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WO2025012262A1 - Synergies antimicrobiennes - Google Patents

Synergies antimicrobiennes Download PDF

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Publication number
WO2025012262A1
WO2025012262A1 PCT/EP2024/069326 EP2024069326W WO2025012262A1 WO 2025012262 A1 WO2025012262 A1 WO 2025012262A1 EP 2024069326 W EP2024069326 W EP 2024069326W WO 2025012262 A1 WO2025012262 A1 WO 2025012262A1
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WO
WIPO (PCT)
Prior art keywords
constituent
group
formula
compound
product
Prior art date
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PCT/EP2024/069326
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English (en)
Inventor
Christin KOCH
Christian-Friedrich OTTO
Steffen NORDZIEKE
Sabine Lange
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Symrise AG
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Symrise AG
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Publication of WO2025012262A1 publication Critical patent/WO2025012262A1/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • A61K8/0229—Sticks
    • 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
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • 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
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Definitions

  • the present invention primarily relates to a mixture comprising or consisting of one or more compound(s) of formula (I) or (II) as defined herein and one or more further antimicrobial agent(s) and it relates to a product comprising a mixture as defined herein. Moreover, the present invention relates to the use of one or more compound(s) of formula (I) or (II) as defined herein to improve the antimicrobial effect of one or more further antimicrobial agent(s) and to the use of one or more further antimicrobial agent(s) to improve the antimicrobial effect of one or more compound(s) of formula (I) or (II) as defined herein.
  • the present invention further relates to the use of a mixture as defined herein as an antimicrobial agent and to a process as defined herein for improving the antimicrobial effect of one or more compound(s) as defined in step (a) and/or of one or more compound(s) as defined in step (b) of the process.
  • the present invention relates to a process for inhibiting or preventing the growth of one or more microorganisms in a product or semifinished product and to a process for inhibiting or preventing the growth of one or more microorganisms on a mammal’s skin or mucosa and/or for inhibiting or preventing the growth of one or more microorganisms on/in a surface.
  • the present invention relates to a mixture or compound as defined herein for use as an antimicrobial agent for inhibiting or preventing the growth of one or more microorganisms on a mammal’s skin or mucosa.
  • the present invention relates to the use of one or more compound(s) as defined herein as antimicrobial agent(s) and to a process as defined herein for inhibiting or preventing the growth of one or more microorganisms on a mammal’s skin or mucosa, and/or for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, and/or for inhibiting or preventing the growth of one or more microorganisms on/in a surface.
  • Personal care, pharmaceutical, and household products usually contain antimicrobial agents to increase their shelf-life and to guarantee safety for the consumer’s health.
  • the aim is to protect consumers of said products from potentially pathogenic microorganisms that might otherwise grow inside the products, and to stop or delay the biological and/or physicochemical deterioration of the product.
  • the same rationale applies to semi-finished products that are used in the production of said personal care, pharmaceutical, and household products.
  • the preservation of said products can be achieved by chemical, physical or physicochemical methods.
  • the most common strategy is the incorporation of antimicrobial agents into said products.
  • Common antimicrobial agents are, for example, parabens, formaldehyde releasers, isothiazolinones, organic acids, triclosan, phenoxyethanol and benzyl alcohol.
  • Some antimicrobial agents have the drawback that they might induce undesirable side effects in consumers. These effects might range from mild skin irritation to allergic reactions to the chemicals used.
  • one or more further antimicrobial agent(s) that are different from the compound(s) of formula (I) as defined in constituent (i)
  • the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • mixtures as defined herein display particularly advantageous antimicrobial properties against various bacteria and fungi commonly found in personal care, pharmaceutical, and household products.
  • Said products often are in direct contact with the skin, mucosa, or hair of the consumer of the product or with other surfaces used by humans, such as, for instance, kitchen and bathroom surfaces.
  • one or more further antimicrobial agent(s) that are different from the compound(s) of formula (II) (and (l-a) and (l-b)) as defined in constituent (i)), preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the one or more compound(s) of formula (II) of constituent (i) is/are selected from the group consisting of
  • the one or more compound(s) of formula (I) or (II) of 5 constituent (i) is/are selected from the group consisting of
  • the one or more compound(s) of formula (I) or (II) of constituent (i) is/are selected from the group consisting of
  • constituent (i) comprises a mixture of the following two compounds of formula (I) or (II): According to another preferred embodiment, constituent (i) comprises a mixture of the following two compounds of formula (I) or (II):
  • the one or more further antimicrobial agent(s) of constituent (ii) of the mixture is/are
  • (ii-1) selected from the group consisting of 1 ,2-decanediol (decylene glycol), 1 ,2- heptanediol, 1 ,2-hexanediol, 1 ,2-nonanediol, 1 ,2-octanediol, 1 ,2-pentanediol, 1 ,2- propanediol, 1 ,3-propanediol, 2,3-decanediol, 2,3-heptanediol, 2,3-hexanediol, 2,3- nonanediol, 2,3-octanediol, 2,3-pentanediol, 2-benzylheptanol, 2- hydroxyacetophenone, 2-methyl 5-cyclohexylpentanol, 3-hydroxypropyl 2- hydroxybenzoate, 4-hydroxyacetophenone, alkyl (C 12-22) trimethyl
  • the one or more further antimicrobial agent(s) of constituent (ii) of the mixture is/are
  • (ii-2) selected from the group consisting of 1 ,2-decanediol (decylene glycol), 1 ,2- heptanediol, 1 ,2-hexanediol, 1 ,2-nonanediol, 1 ,2-octanediol, 1 ,2-pentanediol, 1 ,3- propanediol, 2,3-heptanediol, 2,3-hexanediol, 2,3-nonanediol, 2,3-octanediol, 2,3- pentanediol, 2-benzylheptanol, 2-methyl 5-cyclohexylpentanol, 4- hydroxyacetophenone, anisic acid and salts thereof, anisic acid 3- hydroxypropylester, ascorbic acid and salts thereof, benzalkonium chloride, benzethonium chloride, benzoic acid
  • (ii-3) selected from the group consisting of 1 ,2-decanediol (decylene glycol), 1 ,2- heptanediol, 1 ,2-hexanediol, 1 ,2-nonanediol, 1 ,2-octanediol, 1 ,2-pentanediol, 1 ,3- propanediol, 2,3-heptanediol, 2,3-hexanediol, 2,3-nonanediol, 2,3-octanediol, 2,3- pentanediol, 2-methyl 5-cyclohexylpentanol, 4-hydroxyacetophenone, anisic acid and salts thereof, anisic acid 3-hydroxypropylester, benzoic acid, benzoic acid 3- hydroxypropylester, benzyl alcohol, benzyl salicylate, bisabolol, butylene glycol
  • (ii-4) selected from the group consisting of 1 ,2-decanediol (decylene glycol), 1 ,2- heptanediol, 1 ,2-hexanediol, 1 ,2-nonanediol, 1 ,2-octanediol, 1 ,2-pentanediol (pentylene glycol), 1 ,3-propanediol, 2-methyl 5-cyclohexylpentanol, 4- hydroxyacetophenone, benzoic acid 3-hyroxypropylester, anisic acid 3- hydroxypropylester, benzyl alcohol, benzyl salicylate, bisabolol, butylene glycol, caprylhydroxamic acid, capryloyl glycine, capryloyl/caproyl anhydro methyl glucamide, caprylyl glyceryl ether, chlorphenesin, citronellyl
  • (ii-5) selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2- heptanediol, 1 ,2-nonanediol, 1 ,3-propanediol, 2-methyl-5-cyclohexylpentanol, benzyl salicylate, bisabolol, caprylhydroxamic acid, capryloyl/caproyl anhydro methyl glucamide, chlorphenesin, ethylparaben, glyceryl caprylate, heptylglycerin, hydroxyethoxyphenyl butanol, hydroxyethoxyphenyl butanone, itaconic acid, methylheptylglycerin, methylparaben, potassium sorbate, propanediol caprate, propanediol laurate, propylene glycol caprylate, raspberry ketone,
  • (ii-6) selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2- heptanediol, 1 ,3-propanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin, most preferably is/are
  • (ii-7) selected from the group consisting of 1 ,2-heptanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin.
  • the one or more compound(s) of formula (I) of constituent (i) is/are selected from the group consisting of and the one or more further antimicrobial agent(s) of constituent (ii) is/are selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,3-propanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin.
  • the compound of formula (I) of constituent (i) is and the one or more further antimicrobial agent(s) of constituent (ii) is/are selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,3-propanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin.
  • the compound of formula (I) of constituent (i) is and the one or more further antimicrobial agent(s) of constituent (ii) is/are selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,3-propanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin.
  • the mixture according to the invention comprises or consists of
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and (ii) 1 ,2-nonanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and (ii) chlorphenesin, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • the mixture according to the invention comprises or consists of
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and (ii) methylheptylglycerin, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • the mixture according to the invention comprises or consists of
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • the mixture according to the invention comprises or consists of
  • the mixture according to the invention comprises or consists of and (ii) sodium benzoate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of
  • the mixture according to the invention comprises or consists of and
  • the mixture according to the invention comprises or consists of and
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • the mixture according to the invention comprises or consists of and
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and (ii) capryloyl/caproyl anhydro methyl glucamide, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of (ii) propanediol caprate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of (ii) propylene glycol caprylate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of and
  • constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and/or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
  • the mixture according to the invention comprises or consists of [2-(3,4-dihydroxytetrahydrofuran-2-yl)-2-hydroxy-ethyl] benzoate, preferably of the following structure
  • the mixture according to the invention comprises or consists of [2-(3,4-dihydroxytetrahydrofuran-2-yl)-2-hydroxy-ethyl] 4- methoxybenzoate, preferably of the following structure (constituent (i); compound of formula (I) or (II) as defined herein; cf. column “Constituent (i); compound of formula (I) or (II) as defined herein; cf. column “Constituent
  • the mixture according to the invention comprises or consists of 1 ,4-anhydroarabinitol-5-benzoate, preferably of the following structure
  • the mixture according to the invention comprises or consists of 1 ,4-anhydroarabinitol-5-(4-methoxybenzoate), preferably of the following structure
  • the mixture according to the invention comprises or consists of 2,3,4-trihydroxybutyl (4-methoxybenzoate), preferably of the following structures
  • the mixture according to the invention comprises or consists of 2,3,4,5-tetrahydroxypentyl benzoate, preferably of the following structures
  • the mixture according to the invention comprises or consists of 2,3,4,5,6-pentahydroxyhexyl benzoate, preferably of the following structure ([(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl] benzoate, in the following: mannitol-1- benzoate),
  • Table 7 Specific mixtures of 2,3,4,5,6-pentahydroxyhexyl benzoate, preferably mannitol- 1 -benzoate (constituent (i); compound of formula (I) or (II) as defined herein), with a further antimicrobial agent (constituent (ii)), respectively
  • the mixture according to the invention comprises or consists of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), preferably of the following structure ([(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl] anisate, in the following: mannitol-1- anisate),
  • Table 8 Specific mixtures of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), preferably mannitol-1-anisate (constituent (i); compound of formula (I) or (II) as defined herein), with a further antimicrobial agent (constituent (ii)), respectively
  • the mixture according to the invention comprises or consists of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), preferably of the following structures (a mixture of [(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl] anisate and [(2R,3R,4R,5S)- 2,3,4,5,6-pentahydroxyhexyl] anisate, in the following: sorbitol anisate),
  • Table 10 Specific mixtures of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), preferably sorbitol anisate (constituent (i); compound(s) of formula (I) or (II) as defined herein), with a further antimicrobial agent (constituent (ii)), respectively
  • the mixture according to the invention comprises a total amount of from 10 to 90 wt.%, preferably from 30 to 70 wt.%, more preferably from 40 to 60 wt.%, of the compounds of formula (I) and (II) of constituent (i), based on the total weight of the mixture, and/or the mixture comprises a total amount of from 10 to 90 wt.%, preferably from 30 to 70 wt.%, more preferably from 40 to 60 wt.%, of the one or more further antimicrobial agent(s) of constituent (ii), based on the total weight of the mixture.
  • a product comprising a mixture as defined herein, preferably wherein the product is selected from the group consisting of personal care products, pharmaceutical products, and household products, more preferably wherein the product is i. in the form of a dispersion comprising an oil component in an amount of > 1 wt.%, preferably in an amount of > 3 wt.%, preferably in the form of an emulsion, more preferably an O/W emulsion, a W/O emulsion, a multiple emulsion, a hydrodispersion gel, a balm, a multiple emulsion of the water-in-oil type (W/O/W) or of the oil-in-water type (O/W/O), a PIT emulsion, a Pickering emulsion, a micro-emulsion, a liquid, a lotion, a suspension, a milk, an ointment, a paste, a gel, a cream-based
  • the oil component corresponds to one or more oil body/bodies or wax(es), more preferably selected from the group consisting of natural fats and oils, more preferably selected from the group consisting of prunus amygdalus dulcis (sweet almond) oil, caprylic/capric triglyceride, argania spinosa kernel oil, butyrospermum parkii (shea) butter, cannabis sativa seed oil, olea europaea (olive) fruit oil, persea gratissima (avocado) oil, vitis vinifera (grape) seed oil, ricinus communis (castor) seed oil, sesamum indicum (sesame) seed oil, heliantus annuus (
  • the personal care product is selected from the group consisting of deodorant products, body care and cleansing products, intimate care and cleansing products, foot care and cleansing products, oral care and cleansing products, scalp care and cleansing products, and face care and cleansing products, more preferably wherein the personal care product is selected from the group consisting of deodorant sprays, deodorant roll-ons, deodorant sticks, deodorant creams, foot creams, body washes, mouth washes, toothpastes, shampoos, hair conditioner, styling wax, styling gels, styling foams, styling creams, styling mousses, styling serums, styling pomades, micellar waters, intimate washes, cleansers, toners, serums, moisturizers, eye creams, balms, soaps, facial masks, sunscreens, liquids for wet wipes, primers, concealers, foundations, rouges, bronzers, highlighters, eyebrow pencils, eyebrow creams, eyebrow waxes, eyebrow gels, eyebrow powders, eyeshadows, eyeliners, mascara, lipsticks, lip
  • the product according to the invention comprises from 0.001 to 15 wt.%, preferably from 0.01 to 10 wt.%, more preferably from 0.05 to 2.5 wt.%, most preferably from 0.1 to 1 wt.%, of the mixture according to the invention, based on the total weight of the product.
  • Another aspect of the present invention relates to the use of
  • one or more further antimicrobial agent(s) that are different from the compound(s) of formula (I) and (II) as defined in constituent (i)
  • use of (ii) one or more further antimicrobial agent(s) to, preferably synergistically improve the antimicrobial effect of (i) one or more compound(s) of formula (I)
  • one or more further antimicrobial agent(s) to, preferably synergistically, improve the antimicrobial effect of (i) one or more compound(s) of formula (II).
  • the, preferably synergistically, improved antimicrobial effect is one or more effect(s) selected from the group consisting of an antibacterial effect, an antiviral effect, an antifungal effect, preferably an anti-yeast and/or anti-mold effect.
  • the antimicrobial effect is achieved against one or more microorganism(s) selected from the group consisting of bacteria and fungi, preferably gram positive and gram negative bacteria, yeasts and filamentous fungi, more preferably selected from the group consisting of Staphylococcus aureus, Candida albicans, Aspergillus brasiliensis, Pseudomonas aeruginosa and Escherichia coli.
  • bacteria and fungi preferably gram positive and gram negative bacteria, yeasts and filamentous fungi, more preferably selected from the group consisting of Staphylococcus aureus, Candida albicans, Aspergillus brasiliensis, Pseudomonas aeruginosa and Escherichia coli.
  • Another aspect of the present invention relates to the use of a mixture according to the invention as an antimicrobial agent.
  • Another aspect of the present invention relates to a mixture according to the invention for use as an antimicrobial agent, preferably for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin.
  • Another aspect of the present invention relates to a process for, preferably synergistically, improving the antimicrobial effect of one or more compound(s) as defined in step (a) and/or of one or more compound(s) as defined in step (b) comprising or consisting of the following steps:
  • step (b) providing one or more further antimicrobial agent(s) (that are different from the compound(s) of formula (I) and (II) as defined in step (a)), and
  • Another aspect of the present invention relates to a process for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, comprising or consisting of the following steps:
  • the one or more compound(s) of constituent (i) as provided in step (a) synergistically improve(s) the antimicrobial effect of the one or more compound(s) of constituent (ii) as provided in step (a) and/or the one or more compound(s) of constituent (ii) as provided in step (a) synergistically improve(s) the antimicrobial effect of the one or more compound(s) of constituent (i) as provided in step (a).
  • Another aspect of the present invention relates to a process for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and/or for inhibiting or preventing the growth of one or more microorganisms on/in a surface comprising or consisting of the following steps:
  • step (b) bringing the mixture or constituents or product provided in step (a) in contact with a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, on which the growth of one or more microorganisms is to be inhibited or prevented and/or in contact with a surface on/in which the growth of one or more microorganisms is to be inhibited or prevented.
  • a mammal preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin
  • a preferred embodiment relates to a process for inhibiting or preventing the growth of one or more microorganisms on/in a surface comprising or consisting of the following steps:
  • step (b) bringing the mixture or constituents or product provided in step (a) in contact with a surface on/in which the growth of one or more microorganisms is to be inhibited or prevented.
  • the compound of formula (II) or mixture or composition or product as defined herein is used is as an antimicrobial agent, preferably (i) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and/or
  • antimicrobial agent(s) preferably sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite
  • Another aspect of the present invention relates to a compound as defined herein for use as an antimicrobial agent, preferably for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin.
  • Another aspect of the present invention relates to a process (i) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and/or (ii) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and/or (iii) for inhibiting or preventing the growth of one or more microorganisms on/in a surface, comprising or consisting of the following steps:
  • step (b) bringing the compound or mixture or composition or product provided in step (a) in contact with (i) a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, on which the growth of one or more microorganisms is to be inhibited or prevented and/or in contact with (ii) the other ingredients of the product or semi-finished product in which the growth of one or more microorganisms is to be inhibited or prevented and/or in contact with (iii) a surface on/in which the growth of one or more microorganisms is to be inhibited or prevented.
  • a mammal’s preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, on which the growth of one or more microorganisms is to be inhibited or prevented and/or in contact with (ii) the other ingredients of the product or semi-finished product in which the growth of one or more microorganisms is
  • Another aspect of the present invention relates to a process (i) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and/or (ii) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and/or (iii) for inhibiting or preventing the growth of one or more microorganisms on/in a surface, comprising or consisting of the following steps:
  • step (b) bringing the compound(s) provided in step (a) in contact with (i) a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, on which the growth of one or more microorganisms is to be inhibited or prevented and/or in contact with (ii) the other ingredients of the product or semifinished product in which the growth of one or more microorganisms is to be inhibited or prevented and/or in contact with (iii) a surface, on/in which the growth of one or more microorganisms is to be inhibited or prevented.
  • a mammal’s preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin
  • the other ingredients of the product or semifinished product in which the growth of one or more microorganisms is to be inhibited or prevented and/or in contact with (iii) a surface, on/in which the growth of one or more microorgan
  • step (a) of the process corresponds to or can be derived from the (preferred) embodiments of the products according to the invention which are explained above or vice versa.
  • (Preferred) embodiments of the mixtures according to the invention correspond to or can be derived from the (preferred) embodiments of the uses according to the invention which are explained above or vice versa.
  • (Preferred) embodiments of the mixtures according to the invention correspond to or can be derived from the (preferred) embodiments of the processes according to the invention which are explained above or vice versa.
  • (Preferred) embodiments of the uses according to the invention correspond to or can be derived from the (preferred) embodiments of the processes according to the invention which are explained above or vice versa.
  • the (preferred) embodiments described herein can be arbitrarily combined with each other as long as technically sensible.
  • the compounds of formulae (I) and (II) can be obtained, for instance, by following the synthetic approaches described in Synthesis, 2003, (15), 2373-2377; Journal of the Korean Chemical Society, 2002, 46(5); Tetrahedron Letters, 2015, 56(15), 1973-1975; and JP2011207990A.
  • the compounds of formulae (I) and (II) are accessible not only via precursors of petrochemical origin, but advantageously also in a sustainable and/or cost-efficient way from biobased starting materials comprising only non-fossil fuel-based carbon.
  • Assessment of the biobased carbon in a material can be performed through standard test methods. Using radiocarbon and isotope ratio mass spectrometry analysis, the biobased content of materials can be determined. ASTM International, formally known as the American Society for Testing and Materials, has established a standard test method for assessing the biobased content of materials. The ASTM method is designated ASTM D6866.
  • more than 50% of the carbon atoms contained in a compound of formula (I) are biobased, based on the total number of carbon atoms contained in said compound of formula (I). More preferably, more than 60%, 70%, 75%, 80%, 85%, or 90% of the carbon atoms contained in a compound of formula (I) are biobased, based on the total number of carbon atoms contained in said compound of formula (I). According to another preferred embodiment of the present invention, more than 50% of the carbon atoms contained in a compound of formula (II) are biobased, based on the total number of carbon atoms contained in said compound of formula (II). More preferably, more than 60%, 70%, 75%, 80%, 85%, or 90% of the carbon atoms contained in a compound of formula (II) are biobased, based on the total number of carbon atoms contained in said compound of formula (II).
  • the Minimum Inhibitory Concentration (MIC) test is a test on growth inhibition. The estimation of MICs is executed in 96 well plates. Through the comparison of bacterial growth with positive and negative controls via optical density (OD), different concentrations of given test substances are evaluated.
  • MIC Minimum Inhibitory Concentration
  • substance concentrations are labelled either as inhibiting or not and MIC is defined as the lowest concentration where a complete growth inhibition is visible. Experiments are performed at least twice.
  • the synergistic activity of the compounds of formula (I) or (II) in combination with different further antimicrobial agents was determined by measuring the Minimum Inhibitory Concentrations (MIC) according to the method as described above.
  • Table 17 Table 18: *The MIC value of 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone (hydroxyethoxyphenyl butanone) was determined as being larger than 10000. For the calculation, a MIC value of 10000 was used. The respective SI value is calculated as 0.75. The actual SI value will be lower.
  • Table 21 *The MIC value of hydroxyethoxyphenyl butanol was determined as being larger than 30000. For the calculation, a MIC value of 30000 was used. The respective SI value is calculated as 0.58. The actual SI value will be lower.
  • Table 26 *The MIC value of hydroxyethoxyphenyl butanol was determined as being larger than 30000. For the calculation, a MIC value of 30000 was used. The respective SI value is calculated as 0.88. The actual SI value will be lower.
  • compositions are indicated as % by weight for all formulations.
  • Table 31 Deodorant Aerosol Table 32: Antiperspirant stick
  • HAIR CARE Table 38 Sprayable hair conditioner with zinc pyrithrione, leave-on
  • Table 48 Baby Erythema Cotton Cream
  • Table 49 Weather Protection Cream
  • Table 88 Simple hand dish wash liquid
  • Table 89 Antibacterial HDWL
  • Table 90 High performance HDWL with enzymes

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Abstract

La présente invention concerne principalement un mélange comprenant ou constitué d'un ou plusieurs composé(s) de formule (I) ou (II) tel que défini dans la description et un ou plusieurs autres agents antimicrobiens et elle concerne un produit comprenant un mélange tel que défini dans la description. De plus, la présente invention concerne l'utilisation d'un ou de plusieurs composés de formule (I) ou (II) tels que définis dans la description pour améliorer l'effet antimicrobien d'un ou plusieurs autres agents antimicrobiens et l'utilisation d'un ou plusieurs autres agents antimicrobiens pour améliorer l'effet antimicrobien d'un ou plusieurs composés de formule (I) ou (II) tels que définis dans la description. La présente invention concerne en outre l'utilisation d'un mélange tel que défini dans la description en tant qu'agent antimicrobien et un procédé tel que défini dans la description pour améliorer l'effet antimicrobien d'un ou plusieurs composés tels que définis à l'étape (a) et/ou d'un ou plusieurs composés tels que définis dans l'étape (b) du procédé. De plus, la présente invention concerne un procédé d'inhibition ou de prévention de la croissance d'un ou de plusieurs micro-organismes dans un produit ou un produit semi-fini et un procédé d'inhibition ou de prévention de la croissance d'un ou de plusieurs micro-organismes sur la peau ou la muqueuse d'un mammifère et/ou d'inhibition ou de prévention de la croissance d'un ou de plusieurs micro-organismes sur/dans une surface. De plus, la présente invention concerne un mélange ou un composé tel que défini dans la description destiné à être utilisé en tant qu'agent antimicrobien pour inhiber ou prévenir la croissance d'un ou de plusieurs micro-organismes sur la peau ou les muqueuses d'un mammifère. Enfin, la présente invention concerne l'utilisation d'un ou de plusieurs composés tels que définis dans la description en tant qu'agent(s) antimicrobien(s) et un procédé tel que défini dans la description pour inhiber ou prévenir la croissance d'un ou plusieurs micro-organismes sur la peau ou la muqueuse d'un mammifère, et/ou pour inhiber ou prévenir la croissance d'un ou plusieurs micro-organismes dans un produit ou un produit semi-fini, et/ou pour inhiber ou prévenir la croissance d'un ou plusieurs micro-organismes sur/dans une surface.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011207990A (ja) 2010-03-29 2011-10-20 Sumitomo Chemical Co Ltd 樹脂用の加工安定化剤、該加工安定化剤を含む樹脂組成物、および樹脂の加工安定性を向上させる方法
WO2018068825A1 (fr) * 2016-10-11 2018-04-19 Symrise Ag Compositions antimicrobiennes
WO2018143911A1 (fr) * 2017-01-31 2018-08-09 Kimberly-Clark Worldwide, Inc. Composition antibactérienne comprenant un ester d'acide benzoïque et procédés d'inhibition de la croissance bactérienne utilisant celle-ci

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011207990A (ja) 2010-03-29 2011-10-20 Sumitomo Chemical Co Ltd 樹脂用の加工安定化剤、該加工安定化剤を含む樹脂組成物、および樹脂の加工安定性を向上させる方法
WO2018068825A1 (fr) * 2016-10-11 2018-04-19 Symrise Ag Compositions antimicrobiennes
WO2018143911A1 (fr) * 2017-01-31 2018-08-09 Kimberly-Clark Worldwide, Inc. Composition antibactérienne comprenant un ester d'acide benzoïque et procédés d'inhibition de la croissance bactérienne utilisant celle-ci

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF THE KOREAN CHEMICAL SOCIETY, vol. 46, no. 5, 2002
SYNTHESIS, no. 15, 2003, pages 2373 - 2377
TETRAHEDRON LETTERS, vol. 56, no. 15, 2015, pages 1973 - 1975

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