WO2006005211A1 - Agents d'hygiene buccale contenant un derive du chitosane - Google Patents

Agents d'hygiene buccale contenant un derive du chitosane Download PDF

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Publication number
WO2006005211A1
WO2006005211A1 PCT/CH2005/000389 CH2005000389W WO2006005211A1 WO 2006005211 A1 WO2006005211 A1 WO 2006005211A1 CH 2005000389 W CH2005000389 W CH 2005000389W WO 2006005211 A1 WO2006005211 A1 WO 2006005211A1
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Prior art keywords
chitosan
oral care
oral
product according
methylpyrrolidone
Prior art date
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PCT/CH2005/000389
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German (de)
English (en)
Inventor
Christine Garbers
Dally Moya-Argilagos
Riccardo A. A. Muzzarelli
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Gaba International Ag
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Publication of WO2006005211A1 publication Critical patent/WO2006005211A1/fr

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Classifications

    • 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
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; Derivatives thereof

Definitions

  • the present invention relates to a Mundretemit ⁇ tel comprising a chitosan derivative and its use for the prevention or treatment of caries.
  • Caries is mainly caused by acids that are produced by oral bacteria. These acids demineralize the hydroxyapatite that forms the enamel.
  • An important bacterial species responsible for caries is Streptococcus mutans, which can accumulate in large numbers on the teeth and which is regarded as the bacterial agent chiefly responsible for the disintegration of the tooth enamel. The reduction of this microorganism on the Zahnoberflä ⁇ che is therefore of vital importance in the prevention and treatment of dental caries.
  • Chitosan is obtained by chitin (a polymer of ß ⁇ (l, 4) - glycosidically bound repetitive units of N-acetyl-D-glucosamine) by deacetylation in an alkaline medium ge.
  • chitin a polymer of ß ⁇ (l, 4) - glycosidically bound repetitive units of N-acetyl-D-glucosamine
  • the degree of deacetylation increases with increasingly severe deacetylation conditions, but with harsh deacetylation conditions, cleavage of the polymer backbone is also observed.
  • Commercially available types of chitosan are therefore only partially deacetylated, with degrees of deacetylation typically ranging from 0.70 to 0.90.
  • Chitosan itself has been used in oral care products.
  • Chitosan which is actually present in the formulation of the oral hygiene product and also in the oral cavity, is a cationic polymer because its deacetylated amino groups are protonated at physiological pHs. This is considered essential because the unprotonated chitosan is almost insoluble in aqueous media. It is also believed that this cationic chitosan either attaches to the negatively charged tooth surface, thereby preventing the deposition of oral bacteria, or it attaches to the membranes of the oral bacteria, thereby preventing their attachment to the tooth surface (See, for example, Sano, H. et al., Bull. Tokyo dent. Coli., Vol. 42, No. 4, pp.
  • chitosan can be degraded to low molecular weight fragments by lysozyme present in saliva, and this low molecular weight chitosan has also been found to be active against oral bacteria (see, eg, Sano, H. , et al., Bull. Tokyo dent. Coli., Vol. 42, No. 4, pp. 243-249, 2001).
  • chitosan Some derivatives of chitosan have also been considered as agents for preventing the attachment of oral bacteria to the tooth surface. These are, for example, imidazolyl chitosan (eg Tarsi, R., et al., J. Dent. Res. 76 (2), pp. 665-672, 1997), N-carboxymethyl chitosan (eg Muzzarelli, R. et al., J. Chem Cosmetol 20, pp. 201-208, 2002), ethylene glycol chitin (Sano, H., et al., Bull. Tokyo dent. Coli., Vol. 32, No. 1, pp. 9-17, 1991) and sulfated and phosphorylated chitosan (Sano, H., et al., Bull. Tokyo dent. Coli., Vol. 42, No. 4, pp. 243-249, 2001).
  • imidazolyl chitosan eg Tarsi
  • Tooth decay is that they do not take into account that the oral bacteria are not found in a planktonic state, but are embedded in a biofilm that covers the tooth surface and also contains polysaccharides that are secreted by many of these bacteria. To a certain extent, this biofilm prevents active agents from coming into contact with the bacteria; it can enable individual active agents to pass through the biofilm and enter into contact with the bacteria more easily than other agents, and can thus lead to apparent activities Agen ⁇ zien lead, which differ significantly from those observed in planktonic bacterial cultures were ⁇ the. Prior art studies that do not take into account the influence of biofilm are thus believed not to provide reliable predictions of in vivo activities.
  • the present invention provides an oral hygiene composition
  • R is -NH 2 , -NHCOCH 3 or R 1 , where at least 90 mol% of the R 'methylpyrrolidone groups of the following formula (II):
  • methylpyrrolidone chitosan The above polymer having repeating units (I) is hereinafter referred to as "methylpyrrolidone chitosan".
  • the above polymer reduces the number of colony-forming units (CFU's) of Streptococcus mutans m biofilms containing this bacterium, among other oral bacteria, and that it is therefore effective against caries.
  • CFU's colony-forming units
  • the reduction in the CFUs of Streptococcus mutans could be due to the fact that methylpyrrolidone chitosan prevents the adhesion of Streptococcus mutans to the tooth surface or that it has an antivital effect on Streptococcus mutans.
  • methylpyrrolidone chitosan which has a lower proportion of protomernary amino groups than chitosan, which served as starting material for its preparation, in the aqueous media of oral hygiene products at physiological pH (ie at pH values from about 4 to about 7.5, preferably from about 6 to about 7.5) is nevertheless better soluble than the latter, and that methylpyrrolidone chitosan by the other additives present in these media, in particular those in most Mund ⁇ care agents present gel-forming or moisturizing Po ⁇ polymers or abrasives, which are common in toothpastes are not like or absorbed.
  • the methylpyrrolidone chitosan used in the oral hygiene composition of the present invention may typically comprise at least about 0.5 mol% of repeating units in which R is methylpyrrolidone of the above formula (II).
  • the methylpyrrolidone chitosan comprises about 0.5 to about 60 mol%, more preferably about 0.5 to about 20 mol%, and particularly preferably about 4 to about 20 mol% or on the other hand about 0.5 to about 10 mol% of such repetitive units.
  • the methylpyrrolidone chitosan comprises from about 80 mole% to about 20 mole%, more preferably from about 80 mole% to about 60 mole% of repeat units in which R is -NH 2 .
  • the oral hygiene products according to the invention are water-containing, the water content preferably being in a range from 10 to 90% by weight, more preferably in the range from 50 to 90% by weight. Percent, based on the oral care product, may be.
  • aqueous mouth-care preparations according to the invention are not solutions of 16 g of methylpyrrolidone chitosan per liter.
  • the oral hygiene compositions according to the invention are also not solutions of 4% by weight in distilled water or in acetate buffer pH 5.0.
  • the oral hygiene product according to the invention is a dry preparation which, in addition to the methylpyrrolidone chitosan, optionally contains further solid additives customary for an oral hygiene product and which is directly wetted or dissolved before use with water or with saliva.
  • the oral care compositions according to the invention in the form of a dry preparation are not freeze-dried methylpyrrolidone chitosan.
  • the oral mucosa is able to absorb certain therapeutically or prophylactically active agents, whereby the permeation into the oral mucosa is favored with increasing lipophilicity of the agent.
  • a literature reference known to the Applicant (Eur. Journal of Pharm. Sciences 21, pp. 351-359, February 2004)
  • increasing the penetration of substances with poor permeability into the oral mucosa by means of the methylpyrrolidone chitosan is not the goal of the oral hygiene products of the present invention.
  • the oral hygiene products it is therefore initially preferred that they do not contain acyclovir. Rather preferably, they do not contain any poor permeability into the oral mucosa. even more preferably, they do not contain antivirals which are poorly permeable to the oral mucosa, and more preferably do not contain any agents which are poorly permeable to the oral mucosa and therapeutically or prophylactically active.
  • a “therapeutically or prophylactically active agent” is considered to be “poorly permeable to the oral mucosa” if the log of its partition coefficient between n-octanol and water at room temperature is in the range from -3 to -0.5 the measurement of the partition coefficient after equilibration can be carried out between 50 ml of 1% (w / v) solution of the agent in water and 50 ml of n-octanol.
  • the partition coefficient of a compound between n-octanol and aqueous solutions is used in the art as an approximate guide to the penetration capacity of a compound into biological membranes.
  • the methylpyrrolidone chitosan has an average molecular weight in the range from 10,000 to 1,000,000 daltons, more preferably from 100,000 to 400,000 daltons, particularly preferably from 100,000 to 200,000 daltons.
  • the synthesis of the methylpyrrolidone chitosan which can be used in the present invention is based on chitosan derived from the shells of crustaceans of the sea (eg crabs, shrimps, krill, lobsters, crawfish, duck mutton, steer crabs) Insects, fungi, such as Aspergillus or Agaricus, or molluscs, such as octopus, derived chitin.
  • the chitosan is reacted with levulinic acid, wherein the -NH 2 ⁇ groups in chitosan react with keto groups of levulinate and are converted to imine groups. These imine groups are reduced to secondary amine groups, and the amine groups cyclize to methylpyrrolidone groups of the above formula (II).
  • the reduction of the imine groups to amine groups can be carried out, for example, by means of catalytic hydrogenation, by means of sodium borohydride, sodium cyanoborohydride or by means of formic acid.
  • the cyclization of the amine groups to methylpyrrolidone groups may even occur spontaneously after the reduction of the imine groups.
  • an ester of levulinic acid such as the methyl ester, may be used for imine formation.
  • the chitosan can be previously adjusted in its molecular weight by means of partial hydrolysis (see, for example, Muzzarelli et al., International Journal of Biological Macromolecules). cules 16/4, pages 177-180, 1994).
  • the chitosan can be fractionated into fractions on a preparative scale, whether partially hydrolysed or not, by dissolving the chitosan in acid and then gradually increasing the pH, whereby the gradual precipitation of fractions with sin ⁇ kendem molecular weight is effected.
  • the precipitated chitosan fractions obtained can be reduced to their average molecular weight and their molecular weight distribution in known manner by gel permeation chromatography using, for example, N-acetylglucosamine oligomer or pullulan as retention time standards, or by using a Multi Angle Laser Light Scattering "- (MALLS) detector are examined.
  • MALLS Multi Angle Laser Light Scattering
  • methylpyrrolidone chitosan Purification of the methylpyrrolidone chitosan is primarily intended to remove excess, unreacted lavulanic acid as well as salts and other chemical compounds formed during the reduction step. If these compounds were not removed, they would react with themselves to form black pigments. Since the chemical species to be removed are of low molecular weight, separation is readily accomplished by dialysis against desalted water or by anion exchange or by desalting on suitable chromatographic supports or by precipitation of the polymer at constant pH with ethanol containing the low molecular weight compounds in Lo ⁇ sung, achieved.
  • the oral hygiene compositions according to the invention include methylpyrrolidone chitosan in preferably 0.01 to 2 percent by weight, more preferably in 0.1 to 1 percent by weight, based on the oral hygiene product.
  • the oral hygiene products according to the invention can be prepared in a known manner using customary additives and / or auxiliaries, as are well known to the person skilled in the art.
  • a useful starting point for an oral hygiene product according to the invention may be a previously known oral care composition comprising chitosan, wherein instead of the chitosan an equal amount of methylpyrrolidone chitosan is used.
  • the oral hygiene products according to the invention can be, for example, in the form of a chewable tablet, a toothpaste, a toothpowder, a mouthwash solution, a dental gel, a formulation for bad breath, a chewing gum, a saliva replacement fluid or a touch solution. They are preferably in the form of chewable tablets, toothpastes, toothpowder, mouthwashes, formulations against halitosis, chewing gum, saliva substitute fluids or coating solutions.
  • a pharmaceutically acceptable acid such as hydrochloric acid, hydrofluoric acid, phosphoric acid or lactic acid can be added. This also helps to protonate the -NHa groups of methylpyrrolidone chitosan, thereby increasing its solubility. Preference is given to using hydrofluoric acid, since the fluoride itself also acts as an anti-caries agent.
  • abrasives examples include alkaline earth metal phosphates (eg dicalcium phosphate dihydrate, anhydrous dicalcium phosphate, tricalcium phosphate), insoluble alkali metal metaphosphates, finely ground or colloidal silica gels, aluminum hydroxide hydrates, aluminum silicates, aluminum magnesium silicates and alkaline earth metal carbonates.
  • Suitable plastics for example polyethylenes, can also be used.
  • These scouring agents can typically be used in amounts of from 10 to 60 percent by weight.
  • Binders or thickeners for tooth pastes are gel-forming agents of natural or synthetic origin.
  • Examples of these are water-insoluble alginates, carrageenates, guar gum, tragacanth, water-soluble cellulose ethers (for example methylcellulose, hydroxyethylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose), aerosils and bentonites.
  • the content of binding agent is 0.5 to 10% by weight.
  • plasticizers and humectants for toothpastes according to the invention are polyhydroxylic alcohols, such as glycerol, propylene glycol, glucose syrup, polyethylene glycols, sorbitol, polypropylene glycols and polyvinylpyrrolidone. They can typically be used in amounts of 10 to 40 percent by weight.
  • Mouthwash solutions according to the invention are preferably aqueous, alcoholic or mixed aqueous / alcoholic solutions.
  • Additives and auxiliaries for winding solutions are examples of emulsifiers, humectants as exemplified above for toothpastes, sweeteners such as sorbitol, xylitol and various drug extracts.
  • Dental gels according to the invention may contain as carrier material a swollen mixture of natural or synthetic hydrocolloids.
  • carrier material a swollen mixture of natural or synthetic hydrocolloids.
  • examples thereof are methylcellulose, hydroxyalkylcelluloses, carboxymethylcellulose, water-soluble and swellable salts of polyacrylic acids, algmates,
  • Salivary replacement fluids according to the invention may comprise, as thixotropic agent, hydroxyalkylcelluloses, such as hydroxyethylcellulose, hydroxypropylcellulose or low-substituted hydroxypropylcellulose.
  • the inventive salivary replacement fluids may further comprise inorganic salts typical of human saliva, such as NaCl, MgCl 2 , CaCl 2 and KCl; and they can be buffered by means of, for example, a dihydrogen phosphate / hydrogen phosphate or carbonate / bicarbonate buffer to a pH and a buffering capacity, as are typical of human saliva.
  • the salivary fluids of the invention may further comprise humectants as described above for toothpastes.
  • oral care products are touch preparations, chewable tablets, tooth powders and formulations for bad breath.
  • In Touchierlositch and Formu ⁇ lierungen against halitosis can be used as additives the same sub stances as in Spullosungen.
  • Additives for chewable tablets may be binders and sugars such as sucrose, glucose, lactose or preferably non-cariogenic sugars such as xylitol, mannitol or sorbitol.
  • the oral hygiene products according to the invention can preferably be improved by adding flavorings customary in oral care products and aromatic substances to the taste.
  • these are saccharin, quaternary ammonium saccharinates, cyclamates, coumarin, vanillin, peppermint, cerous minzol, anisole, menthol, anethole, citrusol or other essences such as apple, eucalyptus or mint essence.
  • the oral hygiene compositions according to the invention may also comprise an additional fluoride source customary for oral care products, such as NaF, KF, NaHFPO 3 , SnF 2 or TiF 4 . These fluoride sources are known.
  • amine fluorides examples include amine fluorides.
  • amine fluorides are disclosed in WO-A-98/22727, WO-A-01/39737 and DE-PS-1198493, incorporated herein by reference.
  • amine fluorides N, N-bis (2-hydroxyethyl) aminopropyl-N '- (2-hydroxyethyl) octadecylamine dihydrofluoride is preferred.
  • the oral hygiene products may further comprise an antibacterial agent common in oral hygiene products.
  • the preferred antibacterial agent is chlorhexidine or chlorhexidine digluconate.
  • the amount of antibacterial agent, if used, may preferably be in the range of 0.05 to 0.20 weight percent based on the oral care product.
  • the weight ratio of methylpyrrolidone chitosan to antibacterial agent can be in the range from 5: 1 to 1: 1, and more preferably it is about 2: 1
  • the amounts of methylpyrrolidone chitosan and chlorhexidine (or chlorhexidine digluconate) are 0.2% by weight or 0.1% by weight, based on the oral hygiene product.
  • Titanium dioxide 1, 5 (Kemira AFDC, Kemira)
  • the formulation is prepared as described in Example 1.
  • Methylpyrrolidone chitosan 0.5 sodium fluoride 0.0555 ( 250 ppm F " ) saccharin 0, 07
  • Aroma 0, 2 (peppermint or menthol)
  • the water is added to the mixing kettle.
  • the propylene glycol, the hydrogenated castor oil and the peppermint oil are mixed in the process and this mixture is added to the water under inert conditions. Finally, the remaining additives are added with stirring.
  • Sorbitol 20.00 water QS The preparation involves the dispersion of the hydroxy ethylcell ⁇ lose in water at 7O 0 C by using a homo-mixer for 15 minutes. Thereafter, the anorgani ⁇ 's salts are dissolved in the formulation. The salts are added to adapt the formulation to the physicochemical and organoleptic properties of human saliva. Finally, the Methylpyrrolidonchitosan is dissolved at 40 0 C. The packaging of the formulation is carried out in a sterile environment. It is intended for single dose use.
  • the gel is made by using a homo-mixer her ⁇ by the hydroxyethyl cellulose is dispersed at 65 0 C for 15 minutes in water, is then cooled to 4O 0 C and the reduced sugar xylitol and maltitol are added, thereby obtaining a clear solution becomes.
  • Previously mixed polysorbate-20 and flavor are then added.
  • the methylpyrrolidone chitosan previously dissolved in a minimum amount of water, is added, followed by the chlorhexidine digluconate.
  • Example 6 In vitro test of methylpyrrolidone chitosan against oral bacteria embedded in a biofilm
  • test method is based on that of Guggenheim et al. 80 (1), pp. 363-370 (2001); Shapiro, S., et al., Caries Res. 36, pp. 93-100 (2001); Guggenheim, B., et al., J. Dent. 2002)).
  • the biofilms were cultured using Streptococcus mutans OMZ 918, Streptococcus oralis OMZ 607, Veilonella dispar OMZ 493, Actinomyces naeslundii OMZ 745 and Fusobacterium nucleatum OMZ as bacteria and further using Candida albicans OMZ 110. These microorganisms were obtained from the culture collection of the Institute of Oral Microbiology and General Immunology of the University of Zurich.
  • the pre-cultures of the microorganisms were determined by In ⁇ incubation at 37 C C on Columbia blood agar plates, then incubated at 37 ° C on liquid Universal Medium ( "FUM”; Guggenheim, B., et al, Infect Immun 42, pages 459-470... , 1983) with Sörensen buffer pH 7.2 containing 0.3 glucose (for Veilonella dispar also 1% sodium lactate was added).
  • Methylpyrrolidone chitosan was prepared as described in US-A-5,378,472.
  • methylpyrrolidone chitosan interferes with Streptococcus mutans.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des agents d'hygiène buccale contenant un polymère doté d'unités répétitives de formule (I): (I), dans l'unité répétitive (I) de laquelle R signifie -NH2, -NHCOCH3 ou R', au moins 90 % en moles de R' étant des groupes méthylpyrrolidone. Selon l'invention, ce polymère empêche l'adhérence de Streptococcus mutans à la surface des dents, d'où l'action anti-carrie des agents d'hygiène buccale contenant ce polymère.
PCT/CH2005/000389 2004-07-12 2005-07-07 Agents d'hygiene buccale contenant un derive du chitosane WO2006005211A1 (fr)

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Cited By (9)

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US20110042169A1 (en) * 2006-12-29 2011-02-24 Luciano Faletto Lift with dual traction pulley
WO2011028968A1 (fr) 2009-09-02 2011-03-10 Synedgen, Inc. Procédés et compositions de soins oraux utilisant des composés dérivés de chitosane
WO2012110107A1 (fr) * 2011-02-18 2012-08-23 Gaba International Holding Ag Composition de bain de bouche
WO2012110106A1 (fr) * 2011-02-18 2012-08-23 Gaba International Holding Ag Composition de dentifrice
EP2813214A1 (fr) * 2013-06-12 2014-12-17 Henkel AG&Co. KGAA Crème dentaire liquide aux fluorure(s) d'amines
JP2016074723A (ja) * 2015-12-03 2016-05-12 ガバ・インターナショナル・ホールディング・アクチェンゲゼルシャフト マウスリンス組成物
US10765616B2 (en) 2013-03-12 2020-09-08 Synedgen, Inc. Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar
US11123994B2 (en) 2013-08-30 2021-09-21 Hewlett-Packard Development Company, L.P. Supply authentication via timing challenge response
CN115350116A (zh) * 2022-09-20 2022-11-18 武汉高登齿科材料有限公司 一种口腔抑菌膏及制备方法和应用

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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110042169A1 (en) * 2006-12-29 2011-02-24 Luciano Faletto Lift with dual traction pulley
EP2473043A4 (fr) * 2009-09-02 2015-09-23 Synedgen Inc Procédés et compositions de soins oraux utilisant des composés dérivés de chitosane
WO2011028968A1 (fr) 2009-09-02 2011-03-10 Synedgen, Inc. Procédés et compositions de soins oraux utilisant des composés dérivés de chitosane
JP2018058889A (ja) * 2009-09-02 2018-04-12 シネジェン， インコーポレイテッド キトサン誘導体化合物を用いる口腔ケア方法および組成物
JP2016104819A (ja) * 2009-09-02 2016-06-09 シネジェン， インコーポレイテッド キトサン誘導体化合物を用いる口腔ケア方法および組成物
CN106913470A (zh) * 2011-02-18 2017-07-04 加巴国际控股有限公司 洁齿剂组合物
CN103476386A (zh) * 2011-02-18 2013-12-25 加巴国际控股有限公司 洁齿剂组合物
CN103596544A (zh) * 2011-02-18 2014-02-19 加巴国际控股有限公司 口腔清洗剂组合物
AU2011359109B2 (en) * 2011-02-18 2015-11-05 Gaba International Holding Gmbh Mouthrinse composition
CN103596544B (zh) * 2011-02-18 2016-03-30 加巴国际控股有限公司 口腔清洗剂组合物
US10653605B2 (en) 2011-02-18 2020-05-19 Gaba International Holding Gmbh Dentifrice composition
AU2011359108B2 (en) * 2011-02-18 2016-05-19 Gaba International Holding Gmbh Dentifrice composition
WO2012110107A1 (fr) * 2011-02-18 2012-08-23 Gaba International Holding Ag Composition de bain de bouche
US9370479B2 (en) 2011-02-18 2016-06-21 Gaba International Holding Ag Mouthrinse composition
CN103476386B (zh) * 2011-02-18 2016-10-26 加巴国际控股有限公司 洁齿剂组合物
WO2012110106A1 (fr) * 2011-02-18 2012-08-23 Gaba International Holding Ag Composition de dentifrice
US10765616B2 (en) 2013-03-12 2020-09-08 Synedgen, Inc. Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar
EP2813214A1 (fr) * 2013-06-12 2014-12-17 Henkel AG&Co. KGAA Crème dentaire liquide aux fluorure(s) d'amines
US11123994B2 (en) 2013-08-30 2021-09-21 Hewlett-Packard Development Company, L.P. Supply authentication via timing challenge response
JP2016074723A (ja) * 2015-12-03 2016-05-12 ガバ・インターナショナル・ホールディング・アクチェンゲゼルシャフト マウスリンス組成物
CN115350116A (zh) * 2022-09-20 2022-11-18 武汉高登齿科材料有限公司 一种口腔抑菌膏及制备方法和应用

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