Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents

A compound having the following formula I:

• or a stereoisomer, prodrug or pharmaceutically acceptable salt thereof,
• wherein:
• Q1 is azido or —NR10R11;
• Q2 is —NR10R12;
• each Q3 and Q4 is —OR7;
• Q5 is H, halogen, cyano, azido, —OR8, —NR2R3, a protected amino group or a nitrogen containing heterocyclic radical which optionally includes one or more additional heteroatoms selected from N, O and S wherein the heterocyclic radical is covalently linked through said nitrogen atom;
• each R1 is, independently, H or a hydroxyl protecting group;
• each R2 is, independently, H, an amino protecting group, C1-C12 alkyl or substituted C1-C12 alkyl;
• each R3 is, independently, H, an amino protecting group, cyano, C1-C12 alkyl, substituted C1-C12 alkyl, C2-C12 alkenyl, substituted C2-C12 alkenyl, C2-C12 alkynyl, substituted C2-C12 alkynyl or —(CH2)n-(L1)m-(CH2)nn-E1;
• each R6 is, independently, H or an amino protecting group;
• each R7 is, independently, H, a hydroxyl protecting group or or —(CH2)n-(L1)m—(CH2)nn-E1;
• R8 is H, a hydroxyl protecting group, C1-C12 alkyl, substituted C1-C12 alkyl, C2-C12 alkenyl, substituted C2-C12 alkenyl, C2-C12 alkynyl, substituted C2-C12 alkynyl or or —(CH2)n-(L1)m-(CH2)nn-E1;
• each R10 is, independently, H, C1-C12 alkyl or substituted C1-C12 alkyl;
• each R11 is, independently, cyano, C1-C12 alkyl, substituted C1-C12 alkyl, C2-C12 alkenyl, substituted C2-C12 alkenyl, C2-C12 alkynyl, substituted C2-C12 alkynyl or —(CH2)n-(L1)m-(CH2)nn-E1;
• and
• R12 is a group having the following formula III:
• each L1 is, independently, S, O or NJ1;
• L2 is CH or N;
• each n is, independently, an integer from 1 to 8;
• each m is, independently, 0 or 1;
• each nn is, independently, 0 or an integer from 1 to 8;
• mm is 1 or 2;
• each E1 is, independently, H, hydroxyl, halogen, cyano, —NJ1J2, C2-C12 alkenyl, substituted C2-C12 alkenyl, C2-C12 alkynyl, substituted C2-C12 alkynyl, C5-C20 aryl, substituted C5-C20 aryl, heteroaryl, substituted heteroaryl, a heterocyclic radical, a substituted heterocyclic radical or a substituted or unsubstituted mono or poly cyclic structure that is unsaturated, partially saturated or fully saturated and optionally includes one or more heteroatoms selected from O, N and S;
• each J1 and J2 is, independently, H, C1-C12 alkyl, substituted C1-C12 alkyl, C2-C12 alkenyl, substituted C2-C12 alkenyl, C2-C12 alkynyl, substituted C2-C12 alkynyl, C5-C20 aryl, substituted C5-C20 aryl, —C(═O)—X, a heterocyclic radical or a substituted heterocyclic radical;
• each X is, independently, H, C1-C12 alkyl or substituted C1-C12 alkyl;
• each Z1 and Z2 is, independently, H, hydroxyl or a protected hydroxyl;
• and
• Z3 is a group having the following formula IV:
• wherein when Q2 is —N(H)C(═O)C(H)(OH)CH2CH2NH2 then Q1 is other than —N(H)CH3 or —N(H)CH2CH3 and Q5 is other than —N(H)C(═NH)NH2 or —N(H)CH═NH2.