Back to results
US 2026/0102373 A1Published application
Lymph directing prodrugs
AssigneeMonash University
InventorsChris Porter, Jamie Simpson, Natalie Trevaskis, Tim Quach, Sifei Han, Luojuan Hu
Life of this patent
Estimating the term…
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.
Claims23
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—;
- —Y—represents an optionally substituted —C3-C20alkyl-, —C3-C20alkenyl- or —C3-C20alkynyl-group, wherein one or more of the carbon atoms in the alkyl, alkenyl or alkynyl group may be replaced with NH, S, O, a C5C8aromatic 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;
- represents a residue of a pharmaceutical agent;
- —L—is —X′—or —X′C(O)—;
- X′ is O, S, N, N(R4) or S(O)2NH;
- represents a single bond when X′ is O, S, N(R4) or S(O)2NH;
- or
- represents two separate bonds when X′ is N;
- —Z—is —C(O)—or —C(O)R3—when —L—is —X′—;
- or
- —Z—is absent when —L—is —X′C(O)—;
- R3 is a self-immolative group;
- and
- R4 is H or C1-C4alkyl;
- or
- pharmaceutically acceptable salts thereof.
15 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 —C3-C20alkyl-, —C3-C20alkenyl- or —C3-C20alkynyl-group, 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;
- —Z—is —C(O)—, —C(O)R3—or —CH2—;
- 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.
7 more elements
Dependencies are inferred from the claim text.