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US 2026/0069726 A1Published application
Zwitterionic compounds and uses thereof
AssigneeUniversity of Saskatchewan
InventorsEric William PRICE, Shvan Jassim RAHEEM
Life of this patent
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Abstract
The present application relates to zwitterion compounds of Formula I, to processes of their preparations, to conjugates thereof, to compositions comprising them and to their use in diagnostics and/or therapy. wherein Q is selected from Q1, Q2, Q3, Q4 and Q5:
Claims124
A zwitterion compound of Formula I, or a salt and/or solvate thereof:
- wherein
- R1 is H, OH or a protecting group;
- R2 is OH or a protecting group;
- Q is selected from Q1, Q2, Q3, Q4 and Q5:
- Z2 is selected from C1-15alkylene, C2-15alkenylene and C2-15alkynelene, unsubstituted or substituted with one or more of halo or OH and/or are optionally interrupted by one to three heteromoieties independently selected from O, NH and S;
- R4 and R5 are independently selected from C1-10alkyl, C2-10alkenyl and C2-10alkynyl;
- R6 is selected from H, halo, NO2, SO2 and OH;
- Z1 is selected from C1-15alkylene, C2-15alkenylene and C2-15alkynelene, unsubstituted or substituted with one or more of halo or OH and/or are optionally interrupted by one to three heteromoieties independently selected from O, NH and S;
- R3 is an anion containing group selected from sulfonate, carboxylate, sulfate and phosphate.
6 more elements
A zwitterionic compound of Formula I, or a salt and/or solvate thereof:
- wherein
- R1 is a protecting group;
- R2 is OH;
- Q is selected from Q1, Q2, Q3, Q4 and Q5:
- Z2 is selected from C1-15alkylene, C2-15alkenylene and C2-15alkynelene, unsubstituted or substituted with one or more of halo or OH and/or are optionally interrupted by one to three heteromoieties independently selected from O, N and S;
- R4 and R5 are independently selected from C1-10alkyl, C2-10alkenyl and C2-10alkynyl;
- R6 is selected from H, halo, NO2, SO2 and OH;
- Z1 is selected from C1-15alkylene, C2-15alkenylene and C2-15alkynelene, unsubstituted or substituted with one or more of halo or OH and/or are optionally interrupted by one to three heteromoieties independently selected from O, N and S;
- R3 is a sulfonate;
- provided that when Q is Q1, Q2, Q3 or Q4, then the compound of Formula I is an (R)- or (S)-enantiomer of the carbon to which Z2 is attached.
7 more elements
A conjugate of formula II, or a salt and/or solvate thereof:
- wherein
- Y1 is a complex comprising a chelating agent and one or more radionuclides;
- Y2 is a targeting ligand;
- L is a zwitterionic (ZW) linker of the formula
- wherein
- Q is selected from Q1, Q2, Q3, Q4 and Q5:
- Z2 is selected from C1-15alkylene, C2-15alkenylene and C2-15alkynelene, unsubstituted or substituted with one or more of halo or OH and/or are optionally interrupted by one to three heteromoieties independently selected from O, NH and S;
- R4 and R5 are independently selected from C1-10alkyl, C2-10alkenyl and C2-10alkynyl;
- R6 is selected from H, halo, NO2, SO2 and OH;
- Z1 is selected from C1-15alkylene, C2-15alkenylene and C2-15alkynelene, unsubstituted or substituted with one or more of halo or OH and/or are optionally interrupted by one to three heteromoieties independently selected from O, NH and S;
- R3 is an anion containing group selected from sulfonate, carboxylate, sulfate and phosphate;
- and
- n is an integer 0 to 5.
10 more elements
A conjugate of Formula IV, or a salt and/or solvate thereof:
- wherein
- Y1 is a complex comprising a chelating agent and one or more radionuclides, wherein the chelating agent is desferrioxamine (DFO) or a compound of the following formula;
- wherein
- R7, R8, R9 and R10 are independently selected from H and C1-4alkyl;
- each a, c and e is an integer independently selected from 3, 4, 5, 6 and 7;
- each b and d is an integer independently selected from 1, 2, 3 and 4;
- L1 is a linker group
- Y3 is
- or
- R11 is selected from C1-10alkyl and C1-6alkylenephenyl, optionally substituted by one of NH2, OH, SH, N3, CO2H and
- wherein X is O, S or NH;
- R12, R13, R14, R15 and R16 are independently selected from H and C1-4alkyl;
- f is an integer selected from 1, 2, 3 and 4;
- each g, l and k is an integer independently selected from 3, 4, 5, 6 and 7;
- each h and j is an integer independently selected from 1, 2, 3 and 4;
- Y2 is a targeting ligand;
- S1 is a biomolecule conjugating group;
- L is a zwitterionic (ZW) linker of the formula
- wherein
- Q is selected from Q1, Q2, Q3, Q4 and Q5:
- Z2 is selected from C1-15alkylene, C2-15alkenylene and C2-15alkynelene, unsubstituted or substituted with one or more of halo or OH and/or are optionally interrupted by one to three heteromoieties independently selected from O, NH and S;
- R4 and R5 are independently selected from C1-10alkyl, C2-10alkenyl and C2-10alkynyl;
- R6 is selected from H, halo, NO2, SO2 and OH;
- Z1 is selected from C1-15alkylene, C2-15alkenylene and C2-15alkynelene, unsubstituted or substituted with one or more of halo or OH and/or are optionally interrupted by one to three heteromoieties independently selected from O, NH and S;
- R3 is an anion containing group selected from sulfonate, carboxylate, sulfate and phosphate;
- n is an integer 1 to 5;
- wherein the chelating agent is a compound of Formula V, Y1 is attached to L at R11 of L1 group
- and the L is further optionally attached to one to three additional L groups, or the L is attached between the Y3
- and L1
- groups of Y1, or one L is attached at R11 of L1 group and another L is attached between the Y3 and L1 groups of Y1, and each one of the L is further optionally attached to one to three additional L groups;
- and
- wherein the chelating agent is DFO, the point of attachment of L is at the amine
- and wherein the * indicates the point of attachment.
30 more elements
Dependencies are inferred from the claim text.