WO2016137196A1 - Dérivé de 7-déshydrocholestérol conjugué a un acide gras - Google Patents
Dérivé de 7-déshydrocholestérol conjugué a un acide gras Download PDFInfo
- Publication number
- WO2016137196A1 WO2016137196A1 PCT/KR2016/001748 KR2016001748W WO2016137196A1 WO 2016137196 A1 WO2016137196 A1 WO 2016137196A1 KR 2016001748 W KR2016001748 W KR 2016001748W WO 2016137196 A1 WO2016137196 A1 WO 2016137196A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dehydrocholesterol
- fatty acid
- conjugated
- derivative
- present
- Prior art date
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/63—Steroids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/318—Foods, ingredients or supplements having a functional effect on health having an effect on skin health and hair or coat
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
Definitions
- the present invention relates to a fatty acid conjugated 7-dehydrocholesterol derivative, and more particularly, to a fatty acid conjugated 7-dehydrocholesterol derivative which increases stability and skin absorption, is hydrolyzed in the body to supply vitamin D, and It relates to a wrinkle improvement and anti-aging composition comprising the same.
- vitamin D The main forms of vitamin D include vitamin D 2 (ergocalciferol) and vitamin D 3 (cholecalciferol, compound II), both of which are metabolized in the liver and kidneys (calcitriol, compound III). Will be converted to).
- 7-dehydro-cholesterol (7-dehydrocholesterol: 7-DHC , compound I) is converted into a pro-vitamin (provitamin) of vitamin D 3 form, a vitamin D 3 by sunlight.
- Vitamin D 3 is commonly used to treat osteoporosis patients by stimulating calcium absorption and strengthening bone density. It is also used as a supplement for the elderly and residents of the northern latitudes of poor sunlight.
- 7-dehydrocholesterol known as a precursor of vitamin D
- US Patent Publication No. 2013-0017234 has shown the potential as a joint treatment drug by expressing factors such as Col-1, ALP, OSX, OC, BMP-2, IL-5, etc., which are related to bone formation.
- Patent No. 10-0568600 is reported to have excellent hair protection effect through clinical trials.
- 7-dehydrocholesterol is very unstable outside the skin and is converted into various substances by light, and the converters have no side effects but become very difficult to convert to vitamin D 3 .
- 7-dehydrocholesterol is converted to pyrocalciferol, lumysterol, and isopyrocalciferol, thereby degrading activity.
- US Pat. No. 5,342,833 shows an example of the use of cholecalciferol derivatives for the treatment of skin diseases and psoriasis
- US Pat. No. 5,747,478 uses magnesium oxide and sodium citrate.
- An example of stabilizing cholecalciferol is shown.
- the present inventors have diligently studied to improve the above-described problems of 7-dehydrocholesterol, such as chemical instability, ultraviolet light, temperature, and instability due to contact with air, and as a result, esterified conjugates of 7-dehydrocholesterol to fatty acids
- 7-dehydrocholesterol such as chemical instability, ultraviolet light, temperature, and instability due to contact with air
- Another object of the present invention is to provide an anti-wrinkle and anti-aging composition comprising the fatty acid conjugated 7-dehydrocholesterol derivative.
- Still another object of the present invention is to provide a method for improving wrinkles and anti-aging, comprising administering to a subject a composition comprising the fatty acid conjugated 7-dehydrocholesterol derivative.
- the present invention relates to a fatty acid conjugated 7-dehydrocholesterol derivative of formula (1).
- R is the portion of the fatty acid excluding the carboxyl group.
- R is C 3 -C 27 saturated or unsaturated hydrocarbon chain, in particular C 11 -C 17 saturated hydrocarbon chain, or C 15 -C 21 unsaturated hydrocarbon having 1 to 6 double bonds It can be a chain.
- R is a saturated or unsaturated hydrocarbon chain derived from palmitic acid, lauric acid, linoleic acid, linolenic acid or oleic acid. Can be.
- the fatty acid conjugated 7-dehydrocholesterol derivative of Formula 1 according to the present invention may be prepared according to the method shown in Scheme 1 below.
- the method described in the following reaction scheme is merely exemplary of the method used in the present invention, the order of the unit operation, the reaction reagent, the reaction conditions and the like may be changed as much as the case may be.
- R is as defined in formula (1).
- the fatty acid conjugated 7-dehydrocholesterol derivative of Formula 1 may be prepared by condensing 7-dehydrocholesterol with saturated or unsaturated fatty acids in the presence of a condensing agent and an organic base.
- 7-dehydrocholesterol may be prepared by condensation reaction in the presence of organic base without using a condensation agent with an acid chloride of saturated or unsaturated fatty acid.
- condensing agent examples include N, N, N'N'-tetramethyl- (benzotriazol-1-yl) -uronium tetrafluoroborate (TBTU), and N- (3-dimethylaminopropyl) -N'- Ethyl-carbodiimide (EDC), N, N'-diisopropylcarbodiimide (DIC), N, N'-dicyclohexylcarbodiimide (DCC) and the like can be used, but are not limited thereto.
- EDC Ethyl-carbodiimide
- DIC N, N'-diisopropylcarbodiimide
- DCC N'-dicyclohexylcarbodiimide
- the organic base may be triethylamine (TEA), diisopropylethylamine (DIPEA), 4-dimethylaminopyridine (DMAP), pyridine (Pyridine) and the like, but is not limited thereto.
- TAA triethylamine
- DIPEA diisopropylethylamine
- DMAP 4-dimethylaminopyridine
- Pyridine pyridine
- reaction solvent at least one selected from organic solvents such as dichloromethane (DCM), benzene, toluene, tetrahydrofuran (THF) and dimethylformamide (DMF) may be used, but is not limited thereto.
- organic solvents such as dichloromethane (DCM), benzene, toluene, tetrahydrofuran (THF) and dimethylformamide (DMF) may be used, but is not limited thereto.
- the reaction may proceed in a cooled to warmed state.
- the condensation reaction of the 7-dehydrocholesterol and saturated fatty acid it is preferable to use 0.8 to 3 equivalents of saturated fatty acid based on 7-dehydrocholesterol, and 1 to 3 equivalents of condensing agent and 1 to 2 equivalents of organic base. It is desirable to.
- the acid chloride is preferably used in an amount of 0.8 to 2 equivalents based on 7-dehydrocholesterol, and 2 to 5 equivalents in organic base.
- the condensation reaction of 7-dehydrocholesterol and unsaturated fatty acid it is preferable to use 0.8 to 3 equivalents of unsaturated fatty acid on the basis of 7-dehydrocholesterol, and 1 to 3 equivalents of condensing agent and 0.9 to 2 equivalents of organic base. It is preferable to use.
- the acid chloride is preferably used in the amount of 0.8 to 3 equivalents and the organic base in the amount of 0.9 to 5 equivalents based on 7-dehydrocholesterol.
- Acid chlorides of the saturated or unsaturated fatty acids may be prepared by methods known in the art or may be obtained commercially. Specifically, the reaction of replacing the chloride with a fatty acid carbonyl group may be carried out by reacting the fatty acid with one of thionylchloride and oxalylchloride using an organic amine catalyst as necessary under anhydrous organic solvent.
- the thionyl chloride or oxalyl chloride is preferably used 1 to 5 equivalents based on fatty acid.
- the fatty acid conjugated 7-dehydrocholesterol derivative of Chemical Formula 1 according to the present invention has significantly improved stability against light and heat and increased skin absorption compared to 7-dehydrocholesterol.
- the fatty acid conjugated 7-dehydrocholesterol derivative of Formula 1 according to the present invention is a source of a vitamin D precursor that can be hydrolyzed in the body to supply 7-dehydrocholesterol, a vitamin D precursor, to improve wrinkles and age. It can be effectively used in preventing cosmetic compositions, pharmaceutical compositions and health functional food.
- One embodiment of the present invention relates to a wrinkle improvement and anti-aging cosmetic composition
- a wrinkle improvement and anti-aging cosmetic composition comprising a fatty acid conjugated 7-dehydrocholesterol derivative of the formula (1).
- the cosmetic composition according to the present invention contains the fatty acid conjugated 7-dehydrocholesterol derivative of Formula 1 as an active ingredient in an amount of about 0.001 to 10% by weight, preferably 0.01 to 1% by weight.
- the content of the active ingredient can be appropriately determined according to the purpose of use thereof.
- the cosmetic composition of the present invention is a component commonly used in cosmetic compositions in addition to the fatty acid conjugated 7-dehydrocholesterol derivative of Formula 1 as an active ingredient, such as antioxidants, stabilizers, solubilizers, vitamins, pigments and Conventional adjuvants such as perfumes, and carriers.
- Cosmetic compositions of the present invention may be prepared in any formulation commonly used in the art, and may, for example, be formulated in solutions, suspensions, emulsions, pastes, gels, creams, powders, sprays, and the like.
- the formulation of the present invention is a paste, cream or gel, animal oils, vegetable oils, waxes, paraffins, starches, trachants, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc, zinc oxide and the like may be used as carrier components.
- animal oils, vegetable oils, waxes, paraffins, starches, trachants, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc, zinc oxide and the like may be used as carrier components.
- animal oils vegetable oils, waxes, paraffins, starches, trachants, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc, zinc oxide and the like
- cellulose derivatives polyethylene glycols
- silicones bentonites
- silicas talc
- zinc oxide and the like may be used as carrier components.
- lactose When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, polyamide powder, and the like may be used, and in the case of a spray, additionally, chlorofluorohydrocarbon, Propellant such as propane / butane or dimethylether.
- a carrier for example water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butylglycol oil, glycerol fatty acid ester, polyethylene glycol, fatty acid ester of sorbitan and the like can be used.
- a liquid diluent such as water, ethanol or propylene glycol
- a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester or polyoxyethylene sorbitan ester, and microcrystals
- Castle cellulose, aluminum metahydroxy, bentonite, agar, tracant and the like can be used.
- the cosmetic composition of the present invention is a skin, lotion, cream, essence, pack, foundation, color cosmetics, sun cream, two-way cake, face powder, compact, makeup base, skin cover, eye shadow, lipstick, lip gloss, lip fix, eyebrow pencil It can be applied to such cosmetics.
- Another embodiment of the present invention relates to a wrinkle improvement and anti-aging pharmaceutical composition
- a wrinkle improvement and anti-aging pharmaceutical composition comprising the fatty acid conjugated 7-dehydrocholesterol derivative of Formula 1.
- compositions according to the invention may be administered orally (eg, taken or inhaled) or parenterally (eg, by injection, transdermal absorption, rectal administration), and the injection may be administered, for example, by intravenous injection. , Subcutaneous injection, intramuscular injection or intraperitoneal injection.
- the pharmaceutical composition according to the present invention may be used as tablets, capsules, granules, fine subtilae, powders, sublingual tablets, suppositories, ointments, injections, emulsions, suspensions, syrups, sprays and the like.
- the pharmaceutical compositions according to the present invention in various forms can be prepared by known techniques using pharmaceutically acceptable carriers commonly used in each formulation.
- Examples of pharmaceutically acceptable carriers include excipients, binders, disintegrating agents, lubricants, preservatives, antioxidants, isotonic agents, buffers, coatings, sweeteners, solubilizers, bases, dispersants, wetting agents , Suspending agents, stabilizers, coloring agents and the like.
- the pharmaceutical composition according to the present invention comprises about 0.001 to 10% by weight, preferably 0.01 to 0.1% by weight of the fatty acid conjugated 7-dehydrocholesterol derivative of the formula (1).
- the specific dosage of the pharmaceutical composition of the present invention may vary depending on the type of mammal including the person being treated, weight, sex, degree of disease, judgment of a doctor, and the like.
- 10 to 200 mg of active ingredient is administered per kg of body weight per day.
- the total daily dose may be administered at one time or divided into several times depending on the extent of the disease, the judgment of the doctor.
- Another embodiment of the present invention relates to a wrinkle-improving and anti-aging health functional food comprising the fatty acid conjugated 7-dehydrocholesterol derivative of the formula (1).
- the health functional food of the present invention may be prepared by appropriately using a food-acceptable carrier such as fillers, extenders, binders, wetting agents, disintegrants, sweeteners, fragrances, preservatives, surfactants, lubricants, excipients, etc. Can be.
- a food-acceptable carrier such as fillers, extenders, binders, wetting agents, disintegrants, sweeteners, fragrances, preservatives, surfactants, lubricants, excipients, etc. Can be.
- the content of the fatty acid conjugated 7-dehydrocholesterol derivative of Formula 1 in the manufacture of the health functional food depends on the form of the health functional food, but it is about 0.001 to 10% by weight, preferably 0.1 to 1.0% by weight Concentration.
- Another embodiment of the invention is directed to a method for anti-wrinkle and anti-aging comprising administering to a subject a composition comprising said fatty acid conjugated 7-dehydrocholesterol derivative.
- the fatty acid conjugated 7-dehydrocholesterol derivatives according to the present invention have improved stability, reduced toxicity and improved skin absorption.
- the fatty acid conjugated 7-dehydrocholesterol derivative according to the present invention can be effectively used as a good source of vitamin D, for improving wrinkles and anti-aging cosmetic compositions, pharmaceutical compositions, health foods and the like.
- the fatty acid conjugated 7-dehydrocholesterol derivative according to the present invention is hydrolyzed at pH conditions in vivo to slowly release the precursor of the active vitamin D, or antioxidant, wrinkle improvement, etc. as a compound in the body storage form of the vitamin D precursor It can continuously express the physiological activity of.
- 1 is a graph showing the stability test results for 45 °C temperature harsh conditions of the fatty acid conjugated 7-dehydrocholesterol derivatives according to the present invention.
- Figure 2 is a graph showing the stability test results for the light (solar) harsh conditions of the fatty acid conjugated 7-dehydrocholesterol derivatives according to the present invention.
- Figure 3 is a graph showing the cytotoxicity test results of the fatty acid conjugated 7-dehydrocholesterol derivatives according to the present invention.
- Figure 4 is a graph showing the collagen expression test results of the fatty acid conjugated 7-dehydrocholesterol derivatives according to the present invention.
- 5 is a graph showing the results of MMP-1 inhibition test of the fatty acid conjugated 7-dehydrocholesterol derivatives according to the present invention.
- Figure 6 is a graph showing the tropoelastin expression test results of the fatty acid conjugated 7-dehydrocholesterol derivatives according to the present invention.
- FIG. 7 is a graph showing the skin absorption test results of the fatty acid conjugated 7-dehydrocholesterol derivatives according to the present invention.
- FIG. 8 is a graph illustrating skin absorption test results using a skin absorption enhancer in combination with a fatty acid conjugated 7-dehydrocholesterol derivative according to the present invention.
- reaction solution was washed with 1.0 N aqueous hydrochloric acid solution, the organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, and the obtained mixture was crystallized with 300 ml of ethyl acetate to give 8.7 g (79.8%) of dehydrocholesteryl palmitate. Got it.
- reaction solution was washed with 1.0 N aqueous hydrochloric acid solution, the organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, and the obtained mixture was crystallized with 50 ml of ethyl acetate to give 0.53 g (31.2%) of dehydrocholesteryllaurate. Got it.
- the test compound was prepared by subdividing the compound of Example 1 into a 5 mg brown bottle in powder form, and subdividing 5 mg of 7-dehydrocholesterol in powder form as a comparative substance to prepare the same method as the test substance.
- the prepared test powder was shielded from light and left at a constant temperature of 45 ° C., collected at a predetermined time, dissolved in hexane, and analyzed by HPLC with analyte concentration of 1 mg / ml. The results are shown in FIG.
- HPLC analysis conditions are as follows.
- Example 1 As shown in FIG. 1, the dehydrocholesteryl palmitate obtained in Example 1 was confirmed to have better heat stability than 7-dehydrocholesterol.
- the test compound was prepared by subdividing the compound of Example 1 into a 5 mg transparent bottle in powder form, and subdividing 5 mg of 7-dehydrocholesterol in powder form as a comparative substance to prepare the same method as the test substance.
- the prepared test powder was irradiated with light at room temperature, collected at a predetermined time, dissolved in hexane, and analyzed by HPLC with analyte concentration of 1 mg / ml. The results are shown in FIG.
- HPLC analysis conditions are as follows.
- Example 2 As shown in Figure 2, the dehydrocholesteryl palmitate obtained in Example 1 was confirmed that the stability to light better than 7-dehydrocholesterol.
- Human fibroblast CCD-986SK was inoculated at the bottom of the T-flask, and then a culture medium containing penicillin (100 IU / ml), streptomycin (100 ⁇ g / ml) and 10% FBS was added. C was incubated in an incubator containing 5% CO 2 (g).
- Fatty acid conjugated 7-dehydrocholesterol derivatives obtained in Examples 1 to 5 and 7-dehydrocholesterol as a comparative substance were dissolved in DMSO and diluted, respectively, and then diluted to 50 ⁇ M, 25 ⁇ M, 12.5 ⁇ M, and 6.25 ⁇ M. It was prepared.
- CCD-986SK cells which are human fibroblasts, were dispensed into 96-well plates, and then cultured for 18 hours under cell culture conditions. After removing the medium and washing with PBS, the prepared sample and fresh medium were added and incubated for 18 hours. MTT assay was performed to confirm cell viability (%). The results are shown in Table 1 and FIG. 3.
- Example 2 Example 3
- Example 4 Example 5 6.25 110.47 ⁇ 0.884 120.76 ⁇ 0.024 161.94 ⁇ 0.547 112.49 ⁇ 0.001 115.86 ⁇ 0.073 170.71 ⁇ 0.521 12.5 124.78 ⁇ 0.928 124.48 ⁇ 0.199 179.86 ⁇ 0.067 143.24 ⁇ 0.808 107.51 ⁇ 0.401 165.48 ⁇ 0.594 25 114.45 ⁇ 0.366 134.97 ⁇ 0.241 157.00 ⁇ 0.072 134.74 ⁇ 0.481 108.41 ⁇ 0.222 147.94 ⁇ 0.115 50 103.75 ⁇ 0.042 128.22 ⁇ 0.820 160.05 ⁇ 0.184 102.12 ⁇ 0.312 102.78 ⁇ 0.092 197.71 ⁇ 0.239
- the fatty acid conjugated 7-dehydrocholesterol derivatives obtained in Examples 1 to 5 and 7-dehydrocholesterol as a comparative substance were dissolved and diluted with DMSO, respectively, and the concentrations of 25 ⁇ M, 12.5 ⁇ M, 6.25 ⁇ M, and 3.125 ⁇ M were diluted.
- RNA was extracted, RT-PCR was performed, and the amplified genes were analyzed using Gel Documentation System and Image J program, and collagen and tropoelastin were analyzed.
- the expression rate of (%) and the inhibition rate (%) of MMP-1 (Matrix metalloproteinase-1) was confirmed. The results are shown in Table 2 and FIGS. 4 to 6.
- Pigment (pig) skin was mounted on a transdermal absorption cell (Franz diffusion cell) to perform a skin permeation test.
- a 50% ethanol / water solution was placed in a receptor container (7 ml) of the percutaneous absorption device, and the skin was fixed between the donor and the receptor so that the keratinous portion of the extracted skin face upward.
- the area of the epidermis in contact with the receptor phase was 0.6262 cm 2 , and the mixture was stirred at a speed of 150 rpm while maintaining the temperature at 32 ° C. using an incubator.
- Test compound 1 and test solution 2 were prepared using the compound of Example 1 and the compound of Example 2 at a concentration of 5 mg / ml in 50% ethanol / water, and polyoxyethylene (20) oleyl ether (20). )
- Test solution 3 and test solution 4 were prepared using 50% ethanol / water containing 6% oleyl ether [BrijTM98]) at a concentration of 5 mg / ml.
- Comparative solution 1 was prepared by using 7-dehydrocholesterol as a comparative substance at a concentration of 5 mg / ml in 50% ethanol / water, and polyoxyethylene (20) oleyl ether [BrijTM98].
- Comparative Solution 2 was prepared by mixing 7-dehydrocholesterol at a concentration of 5 mg / ml in 50% ethanol / water containing 6%.
- the comparative compound 7-dehydrocholesterol including the compound of Example 1 and the compound of Example 2, which remained on the transdermal epidermis after the last time sample was collected, it was first separated from the transdermal absorption apparatus and separated into 50% ethanol / water. After washing twice, only the parts contacting with the receptor phase were cut and cut into 1.0 ml of dichloromethane, shaken for 5 minutes, and mixed by ultrasonication (Ultrasonication) for 60 minutes. The lower layer was taken by centrifugation and quantified by HPLC. The results are shown in FIGS. 7 and 8.
- HPLC analysis conditions are as follows.
- Example 7 the dehydrocholesteryl palmitate obtained in Example 1 was confirmed that the skin absorption rate is significantly superior to the comparative 7-dehydrocholesterol.
- the fatty acid conjugated 7-dehydrocholesterol derivatives obtained in Example 1 and Example 2 was found to be significantly increased when the skin absorption enhancer (PE) is used together.
- PE skin absorption enhancer
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Abstract
Cette invention concerne un dérivé de 7-déshydrocholestérol conjugué à un acide gras et une composition destinée à atténuer les rides et à prévenir le vieillissement le contenant. Le dérivé de 7-déshydrocholestérol conjugué à un acide gras selon l'invention peut être efficacement utilisé pour une composition cosmétique, une composition pharmaceutique, et un aliment de santé fonctionnel, pour atténuer les rides et prévenir le vieillissement, dans la mesure où la stabilité et l'absorption par la peau dudit dérivé sont augmentées et que le dérivé est hydrolysé pour fournir un apport en vitamine D au corps.
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US11813272B2 (en) | 2018-06-05 | 2023-11-14 | Flagship Pioneering Innovations V, Inc. | Active agents and methods of their use for the treatment of metabolic disorders and nonalcoholic fatty liver disease |
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KR102175655B1 (ko) * | 2019-04-03 | 2020-11-06 | 연세대학교 원주산학협력단 | 페길레이션된 아이코사펜타엔산 유도체, 이의 제조 방법 및 이를 포함하는 피부 노화 방지용 조성물 |
KR20230164334A (ko) | 2022-05-25 | 2023-12-04 | 주식회사 코스메카코리아 | 7-데하이드로콜레스테롤을 포함하는 니오좀, 이를 유효성분으로 함유하는 화장료 조성물, 및 이의 제조방법 |
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CH311199A (de) * | 1953-01-15 | 1955-11-30 | Ag Dr A Wander | Verfahren zur Herstellung von 7-Dehydro-cholesteryl-n-butyrat. |
KR20010002281A (ko) * | 1999-06-14 | 2001-01-15 | 임병철 | 7-디하이드로콜레스테롤을 함유하는 화장료 조성물 |
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SI2310059T1 (sl) | 2008-05-29 | 2017-04-26 | Numat Biomedical S.L. | Vsadki, pokriti s pufa |
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CH311199A (de) * | 1953-01-15 | 1955-11-30 | Ag Dr A Wander | Verfahren zur Herstellung von 7-Dehydro-cholesteryl-n-butyrat. |
KR20010002281A (ko) * | 1999-06-14 | 2001-01-15 | 임병철 | 7-디하이드로콜레스테롤을 함유하는 화장료 조성물 |
Non-Patent Citations (3)
Title |
---|
OSAMU, NISHIKAWA ET AL.: "An Improved Synthesis of 1alpha-hydroxy-7-dehydrochole- Sterol Derivatives", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 32, no. 8, 1984, pages 3244 - 3247, XP055310741 * |
REZANKA, TOMAS: "Analysis of Sterol Esters from Alga and Yeast by High-Performance Liquid Chromatography and Capillary Gas Chromatography-Mass Spectrometry with Chemical Ionization", JOURNAL OF CHROMATOGRAPHY, vol. 598, no. 2, 15 May 1992 (1992-05-15), pages 219 - 226, XP026531740 * |
WILLIAM, R. NES ET AL.: "The Anthrasteroid Rearrangement. IV. The Preparation of Several New Anthrasteroids and Some Observations on the Dehydrobromination of 7-Bromo-DELTA5- steroids 1", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 78, no. 2, 1956, pages 436 - 440, XP055310737 * |
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US11813272B2 (en) | 2018-06-05 | 2023-11-14 | Flagship Pioneering Innovations V, Inc. | Active agents and methods of their use for the treatment of metabolic disorders and nonalcoholic fatty liver disease |
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