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WO2015078554A1 - Créatine ou créatine comportant des dérivés glucuronolactones - Google Patents

Créatine ou créatine comportant des dérivés glucuronolactones Download PDF

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Publication number
WO2015078554A1
WO2015078554A1 PCT/EP2014/002952 EP2014002952W WO2015078554A1 WO 2015078554 A1 WO2015078554 A1 WO 2015078554A1 EP 2014002952 W EP2014002952 W EP 2014002952W WO 2015078554 A1 WO2015078554 A1 WO 2015078554A1
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Prior art keywords
alkyl
substituted
group
carbon atoms
chain
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German (de)
English (en)
Inventor
Christophe Carola
Marcus Brunner
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Merck Patent GmbH
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Merck Patent GmbH
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom

Definitions

  • the present invention relates to mixtures of creatine or creatinine with Glucuronolactonderivaten of formula I, as described below, and their use in preparations, in particular in formulations for changing the hue of the skin.
  • Glucuronolactone derivatives of the formula I are in part from the
  • the compounds of formula I as described below, and / or their salts, tautomers, stereoisomers and / or solvates, including mixtures thereof in all ratios, are self-tanning substances or act as tanning enhancers for dihydroxyacetone or for a mixture of self-tanning substances containing dihydroxyacetone or they for coloring keratin-containing fibers, in particular animal or human hair, suitable.
  • the compounds of formula I are capable of increasing the hue of the skin
  • the hue obtained in tanning with dihydroxyacetone or by the mixture or preparation containing dihydroxyacetone may also act as a contrast reducing agent.
  • the present invention is concerned with the task of improving the skin feel of preparations containing at least one
  • a first subject of the invention is a mixture of creatine and / or creatinine r formula I.
  • R 1 and R 2 are each independently
  • alkyl group having 1 to 30 carbon atoms and / or the alkenyl group having 1 to 30 carbon atoms may be substituted with aryl, and / or the
  • Aryl group having 6 to 12 carbon atoms by alkyl, OH, OAlkyl, NH 2) NH-alkyl, N (alkyl) 2 , C (O) alkyl, OC (O) alkyl and / or C (O) -OAikyl be substituted can
  • R 3 denotes H, a straight-chain or branched alkyl group having 1 to 30 C atoms or -C (O) R 5 ,
  • R 4 is H or OR 6 ,
  • R 5 represents a straight-chain or branched alkyl group having 1 to 30 C atoms or
  • an aryl group having 6 to 12 C atoms where the aryl group having 6 to 12 C atoms is alkyl, vinyl, OH, O-alkyl, NH 2) NH alkyl, N (alkyl) 2 , C (O) alkyl, OC ( O) alkyl and / or C (O) OAlkyl, or a straight-chain or branched alkenyl group having 2 to 30 carbon atoms, which may be substituted by an aryl group having 6 to 12 carbon atoms, wherein the aryl group with 6 up to 12 C-atoms by alkyl, OH, Oalkyl, NH 2) NH alkyl, N (alkyl) 2 , C (O) alkyl, OC (O) alkyl and / or C (O) O alkyl may be substituted, and
  • R 6 denotes H or a straight-chain or branched alkyl group having 1 to 30 C atoms
  • Aryl is an aryl group having 6 to 12 C atoms, which is optionally substituted by alkyl, OH, OAlkyl, NH 2 , NH-alkyl, N (alkyl) 2 , C (O) alkyl, OC (O) alkyl or C (O) -OAlkyl may be substituted, and
  • Alkyl denotes a straight-chain or branched alkyl group having 1 to 30 C atoms
  • the compounds of formula I may be in an open-chain form or in a furanoid or pyranoid lactone and / or lactol form and / or their salts, tautomers, stereoisomers and / or solvates, including mixtures thereof in all ratios.
  • Another object of the invention is the use of creatine and / or creatinine for the stabilization of at least one compound of formula I,
  • R 1 and R 2 are each independently
  • alkyl group having 1 to 30 carbon atoms and / or the alkenyl group having 1 to 30 carbon atoms may be substituted with aryl, and / or the
  • Aryl group having 6 to 12 carbon atoms by alkyl, OH, OAlkyl, NH 2 , NH-alkyl, N (alkyl) 2 , C (O) alkyl, OC (O) alkyl and / or C (O) -OAikyl be substituted can be substituted.
  • R 3 denotes H, a straight-chain or branched alkyl group having 1 to 30 C atoms or -C (O) R 5 ,
  • R 4 is H or OR 6 ,
  • R 5 represents a straight-chain or branched alkyl group having 1 to 30 C atoms or
  • an aryl group having 6 to 12 carbon atoms wherein the aryl group having 6 to 12 carbon atoms by alkyl, vinyl, OH, OAlkyl, NH 2 , NH alkyl, N (alkyl) 2 , C (O) alkyl, OC (O ) Alkyl or C (O) OAlkyl, or a straight-chain or branched alkenyl group having 2 to 30 carbon atoms, which may be substituted by an aryl group having 6 to 12 carbon atoms, wherein the aryl group with 6 to 12 carbon atoms by alkyl, OH, O-alkyl, NH 2, NHalkyl, N (alkyl) 2, C (O) alkyl, OC (O) alkyl and / or C (O) OAIkyl may be substituted and
  • R 6 denotes H or a straight-chain or branched alkyl group having 1 to 30 C atoms
  • Aryl is an aryl group having 6 to 12 C atoms, which is optionally substituted by alkyl, OH, OAlkyl, NH 2> NH-alkyl, N (alkyl) 2 , C (O) alkyl, OC (O) alkyl or C (O) -OAlkyl may be substituted, and
  • Alkyl denotes a straight-chain or branched alkyl group having 1 to 30 C atoms
  • the compounds of formula I may be in an open-chain form or in a furanoid or pyranoid lactone and / or lactol form and / or their salts, tautomers, stereoisomers and / or solvates, including mixtures thereof in all ratios.
  • Another object of the invention is the use of creatine and / or creatinine to improve the skin feel of a preparation containing at least one compound of formula I.
  • R 1 and R 2 are each independently
  • alkyl group having 1 to 30 carbon atoms and / or the alkenyl group having 1 to 30 carbon atoms may be substituted with aryl and / or the
  • R 3 H may be a straight-chain or branched alkyl group having 1 to 30 C atoms or -C (O) R 5 ,
  • R 4 is H or OR 6 ,
  • R 5 represents a straight-chain or branched alkyl group having 1 to 30 C atoms or
  • an aryl group having 6 to 12 carbon atoms wherein the aryl group having 6 to 12 carbon atoms by alkyl, vinyl, OH, OAlkyl, NH 2 , NH alkyl, N (alkyl) 2 , C (O) alkyl, OC (O ) Alkyl or C (O) OAlkyl, or a straight-chain or branched alkenyl group having 2 to 30 carbon atoms, which may be substituted by an aryl group having 6 to 12 carbon atoms, wherein the aryl group with 6 to 12 C atoms may be substituted by alkyl, OH, OAlkyl, NH 2 , NHalkyl, N (alkyl) 2 , C (O) alkyl, OC (O) alkyl and / or C (O) OAlkyl and
  • R 6 denotes H or a straight-chain or branched alkyl group having 1 to 30 C atoms
  • Aryl is an aryl group having 6 to 12 C atoms, which is optionally substituted by alkyl, OH, OAlkyl, NH 2 , NH-alkyl, N (alkyl) 2 , C (O) alkyl, OC (O) alkyl or C (O) -OAlkyl may be substituted, and
  • Alkyl denotes a straight-chain or branched alkyl group having 1 to 30 C atoms
  • skin according to the invention also includes the scalp.
  • Solvates are e.g. Mono or dihydrate or alcoholates.
  • salts of the compounds of the formula I as described above are preferably pharmaceutically or cosmetically acceptable.
  • a base of formula I can with an acid in the associated
  • Acid addition salt can be converted, for example, by reacting equivalent amounts of the base and the acid in an inert
  • Solvents such as ethanol and subsequent evaporation.
  • Particularly suitable acids for this reaction are those which yield physiologically acceptable salts.
  • compounds of formula I can be converted with bases (e.g., sodium or potassium hydroxide or carbonate) into the corresponding metal, especially alkali metal or alkaline earth metal, or into the corresponding ammonium salts.
  • bases e.g., sodium or potassium hydroxide or carbonate
  • Tautomers are molecules with the same molecular formula whose atoms are linked differently, which rapidly change into each other due to the migration of individual atoms or groups of atoms. H. the two isomers are in rapid chemical equilibrium.
  • Stereoisomers are molecules that have the same bond of the atoms and functional groups in a different spatial structure exhibit. Typical examples of stereoisomers are enantiomers and diastereomers.
  • Enantiomers are molecules that behave like mirror images and can not be converted into each other by twisting bonds. Mixtures of enantiomers in the ratio 1: 1 are referred to as racemates.
  • Diastereomers are all stereoisomeric molecules that do not behave like mirror images.
  • Formula 1-1 visualizes the diastereomers of formula I based on ⁇ -D - (+) - glucuronic acid 3,6-lactone and ⁇ -D - (+) - glucuronic acid 3,6-lactone:
  • R 1 , R 2 , R 3 and R 4 have the meaning given above.
  • a straight-chain or branched alkyl group having 1 to 10 C atoms is, for example, methyl, ethyl, / isopropyl, propyl, butyl, sec-butyl or tert-butyl, pentyl, 1-, 2- or 3-methylbutyl, 1,1 -, 1, 2- or 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-heptyl, n-octyl, n-nonyl or n-decyl.
  • a straight-chain or branched alkyl group having 1 to 30 carbon atoms comprises the previously described group of straight-chain or straight chain alkyl groups
  • alkyl as used herein means a straight-chain or branched alkyl group having 1 to 30 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably methyl, ethyl, isopropyl, n -propyl or n-butyl
  • O-Alkyl is known to the person skilled in the art and denotes a straight-chain or branched alkoxy group having 1 to 30 C atoms.
  • the names are derivable from the names of the alkyl group in which the suffix -oxygen is appended.
  • the alkoxy group OMethyl is, for example, methyloxy.
  • NHalkyl means a monoalkylated amino group wherein the alkyl group may be straight-chain or branched and has 1 to 30 carbon atoms
  • N (alkyl) 2 accordingly denotes a
  • Dialkylamino group wherein the alkyl group is independently
  • a straight-chain or branched alkenyl having 2 to 30 C atoms, wherein several double bonds may also be present, is, for example, ethenyl, allyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, furthermore 4-pentenyl, iso-pentenyl, Hexenyl, heptenyl, octenyl, -C9H17, -C10H19 to -C30H49; preferably ethenyl, allyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, 4-pentenyl, iso-pentenyl, hexenyl or decenyl.
  • Particularly preferred alkenyl groups are ethenyl, 2- or 3-butenyl.
  • An aryl group having 6 to 12 C atoms means phenyl, naphthyl,
  • Anthracenyl or phenanthryl which may be substituted by alkyl, OH, Oalkyl, NH 2) NH-alkyl, N (alkyl) 2 , C (O) alkyl, OC (O) -alkyl or C (O) -Oalkyl.
  • the aryl group is unsubstituted or substituted by alkyl, OH, OAlkyl, NH 2 , NH-alkyl, N (alkyl) 2 , C (O) alkyl, OC (O) -alkyl or C (O) -OAlkyl substituted phenyl.
  • R 1 and R 2 together form a five-membered ring
  • Double bonds may be substituted by at least one
  • Phenyl group may be substituted, wherein the phenyl group by alkyl, OH, Oalkyl, C (O) alkyl, OC (O) alkyl and / or C (O) -OAlkyl may be substituted;
  • Phenyl group may be substituted by alkyl, OH, OAlkyl, C (O) alkyl, O-C (O) alkyl and / or C (O) -OAlkyl,
  • R 3 is H or -C (O) R 5 ,
  • R 4 is H
  • R 5 represents a straight-chain or branched alkyl group having 1 to 12 C atoms or
  • an aryl group having 6 to 12 C atoms wherein the aryl group having 6 to 12 C-atoms by alkyl, vinyl, OH, OAlkyl, NH 2) NH alkyl, N (alkyl) 2 , C (O) alkyl, OC (O ) Alkyl and / or C (O) OAlkyl or a straight-chain or branched alkenyl group having 2 to 12 carbon atoms, which may be substituted by an aryl group having 6 to 12 carbon atoms, wherein the aryl group having 6 to 12 C atoms may be substituted by alkyl, OH, OAlkyl, NH 2 , NHalkyl, N (alkyl) 2 , C (O) alkyl, OC (O) alkyl and / or C (O) OAlkyl
  • Alkyl is a straight-chain or branched alkyl group having 1 to 12 C atoms.
  • R and R 2 are H or
  • R 1 and R 2 together form a five-membered ring
  • R 3 is H or -C (O) R 5 ,
  • R 4 is H
  • R 5 represents a straight-chain or branched alkyl group having 1 to 12 C atoms or
  • an aryl group having 6 to 12 C atoms wherein the aryl group having 6 to 12 C-atoms by alkyl, vinyl, OH, OAlkyl, NH 2 , NH alkyl, N (alkyl) 2 , C (O) alkyl, OC (O ) Alkyl and / or C (O) OAlkyl or a straight-chain or branched alkenyl group having 2 to 12 carbon atoms, which may be substituted by an aryl group having 6 to 12 carbon atoms, wherein the aryl group having 6 to 12 C atoms can be substituted by alkyl, OH, OAlkyl, NH 2 , NHalkyl, N (alkyl) 2 , C (O) alkyl, OC (O) alkyl and / or C (O) OAlkyl
  • Alkyl is a straight-chain or branched alkyl group having 1 to 12 C atoms.
  • mixture according to the invention can also be two or more
  • a very particularly preferred mixture according to the invention consists of creatine and a compound of the formula (1), (2), (3) or (9).
  • creatine is used for stabilization.
  • creatine is used for stabilization.
  • creatine stabilizes a compound of formula (1), (2), (3) or (9) in a preparation.
  • the compounds of the formula I, 1-1, (1) to (29) are in part commercially available or can be prepared by processes which are described in
  • WO 2012/010242 or WO 2013/083225 are described, whose content in this regard expressly also belongs to the disclosure of the present application.
  • the formation of the five-membered ring is formed, for example, by (Lewis) -acid-catalyzed reaction of the corresponding glucuronolactone, in which R 1 and R 2 signify OH, with acetone.
  • Suitable reaction conditions for esterifications with the aid of active esters are described in Esterification: Methods, Reactions, and Applications, Author: Prof. Dr. med. Junzo Otera, Wiley-VCH Verlag GmbH & Co. KGaA, ISBN 9783527304905, described,
  • Another object of the invention are also preparations containing creatine and / or creatinine and at least one compound of formula I or of formula 1-1 and / or their salts, tautomers,
  • Stereoisomers and / or solvates including mixtures thereof in all proportions, as described above or described as being preferred or corresponding to the formulas (1) to (29).
  • Another object of the invention are also preparations containing the inventive mixture of creatine and / or creatinine with one or more compounds of the formula I or the formula 1-1 and / or their salts, tautomers, stereoisomers and / or solvates, including mixtures thereof in all proportions as described above or described as preferred or according to the formulas (1) to (29).
  • Another object of the invention is also the use of a mixture of creatine and / or creatinine with a compound of formula I, as described above or described as preferred, in cosmetic, pharmaceutical or dermatological preparations or
  • the preparations are preferably topically applicable preparations, for example cosmetic or cosmetic preparations
  • compositions in this case contain a cosmetically or dermatologically suitable carrier and, as appropriate
  • the preparations in this case contain a pharmaceutically acceptable carrier and optionally further pharmaceutical active ingredients. If it is a medical device, then a compatible carrier for the medical device is selected.
  • agent or formulation is used synonymously in addition to the term preparation.
  • compositions may comprise or contain, consist essentially of or consist of the stated necessary or optional ingredients. Any compounds or components which may be used in the compositions are either known and commercially available or may be synthesized by known methods.
  • cosmetic or dermatological preparations or medical products are preferred. According to the invention, cosmetic preparations or medical products are particularly preferred.
  • cosmetic preparations are very particularly preferred.
  • the preparation preferably contains creatine and / or creatinine and the compound (s) of the formula I or 1-1, as described above, in a molar ratio of 3: 1 to 0.4: 1, preferably in a molar ratio of 2: 1 up to 0.8: 1. If creatine and creatinine are used together, the total amount for the molar ratio is decisive. The same applies to several compounds of the formula I or of the formula 1-1 in relation to creatine and / or creatinine.
  • Another object of the invention is therefore the preparation as described above or described as preferred, wherein creatine and / or creatinine and the compound (s) of the formula I, as described above or described as preferred, in a molar ratio of 3: 1 to 0.4: 1 are present in the preparation.
  • the preparations according to the invention have a pH which is 3.5 to 5, preferably 4 to 5, more preferably 4.
  • the preparation contains the at least one compound of formula I or 1-1, as described above or described as preferred, in an amount of 0.01 to 20 wt .-%, particularly preferably in an amount of 0.5 to 15 wt .-% and most preferably in an amount of 1 to 8 wt .-%, based on the total amount of the preparation.
  • the preparation according to the invention preferably contains, as before
  • Another object of the invention is therefore the preparation, as described above or described as preferred, wherein at least one further self-tanning substance is included.
  • Suitable self-tanning substances are dihydroxyacetone,
  • Erythrulose and dihydroxyacetone are particularly preferably used. Erythrulose or dihydroxyacetone is particularly preferably used. Most preferably, dihydroxyacetone is preferred.
  • the principle of staining to form melanoid is that
  • the preparation according to the invention preferably contains, as before
  • At least one further active ingredient as "biologically active
  • Tanning substance in which it effects an increase in melanin synthesis, an improvement in melanin transport and / or an improvement in the distribution of melanin in suprabasal layers
  • biologically active self-tanning substances are published in WO 2012/097857.
  • Representative of this class of compounds is the substance hexadecanoic acid 5-hydroxy-2-methyl-4-oxo-4H-chromen-7-yl ester, which is marketed under the name RonaCare® Bronzyl TM by Merck, Darmstadt.
  • Symrise's SymBronze® 1659 microalgae extract
  • MelanoBronze Alcetyl Tyrosine, Vitex agnus-castus extract
  • Mibelle Melatime TM
  • TM butylene Glycol, Palmitoyl Tripeptide-40
  • Melactiva TM maltodextrin, Mucuna pruriens seed extract
  • Unipertan® butylene glycol, acetyl tyrosine, hydrolyzed vegetable protein, riboflavin
  • Phototan® sorbitol, ornithine HCl, tyrosine, arginine, HCI, silica
  • the preparation contains at least dihydroxyacetone in an amount of 0.01 to 20 wt .-%, particularly preferably in an amount of 0.5 to 15 wt .-% and most preferably in an amount of 1 to 8 wt .-%, based on the total amount of the preparation.
  • the preparation according to the invention containing at least one compound of formula I or 1-1, as described above or described as preferred, and the individual compounds and at least one self-tanner, preferably also formaldehyde scavenger, and optionally flavonoids to improve the odor.
  • the formaldehyde scavenger is selected from the group consisting of alkali metal, alkaline earth metal or ammonium metabisulfite.
  • a preparation containing in combination DHA Plus is a product blend containing sodium metabisulfite, equivalent to Na 2 S 2 O 5 or INCI: sodium disulfite, for masking, elimination or neutralization of formaldehyde.
  • flavonoids can be used to improve the fragrance
  • Smell and optionally be included for tanning is a flavonoid in which one or more phenolic hydroxy groups are blocked by etherification or esterification.
  • Flavonoids such as preferably troxerutin, troxequercetin, troxeisoquercetin or troxeluteolin, and flavonoid sulphates or
  • Flavonoid phosphates such as preferably rutin sulfates, proved to be particularly suitable flavonoids.
  • Particularly preferred flavonoids are rutin sulfate and troxerutin.
  • melanogenesis inhibiting substances already causes
  • hyperpigmented skin areas lose their high melanin concentrations and the hue generated by the colorant on the skin surface is widely spread.
  • melanogenesis inhibitors such as e.g.
  • Licorice extract ascorbyl glucoside, 3-O-ethyl ascorbyl ether, 2-O-ethyl ascorbyl ether, kojic acid, kojisuredipalmitate, resorcinol, glutathione, cysteine, mulberry extract, hydrogen peroxide, zinc peroxide, sodium peroxide, benzoyl peroxide, glucosamine, aloesin, oleic acid 4-isopropyl-catechol, Emblica, glycolic acid, ellagic acid, ferulic acid, resveratrol, oxyresveratrol, quercetin, kaempferol,
  • Bile acid Bile acid, hesperidin, p-coumaric acid, epicatechingallate,
  • Epigallocatechin gallate ⁇ -hydroxycarboxylic acids (e.g., lactic acid,
  • Preferred melanogenesis inhibitors are ascorbic acid and its derivatives, niacinamide, emblica, ellagic acid, mulberry extract, kojic acid, liquorice root extract, rucinol,
  • the formulations may preferably contain excipients, such as cosmetic oils (e.g., Caprylic / Capric Triglycerides, C12-15 alkyl benzoates, isopropyl myristate, arylalkyl benzoates, e.g.
  • cosmetic oils e.g., Caprylic / Capric Triglycerides, C12-15 alkyl benzoates, isopropyl myristate, arylalkyl benzoates, e.g.
  • Phenethylbenzoate (X-Tend 226) or Cosmacol brand Olole components such as dimyristyl tartrate, tri C14-C15 alkyl citrate, C12-C13 alkyl lactate, tridecyl salicylate, C12-C13 alkyl octanoate, C12-C13 alkyl maleate, C12-C13 alkyl citrate , C12-C13 alkyl tartrates), or polar protic auxiliaries (eg propylene glycol, glycerol, isopropanol, ethanol) or so-called.
  • Olole components such as dimyristyl tartrate, tri C14-C15 alkyl citrate, C12-C13 alkyl lactate, tridecyl salicylate, C12-C13 alkyl octanoate, C12-C13 alkyl maleate, C12-C13 alkyl citrate , C12-C13 alky
  • Solubilizers e.g., butylphthalimides, isopropylphthalimides,
  • Dimethylisosorbide Dimethylisosorbide.
  • Very particularly preferred cosmetic oils are C12-C13 alkyl lactates, commercially available as Cosmacol ELI and
  • Phenethylbenzoate commercially available as X-Tend 226.
  • the invention also provides a process for the preparation of a preparation as described above, wherein at least one compound according to formula I or 1-1, as described above or described as preferred, mixed with at least one carrier suitable for cosmetic, pharmaceutical, dermatological preparations and, where appropriate, with other excipients or fillers, as well
  • Dihydroxyacetone are added, then added last as dihydroxyacetone and mixed.
  • Suitable excipients and active or auxiliary substances have already been described in detail previously or in the following part.
  • the described preparations may furthermore also contain color pigments, the layer structure of the pigments not being limited.
  • the color pigment when used from 0.5 to 5 wt .-% should be skin-colored or brownish.
  • Pigments is familiar to the skilled person.
  • the preparations described may also contain hydrophilic or lipophilic sunscreen filters that are effective in the UVA range and / or UVB range and / or IR and / or VIS range (absorber). These substances can in particular under
  • Cinnamic acid derivatives Cinnamic acid derivatives, salicylic acid derivatives, camphor derivatives,
  • Suitable organic UV-protective substances are preferably to be selected from the following list:
  • PABA para-aminobenzoic acid and its derivatives: PABA, ethyl PABA, ethyl dihydroxypropyl PABA, ethylhexyl dimethyl PABA, e.g. B. sold under the name "Escalol 507" from the company.
  • ISP glyceryl PABA, PEG-25 PABA, z. B. sold under the name "Uvinul P25” from the company.
  • BASF para-aminobenzoic acid and its derivatives: PABA, ethyl PABA, ethyl dihydroxypropyl PABA, ethylhexyl dimethyl PABA, e.g. B. sold under the name "Escalol 507" from the company.
  • ISP glyceryl PABA, PEG-25 PABA, z. B. sold under the name "Uvinul P25” from the company.
  • BASF para-aminobenzoic acid and its derivatives: PABA
  • Salicylates homosalates sold under the name "Eusolex HMS” by Merck; Ethyl hexyl salicylates, e.g. B. sold under the name “Neo Heliopan OS” from the Fa. Symrise, Dipropylene glycol salicylate, z. B. sold under the name “Dipsal” from the company. Scher, TEA salicylates, z. B. marketed under the name "Neo Heliopan TS" of the Fa. Symrise. ⁇ , ⁇ -diphenylacrylate derivatives: octocrylenes, e.g. B.
  • Benzophenone Derivatives Benzophenone-1, e.g. Sold under the name "Uvinui 400"; Benzophenone-2, e.g. Sold under the name “Uvinui D50”; Benzophenone-3 or oxybenzone, e.g. Sold under the name “Uvinui M40”; benzophenone-4, e.g. Sold under the name "Uvinui MS40”; Benzophenone-9, e.g. B. sold under the
  • Benzophenone-8 e.g. Sold under the name "SpectraSorb UV-24” by American Cyanamid, benzophenone-12 n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate or 2-hydroxy-4-methoxybenzophenone, sold by Merck, Darmstadt under the name Eusolex® 4360.
  • Benzylidene camphor derivatives 3-Benzylidenecamphor, z. Sold under the name "Mexoryl SD” from the company. Chimex, 4-Methylbenzylidene- camphor, z. B.
  • Terephthalylidenedicamphorsulfonic acid e.g. Sold under the name "Mexoryl SX” from the company Chimex, polyacrylamidomethylbenzylidene camphor under the name “Mexoryl SW” from the company. Chimex. Phenylbenzimidazole derivatives: phenylbenzimidazolesulfonic acid, e.g. B.
  • Phenylbenzotriazole derivatives Drometrizole trisiloxanes, e.g. Sold under the name “Silatrizole” by the company. Rhodia Chimie, Methylenebis (benzotriazolyl) tetramethylbutylphenol in solid form, for. B. marketed under the name "MIXXIM BB / 100" from the company. Fairmount Chemical, or in micronized form as an aqueous dispersion, eg. B. marketed under the name "Tinosorb M” from BASF.
  • Triazine derivatives ethylhexyltriazone, e.g. B. sold under the name "Uvinul T150" from the company. BASF, Diethylhexylbutamidotriazone, z. B.
  • Anthraniline derivatives menthyl anthranilate, e.g. B. marketed under the name "Neo Heliopan MA" by Fa. Symrise.
  • Imidazole derivatives ethylhexyldimethoxybenzylidenedioxoimidazoline propionate.
  • Benzalmalonate Derivatives Polyorganosiloxanes containing functional benzalmalonate groups, e.g. Polysilicone-15, e.g. Sold under the name "Parsol SLX” by Hoffmann LaRoche.
  • 4,4-Diarylbutadiene derivatives 1,1-dicarboxy (2,2'-dimethylpropyl) -4,4-diphenylbutadiene.
  • Benzoxazole derivatives 2,4-bis [5- (1-dimethylpropyl) benzoxazol-2-yl (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazines, e.g. B. sold under the name Uvasorb K2A from the company. Sigma 3V and mixtures containing this.
  • organic UV filters are usually incorporated in formulations in an amount of from 0.01 percent by weight to 20 percent by weight, preferably 1 percent by weight to 10 percent by weight.
  • the preparations may also contain inorganic UV filters, so-called particulate UV filters. These combinations with particulate UV filters are possible both as a powder and as a dispersion or paste.
  • coated titanium dioxide for example Eusolex ® T-2000, Eusolex ® T-AQUA,
  • Eusolex ® T-AVO Eusolex ® T-OLEO
  • zinc oxides for example Sachtotec® ®
  • Iron oxides or else cerium oxides and / or zirconium oxides are preferred.
  • the preparations may further be preferred if the preparations contain inorganic UV filters which are prepared by customary methods, such as, for example, in US Pat
  • Aftertreatment components can be selected: amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids
  • fatty acids fatty acid alcohols, anionic surfactants, lecithin, phospholipids, sodium, potassium, zinc, iron or aluminum salts of fatty acids, polyethylenes, silicones, proteins (especially collagen or elastin), alkanolamines, silica, alumina, other metal oxides, Phosphates, such as sodium hexametaphosphate or glycerin.
  • inorganic UV filters are usually incorporated in the formulations in an amount of from 0.1 percent by weight to 25 percent by weight, preferably 2 percent by weight to 10 percent by weight.
  • UV filters can also be used in encapsulated form.
  • organic UV filters it is beneficial to use organic UV filters in
  • Preferred preparations may also comprise at least one further cosmetic active ingredient, for example selected from
  • Antioxidants anti-aging, anti-wrinkle, anti-dandruff, anti-acne, deodorant, anti-cellulite, skin lightening or vitamins.
  • the protective effect against oxidative stress or against the action of free radicals can be improved if the agents or preparations according to the invention contain one or more antioxidants, wherein the expert does not encounter any difficulties in selecting suitable fast or delayed-acting antioxidants.
  • Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives esters, ethers, peptides, lipids, nucleotides, nucleosides and salts
  • sulfoximine compounds for example buthionine sulfoximines
  • Homocysteine sulfoximine, buthionine sulfone, penta-, hexa-, heptathionin sulfoximine) in very low tolerated dosages eg pmol to ⁇ / kg
  • also (metal) chelators eg ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin
  • cc-hydroxy acids eg citric acid, lactic acid, malic acid
  • humic acid Bile acids, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives, vitamin C and derivatives (eg ascorbyl palmitate,
  • ZnO, ZnSO 4 zinc and its derivatives
  • selenium and its derivatives eg selenium methionine
  • stilbenes and their derivatives eg stilbene oxide , trans-stilbene oxide.
  • Suitable antioxidants are also compounds of the general
  • R 1 can be selected from the group -C (O) CH 3 , -CO 2 R 3 , -C (O) NH 2 and -C (O) N (R 4 ) 2 ,
  • X is O or NH
  • R 2 is linear or branched alkyl having 1 to 30 C atoms
  • R 3 is linear or branched alkyl having 1 to 20 C atoms
  • R 4 each independently of one another are H or linear or branched alkyl having 1 to 8 C atoms
  • R 5 is linear or branched alkyl having 1 to 8 C atoms or linear or branched alkoxy having 1 to 8 C atoms and
  • R 6 denotes linear or branched alkyl having 1 to 8 C atoms, preferably derivatives of 2- (4-hydroxy-3,5-dimethoxybenzylidene) malonic acid and / or 2- (4-hydroxy-3,5-dimethoxybenzyl) - malonic acid, particularly preferably 2- (4-hydroxy-3,5-dimethoxybenzylidene) malonic acid bis- (2-ethylhexyl) ester (for example Oxynex ® ST Liquid) and / or 2- (4-hydroxy-3,5 dimethoxybenzy ) malonic acid-bis (2-ethylhexyl) ester (example RonaCare ® AP).
  • antioxidants are also suitable for use in the compositions or preparations according to the invention.
  • Known and commercial mixtures mixtures are, for example comprising, as active ingredients, lecithin, L - (+) - ascorbyl palmitate and citric acid (for example (for example Oxynex ® AP), natural tocopherols, L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and citric acid (for example Oxynex ® K LIQUID), tocopherol extracts from natural sources, L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and citric acid (for example Oxynex ® L LIQUID), DL-tocopherol c, L - (+) - ascorbyl palmitate, citric acid and lecithin (for example Oxynex ® LM) or butylhydroxytoluene (BHT), L - (+) -.
  • lecithin for example
  • antioxidants are reacted with compounds of formula I in such compositions is typically in ratios ranging from 1000: 1 to 1: 1000, preferably used in amounts of 100: 1 to 1: 100.
  • Suitable anti-aging agents especially for skin care
  • Preparations are preferably so-called compatible solutes.
  • compatible solute substances are selected from the group consisting of Pyrimidincarbonklaren (such as ectoine and
  • Additional anti-aging agents such as 5,7-dihydroxy-2-methyl-chromone, marketed under the trade name RonaCare®l_uremine, or the commercial products RonaCare®lsoquercetin, RonaCare®Tilirosid or RonaCare®Cyclopeptide 5 can be used.
  • compositions to be used may be further ingredients
  • vitamins and vitamin derivatives selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamin chloride hydrochloride (vitamin Bi), riboflavin (vitamin B 2 ),
  • Nicotinic acid amide vitamin C (ascorbic acid), vitamin D, ergocalciferol (vitamin D 2 ), vitamin E, DL- ⁇ -tocopherol, tocopherol E acetate, tocopherol hydrogen succinate, vitamin Esculin (vitamin P active ingredient), thiamin (vitamin Bi ), Nicotinic acid (niacin), pyridoxine, pyridoxal, pyridoxamine, (vitamin B 6 ), pantothenic acid, biotin, folic acid and cobalamin (vitamin B 12 ), particularly preferably vitamin A palmitate, vitamin C and its derivatives, DL-a- Tocopherol, tocopherol-E-acetate, nicotinic acid,
  • Pantothenic acid and biotin are usually added to the flavonoid-containing premixes or preparations when applied cosmetically in the range of 0.01% to 5.0% by weight, based on the total weight.
  • retinoids are also effective anti-cellulite agents.
  • Another well-known anti-cellulite drug is caffeine.
  • compounds of the invention can be combined with all active ingredients and excipients, as they are systematically listed in WO2009 / 098139. In particular, these substances belong to those listed therein
  • Agents for stimulating fibroblast or keratinocyte proliferation and / or keratinocyte differentiation include “Agents for promoting the maturation of the horny envelope”, “NO-synthase inhibitors”, “Peripheral benzodiazepine receptor (PBR) antagonists”, “Agents for increasing the activity of the sebaceous glands ",” Agents for stimulating the energy metabolism of cells “,” Tensioning agents ",” Fat-reducing agents “,” Sliming agents “,” Agents for promoting the cutaneous microcirculation ",” Calmatives or anti-irritants " , “Sebo-regulating or anti-seborrhoic agents”, “Astringents”, “Cicatrizing agents”, “Anti-inflammatory agents”, “Anti-acne agents”.
  • the content of WO 2009/098139 expressly also belongs to the disclosure content of the present application.
  • Suitable constituents of the preparation can be incorporated in the usual way, by means of techniques which are well known to the person skilled in the art.
  • Suitable preparations for external use for example as a cream or milk (OW, W / O, O / W / O, W / OW), as a lotion or emulsion, in the form of oily-alcoholic, oily-aqueous or aqueous-alcoholic gels or solutions can be sprayed onto the skin. They can be present as solid pens or be packaged as aerosol.
  • preparations to be used are preferably mentioned: solutions, suspensions, emulsions, PIT emulsions, pastes, Ointments, gels, creams, lotions, powders, soaps, surfactant-based cleansing preparations, oils, aerosol patches, envelopes, bandages and sprays.
  • Preferred excipients come from the group of preservatives, stabilizers, solubilizers, colorants, odor improvers.
  • Ointments, pastes, creams and gels may contain the usual excipients suitable for topical administration, e.g. animal and vegetable fats, waxes, paraffins, starch, tragacanth,
  • Cellulose derivatives Polyethylene glycols, silicones, bentonites, silicic acid, talc and zinc oxide or mixtures of these substances.
  • Powders and sprays may contain the usual carriers, e.g. Lactose, talc, silicic acid, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances.
  • Sprays may additionally contain the usual volatilized, liquefied propellants, e.g.
  • Solutions and emulsions may contain the usual excipients such as solvents, solubilizers and emulsifiers, e.g. Water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 3-butylglycol, oils, in particular cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerin fatty acid esters, polyethylene glycols and fatty acid esters of sorbitan or mixtures thereof Contain substances.
  • solvents e.g. Water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 3-butylglycol, oils, in particular cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, gly
  • a preferred solubilizer in general is 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine methyl ester.
  • Suspensions may be the customary carriers such as liquid diluents, for example water, ethanol or propylene glycol, suspending agents, for example ethoxylated isostearyl alcohols, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar and tragacanth or mixtures of these substances.
  • Soaps may contain the usual excipients such as alkali metal salts of fatty acids, salts of fatty acid monoesters, fatty acid protein hydrolysates, isothionates, lanolin, fatty alcohol, vegetable oils, plant extracts, glycerol, sugars or mixtures of these substances.
  • Surfactant-containing cleaning products may include the usual excipients such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates, sulfosuccinic acid monoesters, fatty acid hydrolysates, isothionates, imidazolinium derivatives, methyltauate, sarcosinates, fatty acid amide ether sulfates, alkyl amidobetaines, fatty alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable and synthetic oils, lanolin derivatives, ethoxylated Glycerine fatty acid esters or mixtures of these substances.
  • excipients such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates, sulfosuccinic acid monoesters, fatty acid hydrolysates, isothionates, imidazolinium derivatives, methyltauate, sarcosinates, fatty acid
  • Facial and body oils may contain the usual carriers such as synthetic oils such as fatty acid esters, fatty alcohols, silicone oils, natural oils such as
  • Vegetable oils and oily vegetable extracts paraffin oils, lanolin oils or mixtures of these substances.
  • the preferred preparation forms include, in particular, emulsions.
  • Emulsions are advantageous and contain z.
  • the lipid phase can advantageously be selected from the following substance group:
  • Oils such as triglycerides of capric or caprylic, further natural oils such. Castor oil;
  • Fats, waxes and other natural and synthetic fats preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes,
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions in the context of the present invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or or unsaturated,
  • branched and / or unbranched alcohols of a chain length of 3 to 30 carbon atoms, from the group of esters of aromatic carboxylic acid and saturated and / or unsaturated, branched and / or
  • unbranched alcohols of a chain length of 3 to 30 carbon atoms unbranched alcohols of a chain length of 3 to 30 carbon atoms.
  • the aqueous phase of the preparations to be used contains
  • alcohols, diols or polyols of low carbon number, and their ethers preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, -monoethyl- or -monobutylether, diethylene glycol monomethyl or -monoethylether and analogous products, furthermore low C-number alcohols, e.g. As ethanol, isopropanol, 1, 2-propanediol,
  • Glycerol and in particular one or more thickening agents which or which can be advantageously selected from the group Silica, aluminum silicates, polysaccharides or their derivatives, for example hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of so-called carbopols, for example Carbopols types 980, 981, 1382, 2984, 5984, respectively individually or in combination.
  • a polyacrylate from the group of so-called carbopols for example Carbopols types 980, 981, 1382, 2984, 5984, respectively individually or in combination.
  • the preparation may contain cosmetic adjuvants which are commonly used in this type of preparations, e.g.
  • Thickeners emollients, moisturizers,
  • surfactants emulsifiers, preservatives, antifoaming agents, perfumes, waxes, lanolin, propellants, dyes and / or pigments, and other ingredients commonly used in cosmetics. Even without further explanation it is assumed that a
  • Glucuronolactone of the formula (1) or glucuronolactone acetonide of the formula (2) are mixed with creatine or creatinine. After 24 hours, the pH is found to be 4 for creatine and 5 for creatinine. This pH remains unchanged for at least 8 weeks.
  • the pH is measured directly with the device Portamess Type 911 XpH from Knick.
  • the error of the measurement is measured at values of 0.2 to 0.3.
  • Formulation example 1 O / W tanning cream
  • phases A and B are heated separately to 75 ° C. Thereafter, phase A is slowly added to phase B with gentle stirring. It is homogenized at 65 ° C for one minute. The mixture is then cooled with stirring to 40 ° C and the phase C was added with stirring, cooled to 35 ° C and the phase D was added, and further cooled.
  • phases A and B are heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A and homogenized. It is then cooled and the phase C at 40 ° C was added.
  • Rhodicare S (7) XANTHAN GUM 0.2 D
  • phases A and B are mixed separately and heated to 75 ° C. Thereafter, phase C is added to phase B and added to phase A with stirring. It is homogenized. It is then cooled with stirring and the phases D and E at 40 ° C was added.
  • Formulation example 4 O / W tanning cream with UV A B protection
  • phases A and B are mixed separately and heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A. It is homogenized and cooled to 40 ° C and added phase C, then cooled to room temperature.
  • phases A and B are heated separately to 75 ° C. Thereafter, Phase A is slowly added to Phase B with stirring. At 60 ° C, Phase C is added to A / B and it is homogenized. It is then cooled to 40 ° C and the phases D and E are added successively.

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  • Life Sciences & Earth Sciences (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne des mélanges de créatine ou de créatine comportant des dérivés glucuronolactones et leur utilisation dans des préparations, en particulier des préparations servant à modifier la couleur de la peau.
PCT/EP2014/002952 2013-11-26 2014-11-04 Créatine ou créatine comportant des dérivés glucuronolactones Ceased WO2015078554A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2569560A (en) * 2017-12-19 2019-06-26 Pz Cussons Beauty Llp Tanning Composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5385938A (en) * 1986-12-23 1995-01-31 Yu; Ruey J. Method of using glycolic acid for treating wrinkles
US5702688A (en) * 1986-12-23 1997-12-30 Tristrata Technology, Inc. Amphoteric compositions and polymeric forms of alpha hydroxyacids, and their therapeutic use
WO2005077327A1 (fr) * 2004-02-11 2005-08-25 Beiersdorf Ag Formulations autobronzantes cosmetiques et dermatologiques contenant de la dihydroxyacetone et de la glycerine
WO2013083225A1 (fr) * 2011-12-08 2013-06-13 Merck Patent Gmbh Dérivés du glucuronolactone comme substances auto-bronzantes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5385938A (en) * 1986-12-23 1995-01-31 Yu; Ruey J. Method of using glycolic acid for treating wrinkles
US5385938B1 (en) * 1986-12-23 1997-07-15 Tristrata Inc Method of using glycolic acid for treating wrinkles
US5702688A (en) * 1986-12-23 1997-12-30 Tristrata Technology, Inc. Amphoteric compositions and polymeric forms of alpha hydroxyacids, and their therapeutic use
WO2005077327A1 (fr) * 2004-02-11 2005-08-25 Beiersdorf Ag Formulations autobronzantes cosmetiques et dermatologiques contenant de la dihydroxyacetone et de la glycerine
WO2013083225A1 (fr) * 2011-12-08 2013-06-13 Merck Patent Gmbh Dérivés du glucuronolactone comme substances auto-bronzantes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2569560A (en) * 2017-12-19 2019-06-26 Pz Cussons Beauty Llp Tanning Composition

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