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US 12,655,114 B2Granted
Ionizable lipid compounds and lipid nanoparticle compositions
AssigneeSunVax mRNA Therapeutics Inc.
InventorsLibin Zhang, Yingzhong Li
Life of this patent
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Abstract
Novel ionizable lipids, compositions, and methods of using the novel ionizable lipids and compositions are disclosed. Lipid nanoparticle compositions include a novel ionizable lipid as well as additional lipids such as phospholipids, structural lipids, and PEG lipids. Lipid nanoparticle compositions further including biologically active agents such as mRNA or DNA are useful in the delivery of biologically active agents to mammalian cells or organs.
Claims21
A compound, wherein the compound is:
- or
- a salt or isomer thereof.
A compound of Formula IV-1
- or a salt or isomer thereof, wherein
- each R1, R2, and R5 is independently selected from C3-C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted alkenyl, substituted alkynyl, acyl, substituted carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- a, b and c are each independently an integer from 0-24, and
- d is an integer from 0-10, wherein when R5 is
- then R2 is selected from C3-C22 alkyl, C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted C3-C24 alkyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- R3 is independently selected from H, C3-C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- a, b and c are each independently an integer from 0-24, and
- d is an integer from 0-10;
- each R6, R7, R8 and R9 is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl,
- a, b and c are each independently an integer from 0-24;
- each X is independently selected from CH, or N;
- each Y is independently selected from CH2, NH, O, or S;
- each Z is independently selected from CH or N.
10 more elements
A compound of Formula IV-2
- or a salt or isomer thereof, wherein
- each R1, R2 and R5 is independently selected from C3-C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- a, b and c are each independently an integer from 0-24, and
- d is an integer from 0-10, wherein when R5 is
- then R2 is selected from C3-C18 alkyl, C20-C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted C2-C24 alkyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- R3 is independently selected from H, C3-C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- a, b and c are each independently an integer from 0-24, and
- d is an integer from 0-10;
- each R6, R7, R8 and R9 is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl,
- a, b and c are each independently an integer from 0-24;
- each X is independently selected from CH, or N;
- each Y is independently selected from CH2, NH, O, or S;
- each Z is independently selected from CH or N.
10 more elements
A compound of Formula IV-3
- or a salt or isomer thereof, wherein
- each R1, R2, and R5 is independently selected from C3-C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- a, b and c are each independently an integer from 0-24, and
- d is an integer from 0-10, wherein when R5 is
- then R2 is selected from C3-C18 alkyl, C20-C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted C3-C24 alkyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- R3 is independently selected from H, C3-C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted alkenyl, alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- a, b and c are each independently an integer from 0-24, and
- d is an integer from 0-10;
- each R6, R7, R8 and R9 is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl,
- a, b and c are each independently an integer from 0-24;
- each X is independently selected from CH, or N;
- each Y is independently selected from CH2, NH, O, or S;
- each Z is independently selected from CH or N.
10 more elements
A compound of Formula IV-4
- or a salt or isomer thereof, wherein
- each R1 and R5 is independently selected from C3-C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- a, b and c are each independently an integer from 0-24, and
- d is an integer from 0-10;
- each R2 is C3-C24 alkenyl, C3-C24 alkynyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl,
- a, b and c are each independently an integer from 0-24, and
- d is an integer from 0-10;
- R3 is independently selected from H, C3-C24 alkyl, C3-C24 alkenyl, C3-C24 alkynyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, and
- a, b and c are each independently an integer from 0-24, and
- d is an integer from 0-10;
- each R6, R7, R8 and R9 is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, acyl, carbocyclyl, heterocyclyl, aryl, heteroaryl,
- each X is independently selected from CH, or N;
- each Y is independently selected from CH2, NH, O, or S;
- each Z is independently selected from CH or N.
11 more elements
A nanoparticle composition comprising a compound of
- and a biologically active agent, a phospholipid, a steroid, a polyethylene glycol (PEG) lipid, or a combination thereof.
Dependencies are inferred from the claim text.