WO2008025755A1 - utilisation d'hÉTÉrocycles contenant de l'azote dans les cosmÉtiques dermatologiques - Google Patents

utilisation d'hÉTÉrocycles contenant de l'azote dans les cosmÉtiques dermatologiques Download PDF

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WO2008025755A1
WO2008025755A1 PCT/EP2007/058904 EP2007058904W WO2008025755A1 WO 2008025755 A1 WO2008025755 A1 WO 2008025755A1 EP 2007058904 W EP2007058904 W EP 2007058904W WO 2008025755 A1 WO2008025755 A1 WO 2008025755A1
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alkyl
formula
dermocosmetics
skin
test substance
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PCT/EP2007/058904
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German (de)
English (en)
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Gerhard Wagenblast
Sylke Haremza
Arne Ptock
Frank HÖFER
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Basf Se
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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
    • A61K8/49—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
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning 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
    • A61Q19/002—Aftershave 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
    • A61Q19/004—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
    • A61Q19/04—Preparations for care of the skin for chemically tanning 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
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to dermocosmetic compositions containing N-containing heterocycles, preferably pyridine / pyrimidine and / or pyridinol / pyrimidinol compound according to the general formula 1.
  • the invention further relates to the use of these compounds in dermokosmetischen preparations and the use of dermocosmetics according to the invention for reducing or Avoidance of radicle-induced skin or hair damage.
  • Another subject of the invention relates to the use of the compounds according to the invention for increasing the shelf life of the dermocosmetic preparations or for stabilizing the oxidation-sensitive ingredients contained in the said preparations. Further embodiments of the present invention can be taken from the claims, the description and the examples. It is understood that the features mentioned above and those yet to be explained of the subject matter according to the invention can be used not only in the particular combination specified, but also in other combinations, without departing from the scope of the invention.
  • Skin aging is today understood as the result of the interaction of chronological (intrinsic) skin aging and exogenous factors of conditioned (extrinsic) skin aging. It is assumed that intrinsic skin aging is the result of genetic processes.
  • Extrinsic skin aging is influenced by exogenous influences, in particular UV radiation (photoaging).
  • UV radiation photoaging
  • ROS reactive oxygen species
  • e.g. Peroxide radicals reactive oxygen species
  • These extremely reactive substances lead to the oxidation of various cell components such as DNA, proteins and membrane lipids.
  • free radicals damage the collagen and elastin and affect the fatty substances.
  • the skin loses its tone and elasticity and the age-spot pigment lipofuscin develops.
  • the free radicals are formed under the influence of numerous factors: pollution, excessive sun exposure, smoking, alcohol and fat consumption.
  • the exposure of the skin to sunlight is responsible for the premature aging of exposed skin areas.
  • the human skin shows a high sensitivity in the short-wave radiation range (UV-B) with wavelengths of 290-320 nm.
  • UV-B short-wave radiation range
  • the named harmful effects cause damage to the cells of the skin itself.
  • the skin's ability to regenerate is reduced.
  • the consequences of aging are thinning of the skin, weaker interlocking of the epidermis and dermis, reduction of the number of cells and the supply of the blood vessels.
  • the same factors also affect hair, where it can also cause damage.
  • the hair becomes brittle, less elastic and lackluster.
  • the surface structure of the hair is damaged.
  • the skin has a variety of its own protective mechanisms.
  • these protective mechanisms are not sufficient to completely prevent oxidative processes and the associated aging processes or damage to the skin (see also "Skin Diseases Associated with Oxidative Damage” in "Oxidative Stress in dermatology", p. 323 et seq., Marcel Decker ine , New York, Basel, Hong Kong, publisher: Jürgen Fuchs, Frankfurt and Lester Packer, Berkeley, California).
  • antioxidant compounds are used in dermocosmetic or cosmetic preparations for the protection and care of skin and hair. In addition, they can also be used as protection against the spoilage of oxidation-sensitive substances.
  • Cosmetic or dermocosmetic care products with properties which counteract the described or comparable processes or whose harmful consequences should be reduced or reversed are often distinguished by the following properties: radical-catching, antioxidant, anti-inflammatory or moisturizing tend. Among other things, they prevent or reduce the activity of the matrix-degrading enzymes or regulate the new synthesis of collagen, elastin or proteoglycans.
  • radical scavengers are added to the dermocosmetic preparations (for example, DE 19739349).
  • said preparations are radical scavengers for oxygen radicals added vitamins E (tocopherols) and C (ascorbic acid).
  • WO 2005/042828 describes the use of various hindered nitroxyl, hydroxylamine and hydroxylamine salts in combination with organic UV filters for the stabilization of personal care products. So far, the actual effect of inactivating radicals by the described substances or enzymatic systems lags behind the hoped-for effects.
  • N-containing heterocycles according to formula 1 and their preparation have long been known from the literature and can also be purchased in part. Examples which may be mentioned are the patents DE 271 1656 (preparation of pyridinols) and US Pat. No. 5,189,166, as well as the publications Acta Chem. Scand. 1987 (37) 127 and 907 and J. Heterocycl. Chem. 1985 (22) 1281 and Tetrahedron 1983, 39 (18), p. 2869
  • Decorative cosmetics means cosmetic aids which are not used primarily for care purposes but to beautify or improve the appearance of skin or hair. These aids are known to the person skilled in the art and include, for example, kohl pencils, mascara, eye shadows, tinted day creams, powders, concealers, Rouge, lipsticks, lip pencils, make-up, nail polish, glamor gel etc.
  • Dermatacosmetics or “dermocosmetic agents” or “dermocosmetic preparations” are agents or preparations (i) for protection against damage to the skin, nails or hair, (ii) for the treatment of skin, nail or hair damage which has already occurred.
  • iii) for the care of the skin, nails or hair comprising skin-cosmetic, nail-cosmetic, hair-cosmetic, dermatological, hygienic or pharmaceutical agents, preparations, formulations and decorative cosmetics Further comprises skin care compositions in which the pharmaceutical dermatological application is achieved taking into account cosmetic aspects
  • Such agents or preparations are used for the support, prevention and treatment of skin diseases and have a biological effect in addition to the cosmetic effect.
  • Dermateutics as defined above contain suitable adjuvants and additives in a cosmetically acceptable medium to the person skilled in the art and from manuals of cosmetics, for example Schrader, bases and formulations of cosmetics, Weghig Verlag, Heidelberg, 1989, ISBN 3-7785-1491-1, or Umbach, cosmetics: development, production and application of ksometischer means, 2nd extended edition, 1995, Georg Thieme Verlag, ISBN 3 13 712602 9, can be removed.
  • “Democosmetic active ingredients” in the context of the present invention are cosmetically compatible substances, for example selected from the group of natural or synthetic polymers, pigments, humectants, oils, waxes, enzymes, minerals, vitamins, sunscreens, dyes, fragrances, antioxidants and preservatives. and pharmaceutical active ingredients which are used for the support, prevention and treatment of skin diseases and have a healing, damage preventive, regenerating or improving the general condition of the skin biological effect.
  • Cosmetically acceptable medium is to be understood broadly and means substances suitable for the preparation of cosmetic or dermocosmetic preparations and mixtures thereof.
  • Cosmetically-compatible substances do not cause irritation or damage on contact with human or animal dermal tissue or hair and are incompatible with other substances, and have low allergenic potential and are approved by the state regulatory authorities for use in cosmetic preparations These substances are familiar to the person skilled in the art and can be found, for example, in the handbooks of cosmetics, for example Schrader, bases and formulations of cosmetics, Weghig Verlag, Heidelberg, 1989, ISBN 3-7785-1491-1.
  • Stabilization in connection with light- and / or oxidation-sensitive cosmetic constituents or dermocosmetic active ingredients means increased shelf-life compared to non-inventive dermocosmetics-otherwise identical composition and equal exposure to light or free radicals, ie prolonged usability of dermocosmetic agents ,
  • Avoidance or "prevention” in connection with radical-induced damage to the skin and hair is the prophylactic prevention of said damage. Avoidance is not necessarily to be understood as 100% avoidance, but I can vary its efficiency depending on the selected preparations, the other ingredients, the concentrations present and the degree of exposure.
  • the present invention relates to dermocosmetics containing at least one compound according to the general formula 1
  • X is nitrogen or CR 5 ;
  • R 1 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl,
  • R 2 is OR 6 , SR 7 , NR 8 R 9 or PR 8 R 9 ;
  • R 3 is hydrogen, OR 10 , SR 11 , NR 12 R 13 , PR 12 R 13 , alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, COOH, COOM, cycloalkylcarbonyl, arylcarbonyl, aminocarbonyl, alkylaminocarbonyl , Dialkylaminocarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkynylcarbonyl or alkynyloxycarbonyl;
  • R 4 is hydrogen, alkyl, cycloalkyl or aryl
  • R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl or
  • R 1 with R 5 may also together represent a divalent bridging group having 1 to 6 atoms between the flanking bonds;
  • R 4 with R 5 may also together be a divalent bridging group having 1 to 6 atoms between the flanking bonds;
  • R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 each independently represent hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl or aryl; or;
  • R 6 with R 1 or R 7 with R 1 may also together represent a divalent bridging group having 1 to 6 atoms between the flanking bonds;
  • R 6 , R 7 or R 8 with R 1 or R 6 , R 7 or R 8 with R 3 may also together represent a divalent bridging group having 1 to 6 atoms between the flanking bonds;
  • R 8 , R 9 , R 12 , R 13 each independently represent hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl or aryl; or R 8 and R 9 and / or R 11 and R 12 together with the heteroatom to which they are attached can form a heterocyclic ring bonded via the heteroatom; and
  • M is a cation equivalent
  • alkyl includes straight-chain or branched hydrocarbon radicals having 1 to 50 carbon atoms (C 1 -C 50 -alkyl).
  • Pentyl 2-methylbutyl, 3-methylbutyl, 1, 2-dimethylpropyl, 1, 1-dimethylpropyl, 2,2-
  • 2-ethylpentyl 1-propylbutyl, n-octyl, 2-ethylhexyl, 2-propylheptyl, 1,1,3,3-tetramethylbutyl, nonyl, decyl, n-undecyl, n-dodecyl, n-tridecyl, iso- Tridecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and n-eicosyl.
  • alkyl also includes alkyl radicals whose carbon chain is replaced by one or more, for. B. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, non-adjacent groups selected from -O-, -S-, -NR 14 - (wherein R 14 is hydrogen or Ci -Cio-alkyl), -CO- and / or -SO 2 - may be interrupted, ie the termini of the alkyl group are formed by carbon atoms.
  • alkyl also includes substituted alkyl groups which generally have 1, 2, 3, 4, 5, 6, 7 or 8, preferably 1, 2, 3 or 4, and more preferably 1 or 2 substituents Substituents on alkyl are hydroxyl, COOH, COOM, halogen, alkoxycarbonyl, cycloalkyl, aryl, heteroaryl, heterocyclyl and NR 15 R 16 , wherein R 15 and R 16 independently of one another represent hydrogen, cycloalkyl, aryl, heteroaryl or heterocyclyl.
  • alkoxy represents a straight-chain or branched alkyl group having generally 1 to 30 carbon atoms which is bonded via the oxygen atom (-O-), for example C 1 -C 10 -alkoxy, for example methoxy, ethoxy or propoxy.
  • cycloalkyl in the context of the present invention comprises an unsubstituted or substituted monocyclic or bicyclic saturated hydrocarbon group having generally 3 to 6, 8, 10, 12 or 15 carbon ring members, such as C 3 -C 5 -cycloalkyl, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, loheptyl Cyc-, cyclooctyl, or C 7 -C 2 bicycloalkyl.
  • the cycloalkyl group may carry one or more, for example one, two, three, four or five substituents. Suitable substituents include alkyl, alkylcarbonyl, alkoxycarbonyl, hydroxy, alkoxy, NR 12 R 13 and halogen.
  • alkenyl in the context of the present invention comprises straight-chain and branched hydrocarbon radicals having generally 2 to 4, 6, 8, 10, 12 or 20
  • Carbon atoms which, depending on the chain length one or more, for. B.
  • C 2 -C 20 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3
  • alkenyl also includes substituted alkenyl groups which are e.g.
  • alkynyl in the context of the present invention comprises straight-chain and branched hydrocarbon radicals having generally 2 to 4, 6, 8, 10, 12 or 20 carbon atoms which, depending on the chain length, have one or more, e.g. B. 2, 3 or 4, can carry triple bonds in any position, for. C 2 -C 20 alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, pentynyl, hexynyl, octynyl.
  • alkynyl also includes substituted alkynyl groups which are e.g. B. 1, 2, 3, 4 or 5 substituents can carry.
  • suitable Substituents are for. Cycloalkyl, heterocycloalkyl, aryl, heteroaryl, hydroxy, alkoxy, nitro, cyano, halogen, NR 12 R 13 .
  • aryl in the context of the present invention comprises a mono-, di- or trinuclear aromatic ring system containing 6 to 14 carbon ring members, which may be unsubstituted or substituted, for. Phenyl, naphthyl and anthracenyl. Preference is given to a mono- or binuclear ring system such as phenyl or naphthyl, more preferably a mononuclear aromatic ring system, phenyl.
  • the aryl group may generally carry 1, 2, 3, 4 or 5, preferably 1, 2 or 3, substituents.
  • Suitable substituents include alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, halogen, NR 12 R 13 , hydroxy, cyano, nitro, COOH, COOM.
  • substituted aryl examples include 2-, 3- and 4-methylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2-, 3- and 4-ethylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diethylphenyl, 2,4,6-triethylphenyl, 2-, 3- and 4-propylphenyl, 2,4-, 2, 5-, 3,5- and 2,6-di-n-propylphenyl, 2,4,6-tri-n-propylphenyl, 2-, 3- and 4-isopropylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diisopropylphenyl, 2,4,6-triisopropylphenyl, 2-, 3- and 4-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6- Dibutylphenyl, 2,4,6-tributylphenyl, 2-, 3- and 4-iso
  • aryloxy stands for an aryl group as mentioned above which is bonded via the oxygen atom (-O-), for example phenyloxy, 1-naphthyloxy or 2-naphthyloxy.
  • heterocycloalkyl in the context of the present invention comprises non-aromatic, unsaturated or fully saturated cycloaliphatic groups having generally 4 to 12 ring atoms, preferably 5 or 9 ring atoms, in which 1, 2 or 3 of the ring carbon atoms are selected from hetero atoms selected from the elements Oxygen, nitrogen and sulfur are replaced.
  • Heterocycloalkyl may be unsubstituted or substituted, wherein in the case of a substitution, these heterocyclic groups generally carry 1, 2 or 3, preferably 1 or 2, particularly preferably one substituent.
  • Suitable substituents include alkyl, alkoxy, aryl, alkoxycarbonyl, COOH, COOM, hydroxyl, halogen, NR 12 R 13 .
  • Exemplary of heterocycloaliphatic groups are pyrrolidinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, imidazoli- dinyl, pyrazolidinyl, oxazolidinyl, morpholidinyl, thiazolidinyl, isothiazolidinyl, isoxazolidinyl, piperazinyl, tetrahydrothiophenyl, dihydro-2-yl, tetrahydrofuranyl, dihydrofuran-2-yl, tetrahydropyranyl, 1, 2-oxazolin-5-yl, 1 , 3-oxazolin-2-yl and dioxanyl.
  • heteroaryl in the context of the present invention comprises aromatic ring systems containing in general 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14 ring atoms, which in addition to carbon atoms 1, 2, 3 or 4
  • heteroaryl include furyl, thiophenyl, pyridiyl, quinolinyl, acridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, indolyl, purinyl, indazolinyl, benzotriazolyl , 1, 2,3-triazolyl, 1, 3,4-triazolyl and carbazoyl
  • heteroaryl generally has 1, 2 or 3 substituents, preferably alkyl, alkoxy, Hydroxyl, COOH, COOM, and NR 12 R 13 are selected.
  • aminocarbonyl denotes an amino group which is bonded via the carbonyl group (-C (O) -).
  • alkoxycarbonyl denotes an alkoxy group as mentioned above which is bonded via the carbonyl group (-C (O) -), for example methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, sec-butoxy- carbonyl, isobutoxycarbonyl, tert-butoxycarbonyl and the like.
  • cycloalkylcarbonyl means a mono- or bicyclic hydrocarbon group having 3 to 15 carbon ring members as mentioned above, which is bonded via the carbonyl group (-C (O) -), for example cyclopentylcarbonyl, cyclohexylcarbonyl, cyclooctylcarbonyl and like.
  • cycloalkoxycarbonyl means a cycloalkoxy group as mentioned above which is linked via the carbonyl group (-C (O) -).
  • alkenylcarbonyl means an alkenyl group as previously defined which is linked via the carbonyl group (-C (O) -).
  • alkenyloxycarbonyl means an alkenyloxy group as previously defined which is linked via the carbonyl group (-C (O) -).
  • alkynylcarbonyl group means an alkynyl group linked via the carbonyl group (-C (O) -).
  • alkynyloxycarbonyl means an alkynyloxy group as previously defined which is linked via the carbonyl group (-C (O) -).
  • Halogen is fluorine, chlorine, bromine or iodine.
  • M stands for a cation equivalent, ie for monovalent cation or the proportion of a polyvalent cation corresponding to a positive single charge.
  • the cation M + serves only as a counterion to the neutralization of the negatively charged COO " group and can in principle be chosen arbitrarily, Therefore, preferably alkali metal, especially sodium, potassium or lithium ions or onium ions, such as ammonium, mono-, Di-, tri-, tetraalkylammonium, phosphonium ions, tetraalkylphosphonium or tetraarylphosphonium ions used.
  • Condensed ring systems may be fused (fused) aromatic, hydroaromatic and cyclic compounds.
  • Condensed ring systems generally consist of two, three or more than three rings, each of which is unsubstituted or may carry the substituents previously mentioned for aryl.
  • the fused ring system may contain carbon atoms as well as oxygen, nitrogen or sulfur selected heteroatoms as ring members.
  • the bridge may also have 1, 2 or 3 in addition to carbon atoms as bridging atoms under nitrogen, Oxygen and sulfur selected heteroatoms.
  • Suitable derivatives of the compounds according to formula 1 include the acid addition salts of the compounds of formula 1.
  • Suitable acids are hydrohalic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, dC 6 carboxylic acids such as formic acid, acetic acid, or sulfonic acids such as p-toluenesulfonic acid or methanesulfonic acid.
  • the dermocosmetics contain compounds according to formula 1, in which in the group CR 5 the substituent R 5 is hydrogen.
  • R 2 is OR 6 .
  • R 6 is preferably hydrogen or C 1 -C 6 -alkyl.
  • compounds according to formula 1 are preferred in which R 6 is hydrogen, ie R 2 is hydroxy.
  • R 3 is hydrogen, hydroxy, C 1 -C 6 -alkyl, hydroxyCrC 6 -alkyl, amino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino-d-Ce -alkyl, di- (Ci-C 6 -alkylamino) -Ci-C 6 alkyl, Ci-Ce-alkylaminocarbonyl, di- (CrC 6 - alkylamino) carbonyl or aminocarbonyl.
  • R 3 is hydrogen, hydroxy, C 1 -C 4 -alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl or sec-butyl, hydroxy-C 1 -C 2 -alkyl, such as hydroxymethyl or hydroxyethyl, or aminocarbonyl.
  • R 1 is hydrogen, d-Ce-alkyl, such as methyl, ethyl or propyl, C r C 6 alkoxycarbonyl, especially dC 4 - alkoxycarbonyl, z.
  • R 1 is hydrogen, d-Ce-alkyl, such as methyl, ethyl or propyl, C r C 6 alkoxycarbonyl, especially dC 4 - alkoxycarbonyl, z.
  • R 1 is hydrogen or COOH.
  • Equally preferred compounds according to formula 1 are those in which R 4 is C 1 -C 6 -alkyl, amino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di- (C 1 -C 6 -alkyl) -amino dC 6 - alkyl, phenyl-Ci-C 6 -alkyl or phenyl, where phenyl may be unsubstituted in the two last-mentioned substituents or one or two 4 alkyl and dC 4 among C - alkoxy may bear substituents selected.
  • R 4 is C 1 -C 4 -alkyl, especially C 1 -C 2 -alkyl, e.g. As methyl or ethyl, di- (Ci-C 4 -alkyl) amino-Ci-C 4 - alkyl, especially di- (Ci-C 2 alkyl) amino-Ci-C 2 alkyl such as dimethylaminomethyl, dimethylaminoethyl , Diethylaminomethyl or diethylaminoethyl, phenyl-dC 2 -alkyl, such as benzyl, 1-phenylethyl or 2-phenylethyl, or phenyl.
  • R 4 and R 5 together represent a divalent bridging group having 1 to 6 atoms, in particular 2, 3, 4 or 5 atoms, between the flanking bonds.
  • compounds according to formula 1 are preferred in which R 4 and R 5 together represent a divalent bridging group having 1 to 6 atoms between the flanking bonds.
  • R 4 and R 5 together with the carbon atoms of the pyridine ring to which they are attached represent a fused ring system.
  • Preferred fused rings are benzene, naphthalene and anthracene rings, which are unsubstituted or substituted by one or two of the substituents previously mentioned for aryl. can.
  • R 4 and R 5 together with the carbon atoms of the pyridine ring to which they are attached are an unsubstituted benzene ring.
  • R 1 and R 5 together represent a divalent bridging group having 1 to 6 atoms, in particular 2, 3, 4 or 5 atoms, between the flanking bonds.
  • R 1 and R 5 together with the carbon atoms of the pyridine ring to which they are attached are a fused ring system.
  • Preferred fused rings are five- or six-membered heterocyclic, partially unsaturated rings containing, in addition to carbon atoms, one or two heteroatoms selected from oxygen, sulfur or nitrogen. More preferably, R 1 and R 5 together with the carbon atoms of the pyridine ring to which they are attached are a 2,5-dihydrofuran ring, 2,5-dihydrothiophene ring or 2,5-dihydro-1 H-pyrrole ring.
  • R 1 and R 5 together with the carbon atoms of the pyridine ring to which they are attached represent a 2,5-dihydrofuran ring.
  • R 7 , R 8 , R 9 , R 11 , R 12 and R 13 preferably have the following meanings:
  • R 7 , R 11 are each independently hydrogen or Ci-Cio-alkyl; and R 8 , R 9 , R 12 , R 13 are independently hydrogen or Ci-Cio-alkyl.
  • such compounds according to formula 1 are used in the dermocosmetics according to the invention, which in the singeing test for checking the antioxidant effect of said substances (the details for carrying out this test are described in Example 4), compared to the reference substance vitamin E, an oxygen consumption after 20 hours incubation with squalene less than 90%, preferably less than 80%, 70% or 60%, most preferably less than 50%, 40%, 30% or 20%, and most preferably less than 10 % exhibit.
  • a preferred subject matter of the present invention are dermocosmetics containing compounds selected from the group comprising 4-phenyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 4-benzyl-6-isopropyl-1 , 3-dihydrofuro [3,4-c] pyridin-7-ol, 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3 hydroxypyridine hydrochloride, 2,3-dihydroxypyridine, 3-hydroxypicolinic acid amide, 3-hydroxy-2-methylquinoline-4-carboxylic acid and 6-methylpyridin-3-ol, more preferably 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine and 3-hydroxypic
  • Dermocosmetics according to the invention preferably contain the abovementioned substances in a proportion of 0.001 to 30% by weight (wt .-%), preferably 0.01 to 0.1 wt .-%, 0.1 to 1 wt .-% based on the total weight of agent.
  • the dermocosmetics contain the above-mentioned compounds in a concentration of 1 to 10 wt .-%, preferably 2 to 8 wt .-%, 3 to 7 wt .-%, 4 to 6 wt .-% based on the Total weight of the agent.
  • the dermocosmetics contain the abovementioned compounds in a concentration of 10 to 20% by weight, preferably 1 to 19% by weight, 12 to 18% by weight, 13 to 17% by weight, 14 to 16 wt .-% based on the total weight of the composition.
  • the dermocosmetics contain the abovementioned compounds in a concentration of 20 to 30% by weight, preferably 21 to 29% by weight, 22 to 28% by weight, 23 to 27% by weight. , 24 to 26 wt .-% based on the total weight of the composition.
  • the dermocosmetics according to the invention contain, in addition to the compounds of the formula 1, one or more cosmetic or dermocosmetic active ingredients.
  • active substances selected from the group of natural or synthetic polymers, pigments, humectants, oils, waxes, enzymes, minerals, vitamins, sunscreens, dyes, fragrances, antioxidants, preservatives and / or pharmaceutical active ingredients, which are used for Support, prevention and treatment of skin diseases are used and have a healing, damage preventive, regenerating or improving the general condition of the skin biological effect.
  • auxiliaries and additives for the production of hair cosmetic or skin cosmetic preparations are familiar to the expert and can from manuals of cosmetics, such as Schrader, bases and formulations of cosmetics, Weghig Verlag, Heidelberg, 1989, ISBN 3-7785-1491-1 , or Limbach, cosmetics: development, production and application of cosmetic products, 2nd extended edition, 1995, Georg Thieme Verlag, ISBN 3 13 712 602 9 are removed.
  • the dermocosmetics according to the invention preferably contain at least one of the compounds defined above and at least one different constituent selected from cosmetically active ingredients, emulsifiers, surfactants, preservatives, perfume oils, thickeners, hair polymers, hair and skin conditioners, graft polymers, water-soluble or dispersible silicone-containing polymers, light stabilizers, bleaching agents, gelling agents, conditioners, dyeing agents, tanning agents, tanning agents, dyes, pigments, bodying agents, moisturizers, restockers, collagen, protein hydrolysates, lipids, antioxidants, defoamers, antistatic agents, emollients and plasticizers.
  • cosmetically active ingredients emulsifiers, surfactants, preservatives, perfume oils, thickeners, hair polymers, hair and skin conditioners, graft polymers, water-soluble or dispersible silicone-containing polymers, light stabilizers, bleaching agents, gelling agents, conditioners, dyeing agents, tanning agents, tanning
  • the active compounds can also be described in encapsulated form as described in the patents / patent applications EP 00974775 B1, DE 2311 712, EP 0278 878, DE 1999 47147, EP 0706822B1 and WO 98/16621, the contents of which are hereby expressly incorporated by reference into the cosmetic Preparations should be included.
  • the amount of such active substances / substances (one or more of the compounds characterized in greater detail hereinafter) in the preparations according to the invention is preferably from 0.001 to 30% by weight, particularly preferably from 0.05 to 20% by weight, in particular from 1 to 10% by weight .-%, based on the total weight of the preparation.
  • the above-mentioned and further active compounds that can be used in the preparations according to the invention are given in DE 103 18 526 A1 on pages 12 to 17, to which reference is made in full at this point.
  • the dermocosmetics according to the invention are preferably skin protection agents, skin care preparations, skin cleansing agents, hair protection agents, hair care preparations, hair cleansing preparations or preparations for decorative cosmetics which, depending on the field of application, are preferably in the form of ointments, creams, emulsions, suspensions, lotions, as milk, Pastes, gels, foams or sprays are applied.
  • the formulation base of dermocosmetics according to the invention preferably contains cosmetically or dermocosmetically / pharmaceutically acceptable excipients.
  • Pharmaceutically acceptable excipients which are known to be usable in the field of pharmacy, food technology and related fields, in particular those listed in relevant pharmacopoeias (for example German Pharmacopoeia) and other auxiliaries whose properties do not preclude physiological application.
  • Suitable cosmetically and / or dermocosmetically active agents are, for example, coloring agents, skin and hair pigmenting agents, toning agents, tanning agents (artificial skin tanning agents), bleaching agents, keratin-hardening substances, antimicrobial agents, light filter active ingredients, repellent active ingredients, hyperemic substances, keratolytic and keratoplastic acting substances, anti-dandruff agents, anti-inflammatory agents, keratinizing substances, antioxidants or free-radical scavengers, skin-moisturizing or moisturizing substances, moisturizing agents, anti-dehydration or anti-allergic active substances, branched fatty acids such as 18-methyl eicosanoic acid, and mixtures thereof.
  • a related embodiment 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.
  • 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.
  • the polymers and dispersions are suitable as auxiliaries in pharmacy, preferably as or in coating agent (s) or binder (s) for solid dosage forms. They can also be used in creams and as tablet coatings and tablet binders.
  • antioxidants are selected which are described on page 17, lines 15-40 of the PCT application with the file reference PCT / EP2006 / 064264.
  • the content of the said text is hereby incorporated by reference in its entirety.
  • the above-mentioned pages and lines, as well as all other references to the contents of the PCT application with the file reference PCT / EP2006 / 064264, refer to the application text filed on July 14, 2006 at the European Patent Office of the cited patent application.
  • Panthenol, pantolactone, nicotinamide and biotin are very particularly preferred according to the invention.
  • compositions according to the invention contain at least one pigment.
  • the pigments are present in undissolved form in the product composition and may be present in an amount of from 0.01 to 25% by weight, more preferably from 5 to 15% by weight.
  • the preferred particle size is 1 to 200 .mu.m, in particular 3 to 150 .mu.m, particularly preferably 10 to 100 .mu.m.
  • the pigments are practically insoluble colorants in the application medium and may be inorganic or organic. Also inorganic-organic mixed pigments are possible. Preference is given to inorganic pigments.
  • the advantage of inorganic pigments is their excellent light, weather and temperature resistance.
  • inorganic pigments examples include inorganic pigments, organic pigments and pearlescing agents.
  • organic pigments examples include inorganic pigments, organic pigments and pearlescing agents.
  • pearlescing agents can be found in pages 19, lines 10-42, page 20, lines 1-9 and 27-39 of PCT Application Serial No. PCT / EP2006 / 064264. The content of the said passages is hereby incorporated by reference in its entirety.
  • the composition according to the invention contains from 0.01 to 10, particularly preferably from 0.05 to 5,% by weight of at least one particulate substance.
  • Suitable substances are e.g. Substances which are solid at room temperature (25 ° C) and in the form of particles. Suitable examples are silica, silicates, aluminates, clays, mica, salts, in particular inorganic metal salts, metal oxides, e.g. Titanium dioxide, minerals and polymer particles.
  • the particles are present in the agent undissolved, preferably stably dispersed form and can be deposited in solid form after application to the application surface and evaporation of the solvent.
  • Preferred particulate substances are silica (silica gel, silica) and metal salts, in particular inorganic metal salts, with silica being particularly preferred.
  • Metal salts are e.g. Alkali or alkaline earth halides such as sodium chloride or potassium chloride; Alkali or alkaline earth sulfates such as sodium sulfate or magnesium sulfate.
  • Typical thickeners in such formulations are crosslinked polyacrylic acids and their derivatives, polysaccharides and their derivatives, such as xanthan gum, agar-agar, alginates or tyloses, cellulose derivatives, e.g. Carboxymethylcellulose or hydroxycarboxymethylcellulose, fatty alcohols, monoglycerides and fatty acids, polyvinyl alcohol and polyvinylpyrrolidone.
  • Nonionic thickeners are preferably used.
  • Artificial skin tanning agents which are suitable for tanning the skin without natural or artificial irradiation with UV rays are, for example, dihydroxyacetone, alloxan and walnut shell extract.
  • Suitable keratin-hardening substances are as a rule active ingredients, as are also used in antiperspirants, for example potassium aluminum sulfate, aluminum hydroxychloride, aluminum lactate, etc.
  • Antimicrobial agents are used to destroy microorganisms or to inhibit their growth and thus serve both as a preservative and as a deodorizing substance, which reduces the formation or intensity of body odor.
  • deodorizing substances are, for example, zinc ricinoleate, triclosan, undecylenic acid alkylolamides, triethyl citronate, chlorhexidine etc.
  • the cosmetic compositions may contain perfume oils.
  • perfume oils are the mixtures of natural and synthetic fragrances mentioned on page 23, lines 1-36 of the PCT application with the file reference PCT / EP2006 / 064264. The content of the said text is hereby incorporated by reference in its entirety
  • compositions according to the invention preferably contain oils, fats and / or waxes.
  • Advantageous constituents of the oil and / or fat phase of the compositions according to the invention fatty acid triglycerides, Guerbet alcohols, cyclic or linear silicone oils, phospholipids are described on pages 23, lines 40-43 and page 29, line 14 of the PCT Application Serial No. PCT / EP2006 / 064264 The contents of the said texts are hereby incorporated by reference in their entirety
  • Suitable cosmetically acceptable oil and fat components are also described in Karl-Heinz Schrader, Fundamentals and formulations of cosmetics, 2nd edition, Verlag Wegig, Heidelberg, p. 319-355, which is incorporated herein by reference in its entirety.
  • the cosmetic or dermatological composition in the sense of the present invention represents a solution or emulsion or dispersion
  • the solvents mentioned on page 29 of the PCT application with the file reference PCT / EP2006 / 064264 can be used.
  • the content of the said text is hereby incorporated by reference in its entirety.
  • compositions of the invention may contain surfactants and polysorbates.
  • surfactants and polysorbates are described, for example, on the page 30 of the PCT application with file number PCT / EP2006 / 064264. The content of the text cited is hereby incorporated by reference in its entirety.
  • surfactants and / or polysorbates are used according to the invention advantageously in a concentration of 0.1 to 5% by weight and in particular in a concentration of 1, 5 to 2.5% by weight, based on the total weight of the composition, individually or as a mixture several polysorbates used.
  • the compositions also contain conditioning agents.
  • Conditioning agents which are preferred according to the invention are, for example, all compounds disclosed in section 4 of the International Cosmetic Ingredient Dictionary and Handbook (Volume 4, published by: RC Pepe, JA Wenninger, GN McEwen, The Cosmetic, Toiletry, and Fragrance Association, 9th Edition, 2002) the terms Hair Conditioning Agents, Humectants, Skin Conditioning Agents, Skin Conditioning Agents Emollient, Skin Conditioning Agents Humectant, Skin Conditioning Agents-Miscellaneous, Skin Conditioning Agents- Occlusive and Skin Protectans are listed as well as all in the EP -An 934 956 (pp.
  • Polyquaternium compounds in particular Polyquaternium-1 to Polyquaternium Suitable conditioning agents include, for example, polymeric quaternary ammonium compounds, cationic cellulose derivatives and polysaccharides.
  • Conditioning agents which are advantageous according to the invention can be selected from those given in Table 1 on page 32 of the PCT application with the file reference PCT / EP2006 / 064264. The content of said table is hereby incorporated by reference in its entirety.
  • guar gum quali- Terni catalyzed derivatives in particular guar, hydroxypropylammonium (eg Jaguar Excel ®, Jaguar C 162 ® (Rhodia), CAS 65497-29-2, CAS 39421-75-5).
  • guar hydroxypropylammonium
  • non-ionic poly N-vinylpyrrolidone / polyvinyl acetate copolymers eg Lu viskol ® VA 64 (BASF)
  • anionic acrylate copolymers eg Luviflex soft ® (BASF)
  • amphoteric amide / acrylate / methacrylate copolymers for example, Amphomer ® ( National Starch)
  • the dermocosmetics according to the invention optionally contain ethoxylated oils. Preferred are the oils disclosed on page 33 from line 19 and page 34, lines 1 to 12 of PCT Application Serial No. PCTVE P2006 / 064264. The contents of the said passages are hereby incorporated by reference in their entirety.
  • sunscreen agents are, in particular, cosmetic or dermatological light stabilizers which contain at least one UV filter substance.
  • the cosmetic and / or dermatological sunscreen compositions of this invention are for cosmetic and / or dermatological photoprotection, further for the treatment and care of the skin and / or the hair and as a make-up product in the decorative cosmetics.
  • These include, for example, sunscreens, lotions, milks, oils, baisams, gels, lip care and lipsticks, masking creams and sticks, moisturizers, lotions, emulsions, face, body and hand creams, hair conditioners and conditioners, Hair fixatives, styling gels, hair sprays, deodorants or eye wrinkle creams, tropicals, sunblocks, aftersun preparations. All preparations contain at least one of the UV filter substances mentioned.
  • Sun oils are usually mixtures of various oils with one or more sunscreen filters and perfume oils.
  • the oil components are selected according to different cosmetic properties. Oils that give good fat and soft feel, such as mineral oils (eg, paraffin oils) and fatty acid triglycerides (eg, peanut oil, sesame oil, avocado oil, medium chain triglycerides) are mixed with oils that promote dispersibility and retraction Improve the sun oils in the skin, reduce the stickiness and make the oil film for air and water vapor (sweat) permeable. These include branched-chain fatty acid esters (eg isopropyl palmitate) and silicone oils (eg dimethylsilicone). When using oils based on unsaturated fatty acids antioxidants, eg.
  • Sun oils as anhydrous formulations usually contain no preservatives.
  • Sunmilk and creams are made as oil-in-water (O / W) emulsions and as water-in-oil (W / O) emulsions.
  • O / W emulsions are easily distributed on the skin, they are usually absorbed quickly and are almost always readily washable with water.
  • W / O emulsions are harder to rub in, they make the skin stronger and thus look a bit stickier, but on the other hand they better protect the skin from drying out.
  • W / O emulsions are mostly waterproof.
  • the emulsion base determines the degree of water resistance.
  • auxiliaries eg polymers
  • the light stabilizers are usually based on a carrier which contains at least one oil phase.
  • a carrier which contains at least one oil phase.
  • compositions based on water are also possible. Accordingly, oils, oil-in-water and water-in-oil emulsions, creams and pastes, lip balm sticks or fat-free gels are contemplated.
  • emulsions u.a. also O / W macroemulsions, O / W microemulsions or O / W / O emulsions having dispersed in surface-coated titanium dioxide particles, wherein the emulsions by phase inversion technology, e.g. according to the technology described in DE-A-197 26 121, are available.
  • Typical film formers are, for example, hydrocolloids such as chitosan, microcrystalline chitosan or quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds.
  • Suitable light filter active substances are substances which absorb UV rays in the UV-B and / or UV-A range. By this are meant organic substances capable of absorbing ultraviolet rays and absorbing the absorbed energy in the form of longer wavelength radiation, e.g. Heat, give it up again.
  • the organic substances may be oil-soluble or water-soluble.
  • Suitable UV filters are e.g. 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.
  • p-aminobenzoic acid esters p-aminobenzoic acid esters, cinnamic acid esters, benzophenones, camphor derivatives and UV-blocking pigments, such as titanium dioxide, talc and zinc oxide. Particular preference is given to pigments based on titanium dioxide.
  • Suitable repellent agents are compounds capable of preventing or repelling certain animals, particularly insects, from humans. These include, for example, 2-ethyl-1, 3-hexanediol, N, N-diethyl-m-toluamide, etc.
  • Suitable active ingredients are on page 39 from line 25 of the PCT application with the file reference PCT / EP2006 / 064264 called. The content of the said text is hereby incorporated by reference in its entirety.
  • the dermocosmetics according to the invention can contain at least one cosmetically or pharmaceutically acceptable polymer as cosmetic and / or pharmaceutical active substance (as well as optionally as adjuvant). These include, in general, cationic, amphoteric and neutral polymers.
  • Suitable polymers are e.g. cationic polymers called polyquaternium according to INCI, e.g. Copolymers of vinylpyrrolidone / N-vinylimidazolium salts, copolymers of N-vinylpyrrolidone / dimethylaminoethyl methacrylate, quaternized with diethyl sulfate (Luviquat PQ 11), copolymers of N-vinylcaprolactam / N-vinylpyrrolidone / N-vinylimidazolium salts (Luviquat E Hold) , cationic cellulose derivatives (polyquaternium-4 and -10), acrylamidocopolymers (polyquaternium-7) and chitosan.
  • polyquaternium cationic polymers called polyquaternium according to INCI, e.g. Copolymers of vinylpyrrolidone / N-vinylimidazolium salts
  • Suitable polymers are mentioned on pages 40 (from line 15) to 41 (to line 9) of the PCT application with the file reference PCT / EP2006 / 064264. The content of the said text is hereby incorporated by reference in its entirety.
  • the active ingredients from the group of refatting substances, for example PurCellin, Eucerit ® and Neocerit® ®.
  • the active ingredient (s) are furthermore advantageously selected from the group of NO synthase inhibitors, in particular when the preparations according to the invention are used for the treatment and prophylaxis of the symptoms of intrinsic and / or extrinsic skin aging and for the treatment and prophylaxis of the harmful effects of ultraviolet radiation on the skin and the hair should serve.
  • Preferred NO synthase inhibitor is nitroarginine.
  • the active substance (s) are selected from the group comprising catechins and bile acid esters of catechins and aqueous or organic extracts from plants or plant parts which have a content of catechins or bile acid esters of catechins.
  • Such active substances and extracts can be found on page 42 from line 4 and page 43 to line 25 of the PCT application with the file reference PCT / EP2006 / 064264. The content of the said text is hereby incorporated by reference in its entirety.
  • the active compounds can also be chosen very advantageously from the group of hydrophilic active substances, in particular from the following group: ⁇ -hydroxy acids such as lactic acid or salicylic acid or salts thereof such as Na lactate, Ca lactate, TEA lactate, urea, allantoin, serine, sorbitol, glycerol, milk proteins, panthenol, chitosan.
  • ⁇ -hydroxy acids such as lactic acid or salicylic acid or salts thereof such as Na lactate, Ca lactate, TEA lactate, urea, allantoin, serine, sorbitol, glycerol, milk proteins, panthenol, chitosan.
  • the dermocosmetics according to the invention are skin cleansers, hair treatment agents, nail care products or preparations for decorative cosmetics, as described on pages 45 (from line 15) to 49 (to line 35) (skin cleanser) and pages 49 (ab Line 37) to 53 (to line 42) (hair treatment agent) of the PCT Application Serial No. PCT / EP2006 / 064264.
  • the content of the said text is hereby incorporated by reference in its entirety.
  • Suitable skin cosmetic agents are also e.g. Face lotions, face masks, deodorants and other cosmetic lotions.
  • Means for use in decorative cosmetics include, for example, masking pens, theatrical paints, mascara and eye shadows, lipsticks, kohl pencils, eyeliners, blushes, powders, and eyebrow pencils.
  • the compounds according to the formulas 1 can be used in pore cleansing nose strips, in anti-acne agents, repellents, shaving agents, after- and pre-shave care products, after-sun care products, hair-removing preparations, hair dyeing preparations, personal care products, foot care products and in baby care.
  • the hair cosmetic or skin cosmetic preparation is used for application to the skin (topically) or hair.
  • Topical preparations are to be understood as meaning those preparations which are suitable for applying the active ingredients to the skin in fine distribution and preferably in a form absorbable by the skin.
  • aqueous and aqueous-alcoholic solutions sprays, foams, foam aerosols, ointments, aqueous gels, emulsions of the O / W or W / O type, microemulsions or cosmetic stick preparations.
  • the agent contains a carrier.
  • a carrier is water, a gas, a water-based liquid, an oil, a gel, an emulsion or microemulsion, a dispersion or a mixture thereof.
  • the mentioned carriers show a good skin Compatibility.
  • Particularly advantageous for topical preparations are aqueous gels, emulsions or microemulsions.
  • Another subject of the invention relates to the use of the compounds of the general formula 1 according to the invention, preferably 4-phenyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 4-benzyl-6-isopropyl-1 , 3-dihydrofuro [3,4-c] pyridin-7-ol, 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3 hydroxypyridine hydrochloride, 2,3-dihydroxypyridine, 3-hydroxypicolinic acid amide, 3-hydroxy-2-methylquinoline-4-carboxylic acid or 6-methylpyridin-3-ol, more preferably 4-dimethlyaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine and 3-
  • Another subject of the invention is the use of the compounds of general formula 1 according to the invention, preferably 4-phenyl-6-methyl-1, 3-dihydrofuro [3,4-c] pyridin-7-ol, 4-benzyl-6-isopropyl-1 , 3-dihydrofuro [3,4-c] pyridin-7-ol, 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3 hydroxypyridine hydrochloride, 2,3-dihydroxypyridine, 3-hydroxypicolinic acid amide, 3-hydroxy-2-methylquinoline-4-carboxylic acid or 6-methylpyridin-3-ol, more preferably 4-dimethlyaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine and 3-hydroxypicolinic
  • the abovementioned compounds are used to increase the shelf life or duration of use of in skin protection agents, skin care preparations, skin cleansing preparations, hair protection preparations, hair care preparations, hair cleansing preparations or in preparations for decorative cosmetics used existing cosmetic or dermocemetic agents / ingredients.
  • a further preferred embodiment of the present invention relates to the use of the compounds of general formula 1 according to the invention, preferably 4-phenyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 4-benzyl 6-isopropyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 2 - (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine, 3-hydroxypicolinic acid amide, 3-hydroxy-2-methylquinoline-4-carboxylic acid or 6-methylpyridin-3-ol, more preferably 4-dimethylaminomethyl-6-methyl -1, 3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine
  • a further preferred embodiment of the present invention relates to the use of the compounds of general formula 1 according to the invention, preferably 4-phenyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 4-benzyl 6-isopropyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 2 - (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine, 3-hydroxypicolinic acid amide, 3-hydroxy-2-methylquinoline-4-carboxylic acid or 6-methylpyridin-3-ol, more preferably 4-dimethylaminomethyl-6-methyl -1, 3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine
  • the invention relates to the use of a compound according to formula 1, preferably 4-phenyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 4-benzyl-6-isopropyl-1,3 - dihydrofuro [3,4-c] pyridin-7-ol, 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine, 3-hydroxypicolinic acid amide, 3-hydroxy-2-methylquinoline-4-carboxylic acid or 6-methylpyridin-3-ol, more preferably 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridine-7 ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine and 3-hydroxypicolinic acid amide, most
  • the compounds according to the invention of the general formula 1 preferably 4-phenyl-6-methyl-1, 3-dihydrofuro [3,4-c] pyridin-7-ol, 4-benzyl-6-isopropyl-1, 3- dihydrofuro [3,4-c] pyridin-7-ol, 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine, 3-hydroxypicolinic acid amide, 3-hydroxy-2-methylquinoline-4-carboxylic acid or 6-methylpyridin-3-ol, more preferably 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3, 4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride, 2,3-dihydroxypyridine and 3-hydroxypicolinic acid amide, most preferably 4-dimethly
  • the cosmetic preparations according to the invention are applied to the skin or hair in the manner customary for cosmetics or dermocosmetics.
  • the dermocosmetics according to the invention can be composed as described above and serve for the preventative treatment, care and cleansing of the skin or hair or as make-up product in cosmetics.
  • the abovementioned compounds for the production of dermocosmetics, and / or for the stabilization of photosensitive and / or oxidation-sensitive substances in dermocosmetics, and / or for the prevention of radical-induced skin and / or hair damage, and / or for improvement the appearance of the skin and / or hair and / or as an antioxidant these are the dermocosmetic agents in a concentration of 0.001 to 30 weight percent (wt .-%), preferably 0.01 to 0.1 wt .-%, 0.1 to 1 wt .-% based on the total weight of the agent added.
  • the compounds according to the invention can be in a concentration of 1 to 10 wt .-%, preferably 2 to 8 wt .-%, 3 to 7 wt .-%, 4 to 6 wt .-%, based on the total weight of the agent used.
  • the compounds according to the invention may be present in a concentration of from 10 to 20% by weight, preferably from 1 to 19% by weight, from 12 to 18% by weight, from 13 to 17% by weight, from 14 to 16 wt .-% based on the total weight of the agent can be used.
  • the compounds according to the invention may be used in a concentration of 20 to 30% by weight, preferably 21 to 29% by weight, 22 to 28% by weight, 23 to 27% by weight, 24 to 26 wt .-% based on the total weight of the agent can be used.
  • (2-amino-2-methyl-propanol) AMP (ethylenediaminetetraacetic acid) EDTA,, (1, 1-difluoroethane) HFC 152, (International Nomenclature of Cosmetic Ingredients) INCI, (minutes) min., (Oil / water) O / W, (polyethylene glycol) PEG-25, (quantum satis) qs, (vinylpyrrolidones) VP, (water / oil) W / O, (active ingredient) WS, (polyvinylpyrrolydone) PVP.
  • Example 3 4-Dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol The preparation was carried out analogously to Example 1.
  • Example 4 Squalene test for the simulation of oxidation-sensitive cosmetic ingredients under oxidative conditions:
  • squalene is incubated in an airtight container in the presence of one test substance each and oxygen.
  • the container is connected to a pressure gauge.
  • the addition of N-hydroxyphthalimide and Cu-1 chloride to the solution induces radical oxidation, which involves consumption of oxygen.
  • the reduction of the oxygen concentration in turn results in a pressure drop in the container, which is documented by the pressure gauge.
  • the pressure drop in the container is a function of the radical oxidation of squalene molecules present in the container. It follows that the antioxidant property of a given test substance is inversely proportional to the decrease in oxygen concentration or the resulting pressure drop in the container after the induction of radical oxidation.
  • Test substance 1 4-Phenyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol
  • Test substance 2 4-Benzyl-6-isopropyl-1,3-dihydrofuro [3,4-c ] pyridin-7-ol
  • test substance 3 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol test substance 4: 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride *
  • Test substance 5 2,3-dihydroxypyridine * Test substance 6: 3-hydroxypicolinic acid amide * Test substance 7: 3-hydroxy-2-methylquinoline-4-carboxylic acid * Test substance 8: 6-methylpyridin-3-ol * *: commercially available, e.g. From Sigma-Aldrich, Germany.
  • V1 Vitamin E.
  • V2 Irganox®1010 from Ciba Specialty Chemicals, Switzerland, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate]; V3: ascorbyl palmitate V4: 2,6-di-tert-butyl-p-cresol (BHT)
  • the compounds of formula 1 have a stabilizing effect and can protect squalene from oxidation. As squalene makes up a large proportion of the skin fat, this also provides direct evidence of a skin-protecting and skin-improving effect and of these compounds. Furthermore, it is shown that the compounds of the formula 1 have a significantly stronger oxidation damage-inhibiting effect with respect to the comparative substances used and are therefore particularly suitable for use as oxidant inhibitors in cosmetic preparations. It is particularly noteworthy that the tested compounds cause almost complete oxidation protection over a long period of time compared to the other oxidants
  • test substance 4 the compounds 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride was used according to the invention for the production of dermocosmetics.
  • this compound is referred to as test substance 4.
  • Example 5 Use of the test substance 4 in a day care emulsion - type O / W
  • Preparation Heat phases A and B separately from each other to about 80 ° C. Stir phase B into phase A and homogenize. Stir phase C into combined phases A and B and homogenize again. Cool to about 40 ° C. with stirring, add phase D, adjust the pH to about 6.5 with phase E, homogenize and cool to room temperature while stirring.
  • the formulation is produced without inert gas.
  • the filling must be in oxygen-impermeable packaging, e.g. Aluminum tubes take place.
  • Example 6 Use of the test substance 4 in a protective day cream type
  • 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 7 Use of the test substance 4 in a facial cleansing lotion - type
  • Example 8 Use of the test substance 4 in a Daily Care Body Spray
  • Example 9 Use of the test substance 4 in a skin care gel
  • Example 10 Use of the test substance 4 in an aftershave lotion
  • Preparation Mix the components of phase A. Dissolve phase B, work in phase A and homogenize.
  • Example 1 1 Use of the test substance 4 in an after-sun lotion WS 1%: test substance 4
  • Preparation Mix the components of phase A. Stir phase B into phase A while homogenizing. Neutralize with Phase C and homogenize again.
  • Example 12 Use of the test substance 4 in a sunscreen lotion WS 1%: test substance 4
  • 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 with stirring to about 40 ° C, add phase D and homogenize again.
  • Example 13 Use of the test substance 4 in a sunscreen lotion - type O / W
  • Example 14 Use of the test substance 4 in a sunscreen lotion - type O / W
  • Example 15 Use of the test substance 4 in a foot balm WS 1%: test substance 4
  • 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 16 Use of the test substance 4 in a W / O emulsion with bisabolol WS 1%: test substance 4
  • test substance 4 q.s. Perfume oil q.s. preservative
  • test substance 4 q.s. Perfume oil q.s. preservative
  • Preparation Mix the components of phase A. Add the components of phase B one by one and dissolve. Fill with phase C.
  • Preparation Mix the components of phase A. Add the components of phase B one by one and dissolve. Fill with phase C.
  • Preparation Mix the components of phase A. Clear the components of phase B, then stir phase B into phase A. Adjust the pH to 6-7, fill with phase C.
  • Preparation Mix the components of phase A. Add the components of phase B one by one and dissolve. Dissolve phase C in the mixture of A and B, then adjust the pH to 6-7. Fill with phase D.
  • Preparation Mix the components of phase A. Add the components of phase B one by one and dissolve. Dissolve phase C in the mixture of A and B, then adjust the pH to 6-7. Fill with phase D.
  • phase A Solubilize phase A. Weigh phase B into phase A and solve it clearly. Adjust the pH to 6-7, fill with phase C.
  • phase A Solubilize phase A. Weigh phase B into phase A and solve it clearly. Adjust the pH to 6-7, fill with phase C.
  • phase A Solubilize phase A. Weigh phase B into phase A and solve it clearly. Adjust the pH to 6-7, fill with phase C.
  • Preparation Mix the components of phase A. Add the components of phase B one by one and dissolve. Fill with phase C.
  • Preparation Mix and dissolve the components of phase A. Adjust the pH to 6-7 with citric acid.
  • Phase B prehomogenising briefly, then stir phase B into phase A and homogenize again ren.Abaffecting to about 40 0 C, add phase C and homogenize thoroughly again. Adjust the pH to 6-7 with citric acid.
  • Preparation Heat phases A and B separately to about 80 ° C. Stir phase B into phase A and homogenize. Cool with stirring to about 40 0 C, add phase C and homogenize again. Allow to cool to room temperature while stirring.
  • Example 35 Liquid Make-up - Type O / W
  • Preparation Heat phases A and B separately to about 80 ° C. Stir phase B into phase A and homogenize. Cool with stirring to about 40 0 C, add phases C and D and thoroughly homogenize again. Allow to cool to room temperature while stirring.
  • test substance 4 the compounds 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride according to the invention are used for the production of the dermocosmetics.
  • this compound is referred to as test substance 4.
  • test substance 4 mentioned is used as an approximately 10% strength by weight solution.
  • the following information is parts by weight.

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Abstract

L'invention concerne des cosmétiques dermatologiques contenant des composés de pyrimidinol et/ou de pyrimidine et l'utilisation de ces cosmétiques dermatologiques pour la diminution des délabrements de la peau ou des cheveux dus à des radicaux, ainsi que pour l'accroissement de la conservation de préparations cosmétiques dermatologiques.
PCT/EP2007/058904 2006-09-01 2007-08-28 utilisation d'hÉTÉrocycles contenant de l'azote dans les cosmÉtiques dermatologiques WO2008025755A1 (fr)

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US8642604B2 (en) 2006-04-04 2014-02-04 The Regents Of The University Of California Substituted pyrazolo[3,2-d]pyrimidines as anti-cancer agents
US8697709B2 (en) 2008-10-16 2014-04-15 The Regents Of The University Of California Fused ring heteroaryl kinase inhibitors
US8703777B2 (en) 2008-01-04 2014-04-22 Intellikine Llc Certain chemical entities, compositions and methods
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US8828998B2 (en) 2012-06-25 2014-09-09 Infinity Pharmaceuticals, Inc. Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors
US8901133B2 (en) 2010-11-10 2014-12-02 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
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US9512125B2 (en) 2004-11-19 2016-12-06 The Regents Of The University Of California Substituted pyrazolo[3.4-D] pyrimidines as anti-inflammatory agents
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