JPS6135166B2 - - Google Patents
Info
- Publication number
- JPS6135166B2 JPS6135166B2 JP51017820A JP1782076A JPS6135166B2 JP S6135166 B2 JPS6135166 B2 JP S6135166B2 JP 51017820 A JP51017820 A JP 51017820A JP 1782076 A JP1782076 A JP 1782076A JP S6135166 B2 JPS6135166 B2 JP S6135166B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- composition
- solvent
- glycol
- mixture
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 claims description 208
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 153
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 72
- 239000002904 solvent Substances 0.000 claims description 70
- 239000003246 corticosteroid Substances 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
- 239000003814 drug Substances 0.000 claims description 49
- 229940079593 drug Drugs 0.000 claims description 48
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 37
- 229960001334 corticosteroids Drugs 0.000 claims description 29
- 239000006071 cream Substances 0.000 claims description 26
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 24
- 239000002480 mineral oil Substances 0.000 claims description 22
- 235000010446 mineral oil Nutrition 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 239000004094 surface-active agent Substances 0.000 claims description 19
- 150000002191 fatty alcohols Chemical class 0.000 claims description 18
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 230000000699 topical effect Effects 0.000 claims description 16
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 14
- 239000002674 ointment Substances 0.000 claims description 14
- 229940126062 Compound A Drugs 0.000 claims description 13
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 13
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 12
- 235000019271 petrolatum Nutrition 0.000 claims description 12
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 10
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 229960000541 cetyl alcohol Drugs 0.000 claims description 9
- 229920002125 Sokalan® Polymers 0.000 claims description 8
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 8
- 239000003871 white petrolatum Substances 0.000 claims description 8
- 239000003242 anti bacterial agent Substances 0.000 claims description 6
- 150000002334 glycols Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 239000008063 pharmaceutical solvent Substances 0.000 claims description 6
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 6
- WJOHZNCJWYWUJD-IUGZLZTKSA-N Fluocinonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)C)[C@@]2(C)C[C@@H]1O WJOHZNCJWYWUJD-IUGZLZTKSA-N 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 claims description 5
- 208000017520 skin disease Diseases 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- 239000004264 Petrolatum Substances 0.000 claims description 4
- 229960000785 fluocinonide Drugs 0.000 claims description 4
- 229940066842 petrolatum Drugs 0.000 claims description 4
- 230000003115 biocidal effect Effects 0.000 claims description 3
- 239000003349 gelling agent Substances 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 2
- 229940043075 fluocinolone Drugs 0.000 claims 3
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 3
- UBOIMZIXNXGQOH-RTWVSBIPSA-N 58497-00-0 Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)CC)[C@@]2(C)C[C@@H]1O UBOIMZIXNXGQOH-RTWVSBIPSA-N 0.000 claims 2
- 239000008180 pharmaceutical surfactant Substances 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 229940096529 carboxypolymethylene Drugs 0.000 claims 1
- 239000002563 ionic surfactant Substances 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 description 32
- 239000003981 vehicle Substances 0.000 description 31
- 210000003491 skin Anatomy 0.000 description 23
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- 239000000243 solution Substances 0.000 description 16
- 238000009472 formulation Methods 0.000 description 15
- 239000000499 gel Substances 0.000 description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
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- 239000006210 lotion Substances 0.000 description 10
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- 235000014113 dietary fatty acids Nutrition 0.000 description 7
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- 239000004615 ingredient Substances 0.000 description 7
- 239000004014 plasticizer Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
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- 239000004480 active ingredient Substances 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 6
- 210000000434 stratum corneum Anatomy 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229930193140 Neomycin Natural products 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 210000002615 epidermis Anatomy 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229960004927 neomycin Drugs 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920000136 polysorbate Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000013022 formulation composition Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000004968 inflammatory condition Effects 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 108010026389 Gramicidin Proteins 0.000 description 2
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- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 229920002584 Polyethylene Glycol 6000 Polymers 0.000 description 2
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- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 description 2
- CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 description 2
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical class O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037368 penetrate the skin Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000003186 pharmaceutical solution Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- 150000003117 prednisolones Chemical class 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 description 1
- 229960000249 pregnenolone Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940093625 propylene glycol monostearate Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000008591 skin barrier function Effects 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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
- A61K9/0012—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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
-
- 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
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/551,811 US3934013A (en) | 1975-02-21 | 1975-02-21 | Pharmaceutical composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51110043A JPS51110043A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-29 |
| JPS6135166B2 true JPS6135166B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-08-12 |
Family
ID=24202770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51017820A Expired JPS6135166B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-21 | 1976-02-20 |
Country Status (18)
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX3864E (es) * | 1975-05-27 | 1981-08-26 | Syntex Corp | Un proceso para prepara el compuesto cristalino 6-fluiro-11b 21-dihiroxi-16 17-isopropilidendioxipregna-1 4-dien-3 20-diona |
| US4070462A (en) * | 1976-10-26 | 1978-01-24 | Schering Corporation | Steroid ointment |
| GB1540948A (en) * | 1976-12-17 | 1979-02-21 | Scherico Ltd | Antibiotic formulations |
| GB2080106B (en) * | 1980-07-18 | 1984-03-07 | Weelcome Foundation Ltd | Acyclovin preparations |
| KR830005852A (ko) * | 1980-07-18 | 1983-09-14 | 미첼 페터 잭슨 | 피부와 점막의 비루스 감염치료에 적합한 국소치료제의 제조방법 |
| US4304765A (en) * | 1980-10-14 | 1981-12-08 | Alza Corporation | Ocular insert housing steroid in two different therapeutic forms |
| US4432964A (en) * | 1981-08-24 | 1984-02-21 | Alza Corporation | Topical composition containing steroid in two forms released independently from polymeric carrier |
| US4478818A (en) * | 1982-12-27 | 1984-10-23 | Alza Corporation | Ocular preparation housing steroid in two different therapeutic forms |
| US4482539A (en) * | 1983-05-13 | 1984-11-13 | Schering Corporation | Betamethasone dipropionate cream |
| US4489070A (en) * | 1983-05-13 | 1984-12-18 | Schering Corporation | Betamethasone dipropionate cream |
| US4557934A (en) * | 1983-06-21 | 1985-12-10 | The Procter & Gamble Company | Penetrating topical pharmaceutical compositions containing 1-dodecyl-azacycloheptan-2-one |
| US4537776A (en) * | 1983-06-21 | 1985-08-27 | The Procter & Gamble Company | Penetrating topical pharmaceutical compositions containing N-(2-hydroxyethyl) pyrrolidone |
| US4552872A (en) * | 1983-06-21 | 1985-11-12 | The Procter & Gamble Company | Penetrating topical pharmaceutical compositions containing corticosteroids |
| YU46838B (sh) * | 1986-02-14 | 1994-06-24 | Pero Dr. Višnjić | Postupak za dobijanje preparata za lečenje kožne bolesti psoriazisa |
| EP0196121A1 (en) * | 1985-02-22 | 1986-10-01 | Pera Dr. Visnjic | Process for obtaining the preparation for the treatment of the disease psoriasis; drug for the treatment of psoriasis and its application |
| US4780455A (en) * | 1985-04-12 | 1988-10-25 | The Trustees Of Columbia University In The City Of New York | Lipophilic complexes of pharmacologically active organic compounds |
| US5002936A (en) * | 1985-04-12 | 1991-03-26 | Seymour Lieberman | Lipophilic complexes of pharmacologically active inorganic mineral acid esters of organic compounds |
| US4792556A (en) | 1985-09-09 | 1988-12-20 | Syntex (U.S.A.) Inc. | Naphthalene anti-psoriatic agents |
| DE3534743A1 (de) * | 1985-09-28 | 1987-04-02 | Beiersdorf Ag | Hydrocortisondiester enthaltende o/w-creme |
| US4740372A (en) * | 1986-09-17 | 1988-04-26 | Ljubomir Boncic | Composition for treating psoriasis vulgaris and a method for its preparation |
| US5171737A (en) * | 1989-03-03 | 1992-12-15 | The Liposome Company, Inc. | Emulsions |
| US5061700A (en) * | 1989-11-16 | 1991-10-29 | Gordon Jay Dow | Glyceryl acetate ointment vehicles |
| DE4234225A1 (de) * | 1992-10-10 | 1994-04-14 | Roehm Pharma Gmbh | Stabile topische Formulierungen mit gutem Wirkstoff-Freisetzungsvermögen enthaltend mindestens ein lipophilisiertes Makrolidantibiotikum |
| AP608A (en) * | 1993-10-22 | 1997-08-28 | Smithkline Beecham Corp | Pharmaceutical or veterinary composition comprising a cream base. |
| WO1996002254A1 (en) * | 1994-07-15 | 1996-02-01 | Michel Cohen | SYNERGISTIC PHARMACEUTICAL COMPOSITONS CONTAINING 16'alpha',17'alpha'-ISOPROPYLIDENEDIOXY SUBSTITUTED PREGNANES |
| US5707981A (en) * | 1994-07-28 | 1998-01-13 | Psorial, L.L.C. | Synergistic pharmaceutical compositions |
| RU2106860C1 (ru) * | 1996-01-30 | 1998-03-20 | Акционерное общество открытого типа "Нижегородский химико-фармацевтический завод" | Состав и способ получения мази противовоспалительного и противозудного действия |
| US7179475B1 (en) | 1998-12-04 | 2007-02-20 | Johnson & Johnson Consumer Companies, Inc. | Anhydrous topical skin preparations |
| CN1350521A (zh) | 1999-03-05 | 2002-05-22 | 宝洁公司 | C16不饱和的fp选择性前列腺素类似物 |
| US20020037914A1 (en) | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| US20020013294A1 (en) | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| US20020172693A1 (en) | 2000-03-31 | 2002-11-21 | Delong Michell Anthony | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US20020146439A1 (en) * | 2000-03-31 | 2002-10-10 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using oximyl and hydroxylamino prostaglandins |
| US6765001B2 (en) * | 2001-12-21 | 2004-07-20 | Medicis Pharmaceutical Corporation | Compositions and methods for enhancing corticosteroid delivery |
| US9623000B2 (en) | 2008-07-31 | 2017-04-18 | Dekel Pharmaceuticals Ltd | Compositions and methods for treating inflammatory disorders |
| US8623918B2 (en) * | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8722739B2 (en) * | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| DK2473161T3 (en) | 2009-08-31 | 2017-09-11 | Dr Reddys Laboratories Ltd | TOPICAL FORMULATIONS INCLUDING A STEROID |
| PL2366408T3 (pl) | 2010-03-01 | 2013-01-31 | Salvat Lab Sa | Klarowne roztwory wodne acetonidu fluocinolonu do leczenia zapalenia uszu |
| US20150258119A1 (en) | 2014-03-11 | 2015-09-17 | Promius Pharma, LLC | Topical corticosteroid compositions |
| US20160184431A1 (en) | 2014-03-11 | 2016-06-30 | Promius Pharma Llc | Topical compositions comprising a corticosteroid |
| PL409156A1 (pl) | 2014-08-11 | 2016-02-15 | Matonis Grzegorz | Kompozycja kosmetyczna i/lub farmaceutyczna łagodząca objawy łuszczycy |
| US20200230082A1 (en) * | 2017-07-11 | 2020-07-23 | University Of Miami | Topical acetaminophen formulations for itch relief |
| EP4188333A1 (en) | 2020-07-28 | 2023-06-07 | Arcutis Biotherapeutics, Inc. | Topical formulation containing jak inhibitor and laureth-4 |
| CA3240662A1 (en) | 2021-12-15 | 2023-06-22 | Herbert R. Brinkman | Stable formulations of shr0302 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3073743A (en) * | 1959-07-30 | 1963-01-15 | Upjohn Co | Antiinflammatory steroid acetonide compositions and therapy |
| US3472931A (en) * | 1969-01-17 | 1969-10-14 | Foster Milburn Co | Percutaneous absorption with lower alkyl amides |
-
1975
- 1975-02-21 US US05/551,811 patent/US3934013A/en not_active Expired - Lifetime
-
1976
- 1976-01-06 ZA ZA760071A patent/ZA7671B/xx unknown
- 1976-01-06 IL IL48797A patent/IL48797A/xx unknown
- 1976-01-28 CA CA244,385A patent/CA1067409A/en not_active Expired
- 1976-01-28 GB GB3426/76A patent/GB1502544A/en not_active Expired
- 1976-01-30 AU AU10682/76A patent/AU504748B2/en not_active Expired
- 1976-02-10 BR BR7600834A patent/BR7600834A/pt unknown
- 1976-02-11 DE DE19762605242 patent/DE2605242A1/de not_active Ceased
- 1976-02-12 FI FI760344A patent/FI67415C/fi not_active IP Right Cessation
- 1976-02-13 ES ES445151A patent/ES445151A1/es not_active Expired
- 1976-02-18 IT IT67379/76A patent/IT1066085B/it active
- 1976-02-18 NZ NZ180042A patent/NZ180042A/xx unknown
- 1976-02-19 IE IE331/76A patent/IE43655B1/en unknown
- 1976-02-19 FR FR7604592A patent/FR2301262A1/fr active Granted
- 1976-02-19 NL NL7601667A patent/NL7601667A/xx not_active Application Discontinuation
- 1976-02-19 BE BE164436A patent/BE838711A/xx not_active IP Right Cessation
- 1976-02-19 DK DK68876*#A patent/DK68876A/da not_active Application Discontinuation
- 1976-02-20 JP JP51017820A patent/JPS6135166B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE838711A (fr) | 1976-08-19 |
| IE43655L (en) | 1976-08-21 |
| IL48797A (en) | 1979-01-31 |
| IE43655B1 (en) | 1981-04-22 |
| ZA7671B (en) | 1977-08-31 |
| ES445151A1 (es) | 1977-05-16 |
| FI67415C (fi) | 1985-03-11 |
| GB1502544A (en) | 1978-03-01 |
| BR7600834A (pt) | 1976-09-14 |
| IL48797A0 (en) | 1976-03-31 |
| NZ180042A (en) | 1978-07-28 |
| FR2301262A1 (fr) | 1976-09-17 |
| DK68876A (da) | 1976-08-22 |
| CA1067409A (en) | 1979-12-04 |
| DE2605242A1 (de) | 1976-09-02 |
| FI67415B (fi) | 1984-11-30 |
| NL7601667A (nl) | 1976-08-24 |
| FI760344A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-08-22 |
| AU504748B2 (en) | 1979-10-25 |
| JPS51110043A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-29 |
| FR2301262B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-04-06 |
| US3934013A (en) | 1976-01-20 |
| AU1085876A (en) | 1977-03-17 |
| IT1066085B (it) | 1985-03-04 |
| AU1068276A (en) | 1977-08-04 |
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