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US 8,008,316 B2Granted
Azonafide derived tumor and cancer targeting compounds
AssigneeThe United States of America, as represented by the Secretary, Department of Health and Human Services
InventorsNadya I. Tarasova, Marcin Dyba, Christopher J. Michejda
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Abstract
An azonafide-based compound of Formula I, a composition comprising the compound, and a method of using the compound to deliver a cytotoxic azonafide derivative to a cell, as well as related compounds and methods for the use thereof to pre-pare an azonafide-based compound of Formula I.
Claims39
A compound of Formula I:
- wherein n is 1-8;
- p is 2-4;
- X is —(CH2)qNH-A, —(CH2)qNH-A-B, —(CH2)qNH-A-W—B, -A, -A-B, -A-W—B, -W-A, —W-A-B, or —W-A-W—B, wherein A is a peptide comprising two or more amino acids, B is a cell-targeting construct, W is a coupling moiety selected from the group consisting of —(CH2)mNH—, —C(O)(CH2)mC(O)—, —C(O)(CH2)m—, and
- m is 1-16 and q is 1-8;
- Z is hydrogen, methyl, or, when n is 2 and R2 is —(CH2)2—, Z is a bond between R2 and the nitrogen to which Z is attached;
- R1 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkynoyl, alkylthiol, formyl, halogen, aryl, nitro, sulfanyl, hydrazino, amino, oxyamino, alkylamino, dialkylamino, and combinations thereof;
- and
- R2 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkynoyl, alkylthiol, formyl, halogen, aryl, nitro, sulfanyl, hydrazino, amino, oxyamino, alkylamino, dialkylamino, and combinations thereof, or R2 is —(CH2)2—.
5 more elements
A compound of Formula II:
- wherein n is 1-8;
- p is 2-4;
- R3 is H, —(CH2)qNH—Y, —(CH2)qNH-A-Y, —Y, or -A-Y, wherein A is a peptide comprising two or more amino acids, Y is a coupling moiety selected from the group consisting of
- m is 1-16 and q is 1-8;
- Z is hydrogen or methyl;
- R1 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkynoyl, alkylthiol, formyl, halogen, aryl, nitro, sulfanyl, hydrazino, amino, oxyamino, alkylamino, dialkylamino, and combinations thereof;
- and
- R2 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkynoyl, alkylthiol, formyl, halogen, aryl, nitro, sulfanyl, hydrazino, amino, oxyamino, alkylamino, dialkylamino, and combinations thereof.
5 more elements
A compound of Formula II:
- wherein n is 1-8;
- p is 2-4;
- R3 is —(CH2)qNH2 and q is 1-8;
- Z is hydrogen, methyl, or, when n is 2 and R2 is —(CH2)2—, Z is a bond between R2 and the nitrogen to which Z is attached;
- R1 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkynoyl, alkylthiol, formyl, halogen, aryl, nitro, sulfanyl, hydrazino, amino, oxyamino, alkylamino, dialkylamino, and combinations thereof;
- and
- R2 is selected from the group consisting of alkyl, alkoxy, alkynoyl, alkylthiol, formyl, halogen, aryl, nitro, sulfanyl, hydrazino, amino, oxyamino, alkylamino, dialkylamino, and combinations thereof, or R2 is —(CH2)2—.
4 more elements
A compound of Formula II:
- wherein n is 1-8;
- p is 2-4;
- R3 is —(CH2)qNH2, —(CH2)qNH—Y, —(CH2)qNH-A-Y, -Y, or -A-Y, wherein A is a peptide comprising two or more amino acids, Y is a coupling moiety selected from the group consisting of
- m is 1-16 and q is 1-8;
- Z is a bond between R2 and the nitrogen to which Z is attached;
- R1 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkynoyl, alkylthiol, formyl, halogen, aryl, nitro, sulfanyl, hydrazino, amino, oxyamino, alkylamino, dialkylamino, and combinations thereof;
- and
- R2 is —(CH2)2—.
5 more elements
Dependencies are inferred from the claim text.