WO2015147137A1 - Composition d'agent externe contenant un céramide - Google Patents

Composition d'agent externe contenant un céramide Download PDF

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Publication number
WO2015147137A1
WO2015147137A1 PCT/JP2015/059315 JP2015059315W WO2015147137A1 WO 2015147137 A1 WO2015147137 A1 WO 2015147137A1 JP 2015059315 W JP2015059315 W JP 2015059315W WO 2015147137 A1 WO2015147137 A1 WO 2015147137A1
Authority
WO
WIPO (PCT)
Prior art keywords
ceramide
type
weight
external preparation
phytosterol
Prior art date
Application number
PCT/JP2015/059315
Other languages
English (en)
Japanese (ja)
Inventor
乾介 今井
敬子 福田
正彦 小森園
Original Assignee
小林製薬株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 小林製薬株式会社 filed Critical 小林製薬株式会社
Priority to CN201580027604.8A priority Critical patent/CN106413681A/zh
Publication of WO2015147137A1 publication Critical patent/WO2015147137A1/fr

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Classifications

    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • 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
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • 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

Definitions

  • the present invention relates to a ceramide-containing external preparation composition.
  • the barrier function of the skin stratum corneum decreases due to various environmental factors such as dryness and ultraviolet rays, aging of the skin with aging, atopic lesions, etc., resulting in rough skin. It is maintained by a lamellar structure consisting of intercellular lipids and keratinocytes.
  • Ceramide is mentioned as a main component of the stratum corneum lipid, and an external preparation composition containing ceramide is known for the purpose of supplementing the barrier function of the skin stratum corneum (Patent Documents 1 and 2).
  • Patent Documents 1 and 2 it is not easy to increase the compounding amount of ceramide in an external preparation composition because ceramide is expensive, difficult to dissolve in a cosmetic base, and crystals precipitate. No external preparation composition containing ceramide and having a sufficient barrier function has been obtained.
  • the keratin intercellular lipid contains cholesterol in addition to ceramide, and the use of phytosterols having a structure similar to cholesterol in an external preparation composition for supplementing the barrier function has also been studied.
  • phytosterol is hardly soluble in fat and insoluble in water, so it is not easy to use it in an external preparation composition, and it contains phytosterol and has a sufficient barrier function. An agent composition has not been obtained.
  • This invention makes it a subject to provide the external preparation composition containing the ceramide which improves the barrier function of skin.
  • type I ceramide As a result of intensive studies, the present inventor has found that the inclusion of type I ceramide, type II ceramide, type III ceramide, and phytosterol effectively improves the skin barrier function, thereby completing the present invention.
  • the present invention relates to an external preparation composition containing type I ceramide, type II ceramide, type III ceramide, and phytosterol.
  • the amount of type I ceramide is preferably 0.002 to 300 parts by weight with respect to 100 parts by weight of type II ceramide.
  • the compounding amount of type III ceramide is preferably 0.24 to 300 parts by weight with respect to 100 parts by weight of type II ceramide.
  • the total content of type I ceramide, type II ceramide, and type III ceramide is preferably 0.01 to 10% by weight.
  • the content of phytosterol is preferably 0.001 to 60% by weight.
  • the external preparation composition of the present invention can improve the skin barrier function by containing type I ceramide, type II ceramide, type III ceramide, and phytosterol.
  • the external preparation composition of the present invention contains type I ceramide, type II ceramide, type III ceramide, and phytosterol.
  • ceramides constituting keratin intercellular lipids seven types of free ceramides (type I to VII) and two types of membrane protein-bound ceramides (types A and B) are known. These ceramides play an important role in maintaining barrier functions such as formation and stability of the lamellar structure of the epidermis, retention of moisture, and prevention of foreign matter intrusion.
  • type I ceramide, type II ceramide, and type III ceramide are included.
  • Type I ceramide is N- ( ⁇ -acyloxy-acyl) phytosphingosine and N- ( ⁇ -acyloxy-acyl) sphingosine, which is obtained by extraction and fractionation from tissues such as animals, plants, and yeasts. Those synthesized by chemical or enzymatic methods can be used.
  • N- ( ⁇ -acyloxy-acyl) phytosphingosine is preferred.
  • phytosphingosine or the acyl group directly amide-bonded to sphingosine is preferably a straight chain and saturated group having about 20 to 38 carbon atoms.
  • the acyl group preferably has 20 to 34 carbon atoms, more preferably 24 to 30 carbon atoms, still more preferably 26 to 30 carbon atoms, and particularly preferably 27 carbon atoms. preferable.
  • the acyl group bonded to phytosphingosine or sphingosine via an ester bond with the acyl group is preferably a saturated group having about 12 to 38 carbon atoms, and may have a hydroxyl group but be linear. More preferably, the acyl group has more preferably 14 to 30 carbon atoms, more preferably 16 to 28, still more preferably 16 to 20, and particularly preferably 18.
  • Type II ceramide is N-acyl sphingosine or N-acyl dihydrosphingosine, which can be obtained by extraction and fractionation from various tissues such as animals, or synthesized by chemical or enzymatic methods. it can.
  • N-acyl dihydrosphingosine is preferable.
  • the acyl group is preferably a saturated or unsaturated group having about 12 to 38 carbon atoms, and more preferably a saturated and straight chain group.
  • the acyl group may have a hydroxyl group, but preferably does not have a hydroxyl group.
  • the number of carbon atoms of the acyl group is more preferably 14 to 30, further preferably 16 to 28, still more preferably 16 to 24, and particularly preferably 18.
  • Type III ceramide is N-acyl phytosphingosine, which can be obtained by extraction and fractionation from tissues such as animals, plants, yeast, etc., or synthesized by chemical or enzymatic methods.
  • the acyl group is preferably a saturated or unsaturated group having about 12 to 38 carbon atoms, and more preferably a saturated and straight chain group.
  • the said acyl group may have a hydroxyl group, the thing which does not have a hydroxyl group is more preferable.
  • the number of carbon atoms of the acyl group is more preferably 14 to 30, further preferably 16 to 28, still more preferably 16 to 24, and particularly preferably 18.
  • the amount of the type I ceramide is preferably 0.002 to 300 parts by weight, and preferably 0.0025 to 300 parts by weight with respect to 100 parts by weight of the type II ceramide. More preferably, the amount is 0.00495 to 100 parts by weight.
  • the compounding amount of the type III ceramide is preferably 0.24 to 300 parts by weight, and preferably 1.25 to 300 parts by weight with respect to 100 parts by weight of the type II ceramide. More preferred is 1.25 to 149.5 parts by weight.
  • the content of type I ceramide is preferably 0.00001 to 10% by weight, more preferably 0.00005 to 8% by weight, and 0.000075 to It is more preferably 5% by weight, still more preferably 0.0001 to 2% by weight.
  • the content of type II ceramide is preferably 0.0001 to 10% by weight, more preferably 0.5 to 8% by weight, and 1 to 5% by weight. %, More preferably 2 to 5% by weight.
  • the content of the type III ceramide is preferably 0.0001 to 10% by weight, more preferably 0.01 to 8% by weight, and more preferably 0.03 to It is more preferably 5% by weight, and even more preferably 0.04 to 3% by weight.
  • the total content of type I ceramide, type II ceramide, and type III ceramide is preferably 0.01 to 10% by weight, more preferably 2 to 8.5% by weight, and more preferably 3 to 5.1%. More preferably, it is% by weight.
  • Phytosterols are plant sterols found in small amounts in vegetable oils such as corn, beans or other vegetable oils. Phytosterol has a structure similar to cholesterol, but the carbon skeleton of the side chain is different from cholesterol.
  • phytosterol is not particularly limited, and examples thereof include ⁇ -sitosterol, campesterol, stigmasterol, and brassicasterol, and may be a mixture thereof.
  • the content of phytosterol is preferably 0.001 to 60% by weight, more preferably 0.03 to 30% by weight, and 0.3 to 5% by weight. Further preferred. If it is less than 0.001% by weight, the ability to form a lamellar structure tends to be poor. If it exceeds 60% by weight, it tends to be difficult to dissolve in the composition.
  • the phytosterol content in the external preparation composition is 0.075 to 60000 parts by weight with respect to 100 parts by weight of the total amount of type I ceramide, type II ceramide and type III ceramide. It is preferably from 0.75 to 1500 parts by weight, more preferably from 7.5 to 375 parts by weight, and even more preferably from 35 to 150 parts by weight.
  • the external preparation composition contains water.
  • water examples include purified water, distilled water, sterilized water, physiological saline, and deep sea water.
  • Examples of the base of the external preparation composition include water, polyol, alcohol, silicone oil, hydrocarbon oil, ester oil, vegetable oil, higher alcohol, and higher fatty acid.
  • the external preparation composition may appropriately contain an active ingredient and an additive depending on each application in addition to the type I ceramide, the type II ceramide, the type III ceramide, and the phytosterol.
  • active ingredients include UV protection agents, whitening agents, anti-inflammatory agents, anti-aging agents, blood circulation promoters, fragrances, bactericides / disinfectants, antiperspirants, deodorants / deodorants, hair growth / hair restorers, hair removers , Hair dyes, permanent wave agents, repellents, anti-inflammatory analgesics and the like.
  • additives include sterols other than phytosterols, fluorine oils, surfactants, hydroxy acids, guanidine derivatives or salts thereof, film-forming polymers, sugars, plant extracts, antioxidants or singlet oxygen scavengers, Sebum secretion suppressant, vitamin, gelling agent, powder, inorganic salt, pH adjuster, viscosity adjuster, antioxidant, preservative, sequestering agent, cooling agent, pigment, solid / semi-solid oil, water-soluble Include a water-soluble polymer, an oil-soluble polymer, a biocompatible polymer, a liposome preparation, a capsule preparation, a pearl luster imparting agent, and a micro / nanoemulsion preparation.
  • An external preparation composition can be manufactured by the method normally used in the said field
  • the amount of type I ceramide, type II ceramide, type III ceramide, and phytosterol and other components as required, and the amount of type I ceramide, type II ceramide, type III ceramide, and phytosterol is within the above range. It can be manufactured by adding to the base and mixing.
  • the external preparation composition has the advantage of improving the skin barrier function, and can be suitably used for the purpose of moisturizing the skin among the barrier functions.
  • the composition for external use is a cosmetic applied to the skin, for example, a cosmetic soap, a facial cleanser, a makeup remover, an eye cream, an eye shadow, a cream, an emulsion, a lotion, a perfume, a foundation, an interesting, a cosmetic oil, a kneading agent.
  • the external preparation composition can be used not only as a cosmetic applied to the skin but also as a cosmetic for hair or nails.
  • hair cosmetics include shampoos, rinses, hair dyes, hair nourishing agents, hair restoring agents, eyebrows, and the like.
  • nail cosmetics include nail cream, beautiful nail enamel, and beautiful nail enamel remover.
  • the external preparation composition can be used as a transdermal pharmaceutical composition and the like in addition to cosmetic use.
  • the transdermal pharmaceutical composition include bactericidal antiseptics, mosquitoes, redheads, purulent diseases, topical analgesics, topical antipruritics, topical astringents, topical antiphlogistics, worms and insecticides And emollients, hair drugs and the like.
  • the external preparation composition can take the form of cream, ointment, lotion, gel, emulsion and the like.
  • the barrier function of the external preparation composition can be measured, for example, by the method described in Examples. That is, type I ceramide, type II ceramide, type III ceramide, and phytosterol are added and dissolved in chloroform to prepare a ceramide solution.
  • a ceramide membrane is produced by impregnating a ceramide solution into a membrane filter (made of cellulose, membrane pressure 0.2 ⁇ m) and evaporating chloroform at room temperature. 1 ml of water is put into a vial and the mouth of the bottle is closed with the ceramide membrane. The bottle is held at 50 ° C. for 3 days, and the amount of water transpiration is calculated from the change in the weight of the vial.
  • the barrier function is calculated by the following formula.
  • Barrier function (%) 100 ⁇ (moisture transpiration amount of specimen (mg) / water transpiration amount when ceramide or phytosterol is not used (mg)) ⁇ 100
  • Example 1 and Comparative Examples 1 and 2 A ceramide solution was prepared by adding the following type I ceramide, type II ceramide, type III ceramide, and phytosterol to chloroform and dissolving them so that the concentrations shown in Table 1 were obtained.
  • Type I ceramide N- (27-stearoyloxyheptacosanoyl) phytosphingosine (CERAMIDE I: Evonik Degussa Japan Co., Ltd.)
  • Type II ceramide Stearoyl dihydrosphingosine (Ceramide TIC-001: Takasago International Corporation)
  • Type III ceramide Stearoyl phytosphingosine (CERAMIDE III: Evonik Degussa Japan Co., Ltd.)
  • Phytosterol Phytosterol (Phytosterol-SKP: Tama Biochemical Co., Ltd.)
  • a ceramide membrane was prepared by impregnating a ceramide solution into a membrane filter (made of cellulose, membrane pressure 0.2 ⁇ m) and evaporating chloroform at room temperature. 1 ml of water was placed in the vial, and the mouth of the bottle was closed with the ceramide membrane. This bottle was kept at 50 ° C. for 3 days, and the amount of water transpiration was calculated from the change in the weight of the vial.
  • the barrier function was calculated by the following calculation formula in comparison with the moisture transpiration amount of Comparative Example 2 (without ceramide). The results are shown in Table 1.
  • Barrier function (%) 100 ⁇ (moisture transpiration amount of specimen (mg) / moisture transpiration amount of comparative example 2 (mg)) ⁇ 100
  • the ceramide solution of Example 1 has a high barrier function by including type I ceramide, type II ceramide, type III ceramide, and phytosterol. Since Comparative Example 1 does not contain phytosterol and Comparative Example 2 does not contain type I-III ceramide, it does not have any barrier function.
  • Examples 2 to 5 and Comparative Examples 3 to 5 The ceramide solution was prepared so that it might become the density
  • the ceramide solutions of Examples 1 and 3 to 5 have a particularly high barrier function by containing 1.25 to 300 parts by weight of III type ceramide with respect to 100 parts by weight of type II ceramide.
  • Example 6 and Comparative Examples 6 to 8 The ceramide solution was prepared so that it might become the density
  • the ceramide solutions of Examples 1 and 6 have a high barrier function.
  • Example 7 to 10 and Comparative Examples 9 to 12 The ceramide solution was prepared so that it might become the density
  • the ceramide solutions of Examples 1, 8 and 9 exhibited a particularly high barrier function by containing 3 to 5.1% by weight of type I ceramide, type II ceramide, and type III ceramide in total.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Toxicology (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

[Problème] Fournir une composition d'agent externe comprenant un céramide, ladite composition présentant une meilleure efficacité protectrice. [Solution] L'invention concerne une composition d'agent externe comprenant un céramide de type I, un céramide de type II, un céramide de type III et un phytostérol. Le céramide de type I représente, de préférence, 0,002 à 300 parties en poids pour 100 parties en poids du céramide de type II.
PCT/JP2015/059315 2014-03-28 2015-03-26 Composition d'agent externe contenant un céramide WO2015147137A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201580027604.8A CN106413681A (zh) 2014-03-28 2015-03-26 配混神经酰胺的外用剂组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014-069419 2014-03-28
JP2014069419A JP6356457B2 (ja) 2014-03-28 2014-03-28 セラミド配合外用剤組成物

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WO2015147137A1 true WO2015147137A1 (fr) 2015-10-01

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JP (1) JP6356457B2 (fr)
CN (1) CN106413681A (fr)
TW (1) TWI671080B (fr)
WO (1) WO2015147137A1 (fr)

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Publication number Priority date Publication date Assignee Title
JP6818421B2 (ja) * 2016-03-30 2021-01-20 小林製薬株式会社 真皮線維芽細胞賦活剤、及びその用途
KR101983566B1 (ko) * 2018-03-09 2019-05-29 닥터 레이몬드 래보라토리 피부 외용제 조성물
JP2020203862A (ja) * 2019-06-18 2020-12-24 小林製薬株式会社 皮膚バリア機能改善用の外用組成物
JP2020203861A (ja) * 2019-06-18 2020-12-24 小林製薬株式会社 外用組成物

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CN106413681A (zh) 2017-02-15
TW201622696A (zh) 2016-07-01
JP6356457B2 (ja) 2018-07-11
JP2015189723A (ja) 2015-11-02
TWI671080B (zh) 2019-09-11

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