[go: up one dir, main page]

WO2012096276A1 - Promoteur d'absorption percutanée et préparation cutanée externe - Google Patents

Promoteur d'absorption percutanée et préparation cutanée externe Download PDF

Info

Publication number
WO2012096276A1
WO2012096276A1 PCT/JP2012/050324 JP2012050324W WO2012096276A1 WO 2012096276 A1 WO2012096276 A1 WO 2012096276A1 JP 2012050324 W JP2012050324 W JP 2012050324W WO 2012096276 A1 WO2012096276 A1 WO 2012096276A1
Authority
WO
WIPO (PCT)
Prior art keywords
derivatives
physiologically active
salt
skin
lipopeptide compound
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2012/050324
Other languages
English (en)
Japanese (ja)
Inventor
将司 泉田
恵広 柳澤
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kaneka Corp
Original Assignee
Kaneka Corp
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 Kaneka Corp filed Critical Kaneka Corp
Priority to JP2012552734A priority Critical patent/JP5906194B2/ja
Publication of WO2012096276A1 publication Critical patent/WO2012096276A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • the present invention relates to a transdermal absorption enhancer containing a lipopeptide compound, and a skin external preparation with improved transdermal absorbability of a physiologically active ingredient.
  • transdermal administration is widely used because it only needs to be brought into contact with the skin and is simple and can be directly administered when the skin is the target action site of a physiologically active ingredient.
  • the skin has a barrier function that prevents foreign substances from entering as a natural role, the permeability (transdermal absorbability) of the physiologically active ingredient may be insufficient. Accordingly, various methods for promoting percutaneous absorption have been studied.
  • a method of promoting percutaneous absorption for example, there is a method of using a percutaneous absorption enhancer that improves the permeability of a physiologically active ingredient, and examples of the percutaneous absorption enhancer include sugar-modified linear silicone.
  • the percutaneous absorption enhancer include sugar-modified linear silicone.
  • Patent Document 1 it has been reported that percutaneous absorption is promoted by an emulsifier.
  • a sucrose fatty acid ester is used as a transdermal absorption enhancer (Patent Document 2).
  • An object of the present invention is to provide a percutaneous absorption enhancer and a skin external preparation that are low in skin irritation and can sufficiently promote percutaneous absorption of a physiologically active ingredient.
  • a lipopeptide compound has an effect of remarkably promoting the percutaneous absorption of a predetermined physiologically active ingredient, and completed the present invention. It was.
  • the present invention relates to a percutaneous absorption enhancer containing a lipopeptide compound or a salt thereof.
  • This transdermal absorption enhancer has a skin permeability of a physiologically active ingredient (log P value of ⁇ 5.5 to 1.0) per 1% by weight of a lipopeptide compound or a salt thereof in a test using a stationary Franz cell. It promotes more than twice as compared with the case of the lipopeptide compound or its salt-free group.
  • the lipopeptide compound is preferably the following formula (1): (In the formula, * represents an optically active point.
  • X represents an amino acid selected from leucine, isoleucine, and valine
  • R represents a linear alkyl group having 9 to 13 carbon atoms and a branched alkyl group.
  • the present invention also includes an external preparation for skin containing this transdermal absorption enhancer and a physiologically active ingredient having a log P value of -5.5 to 1.0.
  • the lipopeptide compound or salt thereof in the transdermal absorption enhancer is 0.1 to 100 parts by weight with respect to 1 part by weight of the physiologically active ingredient.
  • the present invention also includes a method for promoting percutaneous absorption of a physiologically active substance, in which a lipopeptide compound or a salt thereof is mixed with a physiologically active ingredient having a log P value of ⁇ 5.5 to 1.0.
  • the lipopeptide compound or a salt thereof selectively shows an effect of improving the permeability to the skin with respect to a specific physiologically active substance. Therefore, the transdermal absorption enhancer containing the lipopeptide compound or a salt thereof can be effectively used particularly for selective absorption of a physiologically active substance into the skin.
  • the percutaneous absorption enhancer of the present invention is used for the purpose of permeating and absorbing a physiologically active substance into the skin, and is suitably used for external preparations for skin such as pharmaceuticals, cosmetics and quasi drugs.
  • the transdermal absorption enhancer according to the present invention contains a lipopeptide compound or a salt thereof.
  • lipopeptide compounds include natural lipopeptide compounds produced by microorganisms, and these are a kind of compound group called biosurfactants.
  • the lipopeptide compound is not limited to a natural product, and other derived substances such as those obtained by a chemical synthesis method can be used as long as they have the same chemical structure.
  • a lipopeptide compound or a salt thereof has a log P value of ⁇ 5.5 to 1.0 (preferably ⁇ 4.0 to 1 in a skin permeability test using a stationary Franz cell using rat skin or a cultured human skin model. 0.0, more preferably from -3.0 to 1.0, still more preferably from -3.0 to 0, particularly preferably from -2.0 to 0), promoting the skin permeability of the physiologically active ingredient What can be done is preferred.
  • the test can be carried out using a sample comprising lipopeptide compound or salt thereof: 0 to 2% by weight, bioactive ingredient: 1% by weight, glycerin: 10% by weight, water: residue.
  • the skin permeation rate of the physiologically active ingredient when using 1 to 2% by weight of the salt is 1.05 times or more per 1% by weight of the lipopeptide compound or its salt compared to the case where the lipopeptide compound or its salt is not added, Preferably it is promoted 1.5 times or more, more preferably 2 times or more.
  • the log P value is an index representing the hydrophilicity or hydrophobicity of a substance, and as defined in Chemical Review vol71 (6), 525 (1971) etc., the substance between the octanol phase and the aqueous phase ( It is a common logarithmic value of the distribution coefficient of the physiologically active ingredient).
  • the logP value can be calculated by using calculation software (for example, “CS Chem3D ver. 9.0” (trade name) manufactured by Cambridgesoft).
  • lipopeptide compounds include biosurfactants produced by bacteria belonging to the genus Bacillus such as Bacillus subtilis, and preferred examples include surfactin or salts thereof and salts of related compounds. Is mentioned.
  • Surfactin or its salt is represented by the following formula (1):
  • * represents an optically active point.
  • L-Leu represents L-leucine
  • D-Leu represents D-leucine
  • L-Val represents L-valine.
  • X represents any one amino acid selected from L-leucine, L-isoleucine, and L-valine.
  • R represents a linear or branched alkyl group having 9 to 13 carbon atoms.
  • examples of the linear alkyl group having 9 to 13 carbon atoms include nonyl group, decyl group, undecyl group, dodecyl group, and tridecyl group.
  • examples of the branched alkyl group having 9 to 13 carbon atoms include 7-methyloctyl group, 8-methylnonyl group, 9-methyldecyl group, 10-methylundecyl group, 11-methyldodecyl group, and 6-methyloctyl group. 7-methylnonyl group, 8-methyldecyl group, 9-methylundecyl group, 10-methyldodecyl group and the like.
  • linear or branched alkyl groups may be substituted with one or more substituents.
  • substituents include an amino group, a hydroxyl group, a phenyl group, an aryl group, an alkanoyl group, an alkenyl group, an alkynyl group, an alkoxyl group, a nitro group, and a halogen atom.
  • M represents hydrogen, an alkali metal, an alkaline earth metal, an optionally substituted amine (including optionally substituted ammonium) or the like, and is particularly limited as long as it forms a salt with surfactin. It is not a thing.
  • the alkali metal is not particularly limited, but represents lithium, sodium, potassium and the like.
  • Alkaline earth metal is not particularly limited, but represents beryllium, magnesium, calcium and the like.
  • the amine is not particularly limited as long as it becomes the M by reacting with the carboxylic acid of surfactin, and may be substituted.
  • examples of such amines include ammonia (M is ammonium), monosubstituted amines (M is monosubstituted ammonium such as RN (+) H 3 ), disubstituted amines (M is disubstituted).
  • tri-substituted amines M is tri-substituted ammonium
  • M includes tetra-substituted ammonium and the like.
  • substituent of the amine examples include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and tert-butyl group, aralkyl groups such as benzyl group, methylbenzyl group and phenylethyl group. And organic groups such as aryl groups such as a group, phenyl group, toluyl group, and xylyl group.
  • amine examples include methylamine, ethylamine, benzylamine, aniline, diethylamine, dicyclohexylamine, pyrrolidine, morpholine, N-benzyl-N-ethylamine, N-ethylaniline, triethylamine, pyridine and the like. These organic groups may be further substituted with one or more substituents.
  • Preferred M is an alkali metal (sodium, potassium, etc.), particularly sodium.
  • the percutaneous absorption enhancer of the present invention is suitably used for pharmaceutical preparations used for the purpose of permeating and absorbing physiologically active substances into the skin, and for external preparations for skin such as cosmetics and quasi drugs.
  • the physiologically active ingredient means a substance that exhibits physiological action or pharmacological action on a living organism and exhibits anti-inflammatory effect, metabolic activity effect, skin condition improving effect, and the like.
  • the component other than the lipopeptide compound of the percutaneous absorption enhancer of the present invention or a salt thereof is not particularly limited and contains components generally used for pharmaceuticals, cosmetics, quasi drugs, and the like. It may be.
  • the external preparation for skin according to the present invention contains the transdermal absorption enhancer and a physiologically active substance having a log P value of -5.5 to 1.0.
  • the percutaneous absorption enhancer according to the present invention selectively shows an effect of improving the permeability to the skin with respect to such a physiologically active substance.
  • the physiologically active substance preferably has a log P value of ⁇ 4.0 to 1.0, more preferably ⁇ 3.0 to 1.0, still more preferably ⁇ 3.0 to 0, particularly Preferably, it is -2.0 to 0.
  • physiologically active component examples include whitening agents, anti-aging agents, antioxidants, moisturizers, hair restorers, cell activators, vitamins, amino acids and the like.
  • bioactive ingredients include arbutin and its derivatives, L-ascorbic acid and its derivatives (such as ascorbic acid phosphate), hydroquinone and its derivatives, glutathione and its derivatives, placental extract, pantothenic acid And derivatives thereof, tranexamic acid and derivatives thereof, kojic acid and derivatives thereof, cysteine and derivatives thereof, ellagic acid and derivatives thereof, resorcin derivatives such as lucinol, plant extracts such as chamomile extract and licorice extract, superoxide dismutase and Derivatives thereof, mannitol and derivatives thereof, carotenoids such as beta-carotene, astaxanthin and derivatives thereof, rutin and derivatives thereof, bilirubin and derivatives thereof, cholesterol and derivatives thereof, tryptophan and derivatives thereof Histidine and derivatives thereof, flavonoids such as quercetin and quercitrin, catechin and derivatives thereof, gall
  • the blending amount of the physiologically active ingredient in the external preparation for skin can be used without particular limitation as long as it is a physiologically active concentration effective for treatment or the like.
  • the amount of the lipopeptide compound or its salt contained in the external preparation for skin is appropriately adjusted according to the type of the physiologically active ingredient.
  • the lipopeptide compound or a salt thereof is preferably contained in an amount of 0.1 to 100 parts by weight with respect to 1 part by weight of the physiologically active ingredient. More preferably, it is 0.1 to 10 parts by weight.
  • the skin external preparation in addition to the percutaneous absorption enhancer and the physiologically active ingredient, those usually used for external preparations for skin can be used without particular limitation.
  • the skin external preparation includes, for example, a whitening skin external preparation, an anti-aging skin external preparation, a wrinkle removing skin external preparation, a hair removal agent, a poultice, an anti-inflammatory agent, an anti-inflammatory agent, a hair growth agent and the like.
  • the dosage form of the external preparation for skin is not particularly limited, and examples thereof include emulsions, creams, lotions, essences, mousses, sprays, gels, powders, and oily external preparations for skin.
  • components used in the external preparation for skin include, for example, polyhydric alcohol, liquid paraffin, squalane, vegetable oil, higher fatty acid, higher alcohol, and other oils, citric acid, lactic acid and other organic acids, surfactants, pigments, Examples include dyes, preservatives, resins, pH adjusters, antioxidants, ultraviolet absorbers, chelating agents, thickeners, humectants, alcohol, water, and fragrances.
  • the appropriate amount of the external preparation for skin of the present invention may be brought into contact (applied, etc.) with the target application site according to the symptoms. Further, the number of times of contact (application) is not particularly limited, and for example, contact (application) may be performed once or more per day.
  • Examples 1 to 13 and Comparative Example 1 Surfactin sodium added section
  • a skin permeability test for each physiologically active ingredient was performed.
  • Rat skin (“a” is written in the skin column in Table 1 in the application examples) or a cultured human skin model (“TESTSKIN” (trademark) manufactured by Toyobo Co., Ltd. "B") was set at the joint of the Franz cell, and the interior of the Franz cell jacket was kept at 37 ° C.
  • a sample containing a physiologically active ingredient was put in a donor tank (capacity: about 10 mL), and the test was started.
  • the composition of the sample was as follows: Surfactin Na: 2% by weight (in the case of rat skin “a”) or 1 wt% (in the case of cultured human skin model “b”), bioactive component: 1% by weight, glycerin: 10% by weight , Water: the rest.
  • the receptor fluid was sampled, and the amount (W1) of the physiologically active component that permeated through the skin was quantified under the analysis conditions shown in Table 1.
  • “addition effect” in Table 1 is (permeation amount of physiologically active component in surfactin Na added group (W1)) / (permeation amount of physiologically active component in surfactin Na added group (W2)). is there.
  • the accelerating magnification is the addition effect / surfactin Na concentration (% by weight) in the surfactin Na addition section.
  • the log P value in the table is CS Chem3D (trade name) ver. It is the calculated value of each physiologically active ingredient determined using 9.0. Specifically, a chemical structural formula of each physiologically active component was drawn with CS ChemDraw (trade name), which is the related software, and read into the Chem3D (trade name) to obtain a logP value.
  • the percutaneous absorption enhancer of the present invention can be used in combination with various physiologically active ingredients to provide a skin external preparation (whitening skin external preparation, anti-aging skin external preparation, wrinkle removing skin external preparation, hair removal agent, poultice, anti-inflammatory agent. Agent, anti-inflammatory agent, hair restorer, etc.).

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Birds (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Peptides Or Proteins (AREA)

Abstract

L'invention concerne un promoteur d'absorption percutanée qui comprend un composé lipopetidique ou un sel de celui-ci. Dans un test de cellule de Franz statique à l'aide d'un composant physiologiquement actif ayant une valeur de log P de -5,5-1,0, le promoteur d'absorption percutanée peut augmenter le taux de perméation cutanée, par exemple, de deux fois ou plus par % en poids du composé lipopeptidique ou d'un sel de celui-ci, en comparaison à un cas dans lequel le composé lipopeptidique ou un sel de celui-ci n'est pas ajouté. Un exemple du composé lipopeptidique est la surfactine qui est représentée par la formule (1).
PCT/JP2012/050324 2011-01-13 2012-01-11 Promoteur d'absorption percutanée et préparation cutanée externe Ceased WO2012096276A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2012552734A JP5906194B2 (ja) 2011-01-13 2012-01-11 皮膚外用剤

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2011-005117 2011-01-13
JP2011005117 2011-01-13
JP2011-144509 2011-06-29
JP2011144509 2011-06-29

Publications (1)

Publication Number Publication Date
WO2012096276A1 true WO2012096276A1 (fr) 2012-07-19

Family

ID=46507174

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/050324 Ceased WO2012096276A1 (fr) 2011-01-13 2012-01-11 Promoteur d'absorption percutanée et préparation cutanée externe

Country Status (2)

Country Link
JP (1) JP5906194B2 (fr)
WO (1) WO2012096276A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014157169A1 (fr) * 2013-03-25 2014-10-02 株式会社カネカ Agent de nettoyage pour éliminer par lavage un contaminant à base de silicone
JP2016027036A (ja) * 2014-06-30 2016-02-18 ロート製薬株式会社 外用組成物、化粧料、経皮吸収促進用組成物、外用組成物における有効成分の経皮吸収性を高める方法、経皮投与型医薬及び点眼用組成物
JP2016098199A (ja) * 2014-11-21 2016-05-30 花王株式会社 水性組成物
WO2016114340A1 (fr) * 2015-01-15 2016-07-21 株式会社カネカ Agent de protection contre les uv
EP3193823A4 (fr) * 2014-07-31 2018-04-18 Saft Biotechnology Com. Ltd Applications de surfactine dans des produits cosmétiques et produits associés
CN109172430A (zh) * 2018-11-01 2019-01-11 广东芭薇生物科技股份有限公司 一种含小分子团水的促渗透组合物及其在化妆品中的应用
JP2019116484A (ja) * 2013-06-05 2019-07-18 国立大学法人九州大学 親水性薬物を経皮吸収させる方法
WO2020111067A1 (fr) * 2018-11-29 2020-06-04 ロート製薬株式会社 Composition contenant de l'éther d'alcool aliphatique et de glycérine
US10835572B2 (en) 2014-06-30 2020-11-17 Rohto Pharmaceutical Co., Ltd. Composition for external application
CN116172895A (zh) * 2022-12-30 2023-05-30 株式会社资生堂 化妆品组合物
WO2025164298A1 (fr) * 2024-01-29 2025-08-07 株式会社 資生堂 Agent de relaxation à jonction serrée contenant de la surfactine et/ou un sel de sodium associé

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5225013A (en) * 1975-08-20 1977-02-24 Takeda Chem Ind Ltd Insulin pharmaceutical for nasal administration
JP2000327591A (ja) * 1998-05-29 2000-11-28 Showa Denko Kk 皮膚外用剤用界面活性剤及びそれを含有する皮膚外用剤
JP2003128512A (ja) * 2001-10-18 2003-05-08 Showa Denko Kk 化粧料用抗菌性組成物
JP2009062288A (ja) * 2007-09-04 2009-03-26 National Institute Of Advanced Industrial & Technology ソホロリピッドを含む経皮吸収制御剤及びその製造方法
WO2009044279A2 (fr) * 2007-09-30 2009-04-09 Umo Inc., Co. Ltd. Peptide présentant une activité antimicrobienne et/ou bio-tensioactive

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5225013A (en) * 1975-08-20 1977-02-24 Takeda Chem Ind Ltd Insulin pharmaceutical for nasal administration
JP2000327591A (ja) * 1998-05-29 2000-11-28 Showa Denko Kk 皮膚外用剤用界面活性剤及びそれを含有する皮膚外用剤
JP2003128512A (ja) * 2001-10-18 2003-05-08 Showa Denko Kk 化粧料用抗菌性組成物
JP2009062288A (ja) * 2007-09-04 2009-03-26 National Institute Of Advanced Industrial & Technology ソホロリピッドを含む経皮吸収制御剤及びその製造方法
WO2009044279A2 (fr) * 2007-09-30 2009-04-09 Umo Inc., Co. Ltd. Peptide présentant une activité antimicrobienne et/ou bio-tensioactive

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NICOLI S. ET AL.: "Effect of lipopeptides and iontophoresis on aciclovir skin delivery", J PHARM PHARMACOL, vol. 62, no. 6, 2010, pages 702 - 708 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014157169A1 (fr) * 2013-03-25 2014-10-02 株式会社カネカ Agent de nettoyage pour éliminer par lavage un contaminant à base de silicone
JPWO2014157169A1 (ja) * 2013-03-25 2017-02-16 株式会社カネカ シリコーン汚染物を洗浄するための洗浄剤
JP2019116484A (ja) * 2013-06-05 2019-07-18 国立大学法人九州大学 親水性薬物を経皮吸収させる方法
US10835572B2 (en) 2014-06-30 2020-11-17 Rohto Pharmaceutical Co., Ltd. Composition for external application
JP2016027036A (ja) * 2014-06-30 2016-02-18 ロート製薬株式会社 外用組成物、化粧料、経皮吸収促進用組成物、外用組成物における有効成分の経皮吸収性を高める方法、経皮投与型医薬及び点眼用組成物
JP2022141907A (ja) * 2014-06-30 2022-09-29 ロート製薬株式会社 外用組成物、化粧料、経皮吸収促進用組成物、外用組成物における有効成分の経皮吸収性を高める方法、経皮投与型医薬及び点眼用組成物
EP3193823A4 (fr) * 2014-07-31 2018-04-18 Saft Biotechnology Com. Ltd Applications de surfactine dans des produits cosmétiques et produits associés
JP2016098199A (ja) * 2014-11-21 2016-05-30 花王株式会社 水性組成物
WO2016114340A1 (fr) * 2015-01-15 2016-07-21 株式会社カネカ Agent de protection contre les uv
CN109172430A (zh) * 2018-11-01 2019-01-11 广东芭薇生物科技股份有限公司 一种含小分子团水的促渗透组合物及其在化妆品中的应用
WO2020111067A1 (fr) * 2018-11-29 2020-06-04 ロート製薬株式会社 Composition contenant de l'éther d'alcool aliphatique et de glycérine
CN113164799A (zh) * 2018-11-29 2021-07-23 日本乐敦制药株式会社 包含由脂肪醇和甘油合成的醚的组合物
JPWO2020111067A1 (ja) * 2018-11-29 2021-10-28 ロート製薬株式会社 脂肪族アルコールとグリセリンとのエーテルを含む組成物
CN116172895A (zh) * 2022-12-30 2023-05-30 株式会社资生堂 化妆品组合物
WO2025164298A1 (fr) * 2024-01-29 2025-08-07 株式会社 資生堂 Agent de relaxation à jonction serrée contenant de la surfactine et/ou un sel de sodium associé

Also Published As

Publication number Publication date
JP5906194B2 (ja) 2016-04-20
JPWO2012096276A1 (ja) 2014-06-09

Similar Documents

Publication Publication Date Title
JP5906194B2 (ja) 皮膚外用剤
JP6430109B2 (ja) 外用組成物
JP6632495B2 (ja) 抗菌用組成物
JP2005139070A (ja) 皮膚化粧料
JP5951277B2 (ja) アゼライン酸を含有する外用組成物
WO2020111067A1 (fr) Composition contenant de l'éther d'alcool aliphatique et de glycérine
JP2022141907A (ja) 外用組成物、化粧料、経皮吸収促進用組成物、外用組成物における有効成分の経皮吸収性を高める方法、経皮投与型医薬及び点眼用組成物
JP6310788B2 (ja) 外用組成物
JP6043145B2 (ja) 体臭抑制用の皮膚外用組成物
JP5739679B2 (ja) 外用組成物
JP6416473B2 (ja) 外用組成物
JP2016027033A (ja) 外用組成物、眼科用組成物、抗菌剤、及び抗菌方法
JP2019137695A (ja) 皮膚有効成分の浸透方法
JP2015218147A (ja) リラナフタート含有外用医薬組成物
JP6371519B2 (ja) 皮膚外用組成物
JP2021138683A (ja) 外用組成物
JP2016027034A (ja) 外用組成物
WO2016121753A1 (fr) Procédé pour contrôler la pénétration de la peau
JP6702783B2 (ja) 皮膚浸透促進剤
JP2018043946A (ja) メラニン産生抑制剤
JP2003113066A (ja) 化粧料
JP2022167158A (ja) 経皮吸収促進剤
JP2025009674A (ja) 外用組成物
JP4424943B2 (ja) ブライトニング化粧料
AU2023281623A1 (en) Skin care compositions and methods of use

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12734166

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2012552734

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12734166

Country of ref document: EP

Kind code of ref document: A1