CA2785254A1 - Pharmaceutical composition comprising solvent mixture and a vitamin d derivative or analogue - Google Patents
Pharmaceutical composition comprising solvent mixture and a vitamin d derivative or analogue Download PDFInfo
- Publication number
- CA2785254A1 CA2785254A1 CA2785254A CA2785254A CA2785254A1 CA 2785254 A1 CA2785254 A1 CA 2785254A1 CA 2785254 A CA2785254 A CA 2785254A CA 2785254 A CA2785254 A CA 2785254A CA 2785254 A1 CA2785254 A1 CA 2785254A1
- Authority
- CA
- Canada
- Prior art keywords
- composition according
- solvent
- composition
- vitamin
- calcipotriol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000003710 vitamin D derivatives Chemical class 0.000 title claims abstract description 30
- 239000011877 solvent mixture Substances 0.000 title claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 239000003937 drug carrier Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 148
- LWQQLNNNIPYSNX-UROSTWAQSA-N calcipotriol Chemical compound C1([C@H](O)/C=C/[C@@H](C)[C@@H]2[C@]3(CCCC(/[C@@H]3CC2)=C\C=C\2C([C@@H](O)C[C@H](O)C/2)=C)C)CC1 LWQQLNNNIPYSNX-UROSTWAQSA-N 0.000 claims description 57
- 229960002882 calcipotriol Drugs 0.000 claims description 47
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 35
- 150000004665 fatty acids Chemical class 0.000 claims description 20
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 19
- 239000000194 fatty acid Substances 0.000 claims description 19
- 229930195729 fatty acid Natural products 0.000 claims description 19
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 15
- 229930003316 Vitamin D Natural products 0.000 claims description 14
- 239000006184 cosolvent Substances 0.000 claims description 14
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 14
- 235000019166 vitamin D Nutrition 0.000 claims description 14
- 239000011710 vitamin D Substances 0.000 claims description 14
- 229940046008 vitamin d Drugs 0.000 claims description 14
- 239000003961 penetration enhancing agent Substances 0.000 claims description 13
- 201000004681 Psoriasis Diseases 0.000 claims description 12
- 150000005215 alkyl ethers Chemical class 0.000 claims description 12
- 229940057917 medium chain triglycerides Drugs 0.000 claims description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 239000004615 ingredient Substances 0.000 claims description 9
- 239000012188 paraffin wax Substances 0.000 claims description 9
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical group CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 8
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 229940041616 menthol Drugs 0.000 claims description 8
- 230000000699 topical effect Effects 0.000 claims description 8
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000001993 wax Substances 0.000 claims description 6
- 201000004624 Dermatitis Diseases 0.000 claims description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 150000004682 monohydrates Chemical class 0.000 claims description 5
- 229920002545 silicone oil Polymers 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000003246 corticosteroid Substances 0.000 claims description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- 150000003626 triacylglycerols Chemical class 0.000 claims description 4
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 claims description 3
- 229960002535 alfacalcidol Drugs 0.000 claims description 3
- 229960005084 calcitriol Drugs 0.000 claims description 3
- GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 claims description 3
- 235000020964 calcitriol Nutrition 0.000 claims description 3
- 239000011612 calcitriol Substances 0.000 claims description 3
- 229960001334 corticosteroids Drugs 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 201000004700 rosacea Diseases 0.000 claims description 3
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 claims description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 2
- SGRCVQDBWHCTIS-UHFFFAOYSA-N 2-nonanoyloxypropyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(C)OC(=O)CCCCCCCC SGRCVQDBWHCTIS-UHFFFAOYSA-N 0.000 claims description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 claims description 2
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 2
- DTXXSJZBSTYZKE-ZDQKKZTESA-N Maxacalcitol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](OCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C DTXXSJZBSTYZKE-ZDQKKZTESA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 claims description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 241001303601 Rosacea Species 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 150000001412 amines Chemical group 0.000 claims description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 2
- 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 claims description 2
- 229960002537 betamethasone Drugs 0.000 claims description 2
- 229940056318 ceteth-20 Drugs 0.000 claims description 2
- 229960005233 cineole Drugs 0.000 claims description 2
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- 229940086555 cyclomethicone Drugs 0.000 claims description 2
- 239000007857 degradation product Substances 0.000 claims description 2
- 229960003428 dexibuprofen Drugs 0.000 claims description 2
- HEFNNWSXXWATRW-JTQLQIEISA-N dexibuprofen Chemical compound CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-JTQLQIEISA-N 0.000 claims description 2
- 229960001259 diclofenac Drugs 0.000 claims description 2
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 229940008099 dimethicone Drugs 0.000 claims description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 2
- 229960002390 flurbiprofen Drugs 0.000 claims description 2
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004817 gas chromatography Methods 0.000 claims description 2
- 125000005908 glyceryl ester group Chemical group 0.000 claims description 2
- 239000008240 homogeneous mixture Substances 0.000 claims description 2
- 229960000890 hydrocortisone Drugs 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229960001680 ibuprofen Drugs 0.000 claims description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229940093629 isopropyl isostearate Drugs 0.000 claims description 2
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims description 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 2
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- OXROWJKCGCOJDO-JLHYYAGUSA-N lornoxicam Chemical compound O=C1C=2SC(Cl)=CC=2S(=O)(=O)N(C)\C1=C(\O)NC1=CC=CC=N1 OXROWJKCGCOJDO-JLHYYAGUSA-N 0.000 claims description 2
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- XEIOPEQGDSYOIH-MURFETPASA-N propan-2-yl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC(C)C XEIOPEQGDSYOIH-MURFETPASA-N 0.000 claims description 2
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- NEOZOXKVMDBOSG-UHFFFAOYSA-N propan-2-yl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC(C)C NEOZOXKVMDBOSG-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
- A61K31/593—9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
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- 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
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- 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
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
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- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
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- 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
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- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- 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
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- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
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- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK2009000264 | 2009-12-22 | ||
| DKPCT/DK2009/000264 | 2009-12-22 | ||
| US29310810P | 2010-01-07 | 2010-01-07 | |
| US61/293,108 | 2010-01-07 | ||
| PCT/DK2010/000184 WO2011076209A2 (en) | 2009-12-22 | 2010-12-22 | Pharmaceutical composition comprising solvent mixture and a vitamin d derivative or analogue |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2785254A1 true CA2785254A1 (en) | 2011-06-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2785254A Abandoned CA2785254A1 (en) | 2009-12-22 | 2010-12-22 | Pharmaceutical composition comprising solvent mixture and a vitamin d derivative or analogue |
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| US (1) | US20130023501A1 (https=) |
| EP (1) | EP2515866B1 (https=) |
| JP (1) | JP5732471B2 (https=) |
| CN (1) | CN102770121B (https=) |
| AU (1) | AU2010335656B2 (https=) |
| BR (1) | BR112012015437A2 (https=) |
| CA (1) | CA2785254A1 (https=) |
| ES (1) | ES2452872T3 (https=) |
| IL (1) | IL220517A (https=) |
| MX (1) | MX2012007225A (https=) |
| NZ (1) | NZ601001A (https=) |
| RU (1) | RU2559084C2 (https=) |
| WO (1) | WO2011076209A2 (https=) |
| ZA (1) | ZA201204622B (https=) |
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| NZ630169A (en) * | 2013-02-27 | 2017-07-28 | Laurie Robert Batt | Anhydrous transdermal formulations |
| KR102486797B1 (ko) * | 2016-03-09 | 2023-01-11 | 삼성전자 주식회사 | 전자 장치 및 전자 장치의 디스플레이 구동 방법 |
| CN107643354B (zh) * | 2016-07-22 | 2022-02-01 | 重庆华邦胜凯制药有限公司 | 卡泊三醇起始原料a及相关杂质的分离与测定方法 |
| CN106265485A (zh) * | 2016-08-22 | 2017-01-04 | 江苏知原药业有限公司 | 一种稳定性改善的卡泊三醇组合物 |
| CN106265511A (zh) * | 2016-08-22 | 2017-01-04 | 江苏知原药业有限公司 | 一种性能优异的卡泊三醇倍他米松自微乳制剂 |
| CN108904445A (zh) * | 2018-08-06 | 2018-11-30 | 江苏知原药业有限公司 | 钙泊三醇纳米悬浮液 |
| CA3157812C (en) * | 2019-10-25 | 2024-10-22 | Cardiol Therapeutics Inc. | Cannabidiol compositions for use in treating heart conditions |
| BR112023001283A2 (pt) | 2020-07-28 | 2023-02-14 | Arcutis Biotherapeutics Inc | Composição farmacêutica tópica; método para tratar uma doença, distúrbio ou afecção inflamatória de pele em um indivíduo que necessita do mesmo; e método para intensificar a penetração em pele em um indivíduo de uma formulação farmacêutica tópica |
| KR20240125610A (ko) | 2021-12-15 | 2024-08-19 | 아큐티스 바이오테라퓨틱스, 인크. | Shr0302의 안정된 제형 |
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| US4083974A (en) * | 1977-03-07 | 1978-04-11 | The Upjohn Company | Topical steroidal anti-inflammatory preparations containing polyoxypropylene 15 stearyl ether |
| DE4011682A1 (de) * | 1990-04-06 | 1991-10-10 | Schering Ag | 24-oxa-derivate in der vitamin d-reihe |
| US5194431A (en) * | 1992-07-08 | 1993-03-16 | Wisconsin Alumni Research Foundation | 24-cyclopropane vitamin D derivatives |
| GB9300763D0 (en) | 1993-01-15 | 1993-03-03 | Leo Pharm Prod Ltd | Chemical compound |
| GB9611603D0 (en) * | 1996-06-04 | 1996-08-07 | Leo Pharm Prod Ltd | Chemical compounds |
| US8263580B2 (en) * | 1998-09-11 | 2012-09-11 | Stiefel Research Australia Pty Ltd | Vitamin formulation |
| US6267985B1 (en) * | 1999-06-30 | 2001-07-31 | Lipocine Inc. | Clear oil-containing pharmaceutical compositions |
| PL199123B1 (pl) * | 1999-04-23 | 2008-08-29 | Leo Pharm Prod Ltd | Niewodna kompozycja farmaceutyczna do stosowania naskórnego i jej zastosowanie |
| BR0214679A (pt) * | 2001-12-03 | 2004-12-14 | Novacea Inc | Composições farmacêuticas compreendendo compostos a base de vitamina d ativa |
| DK1658263T3 (da) | 2003-07-24 | 2010-09-27 | Leo Pharma As | Aminobenzophenonforbindelser |
| US8741333B2 (en) * | 2004-06-07 | 2014-06-03 | Nuvo Research Inc. | Compositions and methods for treating dermatitis or psoriasis |
| FR2871694B1 (fr) * | 2004-06-17 | 2008-07-04 | Galderma Sa | Composition pharmaceutique comprenant un onguent oleagineux et deux principes actifs solubilises |
| KR101260236B1 (ko) | 2004-12-13 | 2013-05-06 | 레오 파마 에이/에스 | 트리아졸 치환된 아미노벤조페논 화합물 |
| FR2887150B1 (fr) * | 2005-06-17 | 2007-08-03 | Galderma Res & Dev | Composition pharmaceutique comprenant un elastomere organopolysiloxane et un principe actif solubilise |
| FR2909284B1 (fr) * | 2006-11-30 | 2012-09-21 | Galderma Sa | Nouvelles compositions sous forme d'onguent sans vaseline comprenant un derive de vitamine d et eventuellement un anti-inflammatoire steroidien |
| EP2125736B1 (en) | 2006-12-22 | 2011-03-30 | Leo Pharma A/S | Substituted acetophenones useful as pde4 inhibitors |
| CA2676933C (en) | 2007-02-28 | 2015-09-29 | Leo Pharma A/S | Novel phosphodiesterase inhibitors |
| US7909624B2 (en) | 2007-03-26 | 2011-03-22 | Belkin International, Inc. | Carabiner universal serial bus hub |
| JP2010524864A (ja) | 2007-04-19 | 2010-07-22 | レオ ファーマ アクティーゼルスカブ | Ｓｒｃファミリーキナーゼ阻害剤 |
| PL2148661T3 (pl) * | 2007-04-25 | 2013-07-31 | Cytochroma Inc | Doustne kompozycje o kontrolowanym uwalnianiu zawierające związek będący witaminą D i woskowy nośnik |
| CA2685516A1 (en) | 2007-05-11 | 2008-11-20 | Sonneborn Inc. | Petrolatums having silicone-like properties |
| RU2544011C2 (ru) | 2008-12-19 | 2015-03-10 | Лео Фарма А/С | Триазолопиридины в качестве ингибиторов фосфодиэстеразы для лечения кожных заболеваний |
-
2010
- 2010-12-22 NZ NZ601001A patent/NZ601001A/en not_active IP Right Cessation
- 2010-12-22 BR BR112012015437A patent/BR112012015437A2/pt not_active IP Right Cessation
- 2010-12-22 EP EP10803219.4A patent/EP2515866B1/en active Active
- 2010-12-22 WO PCT/DK2010/000184 patent/WO2011076209A2/en not_active Ceased
- 2010-12-22 CN CN201080064576.4A patent/CN102770121B/zh not_active Expired - Fee Related
- 2010-12-22 RU RU2012130411/15A patent/RU2559084C2/ru not_active IP Right Cessation
- 2010-12-22 AU AU2010335656A patent/AU2010335656B2/en not_active Ceased
- 2010-12-22 JP JP2012545092A patent/JP5732471B2/ja not_active Expired - Fee Related
- 2010-12-22 US US13/518,314 patent/US20130023501A1/en not_active Abandoned
- 2010-12-22 ES ES10803219.4T patent/ES2452872T3/es active Active
- 2010-12-22 CA CA2785254A patent/CA2785254A1/en not_active Abandoned
- 2010-12-22 MX MX2012007225A patent/MX2012007225A/es active IP Right Grant
-
2012
- 2012-06-19 IL IL220517A patent/IL220517A/en not_active IP Right Cessation
- 2012-06-21 ZA ZA2012/04622A patent/ZA201204622B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ601001A (en) | 2014-07-25 |
| EP2515866A2 (en) | 2012-10-31 |
| EP2515866B1 (en) | 2014-02-19 |
| CN102770121B (zh) | 2014-10-15 |
| JP5732471B2 (ja) | 2015-06-10 |
| AU2010335656A1 (en) | 2012-07-19 |
| JP2013515020A (ja) | 2013-05-02 |
| MX2012007225A (es) | 2012-07-30 |
| BR112012015437A2 (pt) | 2016-03-15 |
| WO2011076209A2 (en) | 2011-06-30 |
| RU2012130411A (ru) | 2014-01-27 |
| ZA201204622B (en) | 2013-09-25 |
| ES2452872T3 (es) | 2014-04-03 |
| HK1177696A1 (en) | 2013-08-30 |
| RU2559084C2 (ru) | 2015-08-10 |
| IL220517A (en) | 2016-08-31 |
| IL220517A0 (en) | 2012-08-30 |
| CN102770121A (zh) | 2012-11-07 |
| AU2010335656B2 (en) | 2015-05-07 |
| US20130023501A1 (en) | 2013-01-24 |
| WO2011076209A3 (en) | 2012-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20151208 |
|
| FZDE | Discontinued |
Effective date: 20180523 |