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US 12,758,648 B2Granted
Polyoxazoline-lipid conjugates and lipid nanoparticles and pharmaceutical compositions including same
AssigneeSerina Therapeutics (AL), Inc.
InventorsJ Milton Harris, Michael Bentley, Tacey Viegas, Randall Moreadith, Robert J Sharpe, Kunsang Yoon, Zhihao Fang, Rebecca Weimer
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Abstract
POZ-lipid conjugates and lipid nanoparticles (LNPs) including POZ-lipid conjugates used to facilitate delivery of an encapsulated payload. LNPs including POZ-lipid conjugates and a nucleic acid payload such as, but not limited to, mRNA or modified mRNA are disclosed. Such LNPs have no immunogenicity or reduced immunogenicity as compared to a corresponding LNP containing a PEG-lipid.
Claims23
A compound of Formula III
- R-(POZ)na-Z-L-Lipid (III)
- wherein
- R comprises an initiating group,
- POZ comprises a polyoxazoline polymer of the structure [N(COX)CH2CH2], wherein X is independently selected for each repeating unit of the polyoxazoline polymer from an unsubstituted or substituted alkyl, alkenyl, aralkyl, heterocycylalkyl group, alkyne-substituted alkyl, or an active functional group,
- n ranges from 1 to 1,001,
- a indicates a random copolymer or a block copolymer,
- Z comprises S, O, or N, and
- L-Lipid has the structure —CH2CH2—C(O)—N—(R1)x, where R1 is an alkyl and x is at least 2.
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A compound of Formula III
- R-(POZ)na-Z-L-Lipid (III)
- wherein
- R comprises a substituted or unsubstituted alkyl,
- POZ comprises a polyoxazoline polymer of the structure [N (COX) CH2CH2], wherein X is independently selected for each repeating unit of the polyoxazoline polymer from an unsubstituted or substituted alkyl, alkenyl, aralkyl, heterocycylalkyl group, alkyne-substituted alkyl, or an active functional group,
- n ranges from 15 to 35,
- a indicates a random copolymer or a block copolymer,
- Z comprises S, O, or N,
- L comprises an amidase-cleavable amide having the structure —CH2CH2—C(O)—N, and
- Lipid comprises a lipid consisting essentially of two alkyl chains.
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A lipid nanoparticle comprising:
- a compound of Formula III
- R-(POZ)na-Z-L-Lipid III
- wherein R comprises an initiating group;
- POZ comprises a polyoxazoline polymer of the structure [N (COX) CH2CH2]
- wherein X is independently selected for each repeating unit of the polyoxazoline polymer from an unsubstituted or substituted alkyl, alkenyl, aralkyl, heterocycylalkyl group, alkyne-substituted alkyl, or an active functional group;
- n ranges from 1 to 1,000,
- a indicates a random copolymer or a block copolymer,
- Z comprises S, O, or N, and
- L-Lipid has the structure —CH2CH2—C(O)—N—(R1) x, where R1 is an alkyl and x is at least 2;
- an ionizable or cationic lipid;
- a helper lipid;
- and
- a sterol lipid.
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Dependencies are inferred from the claim text.