IP Library Granted Patent US 12,497,385
Granted Patent B2
US 12,497,385 · App. 17/554,725 · Granted Dec 16, 2025

Photoprotective compositions containing

Inventors: Michael Einziger (Malibu, CA); Ann Marie Simpson (Malibu, CA)
Assignee: VERSICOLOR TECHNOLOGIES, LLC
C07D403/06A61K8/494A61K8/4973A61K31/404A61K31/407A61K31/55A61Q19/02C07D405/06C07D487/04C07D519/00
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Quick Facts
Patent No.
US 12,497,385
App. No.
17/554,725
Granted
Dec 16, 2025
Kind
B2
Abstract

The present invention relates to compounds, compositions, and methods for modulating skin pigmentation and treating or preventing UV-induced skin damage, erythema, aging of the skin, sunburn, and hyperpigmentation in a subject. The compounds, compositions, and methods of the present invention generally involve Malassezia -derived compounds, including malassezin and indirubin, and/or chemical analogs thereof. Other applications of the compounds and compositions disclosed herein include, but are not limited to, improving hyperpigmentation caused by a hyperpigmentation disorder, inducing melanocyte apoptosis, and modulating arylhydrocarbon receptor (AhR) activity, melanogenesis, melanin production, melanosome biogenesis, melanosome transfer, melanocyte activity, and melanin concentration.

Claims (49)

1 . A method for brightening skin in a subject, the method comprising contacting the subject with a composition comprising:

a compound having the structure of the following formula:

wherein:

X is selected from the group consisting of NR 14 and O;

Y is CR 5 R 6 , O, or NR 15 ;

R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 10 , and R 11 are independently selected from the group consisting of hydrogen, halogen, CN, hydroxyl, R 16 , and OR 16 ;

R 13 is hydrogen,

R 14 and R 15 are independently hydrogen or R 16 ;

R 5 and R 6 are independently selected from the group consisting of hydrogen, hydroxyl, OR 16 , R 16 , and C 3-6 cycloalkyl, or R 5 and R 6 combine to form an oxo (═O) group or a C 3-6 cycloalkyl;

R 12 is —COR a ;

each R 16 is independently formyl, C 1-9 alkyl, C 2-9 alkenyl, or C 2-9 alkynyl; and,

R a is selected from the group consisting of hydrogen, hydroxyl, and OR 16 ;

wherein:

R 14 is H, or

at least one of R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 10 , and R 11 is C 1-4 alkyl, or

R 14 is H and at least one of R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 10 , and R 11 is C 1-4 alkyl, and

wherein:

if R a is hydrogen, Y is CR 5 R 6 , and R 14 is hydrogen, then

R 5 is selected from the group consisting of hydroxyl, OR 16 , and C 3-6 cycloalkyl, or

R 5 and R 6 combine to form a C 3-6 cycloalkyl,

or a hydrate or cosmetically or pharmaceutically acceptable salt thereof, and a cosmetically or pharmaceutically acceptable vehicle, diluent or carrier.

2 . The method of claim 1 , wherein the compound has the following structure:

or a hydrate or cosmetically or pharmaceutically acceptable salt thereof.

3 . The method of claim 1 ,

wherein:

Y is CR 5R 6 ;

R 5 is hydrogen, and R 6 is hydrogen, C 1-4 alkyl, C 3-6 cycloalkyl, or O—(C 1-4 alkyl);

or R 5 and R 6 combine to form an oxo (═O) group.

4 . The method of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 10 , and R 11 is C 1-4 alkyl.

5 . The method of claim 1 , wherein each of R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 10 , and R 11 is hydrogen.

6 . The method of claim 1 , wherein the compound is selected from the group consisting of:

or a hydrate or cosmetically or pharmaceutically acceptable salt thereof.

7 . The method of claim 1 , wherein the compound is:

or a hydrate or cosmetically or pharmaceutically acceptable salt thereof.

8 . The method of claim 1 , wherein X is NH.

9 . The method of claim 2 , wherein X is NH.

10 . The method of claim 3 , wherein X is NH.

11 . The method of claim 4 , wherein X is NH.

12 . The method of claim 5 , wherein X is NH.

13 . The method of claim 8 , wherein R 12 is CO(—O—C 1-4 alkyl).

14 . The method of claim 9 , wherein R 12 is CO(—O—C 1-4 alkyl).

15 . The method of claim 10 , wherein R 12 is CO(—O—C 1-4 alkyl).

16 . The method of claim 11 , wherein R 12 is CO(—O—C 1-4 alkyl).

17 . The method of claim 12 , wherein R 12 is CO(—O—C 1-4 alkyl).

18 . The method of claim 13 , wherein Y is CH (C 3 H 5 ).

19 . The method of claim 14 , wherein Y is CH (C 3 H 5 ).

20 . The method of claim 15 , wherein Y is CH (C 3 H 5 ).

21 . The method of claim 16 , wherein Y is CH (C 3 H 5 ).

22 . The method of claim 17 , wherein Y is CH (C 3 H 5 ).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 24, 2022
From: EINZIGER, MICHAEL; SIMPSON, ANN MARIE
To: VERSICOLOR TECHNOLOGIES, LLC
Reel/Frame 060307/0752 →
Continuity (8)
Division 16382891 · Apr 12, 2019
Provisional Application 62742657 · Oct 8, 2018
Provisional Application 62722412 · Aug 24, 2018
Provisional Application 62686912 · Jun 19, 2018
Provisional Application 62685800 · Jun 15, 2018
Provisional Application 62668007 · May 7, 2018
Provisional Application 62656769 · Apr 12, 2018
Related Publication 20220106297A1 · Apr 7, 2022
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