Macrocyclic broad spectrum antibiotics

A compound of Formula (II):

• wherein:
• R1 and R2 are each independently H, —(C1-C6)alkyl, —(C1-C6)alkyl-OR23, —CH2CH(OH)CH2NH2, —CH2CH(heterocycloalkyl)CH2NH2, —CH2C(O)NH2, —CH2C(O)N(H)CH2CN, —(C1-C6)alkyl-C(O)OR23, —(C1-C6)alkyl-NR21R22, —(C1-C6)alkyl-C(O)NR25R26, —(C1-C6)alkyl-N(R23)C(O)(C1-C6)alkylNR21R22, —(C1-C6)alkyl-N(R23)C(O)(C1-C6)alkyl, —(C1-C6)alkyl-C(O)N(R23)(C1-C6)alkyl, —(C1-C6)alkyl-C(O)N(R23)(C1-C6)alkyl-heterocycloalkyl, —(C1-C6)alkyl-NR23C(═NH)NR21R22, —(C1-C6)alkyl-NR23C(═NH)R23, —(C1-C6)alkyl-[(C1-C6)alkyl-NR21R22]2, —(C1-C6)heteroalkyl, or optionally substituted heterocycloalkyl;
• or R1 and R2 and the atoms to which they are attached form an optionally substituted heterocycloalkyl ring;
• R3 is H or —(C1-C6)alkyl;
• R4 is H, —(C1-C6)alkyl, —(C1-C6)alkyl-OH, —(C3-C6)cycloalkyl, or —C(O)NH2;
• or R3 and R4 are combined to form a heterocycloalkyl ring;
• R5 is H or —(C1-C6)alkyl;
• or R4 and R5 and the carbon atom to which they are attached form a cyclopropyl ring;
• R6, R7, and R8 are each independently H or —(C1-C6)alkyl;
• R9 is H, —(C1-C6)alkyl, —(C1-C6)haloalkyl, or —(C3-C6)cycloalkyl;
• R10 is H or —(C1-C6)alkyl;
• R11 and R12 are each independently H, —NH2, —(C1-C6)alkyl, —(C1-C6)alkyl-OR23, —(C1-C6)alkyl-SR23, —(C1-C6)alkyl-C(O)OR23, —(C1-C6)alkyl-NR21R22, —(C1-C6)alkyl-NR23OR23, —(C1-C6)alkyl-NHC(O)NR23OR23, —(C1-C6)alkyl-O—(C1-C6)alkyl-NR25R26, —(C1-C6)alkyl-CN, —(C1-C6)alkyl-NR23C(O)R23, —(C1-C6)alkyl-C(O)NR25R26, —(C1-C6)heteroalkyl-CO2H, —(C1-C6)alkyl-S(O)(C1-C6)alkyl, —(C1-C6)alkyl-N(H)CH═NH, —(C1-C6)alkyl-C(NH2)=NH, —(C1-C6)alkyl-N(H)C(═NH)NH2, —(C1-C6)alkyl-N(H)S(O)2NR25R26, —(C1-C6)alkyl-N(H)S(O)2(C1-C6)alkyl, —(C1-C6)alkyl-N(H)—C(O)NR25R26, —(C1-C6)alkylC(O)N(H)[optionally substituted(C2-C6)alkyl]-OR23, —(C1-C6)alkylN(H)C(O)(C1-C6)alkyl-OR23, —(C1-C6)alkylC(O)N(H)heterocycloalkyl, —(C1-C6)alkylC(O)NR25R26, —(C1-C6)alkyl-N(H)—C(O)—(C1-C6)alkyl-NR25R26, —(C1-C6)alkyl-N(H)—(C1-C6)alkylC(O)NR25R26, —(C1-C6)alkyl-heterocycloalkyl, optionally substituted —(C1-C6)alkyl-N(H)heterocycloalkyl, or —(C1-C6)alkyl-heteroaryl;
• R13 and R14 are each independently H, —NH2, —(C1-C6)alkyl, —(C1-C6)alkyl-OR23, —(C1-C6)alkyl-SR23, —(C1-C6)alkyl-C(O)OR23, —(C1-C6)alkyl-NR21R22, —(C1-C6)alkyl-CN, —(C1-C6)alkyl-C(O)NR25R26, —(C1-C6)alkyl-N(H)C(NH)NH2, —(C1-C6)alkyl-heterocycloalkyl, or —(C1-C6)alkyl-heteroaryl;
• or R13 and R19 are combined to form an optionally substituted heterocycloalkyl ring;
• and R14 is H;
• R15, R16, R17, R18, and R19 are each independently H, —(C1-C6)alkyl, —(C3-C6)cycloalkyl, —(C1-C6)alkyl-OR23, —(C1-C6)alkyl-C(O)OR23, or —(C1-C6)alkyl-NR21R22;
• X is optionally substituted —(C1-C6)alkyl-, —(C2-C6)alkenyl-, —(C2-C6)alkynyl, optionally substituted —(C3-C7)cycloalkyl-, optionally substituted heterocycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, —O—(C1-C6)alkyl-, —N(R24)(C1-C6)alkyl-, —N(R24)(C6-C10)aryl-, or —SO2(C1-C6)alkyl-;
• Y is a bond, —O—, —S—, optionally substituted —(C1-C6)alkyl-, —(C2-C6)alkenyl-, —(C2-C6)alkynyl, —(C1-C6)alkyl-N(R24)(C1-C6)alkyl-, —O—(C1-C6)alkyl-, —O(C6-C10)aryl-, —N(R24)(C1-C6)alkyl-, —N(R24)SO2(C1-C6)alkyl-, —N(R24)C(O)(C1-C6)alkyl-, —C(O)(C1-C6)alkyl-, —S(C1-C6)alkyl-, —SO2(C1-C6)alkyl-, —C(O)NH(C1-C6)alkyl-, optionally substituted —(C3-C7)cycloalkyl-, optionally substituted —C(O)N(R24)aryl-, optionally substituted —N(R24)C(O)aryl-, optionally substituted —N(R24)SO2aryl-, optionally substituted heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
• Z is H, halogen, —NH2, —CN, —CF3, —CO2H, —(C1-C12)alkyl, —(C2-C12)alkenyl, —CH═((C3-C7)cycloalkyl), —(C2-C12)alkynyl, —C(O)NR25R26, —O—(C1-C12)alkyl, —S—(C1-C12)alkyl, —O—(C3-C10)[optionally substituted (C3-C7)cycloalkyl], —O—(C1-C6)alkyl-OR23, —(C1-C12)alkyl-OR23, —(C1-C12)alkyl-CN, —S—(C1-C12)alkyl, —N(R24)(C1-C12)alkyl, —N(R24)C(O)(C1-C12)alkyl, optionally substituted —(C3-C7)cycloalkyl, —(C1-C6)alkyl-(C3-C7)cycloalkyl, —(C1-C6)alkyl-heterocycloalkyl, optionally substituted heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
• each R21 and R22 is independently H, —(C1-C6)alkyl, —(C1-C6)heteroalkyl, —(C1-C6)alkyl-CO2H, —C(O)(C1-C6)alkyl, —C(O)N(R31)2, or —SO2N(R31)2;
• or R21 and R22 and the nitrogen atom to which they are attached form a heterocycloalkyl ring;
• each R31 is independently H or —(C1-C6)alkyl;
• or two R31 and the nitrogen atom to which they are attached form a heterocycloalkyl ring;
• each R23 is independently H or —(C1-C6)alkyl;
• each R24 is independently H or —(C1-C6)alkyl;
• each R25 and R26 is independently H or optionally substituted —(C1-C6)alkyl;
• or R25 and R26 and the nitrogen atom to which they are attached form a heterocycloalkyl ring;
• each R27 is independently halogen, —NR23R24, —NHC(O)R23, —NHC(O)NR23R24, nitro, hydroxyl, optionally substituted —(C1-C6)alkyl, optionally substituted —(C1-C6)heteroalkyl, optionally substituted —(C1-C6)heteroalkyloxy, optionally substituted —(C1-C6)heteroalkylamino, —(C1-C6)alkoxy, —C(O)(C1-C6)alkyl, or —S(O)2(C1-C6)alkyl;
• or R1 and R27 and the atoms to which they are attached form an optionally substituted 5- or 6-membered heterocycloalkyl ring;
• each R28 is independently halogen, —NR23R24, —NHC(O)R23, —NHC(O)NR23R24, nitro, hydroxyl, optionally substituted —(C1-C6)alkyl, optionally substituted —(C1-C6)heteroalkyl, optionally substituted —(C1-C6)heteroalkyloxy, optionally substituted —(C1-C6)heteroalkylamino, —(C1-C6)alkoxy, —C(O)(C1-C6)alkyl, or —S(O)2(C1-C6)alkyl;
• or R2 and R28 and the atoms to which they are attached form an optionally substituted 5- or 6-membered heterocycloalkyl ring;
• n is 0 or 1;
• p is 0, 1, or 2;
• and
• q is 0, 1, or 2;
• or a pharmaceutically acceptable salt, solvate, or prodrug thereof.