EP2635120A1 - Zusammensetzungen mit oleuropeinen und flavanoiden und ihre verwendung - Google Patents

Zusammensetzungen mit oleuropeinen und flavanoiden und ihre verwendung

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Publication number
EP2635120A1
EP2635120A1 EP10742237.0A EP10742237A EP2635120A1 EP 2635120 A1 EP2635120 A1 EP 2635120A1 EP 10742237 A EP10742237 A EP 10742237A EP 2635120 A1 EP2635120 A1 EP 2635120A1
Authority
EP
European Patent Office
Prior art keywords
composition
component
acid
oleuropein
pharmaceutically acceptable
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.)
Withdrawn
Application number
EP10742237.0A
Other languages
English (en)
French (fr)
Inventor
Ian Ripley
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.)
Phyto Innovative Products Ltd
Original Assignee
Phyto Innovative Products 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 Phyto Innovative Products Ltd filed Critical Phyto Innovative Products Ltd
Publication of EP2635120A1 publication Critical patent/EP2635120A1/de
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • A01N43/14—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 six-membered rings
    • A01N43/16—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 six-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
    • 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
    • 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
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions
    • A61K2800/5922—At least two compounds being classified in the same subclass of A61K8/18
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • 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 present invention relates to compositions and their uses in eradicating or ameliorating unwanted infestations. More particularly the invention relates to compositions and their uses which comprise a flavanoid component and an oleuropein component. Such compositions are aptly employed to eliminate or reduce the presence of unwanted bacteria or other undesirable organisms.
  • flavanoids have been suggested as anti-microbial agents.
  • PCT/GB2007/002756 and PCT/GB2007/002758 describe particularly effective compositions containing flavanoids.
  • the effectiveness of known compositions of bioflavanoids would benefit from enhancement.
  • the present invention is based on the finding that certain combinations of agents are particularly effective in eliminating or reducing unwanted bacteria and other undesirable organisms.
  • the present invention provides a pharmaceutical composition which comprises a first component being a flavanoid component and a second component being an oleuropein component.
  • the first component will be a one or more flavanoids of Formula (I) :
  • R 1 is hydroxyl or methoxyl and R 2 is hydrogen, hydroxyl or methoxyl and X is hydrogen or a saccharide.
  • the second component will be oleuropein or an acetylated derivative thereof.
  • Oleuropein is (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]- 2-oxoethyl]- 5-ethylidene-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6- (hydroxymethyl)- 2-tetrahydropyranyl]oxy]-4H-pyran-3-carboxylic acid, methyl ester.
  • R 2 is hydrogen and R 1 is in the 3- or 4- position .
  • R 1 is 4-methoxyl .
  • X in a compound of the Formula (I) is H .
  • X in a compound of Formula (I) is a saccharide.
  • X is a disaccharide
  • Suitable disaccharides include combinations of two monosaccharide, suitably pyranoses, linked by a glycosidic bond, for example rhamnose and glucose, for example L-rhamnose and D-glucose.
  • Suitable disaccharides can have the structure:
  • R 3 and R 4 are H and the other OH or both are H or both are OH .
  • R 3 is H and R 4 is OH so that the disaccharide is rutinose.
  • Favoured aglycones of flavonoids for use in this invention are the disaccharides 6-0-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranose, also known as rutinose, and 2-0-(alpha-L-rhamnopyra-nosyl)-beta-D- glucopyra-rose.
  • the first component very suitably comprises narangin or neohesperidin or mixtures thereof.
  • Mixtures of one or both of narangin and neohesperidin with for example, one, two or three other flavanoids of the Formula I are presently believed particularly favoured for use in this invention. Such mixtures can be obtained from extraction from bitter oranges.
  • Suitable compounds of Formula (I) include Neoeriocitrin, Isonaringin, Narangin, Hesperidin, Neohesperidin, Neodiosmin, Naringenin, Poncirin and Rhiofolin.
  • Favoured compositions for use include those which comprise either of naringin and neohespiridin or both.
  • the invention will contain naringin and neohesperidin and other flavonoids of the Formula (I).
  • the mixture of flavonoids may aptly contain more than one of neohesperidin, naringin, isocriocrin, isonaringin, naringin, hesperidine, neohesperidin, neocliomin, naringenin, poncrin and rhiofolin.
  • a mixture of flavonoids can be obtained from bitter oranges, see for example PCT/GB2007/002756.
  • Suitable mixtures can include 2, 3, 4, 5, 6, 7, 8, 9 or more compounds of formula (I).
  • a mixture comprising 2, 3, 5, 6, 7, 8 or 9 of the above named flavonoids is apt, for example containing 3, or containing 4, or containing 5, or containing 6, or containing 7, or containing 8 or containing 9 of said flavonoids.
  • compositions of such flavonoids have advantages over the use of a single flavonoid. It is particularly advantageous that extract of bitter oranges may be employed without the need for isolating individual flavonoids if desired.
  • the use of the composition generally comprising biomass enhances solubility of the flavanoids.
  • the flavanoids are present in mixtures with biomass by about 10% to 75%, more aptly 30% to 60%, for example 40% to 50%, preferably about 45%.
  • the biomass comprises pectins and other sugar derived materials. Typically about 40% of low molecular weight pectins are present.
  • solubilising agents such as dextrins, for example cyclodextrin, may be employed if desired .
  • the mixture of flavonoids will comprise at least 25%, more suitably at least 40% and preferably at least 50% of narangin. More aptly the mixture will contain up to 65% of narangin.
  • the mixture of flavonoids will comprise at least 15%, more suitably at least 20% and preferably at least 25% of neohesperidin. More aptly the mixture will contain up to 35% of neohesperidin. In a favoured form the mixture will contain at least 75% of neohesperidin and narangin.
  • the second component is oleuropein.
  • this is obtained from extraction from the leaf of the olive, for example olea europea.
  • Such extracts typically contain 5% to 80% wt/wt, more aptly 10 to 70%, for example 20% wt/wt.
  • the other components of the extract will often contain pectins and the like.
  • compositions of the invention may employ compounds of natural origin.
  • a first component which may be obtained from bitter oranges
  • a second component which may be obtained from the olive.
  • synthetically or semi-synthetically obtained compounds may be employed if desired instead of the ones directly extracted from natural sources although this tends to be less favourable in view of cost.
  • compositions of this invention may show synergistic anti-microbial effectiveness. Such synergistic compositions are preferred .
  • first component and the second component are present in ratios (wt/wt of flavanoids to oleuropein) of 5 : 1 to 1 :4, more aptly 2 : 1 to 1 : 2, favourably 1 : 2 to 1 : 1 and preferably 3 : 2.
  • compositions may desirably contain a first component which is a mixture of flavanoids of Formula (I) wherein 50% - 100% (wt/wt) is composed of narangin and/or neohesperidin. It is presently believed that the first component may favourably contain a mixture of flavanoids containing 60% - 100% of narangin and neohesperidin, for example 65 - 75% of narangin and neohesperidin.
  • a first component which is a mixture of flavanoids of Formula (I) wherein 50% - 100% (wt/wt) is composed of narangin and/or neohesperidin. It is presently believed that the first component may favourably contain a mixture of flavanoids containing 60% - 100% of narangin and neohesperidin, for example 65 - 75% of narangin and neohesperidin.
  • compositions may preferably contain 3,4-dihydroxyphenylethanol as the second component or a mixture of compounds of formula II in which 3,4-dihydroxyphenylethanol is present by at least 50% (wt/wt), and more aptly at least 80% (wt/wt).
  • compositions of this invention are particularly effective in the presence of a third component, which is one or more organic acids.
  • a surprisingly effective third component is salicylic acid or its pharmaceutically acceptable salt optionally together with a further organic acid or pharmaceutically acceptable salt.
  • a further organic acid if present is similarly in the form of the acid rather than its salt.
  • Suitable further organic acids include acids of up to 8 carbon atoms which are monobasic (i.e. 1 C0 2 H group), di-basic or tri-basic acid which optionally contain 1, 2 or 3 hydroxyl groups.
  • Such further organic acid may be one or more of citric acid, malic acid, latic acid, tartaric acid, fumaric acid and the like.
  • compositions can provide an approximately neutral or acid pH, when used, for example of from 3-8, more aptly 3.5-7, for example 4-5.
  • the weight/weight ratio of the compound(s) of Formula (I) plus the compound(s) of Formula (II) to salicylic acid or pharmaceutically acceptable salt thereof is 2 : 1 to 1 : 7, more aptly 1 : 1 to 1 : 5, favourably 2 : 3 to 1 : 3 and preferably is 2 : 5.
  • the third component also comprises a further organic acid (such as those named above)
  • the weight/weight ratio of salicylic acid to further organic acid may be 2 : 1 to 1 : 5, more aptly 1 : 1 to 1 : 3, for example 3 : 5.
  • compositions may include a solubilising agent for the salicylic acid, for example a dextrin such as cyclodextrin.
  • compositions of the invention may be adapted for application to external surfaces including external surfaces of plants or animals, or for internal administration to an animal. Often the animal is a human.
  • compositions of the invention show activity against a wide range of organisms including gram positive bacteria, gram negative bacteria, fungi, virus, protazoans and insect parasites. Particularly surprising the compositions may be employed against difficult bacteria such as methicillin resistant staphylococcus aureus (MRSA), Clostridium difficile (C.diff) helicobacter pyroli (H.py), and vancomycin resistant enterobacteria.
  • MRSA methicillin resistant staphylococcus aureus
  • C.diff Clostridium difficile
  • H.py helicobacter pyroli
  • vancomycin resistant enterobacteria The compositions of this invention may also be used against norovirus and other pathogens whereby transmission is by contact or air.
  • compositions may be administered systemically or locally if an animal is to be treated .
  • Suitable animals include humans and food and companion animals such as cows, pigs, horses, chickens, sheep, goats, dogs and cats.
  • the compositions may be formulated for oral administration, topical administration, injection or the like as required by the medical practitioner. Particularly suitably such compositions are suitable for use to treat humans.
  • Suitable oral and topical compositions include those analogous to those described in PCT/GB2007/002756 and PCT/GB2007/002758.
  • Injectable forms may be put up in conventional manner, for example as aqueous solutions or dispersions.
  • compositions of the invention are also useful for use in conjunction with a further antibacterial agent.
  • the compositions may be used in conjunction with a ⁇ -lactam or other antibiotic or antibacterial agent.
  • Suitable ⁇ - lactam antibiotics include, a penicillin such as methicillin, flucloxacillin, ampicillin, amoxicillin optionally with clavulanic acid, a cephalosporin, or a carbopenem such as imipenem or the like.
  • the composition as a single composite form or as two or three forms, for example one of dosage form will contain the ⁇ -lactam or other antibiotic and another composition will comprise the first and second components.
  • compositions of the invention containing the first and second components adapted for oral administration and the further antibacterial agent adopted for oral administration (for orally administrable antibiotic such as amoxicillin) or for injection (for injected antibiotics such as methicillin or imipenem) may also be used together with vancomycin.
  • Patients suffering with infections caused by C. diff and H.py may be treated similarly.
  • the preferred route of administration of all three agents is orally when the ⁇ -lactam or other antibiotic is orally effective, especially for the treatment as gastric infections of H.py.
  • an antibiotic is employed that is best administered by injection that may be done in conjunction with the oral administration of the compositions of the invention.
  • compositions of the invention are particularly effective for sterilizing surfaces, they are very suitably formulated in a composition useful for external use.
  • compositions may be used to reduce the bacterial count on body surfaces, clothing and in the general environment particularly in hospitals, ambulances, nursing homes especially for the elderly or the like where it is particularly desirable to reduce the presence of bacteria such as MRSA, C. diff or the like.
  • Compositions suitable for washing the hands are particularly useful.
  • compositions may also be employed to wash stethoscopes.
  • compositions as opposed to rapid diminution of effectiveness of ethanol.
  • compositions used in this way may be in the form of a dispersible liquid, for example akin to the soap or shampoo or skin foaming compositions described hereinafter. These can also be used to what the surfaces to similar ends.
  • a particular use includes antibacterial soaps, detergents, lotions and the like for treating inter alia human skin and hair in order to reduce or eliminate undesired organisms.
  • compositions of this invention prevented in such forms, to treat hands, the face and skin generally and the hair, both on the head and elsewhere.
  • This can be employed to reduce bacterial count and so help to reduce the spread of methicillin resistant staphylococcus aureas, Clostridium difficile and other bacteria.
  • the composition may be used to reduce microorganisms associated with acne, body odor or the like.
  • a further benefit is that such compositions may be used to reduce viral transmission, for example for influenza virus, which can occur by hand contamination.
  • Other virus that may be on the skin or membranes include HIV, herpes and the like which are also minimized by use of the compositions of the invention adapted for administration to the skin or membranes. Parasite infestation may be treated with compositions of the invention.
  • Such parasites include internal parasites such as protozoa which can lead to diseases of humans such as malaria, leishumaniasis and trypanosomiasis and various diarrhoeas.
  • Other internal parasites that may be treated include flukes.
  • External parasites that may be treated include lice, especially head lice, and scabies and fleas. Soaps and shampoos are favoured for such external application although solutions, lotions and gels are also particularly suitable.
  • Fungi for treatment include those responsible for dandruff, thrush, athlete's foot and the like, for example, Candida albicans. Conditions such as dandruff may be treated with soaps and shampoos but other formulation types named herein may also be used . Athlete's foot may also be treated with dusting powder. Candida albicans or other infecting agents in the vagina may be put up in the form or a pessary.
  • compositions of the invention includes mouthwashes, toothpastes and other forms suitable for use in the buccal cavity.
  • Such forms may be formulated as indicated in the PCT applications referred to herein before.
  • compositions of the invention may also be used for the prophylaxis or treatment of dandruff or the like.
  • compositions of the invention may therefore also suitably contain a pharmaceutically acceptable salt of choline such as choline chloride. This can enhance effectiveness further against organisms such as c. diff.
  • Formulations may be composed of conventional carriers as long as they are compatible with the first, second and optionally third component of the compositions herein.
  • soaps, shampoos and the like may aptly contain surfactants.
  • Many conventional surfactants may be employed but it appears certain effective formulations will employ non-ionic surfactants.
  • Particularly effective non- ionic surfactants include alkyl polycyclosides and/or alkenyl polyglycosides (APGs) such as those containing up to 10 sugar residues coupled to a hydrocarbon chain. Oligomerisation of up to about 4 sugar residues can be desirable.
  • APGs alkyl polycyclosides and/or alkenyl polyglycosides
  • Such surfactants are available under the trade name "Plantacare” for example from Henkel as "Plantacare 2000".
  • minor amounts of typical anionic surfactants may be employed together with the non-ionic surfactant.
  • Amphoteric surfactants may also be present, for example and preferably, with the non-ionic surfactants, for example those having secondary or tertiary amino and water solubilising anionic groups, such as sulphate, phosphate, phosphonate or carboxylate groups.
  • amphoteric surfactants include those available under trade names such as Miranol (of Rhone-Poulenc) and Betain, such as Dehyton from Henkel.
  • the compositions of the invention may optionally comprise thickening agents. Suitable thickening agents include polysaccharide thickeners such as xanthan gums, gellan gums, pectins, carageenans and the like.
  • An apt thickening agent is xanthan gum such as Keltrol CG which is a high molecular weight polysaccharide produced by microbial fermentation. Viscosity may also be selected by use of an amphoteric surfactant such as a cocamido-propyl betain or Tego Betain F50 as a thickening as well as surfactant agent.
  • compositions of the invention may be employed for the treatment of food stuffs to reduce or eliminate unwanted pathogens or organisms leading to reduction in storage life of food stuffs.
  • vegetable, fruits and meat may be treated, for example lettuce, tomatoes, cucumbers, peppers, cereals such as wheat and maize, fruit such as apples, grapes, pears and figs, and meats such as beef, pork, lamb, bacon and the like.
  • Methods of treatment include washing, misting and the like.
  • the hand sterilization test method used in the Examples was as follows:
  • Each of the twelve subjects was asked to wash their hands for one minute in soft soap to remove natural commensal organisms and dried thoroughly on a paper towel.
  • the hands were then contaminated with very large numbers of bacteria well in excess of that experienced in normal everyday occurrence.
  • the hands were immersed in the contamination fluid (containing an overnight culture of the test organism in this instance E. coli at a concentration of approximately 10 8 cfu per ml) in a suitable sized container for five seconds.
  • the hands were removed from the contamination fluid and surplus liquid allowed to drain back into the container. This time the hands were allowed to air dry for approximately three minutes holding them horizontally with fingers spread out and rotating them to and fro to avoid the formation of droplets.
  • each of the twelve subjects was asked to rub their fingertips, including the thumbs for one minute on the base of a petri dish, using a separate petri dish for each hand, containing 10ml of maximum recovery diluent (MRD) without neutraliser, in order to assess the release of test organisms before treatment of the hands.
  • Dilutions of these sample fluids were prepared to 10 "3 and 10 "4 .
  • a 1ml aliquot of each dilution for each hand was placed in a separate petri dish 10 - 15ml of Tryptone Soy Agar sterilised and cooled to 45°C added and mixed thoroughly. Plates were allowed to set and incubated at 37°C for twenty four hours. Each plate was then examined for growth of the test organism. 3) Hygienic Handwash procedure.
  • Surgical Sanitizer Water 481.5g; 96.3%) was added to a beaker and stirring commenced .
  • Keltrol CG-SFT (9.0g; 1.8%) was added and stirring continued until dissolved .
  • Citrox HXT powder (2.5g; 0.5%) was added and stirring continued until dissolved.
  • White willow bark extract (2.0g; 0.4%) was added and stirring continued until dissolved.
  • Glycerol (5.0g; 1.0%) was added and stirring continued until dissolved.
  • the resulting viscous gel was de-aerated .
  • the pH was 4-5.
  • the pH may be adjusted with citric acid if required to bring it within the stated range.
  • Citrox HXT powder comprises on a wt/wt basis 7.5% HPLC 45%, citric acid 30%, willow bark extract 50% and olea Europeae extract 12.5%.
  • HPLC-45% contained 45% by weight of a mixed of flavanoids together with residues of extraction from bitter oranges.
  • the Willow Bark extract contains 90% of salicylic acid.
  • the Olea Europeae extract contains 20% of oleuropein.
  • the mixture of flavanoids in HPLC-45 comprises:
  • Plantacare 2000 is an aqueous solution containing 6.78g of the surfactant agent.
  • Tego Betain F50 is an aqueous solution containing 3.22g of the surfactant agent.
  • the gel When tested by the methods detailed in Example 1, the gel provided satisfactory bactericidal activity against the MRSA and satisfactory sporidical activity against the C. difficile.
  • HPLC 45% means a mixture containing 45% of bioflavanoids and 55% of other matter from extraction of bitter oranges.
  • the bioflavanoids comprised narangin (about 52%), neohesperidin 28%, poncirin (4%), naringenin (3%), hesperidin (3%), neodiosmin (3%), isonaringin (3%), isocriocrin (2%), other minor to 100%.
  • Example 3 may be repeated replacing HPLC 45% with an equal weight of a 1 : 1 mixture of narangin and nehesperidin.
  • Example 7
  • Example 3 The hand foam composition of Example 3 is used in a commercial misting device to produce a mist for disinfection of surfaces.
  • a commercial hand held misting device is used to direct mist at the surfaces in an ambulance and to the air space. The misting is continued until the operative is satisfied surfaces have been thoroughly treated .
  • the ambulance may be occupied twenty minutes after the completion of the misting.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Plant Pathology (AREA)
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  • Molecular Biology (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP10742237.0A 2010-08-06 2010-08-06 Zusammensetzungen mit oleuropeinen und flavanoiden und ihre verwendung Withdrawn EP2635120A1 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/GB2010/051301 WO2012017186A1 (en) 2010-08-06 2010-08-06 Compositions comprising oleuropeins and flavanoids and their use

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EP2635120A1 true EP2635120A1 (de) 2013-09-11

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EP (1) EP2635120A1 (de)
CA (1) CA2847661A1 (de)
WO (1) WO2012017186A1 (de)
ZA (1) ZA201301608B (de)

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EP2681996A1 (de) * 2012-07-03 2014-01-08 CeBeC Group Ltd. Biozide Zusammensetzungen
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