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US 12,606,585 B2Granted
Fluorinated hexoses
AssigneeStichting Radboud Universiteit
InventorsJohan Franciscus Adrianus Pijnenborg, Thomas Jan Boltje, Emiel Rossing
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Abstract
The present invention relates to a new class of compounds based on a hexose featuring at least two 6-fluorides. The class is useful as inhibitors of 4,6-dehydratase enzymes. Such inhibitors are suitable for use as a medicament, for example for treating, preventing, or delaying cancer, tumor metastasis, inflammation, infections, or genetic disorders.
Claims15
A compound of general formula (1-man) or (1-gal) or a salt thereof:
- wherein
- f is Hor F;
- X is in each instance independently chosen from hydrogen and a linear, branched, or cyclic C1- 4acyl or alkyl wherein each carbon atom is optionally substituted by a halogen, an alkoxy, or a haloalkoxy moiety, and wherein the acyl or alkyl is optionally unsaturated;
- Xn is —O—X, —NH2, —NH—C1-4alkyl, —N(C1-4alkyl)2, —NH—C1-4acyl, or —N(C1-4acyl)2 wherein each carbon atom is optionally substituted by a halogen, an alkoxy, or a haloalkoxy moiety, and wherein the acyl or alkyl is optionally unsaturated;
- L is O, S, NH, N(CH3), CH2, CHF, or CF2;
- Q is O or S;
- Z1 and Z2 are each independently chosen from
- hydrogen,
- benzyl or a linear, branched, or cyclic C1-6 acyl, alkyl, alkenyl, or alkynyl, wherein each carbon atom is optionally substituted by a halogen, an alkoxy, or a haloalkoxy moiety,
- a C1-4alkyl-Q′-C1-4acyl or a C1-4alkyl-Q′-C1-4alkyl, wherein each carbon atom is optionally substituted by a halogen, an alkoxy, or a haloalkoxy moiety, and wherein Q′ is O or —O—C(═O)—O— or S or —S—S—,
- or Z1 and Z2 together form a C1-4alkyl bridging moiety that is optionally substituted with halogen or a C1-10hydrocarbon,
- or Z1 is H and Z2 together with the O to which it is attached form a nucleotide;
- or OZ1 is an N-linked amino acid.
10 more elements
Dependencies are inferred from the claim text.