Piperidine derivatives useful as CCR5 antagonists

A compound represented by the structural formula I

• or a pharmaceutically acceptable salt thereof;
• wherein:
• R1is
• R2 is benzyl or 4-fluorobenzyl;
• R3 selected from the group consisting of 6-membered heteroaryl, and 6-membered heteroaryl-N-oxide, wherein said, 6-membered heteroaryl or heteroaryl-N-oxide is pyrimidine or pyrimidine-N-oxide respectively, each of which is optionally substituted with 1-4 substituents which can be the same or different and, are independently selected from the group consisting of R11, R12, R13, R14 and R15;
• R4 is 1-3 substituents selected from the group consisting of H, halo, alkyl, haloalkyt, alkoxy, cycloalkyl, amide, CF3, OCF3, aryl, heteroaryl, —XR7, —CN, —CO2H,
• —CO2R22, R8-aryl(C1-C6)alky-, R8-heteroaryl(C1-C6)alkyl-, —C(O)NR21R22, —C(O)NH2, wherein R4 can be the same or different and is independently selected when there is more than one R4 present;
• R7is selected from the group consisting of aryl substituted aryl, heteroaryl, alkyl, haloalkyl and cycloalkyl;
• R8 is 1, 2 or 3 substituents selected from the group consisting of H, halo, (C1-C6)alkyl, (C1-C6)alkoxy, —CF3, —OCF3, CH3C(O)—, —CN, CH3SO2—, CF3SO2— and —NH2, wherein R8 can be the same or different and is independently selected when there are more than one R8 present;
• R9, R10 and B can be the same or different and are each independently selected from the group consisting of hydrogen, (C1-C6)alkyl, and —(C1-C6)heteroalkyl;
• R11 and R12 can be the same or different and are each independently selected from the group consisting of —(C1-C6)alkyl, —(C1-C6)haloalkyl, halogen, —NR19R26, —OH, CF3, —OCH3, —O-acyl, and —OCF3;
• R13 is selected from the group consisting of hydrogen, R11, H, phenyl, NO2, —CN, —CH2F, —CHF2, —CHO, —CH═NOR19, pyridyl-N-oxide, pyrimidinyl, pyrazinyl, N(R20)CO N R20R21, —NHCONH (chloro-(C1-C6)alkyl), —NHCONH ((C3-C10)-cycloalkyl(C1-C6)alkyl), —NHCO(C1-C6)alkyl, —NHCOCF3, —NHCOCF3, —NHSO2N((C1-C6)alkyl, —NHSO2(C1-C6)alkyl, —N(SO2CF3)2, —NHCO2(C1-C6)alkyl, (C3-C10)cycloalkyl, —SR22, SOR22, —SO2R22, —SO2N H(C1-C6)alkyl, —OSO2(C1-C6)alkyl, —OSO2CF3, hydroxy(C1-C6)alkyl, —CONR19R20, —CON (CH2CH2—O—CH3)2, —OCONH(C1-C6)alkyl, —CO2R19, Si(CH3)3 and —B(OC(CH3)2)2;
• R14 is selected from the group consisting of (C1-C6)alkyl, —(C1-C6)haloalkyl —NH2 and R15-phenyl;
• R15 is 1-3 substituents selected from the group consisting of hydrogen, (C1-C6)alkyl, (C1-C6)haloalkyl, —CF3, —CO2R20, —CN, (C1-C6)alkoxy and halogen;
• wherein R15 can be the same or different and is independently selected when there are more than one R15 present;
• R19, R20 and R21 can each be the same or different and are each independently selected from the group consisting of H, (C1-C6)alkyl and (C3-C6)cycloalkyl;
• R22 is selected from the group consisting of —(C1-C6)alkyl, -(C1-C6)haloalkyl, —(C2-C6)hydroxyalkyl, (C2-C6)alkylene, (C3-C6)cycloalkyl, aryl and aryl(C1-C6)alkyl-;
• A is selected from the group consisting of H, (C1-C6)alkyl, and (C2-C6)alkenyl,
• M is aryl optionally substituted with R4;
• and
• X is selected from the group consisting of CH2, SO2, SO, S, and O, with the following proviso:
• when R1 is phenyl, or naphthyl, R2 cannot be H, (C1-C6)alkyf or —C(O)—(C1-C6)alky.