Multi-motif dendrons and their supramolecular structures and uses thereof
OwnerOmar Fizal Khan, Grayson Tilstra +3inventors
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.
Claims78
A dendron of Formula I, or a salt and/or solvate thereof:
- wherein:
- each Repeating Group is the same or different and is:
- n is 1, 2, 3, 4 or 5 and each Ln and each Xn are the same or different and are as defined below, depending on the value for n;
- when n is 1, the dendron is a generation 1 dendron and the compound of Formula I has the following structure:
- wherein each X1 is the same or different and is either H or a Terminal Group, provided at least one X1 is a Terminal Group and each L1 is the same or different and is a Linking Group;
- when n is 2, the dendron is a generation 2 dendron and the compound of Formula I has the following structure:
- wherein each X2 is the same or different and is either H or a Terminal Group, provided at least one X2 is a Terminal Group and each L1 and each L2 is the same or different and is a Linking Group;
- when n is 3, the dendron is a generation 3 dendron and the compound of Formula I has the following structure:
- wherein each X3 is the same or different and is either H or a Terminal Group, provided at least one X3 is a Terminal Group and each L1, each L2 and each L3 is the same or different and is a Linking Group;
- when n is 4, the dendron is a generation 4 dendron and the compound of Formula I has the following structure:
- wherein each X4 is the same or different and is either H or a Terminal Group, provided at least one X4 is a Terminal Group and each L1, each L2, each L3 and each L4 is the same or different and is a Linking Group;
- when n is 5, the dendron is a generation 5 dendron and the compound of Formula I has the following structure:
- wherein each X5 is the same or different and is either H or a Terminal Group, provided at least one X5 is a Terminal Group and each L1, each L2, each L3 each L4 and each L5 is the same or different and is a Linking Group;
- R1 is selected from C1-20alkyl, C2-20alkenyl, C2-20alkynyl, C1-20alkylenearyl, C1-20alkyleneheteroaryl, C1-20alkyleneC3-6heterocycloalkyl, C1-20alkyleneC3-6cycloalkyl and C1-6alkylene-S—S—C1-6alkyl, each of which is unsubstituted or substituted with one or more of halo, OH, OC1-20alkyl, C(O)OC1-20alkyl and NR2R2′, and the aryl, heteroaryl, heterocycloalkyl and cycloalkyl groups are additionally optionally substituted with one or more of C1-10alkyl;
- R2 and R2′ are independently selected from H and C1-10alkyl;
- the Linker Group comprises C1-20 alkylene or C2-20 alkenylene, each of which is optionally interrupted by one or more groups selected from S, S—S, O, NH, N(C1-4alkyl), C(O), C(O)O, OC(O), C(O)NH, NHC(O), NHC(NH), NHC(NC1-4alkyl), C(NH)NH and C(NC1-4alkyl)NH, and each alkyl, alkylene and alkenylene is unsubstituted or substituted with one or more of halo and OH;
- the Terminal Group is selected from C1-40alkyl, C2-40alkenyl, C1-40alkylenearyl and C1-40alkenylenearyl, each alkyl, alkenyl, alkylene and alkenylene being optionally interrupted by one or more groups selected from 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(NC1-20alkyl), and the alkyl, alkenyl, alkylenearyl and alkenylenearyl are optionally substituted with one or more of halo, NR5R5′ and OH;
- and
- R3, R4, R5 and R5′ are independently hydrogen or C1-10alkyl;
- wherein all available hydrogen atoms bonded to carbon are optionally replaced with a fluorine atom.
The dendron of any one of claims 1 to 6, wherein L1, L2, L3, L4 and L5 are independently a linker group comprising C1-10alkylene or C2-10alkenylene, each of which is optionally interrupted by one or two moieties independently selected from S, S—S, O, NH, N(C1-2alkyl), C(O), C(O)O, OC(O), C(O)NH, NHC(O), NHC(NH), NHC(NC1-2alkyl), C(NH)NH, C(NC1-2alkyl)NH, and each alkyl, alkylene and alkenylene is unsubstituted or substituted with one or two OH and/or one or more fluoro.
Dependencies are inferred from the claim text.