Urazole compounds useful as anti-inflammatory agents

A compound having the formula,

• or a pharmaceutically-acceptable salt thereof, in which:
• K and L are independently O or S;
• Q is —O—, —NH—, —S—, —CO2—, —C(═O)—, —OC(═O), —NHC(═O)—, —C(═O)NH—, —N HCO2—, C1-4alkylene, C1-4substituted alkylene, C2-4alkenylene, C2-4substituted alkenylene, or optionally-substituted bivalent C1-4alkoxy, C1-4alkylthio, C1-4aminoalkyl, C0-4sulfonyl, C0-4sulfonamide, C1-4acyl, or C1-4alkoxycarbonyl;
• Z is N or CR4b;
• R1 is aryl or heteroaryl optionally substituted with one to two substituents selected from halogen, alkyl, substituted alkyl, nitro, cyano, OR10, NR10R11, CO2R10, C(═O)R10, C(═O)NR10R11, NR10C(═O)R11, NR10C(═O)OR11, S(O)pR10, NR11SO2R10, SO2NR10R11, —NHCH(alkyl)CO2R10, aryl, cycloalkyl, and heteroaryl;
• R3 is attached to any available carbon atom of ring A and at each occurrence is independently selected from halogen, alkyl, substituted alkyl, alkenyl, nitro, S(O)qR8, NR9SO2R8, SO2NR8R9, A1—CN, A1—OR8, A1—NR8R9, A1—C(═O)R8, A1—OC(═O)R8, A1—OC(═O)NR8R9, A1—NR8C(═O)R9, A1—NR8C(═O)OR9, A2—CO2R8, and A2—C(═O)NR8R9;
• or where R3 is attached to a carbon atom other the Q—R1 substituted carbon atom, R3 may be oxo (═O);
• A1 is a bond, —C1-4alkylene-, —NHC(═O)—, or —NHC(═O)C1-4alkylene-;
• A2 is a bond, —C1-4alkylene-, —NHC(═O)—, —NHC(═O)C1-4alkylene-, —C(═O)— or —C(═O)C1-4alkylene-;
• R4a and R4c are halogen, alkyl, cyano, trifluoromethyl, or nitro;
• R4b is hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, hydroxy, alkoxy, phenyloxy, —CO2H, —C(═O)H, amino, NH(alkyl), N(alkyl)2, CO2alkyl, C(═O)alkyl, alkylthio, —C(═O)NH(CH2)1-4CO2H, —C(═O)NH(CH2)1-4CO2(alkyl), aryl, heteroaryl, or heterocycle, wherein each of the aryl, heteroaryl, and heterocycle groups are optionally substituted with one to two halogen, C1-4alkyl, OMe, CF3, CN, OCF3, CO2H, —C(═O)H, CO2alkyl, or C(═O)alkyl;
• R6 and R7 (i) selected independently of each other are hydrogen, alkyl, substituted alkyl, substituted alkenyl, alkoxy, or optionally-substituted cycloalkyl, aryl, heteroaryl, or heterocyclo;
• or (ii) taken together form a heterocyclo ring;
• R8 and R9 (i) selected independently of each other are hydrogen, alkyl, substituted alkyl, substituted alkenyl, alkoxy, or optionally-substituted cycloalkyl, aryl, heteroaryl, or heterocyclo except R8 is not hydrogen when attached to a sulfonyl group as in S(═O)R8 or S(O)2R8;
• or (ii) taken together form a heterocyclo ring;
• R10 and R11 (i) selected independently of each other are hydrogen, alkyl, substituted alkyl, substituted alkenyl, alkoxy, or optionally-substituted cycloalkyl, aryl, heteroaryl, or heterocyclo except R10 is not hydrogen when attached to a sulfonyl group as in S(═O)R10 or S(O)2R10;
• or (ii) taken together form a heterocyclo;
• p and q are independently 0, 1, or 2;
• r is 1 or 2;
• and
• t is 0, 1 or 2.

A compound having the formula,

• or a pharmaceutically-acceptable salt thereof, in which:
• Q is —O—, —OC(═O) or optionally-substituted bivalent C1-4alkoxy;
• Z is N or CR4b;
• R1 is hydrogen, alkylsilyl, or phenyl optionally substituted with one to two substituents selected from halogen, C1-4alkyl, hydroxy, alkoxy, haloalkoxy, haloalkyl, cyano, and nitro;
• and
• R4a, R4b, and R4c are independently selected from halogen, C1-4alkyl, haloalkyl, haloalkoxy, cyano, and nitro.