EP1881817A2 - Utilisation de decomposeurs de peroxydes dans des produits cosmetiques et pharmaceutiques pour le soin de la peau - Google Patents

Utilisation de decomposeurs de peroxydes dans des produits cosmetiques et pharmaceutiques pour le soin de la peau

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Publication number
EP1881817A2
EP1881817A2 EP06742899A EP06742899A EP1881817A2 EP 1881817 A2 EP1881817 A2 EP 1881817A2 EP 06742899 A EP06742899 A EP 06742899A EP 06742899 A EP06742899 A EP 06742899A EP 1881817 A2 EP1881817 A2 EP 1881817A2
Authority
EP
European Patent Office
Prior art keywords
radicals
skin
alkyl
hydrogen
aryl
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.)
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Application number
EP06742899A
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German (de)
English (en)
Inventor
Axel Jentzsch
Sylke Haremza
Arne Ptock
Gerhard Wagenblast
Manfred Kroll
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.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1881817A2 publication Critical patent/EP1881817A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
    • 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

Definitions

  • the present invention relates to the use of compounds having certain sulfur and optionally nitrogen atom-containing structures as Peroxidzersetzer in cosmetic and pharmaceutical compositions for the treatment of the skin.
  • the invention further relates to cosmetic and pharmaceutical compositions containing compounds having such structures.
  • Human skin is subject to certain aging processes that are partly due to intrinsic processes (chronoaging) and partly due to exogenous factors (environmental, eg photoaging).
  • temporary or permanent changes in the appearance of the skin such as acne, oily or dry skin, keratoses, rosaceae, photosensitive, inflammatory, erythematous, allergic or autoimmune reactions such as dermatoses, photodermatoses and others, their exact causes and factors that influence them, often understood only incompletely.
  • the exogenous factors include, in particular, sunlight or artificial radiation sources with a comparable spectrum, as well as compounds which can be formed by the radiation, such as undefined reactive photoproducts, which can also be free-radical or ionic.
  • These factors include but are not limited to harmful or reactive compounds such as ozone, free radicals such as the hydroxyl radical, singlet oxygen and other reactive oxygen or nitrogen compounds, cigarette smoke, natural and synthetic toxins, and others that interfere with the natural physiology or morphology of the skin.
  • the influence of these factors leads, among other things, to direct damage to the DNA of the skin cells as well as the collagen, elastin or glycosaminoglycan molecules of the extracellular matrix, which are responsible for the firmness of the skin.
  • MMPs matrix metalloproteinases
  • TIMPs tissue inhibitors of matrix metalloproteinases
  • immunoregulatory compounds such as interleukins, prostaglandins and histamines. ne distributed.
  • immunocompetent cells are attracted and the inflammatory response is enhanced.
  • the consequences of aging are thinning of the skin, weaker interlocking of epidermis and dermis, reduction in the number of cells and the supply of blood vessels.
  • the aging process leads to the formation of fine lines and wrinkles, the skin becomes leathery, yellowish and drooping, pigmentation disorders occur.
  • Antioxidants effective as radical scavengers are often used in dermatological or cosmetic preparations for protection against spoilage. In addition, they can also be used to reduce harmful or undesirable oxidative processes that occur in human or animal skin. It is known that such processes play a significant role in skin aging. The skin is permanently exposed to oxidative stress due to the formation of peroxides and hydroperoxides, some of which originate from the external environment of the skin, but are sometimes formed endogenously. To counteract this stress, the skin has a number of its own protective mechanisms. However, these protections are not sufficient to completely prevent oxidative processes in the skin. On the contrary, it is generally accepted that these same oxidative processes make a significant contribution to skin aging, but also to general or pathological changes in the skin.
  • WO 98/51268 describes hair dyes containing at least one pyrazoline-4,5-dione and at least one aromatic or heteroaromatic amine. This amine may be, for example, a thiouracil.
  • DE-A-100 24 886 describes an agent for dyeing keratin-containing fibers containing at least one nitrosopyridine and / or pyrimidine. These compounds may be substituted, inter alia, with mercapto groups.
  • DE-OS-25 23 629 describes a hair dye containing a 5,6-diamino-4-oxopyrimidine derivative which may contain a double bonded sulfur atom in the 2-position of the heterocycle.
  • EP-A-0 422 765 describes a topical composition for promoting hair growth, wherein as hair growth promoters, inter alia, nitrogen and sulfur-containing heterocycles, such as. For example, 5-carboxy-5-hydroxyvalero-1, 4-thiolactone, are used.
  • EP-A-0 540 854 describes a hair growth-promoting composition containing as active ingredient at least one compound selected from purines, pyridylureas, diphenylureas, pyrimidines, imidazoles, benzoylamine ureas and 4-substituted aminopyrrole [2,3-d] pyrimidines. These can, in addition to a variety of other substituents, inter alia, also carry thio groups.
  • EP-A-0 483 426 describes a deodorant composition containing as active ingredient a heterocyclic thiol.
  • CN-A-1075180 describes the bactericidal deodorizing finish of fabrics using, inter alia, thiols and thiocarboxylic acids.
  • JP 05124924-A describes a topical medicament for inhibiting melamine production, which contains as active ingredient at least one pyridine or pyridinethiol.
  • No. 6,383,476 describes anhydrous antiperspirant and deodorant compositions containing, as active ingredient, inter alia nitrogen-containing heterocycles containing sulfur-containing groups, such as thionicotinamide and 2-mercaptothionicotinic acid.
  • WO 01/64206 describes a method of inhibiting or reducing pigment production in a mammal using as its active ingredient a six-membered heterocycle bearing as a substituent a structure derived from an amide or thioamide, including, but not limited to, nitrogen atom-containing Heterocycles can act.
  • WO 02/053101 describes a process for the treatment of fibrotic diseases, wherein the active substance used is certain nitrogen heterocycles which may have in the ring or as substituents sulfur atoms or groups containing sulfur atoms, and wherein this active substance can be administered topically. None of the above-mentioned documents describes a use of the sulfur atom-containing compounds disclosed therein as peroxide decomposers in cosmetic and pharmaceutical agents for the treatment of the skin.
  • DE-A-102 02 065 describes cosmetic or dermatological compositions which contain a) at least one antioxidant effective as an O- or C-radical scavenger and b) at least one organic boron-containing compound as peroxide decomposer.
  • DE-A-100 36 655.4 describes the use of a combination of a) at least one antioxidant effective as an O- or C-radical scavenger and b) at least one organic or inorganic skin-compatible compound which reacts peroxides or hydroperoxides to form the corresponding alcohols without formation as a supplement to cosmetic or dermatological preparations for the prevention of skin damage by peroxides or hydroperoxides formed as a result of endogenous or exogenous factors.
  • the present invention therefore relates to the use of compounds of the general formulas 1.1 to 1.3
  • n is an integer from 1 to 3
  • Z 1 and Z 2 are organyl radical and the other is hydrogen or an organyl radical, where Z 1 and Z 2 may together also represent a bivalent bridging group having 1 to 5 atoms between the flanking bonds,
  • R 1 is hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl or an n-valent cation
  • R 2 is hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, hetaryl, COOR a , COO "
  • R a are each the same or different radicals selected from hydrogen, alkyl,
  • E 1 , E 2 , E 3 are each identical or different radicals selected from hydrogen, alkyl, cycloalkyl, aryl or hetaryl,
  • R b is hydrogen, methyl or ethyl
  • M + is a cation equivalent
  • y is an integer from 1 to 250
  • Peroxidzersetzer in cosmetic and pharmaceutical agents for the treatment of the skin.
  • a "peroxide decomposer” is understood to mean an antioxidant which, in contrast to conventional radical scavengers, already avoids or at least reduces the formation of peroxides and / or hydroperoxides.
  • the compounds of the general formulas 1.1 to 1.3 used according to the invention are capable of effectively preventing damage to the skin at another site by interfering with the mechanism of the scheme depicted above.
  • these compounds already act at an early stage of radical formation, so that multiple radical formation is prevented. This can be done, for example, to an ionic and reducing attack according to the following scheme, but other modes of action are conceivable.
  • the compounds of the formulas 1.1 to 1.3 employed according to the invention are distinguished by a significantly greater (reducing) decomposition and / or hydroperoxide-decomposing effect than skin-containing sulfur-containing compounds such as cystine or cysteine.
  • they are capable, in the form of a solution having a molar concentration of 0.05 mol / l in a polar or nonpolar solvent, of an initial peroxide or hydroperoxide concentration of at least 20%, preferably 50%, and in particular within three minutes To reduce 90%.
  • alkyl includes straight-chain and branched alkyl groups, preferably straight-chained or branched dC ⁇ o-alkyl, preferably C 1 -C 12 -alkyl, more preferably d-C ⁇
  • alkyl groups are, in particular, methyl, ethyl, propyl, isopropyl, n-butyl, 2-butyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 2-methylbutyl, 3-methylbutyl,
  • alkyl also encompasses substituted alkyl groups which generally have 1, 2, 3, 4 or 5, preferably 1, 2 or 3 and particularly preferably 1, substituents which are preferably selected from alkoxy, cycloalkyl, aryl, hetaryl , Hydroxyl, halogen, NE 1 E 2 , NE 1 E 2 E 3+ , carboxylate and sulfonate.
  • a preferred perfluoroalkyl group is trifluoromethyl.
  • alkylene in the context of the present invention stands for straight-chain or branched alkanediyl groups having 1 to 5 carbon atoms.
  • cycloalkyl in the context of the present invention comprises unsubstituted as well as substituted cycloalkyl groups, preferably Cs-C T -cycloalkyl groups, such as cyclopentyl, cyclohexyl or cycloheptyl, which in the case of a substitution, generally 1, 2, 3, 4 or 5 , preferably 1, 2 or 3, and particularly preferably carry 1 substituent .
  • these substituents are selected from alkyl, alkoxy, NE 1 E 2 , NE 1 E 2 E 3+ , and halogen.
  • heterocycloalkyl in the context of the present invention comprises saturated, cycloaliphatic groups having generally 4 to 7, preferably 5 or 6, ring atoms in which 1 or 2 of the ring carbon atoms are represented by heteroatoms selected from the elements oxygen, nitrogen and sulfur, are substituted and which may optionally be substituted, wherein in the case of a substitution, these heterocyclo-aliphatic groups 1, 2 or 3, preferably 1 or 2, particularly preferably 1 Can carry substituents. These substituents are preferably selected from alkyl, alkoxy, aryl, COOR 0 , COO M + , hydroxyl, halogen and NE 1 E 2 , particularly preferred are alkyl radicals.
  • heterocycloaliphatic groups include pyrrolidinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, imidazolidinyl, pyrazolidinyl, oxazolidinyl, morpholidinyl, thiazolidinyl, isothiazolidinyl, isoxazolidinyl, piperazinyl, tetrahydrothiophenyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl.
  • aryl for the purposes of the present invention comprises unsubstituted and substituted aryl groups, and is preferably phenyl, ToIyI, XyIyI, mesityl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl or naphthacenyl, particularly preferably phenyl or naphthyl, said aryl groups im In the case of a substitution in general 1, 2, 3, 4 or 5, preferably 1, 2 or 3 and particularly preferably 1 substituent selected from the groups alkyl, alkoxy, carboxylate, trifluoromethyl, sulfonate, NE 1 E 2 , alkylene NE 1 E 2 , nitro, cyano or halogen.
  • a preferred perfluoroaryl group is pentafluorophenyl.
  • heterocycloaromatic groups preferably the groups furyl, thiophenyl, pyridyl, quinolinyl, acridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, indolyl, purinyl, indazolyl, benzotriazolyl , 1,2,3-triazolyl,
  • these heterocycloaromatic groups may in general carry 1, 2 or 3 substituents selected from among alkyl, alkoxy, hydroxyl, carboxylate, sulfonate, NE 1 E 2 , alkylene-NE 1 E 2 or halogen.
  • Carboxylate and sulfonate in the context of this invention preferably represent a derivative of a carboxylic acid function or a sulfonic acid function, in particular a metal carboxylate or sulfonate, a carboxylic acid ester or sulfonic acid ester function or a carboxylic acid or sulfonic acid amide function.
  • these include z.
  • esters with CrC ⁇ AIkanolen such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol and tert-butanol.
  • acyl in the context of the present invention represents alkanoyl or aroyl groups having generally 2 to 11, preferably 2 to 8, carbon atoms, for example the formyl, acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl, Heptanoyl, 2-ethylhexanoyl, 2-propylheptanoyl, benzoyl or naphthoyl group.
  • the radicals E 1 to E ⁇ are independently selected from hydrogen, alkyl, cycloalkyl and aryl.
  • the groups NE 1 E 2 and NE 4 E 5 are preferably N, N-dimethylamino, N, N-diethylamino, N, N-dipropylamino, N, N-diisopropylamino, N, N-di-n-butylamino, N, N-di-t.-butylamino, N, N-dicyclohexylamino or N, N-diphenylamino.
  • Halogen is fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine.
  • M + stands for a cation equivalent, ie for a monovalent cation or the fraction of a polyvalent cation corresponding to a positive single charge.
  • the cation M + is only used as a counter ion for the neutralization of negatively charged
  • Substituentengrup- pen such as the COO "or sulfonate group, and may be arbitrarily selected in principle
  • anion equivalent X ' which serves merely as a counterion of positively charged substituent groups, such as the ammonium groups, and can be chosen arbitrarily from monovalent anions and the portions of a polyvalent anion corresponding to a negative single charge, where in general halide ions X " preferred are, in particular chloride and bromide.
  • the values for x and y are an integer from 1 to 240, preferably an integer from 2 to 120.
  • Condensed ring systems may be fused (fused) aromatic, hydroaromatic and cyclic compounds.
  • Condensed ring systems consist of two, three or more than three rings. Depending on the type of linkage, a distinction is made in condensed ring systems between an ortho-annulation, d. H. each ring has one edge or two atoms in common with each adjacent ring, and a peri-annulation in which one carbon atom belongs to more than two rings.
  • Preferred among the fused ring systems are ortho-fused ring systems.
  • Preferred fused rings are benzene, naphthalene and anthracene rings which, if desired, may carry one or more of the substituents previously mentioned for aryl.
  • the compounds of the formulas 1.1 to I.3 used according to the invention are preferably selected from compounds 1.1a, 1.1b, 1.2a, 1.2b and 1.3a
  • Q is a divalent bridging group of 2 to 5 atoms between the flanking bonds
  • B n + is a monovalent to trivalent cation
  • n is an integer from 1 to 3
  • R a are each the same or different radicals selected from hydrogen, alkyl, cycloalkyl, aryl or hetaryl,
  • E 1 , E 2 , E 3 are each identical or different radicals selected from hydrogen, alkyl, cycloalkyl, aryl or hetaryl,
  • R b is hydrogen, methyl or ethyl, M + is a cation equivalent,
  • y is an integer from 1 to 250, which recited in claim 1
  • Z 1 and Z 2 independently of one another are hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, amino, aminocarbonyl, aminothiocarbonyl or thiocarbamidyl, where at least one of Z 1 or Z 2 is aryl or heteroaryl.
  • the compounds of the formula 1.1 to 1.3 are selected from
  • G 1 is N or CR 3 ,
  • G 2 is N or CR 4 ,
  • G 3 is N or CR 5 ,
  • G 4 is N or CR 6 .
  • R 3 , R 4 , R 5 and R 6 independently of one another represent hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, COOR 0 , COO M + , SO 3 R C , SO 3 M + , sulfonamide, NE 4 E 5 , (NE 4 E 5 E 6 J + A ' , OR C , SR 0 , (CHR d CH 2 O) w R °, (CH 2 O) W R °,
  • R c are each the same or different radicals selected from hydrogen, alkyl, cycloalkyl, aryl or hetaryl,
  • E 4 , E 5 , E 6 are each identical or different radicals selected from hydrogen, alkyl, cycloalkyl, aryl or hetaryl,
  • R d is hydrogen, methyl or ethyl
  • M + is a cation equivalent
  • a ' represents an anion equivalent
  • w is an integer from 1 to 250
  • two adjacent radicals R 3 to R ⁇ can also form a fused ring system having one, two or three further rings,
  • G 5 is BR 7 , CR 7 R 8 , SiR 7 R 8 , NR 7 , PR 7 , O or S,
  • G 6 is BR 9 , CR 9 R 10 , SiR 9 R 10 , NR 9 , PR 9 , O or S,
  • G 7 is BR 11 , CR 11 R 12 , SiR 11 R 12 , NR 11 , PR 11 , O or S,
  • G 8 is BR 13 , CR 13 R 14 , SiR 13 R 14 , NR 13 , PR 13 , O or S,
  • R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 independently of one another may have the meanings given above for the radicals R 3 to R 6 ,
  • R 7 R 8 , R 9 R 10 , R 11 R 12 and / or R 13 R 14 may together also be a doubly bonded oxygen atom or sulfur atom,
  • G 9 is BR 15 , CR 15 R 16 , SiR 15 R 16 , NR 15 , PR 15 , O or S,
  • G 10 is N or CR 17 ,
  • G 11 stands for N or CR 18 .
  • R 15 , R 16 , R 17 and R 18 may independently of one another have the meanings given above for the radicals R 3 to R 6 ,
  • G 12 is BR 19 , CR 19 R 20 , SiR 19 R 20 , NR 19 , PR 19 , O or S,
  • G 13 is BR 21 , CR 21 R 22 , SiR 21 R 22 , NR 21 , PR 21 , O or S,
  • G 14 is BR 23 , CR 23 R 24 , SiR 23 R 24 , NR 23 , PR 23 , O or S,
  • R 19 , R 20 , R 21 , R 22 , R 23 and R 24 may independently of one another have the meanings given above for the radicals R 3 to R 6 ,
  • R 19 R 20 , R 21 R 22 and / or R 23 R 24 may together also stand for a doubly bonded oxygen atom or sulfur atom, wherein two adjacent radicals R 19 , R 21 and R 23 may also be linked to fused aliphatic or aromatic rings,
  • G 15 is BR 25 , CR 25 R 26 , SiR 25 R 26 , NR 25 , PR 25 , O or S,
  • G 16 is BR 27 , CR 27 R 28 , SiR 27 R 28 , NR 27 , PR 27 , O or S,
  • G 17 is BR 29 , CR 29 R 30 , SiR 29 R 30 , NR 29 , PR 29 , O or S,
  • R 25 , R 26 , R 27 , R 28 , R 29 and R 30 independently of one another may have the meanings given above for the radicals R 3 to R 6 ,
  • R 25 R 26 , R 27 R 28 and / or R 29 R 30 can also together stand for a doubly bound oxygen atom or sulfur atom
  • R ' t R “, R'", R IV and R v are each independently hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, hetaryl, hydroxy, thiol, polyalkylene oxide, polyalkyleneimine, alkoxy, halogen, COOH, carboxylate, SO 3 H, sulfonate, NE 7 E 8 , alkylene-NE 7 E 8 , trifluoromethyl, nitro, alkoxycarbonyl, acyl or cyano, where E 7 and E 8 are each identical or different radicals selected from hydrogen, alkyl, cycloalkyl and aryl, wherein two adjacent radicals R 1 to R v together with the
  • Carbon atoms of the benzene nucleus, to which they are attached, can also be a fused ring system with 1, 2 or 3 further rings, and
  • the compounds of the formulas 1.1 to 1.3 used according to the invention are advantageously suitable for preventing or reducing damage to the skin by peroxides and / or hydroperoxides formed as a result of endogenous or exogenous factors. They are suitable both for the prevention and for the treatment of skin damage of individuals, preferably mammals, in particular humans, domestic animals or domestic animals.
  • the use can take place both in cosmetic products such as personal care products, decorative cosmetics, etc., which are generally not subject to prescription, as well as in dermatics, which are understood to be medicaments for the treatment of diseases of the skin (dermatoses).
  • Dermatics may additionally contain at least one further active ingredient which is preferably selected from antimycotics, antiseptics, antibiotics, sulfonamides, disinfectants, corticosteroids, shale oil and tar sulfonates, astringents, antihidrotic agents, acne, psoriasis, seborrhea and itching agents, keratolytics Etc.
  • at least one further active ingredient which is preferably selected from antimycotics, antiseptics, antibiotics, sulfonamides, disinfectants, corticosteroids, shale oil and tar sulfonates, astringents, antihidrotic agents, acne, psoriasis, seborrhea and itching agents, keratolytics Etc.
  • the treatment according to the invention of the diseased skin can be directed to individual disorders (abnormalities or pathological conditions), but it is also possible, if desired, to treat a plurality of possibly causally linked anomalies by an agent according to the invention which optionally contains an active ingredient combination.
  • Cosmetic and dermatological preparations based on compounds of general formulas 1.1 to 1.3, as described above, and / or salts thereof provide effective protection against oxidative processes, from processes caused by radiation or reactive compounds, from damage directly or indirectly caused by such processes be caused indirectly. They are advantageous for the treatment of cosmetic or dermatological changes to the skin and hair, such as. B. the Skin aging, loss of skin hydration, loss of skin elasticity, formation of wrinkles or wrinkles, or pigmentation or age spots.
  • the present invention relates to the use of compounds of the general formulas 1.1 to 1.3 and / or salts thereof, optionally in combination with at least one further active ingredient and in preparations containing such active ingredients, for the cosmetic and dermatological treatment or prevention of undesired changes in the appearance of the skin, such as acne or oily skin, keratoses, rosaceae and / or photosensitive, inflammatory, erythematous, allergic or autoimmune-reactive reactions, etc.
  • the compounds of formulas 1.1 to 1.3 for rejuvenation and / or revitalization of the skin.
  • energizing effects can also be observed.
  • the compounds of the formulas 1.1 to 1.3 have a positive effect on the function of the mitochondria.
  • improvements for example, the moisture value and / or the elasticity of the skin recorded.
  • the new synthesis of collagen and / or elastin is increased. This generally leads to a, at least partial, smoothing of wrinkles, the complexion looks radiant and fresher.
  • the positive effects mentioned also give rise to a positive subjective feeling of having altogether "youthful" skin.
  • Formulations based on compounds of the general formulas 1.1 to 1.3 are also advantageously suitable for the treatment, care and cleansing of the skin and can serve as make-up product in cosmetics. They preferably contain 0.001% by weight to 30% by weight of the active ingredient. The composition depends z. B. after the penetration properties of the active substance through the stratum corneum and their ability to form a depot in the skin.
  • the inventive use of compounds of formulas 1.1 to I.3, derivatives and / or salts thereof is advantageously carried out by regular application, for.
  • the period of time may extend over the lifetime of the user, preferably over a period of up to three months, more preferably over a week to two months, when the goal is to build a depot in the skin .
  • the application duration in the sense of the invention is considered to be a single application, but preferably a period of at least one day, more preferably over three days to three months, particularly preferably over one to two weeks.
  • Active ingredient amounts and proportions refer to the active ingredient, so that for salts and derivatives, a corresponding conversion has to be made.
  • dosage forms of compounds of formulas 1.1 to 1.3 and optionally additional active ingredients have advantageous penetration properties that allow rapid penetration of the substance into the skin.
  • rapid penetration is generally unimportant, but the ability to build a depot in the skin is beneficial.
  • an effective treatment but also prevention of prematurely aged skin eg wrinkles, age spots, telangiectasias, pigment disorders
  • radiation-related skin damage or radiation-related negative skin changes environmental (ozone, free radicals, singlet oxygen, reactive oxygen or nitrogen compounds, cigarette smoke, toxins)
  • Skin damage or environmental negative changes in the skin photosensitive, inflammatory, erythematous, allergic or autoimmune skin changes (especially acne, oily or dry skin, keratoses, rosaceae, dermatoses, atopic eczema, seborrheic Eczema, photodermatoses, polymorphic light dermatosis), deficient, sensitive or hypoactive states of the skin and / or the skin appendages, itching, dry skin conditions and hom Wegbarrier disorders and / or hair loss and reduced hair growth m öglich.
  • the use according to the invention of compounds of the formulas 1.1 to 1.3 in cosmetic and dermatological preparations also serves to calm sensitive and irritated skin in a surprising and unpredictable manner, regulation of collagen, hyaluronic acid, elastin synthesis, stimulation of DNA synthesis, especially in the case of deficient or hypoactive skin conditions, regulation of transcription and translation of matrix-degrading enzymes, in particular of the matrix metalloproteinases, increase in cell renewal and regeneration of the skin, enhancement of the skin's own protective and repair mechanisms for DNA, lipids and / or proteins and for pre- and post-treatment in surgical Interventions, in particular to counteract skin irritation and to promote the regeneration processes of the injured skin.
  • the cosmetic and dermatological preparations are applied to the skin in a sufficient amount in the manner customary for cosmetics.
  • the compounds according to the invention of the formulas 1.1 to 1.3 or salts thereof in cosmetic cleansing compositions such as bar soaps, toilet soaps, core soaps, transparent soaps, luxury soaps, de-soaps, cream soaps, baby soaps, skin soaps, abrasive soaps, syndets, liquid soaps, pasty soaps, Soft soaps, washing pastes, liquid washing, shower and bath preparations z.
  • cosmetic cleansing compositions such as bar soaps, toilet soaps, core soaps, transparent soaps, luxury soaps, de-soaps, cream soaps, baby soaps, skin soaps, abrasive soaps, syndets, liquid soaps, pasty soaps, Soft soaps, washing pastes, liquid washing, shower and bath preparations z.
  • skin cosmetic preparations such as W / O and O / W skin and body creams, day and night creams, eye creams, sunscreens, after sun products, hand care products, face creams, multiple emulsions, jellies, microemulsions, liposome preparations, nosome preparations, Anti-wrinkle creams, facial oils, lipogels, sports gels, moisturizing creams, bleaching creams, vitamin creams, skin lotions, body lotions, ampoules, after shave lotions, pre-shaves, moisturizing lotions, tanning lotions, cellulite creams, depigmenting agents, massage preparations, body powders, toners, face masks, deodorants, antiperspirants, Nose strips, anti-acne, repellent, shaving, hair removal, personal care, foot care, baby care and others.
  • skin cosmetic preparations such as W / O and O / W skin and body creams, day and night creams, eye creams, sunscreens, after sun products, hand
  • the compounds of formulas 1.1 to 1.3 can be used in hair care cosmetics such as hair conditioners, hair lotions, hair conditioners, hair emulsions, top fluids, perms leveling agents, hot oil treatment preparations, conditioners, setting lotions, shampoos, hair coloring and dyes, hair sprays, hair lotions, conditioners, shine sprays, hair brilliantines, hair styling products, hair lotions, allergy treatments and others.
  • hair care cosmetics such as hair conditioners, hair lotions, hair conditioners, hair emulsions, top fluids, perms leveling agents, hot oil treatment preparations, conditioners, setting lotions, shampoos, hair coloring and dyes, hair sprays, hair lotions, conditioners, shine sprays, hair brilliantines, hair styling products, hair lotions, allergy treatments and others.
  • the compounds of the formulas 1.1 to 1.3 are also suitable for use in cosmetic preparations for decorative cosmetics, for example as make-up, powder, blush, eye shadow, kohl pencils, eyeliner, eyefoundation cream, lipsticks, eyebrow pencils, contour pencil, masking sticks, theatrical make-up, mascara , Eyelash tinting, coloring, make-up removal products and others.
  • the cosmetic, hygienic, dermatological or pharmaceutical preparations can be prepared as a spray (pump spray or aerosol), foam, gel, gel spray, lotion, cream, mousse, ointment, suspensions or powder, depending on the field of application.
  • the preparations may contain cosmetic adjuvants such as are commonly used in such preparations, eg.
  • bactericides As preservatives, bactericides, perfumes, substances for preventing foaming, dyes, pigments, thickeners, surface-active substances, emulsifiers, softening agents, lubricants, fats, oils, waxes or other conventional ingredients of a cosmetic or dermatological formulation such as alcohols, polyols , Polymers, foam stabilizers, solubilizers, electrolytes, organic acids, organic solvents or silicone derivatives.
  • the preparations may contain, in addition to the active substances mentioned, further compounds which act as antioxidants, as free-radical scavengers, skin moisturizing or moisturizing, anti-erythematous, anti-inflammatory or anti-allergic, in order to supplement or enhance their action.
  • these compounds can be selected from the group of vitamins, plant extracts, ⁇ - and ⁇ -hydroxy acids, ceramides, anti-inflammatory, antimicrobial or UV-filtering substances, and their derivatives and mixtures thereof.
  • the cosmetic or dermatological preparations generally contain, based on the finished preparations, 0.0005 to 5 wt .-%, preferably 0.001 to 1 wt .-% of at least one peroxide and / or Hydroperoxidzersetzers of the general formulas 1.1 to 1.3 as before described.
  • the peroxide decomposers used according to the invention are used in combination with at least one antioxidant which acts as a radical scavenger.
  • the cosmetic or dermatological preparations then generally contain, based on the finished preparations, 0.0005 to 5 wt .-%, preferably 0.001 to 1 wt .-%, of at least one effective as a radical scavenger antioxidant.
  • the additional antioxidants are usually compounds known per se.
  • the antioxidants are advantageously selected from the groups of carotenoids, carotenes (for example ⁇ -carotene, ⁇ -carotene, lycopene) and derivatives thereof, chlorogenic acid and derivatives thereof, lipoic acid and derivatives thereof (eg dihydrolipoic acid), Metal) chelators, EDTA, EGTA and their derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (eg ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (eg vitamin A). E-acetate), vitamin A and derivatives (vitamin A palmitate), butylhydroxytoluene, butylated hydroxyanisole, and other antioxidants commonly used in cosmetic preparations.
  • At least one compound of the general formulas 1.1 to 1.3, as defined above, is used in combination with at least one tocopherol or tocopherol derivative.
  • the peroxide decomposers used for the combination are preferably selected from the compounds of the formulas (1) to (28).
  • Special versions are combinations of the compounds (1), (3), (4), (5), (6), (21), (27) and (28) with at least one tocopherol or tocopherol derivative, especially with ⁇ -tocopherol (vitamin E).
  • Suitable tocopherols are generally 2-position with a 4,8,12-trimethyltridecyl substituted chroman-6-ols and derivatives thereof. Suitable derivatives are, for.
  • esters with saturated and unsaturated optionally substituted mono- and polycarboxylic acids, such as formic acid, acetic acid, propionic acid, butyric acid, oxalic acid, malonic acid, succinic acid, nicotinic acid, etc. These include, in particular, the acetates, succinates and nicotinates, especially the acetates.
  • Preferred tocopherols are ⁇ -, ⁇ -, ⁇ -, ⁇ - and ⁇ -tocopherols and their derivatives. Particularly preferred is the ⁇ -tocopherol, which is often equated with the vitamin E, whose main component and most effective ingredient it is, and ⁇ -tocopherol acetate.
  • the cosmetic and dermatological preparations generally contain, based on the finished preparations, from 0.00005 to 5% by weight, preferably from 0.0001 to 1% by weight, in particular from 0.0001 to 0.1% by weight. %, at least one tocopherol or tocopherol derivative.
  • the preparations preferably also contain substances which absorb UV radiation in the UV-B and / or UV-A range. Suitable UV filters are z. B.
  • 2,4,6-triaryl-1,3,5-triazines in which the aryl groups can each carry at least one substituent, which is preferably selected from hydroxy, alkoxy, especially methoxy, alkoxycarbonyl, especially methoxycarbonyl and ethoxycarbonyl, and mixtures from that.
  • substituents which is preferably selected from hydroxy, alkoxy, especially methoxy, alkoxycarbonyl, especially methoxycarbonyl and ethoxycarbonyl, and mixtures from that.
  • 4-aminobenzoic acid esters where the amino group may optionally be alkylated or alkoxylated. This includes z. N, N-dimethyl-4-aminobenzoic acid isooctyl ester.
  • cinnamic acid esters such as benzophenones, camphor derivatives and UV-radiation-inhibiting pigments, such as titanium dioxide, talc and zinc oxide.
  • 2-hydroxybenzoic acid esters such as. B. the isooctyl ester.
  • Other suitable UV filters are 2,4,6-trianilin (o-carbo-2'-ethylhexyl-1 I -oxy) -1, 3,5-triazine, 3-imidazol-4-yl-acrylic acid and their ethyl ester , Methyl o-aminobenzoate, glyceryl p-aminobenzoate, 2,2'-dihydroxy-4-methoxybenzophenone (dioxybenzone),
  • UV filter substances in parenthesis is the respective
  • the preparations may also contain inorganic pigments based on metal oxides and / or other water-insoluble or insoluble metal compounds selected from the group consisting of the oxides of zinc (ZnO), titanium (TiO 2 ), iron (eg. Fe 2 O 3 ), zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (eg MnO 2 ), aluminum (Al 2 O 3 ), cerium (eg Ce 2 O 3 ), mixed oxides of corresponding metals and mixtures of such oxides.
  • inorganic pigments based on metal oxides and / or other water-insoluble or insoluble metal compounds selected from the group consisting of the oxides of zinc (ZnO), titanium (TiO 2 ), iron (eg. Fe 2 O 3 ), zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (eg MnO 2 ), aluminum (Al 2 O 3 ), cerium (eg Ce 2 O 3 ), mixed oxides of corresponding
  • the inorganic pigments may be present in gecoater form, d. they are superficially treated. This surface treatment may be, for example, that the pigments are provided in a conventional manner, as described in DE-A-33 14742, with a thin hydrophobic layer.
  • UV filters which can be used in combination with the active compound combinations according to the invention, is of course not intended to be limiting.
  • the total amount of the filter substances is generally from 0.1% by weight to 30% by weight, preferably from 0.5 to 15% by weight, in particular from 1 to 10% by weight, based on the total weight of the preparations To provide cosmetic preparations that protect the skin from the entire range of ultraviolet radiation.
  • a lipid phase is preferably selected from mineral oils, mineral waxes, branched and / or unbranched hydrocarbons and waxes, triglycerides of saturated and / or unsaturated, branched and / or unbranched C 8 -C 24 -alkanecarboxylic acids; synthetic, semi-synthetic or natural oils such as olive oil, palm oil, almond oil or mixtures; oiling, greasing or waxing; Esters of saturated and / or unsaturated, branched and / or unbranched C 3 -C 30 -alkanecarboxylic acids and saturated and / or unsaturated, branched and / or unbranched C 3 -C 30 -alcohols, esters of aromatic carboxylic acids and saturated and / or unsaturated , branched and / or unbranched
  • C 3 -C 3 o-alcohols for example isopropyl myristate, isopropyl stearate, hexyldecyl stearate, oleyl oleate; synthetic, semi-synthetic and natural mixtures of the aforementioned esters, such as jojoba oil, alkyl benzoates or silicone oils such.
  • An aqueous phase used where appropriate, additionally contains a water-miscible solvent, such as Ci-C 10 -, preferably C 1 -C 5 -alcohols, diols or polyols, and ethers thereof, preferably ethanol, isopropanol, propylene glycol, glycolic cerin, ethylene glycol monoethyl ether etc.
  • a water-miscible solvent such as Ci-C 10 -, preferably C 1 -C 5 -alcohols, diols or polyols, and ethers thereof, preferably ethanol, isopropanol, propylene glycol, glycolic cerin, ethylene glycol monoethyl ether etc.
  • Suitable emulsifiers are preferably known W / O and O / W emulsifiers such as polyglycerol esters, Sobitanester or partially esterified glycerides into consideration.
  • Particularly suitable solubilizers are, in particular, ethoxylated sorbitan esters, ethoxylated lanolin alcohols and ethoxylated castor oil.
  • Common native and synthetic thickeners or gel formers in the formulations are crosslinked polyacrylic acids and their derivatives, polysaccharides such as xanthan gum or alginates, carboxymethylcellulose or hydroxycarboxymethylcellulose, hydrocolloids such as gum arabic or montmorillonite minerals such as bentonites or fatty alcohols, polyvinyl alcohol and polyvinylpyrrolidone.
  • Suitable propellants for aerosols are the customary propellants, for example propane, butane, pentane, dimethyl ether and others.
  • Another object of the invention is a cosmetic or pharmaceutical agent for treating the skin to prevent or reduce damage to the skin by peroxides and / or hydroperoxides formed as a result of endogenous or exogenous factors, comprising:
  • the agents according to the invention are in particular not deodorants, antiperspirants, agents for inhibiting or reducing pigment production, agents for the treatment of fibrotic disorders and hair growth promoting agents.
  • the agents preferably contain component I) in an amount of 0.001 to 30% by weight, in particular 0.01 to 25% by weight, based on the total weight of the composition.
  • agents containing at least one tocopherol or tocopherol derivative as defined above are agents containing at least one tocopherol or tocopherol derivative as defined above.
  • the formulation base of pharmaceutical formulations according to the invention preferably contains pharmaceutically acceptable excipients.
  • Pharmaceutically acceptable excipients known to be useful in the pharmaceutical, food technology and related fields, in particular those listed in relevant pharmacopoeias (eg DAB Ph. Eur. BP NF) and other excipients whose properties do not preclude physiological application.
  • Suitable auxiliaries may be: lubricants, wetting agents, emulsifying and suspending agents, preserving agents, antioxidants, anti-irritants, chelating agents, emulsion stabilizers, film formers, gelling agents, odor masking agents, resins, hydrocolloids, solvents, solubilizers, neutralizing agents, permeation accelerators, pigments, quaternary ammonium compounds, Refatting and superfatting agents, ointment, cream or oil bases, silicone derivatives, stabilizers, sterilants, blowing agents, drying agents, opacifiers, thickeners, waxes, softeners, white oils.
  • An embodiment in this respect is based on expert knowledge, as shown for example in Fiedler, HP Lexicon of excipients for pharmacy, cosmetics and related fields, 4th ed., Aulendorf: ECV Editio-Kantor-Verlag, 1996.
  • suitable dermatological formulations are ointments, creams, hydrogels, pastes or patches, as well as liquid dosage forms, such as solutions, emulsions, in particular oil-in-water emulsions, suspensions, for example lotions, etc. If desired, liposomes or Microspheres are used.
  • the formulations are administered according to the invention transdermally (topically).
  • the active ingredients may be mixed or diluted with a suitable excipient (excipient).
  • excipients may be solid, semi-solid or liquid materials which may serve as a vehicle, carrier or medium for the active ingredient. If desired, the admixing of further auxiliaries takes place in the manner known to the person skilled in the art.
  • active ingredient components can be formulated together. However, they can also first be processed separately and then combined in a suitable dosage form.
  • Another object of the present invention are means in the form of a commercial pack with at least one agent based on
  • the cosmetic and dermatological agents are preferably in the form of emulsions, in particular as water-in-oil (W / O) or oil-in-water (O / W) emulsions.
  • formulations for example, gels, oils, oleogels, multiple emulsions, for example in the form of W / O / W or ONSIIO emulsions, anhydrous ointments or ointment bases, etc.
  • emulsifier-free formulations such as hydrodispersions , Hydrogels or a Pickering emulsion are advantageous embodiments.
  • Emulsions are prepared by known methods.
  • the emulsions contain, in addition to at least one peroxide decomposer 1.1-1.3, as a rule, customary constituents, such as fatty alcohols, fatty acid esters and especially fatty acid triglycerides, fatty acids, lanolin and derivatives thereof, natural or synthetic oils or waxes and emulsifiers in the presence of water.
  • customary constituents such as fatty alcohols, fatty acid esters and especially fatty acid triglycerides, fatty acids, lanolin and derivatives thereof, natural or synthetic oils or waxes and emulsifiers in the presence of water.
  • a skin cream, etc. generally contains an aqueous phase which is emulsified by means of a suitable emulsifier in an oil or fat phase.
  • a polyelectrolyte complex can be used.
  • the measure of the protective effect of a test compound is the factor QS, which is a measure of how strongly a stabilizer reduces the degradation rate.
  • QS x degradation rate / degradation rate x
  • Desmocosmetic preparations according to the invention are described below containing peroxide decomposers according to compounds 1.1-1.3, by way of example compounds which are mentioned in Table 1.
  • Example 11 Use of peroxide decomposers in a protective day cream - Type O / W WS 1%:
  • Preparation Heat phases A and B separately from each other to about 80 ° C. Stir phase B into phase A and homogenize. Incorporate phase C into the combined phases A and B and homogenize. Cool to about 40 ° C. while stirring. Add phase D, adjust the pH to about 6.5 with phase E and homogenize. Cool to room temperature while stirring.
  • Example 12 Use of peroxide decomposers in a facial cleansing lotion - Type O / W WS 1%:
  • Example 13 Use of peroxide decomposers in a Daily Care Body Spray
  • Example 14 Use of peroxide decomposers in a skin care gel WS 1%:% Ingredient (INCI)
  • Example 15 Use of peroxide decomposers in an aftershave lotion
  • Preparation Mix the components of phase A. Dissolve phase B, work in phase A and homogenize.
  • Example 16 Use of peroxide decomposers in an After Sun Lotion WS 1%:
  • Preparation Mix the components of phase A. Stir phase B into phase A while homogenizing. Neutralize with Phase C and homogenize again.
  • Example 17 Use of peroxide decomposers in a sunscreen lotion WS 1%:
  • Preparation Heat the components of phases A and B separately to about 80 ° C. Stir phase B into phase A and homogenize. Heat phase C to about 80 ° C. and stir into the combined phases A and B while homogenizing. Cool to about 40 ° C. while stirring, add phase D and homogenize again.
  • Example 18 Use of peroxide decomposers in a sunscreen lotion - Type O / W WS 1%:
  • Example 20 Use of peroxide decomposers in a foot balm
  • Preparation Heat the components of phases A and B separately to about 80 ° C. Stir phase B into phase A while homogenizing. Cool with stirring to about 40 0 C, add the phases C and D and briefly nachhomogene. Cool to room temperature while stirring.
  • Example 21 Use of peroxide decomposers in a W / O emulsion with bisabolol
  • Desmocosmetic preparations according to the invention are described below containing peroxide decomposer according to compound 1.1-1.3, by way of example compounds which are mentioned in table 1.
  • the said compound are referred to below as Peroxidzersetzer and the amount used is given in weight percent.
  • cosmetic sunscreen preparations comprising a combination of at least one inorganic pigment, preferably zinc oxide and / or titanium dioxide, and organic UV-A and UV-B filters.
  • the content of Peroxidzersetzer according to compound 1.1 to 1.3 refers to 100% active ingredient.
  • the active compounds according to the invention can be used both in pure form and as an aqueous solution. In the case of the aqueous solution, the content of water must be the. be adapted in the respective formulation.

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Abstract

La présente invention concerne l'utilisation de composés présentant des structures déterminées contenant des atomes de soufre et éventuellement d'azote comme décomposeurs de peroxydes dans des produits cosmétiques et pharmaceutiques pour le soin de la peau. L'invention concerne en outre des produits cosmétiques et pharmaceutiques contenant des composés présentant de telles structures.
EP06742899A 2005-05-13 2006-05-12 Utilisation de decomposeurs de peroxydes dans des produits cosmetiques et pharmaceutiques pour le soin de la peau Withdrawn EP1881817A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005022292A DE102005022292A1 (de) 2005-05-13 2005-05-13 Verwendung von Peroxidzersetzern in kosmetischen und pharmazeutischen Mitteln zur Behandlung der Haut
PCT/EP2006/004487 WO2006122721A2 (fr) 2005-05-13 2006-05-12 Utilisation de decomposeurs de peroxydes dans des produits cosmetiques et pharmaceutiques pour le soin de la peau

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EP1881817A2 true EP1881817A2 (fr) 2008-01-30

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US (1) US20080193397A1 (fr)
EP (1) EP1881817A2 (fr)
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DE102008041918A1 (de) * 2008-09-09 2010-03-11 Evonik Degussa Gmbh Silanolkondensationskatalysatoren zur Vernetzung von gefüllten und ungefüllten Polymer-Compounds
JP6022323B2 (ja) * 2012-11-30 2016-11-09 株式会社伊勢半 水中油型日焼け止め化粧料
DE102013213170A1 (de) 2013-07-04 2015-01-08 Beiersdorf Ag Octocrylenfreies, geruchsstabiles Sonnenschutzmittel
FR3118877B1 (fr) * 2021-01-18 2023-11-17 Oreal Stabilisation d’un composé de thiopyridinone et réduction du jaunissement de la composition le comprenant
US20240082132A1 (en) * 2020-12-22 2024-03-14 L'oreal Stabilization of thiopyridinone compound and yellowing reduction of composition comprising same

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EP0483426A1 (fr) * 1990-11-01 1992-05-06 The Procter & Gamble Company Composition et méthode de désodorisation à base d'un composé hétérocyclique contenant un groupement thiol
JPH05124924A (ja) * 1991-04-09 1993-05-21 Sansho Seiyaku Co Ltd メラニン生成抑制外用剤
JP3197602B2 (ja) * 1992-02-17 2001-08-13 久光製薬株式会社 チアゾール類縁化合物及び皮膚外用剤
US5472698A (en) * 1994-12-20 1995-12-05 Elizabeth Arden Co., Division Of Conopco, Inc. Composition for enhancing lipid production in skin
CA2401336C (fr) * 2000-02-29 2014-12-23 Integriderm, Inc. Inhibiteurs de tyrosinase du melanocyte en tant qu'eclaircissants topiques de la peau
DE10036655A1 (de) * 2000-07-26 2002-02-07 Basf Ag Kosmetische oder dermatologische Zubereitungen zur Vermeidung von Hautschädigungen durch Peroxide

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