# US 10,864,185 B2 · Composition containing eicosapentaenoic acid alkyl ester, and method for producing same

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- Number: US 10,864,185 B2
- Document ID: US10864185B2
- Status: Granted
- Kind: B2
- Application number: 16/749,279
- Filed: 2020-01-22
- Published: 2020-07-16
- Granted: 2020-12-15
- Earliest claimed: 2014-09-17
- Assignees: Nippon Suisan Kaisha, Ltd.; Mochida Pharmaceutical Co., Ltd.
- Applicants: Nippon Suisan Kaisha, Ltd; Mochida Pharmaceutical Co., Ltd.
- Inventors: Nobushige Doisaki; Shingo Arato; Takuro Fukae
- Web page: https://patentgrep.com/patent/US10864185B2

## CPC

- A61K 31/232: having three or more double bonds, e.g. etretinate
- A61P 3/06: Antihyperlipidemics
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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]
- A61P 35/00: Antineoplastic agents
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- C07C 67/03: by reacting an ester group with a hydroxy group
- C07C 67/54: by distillation
- C07C 67/56: by solid-liquid treatment; by chemisorption
- C07C 69/587: Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
- C11B 3/12: by distillation
- C11C 3/10: Ester interchange
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)
- C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM

## Abstract

Provided are: a composition containing 96-99 area % of eicosapentaenoic acid alkyl ester, the composition having an arachidonic acid alkyl ester content of 0.7 area % or less, and an eicosapentaenoic-acid-alkyl-ester mono-trans isomer content of 2.5 area % or less; and a method for producing a composition containing a high concentration of eicosapentaenoic acid alkyl ester, the method including performing precision distillation on a composition containing eicosapentaenoic acid alkyl ester, obtained by alkyl esterification of a raw material oil containing eicosapentaenoic acid, under a vacuum of 0.2 Torr or lower and a temperature of 190° C. or lower in the entire column, and performing a concentration treatment on the precision-distilled composition using chromatography.

## Claims

### Claim 1

An eicosapentaenoic acid alkyl ester-containing composition which, upon measurement by gas chromatography, comprises 96-99 area % of an eicosapentaenoic acid alkyl ester,
wherein the content of any one of the mono-trans forms of the eicosapentaenoic acid alkyl ester in which any one of the double bonds at 5-position, 14-position, and 17-position thereof is trans is 0.5 area % or less; and
wherein the content of docosahexaenoic acid (C22:6 n-3) alkyl ester is 0.1 area % or less.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the content of mono-trans forms of the eicosapentaenoic acid alkyl ester is 2.5 area % or less.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the sum of the contents of mono-trans forms and di-trans forms of the eicosapentaenoic acid alkyl ester is 2.5 area % or less.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the sum of the contents of mono-trans forms, di-trans forms and tri-trans forms of the eicosapentaenoic acid alkyl ester is 2.5 area % or less.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the sum of the contents of mono-trans forms, di-trans forms, tri-trans forms and tetra-trans forms of the eicosapentaenoic acid alkyl ester is 2.5 area % or less.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the content of a mono-trans form of the eicosapentaenoic acid alkyl ester in which the double bond at 11-position thereof is trans is 1.0 area % or less.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the content of an arachidonic acid alkyl ester is 0.7 area % or less.