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Resorcinol compounds for dermatological use

Inactive Publication Date: 2014-09-11
CONOPCO INC D B A UNILEVER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text describes methods for reducing or improving the appearance of visible discontinuities in skin, such as age spots, liver spots, and pigmentation disorders. The methods involve applying a therapeutically or cosmetically effective amount of resorcinol derivatives to the skin. The resorcinol derivatives can also be used in a cosmetic or dermatological composition to prevent or treat these skin conditions. The methods can be used on their own or in combination with other skin care products. The resorcinol derivatives work by reducing or preventing the appearance of pigmentation and discoloration in the skin. The patent also describes the use of resorcinol derivatives for reducing or improving the appearance of pigmentation and discoloration in skin.

Problems solved by technology

The supporting dermis is known to thin with age and exposure to the sun and environmental contaminants.
Skin problems in aging individuals can result from a variety of extrinsic or intrinsic factors such as harmful UV radiation from the sun, exposure to the environment, stress, fatigue, disease, or a combination thereof.
However, the enzyme inhibition assays may not be as good an indicator of activity as assays which are more similar to the intended clinical or cosmetic use, such as the MatTek Corporation's MelanoDerm™ Skin Model (a system which consists of normal, human-derived epidermal keratinocytes and melanocytes formed into a multilayered model of human epidermis).
Hydroquinone compositions are effective but have some undesirable side effects.
These can be burning, redness, sensitization and irritation in some patients.
Japanese Patent Application No. 27909 / 86 (JP 61-27909) refers to other hydroquinone derivatives that do not have the drawbacks of hydroquinone but that have relatively poor efficacy.
However, some of these compounds can be difficult to formulate, or may cause skin irritation.

Method used

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  • Resorcinol compounds for dermatological use
  • Resorcinol compounds for dermatological use
  • Resorcinol compounds for dermatological use

Examples

Experimental program
Comparison scheme
Effect test

example 1

4-cyclohexyl-5-methylbenzene-1,3-diol (4,5CHMR)

[0122]

[0123]4-bromo-1,5-bis(methoxymethoxy)-3-methylbenzene. 26.10 g of orcinol and 19.10 g of ammonium bromide were weighed into a 2000 mL 3-neck round bottom flask fitted with a stir bar, thermometer, and nitrogen bubbler. A nitrogen atmosphere was established and maintained. 1000 mL of acetonitrile was added, and the mixture was stirred rapidly to suspend the solids. The suspension was cooled to 10° in an ice bath and 67.88 g of Oxone™ (OXONE is a registered trademark of DuPont for a monopersulfate oxidizing compound) was added in one portion. The ice bath was removed, and the mixture was stirred at 20° for 30 h. The solids were removed by filtration. The solvent was removed from the filtrate to obtain a dark orange solid. The solid was partitioned between 200 mL of 1.0 M hydrochloric acid and 400 mL tert-butyl methyl ether. The phases were separated, and the aqueous phase was extracted with 200 mL tert-butyl methyl ether. The combin...

example 2

4-cyclohexyl-5-fluorobenzene-1,3-diol (4,5CHFR)

[0127]

2-bromo-1-fluoro-3,5-dimethoxybenzene

[0128]28.22 g of 3,5-dimethoxy-5-fluorobenzene was weighed into a 1,000 mL round bottom flask fitted with a stir bar, reflux condenser, nitrogen inlet, and cap. A nitrogen atmosphere was established and maintained throughout the reaction. 200 mL of anhydrous CCl4 was added, followed by 32.61 g of N-bromosuccinimide (NBS). The remaining NBS powder residue was washed into the flask with 100 mL of CCl4. The reaction mixture was stirred at reflux under N, for 4 h, during which time the suspended yellow solids changed color to white. At completion, the precipitated succinimide solids were filtered off and washed thoroughly with 200 mL heptane. The CCl4 was removed from the filtrate by rotary evaporation at 50° C. More succinimide precipitated from the heptane solution and was removed by filtration while the solution was still warm. The remaining heptane was removed in vacuo to obtain a clear, amber ...

example 3

2-Ethyl-1,5-dihydroxy-3-trifluoromethyl-benzene (4,5 ETFMR)

[0133]

1-(2-Iodo-4,6-dimethoxy-phenyl)-ethanone

[0134]To a solution of acetyl chloride (3.12 g, 39 mmol) in dichloromethane (100 mL) was added AlCl3 (6.34 g, 47 mmol) at 0° C. over 30 min. 1-Iodo-3,5-dimethoxy-benzene (10.5 g, 39 mmol) was added to the mixture. The reaction mixture was stirred at room temperature for 1 h. Then ice water (60 mL) was added. The aqueous layer was extracted with dichloromethane (2×30 mL), dried over sodium sulfate and concentrated, and purified by column chromatography (eluted with petroleum ether / ethyl acetate=20:1˜1:1), to give the title compound (6 g, 50%).

1-(2,4-Dimethoxy-6-trifluoromethyl-phenyl)-ethanone

[0135]A mixture of 1-(2-iodo-4,6-dimethoxy-phenyl)-ethanone (3.17 g, 10.1 mmol), difluoro-fluorosulfonyl-acetic acid methyl ester (7.9 g, 41.1 mmol) and CuI (3.8 g, 20 mmol) in NMP (50 mL) was heated at 120° C. under nitrogen overnight. The mixture was filtered and diluted with water (200 mL)...

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Abstract

Provided herein are methods and compositions comprising resorcinol derivatives for the use of treating, regulating or preventing a skin condition characterized by oxidative stress or a degenerative process. Methods of preventing, lightening or reducing the appearance of visible discontinuities of the skin resulting from skin pigmentation, skin aging, or other disorders are also disclosed.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This patent application claims priority benefit of U.S. Provisional Patent Application No. 61 / 775,384, filed Mar. 8, 2013. The entire contents of that application are hereby incorporated by reference herein.TECHNICAL FIELD[0002]Provided herein are cosmetic and dermatological compositions, such as resorcinol derivatives, with anti-aging, skin even-toning, and other useful properties for skin treatment.BACKGROUND[0003]Natural-looking skin is influenced by a number of physiological and genetic factors. Standard definitions of beautiful skin include skin having a transparent quality with uniform undertones of color and no visible or tactile discontinuities. The basis for this natural-looking appearance is in the skin structure itself. The outer layer of human skin is a semi-transparent layer known as the stratum corneum. The transparency of the stratum corneum permits glimpses of the deeper layers of skin, where blood vessels and pigments res...

Claims

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Application Information

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IPC IPC(8): C07C39/17C07C39/10C07C39/15
CPCC07C39/17C07C39/10C07C39/15A61Q19/02A61K8/69A61K8/70A61K2800/522C07C39/08C07C39/24C07C39/367C07C39/42C07C2601/02C07C2601/08C07C2601/14A61K8/347A61Q17/04A61Q19/08A61P17/00A61P17/18A61P3/02A61P43/00A61K8/37
Inventor HINMAN, ANDREW W.DAVIS, DANAKHEIFETS, VIKTORIA
Owner CONOPCO INC D B A UNILEVER
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