# US 2014/0154190 A1 · Skin Lightening Compositions

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- Number: US 2014/0154190 A1
- Document ID: US20140154190A1
- Status: Published application
- Kind: A1
- Application number: 14/175,360
- Filed: 2014-02-07
- Published: 2014-06-05
- Earliest claimed: 2010-01-06
- Assignees: ELC Management LLC
- Inventors: Yoko Niki; Masaki Yoshida; Masamitsu Ichihashi; Hideya Ando; Daniel B. Yarosh; Mary S. Matsui
- Web page: https://patentgrep.com/patent/US20140154190A1

## CPC

- A61K 8/4946: {Imidazoles or their condensed derivatives, e.g. benzimidazoles}
- A61K 8/49: containing heterocyclic compounds
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/16: Emollients or protectives, e.g. against radiation
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- A61Q 19/02: for chemically bleaching or whitening the skin
- A61K 2800/782: Enzyme inhibitors; Enzyme antagonists
- 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

Compositions and methods for lightening and/or depigmenting skin are provided, the compositions comprising compounds having the structure: wherein: R1 and R2 are same or different and are each selected from the group consisting of hydrogen, alkyl, carbomethoxy, carboethoxy, alkoxy, and alkanoyl, any of which may be halogen-substituted, and halogen; R6 is selected from the group consisting of hydrogen, methyl, and ethyl; and R3, R4 and R5 are the same or different and are each selected from the group consisting of hydrogen, methyl, methoxy, ethoxy, methoxyethoxy, ethoxyethoxy, propoxy, propoxymethoxy, and the like, any of which may be halogen-substituted; or having the structure: wherein: R2 is hydrogen, lower alkyl or hydroxy lower alkyl; R3 is lower alkyl, —CH2CN, hydroxy lower alkyl, —NO, —CH2N═C or (wherein R6 and R7 are independently selected from the group consisting of hydrogen and lower alkyl) or hydrogen provided R2 is not hydrogen; R4 is Z-T-W wherein Z represents —O—, —NH— or a single bond; T represents a straight- or branched-chain lower-alkylene group; when Z is a single bond, T also represents an ethenylene or a propenylene group wherein the unsaturated carbon is at the single bond; when Z is —O—, T also represents an allylene group wherein the saturated carbon is at the oxygen; and W represents hydrogen, when T is allylene and Z is —O—, and Ar, wherein Ar is selected from thienyl, pyridinyl, furanyl, phenyl and substituted phenyl wherein there are one or more substituents on the phenyl independently selected from halogen or lower alkyl; and R5 is hydrogen, halogen or lower alkyl; or pharmaceutically-, cosmetically- and dermatologically-acceptable salts, solvates, and bioprecursors, and stereoisomers and enantiomers of these compounds, free from or mixed with other enantiomers or stereoisomers; and such compounds in compositions with a pharmaceutically-, cosmetically- or dermatologically-acceptable carrier thereof comprising a safe and effective amount of the skin lightening or depigmenting compound.

## Claims

### Claim 1

A topically applicable composition for lightening or depigmenting skin, comprising in the range of from about 0.00005% to about 0.5% of at least one compound selected from the group consisting of omeprazole (5- or 6-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole); esomeprazole (S-5-methoxy-2-{(4-methoxy-3,5dimethylpyridin-2-yl)methylsufinyl]-3H-benzoimidazole); lansoprazole (2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl-1H-benzo(d)imidazole); pantoprazole (RS-6-(difluoromethoxy))-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzo(d)imidazole); rabeprazole (pariprazole) (2-([4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo(d)imidazole); leminoprazole (2-((o-(isobutylmethylamino)benzyl)sulfinyl)benzimidazole); timoprazole (2-(pyridine-2-ylmethylsulfinyl)-1H-benzimidazole); and sulfides and sodium salts thereof; and
a cosmetic ingredient which is a further skin lightening compound, a sunscreen, or a combination thereof;
formulated into a topically applicable, cosmetically or dermatologically acceptable vehicle, carrier or diluent therefor.

### Claim 2 (depends on 1)

The topically applicable composition for lightening or depigmenting skin according to claim 1, comprising at least one sulfide of at least one compound selected from the group consisting of omeprazole (5- or 6-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole); esomeprazole (S-5-methoxy-2-{(4-methoxy-3,5dimethylpyridin-2-yl)methylsufinyl]-3H-benzoimidazole); lansoprazole (2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl-1H-benzo(d)imidazole); pantoprazole (RS-6-(difluoromethoxy))-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzo(d)imidazole); rabeprazole (pariprazole) (2-([4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo(d)imidazole); leminoprazole (2-((o-(isobutylmethylamino)benzyl)sulfinyl)benzimidazole); and timoprazole (2-(pyridine-2-ylmethylsulfinyl)-1H-benzimidazole).

### Claim 3 (depends on 2)

The topically applicable composition for lightening or depigmenting skin according to claim 2, comprising a sulfide of omeprazole (5- or 6-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole).

### Claim 4 (depends on 1)

The topically applicable composition for lightening or depigmenting skin according to claim 1, which is in the form of an anhydrous composition, an aqueous-based solution, a suspension, a dispersion, a lotion, a serum, an essence, an emulsion, a milk, a cream, a gel, a paste, an ointment, a spray, a stick, a mousse, an aerosol or microcapsules.

### Claim 5

A method of lightening or depigmenting the skin, comprising topically applying to skin in need of such treatment a topically applicable composition comprising in the range of from about 0.00005% to about 0.5% of at least one compound selected from the group consisting of esomeprazole (S-5-methoxy-2-{(4-methoxy-3,5dimethylpyridin-2-yl)methylsufinyl]-3H-benzoimidazole); lansoprazole (2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl-1H-benzo(d)imidazole); pantoprazole (RS-6-(difluoromethoxy))-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzo(d)imidazole); rabeprazole (pariprazole), (2-([4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo(d)imidazole); leminoprazole (2-((o-(isobutylmethylamino)benzyl)sulfinyl)benzimidazole); timoprazole (2-(pyridine-2-ylmethylsulfinyl)-1H-benzimidazole); and sulfides and sodium salts thereof; and
a cosmetic ingredient which is a further skin lightening compound, a sunscreen, or a combination thereof;
formulated into a topically applicable, cosmetically or dermatologically acceptable vehicle, carrier or diluent therefor.

### Claim 6 (depends on 5)

The method of lightening or depigmenting the skin according to claim 5, wherein the topically applicable composition comprises at least one sulfide of at least one compound selected from the group consisting of omeprazole (5- or 6-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole); esomeprazole (S-5-methoxy-2-{(4-methoxy-3,5dimethylpyridin-2-yl)methylsufinyl]-3H-benzoimidazole); lansoprazole (2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl-1H-benzo(d)imidazole); pantoprazole (RS-6-(difluoromethoxy))-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzo(d)imidazole); rabeprazole (pariprazole) (2-([4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo(d)imidazole); leminoprazole (2-((o-(isobutylmethylamino)benzyl)sulfinyl)benzimidazole); and timoprazole (2-(pyridine-2-ylmethylsulfinyl)-1H-benzimidazole).

### Claim 7 (depends on 5)

The method of lightening or depigmenting the skin according to claim 5, wherein the topically applicable composition comprises a sulfide of omeprazole (5- or 6-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole).

### Claim 8 (depends on 5)

The method of lightening or depigmenting the skin according to claim 5, wherein the topically applicable composition is in the form of an anhydrous composition, an aqueous-based solution, a suspension, a dispersion, a lotion, a serum, an essence, an emulsion, a milk, a cream, a gel, a paste, an ointment, a spray, a stick, a mousse, an aerosol or microcapsules.