ES2452872T3 - Composición farmacéutica que comprende una mezcla solvente y un derivado o análogo de vitamina D - Google Patents
Composición farmacéutica que comprende una mezcla solvente y un derivado o análogo de vitamina D Download PDFInfo
- Publication number
- ES2452872T3 ES2452872T3 ES10803219.4T ES10803219T ES2452872T3 ES 2452872 T3 ES2452872 T3 ES 2452872T3 ES 10803219 T ES10803219 T ES 10803219T ES 2452872 T3 ES2452872 T3 ES 2452872T3
- Authority
- ES
- Spain
- Prior art keywords
- composition according
- solvent
- composition
- calcipotriol
- isopropyl
- 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
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- 239000011877 solvent mixture Substances 0.000 title claims abstract description 33
- 150000003710 vitamin D derivatives Chemical class 0.000 title description 22
- 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 title description 21
- 229930003316 Vitamin D Natural products 0.000 title description 19
- 235000019166 vitamin D Nutrition 0.000 title description 19
- 239000011710 vitamin D Substances 0.000 title description 19
- 229940046008 vitamin d Drugs 0.000 title description 19
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 139
- 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 abstract description 64
- 229960002882 calcipotriol Drugs 0.000 claims abstract description 53
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 37
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 22
- 239000000194 fatty acid Substances 0.000 claims abstract description 22
- 229930195729 fatty acid Natural products 0.000 claims abstract description 22
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 18
- 239000006184 cosolvent Substances 0.000 claims abstract description 15
- 239000003961 penetration enhancing agent Substances 0.000 claims abstract description 15
- 150000005215 alkyl ethers Chemical class 0.000 claims abstract description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 fatty acid triglycerides Chemical class 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 9
- 230000000699 topical effect Effects 0.000 claims abstract description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 4
- SGRCVQDBWHCTIS-UHFFFAOYSA-N 2-nonanoyloxypropyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(C)OC(=O)CCCCCCCC SGRCVQDBWHCTIS-UHFFFAOYSA-N 0.000 claims abstract description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005908 glyceryl ester group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 4
- 229940093629 isopropyl isostearate Drugs 0.000 claims abstract description 4
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 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 abstract description 4
- PZQSQRCNMZGWFT-QXMHVHEDSA-N propan-2-yl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(C)C PZQSQRCNMZGWFT-QXMHVHEDSA-N 0.000 claims abstract description 4
- NEOZOXKVMDBOSG-UHFFFAOYSA-N propan-2-yl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC(C)C NEOZOXKVMDBOSG-UHFFFAOYSA-N 0.000 claims abstract description 4
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- 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
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- 239000001993 wax Substances 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- 229920002545 silicone oil Polymers 0.000 claims description 5
- 201000004624 Dermatitis Diseases 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
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- 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
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- 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 3
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- 229940070710 valerate Drugs 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- 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
- 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
- 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
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- 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
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- 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
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- 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
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- 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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- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 2
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- A61K31/593—9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
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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
- A61K47/10—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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- A61K47/06—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
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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Landscapes
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- 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 |
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| WOPCT/DK2009/000264 | 2009-12-22 | ||
| DK2009000264 | 2009-12-22 | ||
| US29310810P | 2010-01-07 | 2010-01-07 | |
| US293108P | 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 |
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| ES2452872T3 true ES2452872T3 (es) | 2014-04-03 |
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| ES10803219.4T Active ES2452872T3 (es) | 2009-12-22 | 2010-12-22 | Composición farmacéutica que comprende una mezcla solvente y un derivado o análogo de vitamina D |
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| BR112015020707B1 (pt) * | 2013-02-27 | 2022-09-13 | Laurie Robert Batt | Composição transdérmica anidra e método de fabricação da mesma |
| 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 |
| 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 |
| 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 |
| 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 |
| EP4048245A4 (en) * | 2019-10-25 | 2023-12-06 | Cardiol Therapeutics Inc. | Cannabidiol compositions for use in treating heart conditions |
| CA3183916C (en) | 2020-07-28 | 2025-06-10 | Arcutis Biotherapeutics, Inc. | TOPICAL FORMULATIONS CONTAINING LAURETH-4 |
| AU2022413551A1 (en) | 2021-12-15 | 2024-07-04 | Arcutis Biotherapeutics, Inc. | Stable formulations of shr0302 |
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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 |
| EP1178808B2 (en) * | 1999-04-23 | 2019-06-12 | Leo Pharma A/S | Non-aqueous pharmaceutical composition for dermal use to treat psoriasis comprising a vitamin d, a corticosteroid and a solvent component |
| EA008072B1 (ru) * | 2001-12-03 | 2007-02-27 | Новацея, Инк. | Фармацевтические составы, содержащие соединения активного витамина d |
| CA2530302C (en) | 2003-07-24 | 2013-12-03 | Leo Pharma A/S | Novel aminobenzophenone compounds |
| 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 |
| JP5015005B2 (ja) | 2004-12-13 | 2012-08-29 | レオ ファーマ アクティーゼルスカブ | トリアゾール置換アミノベンゾフェノン化合物 |
| 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 |
| JP5342451B2 (ja) | 2006-12-22 | 2013-11-13 | レオ ファーマ アクティーゼルスカブ | Ｐｄｅ４阻害剤として有用な置換アセトフェノン |
| KR101571654B1 (ko) | 2007-02-28 | 2015-11-25 | 레오 파마 에이/에스 | 신규한 포스포디에스테라제 억제제 |
| 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 |
| SI2481400T1 (sl) * | 2007-04-25 | 2014-11-28 | Opko IP Holdings II, Inc. | Nadzorovano oralno sproščanje sestavkov, ki vsebujejo spojino vitamina D in voskasti nosilec |
| EP2146780A1 (en) | 2007-05-11 | 2010-01-27 | Sonneborn Inc. | Petrolatums having silicone-like properties |
| SG172206A1 (en) | 2008-12-19 | 2011-07-28 | Leo Pharma As | Triazolopyridines as phosphodiesterase inhibitors for treatment of dermal diseases |
-
2010
- 2010-12-22 RU RU2012130411/15A patent/RU2559084C2/ru not_active IP Right Cessation
- 2010-12-22 CA CA2785254A patent/CA2785254A1/en not_active Abandoned
- 2010-12-22 BR BR112012015437A patent/BR112012015437A2/pt not_active IP Right Cessation
- 2010-12-22 CN CN201080064576.4A patent/CN102770121B/zh not_active Expired - Fee Related
- 2010-12-22 MX MX2012007225A patent/MX2012007225A/es active IP Right Grant
- 2010-12-22 NZ NZ601001A patent/NZ601001A/en not_active IP Right Cessation
- 2010-12-22 JP JP2012545092A patent/JP5732471B2/ja not_active Expired - Fee Related
- 2010-12-22 ES ES10803219.4T patent/ES2452872T3/es active Active
- 2010-12-22 US US13/518,314 patent/US20130023501A1/en not_active Abandoned
- 2010-12-22 WO PCT/DK2010/000184 patent/WO2011076209A2/en not_active Ceased
- 2010-12-22 EP EP10803219.4A patent/EP2515866B1/en active Active
- 2010-12-22 AU AU2010335656A patent/AU2010335656B2/en not_active Ceased
-
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 |
|---|---|
| JP2013515020A (ja) | 2013-05-02 |
| MX2012007225A (es) | 2012-07-30 |
| WO2011076209A2 (en) | 2011-06-30 |
| EP2515866B1 (en) | 2014-02-19 |
| HK1177696A1 (en) | 2013-08-30 |
| BR112012015437A2 (pt) | 2016-03-15 |
| ZA201204622B (en) | 2013-09-25 |
| RU2559084C2 (ru) | 2015-08-10 |
| US20130023501A1 (en) | 2013-01-24 |
| WO2011076209A3 (en) | 2012-02-23 |
| AU2010335656B2 (en) | 2015-05-07 |
| CN102770121B (zh) | 2014-10-15 |
| RU2012130411A (ru) | 2014-01-27 |
| NZ601001A (en) | 2014-07-25 |
| IL220517A0 (en) | 2012-08-30 |
| IL220517A (en) | 2016-08-31 |
| CN102770121A (zh) | 2012-11-07 |
| AU2010335656A1 (en) | 2012-07-19 |
| CA2785254A1 (en) | 2011-06-30 |
| JP5732471B2 (ja) | 2015-06-10 |
| EP2515866A2 (en) | 2012-10-31 |
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