# US 12,599,580 B2 · Composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same

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- Number: US 12,599,580 B2
- Document ID: US12599580B2
- Status: Granted
- Kind: B2
- Application number: 17/737,761
- Filed: 2022-05-05
- Published: 2023-03-23
- Granted: 2026-04-14
- Earliest claimed: 2013-02-28
- Assignees: BASF SE
- Applicants: BASF AS
- Inventors: Svein Olaf Hustvedt; Preben Houlberg Olesen; Annette Müllertz
- Web page: https://patentgrep.com/patent/US12599580B2

## CPC

- A61K 31/202: having three or more double bonds, e.g. linolenic (eicosanoids, e.g. leukotrienes A61K31/557)
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/107: Emulsions {; Emulsion preconcentrates; Micelles (composition of emulsions A61K47/00)}
- A61K 9/48: Preparations in capsules, e.g. of gelatin, of chocolate {(A61K9/0004 takes precedence; bite capsules A61K9/0056)}
- A61K 31/20: having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/06: Antihyperlipidemics
- A61P 3/08: for glucose homeostasis (pancreatic hormones A61P5/48)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compositions comprising 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, an ester derivative, or a pharmaceutically acceptable salt thereof; a triglyceride; and a surfactant, as well as methods for their use. The present disclosure further relates to self-emulsifying drug delivery systems, such as SEDDS, SMEDDS, or SNEDDS comprising 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid.

## Claims

### Claim 1

A method for the treatment of a disease or condition chosen from:
a dyslipidemic condition; and/or
elevated triglyceride levels, non-HDL cholesterol levels, LDL cholesterol levels, and/or VLDL cholesterol levels; in a subject in need thereof, comprising administering to the subject a pharmaceutically active amount of a composition comprising from 5% to 60% by weight of the total composition of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, and ester derivative, or a pharmaceutically acceptable salt thereof;
from 15% to 60% by weight of the total composition of a medium-chain triglyceride (MCT) oil; and
from 10% to 60% by weight of the total composition of a nonionic surfactant.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the dyslipidemic condition is chosen from hypertriglyceridemia (HTG), dyslipidemia, and mixed dyslipidemia.

### Claim 3

A method for the treatment of a disease or condition chosen from an inflammatory disease or condition and/or atherosclerosis in a subject in need thereof, comprising administering to the subject a pharmaceutically active amount of a composition comprising from 5% to 60% by weight of the total composition of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, and ester derivative, or a pharmaceutically acceptable salt thereof;
from 15% to 60% by weight of the total composition of a medium-chain triglyceride (MCT) oil; and
from 10% to 60% by weight of the total composition of a nonionic surfactant.

### Claim 4

A method for the treatment of a disease or condition chosen from peripheral insulin resistance, a diabetic condition, and/or type 2 diabetes in a subject in need thereof, comprising administering to the subject a pharmaceutically active amount of a composition comprising from 5% to 60% by weight of the total composition of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, and ester derivative, or a pharmaceutically acceptable salt thereof;
from 15% to 60% by weight of the total composition of a medium-chain triglyceride (MCT) oil; and
from 10% to 60% by weight of the total composition of a nonionic surfactant.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the total dose of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, an ester derivative, or a pharmaceutically acceptable salt thereof, administered per day as a total dose ranges from about 50 mg to about 800 mg.

### Claim 6 (depends on 3)

The method according to claim 3, wherein the total dose of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, an ester derivative, or a pharmaceutically acceptable salt thereof, administered per day as a total dose ranges from about 50 mg to about 800 mg.

### Claim 7 (depends on 4)

The method according to claim 4, wherein the total dose of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, an ester derivative, or a pharmaceutically acceptable salt thereof, administered per day as a total dose ranges from about 50 mg to about 800 mg.

### Claim 8 (depends on 1)

The method according to claim 1, wherein the composition is administered once daily.

### Claim 9 (depends on 3)

The method according to claim 3, wherein the composition is administered once daily.

### Claim 10 (depends on 4)

The method according to claim 4, wherein the composition is administered once daily.

### Claim 11 (depends on 1)

The method according to claim 1, wherein the medium chain triglyceride oil consists essentially of C8-C10 triglycerides.

### Claim 12 (depends on 1)

The method according to claim 1, wherein the medium chain triglyceride oil is derived from capric acid and caprylic acid.

### Claim 13 (depends on 3)

The method according to claim 3, wherein the medium chain triglyceride oil consists essentially of C8-C10 triglycerides.

### Claim 14 (depends on 3)

The method according to claim 3, wherein the medium chain triglyceride oil is derived from capric acid and caprylic acid.

### Claim 15 (depends on 4)

The method according to claim 4, wherein the medium chain triglyceride oil consists essentially of C8-C10 triglycerides.

### Claim 16 (depends on 4)

The method according to claim 4, wherein the medium chain triglyceride oil is derived from capric acid and caprylic acid.

### Claim 17 (depends on 1)

The method according to claim 1, wherein the nonionic surfactant is chosen from polyoxyethylene (20) sorbitan monooleate with an HLB value of 15.0 (TWEEN 80) and polyoxyethylene (20) sorbitan monolaurate with an HLB value of 16.0 (TWEEN 20).

### Claim 18 (depends on 3)

The method according to claim 3, wherein the nonionic surfactant is chosen from polyoxyethylene (20) sorbitan monooleate with an HLB value of 15.0 (TWEEN 80) and polyoxyethylene (20) sorbitan monolaurate with an HLB value of 16.0 (TWEEN 20).

### Claim 19 (depends on 4)

The method according to claim 4, wherein the nonionic surfactant is chosen from polyoxyethylene (20) sorbitan monooleate with an HLB value of 15.0 (TWEEN 80) and polyoxyethylene (20) sorbitan monolaurate with an HLB value of 16.0 (TWEEN 20).

### Claim 20 (depends on 2)

The method according to claim 2, wherein the wherein the medium chain triglyceride oil is derived from capric acid and caprylic acid and the nonionic surfactant is chosen from polyoxyethylene (20) sorbitan monooleate with an HLB value of 15.0 (TWEEN 80) and polyoxyethylene (20) sorbitan monolaurate with an HLB value of 16.0 (TWEEN 20).