WO2012039101A1 - 口腔用組成物 - Google Patents

口腔用組成物 Download PDF

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Publication number
WO2012039101A1
WO2012039101A1 PCT/JP2011/005002 JP2011005002W WO2012039101A1 WO 2012039101 A1 WO2012039101 A1 WO 2012039101A1 JP 2011005002 W JP2011005002 W JP 2011005002W WO 2012039101 A1 WO2012039101 A1 WO 2012039101A1
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WO
WIPO (PCT)
Prior art keywords
beans
caries
extract
biofilm formation
composition
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/JP2011/005002
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English (en)
French (fr)
Japanese (ja)
Inventor
貴則 津金
洋二 佐伯
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.)
Lotte Co Ltd
Original Assignee
Lotte Co Ltd
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 Lotte Co Ltd filed Critical Lotte Co Ltd
Priority to EP11826552.9A priority Critical patent/EP2620160A4/en
Priority to US13/824,364 priority patent/US20130189202A1/en
Priority to PH1/2013/500527A priority patent/PH12013500527A1/en
Priority to CN2011800452431A priority patent/CN103140242A/zh
Priority to KR1020187014451A priority patent/KR102015237B1/ko
Priority to BR112013006654A priority patent/BR112013006654A2/pt
Priority to KR1020137009167A priority patent/KR20130106837A/ko
Publication of WO2012039101A1 publication Critical patent/WO2012039101A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A23G3/364—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins
    • A23G3/368—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins containing vitamins, antibiotics
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A23G3/48—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds containing plants or parts thereof, e.g. fruits, seeds, extracts
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/068—Chewing gum characterised by the composition containing organic or inorganic compounds containing plants or parts thereof, e.g. fruits, seeds, extracts
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/12—Chewing gum characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins
    • A23G4/126—Chewing gum characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins containing vitamins, antibiotics
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • A23V2200/312—Foods, ingredients or supplements having a functional effect on health having an effect on dental health

Definitions

  • the present invention relates to a biofilm formation-suppressing oral composition useful for caries prevention, and more particularly to an oral composition using a novel biofilm formation-suppressing method by utilizing quorum sensing of oral microorganisms.
  • microorganisms attached to the surface of the object do not exist alone, but form a biofilm with other microorganisms in a characteristic structure. While this biofilm works beneficially for humans as seen in the use of immobilized microorganisms, it has also become clear that it causes caries and food contamination, and has been actively studied in recent years.
  • Oral biofilm is composed of more than 700 kinds of bacteria, and there are more than 10 8 bacteria in 1 mg. Streptococci, which accounts for a large number (20% to 40%), forms a biofilm under the communication between bacteria via a dynamic bacterial active substance on the oral surface. Among them, Streptococcus mutans (S. mutans) produces sticky exopolysaccharides and plays a central role in pathogenic biofilm formation. Oral biofilms have been found to cause caries and periodontal disease, and these diseases have been regarded as microbial infections caused by bacteria including S. mutans.
  • Quorum sensing inhibition is a candidate for a new oral biofilm removal method.
  • QS quorum sensing
  • CSP autoinducer Competence stimulating peptide
  • Non-Patent Document 1 discloses that a bacterium called S. salivarius inhibits the biofilm formation of S. mutans and that CSP can be controlled by expression of a specific gene.
  • a bacterium called S. salivarius inhibits the biofilm formation of S. mutans and that CSP can be controlled by expression of a specific gene.
  • introducing microorganisms into the oral cavity has safety problems, and control of gene expression is often difficult. Therefore, development of a safer and simpler biofilm formation inhibition method is desired.
  • the polysaccharide outside the oral biofilm prevents the penetration of antibacterial agents, enzyme inhibitors, antibiotics, etc. It is difficult to produce a caries-suppressing effect. Also, the use of antibacterial agents, enzyme inhibitors, antibiotics, etc. is not preferred because of the high risk of resistant bacteria appearing. Therefore, the present invention provides a safer and more effective oral composition for caries suppression by controlling biofilm formation by caries-causing bacteria rather than controlling caries-causing bacteria. With the goal.
  • the oral composition of the present invention inhibits caries-causing bacteria from forming a biofilm.
  • These oral compositions can be added to foods and drinks, pharmaceuticals, toothpastes, etc. and used safely for the prevention and treatment of caries.
  • Non-Patent Document 1 quorum sensing (QS) of S. mutans is controlled by specific microorganisms or gene expression.
  • QS quorum sensing
  • the present invention is characterized by inhibiting caries biofilm formation related to quorum sensing by an oral composition containing a bean extract.
  • composition for oral cavity According to the composition for oral cavity according to the present invention, pathogenic bacteria cannot adhere to the oral cavity because CSP-dependent S. mutans biofilm formation is inhibited. Therefore, biofilms can be suppressed without using mechanical methods such as brushing and scaling.
  • exopolysaccharides of oral biofilms such as caries suppression methods using conventional antibacterial agents, enzyme inhibitors or antibiotics, prevent the penetration of antibacterial agents, enzyme inhibitors, antibiotics, etc. There is no problem that it is difficult to produce a caries-suppressing effect.
  • the kind of beans used in the present invention is not particularly limited, but it is preferable to use an extract extracted from at least one kind of beans selected from cowpea, red beans, purple flower beans, white flower beans, black beans, and golden beans.
  • the method for obtaining the bean extract as the active ingredient of the present invention is not particularly limited, but the bean seeds or fruits (beans) are pulverized by an appropriate pulverizing means, and the extract is prepared by a method such as solvent extraction.
  • the extraction solvent water or a lower alcohol such as methanol, ethanol, n-propanol and n-butanol, or one or more organic solvents such as ether, chloroform, ethyl acetate, acetone, glycerin and propylene glycol are mixed.
  • hot water or a hydrophilic organic solvent is used.
  • the extract of the present invention is often used as a food or drink, it is preferable to use a combination of water and ethanol as an extraction solvent from the viewpoint of safety. Extraction is preferably performed with 90% or less of ethanol, more preferably with 60% or less of ethanol, further preferably with 30% or less of ethanol, and most preferably with hot water.
  • extraction can be performed at any of high temperature, room temperature, and low temperature, but it is preferable to extract at 50 to 90 ° C. for about 1 to 5 hours.
  • the obtained extract may be filtered and the extraction solvent may be distilled off, followed by concentration or lyophilization under reduced pressure.
  • those obtained by fractionating and purifying these extracts using an organic solvent, column chromatography, or the like can also be used.
  • oral compositions such as a mouthwash, toothpaste, deodorant spray, etc., or chewing gum, candy, tablet candy, gummy jelly, chocolate, biscuits , Snacks and other confectionery, ice cream, sorbet, frozen confectionery such as ice confectionery, beverages, bread, hot cakes, dairy products, ham, sausage and other livestock products, sea bream, chikuwa and other fish products, side dishes, pudding, soup and It can be blended into foods and drinks such as jam and used on a daily basis.
  • oral compositions such as a mouthwash, toothpaste, deodorant spray, etc., or chewing gum, candy, tablet candy, gummy jelly, chocolate, biscuits , Snacks and other confectionery, ice cream, sorbet, frozen confectionery such as ice confectionery, beverages, bread, hot cakes, dairy products, ham, sausage and other livestock products, sea bream, chikuwa and other fish products, side dishes, pudding, soup and It can be blended into foods and drinks such as jam and used
  • the blending amount may vary depending on various production conditions, but the bean extract should be blended in the oral composition in an amount of 0.01% to 2.0% by weight, more preferably 0.01% to 1.0% by weight. Is preferred.
  • the present invention uses an extract that has been conventionally edible, there is no problem with its safety even when ingested in the oral cavity or body. In addition, it can be easily ingested by adding it to foods such as chewing gum and dentifrices, and does not require complicated procedures such as gene expression preparation. It becomes possible to do.
  • Example 1 Extract preparation Seven kinds of plant samples were selected: cowpea, red beans (Daidengo), red beans (Nagoya red beans), purple flower beans, white flower beans, black bean, and golden beans. Each plant sample was purchased as a commercial product, and 20 g was finely pulverized with a pulverizer and extracted with 200 ml of water at 70 ° C. for 2 hours. The obtained extract was centrifuged at 3000 rpm for 10 minutes, and the supernatant was filtered and lyophilized to be used as a test for each plant hot water extract.
  • BHI Brain Heart Infusion
  • CSP-derived group biofilm was formed.
  • concentration of CSP was 1 ⁇ M at the final concentration
  • concentration of the hot water extract of each sample was 1 mg / ml at the final concentration.
  • CSP was not added, and culture was performed under the same conditions as above except that a CSP non-induced group biofilm was formed.
  • the CSP induction group and the CSP non-induction group were cultured under the same conditions as above except that the sample hot water extract was not added.
  • FIG. 1 shows the amount of biofilm formed in a group (sample group) and a control group (control group) in which a plant extract was added and cultured for each of the CSP-induced group and the CSP non-induced group.
  • FIG. 2 shows the ratio of the biofilm formation amount of the sample group when the biofilm formation amount of the control group is 100, for each of the CSP induction group and the CSP non-induction group. From FIG. 1, the amount of biofilm formed in the control group was increased in the CSP induction group than in the CSP non-induction group. This increase was thought to be an increase in biofilm due to quorum sensing with CSP as an autoinducer.
  • chewing gum, candy, and toothpaste were prepared in a conventional manner using the red bean extract prepared in Example 1.
  • the prescription is shown below. Note that these do not limit the scope of the product of the present invention.
  • Chewing gum was prepared according to the following formulation. Gum base 20.0% by weight Sugar 55.0 Glucose 15.0 Minamata 9.0 Fragrance 0.5 Erimo red bean hot water extract (Example 1) 0.5 100.0
  • Example 3 Candy was prepared according to the following formulation. 50.0% by weight sugar Minamata 34.0 Fragrance 0.5 Dainago Azuki hot water extract (Example 1) 0.5 Water remaining 100.0
  • Example 4 A toothpaste was prepared according to the following formulation. Calcium carbonate 50.0% by weight Glycerin 20.0 Carboxymethylcellulose 2.0 Sodium lauryl sulfate 2.0 Fragrance 1.0 Saccharin 0.1 Erimo red bean hot water extract (Example 1) 1.0 Chlorhexidine 0.01 Water remaining 100.0

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Botany (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Microbiology (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Inorganic Chemistry (AREA)
  • Nutrition Science (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Mycology (AREA)
  • Biotechnology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Birds (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medical Informatics (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Cosmetics (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Confectionery (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
PCT/JP2011/005002 2010-09-21 2011-09-07 口腔用組成物 Ceased WO2012039101A1 (ja)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP11826552.9A EP2620160A4 (en) 2010-09-21 2011-09-07 COMPOSITIONS FOR ORAL ADMINISTRATION
US13/824,364 US20130189202A1 (en) 2010-09-21 2011-09-07 Oral composition
PH1/2013/500527A PH12013500527A1 (en) 2010-09-21 2011-09-07 Oral composition
CN2011800452431A CN103140242A (zh) 2010-09-21 2011-09-07 口腔用组合物
KR1020187014451A KR102015237B1 (ko) 2010-09-21 2011-09-07 구강용 조성물
BR112013006654A BR112013006654A2 (pt) 2010-09-21 2011-09-07 composição oral
KR1020137009167A KR20130106837A (ko) 2010-09-21 2011-09-07 구강용 조성물

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010211023A JP5906011B2 (ja) 2010-09-21 2010-09-21 口腔用組成物
JP2010-211023 2010-09-21

Publications (1)

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WO2012039101A1 true WO2012039101A1 (ja) 2012-03-29

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PCT/JP2011/005002 Ceased WO2012039101A1 (ja) 2010-09-21 2011-09-07 口腔用組成物

Country Status (9)

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US (1) US20130189202A1 (enExample)
EP (1) EP2620160A4 (enExample)
JP (1) JP5906011B2 (enExample)
KR (2) KR20130106837A (enExample)
CN (1) CN103140242A (enExample)
BR (1) BR112013006654A2 (enExample)
PH (1) PH12013500527A1 (enExample)
TW (1) TW201225962A (enExample)
WO (1) WO2012039101A1 (enExample)

Cited By (3)

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JP2013245164A (ja) * 2012-05-23 2013-12-09 Kao Corp オートインデューサー−２阻害剤
CN103535500A (zh) * 2013-10-22 2014-01-29 深圳职业技术学院 一种保健口香糖及其制备方法
CN104622873A (zh) * 2015-01-21 2015-05-20 四川大学 一种喹喔啉亚胺类化合物作为变异链球菌生物膜抑制剂的制备方法及应用

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Publication number Priority date Publication date Assignee Title
JP6016343B2 (ja) * 2011-09-08 2016-10-26 株式会社ロッテ 口腔用組成物
JP2015166334A (ja) * 2014-02-13 2015-09-24 株式会社ロッテ 口腔用組成物
KR101870239B1 (ko) * 2014-09-24 2018-06-22 서울대학교산학협력단 D-갈락토오스를 포함하는 쿼럼센싱 저해제
KR101656875B1 (ko) * 2015-11-13 2016-09-12 건국대학교 산학협력단 단풍나무 추출물, 당단풍나무 추출물 및 박태기나무 추출물을 이용한 그람음성세균 억제용 정족수 감지 억제제
JP6293177B2 (ja) * 2016-02-08 2018-03-14 株式会社ロッテ 口腔用組成物
GB201607518D0 (en) * 2016-04-29 2016-06-15 Andalay Technologies Ltd Mouthwash composition
CN112971137A (zh) * 2019-12-13 2021-06-18 黔东南苗族侗族自治州农业科学院 一种黑芸豆提取物的提取方法

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JP2009269912A (ja) * 2008-04-07 2009-11-19 Kao Corp Ａｉ−２阻害剤
WO2010050369A1 (ja) * 2008-10-31 2010-05-06 国立大学法人岡山大学 虫歯予防剤
JP2010211023A (ja) 2009-03-11 2010-09-24 Mitsubishi Paper Mills Ltd 洗浄液

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Title
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HONRAET, K. ET AL.: "Use of the modified robbins device and fluorescent staining to screen plant extracts for the inhibition of S. mutans biofilm formation", JOURNAL OF MICROBIOLOGICAL METHODS, vol. 64, no. 2, February 2006 (2006-02-01), pages 217 - 224, XP027926832 *
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013245164A (ja) * 2012-05-23 2013-12-09 Kao Corp オートインデューサー−２阻害剤
CN103535500A (zh) * 2013-10-22 2014-01-29 深圳职业技术学院 一种保健口香糖及其制备方法
CN104622873A (zh) * 2015-01-21 2015-05-20 四川大学 一种喹喔啉亚胺类化合物作为变异链球菌生物膜抑制剂的制备方法及应用

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PH12013500527A1 (en) 2017-08-09
KR20130106837A (ko) 2013-09-30
JP5906011B2 (ja) 2016-04-20
TW201225962A (en) 2012-07-01
EP2620160A4 (en) 2014-05-07
KR102015237B1 (ko) 2019-08-27
JP2012067018A (ja) 2012-04-05
BR112013006654A2 (pt) 2016-06-07
US20130189202A1 (en) 2013-07-25
EP2620160A1 (en) 2013-07-31
CN103140242A (zh) 2013-06-05

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