+

WO2003049713A1 - Utilisation de dihydropinosylvine et de ses derives en tant qu'inhibiteurs de la tyrosinase pour eclaircir la peau ou en tant que substances antimicrobiennes a des fins de conservation ou pour traiter l'acne, les pellicules ou les odeurs corporelles - Google Patents

Utilisation de dihydropinosylvine et de ses derives en tant qu'inhibiteurs de la tyrosinase pour eclaircir la peau ou en tant que substances antimicrobiennes a des fins de conservation ou pour traiter l'acne, les pellicules ou les odeurs corporelles Download PDF

Info

Publication number
WO2003049713A1
WO2003049713A1 PCT/EP2002/014041 EP0214041W WO03049713A1 WO 2003049713 A1 WO2003049713 A1 WO 2003049713A1 EP 0214041 W EP0214041 W EP 0214041W WO 03049713 A1 WO03049713 A1 WO 03049713A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
microorganisms
hydrogen
atoms
formula
Prior art date
Application number
PCT/EP2002/014041
Other languages
German (de)
English (en)
Inventor
Gerhard Schmaus
Martina Herrmann
Holger Joppe
Manfred Meier
Original Assignee
Symrise Gmbh & Co. Kg
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 Symrise Gmbh & Co. Kg filed Critical Symrise Gmbh & Co. Kg
Priority to AU2002366530A priority Critical patent/AU2002366530A1/en
Publication of WO2003049713A1 publication Critical patent/WO2003049713A1/fr

Links

Classifications

    • 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
    • A61Q5/006—Antidandruff preparations
    • 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
    • A61K31/05—Phenols
    • 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
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • 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
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
    • 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
    • A61K8/347—Phenols
    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists
    • 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

Definitions

  • the present invention relates primarily to new uses of dihydropinosylvin and certain derivatives of dihydropinosylvin, namely of compounds of the formula 1 below
  • Ri and R 2 are independently selected from the group consisting of
  • Hydrogen Methyl, straight-chain or branched, saturated or unsaturated alkyl having 2-10 C atoms and alkyl having 2-10 C atoms interrupted by one or more oxygen and / or sulfur atoms, and
  • R 3 and R 4 are independently selected from the group consisting of
  • tyrosinase phenolase
  • tyrosinase phenolase
  • Melanins which are formed from the amino acid tyrosine using tyrosinase via L-dopaquinone, are the pigments responsible for tanning the skin. It is known that inhibition of tyrosinase can cause depigmentation or skin lightening, for example to combat freckles or age spots.
  • Human skin is populated by a variety of different microorganisms. Most of these microorganisms are not pathogenic and are irrelevant to the physiological condition of the skin and its smell. Others, on the other hand, can determine the healthy condition of the skin. influence. Some microorganisms that strongly influence the human skin flora are shown in Table 1.
  • An acne-causing microorganism is Propionibacterium acnes, which is an anaerobically growing germ.
  • the cosmetic industry is constantly looking for agents to treat this germ and other microorganisms that cause acne.
  • mycoses especially dermatomycoses and nail mycoses. Areas of the skin are particularly often affected, on which moisture and heat can build up when wearing clothing, footwear or jewelry. Fungal diseases of the finger and toenail areas are perceived as particularly unpleasant. Various types of Trichophyton and Epidermophyton are often responsible for the formation of mycoses. The cosmetic industry is constantly looking for new agents for the treatment of these and other mycosis-causing microorganisms.
  • treatment is understood to mean any form of influencing the microorganisms in question in which the multiplication of these microorganisms is inhibited and / or the microorganisms are killed.
  • the substances used in cosmetic and / or pharmaceutical products toxicologically harmless, well tolerated by the skin, stable (especially in the usual cosmetic and / or pharmaceutical formulations), preferably odorless and inexpensive to produce (ie using standard methods and / or starting from standard precursors).
  • a particular requirement for the use of an active substance in practice is its stability against chemical substances, which are usually used as accompanying substances in cosmetics, against the oxygen contained in the ambient air and against light.
  • an active ingredient which (a) has a good antimicrobial (ie inhibiting) action against at least one, but preferably more than one of the microorganisms discussed above, (b) has a tyrosinase inhibiting action, and thus can be used as a cosmetic skin lightener or cosmetic depigmenting agent and (c) shows good stability to the effects of air and light.
  • microorganisms selected from the group consisting of (i) dandruff microorganisms, (ii) body odor microorganisms, (iii) acne microorganisms, (iv) mycosis-causing microorganisms and mixtures thereof,
  • dihydropinosylvin has an antimicrobial effect compared to, for example, Aspergillus niger and Escherichia coli.
  • An indication of the antimicrobial effect of Dihydropinosylvin or other compound of formula 1 (with the meanings of the groups R, to R 4) in relation to the above-mentioned other microorganisms but is not shown in the publication.
  • dihydropinosylvin or another compound of the formula 1 as a cosmetic agent.
  • EP 1 029 530 A1 describes the use of 3,5-dihydroxystilbene and 3-hydroxystilbene as deodorants in cosmetic products.
  • EP 1 068 864 A1 describes the use of certain stilbenes as inhibitors of glycosidation of certain proteins (for example skin proteins). Both EP documents give no indication of the use of the corresponding bisbenzyl derivatives.
  • stilbenes such as pinosylvin and pinosylvinmonomethyl ether in topical applications products.
  • Bisbenzyl derivatives such as dihydropinosylvin (formula 4) or dihydropinosylvin monomethyl ether (formula 5) can be prepared by selective catalytic hydrogenation, for example with Pd / H 2 .
  • the educts here are crude extracts containing stilbene from plants containing stilbene (eg Pinus, Alnus, Polygonum, Dalbergia, Scutellaria or Lindera A en), chromatographic fractions of plant extracts with an increased content of stilbenes as well as stilbene obtained from plant extracts in highly pure form.
  • bisbenzyl derivatives of the formula 1 can also be isolated directly from plants containing bisbenzyl derivatives, such as, for example, Pinus or D / oscorea species.
  • bisbenzyl derivatives of the formula 1 can of course also be produced in a targeted manner using synthesis processes known from the literature.
  • the compounds of formula 1 according to the invention are also against Propionibacterium acnes, Malassezia furfur and mycoses causing germs such as Trichophyton rubrum have a good effect, so that they can also be used to treat (combat) acne, as an anti-dandruff agent or in the treatment of mycoses (especially dermatomycoses).
  • Compounds of formula 1 according to the invention also have excellent compositions for preserving, for example, cosmetic and / or pharmaceutical formulations. The use of co-preservatives is therefore normally not necessary when using compounds of the formula 1 (where R-i to R have the meaning given above).
  • dihydropinosylvin derivatives of the formula 1 are also suitable as (cosmetic) agents, in particular for skin lightening. They are suitable for inhibiting the enzyme tyrosinase and thus preventing a key step in melanin synthesis, namely the conversion of tyrosine to L-dopaquinone and the subsequent oxidation to dopaquinone.
  • the compounds of formula 1 according to the invention where R. until R 4 have the meanings given above
  • the said dihydropinosylvin derivatives can be used as cosmetic agents or effective components of cosmetic agents, in particular for the treatment of age spots and freckles.
  • Preferred for the treatment of the microorganisms mentioned and / or for the treatment (inhibition) of tyrosinase, tyrosinase isoenzymes and their mixtures are compounds of the formula 1 in which R T is hydrogen and R 2 is selected from the group consisting of
  • a microorganism selected from the group consisting of (i) dandruff microorganisms, (ii) body odor microorganisms, (iii) acne causing microorganisms, (iv) mycosis causing microorganisms and mixtures thereof, the enzyme and / or the microorganism are contacted with an inhibiting amount of a compound of the formula 1 or a mixture of substances which comprises one or more compounds of the formula 1.
  • the groups R 4 to R 4 have the meanings given above, the information relating to the preferred groups R 1 to R 4 also being applicable. The inhibition occurs regularly for cosmetic reasons, but in exceptional cases can also have a therapeutic character.
  • bisbenzyl derivatives of the formula 1 (where R ⁇ to R 4 have the meanings given) is the inhibition of the bacteria responsible for the formation of body odor (including armpit and foot odor) (in particular Staphylococcus, Corynebacterium and Brevibacterium - Species).
  • bisbenzyl derivatives of the formula 1 can also be used to inhibit mycosis-causing skin and nail fungi (dermatomycoses, nail mycoses; trichophyton and epidermophyton species), to inhibit microorganisms responsible for dandruff formation (Malassezia furfur, Syn .; Pityrosporum ovale or P .
  • the compounds of formula 1 are, in particular insofar as they are used against germs causing body odor and / or for skin lightening, generally topically in the form of solutions, creams, lotions, gels, sprays or the like. applied.
  • it is oral (tablets, capsules, powder, drops), intravenous, intraocular, intraperitoneal or intramuscular application or an application in the form of an impregnated bandage makes sense.
  • the concentration of the active compounds (bisbenzyl derivatives) of the formula 1 in the formulations to be applied (topically) is preferably in the range from 0.0008% to 20% by weight and preferably in the range from 0.05% to 0.5% by weight. -%.
  • the antimicrobial complex of active ingredients can be used (a) prophylactically or (b) if necessary.
  • the concentration of e.g. The amount of active ingredient to be applied daily varies and depends on the physiological state of the test subject and individual-specific parameters such as age or body weight.
  • Bisbenzyl derivatives of the formula 1 can be used either alone, as mixtures or in combination with other antimicrobially active substances.
  • the compounds of formula 1 according to the invention are of course not only intended for application to the human or animal body, but are also suitable, for example, for the treatment of microorganisms on or in inanimate matter and for the preservation of perishable articles.
  • a method for the preservation of a perishable article against attack by microorganisms which are selected from the group consisting of (i) dandruff microorganisms, (ii) body odor causing microorganisms, (iii) acne causing microorganisms, (iv) mycosis causing microorganisms and mixtures thereof, comprises providing the perishable article with an amount of a compound of the formula 1 which has an inhibiting or killing effect on the said microorganisms, the statements made above regarding the residues R 1 to R 4 (also with regard to the preferred selection) being applicable.
  • a particularly preferred fragrance composition comprises (a) a sensorially effective amount of a fragrance, (b) an antimicrobial amount of one or more compounds of formula 1 (where R- to R can have the meanings given above) and optionally (c) one or several carriers and / or additives.
  • a perfume which contains a compound of the formula 1 is preferably approximately 5 to 50% by weight of one or more compounds of the Formula 1 exist. It had been found to be particularly advantageous that the substances of Formula 1 have only a weak intrinsic odor or are completely odorless; because this property predestines it for use in a fragrance composition.
  • a further dilution with the test agar (0.3 ml sample or corresponding dilutions + 8.7 ml agar) each resulted in 30-fold lower final concentrations (corresponding to an initial concentration of 2200 ppm each).
  • concentrations given below refer to the pure substance and are converted into ppm. 2 agar plates were poured per test concentration and nutrient medium.
  • K9 9.0 ml Wilkins-Chalgren agar (uninoculated)
  • K10 8.7 ml M.-H.
  • test plates were inoculated punctually with 1 ⁇ l each of the test germ suspensions listed in the examples below.
  • the aerobically growing bacteria Bactetibacterium epidermidis, Corynebacterium xerosis, Staphylococcus aureus; Pseudomonas aeruginosa, Staphylococcus epidermidis
  • Columbia blood agar BioMerieux, Art. 43049.
  • the Aspergillus niger mold, the yeast Candida albicans and the two skin fungi Trichophyton rubrum and Epidetmophy- ton floccosum were cultivated on Sabouraud agar (BioMerieux, Art. 43555). Malassezia furfur was grown on Sabourad HLT agar with deflowerers (addition of Tween ⁇ O: 1%; lecithin: 0.3%; histidine: 0.1%; Merck, Art. 1J8368). Propionibacterium acnes was cultivated on Schaedler agar (BioMerieux, Art. 43273). Further information on the treated test germs can be found in Table 3.
  • test germ suspensions of the aerobically growing bacterial germs were prepared by incubating Mueller-Hinton broth (Merck, Art. 1 J0293) at 36 ° C., which had been inoculated with a few individual colonies of the respective test germs. After a clear turbidity had been reached, so much sterile nutrient broth was added to the suspensions that their turbidity corresponded to the McFarland standard 0.5 (approx. 1.5 ⁇ 10 8 CFU / ml).
  • test strains were cultivated on the solid nutrient media mentioned above, harvested using a sterile swab and taken up or diluted in so much Mueller-Hinton broth that the turbidity of the suspensions corresponded to the McFarland Standard 0.5.
  • the inoculated plates were incubated under the conditions given in Table 4 and then evaluated.
  • the lowest active substance concentration at which macroscopically no growth is present was regarded as the MIC (minimum inhibitory concentration).
  • Minimal, barely visible growth or a few small single colonies were rated as inhibitions.
  • Tyrosinase is one of the key enzymes in the melanin biogenesis pathway.
  • efforts are therefore made to find substances that inhibit the enzyme tyrosinase and thus a key step in melanin synthesis, namely the conversion of tyrosine to L-dopa and the subsequent oxidation to dopaquinone prevention.
  • melanin is produced, which ultimately lightens the skin.
  • test solutions a) Kojic acid (positive control) or one of the test substances to be examined, b) tyrosinase (SIGMA T7755, isolated from fungi; 10 units, preincubated for 10 minutes together with positive control or test substance on ice ) and c) 5mM tyrosine (SIGMA T8909) are placed together in 50mM phosphate buffer pH 7.5
  • test solutions are incubated at 37 ° C for 1 h
  • the IC50 value (value of the concentration at which 50% inhibition is achieved) for kojic acid in test 1 was 100 ⁇ mol.
  • the IC50 value for dihydropinosylvin could not be determined exactly in test series 1 because it was ⁇ 70 ⁇ mol (i.e. ⁇ 14.9 ⁇ g / ml) below the lowest concentration still tested (see Tables 5 and 6). Because of this, the IC50 for dihydropinosylvin was only determined exactly in test 2.
  • test solutions a) Kojic acid (positive control) or one of the test substances to be examined, b) tyrosinase (SIGMA T7755, isolated from fungi; 10 units, preincubated for 10 minutes together with positive control or test substance on ice ) and c) 5mM tyrosine (SIGMA T8909) are placed together in 50mM phosphate buffer at pH 7.5
  • test solutions are incubated for 1 hour at 37 ° C
  • the IC50 value for kojic acid in test 2 was 390 ⁇ mol.
  • the IC50 values for Pinus sylvestris extract and Pinus sylvestris hydrogenated extract were> 1500 ⁇ g / ml and 140 ⁇ g / ml, respectively (see Tables 5 and 6).

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne de nouvelles utilisations de composés de formule (1) ou de mélanges de substances comprenant un ou plusieurs composés de formule (1). Dans ladite formule, R1 et R2 sont sélectionnés indépendamment l'un de l'autre dans le groupe comprenant : de l'hydrogène ; un méthyle ; un alkyle à chaîne linéaire ou ramifiée, saturé ou insaturé, comprenant 2 à 10 atomes de carbone ; et un alkyle comprenant 2 à 10 atomes de carbone interrompu par un ou plusieurs atomes d'oxygène et/ou de soufre. R3 et R4 sont sélectionnés indépendamment l'un de l'autre dans le groupe comprenant : de l'hydrogène, un hydroxy et un méthoxy. Lesdits composés constituent des agents servant à (a) inhiber des enzymes sélectionnées dans le groupe comprenant la tyrosinase, les isoenzymes de la tyrosinase et leurs mélanges et/ou à (b) traiter des micro-organismes sélectionnés dans le groupe comprenant (i) les micro-organismes provoquant les pellicules, (ii) les micro-organismes provoquant les odeurs corporelles, (iii) les micro-organismes provoquant l'acné, (iv) les micro-organismes provoquant les mycoses et (v) leurs mélanges. L'invention se rapporte en outre à un procédé permettant de conserver des articles périssables et d'éclaircir de manière cosmétique la peau humaine au moyen desdits composés.
PCT/EP2002/014041 2001-12-13 2002-12-11 Utilisation de dihydropinosylvine et de ses derives en tant qu'inhibiteurs de la tyrosinase pour eclaircir la peau ou en tant que substances antimicrobiennes a des fins de conservation ou pour traiter l'acne, les pellicules ou les odeurs corporelles WO2003049713A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002366530A AU2002366530A1 (en) 2001-12-13 2002-12-11 Utilization of dihydropinosylvin and derivatives thereof as tyrosinase inhibitors for skin lightening or as antimicrobial substances for preservation or for the treatment of acne, dandruff or body odors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10161253.2 2001-12-13
DE2001161253 DE10161253A1 (de) 2001-12-13 2001-12-13 Verwendung von Dihydropinosylvin und dessen Derivaten als Inhibitoren

Publications (1)

Publication Number Publication Date
WO2003049713A1 true WO2003049713A1 (fr) 2003-06-19

Family

ID=7709083

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/014041 WO2003049713A1 (fr) 2001-12-13 2002-12-11 Utilisation de dihydropinosylvine et de ses derives en tant qu'inhibiteurs de la tyrosinase pour eclaircir la peau ou en tant que substances antimicrobiennes a des fins de conservation ou pour traiter l'acne, les pellicules ou les odeurs corporelles

Country Status (3)

Country Link
AU (1) AU2002366530A1 (fr)
DE (1) DE10161253A1 (fr)
WO (1) WO2003049713A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004105736A1 (fr) * 2003-05-30 2004-12-09 Symrise Gmbh & Co. Kg Utilisation de derives de diphenylmethane comme inhibiteurs de la tyrosinase
JP2008501030A (ja) * 2004-05-28 2008-01-17 ユニゲン・ファーマシューティカルス・インコーポレーテッド 二核酵素の強力な阻害剤としてのジアリールアルカン類
WO2011051483A1 (fr) * 2009-10-30 2011-05-05 Green Molecular, S.L Ptérostilbène (pter) destiné à être utilisé dans la prévention et/ou le traitement des maladies, des atteintes ou des lésions cutanées
US8362305B2 (en) 2008-07-21 2013-01-29 Unigen, Inc. Series of skin whitening (lightening) compounds
CN102988190A (zh) * 2012-12-28 2013-03-27 广州市白云区新东方日用化工品厂 美白组合物及其应用
US8586799B2 (en) 2011-03-24 2013-11-19 Unigen, Inc. Compounds and methods for preparation of diarylpropanes
US8841350B2 (en) 2011-05-11 2014-09-23 ChromaDex Inc. Method for inducing UDP-glucuronosyltransferase activity using pterostilbene
EP2842607A1 (fr) * 2013-09-02 2015-03-04 Symrise AG Eine Mischung zur Aufhellung von Haut und/oder Haaren
US9717815B2 (en) 2014-07-30 2017-08-01 Georgia-Pacific Consumer Products Lp Air freshener dispensers, cartridges therefor, systems, and methods

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6438009A (en) * 1987-07-31 1989-02-08 Pola Chem Ind Inc Beautifying cosmetic
EP0953345A1 (fr) * 1998-04-10 1999-11-03 L'oreal Utilisation d'au moins un hydroxystilbène en tant qu'agent diminuant l'adhésion des micro-organismes
EP1029530A1 (fr) * 1999-02-17 2000-08-23 L'oreal Utilisation de dérivés substitués en 3 du stilbene comme actifs déodorants dans les compositions cosmétiques
JP2001335472A (ja) * 2000-05-24 2001-12-04 Kansai Koso Kk チロシナーゼ活性阻害剤及び化粧料

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6438009A (en) * 1987-07-31 1989-02-08 Pola Chem Ind Inc Beautifying cosmetic
EP0953345A1 (fr) * 1998-04-10 1999-11-03 L'oreal Utilisation d'au moins un hydroxystilbène en tant qu'agent diminuant l'adhésion des micro-organismes
EP1029530A1 (fr) * 1999-02-17 2000-08-23 L'oreal Utilisation de dérivés substitués en 3 du stilbene comme actifs déodorants dans les compositions cosmétiques
JP2001335472A (ja) * 2000-05-24 2001-12-04 Kansai Koso Kk チロシナーゼ活性阻害剤及び化粧料

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
FAGBOUN D E ET AL: "DIHYDROSTILBENE PHYTOALEXINS FROM DIOSCOREA-ROTUNDATA", PHYTOCHEMISTRY (OXFORD), vol. 26, no. 12, 1987, pages 3187 - 3190, XP001146159, ISSN: 0031-9422 *
MATSUURA H ET AL: "Antibacterial and antifungal compounds from Empetrum nigrum.", PLANTA MEDICA, vol. 61, no. 6, 1995, pages 580, XP009006909, ISSN: 0032-0943 *
PATENT ABSTRACTS OF JAPAN vol. 013, no. 227 (C - 600) 25 May 1989 (1989-05-25) *
PATENT ABSTRACTS OF JAPAN vol. 2002, no. 04 4 August 2002 (2002-08-04) *

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004105736A1 (fr) * 2003-05-30 2004-12-09 Symrise Gmbh & Co. Kg Utilisation de derives de diphenylmethane comme inhibiteurs de la tyrosinase
US9655824B2 (en) 2003-05-30 2017-05-23 Symrise Ag Use of diphenylmethane derivatives as tyrosinase inhibitors
US9126913B2 (en) 2004-05-28 2015-09-08 Unigen, Inc. Diarylalkanes as potent inhibitors of binuclear enzymes
US8592488B2 (en) 2004-05-28 2013-11-26 Unigen, Inc. Diarylalkanes as potent inhibitors of binuclear enzymes
US10548825B2 (en) 2004-05-28 2020-02-04 Unigen, Inc. Diarylalkanes as potent inhibitors of binuclear enzymes
EP1748767A4 (fr) * 2004-05-28 2008-12-24 Unigen Pharmaceuticals Inc Diarylalcanes constituant des inhibiteurs puissants d'enzymes binucleaires
US8729136B2 (en) 2004-05-28 2014-05-20 Unigen, Inc. Diarylalkanes as potent inhibitors of binuclear enzymes
JP2008501030A (ja) * 2004-05-28 2008-01-17 ユニゲン・ファーマシューティカルス・インコーポレーテッド 二核酵素の強力な阻害剤としてのジアリールアルカン類
US7767661B2 (en) 2004-05-28 2010-08-03 Unigen Pharmaceuticals, Inc. Diarylalkanes as potent inhibitors of binuclear enzymes
US8362305B2 (en) 2008-07-21 2013-01-29 Unigen, Inc. Series of skin whitening (lightening) compounds
US8658838B2 (en) 2008-07-21 2014-02-25 Unigen, Inc. Series of skin whitening (lightening) compounds
US9096507B2 (en) 2008-07-21 2015-08-04 Unigen, Inc. Series of skin whitening (lightening) compounds
CN102639126A (zh) * 2009-10-30 2012-08-15 绿色分子有限公司 用于预防和/或治疗皮肤疾病、损害或损伤的紫檀芪（pter）
EP2322159A1 (fr) * 2009-10-30 2011-05-18 Green Molecular, S.L. Utilisation de pterostilbene (pter) en tant que médicament pour la prévention et/ou le traitement des maladies de la peau, dommages ou blessures ou en tant que cosmétiques
WO2011051483A1 (fr) * 2009-10-30 2011-05-05 Green Molecular, S.L Ptérostilbène (pter) destiné à être utilisé dans la prévention et/ou le traitement des maladies, des atteintes ou des lésions cutanées
US8586799B2 (en) 2011-03-24 2013-11-19 Unigen, Inc. Compounds and methods for preparation of diarylpropanes
US9045405B2 (en) 2011-03-24 2015-06-02 Unigen, Inc. Compounds and methods for preparation of diarylpropanes
US8841350B2 (en) 2011-05-11 2014-09-23 ChromaDex Inc. Method for inducing UDP-glucuronosyltransferase activity using pterostilbene
US10039725B2 (en) 2011-05-11 2018-08-07 ChromaDex Inc. Method for treating non-melanoma skin cancer by inducing UDP-glucuronosyltransferase activity using pterostilbene
CN102988190A (zh) * 2012-12-28 2013-03-27 广州市白云区新东方日用化工品厂 美白组合物及其应用
US9889078B2 (en) 2013-09-02 2018-02-13 Symrise Ag Skin and/or hair whitening mixture
EP2842607A1 (fr) * 2013-09-02 2015-03-04 Symrise AG Eine Mischung zur Aufhellung von Haut und/oder Haaren
CN104414869B (zh) * 2013-09-02 2019-09-03 西姆莱斯股份公司 一种皮肤和/或毛发美白混合物
CN104414869A (zh) * 2013-09-02 2015-03-18 西姆莱斯股份公司 一种皮肤和/或毛发美白混合物
US9717815B2 (en) 2014-07-30 2017-08-01 Georgia-Pacific Consumer Products Lp Air freshener dispensers, cartridges therefor, systems, and methods
US10391193B2 (en) 2014-07-30 2019-08-27 Gpcp Ip Holdings Llc Air freshener dispensers, cartridges therefor, systems, and methods

Also Published As

Publication number Publication date
DE10161253A1 (de) 2003-06-26
AU2002366530A1 (en) 2003-06-23

Similar Documents

Publication Publication Date Title
EP1478231B1 (fr) Melanges synergiques de 1,2-alcane-diols
EP1269983B1 (fr) Utilisation du 1,2-décanediol contre des germes responsables d' odeurs corporelles désagréables
EP0556660B1 (fr) Utilisation d'acides gras alpha-hydroxyliques
DE69900081T2 (de) Zusammensetzung zum Aufhellen der Haut und/oder der Haare
EP1427689B1 (fr) 4-methyl-4-aryl-2-pentanols a action antimicrobienne, production et utilisation desdits composes
DE102007035139A1 (de) 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanon und dessen Verwendung als antimikrobieller Wirkstoff
US5200429A (en) Acne vulgaris treating
DE10324567A1 (de) Verwendung von Diphenylmethan-Derivaten als antimikrobielle Wirkstoffe
DE69302439T2 (de) Topisches Präparat zur Verhütung oder Behandlung der Akne Vulgaris
DE69019517T2 (de) Neolignanderivatkomplexen mit Phospolipiden, deren Verwendung und sie enthaltende pharmazeutische und kosmetische Zusammensetzungen.
WO2003049713A1 (fr) Utilisation de dihydropinosylvine et de ses derives en tant qu'inhibiteurs de la tyrosinase pour eclaircir la peau ou en tant que substances antimicrobiennes a des fins de conservation ou pour traiter l'acne, les pellicules ou les odeurs corporelles
EP1501525B1 (fr) Procede de production de preparations enrichies en tocotrienol
DE10335634B4 (de) Verwendung von Perilla-, Geranium- und Citronellsäure sowie ausgewählten Derivaten zur Konservierung, zur Behandlung von Akne, Schuppen oder Dematomykosen sowie zur Bekämpfung Körpergeruch verursachender Mikroorganismen
EP3119206A1 (fr) Extraits de santolina chamaecyparissus
DE20221386U1 (de) Synergistische Mischungen von 1,2-Alkandiolen
EP1338269B1 (fr) Utilisation de créatinine et/ou des dérivés de créatinine pour éclaircir la peau et pour soulager les désordres de pigmentation
EP3290044A1 (fr) Composition anti-bactérienne comprenant un extrait de plante, procédé de production de l'extrait, composition pharmaceutique et son utilisation
DE10022616A1 (de) 6,10-Dimethyl-5,9-undecadien-2-ol
WO2001066097A2 (fr) Principe actif agissant sur des germes de type pseudomonas
KR20210043098A (ko) 영실 추출물 또는 이의 분리화합물을 함유하는 피부 미생물 조절용 화장료 조성물
KR20140099223A (ko) 식물 추출물을 이용한 항균 조성물
DE10308278B4 (de) Antimikrobielle Wirkstoffe gegen Bakterien, Hefen und Schimmelpilze
LU503834B1 (de) Die Anwendung eines pflanzlichen ätherischen Öls in einem entzündungshemmenden, antibakteriellen, freie Radikale hemmenden und reaktive Sauerstoffspezies bekämpfenden Arzneimittel
KR102587124B1 (ko) 보습성 및 롤링성이 향상된 마사지용 화장료 조성물 및 이를 포함하는 젤
KR101470572B1 (ko) 식물 추출물을 이용한 항균 조성물

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LU MC NL PT SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载