IP Library › Granted Patent US 12,324,859
Granted Patent B2
US 12,324,859 · App. 17/029,436 · Granted Jun 10, 2025

Compounds and compositions for intracellular delivery of therapeutic agents

Inventors: Kerry E. Benenato (Sudbury, MA); Ellalahewage Sathyajith Kumarasinghe (Harvard, MA); Mark Cornebise (Arlington, MA)
Assignee: ModernaTX, Inc.
A61K9/5123A61K38/1816A61K48/0033C07C229/24C07C2601/04
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Quick Facts
Patent No.
US 12,324,859
App. No.
17/029,436
Granted
Jun 10, 2025
Kind
B2
Abstract

The disclosure features novel lipids and compositions involving the same. Nanoparticle compositions include a novel lipid as well as additional lipids such as phospholipids, structural lipids, and PEG lipids. Nanoparticle compositions further including therapeutic and/or prophylactics such as RNA are useful in the delivery of therapeutic and/or prophylactics to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.

Claims (19)

1. A compound of Formula (IA):

or its N-oxide, or a salt or isomer thereof, wherein

l is selected from 1, 2, 3, 4, and 5;

m is selected from 5, 6, 7, 8, and 9;

M 1 is a bond or M′;

R 4 is

M and M′ are independently selected from —C(O)O— and —OC(O)—;

R 2 and R 3 are independently selected from the group consisting of C 6-9 alkyl and C 6-9 alkenyl; and

R′ is

2. A nanoparticle composition comprising a lipid component comprising the compound of claim 1 .

3. The nanoparticle composition of claim 2 , wherein the lipid component further comprises a phospholipid, wherein the phospholipid is selected from the group consisting of 1,2-dilinoleoyl-sn-glycero-3-phosphocholine (DLPC), 1,2-dimyristoyl-sn-glycero-phosphocholine (DMPC), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), 1,2-diundecanoyl-sn-glycero-phosphocholine (DUPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), 1,2-di-O-octadecenyl-sn-glycero-3-phosphocholine (18:0 Diether PC), 1-oleoyl-2-cholesterylhemisuccinoyl-sn-glycero-3-phosphocholine (OChemsPC), 1-hexadecyl-sn-glycero-3-phosphocholine (C16 Lyso PC), 1,2-dilinolenoyl-sn-glycero-3-phosphocholine, 1,2-diarachidonoyl-sn-glycero-3-phosphocholine, 1,2-didocosahexaenoyl-sn-glycero-3-phosphocholine, 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), 1,2-diphytanoyl-sn-glycero-3-phosphoethanolamine (ME 16.0 PE), 1,2-distearoyl-sn-glycero-3-phosphoethanolamine, 1,2-dilinoleoyl-sn-glycero-3-phosphoethanolamine, 1,2-dilinolenoyl-sn-glycero-3-phosphoethanolamine, 1,2-diarachidonoyl-sn-glycero-3-phosphoethanolamine, 1,2-didocosahexaenoyl-sn-glycero-3-phosphoethanolamine, 1,2-dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt (DOPG), dipalmitoylphosphatidylglycerol (DPPG), palmitoyloleoylphosphatidylethanolamine (POPE), distearoyl-phosphatidyl-ethanolamine (DSPE), dipalmitoyl phosphatidyl ethanolamine (DPPE), dimyristoylphosphoethanolamine (DMPE), 1-stearoyl-2-oleoyl-phosphatidyethanolamine (SOPE), 1-stearoyl-2-oleoyl-phosphatidylcholine (SOPC), sphingomyelin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, phosphatidic acid, palmitoyloleoyl phosphatidylcholine, lysophosphatidylcholine, lysophosphatidylethanolamine (LPE), and mixtures thereof.

4. The nanoparticle composition of claim 2 , wherein the lipid component further comprises a structural lipid, wherein the structural lipid is selected from the group consisting of cholesterol, fecosterol, sitosterol, ergosterol, campesterol, stigmasterol, brassicasterol, tomatidine, ursolic acid, alpha-tocopherol, and mixtures thereof.

5. The nanoparticle composition of claim 2 , wherein the lipid component further comprises a PEG lipid, wherein the PEG lipid is selected from the group consisting of a PEG-modified phosphatidylethanolamine, a PEG-modified phosphatidic acid, a PEG-modified ceramide, a PEG-modified dialkylamine, a PEG-modified diacylglycerol, a PEG-modified dialkylglycerol, and mixtures thereof.

6. The nanoparticle composition of claim 2 , further comprising a therapeutic and/or prophylactic agent.

7. The nanoparticle composition of claim 6 , wherein the therapeutic and/or prophylactic agent is a nucleic acid.

8. The nanoparticle composition of claim 7 , wherein the nucleic acid is a ribonucleic acid (RNA).

9. The nanoparticle composition of claim 8 , wherein the RNA is an mRNA.

10. A method of delivering a therapeutic and/or prophylactic agent to a mammalian cell within a mammalian subject, the method comprising administering to the mammalian subject the nanoparticle composition of claim 6 to contact the mammalian cell with the therapeutic and/or prophylactic agent and deliver the therapeutic and/or prophylactic agent to the mammalian cell.

11. A method of producing a polypeptide of interest in a mammalian cell, the method comprising contacting the cell with the nanoparticle composition of claim 6 , wherein the therapeutic and/or prophylactic agent is an mRNA, and wherein the mRNA encodes the polypeptide of interest, whereby the mRNA is being translated in the cell to produce the polypeptide of interest.

Assignments (2)
SECURITY INTEREST Recorded Nov 19, 2025
From: MODERNATX, INC.
To: ARES CAPITAL CORPORATION, AS AGENT
Reel/Frame 073634/0354 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 23, 2020
From: BENENATO, KERRY E.; KUMARASINGHE, ELLALAHEWAGE S.; CORNEBISE, MARK
To: MODERNATX, INC.
Reel/Frame 053859/0446 →
Continuity (5)
Continuation 16382423 · Apr 12, 2019
Continuation PCTUS2018022717 · Mar 15, 2018
Provisional Application 62475140 · Mar 22, 2017
Provisional Application 62471937 · Mar 15, 2017
Related Publication 20210154148A1 · May 27, 2021
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