Mebendazole prodrugs with enhanced solubility and oral bioavailability

A compound having the structure of formula (I):

• wherein:
• R2 or R2′ can be absent or present, provided that at least one of R2 and R2′ is present;
• the dashed line indicates a double bond between N1 and C2, in which R2′ is present and R2 is absent, or a double bond between N3 and C2, in which R2 is present and R2′ is absent;
• wherein:
• R2 is H and R1 is:
• wherein n is an integer selected from 1, 2, 3, 4, 5, 6, 7, and 8, and R3 is C1-C6 straight-chain or branched alkyl, each of which can be substituted;
• or
• R1 is H and R2 or R2′ when present is —(CR4R5)m—Ry, wherein m is an integer selected from 1, 2, 3, 4, 5, 6, 7, and 8, and wherein —(CR4R5)m—Ry is selected from the group consisting of:
• —(CR4R5)m—O—(C═O)—O—R6, wherein C4 and C5 are each H and R6 is C1-C6 straight-chain or branched alkyl;
• —(CR4R5)m—O—(C═O)—(CR7R8)p—C(═O)—OR9, wherein R4, R5, R7, R8, and R9 are each H;
• —(CR4R5)m—O—(C═O)—O—(CR7R8)p—R10 or —(CR4R5)m—O—(C═O)—R10, wherein R4, R5, R7, R8, and R9 are each H, and R10 is a monosaccharide;
• —(CR4R5)m—P(═O)(O−)—O—(CR7R8)p—O—(C═O)—O—R6, wherein R4 and R5 are each H, R7 and R8 are each H or C1-C6 substituted or unsubstituted alkyl, and R6 is C1-C6 straight-chain or branched alkyl;
• and
• —(CR4R5)m—O—(C═O)—(CR7R8)p—CR11R12—C(═O)—OR9;
• —(CR4R5)m—O—(C═O)—(CR7R8)p—NR15—(C═O)—CR16R17(NR18—C(═O)—R19), and —(CR4R5)m—R20, wherein each R4, R5, R7, and R8 is H, R9, R11, R15, R16, and R18 are each H;
• R12 is —NR13R14, wherein R13 and R14 are each H;
• and R17 and R19 are each C1-C6 straight-chain or branched alkyl;
• and R20 is an amino acid or a substituted amino acid;
• or a pharmaceutically acceptable salt thereof.