KR20220043362A - New composition for improving skin conditions - Google Patents

Abstract

The present invention relates to a composition for improving skin condition, the composition comprising, as an active ingredient, a derivative of a compound represented by general formula (I) or a pharmaceutically acceptable salt thereof. (In general formula (I), R represents a linear or branched alkyl group having 1 to 20 carbon atoms).

Description

Composition for improving skin condition {New composition for improving skin conditions}

The present invention relates to a composition for skin regeneration and wrinkle improvement, and more particularly, an external preparation for skin, specifically a cosmetic or pharmaceutical composition, has few side effects and is safe for the human body and has excellent skin regeneration and wrinkle improvement effects.

Collagen is a major matrix protein produced by fibroblasts of the skin and is present in the extracellular matrix. Its main functions include skin firmness, connective tissue resistance and bonding, support of cell adhesion, and induction of cell division and differentiation. . This collagen decreases with age and photoaging by UV irradiation, which is closely related to the formation of wrinkles in the skin. In addition, as extensive research on skin aging has recently been developed, an important function of collagen in the skin has been revealed.

Retinoic acid, placental protein, betulinic acid, and the like have been reported as ingredients that promote collagen synthesis and have a wrinkle-improving effect. However, there is a problem in that the use of the ingredients is limited due to safety issues such as irritation and redness when applied to the skin, or the effect of improving the skin function cannot be expected because the efficacy is insignificant.

Therefore, there is an urgent need to develop a material that is safe for the living body, is stable over time, and has superior skin regeneration and anti-wrinkle effects than existing materials.

An object of the present invention is to provide a composition for external application for skin that has no side effects on the skin and has excellent skin regeneration and anti-wrinkle effects.

The above object is a composition for skin improvement comprising a derivative of a compound represented by the following general formula (I) or a pharmaceutically acceptable salt thereof as an active ingredient:

(I)

In the above formula, R is a C ₁ to C ₂₀ straight-chain or branched alkyl group, more preferably a C ₁ to C ₈ straight-chain or branched alkyl group.

Since the compound according to the present invention has no side effects on the skin and exhibits skin regeneration and wrinkle improvement effects, a composition containing the same can be used as a composition for skin regeneration and wrinkle improvement.

The present invention provides a composition for improving skin comprising a derivative of a compound represented by the following general formula (I) or a pharmaceutically acceptable salt thereof, as an active ingredient, which is excellent in skin regeneration and wrinkle improvement effects.

(I)

In the above formula, R is a C ₁ to C ₂₀ straight-chain or branched alkyl group, more preferably a C ₁ to C ₈ straight-chain or branched alkyl group.

Hereinafter, the present invention will be described in more detail.

The compound of the present invention is obtained through an ester reaction by slowly adding an alkyl halide in an appropriate equivalent ratio after dissolving the aromatic compound in a suitable organic solvent as shown in the following reaction scheme, or by re-hydrogenating the reactant. It can be obtained by carrying out In this case, the organic solvent that can be used for the reaction is not particularly limited, and examples thereof include dichloromethane, chloroform, tetrahydrofuran, acetonitrile, dimethylformamide, pyridine, and dimethylformamide. In particular, sodium hydride (NaH) or potassium carbonate (K ₂ CO ₃ ) may be used as a reaction catalyst.

[Scheme 1]

In the above formula, R is a C _1-20 straight-chain or branched alkyl group, more preferably a C _1-8 straight-chain or branched alkyl group.

The present invention also provides a composition for external application for skin regeneration and wrinkle improvement comprising the compound of formula (I) as an active ingredient.

The composition comprising the compound of the present invention may further contain an appropriate carrier, excipient or diluent according to a conventional method.

Carriers, excipients and diluents that may be included in the composition of the present invention include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia gum, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.

The composition comprising the compound of the present invention is formulated in the form of oral dosage forms such as powders, granules, tablets, capsules, suspensions, emulsions, syrups, and aerosols, external preparations, suppositories, or sterile injection solutions, respectively, according to a conventional method. can be used for

Specifically, in the case of formulation, it can be prepared using a diluent or excipient such as a filler, extender, binder, wetting agent, disintegrant, surfactant, etc. usually used. Solid preparations for oral administration include tablets, pills, powders, granules, capsules, etc., and these solid preparations include at least one excipient in the extract, for example, starch, calcium carbonate, sucrose ), lactose, gelatin, etc. can be mixed and prepared. In addition to simple excipients, lubricants such as magnesium stearate and talc may also be used. Liquid formulations for oral use include suspensions, solutions, emulsions, and syrups. In addition to commonly used simple diluents such as water and liquid paraffin, various excipients such as wetting agents, sweeteners, fragrances, and preservatives are included. can Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solutions, suspensions, emulsions, lyophilized formulations and suppositories. Non-aqueous solvents and suspending agents include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate. As the base of the suppository, witepsol, macrogol, tween 61, cacao butter, laurin, glycerogelatin, and the like can be used.

The composition for skin regeneration and wrinkle improvement comprising the compound of formula (I) of the present invention as an active ingredient is a formulation for external application to the skin that can be applied to the skin, such as creams, gels, patches, sprays, ointments, warning agents, lotions, It can be prepared and used as a pharmaceutical composition in the form of an external preparation for the skin of liniment, pasta, or cataplasma, but is not limited thereto.

A preferred dosage of the compound of formula (I) of the present invention or a pharmacologically acceptable salt thereof varies depending on the patient's condition and body weight, the degree of disease, drug form, administration route and period, but may be appropriately selected by those skilled in the art. can However, for desirable effects, the compound of the present invention is preferably administered at 0.0001 to 100 mg/kg per day, preferably 0.001 to 10 mg/kg. Administration may be administered once a day, or may be administered in several divided doses. The above dosage does not limit the scope of the present invention in any way.

The compounding amount of the compounds according to the present invention in the external pharmaceutical composition for skin is preferably 0.0001 to 20% by weight, more preferably 0.001 to 10% by weight, based on the total weight of the composition, which is less than 0.001% by weight. It is because there is a concern and it is difficult to expect an increase in the effect even if it is blended when it exceeds 20% by weight.

In addition, the pharmaceutical dosage forms of the compounds of the present invention may be used in the form of pharmaceutically acceptable salts thereof, and may be used alone or in combination with other pharmaceutically active compounds as well as in an appropriate group.

The present invention provides a composition for external application for skin for skin regeneration and wrinkle improvement comprising the compound of formula (I) as an active ingredient.

The composition comprising the compound of formula (I) of the present invention as an active ingredient can be used in various ways, such as cosmetics and face wash for skin regeneration and anti-wrinkle effect. Products to which the present composition can be added include, for example, cosmetics such as various creams, lotions, and skins, and cleansing agents, face washes, soaps, treatments, and cosmetics.

The cosmetic of the present invention includes a composition selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, polymer peptides, polymer polysaccharides, sphingolipids, and seaweed extract.

As the water-soluble vitamin, any one can be used as long as it can be formulated in cosmetics. Preferably, vitamin B1, vitamin B2, vitamin B6, pyridoxine, pyridoxine hydrochloride, vitamin B12, pantothenic acid, nicotinic acid, nicotinic acid amide, folic acid, vitamin C, vitamin H, etc. are mentioned. Also, their salts (thiamine hydrochloride, sodium ascorbate salt, etc.) and derivatives (ascorbic acid-2-phosphate sodium salt, ascorbic acid-2-phosphate magnesium salt, etc.) are also included in the water-soluble vitamins that can be used in the present invention. Included. Water-soluble vitamins can be obtained by conventional methods, such as a microbial transformation method, a purification method from a microbial culture, an enzymatic method, or a chemical synthesis method.

The oil-soluble vitamin may be any as long as it can be formulated in cosmetics, but preferably includes vitamin A, carotene, vitamin D2, vitamin D3, vitamin E (d1-alpha tocopherol, d-alpha tocopherol, d-alpha tocopherol), etc. , their derivatives (ascorbine palmitate, ascorbine stearate, ascorbine dipalmitate, dl-alpha tocopherol acetate, dl-alpha tocopherol nicotinic acid, vitamin E, DL-pantothenyl alcohol, D-pantothenyl alcohol, pantothenyl ethyl ethers, etc.) are also included in the oil-soluble vitamins used in the present invention. Oil-soluble vitamins can be obtained by conventional methods such as a microbial transformation method, a purification method from a microbial culture, and an enzyme or chemical synthesis method.

The macromolecular peptide may be any type of peptide as long as it can be formulated in cosmetics. Preferably, collagen, hydrolyzed collagen, gelatin, elastin, hydrolyzed elastin, keratin, and the like are mentioned. Polymeric peptides can be purified and obtained by conventional methods such as purification from a microbial culture solution, enzyme method or chemical synthesis method, or can be purified and used from natural products such as dermis of pigs or cattle, silk fiber of silkworms, etc.

The high molecular weight polysaccharide may be any compound as long as it can be formulated in cosmetics, but preferably hydroxyethyl cellulose, xanthan gum, sodium hyaluronate, chondroitin sulfate, or a salt thereof (such as sodium salt). For example, chondroitin sulfate or a salt thereof can be used after purification from mammals or fish.

The sphingolipid may be any as long as it can be formulated in cosmetics, and ceramide, phytosphingosine, sphingoglycolipid and the like are preferred. Sphingo lipids can be purified by conventional methods from mammals, fish, shellfish, yeast or plants, or can be obtained by chemical synthesis.

The seaweed extract may be any one as long as it can be formulated in cosmetics, but preferably brown algae extract, red algae extract, green algae extract, etc., and calrageenan purified from these seaweed extracts, arginic acid, sodium alginate, Potassium alginate and the like are also included in the seaweed extract used in the present invention. The seaweed extract can be obtained by purification from seaweed by a conventional method.

In the cosmetic of the present invention, in addition to the above essential ingredients, if necessary, other ingredients usually blended in cosmetics may be blended.

Other ingredients that may be added include oils and fats, moisturizers, emollients, surfactants, organic and inorganic pigments, organic powders, UV absorbers, preservatives, bactericides, antioxidants, plant extracts, pH adjusters, alcohols, colorants, fragrances, A blood circulation promoter, a cooling agent, a restrictive agent, purified water, etc. are mentioned.

Examples of the fats and oils include ester fats and oils, hydrocarbon oils, silicone oils, fluorine oils, animal fats, and vegetable oils.

As ester-based fats and oils, tri2-ethylhexanoate glyceryl, 2-ethylhexanoate cetyl, isopropyl myristate, butyl myristate, isopropyl palmitate, ethyl stearate, octyl palmitate, isocetyl isostearate, stearic acid Butyl, ethyl linoleate, isopropyl linoleate, ethyl oleate, isocetyl myristate, isostearyl myristate, isostearyl palmitate, octyldodecyl myristate, isocetyl isostearate, diethyl sebacate, adipine Diisopropyl acid, isoalkyl neopentanoate, tri(caprylic acid, capric acid) glyceryl, trimethylol propane tri-2-ethylhexanoate, trimethylol propane triisostearate, pentaelysitol tetra2-ethylhexanoate , cetyl caprylate, decyl laurate, hexyl laurate, decyl myristate, myristyl myristate, cetyl myristate, stearyl stearate, decyl oleate, cetyl ricinoleate, isostea laurate Lil, isotridecyl myristate, isocetyl palmitate, octyl stearate, isocetyl stearate, isodecyl oleate, octyldodecyl oleate, octyldodecyl linoleate, isostearic acid isopropyl, 2-ethylhexanoate cetoster Aryl, 2-ethyl stearyl hexanoate, hexyl isostearate, ethylene glycol dioctanoate, ethylene glycol dioleate, propylene glycol dicapric acid, di(caprylic acid, capric acid) propylene glycol, dicaprylic acid propylene glycol, dicapric acid Neopentyl glycol phosphate, neopentyl glycol dioctanoate, glyceryl tricaprylate, glyceryl triundecyl, glyceryl triisopalmitate, glyceryl triisostearate, octyldodecyl neopentanoate, isostearyl octanoate , isononanoate octyl, neodecanoate hexyldecyl, neodecanoate octyldodecyl, isostearate isocetyl, isostearyl isostearate, isostearic acid octyldecyl, polyglycerol oleate, polyglycerol isostearate, Triisocetyl citrate, triisoalkyl citrate, triisooctyl citrate, lauryl lactate, myristyl lactate, cetyl lactate, octyldecyl lactate, triethyl citrate, acetyl triethyl citrate, acetyl tributyl citrate, trioctyl citrate, dimalate Isostearyl, 2-ethylhexyl hydroxystearate, di2-ethylhexyl succinate, diisobutyl adipate, diisopropyl sebacate, dioctyl sebacate, Cholesteryl stearate, cholesteryl isostearate, cholesteryl hydroxystearate, cholesteryl oleate, dihydrocholesteryl oleate, phytsteryl isostearate, phytsteryl oleate, 12-stealoyl Ester type, such as hydroxy stearate isocetyl, 12-stealoyl hydroxy stearyl stearate, and 12-stealoyl hydroxy stearate isostearyl, etc. are mentioned.

Examples of hydrocarbon-based fats and oils include hydrocarbon-based fats and oils such as squalene, liquid paraffin, alpha-olefin oligomer, isoparaffin, ceresin, paraffin, liquid isoparaffin, polybudene, microcrystalline wax, petrolatum.

Examples of silicone oils and fats include polymethylsilicone, methylphenylsilicone, methylcyclopolysiloxane, octamethylpolysiloxane, decamethylpolysiloxane, dodecamethylcyclosiloxane, dimethylsiloxane methylcetyloxysiloxane copolymer, dimethylsiloxane methylstealloxysiloxane copolymer, and alkyl-modified silicone. Oil, amino-modified silicone oil, etc. are mentioned.

Perfluoropolyether etc. are mentioned as fluorine-type fats and oils.

As animal or vegetable oils, avocado oil, almond oil, olive oil, sesame oil, rice bran oil, saffron oil, soybean oil, corn oil, rapeseed oil, passerine oil, palm kernel oil, palm oil, castor oil, sunflower oil, grape seed oil , Cottonseed Oil, Palm Oil, Kukui Nut Oil, Wheat Germ Oil, Rice Germ Oil, Shea Butter, Wormwood Colostrum, Marcus Damien Nut Oil, Meadow Oil, Egg Yolk Oil, Tallow Oil, Horse Oil, Mink Oil, Orange Raffy Oil, Jojoba Oil , animal or plant oils and fats such as candelabra wax, carnauba wax, liquid lanolin, and hydrogenated castor oil.

Examples of the moisturizing agent include a water-soluble low-molecular moisturizer, a fat-soluble molecular moisturizer, a water-soluble polymer, and a fat-soluble polymer.

As water-soluble low molecular weight moisturizers, serine, glutamine, sorbitol, mannitol, pyrrolidone-sodium carboxylate, glycerin, propylene glycol, 1,3-butylene glycol, ethylene glycol, polyethylene glycol B (polymerization degree n = 2 or more), polypropylene Glycol (polymerization degree n=2 or more), polyglycerol B (polymerization degree n=2 or more), lactic acid, lactic acid salt, etc. are mentioned.

Cholesterol, cholesterol ester, etc. are mentioned as a fat-soluble low molecular weight humectant.

Examples of the water-soluble polymer include carboxyvinyl polymer, polyaspartate, tragacanth, xanthan gum, methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose, water-soluble chitin, chitosan, and dextrin. can

Examples of the fat-soluble polymer include polyvinylpyrrolidone icocene copolymer, polyvinylpyrrolidone hexadecene copolymer, nitrocellulose, dextrin fatty acid ester, and high molecular weight silicone.

Examples of the emollient include long-chain acylglutamic acid cholesteryl ester, hydroxystearic acid cholesteryl, 12-hydroxystearic acid, stearic acid, rosin acid, and lanolin fatty acid cholesteryl ester.

Nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, etc. are mentioned as surfactant.

Nonionic surfactants include self-emulsifying glycerin monostearate, propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerol fatty acid ester, sorbitan fatty acid ester, POE (polyoxyethylene) sorbitan fatty acid ester, POE sorbitan fatty acid ester, POE Glycerin fatty acid ester, POE alkyl ether, POE fatty acid ester, POE hydrogenated castor oil, POE castor oil, POEPOP (polyoxyethylene polyoxypropylene) copolymer, POEPOP alkyl ether, polyether-modified silicone, lauric acid alkanolamide, alkyl Amine oxide, hydrogenated soybean phospholipid, etc. are mentioned.

Examples of the anionic surfactant include fatty acid soap, alpha-acyl sulfonate, alkyl sulfonate, alkyl allyl sulfonate, alkyl naphthalene sulfonate, alkyl sulfate, POE alkyl ether sulfate, alkyl amide sulfate, alkyl phosphate, POE alkyl phosphate, and alkyl amide phosphate. , alkyloylalkyltaurine salts, N-acylamino acid salts, POE alkylethercarboxylate salts, alkylsulfosuccinate salts, alkylsulfoacetate sodium, acylated hydrolyzed collagen peptide salts, perfluoroalkylphosphate esters, and the like. .

Examples of the cationic surfactant include alkyltrimethylammonium chloride, stearyltrimethylammonium chloride, stearyltrimethylammonium bromide, cetostearyltrimethylammonium chloride, distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, behenyltrimethylammonium bromide, chloride Benzalkonium, diethylaminoethylamide stearate, dimethylaminopropylamide stearate, quaternary ammonium salt of lanolin derivative, etc. are mentioned.

Examples of the amphoteric surfactant include carboxybetaine type, amidebetaine type, sulfobetaine type, hydroxysulfobetaine type, amidesulfobetaine type, phosphobetaine type, aminocarboxylate type, imidazoline derivative type, amidamine type, etc. Amphoteric surfactant etc. are mentioned.

Examples of organic and inorganic pigments include silicic acid, silicic anhydride, magnesium silicate, talc, sericite, mica, kaolin, bengala, clay, bentonite, titanium-coated mica, bismuth oxychloride, zirconium oxide, magnesium oxide, zinc oxide, titanium oxide, aluminum oxide. , inorganic pigments such as calcium sulfate, barium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, iron oxide, ultramarine blue, chromium oxide, chromium hydroxide, calamine, and complexes thereof; Polyamide, polyester, polypropylene, polystyrene, polyurethane, vinyl resin, urea resin, phenol resin, fluororesin, silicon resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, divinylbenzene styrene copolymer, silk Organic pigments, such as powder, a cellulose, CI pigment yellow, and CI pigment orange, and the composite pigment of these inorganic pigments and an organic pigment, etc. are mentioned.

Examples of the organic powder include metal soaps such as calcium stearate; alkyl phosphate metal salts such as sodium cetylate, zinc laurylate, and calcium laurylate; acylamino acid polyvalent metal salts such as calcium N-lauroyl-beta-alanine, zinc N-lauroyl-beta-alanine, and calcium N-lauroyl glycine; amidesulfonic acid polyvalent metal salts such as calcium N-lauroyl-taurine and calcium N-palmitoyl-taurine; N such as N-epsilon-lauroyl-L-lysine, N-epsilon-palmitoylizine, N-alpha-paritoylolnithine, N-alpha-lauroylarginine, N-alpha-hydrogenated beef fatty acid acylarginine, etc. -Acyl basic amino acid; N-acyl polypeptides, such as N-lauroyl glycyl glycine; alpha-amino fatty acids such as alpha-aminocaprylic acid and alpha-aminolauric acid; Polyethylene, polypropylene, nylon, polymethyl methacrylate, polystyrene, a divinylbenzene-styrene copolymer, ethylene tetrafluoride, etc. are mentioned.

As UV absorbers, para-aminobenzoic acid, para-aminobenzoate ethyl, para-aminobenzoate amyl, para-aminobenzoate octyl, ethylene glycol salicylate, phenyl salicylate, octyl salicylate, benzyl salicylate, butylphenyl salicylate, homomentyl salicylate, benzyl cinnamate , Para-methoxycinnamic acid-2-ethoxyethyl, para-methoxycinnamic acid octyl, dipara-methoxycinnamic acid mono-2-ethylhexaneglyceryl, para-methoxycinnamic acid isopropyl, diisopropyl diisopropyl cinnamic acid ester mixture, urokanin Acid, ethyl urokanate, hydroxymethoxybenzophenone, hydroxymethoxybenzophenonesulfonic acid and its salts, dihydroxymethoxybenzophenone, sodium dihydroxymethoxybenzophenonedisulfonate, dihydroxybenzophenone, tetrahydroxybenzophenone, 4- tert -butyl-4'-methoxydibenzoylmethane, 2,4,6-trianilino- p- (carbo-2'-ethylhexyl-1'-oxy)-1, 3,5-triazine, 2-(2-hydroxy-5-methylphenyl) benzotriazole, etc. are mentioned.

Examples of disinfectants include hinokitiol, triclosan, trichlorohydroxydiphenyl ether, chlorhexidine gluconate, phenoxyethanol, resorcin, isopropylmethylphenol, azulene, salicylic acid, zinc phyllithione, benzalkonium chloride, photosensitizer. So, No. 301, mononitroguaial sodium, undecyrenic acid, etc. are mentioned.

Examples of the antioxidant include butylhydroxyanisole, propyl gallic acid, and ellisorbic acid.

Examples of the pH adjuster include citric acid, sodium citrate, malic acid, sodium malate, fmalic acid, sodium fumarate, succinic acid, sodium succinate, sodium hydroxide, sodium monohydrogen phosphate, and the like.

As alcohol, higher alcohols, such as cetyl alcohol, are mentioned.

In addition, blending components that may be added in addition to this are not limited thereto, and any of the above components can be blended within a range that does not impair the object and effect of the present invention, but preferably 0.01 to 5% by weight relative to the total weight, More preferably, it is blended at 0.01-3% by weight.

The cosmetic of the present invention may take the form of a solution, an emulsion, a viscous mixture, or the like.

Components included in the cosmetic composition of the present invention may include components commonly used in cosmetic compositions in addition to the compounds of formula (I) as an active ingredient, for example, stabilizers, solubilizers, vitamins, and pigments. and conventional adjuvants and carriers such as perfumes.

The cosmetic composition of the present invention may be prepared in any formulation conventionally prepared in the art, for example, emulsions, creams, lotions, packs, foundations, lotions, cosmetics, hair cosmetics, and the like.

Specifically, the cosmetic composition of the present invention is a skin lotion, skin softener, skin toner, astringent, lotion, milk lotion, moisture lotion, nourishing lotion, massage cream, nourishing cream, moisture cream, hand cream, foundation, essence, nourishing essence, It includes formulations of packs, soaps, cleansing foams, cleansing lotions, cleansing creams, body lotions, and body cleansers.

When the formulation of the present invention is a paste, cream or gel, animal fiber, vegetable fiber, wax, paraffin, starch, tracanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as a carrier component. can

When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component. In particular, in the case of a spray, additional chlorofluorohydrocarbon, propane /may contain propellants such as butane or dimethyl ether.

When the formulation of the present invention is a solution or emulsion, a solvent, solvating agent or emulsifying agent is used as a carrier component, for example, water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 ,3-butylglycol oil, glycerol fatty esters, fatty acid esters of polyethylene glycol or sorbitan.

When the formulation of the present invention is a suspension, as a carrier component, water, a liquid diluent such as ethanol or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, microcrystalline Cellulose, aluminum metahydroxide, bentonite, agar or tracanth may be used.

When the formulation of the present invention is a surfactant-containing cleansing agent, aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyl taurate, sarcosinate, fatty acid amide as carrier components Ether sulfate, alkylamidobetaine, aliphatic alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, linolin derivative or ethoxylated glycerol fatty acid ester and the like may be used.

Hereinafter, the present invention will be described in detail by the following Examples and Experimental Examples.

However, the following Examples and Experimental Examples only illustrate the present invention, and the content of the present invention is not limited by the following Examples and Experimental Examples.

Example 1.

In a two-neck round flask at room temperature, 10 mmol of the compound of Scheme 1 (refer to Table 1) was put into each, and then 50 ml of dimethylformamide was added. After 12 mmol of potassium carbonate (K2CO3) was added as a catalyst, 12 mmol of bromo methane was slowly added dropwise. After the dropwise addition, the reaction was carried out at room temperature for 4 hours. 500ml of purified water was added to the reaction product, and extraction was performed using 100ml of n-hexane. After drying the hexane layer under reduced pressure, silica gel column chromatography was performed using a mixed solvent of n-hexane and ethyl acetate as a developing solvent to obtain a hypothetical reaction product, which was identified using high-speed atomic bombardment mass spectrometry (hereinafter, FAB-MS). did

compound R FAB mass Example 1 CH3 253 [M+H] ⁺ Example 2 C2H5 267 [M+H] ⁺ Example 3 C3H7 281 [M+H] ⁺ Example 4 C4H9 295 [M+H] ⁺ Example 5 C5H11 309 [M+H] ⁺ Example 6 C6H13 323 [M+H] ⁺ Example 7 C8H17 351 [M+H] ⁺ Example 8 C10H21 379 [M+H] ⁺ Example 9 C12H25 407 [M+H] ⁺ Example 10 C14H29 435 [M+H] ⁺ Example 11 C16H33 463 [M+H] ⁺ Example 12 C20H41 519 [M+H] ⁺

Experimental Example 1. Collagen synthesis effect

The compounds prepared according to the methods described in Examples 1 to 12 and vitamin C were added to the culture medium of human-derived fibroblasts to test the effect of promoting collagen synthesis at the cellular level. The measurement of synthesized collagen was quantified using a PICP EIA kit (Procollagen Type I C-peptide enzyme immunoassay kit). Before the experiment, human-derived fibroblasts were evaluated for cytotoxicity at concentrations of 10ppm, 1ppm, and 0.1ppm of the test substance, and collagen synthesis ability was evaluated by selecting a concentration without cytotoxicity.

In the experiment, the final concentration of the compound was 1 ppm and 10 ppm, and each sample was added to the culture medium of human fibroblasts and cultured for 1 day. was used to measure at 450 nm. For comparison of the effects, the collagen synthesis level was measured in the same way for the fibroblast culture medium (control group) to which nothing was added and the sample to which vitamin C was added to a final concentration of 50 ppm. The amount of collagen production was measured as UV absorbance, and the rate of increase in collagen production was calculated as the ratio of collagen production relative to the control group, and the results are summarized in Table 2 below.

Collagen biosynthesis effect (number of repetitions = 3) sample Concentration (ppm) Collagen increase rate (%) Control (no additive) - - vitamin C 50 28 Example 1 compound One 24 10 38 Example 2 compound One 28 10 62 Example 3 compound One 27 10 49 Example 4 compound One 21 10 38 Example 5 compound One 22 10 36 Example 6 compound One 21 10 33 Example 7 compound One 19 10 32 Example 8 compound One 13 10 21 Example 9 compound One 12 10 19 Example 10 compound One 9 10 15 Example 11 compound One 5 10 12 Example 12 compound One 3 10 9

As can be seen from the results in Table 2, the compounds of Examples 1 to 12 exhibited a better collagen synthesis effect at a lower concentration than when vitamin C, which is generally known to have a collagen synthesis ability, was applied.

Preparation Example 1. Preparation of softened lotion

Formulation 1 and Comparative Formulation 1 were prepared with the composition shown in Table 3 below.

Composition (wt%) Formulation 1 Comparative Formulation 1 a b c d material of example 1 0.5 - - - - material of example 2 - 0.5 - - - material of example 7 - - 0.5 - - material of example 9 - - - 0.5 - ethanol 10.0 10.0 10.0 10.0 10.0 Polyoxyethylene hydrogenated castor oil 1.0 1.0 1.0 1.0 1.0 methyl paraoxybenzoate 0.2 0.2 0.2 0.2 0.2 glycerin 5.0 5.0 5.0 5.0 5.0 1,3-butylene glycol 6.0 6.0 6.0 6.0 6.0 incense appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount Purified water to 100 to 100 to 100 to 100 to 100

Preparation Example 2. Preparation of nutrient lotion

Formulation 2 and Comparative Formulation 2 were prepared with the composition shown in Table 4 below.

Composition (wt%) Formulation 2 Comparative Formulation 2 a b c d material of example 1 0.5 - - - - material of example 2 - 0.5 - - - material of example 7 - - 0.5 - - material of example 9 - - - 0.5 - Polyoxyethylene hydrogenated castor oil 1.0 1.0 1.0 1.0 1.0 methyl paraoxybenzoate 0.2 0.2 0.2 0.2 0.2 glycerin 6.0 6.0 6.0 6.0 6.0 1,3-butylene glycol 5.0 5.0 5.0 5.0 5.0 Carbomer 0.2 0.2 0.2 0.2 0.2 triethanolamine 0.3 0.3 0.3 0.3 0.3 propylene glycol 5.0 5.0 5.0 5.0 5.0 ethanol 3.2 3.2 3.2 3.2 3.2 Carboxyvinyl Polymer 0.1 0.1 0.1 0.1 0.1 incense appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount Purified water to 100 to 100 to 100 to 100 to 100

Preparation Example 3. Preparation of cream

Formulation 3 and Comparative Formulation 3 were prepared with the composition shown in Table 5 below.

Composition (wt%) Formulation 3 Comparative Formulation 3 a b c d material of example 1 0.5 - - - - material of example 2 - 0.5 - - - material of example 7 - - 0.5 - - material of example 9 - - - 0.5 - cetanol 2.0 2.0 2.0 2.0 2.0 PEG-20 1.0 1.0 1.0 1.0 1.0 sorbitan monostearate 1.0 1.0 1.0 1.0 1.0 mineral oil 10.0 10.0 10.0 10.0 10.0 trioctanoate 5.0 5.0 5.0 5.0 5.0 triethanolamine 0.5 0.5 0.5 0.5 0.5 Carbomer 0.2 0.2 0.2 0.2 0.2 glycerin 5.0 5.0 5.0 5.0 5.0 propylene glycol 3.0 3.0 3.0 3.0 3.0 antiseptic appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount incense appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount Purified water to 100 to 100 to 100 to 100 to 100

Preparation Example 4. Preparation of ointment for external use on the skin

Formulation 4 and Comparative Formulation 4 were prepared with the composition shown in Table 6 below.

Composition (wt%) Formulation 4 Comparative Formulation 4 a b c d material of example 1 0.5 - - - - material of example 2 - 0.5 - - - material of example 7 - - 0.5 - - material of example 9 - - - 0.5 - diethyl sebacate 8.0 8.0 8.0 8.0 8.0 brazing 5.0 5.0 5.0 5.0 5.0 Polyoxyethylene oleyl ether phosphate 6.0 6.0 6.0 6.0 6.0 sodium benzoate appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount vaseline to 100 to 100 to 100 to 100 to 100

Preparation Example 5. Preparation of Essence

Formulation 5 and Comparative Formulation 5 were prepared with the composition shown in Table 7 below.

Composition (wt%) Formulation 5 Comparative Formulation 5 a b c d material of example 1 0.5 - - - - material of example 2 - 0.5 - - - material of example 7 - - 0.5 - - material of example 9 - - - 0.5 - propylene glycol 10.0 10.0 10.0 10.0 10.0 glycerin 10.0 10.0 10.0 10.0 10.0 Sodium hyaluronate aqueous solution (1%) 5.0 5.0 5.0 5.0 5.0 ethanol 5.0 5.0 5.0 5.0 5.0 Polyoxyethylene hydrogenated castor oil 1.0 1.0 1.0 1.0 1.0 methyl paraoxybenzoate 0.1 0.1 0.1 0.1 0.1 Carbomer 0.4 0.4 0.4 0.4 0.4 incense appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount Purified water to 100 to 100 to 100 to 100 to 100

Preparation Example 6. Preparation of pack

Formulation 6 and Comparative Formulation 6 were prepared with the composition shown in Table 8 below.

Composition (wt%) Formulation 6 Comparative Formulation 6 a b c d material of example 1 0.5 - - - - material of example 2 - 0.5 - - - material of example 7 - - 0.5 - - material of example 9 - - - 0.5 - glycerin 5.0 5.0 5.0 5.0 5.0 propylene glycol 4.0 4.0 4.0 4.0 4.0 polyvinyl alcohol 15.0 15.0 15.0 15.0 15.0 ethanol 8.0 8.0 8.0 8.0 8.0 Polyoxyethylene hydrogenated castor oil 1.0 1.0 1.0 1.0 1.0 Polyoxyethylene oleyl ether phosphate 1.0 1.0 1.0 1.0 1.0 methyl paraoxybenzoate 0.2 0.2 0.2 0.2 0.2 incense appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount Purified water to 100 to 100 to 100 to 100 to 100

Claims (3)

A composition for skin regeneration and/or wrinkle improvement comprising a compound represented by the following general formula (I) and/or a mixture thereof as an active ingredient
(I)

In the above formula, R is a C ₁ to C ₂₀ linear or branched alkyl group. The method of claim 1,
A composition for improving wrinkles, comprising 0.00001 to 10.0% by weight of the compound of Formula 1 and/or a mixture thereof, based on the total amount of the composition. The method according to any one of claims 1 to 2,
The composition is a composition, characterized in that formed in any one formulation selected from the group consisting of skin, lotion, cream, foundation, essence, gel, pack, product cleansing and ointment.