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US 12,649,830 B2Granted
Multi-motif dendrons and their supramolecular structures and uses thereof
AssigneeThe Governing Council of the University of Toronto
InventorsOmar Fizal Khan, Grayson Tilstra, Alanna Margaret Manning, Yan Ming Anson Lau, Julien Couture-Senécal
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Abstract
The present application includes dendrons of Formula I, compositions comprising these dendrons and uses thereof, in particular for the delivery of agents such as nucleic acids and drugs to cells and subjects. wherein each Repeating Group is the same or different.
Claims18
A dendron or a salt and/or solvate thereof, wherein
- Generation 1 of the dendron has Formula (1):
- wherein each X1 is the same and is selected from the group consisting of
- each of which is optionally substituted with one or two OH, one or two NH2 and/or one or more fluorine;
- Generation 2 of the dendron has Formula (2):
- wherein each X2 is the same and is selected from the group consisting of C1-40alkyl and C2-40alkenyl, wherein each alkyl and each alkenyl is optionally interrupted by one or more groups selected from the group consisting of —S—S—, —C(O)—, —OC(O)—, —C(O)O—, —OC(O)O—, —NR3C(O)O—, —OC(O)NR3—, —C(O)S—, —SC(O)—, —NR3C(O)—, —C(O)NR3—, —NR3C(O)NR4— and —C(NC1-20 alkyl)-, wherein the alkyl and alkenyl are optionally substituted with one or more substituents selected from the group consisting of halo, NR5R5′ and OH, and wherein R3, R4, R5 and R5′ are each independently hydrogen or C1-10 alkyl;
- or
- Generation 3 of the dendron has Formula (3):
- wherein each X3 is the same and is selected from the group consisting of C1-40alkyl and C2-40alkenyl, wherein each alkyl and each alkenyl is optionally interrupted by one or more groups selected from the group consisting of —S—S—, —C(O)—, —OC(O)—, —C(O)O—, —OC(O)O—, —NR3C(O)O—, —OC(O)NR3—, —C(O)S—, —SC(O)—, —NR3C(O)—, —C(O)NR3—, —NR3C(O)NR4— and —C(NC1-20 alkyl)-, wherein the alkyl and alkenyl are optionally substituted with one or more substituents selected from the group consisting of halo, NR5R5′ and OH, and wherein R3, R4, R5 and R5′ are each independently hydrogen or C1-10 alkyl;
- wherein in Formula (1), Formula (2), and Formula (3):
- R1 is selected from the group consisting of C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C1-10 alkylenePh, C1-10 alkyleneheteroaryl, C1-10 alkyleneC5-6heterocycloalkyl, C1-10 alkylene C5-6 cycloalkyl and C1-4 alkylene-S—S—C1-4 alkyl, each of which is unsubstituted or substituted with one to four of OH, OC1-15 alkyl, C(O)OC1-15 alkyl and NR2R2′ and/or one or more fluoro, the phenyl, heteroaryl, heterocycloalkyl and cycloalkyl groups are additionally optionally substituted with one to four of C1-4 alkyl and C1-4 fluoroalkyl, wherein R2 and R2′ are independently selected from the group consisting of H and C1-10 alkyl;
- each L1, L2, and L3 is the same or different and is a Linking Group, wherein each Linking Group is independently selected from the group consisting of:
- wherein d, e, f, g, u, v, w, x and y are each independently 1, 2, 3, 4, 5, or 6;
- and
- each available hydrogen atom bonded to a carbon atom is independently optionally replaced with a fluorine atom.
11 more elements
Dependencies are inferred from the claim text.