BR112015016605B1 - Método para processar partículas de um ingrediente farmacêutico em suspensão, método para evitar maturação de ostwald e uso de um método para processar partículas de um ingrediente farmacêutico em forma de pó a partir de uma suspensão do ingrediente farmacêutico - Google Patents
Método para processar partículas de um ingrediente farmacêutico em suspensão, método para evitar maturação de ostwald e uso de um método para processar partículas de um ingrediente farmacêutico em forma de pó a partir de uma suspensão do ingrediente farmacêutico Download PDFInfo
- Publication number
- BR112015016605B1 BR112015016605B1 BR112015016605-9A BR112015016605A BR112015016605B1 BR 112015016605 B1 BR112015016605 B1 BR 112015016605B1 BR 112015016605 A BR112015016605 A BR 112015016605A BR 112015016605 B1 BR112015016605 B1 BR 112015016605B1
- Authority
- BR
- Brazil
- Prior art keywords
- suspension
- pharmaceutical ingredient
- particles
- high pressure
- particle size
- Prior art date
Links
- 239000002245 particle Substances 0.000 title claims abstract description 97
- 239000000725 suspension Substances 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 56
- 239000004615 ingredient Substances 0.000 title claims abstract description 39
- 230000035800 maturation Effects 0.000 title claims abstract description 19
- 239000000843 powder Substances 0.000 title claims abstract description 18
- 238000012545 processing Methods 0.000 title claims abstract description 15
- 230000008569 process Effects 0.000 claims abstract description 27
- 238000000265 homogenisation Methods 0.000 claims abstract description 21
- 238000002955 isolation Methods 0.000 claims abstract description 19
- 239000003381 stabilizer Substances 0.000 claims abstract description 17
- 238000001016 Ostwald ripening Methods 0.000 claims abstract description 15
- 238000001035 drying Methods 0.000 claims description 19
- 239000012296 anti-solvent Substances 0.000 claims description 16
- 238000004064 recycling Methods 0.000 claims description 9
- 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 5
- 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
- 238000001694 spray drying Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- 238000009826 distribution Methods 0.000 description 10
- 239000008186 active pharmaceutical agent Substances 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000000087 stabilizing effect Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium 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
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000004886 process control Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 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
- 239000000428 dust Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229960004123 mometasone furoate monohydrate Drugs 0.000 description 2
- 239000006070 nanosuspension Substances 0.000 description 2
- 238000010951 particle size reduction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 230000001376 precipitating effect Effects 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
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000013019 agitation Methods 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
- 230000008034 disappearance Effects 0.000 description 1
- 229960003668 docetaxel 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
- -1 furoate monohydrate Chemical class 0.000 description 1
- 230000002209 hydrophobic 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
- 239000002609 medium Substances 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
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 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
- 238000012552 review Methods 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
- 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
- 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
Images
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 (3)
| 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 |
| PT106738 | 2013-01-09 | ||
| PCT/GB2014/050055 WO2014108687A1 (en) | 2013-01-09 | 2014-01-09 | Dynamic suspension drying (dsd) to control ostwald ripening |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112015016605A2 BR112015016605A2 (pt) | 2017-07-11 |
| BR112015016605B1 true BR112015016605B1 (pt) | 2022-11-29 |
Family
ID=49999991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112015016605-9A BR112015016605B1 (pt) | 2013-01-09 | 2014-01-09 | Método para processar partículas de um ingrediente farmacêutico em suspensão, método para evitar maturação de ostwald e uso de um método para processar partículas de um ingrediente farmacêutico em forma de pó a partir de uma suspensão do ingrediente farmacêutico |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10151529B2 (https=) |
| EP (1) | EP2874609B1 (https=) |
| JP (1) | JP6316847B2 (https=) |
| CN (1) | CN105007900B (https=) |
| BR (1) | BR112015016605B1 (https=) |
| CA (1) | CA2897277C (https=) |
| DK (1) | DK2874609T3 (https=) |
| ES (1) | ES2659968T3 (https=) |
| HU (1) | HUE036691T2 (https=) |
| IL (1) | IL239845B (https=) |
| PT (1) | PT106738B (https=) |
| SG (1) | SG11201505370RA (https=) |
| WO (1) | WO2014108687A1 (https=) |
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 |
| 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 |
| US5665382A (en) * | 1993-02-22 | 1997-09-09 | Vivorx Pharmaceuticals, Inc. | Methods for the preparation of pharmaceutically active agents for in vivo delivery |
| 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 |
| 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 |
| 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 |
| US5665383A (en) * | 1993-02-22 | 1997-09-09 | Vivorx Pharmaceuticals, Inc. | Methods for the preparation of immunostimulating agents for in vivo delivery |
| US6096331A (en) * | 1993-02-22 | 2000-08-01 | Vivorx Pharmaceuticals, Inc. | Methods and compositions useful for administration of chemotherapeutic agents |
| US5650156A (en) * | 1993-02-22 | 1997-07-22 | Vivorx Pharmaceuticals, Inc. | Methods for in vivo delivery of nutriceuticals and compositions useful therefor |
| NZ262679A (en) * | 1993-02-22 | 1997-08-22 | Vivorx Pharmaceuticals Inc | Compositions for in vivo delivery of pharmaceutical agents where the agents are contained in a polymeric shell |
| HK1045646A1 (zh) * | 1999-05-21 | 2002-12-06 | Abraxis Bioscience, Llc | 蛋白質穩定化的藥理學活性劑，其製備方法及其使用方法 |
| US6318649B1 (en) * | 1999-10-06 | 2001-11-20 | Cornerstone Technologies, Llc | Method of creating ultra-fine particles of materials using a high-pressure mill |
| EP1276465B1 (en) * | 2000-04-20 | 2014-03-12 | Jagotec AG | Improved water-insoluble drug particle process |
| AU2001270302A1 (en) | 2000-07-06 | 2002-01-21 | Cornerstone Technologies, L.L.C. | Multi-stage size reduction, blending and drying system and method |
| IL160103A0 (en) * | 2001-08-06 | 2004-06-20 | Astrazeneca Ab | Aqueous dispersion comprising stable nanoparticles of a water-insoluble active substance and an excipient like middle chain triglycerides (mct) |
| AU2003283954A1 (en) * | 2002-12-06 | 2004-06-30 | Cornerstone Technologies, L.L.C. | High g mill in a blending and drying system |
| JP5571380B2 (ja) * | 2006-07-24 | 2014-08-13 | ルミナス バイオサイエンシズ，インコーポレイテッド | オストワルド熟成を減少させた水不溶性の医薬品物質の固体ナノ粒子処方物 |
| 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 JP JP2015552139A patent/JP6316847B2/ja not_active Expired - Fee Related
- 2014-01-09 CN CN201480011112.5A patent/CN105007900B/zh not_active Expired - Fee Related
- 2014-01-09 HU HUE14701124A patent/HUE036691T2/hu unknown
- 2014-01-09 BR BR112015016605-9A patent/BR112015016605B1/pt not_active IP Right Cessation
- 2014-01-09 WO PCT/GB2014/050055 patent/WO2014108687A1/en not_active Ceased
- 2014-01-09 ES ES14701124.1T patent/ES2659968T3/es active Active
- 2014-01-09 CA CA2897277A patent/CA2897277C/en active Active
- 2014-01-09 EP EP14701124.1A patent/EP2874609B1/en active Active
- 2014-01-09 DK DK14701124.1T patent/DK2874609T3/en active
- 2014-01-09 US US14/760,095 patent/US10151529B2/en active 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 |
|---|---|
| US10151529B2 (en) | 2018-12-11 |
| WO2014108687A1 (en) | 2014-07-17 |
| CN105007900A (zh) | 2015-10-28 |
| US20150354891A1 (en) | 2015-12-10 |
| CN105007900B (zh) | 2019-04-12 |
| HUE036691T2 (hu) | 2018-07-30 |
| SG11201505370RA (en) | 2015-08-28 |
| EP2874609A1 (en) | 2015-05-27 |
| JP6316847B2 (ja) | 2018-04-25 |
| DK2874609T3 (en) | 2018-04-09 |
| BR112015016605A2 (pt) | 2017-07-11 |
| PT106738A (pt) | 2014-07-09 |
| CA2897277C (en) | 2020-09-01 |
| IL239845A0 (en) | 2015-08-31 |
| EP2874609B1 (en) | 2017-12-27 |
| PT106738B (pt) | 2015-06-08 |
| JP2016508989A (ja) | 2016-03-24 |
| IL239845B (en) | 2019-05-30 |
| ES2659968T3 (es) | 2018-03-20 |
| CA2897277A1 (en) | 2014-07-17 |
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