WO2007012080A2 - Oral care composition - Google Patents
Oral care composition Download PDFInfo
- Publication number
- WO2007012080A2 WO2007012080A2 PCT/US2006/028482 US2006028482W WO2007012080A2 WO 2007012080 A2 WO2007012080 A2 WO 2007012080A2 US 2006028482 W US2006028482 W US 2006028482W WO 2007012080 A2 WO2007012080 A2 WO 2007012080A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acids
- hop
- oral care
- care composition
- resins
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
-
- 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
- A61K36/13—Coniferophyta (gymnosperms)
- A61K36/15—Pinaceae (Pine family), e.g. pine or cedar
-
- 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)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- A61K8/9755—Gymnosperms [Coniferophyta]
- A61K8/9767—Pinaceae [Pine family], e.g. pine or cedar
-
- 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
- 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
- Periodontal diseases, gingivitis and dental caries are major public health diseases world-wide. These diseases can be inhibited to a certain extent by frequent brushing of the teeth, although the use of antibacterial agents gives better results.
- Chemical antibacterial agents such as chlorhexidine, triclosan and benzalkonium chloride have traditionally been used. Additionally natural products have shown activity against bacteria, which cause dental caries.
- An object of the invention is to provide oral care products that inhibit the microorganisms that cause dental caries and periodontal disease using natural resins.
- the invention generally provides oral care compositions that inhibit the growth, survival, or proliferation of a microorganism associated with dental caries and periodontal disease that comprise a natural resin.
- This invention is based, at least in part, on the finding that natural tree resins control the growth of common oral microorganisms such as Actinomyces viscosus and Streptococcus mutans both gram- positive organisms. Additionally, these natural resins are active against the gram- negative bacteria Fusobacterium nucleatum. This broad spectrum of activity gives additional benefits over other natural products used in oral care products.
- the present invention provides the use of tree resins or extracts or derivatives thereof to prepare an oral care composition having antibacterial activity against bacteria implicated in dental caries, gingivitis and other periodontal diseases.
- the present invention also provides an oral care composition having antibacterial activity against bacteria implicated in dental caries, gingivitis and other periodontal diseases, comprising a tree resin or derivative thereof and an orally acceptable carrier.
- Such oral care compositions are advantageously combined with hop resins, hop extracts, hop acids or hop acid derivatives.
- hop extract resins such as lupulone and humulone, from the hop plant humulus lupulus, are effective against cariogenic streptococci.
- US Patent No. 5,316,760 describes a mouth care product that contains a combination of Urtica dioica and an extract of Juniperus communis.
- Hop acids include alpha and beta acids.
- oral care compositions comprise alpha acids or reduced isoalpha acids (e.g., rhoisoalpha acids, tetrahydroisoalpha acids or hexahydroisoalpha acids isoalpha acids) or beta acids (e.g., hexahydrobeta acids and tetrahydrobeta acids).
- the hop acids are beta acids selected from the group consisting of lupulone, colupulone, adlupulone and derivatives thereof.
- the beta acids are hexahydrobeta acids or tetrahydrobeta acids.
- the concentration of hop acids present in the oral care composition is between about 0.001 and 0.1% (e.g., 001, 0.0025, 0.005, 0.01, 0.025, 0.05, 0.1%). In another embodiment the concentration of hop acid is between about 1% and 99% (e.g., 1%, 2.5%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 50%, 75%, 85%, or 95%).
- Hop acid derivatives are compounds that are chemically derived (either through natural biosynthetic processes (e.g., living organism metabolism (e.g., mammal, plant, bacteria)) or synthetic processes using human intervention (e.g., chemical synthesis)) from hop acids.
- Alpha acid derivatives e.g., isoalpha acids, rhoisoalpha acids, tetrahydroisoalpha acids, and hexahydroisoalpha acids
- hop alpha acids are compounds derived from hop alpha acids.
- rhoisoalpha acids refers to alpha acids isolated from hops plant product and which subsequently have been isomerized and reduced, using sodium borohydride, including cis and trans forms.
- rhoisoalpha acids include, but are not limited to, rhoisohumulone, rhoisocohumulone, and rhoadhumulone.
- tetrahydroisoalpha acids refers to a class of reduced isoalpha acids produced by hydrogenation of isoalpha acids.
- examples of tetrahydroisoalpha acids include, but are not limited to, tetrahydroisohumulone, tetrahydroisocohumulone and tetrahydroadhumulone.
- hexahydroisoalpha acids refers to a class of reduced isoalpha acids, produced by hydrogenation of isoalpha acids and sodium borohydride reduction of the resulting tetrahydroisoalpha acids.
- hexahydroisoalpha acids include, but are not limited to, hexahydroisohumulone, hexahydroisocohumulone and hexahydroadhumulone.
- beta acids refers to compounds that can be isolated from hops plant products, including but not limited to, lupulone, adlupulone, colupulone, tetrahydrolupulone, tetrahydroadlupulone, tetrahydrocolupulone and their derivatives.
- Exemplary beta acids include, but are not limited to, hexahydrobeta acids and tetrahydrobeta acids.
- extract refers to a concentrated preparation of the essential constituents of a plant (e.g., medicinal plant, hops).
- an extract is prepared by drying and powderizing the plant.
- the plant, the dried plant or the powderized plant may be boiled in solution.
- the extract may be used in liquid form, or it may be mixed with other liquid or solid herbal extracts.
- the herbal extract may be obtained by further precipitating solid extracts from the liquid form.
- An extract can be prepared by drying and subsequently cutting or grinding the dried material.
- the extraction process may then be performed with the help of an appropriate choice of solvent, typically supercritical or liquid carbon dioxide, ethanol/water mixture, methanol, butanol, iso-butanol, acetone, hexane, petroleum ether or other organic solvents by means of maceration, percolation, repercolation, counter-current extraction, turbo-extraction, or by carbon-dioxide hypercritical (temperature/pressure) extraction.
- solvent typically supercritical or liquid carbon dioxide, ethanol/water mixture, methanol, butanol, iso-butanol, acetone, hexane, petroleum ether or other organic solvents by means of maceration, percolation, repercolation, counter-current extraction, turbo-extraction, or by carbon-dioxide hypercritical (temperature/pressure) extraction.
- the extract may then be further evaporated and thus concentrated to yield by means of air drying, spray drying, vacuum oven drying, fluid-bed drying or freeze-drying, the extract product.
- the synthesized compounds can be separated from a reaction mixture and further purified by a method such as column chromatography, high pressure liquid chromatography, or recrystallization. As can be appreciated by the skilled artisan, further methods of synthesizing the compounds herein will be evident to those of ordinary skill in the art. Additionally, the various synthetic steps may be performed in an alternate sequence or order to give the desired compounds. Synthetic chemistry transformations and protecting group methodologies (protection and deprotection) useful in synthesizing the compounds described herein are known in the art and include, for example, those such as described in R. Larock, Comprehensive Organic Transformations, 2nd. Ed., Wiley- VCH Publishers (1999); T. W. Greene and P.G.M.
- An extract can be prepared by drying and subsequently cutting or grinding the dried material.
- the extraction process may then be performed with the help of an appropriate choice of solvent, typically supercritical or liquid carbon dioxide, ethanol/water mixture, methanol, butanol, iso-butanol, acetone, hexane, petroleum ether or other organic solvents by means of maceration, percolation, repercolation, counter-current extraction, turbo-extraction, or by carbon-dioxide hypercritical (temperature/pressure) extraction.
- the extract may then be further evaporated and thus concentrated to yield by means of air drying, spray drying, vacuum oven drying, fluid-bed drying or freeze-drying, the extract product.
- the synthesized compounds can be separated from a reaction mixture and further purified by a method such as column chromatography, high pressure liquid chromatography, or recrystallization. As can be appreciated by the skilled artisan, further methods of synthesizing the compounds herein will be evident to those of ordinary skill in the art. Additionally, the various synthetic steps may be performed in an alternate sequence or order to give the desired compounds. Synthetic chemistry transformations and protecting group methodologies (protection and deprotection) useful in synthesizing the compounds described herein are known in the art and include, for example, those such as described in R. Larock, Comprehensive Organic Transformations, 2nd. Ed., Wiley- VCH Publishers (1999); T. W. Greene and P.G.M.
- the oral care products or compositions of the present invention may include powders, pastes, gums, gels, solutions and the like for rinsing, brushing, washing, chewing or topical application in the oral cavity.
- the oral care products are formulated by conventional means known to those skilled in the art to ensure that the active ingredient comes in contact with the oral cavity such as teeth and gums as well as any calculus or plaque that may be present.
- Toothpastes are generally a slurry of an abrasive, a humectant, a thickening agent, fluoride, surfactants and flavours.
- Suitable abrasives include silica precipitates, anhydrous dicalcium phosphate, dihydrated dicalcium phosphate, hydrated alumina, calcium carbonate, sodium bicarbonate, sodium metaphosphate, and mixtures thereof.
- Suitable humectants include sorbitols, polyethylene glycols and glycerine.
- Suitable thickening agents include cellulose derivatives, silica thickeners, gums such as Xanthan gum, carrageenan, carboxyvinyl polymers etc.
- fluoride salts examples include sodium fluoride, potassium fluoride, sodium hexafluorosilicate and sodium monofluorophosphate.
- Suitable surfactants may be used, such as sodium dodecylbenzene sulfonate, sodium lauryl sulfate, sodium monosulfated monoglyceride of long chain fatty acids and the like.
- Conventional flavours may be added to give a pleasant and refreshing taste to the formulation.
- Mouth washes or oral rinses are typically a water-alcohol mixture.
- the alcohol is typically ethanol or iso-propanol. Additionally, humectants, thickening agents, surfactants, colours and flavouring agents may be added to the water-alcohol mixture.
- Chewable compositions may be formulated using a conventional gum base to prepare an anti-bacterial chewing gum.
- the pine resins can be added in a range of forms such as neat, ground as a fine powder or molten, although it may be preferential to form an aqueous alkaline salt solution of resin acids or as an alcoholic solution. It also may be advantageous to premix the rosin with a surfactant and admix with the other ingredients.
- the antimicrobial resin acids should be present in the formulation in an amount sufficient to produce an effective concentration in the mouth and to be able to come in contact with the microbes. Normally this may involve the formation of oral compositions which contain the resin acid at about 0.001% to 0.1% by weight although it may depend on the resin acid used. In other embodiments, the resins are present in an amount effective to kill bacteria ranging from about 1 to 10,000 ppm, from about 5 to 1,000 ppm, or from about 10 to 100 ppm. In various embodiments, the bottom of the range is any integer between 1 and 9,999 ppm and the top of the range is any integer between 2 and 10,000 ppm.
- Tree resins useable in this invention include especially pine resins, often called colophonium or pine rosin.
- individual components isolated from pine resins such as abietic acid, palustric acid, levopimaric acid, neoabietic acid, dehydroabietic acid, pimaric acid and isopimaric acid may also be used.
- Other tree resins include benzoin, myrrh, and pine balsam.
- tree resins can include synthesised tree resin analogues, modified natural resins such as hydrogenation, polymerisation derivatives and synthesised resin derivatives.
- modified natural resins such as hydrogenation, polymerisation derivatives and synthesised resin derivatives.
- EP 0465663A1 describes the anti-bacterial activity of abietic acid and tetrahydroabietic acid against bacteria associated with acne.
- WO 01/88205 describes a method for using natural food compatible resins to produce sugar.
- Figure 1 is a histogram showing the effect of different concentrations of resin acids on the growth of S. mutans.
- Figure 2 is a graph showing the growth of S. mutans with respect of a control sample.
- a 0.001% rosin mouthrinse formulation was prepared by adding a 0.1% aqueous alkaline solution of Chinese rosin acids (0.2g) to ethanol (5g) and water (14.8g). This gave a clear colourless solution.
- a 0.01% rosin mouthrinse formulation was prepared by adding a 1% aqueous alkaline solution of Chinese rosin acids (0.2g) to ethanol (5g) and water (14.8g) which gave a clear colourless solution.
- a toothpaste formulation containing 0.001% rosin was prepared by adding a 0.1% aqueous alkaline solution of Chinese rosin acids (0.2g) to a toothpaste formulation (19.8g) containing water, silica, glycerin, titanium dioxide, sodium lauryl sulfate, xanthan gum, sodium fluoride, flavourings.
- Assays were conducted by serially diluting the rosin acids in Brain Heart Infusion broth (Oxoid) and Thioglycolate broth (Merck) for Streptococcus mutans (NCTC10449) and Actinomyces viscosus (NCTC10951) respectively and in brain heart infusion agar for Fusobacterium nucleatum (NCTC10562).
- the final concentration of rosin acids in the media ranged from 1 ppm to 80 ppm. All the dilution series were conducted in triplicate and in the case of the broth MIC inoculated with approximately 10 5 freshly cultured (using the same medium) cells per ml of test assay broth. In each assay an inoculated control without any rosin acids was used as a positive control, and un-inoculated media acted as the negative control.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008523009A JP2009514789A (en) | 2005-07-20 | 2006-07-20 | Oral care composition |
AU2006269866A AU2006269866A1 (en) | 2005-07-20 | 2006-07-20 | Oral care composition |
CA002615629A CA2615629A1 (en) | 2005-07-20 | 2006-07-20 | Oral care composition |
EP06800225A EP1919438A2 (en) | 2005-07-20 | 2006-07-20 | Oral care composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0514943.0 | 2005-07-20 | ||
GBGB0514943.0A GB0514943D0 (en) | 2005-07-20 | 2005-07-20 | Oral care compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2007012080A2 true WO2007012080A2 (en) | 2007-01-25 |
WO2007012080A3 WO2007012080A3 (en) | 2007-05-31 |
Family
ID=34897556
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2006/028482 WO2007012080A2 (en) | 2005-07-20 | 2006-07-20 | Oral care composition |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1919438A2 (en) |
JP (1) | JP2009514789A (en) |
KR (1) | KR20080043779A (en) |
AU (1) | AU2006269866A1 (en) |
CA (1) | CA2615629A1 (en) |
GB (1) | GB0514943D0 (en) |
WO (1) | WO2007012080A2 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009023920A (en) * | 2007-07-17 | 2009-02-05 | Lion Corp | Antibacterial agent for oral cavity and composition for oral cavity |
WO2021067992A1 (en) * | 2019-09-30 | 2021-04-08 | The Procter & Gamble Company | Methods of use of oral care compositions comprising hops |
WO2022067141A1 (en) * | 2020-09-28 | 2022-03-31 | The Procter & Gamble Company | Aqueous compositions comprising hops-metal complex |
US20220313595A1 (en) * | 2021-03-25 | 2022-10-06 | The Procter & Gamble Company | Oral Care Compositions Comprising Hops |
CN115282107A (en) * | 2022-08-23 | 2022-11-04 | 广西壮族自治区药用植物园 | Compound traditional Chinese medicine toothpaste and preparation |
US11918681B2 (en) | 2019-09-30 | 2024-03-05 | The Procter & Gamble Company | Oral care compositions comprising hops beta acid and amino acid |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101297823B1 (en) * | 2010-12-13 | 2013-08-19 | 광주과학기술원 | Pharmaceutical Compositions for Preventing or Treating Periodontal Diseases Comprising Photosensitizers and Pine Resin Extracts as an Active Ingredient Using LED irradiation |
KR101232882B1 (en) * | 2010-12-13 | 2013-02-13 | 광주과학기술원 | Compositions for Improving Oral Hygiene Comprising Photosensitizers and Pine Resin Extracts as an Active Ingredient Using LED Irradiation |
KR101728459B1 (en) | 2015-02-13 | 2017-04-19 | 원광대학교산학협력단 | Rosin based dental composition comprising fluoride for releasing fluoride with long-term sustained release pattern and having antibacterial activity, and manufacturing method thereof |
JP6806388B1 (en) | 2019-12-19 | 2021-01-06 | 株式会社ハニック・ホワイトラボ | An anti-inflammatory liquid composition for covering the oral mucosa, and a pharmaceutical composition for preventing and / or treating aphthous ulcer using the same. |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5370863A (en) * | 1992-12-16 | 1994-12-06 | Miller Brewing Company | Oral care compositions containing hop acids and method |
US6129907A (en) * | 1999-08-04 | 2000-10-10 | Colgate Palmolive Company | Stable hydrogenated lupulone antibacterial oral compositions |
US20040057908A1 (en) * | 2001-12-13 | 2004-03-25 | Bowen William H. | Oral compositions and use thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0466523A (en) * | 1990-07-04 | 1992-03-02 | Kanebo Ltd | Agent for suppressing proliferation of pathogen of periodontosis |
AU2002231030A1 (en) * | 2000-12-13 | 2002-06-24 | Universidade Estadual De Campinas | Oral compositions and use thereof |
-
2005
- 2005-07-20 GB GBGB0514943.0A patent/GB0514943D0/en not_active Ceased
-
2006
- 2006-07-20 AU AU2006269866A patent/AU2006269866A1/en not_active Abandoned
- 2006-07-20 KR KR1020087003591A patent/KR20080043779A/en not_active Application Discontinuation
- 2006-07-20 CA CA002615629A patent/CA2615629A1/en not_active Abandoned
- 2006-07-20 JP JP2008523009A patent/JP2009514789A/en active Pending
- 2006-07-20 WO PCT/US2006/028482 patent/WO2007012080A2/en active Application Filing
- 2006-07-20 EP EP06800225A patent/EP1919438A2/en not_active Withdrawn
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5370863A (en) * | 1992-12-16 | 1994-12-06 | Miller Brewing Company | Oral care compositions containing hop acids and method |
US6129907A (en) * | 1999-08-04 | 2000-10-10 | Colgate Palmolive Company | Stable hydrogenated lupulone antibacterial oral compositions |
US20040057908A1 (en) * | 2001-12-13 | 2004-03-25 | Bowen William H. | Oral compositions and use thereof |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009023920A (en) * | 2007-07-17 | 2009-02-05 | Lion Corp | Antibacterial agent for oral cavity and composition for oral cavity |
WO2021067992A1 (en) * | 2019-09-30 | 2021-04-08 | The Procter & Gamble Company | Methods of use of oral care compositions comprising hops |
CN114466651A (en) * | 2019-09-30 | 2022-05-10 | 宝洁公司 | Methods of using oral care compositions comprising hops |
US11690792B2 (en) | 2019-09-30 | 2023-07-04 | The Procter & Gamble Company | Oral care compositions comprising hops beta acids and metal ions |
US11696881B2 (en) | 2019-09-30 | 2023-07-11 | The Procter & Gamble Company | Oral care compositions comprising hops beta acids and fluoride ions |
US11918681B2 (en) | 2019-09-30 | 2024-03-05 | The Procter & Gamble Company | Oral care compositions comprising hops beta acid and amino acid |
WO2022067141A1 (en) * | 2020-09-28 | 2022-03-31 | The Procter & Gamble Company | Aqueous compositions comprising hops-metal complex |
US20220313595A1 (en) * | 2021-03-25 | 2022-10-06 | The Procter & Gamble Company | Oral Care Compositions Comprising Hops |
CN115282107A (en) * | 2022-08-23 | 2022-11-04 | 广西壮族自治区药用植物园 | Compound traditional Chinese medicine toothpaste and preparation |
Also Published As
Publication number | Publication date |
---|---|
WO2007012080A3 (en) | 2007-05-31 |
GB0514943D0 (en) | 2005-08-24 |
AU2006269866A1 (en) | 2007-01-25 |
KR20080043779A (en) | 2008-05-19 |
CA2615629A1 (en) | 2007-01-25 |
EP1919438A2 (en) | 2008-05-14 |
JP2009514789A (en) | 2009-04-09 |
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