DK2874609T3 - Dynamic suspension drying (DSD) to control Ostwald maturation - Google Patents
Dynamic suspension drying (DSD) to control Ostwald maturation Download PDFInfo
- Publication number
- DK2874609T3 DK2874609T3 DK14701124.1T DK14701124T DK2874609T3 DK 2874609 T3 DK2874609 T3 DK 2874609T3 DK 14701124 T DK14701124 T DK 14701124T DK 2874609 T3 DK2874609 T3 DK 2874609T3
- Authority
- DK
- Denmark
- Prior art keywords
- suspension
- pressure conditions
- high pressure
- pharmaceutical ingredient
- particles
- Prior art date
Links
- 239000000725 suspension Substances 0.000 title claims description 66
- 238000001035 drying Methods 0.000 title claims description 22
- 230000035800 maturation Effects 0.000 title claims 2
- 239000002245 particle Substances 0.000 claims description 92
- 238000000034 method Methods 0.000 claims description 48
- 239000004615 ingredient Substances 0.000 claims description 31
- 230000008569 process Effects 0.000 claims description 28
- 238000000265 homogenisation Methods 0.000 claims description 24
- 239000000843 powder Substances 0.000 claims description 17
- 239000012296 anti-solvent Substances 0.000 claims description 15
- 238000002955 isolation Methods 0.000 claims description 14
- 239000003381 stabilizer Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000012545 processing Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- 238000001694 spray drying Methods 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- 238000009413 insulation Methods 0.000 claims 2
- 238000003754 machining Methods 0.000 claims 1
- 230000003134 recirculating effect Effects 0.000 claims 1
- 238000001016 Ostwald ripening Methods 0.000 description 36
- 238000009826 distribution Methods 0.000 description 10
- 230000006641 stabilisation Effects 0.000 description 9
- 238000011105 stabilization Methods 0.000 description 9
- 239000008186 active pharmaceutical agent Substances 0.000 description 8
- 238000004064 recycling Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229960004123 mometasone furoate monohydrate Drugs 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- AQCCVUHZMIMSIB-HRVPQZBTSA-N [(8s,9r,10s,11s,13s,14s,16r,17r)-9-chloro-17-(2-chloroacetyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate;hydrate Chemical compound O.O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 AQCCVUHZMIMSIB-HRVPQZBTSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012369 In process control Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010965 in-process control Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000006070 nanosuspension Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- CTKXFMQHOOWWEB-UHFFFAOYSA-N Ethylene oxide/propylene oxide copolymer Chemical compound CCCOC(C)COCCO CTKXFMQHOOWWEB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000003116 impacting effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 230000005226 mechanical processes and functions Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002159 nanocrystal Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 238000010951 particle size reduction Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 229940044519 poloxamer 188 Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- CZPILLBHPRAPCB-AREMUKBSSA-N tarazepide Chemical compound O=C([C@@H](NC(=O)C=1N2CCCC=3C=CC=C(C2=3)C=1)N=1)N(C)C2=CC=CC=C2C=1C1=CC=CC=C1 CZPILLBHPRAPCB-AREMUKBSSA-N 0.000 description 1
- 229950010940 tarazepide Drugs 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F26—DRYING
- F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
- F26B3/00—Drying solid materials or objects by processes involving the application of heat
- F26B3/02—Drying solid materials or objects by processes involving the application of heat by convection, i.e. heat being conveyed from a heat source to the materials or objects to be dried by a gas or vapour, e.g. air
- F26B3/10—Drying solid materials or objects by processes involving the application of heat by convection, i.e. heat being conveyed from a heat source to the materials or objects to be dried by a gas or vapour, e.g. air the gas or vapour carrying the materials or objects to be dried with it
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1682—Processes
- A61K9/1688—Processes resulting in pure drug agglomerate optionally containing up to 5% of excipient
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1682—Processes
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F26—DRYING
- F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
- F26B1/00—Preliminary treatment of solid materials or objects to facilitate drying, e.g. mixing or backmixing the materials to be dried with predominantly dry solids
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F26—DRYING
- F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
- F26B3/00—Drying solid materials or objects by processes involving the application of heat
- F26B3/02—Drying solid materials or objects by processes involving the application of heat by convection, i.e. heat being conveyed from a heat source to the materials or objects to be dried by a gas or vapour, e.g. air
- F26B3/10—Drying solid materials or objects by processes involving the application of heat by convection, i.e. heat being conveyed from a heat source to the materials or objects to be dried by a gas or vapour, e.g. air the gas or vapour carrying the materials or objects to be dried with it
- F26B3/12—Drying solid materials or objects by processes involving the application of heat by convection, i.e. heat being conveyed from a heat source to the materials or objects to be dried by a gas or vapour, e.g. air the gas or vapour carrying the materials or objects to be dried with it in the form of a spray, i.e. sprayed or dispersed emulsions or suspensions
Landscapes
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT106738A PT106738B (pt) | 2013-01-09 | 2013-01-09 | Método para o controlo do fenómeno de degradação difusional de ostwald (ostwald ripening) no processamento de partículas de um ingrediente farmacêutico |
| PCT/GB2014/050055 WO2014108687A1 (en) | 2013-01-09 | 2014-01-09 | Dynamic suspension drying (dsd) to control ostwald ripening |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2874609T3 true DK2874609T3 (en) | 2018-04-09 |
Family
ID=49999991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK14701124.1T DK2874609T3 (en) | 2013-01-09 | 2014-01-09 | Dynamic suspension drying (DSD) to control Ostwald maturation |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10151529B2 (OSRAM) |
| EP (1) | EP2874609B1 (OSRAM) |
| JP (1) | JP6316847B2 (OSRAM) |
| CN (1) | CN105007900B (OSRAM) |
| BR (1) | BR112015016605B1 (OSRAM) |
| CA (1) | CA2897277C (OSRAM) |
| DK (1) | DK2874609T3 (OSRAM) |
| ES (1) | ES2659968T3 (OSRAM) |
| HU (1) | HUE036691T2 (OSRAM) |
| IL (1) | IL239845B (OSRAM) |
| PT (1) | PT106738B (OSRAM) |
| SG (1) | SG11201505370RA (OSRAM) |
| WO (1) | WO2014108687A1 (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT108368B (pt) | 2015-03-31 | 2018-11-05 | Hovione Farm S A | Produção contínua de partículas |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4826689A (en) | 1984-05-21 | 1989-05-02 | University Of Rochester | Method for making uniformly sized particles from water-insoluble organic compounds |
| US5916596A (en) * | 1993-02-22 | 1999-06-29 | Vivorx Pharmaceuticals, Inc. | Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof |
| US5997904A (en) * | 1993-02-22 | 1999-12-07 | American Bioscience, Inc. | Total nutrient admixtures as stable multicomponent liquids or dry powders and methods for the preparation thereof |
| US6096331A (en) * | 1993-02-22 | 2000-08-01 | Vivorx Pharmaceuticals, Inc. | Methods and compositions useful for administration of chemotherapeutic agents |
| US5665382A (en) * | 1993-02-22 | 1997-09-09 | Vivorx Pharmaceuticals, Inc. | Methods for the preparation of pharmaceutically active agents for in vivo delivery |
| US5439686A (en) * | 1993-02-22 | 1995-08-08 | Vivorx Pharmaceuticals, Inc. | Methods for in vivo delivery of substantially water insoluble pharmacologically active agents and compositions useful therefor |
| US5650156A (en) * | 1993-02-22 | 1997-07-22 | Vivorx Pharmaceuticals, Inc. | Methods for in vivo delivery of nutriceuticals and compositions useful therefor |
| US5498421A (en) * | 1993-02-22 | 1996-03-12 | Vivorx Pharmaceuticals, Inc. | Composition useful for in vivo delivery of biologics and methods employing same |
| US5665383A (en) * | 1993-02-22 | 1997-09-09 | Vivorx Pharmaceuticals, Inc. | Methods for the preparation of immunostimulating agents for in vivo delivery |
| US6749868B1 (en) * | 1993-02-22 | 2004-06-15 | American Bioscience, Inc. | Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof |
| CA2371912C (en) * | 1999-05-21 | 2010-02-16 | American Bioscience, Inc. | Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof |
| US6318649B1 (en) * | 1999-10-06 | 2001-11-20 | Cornerstone Technologies, Llc | Method of creating ultra-fine particles of materials using a high-pressure mill |
| ES2469642T3 (es) * | 2000-04-20 | 2014-06-18 | Jagotec Ag | Procedimiento mejorado para partículas de fármaco insoluble en agua |
| JP2004502530A (ja) | 2000-07-06 | 2004-01-29 | コーナーストーン テクノロジーズ， エル．エル．シー． | 複数ステージのサイズリダクション、ブレンドおよび乾燥システム、ならびに方法。 |
| ES2287293T3 (es) * | 2001-08-06 | 2007-12-16 | Astrazeneca Ab | Dispersion acuosa que comprende nanoparticulas estables de trigliceridos de cadena media (mct) activos, insolubles en agua y de tipo excipiente. |
| WO2004052567A2 (en) * | 2002-12-06 | 2004-06-24 | Cornerstone Technologies, L.L.C. | High g mill in a blending and drying system |
| US8728527B2 (en) * | 2006-07-24 | 2014-05-20 | Luminus Biosciences, Inc. | Solid nanoparticle formulation of water insoluble pharmaceutical substances with reduced ostwald ripening |
| PT105058B (pt) * | 2010-04-21 | 2013-04-17 | Hovione Farmaciencia S A | Processo para processamento de partículas de ingredientes activos farmacêuticos |
-
2013
- 2013-01-09 PT PT106738A patent/PT106738B/pt active IP Right Grant
-
2014
- 2014-01-09 BR BR112015016605-9A patent/BR112015016605B1/pt not_active IP Right Cessation
- 2014-01-09 ES ES14701124.1T patent/ES2659968T3/es active Active
- 2014-01-09 CN CN201480011112.5A patent/CN105007900B/zh not_active Expired - Fee Related
- 2014-01-09 CA CA2897277A patent/CA2897277C/en active Active
- 2014-01-09 JP JP2015552139A patent/JP6316847B2/ja not_active Expired - Fee Related
- 2014-01-09 WO PCT/GB2014/050055 patent/WO2014108687A1/en not_active Ceased
- 2014-01-09 US US14/760,095 patent/US10151529B2/en active Active
- 2014-01-09 EP EP14701124.1A patent/EP2874609B1/en active Active
- 2014-01-09 HU HUE14701124A patent/HUE036691T2/hu unknown
- 2014-01-09 DK DK14701124.1T patent/DK2874609T3/en active
- 2014-01-09 SG SG11201505370RA patent/SG11201505370RA/en unknown
-
2015
- 2015-07-08 IL IL239845A patent/IL239845B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP2874609A1 (en) | 2015-05-27 |
| JP2016508989A (ja) | 2016-03-24 |
| WO2014108687A1 (en) | 2014-07-17 |
| CN105007900A (zh) | 2015-10-28 |
| EP2874609B1 (en) | 2017-12-27 |
| HUE036691T2 (hu) | 2018-07-30 |
| IL239845A0 (en) | 2015-08-31 |
| SG11201505370RA (en) | 2015-08-28 |
| BR112015016605A2 (pt) | 2017-07-11 |
| PT106738A (pt) | 2014-07-09 |
| IL239845B (en) | 2019-05-30 |
| CN105007900B (zh) | 2019-04-12 |
| PT106738B (pt) | 2015-06-08 |
| ES2659968T3 (es) | 2018-03-20 |
| CA2897277A1 (en) | 2014-07-17 |
| JP6316847B2 (ja) | 2018-04-25 |
| US10151529B2 (en) | 2018-12-11 |
| US20150354891A1 (en) | 2015-12-10 |
| BR112015016605B1 (pt) | 2022-11-29 |
| CA2897277C (en) | 2020-09-01 |
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