# US 10,245,252 B2 · Use of alkylamidothiazoles in cosmetic or dermatological preparations for the prophylaxis or treatment of sensitive skin

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- Number: US 10,245,252 B2
- Document ID: US10245252B2
- Status: Granted
- Kind: B2
- Application number: 15/104,463
- Filed: 2014-11-21
- Published: 2016-11-10
- Granted: 2019-04-02
- Earliest claimed: 2013-12-19
- Assignees: Beiersdorf AG
- Applicants: Beiersdorf AG
- Inventors: Ludger Kolbe; Cathrin Scherner; Ursula Wennsorra; Tobias Mann
- Web page: https://patentgrep.com/patent/US10245252B2

## CPC

- A61K 31/426: 1,3-Thiazoles
- A61K 8/062: {Oil-in-water emulsions}
- A61K 8/49: containing heterocyclic compounds
- 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 9/107: Emulsions {; Emulsion preconcentrates; Micelles (composition of emulsions A61K47/00)}
- A61P 17/00: Drugs for dermatological disorders
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61Q 19/005: {Preparations for sensitive skin}
- A61Q 19/007: {Preparations for dry skin}
- C07D 277/46: by carboxylic acids, or sulfur or nitrogen analogues thereof
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Use of alkylamidothiazoles in cosmetic or dermatological preparations for the prophylaxis and treatment of sensitive skin, itching, dry skin, and of inflammatory states of the human skin.

## Claims

### Claim 1

A method for the treatment or prophylaxis of sensitive skin, itching, dry skin, as well as of inflammatory states of the human skin, wherein the method comprises applying to skin of a subject in need thereof a cosmetic or dermatological preparation comprising one or more alkylamidothiazoles of the following formula in an amount which is effective for the treatment or prophylaxis of sensitive skin, itching, dry skin, inflammatory states of the human skin:
in which
R1, R2, X and Y are different, partly identical or completely identical and, independently of one another, represent:
R1=—C1-C24-alkyl (linear and branched), —C1-C24-alkenyl (linear and branched), —C1-C8-cycloalkyl, —C1-C8-cycloalkyl-alkylhydroxy, —C1-C24-alkylhydroxy (linear and branched), —C1-C24 alkylamine (linear and branched), —C1-C24-alkylaryl (linear and branched), —C1-C24-alkylaryl-alkyl-hydroxy (linear and branched), —C1-C24-alkylheteroaryl (linear and branched), —C1-C24-alkyl-O—C1-C24-alkyl (linear and branched), —C1-C24 alkyl-morpholino, —C1-C4 alkyl-piperidino, —C1-C24 alkyl-piperazino, or —C1-C24 alkyl-piperazino-N-alkyl;
R2=H, —C1-C24-alkyl (linear and branched), —C1-C24-alkenyl (linear and branched), —C1-C8-cycloalkyl, —C1-C24-hydroxyalkyl (linear and branched), —C1-C24-alkylaryl (linear and branched), or —C1-C24-alkylheteroaryl (linear and branched);
X=-phenyl, optionally mono- or polysubstituted with —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN, or cetyl;
Y=H, —C1-C24-alkyl (linear and branched), —C1-C24-alkenyl (linear and branched), —C1-C8-cycloalkyl, —C1-C24-aryl, —C1-C24-heteroaryl, —C1-C24-alkylaryl (linear and branched), —C1-C24-alkylheteroaryl (linear and branched), -phenyl, -2,4-dihydroxyphenyl, -2,3-dihydroxyphenyl, -2,4-dimethoxyphenyl, -2,3-dimethoxyphenyl, —COO-alkyl, —COO— alkenyl, —COO-cycloalkyl, —COO-aryl, or —COO-heteroaryl;
and wherein the one or more alkylamidothiazoles are present as a free base and/or as a cosmetically and dermatologically acceptable salt thereof.

### Claim 2 (depends on 1)

The method of claim 1, wherein X represents phenyl mono- or polysubstituted with —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN, or acetyl.

### Claim 3 (depends on 2)

The method of claim 2, wherein the one or more alkylamidothiazoles comprise one or more alkylamidothiazoles of formula
where the substituents Z independently represent —H, —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN, or acetyl.

### Claim 4 (depends on 3)

The method of claim 3, wherein the one or more alkylamidothiazoles comprise one or more alkylamidothiazoles of formula
where Z represents —H, —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN, or acetyl.

### Claim 5 (depends on 1)

The method of claim 1, wherein the preparation comprises one or more alkylamidothiazoles of formula
in which
X=
Y=H;
R1=—C1-C24-alkyl (linear and branched), —C1-C24-alkenyl (linear and branched), —C1-C8-cycloalkyl, —C1-C8-cycloalkyl-alkylhydroxy, —C1-C24 alkylhydroxy (linear and branched), —C1-C24 alkylamine (linear and branched), —C1-C24-alkylaryl (linear and branched), —C1-C24-alkylaryl-alkyl-hydroxy (linear and branched), —C1-C24-alkylheteroaryl (linear and branched), —C1-C24-alkyl-O—C1-C24-alkyl (linear and branched), —C1-C24-alkyl-morpholino, —C1-C24 alkyl-piperidino, —C1-C24 alkyl-piperazino, or —C1-C24 alky-piperazino-N-alkyl;
R2=H, or —C1-C24-alkyl (linear and branched);
and Z=—H, —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN, or acetyl.

### Claim 6 (depends on 1)

The method of claim 1, wherein the preparation comprises one or more alkylamidothiazoles of formula
in which
X=
Y=H;
R1=—C1-C24-alkyl (linear and branched), —C1-C24-alkenyl (linear and branched), —C1-C8-cycloalkyl, —C1-C8-cycloalkyl-alkylhydroxy, —C1-C24-alkylhydroxy (linear and branched), —C1-C24 alkylamine (linear and branched), —C1-C24-alkylaryl (linear and branched), —C1-C24-alkyl-aryl-alkyl-hydroxy (linear and branched), —C1-C24-alkylheteroaryl (linear and branched), —C1-C24-alkyl-O—C1-C24-alkyl (linear and branched), —C1-C24 alkyl-morpholino, —C1-C24 alkyl-piperidino, —C1-C24 alkyl-piperazino, or —C1-C24 alkyl-piperazino-N-alkyl;
and R2=H.

### Claim 7 (depends on 1)

The method of claim 1, wherein the preparation comprises one or more of the following alkylamidothiazoles:
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)pivalamide
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)isobutyramide
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)butyramide
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)heptanamide
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-6-hydroxyhexanamide
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-3-hydroxypropanamide
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-2-methoxyacetamide
3-amino-N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-2-propanamide
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)acetamide
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-4-(hydroxymethyl)cyclohexanecarboxamide
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)cyclohexanecarboxamide
and
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-2-(4-(hydroxymethyl)phenyl)acetamide.

### Claim 8 (depends on 1)

The method of claim 1, wherein the preparation comprises
N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)isobutyramide.

### Claim 9 (depends on 1)

The method of claim 1, wherein the preparation comprises one or more alkylamidothiazoles in the form of one or more of a halide, a carbonate, an ascorbate, a sulfate, an acetate, or a phosphate.

### Claim 10 (depends on 1)

The method of claim 1, wherein the preparation comprises from 0.000001 to 10.0% by weight of the one or more alkylamidothiazoles, based on a total weight of the preparation.

### Claim 11 (depends on 10)

The method of claim 10, wherein the preparation comprises from 0.0001 to 3.0% by weight of the one or more alkylamidothiazoles.

### Claim 12 (depends on 10)

The method of claim 10, wherein the preparation comprises from 0.001 to 1% by weight of the one or more alkylamidothiazoles.

### Claim 13 (depends on 7)

The method of claim 7, wherein the preparation comprises from 0.0001 to 3.0% by weight of the one or more alkylamidothiazoles, based on a total weight of the preparation.

### Claim 14 (depends on 13)

The method of claim 13, wherein the preparation comprises from 0.001 to 1% by weight of the one or more alkylamidothiazoles, based on a total weight of the preparation.

### Claim 15 (depends on 1)

The method of claim 1, wherein itching is treated.

### Claim 16 (depends on 1)

The method of claim 1, wherein sensitive skin is treated.

### Claim 17 (depends on 1)

The method of claim 1, wherein dry skin is treated.

### Claim 18 (depends on 1)

The method of claim 1, wherein inflammatory states in the human skin are treated.

### Claim 19 (depends on 1)

The method of claim 1, wherein sensitive skin is prevented.

### Claim 20 (depends on 1)

The method of claim 1, wherein dry skin is prevented.