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US 2026/0000769 A1Published application
Lymph directing prodrugs
AssigneeMonash University
InventorsChristopher John Porter, Jamie Simpson, Natalie Trevaskis, Tim Quach, Sifei Han, Luojuan Hu
Life of this patent
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Abstract
The present invention relates to compounds and their uses, in particular, compounds in the form of prodrugs that promote transport of a pharmaceutical agent to the lymphatic system and subsequently enhance release of the parent drug.
Claims22
A compound of the formula (I):
- wherein
- R1 and R2 independently represent H, or a residue of a C2-C28 fatty acid;
- —X— is selected from —O—, —NH— and —S—;
- represents a residue of a pharmaceutical agent;
- -L- is —OC(O)— or —X′—;
- —Y— represents an optionally substituted —C1-C20alkylC(O)OCH2—, —C2-C20alkenylC(O)OCH2— or —C2-C20alkynylC(O)OCH2— group when -L- is —OC(O)—;
- wherein one or more of the carbon atoms in the alkyl, alkenyl or alkynyl group may be replaced with NH, S, O, a C5-C8 aromatic or aliphatic cyclic group or a C5-C8 aromatic or aliphatic heterocyclic group, provided that the alkyl, alkenyl or alkynyl group does not exceed a length equivalent to a linear C20alkyl group;
- or
- —Y— represents an optionally substituted —C1-C2alkylC(O)R3— group or a —C2alkenylC(O)R3— or —C2alkynylC(O)R3— group when -L- is —X′—;
- R3 is a self-immolative group;
- X′ is O, S, N(R4) or N(H)S(O)2;
- R4 is H or C1-C4alkyl;
- or
- pharmaceutically acceptable salts thereof.
11 more elements
A method of promoting lymphatic transport and systemic release of a pharmaceutical agent comprising conjugating to the pharmaceutical compound a prodrug residue of the formula (VI):
- wherein
- R1 and R2 independently represent H or a residue of a C2-C28 fatty acid;
- —X— is selected from —O—, —NH— and —S—;
- —Y— represents an optionally substituted —C1-C2alkylC(O)R3— group or a —C2alkenylC(O)R3— or —C2alkynylC(O)R3— group;
- R3 is a self-immolative group;
- and
- denotes the point where the linker is conjugated to the pharmaceutically active agent;
- or
- pharmaceutically acceptable salts thereof.
6 more elements
Dependencies are inferred from the claim text.