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US 12,433,873 B2Granted
Microtubule polymerization inhibitor prodrugs and methods of using the same
AssigneeUniversity of Maryland, Baltimore
InventorsJoseph Kao, Christopher William Ward, Ramzi Khairallah
Life of this patent
Estimating the term…
Abstract
Prodrugs of colchicine, de-acetyl colchicine, colcemid, and nocodazole are provided as therapies for the treatment of diseases ameliorated by the inhibition of microtubule polymerization.
Claims9
A prodrug of formula:
- wherein R1 is a substituent selected from the group consisting of H, and optionally substituted alkyl, -alkyl-CN, alkyl-ester, alkylaryl, alkylhetaryl, alkylheterocycloalkyl, alkenyl, alkenyl-cycloalkyl, alkynyl, alkynyl-cycloalkyl, cycloalkyl, cycloalkyl-alkenyl, cycloalkyl-heterocycloalkyl, cycloalkyl-heteroaryl, aryl, heteroaryl, acyloxy, acyl, aralkyl, ester, fluoroalkyl, heteroalkyl, heteroalkenyl, heteroalkynyl, heteroalkylaryl, heteroalkylheteroaryl, heteroalkylheterocycloalkyl, heteroalkylcycloalkyl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkyl;
- R2 is a substituent selected from the group consisting of H, and optionally substituted alkyl, carboxyl, ester, and —C(═O)O-alkyl-OC(═O)-alkyl;
- R3 is a substituent selected from the group consisting of H, and optionally substituted alkyl, alkylaryl, alkylhetaryl, alkylheterocycloalkyl, alkenyl, alkenyl-cycloalkyl, alkynyl, alkynyl-cycloalkyl, cycloalkyl, cycloalkyl-alkenyl, cycloalkyl-heterocycloalkyl, cycloalkyl-heteroaryl, aryl, heteroaryl, acyloxy, acyl, aralkyl, ester, fluoroalkyl, heteroalkyl, heteroalkenyl, heteroalkynyl, heteroalkylaryl, heteroalkylheteroaryl, heteroalkylheterocycloalkyl, heteroalkylcycloalkyl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkyl;
- R4 is a substituent selected from the group consisting of H, and optionally substituted alkyl, carboxyl, ester, and —C(═O)O-alkyl-OC(═O)-alkyl;
- R5a and R5b are substituents independently selected from the group consisting of H, and optionally substituted alkyl, alkylaryl, alkylhetaryl, alkylheterocycloalkyl, alkenyl, alkenyl-cycloalkyl, alkynyl, alkynyl-cycloalkyl, cycloalkyl, cycloalkyl-alkenyl, cycloalkyl-heterocycloalkyl, cycloalkyl-heteroaryl, aryl, heteroaryl, acyloxy, acyl, aralkyl, ester, fluoroalkyl, heteroalkyl, heteroalkenyl, heteroalkynyl, heteroalkylaryl, heteroalkylheteroaryl, heteroalkylheterocycloalkyl, heteroalkylcycloalkyl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkyl;
- R6 is a substituent selected from the group consisting of H, and optionally substituted alkyl, alkoxy, -(alkoxy) n-alkyl, heteroalkyl, and -(alkyl) n-alkyl;
- n is an integer of 1-250;
- and the pharmaceutically acceptable salts thereof.
5 more elements
Dependencies are inferred from the claim text.