Ibandronate conjugates of nucleoside antimetabolites
AssigneeMbc Pharma, Inc.
InventorsAlexander Karpeisky, Shawn Zinnen
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Abstract
Provided herein are conjugates of nucleoside antimetabolites and their analogs with ibandronate, pharmaceutical compositions including one or more of said conjugates, methods of synthesizing the same as well as methods of treating diseases and or conditions using the same.
Claims18
A compound comprising:
- or a pharmaceutically acceptable acid addition salt thereof,
- wherein;
- X is an anticancer compound comprising a nucleoside antimetabolite having the structure:
- wherein:
- B is a natural or modified nucleic acid base,
- R4=H, and
- R2 and R3 are independently selected from the group consisting of H, OH, F, and Cl;
- and
- Y is selected from the group consisting of H, alkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.
A compound comprising:
- or a pharmaceutically acceptable acid addition salt thereof,
- wherein;
- X is an anticancer compound comprising a nucleoside antimetabolite having the structure:
- wherein:
- B is a natural or modified nucleic acid base,
- R2 and R3 are independently selected from the group consisting of H, OH, F, and Cl;
- and
- Y is selected from the group consisting of H, alkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.
A method of synthesizing nucleoside antimetabolite ibandronate conjugates, the method comprising reacting nucleoside-5′-phosphate or nucleoside-2′- or 3′-phosphate with trifluoroacetic anhydride in the presence of tertiary amine base in organic solvent, followed by addition of nucleophilic catalyst, followed by addition of ibandronate, followed by addition of water and purification by ion-exchange or reverse-phase chromatography.
Dependencies are inferred from the claim text.