WO2006029818A2 - Nouvelles compositions cosmetiques - Google Patents

Nouvelles compositions cosmetiques Download PDF

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Publication number
WO2006029818A2
WO2006029818A2 PCT/EP2005/009832 EP2005009832W WO2006029818A2 WO 2006029818 A2 WO2006029818 A2 WO 2006029818A2 EP 2005009832 W EP2005009832 W EP 2005009832W WO 2006029818 A2 WO2006029818 A2 WO 2006029818A2
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Prior art keywords
composition
prevention
treatment
skin
alkyl
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PCT/EP2005/009832
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English (en)
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WO2006029818A3 (fr
Inventor
Raphael Beumer
Jochen Klock
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Dsm Ip Assets B.V.
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Publication of WO2006029818A2 publication Critical patent/WO2006029818A2/fr
Publication of WO2006029818A3 publication Critical patent/WO2006029818A3/fr

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    • 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
    • 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
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • 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
    • 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
    • A61Q19/004—Aftersun 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
    • A61Q19/005—Preparations for sensitive skin
    • 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
    • A61Q19/007—Preparations for dry skin
    • 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
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth

Definitions

  • the present invention is concerned with novel cosmetic compositions. More particularly, the invention is concerned with novel cosmetic compositions for treating or preventing any symptoms caused by negative developments of the physiological homeostasis of healthy skin, as well as for the promotion of hair growth and protection from hair loss.
  • the present invention is concerned with cosmetic compositions com ⁇ prising a compound of the general formula (I)
  • L is hydrogen, branched alkyl, aryl, heteroaryl,. cycloalkyl, heterocycloalkyl, hydroxyl, OR,
  • HO-(CH 2 -CH 2 -O) n HO-(CH 2 -O) n , HO-(CH 2 -CH 2 -CH 2 -O) n , HO-(CH 2 -CH(CH 3 )- O) n , HO-(CH(CH 3 )-CH 2 -O) n , NR 4 R 5 , C(O)NR 6 R 7 , with R being C 1-4 -alkyl or C 2-18 -alkanoyl; n being an integer from 1 to 8; R 4 , R 5 , R 6 and R 7 being independently from each other hydrogen or
  • R 1 is alkylene, alkenylene or alkinylene, optionally substituted with one or more methyl or ethyl groups;
  • R 2 is hydrogen or alkyl;
  • R 3 is hydrogen, alkyl, or a cosmetically acceptable cation; and a carrier conventionally used in cosmetic compositions.
  • L is hydrogen, phenyl or hydroxyl.
  • alkyl encompasses straight chain as well as branched alkyl groups, i.e. that "C 1-4 -alkyl” encompasses straight chain C 1-4 -alkyl (methyl, ethyl, n-propyl, n-butyl) as well as branched C 3-4 -alkyl (iso-propyl, iso-butyl, tert-butyl). The same applies for "C 1-18 - alkyl”.
  • C 2-18 -alkanoyl encompasses "C 1-17 -alkyl-CO 2 -", wherein the al ⁇ kyl group is straight chain as well as “C 3-17 -alkyl-CO 2 -", wherein the alkyl group is branched.
  • aryl encompasses unsubstituted phenyl as well as phenyl with one to five substituents selected from the group consisting of C 1-4 -alkyl, C 1-4 -alkyloxy and NR 8 R 9 with R 8 and R 9 being independently from each other hydrogen or C 1-4 -alkyl.
  • heteroaryl encompasses aromatic ring systems containing 3 to5 carbon atoms and at least one hetero atom such as oxygen, sulphur and nitrogen. These heteroaryls may optionally be substituted by C 1-4 -alkyl, C 1-4 -alkyloxy and/or NR R with R and R being independently from each other hydrogen or C 1-4 -alkyl. Examples of “heteroaryls” are 1-12-1 3-/4-pyridyl, 2-/3-furyl and 2-/3-thiophenyl.
  • cycloalkyl encompasses saturated cyclic ring systems containing 5 to 8 carbon atoms such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl, as well as these ring systems containing one or two double bonds. These (un)saturated cycloalkyls may option ⁇ ally be substituted by C 1-4 -alkyl, C 1-4 -alkyloxy and/or NR 8 R 9 with R 8 and R 9 being inde ⁇ pendently from each other hydrogen or C 1-4 -alkyl.
  • heterocycloalkyl encompasses saturated cyclic ring systems containing 3 to 7 carbon atoms and at least one hetero atom such as oxygen, sulphur and nitrogen, as well as these ring systems containing one or two double bonds. These (un)saturated heterocycloal- kyls may optionally be substituted by C 1-4 -alkyl, C 1-4 -alkyloxy and/or NR 8 R 9 with R 8 and R 9 being independently from each other hydrogen or C 1-4 -alkyl.
  • alkylene encompasses straight chain or branched alkyl-diradicals which are optionally substituted by methyl and/or ethyl groups. Preferred “alkylenes” (R 1 ) are men ⁇ tioned below.
  • alkenylene encompasses straight chain or branched alkenyl- diradicals which are optionally substituted by methyl and/or ethyl groups, i.e. these diradi- cals contain at least one double bond. Preferred examples (R 1 ) are mentioned below.
  • alkinylene encompasses straight chain or branched alkinyl-diradicals which are optionally substituted by methyl and/or ethyl groups, i.e. these diradicals contain at least one triple bond.
  • R 1 Preferred examples (R 1 ) are mentioned below.
  • a cosmetically acceptable cation is meant any metal cation as well as any organic cation that is not toxic to the skin and/or does not cause allergic reactions.
  • examples of such cations are ammonium salts 4 NR 10 R 11 R 12 R 13 with R 10 , R 11 , R 12 and R 13 being inde- pendently from each other hydrogen or C 1-4 -alkyl.
  • R 1 is non-substituted alkylene, non-substituted alkenylene or non-substituted alkinylene;
  • R 2 is hydrogen or alkyl
  • R 3 is hydrogen, alkyl, or a cosmetically acceptable cation.
  • the invention is concerned with cosmetic compositions comprising a compound of the general formula (I) and/or a compound of the formula (Ia) as defined above, and a retinoid.
  • the invention is concerned with cosmetic compositions comprising at least one compound of the general formula (I)/(Ia) as defined above, and, optionally, at least one retinoid, for the treatment or prevention of symptoms caused by negative devel ⁇ opments of the physiological homeostasis of healthy skin, as well as for the promotion of hair growth and protection from hair loss.
  • the invention is concerned with a method of treatment or prevention of symptoms caused by negative developments of the physiological homeostasis of healthy - A - skin, as well as for the promotion of hair growth and protection from hair loss which method provides topically administering to a person in need of such treatment or preven ⁇ tion an effective amount of a compound of the general formula (I)/(Ia) as defined above, optionally in combination with a retinoid.
  • R 1 is preferably straight chain alkylene, al- kenylene or alkinylene having up to 15 carbon atoms. More preferably, R 1 is straight chain alkylene having from 7 to 13 carbon atoms, such as n-heptylene, n-nonylene, n-undecylene and n-tridecylene.
  • Straight chain alkenylene groups may contain more than one double bond, e.g. up to 4 double bonds.
  • alkenylene groups contain one double bond such as 2-octenylene and 2-dodecenylene.
  • Straight chain alkinylene groups may contain more than one triple bond, e.g. 1 or 2 triple bonds and may additionally contain one or more double bonds.
  • alkinylene groups contain one triple bond, such as 2- octinylene.
  • Alkyl groups represented by R 2 and R 3 preferably contain 1 to 4 carbon atoms such as methyl, ethyl, n-propyl and n-butyl.
  • Examples of cosmetically acceptable cations represented by R 3 are cations conventionally found in cosmetic preparations, e.g., alkali cations such as sodium and potassium ions and alkaline earth metal cations such as calcium und magnesium ions.
  • Particularly preferred compounds of the general formulae (I) and (Ia) are those wherein R 1 is straight chain alkylene having from 7 to 13 carbon atoms; R 2 is hydrogen; and R 3 is hy- drogen.
  • Dodecanoic acid hydroxamide (CAS 10335-68-9)
  • Tetradecanoic acid hydroxamide (CAS 17698-03-2)
  • N-Methoxy-dodecanamide (CAS 185445-14-1) N-Hydroxy-N-methyl-dodecanamide (CAS 52753-89-6)
  • N-Hydroxy-2-dodecenamide (CAS 72070-99-6) N-Hydroxy-2-octinamide (CAS 85594-26-9), as well as the compounds
  • Especially preferred examples of compounds of the formula (I) are octanoic acid hydroxamide, decanoic acid hydroxamide, dodecanoic acid hydroxamide, tetradecanoic acid hydroxamide, hexadecanoic acid hydroxamide, 8-phenyl-octanoic acid hydroxamide, decanoic acid hydroxy-methyl-amide, decanoic acid methoxy-amide and 6-hydroxy- hexanoic acid hydroxyamide.
  • cosmetic composition refers to topical compositions for care of the human skin, see also the heading "Kosmetika” in Rompp Lexikon Chemie, 10th edition 1997, Georg Thieme Verlag Stuttgart, New York.
  • cosmetic compositions are liquid or solid oil-in-water emulsions, water-in-oil emulsions, multiple emulsions, mi- croemulsions, PET-emulsions, bickering emulsions, hydrogels, alcoholic gels, lipogels, one or multiphase solutions, foams, ointments, plasters, suspensions, powders, cremes, cleanser, soaps and other usual compositions, which are applied topically including the application by pens, as masks or as sprays.
  • the cosmetic compositions of this invention are also referred to herein as topical composi ⁇ tions.
  • the cosmetic compositions according to the present invention contain one of the compounds of the general formulae (I) and/or (Ia) above, the invention is not limited to that particular aspect and two or more compounds of the general formulae (I) and/or (Ia) may be present.
  • a retinoid may be additionally present, providing an addi- tive or synergistic cosmetic effect, i.e. an improvement or prevention of symptoms caused by negative developments of the physiological homeostasis of healthy skin, as well as promotion of hair growth and protection from hair loss.
  • two or more retinoids may be present.
  • the ratio of the compound of the general formulae (I) and/or (Ia) to the retinoid is suitably from about 1000: 1 to 1 : 1000, more preferably from about 100: 1 to 1 : 100 and in particular from about 30:1 to 1:30 by weight.
  • the compounds of the general formulae (I) and (Ia) show also an additive or synergistic effect with the retinoids being already present in the human skin.
  • the amount of compound of the general formulae (I) and/or (Ia) is suitably from about 0.0001 to about 50 %, preferably from about 0.001 to about 20 % by weight of the total composition. If a retinoid is present, the amount of the latter is suitably is from about 0.0001 to about 50 % by weight and pref ⁇ erably from about 0.001 to about 20 % by weight of the total composition.
  • compositions according to the present invention can be used for the treatment or prevention of symptoms caused by negative developments of the physiologi ⁇ cal homeostasis of healthy skin, as well as for the promotion of hair growth and protection from hair loss.
  • compositions according to the present invention can further be used for the treatment or prevention of itchy or irritated skin or for fortifying the pigmentation (the latter, however, only, if no retinoid but a tanning active is present.). If retinoid is, however, present in the composition of this invention the composi- tion can be used for the prevention or treatment of pigmentation disorders and/or for pro ⁇ viding an even skin tone, since the boosting of retinoids by compounds of the formula (I)/(Ia) may lead to a depigmentation.
  • compositions of the present invention are used for the treatment or preven ⁇ tion of wrinkles or dry skin or sensitive skin, for the promotion of hair growth, for the pro ⁇ tection from hair loss, for thickening the epidermis, (if retinoid is present) for the preven ⁇ tion or treatment of pigmentation disorders and/or for providing an even skin tone, and/or (if retinoid is absent and a tanning active is present) for fortifying the pigmentation.
  • the composition according to the present invention i.e. the compound of the general formulae (I)/(Ia), may fortify the pigmentation by enhancing the effect of a tanning active.
  • compositions of the invention can also contain usual cosmetic or pharmaceutical adju ⁇ vants and additives, such as preservatives/ antioxidants, fatty substances/ oils, water, or ⁇ ganic solvents, silicones, thickeners, softeners, emulsifiers, sunscreens, antifoaming agents, moisturizers, fragrances, surfactants, fillers, sequestering agents, anionic, cationic, non- ionic or amphoteric polymers or mixtures thereof, propellants, acidifying or basifying agents, dyes, colorants, pigments or nanopigments, e.g. those suited for providing a photo- protective effect by physically blocking out ultraviolet radiation, or any other ingredients usually formulated into cosmetics or medicaments.
  • adju ⁇ vants and additives such as preservatives/ antioxidants, fatty substances/ oils, water, or ⁇ ganic solvents, silicones, thickeners, softeners, emulsifiers, sunscreens, antifoaming agents, moisturizers, fragrances, sur
  • antioxidants/ preservatives are generally preferred. Based on the invention all known antioxidants usually formulated into cosmetics or medicaments can be used. Especially preferred are antioxidants chosen from the group consisting of amino ac- ids (e.g. glycine, histidine, tyrosine, tryptophane) and their derivatives, imidazole (e.g. uro- canic acid) and derivatives, peptides such as D,L-carnosine, D-carnosine, L-carnosine and derivatives (e.g. anserine), carotenoids, carotenes (e.g.
  • amino ac- ids e.g. glycine, histidine, tyrosine, tryptophane
  • imidazole e.g. uro- canic acid
  • peptides such as D,L-carnosine, D-carnosine, L-carnosine and derivatives (e.g. anserine)
  • ⁇ -carotene, ⁇ -carotene, lycopene and derivatives, chlorogenic acid and derivatives, lipoic acid and derivatives (e.g. dihydrol- ipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g.
  • thioredoxine glu- tathione, cysteine, cystine, cystamine and its glycosyl-, N-acetyl-, methyl-, ethyl-, propyl-, amyl-, butyl- and lauryl-, palmitoyl-; oleyl-, y-linoleyl-, cholesteryl- and glycerylester) and the salts thereof, dilaurylthiodipropionate, distearylthiodipropionate, thiodipropionic acid and its derivatives (ester, ether, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (such as buthioninsulfoximine, homocysteinsulfoximine, buthioninsulfone, penta-, hexa-, heptathioninsulfoximine) in very low compatible doses (e.g
  • One or more preservatives/antioxidants may be present in an amount about 0.01 weight% to about 10 weight% of the total weight of the composition of the present invention. Preferably, one or more preservatives/antioxidants are present in an amount about 0.1 weight% to about 1 weight%.
  • topical formulations also contain surface active ingredients like emulsifiers, solubilizers and the like.
  • An emulsifier enables two or more immiscible components to be combined homogeneously. Moreover, the emulsifier acts to stabilize the composition.
  • Emulsifiers that may be used in the present invention in order to form OAV, W/O, 0/W/O or W/OAV emulsions/ microemulsions include sorbitan oleate, sorbitan sesquioleate, sorbi- tan isostearate, sorbitan trioleate, polyglyceryl-3-diisostearate, polyglycerol esters of oleic/isostearic acid, polyglyceryl-6 hexaricinolate, polyglyceryl-4-oleate, polyglyceryl-4 oleate/PEG-8 propylene glycol cocoate, oleamide DEA, TEA myristate, TEA stearate, magnesium stearate, sodium stearate, potassium laurate, potassium ricinoleate, sodium cocoate, sodium tallowate, potassium castorate, sodium oleate, and mixtures thereof.
  • Fur ⁇ ther suitable emulsifiers are phosphate esters and the salts thereof such as cetyl phosphate (Amphisol ® A), diethanolamine cetyl phosphate (Amphisol ® ), potassium cetyl phosphate (Amphisol ® K), sodium glyceryl oleate phosphate, hydrogenated vegetable glyceride phos- phates and mixtures thereof.
  • phosphate esters and the salts thereof such as cetyl phosphate (Amphisol ® A), diethanolamine cetyl phosphate (Amphisol ® ), potassium cetyl phosphate (Amphisol ® K), sodium glyceryl oleate phosphate, hydrogenated vegetable glyceride phos- phates and mixtures thereof.
  • one or more synthetic polymers may be used as an emulsifier.
  • PVP eicosene copolymer acrylates/C lo-3 o alkyl acrylate cross- polymer, acrylates/steareth-20 methacrylate copolymer, PEG-22/dodecyl glycol copolymer, PEG-45/dodecyl glycol copolymer, and mixtures thereof.
  • the preferred emulsifiers are cetyl phosphate (Amphisol ® A), diethanolamine cetyl phosphate (Amphisol ® ), potassium cetyl phosphate (Amphisol ® K), PVP Eicosene copolymer, acrylates/C lo-3 o-alkyl acrylate crosspolymer, PEG-20 sorbitan isostearate, sorbitan isostearate, and mixtures thereof.
  • the one or more emulsifiers are present in a total amount about 0.01 weight% to about 20 weight% of the total weight of the composition of the present invention. Preferably, about 0.1 weight% to about 10 weight% of emulsifiers is used.
  • the lipid phase of the topical compositions can advantageously be chosen from: mineral oils and mineral waxes; oils such as triglycerides of caprinic acid or caprylic acid and castor oil;
  • oils or waxes and other natural or synthetic oils in a preferred embodiment esters of fatty acids with alcohols e.g. isopropanol, propylene glycol, glycerin or esters of fatty alcohols with carboxylic acids or fatty acids; alkylbenzoates; and/or silicone oils such as dimethylpolysiloxane, diethylpolysiloxane, diphenylpolysiloxane, cyclomethicones and mixtures thereof.
  • esters of fatty acids with alcohols e.g. isopropanol, propylene glycol, glycerin or esters of fatty alcohols with carboxylic acids or fatty acids; alkylbenzoates; and/or silicone oils such as dimethylpolysiloxane, diethylpolysiloxane, diphenylpolysiloxane, cyclomethicones and mixtures thereof.
  • Exemplary fatty substances which can be incorporated in the oil phase of the emulsion, microemulsion, oleo gel, hydrodispersion or lipodispersion of the present invention are advantageously chosen from esters of saturated and/or unsaturated, linear or branched alkyl carboxylic acids with 3 to 30 carbon atoms, and saturated and/or unsaturated, linear and/or branched alcohols with 3 to 30 carbon atoms as well as esters of aromatic carboxylic acids and of saturated and/or unsaturated, linear or branched alcohols of 3-30 carbon atoms.
  • esters can advantageously be selected from octylpalmitate, octylcocoate, octyl- isostearate, octyldodecylmyristate, cetearylisononanoate, isopropylmyristate, isopropyl- palmitate, isopropylstearate, isopropyloleate, n-butylstearate, n-hexyllaureate, n-decyloleat, isooctylstearate, isononylstearate, isononylisononanoate, 2- ethyl hexylpalmitate, 2-ethyl- hexyllaurate, 2-hexyldecylstearate, 2-octyldodecylpalmitate, stearylheptanoate, oleyloleate, oleylerucate, e
  • fatty components suitable for use in the topical compositions of the present inven- tion include polar oils such as lecithines and fatty acid triglycerides, namely triglycerol esters of saturated and/or unsaturated, straight or branched carboxylic acid with 8 to 24 carbon atoms, preferably of 12 to 18 carbon-atoms whereas the fatty acid triglycerides are preferably chosen from synthetic, half synthetic or natural oils (e.g.
  • cocoglyceride olive oil, sun flower oil, soybean oil, peanut oil, rape seed oil, sweet almond oil, palm oil, coco- nut oil, castor oil, hydrogenated castor oil, wheat oil, grape seed oil, macadamia nut oil and others); apolar oils such as linear and/ or branched hydrocarbons and waxes e.g.
  • mineral oils vaseline (petrolatum); paraffins, squalane and squalene, polyolefines, hydrogenated polyisobutenes and isohexadecanes, favored polyolefines are polydecenes; dialkyl ethers such as dicaprylylether; linear or cyclic silicone oils such as preferably cyclomethicones (octamethylcyclotetrasiloxane; cetyldimethicone, hexamethylcyclotrisiloxane, polydi- methylsiloxane, poly(methylphenylsiloxane) and mixtures thereof.
  • cyclomethicones octamethylcyclotetrasiloxane
  • cetyldimethicone cetyldimethicone
  • hexamethylcyclotrisiloxane polydi- methylsiloxane
  • Still other fatty components which can advantageously be incorporated in topical com ⁇ positions of the present invention are isoeikosane; neopentylglykoldiheptanoate; pro- pyleneglykoldicaprylate/ dicaprate; caprylic/ capric/ diglycerylsuccinate; butylenglykol caprylat/caprat; C 12-13 -alkyllactate; di-C 12-13 alkyltartrate; triisostearin; dipentaerythrityl hexacaprylat/hexacaprate; propylenglycolmonoisostearate; tricaprylin; dimethylisosorbid.
  • mixtures C 12-15 -alkylbenzoate and 2-ethylhexyliso- stearate mixtures C 12-15 -alkylbenzoate and isotridecylisononanoate as well as mixtures of C 12-15 -alkylbenzoate, 2-ethylhexylisostearate and isotridecylisononanoate.
  • the oily phase of the compositions of the present invention can also contain natural vege ⁇ table or animal waxes such as bee wax, china wax, bumblebee wax and other waxes of insects as well as shea butter and cocoa butter.
  • natural vege ⁇ table or animal waxes such as bee wax, china wax, bumblebee wax and other waxes of insects as well as shea butter and cocoa butter.
  • a moisturizing agent may be incorporated into a topical composition of the present inven ⁇ tion to maintain hydration or rehydrate the skin.
  • Moisturizers that prevent water from evaporating from the skin by providing a protective coating are called emollients. Additionally an emollient provides a softening or soothing effect on the skin surface and is generally considered safe for topical use.
  • Preferred emollients include mineral oils, lanolin, petrolatum, capric/caprylic triglyceraldehydes, cholesterol, silicones such as dimeticone, cyclometicone, almond oil, jojoba oil, avocado oil, castor oil, sesame oil, sunflower oil, coconut oil and grape seed oil, cocoa butter, olive oil aloe extracts, fatty acids such as oleic and stearic, fatty alcohols such as cetyl and hexadecyl (ENJAY), diisopropyl adipate, hy- droxybenzoate esters, benzoic acid esters of Cg -15 -alcohols, isononyl iso-nonanoate, ethers such as polyoxypropylene butyl ethers and polyoxypropylene cetyl ethers, and C 12-15 -alkyl benzoates, and mixtures thereof.
  • silicones such as dimeticone, cyclometicone,
  • the most preferred emollients are hydroxybenzoate es- ters, aloe vera, C 12-15 -alkyl benzoates, and mixtures thereof.
  • An emollient is present in an amount of about 1 weight% to about 20 weight% of the total weight of the composition.
  • the preferred amount of emollient is about 2 weight% to about 15 weight%, and most preferably about 4 weight% to about 10 weight%.
  • humectants Moisturizers that bind water, thereby retaining it on the skin surface are called humectants.
  • Suitable humectants can be incorporated into a topical composition of the present inven ⁇ tion such as glycerin, polypropylene glycol, polyethylene glycol, lactic acid, pyrrolidon carboxylic acid, urea, phopholipids, collagen, elastin, ceramides, lecithin sorbitol, PEG-4, and mixtures thereof.
  • moisturizers are polymeric moisturizers of the family of water soluble and/ or swellable/ and/ or with water gelating polysaccharides such as hyaluronic acid, chitosan and/or a fucose rich polysaccharide which is e.g. available as Fucogel®1000 (CAS-Nr. 178463-23-5) by SOLABIA S.
  • One or more humectants are op ⁇ tionally present at about 0.5 weight% to about 8 weight% in a composition of the present invention, preferably about 1 weight% to about 5 weight%.
  • the aqueous phase of the preferred topical compositions of the present invention can con ⁇ tain the usual cosmetic or pharmaceutical additives such as alcohols, especially lower al ⁇ cohols, preferably ethanol and/ or isopropanol, low diols or polyols and their ethers, pref ⁇ erably propyleneglycol, glycerin, ethyleneglycol, ethyleneglycol monoethyl- or monobu- tylether, propyleneglycol monomethyl- or -monoethyl- or-monobutylether, diethylenegly- col monomethyl-or monoethylether and analogue products, polymers, foam stabilisators; electrolytes and especially one or more thickeners.
  • alcohols especially lower al ⁇ cohols, preferably ethanol and/ or isopropanol, low diols or polyols and their ethers
  • Thickeners that may be used in formulations of the present invention to assist in making the consistency of a product suitable include carbomer, siliciumdioxide, magnesium and/ or aluminium silicates, beeswax, stearic acid, stearyl alcohol polysaccharides and their derivatives such as xanthan gum, hydroxypropyl cellulose, polyacrylamides, acrylate crosspolymers preferably a carbomer, such as carbopole ® of type 980, 981, 1382, 2984, 5984 alone or mixtures thereof.
  • carbomer such as carbopole ® of type 980, 981, 1382, 2984, 5984 alone or mixtures thereof.
  • Suitable neutralizing agents which may be included in the composition of the present in ⁇ vention to neutralize components such as e.g. an emulsifier or a foam builder/stabilizer include but are not limited to alkali hydroxides such as a sodium and potassium hydroxide; organic bases such as diethanolamine (DEA), triethanolamine (TEA), aminomethyl propa- nol, and mixtures thereof; amino acids such as arginine and lysine and any combination of any foregoing.
  • the neutralizing agent can be present in an amount of about 0.01 weight% to about 8 weight% in the composition of the present invention, preferably, 1 weight% to about 5 weight%.
  • the emulsions/ microemulsions of this invention may contain preferably electrolytes of one or several salts including ani- ons such as chloride, sulfates, carbonate, borate and aluminate, without being limited thereto.
  • suitable electrolytes can be on the basis of organic anions such as, but not limited to, lactate, acetate, benzoate, propionate, tartrate and citrate.
  • As cations preferably ammonium, alkylammonium, alkali- or alkaline earth metals, magnesium-, iron- or zinc- ions are selected.
  • Especially preferred salts are potassium and sodium chloride, magnesium sulfate, zinc sulfate and mixtures thereof.
  • Electrolytes can be present in an amount of about 0.01 weight% to about 8 weight% in the composition of the present invention.
  • the topical compositions of the invention can preferably be provided in the form of a lo ⁇ tion, a thickened lotion, a gel, a cream, a milk, an ointment, a powder or a solid tube stick and can be optionally be packaged as an aerosol and can be provided in the form of a mousse, foam or a spray.
  • compositions according to the invention can also be in the form of a suspension or dispersion in solvents or fatty substances, or alternatively in the form of an emulsion or microemulsion (in particular of O/W or W/O type, 0/W/O or W/O/W-type), such as a cream or a milk, a vesicular dispersion, in the form of an oint- ment, a gel, a solid tube stick or an aerosol mousse.
  • the emulsions can also contain ani ⁇ onic, nonionic, cationic or amphoteric surfactants.
  • the topical application is preferably at least once per day, e.g. twice or three times a day. Usually it takes at least two weeks until the desired effect is achieved. However, it can take several weeks or even months until the desired effect is fully maximized.
  • the amount of the topical composition, which is to be applied to the skin depends on the concentration of the active ingredients in the compositions and the desired cosmetic or pharmaceutical effect. For example, application can be such that a cr ⁇ me is applied to the skin. A creme is usually applied in an amount of 2 mg creme/cm 2 skin.
  • the amount of the composition which is applied to the skin is, however, not critical, and if with a certain amount of applied composition the desired effect cannot be achieved, a higher concentra ⁇ tion of the active ingredients can be used e.g. by applying more of the composition or by applying compositions which contain more active ingredient.
  • the active ingredients can be used as such or in an encapsulated form, for example in a liposomal form.
  • Liposomes are preferably formed with lecithins with or without addition of sterols or phytosterols.
  • the encapsulation of the active ingredients can be alone or together with other active ingredi ⁇ ents. It is possible to encapsulate only the compound of formula (I)/(Ia) or only the reti ⁇ noid, but it is also possible to encapsulate both ingredients either together or in separate capsules.
  • inventions include solid or semisolid capsules aiming to protect the retinoid from degradation or for controlled delivery.
  • the capsule may contain the retinoid alone or to ⁇ gether with the compound of formula (I) and/or the compound of the formula (Ia).
  • Suitable encapsulation technologies are for example described in WO 0180823, WO 9903450, WO 9317784 or in Fragrance Journal (2001), 29(2), 83-90.
  • the compound of formula (I) and/or the compound of the formula (Ia) and the retinoid are independently contained in an amount of preferably 0.0001 weight% to about 50 weight%, based on the total weight of the composition. More preferably, the compound of formula (I)/(Ia) and the retinoid are independently contained in the composition in an amount of about 0.001 weight% to about 20 weight%, more pref ⁇ erably in an amount of about 0.01 weight% to about 1 weight%, in particular the com ⁇ pound of formula (I)/(Ia) in an amount of about 0.5 weight% and the retinoid in an amount of about 0.1 weight%, based on the total amount of the composition.
  • composition of the present invention may contain UV-A and UV-B filters.
  • filters or screening agents are disclosed, e.g., in WO 04/000256, see es ⁇ pecially pages 10-12.
  • UV-B or broad spectrum screening agents i.e. substances having ab ⁇ sorption maximums between about 290 and 340 nm, which are preferred for combination with the compositions of the present invention, are the following organic and inorganic compounds:
  • Camphor derivatives such as 4-methyl benzylidene camphor (PARSOL® 5000), 3- benzylidene camphor, camphor benzalkonium methosulfate, polyacrylamidomethyl benzylidene camphor, sulfo benzylidene camphor, sulfomethyl benzylidene cam ⁇ phor, therephthalidene dicamphor sulfonic acid;
  • Cinnamate derivatives such as octyl methoxycinnamate (PARSOL® MCX), eth- oxyethyl methoxycinnamate, diethanolamine methoxycinnamate (PARSOL® Hy ⁇ dro), isoamyl methoxycinnamate and the like as well as cinnamic acid derivatives bond to siloxanes;
  • - p-aminobenzoic acid derivatives such as p-aminobenzoic acid, 2-ethylhexyl p- dimethylaminobenzoate, N-oxypropylenated ethyl p-aminobenzoate, glyceryl p- aminobenzoate, - Benzophenones such as benzophenone-3, benzophenone-4, 2,2',4,4'-tetrahydroxy- benzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone;
  • micro- Pigments such as microparticulated TiO2, and the like.
  • micro- particulated refers to a particle size from about 5 nm to about 200 nm, particularly from about 15 nm to about 100 nm.
  • the TiO2 particles may also be coated by metal oxides such as e.g. aluminium or zirconium oxides or by organic coatings such as e.g. polyols, methicone, aluminium stearate, alkyl silane.
  • 2-phenyl benzimidazole sulfonic acid and its salts PARSOL®HS.
  • Salts of 2-phenyl benzimidazole sulfonic acid are e.g. alkali salts such as sodium- or potassium salts, ammonium salts, morpholine salts and salts of primary, sec. and tert. amines like monoethanolamine salts and diethanol- amine salts.
  • Salicylate derivatives such as isopropylbenzyl salicylate, benzyl salicylate, butyl salicylate, octyl salicylate (NEO HELIOPAN OS), isooctyl salicylate or homomen- thyl salicylate (homosalate, HELIOPAN).
  • Triazine derivatives such as octyl triazone (UVINUL T-150), dioctyl butamido tria- zone (UVASORB HEB), bis ethoxyphenol methoxyphenyl triazine (Tinosorb S) and the like.
  • compositions of the present invention are the following organic and inorganic compounds:
  • Dibenzoylmethane derivatives such as 4-tert. butyl-4'-methoxydibenzoyl-methane (PARSOL® 1789), dimethoxydibenzoylmethane and isopropyldibenzoylmethane;
  • Benzotriazole derivatives such as 2,2'-methylene-bis-(6-(2H-benzotriazole-2-yl)-4- (l,l,3,3,-tetramethylbutyl)-phenol (TINOSORB M);
  • Phenylene-l,4-bis-benzimidazolsulfonic acids or salts such as 2,2-(l,4- phenylene)bis-(lH-benzimidazol-4,6-disulfonic acid) (Neoheliopan AP); - Amino substituted hydroxybenzophenones such as 2-(4-Diethylamino-2-hydroxy- benzoyl)-benzoic acid hexylester as described in EP-A 1 046 391;
  • micropar- ticulated refers to a particle size from about 5 nm to about 200 nm, particularly from about 15 nm to about 100 nm.
  • the particles may also be coated by other metal oxides such as e.g. aluminium or zirconium oxides or by organic coatings such as e.g. polyols, methicone, aluminium stearate, alkyl silane.
  • dibenzoylmethane derivatives have limited photbstability it may be desirable to photostabilize these UV-A screening agents.
  • conventional UV-A screening agent also refers to dibenzoylmethane derivatives such as e.g.
  • PARSOL® 1789 stabilized by, e.g.,
  • UV-A- and UV-B-filters which can be added to the compositions of the present invention can also be found in DE-A 103 27 432. All UV-filter compounds disclosed in this document are also useful as components for the compositions of the pre ⁇ sent invention and are included herein by reference.
  • composition can also contain one or more additional pharmaceutically or cosmetically active ingredients, in particular for preventing or reducing acne, wrinkles, lines, atrophy, inflammation, as well as topical anesthetics, artificial tanning agents and accelerators, an ⁇ timicrobial agents, and antifungal agents and sunscreening additives.
  • additional pharmaceutically or cosmetically active ingredients in particular for preventing or reducing acne, wrinkles, lines, atrophy, inflammation, as well as topical anesthetics, artificial tanning agents and accelerators, an ⁇ timicrobial agents, and antifungal agents and sunscreening additives.
  • peptides e.g., MatrixylTM [pentapeptide derivative]
  • glycerol urea
  • gua- nidine e.g., amino guanidine
  • vitamins and derivatives thereof such as ascorbic acid, vi- tamin A (e.g., retinoid derivatives such as retinyl palmitate or retinyl propionate), vitamin E (e.g., tocopherol acetate), vitamin B3 (e.g., niacinamide) and vitamin B5 (e.g., pan- thenol) and the like and mixtures thereof
  • wax-based synthetic peptides e.g., octyl palmi ⁇ tate and tribehenin and sorbitan isostearate and palmitoyl-oligopeptide
  • anti-acne me- dicaments resorcinol, salicylic acid, and the like
  • antioxidants e.g., phytosterols
  • the present invention further concerns a method of treating or preventing wrinkles or hu ⁇ man dry skin or sensitive skin or any symptoms caused by negative developments of the physiological homeostasis of healthy skin, promotion of hair growth, protection from hair loss, thickening the epidermis, anti-acne, the inhibition of senescence of skin cells, preven- tion or treatment of photodamage, prevention or treatment of oxidative stress phenomena, prevention or treatment of cellulite, prevention and treatment of disturbances in ceramide and lipid synthesis, prevention of excess sebum production, reduction of activities of ma ⁇ trix metallo proteases or other proteases in the skin, treatment and prevention of inflamma ⁇ tory skin conditions including atopic eczema, polymorphic light eruption, psoriasis, ver- tiligo, prevention and treatment of itchy or irritated skin, which method comprises the step of topically administering to a person in need of such treatment or prevention an effective amount of a compound of the general formula (I) as defined
  • a further object of the present invention is a method for the prevention or treatment of pigmentation disorders and/or for providing an even skin tone, which method comprises the step of topically administering to a person in need of such prevention or treatment an effective amount of a composition according to the present invention as defined above, wherein the composition contains a retinoid.
  • Another object of the present invention is a method for fortifying the pigmentation which method comprises the step of topically administering to a person in need of such fortifica ⁇ tion an effective amount of a composition according to the present invention as defined above and topically administering a tanning active, wherein the tanning active may be ad- ministered before, after or simultaneously with the administration of the effective amount of the composition according to the present invention, and wherein any retinoid is essen ⁇ tially absent in such a composition.
  • a preferred embodiment of the present invention is a method of treating or preventing wrinkles or human dry skin or sensitive skin, of promoting hair growth, of protecting from hair loss, of thickening the epidermis, which method comprises the step of topically administering to a person in need of such treatment or prevention an effective amount of a compound of the general formula (I) as defined in claim 1, optionally in combination with a retinoid.
  • a compound of the general formula (I) as defined above for boosting the cos ⁇ metic effects of retinoids and/or tanning actives is also an object of the present invention.
  • the concept of a synergistic effect between a retinoid and a compound of formula (I)/(Ia) may be demonstrated in an in vitro test system using human primary keratinocytes.
  • the marker in the example below is the enzyme Transglutaminase 1, which is a well-known and common differentiation marker in human epidermal cells.
  • Transglutaminase 1 is a well-known and common differentiation marker in human epidermal cells.
  • retinoic acid was used as a representative from the group of retinoids retinoic acid. From the compounds of formula (I)/(Ia) octanoic acid hydroxyamide, decanoic acid hydroxyamide, dodecanoic acid hydroxyamide and tet- radecanoic acid hydroxyamide were elected.
  • Epidermal keratinocytes were isolated from human foreskin biopsies and cultured in keratinocyte serum free medium (KSFM, GIBCO) in a growth chamber with 37°C and 5% CO 2 . At the second passage, cells were transferred to 6 well plates and allowed to reach approximately 50% surface confluence.
  • KSFM keratinocyte serum free medium
  • Retinoic acid and the compounds of formula (I) were solubilized in ethanol or ethanol/ tetrahydrofuran. Retinoic acid solutions were handled under yellow light conditions only.
  • the KSFM medium was supplemented with 1.3 mM calcium, in order to induce keratinocyte differentiation and thus also induce TGl expression, and treatment was started by adding either retinoic acid compound of formula (I) or both substances in combination. For every sample, me- dium and/or treatment substances were changed twice daily.
  • ClO decanoic acid hydroxyamide
  • C 12 dodecanoic acid hydroxyam- ide
  • C 14 tetradecanoic acid hydroxyamide.
  • the differentiation marker of epidermal keratinocytes in the test system for the highest concentration of decanoic acid hydroxyamide was found to be about 12 fold reduced (Ta ⁇ ble 1).
  • the x-fold repression for dodecanoic acid hydroxyamide is about 11 and for the tetradecanoic acid hydroxyamide still above 6 fold.
  • Table 2 Synergism of compounds of formula (Ia) in combination with retinoic acid.
  • concentration of retinoic acid was 1x10 ,-9 M in all cases.
  • Anti-aging formulations containing the ingredients indicated below can be prepared in a manner known per se.
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol 0.50 0.50
  • Anti-aging formulations containing the ingredients indicated below can be prepared in a manner known per se.
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol
  • Facial treatment formulations containing the ingredients indicated below can be prepared in a manner known per se
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol 0.50 0.50 -
  • Facial treatment formulations containing the ingredients indicated below can be prepared in a manner known per se
  • D-Panthenol 0.20 0.20 0.20 Disodium EDTA 0.10 0.10 0.10 Propylene Glycol 4.00 4.00 4.00
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol
  • Hair loss sera containing the ingredients indicated below can be prepared in a manner known per se
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol 0.50 0.50
  • Hair loss sera containing the ingredients indicated below can be prepared in a manner known per se
  • Vitamin E Acetate 0 0..1100 0 0..1100 0 0..1100 0 0..1100
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol 0.50 0.50
  • Skin fortifier lotions containing the ingredients indicated below can be prepared in a man ⁇ ner known per se
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol 0.50 0.50 -
  • Skin fortifier lotions containing the ingredients indicated below can be prepared in a man ⁇ ner known per se
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol
  • Formulations to treat age spots containing the ingredients indicated below can be prepared in a manner known per se
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol 0.50 0.50 -
  • Formulations to treat age spots containing the ingredients indicated below can be prepared in a manner known per se
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol
  • Anti-cellulite formulations containing the ingredients indicated below can be prepared in a manner known per se
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol 0.50 0.50
  • Anti-cellulite formulations containing the ingredients indicated below can be prepared in a manner known per se
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol
  • Skin repair formulations containing the ingredients indicated below can be prepared in a manner known per se
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol 0.50 0.50
  • Skin repair formulations containing the ingredients indicated below can be prepared in a manner known per se
  • Retinol 15D Caprylic/Capric Triglyceride & Retinol
  • the lay ⁇ ers were separated and the aqueous layer was extracted twice with ethyl acetate (40 mL). The organic layers were combined and washed three times with an aqueous solution of 5% hydrochloric acid and once with brine 30 mL). The organic layer was dried over Na 2 SO 4 , filtrated and the solvent removed under reduced pressure. The residue was dried under high vacuum at room temperature to obtain 1.46 g (92 %) of the product as a white solid.
  • N-methyl-hydroxylamine hydrochloride (3.60 g, 43.1 mmol, 2.0 equiva ⁇ lents) in diethyl ether (250 mL) was cooled to 0°C. Then pyridine (5 mL) and sodium car ⁇ bonate anhydrous (9.14 g, 86.21 mmol, 4.0 equivalents) were added and the white suspen ⁇ sion stirred for 15 minutes.
  • Decanoyl chloride (9.54 g, 21.6 mmol, 1.0 equivalents) in di ⁇ ethyl ether (20 mL) was slowly added over 10 minutes. The temperature was held in the range of -5°C to +5°C.
  • the reaction mixture was stirred over night and allowed to warm up to room temperature. Water (200 mL) was added and the layers were separated. The aqueous layer was extracted twice with ethyl acetate (200 mL). The organic layers were combined and extracted once with an aqueous solution of 1 M citric acid (150 mL) and with brine (150 mL). The organic layer was dried over Na 2 SO 4 , filtrated and the solvent removed under reduced pressure. The residue was dried under high vacuum at room tem ⁇ perature to give 3.77 g (87 %) of a white solid.

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Abstract

La présente invention concerne des compositions cosmétiques comprenant un composé de formule générale (I), dans laquelle L est hydrogène, alkyle ramifié, aryle, hétéroaryle, cycloalkyle, hétérocycloalkyle, hydroxyle, OR, HO-(CH2-CH2-O)n, HO-(CH2-O)n, HO-(CH2-CH2-CH2-O)n, HO-(CH2-CH(CH3)-O)n, HO-(CH(CH3)-CH2-O)n, NR4R5, ou C(O)NR6R7, R étant alkyle C1-4 ou alcanoyle C2-18, n étant un nombre entier de 1 à 8, R4, R5, R6 et R7 étant indépendamment les uns des autres hydrogène ou alkyle C1-18, R1 étant alkylène, alcénylène ou alkinylène éventuellement substitué avec un ou plusieurs groupes méthyle ou éthyle, R2 étant hydrogène ou alkyle, et R3 étant hydrogène, alkyle ou un cation cosmétiquement acceptable, ainsi qu'un support habituellement utilisé dans des compositions cosmétiques. De préférence, ces compositions comprennent en outre un rétinoïde. La présente invention concerne également, entre autres, l'utilisation de ces compositions pour traiter ou prévenir les rides ou la peau sèche ou sensible ou tout autre symptôme causé par les évolutions négatives de l'homéostasie physiologique de la peau saine, pour favoriser la croissance des cheveux, pour prévenir la perte des cheveux, pour épaissir l'épiderme, pour traiter l'acné, pour inhiber le vieillissement des cellules cutanées, pour prévenir ou traiter les photodommages, pour prévenir ou traiter le stress oxydatif, pour prévenir ou traiter la cellulite, pour prévenir et traiter les troubles de la synthèse des céramides et des lipides, pour prévenir la production excessive de sébum, pour réduire l'activité des métalloprotéases matricielles ou d'autres protéases dans la peau, pour traiter et prévenir les affections cutanées inflammatoires telles que l'eczéma atopique, l'éruption légère polymorphe, le psoriasis et le vertiligo, et pour prévenir et traiter la dermatite prurigineuse ou l'irritation cutanée. L'invention se rapporte en outre aux méthodes de traitement et de prévention elles-mêmes.
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WO2012003176A1 (fr) * 2010-07-02 2012-01-05 Helix Biomedix, Inc. Dérivés n-acyle d'acide aminé pour traiter des affections cutanées telles que la cellulite
WO2012177986A2 (fr) 2011-06-22 2012-12-27 Vyome Biosciences Promédicaments antifongiques et antibactériens à base d'un conjugué
DE102011088934A1 (de) * 2011-12-19 2013-06-20 Beiersdorf Ag Wirkstoffkombinationen aus einem oder mehreren Polyolen und einer oder mehreren physiologisch unbedenklichen Hydroxamsäuren, sowie kosmetische oder 10 dermatologische Zubereitungen, solche Wirkstoffkombinationen enthaltend
DE102011088926A1 (de) * 2011-12-19 2013-06-20 Beiersdorf Ag Haarstylingformulierung zur Erstellung eines flexiblen Haltes durch Einsatz von Octanohydroxamsäure
WO2013092457A3 (fr) * 2011-12-19 2014-04-03 Beiersdorf Ag Associations de principes actifs à base d'un ou de plusieurs acides carboxyliques, notamment d'acides hydroxycarboxyliques, et d'un ou de plusieurs acides hydroxamiques physiologiquement acceptables, ainsi que préparations cosmétiques ou dermatologiques contenant de telles associations de principes actifs
WO2014195872A1 (fr) 2013-06-04 2014-12-11 Vyome Biosciences Pvt. Ltd. Particules enrobées et compositions les comprenant
EP2868324A4 (fr) * 2012-06-28 2015-12-09 Shiseido Co Ltd Inhibiteur de décomposition d'acide hyaluronique comprenant de l'extrait de romarin et de l'acétate de rétinol
WO2017008974A1 (fr) * 2015-07-14 2017-01-19 Unilever Plc Composition antimicrobienne
WO2017017631A2 (fr) 2015-07-28 2017-02-02 Vyome Biosciences Pvt. Ltd. Agents thérapeutiques antibactériens et agents prophylactiques
KR20170134189A (ko) * 2016-05-26 2017-12-06 인올렉스 인베스트먼트 코포레이션 피부 내의 기질 메탈로프로테이나아제를 억제하고 노화를 감소시키는 방법 및 관련 상승작용 조성물들
KR101914441B1 (ko) * 2017-05-04 2018-11-02 (주)앗코스텍 퓨코스테롤을 유효성분으로 포함하는 피부 보습용 화장료 조성물
WO2023275790A1 (fr) * 2021-06-29 2023-01-05 Eth Zurich Dérivés d'acide hydroxamique insaturés et leur utilisation pour le traitement et la prévention d'une maladie ou d'un trouble associé à l'ammoniac

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WO2008090440A1 (fr) * 2007-01-22 2008-07-31 Carlo Ghisalberti Suppositoire gynécologique à base de lipides
CN103079553B (zh) * 2010-07-02 2016-01-20 赫里克斯生物医疗公司 用于治疗诸如脂肪团的皮肤病症的n-酰基氨基酸衍生物
WO2012003176A1 (fr) * 2010-07-02 2012-01-05 Helix Biomedix, Inc. Dérivés n-acyle d'acide aminé pour traiter des affections cutanées telles que la cellulite
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CN103079553A (zh) * 2010-07-02 2013-05-01 赫里克斯生物医疗公司 用于治疗诸如脂肪团的皮肤病症的n-酰基氨基酸衍生物
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AU2011271466B2 (en) * 2010-07-02 2013-08-22 Helix Biomedix, Inc. N-acyl amino acid derivatives for treating skin conditions such as cellulite
RU2590977C2 (ru) * 2010-07-02 2016-07-10 Хеликс Байомедикс, Инк. Производные n-ациламинокислот для лечения таких патологий кожи, как целлюлит
WO2012177986A2 (fr) 2011-06-22 2012-12-27 Vyome Biosciences Promédicaments antifongiques et antibactériens à base d'un conjugué
DE102011088926A1 (de) * 2011-12-19 2013-06-20 Beiersdorf Ag Haarstylingformulierung zur Erstellung eines flexiblen Haltes durch Einsatz von Octanohydroxamsäure
EP2606934A3 (fr) * 2011-12-19 2014-07-02 Beiersdorf AG Utilisation d'acide octanohydroxamique dans des formules de coiffage de cheveux
WO2013092457A3 (fr) * 2011-12-19 2014-04-03 Beiersdorf Ag Associations de principes actifs à base d'un ou de plusieurs acides carboxyliques, notamment d'acides hydroxycarboxyliques, et d'un ou de plusieurs acides hydroxamiques physiologiquement acceptables, ainsi que préparations cosmétiques ou dermatologiques contenant de telles associations de principes actifs
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