# US 12,215,084 B2 · 2(1H)-pyridinones and their use to treat inflammatory conditions

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- Number: US 12,215,084 B2
- Document ID: US12215084B2
- Status: Granted
- Kind: B2
- Application number: 17/610,242
- Filed: 2020-04-30
- Published: 2022-08-04
- Granted: 2025-02-04
- Earliest claimed: 2019-05-14
- Assignees: Conopco, Inc.
- Applicants: Conopco, Inc.
- Inventors: Guoqiang Chen; Yudong Wang; Dandan Huang
- Web page: https://patentgrep.com/patent/US12215084B2

## CPC

- C07D 213/64: attached in position 2 or 6
- A61K 8/4926: {having six membered rings}
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61Q 5/006: {Antidandruff preparations}
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 5/12: Preparations containing hair conditioners
- A61Q 19/00: Preparations for care of the skin
- A61K 2800/10: General cosmetic use
- A61K 2800/81: Preparation or application process involves irradiation
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

Disclosed is a novel compound and a process of preparing it. It has been shown to have anti-inflammatory activity and can be utilised in a wide range of cosmetic compositions. The compound is a 2(1H)-pyridinone of formula (1) in amide or enol form. It may be prepared by exposing a solution of piroctone olamine in an organic solvent or in water comprising at least one surfactant to UV radiation to degrade the piroctone olamine. The compound of formula (1) is separated from the degradation products by chromatography.

## Claims

### Claim 1

A compound of the formula 1, which may exist in amide form A or enol form B:

### Claim 2 (depends on 1)

The compound as claimed in claim 1, wherein the compound of formula 1 is in enol form B.

### Claim 3 (depends on 1)

A cosmetic composition comprising the compound as claimed in claim 1 and a cosmetically acceptable carrier.

### Claim 4 (depends on 3)

The cosmetic composition as claimed in claim 3, wherein amount of said compound is from 0.01 to 10 wt %.

### Claim 5 (depends on 3)

The cosmetic composition as claimed in claim 3, wherein said composition is a hair care composition.

### Claim 6 (depends on 5)

The hair care composition as claimed in claim 5, wherein said composition is a shampoo, hair conditioner, hair cream, hair gel, hair serum, mousse, or a hair oil.

### Claim 7 (depends on 3)

A method of reducing inflammation on a topical surface of a human or an animal comprising a step of applying thereon the composition as claimed in claim 3.

### Claim 8 (depends on 3)

A method of treating an inflammatory condition of the skin, or scalp or oral cavity of a human or an animal comprising a step of applying thereon the composition as claimed in claim 3.

### Claim 9 (depends on 1)

A process of preparing the compound of the formula 1 as claimed in claim 1 comprising:
i) preparing a solution of piroctone olamine by dissolving piroctone olamine in an organic solvent or in water comprising at least one surfactant;
ii) exposing said solution to UV radiation of 100 mW to 2000 mW in a UV chamber for 0.5 hour to 8 hours to cause degradation of piroctone olamine to form degradation products of said piroctone olamine; and
iii) separating said degradation products of piroctone olamine to a chromatographic technique to get said compound of the formula 1.

### Claim 10 (depends on 1)

A non-therapeutic method of reducing inflammation on a topical surface of a human or an animal comprising a step of applying thereon the compound as claimed in claim 1.

### Claim 11 (depends on 1)

A method of treating an inflammatory condition of the skin, or scalp or oral cavity of a human or an animal comprising a step of applying thereon the compound as claimed in claim 1.