# US 2014/0194399 A1 · Use of pufas for treating skin inflammation

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2014/0194399 A1
- Document ID: US20140194399A1
- Status: Published application
- Kind: A1
- Application number: 14/203,837
- Filed: 2014-03-11
- Published: 2014-07-10
- Earliest claimed: 2009-04-29
- Assignees: Dignity Sciences Limited
- Applicants: Dignity Sciences Limited
- Inventors: Adam Kelliher; Angus Morrison; Phil Knowles
- Web page: https://patentgrep.com/patent/US20140194399A1

## CPC

- A61K 31/202: having three or more double bonds, e.g. linolenic (eicosanoids, e.g. leukotrienes A61K31/557)
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 31/573: substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 13/12: of the kidneys
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/04: Antipruritics
- A61P 17/06: Antipsoriatics
- A61P 17/16: Emollients or protectives, e.g. against radiation
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 37/02: Immunomodulators
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 59/42: containing hydroxy or O-metal groups
- 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

## Abstract

The present invention provides a compound which is a polyunsaturated fatty acid (PUFA) derivative of formula (I), or a pharmaceutically acceptable salt, or solvate thereof, for use in treating various skin disorders.

## Claims

### Claim 1

A method for treating or preventing skin inflammation in a mammal caused by exposure to electromagnetic radiation, the method comprising administering a therapeutically effective amount of a composition comprising 15-HETrE to the skin of the mammal.

### Claim 2 (depends on 1)

The method of claim 1, wherein the composition comprises about 1 mg to about 1,000 mg of 15-HETrE.

### Claim 3 (depends on 1)

The method of claim 1, wherein the 15-HETrE is a pharmaceutically acceptable salt or solvate of 15-HETrE.

### Claim 4 (depends on 1)

The method of claim 1, wherein the electromagnetic radiation comprises ultraviolet radiation.

### Claim 5 (depends on 4)

The method of claim 4, wherein the ultraviolet radiation comprises solar radiation.

### Claim 6 (depends on 1)

The method of claim 1, wherein the composition is administered topically to the skin of the subject.

### Claim 7 (depends on 6)

The method of claim 6, wherein the composition is administered in an amount sufficient to deliver 0.00001 g to 10 g of 15-HETrE per square meter of skin.

### Claim 8 (depends on 6)

The method of claim 6, wherein the composition is administered in an amount sufficient to deliver 0.0001 g to 1 g of 15-HETrE per square meter of skin.

### Claim 9 (depends on 1)

The method of claim 1, wherein the composition is co-administered with a corticosteroid selected from the group consisting of clobetasol diproprionate, betamethasone diproprionate, halbetasol proprionate, diflorasone diacetate, fluocinonide, halcinonide, amcinonide, desoximetasone, triamcinolone acetonide, mometasone furoate, fluticasone proprionate, fluocinolone acetonide, hydrocortisone valerate, hydrocortisone butyrate, triamcinalone acetonide, desonide, prednicarbate, prednisolone, methylprednisolone, dexamethasone, naflocort, deflazacort, halopredone acetate, budesonide, beclomethasone dipropionate, hydrocortisone, clocortolone pivalate, methylprednisolone aceponate, dexamethasone palmitoate, tipredane, hydrocortisone aceponate, alclometasone dipropionate, halometasone, methylprednisolone suleptanate, rimexolone, prednisolone farnesylate, ciclesonide, deprodone propionateloteprednol etabonate, betamethasone butyrate propionate, flunisolide, prednisone, dexamethasone sodium phosphate, triamcinolone, betamethasone 17-valerate, betamethasone, betamethasone dipropionate, hydrocortisone acetate, hydrocortisone sodium succinate, prednisolone sodium phosphate, hydrocortisone probutate, and combinations thereof.

### Claim 10 (depends on 9)

The method of claim 9, wherein the corticosteroid is co-administered in an amount sufficient to provide 50% or less of the recommended daily dosage of said corticosteroid in said mammal.

### Claim 11 (depends on 10)

The method of claim 10, wherein the corticosteroid is hydrocortisone.

### Claim 12 (depends on 1)

The method of claim 1, wherein the composition is co-administered with a further therapeutic agent selected from the group consisting of immunomodulators, antibiotics, immunosuppressants, and anti-itch drugs.

### Claim 13 (depends on 1)

The method of claim 1, wherein the composition further comprises a pharmaceutically acceptable diluent or carrier.

### Claim 14

A method of treating or preventing skin inflammation caused by exposure to ultraviolet radiation in a mammal, the method comprising administering to the mammal a composition comprising a therapeutically effective amount of a compound of Formula (I):
or a pharmaceutically acceptable salt or solvate thereof, wherein
-Alk- is —(CH2)3-[cis]CH═CH—CH2-[cis]CH═CH-[trans]CH═CH—CH(OR2)—;
R1 is selected from the group consisting of: hydrogen; C1-C6 alkyl; C2-C6 alkenyl; C2-C6 alkynyl; C6-C10 aryl; 5- to 10-membered heteroaryl; C3-C7 carbocyclyl or 5- to 10-membered heterocyclyl group; a group of formula —CH2—CH(OR3)—CH2—(OR4) wherein R3 and R4 are each independently hydrogen atoms or —(C═O)—R6, wherein R6 is an aliphatic group having from 3 to 29 carbon atoms; and a group of formula —(CH2OCH2)mOH, wherein m is an integer from 1 to 200;
R2 is selected from the group consisting of:
a hydrogen atom;
a group of formula —(C═O)—R5, wherein R5 is a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6-C10 aryl, 5- to 10-membered heteroaryl, C3-C7 carbocyclyl or 5- to 10-membered heterocyclyl group;
an aliphatic group having from 3 to 29 carbon atoms; and
a group of formula —(CH2OCH2)nOH, wherein n is an integer of from 1 to 200; and
wherein said alkyl, alkenyl, alkynyl and aliphatic groups are the same or different and are each unsubstituted or substituted with 1, 2 or 3 unsubstituted substituents which are the same or different and are selected from halogen atoms and C1-C4 alkoxy, C2-C4 alkenyloxy, C1-C4 haloalkyl, C2-C4 haloalkenyl, C1-C4 haloalkoxy, C2-C4 haloalkenyloxy, hydroxyl, —SR′, and —NR′R″ groups where R′ and R″ are the same or different and represent hydrogen or unsubstituted C1-C2 alkyl; said aryl, heteroaryl, carbocyclyl and heterocyclyl groups are the same or different and are each unsubstituted or substituted by 1, 2, 3 or 4 unsubstituted substituents which are the same or different and are selected from halogen atoms, and cyano, nitro, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkenyloxy, haloalkyl, C2-C4 haloalkenyl, C1-C4 haloalkoxy, C2-C4 haloalkenyloxy, hydroxyl, C1-C4 hydroxyalkyl, —SR′ and —NR′R″ groups wherein each R′ and R″ is the same or different and represents hydrogen or unsubstituted C1-C4 alkyl.

### Claim 15 (depends on 14)

The method of claim 14, wherein:
R1 is hydrogen or C1-C6 alkyl; and
R2 is a hydrogen atom or an aliphatic group having from 3 to 29 carbon atoms.

### Claim 16

A method of treating or preventing skin inflammation caused by exposure to ultraviolet radiation in a mammal, the method comprising administering to the mammal a composition comprising a therapeutically effective amount of a compound of formula:
or a pharmaceutically acceptable salt or solvate thereof.