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WO2018151442A1 - Composition permettant de soulager, de prévenir ou de traiter une atopie - Google Patents

Composition permettant de soulager, de prévenir ou de traiter une atopie Download PDF

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Publication number
WO2018151442A1
WO2018151442A1 PCT/KR2018/001347 KR2018001347W WO2018151442A1 WO 2018151442 A1 WO2018151442 A1 WO 2018151442A1 KR 2018001347 W KR2018001347 W KR 2018001347W WO 2018151442 A1 WO2018151442 A1 WO 2018151442A1
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WIPO (PCT)
Prior art keywords
composition
present
ite
allergic
skin
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Ceased
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PCT/KR2018/001347
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English (en)
Korean (ko)
Inventor
주봉건
정하얀
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Sogang University Research Foundation
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Sogang University Research Foundation
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Publication of WO2018151442A1 publication Critical patent/WO2018151442A1/fr
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    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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 is made by the task number 201621018 under the support of the Ministry of Education of the Republic of Korea, the research management specialized organization of the project is (Foundation) Korea Research Foundation, the research project name is “university center research center project”, the research title is “cell damage control material application System development ", the lead organization is Sogang University Industry-Academic Cooperation Foundation, and the research period is from Sept. 01, 2016 to Aug. 31, 2016.
  • the present invention relates to a composition for improving, preventing or treating atopy.
  • allergic skin diseases such as atopic dermatitis and psoriasis are difficult to cure and cause limitations in the individual's social activities due to secondary skin damage caused by extreme itching and increased scratching behavior. It is a social problem because it leads to suicide.
  • drugs for treating atopic dermatitis include antihistamines, steroid hormones (cortisol, prednisolone, methylprednisolone, dexamethasone injections and ointments), and moisturizers.
  • these drugs are not effective for the treatment of allergic dermatitis, especially in the case of steroid treatments, they show temporary efficacy, but in the long run, they cause enlargement of capillaries and thinning the skin, resulting in worse symptoms.
  • the patient using the steroid treatment is discontinued, it causes a more severe dermatitis symptom called steroid rebound, so it is urgent to develop an appropriate treatment for the treatment of allergic skin diseases.
  • Aryl hydrocarbon receptor (hereinafter referred to as 'AHR') is a receptor protein that is activated by binding to a substance such as dioxin and the like, and acts as a transcription factor. Most of the aryl hydrocarbon receptors that do not bind to the ligand are present in the cytoplasm, but when bound to the ligand, they move to the nucleus and act as transcription factors. These aryl hydrocarbon receptors are heterochromic with the aryl hydrocarbon receptor nuclear translocator (ARNT) in the nucleus, and the cytochrome P450 monooxygenase (CYP1A1, CYP1A2, CYP1B1).
  • ARNT aryl hydrocarbon receptor nuclear translocator
  • GSTs Glutathione-S-transferase
  • NADPH / quinone oxidoreductase NADPH / quinone oxidoreductase
  • aldehyde dehydrogenase 3 gene expression It is known to be responsible for detoxification.
  • PCB polychlorinated biphenyl
  • endogenous tryptophan derivatives arachidonic acid metabolites, such as ITE [2- (1H-Indol-3-ylcarbonyl) -4-thiazolecarboxylic acid methyl ester]
  • ITE 2- (1H-Indol-3-ylcarbonyl) -4-thiazolecarboxylic acid methyl ester
  • Arachidonic acid metabolites, heme metabolites, equilenin and indigoids are known ligands of AHR.
  • the present inventors have tried to develop a novel atopic treatment that can replace the conventional steroidal atopic treatment.
  • ITE 1- H -Indol- 3-ylcarbonyl) -4-thiazolecarboxylic acid
  • a ligand of the aryl hydrocarbon receptor symptoms such as edema, hemorrhage, ulceration, inflammation, and atopic dermatitis by drying
  • the present invention was completed by confirming the effect of mitigating.
  • Another object of the present invention to provide a cosmetic composition for improving the skin condition.
  • Still another object of the present invention is to provide a method for treating an allergic disease.
  • the invention is to improve allergic diseases, prevention comprising the ITE [2- (1 H -Indol- 3-ylcarbonyl) -4-thiazolecarboxylic acid methyl ester] represented by the general formula (1) as an active ingredient Or provide a pharmaceutical composition for treatment.
  • the present inventors have tried to develop a novel atopic treatment that can replace the conventional steroidal atopic treatment.
  • the treatment of ITE which is a ligand of the aryl hydrocarbon receptor, confirmed the effect of alleviating symptoms such as edema, bleeding, ulceration, inflammation and drying caused by atopic dermatitis.
  • the pharmaceutical composition for improving, preventing or treating allergic diseases of the present invention includes the compound of Formula 1 as an active ingredient.
  • the compound of formula (I) is 2- (1 H -Indol-3- ylcarbonyl) -4-thiazolecarboxylic acid methyl ester (ITE).
  • the compound reduces the expression of thymic stromal lymphopoietin (TSP) gene or protein.
  • TSP thymic stromal lymphopoietin
  • the TSLP is a cytokine secreted from keratinocytes of the skin and stimulates the sensory nerves present in the subcutaneous to cause itching or dermatitis.
  • the term “comprising as an active ingredient” means that the compound of Formula 1 contains an amount sufficient to achieve anti-allergic activity.
  • the term “improvement” or “prevention” refers to any action that inhibits allergies or delays progression by administration of a composition of the present invention.
  • treatment refers to the inhibition of the development of allergic diseases; Relief of allergic diseases; And elimination of allergic diseases.
  • allergy refers to a variety of diseases, diseases or abnormalities caused by hypersensitivity to certain substances in the human body, ie, excessive reaction of the body's immune system to substances from outside.
  • Allergic diseases to be applied to the compositions of the present invention are preferably formulation immediate hypersensitivity and formulation delayed hypersensitivity.
  • Type I hypersensitivity reactions are bronchial asthma, allergic rhinitis, atopic dermatitis, allergic conjunctivitis, allergic otitis media, urticaria and anaphylatic shock, and type delayed hypersensitivity reactions are contact hypersensitivity, allergy Sexual contact dermatitis, bacterial allergies, fungal allergies, viral allergies, drug allergies, thyroiditis and allergic encephalitis.
  • Type I immediate hypersensitivity is divided into two stages: the first phase is a Th1 cell response that produces IL-12 and IFN- ⁇ that inhibits the release of IgE and IgG1 and increases the secretion of IgG2a by invasion of allergens.
  • Th2 cell responses that produce IL-4, IL-5, and IL-13 are inclined toward Th2, excessive immune responses of Th2 secrete IL-4 and IL-13, and B cells are produced by the effects.
  • One IgE-specific antibody is attached to the surface of mast cells and basophils to prepare for allergic development. It is said to be sensitized to allergens.
  • the second stage of the onset of allergy is divided into early and late reactions, and the initial reaction is an allergen reinvading the body to stimulate mast cells and induce a degranulation reaction, which is released by histamine, lipid metabolites, cytokines, etc. Expansion and the like is occurring, the late reaction is activated by the infiltration of neutrophils, eosinophils, macrophages, Th2 cells, basophils, etc. in the tissues, causing inflammation, causing atopic dermatitis, rhinitis, asthma.
  • the allergic disease is any one allergic disease selected from the group consisting of atopic dermatitis, contact dermatitis, urticaria, pruritus, edema and allergic dermatitis. .
  • the allergic disease is atopic dermatitis, pruritus or edema.
  • atopic dermatitis is a skin eczema disease accompanied by chronic recurring severe itching, which is a kind of dermatitis.
  • pruritus is itching, accompanied by diseases or conditions such as atopic dermatitis, contact dermatitis, urticaria, nodular benign, scabies, chronic simple thyroid, insect bites, eczema.
  • the term "edema” is a condition in which excessive accumulation of moisture in tissues.
  • composition of the present invention may be prepared as a pharmaceutical composition.
  • the composition of the present invention comprises (a) a pharmaceutically effective amount of the compound of formula 1 of the present invention as described above; And (b) a pharmaceutically acceptable carrier.
  • pharmaceutically effective amount means an amount sufficient to achieve the efficacy or activity of the compounds described above.
  • the pharmaceutical composition of the present invention includes a pharmaceutically acceptable carrier.
  • Pharmaceutically acceptable carriers included in the pharmaceutical compositions of the present invention are those commonly used in the preparation, such as lactose, dextrose, sucrose, sorbitol, mannitol, starch, acacia rubber, calcium phosphate, alginate, gelatin, Calcium silicate, microcrystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrup, methyl cellulose, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil, and the like It doesn't happen.
  • the pharmaceutical composition of the present invention may further include a lubricant, a humectant, a sweetener, a flavoring agent, an emulsifier, a suspending agent, a preservative, and the like.
  • a lubricant e.g., talc, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, a kaolin, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, mannitol, mannitol, mannitol, mannitol, mannitol, mannitol, mannitol, mannitol, mannitol, mann
  • the pharmaceutical composition of the present invention may be administered orally or parenterally, and is preferably applied by parenteral administration.
  • Suitable dosages of the pharmaceutical compositions of the present invention may vary depending on factors such as the formulation method, mode of administration, age, weight, sex, morbidity, condition of food, time of administration, route of administration, rate of excretion and response to response of the patient. Can be. General dosages of the pharmaceutical compositions of the invention are in the range of 0.001-100 mg / kg, but are not limited to adults.
  • compositions of the present invention may be prepared in unit dose form by formulating with a pharmaceutically acceptable carrier and / or excipient according to methods which can be easily carried out by those skilled in the art. Or may be prepared by incorporation into a multi-dose container.
  • the formulation may be in the form of solutions, suspensions, syrups or emulsions in oils or aqueous media, or in the form of extracts, powders, powders, granules, tablets or capsules, and may further comprise dispersants or stabilizers.
  • a cosmetic composition for improving skin conditions comprising ITE represented by the following formula (1) as an active ingredient.
  • the improvement of the skin condition is an improvement of edema, bleeding, ulceration, inflammation or dryness of the skin.
  • the cosmetic composition of the present invention can effectively improve the condition of edema, bleeding, ulceration, inflammation or dryness of the skin.
  • the composition of the present invention may include not only the compound of Formula 1, which is the active ingredient, but also components commonly used in cosmetic compositions, such as antioxidants, stabilizers, and dissolutions. Conventional adjuvants such as agents, vitamins, pigments and flavorings, and carriers.
  • purified water purified water, monohydric alcohols (ethanol or propyl alcohol), polyhydric alcohols (glycerol, 1,3-butylene glycol or propylene glycol), higher fatty acids (palmitylic acid or linolenic acid), fats and oils (wheat embryo oil, Camellia oil, jojoba oil, olive oil, squalene, sunflower oil, macadamia peanut oil, avocado oil, soybean hydrogenated lecithin or fatty acid glycerides), and the like.
  • surfactants, bactericides, antioxidants, ultraviolet absorbers, anti-inflammatory agents and refreshing agents may be added as necessary.
  • polyoxyethylene hardened castor oil, polyoxyethylene, oleyl ether, monooleate polyoxyethylene, polyoxyethylene, glyceryl monostearate, monostearate sorbitan, monooleate polyoxyethylene, sorbitan, Sucrose fatty acid ester, hexaglycerol monolauric acid, polyoxyethylene reduced lanolin, POE, glyceryl pyroglutamic acid, isostearic acid, diester, N-acetylglutamine, isostearyl ester and the like can be used.
  • fungicides examples include hydroxy thiol, trichromic acid, chlorohexidine gluconate, phenoxyethanol, resorcin, isopropylmethylphenol, azulene, salicylic acid, zinc pyrithaone, and the like.
  • any of butylhydroxyanisole, molten acid, molten acid propyl and erythorbic acid can be used.
  • UV absorber examples include benzophenones such as dihydroxy benzophenone, melanin, ethyl paraaminobenzoate, 2-ethylhexyl ester of paradimethylaminobenzoic acid, synoxite and 2-ethylhexyl ester of paramethoxy cinnamic acid, and 2- (2- Hydroxy-5-methylphenyl) benzotriazole, urokanoic acid, metal oxide fine particles and the like can be used.
  • benzophenones such as dihydroxy benzophenone, melanin, ethyl paraaminobenzoate, 2-ethylhexyl ester of paradimethylaminobenzoic acid, synoxite and 2-ethylhexyl ester of paramethoxy cinnamic acid
  • 2- (2- Hydroxy-5-methylphenyl) benzotriazole urokanoic acid, metal oxide fine particles and the like
  • anti-inflammatory agent examples include dipotassium glytilinate, allantoin, and the like, and a refreshing agent may be red pepper tink, 1-menthol, or the like.
  • the present invention provides a method for alleviating or treating an allergic disease, comprising administering to a subject a therapeutically effective amount of a composition comprising an ITE represented by Formula 1 as an active ingredient. to provide.
  • administer refers to administering a therapeutically effective amount of a composition of the invention directly to a subject (an individual) in need thereof so that the same amount is formed in the subject's body. Say that.
  • a “therapeutically effective amount” of a composition means a content of the composition that is sufficient to provide a therapeutic or prophylactic effect to a subject to which the composition is to be administered, and includes a “prophylactically effective amount”.
  • the term “subject” includes, without limitation, human, mouse, rat, guinea pig, dog, cat, horse, cow, pig, monkey, chimpanzee, baboon or rhesus monkey. Specifically, the subject of the present invention is a human.
  • the method for treating the allergic disease of the present invention is the same as the composition comprising the above-described compound of Formula 1 as an active ingredient and the target disease of the present invention, so that the description thereof is omitted in order to avoid excessive complexity of the present specification. do.
  • the present invention provides a pharmaceutical composition for improving, preventing or treating allergic diseases and a cosmetic composition for improving skin condition.
  • composition of the present invention can effectively improve atopic dermatitis by inhibiting the expression of TSLP genes and proteins.
  • Figure 1 shows the result that the increased TSLP mRNA expression by TNF ⁇ or flagellin in HaCaT dermal keratinocytes is reduced by ITE.
  • FIG. 2 shows the result that TS increased TSLP protein expression by TNF ⁇ or flagellin in HaCaT dermal keratinocytes.
  • Figure 3 shows the results of the symptoms of atopic dermatitis alleviated by ITE in an atopic animal model.
  • Dexamethasone (Dex) means a positive control.
  • 5a to 5h show the results of inhibiting the expression of TSLP, IL-4, IL-10, IL-13, IL-22, IL-25, IL-31 and IL-33 by ITE in skin tissue of an atopic animal model, respectively.
  • Dexamethasone (Dex) means a positive control.
  • % used to indicate the concentration of a particular substance is solid / solid (weight / weight)%, solid / liquid (weight / volume)%, and Liquid / Liquid is (volume / volume)%
  • Human keratinocytes HaCaT dermal keratinocytes, contained Dulbecco's Modification of Eagle's Medium (DMEM) containing 10% fetal bovine serum (FBS), 100 units / ml penicillin and 100 ⁇ g / ml streptomycin The medium was incubated in a 37 ° C. incubator maintaining proper humidity and 5% CO 2 .
  • DMEM Dulbecco's Modification of Eagle's Medium
  • FBS fetal bovine serum
  • FBS fetal bovine serum
  • penicillin 100 units / ml
  • streptomycin 100 units / ml bovine serum
  • the medium was incubated in a 37 ° C. incubator maintaining proper humidity and 5% CO 2 .
  • TNF ⁇ 50 ng / ml
  • flagellin 10 ng / ml
  • the human skin epidermal keratinocytes, HaCaT were treated with TNF ⁇ or flagellin, respectively, to induce TSLP expression.
  • the protein was transferred to a polyvinylidene difluoride (PVDF) membrane (Millipore, USA), placed in 5% skim milk / PBST, blocked for 1 hour, and washed with 1 ⁇ PBST.
  • PVDF polyvinylidene difluoride
  • TSLP Abcam, UK
  • ⁇ -actin Santa cruz, USA
  • Secondary antibodies, anti-mouse-HRP and anti-rabbit-HRP (1: 10,000, GenDEPOT, USA) were treated for 1 hour, washed with 1 ⁇ PBST, and then with an enhanced chemiluminescence (ECL) solution (DoGEN, Korea). Reaction for 1 minute and developed by Super RX film (Fuji, Japan) to confirm the expression of the protein.
  • ECL enhanced chemiluminescence
  • the human skin epidermal keratinocytes, HaCaT were treated with TNF ⁇ or flagellin, respectively, to induce TSLP expression.
  • ITE an active ingredient of the present invention, suppresses the expression of TSLP, a cytokine that causes itching or dermatitis by stimulating the sensory nerves of the skin at the cellular level, thereby improving skin condition due to allergic skin diseases or allergies. It turned out that it can be usefully used as a composition for.
  • DNFB 1-Fluoro-2,4-dinitrobenzene
  • ITE 100 ⁇ M
  • dexamethasone 200 ⁇ M
  • PBS PBS
  • atopy dermatitis was induced by applying DNFB (1-Fluoro-2,4-dinitrobenzene). Thereafter, ITE and a positive control group dexamethasone were treated to check the skin condition.
  • DNFB 1,2-Fluoro-2,4-dinitrobenzene
  • ITE and a positive control group dexamethasone were treated to check the skin condition.
  • atopic dermatitis symptoms such as skin edema, bleeding, ulceration, inflammation, and dryness were induced (FIG. 3).
  • the treatment of ITE has an effect of alleviating symptoms similar to the treatment of dexamethasone, a positive control group (FIG. 3).
  • RNA was extracted from the skin tissue and TSLP, IL-4 (interleukin-4), IL-10 (interleukin-10), IL-13 (interleukin-13), and IL-22 (interleukin-22) in the same manner as in Example 1 ), IL-25 (interleukin-25), IL-31 (interleukin-31) and IL-33 (interleukin-33) expression was examined by PCR.
  • the sequences of the primers used for PCR are shown in Table 2:
  • ITE an active ingredient of the present invention, alleviates atopic symptoms in an animal model causing atopic dermatitis and suppresses the expression of cytokines causing atopic dermatitis. It turned out that it can be usefully used as a composition for.
  • Sequence Listing 1st and 2nd Sequence are forward and reverse primers for human GAPDH gene detection, respectively
  • Sequence Listing 3rd and 4th Sequence are forward and reverse primers for human TSLP gene detection, respectively.
  • SEQ ID NOs: 5 and 6 are forward and reverse primers for detecting mouse GAPDH genes, respectively
  • SEQ ID NOs. 7 and 8 are forward and reverse primers for detecting mouse TSLP genes, respectively.
  • SEQ ID NOs: 9 and 10 are forward and reverse primers for detecting mouse IL-4 gene, respectively
  • SEQ ID NO: 11 and 12 are forward and reverse primers for detecting mouse IL-10 gene, respectively.
  • SEQ ID NO: 13 and 14 are forward and reverse primers for the detection of mouse IL-13 gene, respectively
  • SEQ ID NO: 15 and 16 sequences are forward and reverse primers for IL-22 gene detection, respectively
  • SEQ ID NO: 17 and 18 are forward and reverse primers for the detection of mouse IL-25, respectively
  • SEQ ID NO: 19 and 20 are forward and reverse primers for the detection of mouse IL-31 gene, respectively
  • List 21 and 22 are forward and reverse primers for the detection of mouse IL-33 gene, respectively.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
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  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne : une composition pharmaceutique permettant de soulager, de prévenir ou de traiter une maladie allergique ; et une composition cosmétique permettant d'améliorer l'état de la peau. La composition de la présente invention permet de soulager efficacement une dermatite atopique par inhibition de l'expression du gène et de la protéine TSLP.
PCT/KR2018/001347 2017-02-17 2018-01-31 Composition permettant de soulager, de prévenir ou de traiter une atopie Ceased WO2018151442A1 (fr)

Applications Claiming Priority (2)

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KR20170021567 2017-02-17
KR10-2017-0021567 2017-02-17

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WO2018151442A1 true WO2018151442A1 (fr) 2018-08-23

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070043092A1 (en) * 2001-02-14 2007-02-22 Deluca Hector F Use of aryl hydrocarbon receptor ligand as a therapeutic intervention in angiogenesis-implicated disorders
WO2009093207A1 (fr) * 2008-01-23 2009-07-30 Jean Hilaire Saurat Composition a usage topique
KR20150006639A (ko) * 2013-07-09 2015-01-19 주식회사 엘지생활건강 Tslp 분비 저해능 및 이에 의한 알러지성 질환의 개선능을 가지는 조성물
KR20150095012A (ko) * 2014-02-12 2015-08-20 코스맥스 주식회사 코디세핀을 유효성분으로 함유하는 아토피 치료 또는 예방용 피부 외용제 조성물
JP2016150930A (ja) * 2015-02-19 2016-08-22 花王株式会社 ディフェンシン発現促進剤

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070043092A1 (en) * 2001-02-14 2007-02-22 Deluca Hector F Use of aryl hydrocarbon receptor ligand as a therapeutic intervention in angiogenesis-implicated disorders
WO2009093207A1 (fr) * 2008-01-23 2009-07-30 Jean Hilaire Saurat Composition a usage topique
KR20150006639A (ko) * 2013-07-09 2015-01-19 주식회사 엘지생활건강 Tslp 분비 저해능 및 이에 의한 알러지성 질환의 개선능을 가지는 조성물
KR20150095012A (ko) * 2014-02-12 2015-08-20 코스맥스 주식회사 코디세핀을 유효성분으로 함유하는 아토피 치료 또는 예방용 피부 외용제 조성물
JP2016150930A (ja) * 2015-02-19 2016-08-22 花王株式会社 ディフェンシン発現促進剤

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