DE69534306T2 - Arzneimittel - Google Patents
Arzneimittel Download PDFInfo
- Publication number
- DE69534306T2 DE69534306T2 DE69534306T DE69534306T DE69534306T2 DE 69534306 T2 DE69534306 T2 DE 69534306T2 DE 69534306 T DE69534306 T DE 69534306T DE 69534306 T DE69534306 T DE 69534306T DE 69534306 T2 DE69534306 T2 DE 69534306T2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- class
- alcohol
- emulsion
- compositions
- 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 - Lifetime
Links
- 239000003814 drug Substances 0.000 title description 4
- 229940079593 drug Drugs 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical class C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims abstract description 37
- 239000000839 emulsion Substances 0.000 claims abstract description 37
- -1 ether diol Chemical class 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 230000000699 topical effect Effects 0.000 claims abstract description 23
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 21
- 239000003120 macrolide antibiotic agent Substances 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 22
- 239000007764 o/w emulsion Substances 0.000 claims description 11
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 10
- 229940055577 oleyl alcohol Drugs 0.000 claims description 10
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000002562 thickening agent Substances 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 6
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 4
- ZDQSOHOQTUFQEM-PKUCKEGBSA-N ascomycin Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C\C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 ZDQSOHOQTUFQEM-PKUCKEGBSA-N 0.000 claims description 4
- ZDQSOHOQTUFQEM-XCXYXIJFSA-N ascomycin Natural products CC[C@H]1C=C(C)C[C@@H](C)C[C@@H](OC)[C@H]2O[C@@](O)([C@@H](C)C[C@H]2OC)C(=O)C(=O)N3CCCC[C@@H]3C(=O)O[C@H]([C@H](C)[C@@H](O)CC1=O)C(=C[C@@H]4CC[C@@H](O)[C@H](C4)OC)C ZDQSOHOQTUFQEM-XCXYXIJFSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 229940051250 hexylene glycol Drugs 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
- 239000012049 topical pharmaceutical composition Substances 0.000 abstract description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 26
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 10
- 201000004681 Psoriasis Diseases 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 229960000541 cetyl alcohol Drugs 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920002125 Sokalan® Polymers 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000012188 paraffin wax Substances 0.000 description 9
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 9
- 229920000053 polysorbate 80 Polymers 0.000 description 9
- 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 description 7
- 239000002253 acid Substances 0.000 description 7
- 230000001684 chronic effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 7
- 229960002930 sirolimus Drugs 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 6
- 239000003871 white petrolatum Substances 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 5
- 229920001214 Polysorbate 60 Polymers 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 5
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 5
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
- 230000003463 hyperproliferative effect Effects 0.000 description 5
- 230000002757 inflammatory effect Effects 0.000 description 5
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 5
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- 238000000926 separation method Methods 0.000 description 5
- 208000017520 skin disease Diseases 0.000 description 5
- 235000010199 sorbic acid Nutrition 0.000 description 5
- 239000004334 sorbic acid Substances 0.000 description 5
- 229940075582 sorbic acid Drugs 0.000 description 5
- 229940099259 vaseline Drugs 0.000 description 5
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- 206010015150 Erythema Diseases 0.000 description 4
- 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 description 4
- 239000004166 Lanolin Substances 0.000 description 4
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 231100000321 erythema Toxicity 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 229940068196 placebo Drugs 0.000 description 4
- 239000000902 placebo Substances 0.000 description 4
- 229920001983 poloxamer Polymers 0.000 description 4
- 229920001993 poloxamer 188 Polymers 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 3
- OIQOAYVCKAHSEJ-UHFFFAOYSA-N 2-[2,3-bis(2-hydroxyethoxy)propoxy]ethanol;hexadecanoic acid;octadecanoic acid Chemical compound OCCOCC(OCCO)COCCO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O OIQOAYVCKAHSEJ-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 239000007857 degradation product Substances 0.000 description 3
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- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
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- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
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- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
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- VWBHJJNWHBJGKS-UHFFFAOYSA-N 1,2,3-trihydroxypropyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(O)C(O)CO VWBHJJNWHBJGKS-UHFFFAOYSA-N 0.000 description 2
- XLMXUUQMSMKFMH-UZRURVBFSA-N 2-hydroxyethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCO XLMXUUQMSMKFMH-UZRURVBFSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical class CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 2
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- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 description 2
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- WMNULTDOANGXRT-UHFFFAOYSA-N bis(2-ethylhexyl) butanedioate Chemical compound CCCCC(CC)COC(=O)CCC(=O)OCC(CC)CCCC WMNULTDOANGXRT-UHFFFAOYSA-N 0.000 description 2
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
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- Transplantation (AREA)
- Dispersion Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9421612A GB9421612D0 (en) | 1994-10-26 | 1994-10-26 | Organic compounds |
| GB9421612 | 1994-10-26 | ||
| GB9422306A GB9422306D0 (en) | 1994-11-04 | 1994-11-04 | Organic compounds |
| GB9422306 | 1994-11-04 | ||
| GBGB9503553.1A GB9503553D0 (en) | 1995-02-22 | 1995-02-22 | Organic compounds |
| GB9503553 | 1995-02-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69534306D1 DE69534306D1 (de) | 2005-08-11 |
| DE69534306T2 true DE69534306T2 (de) | 2006-04-27 |
Family
ID=27267447
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69534306T Expired - Lifetime DE69534306T2 (de) | 1994-10-26 | 1995-10-26 | Arzneimittel |
| DE69525957T Expired - Lifetime DE69525957T2 (de) | 1994-10-26 | 1995-10-26 | Verwendung eines ungesättigten Fettalkohols |
| DE19581804T Ceased DE19581804T1 (de) | 1994-10-26 | 1995-10-26 | Pharmazeutische Zusammensetzungen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69525957T Expired - Lifetime DE69525957T2 (de) | 1994-10-26 | 1995-10-26 | Verwendung eines ungesättigten Fettalkohols |
| DE19581804T Ceased DE19581804T1 (de) | 1994-10-26 | 1995-10-26 | Pharmazeutische Zusammensetzungen |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6352998B2 (OSRAM) |
| EP (2) | EP1147766B1 (OSRAM) |
| JP (3) | JP4155593B2 (OSRAM) |
| KR (1) | KR100434682B1 (OSRAM) |
| CN (2) | CN100335063C (OSRAM) |
| AT (2) | ATE299017T1 (OSRAM) |
| AU (1) | AU714254B2 (OSRAM) |
| BR (1) | BR9509530A (OSRAM) |
| CA (1) | CA2200966C (OSRAM) |
| CY (1) | CY2211B1 (OSRAM) |
| CZ (1) | CZ289773B6 (OSRAM) |
| DE (3) | DE69534306T2 (OSRAM) |
| DK (2) | DK0786986T3 (OSRAM) |
| ES (2) | ES2173978T3 (OSRAM) |
| FI (2) | FI119754B (OSRAM) |
| GB (1) | GB2308546B (OSRAM) |
| HU (1) | HU223840B1 (OSRAM) |
| MX (1) | MX9702699A (OSRAM) |
| NO (2) | NO316963B1 (OSRAM) |
| NZ (2) | NZ331824A (OSRAM) |
| PL (1) | PL184750B1 (OSRAM) |
| PT (2) | PT786986E (OSRAM) |
| SI (1) | SI0786986T1 (OSRAM) |
| SK (1) | SK284591B6 (OSRAM) |
| WO (1) | WO1996013249A1 (OSRAM) |
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| AR004480A1 (es) * | 1995-04-06 | 1998-12-16 | Amico Derin C D | Compuestos de ascomicina que poseen actividad antiinflamatoria, pro cedimiento para prepararlos, uso de dichos compuestos para preparar agentesfarmaceuticos y composiciones farmaceuticas que los incluyen |
| GB9601120D0 (en) * | 1996-01-19 | 1996-03-20 | Sandoz Ltd | Organic compounds |
| CZ283516B6 (cs) * | 1996-09-12 | 1998-04-15 | Galena A.S. | Léčivé přípravky, zejména pro vnitřní aplikaci, ve formě samomikroemulgujících terapeutických systémů |
| US6495579B1 (en) * | 1996-12-02 | 2002-12-17 | Angiotech Pharmaceuticals, Inc. | Method for treating multiple sclerosis |
| TW450810B (en) | 1997-02-20 | 2001-08-21 | Fujisawa Pharmaceutical Co | Macrolides antibiotic pharmaceutical composition for preventing and treating skin diseases |
| DE19744621A1 (de) * | 1997-10-09 | 1999-04-15 | Muehlbauer Ernst Kg | Mischung zur Verwendung als Wundverband |
| GB9723669D0 (en) | 1997-11-07 | 1998-01-07 | Univ Aberdeen | Skin penetration enhancing components |
| DE19802205A1 (de) * | 1998-01-22 | 1999-07-29 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen, enthaltend erhöhte Elektrolytkonzentrationen |
| ID25908A (id) * | 1998-03-06 | 2000-11-09 | Novartis Ag | Prakonsentrat-prakonsentrat emulsi yang mengandung siklosporin atau makrolida |
| KR100406823B1 (ko) | 1998-04-27 | 2003-11-21 | 후지사와 야꾸힝 고교 가부시키가이샤 | 의약 조성물 |
| GB9814640D0 (en) * | 1998-07-06 | 1998-09-02 | Fujisawa Pharmaceutical Co | New use |
| GB9826656D0 (en) * | 1998-12-03 | 1999-01-27 | Novartis Ag | Organic compounds |
| US20070032853A1 (en) | 2002-03-27 | 2007-02-08 | Hossainy Syed F | 40-O-(2-hydroxy)ethyl-rapamycin coated stent |
| GB0003932D0 (en) * | 2000-02-18 | 2000-04-12 | Novartis Ag | Pharmaceutical compositions |
| IL156887A0 (en) * | 2001-02-16 | 2004-02-08 | Jomed Gmbh | Implants with fk506 |
| GB0108498D0 (en) * | 2001-04-04 | 2001-05-23 | Novartis Ag | Organic Compounds |
| TWI324925B (en) * | 2001-08-23 | 2010-05-21 | Novartis Ag | Ophthalmic composition |
| AR038628A1 (es) * | 2002-03-04 | 2005-01-19 | Novartis Ag | Composicion oftalmica |
| GB0218996D0 (en) * | 2002-08-14 | 2002-09-25 | Novartis Ag | Organic compounds |
| US20060115522A1 (en) * | 2003-02-17 | 2006-06-01 | Cipla Ltd | Pharmaceutical composition |
| US20040214753A1 (en) * | 2003-03-20 | 2004-10-28 | Britten Nancy Jean | Dispersible pharmaceutical composition for treatment of mastitis and otic disorders |
| GB0307869D0 (en) * | 2003-04-04 | 2003-05-14 | Novartis Ag | Pharmaceutical composition |
| GB0307866D0 (en) * | 2003-04-04 | 2003-05-14 | Novartis Ag | Pharmaceutical composition |
| GB0307867D0 (en) * | 2003-04-04 | 2003-05-14 | Novartis Ag | Pharmaceutical composition |
| CA2533101A1 (en) * | 2003-07-31 | 2005-02-03 | Pharmacia & Upjohn Company Llc | Dispersible formulation of an anti-inflammatory agent |
| GB0408070D0 (en) * | 2004-04-08 | 2004-05-12 | Novartis Ag | Pharmaceutical formulations |
| WO2005097068A1 (en) * | 2004-04-08 | 2005-10-20 | Novartis Ag | Pimecrolimus foam composition containing hexylene glycol, optionally oleyl alcohol, dimethylisosorbide and/or medium chain triglycerides |
| GB0508827D0 (en) * | 2005-04-29 | 2005-06-08 | Novartis Ag | Cosmeceutical composition |
| US9205080B2 (en) | 2006-11-16 | 2015-12-08 | Transderm, Inc. | Methods of treating keratin hyperproliferation disorders using mTOR inhibitors |
| EP2016935A1 (en) * | 2007-07-09 | 2009-01-21 | Intendis GmbH | Pharmaceutical composition for topical application of poorly soluble compounds |
| CN101288643B (zh) * | 2008-06-17 | 2012-11-14 | 杨喜鸿 | 含有他克莫司的凝胶剂组合物及其制备方法和药物应用 |
| EP2308468A1 (en) * | 2009-10-08 | 2011-04-13 | Novaliq GmbH | Novel pharmaceutical composition comprising a macrolide immunosuppressant drug |
| GB0917816D0 (en) | 2009-10-12 | 2009-11-25 | Biotica Tech Ltd | Novel compounds and methods for their production |
| GB0917817D0 (en) | 2009-10-12 | 2009-11-25 | Biotica Tech Ltd | Novel compounds and methods for their production |
| EP2366378A1 (en) | 2010-03-01 | 2011-09-21 | Dexcel Pharma Technologies Ltd. | Sustained-release donepezil formulations |
| WO2012011192A1 (ja) * | 2010-07-23 | 2012-01-26 | マルホ株式会社 | タクロリムスを含有する水中油型クリーム状組成物 |
| JP5674786B2 (ja) * | 2010-07-23 | 2015-02-25 | マルホ株式会社 | タクロリムスを含有する水中油型クリーム状組成物 |
| CN102552253A (zh) * | 2012-01-17 | 2012-07-11 | 唯美度科技（北京）有限公司 | 一种祛痘用皮肤外用剂 |
| JP6084579B2 (ja) * | 2012-01-25 | 2017-02-22 | マルホ株式会社 | タクロリムスを含有する水中油型クリーム状組成物 |
| CA2899206C (en) * | 2013-01-24 | 2019-07-09 | Transderm, Inc. | Compositions for transdermal delivery of mtor inhibitors |
| MX367121B (es) * | 2013-08-02 | 2019-08-06 | Laboratorio Raam De Sahuayo S A De C V | Composición sólida estable de inmunosupresores. |
| DE102013222164A1 (de) * | 2013-10-31 | 2015-04-30 | Deb Ip Limited | Stabilisierte multiple Emulsionen als Hautschutzprodukt |
| US10765665B2 (en) | 2015-11-24 | 2020-09-08 | Melin Jeffrey | Composition comprising combination of rapamycin and an activator of AMP kinase and use thereof for treating diseases |
| CN105663027B (zh) * | 2016-04-01 | 2018-12-18 | 中国人民解放军广州军区武汉总医院 | 西罗莫司外用制剂、其制备方法及用途 |
| CA3020157C (en) | 2016-04-04 | 2024-01-16 | Drug Delivery Solutions Limited | Topical composition comprising tacrolimus |
| IL302385B2 (en) | 2017-01-06 | 2024-06-01 | Palvella Therapeutics Inc | Non-aqueous preparations of mTOR inhibitors and methods of use |
| KR101973065B1 (ko) | 2017-09-13 | 2019-04-26 | (주)썬테크 | 풍력 발전기 및 풍력 발전기의 블레이드 팁 |
| EP3542788A1 (en) | 2018-03-19 | 2019-09-25 | MC2 Therapeutics Limited | Topical composition comprising calcipotriol and betamethasone dipropionate |
| KR101995905B1 (ko) | 2018-03-27 | 2019-07-04 | (주)썬테크 | 풍력 발전기 및 풍력 발전기의 발전모터 |
| WO2019233722A1 (en) * | 2018-06-08 | 2019-12-12 | Almirall, S.A. | Pharmaceutical composition comprising tacrolimus |
| JP2021530463A (ja) | 2018-07-02 | 2021-11-11 | パルヴェラ セラピューティクス、インク． | ｍＴＯＲ阻害剤の無水組成物および使用方法 |
| WO2024213629A1 (en) * | 2023-04-11 | 2024-10-17 | Bausch Health Ireland Limited | Topical compositions |
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| US4299826A (en) | 1979-10-12 | 1981-11-10 | The Procter & Gamble Company | Anti-acne composition |
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| GB2212061B (en) | 1987-11-09 | 1991-08-28 | Sandoz Ltd | Topical compositions comprising 11,28-dioxa-4-azatricyclo [22.3.1.0(4,9)] octacos-18-ene derivatives |
| EP0346427B1 (en) | 1987-12-09 | 1995-03-29 | FISONS plc | Macrocyclic compounds |
| KR0159766B1 (ko) * | 1989-10-16 | 1998-12-01 | 후지사와 토모키치로 | 양모제 조성물 |
| DE10299040I2 (de) * | 1989-11-09 | 2006-08-24 | Novartis Ag | Heteroatome enthaltende tricyclische Verbindungen |
| US5061700A (en) | 1989-11-16 | 1991-10-29 | Gordon Jay Dow | Glyceryl acetate ointment vehicles |
| JPH05504956A (ja) | 1990-03-12 | 1993-07-29 | 藤沢薬品工業株式会社 | トリシクロ化合物 |
| WO1991019495A1 (en) | 1990-06-11 | 1991-12-26 | Fujisawa Pharmaceutical Co., Ltd. | Use of a macrolide compound such as fk 506 for manufacturing a medicament for treating idiopathic thrombocytopenic purpura and basedow's disease |
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| US5143918A (en) * | 1990-10-11 | 1992-09-01 | Merck & Co., Inc. | Halomacrolides and derivatives having immunosuppressive activity |
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| US5252732A (en) | 1991-09-09 | 1993-10-12 | Merck & Co., Inc. | D-heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and O-alkynylheteroarylmacrolides having immunosuppressive activity |
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| JPH06183970A (ja) * | 1992-12-16 | 1994-07-05 | Fujisawa Pharmaceut Co Ltd | 医薬用組成物 |
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-
1995
- 1995-10-26 GB GB9707484A patent/GB2308546B/en not_active Expired - Lifetime
- 1995-10-26 SK SK520-97A patent/SK284591B6/sk not_active IP Right Cessation
- 1995-10-26 KR KR1019970702752A patent/KR100434682B1/ko not_active Expired - Lifetime
- 1995-10-26 DK DK95936554T patent/DK0786986T3/da active
- 1995-10-26 AT AT01117396T patent/ATE299017T1/de active
- 1995-10-26 PT PT95936554T patent/PT786986E/pt unknown
- 1995-10-26 CZ CZ19971232A patent/CZ289773B6/cs not_active IP Right Cessation
- 1995-10-26 AU AU38451/95A patent/AU714254B2/en not_active Expired
- 1995-10-26 PL PL95319599A patent/PL184750B1/pl unknown
- 1995-10-26 BR BR9509530A patent/BR9509530A/pt not_active Application Discontinuation
- 1995-10-26 DK DK01117396T patent/DK1147766T3/da active
- 1995-10-26 WO PCT/EP1995/004208 patent/WO1996013249A1/en not_active Ceased
- 1995-10-26 PT PT01117396T patent/PT1147766E/pt unknown
- 1995-10-26 CN CNB021243700A patent/CN100335063C/zh not_active Expired - Lifetime
- 1995-10-26 EP EP01117396A patent/EP1147766B1/en not_active Expired - Lifetime
- 1995-10-26 AT AT95936554T patent/ATE214593T1/de active
- 1995-10-26 NZ NZ331824A patent/NZ331824A/xx not_active IP Right Cessation
- 1995-10-26 DE DE69534306T patent/DE69534306T2/de not_active Expired - Lifetime
- 1995-10-26 ES ES95936554T patent/ES2173978T3/es not_active Expired - Lifetime
- 1995-10-26 CN CN95195900A patent/CN1089233C/zh not_active Expired - Lifetime
- 1995-10-26 CA CA002200966A patent/CA2200966C/en not_active Expired - Lifetime
- 1995-10-26 HU HU9701928A patent/HU223840B1/hu active IP Right Revival
- 1995-10-26 JP JP51431096A patent/JP4155593B2/ja not_active Expired - Lifetime
- 1995-10-26 NZ NZ295170A patent/NZ295170A/xx not_active IP Right Cessation
- 1995-10-26 SI SI9530589T patent/SI0786986T1/xx unknown
- 1995-10-26 DE DE69525957T patent/DE69525957T2/de not_active Expired - Lifetime
- 1995-10-26 DE DE19581804T patent/DE19581804T1/de not_active Ceased
- 1995-10-26 MX MX9702699A patent/MX9702699A/es active IP Right Grant
- 1995-10-26 EP EP95936554A patent/EP0786986B1/en not_active Expired - Lifetime
- 1995-10-26 ES ES01117396T patent/ES2243369T3/es not_active Expired - Lifetime
-
1997
- 1997-03-11 FI FI971018A patent/FI119754B/fi not_active IP Right Cessation
- 1997-04-25 NO NO19971951A patent/NO316963B1/no not_active IP Right Cessation
-
2000
- 2000-12-01 CY CY0000067A patent/CY2211B1/xx unknown
-
2001
- 2001-01-23 US US09/767,656 patent/US6352998B2/en not_active Expired - Lifetime
-
2004
- 2004-09-08 NO NO2004005C patent/NO2004005I2/no unknown
-
2007
- 2007-02-27 JP JP2007047216A patent/JP2007145860A/ja not_active Withdrawn
- 2007-12-28 FI FI20071025A patent/FI119755B/fi not_active IP Right Cessation
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2012
- 2012-03-29 JP JP2012077545A patent/JP5599422B2/ja not_active Expired - Lifetime
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