WO2023214706A1 - Nouveau composé dérivé de diaryl-propanedione, son procédé de préparation et composition pharmaceutique le comprenant pour la prévention ou le traitement de maladies inflammatoires ou allergiques - Google Patents

Nouveau composé dérivé de diaryl-propanedione, son procédé de préparation et composition pharmaceutique le comprenant pour la prévention ou le traitement de maladies inflammatoires ou allergiques Download PDF

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WO2023214706A1
WO2023214706A1 PCT/KR2023/004942 KR2023004942W WO2023214706A1 WO 2023214706 A1 WO2023214706 A1 WO 2023214706A1 KR 2023004942 W KR2023004942 W KR 2023004942W WO 2023214706 A1 WO2023214706 A1 WO 2023214706A1
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Prior art keywords
inflammatory
formula
compound
allergic diseases
pharmaceutically acceptable
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PCT/KR2023/004942
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English (en)
Korean (ko)
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강태봉
이광호
서승용
비상
Original Assignee
엘림랜드 주식회사
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Publication of WO2023214706A1 publication Critical patent/WO2023214706A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • 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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/54—Radicals substituted by oxygen atoms

Definitions

  • the present invention relates to a novel diarylpropanedinone derivative compound, a method for producing the same, and a pharmaceutical composition containing the same for preventing or treating inflammatory or allergic diseases.
  • Inflammation is generally caused by factors such as stress, physical injury, and excessive intake of high-calorie foods, and has been reported to be closely related to chronic diseases such as neurological diseases, metabolic diseases, and cancer. Many aspects of the reaction process and the induction process between inflammatory reactions and chronic diseases have not yet been clarified.
  • inflammation can be broadly divided into acute inflammation and chronic inflammation, and acute inflammation is the initial stage of inflammation that repairs damage caused by invasion that causes any organic changes to cells or tissues of the living body. It acts as a biological defense reaction process for regeneration, and can be said to be a normal body reaction induced against external invading bacteria.
  • chronic inflammation is a dangerous disease in which an excessive inflammatory response is induced, abnormal free radicals are generated, tissues are damaged or worsened, and this reaction process causes chronic diseases such as heart disease and cancer.
  • chronic inflammation is limited to preventing the initial inflammation stage, so research into new anti-inflammatory substances is urgently needed.
  • allergic diseases have increased significantly over the past few decades. It is known that various factors such as environment, genetics, hygiene, and food affect the development of allergic diseases such as atopy, asthma, and rhinitis.
  • Several effective treatment methods, such as corticosteroids and antihistamines, are being developed, but the causative mechanism or complete treatment method is still not well known.
  • Patent Document 1 Korean Patent No. 10-1808950
  • the purpose of the present invention is to provide a diarylpropanedinone derivative compound represented by Formula 1, or a pharmaceutically acceptable salt thereof.
  • the present invention provides a pharmaceutical composition for preventing or treating inflammatory or allergic diseases, comprising the compound according to the present invention or a pharmaceutically acceptable salt thereof as an active ingredient.
  • the present invention provides a health functional food composition for preventing or improving inflammatory or allergic diseases, comprising the compound according to the present invention or a pharmaceutically acceptable salt thereof as an active ingredient.
  • the present invention provides a cosmetic composition for preventing or improving inflammatory or allergic diseases, comprising the compound according to the present invention or a pharmaceutically acceptable salt thereof as an active ingredient.
  • the present invention provides a method for producing a diarylpropanedinone derivative compound represented by Formula 1.
  • R 1 to R 3 are the same or different from each other, and are each independently H, OH, OCH 3 , NRR' (where R and R' are each independently H, a C 1 to C 10 alkyl group) , and a C 1 to C 10 allyl group), a C 1 to C 60 alkyl group, and -OCH 2 O-.
  • R 1 to R 3 are the same as or different from each other, and may each independently be selected from H, OH, OCH 3 , and -OCH 2 O-.
  • the diarylpropanedinone derivative compound represented by Formula 1 is 1-(benzo[d][1,3]dioxol-5-yl)-3-(4-meth) represented by Formula 2 below: Toxyphenyl)-2-(3,4,5-trimethoxybenzylidene)propane-1,3-dione, or 2-(benzo[d][1,3]dioxole-5 represented by the following formula 3 -ylmethylene)-1-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)propane-1,3-dione.
  • the diarylpropanedinone derivative compound represented by Formula 1 is a NLRP3 (nucleotide-binding oligomerization domain (NOD)-like receptor family, pyrin domain containing 3) inflammasome, which is a mediator of inflammatory diseases, or a mediator of allergic diseases. It may have the activity of inhibiting the release of ⁇ -hexosaminidase secreted from RBL-2H3 cells. This may be useful for preventing or treating inflammatory or allergic diseases.
  • the diarylpropanedinone derivative compound has the advantage of excellent stability as it does not show cytotoxicity in weakened cells induced by inflammation or allergy.
  • the inflammatory disease may be any one selected from the group consisting of inflammatory bowel disease, systemic lupus erythematosus, inflammatory collagen vascular disease, glomerulonephritis, inflammatory skin disease, sarcoidosis, retinitis, gastritis, hepatitis, enteritis, pancreatitis, and nephritis. However, it is not limited to this.
  • the allergic disease may be any one selected from the group consisting of hypersensitivity, allergic rhinitis, asthma, allergic conjunctivitis, allergic dermatitis, atopic dermatitis, contact dermatitis, and urticaria, but is not limited thereto.
  • the compound represented by Formula 2 is used in an amount of 0.625 to 5 uM, preferably 1.25 to 5 uM, and most preferably to inhibit the release of ⁇ -hexosaminidase secreted from RBL-2H3 cells, which is a mediator of allergic diseases. It may be included at a concentration of 2.5 to 5 uM.
  • the appropriate dosage of the pharmaceutical composition varies depending on factors such as formulation method, administration method, patient's age, weight, sex, pathological condition, food, administration time, administration route, excretion rate, and reaction sensitivity, and is usually A skilled physician can easily determine and prescribe an effective dosage for desired treatment or prevention.
  • the daily dosage of the pharmaceutical composition is 0.001 to 10 g/kg.
  • the pharmaceutical composition is prepared by adding at least one selected from the group consisting of pharmaceutically acceptable carriers, excipients and diluents according to a method that can be easily performed by a person skilled in the art to which the invention pertains. It can be manufactured in unit dosage form by formulating it, or it can be manufactured by placing it in a multi-dose container. At this time, the dosage form may be any one selected from the group consisting of granules, powders, tablets, coatings, capsules, solutions, syrups, juices, suspensions, emulsions, drops, and injection solutions.
  • the present invention provides a health functional food composition for preventing or improving inflammatory or allergic diseases containing the compound according to the present invention, or a pharmaceutically acceptable salt thereof, as an active ingredient.
  • the health functional food composition may contain not only the diarylpropanedinone derivative compound of the present invention as an active ingredient, but also ingredients commonly added during food production, such as proteins, carbohydrates, fats, nutrients, and seasonings. It may include agents and flavoring agents.
  • examples of the above-mentioned carbohydrates include monosaccharides such as glucose, fructose, etc.; Disaccharides such as maltose, sucrose, oligosaccharides, etc.; and polysaccharides, such as common sugars such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol.
  • the present invention provides a cosmetic composition for preventing or improving inflammatory or allergic diseases, comprising the compound according to the present invention, or a pharmaceutically acceptable salt thereof, as an active ingredient.
  • Ingredients included in the cosmetic composition include ingredients commonly used in cosmetic compositions in addition to the diarylpropanedinone derivative compound as an active ingredient, for example, antioxidants, stabilizers, solubilizers, vitamins, and fragrances. It may further include phosphorus adjuvants and detergents.
  • the carrier ingredients include water, liquid diluents such as ethanol and propylene glycol, and suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester, and polyoxyethylene sorbitan ester. , microcrystalline cellulose, aluminum metahydroxide, bentonite, agar, etc. may be further included.
  • the present invention includes the steps of preparing compound 3 by mixing compound 1 and compound 2 in a first organic solvent, as shown in Scheme 1 below; Washing and drying the compound 3; Preparing a reaction mixture by mixing Compound 3 and Compound 4 in a second organic solvent; and refluxing the reaction mixture and purifying it to prepare a diarylpropanedinone derivative compound represented by Formula 1 according to the present invention.
  • a method for producing a diarylpropanedinone derivative compound represented by Formula 1, comprising: to provide.
  • the diarylpropanedinone derivative compound represented by Formula 1 is 1-(benzo[d][1,3]dioxol-5-yl)-3-(4-meth) represented by Formula 2 below: Toxyphenyl)-2-(3,4,5-trimethoxybenzylidene)propane-1,3-dione, or 2-(benzo[d][1,3]dioxole-5 represented by the following formula 3 -ylmethylene)-1-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)propane-1,3-dione.
  • the first organic solvent or the second organic solvent may be the same or different from each other, and may be tetrahydrofuran (THF), glacial acetic acid, piperidine, 1,4-dioxane, acetonitrile (MeCN), ethanol (EtOH), diethyl Ether, diphenyl ether, diisopropyl ether (DIPE), dimethylformamide (DMF), dimethylacetamide (DMA), dichloromethane (DCM), chlorobenzene, benzene, carbon tetrachloride (CCl 4 ), It may be one or more selected from the group consisting of acetone and chloroform (CHCl 3 ).
  • the first organic solvent or the second organic solvent are different from each other, the first organic solvent may be tetrahydrofuran (THF), and the second organic solvent may be a mixture of glacial acetic acid and piperidine. there is.
  • THF tetrahydrofuran
  • the second organic solvent may be a mixture of glacial acetic acid and piperidine.
  • SPD1 was prepared in the following manner.
  • the 1 H-NMR data of SPD 1 is as follows.
  • SPD2 was prepared in the following manner.
  • BMDM bone marrow-derived macrophages
  • LPS 100 ng/ml
  • Opti-MEM medium-derived macrophages
  • the cells were cultured for 1 hour in the presence or absence of the sample containing the compound SPD 1 or SPD 2 prepared in Examples 1 and 2, and stimulated with KCL (150 mM) and Nigericin (5 uM) for 40 minutes.
  • SPD 1 and SPD 2 prepared in Examples 1 and 2 were analyzed for cell viability, cytotoxicity, and inhibitory activity on NLRP3 inflammasome activation induced by LPS+Nigericin.
  • the concentrations of the compounds SPD 1 and SPD 2 were 0.625, 1.25, 2.5, 5, 10, and 20 uM.
  • RBL-2H3 cells were inoculated into a 24 well plate and cultured for 16 hours, and then the cells were sensitized with anti-DNP IgE for 2 hours. Thereafter, the cells were treated with the compounds SPD 1 or SPD 2 prepared in Examples 1 and 2 at levels of 0.625, 1.25, 2.5, and 5 uM, and then treated with DNP-HSA or A23187 to cross-link with IgE to degranulate the cells. After induction, ⁇ -hexosaminidase release was calculated 15 minutes later.
  • the compounds SPD 1 and SPD 2 showed a cell viability of more than 99% in the concentration range of 0.625 to 5 uM for RBL-2H3 cells, and no significant cytotoxicity was observed.
  • Table 1 shows the results of the inhibitory effect on IgE-DNP-induced ⁇ -hexosaminidase release by SPD1 and 2 treatment.

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Abstract

La présente invention concerne un nouveau composé dérivé de diaryl-propanedione, son procédé de préparation, et une composition pharmaceutique le comprenant pour la prévention ou le traitement de maladies inflammatoires ou allergiques. Plus particulièrement, le nouveau composé dérivé de diaryl-propanedinone selon la présente invention a l'activité de supprimer l'inflammasome NLRP3, qui est un médiateur dans des maladies inflammatoires, ou la libération de bêta-hexosaminidase, qui est un médiateur dans des maladies allergiques et sécrétée à partir de cellules RBL-2H3, et peut ainsi avoir une excellente suppression d'inflammation ou d'allergies. En outre, aucune cytotoxicité n'apparaît dans des cellules affaiblies induites par une inflammation ou une allergie, ce qui permet d'obtenir une excellente stabilité, le composé peut être ainsi utilisé en tant que composition pour le traitement, la prévention ou le soulagement de maladies inflammatoires ou allergiques.
PCT/KR2023/004942 2022-05-04 2023-04-12 Nouveau composé dérivé de diaryl-propanedione, son procédé de préparation et composition pharmaceutique le comprenant pour la prévention ou le traitement de maladies inflammatoires ou allergiques WO2023214706A1 (fr)

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KR10-2022-0055563 2022-05-04
KR1020220055563A KR102575347B1 (ko) 2022-05-04 2022-05-04 신규한 다이아릴프로판다이논 유도체 화합물, 이의 제조방법 및 이를 포함하는 염증 또는 알레르기 질환의 예방 또는 치료용 약학 조성물

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003076407A1 (fr) * 2002-03-14 2003-09-18 The Walter And Eliza Hall Institute Of Medical Research Nouveaux derives de chalcone et leurs utilisations
KR20110022589A (ko) * 2008-05-08 2011-03-07 노바 사우쓰이스턴 유니버시티 혈관 내피 성장 인자 수용체에 대한 특이적 억제제
US20110086868A1 (en) * 2006-09-21 2011-04-14 Nova Southeastern University Specific inhibitors for vascular endothelial growth factor receptors
KR20200071409A (ko) * 2018-12-11 2020-06-19 건국대학교 글로컬산학협력단 우엉 추출물을 유효성분으로 함유하는 nlrp3 인플라마좀의 과활성에 의한 만성 염증질환의 개선, 예방 또는 치료용 조성물

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
KR101808950B1 (ko) 2016-07-27 2017-12-13 충북대학교 산학협력단 디메톡시페닐 유도체, 이의 제조방법 및 이를 포함하는 항염증 및 피부 미백용 조성물

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003076407A1 (fr) * 2002-03-14 2003-09-18 The Walter And Eliza Hall Institute Of Medical Research Nouveaux derives de chalcone et leurs utilisations
US20110086868A1 (en) * 2006-09-21 2011-04-14 Nova Southeastern University Specific inhibitors for vascular endothelial growth factor receptors
KR20110022589A (ko) * 2008-05-08 2011-03-07 노바 사우쓰이스턴 유니버시티 혈관 내피 성장 인자 수용체에 대한 특이적 억제제
KR20200071409A (ko) * 2018-12-11 2020-06-19 건국대학교 글로컬산학협력단 우엉 추출물을 유효성분으로 함유하는 nlrp3 인플라마좀의 과활성에 의한 만성 염증질환의 개선, 예방 또는 치료용 조성물

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KERR, D.J. HAMEL, E. JUNG, M.K. FLYNN, B.L.: "The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 15, no. 9, 29 March 2007 (2007-03-29), AMSTERDAM, NL, pages 3290 - 3298, XP022006417, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2007.02.006 *

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