Triazinone and diazinone derivatives useful as HSP90 inhibitors

A compound represented by the following structural formula:

• or a tautomer, pharmaceutically acceptable salt, or a prodrug thereof, wherein:
• X is —C(R7)2—, —NH—, —O—, or —S—;
• X1 is O or S;
• X20 is a C1-C4 alkyl, NR7, C(O), C(S), C(NR8), or S(O)p;
• Z is an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocyclyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, an optionally substituted haloalkyl, an optionally substituted heteroalkyl, optionally substituted alkoxy, —C(O)NR28R29, —C(S)NR28R29, —C(NR32)NR28R29, —NR33C(O)R31, —NR33C(S)R31, —NR33C(NR32)R31, halo, —OR33, cyano, nitro, haloalkoxy, —C(O)R33, —C(S)R33, —C(NR32)R33, —NR28R29, —C(O)OR33, —C(S)OR33, —C(NR32)OR33, —OC(O)R33, —OC(S)R33, —OC(NR32)R33, —NR30C(O)NR28R29, —NR33C(S)NR28R29, —NR33C(NR32)NR28R29, —OC(O)NR28R29, —OC(S)NR28R29, —OC(NR32)NR28R29, —NR33C(O)OR31, —NR33C(S)OR31, —NR33C(NR32)OR31, —S(O)hR33, —OS(O)pR33, —NR33S(O)pR33, —S(O)pNR28R29, —OS(O)pNR28R29, or —NR33S(O)pNR28R29 guanadino, —C(O)SR31, —C(S)SR31, —C(NR32)SR31, —OC(O)OR31, —OC(S)OR31, —OC(NR32)OR31, —SC(O)R33, —SC(O)OR31, —SC(NR32)OR31, —SC(S)R33, —SC(S)OR31, —SC(O)NR28R29, —SC(NR32)NR28R28, —SC(S)NR28R29, —SC(R32)R33, —OS(O)pOR31, —S(O)pOR31, —NR30S(O)pOR31, —SS(O)pR33, —SS(O)pOR31, —SS(O)pNR28R29, —OP(O)(OR31)2, or —SP(O)(OR31)2;
• R2 and R3 are each independently —NR7H, —OR7, —SR7, —O(CH2)mOH, —O(CH2)mSH, —O(CH2)mNR7H, —S(CH2)mOH, —S(CH2)mSH, —S(CH2)mNR7H, —OC(O)NR10R11, —SC(O)NR10R11, —NR7C(O)NR10R11, —OC(O)R7, —SC(O)R7, —NR7C(O)R7, —OC(O)OR7, —SC(O)OR7, —NR7C(O)OR7, —OCH2C(O)R7, —SCH2C(O)R7, —NR7CH2C(O)R7, —OCH2C(O)OR7, —SCH2C(O)OR7, —NR7CH2C(O)OR7, —OCH2C(O)NR10R11, —SCH2C(O)NR10R11, —NR7CH2C(O)NR10R11, —OS(O)R7, —SS(O)R7, —S(O)pOR7, —NR7S(O)pR7, —OS(O)pNR10R11, —SS(O)pNR10R11, —NR7S(O)pNR10R11, —OS(O)pOR7, —SS(O)pOR7, —NR7S(O)pOR7, —OC(S)R7, —SC(S)R7, —NR7C(S)R7, —OC(S)OR7, —SC(S)OR7, —NR7C(S)OR7, —OC(S)NR10R11, —SC(S)NR10R11, —NR7C(S)NR10R11, —OC(NR8)R7, —SC(NR8)R7, —NR7C(NR8)R7, —OC(NR8)OR7, —SC(NR8)OR7, —NR7C(NR8)OR7, —OC(NR8)NR10R11, —SC(NR8)NR10R11, —NR7C(NR8)NR10R11, —OP(O)(OR7)2, or —SP(O)(OR7)2;
• R5 is —X20R50, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocyclyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
• R7 and R8, for each occurrence, are independently, —H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocyclyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
• R10 and R11, for each occurrence, are independently —H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocyclyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
• or R10 and R11, taken together with the nitrogen to which they are attached, form an optionally substituted heterocyclyl or an optionally substituted heteroaryl;
• R28 and R29, for each occurrence is independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocyclyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
• R33 and R31 for each occurrence is independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocyclyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
• and
• R32, for each occurrence is independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocyclyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —C(O)R33, —C(O)NR28R29, —S(O)pR33, or —S(O)pNR28R29;
• R50 is an optionally substituted aryl or an optionally substituted heteroaryl;
• h is 0, 1 or 2;
• p, for each occurrence, is independently, 0, 1 or 2;
• m for each occurrence, is independently 1, 2, 3, or 4;
• and
• n is 0, 1, 2, or 3.