# US 10,369,122 B2 · Benzene-1,3,5-tricarboxamide derivatives and uses thereof

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- Number: US 10,369,122 B2
- Document ID: US10369122B2
- Status: Granted
- Kind: B2
- Application number: 15/575,919
- Filed: 2016-05-20
- Published: 2018-05-31
- Granted: 2019-08-06
- Earliest claimed: 2015-05-21
- Assignees: Ohio State Innovation Foundation
- Applicants: Ohio State Innovation Foundation
- Inventors: Yizhou Dong; Bin Li
- Web page: https://patentgrep.com/patent/US10369122B2

## CPC

- A61K 31/166: having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
- A61K 9/127: Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K 9/1272: comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers (lipids as modifying agents {A61K47/543})
- A61K 9/5123: {Organic compounds, e.g. fats, sugars}
- A61K 31/713: Double-stranded nucleic acids or oligonucleotides
- A61K 47/06: Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- C07C 233/78: with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to compounds, compositions, lipid-like nanoparticles, and methods for delivery of therapeutic, diagnostic, or prophylactic agents (for example, a polynucleotide).

## Claims

### Claim 1

A compound of Formula I:
and salts thereof; wherein
each R1 is independently unsubstituted alkyl;
each R2 is independently unsubstituted alkyl;
each R3 is independently hydrogen or substituted or unsubstituted alkyl; and
each m is independently 3, 4, 5, 6, 7, or 8;
wherein at least one R1 is unsubstituted C10-12 alkyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein at least one R1 is C11H23.

### Claim 3 (depends on 1)

The compound of claim 1, wherein at least one R2 is C11H23.

### Claim 4 (depends on 1)

The compound of claim 1, wherein at least one R3 is hydrogen.

### Claim 5 (depends on 1)

The compound of claim 1, wherein at least one m=3.

### Claim 6 (depends on 1)

The compound of claim 1, having the structure:
and salts thereof, wherein m=3.

### Claim 7 (depends on 1)

The compound of claim 1, wherein at least one R1 is C12H25.

### Claim 8 (depends on 1)

The compound of claim 1, wherein at least one R2 is C12H25.

### Claim 9 (depends on 1)

The compound of claim 1, having the structure:
and salts thereof, wherein m=3.

### Claim 10

A nanoparticle comprising:
a compound of Formula I;
and salts thereof; wherein
each R1 is independently substituted or unsubstituted alkyl;
each R2 is independently substituted or unsubstituted alkyl;
each R3 is independently hydrogen or substituted or unsubstituted alkyl; and
each m is independently 1, 2, 3, 4, 5, 6, 7, or 8;
a non-cationic lipid;
a polyethylene glycol-lipid; and
a sterol.

### Claim 11 (depends on 10)

The nanoparticle of claim 10, wherein the compound of Formula I is:
and salts thereof, wherein m=3.

### Claim 12 (depends on 10)

The nanoparticle of claim 10, wherein the phosphatidylethanolamine lipid is selected from 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (POPE), 1,2-di stearoyl-sn-glycero-3-phosphocholine (DSPC), 1-stearoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (SOPE), or combinations thereof.

### Claim 13 (depends on 12)

The nanoparticle of claim 12, wherein the phosphatidylethanolamine lipid is 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE).

### Claim 14 (depends on 10)

The nanoparticle of claim 10, wherein the polyethylene glycol-lipid is selected from 1,2-dimyristoyl-sn-glycerol, methoxypolyethylene glycol (DMG-PEG), DLPE-PEGs, DMPE-PEGs, DPPC-PEGs, and DSPE-PEGs.

### Claim 15 (depends on 14)

The nanoparticle of claim 14, wherein the polyethylene glycol-lipid is 1,2-dimyristoyl-sn-glycerol, methoxypolyethylene glycol (DMG-PEG).

### Claim 16 (depends on 10)

The nanoparticle of claim 10, wherein the sterol is selected from cholesterol, campesterol, ergosterol, or sitosterol.

### Claim 17 (depends on 16)

The nanoparticle of claim 16, wherein the sterol is cholesterol.

### Claim 18

A method for the delivery of an agent into a cell comprising;
introducing into the cell a composition comprising;
a nanoparticle comprising;
a compound of Formula I;
and salts thereof; wherein
each R1 is independently substituted or unsubstituted alkyl;
each R2 is independently substituted or unsubstituted alkyl;
each R3 is independently hydrogen or substituted or unsubstituted alkyl; and
each m is independently 1, 2, 3, 4, 5, 6, 7, or 8;
a non-cationic lipid;
a polyethylene glycol-lipid;
a sterol; and
an agent.

### Claim 19 (depends on 18)

The method of claim 18, wherein the agent is a polynucleotide.

### Claim 20

A compound of Formula I:
and salts thereof; wherein
each R1 is independently substituted or unsubstituted alkyl;
each R2 is independently substituted or unsubstituted alkyl;
each R3 is independently hydrogen or substituted or unsubstituted alkyl; and
each m is independently 1, 2, 3, 4, 5, 6, 7, or 8;
wherein at least one R1 is C12H25.

### Claim 21 (depends on 20)

The compound of claim 20, wherein at least one R2 is C12H25.