# US 10,307,353 B2 · 1-phenylmono- or -polyhydroxypropane compounds, compositions and cosmetic uses thereof

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

- Number: US 10,307,353 B2
- Document ID: US10307353B2
- Status: Granted
- Kind: B2
- Application number: 15/534,190
- Filed: 2015-12-11
- Published: 2017-12-21
- Granted: 2019-06-04
- Earliest claimed: 2015-12-11
- Assignees: L'oreal
- Applicants: L'oreal
- Inventors: Maria Dalko; Julien Hitce
- Web page: https://patentgrep.com/patent/US10307353B2

## CPC

- A61K 8/347: {Phenols}
- A61K 8/34: Alcohols
- A61K 8/345: {containing more than one hydroxy group}
- A61K 31/085: having an ether linkage to aromatic ring nuclear carbon
- A61K 31/09: having two or more such linkages
- A61P 17/00: Drugs for dermatological disorders
- A61Q 19/08: Anti-ageing preparations
- C07C 43/23: 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
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to novel compounds of formula (I) to compositions comprising same, and also to the use thereof for preventing and/or cosmetically treating the signs of aging of the skin.

## Claims

### Claim 1

A process for retarding the onset of and/or reducing the signs of aging of the skin which comprises applying to the skin an effective amount for retarding the onset of and/or reducing the signs of aging of the skin of a composition comprising a physiologically acceptable medium and a compound of formula (I)
in which
n=0; 1; 2 or 3
m=0; 1; 2 or 3
with 1≤m+n≤3
R1 independently denotes a linear C1-C6 alkyl radical or a branched C3-C6 alkyl radical or a linear C1-C6 acyl radical,
R2 denotes a hydrogen atom and R3 denotes a hydrogen atom or an OH radical, an optical isomer, stereoisomer and/or diastereoisomer thereof and/or salt thereof
wherein the compound of formula (I) is present at a concentration of between 0.01% and 30% by weight relative to the total weight of the composition.

### Claim 2

A process for retarding the onset of and/or reducing the signs of aging of the skin which comprises applying to the skin a composition comprising a physiologically acceptable medium and a compound of formula (I)
in which
n=0; 1; 2 or 3
m=0; 1; 2 or 3
with 2≤m+n≤3
R1 independently denotes a linear C1-C6 alkyl radical or a branched C3-C6 alkyl radical or a linear C1-C6 acyl radical,
R2 denotes a hydrogen atom and R3 denotes a hydrogen atom or an OH radical, an optical isomer, stereoisomer and/or diastereoisomer thereof and/or salt thereof
wherein the compound of formula (I) is present at a concentration of between 0.01% and 30% by weight relative to the total weight of the composition.

### Claim 3 (depends on 1)

The process as claimed in claim 1, wherein, in the compound of formula (I):
2≤m+n≤3
each of the substituents R1 independently denotes a linear C1-C4 alkyl radical.

### Claim 4 (depends on 1)

The process as claimed in claim 1, wherein the compound of formula (I) is a compound of formula (II):
in which:
2≤m+n≤3.

### Claim 5 (depends on 4)

The process as claimed in claim 4, in which:
each of the substituents R1 independently denotes a linear C1-C4 alkyl radical.

### Claim 6 (depends on 1)

The process as claimed in claim 1, wherein the compound of formula (I) is chosen from compounds 1 to 4 below, the optical isomers, stereoisomers and diastereoisomers thereof and/or geometrical isomers thereof and/or salts thereof:
Compound
Structure
1
2
3
4

### Claim 7 (depends on 1)

The process as claimed in claim 1, wherein the compound of formula (I) is a compound of formula (III):
in which:
n=0; 1; 2 or 3
m=0; 1; 2 or 3
with 1≤m+n≤3
each of the substituents R1 independently denotes a linear C1-C6 alkyl radical or a branched C3-C6 alkyl radical or a linear C2-C6 acyl radical.

### Claim 8 (depends on 1)

The process as claimed in claim 1, wherein the compound of formula (I) is chosen from compounds 5 and 6 below, the optical isomers, stereoisomers and diastereoisomers thereof or geometrical isomers thereof and/or salts thereof:
Compound
Structure
5
6

### Claim 9 (depends on 1)

The process as claimed in claim 1 which is a cosmetic treatment process for retarding the onset of and/or reducing the signs of aging of mature and/or wrinkled skin, characterized in that a compound of formula (I) or a composition containing it, is applied to the mature and/or wrinkled skin.

### Claim 10 (depends on 9)

The cosmetic treatment process as claimed in claim 9 which is intended for promoting the renewal of the keratinocytes and for retarding the onset of and/or reducing signs chosen from thinning of the epidermis, surface wrinkles and impairment of the barrier function.

### Claim 11 (depends on 1)

The process as claimed in claim 1, wherein the signs on the skin are chosen from wrinkled skin, skin exhibiting impairment of its viscoelastic or biomechanical properties, skin exhibiting impairment in the cohesion of its tissues, thinned skin, and skin exhibiting impairment of its surface appearance.

### Claim 12 (depends on 1)

The process as claimed in claim 1, wherein the compound of formula (I) is present, in a composition containing a physiologically acceptable medium, at a concentration of between 0.1% and 10% by weight relative to the total weight of the composition.

### Claim 13 (depends on 1)

The process as claimed in claim 1, wherein the compound of formula (I) is present, in a composition containing a physiologically acceptable medium, at a concentration of between 0.5% and 5% by weight relative to the total weight of the composition.

### Claim 14 (depends on 1)

The process as claimed in claim 1, wherein the compound of formula (I) is present, in a composition containing a physiologically acceptable medium, wherein the composition does not contain hydrogen peroxide.