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WO2024144327A1 - Nouvelle composition pour le traitement de maladies inflammatoires de la peau - Google Patents

Nouvelle composition pour le traitement de maladies inflammatoires de la peau Download PDF

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Publication number
WO2024144327A1
WO2024144327A1 PCT/KR2023/021921 KR2023021921W WO2024144327A1 WO 2024144327 A1 WO2024144327 A1 WO 2024144327A1 KR 2023021921 W KR2023021921 W KR 2023021921W WO 2024144327 A1 WO2024144327 A1 WO 2024144327A1
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WO
WIPO (PCT)
Prior art keywords
composition
inflammatory skin
pharmaceutical composition
acid
expression
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/KR2023/021921
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English (en)
Korean (ko)
Inventor
서영거
김동현
김아람
이승범
김현수
신정우
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.)
Industry Academic Cooperation Foundation of College of Medicine Pochon CHA University
Original Assignee
Industry Academic Cooperation Foundation of College of Medicine Pochon CHA University
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 Industry Academic Cooperation Foundation of College of Medicine Pochon CHA University filed Critical Industry Academic Cooperation Foundation of College of Medicine Pochon CHA University
Publication of WO2024144327A1 publication Critical patent/WO2024144327A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • 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
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • 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
    • A23V2250/00—Food ingredients
    • A23V2250/30—Other Organic compounds

Definitions

  • One aspect is to provide a pharmaceutical composition for preventing or treating inflammatory skin diseases.
  • Another aspect provides a health functional food composition for preventing or improving inflammatory skin diseases, comprising a compound represented by the following formula (1), an isomer thereof, or a foodologically acceptable salt.
  • ingredients included in the cosmetic composition include, in addition to the active ingredient and carrier ingredient, ingredients commonly used in cosmetic compositions, and may include conventional auxiliaries such as antioxidants, stabilizers, solubilizers, vitamins, pigments, and fragrances. You can. Additionally, in addition to the component represented by Chemical Formula 1 and the components described above, the cosmetic composition may be blended with other components usually mixed in cosmetics, if necessary. Other ingredients that may be added include oils and fats, moisturizers, emollients, surfactants, organic and inorganic pigments, organic powders, ultraviolet absorbers, preservatives, disinfectants, antioxidants, plant extracts, pH adjusters, alcohol, colorants, and fragrances. , blood circulation promoters, cooling agents, antiperspirants, purified water, etc.
  • Another aspect provides a method of treating inflammatory skin disease in a subject comprising administering the pharmaceutical composition to the subject.
  • Another aspect provides use of the pharmaceutical composition for treating inflammatory skin disease.
  • the novel compound can significantly improve thickening and dry skin conditions, which are symptoms of inflammatory skin diseases, especially atopic dermatitis, and can significantly suppress the expression of representative markers expressed in atopic dermatitis, including atopic dermatitis. It can be widely used in the field of treating inflammatory skin diseases.
  • Figure 1 is a diagram showing changes in expression of the filaggrin gene after treating immortalized human skin keratinocytes with atopic dermatitis with compounds.
  • Figure 2a is a diagram showing the treatment of atopy-induced human immortalized skin keratinocytes with compounds and then confirmed through Western blot to confirm changes in the expression of filaggrin protein
  • Figure 2b is the result of quantifying the results confirmed in Figure 2a. am.
  • Figure 4 shows the atopic dermatitis improvement effect according to the concentration of the compound in a 2D in vitro model. Specifically, the results confirm the expression levels of phosphorylated STAT3, STAT3, filaggrin, loricrin, and involucrin proteins.
  • Figure 5 shows the results of confirming the expression levels of filaggrin, loricrin, and involucrin mRNA in an atopic animal model to confirm whether a 3D in vitro model was created by treatment with IL-4 and IL-13.
  • Figure 7 is a diagram showing the observation of skin tissue after treating a 3D in vitro model made by injecting AD biostir with a compound.
  • Figure 8 is a diagram showing the expression level of phosphorylated STAT3 after treating the compound in a 3D in vitro model created by injecting AD biostir.
  • reaction mixture was heated under recycle conditions and then stirred until the reaction was completed.
  • the membrane was blocked with PBS containing 3% (w/v) BSA containing 0.1% (v/v) Tween-20 for 60 minutes at room temperature, and then incubated with anti-FLG (1:1000, sc-66192, Santa Cruz), anti-IVL (1:1000, sc-28557, SantaCruz), and anti-LOR (1:1000, GTX116013, GeneTex) antibodies.
  • Secondary antibodies used were HRP-conjugated goat anti-mouse IgG (1:1000; sc 2005, SantaCruz) and HRP-conjugated anti-rabbit IgG (1:3000, Abcam), and ECL lumi Femto solution A/B ( The blots were developed and analyzed using Dogen, Seoul, Korea.
  • 3D artificial skin was fabricated, IL-4 and IL-13 were treated to create a 3D in-vitro model of atopy, and SKSI-2114 was treated to confirm changes in the same biomarkers as in the 2D experiment.
  • 3D artificial skin can be largely divided into the dermis layer and the epidermis layer, and the construction of the dermis layer proceeds as follows. Dermal fibroblasts isolated from human skin were grown in dermal fibroblast culture medium [DMEM (Hyclone, SH30243.01) with 10% FBS (Hyclone, Sh30084.03) and 1% Penicillin-Streptomycin (Welgene, LS202). -02) was prepared by culturing at 37°C and 5% CO2 culture conditions.
  • the epidermal layer of 3D artificial skin is made by mixing keratinocytes isolated from human skin with keratinocyte culture medium [Dermal Cell Basal Medium (ATCC, PCS-200-030), Keratinocyte Growth Kit (ATCC, PCS-200-040), 0.1% It is manufactured by mixing Penicillin-Streptomycin (Welgene, LS202-02), and 10uM of ROCK inhibitor (Millipore, SCM075) is added to inhibit the differentiation of keratinocytes] and cultured at 37°C and 5% CO2 for about a week. Ready.
  • keratinocyte culture medium [Dermal Cell Basal Medium (ATCC, PCS-200-030), Keratinocyte Growth Kit (ATCC, PCS-200-040), 0.1% It is manufactured by mixing Penicillin-Streptomycin (Welgene, LS202-02), and 10uM of ROCK inhibitor (Millipore, SCM075) is added to inhibit the differentiation of keratinocytes] and cultured at 37°C and

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Mycology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Birds (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Ce nouveau composé peut atténuer remarquablement les affections de peau épaissie et sèche, qui sont des symptômes de maladies inflammatoires de la peau, en particulier la dermatite atopique, et peut inhiber remarquablement l'expression de marqueurs représentatifs exprimés dans la dermatite atopique, et peut ainsi être largement utilisé dans des domaines pour le traitement de la dermatite atopique.
PCT/KR2023/021921 2022-12-29 2023-12-28 Nouvelle composition pour le traitement de maladies inflammatoires de la peau Ceased WO2024144327A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020220189741A KR20240106731A (ko) 2022-12-29 2022-12-29 염증성 피부질환 치료용 신규 조성물
KR10-2022-0189741 2022-12-29

Publications (1)

Publication Number Publication Date
WO2024144327A1 true WO2024144327A1 (fr) 2024-07-04

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Family Applications (1)

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PCT/KR2023/021921 Ceased WO2024144327A1 (fr) 2022-12-29 2023-12-28 Nouvelle composition pour le traitement de maladies inflammatoires de la peau

Country Status (2)

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KR (1) KR20240106731A (fr)
WO (1) WO2024144327A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120079274A (ko) * 2011-01-04 2012-07-12 서울대학교산학협력단 신규한 데구엘린 유도체 또는 이의 약학적으로 허용가능한 염 및 이를 유효성분으로 함유하는 약학적 조성물
KR20200022759A (ko) * 2018-08-23 2020-03-04 고려대학교 산학협력단 신규한 벤조파이란 유도체 또는 이의 약학적으로 허용가능한 염 및 이를 유효성분으로 함유하는 약학적 조성물

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120079274A (ko) * 2011-01-04 2012-07-12 서울대학교산학협력단 신규한 데구엘린 유도체 또는 이의 약학적으로 허용가능한 염 및 이를 유효성분으로 함유하는 약학적 조성물
KR20200022759A (ko) * 2018-08-23 2020-03-04 고려대학교 산학협력단 신규한 벤조파이란 유도체 또는 이의 약학적으로 허용가능한 염 및 이를 유효성분으로 함유하는 약학적 조성물

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
JO DONG HYUN, LEE SEUNGBEOM, BAK EUNOO, CHO CHANG SIK, HAN YOUNG TAEK, KIM KYEOJIN, SUH YOUNG-GER, KIM JEONG HUN: "Antitumor Activity of Novel Signal Transducer and Activator of Transcription 3 Inhibitors on Retinoblastoma", MOLECULAR PHARMACOLOGY, AMERICAN SOCIETY FOR PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, US, vol. 100, no. 1, 1 July 2021 (2021-07-01), US , pages 63 - 72, XP093185549, ISSN: 0026-895X, DOI: 10.1124/molpharm.120.000231 *
KIM KYEOJIN; KIM SU-JUNG; HAN YOUNG TAEK; HONG SUNG-JUN; AN HONGCHAN; CHANG DONG-JO; KIM TAEWOO; LIM BUMHEE; LEE JEEYEON; SURH YOU: "Identification of small molecule inhibitors of the STAT3 signaling pathway: Insights into their structural features and mode of action", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM NL, vol. 25, no. 22, 26 July 2015 (2015-07-26), Amsterdam NL , pages 5444 - 5448, XP029321375, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2015.07.063 *
PARK SOO KYUNG; BYUN WOONG SUB; LEE SEUNGBEOM; HAN YOUNG TAEK; JEONG YOO-SEONG; JANG KYUNGKUK; CHUNG SUK-JAE; LEE JEEYEON; SUH YOU: "A novel small molecule STAT3 inhibitor SLSI-1216 suppresses proliferation and tumor growth of triple-negative breast cancer cells through apoptotic induction", BIOCHEMICAL PHARMACOLOGY, ELSEVIER, US, vol. 178, 23 May 2020 (2020-05-23), US , XP086219957, ISSN: 0006-2952, DOI: 10.1016/j.bcp.2020.114053 *

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