WO2008025755A1

WO2008025755A1 - Use of n-containing heterocycles in dermocosmetics

Info

Publication number: WO2008025755A1
Application number: PCT/EP2007/058904
Authority: WO
Inventors: Gerhard Wagenblast; Sylke Haremza; Arne Ptock; Frank HÖFER
Original assignee: Basf Se
Priority date: 2006-09-01
Filing date: 2007-08-28
Publication date: 2008-03-06

Abstract

The present invention relates to dermocosmetics comprising pyrimidinol and/or pyrimidine compounds and to the use of said dermocosmetics in order to reduce skin or hair damage caused by radicals and increase the shelf live of dermocosmetic preparations.

Description

Use of N-containing heterocycles in dermocosmetics.

description

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). As an essential mechanism leading to extrinsic aging of the skin, the formation of free carbon radicals or reactive oxygen species (ROS), e.g. Peroxide radicals, considered. These extremely reactive substances lead to the oxidation of various cell components such as DNA, proteins and membrane lipids. In the skin area, free radicals damage the collagen and elastin and affect the fatty substances. As a result, 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. For chronic UV damages predominantly the UV-A range (320-400 nm) is made responsible. Furthermore, the following clinical pictures of sun exposure are negatively influenced: lupus erythematosus, solar urticaria, hydroa vacciniformis, photoagainst atopic dermatitis, xeroderma pigmentosum, vitiligo, chronic actinia see dermatitis, herpes simplex infections as well as the so-called Mallorca Acne (is triggered by persons exposed to peroxides with simultaneous UV irradiation (phototoxic chemotoxic skin reaction).) Furthermore, the expression of metalloproteinases is induced by UVA radiation Clinically, extrinsic skin aging typically occurs on skin areas exposed to environmental factors, superimposing the symptoms of intrinsic skin aging, thus protecting the skin from the effects of intense sunlight is of great importance to human health.

Furthermore, the named harmful effects cause damage to the cells of the skin itself. As a consequence, for example, 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.

To counteract the stress described above, the skin has a variety of its own protective mechanisms. However, 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 Injury" 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).

The importance of radicals in the context of skin aging has led in recent years to an intensive search for drugs that are harmful

Eliminate the effects of radicals and thus protect the tissue from oxidative damage. Such 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.

In order to achieve the above-mentioned properties, radical scavengers are added to the dermocosmetic preparations (for example, DE 19739349). Of particular importance are the said preparations as 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

US 5001 136 (Pfizer Inc.) describes the use of aminopyridines as leukotrienase inhibitors.

US 4374136 (May & Baker Ltd.) describes the synthesis of aminopyrimidinols and their use as an antimalarial drug.

A use of these substances as radical scavengers or antioxidants in cosmetic preparations is not described in the prior art.

Due to the ever-increasing demand for active ingredients to prevent the above-mentioned damage to the skin and / or hair or the reduction of existing damage to the skin and / or hair, especially as a result of phototoxic chemotoxic reactions, it was the task of the present To identify active substances which (i) have the lowest possible irritation potential for the skin, (ii) have a high radical-inactivating effect and (iii) are also suitable for the production of cosmetic and / or dermocosmetic formulations or preparations. In particular, it was an object of the present invention to provide active substances and agents containing these active ingredients which have a radical-decomposing effect and can be used to prevent or reduce skin and / or hair damage caused by the radicals mentioned. It was also of particular interest to identify active substances which stabilize oxidation-sensitive dermocosmetically active substances and which Extend the shelf life of such preparations. It was therefore also an object of the invention to provide dermocosmetic preparations which are suitable for the prophylaxis and treatment of photosensitive skin, in particular photodermatoses or polymorphic photodermatoses as described in the literature (eg Aa. Voelckel et al., Zentralblatt Haut- und Verskrankkrankheiten (1989) ), 156, p.2).

Surprisingly, it has been found that compounds according to the general formula 1 have the desired properties and that the stated objects could be achieved by their use in dermocosmetic preparations.

definitions

"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.

"Dermocosmetics" 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. "Dermocosmetics" 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, Hüthig 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, Hüthig 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.

Detailed description of the invention

The present invention relates to dermocosmetics containing at least one compound according to the general formula 1

wherein

X is nitrogen or CR ⁵ ;

R ^{1 is} hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl,

Heteroaryl, alkylcarbonyl, alkoxycarbonyl, COOH, COOM, aminocarbonyl,

Alkylaminocarbonyl, dialkylaminocarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkynylcarbonyl or alkynyloxycarbonyl;

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

Heteroaryl stands;

or R ¹ with R ^{5 may} also together represent a divalent bridging group having 1 to 6 atoms between the flanking bonds;

or 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;

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; or

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;

In detail, the collective terms given for various substituents R ¹ to R ^{13 have} the following meanings:

For the purpose of the present invention, the term "alkyl" includes straight-chain or branched hydrocarbon radicals having 1 to 50 carbon atoms (C 1 -C ₅₀ -alkyl).

It is preferably straight-chain or branched C 1 -C 5 -alkyl, such as

Methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-

Pentyl, 2-methylbutyl, 3-methylbutyl, 1, 2-dimethylpropyl, 1, 1-dimethylpropyl, 2,2-

Dimethylpropyl, 1-ethylpropyl, n-hexyl, 2-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,3-dimethylbutyl, 1, 1-dimethyl- butyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-2-methylpropyl, n- Heptyl, 2-heptyl, 3-heptyl,

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.

The term 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.

The term "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.

The term "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.

The term "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. In the case of a substitution, 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.

The term "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.

2, 3 or 4, can carry double bonds in any position, z. C ₂ -C ₂₀ alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3

Butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl. The term "alkenyl" also includes substituted alkenyl groups which are e.g.

B. 1, 2, 3, 4 or 5 substituents can carry. Suitable substituents are, for. B.

Cycloalkyl, heterocycloalkyl, aryl, heteroaryl, hydroxy, alkoxy, nitro, cyano, halogen,

NR ¹² R ¹³ .

The term "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. The term "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 .

The term "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.

In the case of a substitution, 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. Examples of substituted aryl 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-isobutylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diisobutylphenyl, 2,4,6-triisobutylphenyl , 2-, 3- and 4-sec-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6-di-sec-butyl-phenyl, 2,4,6-tri-sec- butylphenyl, 2-, 3- and 4-tert-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6-di-tert-butylphenyl and 2,4,6-tri-tert-butylphenyl ; 2-, 3- and 4-methoxyphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2-, 3- and 4-ethoxyphenyl, 2 , 4-, 2,5-, 3,5- and 2,6-diethoxyphenyl, 2,4,6-triethoxyphenyl, 2-, 3- and 4-propoxyphenyl, 2,4-, 2,5-, 3,5- and 2,6-dipropoxyphenyl, 2-, 3- and 4-isopropoxyphenyl, 2,4-, 2,5-, 3,5- and 2,6-diisopropoxyphenyl and 2-, 3- and 4- butoxyphenyl.

The term "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.

The term "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.

The term "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 Examples of 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 These heteroaromatic groups may be unsubstituted or substituted In the case of substitution, heteroaryl generally has 1, 2 or 3 substituents, preferably alkyl, alkoxy, Hydroxyl, COOH, COOM, and NR ¹² R ^{13 are} selected.

The term "aminocarbonyl" denotes an amino group which is bonded via the carbonyl group (-C (O) -).

The term "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.

The term "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.

The term "cycloalkoxycarbonyl" means a cycloalkoxy group as mentioned above which is linked via the carbonyl group (-C (O) -).

The term "alkenylcarbonyl" means an alkenyl group as previously defined which is linked via the carbonyl group (-C (O) -).

The term "alkenyloxycarbonyl" means an alkenyloxy group as previously defined which is linked via the carbonyl group (-C (O) -).

The term "alkynylcarbonyl group" means an alkynyl group linked via the carbonyl group (-C (O) -). The term "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.

If two substituents, for example R ¹ with R ⁵ or R ⁴ with R ⁵ , together represent a divalent bridging group having 1 to 6 atoms between the flanking bonds, 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.

Particular preference is given to dermocosmetics containing the compounds of the formula I listed below in which the substituents, in each case alone or in combination, have the following meaning:

Compounds according to formula 1 are preferred in which X is N. Also preferred are compounds according to formula 1, in which X is CR ⁵ .

In a preferred embodiment, the dermocosmetics contain compounds according to formula 1, in which in the group CR ⁵ the substituent R ^{5 is} hydrogen. In addition, compounds according to formula 1 are preferred in which R ^{2 is} OR ⁶ . In the group OR ⁶ R ^{6 is} preferably hydrogen or C 1 -C ₆ -alkyl. In particular, compounds according to formula 1 are preferred in which R ^{6 is} hydrogen, ie R ² is hydroxy.

Furthermore, compounds according to formula 1 are preferred in which 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. Most preferably, 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.

Furthermore, compounds according to formula 1 are preferred in which R ^{1 is} hydrogen, d-Ce-alkyl, such as methyl, ethyl or propyl, C _r C ₆ alkoxycarbonyl, especially dC ₄ - alkoxycarbonyl, z. For example, methoxycarbonyl or ethoxycarbonyl, COOM, such as COONa, COOK or COOMg ₀ , 5, or COOH. In particular, compounds according to formula 1 are preferred in which R ^{1 is} hydrogen or COOH.

Also preferred are compounds according to formula 1, in which R ^{4 is} hydrogen.

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. More preferably 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.

Equally preferred are compounds according to formula 1, wherein 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. In particular, 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. In particular, 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. Most preferably, R ⁴ and R ⁵ together with the carbon atoms of the pyridine ring to which they are attached are an unsubstituted benzene ring. Equally preferred are compounds according to formula 1, wherein 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.

In particular, 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.

Most preferably, 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.

Furthermore, 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.

In a further preferred embodiment, 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-hydroxypicolinic acid amide, most preferably 4-dimethlyaminomethyl-6-methyl-1, 3 dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride and 2,3-dihydroxypyridine, most preferably 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride and 2,3-dihydroxypyridine.

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. In a further embodiment, 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. In a likewise preferred embodiment, 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. In a furthermore preferred embodiment, 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.

In another preferred embodiment, the dermocosmetics according to the invention contain, in addition to the compounds of the formula 1, one or more cosmetic or dermocosmetic active ingredients.

These are preferably 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.

Suitable 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, Hüthig 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. 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.

To prepare the dermocosmetic agents of the invention, 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. Furthermore, 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.

Particular preference is given to dermocosmetics containing the dermocosmetically / pharmaceutically acceptable auxiliaries / active substances listed below:

Advantageously, 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.

For the vitamins, provitamins or vitamin precursors of the vitamin B group or derivatives thereof preferably to be used according to the invention, reference is made to the substances mentioned on page 18, lines 1-41 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.

Panthenol, pantolactone, nicotinamide and biotin are very particularly preferred according to the invention.

Dyes which may be used are those which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Kosmetische Färbemittel" of the Farbstoffkommission of the Deutsche Forschungsgemeinschaft, published by Verlag Chemie, Weinheim, 1984. These dyes are usually used in concentrations of 0.001 to 0.1 wt .-%, based on the total mixture. In a preferred embodiment, the 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.

Examples of inorganic pigments, organic pigments and 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.

In one embodiment, 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. These include, for example, customary preservatives known to the person skilled in the art, such as p-hydroxybenzoic acid ester, imidazolidinyl urea, formaldehyde, sorbic acid, benzoic acid, salicylic acid, etc. Such deodorizing substances are, for example, zinc ricinoleate, triclosan, undecylenic acid alkylolamides, triethyl citronate, chlorhexidine etc.

Preservatives or compounds having bactericidal, fungicidal or germ-inhibiting effects which are advantageous according to the invention are mentioned on page 21, from line 31 and page 22 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.

Optionally, the cosmetic compositions may contain perfume oils. Suitable 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

The 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 Hüthig, Heidelberg, p. 319-355, which is incorporated herein by reference in its entirety.

If 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.

The compositions of the invention may contain surfactants and polysorbates. Such 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.

These 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.

In a preferred embodiment of the invention, 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. 1-13) under "water soluble conditioning agent" and "oil soluble conditioning agent", the contents of which are hereby incorporated by reference in their entirety INCI referred to as 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.

Further inventively conditioners advantageous cellulose derivatives and 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). Also, non-ionic poly N-vinylpyrrolidone / polyvinyl acetate copolymers (eg Lu viskol ^® VA 64 (BASF)), anionic acrylate copolymers (eg Luviflex soft ^® (BASF)), and / or amphoteric amide / acrylate / methacrylate copolymers (for example, Amphomer ^® ( National Starch)) can be advantageously used according to the invention as a conditioner.

An addition of powder raw materials can be generally advantageous. Particularly preferred is the use of talc. 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.

In a particularly preferred embodiment of the present invention, 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. As vitamin E, added to prevent rancidity. 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. Depending on the type of emulsion, the properties of the preparations are very different: 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. In the case of O / W emulsions, the emulsion base, the selection of suitable light stabilizers and, if appropriate, the use of auxiliaries (eg polymers) determine the degree of water resistance. The basis of liquid and creamy O / W-Ernulsen resemble in their composition the usual emulsions in skin care. Sonnenmil- It is recommended that the skin dried out by the sun, water and wind should be sufficiently greasy. They must not be sticky, as this is particularly uncomfortable in the heat and in contact with sand.

The light stabilizers are usually based on a carrier which contains at least one oil phase. However, 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.

As 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. Also suitable are 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.

Particularly suitable are the organic and inorganic UV filters disclosed on pages 36-39 of PCT Application Serial No. PCT / EP2006 / 064264. The content of the said text is hereby incorporated by reference in its entirety.

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.

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.

It is also advantageous to choose 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.

Further advantageously, 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.

In addition, the active compounds (one or more compounds) can also be chosen very advantageously from the group of hydrophilic active substances, in particular from the following group: α-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.

It goes without saying that the list of the stated ingredients which can be used in the preparations according to the invention should not be regarded as conclusive or limiting. The ingredients may be used alone or in any combination with each other.

According to a preferred embodiment, 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.

In addition, 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.

As a rule, 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. For this purpose, e.g. 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.

According to a preferred embodiment of the cosmetic agent according to the invention, the agent contains a carrier. Preferred as 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-hydroxypicolinic acid amide, most preferably 4-dimethlyaminomethyl-6-methyl-1, 3 dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3-dihydroxypyridine, most preferably 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3 Dihydroxypyridine as an additive to the preparation of the above-described he Dermocosmetics according to the invention, preferably these are skin protection agents, skin care products, skin cleansing agents, hair protection agents, hair care products, hair cleaners or in preparations for decorative cosmetics.

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 acid amide, most preferably 4-dimethlyaminomethyl-6-methyl-1, 3 dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3-dihydroxypyridine, most preferably 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3 Dihydroxypyridine in dermocosmetics or cosmetic preparations for stabilization tion of the abovementioned light- and / or oxidation-sensitive dermatologically / pharmaceutically active substances, preferably for preventing radical-induced damage / inactivation of the active ingredients, with the result that the shelf life or duration of use of the cosmetic or dermocosmetic agents is increased ,

Preferably, 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 and 3-hydroxypicolinic acid amide, most preferably 4-dimethylaminomethyl-6- Methyl-1, 3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3-dihydroxypyridine, most preferably 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3-dihydroxypyridine in dermocosmet ika for the prevention or reduction of radical-induced damage to the skin or hair. The use according to the invention of the abovementioned compounds in dermocosmetics offers i.a. protection against damage caused directly or indirectly by processes caused by UV radiation or by reactive compounds, e.g. skin aging, loss of skin hydration, loss of skin elasticity, formation of wrinkles or wrinkles or pigmentation and age spots or brittle, dull and inelastic hair. 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 and 3-hydroxypicolinic acid amide, most preferably 4-dimethylaminomethyl-6- Methyl-1, 3-dihydrofuro [3,4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3-dihydroxypyridine, most preferably 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3-dihydroxypyridine in dermocosmetics a to improve the appearance of the skin and / or hair.

Furthermore, 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 preferably 4-dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridine-7 -ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3-dihydroxypyridine, most preferably 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3-dihydroxypyridine as Antioxi- dationsmittel in dermocosmetics.

Furthermore, 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-dimethlyaminomethyl-6-methyl-1,3-dihydrofuro [3 , 4-c] pyridin-7-ol, 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3-dihydroxypyridine, most preferably 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride or 2,3- Dihydroxypyridine in hair cosmetic preparations protects against premature aging of me hair and can thus be used as active ingredients in the cosmetic treatment of brittle, dull and inelastic hair.

For use, 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. For the inventive use of 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. In a further embodiment of the present invention, 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. In a likewise preferred embodiment, 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. In a furthermore preferred embodiment of the invention, 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.

Experimental examples

The following examples are disclosed to illustrate preferred embodiments of the present invention. These examples are not to be considered as limiting or limiting the invention.

In the experimental description, the following abbreviations are 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.

The following examples are intended to illustrate the invention without, however, limiting it

I. Preparation Examples

Example 1: 6-Methyl-4-phenyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol

The preparation was carried out as described in Example 2 of DE 2711656.

Example 2: 4-Benzyl-6-isopropyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol

The preparation was carried out as described in Example 22 of DE 2711656.

Example 3 4-Dimethylaminomethyl-6-methyl-1,3-dihydrofuro [3,4-c] pyridin-7-ol The preparation was carried out analogously to Example 1.

II. Application examples

Example 4 Squalene test for the simulation of oxidation-sensitive cosmetic ingredients under oxidative conditions:

To demonstrate an improved protective effect of the compounds according to formula 1 in comparison with the known antioxidants, a squalene oxidation test was carried out. In the human body squalene is produced in the liver and transported to the skin. Squalene accounts for up to 5% of the fat present in human skin. Squalene is sensitive to radical oxidation by atmospheric oxygen. For this reason, squalene is very well suited to prove both the skin protection effect and the oxidation protection effect of the compounds according to formula 1. Furthermore, it is demonstrated by these experiments that oxidation-sensitive substances can be protected against inactivation or spoilage over a relatively long period of time by using the compounds according to formula 1 in comparison with known anti-oxidation protection agents.

In this test, 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. Thus, 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.

When comparing the antioxidant properties (determined by the test described above), it is evident that α-CEHC, in comparison with the other test substances (α-tocopherol, 2,5,7,8-tetramethyl-2-carboxyl-6 Chromanol and 2,2,5,7,8-pentamethyl-6-chromanol) is a prominent inhibitor of radical oxidation.

In a storage experiment of squalene with a free radical source of copper and hydroxyphthalimide, the oxidation of squalene under air at room temperature was studied in the presence of stabilizers. Squalene served as a substitute. The addition of stabilizers makes it possible to prevent or reduce the breakdown of squalene. slow. The slowing down of squalene by the use of a stabilizer allows the evaluation of these compounds as antioxidants.

In the experiment, to a solution of 5 g squalene (12 mmol) in 5 g acetonitrile N-hydroxyphthalimide (80%, 126 mg), the compound to be tested (2.5 mg) and copper (I) chloride (0.2 mg). The flask with a volume of approximately 1.15 l was closed and the oxygen consumption was measured by means of a pressure cell (T ransmitter 0-1.6 bar, Alexander Wiegand GmbH, Germany) and a pen (Fa. Linseis, Germany) the course of the internal pressure at 20 ⁰ C (termperiert) measured. The value of the internal pressure was detected in the interval of 30 minutes. The following Table 1 shows the course of oxygen uptake of squalene in the presence of antioxidants. The control was a sample containing no stabilizer.

The following stabilizers of the formula I used according to the invention were investigated:

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.

The following stabilizers were used as comparison: 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)

Table 1 :

The results from Table 1 show that the compounds 1 used according to the invention reduce the oxidative degradation of squalene compared to phenolic antioxidants such as vitamin E, Irganox® 1010 or 2,6-di-tert-butyl-p-cresol, or ascorbyl Slow palmitate.

From the results of this experiment it can be seen that 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

The person skilled in the art is, of course, aware that the results obtained for squalene can be transferred to other oxidation-sensitive skin constituents and ingredients of cosmetic preparations.

In the following application examples, the compounds 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride was used according to the invention for the production of dermocosmetics. In the following, 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

Active substance [WS] 1%: test substance 4 % Ingredient (INCI)

A 1, 7 Ceteareth-6, Stearyl Alcohol

0.7 Ceteareth-25

2.0 diethylamino hydroxybenzoyl hexyl benzoate

2.0 PEG-14 Dimethicone

3.6 Cetearyl Alcohol

6.0 ethylhexyl methoxycinnamate

2.0 dibutyl adipate

B 5.0 glycerin

0.2% disodium EDTA

1, 0 panthenol q.s. preservative

67.8 Aqua the.

C 4.0 Caprylic / Capric Triglyceride, Sodium Acrylate Copolymer

D 0.2 Sodium Ascorbyl Phosphate

1, 0 tocopheryl acetate

0.2 bisabolol

1, 0 Caprylic / Capric Triglyceride, Sodium Ascorbate, Tocopherol, Retinol

1, 0 1% test substance 4

E q.s. Sodium hydroxides

WS 5%: test substance 4

% Ingredient (INCI)

A 1, 7 Ceteareth-6, Stearyl Alcohol

0.7 Ceteareth-25

2.0 diethylamino hydroxybenzoyl hexyl benzoate

2.0 PEG-14 Dimethicone

3.6 Cetearyl Alcohol

6.0 ethylhexyl methoxycinnamate

2.0 dibutyl adipate

B 5.0 glycerin

0.2% disodium EDTA

1, 0 panthenol q.s. preservative

63.8 Aqua the.

C 4.0 Caprylic / Capric Triglyceride, Sodium Acrylate Copolymer

D 0.2 Sodium Ascorbyl Phosphate

1, 0 tocopheryl acetate

0.2 bisabolol

1, 0 Caprylic / Capric Triglyceride, Sodium Ascorbate, Tocopherol, Retinol 5.0 5% test substance 4 E qs Sodium Hydroxide

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.

Note: 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

O / W r

WS 1%: test substance 4

% Ingredient (INCI)

A 1, 7 Ceteareth-6, Stearyl Alcohol

0.7 Ceteareth-25

2.0 diethylamino hydroxybenzoyl hexyl benzoate

2.0 PEG-14 Dimethicone

3.6 Cetearyl Alcohol

6.0 ethylhexyl methoxycinnamate

2.0 dibutyl adipate

B 5.0 glycerin

0.2% disodium EDTA

1, 0 panthenol q.s. preservative

68.6 Aqua the.

C 4.0 Caprylic / Capric Triglyceride, Sodium Acrylate Copolymer

D 1, 0 Sodium ascorbyl phosphates

1, 0 tocopheryl acetate

0.2 bisabolol

1, 0 test substance 4

E q.s. Sodium hydroxides

WS 5%: test substance 4

% Ingredient (INCI)

A 1, 7 Ceteareth-6, Stearyl Alcohol

0.7 Ceteareth-25

2.0 diethylamino hydroxybenzoyl hexyl benzoate

2.0 PEG-14 Dimethicone 3.6 Cetearyl Alcohol

6.0 ethylhexyl methoxycinnamate

2.0 dibutyl adipate

B 5.0 glycerin

0.2% disodium EDTA

1, 0 panthenol q.s. preservative

64.6 Aqua the.

C 4.0 Caprylic / Capric Triglyceride, Sodium Acrylate Copolymer

D 1, 0 Sodium ascorbyl phosphates

1, 0 tocopheryl acetate

0.2 bisabolol

5.0 test substance 4

E q.s. Sodium hydroxides

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

O / W

WS 1%: test substance 4

% Ingredient (INCI)

A 10.0 Cetearyl ethylhexanoate

10.0 Caprylic / Capric Triglycerides

1, 5 cyclopentasiloxanes, cyclohexasilosans

2.0 PEG-40 Hydrogenated Castor OiI

B3.5 Caprylic / Capric Triglycerides, Sodium Acrylates Copolymer

C 1, 0 tocopheryl acetate

0.2 bisabolol q.s. Preservatives q.s. perfume oil

D 3.0 polyquaternium-44

0.5 cocotrimonium methosulfates

0.5 ceteareth-25

2.0 Panthenol, Propylene Glycol

4.0 Propylene Glycol

0.1% disodium EDTA 1, 0 test substance 4

60.7 Aqua.

WS 5%: test substance 4

% Ingredient (INCI)

A 10.0 Cetearyl ethylhexanoate

10.0 Caprylic / Capric Triglycerides

1, 5 cyclopentasiloxanes, cyclohexasilosans

2.0 PEG-40 Hydrogenated Castor OiI

B3.5 Caprylic / Capric Triglycerides, Sodium Acrylates Copolymer

C 1, 0 tocopheryl acetate

0.2 bisabolol q.s. Preservatives q.s. perfume oil

D 3.0 polyquaternium-44

0.5 cocotrimonium methosulfates

0.5 ceteareth-25

2.0 Panthenol, Propylene Glycol

4.0 Propylene Glycol

0.1% disodium EDTA

5.0 test substance 4

56.7 Aqua the.

Preparation: Release phase A. Stir phase B into phase A, incorporate phase C into combined phases A and B. Dissolve phase D, stir into the combined phases A, B and C and homogenize. 15 minutes. stirred.

Example 8: Use of the test substance 4 in a Daily Care Body Spray

WS 1%: test substance 4% ingredient (INCI)

A 3.0 ethylhexyl methoxycinnamate

2.0 diethylamino hydroxybenzoyl hexyl benzoate

1, 0 Polyquaternium-44

3.0 Propylene Glycol 2.0 Panthenol, Propylene Glycol

1, 0 cyclopentasiloxanes, cyclohexasiloxanes

10.0 octyldodecanol

0.5 PVP

10.0 Caprylic / Capric Triglycerides 3.0 C12-15 Alkyl Benzoates

3.0 glycerin 1, 0 tocopheryl acetate

0.3 bisabolol

1, 0 test substance 4

59.2 Alcohol

WS 5%: test substance 4

% Ingredient (INCI)

A 3.0 ethylhexyl methoxycinnamate

2.0 diethylamino hydroxybenzoyl hexyl benzoate

1, 0 Polyquaternium-44

3.0 Propylene Glycol

2.0 Panthenol, Propylene Glycol

1, 0 cyclopentasiloxanes, cyclohexasiloxanes

10.0 octyldodecanol

0.5 PVP

10.0 Caprylic / Capric Triglycerides

3.0 C12-15 alkyl benzoates

3.0 glycerin

1, 0 tocopheryl acetate

0.3 bisabolol

5.0 test substance 4

55.2 Alcohol

Preparation: Weigh in the components of phase A and dissolve clearly.

Example 9: Use of the test substance 4 in a skin care gel

WS 1%: test substance 4

% Ingredient (INCI)

A 3.6 PEG-40 Hydrogenated Castor OiI

15.0 Alcohol

0.1 bisabolol

0.5 tocopheryl acetate q.s. perfume oil

B 3.0 Panthenol

0.6 carbomer

1, 0 test substance 4

75.4 Aqua,

C 0.8 triethanolamine

WS 5%: test substance 4 % Ingredient (INCI)

A 3.6 PEG-40 Hydrogenated Castor OiI

15.0 Alcohol

0.1 bisabolol

0.5 tocopheryl acetate q.s. perfume oil

B 3.0 Panthenol

0.6 carbomer

5.0 test substance 4

71, 4 Aqua,

C 0.8 triethanolamine

Preparation: Clear phase A clearly. Swell phase B and neutralize with phase C. Stir phase A into the homogenized phase B and homogenize.

Example 10: Use of the test substance 4 in an aftershave lotion

WS 1%: test substance 4

% Ingredient (INCI) A 10.0 Cetearyl Ethylhexanoate

5.0 tocopheryl acetates

1, 0 Bisabolol

0.1 perfume oil

0.3 Acrylates / CI 0-30 Alkyl Acrylate Crosspolymer B 15.0 Alcohol

1, 0 panthenol

3.0 glycerin

1, 0 test substance 4

0.1 triethanolamine 63.5 aqua dem.

WS 5%: test substance 4

% Ingredient (INCI)

A 10.0 Cetearyl Ethylhexanoate 5.0 Tocopheryl Acetates

1, 0 Bisabolol

0.1 perfume oil

0.3 acrylates / C10-30 alkyl acrylate crosspolymer

B 15.0 Alcohol 1, 0 Panthenol

3.0 glycerin 5.0 test substance 4 0.1 triethanolamine 59.5 aqua dem.

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

% Ingredient (INCI)

A 0.4 acrylates / C 10-30 alkyl acrylate crosspolymer

15.0 Cetearyl ethylhexanoates

0.2 bisabolol 1, 0 tocopheryl acetate q.s. perfume oil

B 1, 0 panthenol

15.0 Alcohol

3.0 glycerol 1, 0 test substance 4

63.2 Aqua,

C 0.2 triethanolamine

WS 5%: test substance 4% ingredient (INCI)

A 0.4 acrylates / C 10-30 alkyl acrylate crosspolymer

15.0 Cetearyl ethylhexanoates

0.2 bisabolol

1, 0 tocopheryl acetate q.s. perfume oil

B 1, 0 panthenol

15.0 Alcohol

3.0 glycerin

5.0 test substance 4 59.2 Aqua dem,

C 0.2 triethanolamine

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

% Ingredient (INCI)

A 4,5 ethylhexyl methoxycinnamate

2.0 Diethylamino Hydroxybenzoyl Hexyl Benzoate 3.0 Octocrylene

2.5 di-C12-13 alkyl malates

0.5 tocopheryl acetate

4.0 polyglyceryl-3 methyl glucose distearate

B 3.5 Cetearyl isononanoate 1, 0 VP / eicosene copolymer

5.0 isohexadecane

2.5% Di-CI 2-13 alkyl malate

3.0 Titanium dioxides, trimethoxycaprylylsilanes

C 5.0 Glycerin 1, 0 Sodium Cetearyl Sulfate

0.5 xanthan gum

59.7 Aqua the.

D 1, 0 test substance 4

1, 0 phenoxyethanol, methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben

0.3 bisabolol

WS 5%: test substance 4

% Ingredient (INCI) A 4,5 Ethylhexyl Methoxycinnamate

2.0 diethylamino hydroxybenzoyl hexyl benzoate

3.0 octocrylene

2.5% Di-CI 2-13 alkyl malate

0.5 Tocopheryl Acetate 4.0 Polyglyceryl-3 Methyl Glucose Distearate

B 3,5 Cetearyl isononanoate

1, 0 VP / eicosene copolymer

5.0 isohexadecane

2.5 Di-CI 2-13 Alkyl Malate 3.0 Titanium Dioxide, Trimethoxycaprylyl silanes

C 5.0 glycerin

1, 0 Sodium Cetearyl Sulfate

0.5 xanthan gum

55.7 Aqua. D 5.0 test substance 4

1, 0 phenoxyethanol, methylparaben, ethylparaben, butylparaben, propyl paraben, isobutyl paraben 0.3 bisabolol

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

WS 1%: Uvinul 5050 H

% Ingredient (INCI) A 2.0 Ceteareth-6, Stearyl Alcohol

2.0 Ceteareth-25

3.0 tribehenin

2.0 Cetearyl Alcohol

2.0 Cetearyl Ethylhexanoate 5.0 Ethylhexyl Methoxycinnamate

1, 0 ethylhexyl triazone

1, 0 VP / eicosene copolymer

7.0 isopropyl myristate

B 5.0 Zinc oxides, triethoxycaprylylsilanes C 0.2 xanthan gum

0.5 hydroxyethyl acrylate / sodium acryloyl dimethyl taurate copolymer,

Squalane, polysorbate 60

0.2% disodium EDTA

5.0 Propylene Glycol 0.5 Panthenol

60,9 Aqua the.

D 1, 0 test substance 4

0.5 phenoxyethanol, methylparaben, butylparaben, ethylparaben, propylparaben, isopropylparaben 1, tocopheryl acetates

0.2 bisabolol

WS 5%: test substance 4

% Ingredient (INCI) A 2.0 Ceteareth-6, Stearyl Alcohol

2.0 Ceteareth-25 3.0 tribehenin

2.0 Cetearyl Alcohol

2.0 cetearyl ethylhexanoate

5.0 ethylhexyl methoxycinnamate 1, 0 ethylhexyl triazone

1, 0 VP / eicosene copolymer

7.0 isopropyl myristate

B 5.0 Zinc oxides, triethoxycaprylylsilanes

C 0.2 xanthan gum 0.5 hydroxyethyl acrylate / sodium acryloyl dimethyl taurate copolymer,

Squalane, polysorbate 60

0.2% disodium EDTA

5.0 Propylene Glycol

0.5 Panthenol 56.9 Aqua dem.

D 5.0 test substance 4

0.5 phenoxyethanol, methylparaben, butylparaben, ethylparaben, propylpaben, isopropylparaben

1, 0 tocopheryl acetate 0.2 bisabolol

Preparation: Heat phase A to approx. 80 ^° C., stir in phase B and homogenize for 3 minutes. Also heat phase C to 80 ^° C. and stir into the combined phases A and B while homogenizing. Cool to about 40 ° C, stir in phase D and homogenize again.

Example 14: Use of the test substance 4 in a sunscreen lotion - type O / W

WS 1%: test substance 4

% Ingredient (INCI)

A 3,5 Ceteareth-6, Stearyl Alcohol

1, 5 Ceteareth-25

7.5 ethylhexyl methoxycinnamate

2.0 diethylamino hydroxybenzoyl hexyl benzoate

2.0 cyclopentasiloxanes, cyclohexasiloxanes

0.5 Bees Wax

3.0 Cetearyl Alcohol

10.0 Caprylic / Capric Triglycerides

B 5.0 Titanium Dioxide, Silica, Methicone, Alumina

C 3.0 glycerin

0.2% disodium EDTA

0.3 xanthan gum 1, 0 decyl glucosides

2.0 Panthenol, Propylene Glycol

56.3 Aqua the.

D 1, 0 test substance 4

1, 0 tocopheryl acetate

0.2 bisabolol q.s. Perfume oil q.s. preservative

WS 5%: test substance 4

% Ingredient (INCI)

A 3,5 Ceteareth-6, Stearyl Alcohol

1, 5 Ceteareth-25

7.5 ethylhexyl methoxycinnamate

2.0 diethylamino hydroxybenzoyl hexyl benzoate

2.0 cyclopentasiloxanes, cyclohexasiloxanes

0.5 Bees Wax

3.0 Cetearyl Alcohol

10.0 Caprylic / Capric Triglycerides

B 5.0 Titanium Dioxide, Silica, Methicone, Alumina

C 3.0 glycerin

0.2% disodium EDTA

0.3 xanthan gum

1, 0 decyl glucosides

2.0 Panthenol, Propylene Glycol

52.3 Aqua the.

D 5.0 test substance 4

1, 0 tocopheryl acetate

0.2 bisabolol q.s. Perfume oil q.s. preservative

Preparation: Heat phase A to approx. 80 ^° C., stir in phase B and homogenize for 3 minutes. Likewise heat phase C to 80 ⁰ C and stir with homogenization in the com- bined phases A and B. Cool to about 40 ⁰ C, stir in phase D and homogenize again.

Example 15: Use of the test substance 4 in a foot balm WS 1%: test substance 4

% Ingredient (INCI)

A 2.0 Ceteareth-6, Stearyl Alcohol

2.0 Ceteareth-25

5.0 Cetearyl ethylhexanoate

4.0 Cetyl Alcohol

4.0 glyceryl stearate

5.0 mineral oil

0.2 menthol

0.5 camphor

B 69.3 Aqua the. q.s. preservative

C 1, 0 bisabolol

1, 0 tocopheryl acetate

D 1, 0 test substance 4

5.0 Witch Hazel Extract

WS 5%: test substance 4

% Ingredient (INCI)

A 2.0 Ceteareth-6, Stearyl Alcohol

2.0 Ceteareth-25

5.0 Cetearyl ethylhexanoate

4.0 Cetyl Alcohol

4.0 glyceryl stearate

5.0 mineral oil

0.2 menthol

0.5 camphor

B 65,3 Aqua the. q.s. preservative

C 1, 0 bisabolol

1, 0 tocopheryl acetate

D 5.0 test substance 4

5.0 Witch Hazel Extract

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 nachhomogenisieren. 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

% Ingredient (INCI)

A 6.0 PEG-7 Hydrogenated Castor OiI

8.0 Cetearyl ethylhexanoates

5.0 isopropyl myristate

15.0 mineral oil

0.3 mg stearate

0.3 Aluminum Stearate

2.0 PEG-45 / Dodecyl Glycol Copolymer B 5.0 Glycerol

0.7 magnesium sulphates

55.6 Aqua the.

1, 0 test substance 4

0.5 tocopheryl acetate

0.6 bisabolol

WS 5%: test substance 4

% Ingredient (INCI) A 6.0 PEG-7 Hydrogenated Castor OiI

8.0 Cetearyl ethylhexanoates

5.0 isopropyl myristate

15.0 mineral oil

0.3 mg stearate

0.3 Aluminum Stearate

2.0 PEG-45 / dodecyl glycol copolymer

B 5.0 glycerin

0.7 magnesium sulphates

51, 6 Aqua the.

5.0 test substance 4

0.5 tocopheryl acetate

Preparation: Heat phases A and B separately from each other to approx. 85 ° C. Stir phase B into phase A and homogenize. Cool with stirring to about 40 ⁰ C, add phase C and briefly homogenize again. Cool to room temperature while stirring.

Example 17: Foam Conditioner with Fixer

WS 1%: test substance 4% ingredient (INCI) A 10.0 PVP / VA copolymer

0.2 hydroxyethyl cetyldimonium phosphates

0.2 Ceteareth-25

0.5 Dimethicone Copolyol q.s. perfume oil

10.0 Alcohol

1, 0 test substance 4

68.1 Aqua.

10.0 propane / butane

WS 5%: test substance 4

% Ingredient (INCI)

A 10.0 PVP / VA copolymer

0.2 hydroxyethyl cetyldimonium phosphates

0.2 Ceteareth-25

0.5 Dimethicone Copolyol q.s. perfume oil

10.0 Alcohol

5.0 test substance 4

64.1 Aqua.

10.0 propane / butane

Preparation: Weigh the components of phase A together, stir until everything is dissolved and bottled.

Example 18: Foam conditioner

WS 1%: test substance 4

% Ingredient (INCI) A 1, 0 Polyquaternium-4

0.5 hydroxyethyl cetyldimonium phosphates

1, 0 test substance 4 q.s. Perfume oil q.s. Preservatives 91, 5 Aqua dem.

6.0 propanes / butanes

WS 5%: test substance 4

% Ingredient (INCI) A 1, 0 Polyquaternium-4

0.5 hydroxyethyl cetyldimonium phosphates 5.0 test substance 4 qs perfume oil qs preservative

87.5 Aqua the.

6.0 propanes / butanes

Production: Weigh the components of phase A together, stir until everything is clearly dissolved and bottled.

Example 19: Foam conditioner

l%: test substance 4

% Ingredient (INCI)

1, 0 Polyquaternium-1 1

0.5 hydroxyethyl cetyldimonium phosphates

1, 0 test substance 4 q.s. Perfume oil q.s. preservative

91, 5 Aqua the.

6.0 propanes / butanes

5%: test substance 4

% Ingredient (INCI)

A 1, 0 Polyquaternium-1 1

0.5 hydroxyethyl cetyldimonium phosphates

5.0 test substance 4 q.s. Perfume oil q.s. preservative

87.5 Aqua the.

6.0 propane / butane

Example 20: Styling foam

WS 1%: test substance 4

% Ingredient (INCI)

A 0.5 Laureth-4 qs perfume oil B 77.3 Aqua the.

10.0 polyquaternium-28

1, 0 test substance 4

0.5 dimethicone copolyol

0.2 Ceteareth-25

0.2 panthenol

0.1 PEG-25 PABA

0.2 hydroxyethylcellulose

C 10.0 HFC 152 A

5%: test substance 4

% Ingredient (INCI)

0.5 Laureth-4 q.s. perfume oil

B 73,3 Aqua the.

10.0 polyquaternium-28

5.0 test substance 4

0.5 dimethicone copolyol

0.2 Ceteareth-25

0.2 panthenol

0.1 PEG-25 PABA

0.2 hydroxyethylcellulose

10.0 HFC 152 A

Preparation: Mix the components of phase A. Add the components of phase B one by one and dissolve. Fill with phase C.

Example 21: Styling foam

l%: test substance 4

% Ingredient (INCI) A 2.0 Cocotrimony Methosulfate q.s. perfume oil

B 78.5 Aqua the.

6,7 acrylates copolymer

0.6 AMP

1, 0 test substance 4 0.5 dimethicone copolyol

0.2 Ceteareth-25

0.2 panthenol

0.1 PEG-25 PABA

0.2 hydroxyethylcellulose

C 10.0 HFC 152 A

5%: test substance 4

% Ingredient (INCI)

2.0 cocotrimony methosulfate q.s. perfume oil

B 74.5 Aqua the.

6,7 acrylates copolymer

0.6 AMP

5.0 test substance 4

0.5 dimethicone copolyol

0.2 Ceteareth-25

0.2 panthenol

0.1 PEG-25 PABA

0.2 hydroxyethylcellulose

C 10.0 HFC 152 A

Example 22: Styling foam

WS 1%: test substance 4

% Ingredient (INCI)

A 2.0 cocotrimony methosulfate q.s. perfume oil

B 7.70 Polyquaternium-44

1, 0 test substance 4 q.s. preservative

79.3 Aqua the. C 10.0 propane / butane

5%: Uvinul 505 H

% Ingredient (INCI) A 2.0 Cocotrimony Methosulfate q.s. perfume oil

B 7.70 Polyquaternium-44

5.0 test substance 4 q.s. preservative

75.3 Aqua the.

C 10.0 propane / butane

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.

Example 23: Styling foam

WS 1%: test substance 4

% Ingredient (INCI)

A 2.00 cocotrimonium methosulfate q.s. perfume oil

B 72,32 Aqua the.

2.00 VP / Acrylates / Lauryl Methacrylate Copolymer

0.53 AMP

1, 00 test substance 4 0.20 ceteareth-25

0.50 panthenol

0.05 benzophenone-4

0.20 Amodimethicone, Cetrimonium Chloride, Trideceth-12

15.00 Alcohol

C 0.20 hydroxyethylcellulose

D 6,00 Propane / Butane

WS 5%: test substance 4

% Ingredient (INCI) A 2.00 cocotrimonium methosulfate qs perfume oil

B 68,32 Aqua the.

2.00 VP / Acrylates / Lauryl Methacrylate Copolymer

0.53 AMP

5.00 test substance 4

0.20 Ceteareth-25

0.50 panthenol

0.05 benzophenone-4

0.20 Amodimethicone, Cetrimonium Chloride, Trideceth-12

15.00 Alcohol

C 0.20 hydroxyethylcellulose

D 6,00 Propane / Butane

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.

Example 24: Styling foam

WS 1%: test substance 4% ingredient (INCI)

A 2.00 Cetrimonium Chloride q.s. perfume oil

B 67,85 Aqua the. 7.00 Polyquaternium-46

1, 00 test substance 4

0.20 Ceteareth-25

0.50 panthenol

0.05 Benzophenone-4 0.20 Amodimethicone, Cetrimonium Chloride, Trideceth-12

15.00 Alcohol

C 0.20 hydroxyethylcellulose

D 6,00 Propane / Butane WS 5%: test substance 4

% Ingredient (INCI)

A 2.00 Cetrimonium Chloride q.s. perfume oil

B 63,85 Aqua the.

7.00 Polyquaternium-46

5.00 test substance 4

0.20 Ceteareth-25

0.50 panthenol

0.05 benzophenone-4

0.20 Amodimethicone, Cetrimonium Chloride, Trideceth-12

15.00 Alcohol

C 0.20 hydroxyethylcellulose

D 6,00 Propane / Butane

Example 25: Styling foam

WS 1%: test substance 4

% Ingredient (INCI) A q.s. PEG-40 Hydrogenated Castor OiI q.s. perfume oil

85.5 Aqua dem.

B 7.0 Sodium Polystyrene Sulfonate

1, 0 test substance 4

0.5 Cetrimonium Bromide q.s. preservative

C 6.0 propane / butane

Styling foam

WS 5%: test substance 4

% Ingredient (INCI) A q.s. PEG-40 Hydrogenated Castor OiI q.s. perfume oil

81, 5 Aqua the.

B 7.0 Sodium Polystyrene Sulfonate

5.0 test substance 4

0.5 Cetrimonium Bromide q.s. preservative

C 6.0 propane / butane

Preparation: Solubilize phase A. Weigh phase B into phase A and solve it clearly. Adjust the pH to 6-7, fill with phase C.

Example 26: Styling foam

WS 1%: test substance 4

% Ingredient (INCI)

A qs PEG-40 Hydrogenated Castor OiI qs Perfume oil 92.0 Aqua dem. B 0.5 polyquaternium-10

1, 0 test substance 4

0.5 Cetrimonium Bromide q.s. preservative

C 6.0 propane / butane

WS 5%: test substance 4

% Ingredient (INCI)

A q.s. PEG-40 Hydrogenated Castor OiI q.s. perfume oil

88.0 Aqua the.

B 0.5 Polyquaternium-10 5.0 Test substance 4

0.5 Cetrimonium Bromide q.s. preservative

C 6.0 propane / butane

Example 27: Styling Foam

WS 1%: test substance 4

% Ingredient (INCI)

A q.s. PEG-40 Hydrogenated Castor OiI q.s. Perfume oil 82.5 Aqua dem.

B 10.0 Polyquaternium-16

1, 0 test substance 4

0.5 hydroxyethyl cetyldimonium phosphates q.s. preservative

C 6.0 propane / butane WS 5%: test substance 4

% Ingredient (INCI)

A q.s. PEG-40 Hydrogenated Castor OiI q.s. perfume oil

78.5 Aqua the.

B 10.0 Polyquaternium-16

5.0 test substance 4

0.5 hydroxyethyl cetyldimonium phosphates q.s. preservative

C 6.0 propane / butane

Example 28: Styling foam

l%: test substance 4

% Ingredient (INCI)

A 2.0 cocotrimony methosulfate q.s. perfume oil

B 84.0 Aqua dem.

2.0 Chitosan

1, 0 test substance 4

0.5 dimethicone copolyol

0.2 Ceteareth-25

0.2 panthenol

0.1 PEG-25 PABA

C 10.0 HFC 152 A

WS 5%: test substance 4% ingredient (INCI)

A 2.0 cocotrimony methosulfate q.s. perfume oil

B 80.0 Aqua dem. 2.0 Chitosan

5.0 test substance 4

0.5 dimethicone copolyol

0.2 Ceteareth-25

0.2 panthenol

0.1 PEG-25 PABA

C 10.0 HFC 152 A

Example 29: care shampoo

WS 1%: test substance 4

% Ingredient (INCI)

A 30.0 Sodium Laureth Sulfate

6.0 Sodium Cocoamphoacetate

6.0 Cocamidopropyl Betaine 3.0 Sodium Laureth Sulfate, Glycol Distearate, Cocamide MEA, Laureth-10

1, 0 test substance 4

7.7 polyquaternium-44

2.0 Amodimethicone q.s. Perfume oil q.s. preservative

1, 0 Sodium Chloride

43.3 Aqua the.

B q.s. Citric Acid

WS 5%: test substance 4

% Ingredient (INCI)

A 30.0 Sodium Laureth Sulfate

6.0 Sodium Cocoamphoacetate 6.0 Cocamidopropyl Betaine

3.0 Sodium Laureth Sulfate, Glycol Distearate, Cocamide MEA, Laureth-10

5.0 test substance 4

7.7 polyquaternium-44

2.0 Amodimethicone qs perfume oil qs preservative 1, 0 Sodium Chloride 39.3 Aqua dem.

B q.s. Citric Acid

Preparation: Mix and dissolve the components of phase A. Adjust the pH to 6-7 with citric acid.

Example 30: shower gel

l%: test substance 4

% Ingredient (INCI)

A 40.0 Sodium Laureth Sulfate

5.0 decyl glucosides

5.0 Cocamidopropyl betaines

1, 0 test substance 4

1, 0 panthenol q.s. Perfume oil q.s. preservative

2.0 Sodium Chloride

46.0 Aqua the.

B q.s. Citric Acid

W 5%: test substance 4

% Ingredient (INCI)

40.0 Sodium Laureth Sulfate

5.0 decyl glucosides

5.0 Cocamidopropyl betaines

5.0 test substance 4

1, 0 panthenol q.s. Perfume oil q.s. preservative

2.0 Sodium Chloride

42.0 Aqua the.

B q.s. Citric Acid

Preparation: Mix and dissolve the components of phase A. Adjust the pH to 6-7 with citric acid. Example 31: Shampoo

WS 1%: test substance 4

% Ingredient (INCI)

A 40.0 Sodium Laureth Sulfate

5.0 Sodium C12-15 Pareth-15 Sulfonates

5.0 Decyl Glucosides q.s. perfume oil

0.1 phytantriol

44.6 Aqua the.

1, 0 test substance 4

0.3 polyquaternium-10 1, 0 panthenol q.s. preservative

1, 0 Laureth-3

2.0 Sodium Chloride

WS 5%: test substance 4

% Ingredient (INCI)

A 40.0 Sodium Laureth Sulfate

5.0 Sodium C12-15 Pareth-15 Sulfonates

5.0 Decyl Glucosides q.s. perfume oil

0.1 phytantriol

40.6 Aqua the.

5.0 test substance 4

0.3 polyquaternium-10 1, 0 panthenol q.s. preservative

1, 0 Laureth-3

2.0 Sodium Chloride

Preparation: Mix and dissolve the components of phase A. Adjust the pH to 6-7 with citric acid. Example 32: Shampoo

1%: test substance 4

% Ingredient (INCI)

A 15.00 cocamidopropyl betaines

10.00 Disodium Cocoamphodiacetate

5.00 Polysorbate 20

5.00 decyl glucosides q.s. Perfume oil q.s. preservative

1, 00 test substance 4

0.15 guar hydroxypropyltrimonium chlorides

2.00 laureth-3

58.00 Aqua the. q.s. Citric Acid

B 3.00 PEG-150 distearate

5%: test substance 4

% Ingredient (INCI)

A 15.00 cocamidopropyl betaines

10.00 Disodium Cocoamphodiacetate

5.00 Polysorbate 20

5.00 decyl glucosides q.s. Perfume oil q.s. preservative

5.00 test substance 4

0.15 guar hydroxypropyltrimonium chlorides

2.00 laureth-3

54.00 Aqua the. q.s. Citric Acid

B 3.00 PEG-150 distearate

Production: Weigh in the components of phase A and dissolve. Adjust the pH to 6-7. Add phase B and heat to approx. 50 ^° C. Cool to room temperature while stirring. Example 33: Moisturizing Body Care Cream

WS 1%: test substance 4

% Ingredient (INCI)

A 2.0 Ceteareth-25

2.0 Ceteareth-6, Stearyl Alcohol

3.0 Cetearyl ethylhexanoate

1, 0 dimethicone

4.0 Cetearyl Alcohol

3.0 Glyceryl Stearate SE

5.0 mineral oil

4.0 Simmondsia Chinensis (Jojoba) Seed OiI

3.0 Mineral OiI, Lanolin Alcohol

B 5.0 Propylene Glycol

1, 0 test substance 4

1, 0 panthenol

0.5 Mg Aluminum Silicate Q.s Preservative

65.5 Aqua the.

q.s. perfume oil

D q.s. Citric Acid

5%: test substance 4

% Ingredient (INCI)

A 2.0 Ceteareth-25

2.0 Ceteareth-6, Stearyl Alcohol

3.0 Cetearyl ethylhexanoate

1, 0 dimethicone

4.0 Cetearyl Alcohol

3.0 Glyceryl Stearate SE

5.0 mineral oil

4.0 Simmondsia Chinensis (Jojoba) Seed OiI

3.0 Mineral OiI, Lanolin Alcohol

B 5.0 Propylene Glycol

5.0 test substance 4

1, 0 panthenol

0.5 Magnesium Aluminum Silicate qs preservative

61, 5 Aqua the.

C q.s. perfume oil

D q.s. Citric Acid

Preparation: Heat phases A and B separately to about 80 ^° C. Phase B prehomogenising briefly, then stir phase B into phase A and homogenize again ren.Abkühlen to about 40 ⁰ C, add phase C and homogenize thoroughly again. Adjust the pH to 6-7 with citric acid.

Example 34: Moisturizing Body Care Cream

WS 1%: test substance 4

% Ingredient (INCI) A 6.0 PEG-7 Hydrogenated Castor OiI

10.0 Cetearyl ethylhexanoates

5.0 isopropyl myristate

7.0 Mineral OiI

0.5 Shea Butter (Butyrospermum Parkii)

0.5 Aluminum Stearate

0.5 mg stearate

0.2 bisabolol

0.7 Quaternium-18 hectorites

B 5.0 Dipropylene glycol

0.7 magnesium sulfates q.s. preservative

62.9 Aqua.

q.s. perfume oil

1, 0 test substance 4

5%: test substance 4

% Ingredient (INCI)

6.0 PEG-7 Hydrogenated Castor OiI

10.0 Cetearyl ethylhexanoates

5.0 isopropyl myristate

7.0 Mineral OiI

0.5 Shea Butter (Butyrospermum Parkii) 0.5 Aluminum Stearate

0.5 mg stearate

0.2 bisabolol

0.7 Quaternium-18 hectorites

B 5.0 Dipropylene glycol

0.7 magnesium sulfates q.s. preservative

58.9 Aqua.

C q.s. perfume oil

5.0 test substance 4

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

l%: test substance 4

% Ingredient (INCI)

2.0 Ceteareth-6, Stearyl Alcohol

2.0 Ceteareth-25

6.0 glyceryl stearates

1, 0 Cetyl Alcohol

8.0 mineral OiI

7.0 cetearyl ethylhexanoate

0.2 dimethicone

B 3.0 Propylene glycol

1, 0 panthenol q.s. preservative

61, 9 Aqua the.

0.1 bisabolol

1, 0 test substance 4 qs perfume oil D 5.7 CI 77 891, Titanium Dioxide

1, 1 Iron Oxides

WS 5%: test substance 4

% Ingredient (INCI)

A 2.0 Ceteareth-6, Stearyl Alcohol

2.0 Ceteareth-25

6.0 glyceryl stearates

1, 0 Cetyl Alcohol

8.0 mineral OiI

7.0 cetearyl ethylhexanoate

0.2 dimethicone

B 3.0 Propylene glycol

1, 0 panthenol q.s. preservative

57.9 Aqua the.

C 0.1 bisabolol

5.0 test substance 4 q.s. perfume oil

D 5.7 C.I. 77 891, Titanium Dioxide

1, 1 Iron Oxides

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.

Example 36

In the following dermocosmetic preparations, the compounds 2- (hydroxymethyl) -3-hydroxypyridine hydrochloride according to the invention are used for the production of the dermocosmetics. In the following, this compound is referred to as test substance 4.

The test substance 4 mentioned is used as an approximately 10% strength by weight solution. The following information is parts by weight.

Clear shampoo

Clear conditioner shampoo

Foam O / W emulsions

Conditioner Shampoo with pearlescent

Adjust pH to 6.0

Clear conditioner shampoo

Adjust pH to 6.0

Clear conditioner shampoo with volume effect

Adjust pH to 6.0

Gel Cream

OW Sunscreen formulation

Hydro dispersion

Sticks

PIT emulsion

Gel Cream

OW Formulations self-tanner

Hydrodispersion self-tanner

Sticks

PIT emulsions self-tanner

oil gel

Claims

claims

1. dermocosmetics containing at least one compound of general formula 1,

wherein

X is nitrogen or CR ⁵ ;

Heteroaryl, alkylcarbonyl, alkoxycarbonyl, COOH, COOM, aminocarbonyl,

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 heteroaryl;

M is a cation equivalent;

2. dermocosmetics according to claim 1, wherein X in formula 1 is CR ⁵ .

3. dermocosmetics according to claim 1 or 2, wherein R ² in formula 1 is hydroxy.

4. Dermocosmetics according to one of the preceding claims, wherein R ³ in the compound of formula 1 is hydrogen, hydroxy, C 1 -C 6 -alkyl, hydroxy-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 -alkylamino) C 1 -C 6 -alkyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 6 -alkylamino) carbonyl or amino carbonyl.

5. dermocosmetics according to any one of the preceding claims, wherein R ¹ in the compound of formula 1 is hydrogen, Ci-C6-alkyl, Ci-Cβ-alkoxycarbonyl, COOM or COOH.

6. dermocosmetics according to any one of the preceding claims, wherein in the group CR ⁵ in the compound of formula 1 R ^{5 is} hydrogen.

7. dermocosmetics according to any one of the preceding claims, wherein R ⁴ in the compound of formula I is hydrogen.

8. dermocosmetics according to claim 1 to 6, wherein R ⁴ in the compound of formula 1 for d-Ce-alkyl, amino-d-Ce-alkyl, (Ci-C6-alkyl) amino-Ci-C ₆ -alkyl, di - (C ₁ -C ₆ -alkyl) amino-C 1 -C 6 -alkyl, phenyl-C 1 -C 6 -alkyl or phenyl, where phenyl is unsubstituted in the latter two substituents or one or two of C 1 -C ₄ -alkyl and C 1 -C ₄ -alkoxy may carry selected substituents

9. dermocosmetics according to claim 1 to 5, wherein R ⁴ and R ⁵ in the compound of formula I together with the carbon atoms of the pyridine ring to which they are attached, represent a fused ring system

10. dermocosmetics according to claim 9, wherein R ⁴ and R ⁵ in the compound of formula 1 together with the carbon atoms of the pyridine ring to which they are attached, stand for a benzene ring.

1 derermocosmetics according to claim 1 to 4, wherein R ¹ and R ^{5 are} in compounds of formula 1 together with the carbon atoms of the pyridine ring to which they are attached, a fused ring system.

12. Dermocosmetics according to claim 11, wherein R ¹ and R ⁵ in compounds of formula 1 together with the carbon atoms of the pyridine ring to which they are attached represent a 2,5-dihydrofuran ring.

13. dermocosmetic according to claim 1, characterized in that the compound according to formula 1 is 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, 6-methylpyridin-3-ol.

14. dermocosmetic according to claim 1 or 2, characterized in that at least one compound of formula 1 in a concentration of 0.001 to 30 wt.% Based on the total weight of dermokosmetischen preparation.

15. Dermocosmetics according to claims 1 to 14, characterized in that they contain at least one further cosmetic and / or dermocosmetic active ingredient in addition to at least one compound according to formula 1.

16. dermocosmetic according to claim 15, characterized in that the cosmetic and / or democosmetic active ingredient is selected from the group of natural or synthetic polymers, pigments, humectants, oils, Waxes, enzymes, minerals, vitamins, sunscreens, dyes, fragrances, antioxidants and preservatives.

17. dermocosmetics according to claims 1 to 16 in the form of an ointment, cream, emulsion, suspension, lotion, milk, paste, a gel, foam or spray.

18. Dermocosmetics according to claim 6, in the form of a skin protection agent, skin care agent, skin cleanser, hair protection agent, hair care product, hair cleanser or preparation for decorative cosmetics.

19. Use of a compound according to formula 1 as an additive for the production of dermocosmetics.

20. Use of a compound according to formula 1 for the stabilization of photosensitive and / or oxidation-sensitive substances in dermocosmetics.

21. Use according to claims 19 and 20, wherein the dermocosmetic is selected from the group of skin protection agents, skin care products, skin cleansing agents, hair protection agents, hair care products, hair cleansing preparations and preparations for decorative cosmetics.

22. Use of Dermokosmetila according to claims 1 to 18 for the prevention of radical-induced skin and / or hair damage.

23. Use of Dermokosmetila according to claims 1 to 18 for improving the appearance of the skin and / or the hair.

24. Use of a compound according to formula 1 as an antioxidant in dermocosmetics.

25. Use according to claims 19 to 23, characterized in that the compound of formula 1 is present in a concentration of 0.001 to 30 wt.% Based on the total weight of dermokosmetischen preparations.