CXCR3 antagonists

A compound having the formula:

• wherein
• {circle around (A)} is
• optionally independently substituted with one to four Ra groups, where each Ra is independently selected from the group consisting of halogen, —OR′, —OC(O)R′, —NR′R″, —SR′, —R′, —CN, —NO2, —CO2R′, —CONR′R″, —C(O)R′, —OC(O)NR′R″, —NR″C(O)R′, —NR″C(O)2R′, —NR′—C(O)NR″R′″, —NH—C(NH2)═NH, —NR′C(NH2)═NH, —NH—C(NH2)═NR′, —S(O)R′, —S(O)2R′, S(O)2NR′R″, —N3, —CH(Ph)2, perfluoro(C1–C4)alkoxy, and perfluoro(C1–C4)alkyl, wherein R′, R″ and R′″ are each independently selected from the group consisting of hydrogen, (C1–C8)alkyl, (C2–C8)heteroalkyl, unsubstituted aryl, unsubstituted heteroaryl, (unsubstituted aryl)-(C1–C4)alkyl, and (unsubstituted aryl)oxy-(C1–C4)alkyl;
• L is a member selected from the group consisting of a bond, C(O)—(C1–C8)alkylene, (C1–C8)alkylene and (C2–C8)heteroalkylene;
• Q is a member selected from the group consisting of a bond, (C1–C8)alkylene, (C2–C8)heteroalkylene, —C(O)—, —OC(O)—, —N(R8)C(O)—, —CH2CO—, —CH2SO— and —CH2SO2—;
• optionally L and Q can be linked together to form a 5- or 6-membered heterocyclic group having from 1 to 3 heteroatoms;
• R1 and R2 are members independently selected from the group consisting of H, (C1–C8)alkyl, (C2–C8)heteroalkyl, aryl and heteroaryl, or optionally are combined to form a 3 to 8-membered ring having from 0 to 2 heteroatoms as ring vertices;
• R3 is a member selected from the group consisting of hydroxy, (C1–C8)alkoxy, amino, (C1–C8)alkylamino, di(C1–C8)alkylamino, (C2–C8)heteroalkyl, (C3–C9)heterocyclyl, (C1–C8)acylamino, amidino, guanidino, ureido, cyano, heteroaryl, —CONR9R10 and —CO2R11;
• R4 is a member selected from the group consisting of (C1–C20)alkyl, (C2–C20)heteroalkyl, heteroaryl, aryl, heteroaryl(C1–C6)alkyl, heteroaryl(C2–C6)heteroalkyl, aryl(C1–C6)alkyl and aryl(C2–C6)heteroalkyl;
• R8 is selected from the group consisting of H, (C1–C8)alkyl, (C2–C8)heteroalkyl, heteroaryl and aryl;
• each R9, R10 and R11 is independently selected from the group consisting of H, (C1–C8)alkyl, (C2–C8)heteroalkyl, heteroaryl, aryl, heteroaryl(C1–C6)alkyl, heteroaryl(C2–C8)heteroalkyl, aryl(C1–C8)alkyl and aryl(C2–C8)heteroalkyl;
• and
• R14 is a member selected from the group consisting of(C1–C8)alkyl, (C2–C8)heteroalkyl, aryl(C1–C8)alkyl, aryl(C2–C8)heteroalkyl, heteroaryl(C1–C8)alkyl, heteroaryl(C2–C8)heteroalkyl, heteroaryl and aryl.