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
  • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
  • A01N31/02—Acyclic compounds
• • 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
  • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
• • 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
  • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
  • A61K31/19—Carboxylic acids, e.g. valproic acid
  • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
  • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
• • 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
  • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
  • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
  • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
  • A61K31/355—Tocopherols, e.g. vitamin E
• • 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
  • A61K8/34—Alcohols
• • 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
  • A61K8/34—Alcohols
  • A61K8/345—Alcohols 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/42—Amides
• • 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
  • A61K8/67—Vitamins
  • A61K8/678—Tocopherol, i.e. vitamin E
• • 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
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
  • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
  • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

• the invention relates to a virucidal composition, especially for the virucidal disinfection of hands, and to a method for the virucidal disinfection of mammalian skin.
• Skin disinfectants especially for disinfecting hands are used in several fields where a contamination with viruses should be avoided.
• Many viruses e.g. influenza
• viruses have viral envelopes covering their protein capsids. These viruses can normally be easily inactivated by compounds destroying this lipoid envelope.
• non enveloped viruses which do not have a lipoid envelope, such as poliovirus are quite more stable against conventional disinfectants and constitute an important class of medically significant pathogens.
• poliovirus There are three types of poliovirus and many strains of each type. Type 1 poliovirus is the most virulent and common. For the classification of virucidal disinfectants, in the European standard EN14476 (February 2007) the test methods, the test viruses, and the conditions for measuring the inactivation of specific test viruses are described.
• virucidal if they can inactivate certain viruses within a certain time and to a specific extent.
• EN 14476 poliovirus and adenovirus can be used as test virus for virucidal compositions for hand disinfection.
• the standard EN 14476 also describes the test procedure and the way of measuring the inactivation of the test viruses. If a virucidal disinfectant inactivates the test virus according to the standard EN14476 within a given contact time by 4 logio units, the inactivation of the virus is 99.99 %.
• a non-enveloped virus which is very difficult to inactivate is poliovirus.
• virucidal disinfectants usually high concentrations of ethanol are necessary to inactivate these non ED 40321 / SAM:AL enveloped viruses such as poliovirus.
• a disadvantage is that ethanol evaporates very fast and that the necessary ethanol concentration decreases during the treatment to a level which is no longer high enough to inactivate the viruses sufficiently. For example, after one minute contact time a high ethanol concentration can decrease to between one forth and one third lower than at the beginning of the treatment. But normally contact times of at least two minutes are required for sufficient virucidal effect. As a consequence, it is necessary to apply an ethanol based virucidal composition again after a contact time of one minute to avoid a decrease in the ethanol concentration because of evaporation from the skin.
• Document WO 2011/072728 describes an ethanol-based virucidal composition in form of a gel to reduce the evaporation during use of the virucidal composition on the skin.
• Sterillium Virugard® (Bode Chemie, Hamburg). This product is based on 95% ethanol and further contains butanone, glycerol, myristyl alcohol and petrol ether.
• EP 0 176 720 Al which describes a disinfectant for naked viruses comprising at least 70% methanol and/or ethanol and 1 to 10% glycerol.
• Sterillium Virugard® contains a high concentration of 95% ethanol which suffers rapid evaporation. Further disadvantageously, if the product is used frequently the skin desiccates and starts itching.
• the object underlying the present invention was to provide a virucidal disinfectant having sufficient activity against poliovirus, as well as having a low ethanol concentration.
• virucidal composition comprising:
• the efficacy of the virucidal composition according to the invention against poliovirus is increased by the addition of the excipients although comprising a rather low amount of ethanol.
• the present invention has the advantage of providing a fast acting hand disinfectant with excellent skin compatibility.
• the virucidal composition is suitable for skin and hand disinfection and inactivates a most resistant virus but also is skin- compatible even if frequently used. Hence, the virucidal composition fulfils two conditions which are quite difficult to meet.
• a method for the virucidal disinfection of mammalian skin comprising the steps of:
• the virucidal composition for at most 2 min contact time, preferably for at most 1 min contact time, to reduce the virus titre for at least 4 log 10 reduction steps.
• viral disinfection means an inactivation of the test virus by at least 4 log units in at most two minutes contact time under the conditions and methods according to the European standard EN14476 (February 2007).
• Weight percent, weight- % or wt.-% are synonyms that refer to the concentration of a substance as the weight of the substance divided by the weight of the composition and multiplied by 100.
• the weight- % (wt.-%) of the components are calculated based on the total weight amount of the composition, if not otherwise stated.
• the total amount of all components of the composition does not exceed 100 wt.- .
• the remainder up to 100 wt.-% of the virucidal composition of the invention can be water.
• the water content of the virucidal composition is simply determined by subtracting the amounts of all the other ingredients from 100 wt.- .
• - equal or more than about 0.01 wt.-% to equal or less than about 1 wt.- of panthenol; equal or more than about 0.1 wt.-% to equal or less than about 5 wt.-% of glycerol, provides inactivation activity against poliovirus faster than pure ethanol although comprising a rather low amount of alcohol, particularly ethanol.
• Virucidal compositions which have an acceptable inactivation activity against poliovirus known from the state of the art usually contain far higher amounts of alcohol.
• the virucidal composition comprises from equal or more than about 0.01 wt.-% to equal or less than about 5 wt.-%, preferably from equal or more than about 0.5 wt.-% to equal or less than about 1.5 wt.-%, further preferred from equal or more than about 0.8 wt.-% to equal or less than about 1 wt.-%, myristyl alcohol.
• 1-Tetradecanol commonly is denoted myristyl alcohol.
• a virucidal composition comprising ethanol, tocopheryl acetate, panthenol, glycerol, and myristyl alcohol in comparison to pure ethanol of the same concentration achieved superior virucidal efficacy against poliovirus.
• the virucidal composition provides sufficient inactivation of poliovirus by at least 4 log 10 units within one minute contact time. This provides a very fast acting virucidal composition which for example can advantageously be used as a hand disinfectant.
• the virucidal composition can comprise skin care components.
• the virucidal composition comprises:
• C12-15 alkyl benzoate as used herein means the ester of benzoic acid and C12-15 alcohols.
• the C12-15 alcohols can be a mixture of C12 to C15 primary and branched alcohols.
• Polydimethylsiloxane (PDMS) is a polymeric organosilicon according to the formula CH 3 [Si(CH 3 ) 2 0] n Si(CH 3 )3 wherein n is the number of repeating monomer
• a virucidal composition comprising tocopheryl acetate, panthenol, glycerol, isopropyl palmitate, aloe vera, alkyl benzoate and polydimethylsiloxane but only 85 wt.-% of ethanol achieved comparable virucidal efficacy as pure ethanol at a higher concentration.
• This provides a virucidal composition with excellent skin compatibility, which advantageously can be used as a hand disinfectant for frequent use.
• the virucidal composition according to the invention has a broad virucidal activity and is particularly skin-compatible.
• the virucidal composition meets the obligations of the European standard EN 14476 (2007) and achieves an inactivation of the test viruses poliovirus and adenovirus by at least 4 logio units in at most two minutes contact time according to the test procedure described in EN 14476 (2007).
• the virucidal composition can inactivate the virus titre of poliovirus (type 1 strain LSc-2ab) within 2 min contact time by at least 4 logio reduction steps.
• the virucidal composition can inactivate the virus titre of poliovirus (type 1 strain LSc-2ab) within 1 min contact time by at least 4 logio reduction steps.
• the C2 to C3 monoalcohol can be selected from the group consisting of ethanol, 1-propanol and 2-propanol or mixtures thereof. In a preferred embodiment the monoalcohol is ethanol.
• the virucidal composition comprises from equal or more than about 70 wt.-% to less than about 95 wt.-% of ethanol.
• the virucidal composition comprises from equal or more than about 80 wt.-% to less than about 95 wt.-% of ethanol. According to another embodiment, the virucidal composition comprises from equal or more than about 80 wt.-% to equal or less than about 92 wt.-% of ethanol. According to another embodiment, the virucidal composition comprises from equal or more than about 85 wt.-% to equal or less than about 90 wt.-% of ethanol. In embodiments, the virucidal composition can comprise about 84 wt.-%, 85 wt.-% or about 89 wt.-% of ethanol.
• the tocopheryl derivative can be tocopheryl acetate.
• the virucidal composition can comprise from equal or more than about 0.02 wt.-% to equal or less than about 0.1 wt.-%, preferably from equal or more than about 0.04 wt.-% to equal or less than about 0.06 wt.-%, of tocopheryl acetate.
• the virucidal composition can comprise from equal or more than about 0.1 wt.-% to equal or less than about 0.2 wt.-%, preferably from equal or more than about 0.13 wt.-% to equal or less than about 0.16 wt.-%, of panthenol.
• the virucidal composition can comprise from equal or more than about 0.2 wt.-% to equal or less than about 4 wt.-%, preferably from equal or more than about 0.4 wt.-% to equal or less than about 2 wt.-%, more preferably from equal or more than about 0.4 wt.-% to equal or less than about 0.6 wt.-%, of glycerol.
• the virucidal composition comprises:
• panthenol - equal or more than about 0.01 wt.-% to equal or less than about 1 wt.-% of panthenol
• - equal or more than about 0.1 wt.-% to equal or less than about 5 wt.-% of glycerol; - equal or more than about 0.5 wt.-% to equal or less than about 1.5 wt.-% of myristyl alcohol.
• the virucidal composition comprises:
• panthenol - equal or more than about 0.13 wt.-% to equal or less than about 0.16 wt.-% of panthenol
• a virucidal composition comprising ethanol, tocopheryl acetate, panthenol, glycerol, and myristyl alcohol in comparison to pure ethanol of the same concentration provides superior virucidal efficacy against poliovirus, especially an inactivation of poliovirus by at least 4 log 10 units within one minute contact time.
• the virucidal composition comprises:
• the virucidal composition comprises: - equal or more than about 0.3 wt.-% to equal or less than about 0.4 wt.- , of isopropyl palmitate;
• a virucidal composition comprising tocopheryl acetate, panthenol, glycerol, isopropyl palmitate, aloe vera, alkyl benzoate and polydimethylsiloxane but only 85 wt.-% of ethanol can achieve comparable virucidal efficacy as pure ethanol at higher concentration.
• a virucidal composition comprising tocopheryl acetate, panthenol, glycerol, isopropyl palmitate, aloe vera, alkyl benzoate and polydimethylsiloxane provides excellent skin compatibility.
• the virucidal composition further can comprise lactic acid. According to a further
• the virucidal composition comprises from equal or more than about 0.001 wt.-% to equal or less than about 0.5 wt.-%, preferably from equal or more than about 0.001 wt.-% to equal or less than about 0.1 wt.-%, further preferred from equal or more than about 0.002 wt.-% to equal or less than about 0.01 wt.-%, lactic acid.
• the virucidal composition only comprises low amounts of lactic acid.
• a low amount of lactic acid provides for a low acidity of the composition which allows for a skin-compatible pH value of the virucidal composition.
• high amounts of acids which often are used as a virucidal enhancer in
• compositions of the state of the art damage the skin especially if the composition is more frequently used.
• an additional advantage of the virucidal composition according to the invention is that the pH value is skin friendly, and as a consequence the skin is not irritated even if the composition is used frequently.
• the virucidal composition according to the invention preferably does not contain percarboxylic acid. Percarboxylic acids damage the skin.
• the virucidal composition according to the invention is prepared by usual production processes, for example by mixing together the components of the virucidal composition in a mixing device.
• the virucidal composition is normally in the form of a liquid. However, for specific uses the virucidal composition can also be in the form of a gel, a foam, or an emulsion.
• the composition can further comprise additives selected from the group consisting of stabilisers, fragrance, colorants, emulsifiers, thickeners, neutralizers, denaturants, wetting agents, or mixtures thereof.
• the virucidal composition can comprise from equal or more than about 0.01 wt.-% to equal or less than about 0.2 wt.- fragrance, for example 0.07 wt.- fragrance. It should be understood that additives are optional components and can be omitted.
• the virucidal composition especially is usable for the inactivation of poliovirus (type 1 strain LSc-2ab).
• the virucidal composition according to the invention is highly active against poliovirus.
• a virucidal composition comprising composition comprising ethanol, tocopheryl acetate, panthenol, glycerol, and myristyl alcohol is capable of reducing the virus titre of Poliovirus type 1 by at least 4 logio reduction steps within a minute. This is particularly advantageous as usual compositions of the state of the art for the inactivation of poliovirus need longer contact periods to achieve the same 4 logio reduction.
• the virucidal composition can be used for the virucidal disinfection of human or animal skin. Especially, the virucidal composition is usable for the virucidal disinfection of hands.
• the virucidal composition fulfils the European testing standard EN14476.
• Hand disinfection is important for example in surgery or nursery. Hand disinfectants are normally used in hospitals, nursing homes, and in the surgical field. Particularly in the medical field it is especially advantageous that even after a short contact period the virus titre is sufficiently reduced.
• the virucidal composition is highly compatible to skin even if used very frequently during a day as is essential for example in hospitals.
• the composition can be used as virucidal hand disinfectant for frequent use.
• the virucidal composition also can be used in the field of food processing, for example meat and/or poultry processing, or in the processing of beverages.
• the virucidal composition is suitable for the virucidal disinfection of various virus- contaminated surfaces.
• the virus-contaminated surface preferably is human or animal skin.
• the invention further relates to a method for the virucidal disinfection of mammalian skin comprising the steps of:
• the virus is poliovirus (type 1 strain LSc-2ab).
• the skin is contacted with the virucidal composition for at most 1 min contact time to reduce the virus titre for at least 4 logio reduction steps.
• the method provides that even after a short contact time the virus is sufficiently inactivated.
• the method can be used for virucidal hand disinfection.
• the composition can be applied in liquid form, in the form of a gel, as a foam, or as an emulsion. It is preferred that the composition is applied in liquid form. The composition comes into contact with the skin by applying it with the hands followed by rubbing and distributing the composition evenly over the skin.
• the composition can come into contact with the skin by spraying it onto the skin.
• the virucidal composition can be applied by using a dispenser or solid support soaked with the virucidal composition.
• the support can be a woven or non- woven fabric, a textile, a paper towel, cotton wool, an absorbent polymer sheet or a sponge.
• the composition may be used at any temperature, preferably at ambient temperature.
• compositions of the invention are provided.
• Example 1 Example 2
• Example 5 Example 6 ethanol
• panthenol [wt.-%] - - - - glycerol [wt.-%] - - 0.5 (86%) 1 (86%) isopropyl palmitate
• examples 3 and 4 are examples according to the invention with an ethanol concentration of 89 % w/w and 85 % w/w, respectively, and with further components.
• Comparative examples 1 and 2 are examples only containing 89 % w/w or 85 % w/w ethanol without any further components, while comparative examples 5 and 6 contain 89 % w/w ethanol, myristyl alcohol and glycerol, or ethanol and glycerol.
• compositions of the invention as shown above in Table 1 and the compositions for comparison as shown above in Table 2 were prepared by adding the components to water and mixing.
• the antiviral efficacy of the examples against the non-enveloped Polio virus was investigated in a quantitative suspension test. The investigations were performed according to the procedure described in European norm DIN EN 14476 (February 2007).
• the virus used was Polio virus Type 1 strain LSc-2ab (Chiron Behring GmbH & Co, Marburg, Germany). Stock virus suspensions were kept frozen at -80°C. The stock viruses were multiplied in the appropriate cell line BGM, kidney cells from African green monkeys (Mikrolab, Bremen, Germany) to produce high titres of infectious viruses. The suspensions with cell detritus were frozen and thawed two times. The cell detritus was then separated by low speed centrifugation. Virus suspensions were stored at -80°C.
• a defined suspension of the virus was incubated with the undiluted disinfectant resulting in a dilution of disinfectant in the test mixture and inoculated on cultures of the BGM cell line. After 7 days the infected cells were checked for cytotoxic and cytopathogenic effects. If no cytopathogenic effects were visible, the virus has successfully been inactivated by the disinfectant.
• the antiviral activity of the undiluted disinfectant against Polio virus was tested at a time interval of 15, 30, 60, and 120 seconds using phosphate buffered saline (PBS) as interfering substance. At first, one part of interfering substance was mixed with 8 parts of the disinfectant.
• PBS phosphate buffered saline
• the virus suspension was added, mixed and incubated by vortexing the sample for 15, 30, 60, and 120 seconds. After the incubation time, an aliquot was taken and the virucidal activity was immediately suppressed by serial dilution steps with ice-cold medium. The dilutions were were stored in an ice bath until further processing. At the end of collecting and diluting of the sample, all dilutions were transferred, at 100 ⁇ for each well, into cell culture suspensions and incubated at 37°C + 1°C. After 7 days the cells were checked for cytopathogenic effects (CPE) and 50% infectious endpoint TCIDso/ml was determined. The detectable titre reduction should be at least 4 logi 0 .
• the viral infectivity titre was calculated according to the Spaermann-Karber method:
• Logic TCIDso - (Xo - 0.5 + ⁇ r/n)
• n number of all reactants per dilution step. Furthermore, the invectivity of the test virus suspension was determined under test conditions but without exposure to the disinfectant at a contact time of 120 seconds. Instead of disinfectant water was used.
• virucidal efficacy for a disinfectant is shown by demonstrating a virus titre reduction of at least 4 logio within the advised exposure time.
• Table 3 shows the results of the examples 1 to 6 for the contact times of 15, 30, 60, and 120 seconds.
• compositions according to the invention provide inactivation activity against poliovirus although comprising a low amount of ethanol.
• the example 3 provides a very fast acting disinfectant.

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• Agronomy & Crop Science (AREA)
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• Wood Science & Technology (AREA)
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• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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• 2012
  • 2012-08-28 EP EP12753706.6A patent/EP2890242A1/de not_active Withdrawn
  • 2012-08-28 EP EP17160863.1A patent/EP3205211B1/de active Active
  • 2012-08-28 ES ES17160863T patent/ES2934722T3/es active Active
  • 2012-08-28 PL PL17160863.1T patent/PL3205211T3/pl unknown
  • 2012-08-28 WO PCT/EP2012/066651 patent/WO2014032696A1/en not_active Ceased

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