# US 11,077,084 B2 · Oils with anti-inflammatory activity containing natural specialized proresolving mediators and their precursors

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- Number: US 11,077,084 B2
- Document ID: US11077084B2
- Status: Granted
- Kind: B2
- Application number: 17/163,722
- Filed: 2021-02-01
- Published: 2021-05-27
- Granted: 2021-08-03
- Earliest claimed: 2012-05-10
- Assignees: Solutex NA LLC
- Applicants: Solutex NA LLC
- Inventors: Gerhardus Lucas Bannenberg; Charles Nicholas Serhan; Fernando Moreno Egea
- Web page: https://patentgrep.com/patent/US11077084B2

## CPC

- A61K 31/202: having three or more double bonds, e.g. linolenic (eicosanoids, e.g. leukotrienes A61K31/557)
- A61K 31/557: Eicosanoids, e.g. leukotrienes {or prostaglandins}
- A61K 35/60: Fish, e.g. seahorses; Fish eggs
- A61K 35/612: Crustaceans, e.g. crabs, lobsters, shrimps, krill or crayfish; Barnacles
- A61K 35/618: Molluscs, e.g. fresh-water molluscs, oysters, clams, squids, octopus, cuttlefish, snails or slugs
- A61K 36/02: Algae
- 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

The present invention encompasses oils that have anti-inflammatory or resolution-stimulating activity that contain or are enriched with Specialized Proresolving Mediators (SPM) or SPM precursors, which originate from an oil obtained from organisms containing long chain omega-3 polyunsaturated fatty acids, such as fish, crustaceae, algae, and mollusks. The invention also encompasses a method for the production of these oils, and the utilization of the oils for nutritional supplements, pharmaceutical formulations, and cosmetic formulations, which can be employed for treating an inflammatory condition.

## Claims

### Claim 1

A method of reducing inflammation or stimulating resolution of inflammation in a subject in need thereof, the method comprising administering to the subject an effective amount of a composition comprising 18-hydroxy-eicosapentaenoic acid (18-HEPE), 17-hydroxy-docosahexaenoic acid (17-HDHA), 14-hydroxy-docosahexaenoic acid (14-HDHA), 10-hydroxy-docosahexaenoic acid (10-HDHA), and 4-hydroxy-docosahexaenoic acid (4-HDHA), wherein 17-HDHA is present in an amount of at least 100 mg/L.

### Claim 2 (depends on 1)

The method of claim 1, wherein the composition further comprises eicosapentaenoic acid (EPA) and/or docosahexaenoic acid (DHA).

### Claim 3 (depends on 1)

The method of claim 1, wherein 18-HEPE, 17-HDHA, 14-HDHA, 10-HDHA, and 4-HDHA are in a form selected from the group consisting of a free fatty-acid, an ester, a phospholipid, a mono-glyceride, a di-glyceride, a tri-glyceride, a remodeled tri-glyceride, and combinations thereof.

### Claim 4 (depends on 1)

The method of claim 1, wherein 18-HEPE, 17-HDHA, 14-HDHA, 10-HDHA, and 4-HDHA are in are in a form selected from the group consisting of an ethyl ester, a remodeled tri-glyceride, and combinations thereof.

### Claim 5 (depends on 4)

The method of claim 4, wherein 18-HEPE, 17-HDHA, 14-HDHA, 10-HDHA, and 4-HDHA are in the ethyl ester form.

### Claim 6 (depends on 4)

The method of claim 4, wherein 18-HEPE, 17-HDHA, 14-HDHA, 10-HDHA, and 4-HDHA are in the remodeled tri-glyceride form.

### Claim 7 (depends on 1)

The method of claim 1, wherein the composition further comprises a compound selected from the group consisting of:
5S-HEPE (5S-hydroxy-eicosa-6E,8Z,11Z,14Z,17Z-pentaenoic acid),
11S-HEPE (11S-hydroxy-eicosa-5Z,8Z,12E,14Z,17Z-pentaenoic acid),
12S-HEPE (12S-hydroxy-eicosa-5Z,8Z,10E,14Z,17Z-pentaenoic acid),
12R-HEPE (12R-hydroxy-eicosa-5Z,8Z,10E,14Z,17Z-pentaenoic acid),
15S-HEPE (15S-hydroxy-eicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid),
7S-HDHA (7S-hydroxy-docosa-4Z,8E,10Z,13Z,6Z,19Z-hexaenoic acid),
11S-HDHA (11S-hydroxy-docosa-4Z,7Z,9E,13Z,16Z,19Z-hexaenoic acid),
20S-HDHA (20S-hydroxy-docosa-4Z,7Z,10Z,13Z,16Z,19Z-hexaenoic acid),
17S-HDPAn-6 (17S-hydroxy-docosa-4Z,7Z,10Z,13Z,15E-pentaenoic acid),
14S-HDPAn-6 (14S-hydroxy-docosa-4Z,7Z,10Z,12E,16Z-pentaenoic acid),
10S-HDPAn-6 (10S-hydroxy-docosa-4Z,7Z,11E,13Z,16Z-pentaenoic acid),
17S-HDPAn-3 (17S-hydroxy-docosa-7Z,10Z,13Z,15E,19Z-pentaenoic acid),
14S-HDPAn-3 (14S-hydroxy-docosa-7Z,10Z,12E,16Z,19Z-pentaenoic acid),
10S-HDPAn-6 (10S-hydroxy-docosa-4Z, 7Z,11E,13Z,16Z-pentaenoic acid),
15S-HETE (15S-hydroxy-eicosa-5Z,8Z,11Z,13E-tetraenoic acid).

### Claim 8 (depends on 1)

The method of claim 1, wherein said administration lowers macroscopic and physical signs of inflammation.

### Claim 9 (depends on 1)

The method of claim 1, wherein said administration treats pain relating to an inflammatory condition.

### Claim 10 (depends on 1)

The method of claim 1, wherein said administration stimulates resolution of inflammation.

### Claim 11

A method of stimulating resolution of inflammation in a subject in need thereof, the method comprising administering to the subject an effective amount of a composition comprising fatty acids including 18-hydroxy-eicosapentaenoic acid (18-HEPE), 17-hydroxy-docosahexaenoic acid (17-HDHA), 14-hydroxy-docosahexaenoic acid (14-HDHA), 10-hydroxy-docosahexaenoic acid (10-HDHA), 4-hydroxy-docosahexaenoic acid (4-HDHA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), wherein the fatty acids are in ethyl ester form and the 17-HDHA is present in an amount of at least 100 mg/L.

### Claim 12 (depends on 11)

The method of claim 11, wherein the composition further comprises a compound selected from the group consisting of:
5S-HEPE (5S-hydroxy-eicosa-6E,8Z,11Z,14Z,17Z-pentaenoic acid),
11S-HEPE (11S-hydroxy-eicosa-5Z,8Z,12E,14Z,17Z-pentaenoic acid),
12S-HEPE (12S-hydroxy-eicosa-5Z,8Z,10E,14Z,17Z-pentaenoic acid),
12R-HEPE (12R-hydroxy-eicosa-5Z,8Z,10E,14Z,17Z-pentaenoic acid),
15S-HEPE (15S-hydroxy-eicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid),
7S-HDHA (7S-hydroxy-docosa-4Z,8E,10Z,13Z,6Z,19Z-hexaenoic acid),
11S-HDHA (11S-hydroxy-docosa-4Z,7Z,9E,13Z,16Z,19Z-hexaenoic acid),
20S-HDHA (20S-hydroxy-docosa-4Z,7Z,10Z,13Z,16Z,19Z-hexaenoic acid),
17S-HDPAn-6 (17S-hydroxy-docosa-4Z,7Z,10Z,13Z,15E-pentaenoic acid),
14S-HDPAn-6 (14S-hydroxy-docosa-4Z,7Z,10Z,12E,16Z-pentaenoic acid),
10S-HDPAn-6 (10S-hydroxy-docosa-4Z,7Z,11E,13Z,16Z-pentaenoic acid),
17S-HDPAn-3 (17S-hydroxy-docosa-7Z,10Z,13Z,15E,19Z-pentaenoic acid),
14S-HDPAn-3 (14S-hydroxy-docosa-7Z,10Z,12E,16Z,19Z-pentaenoic acid),
10S-HDPAn-6 (10S-hydroxy-docosa-4Z, 7Z,11E,13Z,16Z-pentaenoic acid),
15S-HETE (15S-hydroxy-eicosa-5Z,8Z,11Z,13E-tetraenoic acid).

### Claim 13 (depends on 11)

The method of claim 11, wherein said administration lowers macroscopic and physical signs of inflammation.

### Claim 14 (depends on 11)

The method of claim 11, wherein said administration treats pain relating to an inflammatory condition.