, optional heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• wherein any substituted cyclic moiety is substituted with up to three substituents selected independently from:
• 1) hydroxyl;
• 2) an alkyl or a heteroaryl, any of which having up to 12 carbon atoms, wherein any heteroaryl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, or >NR6;
• or 3) COOR13, -Z-(CH2)n-R13, —COR13, —CO2—(CH2)n-R13, —CO(CH2)n-O—R13, —(CH2)n-CO2—R13, —SO2R8, —SO2NR′R″, or —NR′R″;
• wherein the —(CH2)n- linking moiety, in any occurrence, is optionally substituted with at least one group selected independently from hydroxyl, amino, or an alkyl having up to 3 carbon atoms.

A composition comprising a pharmaceutically acceptable carrier and at least one compound having the formula:

• or a salt, a prodrug, a diastereomeric mixture, an enantiomer, a tautomer, a racemic mixture thereof, or any combination thereof, wherein:
• R1 is an alkyl, a cycloalkyl, an aryl, an aralkyl, or a heterocyclyl, any of which having up to 12 carbon atoms;
• wherein the heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• R2 is selected from an alkyl, a haloalkyl, a cycloalkyl, or a cycloalkyl-substituted alkyl, any of which having up to 12 carbon atoms, or hydrogen;
• R3 is selected from:
• 1) an alkyl having up to 12 carbon atoms;
• 2) CO2R6, COR8, SO2R8, SO2NR6R7, or CONR6R7;
• 3) a substituted or an unsubstituted aryl, or a substituted or an unsubstituted 5-, 6-, or 7-membered heterocyclyl or heteroaryl, comprising from 1 to 4 heteroatoms or heterogroups, selected independently from >O, >N—, >S, or >NR6, any of which having up to 12 carbon atoms;
• or 4) hydrogen or cyano;
• wherein when R3 is an aryl, a heterocyclyl, or a heteroaryl, R3 is optionally substituted with up to three substituents selected independently from a halide, a hydroxyl, a cyano, an alkoxy having up to 12 carbon atoms, or R11;
• R4, in each occurrence, is selected independently from:
• 1) an alkyl, a cycloalkyl, a haloalkyl, an alkoxy, an aryloxy, a haloalkoxy, an aryl, or a heteroaryl, any of which having up to 12 carbon atoms, wherein any heteroaryl comprises at least one heteroatom or heterogroup selected from >O, >N—, >S, or >NR6;
• or 2) halogen, hydroxy, or cyano;
• m is an integer selected from 0, 1, 2, or 3;
• R5 is selected from:
• 1) an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, or an aryl, any of which having up to 12 carbon atoms;
• 2) CO2R6 or COR8;
• or 3) hydrogen, cyano, or hydroxyl;
• R6 and R7 are independently an alkyl or a haloalkyl, any of which having up to 12 carbon atoms, or hydrogen;
• R8 is an alkyl having up to 12 carbon atoms;
• and
• R10 is selected from:
• 1) an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, or an aryl, any of which having up to 12 carbon atoms;
• 2) CO2R6 or COR8;
• or 3) hydrogen, halogen, or cyano.
• R11 is selected independently from:
• 1) an alkyl, a haloalkyl, a cycloalkyl, or an alkoxycarbonyl, any of which having up to 12 carbon atoms;
• 2) a substituted or an unsubstituted heteroaryl or heterocyclyl, any of which having up to 12 carbon atoms, comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO, wherein any substituted heteroaryl or heterocyclyl is substituted with up to three substituents selected independently from an alkyl having up to 12 carbon atoms or a hydroxyl;
• or
• 3) —CO-Z-R13, —CO—R12, —CO-Z-(CH2)n-CO-Z-R13, —NR15R16, -Z-CO—(CH2)n-Z-R13, -Z-CO—(CH2)n-CO-Z-R13, —O—(CH2)n-CO-Z-R13, —O—(CH2)n-R14, —O—R12—(CH2)n-R13, —O—R14—CO—O—R13, —O—(CH2)n-R12, —O—(CH2)n-NR′R″, —O—(CH2)n-CO2—(CH2)n-R13, —O—(CH2)n-CONR′R″, —O—(CH2)n-SR8, —O—(CH2)n-CO2—R13, —O—(CH2)n-O—(CH2)n-OR13, —O—(CH2)n-CONR′R″, —O—(CH2)n-CONH—(CH2)n-OR13, —O—(CH2)n-SO2R8, —O—(CH2)n-R13, —O—(CH2)n-OR13, —O—(CH2)n-O—(CH2)n-OR13, —S—(CH2)n-CONR′R″, —SO2—(CH2)n-OR13, —SO2—(CH2)n-CONR′R″, —(CH2)n-O—CO—R8, —(CH2)n-R12, —(CH2)n-R13, —(CH2)n-N—(CH2)n-OR13, —(CH2)n-CO-Z-R13, —(CH2)n-Z-R13, or -alkenylene-CO2—(CH2)n-R13;
• n, in each occurrence, is independently 1, 2, or 3;
• R12, in each occurrence, is independently selected from a substituted or an unsubstituted heterocyclyl having up to 12 carbon atoms, comprising at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO, wherein any substituted heterocyclyl is substituted with up to three substituents selected independently from an acyl, an alkyl, or an alkoxycarbonyl, any of which having up to 12 carbon atoms, or —COOH;
• R13, in each occurrence, is independently selected from:
• 1) hydrogen;
• or 2) a cycloalkyl, an aryl, a haloalkyl, a heterocyclyl, or an alkyl group optionally substituted with at least one hydroxyl, any of which having up to 12 carbon atoms, wherein any heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• R14, in each occurrence, is independently selected from a heterocyclyl, a cycloalkyl, or an aryl, any of which having up to 12 carbon atoms, wherein any heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• Z, in each occurrence, is independently >O or >NR6;
• R′ and R″, in each occurrence, are independently selected from hydrogen or an alkyl having up to 12 carbon artoms;
• and
• R15 and R16, in each occurrence, are independently selected from:
• 1) hydrogen;
• 2) an alkyl having up to 12 carbon atoms;
• or 3) —(CH2)n-O—R13, —(CH2)n-R14, —COR13, —(CH2)n-CO-Z-R13, —CO2R13, —CO2—(CH2)n-R13, —CO2—(CH2)n-R12, —CO2—(CH2)n-CO-Z-R13, —CO2—(CH2)n-OR13, —CO—(CH2)n-O—(CH2)n-O—(CH2)n-R13, —CO—(CH2)n-O(CH2)n-OR13, or —CO—NH—(CH2)n-OR13;
• or R15 and R16 together form a substituted or an unsubstituted cyclic moiety comprising up to 12 carbon atoms, further comprising at least one additional, optional heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• wherein any substituted cyclic moiety is substituted with up to three substituents selected independently from:
• 1) hydroxyl;
• 2) an alkyl or a heteroaryl, any of which having up to 12 carbon atoms, wherein any heteroaryl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, or >NR6;
• or 3) COOR13, -Z-(CH2)n-R13, —COR13, —CO2—(CH2)n-R13, —CO(CH2)n-O—R13, —(CH2)n-CO2—R13, —SO2R8, —SO2NR′R″, or —NR′R″;
• wherein the —(CH2)n- linking moiety, in any occurrence, is optionally substituted with at least one group selected independently from hydroxyl, amino, or an alkyl having up to 3 carbon atoms.

A composition comprising a pharmaceutically acceptable carrier and at least one compound having the formula:

• or a salt, a prodrug, a diastereomeric mixture, an enantiomer, a tautomer, a racemic mixture thereof, or any combination thereof, wherein:
• R1 is an alkyl, a cycloalkyl, an aryl, an aralkyl, or a heterocyclyl, any of which having up to 12 carbon atoms;
• wherein the heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• R2 is selected from an alkyl, a haloalkyl, a cycloalkyl, or a cycloalkyl-substituted alkyl, any of which having up to 5 carbon atoms, or hydrogen;
• R3 is selected from:
• 1) an alkyl having up to 12 carbon atoms;
• 2) CO2R6, COR8, SO2R8, SO2NR6R7, or CONR6R7;
• 3) a substituted or an unsubstituted aryl, or a substituted or an unsubstituted 5-, 6-, or 7-membered heterocyclyl or heteroaryl, comprising from 1 to 4 heteroatoms or heterogroups, selected independently from >O, >N—, >S, or >NR6, any of which having up to 12 carbon atoms;
• or 4) hydrogen or cyano;
• wherein when R3 is an aryl, a heterocyclyl, or a heteroaryl, R3 is optionally substituted with up to three substituents selected independently from a halide, a hydroxyl, a cyano, an alkoxy having up to 12 carbon atoms, or R11;
• R4, in each occurrence, is selected independently from:
• 1) an alkyl, a cycloalkyl, a haloalkyl, an alkoxy, an aryloxy, a haloalkoxy, an aryl, or a heteroaryl, any of which having up to 5 carbon atoms, wherein any heteroaryl comprises at least one heteroatom or heterogroup selected from >O, >N—, >S, or >NR6;
• or 2) halogen, hydroxy, or cyano;
• m is an integer selected from 0, 1, 2, or 3;
• R5 is selected from:
• 1) an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, or an aryl, any of which having up to 12 carbon atoms;
• or 2) hydrogen or hydroxyl;
• R6 and R7 are independently an alkyl or a haloalkyl, any of which having up to 12 carbon atoms, or hydrogen;
• R8 is an alkyl having up to 12 carbon atoms;
• and
• R10 is selected from:
• 1) an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, or an aryl, any of which having up to 12 carbon atoms;
• or 2) hydrogen, halogen, or cyano;
• R11 is selected independently from:
• 1) an alkyl, a haloalkyl, a cycloalkyl, or an alkoxycarbonyl, any of which having up to 12 carbon atoms;
• 2) a substituted or an unsubstituted heteroaryl or heterocyclyl, any of which having up to 12 carbon atoms, comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO, wherein any substituted heteroaryl or heterocyclyl is substituted with up to three substituents selected independently from an alkyl having up to 12 carbon atoms or a hydroxyl;
• or
• 3) —CO-Z-R13, —CO—R12, —CO-Z-(CH2)n-CO-Z-R13, —NR15R16, -Z-CO—(CH2)n-Z-R13, -Z-CO—(CH2)n-CO-Z-R13, —O—(CH2)n-CO-Z-R13, —O—(CH2)n-R14, —O—R12—(CH2)n-R13, —O—R14—CO—O—R13, —O—(CH2)n-R12, —O—(CH2)n-NR′R″, —O—(CH2)n-CO2—(CH2)n-R13, —O—(CH2)n-CONR′R″, —O—(CH2)n-SR8, —O—(CH2)n-CO2—R13, —O—(CH2)n-O—(CH2)n-OR13, —O—(CH2)n-CONR′R″, —O—(CH2)n-CONH—(CH2)n-OR13, —O—(CH2)n-SO2R8, —O—(CH2)n-R13, —O—(CH2)n-OR13, —O—(CH2)n-O—(CH2)n-OR13, —S—(CH2)n-CONR′R″, —SO2—(CH2)n-OR13, —SO2—(CH2)n-CONR′R″, —(CH2)n-O—CO—R8, —(CH2)n-R12, —(CH2)n-R13, —(CH2)n-N—(CH2)n-OR13, —(CH2)n-CO-Z-R13, —(CH2)n-Z-R13, or -alkenylene-CO2—(CH2)n-R13;
• n, in each occurrence, is independently 1, 2, or 3;
• R12, in each occurrence, is independently selected from a substituted or an unsubstituted heterocyclyl having up to 12 carbon atoms, comprising at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO, wherein any substituted heterocyclyl is substituted with up to three substituents selected independently from an acyl, an alkyl, or an alkoxycarbonyl, any of which having up to 12 carbon atoms, or —COOH;
• R13, in each occurrence, is independently selected from:
• 1) hydrogen;
• or 2) a cycloalkyl, an aryl, a haloalkyl, a heterocyclyl, or an alkyl group optionally substituted with at least one hydroxyl, any of which having up to 12 carbon atoms, wherein any heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• R14, in each occurrence, is independently selected from a heterocyclyl, a cycloalkyl, or an aryl, any of which having up to 12 carbon atoms, wherein any heterocyclyl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• Z, in each occurrence, is independently >O or >NR6;
• R′ and R″, in each occurrence, are independently selected from hydrogen or an alkyl having up to 12 carbon artoms;
• and
• R15 and R16, in each occurrence, are independently selected from:
• 1) hydrogen;
• 2) an alkyl having up to 12 carbon atoms;
• or 3) —(CH2)n-O—R13, —(CH2)n-R14, —COR13, —(CH2)n-CO-Z-R13, —CO2R13, —CO2—(CH2)n-R13, —CO2—(CH2)n-R12, —CO2—(CH2)n-CO-Z-R13, —CO2—(CH2)n-OR13, —CO—(CH2)n-O—(CH2)n-O—(CH2)n-R13, —CO—(CH2)n-O(CH2)n-OR13, or —CO—NH—(CH2)n-OR13;
• or R15 and R16 together form a substituted or an unsubstituted cyclic moiety comprising up to 12 carbon atoms, further comprising at least one additional, optional heteroatom or heterogroup selected independently from >O, >N—, >S, >NR6, >SO2, or >CO;
• wherein any substituted cyclic moiety is substituted with up to three substituents selected independently from:
• 1) hydroxyl;
• 2) an alkyl or a heteroaryl, any of which having up to 12 carbon atoms, wherein any heteroaryl comprises at least one heteroatom or heterogroup selected independently from >O, >N—, >S, or >NR6;
• or 3) COOR13, -Z-(CH2)n-R13, —COR13, —CO2—(CH2)n-R13, —CO(CH2)n-O—R13, —(CH2)n-CO2—R13, —SO2R8, —SO2NR′R″, or —NR′R″;
• wherein the —(CH2)n- linking moiety, in any occurrence, is optionally substituted with at least one group selected independently from hydroxyl, amino, or an alkyl having up to 3 carbon atoms.