JP6006272B2 - 水及び水混和性有機溶媒中に懸濁する低濃度過酸化ベンゾイルを含む局所用医薬品製剤 - Google Patents
水及び水混和性有機溶媒中に懸濁する低濃度過酸化ベンゾイルを含む局所用医薬品製剤 Download PDFInfo
- Publication number
- JP6006272B2 JP6006272B2 JP2014188286A JP2014188286A JP6006272B2 JP 6006272 B2 JP6006272 B2 JP 6006272B2 JP 2014188286 A JP2014188286 A JP 2014188286A JP 2014188286 A JP2014188286 A JP 2014188286A JP 6006272 B2 JP6006272 B2 JP 6006272B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- benzoyl peroxide
- concentration
- formulation
- propylene glycol
- 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.)
- Active
Links
- 239000004342 Benzoyl peroxide Substances 0.000 title claims description 87
- 235000019400 benzoyl peroxide Nutrition 0.000 title claims description 87
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 title claims description 86
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 31
- 230000000699 topical effect Effects 0.000 title claims description 11
- 239000003960 organic solvent Substances 0.000 title description 27
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 101
- 238000009472 formulation Methods 0.000 claims description 78
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 60
- 238000002360 preparation method Methods 0.000 claims description 30
- 206010000496 acne Diseases 0.000 claims description 27
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 26
- 239000004520 water soluble gel Substances 0.000 claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 14
- 239000003349 gelling agent Substances 0.000 claims description 13
- 239000000725 suspension Substances 0.000 claims description 12
- 229920002125 Sokalan® Polymers 0.000 claims description 9
- UFUVLHLTWXBHGZ-MGZQPHGTSA-N [(2r,3r,4s,5r,6r)-6-[(1s,2s)-2-chloro-1-[[(2s,4r)-1-methyl-4-propylpyrrolidine-2-carbonyl]amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](OP(O)(O)=O)[C@@H](SC)O1 UFUVLHLTWXBHGZ-MGZQPHGTSA-N 0.000 claims description 2
- 229960002291 clindamycin phosphate Drugs 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- 229960001631 carbomer Drugs 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 description 13
- 229940088710 antibiotic agent Drugs 0.000 description 12
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 11
- 229960002227 clindamycin Drugs 0.000 description 10
- 230000003902 lesion Effects 0.000 description 10
- 230000007794 irritation Effects 0.000 description 8
- 230000002757 inflammatory effect Effects 0.000 description 7
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 6
- 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 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 229960005287 lincomycin Drugs 0.000 description 6
- OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 description 6
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 229960003276 erythromycin Drugs 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000003120 macrolide antibiotic agent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 201000004700 rosacea Diseases 0.000 description 3
- 208000017520 skin disease Diseases 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940112144 benzaclin Drugs 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000012049 topical pharmaceutical composition Substances 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 235000014653 Carica parviflora Nutrition 0.000 description 1
- AUODDLQVRAJAJM-XJQDNNTCSA-N Clindamycin hydrochloride Chemical compound Cl.CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 AUODDLQVRAJAJM-XJQDNNTCSA-N 0.000 description 1
- 241000243321 Cnidaria Species 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 206010033733 Papule Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- HDSBZMRLPLPFLQ-UHFFFAOYSA-N Propylene glycol alginate Chemical compound OC1C(O)C(OC)OC(C(O)=O)C1OC1C(O)C(O)C(C)C(C(=O)OCC(C)O)O1 HDSBZMRLPLPFLQ-UHFFFAOYSA-N 0.000 description 1
- 206010037888 Rash pustular Diseases 0.000 description 1
- 229930194936 Tylosin Natural products 0.000 description 1
- 239000004182 Tylosin Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 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 description 1
- 229960002916 adapalene Drugs 0.000 description 1
- 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 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229960002255 azelaic acid Drugs 0.000 description 1
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 1
- 229960004099 azithromycin Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229960002626 clarithromycin Drugs 0.000 description 1
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 1
- 229960001200 clindamycin hydrochloride Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940055366 duac Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000770 propane-1,2-diol alginate Substances 0.000 description 1
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960000565 tazarotene Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JTSDBFGMPLKDCD-XVFHVFLVSA-N tilmicosin Chemical compound O([C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CCN1C[C@H](C)C[C@H](C)C1)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@@H]1O[C@H](C)[C@@H](O)[C@H](N(C)C)[C@H]1O JTSDBFGMPLKDCD-XVFHVFLVSA-N 0.000 description 1
- 229960000223 tilmicosin Drugs 0.000 description 1
- 229940042129 topical gel Drugs 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 1
- 229960004059 tylosin Drugs 0.000 description 1
- 235000019375 tylosin Nutrition 0.000 description 1
- 229940045136 urea Drugs 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- 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
- A61K9/08—Solutions
-
- 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
- A61K9/10—Dispersions; Emulsions
-
- 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
- A61K31/075—Ethers or acetals
-
- 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
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- 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
- A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or 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
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/042—Gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/044—Suspensions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/38—Percompounds, e.g. peracids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
-
- 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
- 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
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/30—Characterized by the absence of a particular group of ingredients
- A61K2800/33—Free of surfactant
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/413—Nanosized, i.e. having sizes below 100 nm
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Dispersion Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
(1)水混和性がある
(2)0℃から40℃の間の温度で過酸化ベンゾイルと化学的に反応しない
(3)0℃から40℃の間の温度で液体である
(4)少なくとも0.1%の濃度で、外界温度において、過酸化ベンゾイルを溶解可能である
(5)界面活性剤の非存在下で水溶性ゲル状の過酸化ベンゾイルを分散可能である
本発明の医薬品製剤を図1に示される以下の成分を含むように製剤した。
過酸化ベンゾイルに加えニキビ抑制薬剤を含む本発明の医薬品製剤を、図2に示される以下の成分を含むように製剤した。
前記実施例2の水溶性ゲル製剤であり、過酸化ベンゾイル2.5%、プロピレングリコール5%、水89%、およびクリンダマイシン1%を含む前記水溶性ゲル製剤のニキビ病変に対するその有効性を399名の患者が治療される大規模な臨床調査においてテストした。本発明による製剤を製剤Aとする。過酸化ベンゾイル5.0%、プロピレングリコール10%、水82.5%、およびクリンダマイシン1.0%を含む類似の水溶性ゲル製剤を調整し、ニキビ病変に対するその有効性をよく似た設定の第2の臨床調査でテストした。この製剤(本発明によるものではない)を製剤Bとする。これらの結果を過酸化ベンゾイル5.0%、クリンダマイシン1%、ジオクチルスルホコハク酸ナトリウム(界面活性剤)、及び水を含む水溶性ゲル市販製品(BenzaClin(登録商標)局所ゲル、ダーミック・ラボラトリーズ社、ブリッジウォーター、ニュージャージー州)の有効性について処方情報に提供されたデータと比較した。本先行技術製剤を製剤Cとする。製剤AおよびBは界面活性剤を含まない。製剤Aは1日1回のみ塗布したが、製剤B及びC(それぞれ過酸化ベンゾイルを5.0%含む)は、12週間の治療期間中1日2回塗布した。製剤Aを12週間の塗布の後にテストした。製剤B及びCのデータは10週間の塗布の後のものである。
実施例3の製剤AおよびBはそれぞれ過酸化ベンゾイルと1.0%のクリンダマイシンを含み、これら2つの製剤の刺激の可能性の比較を検証するためのテストが行われた。本発明による製剤Aは過酸化ベンゾイルを2.5%、過酸化ベンゾイルの濃度の2倍のプロピレングリコール、プロピレングリコールの濃度の17.8倍の水を含む。製剤Bは過酸化ベンゾイルを5.0%、過酸化ベンゾイルの濃度の2倍のプロピレングリコール、プロピレングリコールの濃度の8.25倍の水を含む。
Claims (8)
- 界面活性剤を含まない、皮膚に局所塗布するための水溶性ゲル製剤であって、水と、プロピレングリコールと、ゲル化剤と、過酸化ベンゾイルとを有し、
前記ゲル化剤はカルボマーであり、
前記プロピレングリコールの濃度は、前記製剤中に界面活性剤を含めることなく前記水溶性ゲル製剤中において安定な過酸化ベンゾイル懸濁物を与えるのに十分な濃度であり、
前記プロピレングリコールの濃度は、前記過酸化ベンゾイルの濃度の1から4倍であり、
前記プロピレングリコールに対する前記水の比率(w/w)は少なくとも12:1であり、および、
前記ゲル製剤中の過酸化ベンゾイルの濃度は、5.0%(w/w)未満かつ少なくとも1.0%(w/w)の濃度である、水溶性ゲル製剤。 - 請求項1記載の界面活性剤を含まない水溶性ゲル製剤において、前記ゲル製剤中の前記プロピレングリコールに対する前記水の比率(w/w)は少なくとも17.8:1である、水溶性ゲル製剤。
- 請求項1または請求項2に記載の界面活性剤を含まない水溶性ゲル製剤において、前記ゲル化剤はCarbopol(登録商標)980である、水溶性ゲル製剤。
- 請求項3記載の界面活性剤を含まない水溶性ゲル製剤であって、1.75%(w/w)Carbopol(登録商標)980を有する、水溶性ゲル製剤。
- 請求項1記載の界面活性剤を含まない水溶性ゲル製剤であって、さらに、1.2%(w/w)リン酸クリンダマイシンを有する、水溶性ゲル製剤。
- 請求項1記載の界面活性剤を含まない水溶性ゲル製剤であって、基本的に2.5%(w/w)過酸化ベンゾイル、5%(w/w)プロピレングリコール、および1.75%(w/w)Carbopol(登録商標)980からなる、水溶性ゲル製剤。
- 皮膚に局所塗布し、及びニキビを治療するための、界面活性剤を含まない水溶性ゲル製剤を製造するための、水、プロピレングリコール、カルボマーゲル化剤、および過酸化ベンゾイルの使用であって、
前記プロピレングリコールの濃度は、前記製剤中に界面活性剤を含めることなく前記水溶性ゲル製剤中において安定な過酸化ベンゾイル懸濁物を与えるのに十分な濃度であり、
前記プロピレングリコールの濃度は、前記過酸化ベンゾイルの濃度の1から4倍であり、
前記プロピレングリコールに対する前記水の比率(w/w)は少なくとも12:1であり、および、
前記ゲル製剤中の過酸化ベンゾイルの濃度は、5.0%(w/w)未満かつ少なくとも1.0%(w/w)の濃度である、使用。 - 請求項7記載の使用において、前記界面活性剤を含まない水溶性ゲル製剤における過酸化ベンゾイルの濃度が2.5%(w/w)であり、前記界面活性剤を含まない水溶性ゲル製剤におけるプロピレングリコールの濃度が5%(w/w)であり、前記ゲル化剤はCarbopol(登録商標)980であり、および前記界面活性剤を含まない水溶性ゲル製剤における前記ゲル化剤の濃度は1.75%(w/w)である、使用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13101408P | 2008-06-05 | 2008-06-05 | |
US61/131,014 | 2008-06-05 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011512469A Division JP5677693B2 (ja) | 2008-06-05 | 2009-06-03 | 水及び水混和性有機溶媒中に懸濁する低濃度過酸化ベンゾイルを含む局所用医薬品製剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015038093A JP2015038093A (ja) | 2015-02-26 |
JP6006272B2 true JP6006272B2 (ja) | 2016-10-12 |
Family
ID=41398394
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011512469A Active JP5677693B2 (ja) | 2008-06-05 | 2009-06-03 | 水及び水混和性有機溶媒中に懸濁する低濃度過酸化ベンゾイルを含む局所用医薬品製剤 |
JP2014188286A Active JP6006272B2 (ja) | 2008-06-05 | 2014-09-16 | 水及び水混和性有機溶媒中に懸濁する低濃度過酸化ベンゾイルを含む局所用医薬品製剤 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011512469A Active JP5677693B2 (ja) | 2008-06-05 | 2009-06-03 | 水及び水混和性有機溶媒中に懸濁する低濃度過酸化ベンゾイルを含む局所用医薬品製剤 |
Country Status (15)
Country | Link |
---|---|
US (13) | US8288434B2 (ja) |
EP (1) | EP2299810B1 (ja) |
JP (2) | JP5677693B2 (ja) |
KR (1) | KR20110014651A (ja) |
CN (1) | CN102056481A (ja) |
AU (1) | AU2009255679B2 (ja) |
BR (1) | BRPI0913326C1 (ja) |
CA (1) | CA2723029C (ja) |
ES (1) | ES2773931T3 (ja) |
HR (1) | HRP20200450T1 (ja) |
MX (1) | MX2010013152A (ja) |
PT (1) | PT2299810T (ja) |
RU (2) | RU2493847C2 (ja) |
WO (1) | WO2009148584A1 (ja) |
ZA (1) | ZA201008265B (ja) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007015243A2 (en) | 2005-08-02 | 2007-02-08 | Sol-Gel Technologies Ltd. | Metal oxide coating of water insoluble ingredients |
ES2773931T3 (es) | 2008-06-05 | 2020-07-15 | Bausch Health Ireland Ltd | Formulaciones farmacéuticas tópicas que contienen una baja concentración de peróxido de benzoílo en suspensión en agua y un solvente orgánico miscible en agua |
JP5753089B2 (ja) * | 2008-10-20 | 2015-07-22 | ドウ ファーマシューティカル サイエンシーズ、インク. | 過酸化ベンゾイルの安定分散液を得る方法 |
US9744150B2 (en) | 2009-10-21 | 2017-08-29 | Dow Pharmaceutical Sciences Inc. | Suspension containing micronized benzoyl peroxide |
RU2572693C2 (ru) * | 2009-10-21 | 2016-01-20 | Дау Фармасьютикал Сайенсиз, Инк. | Способ смачивания порошка, содержащего пероксид бензоила |
CN108159425A (zh) * | 2012-11-27 | 2018-06-15 | 索尔-格尔科技有限公司 | 用于治疗红斑痤疮的组合物 |
US9687465B2 (en) | 2012-11-27 | 2017-06-27 | Sol-Gel Technologies Ltd. | Compositions for the treatment of rosacea |
WO2017068673A1 (ja) * | 2015-10-21 | 2017-04-27 | マルホ株式会社 | 皮膚用の医薬組成物 |
CN107304177B (zh) * | 2016-04-20 | 2020-09-15 | 武汉诺安药业有限公司 | 一种过氧苯甲酰微粉化的化学制备方法 |
EP3654988B1 (en) * | 2017-07-21 | 2023-09-06 | Almirall, LLC | Sarecycline for the treatment of non-inflammatory acne lesions |
CN107375209A (zh) * | 2017-08-30 | 2017-11-24 | 江苏嘉逸医药有限公司 | 一种过氧苯甲酰的局部药物制剂 |
CN107737135A (zh) * | 2017-11-28 | 2018-02-27 | 江苏万川医疗健康产业集团有限公司 | 一种药物制剂及其制备方法与应用 |
JP6811213B2 (ja) * | 2018-07-03 | 2021-01-13 | ソル − ゲル テクノロジーズ リミテッド | 酒さの治療のための組成物 |
CA3130362A1 (en) | 2019-02-19 | 2020-08-27 | Sol-Gel Technologies Ltd. | Method for providing early onset of action in the treatment of rosacea |
AU2020322173A1 (en) * | 2019-08-01 | 2022-02-17 | Bausch Health Ireland Limited | Topical compositions |
CN113577022B (zh) * | 2021-05-18 | 2023-03-17 | 南京欣通瑞亿医药科技有限公司 | 一种氨苯砜类化合物混悬液及其制备方法和应用 |
Family Cites Families (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3535442A (en) | 1967-10-19 | 1970-10-20 | John E Jennings | Anti-shoplifting and surveillance system |
US4056611A (en) | 1973-04-16 | 1977-11-01 | Stiefel Laboratories, Inc. | Therapeutic composition |
US4497794A (en) * | 1980-12-08 | 1985-02-05 | Dermik Laboratories, Inc. | Erythromycin/benzoyl peroxide composition for the treatment of acne |
US4075353A (en) | 1976-06-09 | 1978-02-21 | Dermatologics For Veterinary Medicine, Inc. | Process for the treatment of acarid skin infections in animals |
FR2378523A1 (fr) | 1977-01-26 | 1978-08-25 | Grupper Charles | Medicament pour le traitement de l'acne |
US4189501A (en) | 1977-10-07 | 1980-02-19 | A. H. C. Pharmacal, Inc. | Composition and method for the treatment of acne |
NZ194326A (en) | 1979-07-25 | 1982-05-31 | Dermik Lab Inc | Stable aqueous benzoyl peroxide compositions and therapeutic compositions |
US4387107A (en) | 1979-07-25 | 1983-06-07 | Dermik Laboratories, Inc. | Stable benzoyl peroxide composition |
IT1210608B (it) * | 1980-12-08 | 1989-09-14 | Rorer Int Overseas | Composizione per il trattamento topico dell'acne |
US4411893A (en) | 1981-08-14 | 1983-10-25 | Minnesota Mining And Manufacturing Company | Topical medicament preparations |
US4401835A (en) * | 1981-09-17 | 1983-08-30 | Warner-Lambert Company | Method for preparing small sized benzoyl peroxide crystals |
US4923900A (en) * | 1985-01-24 | 1990-05-08 | Board Of Regents, The University Of Texas System | Therapeutic compositions containing benzoyl peroxide |
US5446028A (en) * | 1985-12-12 | 1995-08-29 | Dermik Laboratories, Inc. | Anti-acne method and composition |
FR2604435B1 (fr) | 1986-09-30 | 1988-12-02 | Oreal | Peroxydes aromatiques insatures et leur utilisation en therapeutique et cosmetique |
US6117843A (en) * | 1992-02-18 | 2000-09-12 | Lloyd J. Baroody | Compositions for the treatment of acne containing clindamycin and benzoyl peroxide |
TW203552B (en) * | 1992-02-18 | 1993-04-11 | J Baroody Lloyd | Compositions of clindamycin and benzoyl peroxide for acne treatment |
IL105217A0 (en) | 1992-04-09 | 1993-07-08 | Allergan Inc | Method and composition for treating acne |
US5466446A (en) * | 1994-02-16 | 1995-11-14 | Stiefel Laboratories, Inc. | Topical compositions containing bensoyl peroxide and clindamycin and method of use thereof |
US5470884A (en) | 1994-05-19 | 1995-11-28 | Procter & Gamble | Anti-acne compositions |
DE4418096A1 (de) | 1994-05-24 | 1995-11-30 | Cassella Ag | Verwendung von Pteridin-Derivaten als Hemmstoffe der NO-Synthase |
US5445823A (en) | 1994-10-20 | 1995-08-29 | The Procter & Gamble Company | Dermatological compositions and method of treatment of skin lesions therewith |
US20020039561A1 (en) | 1995-11-15 | 2002-04-04 | Doughty Darrell Gene | Topical skin care compositions containing thickened polyol carboxylic acid esters as skin conditioning agents |
US6071541A (en) * | 1998-07-31 | 2000-06-06 | Murad; Howard | Pharmaceutical compositions and methods for managing skin conditions |
US6433024B1 (en) | 2000-05-08 | 2002-08-13 | Karl F. Popp | Topical anti-acne composition |
US6387383B1 (en) | 2000-08-03 | 2002-05-14 | Dow Pharmaceutical Sciences | Topical low-viscosity gel composition |
US6837383B1 (en) | 2001-01-25 | 2005-01-04 | Mcelhaney Jr Wayne | Tool organizer mounted to a vehicle lift rack |
US20030064084A1 (en) | 2001-09-24 | 2003-04-03 | Bradley Pharmaceuticals, Inc. | Novel benzoyl peroxide compositions for the treatment of dermatological disorders and methods for their use |
US7820186B2 (en) * | 2001-12-21 | 2010-10-26 | Galderma Research & Development | Gel composition for once-daily treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt |
FR2833841B1 (fr) * | 2001-12-21 | 2005-07-22 | Galderma Res & Dev | Gel comprenant au moins un retinoide et du peroxyde de benzoyle |
US20040101566A1 (en) | 2002-02-04 | 2004-05-27 | Elan Pharma International Limited | Novel benzoyl peroxide compositions |
AU2004206769B2 (en) | 2003-01-24 | 2009-11-26 | Stiefel Research Australia Pty Ltd | Clindamycin phosphate foam |
GB0403702D0 (en) * | 2004-02-19 | 2004-03-24 | Boots Co Plc | Skincare compositions |
US20050239723A1 (en) * | 2004-04-27 | 2005-10-27 | Amin Avinash N | Compositions and methods useful for treatment of acne |
US7153888B2 (en) * | 2004-12-21 | 2006-12-26 | Alpharx Inc. | Stabilization of benzoyl peroxide in solution |
AU2006223251B2 (en) * | 2005-03-10 | 2011-08-25 | Jr Chem, Llc | Benzoyl peroxide compositions and methods of use |
AR054805A1 (es) * | 2005-06-29 | 2007-07-18 | Stiefel Laboratories | Composiciones topicas para el tratamiento de la piel |
BRPI0709674A2 (pt) | 2006-03-31 | 2011-12-06 | Stiefel Res Australia Pty Ltd | gel de suspensão espumante |
MXPA06008988A (es) | 2006-08-08 | 2008-02-07 | Fernando Ahumada Ayala | Preparaciones topicas antiacne que contienen retinoide (tazaroteno o adapaleno), antibiotico (fosfato de clindamicina) y/o queratolitico (peroxido de bonzoilo en microesponjas). |
FR2910321B1 (fr) | 2006-12-21 | 2009-07-10 | Galderma Res & Dev S N C Snc | Gel creme comprenant au moins un retinoide et du peroxyde de benzole |
EP1967180A1 (de) | 2007-03-06 | 2008-09-10 | Almirall Hermal GmbH | Topische Zusammensetzung enthaltend einen Retinoid-Rezeptor-Agonist |
ES2773931T3 (es) * | 2008-06-05 | 2020-07-15 | Bausch Health Ireland Ltd | Formulaciones farmacéuticas tópicas que contienen una baja concentración de peróxido de benzoílo en suspensión en agua y un solvente orgánico miscible en agua |
EP2788010B1 (en) * | 2011-12-09 | 2018-10-24 | Mary Kay Inc. | Skin care formulation |
EP3941454A1 (en) * | 2019-03-18 | 2022-01-26 | Bausch Health Ireland Limited | Topical compositions and methods for treating acne vulgaris |
-
2009
- 2009-06-03 ES ES09758748T patent/ES2773931T3/es active Active
- 2009-06-03 WO PCT/US2009/003367 patent/WO2009148584A1/en active Application Filing
- 2009-06-03 PT PT97587489T patent/PT2299810T/pt unknown
- 2009-06-03 CA CA2723029A patent/CA2723029C/en active Active
- 2009-06-03 AU AU2009255679A patent/AU2009255679B2/en active Active
- 2009-06-03 JP JP2011512469A patent/JP5677693B2/ja active Active
- 2009-06-03 CN CN2009801207389A patent/CN102056481A/zh active Pending
- 2009-06-03 US US12/455,525 patent/US8288434B2/en active Active
- 2009-06-03 RU RU2010146038/15A patent/RU2493847C2/ru active
- 2009-06-03 EP EP09758748.9A patent/EP2299810B1/en active Active
- 2009-06-03 MX MX2010013152A patent/MX2010013152A/es active IP Right Grant
- 2009-06-03 BR BRPI0913326A patent/BRPI0913326C1/pt active IP Right Grant
- 2009-06-03 KR KR1020107028278A patent/KR20110014651A/ko not_active Application Discontinuation
-
2010
- 2010-11-18 ZA ZA2010/08265A patent/ZA201008265B/en unknown
-
2012
- 2012-09-13 US US13/613,401 patent/US9693988B2/en active Active
-
2013
- 2013-04-24 US US13/869,494 patent/US8663699B2/en active Active
- 2013-05-15 RU RU2013122395A patent/RU2645087C2/ru active
- 2013-10-28 US US14/065,186 patent/US8895070B2/en active Active
- 2013-10-28 US US14/065,207 patent/US20140051649A1/en not_active Abandoned
- 2013-10-28 US US14/065,199 patent/US9078870B2/en active Active
-
2014
- 2014-04-23 US US14/260,211 patent/US9504704B2/en active Active
- 2014-09-16 JP JP2014188286A patent/JP6006272B2/ja active Active
-
2016
- 2016-04-08 US US15/094,895 patent/US9561208B2/en active Active
- 2016-10-24 US US15/332,933 patent/US10137142B2/en active Active
-
2017
- 2017-02-06 US US15/425,844 patent/US10220049B2/en active Active
-
2018
- 2018-10-26 US US16/171,862 patent/US10624918B2/en active Active
-
2020
- 2020-03-18 HR HRP20200450TT patent/HRP20200450T1/hr unknown
- 2020-04-20 US US16/853,361 patent/US11478498B2/en active Active
-
2022
- 2022-10-19 US US17/969,638 patent/US20230047106A1/en active Pending
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6006272B2 (ja) | 水及び水混和性有機溶媒中に懸濁する低濃度過酸化ベンゾイルを含む局所用医薬品製剤 | |
US10821075B1 (en) | Compositions for topical application of a medicaments onto a mammalian body surface | |
US20100029765A1 (en) | Topical aqueous composition comprising tretinoin | |
WO2020170034A1 (en) | Method for long-term treatment of rosacea | |
JPH111433A (ja) | トルナフテ−ト含有液剤 | |
JP2018529723A (ja) | イベルメクチンを含むすすぎのいらないケミカルフォーム |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150929 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160104 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160129 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160226 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160329 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160809 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160908 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6006272 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R371 | Transfer withdrawn |
Free format text: JAPANESE INTERMEDIATE CODE: R371 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
R371 | Transfer withdrawn |
Free format text: JAPANESE INTERMEDIATE CODE: R371 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |