WO2024126876A2 - Antimicrobial compounds for oral care - Google Patents

Antimicrobial compounds for oral care Download PDF

Info

Publication number
WO2024126876A2
WO2024126876A2 PCT/EP2024/058509 EP2024058509W WO2024126876A2 WO 2024126876 A2 WO2024126876 A2 WO 2024126876A2 EP 2024058509 W EP2024058509 W EP 2024058509W WO 2024126876 A2 WO2024126876 A2 WO 2024126876A2
Authority
WO
WIPO (PCT)
Prior art keywords
isosorbide
causing microorganisms
sorbitan
oral care
gingivitis
Prior art date
Application number
PCT/EP2024/058509
Other languages
French (fr)
Inventor
Tom Fricke
Ute Back
Joerg Peter GROHMANN
Petra Riederle
Original Assignee
Clariant International 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 Clariant International Ltd filed Critical Clariant International Ltd
Publication of WO2024126876A2 publication Critical patent/WO2024126876A2/en

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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • 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 the use of certain compounds as antimicrobial agents against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms, as well as to oral care formulations.
  • the present invention also relates to certain compounds for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms, to certain compounds for use in the prevention or treatment of dental caries, dental plaque or gingivitis, to oral care formulations for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms, and to oral care formulations for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
  • Oral care is important for general hygiene and overall well-being.
  • Oral care includes, among others, brushing the teeth with toothpaste and rinsing the mouth with mouthwash.
  • S. mutans Streptococcus mutans
  • S. mutans produces sticky, adhesive glucans and fructans from fermentable sugars, particularly sucrose, which promote the adhesion of bacteria to the oral surfaces.
  • Dental plaque is a sticky biofilm or mass of bacteria that is commonly found on the teeth, along the gum line, and below the gum line margins. Dental plaque can give rise to dental caries and gingivitis.
  • the present invention relates to the use of compound X selected from compounds of Formula (I) wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • the compounds used in the present invention have a high renewable carbon content, i.e. they are sustainable.
  • the compounds used in the present invention can be incorporated into an oral care formulation.
  • compound X selected from compounds of Formula (I) wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • compound X is selected from compounds of Formula (I) wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters.
  • compound X selected from compounds of Formula (I) wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • compound X is selected from compounds of Formula (I) wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.
  • R in Formula (I) is selected from saturated hydrocarbon chains having 5 to 17 carbon atoms, unsaturated hydrocarbon chains having 5 to 17 carbon atoms, and mixtures thereof.
  • R in Formula (I) is selected from saturated hydrocarbon chains having 5 to 13 carbon atoms, unsaturated hydrocarbon chains having 5 to 13 carbon atoms, and mixtures thereof.
  • R in Formula (I) is selected from saturated hydrocarbon chains having 7 to 9 carbon atoms, unsaturated hydrocarbon chains having 7 to 9 carbon atoms, and mixtures thereof.
  • the weight ratio of compounds according to Formula (I) wherein R is - (CH2)eCH3 and compounds according to Formula (I) wherein R is -(CF ⁇ sCHs is from 1 :9 to 9:1 , preferably from 3:7 to 7:3.
  • the weight ratio of compounds according to Formula (I) wherein R is - (CH 2 )IOCH 3 and compounds according to Formula (I) wherein R is -(CH2)i2CH3 is from 1 :9 to 9:1 , preferably from 3:7 to 7:3.
  • the compound of Formula (I) is soluble in water. Therefore, the compound of Formula (I) is suitable for use in mouth wash formulations.
  • compound X selected from glyceryl ethers is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • compound X is selected from glyceryl ethers.
  • the glyceryl ethers are mono- or diethers of glycerin and one or more C6-C20 fatty alcohols. More preferably, the glyceryl ethers are mono- or diethers of glycerin and one or more C8-C14 fatty alcohols. Particularly preferably, the glyceryl ethers are monoethers of glycerin and one or more C8 fatty alcohols.
  • the glyceryl ethers are selected from ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, and mixtures thereof.
  • compound X selected from sorbitan esters and isosorbide esters is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • compound X is selected from sorbitan esters and isosorbide esters.
  • compound X selected from sorbitan esters is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • compound X is selected from sorbitan esters.
  • the sorbitan esters are mono-, di- or triesters of sorbitan and one or more C6-C20 fatty acids. More preferably, the sorbitan esters are mono- or diesters of sorbitan and one or more C8-C14 fatty acids. Particularly preferably, the sorbitan esters are mono- or diesters of sorbitan and caprylic acid.
  • the sorbitan esters are selected from sorbitan caprylate, sorbitan stearate, sorbitan olivate, sorbitan oleate, sorbitan caprate, sorbitan laurate, sorbitan myristate, sorbitan caproate, and mixtures thereof. Particularly preferably, the sorbitan ester is sorbitan caprylate.
  • compound X selected from isosorbide esters is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • compound X is selected from isosorbide esters.
  • the isosorbide esters are mono- or diesters of isosorbide and one or more C6-C20 fatty acids. More preferably, the isosorbide esters are mono- or diesters of isosorbide and one or more C8-C14 fatty acids. Particularly preferably, the isosorbide esters are mono- or diesters of isosorbide and caprylic acid.
  • the isosorbide esters are selected from isosorbide caprylate, isosorbide stearate, isosorbide olivate, isosorbide oleate, isosorbide caprate, isosorbide laurate, isosorbide myristate, isosorbide caproate, and mixtures thereof.
  • the isosorbide ester is isosorbide caprylate.
  • compound X is suitable for use in toothpaste formulations.
  • compound X as defined herein is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • microorganisms are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
  • the dental caries causing microorganisms are dental caries causing bacteria.
  • the dental plaque causing microorganisms are dental plaque causing bacteria.
  • the gingivitis causing microorganisms are gingivitis causing bacteria.
  • compound X as defined herein is used as an antibacterial agent against dental caries causing bacteria, dental plaque causing bacteria or gingivitis causing bacteria.
  • examples of such bacteria are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
  • Streptococcus mutans, Streptococcus sanguinis and Streptococcus sobrinus are film formers.
  • Streptococcus gordonii is a film former and an acid former.
  • Lactobacillus acidophilus is an acid former. It attacks the dental enamel. Fusobacterium nucleatum is a film former. Porphyromonas gingivalis is responsible for periodentosis.
  • compound X as defined herein is used in combination with a further antimicrobial agent.
  • the antimicrobial agent is selected from the group consisting of: aromatic alcohols, organic acids and salts thereof, hydroxamic acids and salts thereof, hydroxyacetophenone, compounds according to Formula (P), alkyl diols, halogenated compounds, isothiazolinones, and mixtures thereof; wherein Formula (P) is as follows:
  • R1 is H, an unsubstituted or halogen-substituted, branched or unbranched C-i- C2o-alkyl radical, an unsubstituted or halogen-substituted Cs-Cs-cycloalkyl radical, an unsubstituted or halogen-substituted Ce-C -aryl radical or an unsubstituted or halogen-substituted, branched or unbranched C7-C20- aralkyl radical;
  • R2’ is 0 or S
  • R3’ is H or a Ci-C4-alkyl radical
  • X + is a cation
  • R3' is methyl
  • the aromatic alcohols are selected from the group consisting of benzyl alcohol, phenoxyethanol, veratryl alcohol, propylene phenoxyethanol, phenethyl alcohol, phenylpropanol, vanillin, 2-methyl-1 -phenyl- 2-propanol, and mixtures thereof.
  • the organic acids and salts thereof are selected from the group consisting of benzoic acid, sorbic acid, dehydroacetic acid, lactic acid, salicylic acid, p-anisic acid, undecylenic acid, glycolic acid, propionic acid, levulinic acid, and mixtures thereof.
  • the hydroxamic acid is selected from hydroxamic acids of Formula (III) wherein R 1 is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.
  • R 1 in Formula (III) is selected from saturated hydrocarbon chains having 5 to 17 carbon atoms, unsaturated hydrocarbon chains having 5 to 17 carbon atoms, and mixtures thereof. More preferably, R 1 in Formula (III) is selected from saturated hydrocarbon chains having 5 to 13 carbon atoms, unsaturated hydrocarbon chains having 5 to 13 carbon atoms, and mixtures thereof. Particularly preferably, R 1 in Formula (III) is selected from saturated hydrocarbon chains having 7 carbon atoms, unsaturated hydrocarbon chains having 7 carbon atoms, and mixtures thereof.
  • Preferred hydroxamic acids are selected from caprylhydroxamic acid, hexanohydroxamic acid, caprohydroxamic acid, laurohydroxamic acid, and mixtures thereof.
  • a particularly preferred hydroxamic acid is caprylhydroxamic acid.
  • Caprylhydroxamic acid may also be referred to as caprylohydroxamic acid or octanohydroxamic acid.
  • Hydroxamic acids are described in, e.g., EP2224973.
  • salts of hydroxamic acids are alkali metal salts of hydroxamic acids (e.g. sodium salts of hydroxamic acids or potassium salts of hydroxamic acids) or alkaline earth metal salts of hydroxamic acids (e.g. magnesium salts of hydroxamic acids or calcium salts of hydroxamic acids).
  • the compound according to Formula (P) is selected from the group consisting of 2-hydroxypyridine-N-oxide, 2-pyridinethiol-1 -oxide and salts thereof, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1 H)-pyridone and salts thereof (preferably the monoethanolamine salt), and mixtures thereof.
  • Formula (P) discloses and encompasses the tautomeric equivalents of these compounds, since an equilibrium always exists.
  • the compound according to Formula (P) is piroctone olamine (Octopirox).
  • the alkyl diols are selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,6-hexanediol, 1 ,2-octanediol, 1 ,2- heptanediol, 1 ,2-decanediol, methylpropanediol, and mixtures thereof.
  • the halogenated compounds are selected from the group consisting of chlorhexidine and salts thereof, triclosan, chlorphenesin, trichlorcarban, chloroxylenol, bronopol, climbazole, and mixtures thereof.
  • the isothiazolinones are selected from the group consisting of methylisothiazolinone, methylchloroisothiazolinone, benzylisothiazolinone, and mixtures thereof.
  • the antimicrobial agent is selected from the group consisting of aromatic alcohols, organic acids and salts thereof, hydroxamic acids and salts thereof, hydroxyacetophenone, hydroxypyridones, alkyl diols, halogenated compounds, isothiazolinones, and mixtures thereof.
  • the antimicrobial agent is selected from the group consisting of phenoxyethanol, benzyl alcohol, phenethyl alcohol, benzoic acid and salts thereof, caprylhydroxamic acid, hydroxyacetophenone, piroctone olamine, and mixtures thereof.
  • the antimicrobial agent is 1 ,2-octanediol, in particular bio-based 1 ,2-octanediol, for example bio-1 ,2-octanediol as disclosed in WO 2019/152569.
  • Suitable antimicrobial agents are also listed in Annex V (updated on 28/2022) of the REGULATION (EC) No 1223/2009 OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 30 November 2009 on cosmetic products.
  • the weight ratio of compound X as defined herein to the further antimicrobial agent, if present, is from 20:1 to 1 :20, more preferably from 15:1 to 1 :15, even more preferably from 10:1 to 1 :10, particularly preferably from 5:1 to 1 :5, for example 1 :1.
  • the present invention also relates to an oral care formulation comprising from 0.1 to 20 wt.-%, preferably from 0.2 to 10 wt.-%, more preferably from 0.3 to 5 wt.-%, even more preferably from 0.4 to 3 wt.-%, particularly preferably from 0.5 to 2 wt.-%, based on the total weight of the oral care formulation, of compound X as defined herein.
  • the oral care formulation is selected from the group consisting of toothpaste, oral gel, mouth wash, tooth powder and chewing gum.
  • the oral care formulation is selected from the group consisting of toothpaste and mouth wash.
  • the oral care formulation is a toothpaste.
  • the oral care formulation is a mouth wash.
  • the oral care formulation comprises a solvent.
  • the solvent is preferably selected from water, propylene glycol, isopropanol, and mixtures thereof.
  • the oral care formulation comprises a humectant.
  • the humectant is preferably selected from sorbitol, glycerol, xylitol, and mixtures thereof.
  • the humectant may, for example, be present in an amount of from 10 to 70 wt.-%, preferably from 30 to 60 wt.-%, for example from 40 to 55 wt.-%, based on the total weight of the oral care formulation.
  • the oral care formulation comprises an abrasive.
  • the abrasive is preferably selected from silica abrasives, hydrated silica, hydrated alumina, calcium abrasives, tricalcium phosphate, hydroxyapatite, dicalcium phosphate dihydrate, calcium pyrophosphate, calcium carbonate, sodium metaphosphate, potassium metaphosphate, aluminum silicate, calcined alumina, bentonite, sodium bicarbonate, and mixtures thereof.
  • the abrasive may, for example, be present in an amount of from 10 to 30 wt.-%, preferably from 15 to 25 wt.-%, based on the total weight of the oral care formulation.
  • the oral care formulation comprises an anticalculus agent.
  • the anticalculus agent is preferably selected from phosphates, polyphosphates, pyrophosphates, e.g. tetrasodium pyrophosphate, polyaminopropanesulfonic acid, hexametaphosphate salts, zinc citrate trihydrate, polypeptides, polyolefin sulfonates, polyolefin phosphates, diphosphonates, and mixtures thereof.
  • the anticalculus agent may, for example, be present in an amount of from 0.01 to 20 wt.-%, preferably from 0.1 to 10 wt.-%, based on the total weight of the oral care formulation.
  • the oral care formulation comprises a fluoride source.
  • the fluoride source is preferably selected from stannous fluoride, sodium fluoride, potassium fluoride, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride, ammonium fluoride, calcium fluoride, aluminum fluoride, fluorohydroxyapatite, and mixtures thereof.
  • the fluoride source is preferably selected from stannous fluoride, sodium fluoride, potassium fluoride, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride, ammonium fluoride, and mixtures thereof.
  • the fluoride source may, for example, be present in an amount of from 0.01 to 10 wt.-%, preferably from 0.1 to 2 wt.-%, based on the total weight of the oral care formulation.
  • the fluoride source may, for example, be present in an amount of from 0.01 to 1 wt.-%, preferably from 0.02 to 0.5 wt.-%, more preferably from 0.03 to 0.3 wt.-%, even more preferably from 0.04 to 0.2 wt.-%, particularly preferably from 0.05 to 0.15 wt.-%, based on the total weight of the oral care formulation.
  • the fluoride source may, for example, be present in an amount of from 0.01 to 0.15 wt.-%, preferably from 0.02 to 0.15 wt.-%, more preferably from 0.03 to 0.15 wt.-%, even more preferably from 0.04 to 0.15 wt.-%, particularly preferably from 0.05 to 0.15 wt.-%, based on the total weight of the oral care formulation.
  • the oral care formulation is a toothpaste
  • the toothpaste comprises a fluoride source.
  • the oral care formulation comprises a polymer.
  • the polymer is preferably selected from polyethylene glycols, polysaccharides, for example cellulose derivatives, for example carboxymethyl cellulose, hydroxymethyl cellulose, ethyl cellulose, microcrystalline cellulose, or polysaccharide gums, for example xanthan gum, guar gum or carrageenan gum, or polyacrylates or polymers based on N-vinylpyrrolidone, and mixtures thereof.
  • the polymer may, for example, be present in an amount of from 0.1 to 10 wt.-%, preferably from 0.5 to 5 wt.-%, based on the total weight of the oral care formulation.
  • the oral care formulation comprises an anionic polymer.
  • the anionic polymer is preferably selected from polycarboxylates, polyacrylic acids, polyacrylates, polyphosphonic acids, cross-linked carboxyvinyl copolymers, and mixtures thereof.
  • the anionic polymer may, for example, be present in an amount of from 1 to 20 wt.-%, preferably from 5 to 15 wt.-%, based on the total weight of the oral care formulation.
  • the oral care formulation comprises a thickening agent.
  • the thickening agent is preferably selected from silica thickening agents, carboxy vinyl polymers, carrageenan, hydroxyethyl cellulose, salts of cellulose ethers such as sodium carboxymethyl cellulose or sodium carboxymethyl hydroxyethyl cellulose, karaya, gum arabic, gum tragacanth, colloidal magnesium aluminum silicate, and mixtures thereof.
  • the thickening agent may, for example, be present in an amount of from 0.1 to 10 wt.-%, preferably from 0.5 to 5 wt.-%, based on the total weight of the oral care formulation.
  • the oral care formulation comprises a foaming agent.
  • the foaming agent is preferably selected from polyethylene glycol, alginate polymers, and mixtures thereof.
  • the foaming agent may, for example, be present in an amount of from 0.1 to 20 wt.-%, preferably from 1 to 10 wt.-%, based on the total weight of the oral care formulation.
  • the oral care formulation comprises a surfactant.
  • the surfactant may, for example, be present in an amount of from 0.1 to 20 wt.-%, preferably from 1 to 10 wt.-%, based on the total weight of the oral care formulation.
  • the surfactant is an anionic surfactant.
  • the anionic surfactant is preferably selected from alkyl sulfates, for example sodium lauryl sulfate, alkyl ether sulfates, for example sodium laureth-2 sulfate, alkyl aryl sulfonates, for example sodium lauryl benzene sulfonate, alkyl sulfoacetates, for example sodium lauryl sulfoacetate, and mixtures thereof.
  • the surfactant is a sulfur-free anionic surfactant.
  • the sulfur-free anionic surfactant is preferably selected from taurates, for example sodium methyl cocoyl taurate, glycinates, for example sodium cocoyl glycinate, sarcosinates, for example sodium lauroyl sarcosinate, quaternary ammonium compounds, for example benzalkonium chloride or cetylpyridinium chloride, and mixtures thereof.
  • the surfactant is a non-ionic surfactant.
  • the surfactant is a glucamide.
  • the surfactant is a glucamide of Formula X: wherein R is selected from saturated or unsaturated hydrocarbon chains having 5 to 23 carbon atoms.
  • R in Formula (X) is selected from saturated or unsaturated hydrocarbon chains having 7 to 17 carbon atoms.
  • glucamides of Formula (X) are capryloyl/caproyl methyl glucamide, lauroyl/myristoyl methyl glucamide, cocoyl methyl glucamide, oleyl methyl glucamide, or mixtures thereof.
  • Such glucamides are commercially available from Clariant (GlucoTain® Clear, GlucoTain® Plus, GlucoTain® Flex, GlucoTain® Care, GlucoTain® Sense).
  • glucamides of Formula (X) are N-9-decenoyl-N- methylglucamine, N-9-dodecenoyl-N-methylglucamine, or mixtures thereof.
  • the surfactant is an alkyl polyglycoside (APG), preferably an alkyl polyglucoside.
  • APG alkyl polyglycoside
  • the surfactant is a zwitterionic surfactant, for example a betaine surfactant, for example cocam idopropyl betaine. In one embodiment, the surfactant is a cationic surfactant.
  • the oral care formulation comprises a buffer or pH adjusting agent.
  • the oral care formulation has a pH in the range of from 4 to 8, preferably from 4.5 to 7.5, more preferably from 5 to 7, particularly preferably from 5 to 6, also particularly preferably from 5.5 to 6.5, also particularly preferably from 6 to 7.
  • the oral care formulation is a toothpaste, and the toothpaste has a pH in the range of from 4 to 8, preferably from 4.5 to 7.5, more preferably from 5 to 7, particularly preferably from 5 to 6, also particularly preferably from 5.5 to 6.5, also particularly preferably from 6 to 7.
  • the oral care formulation comprises a flavoring agent, sweetening agent, and/or pigment or dye.
  • flavors are mint, peppermint, spearmint, Wintergreen, menthol, or strawberry.
  • An example of a sweetening agent is sodium saccharin.
  • pigments are titanium dioxide or zinc oxide.
  • the oral care formulation may, for example, be prepared by mixing its ingredients.
  • the present invention also relates to compound X selected from compounds of Formula (I) wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • microorganisms examples include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
  • the dental caries causing microorganisms are dental caries causing bacteria.
  • the dental plaque causing microorganisms are dental plaque causing bacteria.
  • the gingivitis causing microorganisms are gingivitis causing bacteria.
  • a preferred embodiment relates to compound X selected from compounds of Formula (I) wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters for use in reducing the effects of dental caries causing bacteria, dental plaque causing bacteria or gingivitis causing bacteria.
  • bacteria examples include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
  • the present invention also relates to an oral care formulation as defined herein for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
  • microorganisms examples include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L. acidophilus).
  • the dental caries causing microorganisms are dental caries causing bacteria.
  • the dental plaque causing microorganisms are dental plaque causing bacteria.
  • the gingivitis causing microorganisms are gingivitis causing bacteria.
  • a preferred embodiment relates to an oral care formulation as defined herein for use in reducing the effects of dental caries causing bacteria, dental plaque causing bacteria or gingivitis causing bacteria.
  • examples of such bacteria are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
  • the present invention also relates to compound X selected from compounds of Formula (I) wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
  • R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
  • microorganisms examples include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L. acidophilus).
  • the dental caries causing microorganisms are dental caries causing bacteria.
  • the dental plaque causing microorganisms are dental plaque causing bacteria.
  • the gingivitis causing microorganisms are gingivitis causing bacteria.
  • a preferred embodiment relates to compound X selected from compounds of Formula (I) wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
  • bacteria examples include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
  • the present invention also relates to an oral care formulation as defined herein for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
  • microorganisms examples include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L. acidophilus).
  • the dental caries causing microorganisms are dental caries causing bacteria.
  • the dental plaque causing microorganisms are dental plaque causing bacteria.
  • the gingivitis causing microorganisms are gingivitis causing bacteria.
  • a preferred embodiment relates to an oral care formulation as defined herein for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
  • bacteria examples include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
  • the present invention also relates to a method of reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms, wherein the method comprises contacting the dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms with compound X as defined herein or an oral care formulation as defined herein.
  • microorganisms are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L. acidophilus).
  • the dental caries causing microorganisms are dental caries causing bacteria.
  • the dental plaque causing microorganisms are dental plaque causing bacteria.
  • the gingivitis causing microorganisms are gingivitis causing bacteria.
  • a preferred embodiment relates to a method of reducing the effects of dental caries causing bacteria, dental plaque causing bacteria or gingivitis causing bacteria, wherein the method comprises contacting the dental caries causing bacteria, dental plaque causing bacteria or gingivitis causing bacteria with compound X as defined herein or an oral care formulation as defined herein.
  • examples of such bacteria are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis.
  • Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
  • the present invention also relates to a method of prevention or treatment of dental caries, dental plaque or gingivitis, wherein the method comprises contacting the oral cavity of a subject in need thereof with compound X as defined herein or an oral care formulation as defined herein.
  • the present invention also relates to the use of compound X as defined herein or an oral care formulation as defined herein for the prevention or treatment of dental caries, dental plaque or gingivitis.
  • Molecular weight or “M.Wt.” or “MW’ and grammatical equivalents mean the number average molecular weight.
  • Viscosity is measured at 25°C using a HAAKE Rotation Viscometer VT 550 with cooling/heating vessel and sensor systems according to DIN 53019 at a shear rate of 12.9 s- 1 .
  • Water-soluble refers to any material that is sufficiently soluble in water to form a clear solution to the naked eye at a concentration of 0.1 % by weight of the material in water at 25°C.
  • water-insoluble refers to any material that is not “water-soluble”.
  • “Dry” or “substantially dry” means comprising less than 5 %, less than 3 %, less than 2 %, less than 1 %, or about 0 % of any compound or composition being in liquid form when measured at 25°C at ambient conditions. Such compounds or compositions being in liquid form include water, oils, organic solvents and other wetting agents. 'Anhydrous" means that the composition comprises less than 5 %, less than 3 %, less than 2 %, less than 1 %, or about 0 % water by total weight of the composition.
  • “Substantially free from” or “substantially free of” means less than 1 %, or less than 0.8 %, or less than 0.5 %, or less than 0.3 %, or about 0 %, by total weight of the composition.
  • “Derivatives” includes but is not limited to amide, ether, ester, amino, carboxyl, acetyl, acid, salt and/or alcohol derivatives of a given compound. In at least one embodiment, “derivatives thereof” means the amide, ether, ester, amino, carboxyl, acetyl, acid, salt and alcohol derivatives.
  • Capryloyl/Caproyl Anhydro Methyl Glucamide is a mixture of compounds of Formula (I) wherein R is -(CFhjsCHs and compounds of Formula (I) wherein R is - (CH 2 ) 6 CH 3 .
  • Velsan® EHG is commercially available from Clariant. Chemical name: Ethylhexylglycerin.
  • Example 1 Microbiological test
  • microbiological test was carried out according to BS EN 1040:2005.
  • sample solutions 1 . 1 %, 2%, 3% and 5% sample solutions were prepared in sterilized tap water.
  • Example 2 Examples of toothpaste formulations (amounts are given in wt-%)
  • Example 3 Examples of toothpaste formulations (amounts are given in wt-%)
  • Example 4 Examples of toothpaste formulations (amounts are given in wt-%)
  • Example 5 Examples of toothpaste formulations (amounts are given in wt-%)
  • Example 6 Examples of toothpaste formulations (amounts are given in wt-%)
  • Example 7 Example of a mouthwash formulation (amounts are given in wt-%)
  • the reducing effect of toothpaste samples on biofilm-forming bacteria such as streptococci was tested over a period of up to 5 minutes.
  • a biofilm of the test bacteria (Streptococcus mutans) was cultured, and then the toothpaste solution (40% toothpaste in tap water) was applied to the biofilm. After the elapsed time, the reducing effect was quantified by determining the number of germs.
  • a control with tap water serves as a reference to rule out that the tap water influences the bacteria.

Landscapes

  • 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)
  • Emergency Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)

Abstract

The present invention relates to the use of compound X selected from compounds of Formula (I) wherein R is selected from saturated hydrocarbon chains having to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.

Description

ANTIMICROBIAL COMPOUNDS FOR ORAL CARE
The present invention relates to the use of certain compounds as antimicrobial agents against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms, as well as to oral care formulations. The present invention also relates to certain compounds for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms, to certain compounds for use in the prevention or treatment of dental caries, dental plaque or gingivitis, to oral care formulations for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms, and to oral care formulations for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
Oral care is important for general hygiene and overall well-being. Oral care includes, among others, brushing the teeth with toothpaste and rinsing the mouth with mouthwash.
Dental caries is caused by the production of acid by certain bacteria, including Streptococcus mutans (S. mutans). S. mutans produces sticky, adhesive glucans and fructans from fermentable sugars, particularly sucrose, which promote the adhesion of bacteria to the oral surfaces.
Dental plaque is a sticky biofilm or mass of bacteria that is commonly found on the teeth, along the gum line, and below the gum line margins. Dental plaque can give rise to dental caries and gingivitis.
There is an ongoing need for antimicrobial agents that can be used in oral care formulations.
It has been found that certain compounds are useful as antimicrobial agents against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms. Accordingly, the present invention relates to the use of compound X selected from compounds of Formula (I)
Figure imgf000003_0001
wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
Advantageously, the compounds used in the present invention have a high renewable carbon content, i.e. they are sustainable. The compounds used in the present invention can be incorporated into an oral care formulation.
According to the invention, compound X selected from compounds of Formula (I)
Figure imgf000003_0002
wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
According to the invention, compound X is selected from compounds of Formula (I)
Figure imgf000004_0001
wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters.
In one embodiment, compound X selected from compounds of Formula (I)
Figure imgf000004_0002
wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
In one embodiment, compound X is selected from compounds of Formula (I)
Figure imgf000005_0001
wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.
Preferably, R in Formula (I) is selected from saturated hydrocarbon chains having 5 to 17 carbon atoms, unsaturated hydrocarbon chains having 5 to 17 carbon atoms, and mixtures thereof.
More preferably, R in Formula (I) is selected from saturated hydrocarbon chains having 5 to 13 carbon atoms, unsaturated hydrocarbon chains having 5 to 13 carbon atoms, and mixtures thereof.
Particularly preferably, R in Formula (I) is selected from saturated hydrocarbon chains having 7 to 9 carbon atoms, unsaturated hydrocarbon chains having 7 to 9 carbon atoms, and mixtures thereof.
In at least one embodiment, R in Formula (I) is selected from -(CF^eCHs, - (CH2)8CH3, and mixtures thereof; or R in Formula (I) is selected from -(CH2)-IOCH3, -(CH2)i2CH3, and mixtures thereof; or R in Formula (I) is selected from - (CH2)?CH=CH2, -(CH2)7CH=CHCH2CH3, and mixtures thereof; or the R-C=O residue in Formula (I) is derived from coconut fatty acids; or the R-C=O residue in Formula (I) is derived from soybean fatty acids.
In at least one embodiment, R in Formula (I) is selected from -(CF^eCF , - (CH2)8CH3, and mixtures thereof. In at least one embodiment, R in Formula (I) is selected from -(CH2)-IOCH3, -(CH2)i2CH3, and mixtures thereof. In at least one embodiment, R in Formula (I) is selected from -(CH2)?CH=CH2, - (CH2)7CH=CHCH2CH3, and mixtures thereof. In at least one embodiment, the R- C=O residue in Formula (I) is derived from coconut fatty acids. In at least one embodiment, the R-C=O residue in Formula (I) is derived from soybean fatty acids.
As used herein, the expression “the R-C=O residue in Formula (I) is derived from coconut fatty acids” preferably means that the carbon chain length distribution in the R-C=O residue in Formula (I) corresponds to the carbon chain length distribution of the fatty acids (e.g. bound as triglycerides) in coconut oil.
As used herein, the expression “the R-C=O residue in Formula (I) is derived from soybean fatty acids” preferably means that the carbon chain length distribution in the R-C=O residue in Formula (I) corresponds to the carbon chain length distribution of the fatty acids (e.g. bound as triglycerides) in soybean oil.
Preferably, the weight ratio of compounds according to Formula (I) wherein R is - (CH2)eCH3 and compounds according to Formula (I) wherein R is -(CF^sCHs is from 1 :9 to 9:1 , preferably from 3:7 to 7:3.
Preferably, the weight ratio of compounds according to Formula (I) wherein R is - (CH2)IOCH3 and compounds according to Formula (I) wherein R is -(CH2)i2CH3 is from 1 :9 to 9:1 , preferably from 3:7 to 7:3.
Preferably, the weight ratio of compounds according to Formula (I) wherein R is - (CH2)?CH=CH2 and compounds according to Formula (I) wherein R is - (CH2)?CH=CHCH2CH3 is from 1 :9 to 9:1 , preferably from 3:7 to 7:3.
Advantageously, the compound of Formula (I) is soluble in water. Therefore, the compound of Formula (I) is suitable for use in mouth wash formulations.
Compounds of Formula (I) are described in, e.g., WO 2018/002100 and EP application number EP21200587.0.
In one embodiment, compound X selected from glyceryl ethers is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
In one embodiment, compound X is selected from glyceryl ethers.
Preferably, the glyceryl ethers are mono- or diethers of glycerin and one or more C6-C20 fatty alcohols. More preferably, the glyceryl ethers are mono- or diethers of glycerin and one or more C8-C14 fatty alcohols. Particularly preferably, the glyceryl ethers are monoethers of glycerin and one or more C8 fatty alcohols.
In at least one embodiment, the glyceryl ethers are selected from ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, and mixtures thereof.
In one embodiment, compound X selected from sorbitan esters and isosorbide esters is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
In one embodiment, compound X is selected from sorbitan esters and isosorbide esters.
In one embodiment, compound X selected from sorbitan esters is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
In one embodiment, compound X is selected from sorbitan esters.
Preferably, the sorbitan esters are mono-, di- or triesters of sorbitan and one or more C6-C20 fatty acids. More preferably, the sorbitan esters are mono- or diesters of sorbitan and one or more C8-C14 fatty acids. Particularly preferably, the sorbitan esters are mono- or diesters of sorbitan and caprylic acid. Preferably, the sorbitan esters are selected from sorbitan caprylate, sorbitan stearate, sorbitan olivate, sorbitan oleate, sorbitan caprate, sorbitan laurate, sorbitan myristate, sorbitan caproate, and mixtures thereof. Particularly preferably, the sorbitan ester is sorbitan caprylate.
In one embodiment, compound X selected from isosorbide esters is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
In one embodiment, compound X is selected from isosorbide esters.
Preferably, the isosorbide esters are mono- or diesters of isosorbide and one or more C6-C20 fatty acids. More preferably, the isosorbide esters are mono- or diesters of isosorbide and one or more C8-C14 fatty acids. Particularly preferably, the isosorbide esters are mono- or diesters of isosorbide and caprylic acid.
Preferably, the isosorbide esters are selected from isosorbide caprylate, isosorbide stearate, isosorbide olivate, isosorbide oleate, isosorbide caprate, isosorbide laurate, isosorbide myristate, isosorbide caproate, and mixtures thereof. Particularly preferably, the isosorbide ester is isosorbide caprylate.
Advantageously, compound X is suitable for use in toothpaste formulations.
According to the invention, compound X as defined herein is used as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms. Examples of such microorganisms are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
In a preferred embodiment, the dental caries causing microorganisms are dental caries causing bacteria. In a preferred embodiment, the dental plaque causing microorganisms are dental plaque causing bacteria. In a preferred embodiment, the gingivitis causing microorganisms are gingivitis causing bacteria.
In a preferred embodiment, compound X as defined herein is used as an antibacterial agent against dental caries causing bacteria, dental plaque causing bacteria or gingivitis causing bacteria. Examples of such bacteria are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
Streptococcus mutans, Streptococcus sanguinis and Streptococcus sobrinus are film formers. Streptococcus gordonii is a film former and an acid former.
Lactobacillus acidophilus is an acid former. It attacks the dental enamel. Fusobacterium nucleatum is a film former. Porphyromonas gingivalis is responsible for periodentosis.
Optionally, compound X as defined herein is used in combination with a further antimicrobial agent.
In at least one embodiment, the antimicrobial agent is selected from the group consisting of: aromatic alcohols, organic acids and salts thereof, hydroxamic acids and salts thereof, hydroxyacetophenone, compounds according to Formula (P), alkyl diols, halogenated compounds, isothiazolinones, and mixtures thereof; wherein Formula (P) is as follows:
Figure imgf000009_0001
O‘X + wherein R1 ’ is H, an unsubstituted or halogen-substituted, branched or unbranched C-i- C2o-alkyl radical, an unsubstituted or halogen-substituted Cs-Cs-cycloalkyl radical, an unsubstituted or halogen-substituted Ce-C -aryl radical or an unsubstituted or halogen-substituted, branched or unbranched C7-C20- aralkyl radical;
R2’ is 0 or S;
R3’ is H or a Ci-C4-alkyl radical;
X+ is a cation.
Preferably, R3' is methyl.
In at least one embodiment, the aromatic alcohols are selected from the group consisting of benzyl alcohol, phenoxyethanol, veratryl alcohol, propylene phenoxyethanol, phenethyl alcohol, phenylpropanol, vanillin, 2-methyl-1 -phenyl- 2-propanol, and mixtures thereof.
In at least one embodiment, the organic acids and salts thereof are selected from the group consisting of benzoic acid, sorbic acid, dehydroacetic acid, lactic acid, salicylic acid, p-anisic acid, undecylenic acid, glycolic acid, propionic acid, levulinic acid, and mixtures thereof.
In at least one embodiment, the hydroxamic acid is selected from hydroxamic acids of Formula (III)
Figure imgf000010_0001
wherein R1 is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.
Preferably, R1 in Formula (III) is selected from saturated hydrocarbon chains having 5 to 17 carbon atoms, unsaturated hydrocarbon chains having 5 to 17 carbon atoms, and mixtures thereof. More preferably, R1 in Formula (III) is selected from saturated hydrocarbon chains having 5 to 13 carbon atoms, unsaturated hydrocarbon chains having 5 to 13 carbon atoms, and mixtures thereof. Particularly preferably, R1 in Formula (III) is selected from saturated hydrocarbon chains having 7 carbon atoms, unsaturated hydrocarbon chains having 7 carbon atoms, and mixtures thereof.
Preferred hydroxamic acids are selected from caprylhydroxamic acid, hexanohydroxamic acid, caprohydroxamic acid, laurohydroxamic acid, and mixtures thereof. A particularly preferred hydroxamic acid is caprylhydroxamic acid. Caprylhydroxamic acid may also be referred to as caprylohydroxamic acid or octanohydroxamic acid. Hydroxamic acids are described in, e.g., EP2224973.
Examples of salts of hydroxamic acids are alkali metal salts of hydroxamic acids (e.g. sodium salts of hydroxamic acids or potassium salts of hydroxamic acids) or alkaline earth metal salts of hydroxamic acids (e.g. magnesium salts of hydroxamic acids or calcium salts of hydroxamic acids).
In at least one embodiment, the compound according to Formula (P) is selected from the group consisting of 2-hydroxypyridine-N-oxide, 2-pyridinethiol-1 -oxide and salts thereof, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1 H)-pyridone and salts thereof (preferably the monoethanolamine salt), and mixtures thereof. Formula (P) discloses and encompasses the tautomeric equivalents of these compounds, since an equilibrium always exists. In at least one embodiment, the compound according to Formula (P) is piroctone olamine (Octopirox).
In at least one embodiment, the alkyl diols are selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,6-hexanediol, 1 ,2-octanediol, 1 ,2- heptanediol, 1 ,2-decanediol, methylpropanediol, and mixtures thereof.
In at least one embodiment, the halogenated compounds are selected from the group consisting of chlorhexidine and salts thereof, triclosan, chlorphenesin, trichlorcarban, chloroxylenol, bronopol, climbazole, and mixtures thereof. In at least one embodiment, the isothiazolinones are selected from the group consisting of methylisothiazolinone, methylchloroisothiazolinone, benzylisothiazolinone, and mixtures thereof.
In at least one embodiment, the antimicrobial agent is selected from the group consisting of aromatic alcohols, organic acids and salts thereof, hydroxamic acids and salts thereof, hydroxyacetophenone, hydroxypyridones, alkyl diols, halogenated compounds, isothiazolinones, and mixtures thereof.
In at least one embodiment, the antimicrobial agent is selected from the group consisting of phenoxyethanol, benzyl alcohol, phenethyl alcohol, benzoic acid and salts thereof, caprylhydroxamic acid, hydroxyacetophenone, piroctone olamine, and mixtures thereof.
In a preferred embodiment, the antimicrobial agent is 1 ,2-octanediol, in particular bio-based 1 ,2-octanediol, for example bio-1 ,2-octanediol as disclosed in WO 2019/152569.
Suitable antimicrobial agents are also listed in Annex V (updated on 28/09/2022) of the REGULATION (EC) No 1223/2009 OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 30 November 2009 on cosmetic products.
Preferably, the weight ratio of compound X as defined herein to the further antimicrobial agent, if present, is from 20:1 to 1 :20, more preferably from 15:1 to 1 :15, even more preferably from 10:1 to 1 :10, particularly preferably from 5:1 to 1 :5, for example 1 :1.
The present invention also relates to an oral care formulation comprising from 0.1 to 20 wt.-%, preferably from 0.2 to 10 wt.-%, more preferably from 0.3 to 5 wt.-%, even more preferably from 0.4 to 3 wt.-%, particularly preferably from 0.5 to 2 wt.-%, based on the total weight of the oral care formulation, of compound X as defined herein. In a preferred embodiment, the oral care formulation is selected from the group consisting of toothpaste, oral gel, mouth wash, tooth powder and chewing gum. In a more preferred embodiment, the oral care formulation is selected from the group consisting of toothpaste and mouth wash. In a particularly preferred embodiment, the oral care formulation is a toothpaste. In another particularly preferred embodiment, the oral care formulation is a mouth wash.
In one embodiment, the oral care formulation comprises a solvent. The solvent is preferably selected from water, propylene glycol, isopropanol, and mixtures thereof.
In one embodiment, the oral care formulation comprises a humectant. The humectant is preferably selected from sorbitol, glycerol, xylitol, and mixtures thereof.
The humectant may, for example, be present in an amount of from 10 to 70 wt.-%, preferably from 30 to 60 wt.-%, for example from 40 to 55 wt.-%, based on the total weight of the oral care formulation.
In one embodiment, the oral care formulation comprises an abrasive. The abrasive is preferably selected from silica abrasives, hydrated silica, hydrated alumina, calcium abrasives, tricalcium phosphate, hydroxyapatite, dicalcium phosphate dihydrate, calcium pyrophosphate, calcium carbonate, sodium metaphosphate, potassium metaphosphate, aluminum silicate, calcined alumina, bentonite, sodium bicarbonate, and mixtures thereof.
The abrasive may, for example, be present in an amount of from 10 to 30 wt.-%, preferably from 15 to 25 wt.-%, based on the total weight of the oral care formulation.
In one embodiment, the oral care formulation comprises an anticalculus agent.
The anticalculus agent is preferably selected from phosphates, polyphosphates, pyrophosphates, e.g. tetrasodium pyrophosphate, polyaminopropanesulfonic acid, hexametaphosphate salts, zinc citrate trihydrate, polypeptides, polyolefin sulfonates, polyolefin phosphates, diphosphonates, and mixtures thereof. The anticalculus agent may, for example, be present in an amount of from 0.01 to 20 wt.-%, preferably from 0.1 to 10 wt.-%, based on the total weight of the oral care formulation.
In one embodiment, the oral care formulation comprises a fluoride source. The fluoride source is preferably selected from stannous fluoride, sodium fluoride, potassium fluoride, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride, ammonium fluoride, calcium fluoride, aluminum fluoride, fluorohydroxyapatite, and mixtures thereof. The fluoride source is preferably selected from stannous fluoride, sodium fluoride, potassium fluoride, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride, ammonium fluoride, and mixtures thereof.
The fluoride source may, for example, be present in an amount of from 0.01 to 10 wt.-%, preferably from 0.1 to 2 wt.-%, based on the total weight of the oral care formulation. The fluoride source may, for example, be present in an amount of from 0.01 to 1 wt.-%, preferably from 0.02 to 0.5 wt.-%, more preferably from 0.03 to 0.3 wt.-%, even more preferably from 0.04 to 0.2 wt.-%, particularly preferably from 0.05 to 0.15 wt.-%, based on the total weight of the oral care formulation. The fluoride source may, for example, be present in an amount of from 0.01 to 0.15 wt.-%, preferably from 0.02 to 0.15 wt.-%, more preferably from 0.03 to 0.15 wt.-%, even more preferably from 0.04 to 0.15 wt.-%, particularly preferably from 0.05 to 0.15 wt.-%, based on the total weight of the oral care formulation. In a preferred embodiment, the oral care formulation is a toothpaste, and the toothpaste comprises a fluoride source.
In one embodiment, the oral care formulation comprises a polymer. The polymer is preferably selected from polyethylene glycols, polysaccharides, for example cellulose derivatives, for example carboxymethyl cellulose, hydroxymethyl cellulose, ethyl cellulose, microcrystalline cellulose, or polysaccharide gums, for example xanthan gum, guar gum or carrageenan gum, or polyacrylates or polymers based on N-vinylpyrrolidone, and mixtures thereof.
The polymer may, for example, be present in an amount of from 0.1 to 10 wt.-%, preferably from 0.5 to 5 wt.-%, based on the total weight of the oral care formulation.
In one embodiment, the oral care formulation comprises an anionic polymer. The anionic polymer is preferably selected from polycarboxylates, polyacrylic acids, polyacrylates, polyphosphonic acids, cross-linked carboxyvinyl copolymers, and mixtures thereof.
The anionic polymer may, for example, be present in an amount of from 1 to 20 wt.-%, preferably from 5 to 15 wt.-%, based on the total weight of the oral care formulation.
In one embodiment, the oral care formulation comprises a thickening agent. The thickening agent is preferably selected from silica thickening agents, carboxy vinyl polymers, carrageenan, hydroxyethyl cellulose, salts of cellulose ethers such as sodium carboxymethyl cellulose or sodium carboxymethyl hydroxyethyl cellulose, karaya, gum arabic, gum tragacanth, colloidal magnesium aluminum silicate, and mixtures thereof.
The thickening agent may, for example, be present in an amount of from 0.1 to 10 wt.-%, preferably from 0.5 to 5 wt.-%, based on the total weight of the oral care formulation.
In one embodiment, the oral care formulation comprises a foaming agent. The foaming agent is preferably selected from polyethylene glycol, alginate polymers, and mixtures thereof.
The foaming agent may, for example, be present in an amount of from 0.1 to 20 wt.-%, preferably from 1 to 10 wt.-%, based on the total weight of the oral care formulation.
In one embodiment, the oral care formulation comprises a surfactant. The surfactant may, for example, be present in an amount of from 0.1 to 20 wt.-%, preferably from 1 to 10 wt.-%, based on the total weight of the oral care formulation.
In one embodiment, the surfactant is an anionic surfactant. The anionic surfactant is preferably selected from alkyl sulfates, for example sodium lauryl sulfate, alkyl ether sulfates, for example sodium laureth-2 sulfate, alkyl aryl sulfonates, for example sodium lauryl benzene sulfonate, alkyl sulfoacetates, for example sodium lauryl sulfoacetate, and mixtures thereof.
In one embodiment, the surfactant is a sulfur-free anionic surfactant.
The sulfur-free anionic surfactant is preferably selected from taurates, for example sodium methyl cocoyl taurate, glycinates, for example sodium cocoyl glycinate, sarcosinates, for example sodium lauroyl sarcosinate, quaternary ammonium compounds, for example benzalkonium chloride or cetylpyridinium chloride, and mixtures thereof.
In one embodiment, the surfactant is a non-ionic surfactant. In one embodiment, the surfactant is a glucamide. In one embodiment, the surfactant is a glucamide of Formula X:
Figure imgf000016_0001
wherein R is selected from saturated or unsaturated hydrocarbon chains having 5 to 23 carbon atoms. Preferably, R in Formula (X) is selected from saturated or unsaturated hydrocarbon chains having 7 to 17 carbon atoms. Also preferably, the R-C=O residue in Formula (X) is derived from caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, coconut fatty acids, or mixtures thereof. Also preferably, the R-C=O residue in Formula (X) is derived from 9-decenoic acid, 9-dodecenoic acid, or mixtures thereof.
Particularly preferred glucamides of Formula (X) are capryloyl/caproyl methyl glucamide, lauroyl/myristoyl methyl glucamide, cocoyl methyl glucamide, oleyl methyl glucamide, or mixtures thereof. Such glucamides are commercially available from Clariant (GlucoTain® Clear, GlucoTain® Plus, GlucoTain® Flex, GlucoTain® Care, GlucoTain® Sense).
Also particularly preferred glucamides of Formula (X) are N-9-decenoyl-N- methylglucamine, N-9-dodecenoyl-N-methylglucamine, or mixtures thereof.
In one embodiment, the surfactant is an alkyl polyglycoside (APG), preferably an alkyl polyglucoside.
In one embodiment, the surfactant is a zwitterionic surfactant, for example a betaine surfactant, for example cocam idopropyl betaine. In one embodiment, the surfactant is a cationic surfactant.
In one embodiment, the oral care formulation comprises a buffer or pH adjusting agent. In a preferred embodiment, the oral care formulation has a pH in the range of from 4 to 8, preferably from 4.5 to 7.5, more preferably from 5 to 7, particularly preferably from 5 to 6, also particularly preferably from 5.5 to 6.5, also particularly preferably from 6 to 7. In a preferred embodiment, the oral care formulation is a toothpaste, and the toothpaste has a pH in the range of from 4 to 8, preferably from 4.5 to 7.5, more preferably from 5 to 7, particularly preferably from 5 to 6, also particularly preferably from 5.5 to 6.5, also particularly preferably from 6 to 7.
In one embodiment, the oral care formulation comprises a flavoring agent, sweetening agent, and/or pigment or dye. Examples of flavors are mint, peppermint, spearmint, Wintergreen, menthol, or strawberry. An example of a sweetening agent is sodium saccharin. Examples of pigments are titanium dioxide or zinc oxide.
The oral care formulation may, for example, be prepared by mixing its ingredients.
The present invention also relates to compound X selected from compounds of Formula (I)
Figure imgf000018_0001
wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
Examples of such microorganisms are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
In a preferred embodiment, the dental caries causing microorganisms are dental caries causing bacteria. In a preferred embodiment, the dental plaque causing microorganisms are dental plaque causing bacteria. In a preferred embodiment, the gingivitis causing microorganisms are gingivitis causing bacteria.
A preferred embodiment relates to compound X selected from compounds of Formula (I)
Figure imgf000018_0002
wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters for use in reducing the effects of dental caries causing bacteria, dental plaque causing bacteria or gingivitis causing bacteria.
Examples of such bacteria are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
The present invention also relates to an oral care formulation as defined herein for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
Examples of such microorganisms are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L. acidophilus).
In a preferred embodiment, the dental caries causing microorganisms are dental caries causing bacteria. In a preferred embodiment, the dental plaque causing microorganisms are dental plaque causing bacteria. In a preferred embodiment, the gingivitis causing microorganisms are gingivitis causing bacteria.
A preferred embodiment relates to an oral care formulation as defined herein for use in reducing the effects of dental caries causing bacteria, dental plaque causing bacteria or gingivitis causing bacteria. Examples of such bacteria are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
The present invention also relates to compound X selected from compounds of Formula (I)
Figure imgf000020_0001
wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
Examples of such microorganisms are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L. acidophilus).
In a preferred embodiment, the dental caries causing microorganisms are dental caries causing bacteria. In a preferred embodiment, the dental plaque causing microorganisms are dental plaque causing bacteria. In a preferred embodiment, the gingivitis causing microorganisms are gingivitis causing bacteria.
A preferred embodiment relates to compound X selected from compounds of Formula (I)
Figure imgf000021_0001
wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
Examples of such bacteria are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
The present invention also relates to an oral care formulation as defined herein for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
Examples of such microorganisms are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L. acidophilus).
In a preferred embodiment, the dental caries causing microorganisms are dental caries causing bacteria. In a preferred embodiment, the dental plaque causing microorganisms are dental plaque causing bacteria. In a preferred embodiment, the gingivitis causing microorganisms are gingivitis causing bacteria. A preferred embodiment relates to an oral care formulation as defined herein for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
Examples of such bacteria are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
The present invention also relates to a method of reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms, wherein the method comprises contacting the dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms with compound X as defined herein or an oral care formulation as defined herein. Examples of such microorganisms are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L. acidophilus).
In a preferred embodiment, the dental caries causing microorganisms are dental caries causing bacteria. In a preferred embodiment, the dental plaque causing microorganisms are dental plaque causing bacteria. In a preferred embodiment, the gingivitis causing microorganisms are gingivitis causing bacteria.
A preferred embodiment relates to a method of reducing the effects of dental caries causing bacteria, dental plaque causing bacteria or gingivitis causing bacteria, wherein the method comprises contacting the dental caries causing bacteria, dental plaque causing bacteria or gingivitis causing bacteria with compound X as defined herein or an oral care formulation as defined herein. Examples of such bacteria are Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans (S. mutans) or Lactobacillus acidophilus (L acidophilus).
The present invention also relates to a method of prevention or treatment of dental caries, dental plaque or gingivitis, wherein the method comprises contacting the oral cavity of a subject in need thereof with compound X as defined herein or an oral care formulation as defined herein.
The present invention also relates to the use of compound X as defined herein or an oral care formulation as defined herein for the prevention or treatment of dental caries, dental plaque or gingivitis.
In this document, the following definitions apply unless specifically stated otherwise. All percentages are by weight (w/w) of the total composition. All ratios are weight ratios. “wt.-%” means percentage by weight.
“Molecular weight” or “M.Wt.” or “MW’ and grammatical equivalents mean the number average molecular weight.
“Viscosity” is measured at 25°C using a HAAKE Rotation Viscometer VT 550 with cooling/heating vessel and sensor systems according to DIN 53019 at a shear rate of 12.9 s-1.
“Water-soluble” refers to any material that is sufficiently soluble in water to form a clear solution to the naked eye at a concentration of 0.1 % by weight of the material in water at 25°C. The term “water-insoluble” refers to any material that is not “water-soluble”.
“Dry” or “substantially dry” means comprising less than 5 %, less than 3 %, less than 2 %, less than 1 %, or about 0 % of any compound or composition being in liquid form when measured at 25°C at ambient conditions. Such compounds or compositions being in liquid form include water, oils, organic solvents and other wetting agents. 'Anhydrous" means that the composition comprises less than 5 %, less than 3 %, less than 2 %, less than 1 %, or about 0 % water by total weight of the composition.
“Substantially free from” or “substantially free of” means less than 1 %, or less than 0.8 %, or less than 0.5 %, or less than 0.3 %, or about 0 %, by total weight of the composition.
“Derivatives” includes but is not limited to amide, ether, ester, amino, carboxyl, acetyl, acid, salt and/or alcohol derivatives of a given compound. In at least one embodiment, “derivatives thereof” means the amide, ether, ester, amino, carboxyl, acetyl, acid, salt and alcohol derivatives.
The examples which follow are intended to illustrate the subject matter of the invention without restricting it thereto.
Examples
Materials
Velsan® Flex is commercially available from Clariant. Chemical name: Capryloyl/Caproyl Anhydro Methyl Glucamide (and) Water, active content: 70 wt.- %. Capryloyl/Caproyl Anhydro Methyl Glucamide is a mixture of compounds of Formula (I) wherein R is -(CFhjsCHs and compounds of Formula (I) wherein R is - (CH2)6CH3.
Velsan® EHG is commercially available from Clariant. Chemical name: Ethylhexylglycerin.
Example 1 : Microbiological test
The microbiological test was carried out according to BS EN 1040:2005.
1 . 1 %, 2%, 3% and 5% sample solutions were prepared in sterilized tap water.
2. An inoculum suspension with Streptococcus mutans was prepared. 3. 1.0 ml sterilized tap water and 1.0 ml inoculum were placed in a test tube.
4. 8 ml of sample solution was added, a stopwatch was started, the mixture was homogenized.
5. 1 ml of solution was taken from the resulting solution after 2 minutes and a plate count was performed from it using standard pour plate method.
This was also done with a blank sample to prove that only the contained active substance is responsible for the reduction of Streptococcus mutans.
Figure imgf000025_0001
Figure imgf000025_0002
Example 2: Examples of toothpaste formulations (amounts are given in wt-%)
Figure imgf000025_0004
Figure imgf000025_0003
Figure imgf000026_0001
Example 3: Examples of toothpaste formulations (amounts are given in wt-%)
Figure imgf000027_0001
Figure imgf000028_0001
Example 4: Examples of toothpaste formulations (amounts are given in wt-%)
Figure imgf000028_0002
Figure imgf000029_0001
Example 5: Examples of toothpaste formulations (amounts are given in wt-%)
Figure imgf000029_0002
Figure imgf000030_0001
Example 6: Examples of toothpaste formulations (amounts are given in wt-%)
Figure imgf000030_0002
Figure imgf000031_0001
Example 7: Example of a mouthwash formulation (amounts are given in wt-%)
Figure imgf000031_0002
Example 8: Toothpaste against biofilm formers from the oral cavity
The reducing effect of toothpaste samples on biofilm-forming bacteria such as streptococci was tested over a period of up to 5 minutes. A biofilm of the test bacteria (Streptococcus mutans) was cultured, and then the toothpaste solution (40% toothpaste in tap water) was applied to the biofilm. After the elapsed time, the reducing effect was quantified by determining the number of germs. A control with tap water serves as a reference to rule out that the tap water influences the bacteria.
The toothpastes shown in the following Table were used:
Figure imgf000032_0001
The toothpastes were tested with and without the addition of Velsan Flex (2% and 3%).
The following Table shows the colony forming units/ml or g of sample after 5 minutes:
Figure imgf000032_0002
Conclusion:
The addition of Velsan Flex leads to a reduction of the test bacteria.

Claims

Claims
1. Use of compound X selected from compounds of Formula (I)
Figure imgf000033_0001
wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof, glyceryl ethers, sorbitan esters, and isosorbide esters as an antimicrobial agent against dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
2. The use according to claim 1 , wherein
R in Formula (I) is selected from saturated hydrocarbon chains having 5 to
17 carbon atoms, unsaturated hydrocarbon chains having 5 to 17 carbon atoms, and mixtures thereof, preferably is selected from saturated hydrocarbon chains having 5 to 13 carbon atoms, unsaturated hydrocarbon chains having 5 to 13 carbon atoms, and mixtures thereof, particularly preferably is selected from saturated hydrocarbon chains having 7 to 9 carbon atoms, unsaturated hydrocarbon chains having 7 to 9 carbon atoms, and mixtures thereof.
3. The use according to claim 1 or 2, wherein the glyceryl ethers are mono- or diethers of glycerin and one or more C6-C20 fatty alcohols, preferably mono- or diethers of glycerin and one or more C8-C14 fatty alcohols, particularly preferably monoethers of glycerin and one or more C8 fatty alcohols.
4. The use according to any of claims 1 to 3, wherein the sorbitan esters are mono-, di- or triesters of sorbitan and one or more C6-C20 fatty acids, preferably mono- or diesters of sorbitan and one or more C8-C14 fatty acids, particularly preferably mono- or diesters of sorbitan and caprylic acid.
5. The use according to any of claims 1 to 4, wherein the sorbitan esters are selected from sorbitan caprylate, sorbitan stearate, sorbitan olivate, sorbitan oleate, sorbitan caprate, sorbitan laurate, sorbitan myristate, sorbitan caproate, and mixtures thereof, preferably is sorbitan caprylate.
6. The use according to any of claims 1 to 5, wherein the isosorbide esters are mono- or diesters of isosorbide and one or more C6-C20 fatty acids, preferably mono- or diesters of isosorbide and one or more C8-C14 fatty acids, particularly preferably mono- or diesters of isosorbide and caprylic acid.
7. The use according to any of claims 1 to 6, wherein the isosorbide esters are selected from isosorbide caprylate, isosorbide stearate, isosorbide olivate, isosorbide oleate, isosorbide caprate, isosorbide laurate, isosorbide myristate, isosorbide caproate, and mixtures thereof, preferably is isosorbide caprylate.
8. Compound X as defined in any of claims 1 to 7 for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
9. Compound X as defined in any of claims 1 to 7 for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
10. An oral care formulation comprising from 0.1 to 20 wt.-%, preferably from 0.2 to 10 wt.-%, more preferably from 0.3 to 5 wt.-%, even more preferably from 0.4 to 3 wt.-%, particularly preferably from 0.5 to 2 wt.-%, based on the total weight of the oral care formulation, of compound X as defined in any of claims 1 to 7.
11 . The oral care formulation according to claim 10, wherein the oral care formulation is selected from the group consisting of toothpaste, oral gel, mouth wash, tooth powder and chewing gum.
12. An oral care formulation as defined in claim 10 or 11 for use in reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms.
13. An oral care formulation as defined in claim 10 or 11 for use in the prevention or treatment of dental caries, dental plaque or gingivitis.
14. A method of reducing the effects of dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms, wherein the method comprises contacting the dental caries causing microorganisms, dental plaque causing microorganisms or gingivitis causing microorganisms with compound X as defined in any of claims 1 to 7 or an oral care formulation as defined in claim 10 or 11 .
PCT/EP2024/058509 2023-03-31 2024-03-28 Antimicrobial compounds for oral care WO2024126876A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP23165977 2023-03-31
EP23165977.2 2023-03-31

Publications (1)

Publication Number Publication Date
WO2024126876A2 true WO2024126876A2 (en) 2024-06-20

Family

ID=85800372

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2024/058509 WO2024126876A2 (en) 2023-03-31 2024-03-28 Antimicrobial compounds for oral care

Country Status (1)

Country Link
WO (1) WO2024126876A2 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2224973A1 (en) 2007-11-29 2010-09-08 Inolex Investment Corporation Preservatives for cosmetic, toiletry and pharmaceutical compositions
WO2018002100A1 (en) 2016-06-29 2018-01-04 Clariant International Ltd Composition for inhibiting micro-organisms
WO2019152569A2 (en) 2018-01-30 2019-08-08 Inolex Investment Corporation Natural 1,2-alkanediols, compositions having natural 1,2-alkanediols and processes for making the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2224973A1 (en) 2007-11-29 2010-09-08 Inolex Investment Corporation Preservatives for cosmetic, toiletry and pharmaceutical compositions
WO2018002100A1 (en) 2016-06-29 2018-01-04 Clariant International Ltd Composition for inhibiting micro-organisms
WO2019152569A2 (en) 2018-01-30 2019-08-08 Inolex Investment Corporation Natural 1,2-alkanediols, compositions having natural 1,2-alkanediols and processes for making the same

Similar Documents

Publication Publication Date Title
CA2787393C (en) Oral care product for sensitive enamel care
US3342687A (en) Oral preparation
RU2722821C2 (en) Oral care composition
US6770268B1 (en) Non-foaming anti-infective periodontic compositions
JPS6038321A (en) Foamable, fluoride-stable antiplaque dentifirice
WO1992008441A1 (en) Improved anti-plaque compositions comprising a combination of morpholinoamino alcohol and metal salts
JP5054914B2 (en) Oral composition
JP2006347987A (en) Composition for oral cavity and method for enhancing foamability of composition for oral cavity
RU2671835C2 (en) Oral care composition
WO2024126876A2 (en) Antimicrobial compounds for oral care
JP2006347986A (en) Composition for oral cavity
US20070292360A1 (en) Process and composition for oral hygiene
JPH021402A (en) Dentifrice composition
JP2002234825A (en) Composition for oral cavity application
JPH0211511A (en) Composition for oral cavity
JP2012097018A (en) Anti-dental caries agent, antiseptic agent, composition for oral cavities and composition
KR102579556B1 (en) Oral composition
KR102574022B1 (en) oral composition
EA030855B1 (en) Oral care compositions
JP2806024B2 (en) Oral composition
JP2002047162A (en) Composition for oral cavity
US8852617B2 (en) Antimicrobial dental care preparation
WO2002050002A1 (en) Non-halogenated phenyl substituted phenols, antimicrobial compositions containing the same, and methods of using the same
KR102642592B1 (en) Oral composition
JP3065947B2 (en) Oral composition