# US 11,077,046 B2 · Gamma-diketones for treatment and prevention of aging skin and wrinkles

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- Number: US 11,077,046 B2
- Document ID: US11077046B2
- Status: Granted
- Kind: B2
- Application number: 16/534,455
- Filed: 2019-08-07
- Published: 2020-07-16
- Granted: 2021-08-03
- Earliest claimed: 2014-08-20
- Assignees: BioSplice Therapeutics, Inc.
- Applicants: BioSplice Therapeutics, Inc.
- Inventors: John Hood; Sunil Kumar KC; Osman Kibar; Charlene F. Barroga
- Web page: https://patentgrep.com/patent/US11077046B2

## CPC

- A61K 8/4986: {with sulfur as the only hetero atom}
- A61K 8/35: Ketones, e.g. benzophenone
- A61K 8/41: Amines
- A61K 8/49: containing heterocyclic compounds
- A61K 8/4913: {having five membered rings, e.g. pyrrolidone carboxylic acid}
- A61K 8/492: {having condensed rings, e.g. indol}
- A61K 8/4926: {having six membered rings}
- A61K 8/494: {with more than one nitrogen as the only hetero atom}
- A61K 8/4946: {Imidazoles or their condensed derivatives, e.g. benzimidazoles}
- A61K 8/4953: {containing pyrimidine ring derivatives, e.g. minoxidil}
- A61K 8/4973: {with oxygen as the only hetero atom}
- A61K 8/498: {having 6-membered rings or their condensed derivatives, e.g. coumarin}
- A61K 8/69: containing fluorine
- A61K 8/70: containing perfluoro groups, e.g. perfluoroethers
- A61Q 19/007: {Preparations for dry skin}
- A61Q 19/02: for chemically bleaching or whitening the skin
- A61Q 19/08: Anti-ageing preparations
- A61K 2800/10: General cosmetic use
- 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)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

The present disclosure relates to compounds, cosmetic or dermopharmaceutical compositions comprising the same, and methods for using the compounds or compositions for treating, protecting, and/or improving the condition and/or aesthetic appearance of skin, for example, treating, preventing, ameliorating, reducing and/or eliminating fine lines and/or wrinkles of skin, or improving the appearance of fine lines and/or or wrinkles of skin comprising application of the compounds or compositions disclosed.

## Claims

### Claim 1

A method for improving the aesthetic appearance of a subject's skin, the method comprising administering to the subject an effective amount of a compound of Formula IIIa, or a dermatologically acceptable salt thereof:
wherein:
R10 is selected from the group consisting of H, unsubstituted —C1-6 alkyl, —C1-3 haloalkyl, halide, —OR13, and CN;
R11 is selected from the group consisting of unsubstituted —C1-6 alkyl, —CH2OH, —CH2N(R13b)2, —C1-3 haloalkyl, halide, —OR13, and CN;
R12 is a substituent attached to the phenyl ring and is independently selected at each occurrence from the group consisting of unsubstituted —C1-6 alkyl, —CH2OH, —CH2N(R13b)2, —C1-3 haloalkyl, halide, —OR13, and CN;
each R13 is independently selected from the group consisting of unsubstituted —C1-6 alkyl, and —C1-3 haloalkyl;
each R13b is independently selected from the group consisting of H and unsubstituted —C1-3 alkyl; and
each q is 0 to 5.

### Claim 2 (depends on 1)

The method of claim 1, wherein the compound of Formula IIIa is selected from the group consisting of:
or a dermatologically acceptable salt thereof.

### Claim 3

A method for improving the aesthetic appearance of a subject's skin, the method comprising administering to skin an effective amount of a cosmetic or dermopharmaceutical composition comprising a compound according to Formula IIIa, or a dermatologically acceptable salt thereof:
wherein:
R10 is selected from the group consisting of H, unsubstituted —C1-6 alkyl, —C1-3 haloalkyl, halide, —OR13, and CN;
R11 is selected from the group consisting of unsubstituted —C1-6 alkyl, —CH2OH, —CH2N(R13b)2, —C1-3 haloalkyl, halide, —OR13, and CN;
R12 is a substituent attached to the phenyl ring and is independently selected at each occurrence from the group consisting of unsubstituted —C1-6 alkyl, —CH2OH, —CH2N(R13b)2, —C1-3 haloalkyl, halide, —OR13, and CN;
each R13 is independently selected from the group consisting of unsubstituted —C1-6 alkyl, and —C1-3 haloalkyl;
each R13b is independently selected from the group consisting of H and unsubstituted —C1-3 alkyl; and
each q is 0 to 5.

### Claim 4 (depends on 1)

The method of claim 1, wherein the improvement in aesthetic appearance is improvement in one or more of skin tone, radiance, clarity, tautness, skin firmness, plumpness, suppleness, softness, skin texture, skin texturization and moisturization, appearance of skin contours, appearance of hollow cheeks, appearance of sunken, baggy, or dark circles under eyes, skin luster, brightness, skin thickness, and skin elasticity and/or resiliency.

### Claim 5 (depends on 1)

The method of claim 1, wherein the improvement in aesthetic appearance is the reduction and/or prevention of fine lines or wrinkles.

### Claim 6 (depends on 1)

The method of claim 1, wherein the improvement in aesthetic appearance is the improvement in procollagen and/or collagen production.

### Claim 7 (depends on 1)

The method of claim 1, wherein the compound is administered as a cosmetic or dermopharmaceutical composition.

### Claim 8 (depends on 7)

The method according to claim 7, wherein the cosmetic or dermopharmaceutical composition is a topical composition.

### Claim 9 (depends on 7)

The method according to claim 7, wherein the cosmetic composition is intended for use as a non-therapeutic treatment.

### Claim 10 (depends on 1)

The method according to claim 1, wherein the subject is human.

### Claim 11 (depends on 3)

The method according to claim 3, wherein the subject is human.