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EP2493463A1 - Utilisation d'éthers de menthyle en tant que principes actifs antibactériens, antimycosiques ou antiviraux - Google Patents

Utilisation d'éthers de menthyle en tant que principes actifs antibactériens, antimycosiques ou antiviraux

Info

Publication number
EP2493463A1
EP2493463A1 EP10737518A EP10737518A EP2493463A1 EP 2493463 A1 EP2493463 A1 EP 2493463A1 EP 10737518 A EP10737518 A EP 10737518A EP 10737518 A EP10737518 A EP 10737518A EP 2493463 A1 EP2493463 A1 EP 2493463A1
Authority
EP
European Patent Office
Prior art keywords
cosmetic
substances
skin
menthyl
bacterial
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
EP10737518A
Other languages
German (de)
English (en)
Inventor
Kathrin Thiesen
Bernd Traupe
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.)
Beiersdorf AG
Original Assignee
Beiersdorf AG
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 Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP2493463A1 publication Critical patent/EP2493463A1/fr
Ceased legal-status Critical Current

Links

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
    • A61K31/075—Ethers or acetals
    • A61K31/08—Ethers or acetals acyclic, e.g. paraformaldehyde
    • 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
    • A61K31/075—Ethers or acetals
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • 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
    • 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
    • A61P31/10—Antimycotics
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/87—Application Devices; Containers; Packaging
    • A61K2800/874—Roll-on
    • 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

Definitions

  • menthyl ethers as antibacterial, antimycotic or antiviral agents
  • the present invention relates to the use of substances known per se as active against bacteria, mycota and viruses substances.
  • the present invention relates to cosmetic and dermatological preparations containing such substances.
  • the healthy warm-blooded organism especially the healthy human skin, is populated with a variety of non-pathogenic microorganisms.
  • This so-called microflora of the skin is not only harmless, it represents an important protection against opportunistic or pathogenic germs.
  • Bacteria belong to the prokaryotic unicellular organisms. They can be roughly distinguished according to their shape (sphere, cylinder, curved cylinder) and the structure of their cell wall (gram-positive, gram-negative). Finer subdivisions also take into account the physiology of the organisms. There are aerobic, anaerobic and facultative anaerobic bacteria. Some individuals are of medical importance in their capacity as pathogenic agents, while others are completely harmless.
  • Antibiotics for example, which is not applicable to all antimicrobial substances, can be dated to the year 1941, although the first findings on penicillin were already found in 1929. Antibiotics in the modern sense are not for all medical, even not suitable for cosmetic applications, since often the warm-blooded organism, so for example the diseased patient, at
  • Gram-negative bacteria are, for example, Escherichia coli, Pseudomonas species and Enterobacteriaceae, such as Citrobacter.
  • Gram-positive bacteria also play a role in cosmetics and dermatology.
  • bacterial secondary infections of etiological importance are, among other influences.
  • One of the most important microorganisms associated with impure skin is Propionibacterium acnes.
  • Impure skin and / or comedones affect the well-being of those affected but even in mild cases. Since virtually every adolescent or person is affected by blemished skin of some kind, many people need to remedy this condition.
  • a particular object of the present invention was therefore to find a substance or combination of substances which is effective against impure skin or Propionibacterium acnes.
  • the present invention relates in a further embodiment cosmetic deodorants.
  • Such formulations serve to eliminate body odor, which arises when the per se odorless fresh sweat is decomposed by especially gram-positive microorganisms.
  • Microorganisms that are responsible for the formation of odor are Coryneform bacteria, staphylococci, propionibacteria, micrococci and anaerobic bacteria.
  • the usual cosmetic deodorants are based on different active principles. Both known and customary are liquid deodorants, for example aerosol sprays, roll-ons and the like, as well as solid preparations, for example deodorant sticks ("sticks"), powders, powder sprays, intimate cleaners, etc.
  • antiperspirants can be prevented by astringents - mainly aluminum salts such as aluminum hydroxychloride (Aluchlorhydrat) - the formation of sweat.
  • astringents mainly aluminum salts such as aluminum hydroxychloride (Aluchlorhydrat) - the formation of sweat.
  • the bacterial flora on the skin can be reduced.
  • only the odor causing microorganisms should be effectively reduced. In practice, however, it has been found that the entire microflora of the skin can be affected.
  • the sweat flow itself is not influenced by this, ideally only the microbial decomposition of the sweat is temporarily stopped.
  • body odor can also be masked by fragrances, a method that is least in line with the consumer's aesthetic needs, as the mixture of body odor and perfume smells rather unpleasant.
  • Another object of the present invention was therefore to develop cosmetic deodorants which do not have the disadvantages of the prior art.
  • the deodorants should protect the microflora of the skin largely, but selectively reduce the number of microorganisms that are responsible for the body odor.
  • a further object was to develop cosmetic deodorants which harmonize with the widest possible variety of customary cosmetic auxiliaries and additives, in particular with the perfume ingredients which are especially important in deodorizing or antiperspirant formulations.
  • Yet another object of the invention was to provide cosmetic deodorants which are effective over a prolonged period, on the order of at least half a day, without noticeably reducing their effect.
  • Eucaryotes are organisms whose cells (Eucytes), unlike those of the so-called procaryotes (Procytes), have a nucleus delimited by the nuclear envelope and the nuclear membrane from the rest of the cytoplasm. The nucleus contains the genetic information stored in chromosomes.
  • mycobionts include, for example, yeasts (Protoascomycetes), molds (Plectomycetes), mildew (Pyrenomycetes), downy mildew (Phycomycetes), and wild mushrooms (Basidiomycetes).
  • Dermatomycoses are diseases in which certain types of fungi, in particular dermatophytes, invade the skin and hair follicles.
  • the symptoms of dermatomycoses include blisters, exfoliation, rhagades and erosion, usually associated with itching or allergic eczema.
  • Dermatomycoses can be subdivided essentially into the following four groups: dermatophytoses (eg, epidermophytia, favus, microsporia, trichophytia), yeast mecoses (eg, pityriasis and other myrotic pityrosporum, candidal infections, blastomycosis, Busch-Buske disease, torulosis, Piedra alba, torulopsidosis, trichosporosis), mold mycoses (eg aspergillosis, cephalosporidosis, phycomycosis and scopular isopidemia), systemic mycoses (eg chromomycosis, coccidiomycosis, stroke stop masmosis).
  • dermatophytoses eg, epidermophytia, favus, microsporia, trichophytia
  • yeast mecoses eg, pityriasis and other
  • the object of the present invention was to eliminate the disadvantages of the prior art and to provide substances and preparations containing such substances, by the use of which superinfections can be cured, wherein the physiological skin flora suffers no significant loss.
  • viruses are biological structures that require a host cell for biosynthesis.
  • Extracellular viruses also called “virions” consist of a single- or double-stranded nucleic acid sequence (DNA or RNA) and a protein coat (called capsid), optionally surrounded by an additional lipid-containing envelope (Envelope).
  • the classification of the viruses was classed according to clinical criteria, but nowadays mostly according to their structure, their morphology, but in particular according to the nucleic acid sequence.
  • Viruses of dermatological importance are, for example, herpes viruses (herpes simplex type 1 and 2, varicella zoster) and papillomaviruses.
  • Viruzide ie virus killing substances in the true sense does not exist because viruses do not have their own metabolism. It was therefore also discussed whether viruses should be classified as living things. At any rate, pharmacological interventions without damaging the unaffected cells are difficult. possible The primary mechanisms of action in the fight against the viruses are primarily the disruption of their replication, for example by blocking the enzymes that are important for replication and which are present in the host cell. Furthermore, the release of the viral nucleic acids into the host cell can be prevented.
  • antiviral or “effective against viruses”, “virucidal” or the like are understood to mean the property of a substance, a single or multicellular organism against harmful consequences of a viral infection, be it prophylactically or therapeutically regardless of what the actual mechanism of action of the substance is in an individual case.
  • An object of the present invention was therefore to remedy this situation, that is to say to find substances which effectively protect a monocellular or multicellular organism from harmful consequences of a viral infection, be it prophylactically or therapeutically.
  • R represents a branched or unbranched alkyl radical having up to 10 carbon atoms which is optionally mono- or polysubstituted by hydroxyl groups, as antibacterial, antimycotic or antiviral active compounds, which remedies the disadvantages of the prior art.
  • the individual active ingredients used according to the invention are particularly suitable for use as a deodorizing agent in cosmetic deodorants as well as against blemished skin and mild forms of acne.
  • the individual active ingredients used according to the invention can prevent spoilage of organic substances, in particular cosmetic and dermatological preparations, by infestation with Gram-positive and Gram-negative bacteria, mycobionts and viruses when added to these preparations.
  • the preferred ester used according to the invention is the glycerol ether of the menthol having the structure
  • the menthyl esters used in accordance with the invention are preferably used in cosmetic or dermatological compositions in a content of 0.005-50.0% by weight, in particular 0.01-20.0% by weight, based on the total weight of the composition.
  • the compositions advantageously contain 0.02-10.0% by weight, more preferably 0.02-5.0% by weight, of one or more menthyl esters used in accordance with the invention, very particularly preferably 0.3-3.0% by weight. %, in each case based on the total weight of the composition.
  • the individual active ingredients used according to the invention can be incorporated without difficulty into common cosmetic or dermatological formulations.
  • the individual active ingredients used according to the invention are very particularly advantageously present in the form of cosmetic deodorants, for example as aerosols from aerosol containers, squeeze bottles or preparations which can be sprayed by a pump device or in the form of liquid compositions which can be applied by means of roll-on devices, as deodorant sticks (deodorant sticks) ) or in the form of W / O or O / W emulsions which can be applied from normal bottles and containers, for example creams or lotions.
  • the cosmetic formulations may advantageously be in the form of tinctures, wipes, personal cleansers, shampoos, shower or bath preparations, powders or powder sprays, as well as nail care products (e.g., nail polishes, nail polish removers, nail balms).
  • nail care products e.g., nail polishes, nail polish removers, nail balms.
  • compositions according to the invention may also be advantageous to buffer the compositions according to the invention.
  • a pH range of 3.5 to 7.5 is advantageous.
  • the cosmetic and / or dermatological formulations according to the invention may be composed as usual and used for the treatment of the skin and / or the hair and / or the nails in the sense of a dermatological treatment or a treatment in terms of nourishing cosmetics. But they can also be used in make-up products in decorative cosmetics.
  • the cosmetic and / or dermatological formulations according to the invention are applied in sufficient quantities to the skin and / or the hair and / or the nails in the manner customary for cosmetics and dermatological agents.
  • the cosmetic preparations according to the invention may contain cosmetic adjuvants conventionally used in such preparations, for example preservatives, antioxidants, perfumes, foaming inhibitors, colorants, pigments which have a coloring effect, thickeners, surface-active substances, emulsifiers, softening substances, moisturizing and / or moisturizing substances, preservatives, anti-inflammatory substances, additional active substances such as vitamins or proteins, light stabilizers, salts, proteolytic or keratinolytic substances, fats, oils, waxes or other customary constituents of a cosmetic formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic adjuvants conventionally used in such preparations, for example preservatives, antioxidants, perfumes, foaming inhibitors, colorants, pigments which have a coloring effect, thickeners, surface-active substances, emulsifiers, softening substances, moisturizing and / or moisturizing substances, preserv
  • Emulsions are advantageous according to the invention and contain e.g. the said fats, oils, waxes and other fatty substances, as well as water and an emulsifier, as commonly used for such a type of formulation.
  • Gels according to the invention usually contain low C number alcohols, e.g. Ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an above-mentioned oil in the presence of a thickening agent which is preferably silica or an aluminosilicate in oily-alcoholic gels, in aqueous-alcoholic or alcoholic gels, preferably a polyacrylate.
  • a thickening agent which is preferably silica or an aluminosilicate in oily-alcoholic gels, in aqueous-alcoholic or alcoholic gels, preferably a polyacrylate.
  • Fixed pins according to the invention contain e.g. natural or synthetic waxes, fatty alcohols or fatty acid esters. Preference is given to lip balms and deodorant sticks ("deodorant sticks").
  • Suitable propellants for cosmetic or dermatological preparations which can be sprayed from aerosol containers according to the invention are the customary known highly volatile, liquefied propellants, e.g. Hydrocarbons (propane, butane, isobutane) suitable, which can be used alone or in combination with each other. Also, compressed air is advantageous to use.
  • Hydrocarbons propane, butane, isobutane
  • Cosmetic preparations which are a shampoo or a washing, shower or bath preparation preferably comprise at least one anionic, nonionic or amphoteric surfactant or mixtures thereof, at least one dialkyl substituted carboxylic acid in the aqueous medium and adjuvants conventionally used therefor ,
  • the following examples are intended to illustrate the embodiments of the present inventions. The information always refers to weight%, unless otherwise stated.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Dermatology (AREA)
  • Virology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation d'éthers de menthyle de structure (I), dans laquelle R représente un radical alkyle contenant jusqu'à 10 atomes de carbone, ramifié ou non ramifié, éventuellement substitué par un ou plusieurs groupes hydroxy, en tant que principes actifs antibactériens, antimycosiques ou antiviraux.
EP10737518A 2009-10-27 2010-07-26 Utilisation d'éthers de menthyle en tant que principes actifs antibactériens, antimycosiques ou antiviraux Ceased EP2493463A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009050854A DE102009050854A1 (de) 2009-10-27 2009-10-27 Verwendung von Menthylethern als antibakterielle, antimycotische oder antivirale Wirkstoffe
PCT/EP2010/004556 WO2011050871A1 (fr) 2009-10-27 2010-07-26 Utilisation d'éthers de menthyle en tant que principes actifs antibactériens, antimycosiques ou antiviraux

Publications (1)

Publication Number Publication Date
EP2493463A1 true EP2493463A1 (fr) 2012-09-05

Family

ID=42666312

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10737518A Ceased EP2493463A1 (fr) 2009-10-27 2010-07-26 Utilisation d'éthers de menthyle en tant que principes actifs antibactériens, antimycosiques ou antiviraux

Country Status (4)

Country Link
EP (1) EP2493463A1 (fr)
BR (1) BR112012009730A2 (fr)
DE (1) DE102009050854A1 (fr)
WO (1) WO2011050871A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5803047B2 (ja) * 2011-06-30 2015-11-04 高砂香料工業株式会社 抗菌剤組成物
USRE46698E1 (en) 2011-12-21 2018-02-06 Merck Patent Gmbh Use of cyclohexanol derivatives as antimicrobial active compounds
EP2846763B1 (fr) * 2012-05-08 2017-02-08 Merck Patent GmbH Utilisation d'ethers de cyclohexanol antimicrobiens

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100589930B1 (ko) * 2000-06-12 2006-06-15 짐리즈 게엠베하 운트 캄파니 카게 비독성 코팅 조성물, 이의 사용 방법 및 바이오파울링유기체의 부착이 방지된 제품
JP2004018470A (ja) * 2002-06-18 2004-01-22 Takasago Internatl Corp 抗菌香料組成物および口臭抑制香料組成物ならびにそれらを含有する口腔用組成物
DE102005002644A1 (de) * 2005-01-19 2006-07-20 Schülke & Mayr GmbH Zusammensetzungen für die hygienische Händedesinfektion und die desinfizierende Händewaschung
JP4294640B2 (ja) * 2005-12-15 2009-07-15 株式会社マンダム 防腐殺菌剤、該防腐殺菌剤を配合した化粧品又は医薬品、及び防腐殺菌方法
JP4743704B2 (ja) * 2006-01-16 2011-08-10 株式会社マンダム 腋臭菌用抗菌剤、並びに該抗菌剤を含有する腋臭防止剤及び皮膚外用剤
EP2014273A1 (fr) * 2007-06-14 2009-01-14 Symrise GmbH & Co. KG Utilisation d'éther de menthyl méthyl et autre éther pour apporter d'une sensation de propreté et de pureté

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
None *
See also references of WO2011050871A1 *

Also Published As

Publication number Publication date
WO2011050871A1 (fr) 2011-05-05
DE102009050854A1 (de) 2011-04-28
BR112012009730A2 (pt) 2020-08-18

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