US20080305055A1 - Anti-Radical Agents - Google Patents

Anti-Radical Agents Download PDF

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US20080305055A1
US20080305055A1 US11/792,745 US79274505A US2008305055A1 US 20080305055 A1 US20080305055 A1 US 20080305055A1 US 79274505 A US79274505 A US 79274505A US 2008305055 A1 US2008305055 A1 US 2008305055A1
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alkyl
acid
formula
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Werner Baschong
Oliver Reich
Sebastien Mongiat
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BASF SE
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Definitions

  • the present invention relates to the use especially of carbon or ester/amide bridged phenols or lactones thereof, or some sterically hindered amines, as pharmaceutically active agents and to pharmaceutical, especially dermatological, compositions containing them.
  • the invention further relates to the use of these compounds for the preparation of medicaments or formulations for the treatment of radical induced impairments such as inflammatory or allergic conditions, collagen damages, DNA-damage, or reperfusion-damage (use as anti aging).
  • glucocorticoids for the topical treatment of inflammatory and allergic conditions. It is common knowledge that these compounds can have unwanted side-effects.
  • nonsteroidal antiinflammatory medicaments containing therapeutic agents such as ketoprofen, BW755c, piroxicam, diclofenac or indomethazin cannot effectively be applied topically, but only systemically.
  • some phenol ethers have been proposed having antioxidant, anti-inflammatory and antiallergic properties (see EP-A-1366763 and literature cited therein).
  • compositions having surprisingly good pharmacologically properties, in particular antioxidant, anti-inflammatory and antiallergic properties, especially when administered locally.
  • G 3 is propyl substituted by OH or C 2 -C 22 alkanoyloxy; if
  • ROS Radical Oxygen Species
  • MMPs are a group of Zinc-dependent endopeptidases capable of degrading Extra Cellular Matrix (ECM) components such as collagen, elastin, fibronectin, gelatine, laminin, leading to photo-aged skin with wrinkle lines and dispigmentation reactions.
  • ECM Extra Cellular Matrix
  • the present compounds are able to enhance the endogeneous antioxidant defense system which includes enzymatic components such as Glutathione peroxidase, Catalase, Superoxide dismutase, Methallothionein; or non enzymatic components such as Glutathione, vitamin E, Vitamin C, Ubiquinol, ⁇ -carotene.
  • the compounds can protect intercellular and intracellular lipids, lipoproteins, cell membranes, low molecular compounds, such as lipids, sugars, labile amino acids (e.g. with thiol group), glutathione, and further macromolecules such as proteins, proteoglycanes and glycosaminoglycanes against direct oxidation.
  • low molecular compounds such as lipids, sugars, labile amino acids (e.g. with thiol group), glutathione, and further macromolecules such as proteins, proteoglycanes and glycosaminoglycanes against direct oxidation.
  • a part of pharmaceutical or cosmetic carrier emulsions are lipids and also emulsifiers containing lipid segments, which makes them easily prone to chemical conversions induced by reaction with oxygen.
  • the compounds may be hydrophilic or lipophilic.
  • the choice of an optimum antioxidant does not depend just on the solubility in a certain carrier system, but it is also affected by undesirable interactions with a carrier, skin penetration ability after a topical application of the preparation, possibly the production of cytotoxic or immunosuppressive products of a reaction with free radicals, with or without combined action of UV light.
  • the present compounds are useful for the treatment of inflammatory and allergic conditions (e.g. as described by Skaper et al., Free Radical Biology and Medicine 22, 669-78 (1997)), as well as for the treatment of conditions involving disturbances of cell proliferation. They are preferably used for the local treatment of radical-induced adverse reactions such as inflammatory and allergic conditions collagen damage, reperfusion damage, DNA-damage; especially for the skin treatment.
  • inflammatory and allergic conditions e.g. as described by Skaper et al., Free Radical Biology and Medicine 22, 669-78 (1997)
  • radical-induced adverse reactions such as inflammatory and allergic conditions collagen damage, reperfusion damage, DNA-damage; especially for the skin treatment.
  • the present compounds take effect as radical inhibitor. They represent lipoxygenase/-cyclooxigenase inhibitors, i.e. they can intervene in the inflammatory cascade. It can be shown that they take effect as anti-inflammatory agent for the UV induced erythema. They show anti-inflammatory and antioxidant effect, which in certain applications is comparable to the one of vitamin E.
  • the hindered nitroxyl, hydroxylamine and hydroxylamine salt compounds (3) are for example of formulae A to EE and A* to EE*
  • the compounds (3) are those of formulas A, A*, B, B*, C, C*, D, D*, Q, Q*, R, R*, S, S*, X, X*, Y, Y*, Z and Z*,
  • the compounds (3) are those of formulas A, A*, B, B*, C, C*, D, D*, Q, Q*, R and R*,
  • the selected hindered nitroxyl, hydroxylamine and hydroxylamine salt compound (3) preferably conforms to the formula
  • E is oxyl or hydroxyl and G 3 , V, c are as defined for formula (1), or a salt thereof.
  • Compounds (3) such as those of formulae A to EE, especially those of the above formula (3), may be used as such or in form of suitable acid addition salts, as indicated, for example, in the above formulae A* to EE*.
  • suitable acid addition salts include those with inorganic acids, such as chlorides or sulfates, or with organic acids, e.g. sulfonic or carbonic acids, e.g.
  • the salts are preferably pharmaceutically acceptable salts.
  • Pharmaceutically acceptable salts are salts of acids mostly known in the art, e.g. of acids like alkanecarboxylic acids (especially of C 1 -C 4 acids); di- or polycarboxylic and/or hydroxycarboxylic acids such as oxalic, malonic, succinic, fumaric, citric, maleic, tartaric, lactic acid, glucuronic acid and other acids derived from sugars, each of these acids in both enantiomeric forms where optically active; phosphoric, sulfuric, methylsulfonic, toluenesulfonic, benzoic acid; some preferred salts include hydrochlorides, hydrobromides, hydroiodides, benzoates, phosphates, hydrogenphosphates, sulfates, hydrogensulfates and especially citrates. Preferred are, for example, citrates, hydrochlorides, oxalates.
  • C 1 -C 22 Alkyl is straight-chain or branched alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or eicosyl.
  • alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl,
  • C 1 -C 22 Alkylthio is straight-chain or branched alkylthio radicals, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, tert-butylthio, amylthio, heptylthio, octylthio, isooctylthio, nonylthio, decylthio, undecylthio, dodecylthio, tetradecylthio, pentadecylthio, hexadecylthio, heptadecylthio, octadecylthio or eicosylthio.
  • alkylthio radicals such as methylthio, ethylthio, n-propylthio, isopropylthio, n-but
  • C 2 -C 22 Alkylthioalkyl is alkylthio as described above attached by its sulfur atom to alkyl, where the total residue contains 2-22 carbon atoms.
  • C 2 -C 18 Alkenyl is, for example, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, n-dodec-2-enyl or n-octadec-4-enyl.
  • Cycloalkyl is cyclopentyl, cycloheptyl or, preferably, cyclohexyl.
  • C 7 -C 9 -Phenylalkyl includes phenylpropyl (such as cumyl), phenylethyl and, preferably, benzyl.
  • M as alkali often is Li, Na, K, Cs.
  • Useful compounds of present formulae (1) and (2) include those listed in Table 1:
  • Useful hindered amine compounds (3) include the following ones: hindered nitroxyl, hydroxylamine and hydroxylamine salt compounds selected from bis(1-oxy-2,2-6-6-tetramethylpiperidin-4-yl) sebacate; bis(1-hydroxy-2,2-6-6-tetramethyl piperidin-4-yl) sebacate; 1-hydroxy-2,2-6-tetramethyl-4-acetoxypiperidinium citrate; 1-oxyl-2,2,6,6-tetramethyl-4-acetamidopiperidine; 1-hydroxy-2,2,6,6-tetramethyl-4-acetamidopiperidine; 1-hydroxy-2,2,6,6-tetramethyl-4-acetamidopiperidinium bisulfate; 1-oxyl-2,2,6,6-tetramethyl-4-oxo-piperidine; 1-hydroxy-2,2,6,6-tetramethyl-4-oxo-piperidine; 1-hydroxy-2,2,6,6-tetramethyl-4-oxo-piperidinium a
  • Preferred hindered nitroxyl, hydroxylamine and hydroxylamine salt compounds of formula (3) are selected from 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine; 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidine; 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium chloride; 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium acetate; 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium bisulfate; 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperi-dinium citrate; bis(1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium) citrate; tris(1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium) citrate; tetra(1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium) ethylenediaminetetraacetate; tetra
  • the compounds of formula (3) are hydroxylamine salts selected from 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium citrate; bis(1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium) citrate; tris(1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium) citrate; 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium DTPA; bis(1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium) DTPA; tris(1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium) DTPA; tetrakis(1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium) DTPA; pentakis(1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium) DTPA; 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium EDTA;
  • EDTA ethylenediaminetetraacetic acid
  • DTPA diethylene-triaminepentaacetic acid
  • HEDTA hydroxyethylethylenediaminetriacetic acid
  • NTA nitrilotriacetic acid
  • DTPMPA diethylenetriaminepentamethylenephosphonic acid
  • G 1 and G 2 preferably are, independently of each other, C 1 -C 18 alkyl and, in particular, C 1 -C 5 alkyl, especially tert.-butyl.
  • G 1 is located in meta-position relative to G 2 .
  • G 3 is most preferred as hydrogen; C 1 -C 22 alkyl; SO 3 M; propyl substituted by OH and/or by C 2 -C 22 alkanoyloxy; a direct bond; —CH 2 —;
  • Preferred G 4 and G 5 independently are H or C 1 -C 4 alkyl, especially methyl.
  • Particularly interesting compounds (1) include those of formula
  • G 1 and G 2 are the tert-butyl radical; and a is 1.
  • they can be used as individual compounds or as mixtures of several individual compounds. Owing to their good solubility, they can be easily incorporated into the respective formulations.
  • Present compounds e.g. those of formulae (1), (2), (3), can also be used together with tocopherol and/or tocopherol acetate, ascorbic acid and/or derivatives or esters thereof, retinal, retinal, retinoic acid and/or derivatives thereof.
  • Such further hydrophilic or lipophilic components are usually contained within the concentration range from 0.001% to 10% of the total weight of the preparation.
  • Those additional components are preferably selected from the group consisting of
  • R is hydrogen atom or OH group
  • m, n are integral numbers from 0 to 22 where m+n sum is maximally 22;
  • R is hydrogen atom or OH group
  • m, n are integral numbers from 0 to 20 where m+n sum is maximally 21;
  • antioxidants that interrupts the photochemical reaction chain triggered when UV radiation penetrates the skin or hair.
  • Typical examples of such antioxidants are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (e.g. urocanic acid) and derivatives thereof, peptides, such as D,L-carnosine, D-carnosine, L-carnosine and derivatives thereof (e.g. anserine), carotinoids, carotenes, lycopene and derivatives thereof, chlorogenic acid and derivatives thereof, lipoic acid and derivatives thereof (e.g.
  • thiols e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and the glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl, lauryl, palmitoyl, oleyl, linoleyl, cholesteryl and glyceryl esters thereof
  • salts thereof dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and also sulfoximine compounds (e.g.
  • buthionine sulfoximines e.g. hydroxy fatty acids, palmitic acid phytic acid, lactoferrin, chitosan and derivatives such as phosphonomethylated chitosan
  • metal chelating agents e.g. hydroxy fatty acids, palmitic acid phytic acid, lactoferrin, chitosan and derivatives such as phosphonomethylated chitosan
  • hydroxy acids e.g.
  • citric acid citric acid, lactic acid, malic acid
  • humic acid bile acid, bile extracts, bilirubin, biliverdin, EDTA, EDDS, EGTA and derivatives thereof
  • unsaturated fatty acids and derivatives thereof e.g. linolenic acid, linoleic acid, oleic acid
  • folic acid and derivatives thereof ubiquinone and ubiquinol and derivatives thereof
  • vitamin C and derivatives e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate
  • tocopherols and derivatives e.g. vitamin E acetate
  • vitamin A and derivatives e.g.
  • vitamin A palmitate and also coniferyl benzoate of benzoin resin, rutinic acid and derivatives thereof, glycosylrutin, ferulic acid, furfurylidene glucitol, carnosine, butyl hydroxytoluene, butyl hydroxyanisole, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, superoxide dismutase, N-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl]sulfanilic acid (and salts thereof, for example the disodium salts), zinc and derivatives thereof (e.g.
  • ZnO, ZnSO 4 selenium and derivatives thereof (e.g. selenium methionine), stilbene and derivatives thereof (e.g. stilbene oxide, trans-stilbene oxide) and the derivatives suitable according to the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of those mentioned active ingredients.
  • HALS Hindered Amine Light Stabilizers
  • the topical application may additionally contain at least one further component with anti-inflammatory effect, preferably from 0.01% to 10% more preferably about 0.5% to about 5%, of the composition, such as:
  • R1 and R2 are hydrogen atoms or OH group, m, n are integral numbers from 0 to 17 where m+n sum is maximally 21; phytosterols and their polyethoxylate derivatives of the general formulas (6) and(7) below, where R is isoalkyl or isoalkenyl group with 8-10 carbon atoms, where n is integral number from 0 to 50, especially campesterol, ⁇ -sitosterol, stigmasterol, cholesterol, ⁇ -5-avenasterol, ⁇ -7-avenasterol, brassicasterol, spinasterol and fukosterol
  • the pharmaceutical compositions include liquid, semisolid or solid preparations.
  • liquid pharmaceutical compositions are injectable solutions, infusion solutions, drops, sprays, aerosols, emulsions, lotions, suspensions, drinking solutions, gargles and inhalants.
  • semisolid pharmaceutical compositions are ointments, creams (O/W emulsions), rich creams (W/O emulsions), gels, lotions, foams, pastes, suspensions, ovula, plasters, including applications for transdermal systems such as masks, compresses, pads.
  • solid pharmaceutical compositions are tablets, coated tablets, capsules, granules, effervescent granules, effervescent tablets, lozenges, sucking and chewing tablets, suppositories, implants, lyophilisates, adsorbates or powders.
  • Galenic pharmaceutical compositions comprising the present compounds will be understood as meaning in particular emulsions, ointments, gels, sprays and powders; for example creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations such as lip sticks or deodorants, powders or ointments.
  • Nanoemulsions and nanoparticles are mainly based on lecithin or fractionated phospholipids, especially
  • the compounds of the invention may, for example, be incorporated into the bi-layers, into the aqueous core or distributed in both.
  • Microcapsules with particle size >1 ⁇ m based on matrix or encapsulation layer (spherical system based on a core material containing the active; the core is, then, surrounded by one or several coating layers or shells).
  • Polymers used to form those microcapsules include natural gums, cellulosic ingredients, polysaccharides, synthetic polyacrylates or polyacrylamides, polyvinyl alcohol (PVA), lipids, inorganics (silicates/clays), high molecular weight proteins such as gelatin, albumin etc.; examples include Nylon micro-porous spheres (Orgasol range from Elf Atochem), Mineral fillers such as sericite surface-treated by bifunctional coating (reaction between reactive fatty acid derivatives and the aqueous solution of sericite); Glycospheres (core based on modified starch and outer lipid membrane based on fatty acids and polar lipids); carbon nanotubes; Silica shells, made of silicates, for non aqueous and solid end-products such as sticks, dry powders etc.
  • PVA polyvinyl alcohol
  • lipids inorganics
  • inorganics silicates/clays
  • high molecular weight proteins such as gelatin, album
  • Multi-walled delivery systems e.g. systems similar to liposome structures but made only of non-phospholipidic “membrane-mimetic” amphiphiles such as oleic acid, saturated or unsaturated fatty acids, long-chain soaps combined with non ionic surfactants, derivatives of polyglycerol, di-ammonium amphiphiles, cationic surfactants, cationic amphiphiles involving aminoacid residues, sucrose fatty acid esters, aqueous mixture of anionic and cationic surfactants.
  • non-phospholipidic “membrane-mimetic” amphiphiles such as oleic acid, saturated or unsaturated fatty acids, long-chain soaps combined with non ionic surfactants, derivatives of polyglycerol, di-ammonium amphiphiles, cationic surfactants, cationic amphiphiles involving aminoacid residues, sucrose fatty acid esters, aqueous mixture of anionic
  • Microsponge technology such as a system based on microscopic polymer-based sphere that consist of interconnecting voids within a non collapsible structure (non continuous shell); examples include a copolymer of styrene and divinylbenzene, or vinyl derivatives, water-swellable particles made of lactose, cellulose and cellulose derivatives such as Unispheres from Induchem etc.
  • Silicone-based vesicles such as multi-layers vesicles similar to liposome structures, where layers are made of polyether-modified dimethicone (dimethicone copolyol), silicone elastomers, blends of dimethicone crosspolymer, dimethicone/vinyidimethicone crosspolymer or PEG-modified dimethicone crosspolymer etc.
  • Cyclodextrins usually oligomeric and cyclic carbohydrate compounds containing 6 to 8 glucose units such as ⁇ -, ⁇ - and ⁇ -cyclodextrin.
  • the present compounds are applied in nanodispersed or encapsulated form such as described in US-2005-0191330 (see especially sections [0007-0079], [0120-0133] and examples) and US-2003-0190347 (see especially sections [0005-0087] and examples).
  • a further aspect of technical importance within the present invention is the finding that the present compounds are able to protect other active ingredients, especially oxidizable natural substances or active ingredients such as vitamins, plant extracts, fragrances etc., most effectively from premature degradation when encapsulated together with the ingredient.
  • the present compounds in such cases thus are also useful in purely cosmetic formulations, where none of their pharmacological advantages are required, but the protection of another active, e.g. a vitamin such as vitamin A, E or C is sought.
  • preparations for the skin are daily care and/or anti-aging preparations, including light-protective preparations, such as sun milks, lotions, creams, oils, sunblocks or topicals, pretanning preparations or after-sun preparations, also skin-tanning preparations, for example self-tanning creams, skin whitener preparations, skin lightener preparations or combinations of such systems.
  • light-protective preparations such as sun milks, lotions, creams, oils, sunblocks or topicals
  • pretanning preparations or after-sun preparations also skin-tanning preparations, for example self-tanning creams, skin whitener preparations, skin lightener preparations or combinations of such systems.
  • anti-aging preparations in combination with UV-protecting systems such as dayly care creams, dayly care lotions, dayly care milk and dayly care preparations in the form of a spray.
  • compositions/preparations according to the invention may, where appropriate, also contain one or one more additional compounds as described below, especially in preparations for skin treatment:
  • ester oils are isopropylmyristate, isopropylpalmitate, isopropylstearate, isopropyl isostearate, isopropyloleate, n-butylstearate, n-hexyllaurate, n-decyloleate, isooctyl-stearate, iso-nonylstearate, isononyl isononanoate, 2-ethylhexylpalmitate, 2-hexyllaurate, 2-hexyldecylstearate, 2-octyldodecylpalmitate, oleyloleate, oleylerucate, erucyloleate, erucylerucate, cetearyl octanoate, cetyl palmitate, cetyl stearate, cetyl oleate, cetyl behenate, cetyl acetate, myristyl
  • alpha glucosylrutin (CAS No. 130603-71-3), 2-butyloctyl o-hydroxybenzoate (CAS No. 190085-41-7), vitamin E (CAS No. 1406-18-4), vitamin E acetate(CAS No. 58-95-7), diethylhexyl 2,6-naphthalate, di-n-butyl adipate, di(2-ethylhexyl)-adipate, di(2-ethylhexyl)-succinate and diisotridecylvestat, and also diol esters, such as ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di(2-ethylhexanoate), propylene glycol diisostearate, propylene glycol dipelargonate, butanediol diisostearate and neopentyl glycol dicaprylate.
  • diol esters such as ethylene glycol dio
  • Di- or tri-glycerides based on C 6 -C 18 fatty acids, modified by reaction with other alcohols (caprylic/capric triglyceride, wheat germ glycerides, etc.).
  • Fatty acid esters of polyglycerin polyglyceryl-n such as polyglyceryl-4 caprate, polyglyceryl-2 isostearate, etc.
  • castor oil hydrogenated vegetable oil, sweet almond oil, wheat germ oil, sesame oil, hydrogenated cottonseed oil, coconut oil, avocado oil, corn oil, hydrogenated castor oil, shea butter, cocoa butter, soybean oil, mink oil, sunflower oil, safflower oil, macadamia nut oil, olive oil, hydrogenated tallow, apricot kernel oil, hazelnut oil, borago oil, etc.
  • Waxes including esters of long-chain acids and alcohols as well as compounds having wax-like properties, e.g., carnauba wax, beeswax (white or yellow), lanolin wax, candellila wax, ozokerite, japan wax, paraffin wax, microcrystalline wax, ceresin, cetearyl esters wax, synthetic beeswax, etc. Also, hydrophilic waxes as Cetearyl Alcohol or partial glycerides.
  • Ikylene glycol esters especially ethylene glycol distearate; fatty acid alkanolamides, especially coco fatty acid diethanolamide; partial glycerides, especially stearic acid monoglyceride; esters of polyvalent, unsubstituted or hydroxy-substituted carboxylic acids with fatty alcohols having from 6 to 22 carbon atoms, especially long-chained esters of tartaric acid; fatty substances, for example fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which in total have at least 24 carbon atoms, especially laurone and distearyl ether; fatty acids, such as stearic acid, hydroxystearic acid or behenic acid, ring-opening products of olefin epoxides having from 12 to 22 carbon atoms with fatty alcohols having from 12 to 22 carbon atoms and/or polyols having from 2 to 15 carbon atoms and from 2 to 10
  • Mineral oil (light or heavy), petrolatum (yellow or white), microcrystalline wax, paraffinic and isoparaffinic compounds, hydrogenated isoparaffinic molecules as polydecenes and polybutene, hydrogenated polyisobutene, squalane, isohexadecane, isododecane and others from plant and animal kingdom.
  • Siloxanes Organics or Siloxanes (Organosubstituted Polysiloxanes)
  • simethicones which are mixtures of dimethicones having an average chain length of from 200 to 300 dimethylsiloxane units with hydrogenated silicates.
  • a detailed survey by Todd et al. of suitable volatile silicones may in addition be found in Cosm. Toil. 91, 27 (1976).
  • silicones stands for any organosilicon polymer or oligomer having a linear or cyclic, branched or crosslinked structure, of variable molecular weight, and essentially is based on recurring structural units in which the silicone atoms are linked to each other by oxygen atoms (siloxane bond SiOSi), optionally substituted hydrocarbon radicals being directly linked via a carbon atom to the silicone atoms.
  • Cyclic siloxane polymers Cyclomethicones of the general formula
  • cyclopentasiloxane such as cyclopentasiloxane, cyclohexasiloxane (low viscous, volatile fluid;
  • the INCI names for labeling specific cyclic dimethyl polysiloxane compounds are: Cyclotrisiloxane (q.v.) when n is equal to 3, Cyclotetrasiloxane (q.v.) when n is equal to 4, Cyclopentasiloxane (q.v.) when n is equal to 5, Cyclohexasiloxane (q.v.) when n is equal to 6, and Cycloheptasiloxane when n is equal to 7 (q.v.));
  • Silicone elastomers and resins obtained by crosslinking of siloxane structures such as Dimethicones (elastomer: medium crosslinking with a density that allows elongation/distortion of the molecule, usually excluding PEG-modified Dimethicone Crosspolymers; resin: high crosslinking with a density that provides some rigidity to the molecule).
  • siloxane structures such as Dimethicones (elastomer: medium crosslinking with a density that allows elongation/distortion of the molecule, usually excluding PEG-modified Dimethicone Crosspolymers; resin: high crosslinking with a density that provides some rigidity to the molecule).
  • Silicone elastomers useful as co-emulsifier systems include Dimethicone Crosspolymer in Cyclopentasiloxane (e.g. DC 9045 silicone elastomer blend by Dow Corning); Dimethicone Crosspolymer in Dimethicone (e.g. DC 9041 silicone elastomer blend by Dow Corning); polymer of Dimethicone (q.v.) crosslinked with a C 3 to C 20 alkyl group; Dimethicone/Vinyidimethicone Crosspolymer (DC 9506 powder, Dow Corning); Dimethicone/Vinyidimethicone Crosspolymer in Cyclopentasiloxane (e.g. SFE 839 (GE silicones) or KSG 15 (Shin-Etsu));
  • Cyclopentasiloxane e.g. DC 9045 silicone elastomer blend by Dow Corning
  • Resin silicones include dispersing agents such as KP-545 (Shin-Etsu);
  • film-forming and water-resistant agents such as Trimethylsiloxysilicate (e.g. SR 399 (GE Silicones) or Wacker-Belsil TMS803 (Wacker Chemie), mixtures from Dow Corning such as DC 749 cosmetic fluid (Trimethylsiloxysilicate in Cyclopentasiloxane) or DC 593 fluid (Trimethylsiloxysilicate in Dimethicone)); alkyl-modified siloxanes (AMS), which improve spreadability and wash-off resistance or, e.g. for inorganic sunscreens, improve particle dispersion, reduce re-agglomeration, improve long-lasting effect on skin.
  • Trimethylsiloxysilicate e.g. SR 399 (GE Silicones) or Wacker-Belsil TMS803 (Wacker Chemie)
  • mixtures from Dow Corning such as DC 749 cosmetic fluid (Trimethylsiloxysilicate in Cyclopentasiloxane) or DC 593 fluid (Trimethyls
  • R is —(CH2)n-CH3 such as bis-phenylpropyl Dimethicone (SF 1555 fluid; GE Silicone);
  • R is —(CH2)n-CH3 i.e. silicone waxes such as DC 2503 cosmetic wax (Dow Corning); Stearyl Dimethicone DC 2502 fluid (Dow Corning); Cetyl Dimethicone; DC AMS-C30 wax (Dow Corning); 30-C45 Alkyl Methicone; DC 580 wax (Dow Corning); Stearoxytrimethylsilane and Stearyl Alcohol.
  • silicone waxes such as DC 2503 cosmetic wax (Dow Corning); Stearyl Dimethicone DC 2502 fluid (Dow Corning); Cetyl Dimethicone; DC AMS-C30 wax (Dow Corning); 30-C45 Alkyl Methicone; DC 580 wax (Dow Corning); Stearoxytrimethylsilane and Stearyl Alcohol.
  • Perfluorhexane dimethylcyclohexane, ethylcyclopentane, polyperfluoromethylisopropyl ether.
  • Emulsifier systems may comprise for example: carboxylic acids and their salts: alkaline soap of sodium, potassium and ammonium, metallic soap of calcium or magnesium, organic basis soap such as Lauric, palmitic, stearic and oleic acid etc. . . . Alkyl phosphates or phosphoric acid esters, acid phosphate, diethanolamine phosphate, potassium cetyl phosphate. Ethoxylated carboxylic acids or polyethyleneglycol esters, PEG-n acylates.
  • Linear fatty alcohols having from 8 to 22 carbon atoms, branched from 2 to 30 mol of ethylene oxide and/or from 0 to 5 mol propylene oxide with fatty acids having from 12 to 22 carbon atoms and with alkylphenols having from 8 to 15 carbon atoms in the alkyl group.
  • Fatty alcohol polyglycolether such as laureth-n, ceteareth-n, steareth-n, oleth-n.
  • Fatty acid polyglycolether such as PEG-n stearate, PEG-n oleate, PEG-n cocoate.
  • Monoglycerides and polyol esters Monoglycerides and polyol esters.
  • Fatty acid and polyglycerol ester such as monostearate glycerol, diisostearoyl polyglyceryl-3-diisostearates, polyglyceryl-3-diisostearates, triglyceryl diisostearates, polyglyceryl-2-sesquiisostearates or polyglyceryl dimerates. Mixtures of compounds from a plurality of those substance classes are also suitable.
  • Fatty acid polyglycolesters such as monostearate diethylene glycol, fatty acid and polyethylene glycol esters, fatty acid and saccharose esters such as sucro esters, glycerol and saccharose esters such as sucro glycerides.
  • sorbitan esters such as sesquiisostearate, sorbitan, PEG-(6)-isostearate sorbitan, PEG-(10)-sorbitan laurate, PEG-17-dioleate sorbitan.
  • Glucose derivatives C 8 -C 22 alkyl-mono and oligo-glycosides and ethoxylated analogues with glucose being preferred as the sugar component.
  • O/W emulsifiers such as methyl gluceth-20 sesquistearate, sorbitan stearate/sucrose cocoate, methyl glucose sesquistearate, cetearyl alcohol/cetearyl glucoside.
  • W/O emulsifiers such as methyl glucose dioleate/methyl glucose isostearate.
  • Sulfates and sulfonated derivatives dialkylsulfosuccinates, dioctyl succinate, alkyl lauryl sulfonate, linear sulfonated parafins, sulfonated tetraproplyne sulfonate, sodium lauryl sulfates, ammonium and ethanolamine lauryl sulfates, lauyl ether sulfates, sodium laureth sulfates, sulfosuccinates, aceyl isothionates, alkanolamide sulfates, taurines, methyl taurines, imidazole sulfates.
  • Amine derivatives, amine salts, ethoxylated amines, oxide amine with chains containing an heterocycle such as alkyl imidazolines, pyridine derivatives, isoquinoteines, cetyl pyridinium chlorure, cetyl pyridinium bromide, quaternary ammonium such as cetyltrimethylbroide amonium broide (CTBA), stearylalkonium.
  • Amide derivatives alkanolamides such as acylamide DEA, ethoxylated amides such as PEG-n acylamide, oxy-deamide.
  • Propoxylated or POE-n ethers (Meroxapols), Polaxamers or poly(oxyethylene)m-block-poly(oxypropylene)n-block(oxyethylene).
  • Zwitterionic surfactants that carry at least one quaternary ammonium group and at least one carboxylate and/or sulfonate group in the molecule.
  • Zwitterionic surfactants that are especially suitable are betaines, such as N-alkyl-N,N-dimethylammonium glycinates, cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinates, cocoacylaminopropyldimethylammonium glycinate and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines each having from 8 to 18 carbon atoms in the alkyl or acyl group and also cocoacylaminoethylhydroxyethylcarboxymethylglycinate, N-alkylbetaine, N-alkylaminobetaines.
  • betaines such as N-alkyl-N,N-dimethylammonium glycinates, cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium g
  • Non ionic emulsifiers such as PEG-6 beeswax (and) PEG-6 stearate (and) polyglyceryl-2-isostearate [Apifac], glyceryl stearate (and) PEG-100 stearate.
  • Anionic emulsifiers such as PEG-2 stearate SE, glyceryl stearate SE [Monelgine, Cutina KD], propylene glycol stearate [Tegin P], cetearyl Alcohol and Sodium cetearyl sulfate [Lanette N. Cutina LE, Crodacol GP], cetearyl alcohol and sodium lauryl sulfate [Lanette W], trilaneth-4 phopshate and glycol stearate and PEG-2 stearate [Sedefos 75], glyceryl stearate and sodium lauryl Sulfate [Teginacid Special].
  • Cationic acid bases such as cetearyl alcohol and cetrimonium bromide.
  • Silicone emulsifiers particularly suitable for W/Si emulsions are those corresponding to the following formula:
  • These compounds represent the oxyalkylenated organo-modified silicones.
  • Other denominations used are PEG/PPG Dimethicones (Dimethicone copolyols) or Silicone polyethers that clearly show surface active properties necessary to emulsify.
  • Oxyalkylenated organo-modified slicones PEG/PPG Dimethicones & Silicone polyethers Bis-PEG/PPG-14/14 Dimethicone Bis-PEG/PPG-20/20 Dimethicone Bis-PEG/PPG-16/16 PEG/PPG-16/16Dimethicone Bis_PEG-15 Methyl Ether Dimethicone Bis(PPG-7 Undeceneth-21) Dimethicone Cetyl PEG/PPG-15/15 Butyl Ether Dimethicone Cetyl PEG/PPG-7/3 Dimethicone Cetyl PEG/PPG-10/1 Dimethicone Dimethicone Copolyol Dimethicone PEG-8 Adipate Dimethicone PEG-7 Avocadoate Dimethicone PEG-8 Avocadoate Dimethicone PEG-8 Beeswax Dimethicone PEG-n esters .
  • Dimethicone PEG/PPG-7/4 Phosphate Dimethicone PEG/PPG-12/4 Phosphate Dimethicone PEG-7 Undecylenate Laurylmethicone copolyol PEG-10 Dimethicone crosspolymer PEG-12 Dimethicone crosspolymer PEG-10 Lauryl Dimethicone Crosspolymer PEG-15 Lauryl Dimethicone Crosspolymer PEG-6 Methyl ether Dimethicone PEG-n Methyl ether Dimethicones . . .
  • the emulsifiers may be used in an amount of, for example, from 1 to 30% by weight, especially from 4 to 20% by weight and preferably from 5 to 10% by weight, based on the total weight of the composition.
  • the preferably amount of such emulsifier system could represent 5% to 20% of the oil phase.
  • Cosmetic/pharmaceutical preparations for example creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders or ointments, may in addition contain, as further adjuvants and additives, mild surfactants, super-fatting agents, consistency regulators, thickeners, polymers, stabilisers, biogenic active ingredients, deodorising active ingredients, anti-dandruff agents, film formers, swelling agents, further UV light-protective factors, antioxidants, hydrotropic agents, preservatives, insect repellents, self-tanning agents, solubilisers, perfume oils, colourants, bacteria-inhibiting agents and the like.
  • mild surfactants for example creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders or ointments
  • Substances suitable for use as super-fatting agents are, for example, lanolin and lecithin and also polyethoxylated or acrylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the latter simultaneously acting as foam stabilisers.
  • composition of the present preparation may further comprise suitable anti-wrinkle agents including sulfur-containing D and L amino acids and their derivatives and salts, particularly the N-acetyl derivatives, a preferred example of which is N-acetyl-L-cyteine; thiols; hydroxy acids (salicylic acid, glycolic acid), keto acids (pyruvic acid), phytic acid, lipoic acid; lysophophatidic acid, skin peel agents, flavonoids, stilbenes, cinnamates, resveratrol, kijnetin, zeatin, dimethylaminoethanol, peptides from natural and synthetic sources, salts of sugar acids (Mn gluconate), terpene alcohols, vitamin B compounds such as vitamin B3, vitamin B1 (Thiamine), vitamin B2 (riboflavin), vitamin B5 (Pantothenic acid), vitamin Bt (carnitine), Vitamin B12 (cobalamine), vitamin B15 (pangamic acid or diisopropyl
  • composition of the present preparation may further comprise suitable skin lightening ingredients including kojic acid, arbutin, tranexamic acid, ascorbic acid and derivatives thereof, e.g., magnesium ascorbyl phosphate or sodium ascorbyl phosphateor other salts of ascorbyl phosphate. Also those ingredient displayed in the PCT application N o US 95/07432, filed on Feb. 24, 1995 and PCT application N o US 95/02809, filed on Jan. 3, 1995.
  • suitable skin lightening ingredients including kojic acid, arbutin, tranexamic acid, ascorbic acid and derivatives thereof, e.g., magnesium ascorbyl phosphate or sodium ascorbyl phosphateor other salts of ascorbyl phosphate.
  • suitable skin lightening ingredients including kojic acid, arbutin, tranexamic acid, ascorbic acid and derivatives thereof, e.g., magnesium ascorbyl phosphate or sodium ascorbyl phosphateor other salt
  • Suitable mild surfactants include fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and/or di-alkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ⁇ -olefin sulfonates, ethercarboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkylamidobetaines and/or protein fatty acid condensation products, the latter preferably being based on wheat proteins.
  • Silicium dioxide magnesium silicates, aluminium silicates, polysaccharides or derivatives thereof for example hyaluronic acid, xanthan gum, guar-guar, agar-agar, alginates, carraghenan, gellan, pectines, or modified cellulose such as hydroxycellulose, hydroxypropyl-methylcellulose.
  • polyacrylates or homopolymer of reticulated acrylic acids and polyacrylamides carbomer (carbopol types 980, 981, 1382, ETD 2001, ETD2020, Ultrez 10) or Salcare range such as Salcare SC80(steareth-10 alkyl ether/acrylates copolymer), Salcare SC81 (acrylates copolymer), Salcare SC91 and Salcare AST(sodium acrylates copolymer/PPG-1 trideceth-6), sepigel 305(polyacrylamide/laureth-7), Simulgel NS and Simulgel EG (hydroxyethyl acrylate/sodium acryloyidimethyl taurate copolymer), Stabilen 30 (acrylates/vinyl isodecanoate crosspolymer), Pemulen TR-1 (acrylates/C10-30 alkyl acrylate crosspolymer), Luvigel EM (sodium acrylates copolymer), Aculyn 28 (acrylates/beheneth
  • Viscosity additives set up network structures throughout the base fluid, and exhibit the “yield value”. Clay and polymer additives possess high yield values, and are therefore used to positively support suspension problems. Regarding particle suspension, the addition of such viscosity building agents will help to decrease the density difference between the particle and the fluid media surrounding, and therefore will lead to better resistance to the settling down of the particles.
  • Thickeners can be divided into at least 2 general categories: those that show the best performance in water, and those that show the best performance in oils.
  • Quaternized compounds such as Stearalkonium Bentonite RM 13 Magnesium Silicates or Hectorites such as Bentone Series (from Elementis Specialties) and Quaternized compounds such as Disteardimonium Hectorite (to disperse in lipophilic media) RM 14 Magnesium sodium Fluorosilicate or modified Mica RM 15 Synthetic layered Silicates; similar structure to Hectorites; Sodium Magnesium Silicates (Laponite range from Solvay) RM 16 Fumed Silicas such as Aerosil range from Degussa
  • “Hydro Swelling Droplets” concept RM 21 - Glyceryl Polyacrylates (e.g., Hispagel 100) or Polymethacrylates (e.g., Lubrajel range from ISP Corp.) RM 22 Poly(Acrylamide) PAAm and its copolymers; copolymers of ammonium acrylate and acrylamide; copolymers of AAam with long hydrophobic chain and acrylates RM 23 Poly(Ethylene oxide) PEO and Poly (Propylene oxide) PPO and their copolymers; these are block terpolymers of EO and PO with the structure ABA or BAB; A: PEO with good water solubility B: PPO with limited water solubility RM 24 Poly(VinylPyrrolidone)PVP homopoplymers or Poly(VinylPyrrolidone)/Vinyl Acetate coplymers RM 25 Poly (vinylalcohol) PVA RM 26 VA/Crot
  • Phospholipid derivatives RM 35 Alkylated Phosphatidyl Choline forming fluid lamellar assembly as the stableliquid crystalline phase of general formula: wherein R is C 2 -C 4 alkyl RM 36 Phosphobetaines (amphoteric ingredients); alkylamido Phosphobetaine ofgerneral formula wherein R is C 2 -C 14 alkyl RM 37 Alkyl Phosphate Quaternary compounds of general formula wherein R is C 2 -C 14 alkyl
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, for example a quaternised hydroxymethyl cellulose obtainable under the name Polymer JR 400 from Amerchol, cationic starches, copolymers of diallylammonium salts and acrylamides, quarternised vinyl-pyrrolidone/vinyl imidazole polymers, for example Luviquat® (BASF), condensation products of polyglycols and amines, quaternised collagen polypeptides, for example lauryidimonium hydroxypropyl hydrolyzed collagen (Lamequat®L/Grünau), quaternised wheat polypeptides, polyethyleneimine, cationic silicone polymers, for example amidomethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine(Cartaretin/Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat 550/
  • anionic, zwitterionic, amphoteric and non-ionic polymers there come into consideration, for example, vinyl acetate/crotonic acid copolymers, vinylpyrrolidone/vinyl acrylate copolymers, vinyl acetate/butyl maleate/isobornyl acrylate copolymers, methyl vinyl ether/maleic anhydride copolymers and esters thereof, uncrosslinked polyacrylic acids and polyacrylic acids crosslinked with polyols, acrylamidopropyl-trimethylammonium chloride/acrylate copolymers, octyl acrylamide/methyl methacrylatetert-butylaminoethyl methacrylate/2-hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone/vinyl acetate copolymers, vinylpyrrolidone/dimethylaminoethyl methacrylate/vinyl caprolactam terpol
  • Biogenic active ingredients are to be understood as meaning, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes.
  • deodorising active ingredients there come into consideration, for example, antiperspirants, for example aluminium chlorohydrates (see J. Soc. Cosm. Chem. 24, 281 (1973)). Under the trade mark Locron® of Hoechst AG, Frankfurt (FRG), there is available commercially, for example, an aluminium chlorohydrate corresponding to formula Al 2 (OH) 5 Cl ⁇ 2.5H 2 O, the use of which is especially preferred (see J. Pharm. Pharmacol. 26, 531 (1975)). Besides the chlorohydrates, it is also possible to use aluminium hydroxyacetates and acidic aluminium/zirconium salts. Esterase inhibitors may be added as further deodorising active ingredients.
  • Such inhibitors are preferably trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and especially triethyl citrate (Hydagen CAT, Henkel), which inhibit enzyme activity and hence reduce odour formation.
  • trialkyl citrates such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and especially triethyl citrate (Hydagen CAT, Henkel), which inhibit enzyme activity and hence reduce odour formation.
  • esterase inhibitors are sterol sulfates or phosphates, for example lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof, for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester and hydroxycarboxylic acids and esters thereof, for example citric acid, malic acid, tartaric acid or tartaric acid diethyl ester.
  • dicarboxylic acids and esters thereof for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic
  • Antibacterial active ingredients that influence the germ flora and kill or inhibit the growth of sweat-decomposing bacteria can likewise be present in the preparations (especially in stick preparations).
  • Examples include chitosan, phenoxyethanol and chlorhexidine gluconate.
  • 5-chloro-2-(2,4-dichlorophenoxy)-phenol Triclosan, Irgasan, Ciba Specialty Chemicals Inc. has also proved especially effective.
  • Customary film formers include, for example, chitosan, microcrystalline chitosan, qua ternised chitosan, polyvinylpyrrolidone, vinylpyrrolidone/vinyl acetate copolymers, polymers of quaternary cellulose derivatives containing a high proportion of acrylic acid, collagen, hyaluronic acid and salts thereof and similar compounds.
  • hydrotropic agents for example ethoxylated or non ethoxylated mono-alcohols, diols or polyols with a low number of carbon atoms or their ethers (e.g. ethanol, isopropanol, 1,2-dipropanediol, propyleneglycol, glyerin, ethylene glycol, ethylene glycol monoethylether, ethylene glycol monobutylether, propylene glycol monomethylether, propylene glycol monoethylether, propylene glycol monobutylether, diethylene glycol monomethylether; diethylene glycol monoethylether, diethylene glycol monobutylether and similar products).
  • ethers e.g. ethanol, isopropanol, 1,2-dipropanediol, propyleneglycol, glyerin, ethylene glycol, ethylene glycol monoethylether, ethylene glycol monobutylether, propylene glycol
  • the polyols that come into consideration for that purpose have preferably from 2 to 15 carbon atoms and at least two hydroxy groups.
  • the polyols may also contain further functional groups, especially amino groups, and/or may be modified with nitrogen.
  • Typical examples are as follows: glycerol, alkylene glycols, for example ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and also polyethylene glycols having an average molecular weight of from 100 to 1000 Dalton; technical oligoglycerol mixtures having an intrinsic degree of condensation of from 1.5 to 10, for example technical diglycerol mixtures having a diglycerol content of from 40 to 50% by weight; methylol compounds, such as, especially, trimethylolethane, trimethylol-propane, trimethylolbutane, pentaerythritol and dipentaerythritol; lower alkyl-glucosides, especially those having from 1 to 8 carbon atom
  • Suitable preservatives include, for example, Methyl-, Ethyl-, Propyl-, Butyl-parabens, Benzal-konium chloride, 2-Bromo-2-nitro-propane-1,3-diol, Dehydroacetic acid, Diazolidinyl Urea, 2-Dichloro-benzyl alcohol, DMDM hydantoin, Formaldehyde solution, Methyldibromoglutanitrile, Phenoxyethanol, Sodium Hydroxymethylglycinate, Imidazolidinyl Urea, Triclosan and further substance classes listed in the following reference: K. F. DePolo—A short textbook of cosmetology, Chapter 7, Table 7-2, 7-3, 7-4 and 7-5, p210-219.
  • bacteria-inhibiting agents are preservatives that have a specific action against gram-positive bacteria, such as 2,4,4′-trichloro-2′-hydroxydiphenyl ether, chlorhexidine (1,6-di(4-chlorophenyl-biguanido)hexane) or TCC (3,4,4′-trichlorocarbanilide).
  • gram-positive bacteria such as 2,4,4′-trichloro-2′-hydroxydiphenyl ether, chlorhexidine (1,6-di(4-chlorophenyl-biguanido)hexane) or TCC (3,4,4′-trichlorocarbanilide).
  • TCC 3,4,4′-trichlorocarbanilide
  • a large number of aromatic substances and ethereal oils also have antimicrobial properties.
  • Typical examples are the active ingredients eugenol, menthol and thymol in clove oil, mint oil and thyme oil.
  • a natural deodorising agent of interest is the terpene alcohol farnesol (3,7,11-tri-methyl-2,6,10-dodecatrien-1-ol), which is present in lime blossom oil.
  • Glycerol monolaurate has also proved to be a bacteriostatic agent.
  • the amount of the additional bacteria-inhibiting agents present is usually from 0.1 to 2% by weight, based on the solids content of the preparations.
  • mixtures of natural and/or synthetic aromatic substances for example, extracts from blossom (lilies, lavender, roses, jasmine, neroli, ylang-ylang), from stems and leaves (geranium, patchouli, petitgrain), from fruit (aniseed, coriander, carraway, juniper), from fruit peel (bergamot, lemons, oranges), from roots (mace, angelica, celery, cardamom, costus , iris, calmus), from wood (pinewood, sandalwood, guaiacum wood, cedarwood, rosewood), from herbs and grasses (tarragon, lemon grass, sage, thyme), from needles and twigs (spruce, pine, Scots pine, mountain pine), from resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic aromatic substances are, for example, products of the ester, ether, aldehyde, ketone, alcohol or hydrocarbon type.
  • Aromatic substance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethylmethylphenyl glycinate, allylcyclohexyl propionate, styrallyl propionate and benzyl salicylate.
  • the ethers include, for example, benzyl ethyl ether;
  • the aldehydes include, for example, the linear alkanals having from 8 to 18 hydrocarbon atoms, citral, citronellal, citronellyl oxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal;
  • the ketones include, for example, the ionones, isomethylionone and methyl cedryl ketone;
  • the alcohols include, for example, anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenyl ethyl alcohol and terpinol; and
  • the hydrocarbons include mainly the terpenes and balsams.
  • Ethereal oils of relatively low volatility which are chiefly used as aroma components, are also suitable as perfume oils, e.g. sage oil, camomile oil, clove oil, melissa oil, oil of cinnamon leaves, lime blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, labolanum oil and lavandin oil.
  • colourants there may be used as colourants the substances that are suitable and permitted for cosmetic purposes, as compiled, for example, in the publication “Kosmetician Anlagenrbesch” of the Farbstoffkommission der Deutschen Deutschen Deutschen Anlagenstician, Verlag Chemie, Wein-heim, 1984, pages 81 to 106.
  • the colourants are usually used in concentrations of from 0.001 to 0.1% by weight, based on the total mixture.
  • Anti-foams such as silicones, structurants, such as maleic acid, solubilisers, such as ethylene glycol, propylene glycol, glycerol or diethylene glycol, opacifiers, such as latex, styrene/PVP or styrene/acrylamide copolymers, complexing agents, such as EDTA, NTA, alaninediacetic acid or phosphonic acids, propellants, such as propane/butane mixtures, N 2 O, dimethyl ether, CO 2 , N 2 or air, so-called coupler and developer components as oxidation dye precursors, reducing agents, such as thioglycolic acid and derivatives thereof, thiolactic acid, cysteamine, thiomalic acid or mercaptoethanesulfonic acid, or oxidising agents, such as hydrogen peroxide, potassium bromate or sodium bromate.
  • solubilisers such as ethylene glycol, propylene glycol, g
  • Suitable insect repellents are, for example, N,N-diethyl-m-toluamide, 1,2-pentanediol or insect repellent 3535; suitable self-tanning agents are, for example, dihydroxyacetone and/or erythrulose or dihydroxy acetone and/or dihydroxy acetone precursors as described in WO 01/85124 and/or erythrulose.
  • Polymeric beads or hollow spheres may be used as SPF enhancers.
  • Present compounds may also be contained in liposomes or used in pharmacological compositions with conventional carriers and penetration enhancers, for example urea, dextrane, propylene glycol, oleic acid and the like.
  • the pharmaceutical composition will usually contain the present compounds in amounts of 0.001 to 10% by weight, preferably of 0.01 to 5%, especially 0.01 to 2% by weight, of the total mixture.
  • the pharmaceutical composition of this invention may contain, in addition to the present compounds, further pharmaceutical or cosmetic agents, e.g. having antiphlogistic activity, typically including antiinflammatory agents, vitamins, and/or, where appropriate, antipsoriatic agents, further skin actives, cell proliferation regulators, antiallergic, UV protecting, moisturizing, antiageing, gastroprotective, antiasthmatic agents, DNA-protectants.
  • the pharmaceutical composition of this invention may contain antioxidants and/or light stabilisers apart from present formulae (1)-(3), especially UV absorbers.
  • Suitable components of these classes include those described in EP-A-955355, WO00/25730, WO00/25731, WO03/103622, EP-A-1366763.
  • Suitable UV filter substances which can be additionally used with the present compounds p-aminobenzoic acid derivatives, for example 4-dimethylaminobenzoic acid 2-ethylhexyl ester; salicylic acid derivatives, for example salicylic acid 2-ethylhexyl ester; benzophenone derivatives, for example 2-hydroxy-4-methoxybenzophenone and its 5-sulfonic acid derivative; dibenzoylmethane derivatives, for example 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)- propane-1,3-dione; diphenylacrylates, for example 2-ethylhexyl 2-cyano-3,3-diphenylacrylate, and 3-(benzo- furanyl) 2-cyanoacrylate; 3-imidazol-4-ylacrylic acid and esters; benzofuran derivatives, especially 2-(p-aminophenyl)benzofuran derivatives, described in EP-A-582
  • the primary particle size is an average of 15 nm-35 nm and the particle size in dispersion is in the range of 100 nm-300 nm.
  • UV absorbers described in “Sunscreens”, Eds. N. J. Lowe, N. A. Shaath, Marcel Dekker, Inc., New York and Basle or in Cosmetics & Toiletries (107), 50ff (1992) also can be used as additional UV protective substances.
  • Helioguard 365 from Milbelle AG, isolated mycosporine like amino acids from the red alga porphyra umbilicalis (INCI: Porphyra Umbilicalis) that are encapsulated into liposomes,) 70 alpha-lipoic-acid as described in DE 10229995 71 synthetic organic polymers as described in EP 1371358, [0033]- [0041] 72 phyllosilicates as described in EP 1371357 [0034]-[0037] 73 silica compounds as described in EP1371356, [0033]-[0041] 74 inorganic particles as described in DE10138496 [0043]-[0055] 75 latex particles as described in DE10138496 [0027]-[0040] 76 1H-Benzimidazole-4,6-disulfonic acid, 2,2′-(1,4-phenylene)bis-, 180898-37-7 disodium salt; Bisimidazylate; Neo Heliopan APC
  • Suitable UV filter substances which can be additionally used (Abbreviations T: table, R: row, Comp: compound, Ex: compound(s) of patent example, p: page); the generic scope of the UV absorbers is described in the left-hand column; specific compounds are indicated in the right-hand column DE 100331804 Tab 1 p 4, tab 2 + 3 p 5 EP 613893 Ex 1-5 + 15, T 1, pp 6-8 EP 1000950 Comp.
  • the preparations contain, for example, from 0.1 to 30% by weight, preferably from 0.1 to 15% by weight and especially from 0.5 to 10% by weight, based on the total weight of the composition, of one or more UV absorbers, from 1 to 60% by weight, especially from 5 to 50% by weight and preferably from 10 to 35% by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30% by weight, especially from 1 to 30% by weight and preferably from 4 to 20% by weight, based on the total weight of the composition, of at least one emulsifier, from 10 to 90% by weight, especially from 30 to 90% by weight, based on the total weight of the composition, of water, and from 0 to 88.9% by weight, especially from 1 to 50% by weight, of further cosmetically acceptable adjuvants.
  • UV absorbers from 1 to 60% by weight, especially from 5 to 50% by weight and preferably from 10 to 35% by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30% by weight, especially
  • Cosmetic or pharmaceutical preparations in general can be prepared by physically mixing the active component(s) with the adjuvant using customary methods, for example by simply stirring together the individual components.
  • HDF-N2 Primary human dermal fibroblasts (HDF-N2) are maintained in Dulbecco's culture media (DMEM; 1 g/l glucose), supplemented with 10% of fetal calf serum (FCS), 100 ⁇ g/ml of streptomycin sulphate, 100 U/ml of penicillin and 2 mM of L-glutamine, all of them from Biowhitaker, USA. Confluent cells are detached by incubation for 3 minutes in 0.055 trypsin/0.53 mM EDTA at 37° C. and plated at the established cell density (normally, 15 ⁇ 10 4 cells/cm 2 ).
  • DMEM Dulbecco's culture media
  • FCS fetal calf serum
  • test media thus obtained are added for 24 h to 48h-cultures of Human Dermal Fibroblast (HDF) described above, and the rate of survival is measured via a specific color marker penetrating only into live-cells (The more absorption at OD 450 , the more viable cells: Living dermal fibroblast possess an esterase that liberates a color, which absorbs at 450 nm. Dead cells do not. Measuring in cell cultures in presence of test substances the OD450 and comparing it to non-treated controls yields thus a measure for cell toxicity).
  • HDF Human Dermal Fibroblast
  • Results are compiled in the following table.
  • Cytotoxicity of the present test compounds is in an acceptable range.
  • test compounds are cultured in 24 well culture plates for 3 days. Before treatment confluent cells are arrested for 24 h with culture media containing 1% FCS and then treated for 18-24 h with selected concentrations of the test compounds.
  • Each of the test compounds AO3, AO5, AO6 and AO7, respectively, is applied in dilutions 1:500, 1:1000 and 1:1500, each prepared by adding appropriate amounts of the stock solution described in example 1 to the culture medium.
  • Morphological control of culture at 24 h of product application is performed by phase contrast microscopy.
  • Anti-oxidant activity in vivo is measured via the capacity of a test compound to reduce radical induced lipid-peroxidation.
  • Evaluation method Determination of squalene Determination of squalenehydroperoxide Time of Evaluation: after UVA radiation Evaluation: Descriptive statistics: average, median, minimum, maximum, variance, standard error, standard deviation; Multiple range test.
  • test compound active
  • test solution 1% b.w. solution in ethanol, except for A07 where a 0.1% b.w. solution in ethanol is applied; in the following, these test solutions are also recalled as formulation.
  • On the inner forearm of each subject symmetrically opposed areas are defined.
  • the different formulations are applied once a day at a dose of about 2 mg of test solution/cm 2 for one week (application with a syringe for fine dosage: Omnifix®-F 1 ml; manufacturer: Braun Mels Institute AG, Germany).
  • the fluorometer is used as a photon detector with the excitation source turned off.
  • This assay measures the hydroperoxy groups themselves and not indirect indices of lipid peroxidation such as conjugated dienes or breakdown products of lipid hydroperoxides. Chemiluminescence also detects ubiquinols. To confirm that any chemiluminescence observed in this assay was due to a hydroperoxide, not a hydroquinone, some samples were reduced with triphenyl phosphine and rerun. Since the chemiluminescence response of hydroperoxides, but not of hydroquinones, is eliminated by triphenyl phosphine, the disappearance of chemiluminescence peaks in the treated samples indicated that chemiluminescence observed in this assay was due to hydroperoxides and not hydroquinones.
  • Measuring data are centrally computerised after validity check and quality assurance. Evaluation is done using the software Statgraphics for Windows, Version 5.0—Manugistics, USA. Data are analysed by multiple range test (LSD: Least Significant Differences). The 0.05 level is selected as the point of minimal acceptance statistical significance.
  • the present skincare formulations significantly (p ⁇ 0.05) reduce squalene peroxidation, compared to UV radiated non-treated control.
  • a clear homogenous prephase is obtained by mixing
  • a coemulsifier e.g. a polyethoxylated sorbitan fatty acid ester, polyethoxylated fatty alcohol, polyethoxylated fatty acid, polyethoxylated vitamin E derivative, polyethoxylated lanoline or lanoline derivative, polyethoxylated fatty acid glyceride or partial glyceride, polyethoxylated alkylphenol, sulfuric acid semiester of a polyethoxylated fatty alcohol or salt thereof, polyethoxylated fatty amine or amide, polyethoxylated carbon hydrate), (c) 30 to 70% by weight of a lipophilic component consisting of a triglyceride, a compound of the invention such as AO3-AO8, and optionally a further active agent, where the weight ratio of active agent(s): triglycer
  • a coemulsifier e.g. a polyethoxylated sorbitan fatty acid ester,
  • the water phase (e.g. 90 kg) is placed, with stirring (e.g. magnetic agitator), at 50° C. in a vessel.
  • the liquid prephase (e.g. 10 kg) is added to the water phase with stirring (e.g. with a magnetic agitator).
  • the formulation thus obtained may be further diluted or admixed.
  • a dispersion is obtained by mixing a clear prephase containing: vitamin A palmitate (1.7 ⁇ 10 6 IU/g) 0.45% compound AO7 0.45% soybean lecithin 1.73% miglyol 812 3.00% polysorbate 80 3.40% ethanol 1.42% to a water phase: 10 mm phosphate buffer, pH 6 ad 100.00%
  • Final preparation contains: cetyl alcohol 10.00% hydrogenated groundnut oil 20.00% polysorbate 60 5.00% propylene glycol 20.00% phenoxyethanol 0.50% dispersion shown above 23.00% aqua purificata ad 100.00%
  • a dispersion is obtained by mixing a clear prephase containing: solcoseryl 1.00% compound AO7 1.00% soybean lecithin 1.73% polysorbate 80 3.40% miglyol 812 3.45% ethanol 1.42% to a water phase: 10 mm phosphate buffer, pH 6 ad 100.00%
  • Final preparation contains: sodium carboxymethylcellulose 450 cP 3.50% dispersion shown above 50.00% aqua purificata ad 100.00%
  • the preparation is pleasantly cooling and has good antiphlogistic action.
  • a dispersion is obtained by mixing a clear prephase containing: vitamin E acetate 2.00% compound AO3 1.00% soybean lecithin 0.49% polysorbate 80 1.86% miglyol 812 0.71% ethanol 0.63% to a water phase: aqua purificata ad 100.00%
  • Final preparation contains: glycerol sorbitan fatty acid ester 2.0% polyethoxy fatty acid ester 2.0% isopropylisostearate 5.0% mineral oil 7.0% isopropylpalmitate 4.0% wheat germ oil 3.0% propylene glycol 3.8% dispersion shown above 5.0% MgSO 4 ⁇ 7H2O 0.7% perfume 0.5% perservative, water
  • a dispersion is obtained by mixing a clear prephase containing: parsol MCX 2.59% (octyl methoxycinnamate) Parsol 5000 1.11% (4-methylbenzylidene camphor) compound AO7 1.00% miglyol 812 1.30% soybean lecithin 0.50% polysorbate 80 3.40% ethanol 1.10% to a water phase: aqua purificata ad 100.00%
  • Final preparation contains: PEG-5 glycerol stearate 5.0% steareth-21 2.0% mineral oil 30.0% cetyl alcohol 2.0% microcrystalline wax 1.0% propylene glycol 6.0% dispersion shown above 10.0% phenoxyethanol + methyl-, ethyl-, propyl-, butylparabene 0.3% water ad 100.0%

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US20080095831A1 (en) * 2006-08-10 2008-04-24 Mc Graw Thomas L Topical formulation of multilamellar vesicles composition for percutaneous absorption of pharmaceutically active agent
US20090017120A1 (en) * 2007-03-23 2009-01-15 Humco Holding Group, Inc. Phase stable lecithin organogel composition
US8877713B2 (en) 2009-01-09 2014-11-04 Isp Investments Anti-aging peptides and cosmetic and/or pharmaceutical composition containing same
WO2010106433A2 (en) * 2009-03-20 2010-09-23 Himalaya Global Holdings Ltd. Herbal cleansing composition and method of preparing the same
WO2010106433A3 (en) * 2009-03-20 2010-11-18 Himalaya Global Holdings Ltd. Herbal cleansing composition and method of preparing the same
WO2011018472A2 (en) 2009-08-14 2011-02-17 Basf Se Methods in cell cultures, and related inventions, employing certain additives
US20120164162A1 (en) * 2009-08-14 2012-06-28 Basf Se Methods in cell cultures, and related inventions, employing certain additives
US8859235B2 (en) * 2009-08-14 2014-10-14 Basf Se Methods in cell cultures, and related inventions, employing certain additives
WO2011018472A3 (en) * 2009-08-14 2011-05-05 Basf Se Methods in cell cultures, and related inventions, employing certain additives
US20110112491A1 (en) * 2009-11-12 2011-05-12 Graham Janet R Skin Rejuvenation System and Method
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WO2012110435A1 (en) 2011-02-14 2012-08-23 Basf Se Bio process additives
FR2978661A1 (fr) * 2011-08-03 2013-02-08 Beaute Luxe Simplicite Composition lipidique pour application cosmetique
US20150098986A1 (en) * 2013-10-09 2015-04-09 Sky Tree and Camellias Co., Ltd. Method for Producing Elastic Vesicles
US9308154B2 (en) * 2013-10-09 2016-04-12 Greenjoy Biotech Co., Ltd. Method for producing elastic vesicles
WO2016044412A1 (en) * 2014-09-17 2016-03-24 Alps South Europe S.R.O. Topical composition containing antioxidants

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JP5191739B2 (ja) 2013-05-08
JP2008524304A (ja) 2008-07-10
BRPI0518569A2 (pt) 2008-11-25
US10098849B2 (en) 2018-10-16
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ATE475413T1 (de) 2010-08-15
US20120328541A1 (en) 2012-12-27

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