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US 2013/0252918 A1Published application
Phosphoramidite derivatives of gemcitabine for use in the treatment cancer
AssigneeNuCana BioMed Limited
InventorChristopher McGuigan
Life of this patent
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Abstract
Phosphorodiamidate derivatives of e.g. gemcitabine are provided for use in treating cancer. In one embodiment, the two amidate motifs each comprises NR′R″ where R′ is H and R″ is CR5R6CO2R7, where R6 is H, R5 is the side chain, including H and C1, of a naturally occurring alpha amino acid, and R7 is branched or unbranched, substituted or unsubstituted, acyclic or cyclic alkyl, including t-butyl-CH2-, benzyl and C3 to C6 cycloalkyl. Formula (I).
Claims28
A chemical compound having formula I:
- wherein:
- R2 is selected from CR5R6CO2R7 and C1-C6 alkyl and R1 is selected from H and C1-C6 alkyl,
- or R1 and R2 together with the N atom to which they are attached form a ring moiety comprising 5 to 8 ring atoms;
- R4 is selected from CR5R6CO2R7 and C1-C6 alkyl and R3 is selected from H and C1-C6 alkyl,
- or R3 and R4 together with the N atom to which they are attached form a ring moiety comprising 5 to 8 ring atoms;
- where, independently for each of R2 and R4:
- R5 and R6 are selected, independently, from the side chains of naturally occurring alpha amino acids, and
- R7 is selected from C1-C18 alkyl;
- Y is selected from H and C(O)R, where R is C1-C18 alkyl;
- Z is selected from H and C(O)R, where R is C1-C18 alkyl,
- or a pharmaceutically acceptable derivative thereof.
8 more elements
A compound selected from the group consisting of:
- 2′-Deoxy-2′,2′-difluoro-D-cytidine-5′-O-bis(ethoxy-L-alaniny1)-phosphate;
- 2′-Deoxy-2′,2′-difluoro-D-cytidine-5′-O-bis(benzoxy-L-alaniny1)-phosphate;
- 2′-Deoxy-2′,2′-difluoro-D-cytidine-5′-O-bis(cyclohexoxy-L-alaniny1)-phosphate;
- 2′-Deoxy-2′,2′-difluoro-D-cytidine-5′-O-bis(2,2-dimethylpropoxy-L-alaniny1)-phosphate;
- and
- 2′-Deoxy-2′,2′-difluoro-D-cytidine-5′-O-bis(iso-propoxy-L-alaninyl)-phosphate.
3 more elements
-25. (canceled)
Dependencies are inferred from the claim text.