CA2662122A1 - Controlled release solid oral dosage formulations comprising nisoldipine - Google Patents
Controlled release solid oral dosage formulations comprising nisoldipine Download PDFInfo
- Publication number
- CA2662122A1 CA2662122A1 CA002662122A CA2662122A CA2662122A1 CA 2662122 A1 CA2662122 A1 CA 2662122A1 CA 002662122 A CA002662122 A CA 002662122A CA 2662122 A CA2662122 A CA 2662122A CA 2662122 A1 CA2662122 A1 CA 2662122A1
- Authority
- CA
- Canada
- Prior art keywords
- formulation
- calcium channel
- channel blocker
- nisoldipine
- core
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 234
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 title claims abstract description 159
- 238000009472 formulation Methods 0.000 title claims abstract description 145
- 229960000227 nisoldipine Drugs 0.000 title claims abstract description 95
- 238000013270 controlled release Methods 0.000 title claims abstract description 55
- 239000007787 solid Substances 0.000 title claims description 7
- 229940127291 Calcium channel antagonist Drugs 0.000 claims abstract description 104
- 239000000480 calcium channel blocker Substances 0.000 claims abstract description 102
- 230000004888 barrier function Effects 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 45
- 229940127292 dihydropyridine calcium channel blocker Drugs 0.000 claims abstract description 9
- 239000002866 dihydropyridine calcium channel blocker Substances 0.000 claims abstract description 9
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
- 238000000576 coating method Methods 0.000 claims description 51
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 39
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 32
- 235000020937 fasting conditions Nutrition 0.000 claims description 31
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 30
- 239000011248 coating agent Substances 0.000 claims description 27
- 239000002552 dosage form Substances 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 21
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 17
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 235000019359 magnesium stearate Nutrition 0.000 claims description 10
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 8
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims description 8
- 238000009505 enteric coating Methods 0.000 claims description 8
- 239000002702 enteric coating Substances 0.000 claims description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 8
- 239000008107 starch Substances 0.000 claims description 8
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 7
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 7
- 235000010980 cellulose Nutrition 0.000 claims description 7
- 229920002678 cellulose Polymers 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims description 6
- 239000000314 lubricant Substances 0.000 claims description 6
- 238000003801 milling Methods 0.000 claims description 6
- 229960001597 nifedipine Drugs 0.000 claims description 6
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims description 6
- 229940079470 nisoldipine 40 mg Drugs 0.000 claims description 6
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 6
- 239000000454 talc Substances 0.000 claims description 6
- 229910052623 talc Inorganic materials 0.000 claims description 6
- 235000012222 talc Nutrition 0.000 claims description 6
- 239000001856 Ethyl cellulose Substances 0.000 claims description 5
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 5
- 229920001249 ethyl cellulose Polymers 0.000 claims description 5
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 5
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 5
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 5
- 229920000609 methyl cellulose Polymers 0.000 claims description 5
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- 239000001923 methylcellulose Substances 0.000 claims description 5
- 229960002900 methylcellulose Drugs 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 150000003626 triacylglycerols Chemical class 0.000 claims description 5
- HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 claims description 4
- UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 claims description 4
- RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 claims description 4
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 4
- 229920001503 Glucan Polymers 0.000 claims description 4
- 229920000057 Mannan Polymers 0.000 claims description 4
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 claims description 4
- 229920002732 Polyanhydride Polymers 0.000 claims description 4
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- 235000010443 alginic acid Nutrition 0.000 claims description 4
- 229920000615 alginic acid Polymers 0.000 claims description 4
- 229960000528 amlodipine Drugs 0.000 claims description 4
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims description 4
- 239000004359 castor oil Substances 0.000 claims description 4
- 235000019438 castor oil Nutrition 0.000 claims description 4
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 4
- 230000003111 delayed effect Effects 0.000 claims description 4
- 229960003580 felodipine Drugs 0.000 claims description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 4
- 229960004427 isradipine Drugs 0.000 claims description 4
- 229960004340 lacidipine Drugs 0.000 claims description 4
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 4
- ZDXUKAKRHYTAKV-UHFFFAOYSA-N lercanidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZDXUKAKRHYTAKV-UHFFFAOYSA-N 0.000 claims description 4
- 229960004294 lercanidipine Drugs 0.000 claims description 4
- 229960001783 nicardipine Drugs 0.000 claims description 4
- 229960000715 nimodipine Drugs 0.000 claims description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 4
- 230000002459 sustained effect Effects 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 229920000858 Cyclodextrin Polymers 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229920002305 Schizophyllan Polymers 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- 229960001777 castor oil Drugs 0.000 claims description 3
- 229960000541 cetyl alcohol Drugs 0.000 claims description 3
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- 125000005456 glyceride group Chemical group 0.000 claims description 3
- 229940075507 glyceryl monostearate Drugs 0.000 claims description 3
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 3
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 3
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
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- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 claims description 2
- RWHRFHQRVDUPIK-UHFFFAOYSA-N 50867-57-7 Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O RWHRFHQRVDUPIK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004925 Acrylic resin Substances 0.000 claims description 2
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- 229920002785 Croscarmellose sodium Polymers 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 2
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Landscapes
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| US60/824,043 | 2006-08-30 | ||
| US60/824,054 | 2006-08-30 | ||
| PCT/EP2007/007545 WO2008025532A1 (en) | 2006-08-30 | 2007-08-29 | Controlled release solid oral dosage formulations comprising nisoldipine |
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| CA2662122A1 true CA2662122A1 (en) | 2008-03-06 |
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| CA2662123A Active CA2662123C (en) | 2006-08-30 | 2007-08-29 | Controlled release oral dosage formulations comprising a core and one or more barrier layers |
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| WO (2) | WO2008025532A1 (enExample) |
| ZA (1) | ZA200901688B (enExample) |
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| US7431710B2 (en) | 2002-04-08 | 2008-10-07 | Glaukos Corporation | Ocular implants with anchors and methods thereof |
| MX2009001248A (es) | 2006-08-03 | 2009-02-11 | Nitec Pharma Ag | Tratamiento con glucocorticoide de liberacion prolongada de enfermedad reumatoide. |
| KR20090065519A (ko) | 2006-08-30 | 2009-06-22 | 자고텍 아게 | 니솔디핀을 포함하는 방출 제어형 고형 경구 투여 제제 |
| BRPI0721883A2 (pt) * | 2007-07-23 | 2014-02-18 | Pharmathen Sa | Composição farmacêutica contendo antagonista de canal de cálcio de dihidropiridina e processo para a preparação da mesma |
| MX336789B (es) * | 2007-08-13 | 2016-02-02 | Inspirion Delivery Technologies Llc | Farmacos resistentes al abuso, metodo de uso y metodo de fabricacion. |
| CN104127368A (zh) | 2008-03-11 | 2014-11-05 | 武田药品工业株式会社 | 口腔崩解固体制剂 |
| CN102170874A (zh) | 2008-08-06 | 2011-08-31 | 高思福斯中心（控股）有限公司 | 治疗精神病学障碍的组合物和方法 |
| CA2735460A1 (en) * | 2008-08-29 | 2010-03-04 | The Uab Research Foundation | Novel anti-arrhythmia agent |
| KR20100069170A (ko) * | 2008-12-16 | 2010-06-24 | 삼일제약주식회사 | 라시디핀 함유 과립 및 이를 포함하는 약학 조성물 |
| EP2391369A1 (en) * | 2009-01-26 | 2011-12-07 | Nitec Pharma AG | Delayed-release glucocorticoid treatment of asthma |
| US20100247646A1 (en) * | 2009-03-26 | 2010-09-30 | Ranbaxy Laboratories Limited | Extended release tablets of nisoldipine |
| US20100260842A1 (en) * | 2009-04-06 | 2010-10-14 | Rashmi Nair | Pseudoephedrine pharmaceutical formulations |
| US20100285125A1 (en) * | 2009-05-07 | 2010-11-11 | Padma Venkitachalam Devarajan | Delivery system for poorly soluble drugs |
| US10206813B2 (en) | 2009-05-18 | 2019-02-19 | Dose Medical Corporation | Implants with controlled drug delivery features and methods of using same |
| EP4289416A3 (en) | 2009-05-18 | 2024-01-03 | Dose Medical Corporation | Drug eluting ocular implant |
| US12478503B2 (en) | 2009-05-18 | 2025-11-25 | Glaukos Corporation | Implants with controlled drug delivery features and methods of using same |
| EP2451274B1 (en) | 2009-07-08 | 2017-10-04 | Charleston Laboratories, Inc. | Pharmaceutical compositions |
| MX365650B (es) | 2009-12-02 | 2019-06-10 | Adamas Pharmaceuticals Inc | Composiciones de amantadina y metodos para su uso. |
| US20110217373A1 (en) * | 2010-01-29 | 2011-09-08 | Kumaravel Vivek | Extended release pharmaceutical compositions of guanfacine hydrochloride |
| CN102858373B (zh) * | 2010-03-31 | 2014-11-26 | 持田制药株式会社 | 易服用性固体制剂 |
| EP2643001A4 (en) * | 2010-11-22 | 2014-02-19 | Glaxosmithkline Ip Dev Ltd | METHOD OF TREATING CANCER |
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| AP3815A (en) | 2010-12-22 | 2016-09-30 | Purdue Pharma Lp | Encased tamper resistant controlled release dosage forms |
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2007
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- 2007-08-29 US US11/847,012 patent/US20080057123A1/en not_active Abandoned
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- 2007-08-29 MX MX2009002235A patent/MX2009002235A/es unknown
- 2007-08-29 JP JP2009525976A patent/JP2010501609A/ja active Pending
- 2007-08-29 AU AU2007291506A patent/AU2007291506A1/en not_active Abandoned
- 2007-08-29 EP EP07801966A patent/EP2063871A1/en not_active Withdrawn
- 2007-08-29 US US11/846,896 patent/US9101544B2/en active Active
- 2007-08-29 JP JP2009525973A patent/JP2010501607A/ja not_active Abandoned
- 2007-08-29 WO PCT/EP2007/007545 patent/WO2008025532A1/en not_active Ceased
- 2007-08-29 KR KR1020097006438A patent/KR101575679B1/ko active Active
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2009
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| ES2547226T5 (es) | 2020-06-12 |
| US20080063711A1 (en) | 2008-03-13 |
| JP5788547B2 (ja) | 2015-09-30 |
| MX2009002236A (es) | 2009-03-13 |
| ES2547226T3 (es) | 2015-10-02 |
| ZA200901688B (en) | 2014-02-26 |
| EP2063872B1 (en) | 2015-05-06 |
| EP2063872A1 (en) | 2009-06-03 |
| AU2007291509B2 (en) | 2013-05-02 |
| WO2008025532A1 (en) | 2008-03-06 |
| US20160008288A1 (en) | 2016-01-14 |
| WO2008025535A1 (en) | 2008-03-06 |
| US9101544B2 (en) | 2015-08-11 |
| KR20090065520A (ko) | 2009-06-22 |
| AU2007291506A1 (en) | 2008-03-06 |
| CA2662123A1 (en) | 2008-03-06 |
| JP2010501609A (ja) | 2010-01-21 |
| JP2014114323A (ja) | 2014-06-26 |
| MX2009002235A (es) | 2009-03-13 |
| KR20090065519A (ko) | 2009-06-22 |
| EP2063871A1 (en) | 2009-06-03 |
| JP2010501607A (ja) | 2010-01-21 |
| CA2662123C (en) | 2015-12-01 |
| US9622980B2 (en) | 2017-04-18 |
| KR101575679B1 (ko) | 2015-12-08 |
| EP2063872B2 (en) | 2019-12-04 |
| AU2007291509A1 (en) | 2008-03-06 |
| US20080057123A1 (en) | 2008-03-06 |
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