Combretastatin A-1 phosphate and combretastatin B-1 phosphate prodrugs
AssigneeArizona Board of Regents
InventorsGeorge R. Pettit, John W. Lippert, III
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Abstract
The present invention relates to the syntheses and structural elucidation of Combretastatin A1-Phosphate Prodrugs and Combretastatin B1-Phosphate Prodrugs and the utilization of those prodrugs in the treatment of neoplastic diseases. The prodrugs described herein have the structure: Combretastin A-1 Phosphate Prodrug (I) and Combretastin B-1 Phosphate Prodrug (II).
Claims39
A compound of Formula I,
- wherein:
- X represents a cis-or trans-alkenyl or alkanyl group represented by -(CH=CH)1-or-(CH2—CH2)1—;
- at least one of —OR1, —OR2,—OR3, or -OR4 or —O+Q−, and the remainder are hydroxyl or —O+Q−;
- and
- Q− is a metal or ammonium cation.
A compound having the following structure:
A compound having the following structure:
A compound having the following structure:
- wherein R is selected from the group consisting of:
- lithium, potassium, calcium, magnesium, cesium, manganese, zinc, morpholine, piperazine, nicotinamide, quinine, quinidine, verapamil and papaverine.
A compound formed by the method comprising the steps of:
- (a) providing Combretastatin A-1;
- (b) reacting Combretastatin A-1 with a phosphorylation reagent;
- and
- (c) reacting the compound of step (b) with a cleavage reagent.
A compound having the following structure:
Dependencies are inferred from the claim text.