US20100047357A1 - Compositions for topical application comprising a peroxide and retinoid - Google Patents
Compositions for topical application comprising a peroxide and retinoid Download PDFInfo
- Publication number
- US20100047357A1 US20100047357A1 US12/525,329 US52532908A US2010047357A1 US 20100047357 A1 US20100047357 A1 US 20100047357A1 US 52532908 A US52532908 A US 52532908A US 2010047357 A1 US2010047357 A1 US 2010047357A1
- Authority
- US
- United States
- Prior art keywords
- composition
- metal oxide
- particulate matter
- coated
- active ingredient
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 139
- 150000004492 retinoid derivatives Chemical class 0.000 title claims abstract description 47
- 150000002978 peroxides Chemical class 0.000 title claims abstract description 46
- 230000000699 topical effect Effects 0.000 title claims abstract description 15
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 180
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 179
- 239000013618 particulate matter Substances 0.000 claims abstract description 174
- 238000000034 method Methods 0.000 claims abstract description 97
- 239000004480 active ingredient Substances 0.000 claims abstract description 91
- 239000007787 solid Substances 0.000 claims abstract description 58
- 239000011859 microparticle Substances 0.000 claims abstract description 46
- 239000000654 additive Substances 0.000 claims description 132
- 230000000996 additive effect Effects 0.000 claims description 128
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 89
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 77
- 239000010410 layer Substances 0.000 claims description 77
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 72
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 71
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 71
- 229930002330 retinoic acid Natural products 0.000 claims description 68
- 238000000576 coating method Methods 0.000 claims description 56
- 239000011248 coating agent Substances 0.000 claims description 49
- 239000012736 aqueous medium Substances 0.000 claims description 36
- 230000032683 aging Effects 0.000 claims description 35
- 239000006185 dispersion Substances 0.000 claims description 33
- 239000000377 silicon dioxide Substances 0.000 claims description 33
- 239000011247 coating layer Substances 0.000 claims description 30
- 239000013543 active substance Substances 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- OGQICQVSFDPSEI-UHFFFAOYSA-N Zorac Chemical compound N1=CC(C(=O)OCC)=CC=C1C#CC1=CC=C(SCCC2(C)C)C2=C1 OGQICQVSFDPSEI-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 229960000565 tazarotene Drugs 0.000 claims description 15
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 13
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- 208000002874 Acne Vulgaris Diseases 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 8
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 8
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
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- 206010051246 Photodermatosis Diseases 0.000 claims description 4
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- SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
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- LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 claims description 2
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- 230000001747 exhibiting effect Effects 0.000 abstract 1
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- 239000003093 cationic surfactant Substances 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
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- 239000004115 Sodium Silicate Substances 0.000 description 13
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- 238000003756 stirring Methods 0.000 description 11
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 10
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- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 10
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- 125000000129 anionic group Chemical group 0.000 description 7
- 239000000499 gel Substances 0.000 description 7
- 238000001694 spray drying Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000003863 ammonium salts Chemical group 0.000 description 6
- 239000013065 commercial product Substances 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229920002518 Polyallylamine hydrochloride Polymers 0.000 description 4
- 229920002873 Polyethylenimine Polymers 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 4
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
- 235000019345 sodium thiosulphate Nutrition 0.000 description 4
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- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 description 2
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- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000008309 hydrophilic cream Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229920000592 inorganic polymer Polymers 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000005300 metallic glass Substances 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- BKXVGDZNDSIUAI-UHFFFAOYSA-N methoxy(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OC)C1=CC=CC=C1 BKXVGDZNDSIUAI-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001682 microtransfer moulding Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PZNOBXVHZYGUEX-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine;hydrochloride Chemical compound Cl.C=CCNCC=C PZNOBXVHZYGUEX-UHFFFAOYSA-N 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000005324 oxide salts Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- KVOIJEARBNBHHP-UHFFFAOYSA-N potassium;oxido(oxo)alumane Chemical compound [K+].[O-][Al]=O KVOIJEARBNBHHP-UHFFFAOYSA-N 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000005464 sample preparation method Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- GROMGGTZECPEKN-UHFFFAOYSA-N sodium metatitanate Chemical compound [Na+].[Na+].[O-][Ti](=O)O[Ti](=O)O[Ti]([O-])=O GROMGGTZECPEKN-UHFFFAOYSA-N 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical group [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940126702 topical medication Drugs 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- DWAWYEUJUWLESO-UHFFFAOYSA-N trichloromethylsilane Chemical compound [SiH3]C(Cl)(Cl)Cl DWAWYEUJUWLESO-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- TUQLLQQWSNWKCF-UHFFFAOYSA-N trimethoxymethylsilane Chemical compound COC([SiH3])(OC)OC TUQLLQQWSNWKCF-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000000733 zeta-potential measurement Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/203—Retinoic acids ; Salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/327—Peroxy compounds, e.g. hydroperoxides, peroxides, peroxyacids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
Definitions
- Sol-Gel process has been used to encapsulate various active ingredients, thus isolating the active ingredient from the environments.
- FIG. 1 depicts the irritation test results performed according to Example 6.
- the mean size of a side may be in the range 0.3 to 80 microns, preferably 0.3 to 40 microns, more preferably 0.8 to 40, even more preferably 4 to 15 microns.
- the microparticles (coated particulate matter) have a diameter (d90) of 0.5 to 100 ⁇ m or preferably the diameter of the microparticles is in the range of 1 to 50 ⁇ m and most preferably in the range of 5 to 30 ⁇ m. It is appreciated that the microparticles of the present invention are composed of distinct regions of the metal oxide layer in the core material (i.e. the water insoluble particulate matter).
- microparticles are preferably characterized in that the core material is substantially free of the metal oxide and further in that the metal oxide layer is substantially free of said core material, e.g. either as particle dispersion (in the nano-metric range of below 0.1 ⁇ m) of the particulate matter or as molecular dispersion of said particulate matter.
- said coated form of the active ingredient is second microparticles comprising a solid particulate matter of the active ingredient coated by a metal oxide layer.
- said peroxide is in the form of first microparticles comprising solid particulate matter of peroxide coated by a metal oxide layer and said retinoid is in the form of second microparticles comprising a solid particulate matter of the retinoid coated by a metal oxide layer.
- the final form of the composition may be any of the above forms, mentioned with respect to the carrier, where the microparticles are dispersed in the carrier.
- the final form of the composition may also be in the form of a wash or cleanser.
- said first microparticles are prepared by deposition of metal oxide on the surface of the solid particulate matter.
- the deposition of metal oxide on the surface of the particulate matter may be performed by precipitation of a metal oxide salt onto the surface of the particulate matter, forming a metal oxide layer thereon as will be described below or by a spray drying method.
- the first microparticles are prepared by a process comprising:
- the solid, water-insoluble particulate matter refers to the peroxide or retinoid.
- the process described may also be used to coat additional active ingredients (e.g. antibiotics) which may be incorporated into the composition described in the present invention.
- step (b2) subjecting the particulate matter obtained in step (b1) to a coating procedure as in step (b);
- step (c) is repeated 3 to about 1000 times.
- step (c) is repeated 3 to about 300 times, and more preferably 3 to about 100 times. This means that preferably steps (b1) and (b2) are repeated as indicted above with respect to step (c).
- the cationic surfactant selected from monoalkylquaternary ammonium salts, dialkyl quaternary ammonium salts, and mixtures thereof.
- the ionic additive may be an anionic surfactant.
- the weight ratio of the further processed coated particulate matter (e.g. in the repeated steps described in step (c)) to the second cationic additive is in the range of about 25,000/1 to about 50/1, more preferably about 5,000/1 to about 100/1, most preferably about 2000/1 to about 200/1.
- the surface chemical modification preferably comprises modifying the metal oxide surface with organic groups, preferably hydrophobic groups.
- the halo group may be for example chloro, bromo, iodo, fluoro. Most preferably the halo groups are chloro and bromo.
- the positive zeta potential in step (a) is less than +150 mV, more preferably zeta potential in the range +60 mV to +130 mV.
- the preferred zeta potential in step (d) is less than +150 mV, more preferably in the range +5 mV to +130 mV, and most preferably +10 mV to +100 mV. This is the preferred zeta potential also in the further, optional, processing steps.
- the monoalkylquaternary ammonium salt is cetyltrimethylammonium chloride.
- the weight ratio of the second cationic additive to the further processed coated particulate matter is in the range 1:1000-1:10, more preferably 1:200-1:50, most preferably about 1:100.
- the first microparticles may also prepared by spray drying as described for example in:
- the side effects are selected from irritation, erythema, stringing, itching, scaling, dryness, and combinations thereof.
- the aging step The coated BPO suspension at pH 6.5 was kept for aging at room temperature under gentle agitation for 24 hrs.
- the aging step The coated ATRA suspension at pH 4.5 was kept for aging at room temperature under gentle agitation for 24 hrs.
- ATRA All-trans-Retinoic acid
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Toxicology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US12/525,329 US20100047357A1 (en) | 2007-02-01 | 2008-02-03 | Compositions for topical application comprising a peroxide and retinoid |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US89870107P | 2007-02-01 | 2007-02-01 | |
PCT/IL2008/000140 WO2008093346A2 (fr) | 2007-02-01 | 2008-02-03 | Compositions d'application topique comprenant un peroxyde et un rétinoïde |
US12/525,329 US20100047357A1 (en) | 2007-02-01 | 2008-02-03 | Compositions for topical application comprising a peroxide and retinoid |
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Application Number | Title | Priority Date | Filing Date |
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PCT/IL2008/000140 A-371-Of-International WO2008093346A2 (fr) | 2007-02-01 | 2008-02-03 | Compositions d'application topique comprenant un peroxyde et un rétinoïde |
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US13/495,701 Continuation US8617580B2 (en) | 2007-02-01 | 2012-06-13 | Compositions for topical application comprising a peroxide and retinoid |
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US20100047357A1 true US20100047357A1 (en) | 2010-02-25 |
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US13/495,701 Active US8617580B2 (en) | 2007-02-01 | 2012-06-13 | Compositions for topical application comprising a peroxide and retinoid |
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US13/495,701 Active US8617580B2 (en) | 2007-02-01 | 2012-06-13 | Compositions for topical application comprising a peroxide and retinoid |
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---|---|
US (2) | US20100047357A1 (fr) |
EP (1) | EP2109445B1 (fr) |
JP (2) | JP2010517996A (fr) |
KR (1) | KR20090125243A (fr) |
AU (1) | AU2008211553B2 (fr) |
BR (1) | BRPI0808163A2 (fr) |
CA (1) | CA2677184C (fr) |
EA (1) | EA200970724A1 (fr) |
ES (1) | ES2912051T3 (fr) |
MX (1) | MX2009008250A (fr) |
WO (1) | WO2008093346A2 (fr) |
Cited By (7)
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US20100016443A1 (en) * | 2007-02-01 | 2010-01-21 | Sol-Gel Technologies Ltd. | Method for preparing particles comprising metal oxide coating and particles with metal oxide coating |
US20130095185A1 (en) * | 2011-06-29 | 2013-04-18 | Medicis Pharamaceutical Corporation | Stabilized topical formulations containing core-shell microcapsules |
US9687465B2 (en) | 2012-11-27 | 2017-06-27 | Sol-Gel Technologies Ltd. | Compositions for the treatment of rosacea |
US9868103B2 (en) | 2005-08-02 | 2018-01-16 | Sol-Gel Technologies Ltd. | Metal oxide coating of water insoluble ingredients |
US10512796B2 (en) | 2009-12-31 | 2019-12-24 | Sol-Gel Technologies Ltd. | Core stabilized microcapsules, method of their preparation and uses thereof |
US10653899B2 (en) | 2009-12-31 | 2020-05-19 | Sol-Gel Technologies Ltd. | Core stabilized microcapsules, method of their preparation and uses thereof |
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JP2011529392A (ja) | 2008-07-31 | 2011-12-08 | ゾル−ゲル テクノロジー リミテッド | 活性成分および金属酸化物シェルを含むマイクロカプセル、その製造方法およびその使用 |
BRPI1006011A2 (pt) * | 2009-01-05 | 2016-04-05 | Sol Gel Technologies Ltd | sistema tópico de múltiplos componentes, métodos para tratar, melhorar a aparência de ou evitar uma doença ou condição da pele ou de uma membrana de mucosa, para tratar lesões da pela, para tratar comedões de pele, e para tratar acne, uso de um sistema, e, kit. |
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WO2011154421A1 (fr) * | 2010-06-09 | 2011-12-15 | Basf Se | Microcapsules contenant du principe actif et présentant une enveloppe qui contient de l'oxyde métallique |
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Citations (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4350681A (en) * | 1977-10-07 | 1982-09-21 | A.H.C. Pharmacal, Inc. | Stabilized benzoyl peroxide compositions |
US4361584A (en) * | 1977-10-07 | 1982-11-30 | A.H.C. Pharmacal, Inc. | Composition and method for the treatment of acne |
US4387107A (en) * | 1979-07-25 | 1983-06-07 | Dermik Laboratories, Inc. | Stable benzoyl peroxide composition |
US4497794A (en) * | 1980-12-08 | 1985-02-05 | Dermik Laboratories, Inc. | Erythromycin/benzoyl peroxide composition for the treatment of acne |
US4671956A (en) * | 1983-12-01 | 1987-06-09 | L'oreal | Antiacne composition containing benzoic peroxide in association with at least one sun filter |
US4690825A (en) * | 1985-10-04 | 1987-09-01 | Advanced Polymer Systems, Inc. | Method for delivering an active ingredient by controlled time release utilizing a novel delivery vehicle which can be prepared by a process utilizing the active ingredient as a porogen |
US4931362A (en) * | 1987-08-18 | 1990-06-05 | F.Joh.Kwizda Gesellschaft M.B.H. | Microcapsule and micromatrix bodies and method for their formation |
US4960772A (en) * | 1988-03-09 | 1990-10-02 | L'oreal | Benzoyl peroxide and quaternary ammonium based pharmaceutical and cosmetic compositions |
US5086075A (en) * | 1985-01-24 | 1992-02-04 | Board Of Regents, The University Of Texas System | Therapeutic compositions containing benzoyl peroxide |
US5145675A (en) * | 1986-03-31 | 1992-09-08 | Advanced Polymer Systems, Inc. | Two step method for preparation of controlled release formulations |
US5466446A (en) * | 1994-02-16 | 1995-11-14 | Stiefel Laboratories, Inc. | Topical compositions containing bensoyl peroxide and clindamycin and method of use thereof |
US5632996A (en) * | 1995-04-14 | 1997-05-27 | Imaginative Research Associates, Inc. | Benzoyl peroxide and benzoate ester containing compositions suitable for contact with skin |
US5767098A (en) * | 1985-12-12 | 1998-06-16 | Dermik Laboratories, Inc. | Anti-acne method and composition |
US5851538A (en) * | 1995-12-29 | 1998-12-22 | Advanced Polymer Systems, Inc. | Retinoid formulations in porous microspheres for reduced irritation and enhanced stability |
US5879716A (en) * | 1985-12-18 | 1999-03-09 | Advanced Polymer Systems, Inc. | Methods and compositions for topical delivery of benzoyl peroxide |
US5955109A (en) * | 1985-12-18 | 1999-09-21 | Advanced Polymer Systems, Inc. | Methods and compositions for topical delivery of retinoic acid |
US5998392A (en) * | 1996-04-10 | 1999-12-07 | Gattefosse S.A. | Benzoyl peroxide flocculent materials and methods of their preparation |
US6013637A (en) * | 1998-06-12 | 2000-01-11 | Dermik Laboratories Inc. | Anti-acne method and composition |
US6096765A (en) * | 1998-07-28 | 2000-08-01 | Bershad; Susan | Short contact treatment of acne with topical retinoids |
US6117843A (en) * | 1992-02-18 | 2000-09-12 | Lloyd J. Baroody | Compositions for the treatment of acne containing clindamycin and benzoyl peroxide |
US6238650B1 (en) * | 1999-05-26 | 2001-05-29 | Sol-Gel Technologies Ltd. | Sunscreen composition containing sol-gel microcapsules |
US6251313B1 (en) * | 1998-03-12 | 2001-06-26 | Wacker-Chemie Gmbh | Process for the preparation of microencapsulated products having organopolysiloxane walls |
US6303149B1 (en) * | 1998-08-13 | 2001-10-16 | Sol-Gel Technologies, Ltd. | Method for the preparation of oxide microcapsules loaded with functional molecules and the products obtained thereof |
US6337089B1 (en) * | 1998-02-06 | 2002-01-08 | Seiwa Kasei Company, Limited | Microcapsule containing core material and method for producing the same |
US20020064541A1 (en) * | 2000-04-21 | 2002-05-30 | Noa Lapidot | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
US6436375B1 (en) * | 1999-05-25 | 2002-08-20 | Sol-Gel Technologies Ltd. | Method for obtaining photostable sunscreen compositions |
US6468509B2 (en) * | 1998-12-18 | 2002-10-22 | Sol-Gel Technologies Ltd. | Sunscreen composition containing sol-gel microcapsules |
US20030170196A1 (en) * | 2001-12-21 | 2003-09-11 | Sandrine Orsoni | Dermatological/cosmetic gels comprising at least one retinoid and benzoyl peroxide |
US6855335B2 (en) * | 2003-06-17 | 2005-02-15 | Unitech Co., Ltd. | Process for preparing silica microcapsules |
US20050037087A1 (en) * | 2001-11-08 | 2005-02-17 | Noa Lapidot | Compositions containing oils having a specific gravity higher than the specific gravity of water |
US20050276807A1 (en) * | 2004-06-15 | 2005-12-15 | Advanced Biotherapy, Inc. | Treatment of acne |
Family Cites Families (100)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2885366A (en) | 1956-06-28 | 1959-05-05 | Du Pont | Product comprising a skin of dense, hydrated amorphous silica bound upon a core of another solid material and process of making same |
US3785798A (en) | 1967-04-26 | 1974-01-15 | Gaf Corp | Biologically active particulate material and the process for manufacturing same |
GB1399344A (en) | 1971-06-03 | 1975-07-02 | Ici Ltd | Method of producing vesiculated particles of inorganic materials |
US3826670A (en) | 1972-11-07 | 1974-07-30 | Sherwin Williams Co | Encapsulation of organic pigments |
US3957971A (en) | 1974-07-29 | 1976-05-18 | Lever Brothers Company | Moisturizing units and moisturizing compositions containing the same |
US4087555A (en) | 1975-09-08 | 1978-05-02 | Helena Rubinstein, Inc. | Skin cream containing milk protein |
US4349456A (en) | 1976-04-22 | 1982-09-14 | Minnesota Mining And Manufacturing Company | Non-vitreous ceramic metal oxide microcapsules and process for making same |
DE2642032C2 (de) | 1976-09-18 | 1987-04-30 | Rupprecht, Herbert, Prof. Dr., 8400 Regensburg | Verfahren zur Inkorporierung von Wirkstoffen in siliciumdioxidhaltige Trägermaterialien und eine siliciumdioxidhaltige Zubereitung |
US4606913A (en) | 1978-09-25 | 1986-08-19 | Lever Brothers Company | High internal phase emulsions |
US4464317A (en) | 1980-01-28 | 1984-08-07 | The Washington University | Method of encapsulating active agents with inorganic coatings |
US4692329A (en) | 1980-12-08 | 1987-09-08 | William H. Rorer, Inc. | Erythromycin/benzoyl peroxide antiacne compositions |
GB2110083B (en) | 1981-11-24 | 1985-05-30 | Colgate Palmolive Co | Visually clear coloured dentifrice |
JPS6191137A (ja) | 1984-10-11 | 1986-05-09 | Kao Corp | 外用薬剤組成物 |
US4769080A (en) | 1985-06-24 | 1988-09-06 | The Dow Chemical Company | Insoluble pigments and preparation thereof |
US4880851A (en) | 1987-02-26 | 1989-11-14 | Tohru Yamamoto | Aromatic composition and method for the production of the same |
US4891211A (en) | 1988-06-29 | 1990-01-02 | Church & Dwight Co., Inc. | Stable hydrogen peroxide-releasing dentifice |
US5126915A (en) | 1989-07-28 | 1992-06-30 | E. I. Du Pont De Nemours And Company | Metal oxide-coated electrically conductive powders and compositions thereof |
IL93134A (en) | 1990-01-23 | 1997-11-20 | Yissum Res Dev Co | Doped sol-gel glasses for obtaining chemical interactions |
US5318797A (en) | 1990-06-20 | 1994-06-07 | Clarkson University | Coated particles, hollow particles, and process for manufacturing the same |
GB9021061D0 (en) | 1990-09-27 | 1990-11-07 | Unilever Plc | Encapsulating method and products containing encapsulated material |
US5223250A (en) | 1991-02-05 | 1993-06-29 | Sun Smart, Inc. | Visibly transparent UV sunblock cosmetic compositions |
US5733531A (en) | 1991-02-05 | 1998-03-31 | Sunsmart, Inc. | Composite UV sunblock compositions |
US5165914A (en) | 1991-03-04 | 1992-11-24 | David G. Vlock | Oral compositions containing zinc lactate complexes |
FR2675398B1 (fr) | 1991-04-19 | 1994-04-01 | Roussel Uclaf | Micro-capsules de filtres solaires, leur procede de preparation, les compositions cosmetiques et pharmaceutiques les comprenant et leurs applications. |
US5200334A (en) | 1991-08-13 | 1993-04-06 | The Regents Of The University Of California | Sol-gel encapsulated enzyme |
FR2681248B1 (fr) | 1991-09-13 | 1995-04-28 | Oreal | Composition pour un traitement cosmetique et/ou pharmaceutique de longue duree des couches superieures de l'epiderme par une application topique sur la peau. |
US5269840A (en) | 1992-02-04 | 1993-12-14 | Minnesota Mining And Manufacturing Company | Sol bonded colorant clusters and process for making |
US5520917A (en) | 1992-07-27 | 1996-05-28 | Suzuki Yushi Industries Co., Ltd. | Materials in the form of colored spherical fine particles |
FR2694894B1 (fr) | 1992-08-20 | 1994-11-10 | Coletica | Utilisation d'une réaction de transacylation entre un polysaccharide estérifié et une substance polyaminée ou polyhydroxylée pour la fabrication de microparticules, procédé et composition. |
FR2694895B1 (fr) | 1992-08-20 | 1994-11-10 | Coletica | Procédé de fabrication de microparticules en émulsion par modification de la composition chimique de la phase dispersée après émulsification. |
FR2703927B1 (fr) | 1993-04-13 | 1995-07-13 | Coletica | Utilisation d'une réaction de transacylation entre un polysaccharide estérifié et une polyamine pour former en milieu aqueux une membrane au moins en surface de particules gélifiées. |
DE4321005A1 (de) | 1993-06-24 | 1995-01-05 | Merck Patent Gmbh | Perlglanzpigment für Wasserlacksysteme |
US5895757A (en) | 1993-06-30 | 1999-04-20 | Pope; Edward J. A. | Encapsulation of living tissue cells in inorganic microspheres prepared from an organosilicon |
US5739020A (en) | 1995-01-10 | 1998-04-14 | Pope; Edward J. A. | Encapsulation of animal and microbial cells in an inorganic gel prepared from an organosilicon |
US5846554A (en) | 1993-11-15 | 1998-12-08 | Zeneca Limited | Microcapsules containing suspensions of biologically active compounds and ultraviolet protectant |
DE4341113B4 (de) | 1993-12-02 | 2006-04-13 | IFAC Institut für angewandte Colloidtechnologie GmbH & Co. KG | Stabile multiple X/O/Y-Emulsion |
FR2719218B1 (fr) | 1994-04-28 | 1996-07-05 | Oreal | Utilisation d'une suspension colloïdale à base de charges minérales comme composition cosmétique permettant de former un film sur les cheveux, la peau et/ou les ongles. |
DE4416003C2 (de) | 1994-05-06 | 1999-02-11 | Feinchemie Gmbh Sebnitz | Metalloxidpulver und -filme mit inkorporierten organischen Flüssigkeiten und Ölen, ihre Herstellung und Verwendung |
EP0680753A3 (fr) | 1994-05-06 | 1996-08-28 | Feinchemie Gmbh Sebnitz | Composite d'oxyde de métal à libération réglable. |
FR2720632B1 (fr) | 1994-06-03 | 1996-07-05 | Oreal | Compositions cosmétiques photoprotectrices contenant un système filtrant les rayons UV et des polymères particuliers et utilisations. |
US5591453A (en) | 1994-07-27 | 1997-01-07 | The Trustees Of The University Of Pennsylvania | Incorporation of biologically active molecules into bioactive glasses |
US5445823A (en) | 1994-10-20 | 1995-08-29 | The Procter & Gamble Company | Dermatological compositions and method of treatment of skin lesions therewith |
US5576097A (en) | 1995-04-24 | 1996-11-19 | Brite-Line Industries, Inc. | High brightness durable retro-reflecting microspheres and method of making the same |
US5700451A (en) | 1995-05-24 | 1997-12-23 | The Procter & Gamble Company | Sunscreen composition |
US5874105A (en) | 1996-01-31 | 1999-02-23 | Collaborative Laboratories, Inc. | Lipid vesicles formed with alkylammonium fatty acid salts |
US5785977A (en) | 1996-02-07 | 1998-07-28 | Breithbarth; Richard | Non-metallic microparticle carrier materials |
FR2747668B1 (fr) | 1996-04-22 | 1998-05-22 | Rhone Poulenc Chimie | Procede de preparation de silice comprenant une ecorce de silice et un coeur en un materiau autre |
US5876699A (en) | 1996-05-14 | 1999-03-02 | Disomma; Joseph | Sunblock composition suitable for sensitive skin areas |
DE19625267A1 (de) | 1996-06-25 | 1998-01-08 | Bayer Ag | Verfahren zur Herstellung anorganisch beschichteter Pigmente und Füllstoffe |
GB9616978D0 (en) | 1996-08-13 | 1996-09-25 | Tioxide Specialties Ltd | Zinc oxide dispersions |
FR2755856B1 (fr) | 1996-11-21 | 1999-01-29 | Merck Clevenot Laboratoires | Microcapsules de chitine ou de derives de chitine contenant une substance hydrophobe, notamment un filtre solaire et procede de preparation de telles microcapsules |
IL120022A (en) | 1997-01-16 | 2003-02-12 | Yissum Res Dev Co | Sunscreens for protection from sun radiation |
FR2758826B1 (fr) | 1997-01-27 | 1999-04-16 | Rhodia Chimie Sa | Nouveau pigment de dioxide de titane, son procede de preparation et son utilisation dans les compositions de peinture |
US5962517A (en) | 1997-01-31 | 1999-10-05 | Murad; Howard | Pharmaceutical compositions and methods for treating acne |
US5906811A (en) | 1997-06-27 | 1999-05-25 | Thione International, Inc. | Intra-oral antioxidant preparations |
FR2766090B1 (fr) | 1997-07-15 | 1999-10-08 | Coletica | Particules, en particulier micro- ou nanoparticules de proteines vegetales reticulees, leur procede de preparation et compositions cosmetiques, pharmaceutiques ou alimentaires en contenant |
US6280746B1 (en) | 1997-10-17 | 2001-08-28 | International Flora Technologies Ltd. | Dry emollient compositions |
US6090399A (en) | 1997-12-11 | 2000-07-18 | Rohm And Haas Company | Controlled release composition incorporating metal oxide glass comprising biologically active compound |
US6015548A (en) | 1998-07-10 | 2000-01-18 | Shaklee Corporation | High efficiency skin protection formulation with sunscreen agents and antioxidants |
FR2774906B1 (fr) | 1998-02-13 | 2000-05-12 | Rhodia Chimie Sa | Systeme d'encapsulation a coeur organique et a ecorce minerale a base d'hydroxycarbonate d'aluminium et son procede de preparation |
DE19811900C2 (de) | 1998-03-18 | 2003-12-11 | Kallies Feinchemie Ag | Biokompatibles Kompositmaterial, Verfahren zu seiner Herstellung und seine Verwendung |
EP0972563A1 (fr) | 1998-07-15 | 2000-01-19 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Fabrication de particules et coquilles vides revêtues de plusieurs couches par autoassemblage électrostatique de multicouche nanocomposite sur des matrices colloidales décomposables |
JP2003522621A (ja) | 1998-03-19 | 2003-07-29 | マックス−プランク−ゲゼルシャフト・ツア・フェルデルング・デア・ヴィッセンシャフテン・エー・ファオ | 分解性コロイド原型上のナノ複合多層の静電的自己集成体による多層被覆粒子及び中空シェルの製造 |
FR2780901B1 (fr) | 1998-07-09 | 2000-09-29 | Coletica | Particules, en particulier micro- ou nanoparticules de monosaccharides et oligosaccharides reticules, leurs procedes de preparation et compositions cosmetiques, pharmaceutiques ou alimentaires en contenant |
US6146664A (en) | 1998-07-10 | 2000-11-14 | Shaklee Corporation | Stable topical ascorbic acid compositions |
US6103267A (en) | 1998-07-27 | 2000-08-15 | Sunsmart, Inc. | Stabilized ascorbic acid, composition, and method of use |
US6074629A (en) | 1998-07-27 | 2000-06-13 | J. M. Huber Corporation | Dentifrice with a dye absorbing silica for imparting a speckled appearance thereto |
US6217852B1 (en) | 1998-08-15 | 2001-04-17 | Skinnovative Dermatologic Concepts, L.L.C. | Personal cleansing compositions having photoprotective agents |
DE19842766A1 (de) | 1998-09-18 | 2000-03-23 | Beiersdorf Ag | Emulgatorfreie feindisperse Systeme vom Typ Öl-in-Wasser und Wasser-in-Öl |
FR2785199B1 (fr) | 1998-10-30 | 2001-01-05 | Rhodia Chimie Sa | Procede de preparation de capsules constituees d'un noyau de matiere active liquide entoure d'une ecorce minerale |
FR2785292B1 (fr) | 1998-10-30 | 2002-06-28 | Rhodia Chimie Sa | Capsules a ecorce minerale poreuse dans lesquelles sont immobilisees dans un milieu biologique liquide, une ou plusieurs matieres biologiques, leurs procede de preparation et utilisations |
EP1167462B1 (fr) | 1999-01-11 | 2010-12-22 | Showa Denko K.K. | Preparation cosmetique, particules d'oxyde metallique enrobees d'un sol de silice rendues hydrophobes en surface, oxyde metallique revetu de sol de silice rendues hydrophobes et procedes de production |
AU772153B2 (en) | 1999-02-12 | 2004-04-08 | Molecular Insight Pharmaceuticals, Inc. | Matrices for drug delivery and methods for making and using the same |
US6495352B1 (en) | 1999-04-15 | 2002-12-17 | Sandia Corporation | Sol-gel method for encapsulating molecules |
US6143280A (en) | 1999-05-18 | 2000-11-07 | J. M. Huber Corporation | Color containing silica resistant to dye migration and method of making the same |
FR2799119B1 (fr) | 1999-10-01 | 2001-11-30 | Oreal | Procede pour ameliorer la stabilite vis-a-vis du rayonnement uv de filtres solaires photosensibles |
DE10001172A1 (de) | 2000-01-13 | 2001-07-26 | Max Planck Gesellschaft | Templatieren von Feststoffpartikeln mit Polymermultischichten |
NZ520554A (en) | 2000-02-08 | 2005-08-26 | Euro Celtique S | Tamper-resistant oral opioid agonist formulations |
JP4979109B2 (ja) * | 2000-04-21 | 2012-07-18 | ゾル−ゲル テクノロジーズ リミテッド | 局所的有効成分の増強された配合安定性および送達を示す組成物 |
US6303290B1 (en) | 2000-09-13 | 2001-10-16 | The Trustees Of The University Of Pennsylvania | Encapsulation of biomaterials in porous glass-like matrices prepared via an aqueous colloidal sol-gel process |
US20020193321A1 (en) | 2000-12-12 | 2002-12-19 | Mohan Vishnupad | Dual dispenser for aesthitically acceptable delivery of anhydrous skin treatment compositions |
US7060732B2 (en) | 2000-12-12 | 2006-06-13 | Imaginative Research Associates, Inc. | Antibiotic/benzoyl peroxide dispenser |
US20020151527A1 (en) | 2000-12-20 | 2002-10-17 | Benjamin Wiegand | Method for reducing acne or improving skin tone |
GB2377078B (en) | 2001-06-27 | 2003-06-04 | Morgan Crucible Co | Fuel cell or electrolyser construction |
JP3900863B2 (ja) | 2001-06-28 | 2007-04-04 | シャープ株式会社 | データ転送制御装置、半導体記憶装置および情報機器 |
US6913825B2 (en) | 2001-09-20 | 2005-07-05 | University Of Notre Dame Du Lac | Process for making mesoporous silicate nanoparticle coatings and hollow mesoporous silica nano-shells |
US7037513B1 (en) | 2005-01-31 | 2006-05-02 | Aquea Scientific Corporation | Bodywash additives |
FR2833841B1 (fr) | 2001-12-21 | 2005-07-22 | Galderma Res & Dev | Gel comprenant au moins un retinoide et du peroxyde de benzoyle |
GB0202853D0 (en) | 2002-02-07 | 2002-03-27 | Dow Corning | Encapsulation process and encapsulated compositions |
US6875264B2 (en) | 2003-01-17 | 2005-04-05 | Engelhard Corporation | Multi-layer effect pigment |
WO2004064769A2 (fr) * | 2003-01-21 | 2004-08-05 | Hector Herrera | Methodes de production et d'utilisation d'agents d'administration topique |
GB0301577D0 (en) | 2003-01-23 | 2003-02-26 | Edko Pazarlama Tanitim Ltd Sti | Topical pharmaceutical and/or cosmetic dispense systems |
FR2850576B1 (fr) | 2003-02-05 | 2007-03-23 | Ethypharm Sa | Composition comprenant un melange de principes actifs, et procede de preparation |
US7923030B2 (en) | 2003-03-14 | 2011-04-12 | Sol-Gel Technologies, Inc. | Agent-encapsulating micro- and nanoparticles, methods for preparation of same and products containing same |
CA2533406C (fr) | 2003-07-31 | 2013-01-22 | Sol-Gel Technologies Ltd. | Microcapsules chargees d'ingredients actifs et procede de preparation |
US20050208134A1 (en) | 2004-02-25 | 2005-09-22 | Shlomo Magdassi | Biocompatible polymeric beads and use thereof |
GB2416524A (en) | 2004-07-24 | 2006-02-01 | Dow Corning | Microcapsules with siloxane walls formed in situ |
US7001592B1 (en) | 2005-01-31 | 2006-02-21 | Aquea Scientific Corporation | Sunscreen compositions and methods of use |
AR054805A1 (es) | 2005-06-29 | 2007-07-18 | Stiefel Laboratories | Composiciones topicas para el tratamiento de la piel |
JP5164840B2 (ja) | 2005-08-02 | 2013-03-21 | ソル − ゲル テクノロジーズ リミテッド | 水不溶性成分の金属酸化物被覆 |
-
2008
- 2008-02-03 EA EA200970724A patent/EA200970724A1/ru unknown
- 2008-02-03 WO PCT/IL2008/000140 patent/WO2008093346A2/fr active Application Filing
- 2008-02-03 KR KR1020097018024A patent/KR20090125243A/ko not_active Application Discontinuation
- 2008-02-03 EP EP08702719.9A patent/EP2109445B1/fr active Active
- 2008-02-03 CA CA2677184A patent/CA2677184C/fr active Active
- 2008-02-03 BR BRPI0808163-8A2A patent/BRPI0808163A2/pt not_active IP Right Cessation
- 2008-02-03 JP JP2009547810A patent/JP2010517996A/ja active Pending
- 2008-02-03 US US12/525,329 patent/US20100047357A1/en not_active Abandoned
- 2008-02-03 AU AU2008211553A patent/AU2008211553B2/en not_active Ceased
- 2008-02-03 MX MX2009008250A patent/MX2009008250A/es active IP Right Grant
- 2008-02-03 ES ES08702719T patent/ES2912051T3/es active Active
-
2012
- 2012-06-13 US US13/495,701 patent/US8617580B2/en active Active
-
2013
- 2013-07-18 JP JP2013149000A patent/JP5923065B2/ja active Active
Patent Citations (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4350681A (en) * | 1977-10-07 | 1982-09-21 | A.H.C. Pharmacal, Inc. | Stabilized benzoyl peroxide compositions |
US4361584A (en) * | 1977-10-07 | 1982-11-30 | A.H.C. Pharmacal, Inc. | Composition and method for the treatment of acne |
US4387107A (en) * | 1979-07-25 | 1983-06-07 | Dermik Laboratories, Inc. | Stable benzoyl peroxide composition |
US4497794A (en) * | 1980-12-08 | 1985-02-05 | Dermik Laboratories, Inc. | Erythromycin/benzoyl peroxide composition for the treatment of acne |
US4671956A (en) * | 1983-12-01 | 1987-06-09 | L'oreal | Antiacne composition containing benzoic peroxide in association with at least one sun filter |
US5086075A (en) * | 1985-01-24 | 1992-02-04 | Board Of Regents, The University Of Texas System | Therapeutic compositions containing benzoyl peroxide |
US4690825A (en) * | 1985-10-04 | 1987-09-01 | Advanced Polymer Systems, Inc. | Method for delivering an active ingredient by controlled time release utilizing a novel delivery vehicle which can be prepared by a process utilizing the active ingredient as a porogen |
US5767098A (en) * | 1985-12-12 | 1998-06-16 | Dermik Laboratories, Inc. | Anti-acne method and composition |
US5879716A (en) * | 1985-12-18 | 1999-03-09 | Advanced Polymer Systems, Inc. | Methods and compositions for topical delivery of benzoyl peroxide |
US5955109A (en) * | 1985-12-18 | 1999-09-21 | Advanced Polymer Systems, Inc. | Methods and compositions for topical delivery of retinoic acid |
US5145675A (en) * | 1986-03-31 | 1992-09-08 | Advanced Polymer Systems, Inc. | Two step method for preparation of controlled release formulations |
US4931362A (en) * | 1987-08-18 | 1990-06-05 | F.Joh.Kwizda Gesellschaft M.B.H. | Microcapsule and micromatrix bodies and method for their formation |
US4960772A (en) * | 1988-03-09 | 1990-10-02 | L'oreal | Benzoyl peroxide and quaternary ammonium based pharmaceutical and cosmetic compositions |
US6117843A (en) * | 1992-02-18 | 2000-09-12 | Lloyd J. Baroody | Compositions for the treatment of acne containing clindamycin and benzoyl peroxide |
US5466446A (en) * | 1994-02-16 | 1995-11-14 | Stiefel Laboratories, Inc. | Topical compositions containing bensoyl peroxide and clindamycin and method of use thereof |
US5632996A (en) * | 1995-04-14 | 1997-05-27 | Imaginative Research Associates, Inc. | Benzoyl peroxide and benzoate ester containing compositions suitable for contact with skin |
US5851538A (en) * | 1995-12-29 | 1998-12-22 | Advanced Polymer Systems, Inc. | Retinoid formulations in porous microspheres for reduced irritation and enhanced stability |
US5998392A (en) * | 1996-04-10 | 1999-12-07 | Gattefosse S.A. | Benzoyl peroxide flocculent materials and methods of their preparation |
US6337089B1 (en) * | 1998-02-06 | 2002-01-08 | Seiwa Kasei Company, Limited | Microcapsule containing core material and method for producing the same |
US6251313B1 (en) * | 1998-03-12 | 2001-06-26 | Wacker-Chemie Gmbh | Process for the preparation of microencapsulated products having organopolysiloxane walls |
US6013637A (en) * | 1998-06-12 | 2000-01-11 | Dermik Laboratories Inc. | Anti-acne method and composition |
US6096765A (en) * | 1998-07-28 | 2000-08-01 | Bershad; Susan | Short contact treatment of acne with topical retinoids |
US6303149B1 (en) * | 1998-08-13 | 2001-10-16 | Sol-Gel Technologies, Ltd. | Method for the preparation of oxide microcapsules loaded with functional molecules and the products obtained thereof |
US6468509B2 (en) * | 1998-12-18 | 2002-10-22 | Sol-Gel Technologies Ltd. | Sunscreen composition containing sol-gel microcapsules |
US6436375B1 (en) * | 1999-05-25 | 2002-08-20 | Sol-Gel Technologies Ltd. | Method for obtaining photostable sunscreen compositions |
US6238650B1 (en) * | 1999-05-26 | 2001-05-29 | Sol-Gel Technologies Ltd. | Sunscreen composition containing sol-gel microcapsules |
US20020064541A1 (en) * | 2000-04-21 | 2002-05-30 | Noa Lapidot | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
US7758888B2 (en) * | 2000-04-21 | 2010-07-20 | Sol-Gel Technologies Ltd. | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
US8039020B2 (en) * | 2000-04-21 | 2011-10-18 | Sol-Gel Technologies Ltd. | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
US20050037087A1 (en) * | 2001-11-08 | 2005-02-17 | Noa Lapidot | Compositions containing oils having a specific gravity higher than the specific gravity of water |
US20030170196A1 (en) * | 2001-12-21 | 2003-09-11 | Sandrine Orsoni | Dermatological/cosmetic gels comprising at least one retinoid and benzoyl peroxide |
US6855335B2 (en) * | 2003-06-17 | 2005-02-15 | Unitech Co., Ltd. | Process for preparing silica microcapsules |
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Also Published As
Publication number | Publication date |
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MX2009008250A (es) | 2009-08-27 |
WO2008093346A2 (fr) | 2008-08-07 |
ES2912051T3 (es) | 2022-05-24 |
WO2008093346A3 (fr) | 2009-05-28 |
KR20090125243A (ko) | 2009-12-04 |
US8617580B2 (en) | 2013-12-31 |
JP5923065B2 (ja) | 2016-05-24 |
AU2008211553A1 (en) | 2008-08-07 |
JP2010517996A (ja) | 2010-05-27 |
EP2109445A2 (fr) | 2009-10-21 |
JP2013213063A (ja) | 2013-10-17 |
EA200970724A1 (ru) | 2010-02-26 |
AU2008211553B2 (en) | 2013-06-20 |
CA2677184A1 (fr) | 2008-08-07 |
US20120269874A1 (en) | 2012-10-25 |
BRPI0808163A2 (pt) | 2014-11-04 |
CA2677184C (fr) | 2014-12-23 |
EP2109445B1 (fr) | 2022-04-20 |
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