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WO2023224051A1 - Agent antibactérien ou antiviral - Google Patents

Agent antibactérien ou antiviral Download PDF

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Publication number
WO2023224051A1
WO2023224051A1 PCT/JP2023/018342 JP2023018342W WO2023224051A1 WO 2023224051 A1 WO2023224051 A1 WO 2023224051A1 JP 2023018342 W JP2023018342 W JP 2023018342W WO 2023224051 A1 WO2023224051 A1 WO 2023224051A1
Authority
WO
WIPO (PCT)
Prior art keywords
antibacterial
antiviral
trans
test
present disclosure
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2023/018342
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English (en)
Japanese (ja)
Inventor
昌子 濱田
さやか 南
一宏 鳥井
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kobayashi Pharmaceutical Co Ltd
Original Assignee
Kobayashi Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kobayashi Pharmaceutical Co Ltd filed Critical Kobayashi Pharmaceutical Co Ltd
Priority to JP2024521952A priority Critical patent/JPWO2023224051A1/ja
Priority to CN202380041211.7A priority patent/CN119212556A/zh
Publication of WO2023224051A1 publication Critical patent/WO2023224051A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • 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
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/11—Aldehydes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
    • A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/14—Disinfection, sterilisation or deodorisation of air using sprayed or atomised substances including air-liquid contact processes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations

Definitions

  • the present disclosure relates to an antibacterial or antiviral agent that can impart antibacterial or antiviral effects to spaces, articles, the human body, etc.
  • antibacterial or antiviral agents are used as countermeasures.
  • Most conventional antibacterial or antiviral agents are nonvolatile, but volatile agents are also known.
  • Non-volatile antibacterial or antiviral agents must be directly attached to or contained in the target object, while volatile antibacterial or antiviral agents need to be installed in the target space or the space where the target object exists. By simply vaporizing it, the antibacterial or antiviral effect can be spread to every corner of the target space or object, and it is excellent in terms of ease of use.
  • volatile antibacterial agents include diacetyl, thymol, trans-2-hexenal, trans-2-hexenyl acetate, linalool, 1,8-cineole, and acetoin (see Patent Document 1 above).
  • 2-methylpropanoic acid 2,2-dimethyl-1-(2-hydroxy-1-methylethyl)propyl ester or its derivatives see Patent Document 2
  • capilin Patent Document 3
  • the purpose of the present disclosure is to provide a new antibacterial or antiviral agent that can impart antibacterial or antiviral effects to spaces, articles, the human body, etc.
  • the present inventor conducted intensive studies to solve the above problems and found that 2-cyclohexen-1-one, ⁇ -angelicalactone, 2-cyclopenten-1-one, trans,trans-2,4-hexadienal It has been found that propionaldehyde, butyraldehyde, branched aldehydes with a molecular weight of 150 or less, and cyclic aldehydes have excellent antibacterial or antiviral effects and can be used as antibacterial or antiviral agents. Furthermore, the present inventors have discovered that the compound is volatile and can impart antibacterial or antiviral effects to a target object even in a volatilized state. The present invention was completed through further studies based on these findings.
  • Item 1 2-cyclohexen-1-one, ⁇ -angelicalactone, 2-cyclopenten-1-one, trans, trans-2,4-hexadienal, propionaldehyde, butyraldehyde, branched aldehyde with a molecular weight of 150 or less, and cyclic aldehyde
  • the active ingredients include 2-cyclohexen-1-one, ⁇ -angelicalactone, 2-cyclopenten-1-one, trans,trans-2,4-hexadienal, propionaldehyde, butyraldehyde, 2-ethylbutanal, Item 1.
  • the antibacterial or antibacterial agent according to item 1 which is at least one selected from the group consisting of 2-methylbutanal, trans-2-methyl-2-pentenal, 2-methyl-2-pentenal, phenylacetaldehyde, and furfural. Viral agent.
  • Item 3. An antibacterial or antiviral composition for use in spaces, comprising the antibacterial or antiviral agent according to item 1 or 2, and a solvent.
  • An antibacterial or antiviral composition for articles comprising the antibacterial or antiviral agent according to item 1 or 2, and a solvent.
  • Item 5. The antibacterial or antiviral composition for an article according to Item 4, wherein the article is a textile product.
  • the above compound is 2-cyclohexen-1-one, ⁇ -angelicalactone, 2-cyclopenten-1-one, trans,trans-2,4-hexadienal, propionaldehyde, butyraldehyde, 2-ethylbutanal, -
  • the above compound is 2-cyclohexen-1-one, ⁇ -angelicalactone, 2-cyclopenten-1-one, trans,trans-2,4-hexadienal, propionaldehyde, butyraldehyde, 2-ethylbutanal, -Methylbutanal, trans-2-methyl-2-pentenal, 2-methyl-2-pentenal, phenylacetaldehyde, and furfural, the method according to item 11.
  • Item 13 The object that requires antibacterial or antiviral treatment is space, Item 13.
  • the method according to Item 11 or 12 wherein the space is treated with the compound.
  • Section 14 The object that requires antibacterial or antiviral properties is a product, 13.
  • the method according to item 11 or 12, wherein the article is treated with the compound.
  • a novel antibacterial or antiviral agent is provided. Furthermore, by volatilizing within the space, the antibacterial or antiviral agent of the present disclosure exerts an antibacterial or antiviral effect not only on the space but also on articles existing in the space and members partitioning the space. This makes it possible to make the living space a sanitary environment using a simple method and reduce the risk of contracting infectious diseases. In addition, since bacteria present in living spaces also cause bad odors, the antibacterial or antiviral agent of the present disclosure can prevent or remove bad odors and create a comfortable living space.
  • a branched aldehyde is an aldehyde having a branched carbon skeleton.
  • volatility refers to volatilization at normal temperature and normal pressure (20° C., 1 atm).
  • antibacterial refers to reducing the activity of bacteria and causing sterilization or growth inhibition of bacteria.
  • antiviral refers to reducing the activity of the virus, reducing the number of viruses, reducing the infectivity of the virus, or suppressing the proliferation of the virus.
  • an antibacterial or antiviral agent refers to a substance used for antibacterial or antiviral applications.
  • an antibacterial or antiviral composition for a space refers to a composition that is used by treating a space with an antibacterial or antiviral agent for the purpose of making the space antibacterial or antiviral.
  • an antibacterial or antiviral composition for an article refers to a composition that is used by treating the article with an antibacterial or antiviral agent for the purpose of making the article antibacterial or antiviral.
  • an antibacterial or antiviral external composition refers to a composition that is applied to the skin for antibacterial or antiviral purposes.
  • an antibacterial or antiviral method refers to a method of imparting an antibacterial or antiviral effect to a subject in need of antibacterial or antiviral action.
  • a hard surface refers to the surface of a hard member such as resin, ceramic, glass, etc.
  • the antibacterial or antiviral agent of the present disclosure includes 2-cyclohexen-1-one, ⁇ -angelicalactone, 2-cyclopenten-1-one, trans,trans-2,4-hexadienal, propionaldehyde. , butyraldehyde, branched aldehydes with a molecular weight of 150 or less, cyclic aldehydes, and trans,trans-2,4-hexadienal as an active ingredient.
  • the antibacterial or antiviral agent of the present disclosure will be described in detail below.
  • one of the active ingredients is 2-cyclohexenone (CAS 930-67-7).
  • 2-Cyclohexen-1-one is a type of volatile cyclic ketone.
  • one of the active ingredients is alpha-angelicalactone (CAS 591-12-8).
  • ⁇ -angelicalactone is a type of volatile lactone.
  • one of the active ingredients is 2-Cyclopentenone (CAS 930-30-3).
  • 2-Cyclopenten-1-one is a type of volatile cyclic ketone.
  • trans,trans-2,4-hexadienal is a type of volatile linear aldehyde.
  • propionaldehyde (CAS 123-38-6).
  • Propionaldehyde is a type of volatile linear aldehyde.
  • butyraldehyde (CAS 123-72-8).
  • Butyraldehyde is a type of volatile linear aldehyde.
  • one of the active ingredients is a branched aldehyde with a molecular weight of 150 or less.
  • Branched aldehydes with a molecular weight of 150 or less are volatile compounds.
  • the molecular weight of the branched aldehyde may be 150 or less, specifically 72 to 150, preferably 72 to 120, more preferably 85 to 110.
  • the branched aldehydes with a molecular weight of 150 or less include 2-ethylbutanal (CAS 97-96-1), 2-methylbutanal (CAS 96-17-3), trans-2-methyl-2-pentenal; CAS 14250-96-5, 2-methyl-2-pentenal; CAS 623-36-9 ), isovaleraldehyde (CAS 590-86-3), melonal (CAS 106-72-9), etc.
  • one of the active ingredients is a cyclic aldehyde.
  • the aldehyde group may be directly bonded to the atoms constituting the cyclic structure, or the aldehyde group may be bonded to the atoms constituting the cyclic structure via one or more atoms.
  • the cyclic structure in the cyclic aldehyde may be any of an alicyclic ring, a heterocyclic ring, or an aromatic ring, and may be monocyclic or polycyclic.
  • the cyclic aldehyde used in the antibacterial or antiviral agents of the present disclosure is volatile.
  • Examples of volatile cyclic aldehydes include phenylacetaldehyde (CAS 122-78-1), furfural (CAS98-01-1), benzaldehyde (CAS 100-52-7), and tripral. (triplal: CAS 68039-49-6) cinnamic aldehyde (CAS 104-55-2), anisaldehyde (CAS 123-11-5), (4-methylphenyl)acetaldehyde: CAS 104-09-6), 5-methyl furfural (CAS 620-02-2), 2-furancarboxaldehyde (CAS 98-01-1), 2-pyrrolylcarbaldehyde (2-pyrrolylcarbaldehyde: CAS 1003-29-8), 3-thienylcarbaldehyde (3-thienylcarbaldehyde: CAS 498-62-4), p-tolualdehyde (CAS 104-87-0), ⁇ - Examples include methylcinnamaldehyde ( ⁇ -methylcin
  • the active ingredients include 2-cyclohexen-1-one, ⁇ -angelicalactone, 2-cyclopenten-1-one, trans,trans-2,4-hexadienal, propionaldehyde,
  • One type may be selected from butyraldehyde, a branched aldehyde having a molecular weight of 150 or less, and a cyclic aldehyde and used alone, or two or more types thereof may be used in combination.
  • antibacterial or antiviral agents of the present disclosure can inhibit the growth of a wide variety of bacteria or viruses.
  • the type of bacteria to which the antibacterial or antiviral agent of the present disclosure is applied is not particularly limited, and may be either gram-positive bacteria or gram-negative bacteria.
  • the Gram-positive bacteria to which the antibacterial or antiviral agent of the present disclosure is applied include Staphylococci such as Staphylococcus aureus; Bacillus bacteria; Listeria bacteria; Alicyclobacillus bacteria, and the like.
  • Gram-negative bacteria to which the antibacterial or antiviral agent of the present disclosure is applicable include Escherichia bacteria such as Escherichia coli; Klebsiella bacteria such as Klebsiella pneumoniae; Pseudomonas bacteria such as Pseudomonas aeruginosa; Salmonella bacteria; Vibrio Bacteria of the genus Acinetobacter; examples thereof include bacteria of the genus Acinetobacter.
  • suitable examples to which the antibacterial or antiviral agent of the present disclosure is applied include Staphylococcus, Escherichia bacteria, and Klebsiella bacteria.
  • the type of virus to which the antibacterial or antiviral agent of the present disclosure is applicable is not particularly limited, and may be either an enveloped virus or a non-enveloped virus.
  • the enveloped viruses to which the antibacterial or antiviral agent of the present disclosure is applicable include influenza viruses, coronaviruses (HCoV-229E, HCoV-OC43, HCoV-NL63, HCoV-HKU1), and new coronaviruses ( Examples include SARS-CoV-2), herpesvirus, and respiratory syncytial virus.
  • non-enveloped viruses to which the antibacterial or antiviral agent of the present disclosure is applicable include feline calicivirus, norovirus, rotavirus, poliovirus, adenovirus, and the like.
  • preferred examples to which the antibacterial or antiviral agent of the present disclosure is applied include influenza virus, feline calicivirus, and norovirus.
  • the antibacterial or antiviral agent of the present disclosure is used to impart antibacterial or antiviral effects to a target by treating the target for which antibacterial or antiviral properties are desired.
  • Targets for which antibacterial or antiviral treatment is required include not only spaces or articles where bacteria or viruses exist or are attached, but also prevention of adhesion or proliferation of bacteria or viruses even when bacteria or viruses are not present or attached. It also includes spaces or articles that require the same.
  • the antibacterial or antiviral agent of the present disclosure may be volatilized or sprayed within the space.
  • the antibacterial or antiviral agent of the present disclosure is mixed with a volatile solvent to form an antibacterial or antiviral composition for spaces. Just provide it.
  • the content of the antibacterial or antiviral agent of the present disclosure in the antibacterial or antiviral composition for space may be set as appropriate depending on the type and size of the space to which it is applied, but for example, the content of the above compound
  • the amount may be 0.1 to 99.9% by weight, preferably 1 to 99.9% by weight, more preferably 1 to 80% by weight.
  • the solvent used in the antibacterial or antiviral composition for space may be any solvent as long as it can solubilize or disperse the antibacterial or antiviral agent of the present disclosure and can volatilize at room temperature, such as water,
  • Examples include paraffinic hydrocarbons (plasmid isoparaffin, plasma-fluid normal paraffin), 3-methoxy-3-methyl-1-butanol, propylene glycol monomethyl ether, and the like. These solvents may be used alone or in combination of two or more.
  • the content of the solvent may be the balance other than the antibacterial or antiviral agent of the present disclosure and additives added as necessary.
  • antibacterial or antiviral composition for space may contain other additives in addition to the antibacterial or antiviral agent of the present disclosure.
  • additives that can be incorporated into antibacterial or antiviral compositions for spaces include, for example, surfactants, antioxidants, pH adjusters, fragrances, deodorants, disinfectants, ultraviolet absorbers, and insecticides. ingredients, insect repellent ingredients, repellent ingredients, gelling agents, etc.
  • the shape of the antibacterial or antiviral composition for space is not particularly limited as long as the antibacterial or antiviral agent of the present disclosure can be volatilized or sprayed; For example, it may be in liquid or gel form, and in the case of spraying, it may be in liquid form.
  • the antibacterial or antiviral composition for space can be volatilized into the space using the same method as for conventional stationary air fresheners. Just leave it still.
  • a spray or aerosol container may be used to spray the space antibacterial or antiviral composition into the space.
  • the space to which the antibacterial or antiviral composition for space can be applied may be any space that is partitioned off from the outdoors, such as box spaces such as trash cans and shoe racks; living rooms, toilets, bathrooms, washrooms, etc. Examples include indoor spaces such as entrances and closets; interior spaces of automobiles, buses, and trucks; and spaces within facilities such as restaurants, factories, offices, and conference rooms.
  • a suitable example of a space in which the antibacterial or antiviral agent of the present disclosure is volatilized includes a trash can or a space where a trash can is installed.
  • trash cans are a source of bad odors as bacteria tend to propagate therein, bad odors can be prevented or removed by volatilizing the antibacterial or antiviral agent of the present disclosure in the trash cans or in the space where the trash cans are installed. Can be done.
  • the article may be coated or sprayed with the antibacterial or antiviral agent of the present disclosure.
  • the antibacterial or antiviral agent of the present disclosure may be mixed with a solvent and provided as an antibacterial or antiviral composition for articles. good.
  • the content of the antibacterial or antiviral agent of the present disclosure in the antibacterial or antiviral composition for articles may be set as appropriate depending on the space to which it is applied, the type of article, etc.; is 0.1 to 99.9% by weight, preferably 1 to 99.9% by weight, more preferably 1 to 80% by weight.
  • the solvent used in the antibacterial or antiviral composition for articles may be any solvent as long as it can solubilize or disperse the antibacterial or antiviral agent of the present disclosure, and examples thereof include water, ethanol, propanol, etc. . These solvents may be used alone or in combination of two or more.
  • the content of the solvent may account for the balance other than the antibacterial or antiviral agent of the present disclosure and additives added as necessary.
  • the antibacterial or antiviral composition for articles may contain other additives in addition to the antibacterial or antiviral agent of the present disclosure.
  • additives that can be incorporated into volatile antibacterial or antiviral compositions include, for example, surfactants, antioxidants, pH adjusters, fragrances, deodorants, disinfectants, ultraviolet absorbers, and insecticides. ingredients, insect repellent ingredients, repellent ingredients, etc.
  • the antibacterial or antiviral composition for articles may be provided in the form of a wiping sheet, for example, by impregnating a fabric such as a nonwoven fabric, in order to make it easier to apply or spray onto the article to which it is applied. It may also be provided in the form of a spray or aerosol.
  • Examples of articles to which antibacterial or antiviral compositions can be applied include textile products such as cloth sofas, bedding, clothing, curtains, masks, diapers, wet towels, and carpets; toilet bowls, bathtubs, washbasins, and sinks. , hard surfaces such as tiles and glass; architectural structures such as wallpaper, doors, handrails, floors, windows, and ceilings; trash cans, chairs, desks, electrical appliances, storage furniture, shoe cabinets, shoes, leather products, etc.
  • a trash can is a suitable example of an article to which the antibacterial or antiviral agent of the present disclosure is applied.
  • Trash cans are a breeding ground for bacteria and are a source of bad odors, so by treating the trash cans with the antibacterial or antiviral agent of the present disclosure, bad odors can be prevented or removed.
  • textile products are another suitable example of articles to which the antibacterial or antiviral agent of the present disclosure is applied.
  • an article to which the antibacterial or antiviral agent of the present disclosure is applied is a hard surface, particularly a hard surface made of plastic.
  • One preferred embodiment of treating a hard surface with the antibacterial or antiviral agent of the present disclosure is to use propionaldehyde and/or butyraldehyde as the antibacterial or antiviral agent of the present disclosure.
  • Antibacterial or antiviral use in the body By applying the antibacterial or antiviral agent of the present disclosure to the skin, it can impart an antibacterial or antiviral effect to the skin and make the skin in a sanitary state.
  • the antibacterial or antiviral agent of the present disclosure When applying the antibacterial or antiviral agent of the present disclosure to the skin, it may be provided as an external antibacterial or antiviral composition containing the antibacterial or antiviral agent of the present disclosure.
  • the content of the antibacterial or antiviral agent of the present disclosure in the external antibacterial or antiviral composition may be appropriately set depending on the formulation form of the external composition. For example, if the amount of the compound is 0.1 -50% by weight, preferably 0.1-30% by weight, more preferably 0.1-10% by weight.
  • the antibacterial or antiviral external composition may be formulated by blending the antibacterial or antiviral agent of the present disclosure with additives and base materials.
  • the antibacterial or antiviral composition for external use may be in any formulation form, such as a pharmaceutical for external use on the skin, a cosmetic, a skin cleansing agent, etc., as long as it is applied to the skin.
  • Specific formulation forms of antibacterial or antiviral external compositions include creams, lotions, gels, emulsions, liquids, poultices, patches, liniments, aerosols, aqueous ointments, and packs.
  • External skin medicines such as hand gels and hand disinfectants; Cosmetics such as aqueous ointments, creams, milky lotions, lotions, lotions, packs, and gels; Skin cleansers such as body shampoos, hair shampoos, conditioners, and wet wipes. Examples include fees.
  • the antibacterial or antiviral agent of the present disclosure plays a role as a preservative when added to products that require antibacterial or antiviral properties, and improves the preservability of the product. Alternatively, durability can also be improved.
  • the types of products that require antibacterial or antiviral properties are not particularly limited, but include, for example, foods, pharmaceuticals, cosmetics, textile products, resin products, paper products, etc.
  • the content of the antibacterial or antiviral agent of the present disclosure in the product may be appropriately set depending on the type of the product, but for example, the content of the compound may be 0.1 to 50% by weight, preferably 0.1% by weight. 1 to 30% by weight, more preferably 0.1 to 10% by weight.
  • the antibacterial or antiviral agent of the present disclosure may be added as an additive. Further, if the product is a textile product, a resin product, or a paper product, the antibacterial or antiviral agent of the present disclosure may be kneaded into the material used for manufacturing these products.
  • Test Example 1 Evaluation of antibacterial effect on bacteria smeared on agar medium 1. Test Materials and Test Methods In this test, volatile substances and test bacterial strains were allowed to stand in a closed space without contact, and the antibacterial effect exerted by volatilization of the test specimen was evaluated. Specific test materials and test methods are as shown below.
  • Test strain Staphylococcus aureus NBRC12732 and Escherichia coli NBRC3972 were prepared as test strains.
  • test bacterial suspension The test bacterial strain cultured on SCD agar medium is scraped off using a 10 ⁇ l disposable loop, one full colony is scraped off, and added to 10 ml of sterile physiological saline and thoroughly stirred to prepare a test bacterial suspension. did. Next, the number of bacteria in the test bacteria suspension was counted by colony forming unit (CFU) counting method (smear plate culture method), and the test bacteria suspension was diluted with sterile physiological saline to approximately 1.0 ⁇ 10 7 cfu. /mL test bacterial solution was prepared.
  • CFU colony forming unit
  • test bacteria plates 0.1 mL of each test bacteria solution was smeared onto an SCD plate medium (using a Petri dish with a diameter of 9.0 cm and a height of 2.0 cm) to prepare test bacteria plates.
  • SCD plate medium using a Petri dish with a diameter of 9.0 cm and a height of 2.0 cm
  • test container (diameter 2.6cm, height 1.2cm) to the center of the inside bottom of glass Petri dish A (diameter 8.5cm, height 3.0cm) with double-sided tape. It was fixed and used as a test container.
  • test specimens were stock solutions (100%) of each volatile substance shown in Tables 1 and 2, and diluted solutions obtained by diluting them with isoparaffin to the concentrations shown in Tables 1 and 2. .
  • Antibacterial test 1 ml of the test specimen was added to glass Petri dish B of the test container. Next, place the test bacteria plate on the test container so that the inner bottom of the glass petri dish A of the test container and the inner bottom of the test bacteria plate (the SCD plate medium side on which the test bacteria solution has been smeared) are facing each other, and place the test bacteria plate on the test container. By wrapping the surrounding area with parafilm and sealing it so that no gap was left at the interface with the test bacteria plate, the test specimen and the test bacterial strain were allowed to stand in a closed space without contact, and incubated at 37°C for 24 hours. .
  • Test example 2 Evaluation of antibacterial effect on fiber surface 1. Test materials and test methods In this test, after a piece of fiber was left standing in an environment where volatile substances had been volatilized, the piece of fiber and the test bacterial strain were left standing in contact with each other, and the antibacterial effect of the piece of fiber was evaluated. . Specific test materials and test methods are as shown below.
  • Test strain Klebsiella pneumoniae NBRC13277 and Staphylococcus aureus NBRC12732 were prepared as test strains.
  • test bacterial solution One loop of the test bacterial strain cultured on the SCD agar medium was taken, suspended in 20 mL of NB liquid medium, and cultured with shaking at 37°C for 18 to 24 hours. 0.4 mL of the shaking culture solution and culture solution was taken, suspended in 20 mL of NB liquid medium, and cultured with shaking at 37°C for 2 to 4 hours. Next, the number of bacteria in the obtained culture solution was measured by colony forming unit (CFU) counting method (smear plate culture method), and the culture solution was diluted with 1/20 NB liquid medium to 1.0 to 3.0 ⁇ 10 5 cfu. /mL test bacterial solution was prepared.
  • CFU colony forming unit
  • test specimen treated fibers and untreated fibers Place 0.4 g of cut cotton cloth (2 cm x 2 cm square) and glass Petri dish B (diameter 2.6 cm, height 1.2 cm) are placed side by side, 0.5 mL of the test sample is added to the inside of glass petri dish B, and the lid is placed on glass petri dish A, so that the test sample and cotton cloth are not in contact with each other in a closed space. did. In this state, it was left standing at room temperature for 30 minutes to obtain a test sample treated fiber. The test sample treated fibers were prepared immediately before the antibacterial test described below. In addition, 0.4 g (2 cm x 2 cm square) of cotton cloth that had not been subjected to the above treatment was prepared as an untreated fiber.
  • the antibacterial effect was evaluated based on the antibacterial activity value according to the following criteria. ⁇ Judgment criteria for antibacterial action> A: Antibacterial activity value is 3.0 or higher (high antibacterial effect) B: Antibacterial activity value is 2.0 or more and less than 3.0 (has antibacterial effect) C: Antibacterial activity value less than 2.0 (no antibacterial effect)
  • Test example 3 Evaluation of antibacterial effect on hard surfaces (1) 1. Test materials and test methods In this test, a polyvinyl chloride plate is left standing in an environment where volatile substances have been volatilized, and then the plate and the test bacterial strain are left standing in contact with each other to evaluate the antibacterial effect of the plate. did. Specific test materials and test methods are as shown below.
  • Test strain Escherichia coli NBRC3972 and Staphylococcus aureus NBRC12732 were prepared as test strains.
  • test bacterial solution Take one loopful of the test bacterial strain cultured on SCD agar medium at 34 to 36°C for 16 to 24 hours, dilute the culture liquid with 1/500 NB liquid medium, and add 2.5 to 10 ⁇ 10 A test bacterial solution of 5 cfu/mL was prepared.
  • test specimens A stock solution (100%) of each volatile substance shown in Table 4 and a diluted solution obtained by diluting it with isoparaffin to the concentration shown in Table 4 were used as test specimens.
  • test sample treated plate and untreated plate Place a cut polyvinyl chloride plate (4.8 cm x 4.8 cm square) and a glass plate on the inside bottom of glass petri dish A (diameter 8.5 cm, height 3.0 cm). Place petri dishes B (diameter 2.6 cm, height 1.2 cm) side by side, add 0.5 mL of test sample to the inside of glass petri dish B, and cover glass petri dish A to keep the test sample and cotton cloth away in a closed space. made contact. In this state, the plate was left standing at room temperature for 30 minutes to obtain a test sample treatment plate. The test specimen processing plate was prepared immediately before the antibacterial test described below. In addition, a polyvinyl chloride plate (4.8 cm x 4.8 cm square) which had not been subjected to the above treatment was prepared as an untreated plate.
  • Antibacterial test Inoculate 400 ⁇ L of test bacterial solution uniformly over the entire surface of the test sample treated plate or untreated plate, cover with parafilm (4 cm x 4 cm square), and keep at 35°C and relative humidity 90%. It was left standing at RH or above for 24 hours.
  • transfer the test specimen treated plate or untreated plate to a vinyl bag while still covered with parafilm add 10 mL of SCDLP liquid medium, and thoroughly massage the bacteria from the outside of the vinyl bag by hand to remove the bacteria into the SCDLP liquid medium. to obtain a bacterial dispersion. Thereafter, the number of bacteria in the bacterial dispersion was measured by colony forming unit (CFU) counting method (smear plate culture method), and the antibacterial activity value was calculated according to the following formula.
  • CFU colony forming unit
  • the antibacterial effect was evaluated based on the antibacterial activity value according to the following criteria. ⁇ Judgment criteria for antibacterial action> A: Antibacterial activity value is 3.0 or higher (high antibacterial effect) B: Antibacterial activity value is 2.0 or more and less than 3.0 (has antibacterial effect) C: Antibacterial activity value less than 2.0 (no antibacterial effect)
  • Test example 4 Evaluation of antibacterial effect on hard surfaces (2) 1. Test Materials and Test Methods In this test, a polyurethane plate was left standing in an environment where volatile substances had been volatilized, and then the plate and the test bacterial strain were left standing in contact with each other to evaluate the antibacterial activity of the plate. The test materials and test method were the same as in Test Example 3, except that a polyurethane plate (4.8 cm x 4.8 cm square) was used instead of the polyvinyl chloride plate.
  • polyurethane plates thus prepared exhibited excellent antibacterial activity against Staphylococcus aureus (Examples 1 to 4, 6 to 8, and 12).
  • Test Example 5 Evaluation of antiviral effect on fiber surface 1. Test materials and test methods In this test, a piece of fiber is left standing in an environment where volatile substances have been volatilized, and then the piece of fiber and the test virus are left in contact with each other to evaluate the antiviral effect of the piece of fiber. did. Specific test materials and test methods are as shown below.
  • Test virus Test strains include influenza virus (Influenza A virus (H1N1); Strain: ATCC VR-1469, host cell: MDCK (NBL-2) cell) and feline calicivirus (Strain: ATCC VR-782). , host cells: CRFK cells) were prepared.
  • test virus solution Inoculate the prepared host cells with the test strain solution diluted with EMEM(-), culture overnight at 37°C in the presence of 5% CO2 , and then centrifuge and collect the supernatant. By this, a virus suspension of 1.0 ⁇ 10 7 to 1.0 ⁇ 10 8 pfu/mL was prepared. Next, the obtained virus suspension was diluted 10 times with sterile purified water to prepare a test virus solution.
  • test specimen treated fibers and untreated fibers Place 0.4 g of cut cotton cloth (2 cm x 2 cm square) and glass Petri dish B (diameter 2.6 cm, height 1.2 cm) are placed side by side, 0.5 mL of the test sample is added to the inside of glass petri dish B, and the lid is placed on glass petri dish A, so that the test sample and cotton cloth are not in contact with each other in a closed space. did. In this state, it was left standing at room temperature for 30 minutes to obtain a test sample treated fiber. The test sample treated fibers were prepared immediately before the antibacterial test described below. In addition, 0.4 g (2 cm x 2 cm square) of cotton cloth that had not been subjected to the above treatment was prepared as an untreated fiber.
  • Antiviral test Put the test sample treated fiber or untreated fiber into a vial, inoculate 200 ⁇ L of test virus solution evenly over the whole of the test sample treated fiber or untreated fiber, and place it in the vial. The lid was closed and the mixture was allowed to stand at 25°C for 18 hours. Next, 20 mL of SCDLP liquid medium was added into the vial and thoroughly stirred to disperse the bacteria in the SCDLP liquid medium to obtain a virus dispersion. Thereafter, 0.1 mL of the virus dispersion liquid was added to 0.9 mL of EMEM(-), the number of plaques was measured by the plaque measurement method, and the antiviral activity value was calculated according to the following formula.
  • the antibacterial effect was evaluated based on the antiviral activity value according to the following criteria. ⁇ Judgment criteria for antiviral effect> A: Antiviral activity value is 3.0 or higher (high antiviral effect) B: Antiviral activity value is 2.0 or more and less than 3.0 (has antiviral effect) C: Antiviral activity value less than 2.0 (no antiviral effect)
  • Test Example 6 Evaluation of antiviral effect on hard surfaces 1. Test materials and test methods In this test, a polyurethane plate was left standing in an environment where volatile substances were volatilized, and then the plate and the test virus were left standing in contact with each other to evaluate the antiviral effect of the plate. .
  • the test materials and test method were the same as those described above, except that a polyurethane plate (4.8 cm x 4.8 cm square) was used instead of the fiber piece, and the amount of test virus solution in the vial was changed to 400 ⁇ L. This is the same as in Example 5.

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Abstract

Le but de la présente invention est de fournir un nouvel agent antibactérien ou antiviral capable de conférer un effet antibactérien ou antiviral à des espaces, des articles, des corps humains, etc. L'invention concerne un agent antibactérien ou antiviral contenant au moins un composé choisi dans le groupe constitué de 2-cyclohexén-1-one, d'α-angélicalactone, de 2-cyclopentène-1-one, de trans, de trans-2,4-hexadiénal, de propionaldéhyde, de butyraldéhyde, d'un aldéhyde à chaîne ramifiée ayant un poids moléculaire inférieur ou égal à 150 et d'un aldéhyde cyclique.
PCT/JP2023/018342 2022-05-19 2023-05-16 Agent antibactérien ou antiviral Ceased WO2023224051A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19826499A1 (de) * 1998-06-13 1999-12-16 Beiersdorf Ag Gegen Bakterien, Mycota, Viren, Parasiten und Protozoen wirksame Substanzen
JP2000026287A (ja) * 1994-09-09 2000-01-25 Shozo Koyama 分子発現機能抑制剤
JP2013526604A (ja) * 2010-05-23 2013-06-24 高砂香料工業株式会社 抗菌組成物
JP2013537430A (ja) * 2010-08-27 2013-10-03 アニトックス コーポレーション 抗菌性処方剤
JP2015504312A (ja) * 2011-11-30 2015-02-12 アニトックス コーポレーション アルデヒド、有機酸及び有機酸エステルの抗微生物混合物
JP2017206466A (ja) * 2016-05-19 2017-11-24 株式会社もんじゅ テルペンアルデヒドを含有する併用剤

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000026287A (ja) * 1994-09-09 2000-01-25 Shozo Koyama 分子発現機能抑制剤
DE19826499A1 (de) * 1998-06-13 1999-12-16 Beiersdorf Ag Gegen Bakterien, Mycota, Viren, Parasiten und Protozoen wirksame Substanzen
JP2013526604A (ja) * 2010-05-23 2013-06-24 高砂香料工業株式会社 抗菌組成物
JP2013537430A (ja) * 2010-08-27 2013-10-03 アニトックス コーポレーション 抗菌性処方剤
JP2015504312A (ja) * 2011-11-30 2015-02-12 アニトックス コーポレーション アルデヒド、有機酸及び有機酸エステルの抗微生物混合物
JP2017206466A (ja) * 2016-05-19 2017-11-24 株式会社もんじゅ テルペンアルデヒドを含有する併用剤

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