Skin whitening agent containing novel cyclic compound

Abstract

The present invention provides a cyclic derivative compound having remarkable whitening effects and a chemical structure of general formula (I), or a pharmaceutically acceptable salt thereof. In the formula: A is derived from an aromatic cyclic compound; B is hydrogen, oxo (=O), amino (-NH2), imino (=NH), a C1-C10 saturated or unsaturated linear or branched alkyl group, an alkoxy group, a monoalkylamino group, or a dialkylamino group; Cn, Cn+1 and Cn+2 are three adjacent carbons present in the cyclic compound; and n is a positive integer. R1 is hydrogen, hydroxyl, a saturated or unsaturated linear or branched alkyl group or an alkoxy group, X and Y are selected from hydrogen, hydroxyl, a saturated or unsaturated linear or branched alkoxy group or an acyloxy group, and one of X and Y is hydrogen. Each of R2, R3, R4 and R5 is at least one substituent independently selected from hydrogen, alkyl, alkoxy, acyloxy, acyloxymethyl, oxo, hydroxyl, vinyl, nitrile, carboxaldehyde, carbonitrile and aldehyde.

Description

technical field

[0001] The present invention relates to novel skin lightening agents, more particularly to topical skin treatment agents for topical application, and in particular to topical treatment compositions for topical application to the skin having excellent whitening effects. Background technique

[0002] Melanogenesis is the result of a process in which the production of melanin is increased by the protective mechanism of melanocytes caused by various forms of stimulation such as ultraviolet light; this in turn results in the transfer of large amounts of the melanin thus produced to the keratinocytes The cells then accumulate in the epidermal layer of the skin. Although melanin plays a role in protecting the skin, excessive pigmentation of the skin may cause liver spots, freckles, melanin production after skin inflammation, or senile pigmentation, which causes not only aesthetic inconvenience but also negative mental effects, This in turn causes discomfort in the ...

Examples

Embodiment 1

[0118] The preparation of embodiment 1.2-ethoxy ethyl benzoate

[0119] Into a round bottom flask with two openings was poured 10 mmol of 2-hydroxybenzoic acid at room temperature. Then, 50ml of dimethylformamide was added to the flask, and 24mmol of potassium carbonate (K 2 CO 3 ). Then 24 mmol ethyl bromide was slowly added dropwise thereto. After the dropwise addition was completed, the mixture was allowed to react at room temperature for 6 hours. 500ml of purified water was added to the reactant, and extracted with 100ml of n-hexane. After drying the hexane layer under reduced pressure, separation and purification were performed using silica gel column chromatography (ethyl acetate:hexane=1:50) to produce ethyl 2-ethoxybenzoate. The obtained product was identified by fast atom bombardment mass spectrometry (FAB-MS).

[0120] FAB quality: 195[M+H] +

Embodiment 2

[0121] The preparation of embodiment 2.2-propoxypropyl benzoate

[0122] Propyl 2-propoxybenzoate having the following physical properties was synthesized and obtained according to the same procedure as described in Example 1, except that bromopropane was used instead of bromoethane.

[0123] FAB quality: 223[M+H] +

Embodiment 3

[0124] The preparation of embodiment 3.2-butoxybutylbenzoate

[0125] Butyl 2-butoxybenzoate having the following physical properties was synthesized and obtained according to the same procedure as described in Example 1, except that bromobutane was used instead of bromoethane.

[0126] FAB quality: 251[M+H] +

technical field

[0001] The present invention relates to novel skin lightening agents, more particularly to topical skin treatment agents for topical application, and in particular to topical treatment compositions for topical application to the skin having excellent whitening effects. Background technique

[0002] Melanogenesis is the result of a process in which the production of melanin is increased by the protective mechanism of melanocytes caused by various forms of stimulation such as ultraviolet light; this in turn results in the transfer of large amounts of the melanin thus produced to the keratinocytes The cells then accumulate in the epidermal layer of the skin. Although melanin plays a role in protecting the skin, excessive pigmentation of the skin may cause liver spots, freckles, melanin production after skin inflammation, or senile pigmentation, which causes not only aesthetic inconvenience but also negative mental effects, This in turn causes discomfort in the ...

Examples

Embodiment 1

[0118] The preparation of embodiment 1.2-ethoxy ethyl benzoate

[0119] Into a round bottom flask with two openings was poured 10 mmol of 2-hydroxybenzoic acid at room temperature. Then, 50ml of dimethylformamide was added to the flask, and 24mmol of potassium carbonate (K 2 CO 3 ). Then 24 mmol ethyl bromide was slowly added dropwise thereto. After the dropwise addition was completed, the mixture was allowed to react at room temperature for 6 hours. 500ml of purified water was added to the reactant, and extracted with 100ml of n-hexane. After drying the hexane layer under reduced pressure, separation and purification were performed using silica gel column chromatography (ethyl acetate:hexane=1:50) to produce ethyl 2-ethoxybenzoate. The obtained product was identified by fast atom bombardment mass spectrometry (FAB-MS).

[0120] FAB quality: 195[M+H] +

Embodiment 2

[0121] The preparation of embodiment 2.2-propoxypropyl benzoate

[0122] Propyl 2-propoxybenzoate having the following physical properties was synthesized and obtained according to the same procedure as described in Example 1, except that bromopropane was used instead of bromoethane.

[0123] FAB quality: 223[M+H] +

Embodiment 3

[0124] The preparation of embodiment 3.2-butoxybutylbenzoate

[0125] Butyl 2-butoxybenzoate having the following physical properties was synthesized and obtained according to the same procedure as described in Example 1, except that bromobutane was used instead of bromoethane.

[0126] FAB quality: 251[M+H] +

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