RU2597790C2 - Способ обработки частиц активных фармацевтических ингредиентов - Google Patents
Способ обработки частиц активных фармацевтических ингредиентов Download PDFInfo
- Publication number
- RU2597790C2 RU2597790C2 RU2012149459/15A RU2012149459A RU2597790C2 RU 2597790 C2 RU2597790 C2 RU 2597790C2 RU 2012149459/15 A RU2012149459/15 A RU 2012149459/15A RU 2012149459 A RU2012149459 A RU 2012149459A RU 2597790 C2 RU2597790 C2 RU 2597790C2
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- RU
- Russia
- Prior art keywords
- active pharmaceutical
- ingredient
- active
- pharmaceutical ingredient
- cavitation
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 63
- 239000008186 active pharmaceutical agent Substances 0.000 title claims abstract description 45
- 239000002245 particle Substances 0.000 title claims abstract description 45
- 238000009826 distribution Methods 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 210000004072 lung Anatomy 0.000 claims abstract description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 239000000725 suspension Substances 0.000 claims description 35
- 239000000843 powder Substances 0.000 claims description 17
- 238000001694 spray drying Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 10
- 229960004123 mometasone furoate monohydrate Drugs 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims description 5
- 229960000289 fluticasone propionate Drugs 0.000 claims description 5
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims description 5
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 claims description 4
- 229960001469 fluticasone furoate Drugs 0.000 claims description 4
- XTULMSXFIHGYFS-VLSRWLAYSA-N fluticasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(F)[C@@]4(C)C=CC(=O)C=C4[C@@H](F)C[C@H]3[C@@H]2C[C@H]1C)C(=O)SCF)C(=O)C1=CC=CO1 XTULMSXFIHGYFS-VLSRWLAYSA-N 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
- 239000000203 mixture Substances 0.000 claims description 4
- 229960000257 tiotropium bromide Drugs 0.000 claims description 4
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 3
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 claims description 3
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 3
- 229960002848 formoterol Drugs 0.000 claims description 3
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 3
- 229960001888 ipratropium Drugs 0.000 claims description 3
- OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 claims description 3
- 229960002052 salbutamol Drugs 0.000 claims description 3
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- 150000003839 salts Chemical class 0.000 claims description 3
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- 229960002537 betamethasone 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
- 229960004648 betamethasone acetate Drugs 0.000 claims description 2
- AKUJBENLRBOFTD-QZIXMDIESA-N betamethasone acetate 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)COC(C)=O)(O)[C@@]1(C)C[C@@H]2O AKUJBENLRBOFTD-QZIXMDIESA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229960002714 fluticasone Drugs 0.000 claims description 2
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims description 2
- 229960000890 hydrocortisone Drugs 0.000 claims description 2
- 229960001067 hydrocortisone acetate Drugs 0.000 claims description 2
- 229960001664 mometasone Drugs 0.000 claims description 2
- QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical group C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 claims description 2
- 229960002744 mometasone furoate Drugs 0.000 claims description 2
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical group 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 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 claims description 2
- 229960005018 salmeterol xinafoate Drugs 0.000 claims description 2
- 229940110309 tiotropium Drugs 0.000 claims description 2
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 claims description 2
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims 2
- 229960004436 budesonide Drugs 0.000 claims 2
- 230000000699 topical effect Effects 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- MQLXPRBEAHBZTK-SEINRUQRSA-M tiotropium bromide hydrate Chemical compound O.[Br-].C[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 MQLXPRBEAHBZTK-SEINRUQRSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 22
- 238000010951 particle size reduction Methods 0.000 description 13
- 230000008569 process Effects 0.000 description 11
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- 239000011521 glass Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- -1 mometasone furoate Chemical class 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
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- 238000001238 wet grinding Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
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- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 238000004497 NIR spectroscopy Methods 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
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- GVLGAFRNYJVHBC-UHFFFAOYSA-N hydrate;hydrobromide Chemical compound O.Br GVLGAFRNYJVHBC-UHFFFAOYSA-N 0.000 description 1
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- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- CBHOWTTXCQAOID-UHFFFAOYSA-L sodium ethane formaldehyde mercury(2+) molecular iodine 2-sulfidobenzoate Chemical compound [Na+].[Hg++].C[CH2-].II.C=O.[O-]C(=O)c1ccccc1[S-] CBHOWTTXCQAOID-UHFFFAOYSA-L 0.000 description 1
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- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61J—CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE
- A61J3/00—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms
- A61J3/02—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms into the form of powders
-
- 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
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- 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
-
- 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
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- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT105058 | 2010-04-21 | ||
| PT105058A PT105058B (pt) | 2010-04-21 | 2010-04-21 | Processo para processamento de partículas de ingredientes activos farmacêuticos |
| PCT/GB2011/000631 WO2011131947A2 (en) | 2010-04-21 | 2011-04-21 | A process for particle processing of active pharmaceutical ingredients |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012149459A RU2012149459A (ru) | 2014-05-27 |
| RU2597790C2 true RU2597790C2 (ru) | 2016-09-20 |
Family
ID=44194836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012149459/15A RU2597790C2 (ru) | 2010-04-21 | 2011-04-21 | Способ обработки частиц активных фармацевтических ингредиентов |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9956144B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2560620B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP6347608B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102970978B (cg-RX-API-DMAC7.html) |
| BR (1) | BR112012026941A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2796978C (cg-RX-API-DMAC7.html) |
| IL (1) | IL222596B (cg-RX-API-DMAC7.html) |
| MX (1) | MX338594B (cg-RX-API-DMAC7.html) |
| PL (1) | PL2560620T3 (cg-RX-API-DMAC7.html) |
| PT (1) | PT105058B (cg-RX-API-DMAC7.html) |
| RU (1) | RU2597790C2 (cg-RX-API-DMAC7.html) |
| SG (1) | SG185003A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011131947A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8691145B2 (en) | 2009-11-16 | 2014-04-08 | Flodesign Sonics, Inc. | Ultrasound and acoustophoresis for water purification |
| US10993879B2 (en) | 2010-02-08 | 2021-05-04 | Shenzhen Evergreen Therapeutics Co., Ltd. | Pulmonary delivery of progestogen |
| US10987361B2 (en) | 2010-02-08 | 2021-04-27 | Shenzhen Evergreen Therapeutics Co., Ltd. | Treating auto-immune and auto-inflammatory diseases |
| CN102811730B (zh) | 2010-02-08 | 2014-07-09 | 杜涛 | 孕激素作为糖皮质激素增敏剂的使用 |
| US9421553B2 (en) | 2010-08-23 | 2016-08-23 | Flodesign Sonics, Inc. | High-volume fast separation of multi-phase components in fluid suspensions |
| US10322949B2 (en) | 2012-03-15 | 2019-06-18 | Flodesign Sonics, Inc. | Transducer and reflector configurations for an acoustophoretic device |
| US9796956B2 (en) | 2013-11-06 | 2017-10-24 | Flodesign Sonics, Inc. | Multi-stage acoustophoresis device |
| US9688958B2 (en) | 2012-03-15 | 2017-06-27 | Flodesign Sonics, Inc. | Acoustic bioreactor processes |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN102970978B (zh) | 2017-05-10 |
| BR112012026941A2 (pt) | 2016-07-12 |
| SG185003A1 (en) | 2012-11-29 |
| MX338594B (es) | 2016-04-25 |
| EP2560620B1 (en) | 2020-09-16 |
| CN102970978A (zh) | 2013-03-13 |
| WO2011131947A3 (en) | 2012-01-05 |
| JP6857467B2 (ja) | 2021-04-14 |
| JP6347608B2 (ja) | 2018-06-27 |
| JP2017019845A (ja) | 2017-01-26 |
| IL222596B (en) | 2019-03-31 |
| PL2560620T3 (pl) | 2021-04-06 |
| WO2011131947A2 (en) | 2011-10-27 |
| US20130203717A1 (en) | 2013-08-08 |
| PT105058A (pt) | 2011-10-21 |
| EP2560620A2 (en) | 2013-02-27 |
| CA2796978C (en) | 2019-07-02 |
| MX2012012215A (es) | 2013-05-09 |
| JP2013525338A (ja) | 2013-06-20 |
| CA2796978A1 (en) | 2011-10-27 |
| US9956144B2 (en) | 2018-05-01 |
| IL222596A0 (en) | 2012-12-31 |
| PT105058B (pt) | 2013-04-17 |
| RU2012149459A (ru) | 2014-05-27 |
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