CCR5 antagonists useful for treating aids

A compound represented by the structural formula I

• or a diastereomer, enantiomer, atropisomer or pharmaceutically acceptable salt thereof, wherein:
• X is N;
• Q and Z are independently selected from the group consisting of CH and N, provided that one or both of Q and Z is N;
• R, R5, R6 and R7 are independently selected from the group consisting of H and (C1-C6)alkyl;
• R4 is (C1-C6)alkyl;
• R1 is H, (C1-C6)alkyl, fluoro-(C1-C6)alkyl-, R9-aryl(C1-C6)alkyl-, R9-heteroaryl-(C1-C6)alkyl-, (C1-C6)alkyl-SO2—, (C3-C6)cycloalkyl-SO2—, fluoro-(C1-C6)alkyl-SO2—, R9-aryl-SO2—, R9-heteroaryl-SO2—, N(R22)(R23)—SO2—, (C1-C6)alkyl-C(O)—, (C3-C6)cyclo-alkyl-C(O)—, fluoro-(C1-C6)alkyl-C(O)—, R9-aryl-C(O)—, NH—(C1-C6)alkyl-C(O)— or R9-aryl-NH—C(O)—;
• R2 is H or (C1-C6)alkyl, and R3 is H, (C1-C6)alkyl, (C1-C6)alkoxyl(C1-C6)alkyl-, (C3-C10)-cycloalkyl-, (C3-C10)cycloalkyl(C1-C6)alkyl-, R9-aryl, R9-aryl(C1-C6)-alkyl-, R9- heteroaryl, or R9-heteroaryl(C1-C6)alkyl-, provided that both X and Z are not each N;
• or R2 and R3 together are ═O, ═NOR10, or ═N—NR11R12;
• R8 is (R14, R15, R16)-substituted phenyl, (R14, R15, R16)-substituted pyridyl, (R14, R15, R16)-substituted pyridyl N-oxide, or (R14, R15, R16)-substituted pyrimidyl,
• R9 is 1, 2 or 3 substituents independently selected from the group consisting of H, halogen, (C1-C6)alkyl, (C1-C6)alkoxy, —CF3, —OCF3, CH3C(O)—, —CN, CH3SO2—, CF3SO2— and —N(R22)(R23);
• R10 is H, (C1-C6)alkyl, fluoro(C1-C6)alkyl-, (C3-C10)cycloalkyl(C1-C6)alkyl-, hydroxy(C2-C6)alkyl-, (C1-C6)alkyl-O—(C2-C6)alkyl-, (C1-C6)alkyl-O—C(O)—(C1-C6)alkyl- or N(R22)(R23)—C(O)—(C1-C6)alkyl-;
• R11 and R12 are independently selected from the group consisting of H, (C1-C6)alkyl and (C3-C10)cycloalkyl, or R11 and R12 together are C2-C6 alkylene and form a ring with the nitrogen to which they are attached;
• R14 and R15 are independently selected from the group consisting of (C1-C6)alkyl, halogen, —NR22R23, —OH, —CF3, —OCH3, —O-acyl and —OCF3;
• R16 is R14, hydrogen, phenyl, —NO2, —CN, —CH2F, —CHF2, —CHO, —CH═NOR24, pyridyl, pyridyl N-oxide, pyrimidinyl, pyrazinyl, —N(R24)CONR25R26, —NHCONH(chloro-(C1-C6)alkyl), —NHCONH((C3-C10)cycloalkyl(C1-C6)alkyl), —NHCO(C1-C6)alkyl, —NHCOCF3, —NHSO2N(R22)(R23), —NHSO2(C1-C6)alkyl, —N(SO2CF3)2, —NHCO2—(C1-C6)alkyl, C3-C10 cycloalkyl, —SR27, —SOR27, —SO2R27, —SO2NH(R22), —OSO2(C1-C6)alkyl, —OSO2CF3, hydroxy(C1-C6)alkyl-, —CON R24R25, —CON(CH2CH2OCH3)2, —OCONH(C1-C6)alkyl, —CO2R24, —Si(CH3)3 or —B(OC(CH3)2)2;
• R17 is (C1-C6)alkyl, —N(R22)(R23) or R19 -phenyl;
• R18, R22, R23, R24, R25 and R26 are independently selected from the group consisting of H and (C1-C6)alkyl;
• and
• R27 is (C1-C6)alkyl or phenyl;
• wherein heteroaryl is selected from the group consisting of thienyl, pyridyl and pyrimidyl.