Piperazinylpiperidine derivatives as chemokine receptor antagonists

A compound of Formula I:

• or pharmaceutically acceptable salt or prodrug thereof, wherein:
• R1 is heteroaryl optionally substituted by one or more R6;
• R2 is H, halo, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, aryl, heteroaryl, C3-C7 cycloalkyl, heterocycloalkyl, SOR7, SO2R7, COR8, OR9, SR9, COOR9, NR10R11 or NR10COR8;
• R3 is F, Cl, Br, I, C1-C4 haloalkyl, C1-C4 haloalkoxy or heteroaryl;
• R4 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C1-C6 haloalkyl;
• R5 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C1-C6 haloalkyl;
• R6 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, amino, (C1-C6 alkyl)amino or di(C1-C6 alkyl)amino;
• R7 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, aryl, heteroaryl, C3-C7 cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, (C3-C7 cycloalkyl)alkyl, heterocycloalkylalkyl, or NR12R13;
• R8 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, aryl, heteroaryl, C3-C7 cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, (C3-C7 cycloalkyl)alkyl, heterocycloalkylalkyl, or NR12R13;
• R9 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, alkoxyalkyl, haloalkoxyalkyl, aryloxyalkyl, heteroaryloxyalkyl, cycloalkyloxyalkyl, heterocycloalkyloxyalkyl, aryl, heteroaryl, C3-C7 cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl;
• (C3-C7 cycloalkyl)alkyl or heterocycloalkylalkyl;
• R10 and R11 are each, independently, H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, aryl, heteroaryl, C3-C7 cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl;
• (C3-C7 cycloalkyl)alkyl or heterocycloalkylalkyl;
• or R10 and R11 together with the N atom to which they are attached form a 3-, 4-, 5-, 6-, or 7-membered heterocycloalkyl group;
• R12 and R13 are each, independently, H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, aryl, heteroaryl, C3-C2 cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl;
• (C3-C7 cycloalkyl)alkyl or heterocycloalkylalkyl;
• or R12 and R13 together with the N atom to which they are attached form a 3-, 4-, 5-, 6-, or 7-membered heterocycloalkyl group;
• r is 1, 2 or 3.