Method of treating HIV infection

A method of treating human immunodeficiency virus (HIV) infection in an antiretroviral treatment-experienced mammal, the method comprising administering to the mammal an effective amount of a compound of the formula:

• or a pharmaceutically acceptable salt, a prodrug, or an ester thereof, or a pharmaceutically acceptable composition of said compound, said salt, said prodrug, or said ester thereof, wherein:
• A is of the formula:
• R1 is H or an alkyl, an alkenyl, an alkynyl, a cycloalkyl, a cycloalkylalkyl, an aryl, an aralkyl, a heterocycloalkyl, a heterocycloalkylalkyl, a heteroaryl, or a heteroaralkyl, in which at least one hydrogen atom is optionally substituted with a substituent selected from the group consisting of OR7, SR7, CN, NO2, N3, and a halogen, wherein R7 is H, an unsubstituted alkyl, an unsubstituted alkenyl, or an unsubstituted alkynyl;
• Y and Z are the same or different and each is selected from the group consisting of CH2, O, S, SO, SO2, NR8, R8C(O)N, R8C(S)N, R8OC(O)N, R8OC(S)N, R8SC(O)N, R8R9NC(O)N, and R8R9NC(S)N, wherein R8 and R9 are each selected from the group consisting of H, an unsubstituted alkyl, an unsubstituted alkenyl, and an unsubstituted alkynyl;
• n is an integer from 1 to 5;
• X is a covalent bond, CHR10, CHR10CH2, CH2CHR10, O, NR10, or S, wherein R10 is H, an unsubstituted alkyl, an unsubstituted alkenyl, or an unsubstituted alkynyl;
• Q is C(O), C(S), or SO2;
• R2 is H, a C1-C6 alkyl, a C2-C6 alkenyl, or a C2-C6 alkynyl;
• m is an integer from 0 to 6;
• R3 is a cycloalkyl, a heterocycloalkyl, an aryl, or a heteroaryl in which at least one hydrogen atom is optionally substituted with a substituent selected from the group consisting of alkyl, (CH2)pR11, OR12, SR12, CN, N3, NO2, NR12R13, C(O)R12, C(S)R12, CO2R12, C(O)SR12, C(O)NR12R13, C(S)NR12R13, NR12C(O)R13, NR12C(S)R13, NR12CO2R13, NR12C(O)SR13, and a halogen, wherein:
• p is an integer from 0 to 5;
• R11 is a cycloalkyl, a heterocycloalkyl, an aryl, or a heteroaryl in which at least one hydrogen atom is optionally substituted with a substituent selected from the group consisting of a halogen, OH, OCH3, NH2, NO2, SH, and CN;
• and
• R12 and R13 are the same or different and each is selected from the group consisting of H, an unsubstituted alkyl, an unsubstituted alkenyl, and an unsubstituted alkynyl;
• R4 is OH, ═O (keto), or NH2, wherein, when R4 is OH, it is optionally in the form of a pharmaceutically acceptable ester or prodrug, and when R4 is NH2, it is optionally an amide, a hydroxylamino, a carbamate, a urea, an alkylamino, a dialkylamino, a protic salt thereof, or a tetraalkylammonium salt thereof;
• R5 is H, a C1-C6 alkyl radical, a C2-C6 alkenyl radical, or (CH2)qR14, wherein q is an integer from 0 to 5, and R14 is a cycloalkyl, a heterocycloalkyl, an aryl, or a heteroaryl radical in which at least one hydrogen atom is optionally substituted with a substituent selected from the group consisting of a halogen, OH, OCH3, NH2, NO2, SH, and CN;
• W is C(O), C(S), or SO2;
• and
• R6 is a cycloalkyl, heterocycloalkyl, aryl, or heteroaryl radical in which at least one hydrogen atom is optionally substituted with a substituent selected from the group consisting of a halogen, OR15, SR15, S(O)R15, SO2R15, SO2NR15R16, SO2N(OH)R15, CN, CR15═NR16, CR15═N(OR16), N3, NO2, NR15R16, N(OH)R15, C(O)R15, C(S)R15, CO2R15, C(O)SR15, C(O)NR15R16, C(S)NR15R16, C(O)N(OH)R15, C(S)N(OH)R15, NR15C(O)R16, NR15C(S)R16, N(OH)C(O)R15, N(OH)C(S)R15, NR15CO2R16, N(OH)CO2R15, NR15C(O)SR16, NR15C(O)NR16R17, NR15C(S)NR16R17, N(OH)C(O)NR15R16, N(OH)C(S)NR15R16, NR15C(O)N(OH)R16, NR15C(S)N(OH)R16, NR15SO2R16, NHSO2NR15R16, NR15SO2NHR16, P(O)(OR15)(OR16), an alkyl, an alkoxy, an alkylthio, an alkylamino, a cycloalkyl, a cycloalkylalkyl, a heterocycloalkyl, a heterocycloalkylalkyl, an aryl, an aryloxy, an arylamino, an arylthio, an aralkyl, an aryloxyalkyl, an arylaminoalkyl, an aralkoxy, an (aryloxy)alkoxy, an (arylamino)alkoxy, an (arylthio)alkoxy, an aralkylamino, an (aryloxy)alkylamino, an (arylamino)alkylamino, an (arylthio)alkylamino, an aralkylthio, an (aryloxy)alkylthio, an (arylamino)alkylthio, an (arylthio)alkylthio, a heteroaryl, a heteroaryloxy, a heteroarylamino, a heteroarylthio, a heteroaralkyl, a hetero aralkoxy, a heteroaralkylamino, and a heteroaralkylthio,
• wherein R15, R16, and R17 are the same or different and each is H, an unsubstituted alkyl, or an unsubstituted alkenyl,
• wherein, when at least one hydrogen atom of R6 is substituted with a substituent other than a halogen, OR15, SR15, CN, N3, NO2, NR15R16, C(O)R15, C(S)R15, CO2R15, C(O)SR15, C(O)NR15R16, C(S)NR15R16, NR15C(O)R16, NR15C(S)R16, NR15CO2R16, NR15C(O)SR16, NR15C(O)NR16R17, or NR15C(S)NR16R17, at least one hydrogen atom on said substituent is optionally substituted with a halogen, OR15, SR15, CN, N3, NO2, NR15R16, C(O)R15, C(S)R15, CO2R15, C(O)SR15, C(O)NR15R16, C(S)NR15R16, NR15C(O)R15, NR15C(S)R16, NR15CO2R16, NR15C(O)SR16, NR15C(O)NR16R17, or NR15C(S)NR16R17.