WO2021261870A1 - Composition comprenant de la 6'-hydroxy justicidine-b pour prévenir, améliorer ou traiter des maladies allergiques - Google Patents
Composition comprenant de la 6'-hydroxy justicidine-b pour prévenir, améliorer ou traiter des maladies allergiques Download PDFInfo
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- WO2021261870A1 WO2021261870A1 PCT/KR2021/007775 KR2021007775W WO2021261870A1 WO 2021261870 A1 WO2021261870 A1 WO 2021261870A1 KR 2021007775 W KR2021007775 W KR 2021007775W WO 2021261870 A1 WO2021261870 A1 WO 2021261870A1
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- Prior art keywords
- hydroxy
- justicidin
- allergic
- composition
- preventing
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
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- A61K31/365—Lactones
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/304—Foods, ingredients or supplements having a functional effect on health having a modulation effect on allergy and risk of allergy
Definitions
- the present invention relates to a composition comprising 6'-hydroxy justicidin-B as an active ingredient.
- the present invention relates to a pharmaceutical composition for preventing or treating allergic diseases comprising 6'-hydroxy justicidin-B as an active ingredient.
- the present invention relates to a food composition for preventing or improving allergic diseases containing 6'-hydroxy justicidin-B.
- the present invention relates to a cosmetic composition for preventing or improving allergic diseases comprising 6'-hydroxy justicidin-B as an active ingredient.
- 6'-hydroxyjusticidin-B is also one of the lignan-based compounds present in Rathornwort. Although there is a difference in efficacy and superiority with other lignan-based drugs depending on the type of cancer cell line, the cytotoxic effect in various cancer cells, etc. is known (Cytotoxic activity of lignans from Justicia procumbens, Hong Jin et al, Fitorick, 2014;94:70-6).
- Allergy is defined as a phenomenon in which a living body in contact with a foreign substance called an allergen exhibits a different reaction from the normal to the substance. Allergies can be caused not only by various allergens such as pollen, drugs, vegetable fibers, bacteria, food, hair dye, and chemicals, but also by humidity, temperature, and exercise. , allergic otitis media, allergic enteritis, anaphylaxis and urticaria.
- Th2 lymphocytes which are activated by Th2 lymphocytes and contain several bioactive substances (cytokines) such as interleukin-4 (IL-4) or interleukin-5 (IL-5). and these physiologically active substances stimulate B lymphocytes to promote IgE antibody secretion (Lack of IL-4-induced Th2 response and IgE class switching in mice with disrupted Stat6 gene, Shimoda K et al, Nature 1996;380 ( 6575):630-3).
- the secreted IgE antibody binds to FceR1 on the surface of cells such as mast cells and basophils and activates these cells.
- Activated cells promote secretion of various physiologically active substances as well as histamine, leukotriene, and prostaglandin D2 through degranulation, resulting in various allergic reactions such as vasodilation, smooth muscle contraction, and mucous secretion.
- One object of the present invention is to provide a pharmaceutical composition for preventing or treating allergic diseases comprising 6'-hydroxy justicidin-B as an active ingredient.
- One object of the present invention is to provide a food composition for preventing or improving allergic diseases, comprising 6'-hydroxy justicidin-B as an active ingredient.
- One object of the present invention is to provide a cosmetic composition for preventing or improving allergic diseases, comprising 6'-hydroxy justicidin-B as an active ingredient.
- One object of the present invention is to provide a method for preventing, improving or treating an allergic disease, comprising administering to a subject in need thereof 6'-hydroxy justicidin-B or a composition comprising the same as an active ingredient will be.
- One object of the present invention is to provide a use of 6'-hydroxy justicidin-B or a composition comprising the same for the prevention, improvement, or treatment of allergic diseases.
- One object of the present invention is to provide a use of 6'-hydroxy justicidin-B or a composition comprising the same for the preparation of a medicament for the prevention, improvement, or treatment of allergic diseases.
- the present invention provides a pharmaceutical composition for preventing or treating allergic diseases, comprising 6'-hydroxy justicidin-B as an active ingredient.
- the allergic disease may be any one or more selected from the group consisting of allergic rhinitis, allergic asthma, allergic conjunctivitis, atopic dermatitis, allergic enteritis, allergic otitis media, anaphylaxis, and urticaria.
- the pharmaceutical composition may contain 0.1 mg/g to 200 mg/g of 6'-hydroxy justicidin-B.
- the pharmaceutical composition may include only 6'-hydroxy justicidin-B as an active ingredient.
- 6'-hydroxy justicidin-B shows excellent bioavailability in the human body when administered orally. Accordingly, the pharmaceutical composition of an embodiment comprising 6'-hydroxy justicidin-B may exhibit excellent bioavailability.
- the present invention provides a food composition for preventing or improving allergic diseases, comprising 6'-hydroxy justicidin-B as an active ingredient.
- the food composition may be a health functional food.
- the food composition may be a beverage.
- the present invention provides a cosmetic composition for preventing or improving allergic diseases, comprising 6'-hydroxy justicidin-B as an active ingredient.
- the present invention provides a method for preventing, ameliorating or treating an allergic disease, comprising administering to a subject in need thereof 6'-hydroxy justicidin-B or a composition comprising the same as an active ingredient.
- the composition may be a pharmaceutical composition, a food composition and/or a cosmetic composition of the present invention.
- the present invention provides a method for preventing or treating an allergic disease, comprising administering 6'-hydroxy justicidin-B or a pharmaceutical composition comprising the same as an active ingredient to a subject in need thereof.
- the present invention provides a method for preventing or improving an allergic disease, comprising administering to a subject in need thereof 6'-hydroxy justicidin-B or a food composition comprising the same as an active ingredient.
- the present invention provides a method for preventing or improving an allergic disease, comprising applying 6'-hydroxy justicidin-B or a cosmetic composition comprising the same as an active ingredient to a subject in need thereof.
- the present invention provides the use of 6'-hydroxy justicidin-B or a composition comprising the same for the prevention, improvement, or treatment of allergic diseases.
- the composition may be a pharmaceutical composition, a food composition and/or a cosmetic composition of the present invention.
- the present invention provides the use of 6'-hydroxy justicidin-B or a pharmaceutical composition comprising the same for the prevention or treatment of allergic diseases.
- the present invention provides the use of 6'-hydroxy justicidin-B or a food composition or cosmetic composition comprising the same for the prevention or improvement of allergic diseases.
- the present invention provides the use of 6'-hydroxy justicidin-B or a composition comprising the same for the preparation of a medicament for the prevention, improvement, or treatment of allergic diseases.
- the composition may be a pharmaceutical composition, a food composition and/or a cosmetic composition of the present invention.
- the present invention provides the use of 6'-hydroxy justicidin-B or a pharmaceutical composition comprising the same for the preparation of a medicament for the prevention, improvement or treatment of allergic diseases.
- the present invention provides a use of 6'-hydroxy justicidin-B or a food composition or cosmetic composition comprising the same for the preparation of a medicament for the prevention or improvement of allergic diseases.
- 6'-hydroxy justicidin-B may be synthesized through organic synthesis.
- 6'-hydroxy justicidin-B of the present invention can inhibit the secretion of Th2 inflammatory cytokines, and exhibits an allergic asthma inhibitory effect and an anaphylactic inhibitory effect, and thus effectively prevents, treats or improves allergic diseases can do.
- the allergic disease may include, without limitation, various diseases caused by various triggers.
- the allergic disease may be one or more selected from the group consisting of allergic rhinitis, allergic asthma, allergic conjunctivitis, atopic dermatitis, allergic enteritis, allergic otitis media, anaphylaxis, and urticaria.
- the allergic disease may be an allergic respiratory disease.
- the term "subject" refers to an animal, typically a mammal capable of exhibiting a beneficial effect by treatment with the composition of the present invention.
- mammal mammals, including humans, and the term “administering” means providing a given substance to a subject by any suitable method. It is apparent to those skilled in the art that the therapeutically effective dosage and frequency of administration for the active ingredient of the present invention will vary depending on the desired effect.
- mamal including humans refers to mammals such as monkeys, cattle, horses, dogs, cats, rabbits, rats, and mice, and in particular includes humans. Also, such subjects include all subjects having or at risk of having symptoms of allergic disease.
- prevention means delaying the onset of a disease, disorder or condition. Prevention may be considered complete if the onset of the disease, disorder or condition is delayed for a predetermined period.
- the term “amelioration” means partially or completely alleviating, alleviating, inhibiting or delaying the onset of a disease, disorder or condition, reducing the severity, or reducing the occurrence of one or more symptoms or features. .
- treatment refers to partially or completely alleviating, ameliorating, alleviating, inhibiting or delaying the onset of a particular disease, disorder and/or condition, reducing the severity, or preventing the occurrence of one or more symptoms or features. means to reduce
- the pharmaceutical composition of the present invention is in the form of tablets, pills, powders, granules, capsules, suspensions, internal solutions, emulsions, syrups, aerosols, injection solutions, etc. according to conventional methods for preventing and treating allergic diseases. It can be formulated and used.
- carriers, excipients and diluents that may be included in the pharmaceutical composition of the present invention include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, gum acacia, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.
- it is prepared using commonly used diluents or excipients such as fillers, extenders, binders, wetting agents, disintegrants, and surfactants.
- composition of the present invention may be administered orally or parenterally (eg, application or intravenous, subcutaneous, intraperitoneal injection).
- oral administration is a method of injecting a drug by mouth for alleviating pathological symptoms
- parenteral administration refers to subcutaneous, intramuscular, It refers to a method of intraperitoneal administration using an intravenous or tube.
- Solid preparations for oral administration include tablets, pills, powders, granules, capsules, etc., and these solid preparations include at least one excipient in the complex composition, for example, starch, calcium carbonate, sucrose, lactose, gelatin, etc. It can be prepared by mixing. In addition to simple excipients, lubricants such as magnesium stearate and talc may also be used.
- Liquid formulations for oral administration include suspensions, internal solutions, emulsions, syrups, etc., and various excipients, for example, wetting agents, sweeteners, fragrances, preservatives, etc. in addition to commonly used simple diluents such as water and liquid paraffin. can be used
- Formulations for parenteral administration may include sterile aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, suppositories, and the like.
- non-aqueous solvent and suspending agent vegetable oils such as propylene glycol, polyethylene glycol, and olive oil, and injectable esters such as ethyl oleate may be used.
- the pharmaceutical composition of the present invention may further include a carrier, excipient or diluent.
- Carriers, excipients or diluents include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, gum acacia, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, hydroxy Minerals such as propyl methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methyl hydroxy benzoate, ethyl hydroxy benzoate, propyl hydroxy benzoate, talc, magnesium stearate, silicon dioxide, etc. may be used. .
- the pharmaceutically acceptable additive according to the present invention may be included in an amount of 0.1 to 99.9 parts by weight based on the composition, specifically, 0.1 to 50 parts by weight, but the embodiment is not limited thereto.
- the dosage of the pharmaceutical composition according to the present invention should be a pharmaceutically effective amount.
- “Pharmaceutically effective amount” means an amount sufficient to prevent or treat a disease with a reasonable benefit/risk ratio applicable to medical treatment, and the effective dose level includes the formulation method, the patient's condition and weight, the patient's sex, and age. , can be variously selected by those skilled in the art according to factors such as the degree of disease, drug form, administration route and duration, excretion rate, reaction sensitivity, and the like. An effective amount will vary depending on the route of treatment, the use of excipients, and the potential for use with other agents, as will be appreciated by those skilled in the art.
- An amount effective to prevent or treat an allergic disease is administered in single or multiple doses, alone or in combination with one or more other compositions (such as other therapeutic agents for allergic diseases), which provides the desired performance or objective or subjective benefit in the subject. It can mean quantity.
- the dosage or dosage of the pharmaceutical composition according to the present invention varies depending on the patient's weight, age, sex, health status, diet, administration time, administration method, excretion rate, and severity of disease, but is 0.001 on an adult basis mg/kg to 1000 mg/kg may be administered in one to several divided doses.
- a cosmetic composition for preventing or improving allergic diseases comprising 6'-hydroxy justicidin-B as an active ingredient.
- the cosmetic composition is a softening lotion, astringent lotion, nutrient lotion, nutrition cream, massage cream, essence, eye cream, eye essence, cleansing cream, cleansing foam, cleansing water, pack, powder, body lotion, body cream, It may be a formulation selected from the group consisting of body oil, body essence, makeup base, foundation, hair dye, shampoo, conditioner and body cleanser.
- the cosmetic composition of the present invention can be prepared in various forms according to a conventional cosmetic preparation method using the 6'-hydroxy justicidin-B, and a stabilizer, solubilizer, It may contain conventional adjuvants such as vitamins, pigments, and flavorings.
- the cosmetic composition is prepared in the form of cosmetic products containing the 6'-hydroxy justicidin-B, shampoo, hair lotion, hair cream, hair gel, etc. It can be used after dilution.
- the cosmetic composition of the present invention is particularly preferably prepared in the form of a lotion, lotion, cream, or essence.
- 6'-hydroxy justicidin-B may be added to the cosmetic in an amount of 0.1% to 10% by weight based on the total liquid weight, and 0.001 to about the total dry weight of the cosmetic composition. It may be added to the cosmetic in an amount of 5% by weight, preferably 0.01 to 3% by weight.
- the 6'-hydroxy justicidin-B of the present invention excellently inhibited the differentiation of Th2 cells related to allergic diseases, and was effective in inhibiting asthma diseases even when administered at low concentrations in the Balb/c mouse model of allergic asthma. shows an excellent effect. Accordingly, the pharmaceutical composition, food composition, and cosmetic composition comprising 6'-hydroxy justicidin-B according to the present invention can be widely used as an agent for preventing, treating or improving allergic diseases.
- 1 is a diagram showing the chemical structure of 6'-hydroxy justicidin-B according to the present invention.
- 6'-hydroxy justicidin-B was synthesized through the following process.
- the structure of 6'-hydroxy justicidin-B is as shown in FIG. 1 .
- Step 1 6,7-dimethoxy-3-oxo-1,3-dihydronaphtho [2,3-c] furan-4-yl trifluoromethanesulfonate (3.0 g, 7.65 mmol) was mixed with dioxane (90ml) After dissolving in a solvent, 5-methoxymethoxy-6-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1 ,3]dioxole (2.83g, 9.18mmol), [1,1'-bis(diphenyl phosphino)ferrocene]dichloropalladium(II) (1.12g, 1.53mmol) and lithium hydroxide monohydrate (642mg, 15.3mmol) ) were sequentially added under a nitrogen atmosphere.
- Step 2 6,7-dimethoxy-9-(6-methoxymethoxy-benzo[1,3]dioxol-5-yl)-3H-naphtho[2,3-c]furan-1-one (8g, 18.9mmol) was dissolved in ethanol (80ml), and 44ml of 12M HCl was added dropwise, followed by reaction at 50°C for 12 hours. After the reaction was completed, 100 ml of water was added, and the mixture was extracted with dichloromethane (200 ml, 100 ml, 50 ml). The obtained organic layer was washed with water (150ml) and brine (100ml), dried over anhydrous Na 2 SO 4 , filtered and concentrated.
- Example 1 Comparative experiment on the effect of inhibiting differentiation from CD4 T cells to Th2 cells
- interleukin-2 20 ng/mL of interleukin-2 (IL-2) was additionally treated, and to induce Th0 cells into Th2 cells, 20 ng/mL of interleukin-2 (IL-2), 100 ng/mL of interleukin-4 (IL-4), 10 ⁇ g/mL of interferon-gamma antibody (anti-IFN ⁇ antibody), 10 ⁇ g/mL of interleukin-12 antibody (anti-IL12 antibody) was added, and at this time, 6'-hydroxy justicidin-B prepared in Preparation Example 1 was treated. The medium of the 24-well plate was used to measure the secretion level of interleukin-5 (IL-5), a Th2 inflammatory cytokine.
- IL-5 interleukin-5
- Th2 inflammatory cytokine 6'-hydroxy justicidin-B prepared in Preparation Example 1
- the excellent inhibitory effect on interleukin-5 secretion of 6'-hydroxy justicidin-B is confirmed.
- 6'-hydroxy justicidin-B achieves an excellent IL-5 secretion inhibitory effect even at a low concentration. From this, the excellent inhibitory effect of 6'-hydroxy justicidin-B into Th2 cells and the excellent prevention, improvement, or therapeutic effect of 6'-hydroxy justicidin-B on allergic diseases were confirmed. .
- Blood and lung lavage were obtained by autopsy 5 hours after the final sensitization (day 30), and lung tissue was fixed in 10% neutral formalin. After that, blood and lung lavage were used for IgE and Th2 cytokines and immune cytometry, and the lung tissue was cut to make a slide, and the tissue was observed by performing H&E staining. Observation of lung tissue was photographed at 400 times the microscope, and the thickness of the lung epithelium of the photographed tissue was measured using the Image-pro Plus 6.0 program. The results are shown in Tables 2 and 3, and the inhibitory ability was calculated using [Equation 1] described above in Example 1.
- 6-week-old ICR mice were grouped based on body weight, and anaphylaxis was induced by intraperitoneal administration of Compound 48/80 (Sigma #C2313) at a concentration of 16 mg/kg.
- Compound 48/80 Sigma #C2313
- the 6'-hydroxy justicidin-B and the positive control group DSCG (Cromolyn sodium, Sigma #C0399) 250 mg/kg were administered intraperitoneally 1 hour before anaphylaxis induction, respectively, and mortality (mortality) for 30 minutes after anaphylaxis induction. ) was observed, and the results are shown in Table 4.
- Anaphylaxis inhibitory ability was calculated using the following [Equation 2].
- the above ingredients are mixed and filled in an airtight bag to prepare a powder.
- tablets are prepared by tableting according to a conventional manufacturing method of tablets.
- the above ingredients are mixed and filled in a gelatin capsule to prepare a capsule.
- the content of the above ingredients per 1 ampoule (2 ml) is prepared.
- the above ingredients are mixed and filled in a container.
- Vitamin B6 0.5 mg
- composition ratio of the above vitamin and mineral mixture is mixed composition with ingredients suitable for health functional food as a preferred embodiment, but the mixing ratio may be arbitrarily modified, and the above ingredients are mixed according to a conventional health functional food manufacturing method.
- a health functional food composition eg, nutritional candy, etc.
- the resulting solution is filtered and acquired in a sterilized 2L container, sealed and sterilized, then refrigerated. It is used to prepare the health functional beverage composition of the present invention.
- the composition ratio is prepared by mixing ingredients suitable for relatively favorite beverages in a preferred embodiment, the blending ratio may be arbitrarily modified according to regional and national preferences such as demand class, demanding country, and use purpose.
- the above ingredients were mixed to prepare a cosmetic.
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Abstract
La présente invention concerne une composition pharmaceutique destinée à prévenir ou traiter des maladies allergiques, ou une composition alimentaire destinée à améliorer des maladies allergiques, comprenant de la 6'-hydroxy justicidine-B en tant que principe actif. La 6'-hydroxy justicidine-B de la présente invention présente un excellent effet inhibiteur de la cytokine Th2 et démontre un excellent effet antiallergique et antiasthmatique. En outre, il est confirmé que la 6'-hydroxy justicidine-B a un excellent effet inhibiteur de l'anaphylaxie. Par conséquent, il est possible de prévenir, traiter ou améliorer efficacement des maladies allergiques en utilisant la 6'-hydroxy justicidine-B comme principe actif.
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KR20170118613A (ko) * | 2016-04-15 | 2017-10-25 | 동화약품주식회사 | 쥐꼬리망초 추출물을 포함하는 호흡기 질환의 예방 또는 치료용 약학적 조성물 |
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CN102293798A (zh) * | 2010-06-25 | 2011-12-28 | 中国医学科学院药用植物研究所 | 爵床药材的质量控制方法 |
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KR20170118613A (ko) * | 2016-04-15 | 2017-10-25 | 동화약품주식회사 | 쥐꼬리망초 추출물을 포함하는 호흡기 질환의 예방 또는 치료용 약학적 조성물 |
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