WO2011047981A1 - Utilisation d'une dialkylphényl-4-aminopipéridine en tant qu'agent pour le traitement de la perspiration humaine ; nouveaux composés et compositions associés - Google Patents

Utilisation d'une dialkylphényl-4-aminopipéridine en tant qu'agent pour le traitement de la perspiration humaine ; nouveaux composés et compositions associés Download PDF

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Publication number
WO2011047981A1
WO2011047981A1 PCT/EP2010/065182 EP2010065182W WO2011047981A1 WO 2011047981 A1 WO2011047981 A1 WO 2011047981A1 EP 2010065182 W EP2010065182 W EP 2010065182W WO 2011047981 A1 WO2011047981 A1 WO 2011047981A1
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Prior art keywords
saturated
denotes
unsaturated
linear
cox
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PCT/EP2010/065182
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English (en)
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Maria Dalko
Alexandre Cavezza
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L'oreal
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Publication of WO2011047981A1 publication Critical patent/WO2011047981A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants

Definitions

  • the invention relates to the use of a dialkylphenyl-4-aminopiperidine compound as agent for the treatment of human perspiration in a cosmetic composition .
  • the invention also relates to a cosmetic method for treating perspiration and optionally the body odours related to human perspiration, in particular axillary odours.
  • aluminium and/or zirconium salts in topical application as antiperspirants , which salts have the effect of limiting, indeed even suppressing, the flow of sweat.
  • Metal salts of this type are effective as antiperspirant active principle but some people find that the application of such products results in skin irritation. Furthermore, the aluminium salts block a portion of the sweat by the formation of a partial plug in the sweat duct and give the consumer the impression of an unnatural control of the perspiration.
  • dialkylphenyl-4-aminopiperidine compounds make it possible to achieve this objective and can easily be formulated in numerous products intended to reduce perspiration, without it being necessary to use conventional astringent salts.
  • the invention thus relates to the use of a dialkylphenyl-4-aminopiperidine compound as agent for the treatment of human perspiration in a composition comprising a cosmetically acceptable vehicle.
  • Another subject-matter of the present invention is a cosmetic method for the treatment of human perspiration and optionally of body odours, in particular axillary odours, which consists in applying, to the surface of the skin, a composition comprising, in a cosmetically acceptable medium, at least one dialkylphenyl-4-aminopiperidine compound .
  • cosmetically acceptable is understood to mean compatible with the skin and/or its superficial body growths, exhibiting a pleasant colour, a pleasant odour and a pleasant feel, and not causing unacceptable discomfort (smarting, tightness, redness) liable to dissuade the consumer from using this composition.
  • agent for the treatment of perspiration is understood to mean any substance which has the effect of reducing the flow of sweat and/or of reducing the feeling of dampness related to human sweat and/or of masking human sweat.
  • dialkylphenyl-4-aminopiperidine compounds in accordance with the invention are chosen in particular from those corresponding to the following formula (I) :
  • Alki and Alk2 denote, independently of one another, a saturated Ci-Cio or unsaturated C2-C 1 0 linear or saturated or unsaturated C3-C 10 branched alkylene radical (divalent radical) ;
  • - Ari denotes a phenyl group optionally substituted by one or more identical or different radicals chosen from -F, -CF 3 , -R 1 , -OR 1 , -NR X R 2 or -COX;
  • - Ar 2 denotes a phenyl group optionally substituted by one or more identical or different radicals chosen from -F, -CF 3 , -NR X R 2 or -COX;
  • - X denotes OR 1 , NHR 1 or NR X R 2 ;
  • - R denotes a hydrogen atom or a saturated or unsaturated Ci-Cio linear or C3-C10 branched alkyl radical optionally substituted by a group chosen from -Ari, -OR 1 or -NR X R 2 ;
  • R 1 and R 2 denote, independently of one another, a saturated C 1 -C7 or unsaturated C 2 -C 7 linear or saturated or unsaturated C3-C 7 branched or cyclic alkyl radical; and their salts, optical isomers and solvates.
  • the alkyl groups can in particular be chosen, as the case may be, from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl groups.
  • the divalent alkylene groups can be chosen from methylene, ethylene, n-propylene, isopropylene, n-butylene, isobutylene, tert-butylene, pentylene, hexylene, heptylene, octylene, nonylene or decylene radicals.
  • Alki and Alk 2 denote, independently of one another, a saturated C 1 -C4 linear alkylene radical
  • R 1 is a saturated C 1 -C4 linear or branched alkyl.
  • Ar 2 denotes an unsubstituted phenyl group.
  • - Alki denotes -CH 2 -CH 2 -
  • - Alk 2 denotes -CH 2 CH 2 CH 2 -.
  • the acceptable salts of the compounds described in the present invention comprise conventional nontoxic salts of the said compounds, such as those formed from organic or inorganic acids. Mention may be made, for example, of the salts of inorganic acids, such as sulphuric acid, hydrochloric acid, hydrobromic acid or phosphoric acid. Mention may also be made of the salts of organic acids which can comprise one or more carboxylic, sulphonic or phosphonic acid groups. They can be linear, branched or cyclic aliphatic acids or also aromatic acids. These acids can additionally comprise one or more heteroatoms chosen from 0 and N, for example in the form of hydroxyl groups.
  • the preferred salts are those obtained from hydrochloric acid, sulphuric acid, acetic acid, tartaric acid, citric acid or lactic acid.
  • the acceptable solvates of the compounds described in the present invention comprise conventional solvates, such as those formed during the final stage of preparation of the said compounds due to the presence of solvents. Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.
  • dialkylphenyl-4-aminopiperidine compounds in accordance with the invention are preferably used in amounts ranging from 0.001% to 20% of the total weight of the composition and more preferably in an amount representing from 0.01% to 10% of the total weight of the composition and more preferably still from 0.1 to 5%.
  • the amounts of active principle will be adjusted according to the formulation form of the composition comprising them.
  • the compounds of formula (I) can be prepared according to the methods of preparation described in Application EP 1 849 456.
  • the aldehyde (II) (1 equivalent) is dissolved in an organic solvent (for example CH 2 CI 2 ) and reacted with 4-piperidone monohydrate hydrochloride (1 equivalent) and an organic base (for example triethylamine) (1 equivalent) .
  • Bead molecular sieve is added to the reaction mixture, which is stirred at between 20 and 60°C for from 1 h to 5 h.
  • 1 to 5 equivalents of a hydride for example sodium triacetoxyborohydride
  • the molecular sieve beads are subsequently filtered off.
  • the organic phase is washed with water and then with a saturated sodium chloride solution.
  • the organic phase is subsequently dried and then concentrated as much as possible.
  • the oil obtained is purified by chromatography on silica gel.
  • Another subject-matter of the invention is a cosmetic composition
  • a cosmetic composition comprising, in a cosmetically acceptable medium, at least one compound of formula (I) as defined above in which one of the phenyl groups Ari and Ar 2 is substituted by at least one COX group, in particular just one COX group.
  • composition according to the invention can be provided in all the formulation forms conventionally used for a topical application and in particular in the form of aqueous gels or of aqueous or aqueous/alcoholic solutions. They can also, by addition of a fatty or oily phase, be provided in the form of dispersions of the lotion type, of emulsions with a liquid or semiliquid consistency of the milk type, obtained by dispersion of a fatty phase in an aqueous phase (O/W) or vice versa (W/O), or of suspensions or emulsions with a soft, semisolid or solid consistency of the cream or gel type, or also of multiple (W/O/W or 0/W/O) emulsions, of microemulsions , of vesicular dispersions of ionic and/or nonionic type, or of wax/aqueous phase dispersions. These compositions are prepared according to the normal methods.
  • the invention also relates to compositions packaged in pressurized form in an aerosol device or in a pump-action spray, packaged in a device equipped with an openwork wall, in particular a grating, or packaged in a device equipped with a ball applicator (roll-on) , characterized in that they comprise at least perlite particles as defined above.
  • they comprise the ingredients generally used in products of this type which are well known to a person skilled in the art .
  • compositions according to the invention can be anhydrous .
  • Anhydrous composition is understood to mean a composition comprising less than 2% by weight of water, indeed even less than 0.5% by weight of water, and in particular devoid of water, the water not being added during the preparation of the composition but corresponding to the residual water contributed by the mixed ingredients.
  • antiperspirant compositions according to the invention can also be provided in the form of sticks.
  • compositions for treating perspiration according to the invention can also be provided in the form of a loose or compact powder.
  • compositions according to the invention intended for cosmetic use can comprise at least one aqueous phase.
  • They are in particular formulated as aqueous lotions, as a water-in-oil or oil-in-water emulsion or as a multiple emulsion (oil-in-water-in-oil or water-in-oil-in-water triple emulsion) (such emulsions are known and described, for example, by C. Fox in "Cosmetics and Toiletries", November 1986, Vol. 101, pages 101-112).
  • the aqueous phase of the said compositions comprises water and generally other solvents which are soluble or miscible in water.
  • the solvents which are soluble or miscible in water comprise short-chain, for example C1-C4, monoalcohols , such as ethanol or isopropanol ; or diols or polyols, such as ethylene glycol, 1 , 2-propylene glycol, 1,3-butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether and sorbitol.
  • Use will more particularly be made of propylene glycol and glycerol, 1 , 3-propanediol .
  • emulsifiers which can be used in oil-in-water emulsions or oil-in-water-in-oil triple emulsions, for example, of nonionic emulsifiers, such as oxyalkylenated (more particularly polyoxyethylenated) esters of fatty acids and of glycerol; oxyalkylenated esters of fatty acids and of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) esters of fatty acids; oxyalkylenated (oxyethylenated and/or oxypropylenated) ethers of fatty alcohols; sugar esters, such as sucrose stearate; and their mixtures, such as the mixture of glyceryl stearate and of PEG-40 stearate.
  • nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) esters of
  • fatty alcohol/alkylpolyglycoside emulsifying mixtures such as are described in Applications WO 92/06778, WO 95/13863 and WO 98/47610, for example the commercial products sold by SEPPIC under the MONTANOV® names.
  • fatty alcohol/alkylpolyglycoside emulsifying mixtures such as are described in Applications WO 92/06778, WO 95/13863 and WO 98/47610, for example the commercial products sold by SEPPIC under the MONTANOV® names.
  • Water-in-oil emulsifiers such as are described in Applications WO 92/06778, WO 95/13863 and WO 98/47610, for example the commercial products sold by SEPPIC under the MONTANOV® names.
  • emulsifiers which can be used in water-in-oil emulsions or water-in-oil- in-water-in-oil triple emulsions or triple emulsions, by way of example, of alkyl dimethicone copolyols corresponding to the following formula (I) :
  • Ri denotes a linear or branched C 1 2-C20 and preferably -Ci8 alkyl group
  • R3 denotes a hydrogen atom or a linear or branched alkyl radical comprising from 1 to 12 carbon atoms;
  • a is an integer ranging from 1 to approximately 500;
  • b denotes an integer ranging from 1 to approximately 500;
  • n is an integer ranging from 2 to 12 and preferably from 2 to 5;
  • x denotes an integer ranging from 1 to approximately 50 and preferably from 1 to 30;
  • y denotes an integer ranging from 0 to approximately 49 and preferably from 0 to 29, with the proviso that, when y is other than zero, the ratio x/y is greater than 1 and preferably varies from 2 to 11.
  • R 4 denotes the group : --C m H 2m -- ( -OC 2 H 4 - ) s -- ( -OC 3 H 6 - ) t __ 0—R 5 ;
  • R5 denotes a hydrogen atom or a linear or branched alkyl radical comprising from 1 to 12 carbon atoms;
  • c is an integer ranging from 1 to approximately 500;
  • d denotes an integer ranging from 1 to approximately
  • n is an integer ranging from 2 to 12 and preferably from 2 to 5;
  • s denotes an integer ranging from 1 to approximately 50 and preferably from 1 to 30;
  • t denotes an integer ranging from 0 to approximately 50 and preferably from 0 to 30;
  • Use will more particularly be made of a mixture of PEG-18/PPG-18 Dimethicone and Cetyl PEG/PPG-10/1 Dimethicone and more particularly still of a mixture of Cyclopentasiloxane (and) PEG-18/PPG-18 Dimethicone and of Cetyl PEG/PPG-10/1 Dimethicone and Dimethicone or of Polyglyceryl-4 Stearate and Cetyl PEG/PPG-10 (and) Dimethicone (and) Hexyl Laurate .
  • APG alkylpolyglycosides
  • nonionic emulsifiers derived from fatty acid and from polyol of esters of fatty acid and of polyol, the fatty acid having in particular a C8-C24 alkyl chain and the polyols being, for example, glycerol and sorbitan.
  • esters of fatty acid and of polyol Mention may in particular be made, as esters of fatty acid and of polyol, of esters of isostearic acid and of polyols, esters of stearic acid and of polyols, and their mixtures, in particular the esters of isostearic acid and of glycerol and/or of sorbitan.
  • esters of stearic acid and of polyols of the polyethylene glycol esters, such as PEG-30 Dipolyhydroxystearate, such as the product sold under the name Arlacel P135 by ICI.
  • esters of glycerol and/or of sorbitan for example of polyglycerol isostearate, such as the product sold under the name Isolan GI 34 by Goldschmidt ; sorbitan isostearate, such as the product sold under the name Arlacel 987 by ICI; sorbitan isostearate and glycerol, such as the product sold under the name Arlacel 986 by ICI; the mixture of sorbitan isostearate and of polyglycerol (3 mol) isostearate sold under the name Arlacel 1690 by Uniqema; and their mixtures.
  • polyglycerol isostearate such as the product sold under the name Isolan GI 34 by Goldschmidt
  • sorbitan isostearate such as the product sold under the name Arlacel 987 by ICI
  • sorbitan isostearate and glycerol such as the product sold under the name Arlacel 986 by ICI
  • the emulsifier can also be chosen from alkylpolyglycosides having an HLB of less than 7, for example those represented by the following general formula ( 1 ) :
  • R represents a branched and/or unsaturated alkyl radical comprising from 14 to 24 carbon atoms
  • G represents a reduced sugar comprising from 5 to 6 carbon atoms and x denotes a value ranging from 1 to 10 and preferably from 1 to 4, and G denotes in particular a glucose, fructose or galactose.
  • the unsaturated alkyl radical can comprise one or more ethylenic unsaturations and in particular one or two ethylenic unsaturations.
  • This alkylpolyglucoside can be used as a mixture with a coemulsifier, more especially with a fatty alcohol and in particular a fatty alcohol having the same fatty chain as that of the alkylpolyglucoside, that is to say comprising from 14 to 24 carbon atoms and having a branched and/or unsaturated chain, for example isostearyl alcohol when the alkylpolyglucoside is isostearyl glucoside and oleyl alcohol when the alkylpolyglucoside is oleyl glucoside, optionally in the form of a self-emulsifying composition, such as described, for example, in the document WO-A-92/06778.
  • Use may be made, for example, of the isostearyl glucoside and isostearyl alcohol mixture sold under the name Montanov WO 18 by SEPPIC and the octyldodecanol and octyldodecyl xyloside mixture sold under the name Fludanov 20X by SEPPIC.
  • polyolefins comprising a succinic ending such as polyisobutylenes comprising an esterified succinic ending and their salts, in particular the diethanolamine salts, such as the products sold under the names Lubrizol 2724, Lubrizol 2722 and Lubrizol 5603 by Lubrizol or the commercial product Chemcinnate 2000.
  • the total amount of emulsifiers in the composition will preferably be in the composition according to the invention at active material contents ranging from 1 to 8% by weight and more particularly from 2 to 6% by weight, with respect to the total weight of the composition.
  • compositions according to the invention can comprise at least one water-immiscible liquid organic phase.
  • the latter generally comprises one or more hydrophobic compounds which render the said phase immiscible in water.
  • the said phase is liquid (in the absence of structuring agent) at ambient temperature (20-25°C).
  • the water-immiscible liquid organic phase in accordance with the invention generally comprises at least one volatile oil and/or one nonvolatile oil and optionally at least one structuring agent.
  • Oil is understood to mean a fatty substance which is liquid at ambient temperature (25°C) and atmospheric pressure (760 mmHg, i.e. 105 Pa) .
  • the oil can be volatile or nonvolatile.
  • Volatile oil is understood to mean, within the meaning of the invention, an oil capable of evaporating on contact with the skin or keratinous fibre in less than one hour, at ambient temperature and atmospheric pressure.
  • the volatile oils of the invention are volatile cosmetic oils which are liquid at ambient temperature and which have a nonzero vapour pressure, at ambient temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40 000 Pa (10 ⁇ 3 to 300 mmHg), in particular ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg), and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg) .
  • Nonvolatile oil is understood to mean an oil which remains on the skin or keratinous fibre, at ambient temperature and atmospheric pressure, for at least several hours and which has in particular a vapour pressure of less than 10 ⁇ 3 mmHg (0.13 Pa) .
  • the oil can be chosen from any physiologically acceptable and in particular cosmetically acceptable oil, especially mineral, animal, vegetable or synthetic oils, in particular volatile or nonvolatile hydrocarbon and/or silicone and/or fluorinated oils and their mixtures .
  • hydrocarbon oil is understood to mean an oil comprising mainly carbon and hydrogen atoms and optionally one or more functional groups chosen from hydroxyl, ester, ether or carboxyl functional groups.
  • the oil exhibits a viscosity of 0.5 to 100 000 mPa-s, preferably of 50 to 50 000 mPa-s and more preferably of 100 to 300 000 mPa-s.
  • volatile hydrocarbon oils chosen from hydrocarbon oils having from 8 to 16 carbon atoms and in particular Cs-Ci 6 isoalkanes of petroleum origin (also known as isoparaffins ) , such as isododecane (also known as 2 , 2 , 4 , 4 , 6-pentamethylheptane) , isodecane, isohexadecane and, for example, the oils sold under the Isopar or Permethyl trade names, branched Cs-Ci 6 esters, isohexyl neopentanoate and their mixtures.
  • Other volatile hydrocarbon oils such as petroleum distillates, in particular those sold under the name Shell Solt by Shell, can also be used; volatile linear alkanes, such as those described in Patent Application WO 2007/068371.
  • volatile silicones such as, for example, volatile linear or cyclic silicone oils, in particular those having a viscosity ⁇ 8 centistokes (8 ⁇ 10 ⁇ 6 m 2 /s) and having in particular from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups having from 1 to 10 carbon atoms.
  • volatile silicone oil which can be used in the invention, of octamethyl- cyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyl- trisiloxane, heptamethyloctyltrisiloxane, hexamethyl- disiloxane, octamethyltrisiloxane, decamethyl- tetrasiloxane or dodecamethylpentasiloxane, and
  • R represents an alkyl group comprising from 2 to 4 carbon atoms, one or more hydrogen atoms of which can be replaced by a fluorine or chlorine atom.
  • nonvolatile oil which can be used in the invention, of:
  • hydrocarbon oils of animal origin such as perhydrosqualene
  • - vegetable hydrocarbon oils such as liquid triglycerides of fatty acids having from 4 to 24 carbon atoms, such as triglycerides of heptanoic or octanoic acids or also wheat germ, olive, sweet almond, palm, rapeseed, cottonseed, alfalfa, poppy, pumpkinseed, cucumber, blackcurrant seed, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, musk rose, sunflower, maize, soybean, grape seed, sesame, hazelnut, apricot, macadamia, castor or avocado oils, triglycerides of caprylic/capric acids, such as those sold by Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by Dynamit Nobel, jojoba oil or shea butter;
  • hydrocarbons of mineral or synthetic origin such as liquid paraffins and their derivatives, liquid petrolatum, polydecenes, polybutenes, hydrogenated polyisobutene, such as Parleam, or squalane;
  • esters in particular of fatty acids, such as oils of formula R 1 COOR 2 in which Ri represents the residue of a linear or branched higher fatty acid comprising from 1 to 40 carbon atoms and R 2 represents a hydrocarbon chain, in particular a branched hydrocarbon chain, comprising from 1 to 40 carbon atoms with R x + R 2 ⁇ 10, such as, for example, Purcellin oil (cetearyl octanoate) , isononyl isononanoate, isopropyl myristate, isopropyl palmitate, C12 to C15 alkyl benzoate, hexyl laurate, diisopropyl adipate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate or tridecyl trimellitate
  • - fatty alcohols which are liquid at ambient temperature and which comprise a branched and/or unsaturated carbon chain having from 12 to 26 carbon atoms, such as octyldodecanol , isostearyl alcohol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol or oleyl alcohol;
  • - higher fatty acids such as oleic acid, linoleic acid or linolenic acid
  • oils which optionally comprise a hydrocarbon and/or silicone part, such as fluorosilicone oils, fluoropolyethers or fluorosilicones, such as described in the document EP-A-847752;
  • silicone oils such as nonvolatile linear or cyclic polydimethylsiloxanes (PDMSs) ; polydimethylsiloxanes comprising pendant alkyl, alkoxy or phenyl groups or alkyl, alkoxy or phenyl groups at the end of the silicone chain, which groups have from 2 to 24 carbon atoms; or phenylated silicones, such as phenyl trimethicones , phenyl dimethicones , phenyl (trimethyl- siloxy) diphenylsiloxanes , diphenyl dimethicones, diphenyl (methyldiphenyl ) trisiloxanes or (2-phenyl- ethyl) trimethylsiloxysilicates, and
  • PDMSs nonvolatile linear or cyclic polydimethylsiloxanes
  • phenylated silicones such as phenyl trimethicones , phenyl dimethicones ,
  • compositions according to the invention comprising a fatty phase can additionally comprise at least one structuring agent for the said fatty phase which can preferably be chosen from waxes, pasty compounds, inorganic or organic lipophilic gelling agents and their mixtures.
  • the wax is generally a lipophilic compound which is solid at ambient temperature (25°C), which exhibits a reversible solid/liquid change in state and which has a melting point of greater than or equal to 30°C which can range up to 200°C and in particular up to 120°C.
  • the waxes suitable for the invention can exhibit a melting point of greater than or equal to 45°C and in particular of greater than or equal to 55°C.
  • the melting point corresponds to the temperature of the most endothermic peak observed by thermal analysis (DSC) as described in Standard ISO 11357-3; 1999.
  • the melting point of the wax can be measured using a differential scanning calorimeter (DSC) , for example the calorimeter sold under the name "MDSC 2920" by TA Instruments.
  • the measurement protocol is as follows: A 5 mg sample of wax placed in a crucible is subjected to a first rise in temperature ranging from -20°C to 100°C at a heating rate of 10°C/minute, is then cooled from 100°C to -20°C at a cooling rate of 10°C/minute and, finally, is subjected to a second rise in temperature ranging from -20°C to 100°C at a heating rate of 5°C/minute. During the second rise in temperature, the variation in the difference in power absorbed by the empty crucible and by the crucible comprising the sample of wax is measured as a function of the temperature.
  • the melting point of the compound is the value of the temperature corresponding to the tip of the peak of the curve representing the variation in the difference in power absorbed as a function of the temperature.
  • the waxes capable of being used in the compositions according to the invention are chosen from waxes of animal, vegetable, mineral or synthetic origin, and their mixtures, which are solid at ambient temperature .
  • waxes suitable for the invention of hydrocarbon waxes, such as beeswax, lanolin wax and Chinese insect waxes; rice bran wax, carnauba wax, candelilla wax, ouricury wax, alfa wax, berry wax, shellac wax, Japan wax and sumac wax; montan wax, orange and lemon waxes, refined sunflower wax, sold under the name sunflower wax by Koster Keunen, microcrystalline waxes, paraffin waxes and ozokerite; polyethylene waxes, the waxes obtained by the Fischer- Tropsch synthesis and waxy copolymers, and their esters .
  • hydrocarbon waxes such as beeswax, lanolin wax and Chinese insect waxes
  • montan wax, orange and lemon waxes, refined sunflower wax sold under the name sunflower wax by Koster Ke
  • Mention may also be made of waxes obtained by catalytic hydrogenation of animal or vegetable oils having linear or branched C8-C32 fatty chains. Mention may in particular be made, among these, of isomerized jojoba oil, such as the transisomerized partially hydrogenated jojoba oil manufactured or sold by Desert Whale under the commercial reference Iso-Joj oba-50®, hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil and di ( 1 , 1 , 1-trimethylolpropane) tetrastearate, sold under the name of Hest 2T-4S® by Heterene.
  • isomerized jojoba oil such as the transisomerized partially hydrogenated jojoba oil manufactured or sold by Desert Whale under the commercial reference Iso-Joj oba-50®, hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil and di ( 1 , 1 , 1-trimethylolpropan
  • silicone waxes C30-45 alkyl dimethicone
  • fluorinated waxes C30-45 alkyl dimethicone
  • waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol which are sold under the names of Phytowax Castor 16L64® and 22L73® by Sophim. Such waxes are described in Application FR-A-2 792 190.
  • Use may be made, as wax, of a C2o _ C 4 o alkyl (hydroxystearyloxy) stearate (the alkyl group comprising from 20 to 40 carbon atoms), alone or as a mixture.
  • Such a wax is sold in particular under the names “Kester Wax K 82 P®”, “Hydroxypolyester K 82 P®” and “Kester Wax K 80 P®” by Koster Keunen.
  • microwaxes which can be used in the compositions according to the invention, of carnauba microwaxes, such as that sold under the name of MicroCare 350® by Micro Powders, synthetic wax microwaxes, such as that sold under the name of MicroEase 114S® by Micro Powders, the microwaxes composed of a mixture of carnauba wax and of polyethylene wax, such as those sold under the names of MicroCare 300® and 310® by Micro Powders, the microwaxes composed of a mixture of carnauba wax and of synthetic wax, such as that sold under the name MicroCare 325® by Micro Powders, polyethylene microwaxes, such as those sold under the names of Micropoly 200®, 220®, 220L® and 250S® by Micro Powders, the commercial products Perfomalen 400 Polyethylene and Performalene 500-L Polyethylene from New Phase Technologies, Performalene 655 Polyethylene or paraffin waxes, such as the wax having the INCI name Microcristall
  • composition according to the invention will preferably comprise a content of wax(es) ranging from 3 to 20% by weight, with respect to the total weight of the composition, in particular from 5 to 15% by weight and more particularly from 6 to 15% by weight.
  • Pasty compound is understood to mean, within the meaning of the present invention, a lipophilic fatty compound which exhibits a reversible solid/liquid change in state, which exhibits an anisotropic crystalline arrangement in the solid state and which comprises, at a temperature of 23°C, a liquid fraction and a solid fraction.
  • the pasty compound is preferably chosen from synthetic compounds and compounds of vegetable origin.
  • a pasty compound can be obtained by synthesis from starting materials of vegetable origin.
  • esters of an oligomeric glycerol in particular diglycerol esters, in particular condensates of adipic acid and of glycerol, for which a portion of the hydroxyl groups of the glycerols have reacted with a mixture of fatty acids, such as stearic acid, capric acid, stearic acid, isostearic acid and 12-hydroxy- stearic acid, such as in particular those sold under the Softisan 649 brand by Sasol,
  • the choice will preferably be made, among pasty compounds of vegetable origin, of a mixture of soybean sterols and of oxyethylenated (5 EO) /oxypropylenated (5 PO) pentaerythritol sold under the reference Lanolide by Vevy.
  • inorganic lipophilic gelling agent of optionally modified clays, such as hectorites modified by a Cio to C22 ammonium chloride, such as hectorite modified by distearyldimethylammonium chloride, such as, for example, that sold under the name Bentone 38V® by Elementis.
  • optionally modified clays such as hectorites modified by a Cio to C22 ammonium chloride, such as hectorite modified by distearyldimethylammonium chloride, such as, for example, that sold under the name Bentone 38V® by Elementis.
  • pyrogenic silica optionally hydrophobically treated at the surface, the size of the particles of which is less than 1 ym. This is because it is possible to chemically modify the surface of the silica by chemical reaction which results in a decrease in the number of silanol groups present at the surface of the silica.
  • Silanol groups can in particular be replaced by hydrophobic groups: a hydrophobic silica is then obtained.
  • the hydrophobic groups can be trimethylsiloxyl groups, which are obtained in particular by treatment of pyrogenic silica in the presence of hexamethyldisilazane .
  • Silicas thus treated are named "Silica silylate" according to the CTFA (8th edition, 2000) .
  • Silicas thus treated are named "Silica dimethyl silylate” according to the CTFA (8th edition, 2000) . They are, for example, sold under the references Aerosil R972® and Aerosil R974® by Degussa and Cab-O-Sil TS-610® and Cab-O-Sil TS-720® by Cabot.
  • the hydrophobic pyrogenic silica exhibits in particular a particle size which can be from nanometric to micrometric, for example ranging approximately from 5 to 200 nm.
  • the polymeric organic lipophilic gelling agents are, for example, partially or completely crosslinked organopolysiloxane elastomers with a three-dimensional structure, such as those sold under the names of KSG6®, KSG16® and KSG18® by Shin-Etsu, of Trefil E-505C® and Trefil E-506C® by Dow Corning, of Gransil SR-CYC®, SR DMF10®, SR-DC556®, SR 5CYC gel®, SR DMF 10 gel® and SR DC 556 gel® by Grant Industries and of SF 1204® and JK 113® by General Electric; ethylcellulose, such as that sold under the name Ethocel® by Dow Chemical; galactomannans comprising from one to six and in particular from two to four hydroxyl groups per monosaccharide and substituted by a saturated or unsaturated alkyl chain, such as guar gum alkylated by Ci to C6 and in particular Ci to C3
  • lipophilic gelling agent of polymers with a weight-average molecular weight of less than 100 000 comprising a) a polymer backbone having hydrocarbon repeat units provided with at least one heteroatom and optionally b) at least one optionally functionalized pendant fatty chain and/or at least one optionally functionalized terminal fatty chain having from 6 to 120 carbon atoms and being bonded to these hydrocarbon units, such as described in Applications WO-A-02/056847, WO-A-02/47619, the contents of which are incorporated by way of reference, in particular polyamide resins (especially comprising alkyl groups having from 12 to 22 carbon atoms) , such as those described in US-A-5783657, the content of which is incorporated by way of reference.
  • lipophilic gelling agents which can be used in the compositions according to the invention, of esters of dextrin and of fatty acid, such as dextrin palmitates, in particular such as those sold under the names Rheopearl TL® and Rheopearl KL® by Chiba Flour.
  • silicone polyamides of the polyorganosiloxane type such as those described in the documents US-A-5 874 069, US-A-5 919 441, US-A- 6 051 216 and US-A-5 981 680.
  • silicone polymers can belong to the following two families:
  • compositions according to the invention can additionally comprise one or more aluminium and/or zirconium salts or complexes.
  • the antiperspirant salts or complexes in accordance with the invention are generally chosen from aluminium and/or zirconium salts or complexes. They are preferably chosen from aluminium hydrohalides; aluminium zirconium hydrohalides, or complexes of zirconium hydroxychloride and of aluminium hydroxychloride, with or without an amino acid, such as those described in Patent US-3 792 068.
  • aluminium salts of aluminium chlorohydrate in the activated or nonactivated form, aluminium chlorohydrex, the aluminium chlorohydrex polyethylene glycol complex, the aluminium chlorohydrex propylene glycol complex, aluminium dichlorohydrate, the aluminium dichlorohydrex
  • aluminium zirconium salts of aluminium zirconium octachloro- hydrate, aluminium zirconium pentachlorohydrate,
  • aluminium zirconium tetrachlorohydrate or aluminium zirconium trichlorohydrate aluminium zirconium tetrachlorohydrate or aluminium zirconium trichlorohydrate .
  • the complexes of zirconium hydroxychloride and of aluminium hydroxychloride with an amino acid are generally known under the name ZAG (when the amino acid
  • glycine 3 is glycine (glycine) . Mention may be made, among these products, of the aluminium zirconium octachlorohydrex glycine, aluminium zirconium pentachlorohydrex glycine, aluminium zirconium tetrachlorohydrex glycine and aluminium zirconium trichlorohydrex glycine complexes.
  • the antiperspirant salts or complexes can be present in the composition according to the invention in a proportion of approximately 0.5 to 25% by weight, with respect to the total weight of the composition.
  • compositions according to the invention can additionally comprise one or more deodorant active principles .
  • the deodorant active principles can be bacteriostatic agents or bactericidal agents acting on the microorganisms of axillary odours, such as 2,4,4'- trichloro-2 ' -hydroxydiphenyl ether ( Triclosan) , 2,4- dichloro-2 ' -hydroxydiphenyl ether, 3' , 4' , 5' -trichlorosalicylanilide, 1- (3' , 4' -dichloro- phenyl ) -3- ( 4 ' -chlorophenyl ) urea ( Triclocarban) or 3, 7, ll-trimethyldodeca-2, 5, 10-trienol ( ® Farnesol) ; quaternary ammonium salts, such as cetyltrimethyl- ammonium salts or cetylpyridinium salts, DPTA ( 1 , 3-di
  • zinc salts such as zinc salicylate, zinc gluconate, zinc pidolate, zinc sulphate, zinc chloride, zinc lactate, zinc phenolsulphonate or zinc ricinoleate ;
  • spherules in particular vesicles, which may be ionic or nonionic, and/or nanoparticles (nanocapsules and/or nanospheres) .
  • the deodorant active principles can preferably be present in the compositions according to the invention in concentrations by weight ranging from 0.01 to 5% by weight, with respect to the total weight of the composition .
  • suspending agents which are preferably chosen from hydrophobic modified montmorillonite clays, such as hydrophobic modified bentonites or hectorites.
  • CFA name Stearalkonium Bentonite
  • CTFA name reaction product of bentonite and of the quaternary ammonium stearalkonium chloride
  • CTFA name Disteardimonium Hectorite
  • the suspending agents are preferably present in amounts ranging from 0.1 to 5% by weight and more preferably from 0.2 to 2% by weight, with respect to the total weight of the composition.
  • the antiperspirant compositions according to the invention will additionally comprise an organic powder.
  • organic powder is understood to mean any solid which is insoluble in the medium at ambient temperature (25°C) .
  • organic powders which can be used in the composition of the invention, for example, of polyamide particles and in particular those sold under the Orgasol names by Atochem; polyethylene powders; microspheres based on acrylic copolymers, such as those made of ethylene glycol dimethacrylate/lauryl methacrylate copolymer sold by Dow Corning under the name of Polytrap; polymethyl methacrylate microspheres, sold under the name Microsphere M-100 by Matsumoto or under the name Covabead LH85 by Wackherr; hollow polymethyl methacrylate microspheres (particle size: 6.5-10.5 ym) sold under the name Ganzpearl GMP 0800 by Ganz Chemical; methyl methacrylate/ethylene glycol dimethacrylate copolymer microbeads (size: 6.5-10.5 ym) sold under the name Ganzpearl GMP 0820 by Ganz Chemical or Microsponge 5640 by Amcol Health & Beauty Solutions; ethylene/acrylate copolymer
  • the cosmetic compositions according to the invention can additionally comprise cosmetic adjuvants chosen from softeners, antioxidants, opacifiers, stabilizers, moisturizing agents, vitamins, bactericides, preservatives, polymers, fragrances, thickening agents, propellants or any other ingredient commonly used in cosmetics for this type of application .
  • cosmetic adjuvants chosen from softeners, antioxidants, opacifiers, stabilizers, moisturizing agents, vitamins, bactericides, preservatives, polymers, fragrances, thickening agents, propellants or any other ingredient commonly used in cosmetics for this type of application .
  • the thickeners preferably nonionic thickeners, can be chosen from modified or unmodified guar gums and celluloses, such as hydroxypropylated guar gum or cetylhydroxyethylcellulose, or silicas, such as, for example, Bentone Gel MIO, sold by NL Industries, or Veegum Ultra, sold by Polyplastic.
  • the thickeners can also be cationic thickeners, such as, for example, Polyquaternium-37 , sold under the name Salcare SC95 (Polyquaternium-37 (And) Mineral Oil (And) PPG-1 Trideceth-6) or Salcare SC96
  • the amounts of these various constituents which can be present in the cosmetic composition according to the invention are those conventionally used in compositions for the treatment of perspiration.
  • compositions according to the invention can also be pressurized and be packaged in an aerosol device composed of:
  • the propellants generally used in products of this type are such as, for example, dimethyl ether (DME) , volatile hydrocarbons, such as n-butane, propane or isobutane, and their mixtures, optionally with at least one chlorinated and/or fluorinated hydrocarbon; mention may be made, among the latter, of the compounds sold by Dupont de Nemours under the Freon® and Dymel® names, in particular monofluorotrichloromethane, difluorodi- chloromethane, tetrafluorodichloroethane and 1,1-di- fluoroethane, sold in particular under the trade name Dymel 152 A by Dupont. Use may also be made, as propellant, of carbon dioxide gas, nitrous oxide, nitrogen or compressed air.
  • DME dimethyl ether
  • volatile hydrocarbons such as n-butane, propane or isobutane
  • volatile hydrocarbons such as n-butane, propane or isobutane
  • compositions comprising the perlite particles as defined above and the propellant or propellants can occur in the same compartment or in different compartments in the aerosol container.
  • concentration of propellant generally varies from 5 to 95% by weight under pressure and more preferably from 50 to 85% by weight, with respect to the total weight of the pressurized composition.
  • the dispensing means which forms a part of the aerosol device, is generally composed of a dispensing valve controlled by a dispensing head, itself comprising a nozzle via which the aerosol composition is vaporized.
  • the container comprising the pressurized composition can be opaque or transparent. It can be made of glass, of polymer or of metal, optionally covered with a protective lacquer layer.
  • Example 1 Ethyl 2- (3- ⁇ 4- [ (3-phenylpropyl) amino] - piperidin-1-yl ⁇ propyl) benzoate hydrochloride a) Synthesis of the intermediate amine (III) : methyl 2- [3- (4-oxopiperidin-l-yl) propyl] benzoate
  • the methyl ester of 2- ( 3-oxopropyl ) benzoic acid (5 g, 26.2 mmol) is diluted in 50 ml of dichloromethane in a 100 ml round-bottomed flask surmounted by a reflux condenser, to which 4-piperidone monohydrate hydrochloride (4 g, 26.2 mmol) and triethylamine (3.65 ml, 26.2 mmol) are added.
  • Bead molecular sieve is added to the reaction mixture, which is stirred at ambient temperature for 1 h 30.
  • Sodium triacetoxy- borohydride (6.1 g, 28.8 mmol) is then added to the reaction medium and then stirring is maintained at ambient temperature overnight.
  • the molecular sieve beads are filtered off.
  • the organic phase is washed with water and then with a saturated sodium chloride solution.
  • the organic phase is subsequently dried over sodium sulphate and then filtered and concentrated under vacuum as much as possible.
  • the oil obtained is purified on silica gel (gradient CH 2 CI 2 and then CH 2 Cl 2 /MeOH 95/5) .
  • 3-phenylpropylamine (1 ml, 6.8 mmol) and acetic acid (0.4 ml, 6.2 mmol) are added.
  • the reaction medium is stirred at ambient temperature for 2 h.
  • Sodium triacetoxyborohydride (2.7 g, 12.4 mmol) is then added to the reaction medium and the mixture is left stirring at ambient temperature overnight.
  • Water is subsequently added to the mixture and then the pH is brought to pH 7 with a 10% aqueous HC1 solution.
  • the aqueous phase is extracted with butanol and then the organic phases are combined and dried and finally concentrated under vacuum as much as possible.
  • the crude product is purified by chromatography on silica gel (gradient CH 2 Cl 2 /MeOH 95/5 and then CH 2 Cl 2 /MeOH 90/10) .
  • the ethyl ester of 3- (4-carboxyphenyl) propionaldehyde (5 g, 24 mmol) is diluted in 50 ml of dichloromethane in a 100 ml round-bottomed flask surmounted by a reflux condenser, to which 4-piperidone monohydrate hydrochloride (3.72 g, 24 mmol) and triethylamine (3.40 ml; 24 mmol) are added.
  • Bead molecular sieve is added to the reaction mixture, which is stirred at ambient temperature for 1 h 30.
  • Sodium triacetoxy- borohydride (5.65 g, 26.6 mmol) is then added to the reaction medium and stirring is carried out at ambient temperature overnight.
  • the molecular sieve beads are filtered off and the organic phase is washed with water and then with a saturated sodium chloride solution. The organic phase is subsequently dried over sodium sulphate and then filtered and concentrated under vacuum as much as possible.
  • the cyclopentasiloxane is heated to 65°C.
  • the other ingredients are added (one by one) while remaining at 65-70°C.
  • the combined mixture is homogenized (transparent solution) for 15 minutes.
  • the perlite or the superabsorbent polymer is added.
  • the mixture is cooled to approximately 55°C (a few °C above the thickening of the mixture) and poured into the sticks. They are brought to 4°C for 30 minutes.
  • Example 4 Aerosol
  • the Optimat® 1430 OR is dispersed in the mixture of the other starting materials using a paddle, constituting the phase A. Pressurization is carried out in an aerosol can with the isobutane.

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Abstract

La présente invention concerne l'utilisation d'un composé de dialkylphényl- 4-aminopipéridine en tant qu'agent pour le traitement de la perspiration dans une composition cosmétique et en particulier d'un composé correspondant à la formule (I) suivante : dans laquelle : - Alk1 et Alk2 indiquent, indépendamment l'un de l'autre, un radical alkylène linéaire en C1 à C10 saturé ou en C2 à C10 insaturé ou ramifié en C3 à C10 saturé ou insaturé (radical bivalent) ; - Ar1 et Ar2 indiquent, indépendamment l'un de l'autre, un groupe phényle éventuellement substitué par un ou plusieurs radicaux identiques ou différents choisis parmi -F, -CF3, -R1, -OR1, -NR1R2 ou -COX, X indiquant OR1, NHR1 ou NR1R2 ; - R indique un atome d'hydrogène ou un radical alkyle linéaire en C1 à C10 ou ramifié en C3 à C10 saturé ou insaturé éventuellement substitué par un groupe choisi parmi -Ar1, -OR1 ou -NR1R2 ; - R1 et R2 indiquent, indépendamment l'un de l'autre, un radical alkyle linéaire en C1 à C7 saturé ou en C2 à C7 insaturé ou ramifié en C3 à C7 ou cyclique saturé ou insaturé ; et ses sels, ses isomères optiques et ses solvates. L'invention concerne également de nouveaux composés de formule (I) pour laquelle l'un des groupes phényle Ar1 et Ar2 est substitué par au moins un groupe COX et les compositions cosmétiques associées.
PCT/EP2010/065182 2009-10-22 2010-10-11 Utilisation d'une dialkylphényl-4-aminopipéridine en tant qu'agent pour le traitement de la perspiration humaine ; nouveaux composés et compositions associés WO2011047981A1 (fr)

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FR0957429 2009-10-22
FR0957429A FR2951717B1 (fr) 2009-10-22 2009-10-22 Utilisation d'un dialkylphenyl-4-aminopiperidine comme agent de traitement de la transpiration humaine; nouveaux composes, compositions les contenant
US25708809P 2009-11-02 2009-11-02
US61/257,088 2009-11-02

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