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WO2007037492A1 - Agent thérapeutique pour une parodontopathie contenant un ingrédient extrait d’une plante appartenant à la famille des salicacées, genre salix - Google Patents

Agent thérapeutique pour une parodontopathie contenant un ingrédient extrait d’une plante appartenant à la famille des salicacées, genre salix Download PDF

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Publication number
WO2007037492A1
WO2007037492A1 PCT/JP2006/319736 JP2006319736W WO2007037492A1 WO 2007037492 A1 WO2007037492 A1 WO 2007037492A1 JP 2006319736 W JP2006319736 W JP 2006319736W WO 2007037492 A1 WO2007037492 A1 WO 2007037492A1
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WIPO (PCT)
Prior art keywords
salix
periodontal disease
agent
solvent
willow
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Application number
PCT/JP2006/319736
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English (en)
Japanese (ja)
Inventor
Hideaki Kitagori
Keisuke Kajita
Young-Soo Kim
Original Assignee
Kobayashi Pharmaceutical 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 Kobayashi Pharmaceutical Co., Ltd. filed Critical Kobayashi Pharmaceutical Co., Ltd.
Publication of WO2007037492A1 publication Critical patent/WO2007037492A1/fr

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Classifications

    • 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)
    • A61K36/76—Salicaceae (Willow family), e.g. poplar
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • 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
    • 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

Definitions

  • the present invention relates to a novel agent for periodontal disease that inhibits abnormal extension of gingival epithelial tissue involved in the cause of oral diseases such as gingivitis and periodontitis (periodontal disease).
  • Periodontal tissue that surrounds the tooth neck and root of a mammalian tooth is composed of gingiva (gum), periodontal ligament, cementum, and alveolar bone, and plays a role in supporting the tooth. Inflammatory symptoms appear in this periodontal tissue, and the inflamed area stops at the gingiva, which is called “gingivitis”, and the inflamed area extends beyond the gingiva to the periodontal ligament and alveolar bone. The state that has reached is distinguished from "periodontitis”. In both gingivitis and periodontitis, inflammation in the periodontal tissue is affected by plaques formed by the growth of bacteria attached to food residues in the oral cavity and other environmental factors.
  • gingivitis Due to As for gingivitis, the site of inflammation is limited to the gingiva, and inflammation has not spread to the periodontal ligament or alveolar bone. Can be relieved or cured.
  • the connective tissue adhesion between the gingiva and the tooth is lost, so not only the tooth swings but also the periodontal ligament and alveolar bone. Injury's destruction and simply physically cleaning the oral cavity will make it difficult to expect periodontitis to recover.
  • the gingival epithelial cells expand toward the root of the tooth (down-gloss), resulting in a periodontitis that is characteristic between the gum and the tooth. Gingival sulcus, the so-called periodontal pocket, is formed.
  • ⁇ -aminocaproic acid having an excellent anti-inflammatory effect is used.
  • Techniques that suppress the onset of gingivitis and periodontitis symptoms by antiplasmin action are used.
  • a drug to remove Tetracycline-resistant Sraphylococci which is the causative agent of periodontal and inflammatory inflammation, that is, tetracycline
  • minocycline hydrochloride is also a technique using minocycline hydrochloride.
  • macrolide antibiotics specifically, lactone ring is used.
  • 14-membered to 16-membered substances such as erythromycins, 16-membered macrolide josamycins, clarithromycins and the like.
  • 14-membered macrolide antibiotics are useful because they can effectively prevent and eliminate biofilm formation.
  • Patent Document 1 JP-A-9-268117
  • the present invention inhibits the abnormal extension of gingival epithelial tissue in mammals and prevents the formation of periodontal pockets, thereby effectively inhibiting the progression of oral diseases such as periodontitis.
  • the purpose is to provide a new agent for periodontal disease that maintains healthy gingival tissue.
  • the gist of the present invention is a plant belonging to the genus Salix belonging to the genus Salix that has been confirmed to be safe for humans in addition to being a well-known medicinal plant since ancient times, ie, willow.
  • a plant belonging to the genus Willow genus (hereinafter simply referred to as “willow plant”) is selected as a raw material plant, contains a separated component obtained by extracting it with a solvent, and does not cause gingival epithelial tissue in mammals. It is in a periodontal disease agent that inhibits normal extension.
  • the composition for oral cavity containing the periodontal disease agent of this invention is also provided.
  • a separated component obtained by extracting a willow plant with a solvent is an abnormal extension of gingival epithelial tissue, particularly gingival epithelial tissue in mammals.
  • gingival epithelial tissue particularly gingival epithelial tissue in mammals.
  • a novel agent for periodontal disease that can inhibit the abnormal extension of the gingival epithelial thread and tissue and can effectively suppress the formation of periodontal pockets is realized.
  • an agent for periodontal disease comprising a separated component obtained by extracting a willow plant with a solvent and inhibiting abnormal extension of gingival epithelial tissue in a mammal.
  • peripheral agents are effective not only in an in vitro test system but also in an in vivo test system for inhibiting the abnormal extension of gingival epithelial tissue and the formation of periodontal pockets. Substances or compositions that have both been confirmed to have a deterrent effect are collectively referred to as “periodontal agents”.
  • the term "gingival epithelial cell” as used herein refers to an epithelial cell (oral cavity) of the oral cavity mucosa that surrounds the tooth neck and root and serves as a supporting structure for adjacent tissues. This epithelial cell adheres to the surface of the tooth enamel layer and forms a periodontal pocket as the periodontitis progresses.
  • the oral mucosal epithelial cells are always placed in an environment that is exposed to the risk of infection by bacteria, and therefore, the oral mucosal epithelial cells in other parts of the oral cavity are excellent, such as cell division. It has a distinction from the nature it has.
  • Yezo willow (Salix daphnoides), Murasaki willow (Salix purpurea), Pokkiriyanagi (Salix fragilis), Inukoriyanagi (Salix integra), Unryu willow (Salix matsudana), Ezonokinananagi (Salix pet-susu), Ezonotakaneanagi (Salix yezoalpina),
  • nakamurana or any combination thereof can be used in the present invention, but is not limited thereto.
  • any combination thereof can be used in the present invention, but is not limited thereto.
  • the selected willow plant is applied to an extraction step using a solvent.
  • the whole willow plant or any part of it eg crusts or shoots
  • the force can be applied to the extraction process by drying and grinding into a powder.
  • a solvent well known in the art can be used.
  • a lower alcohol, a polyhydric alcohol, a nonpolar solvent, a polar solvent, and the like can be used.
  • Examples of the lower alcohol include alcohols having 1 to 4 carbon atoms such as methanol, ethanol, propanol, isopropyl alcohol, and butanol; examples of the polyhydric alcohol include glycerin and polyethylene glycol; and examples of the nonpolar solvent include pentane. Saturated hydrocarbons such as hexane, heptane, octane, nonane and decane; polar solvents include water, warm water (hot water), acetone, ethyl acetate, and methyl acetate.
  • the solvent it is possible to select and use any one of the above-mentioned solvents, and it is also possible to use two or more kinds of solvents in combination.
  • the degreasing extraction treatment with a non-polar solvent may be followed by the extraction treatment with an arbitrary solvent or the extraction treatment with a water-containing organic solvent. .
  • a method for extracting a willow plant a method well known in the art can be used. For example, a method of immersing a willow plant itself, or a coarsely pulverized or cut product thereof, or a dried crushed product (powder) thereof in a solvent by cold immersion, digestion, etc., or heating and stirring.
  • a method of performing extraction and obtaining an extract containing a desired separated component through filtration, a bar-collation method, and the like can be used.
  • the extract thus obtained is used as it is depending on the use mode after removing unnecessary solids by filtration or centrifugation, if necessary, or the solvent is distilled off. And partially concentrated or dried.
  • the isolated product obtained by concentration or drying may be used after being purified by washing with a non-soluble solvent, or may be used by further dissolving or suspending the product in an appropriate solvent. You can also.
  • a fraction having a desired inhibitory activity is obtained and purified by using a conventional purification method such as a countercurrent distribution method or liquid chromatography. It is also possible to use it.
  • the solvent extract obtained as described above can be processed into a dried concentrated extract form by ordinary drying means such as vacuum drying and freeze drying.
  • an oral composition containing the periodontal disease agent of the present invention as an active ingredient.
  • the inhibitory effect of the periodontal disease agent of the present invention is not adversely affected, other components commonly used in oral compositions, such as adhesives, refreshing agents, binding agents, etc.
  • Agents, sweeteners, flavors, disintegrants, lubricants, colorants, sustained release regulators, surfactants, solubilizers, wetting agents, pH adjusters, etc. can be added as desired.
  • Examples of the pressure-sensitive adhesive include water-soluble polymer materials derived from polysaccharides, cellulose-based polymer materials, synthetic polymer materials, natural polymer materials, amino acid polymer materials, rubber polymer materials, etc. Is available.
  • polysaccharides such as pullulan, pullulan derivatives and starch; hydroxypropyl cellulose, hydroxyethyl cellulose, hydroxypropyl methenoresenorelose, hydroxyethino retino resenorelose, canoleboxy methino rescenellose salts (carboxymethyl cellulose, Sodium carboxymethylcellulose and potassium ruboxymethylcellulose), methinoresanolose, ethylcellulose, polyacrylic acid, polyacrylate (such as sodium polyacrylate and acrylic acid / octyl acrylate copolymer), meta Copolymers of acrylic acid (polymers of methacrylic acid and n-butyl acrylate, polymers of methacrylic acid and
  • Examples of the refreshing agent include 1-menthol, cQ-menthol, heart force oil, camphor, heart force water, borneol, peppermint essential oil, spearmint essential oil, and the like that can be used in the present invention. Any one of these can be used alone, or two or more can be used in combination.
  • binders include sugars (such as glucose), sugar alcohols (such as sorbitol, xylitol, erythritol, and mannitol), polybulurpyrrolidone, starches, macrogol, dextrin, tragacanth, gelatin, polybulul alcohol, Shellac, gum arabic, sodium alginate, hydroxypropylcellulose, and the like are available in the present invention, but are not limited to these. The above can also be used together.
  • sugars such as glucose
  • sugar alcohols such as sorbitol, xylitol, erythritol, and mannitol
  • polybulurpyrrolidone starches
  • macrogol dextrin
  • tragacanth gelatin
  • polybulul alcohol such as sorbitol, xylitol, erythritol, and mannitol
  • polybulurpyrrolidone starches
  • macrogol dextrin
  • sweeteners include saccharin sodium, stepioside, stevia extract, aspartame, xylitol, starch syrup, honey, sorbitol, maltitol, mannitol, saccharides (lactose, sucrose, fructose, glucose, etc.).
  • saccharin sodium saccharin sodium
  • stepioside stevia extract
  • aspartame aspartame
  • xylitol starch syrup
  • honey sorbitol
  • maltitol maltitol
  • mannitol saccharides
  • Natural flavors (spearmint oil, varnish oil, eucalyptus oil, wintergreen oil, cassia oil, clove oil, thyme oil, sage oil, lemon oil, orange oil, heart power oil, power rudamon oil, Coriander oil, mandarin oil, lime oil, lavender oil, rosemary oil, laurel oil, camomil oil, caraway oil, marjoram oil, bay oil, lemongrass oil, orina gum oil, pine-dollar oil, etc.), synthetic Perfume (Carbon, Anethole, Cineol, Methyl salicylate, Cynamic aldehyde, Eugenol, Thymol, Linalol, Linalyl acetate, Limonene, Menthone, Menthyl acetate, Pinene, Octylaldehyde, Citral, Pregon, Calbele acetate, Anisaldehyde Natural fragrances listed above and , Or the like blended fragrance obtained by mixing the selected fragrance arbitrarily
  • Examples of the disintegrant used in the present invention include starches, methylcellulose, crystalline cellulose, cellulose derivatives (such as sodium carboxymethylcellulose), alginic acid, alginates, carbonates, organic acids, polyvinylpyrrolidone, and crosslinked polybutyropyrrolidone. It can be used, but not limited to these, only one of these can be used, or two or more can be used in combination.
  • Lubricants include talc, metal sarcophagus, fatty acids (such as stearic acid), stearates (such as magnesium stearate), talc, sucrose fatty acid esters, hydrous silicon dioxide, light anhydrous key acid, dry water Acid-aluminum gel, macrogol, etc. can be used in the present invention, but are not limited to these, use only one of these V, or use two or more together You can also.
  • blue 1, No. 4 titanium dioxide, copper chlorophyllin sodium and the like can be used in the invention of the present application. Can be used, or two or more types can be used in combination.
  • Preservatives include benzoic acids, salicylic acids, sorbic acids, norabens, cetylpyridinium chloride, decalinium chloride, benzethonium chloride, benzalkonium chloride, chlorhexidine chloride, chlorhexidine darconate, isopropylmethylphenol, Forces that can be used in the present invention, such as trickle san, hinokitiol, phenol, etc., are not limited to these. Any one of these forces can be used, or two or more can be used in combination.
  • sustained release modifier polyvinyl acetate, ethyl cellulose, aminoalkyl metaacrylate copolymer and the like that can be used in the present invention S, and any one of these not limited to these 1 It is possible to use only one type or use both.
  • sucrose fatty acid ester polyoxyethylene hydrogenated castor oil, sorbitan monostearate, polysorbate, glyceryl monostearate, sodium lauryl sulfate, lauromacrogol and the like can be used in the present invention.
  • a certain force is not limited to these. Either one of these may be used, or two or more may be used. The above can also be used together.
  • solubilizer glycerin, concentrated glycerin, propylene glycol, ethanol, fluidized oil ⁇ raffin, purified water, macrogol, polysorbate and the like can be used in the present invention, but are not limited thereto. Either one of these forces can be used, or two or more can be used in combination.
  • wetting agent glycerin, propylene glycol, sorbitol solution, water, ethanol, dilute ethanol and the like are usable in the present invention. Or, use two or more types together.
  • pH adjuster lactic acid, pantothenic acid, phosphate, malic acid, citrate, and the like can be used in the present invention. Can be used, or two or more types can be used in combination.
  • any of tablets, pills, granules, solutions, sheets, gels, pastes and the like can be used.
  • periodontitis, gingivitis, periodontitis, wisdom teeth can be obtained by using a toothpaste, mouthwash, oral pasta, troche, etc.
  • a toothpaste, mouthwash, oral pasta, troche, etc. Can effectively deal with prevention and treatment of oral diseases caused by destruction of periodontal tissues such as peritonitis and peri-implantitis
  • a conventionally known plant extract that exerts an effect of inhibiting the extension of gingival epithelial tissue is added to the periodontal disease agent or oral cavity composition of the present invention. It is also possible to add substances and medicinal compounds (compositions) arbitrarily, and the addition amount thereof can be easily adjusted by those skilled in the art.
  • Gingival epithelial tissue (about 5.0 mm ⁇ about 5.0 mm slice) was collected from the oral cavity of a healthy human gingival tissue. Collected tissue pieces are washed with phosphate buffer (1 X 10 5 U / ml). It was immersed in penicillin, 100 ⁇ g / ml streptomycin, and 80 ⁇ g / ml kanamycin), and was cut into small sections of about 0.5 mm ⁇ about 0.5 mm with a scalpel within 24 hours. The small section was placed on a well of a type I collagen-coated 6-well plate. After confirming adhesion between the small section and collagen, the primary culture medium (L-glutamine,
  • DMEM / Ham's F12 medium (manufactured by Dainippon Pharmaceutical) containing 10% FBS 10 pg / ml EGF 80 ⁇ g / ml kanamycin was gently poured into the well.
  • the culture system thus prepared was cultured under conditions of 37 ° C and 5% carbon dioxide, and the primary culture medium was replaced with a fresh one once every two days.
  • the culture solution was transferred to a type I collagen-coated T75 flask, and a confluence of 2500 cells / cm 2 was used as the medium, and subculture was performed according to the cell growth rate to obtain gingival epithelial cells used in the following examples. It was.
  • an inflammation induction medium for artificially inducing periodontitis was prepared.
  • Recombinant human TNF- ⁇ an inflammation-inducing substance, was purchased from PEPROTECH (Size B).
  • vial 50 ⁇ g 300-01A; Lot No. 121CY25).
  • 50 ⁇ g of recombinant human TNF-a was allowed to stand at room temperature for 1 hour and then applied to a tabletop centrifuge. Dissolve the precipitate obtained by centrifugation in 500 ⁇ l of distilled water and add 0.1 mg / ml.
  • aqueous solution was further dissolved in 3.564 ml of physiological saline (PBS ( ⁇ )).
  • PBS physiological saline
  • the PBS solution thus obtained was dispensed in 1.2 ml portions into a serum tube and stored at a temperature of 20 ° C.
  • the remaining aqueous solution was dispensed 100 ⁇ l into a serum tube and stored at a temperature of 20 ° C.
  • cort extr. a. Ask Pharmaceutical Co., Ltd.
  • a solvent purified water
  • the assay was performed according to the procedure reported in the literature of pp. 1219-1224 (2003).
  • gingival epithelial cells are placed on a 24-well plate (1.8 cm 2 Z-well) at a ratio of 2 ⁇ 10 4 Z-wells. Once every two days, the subculture medium was replaced with fresh one and the culture was continued until the cells covered the entire well. After confirming that the cells covered the entire well, half the cells of the well were scraped with the tip of the pipette tip. After washing the well with PBS, pour the inflammation-inducing medium and a solution containing extract components (concentration of 1.0% or 0.1%) from the willow plant and grow under conditions of 37 ° C and 5% carbon dioxide. At 0, 24, and 48 hours after the start of culture, the wells were photographed to verify the extent of cell spreading (FIG. 1 (b)). In addition, the control group was subjected to the same procedure except that only the culture medium for inflammation induction was poured after washing the well with PBS (Fig. L (a)).
  • a cocoon of wood in a tree [0051] A cocoon of wood in a tree.
  • the assay was performed according to the procedure reported in the literature of Periodont Res, vol.38, pp.591-596 (2003). That is, with the progress of periodontal tissue destruction due to the development of periodontitis, healthy gingival epithelial cells (Fig. 2 (a)) downgrow towards the root of the tooth (Fig. 2 (b)), As a result, we focused on the unique phenomenon of the formation of a gingival crevice (periodontal pocket) peculiar to periodontitis between the gingiva and the tooth, and examined the effect of inhibiting the growth of gingival epithelial cells in vivo.
  • dipotassium glycyrrhizate 5% aqueous solution (positive control: 5 animals), willow plant extract 5% aqueous solution (present invention: 5 animals), and purified water (negative control: 5 animals).
  • Each dose was administered and allowed to act for an additional 5 minutes. This series of work was carried out every day for four weeks.
  • the sample was immersed in a phosphate buffer (PH7.4) at 4 ° C overnight.
  • the sample thus obtained was embedded in an OCT compound (Sakura Seiki), and then a section in the tongue direction of 8 ⁇ m thickness was prepared with Cryostat (Leica).
  • the sections were stained with hematoxylin and eosin, and microscopically observed to measure the downgrowth ( ⁇ m) of gingival epithelial tissue.
  • the downgrowth of the gingival epithelial tissue is the position where the gingival epithelium and the tooth are in contact (Central
  • the distance from the Enamel Junction (CEJ): position X) to the leading edge (position Y) of the gingival epithelial cells invading the tissue was measured with an eyepiece micrometer.
  • the measurement results are summarized in Table 2 below.
  • the number of rats with a distance a of zero, that is, rats that did not have any double wings (the number of non-extending individuals) was also shown in Table 2 below.
  • Oral compositions for various uses were prepared by blending willow plant extract (0.5%), which demonstrated the effect of inhibiting the growth of gingival epithelial cells in Example C. Note that the unit of the amount of component in this example is expressed in weight% unless otherwise specified.
  • Toothpastes were prepared by mixing and kneading the materials listed in Table 4 below at room temperature.
  • the agent for periodontal disease of the present invention is useful as a means for preventing and treating oral diseases such as gingivitis and periodontitis.
  • FIG. 1 is a schematic diagram illustrating the principle of a gingival epithelial cell extension inhibition test.
  • FIG. 2 is a schematic diagram illustrating the principle of extension of gingival epithelial tissue.
  • FIG. 3 is a photograph showing the extension of gingival epithelial tissue in rats treated with (a) purified water, (b) willow plant extract, and (c) dipotassium glycyrrhizinate.

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Abstract

Le problème à résoudre dans le cadre de la présente invention consiste à fournir un nouvel agent thérapeutique d’une parodontopathie qui soit excellent en termes d’effet préventif de la prolifération anormale de l’épithélium gingival. La solution proposée consiste en un agent thérapeutique d’une parodontopathie comprenant un ingrédient séparé produit par extraction d’un matériau brut d’une plante appartenant à la famille des salicacées, du genre Salix, au moyen d’un solvant ; et en une composition pour une application buccale qui peut être utilisée pour le traitement d’une pathologie buccale telle qu’une gingivite et une parodontite.
PCT/JP2006/319736 2005-09-30 2006-10-02 Agent thérapeutique pour une parodontopathie contenant un ingrédient extrait d’une plante appartenant à la famille des salicacées, genre salix WO2007037492A1 (fr)

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JP2005288572A JP4921763B2 (ja) 2005-09-30 2005-09-30 ヤナギ科ヤナギ属植物の抽出成分を配合した歯周病用剤
JP2005-288572 2005-09-30

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011109951A (ja) * 2009-11-26 2011-06-09 Kao Corp 歯周炎モデル作製方法及び歯周炎モデル非ヒト動物
WO2013035333A1 (fr) * 2011-09-08 2013-03-14 株式会社ロッテ Composition orale

Citations (3)

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Publication number Priority date Publication date Assignee Title
JPH09268117A (ja) * 1996-04-02 1997-10-14 Lion Corp 口腔用組成物
JP2002173424A (ja) * 2000-12-04 2002-06-21 Maruzen Pharmaceut Co Ltd マトリックスメタロプロテアーゼ阻害剤
JP2005206533A (ja) * 2004-01-23 2005-08-04 Fancl Corp 血管新生阻害用組成物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0926817A (ja) * 1995-07-12 1997-01-28 Toshiba Eng Co Ltd 点検データ管理装置

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09268117A (ja) * 1996-04-02 1997-10-14 Lion Corp 口腔用組成物
JP2002173424A (ja) * 2000-12-04 2002-06-21 Maruzen Pharmaceut Co Ltd マトリックスメタロプロテアーゼ阻害剤
JP2005206533A (ja) * 2004-01-23 2005-08-04 Fancl Corp 血管新生阻害用組成物

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011109951A (ja) * 2009-11-26 2011-06-09 Kao Corp 歯周炎モデル作製方法及び歯周炎モデル非ヒト動物
WO2013035333A1 (fr) * 2011-09-08 2013-03-14 株式会社ロッテ Composition orale
JP2013056855A (ja) * 2011-09-08 2013-03-28 Lotte Co Ltd 口腔用組成物
CN103781466A (zh) * 2011-09-08 2014-05-07 罗蒂株式会社 口腔用组合物
US10201493B2 (en) 2011-09-08 2019-02-12 Lotte Co., Ltd. Method of reducing oral biofilm

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JP4921763B2 (ja) 2012-04-25

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