CA2840401C - Process for the preparation of fluticasone propionate form 1 - Google Patents
Process for the preparation of fluticasone propionate form 1 Download PDFInfo
- Publication number
- CA2840401C CA2840401C CA2840401A CA2840401A CA2840401C CA 2840401 C CA2840401 C CA 2840401C CA 2840401 A CA2840401 A CA 2840401A CA 2840401 A CA2840401 A CA 2840401A CA 2840401 C CA2840401 C CA 2840401C
- Authority
- CA
- Canada
- Prior art keywords
- fluticasone propionate
- solvent
- solution
- process according
- slurry
- 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.)
- Expired - Fee Related
Links
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical group 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 title claims abstract description 112
- 238000000034 method Methods 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title description 2
- 229960000289 fluticasone propionate Drugs 0.000 claims abstract description 100
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 76
- 239000002245 particle Substances 0.000 claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims description 26
- 239000002002 slurry Substances 0.000 claims description 24
- 238000001035 drying Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000005054 agglomeration Methods 0.000 claims description 3
- 230000002776 aggregation Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 43
- 238000002425 crystallisation Methods 0.000 abstract description 22
- 239000012296 anti-solvent Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 27
- 239000013078 crystal Substances 0.000 description 10
- 238000001144 powder X-ray diffraction data Methods 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 239000000556 agonist Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 229960001375 lactose Drugs 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 4
- 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 description 4
- 238000013019 agitation Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003149 muscarinic antagonist Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940112141 dry powder inhaler Drugs 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000005185 salting out Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960002848 formoterol Drugs 0.000 description 2
- 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 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010902 jet-milling Methods 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000011027 product recovery Methods 0.000 description 2
- 229960004017 salmeterol Drugs 0.000 description 2
- 229960005018 salmeterol xinafoate Drugs 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
- YREYLAVBNPACJM-UHFFFAOYSA-N 2-(tert-butylamino)-1-(2-chlorophenyl)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC=CC=C1Cl YREYLAVBNPACJM-UHFFFAOYSA-N 0.000 description 1
- LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 description 1
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
- 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 group 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 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 229960003060 bambuterol Drugs 0.000 description 1
- ANZXOIAKUNOVQU-UHFFFAOYSA-N bambuterol Chemical compound CN(C)C(=O)OC1=CC(OC(=O)N(C)C)=CC(C(O)CNC(C)(C)C)=C1 ANZXOIAKUNOVQU-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960001022 fenoterol Drugs 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005111 flow chemistry technique Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 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 description 1
- 229960001888 ipratropium Drugs 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- NVOYVOBDTVTBDX-PMEUIYRNSA-N oxitropium Chemical compound CC[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1 NVOYVOBDTVTBDX-PMEUIYRNSA-N 0.000 description 1
- 229960000797 oxitropium Drugs 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 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 description 1
- 229940110309 tiotropium Drugs 0.000 description 1
- 229960000257 tiotropium bromide Drugs 0.000 description 1
- 229960000859 tulobuterol Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161505612P | 2011-07-08 | 2011-07-08 | |
| US61/505,612 | 2011-07-08 | ||
| PCT/US2012/045660 WO2013009591A1 (en) | 2011-07-08 | 2012-07-06 | Process for the preparation of fluticasone propionate form 1 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2840401A1 CA2840401A1 (en) | 2013-01-17 |
| CA2840401C true CA2840401C (en) | 2016-05-17 |
Family
ID=47506422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2840401A Expired - Fee Related CA2840401C (en) | 2011-07-08 | 2012-07-06 | Process for the preparation of fluticasone propionate form 1 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US10370402B2 (enExample) |
| EP (1) | EP2729480A4 (enExample) |
| JP (2) | JP2014520848A (enExample) |
| KR (3) | KR20140048237A (enExample) |
| CN (2) | CN103649104A (enExample) |
| AU (1) | AU2012282936B2 (enExample) |
| CA (1) | CA2840401C (enExample) |
| MX (2) | MX376564B (enExample) |
| WO (1) | WO2013009591A1 (enExample) |
| ZA (1) | ZA201309531B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013009591A1 (en) * | 2011-07-08 | 2013-01-17 | Pfizer Limited | Process for the preparation of fluticasone propionate form 1 |
| PL3517541T3 (pl) | 2012-05-08 | 2020-12-28 | Nicox Ophthalmics, Inc. | Postać polimorficzna propionianu flutykazonu |
| WO2015118474A1 (en) * | 2014-02-07 | 2015-08-13 | Mylan Laboratories Ltd. | Process for the purification of fluticasone propionate using a ketone solvent and water as anti-solvent |
| CN111662353A (zh) * | 2019-03-05 | 2020-09-15 | 上海谷森医药有限公司 | 一种糠酸氟替卡松晶型1的制备方法 |
| CA3136619A1 (en) * | 2019-04-10 | 2020-10-15 | Eupraxia Pharmaceuticals Inc. | Process for making drug crystals of desired size distribution and morphology |
| CN110759960B (zh) * | 2019-10-30 | 2021-03-23 | 山东赛托生物科技股份有限公司 | 一种丙酸氟替卡松的精制方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CY1291A (en) | 1980-02-15 | 1985-10-18 | Glaxo Group Ltd | Androstane 17 beta carbothioates |
| GB9001635D0 (en) * | 1990-01-24 | 1990-03-21 | Ganderton David | Aerosol carriers |
| SE9501384D0 (sv) * | 1995-04-13 | 1995-04-13 | Astra Ab | Process for the preparation of respirable particles |
| GB9622173D0 (en) * | 1996-10-24 | 1996-12-18 | Glaxo Group Ltd | Particulate Products |
| GB9828721D0 (en) * | 1998-12-24 | 1999-02-17 | Glaxo Group Ltd | Novel apparatus and process |
| GB9925934D0 (en) * | 1999-11-03 | 1999-12-29 | Glaxo Group Ltd | Novel apparatus and process |
| GB0015981D0 (en) * | 2000-06-29 | 2000-08-23 | Glaxo Group Ltd | Novel process for preparing crystalline particles |
| GB0125604D0 (en) * | 2001-10-25 | 2001-12-19 | Glaxo Group Ltd | Novel process |
| GB0201400D0 (en) * | 2002-01-22 | 2002-03-13 | Glaxo Group Ltd | Novel apparatus and process |
| GB0202564D0 (en) * | 2002-02-04 | 2002-03-20 | Glaxo Group Ltd | Process |
| AU2003263575A1 (en) * | 2002-06-20 | 2004-01-06 | Sun Pharmaceutical Industries Limited | Convenient synthesis of s-fluoromethyl 6alpha, 9alpha-difluoro-11beta-hydroxy-16alpha- methyl-17alpha-propionyloxy-3-oxoandrosta-1, 4-diene-17beta-carbothioate |
| GB0315509D0 (en) | 2003-07-02 | 2003-08-06 | Meridica Ltd | Dispensing device |
| US7314516B2 (en) * | 2004-12-29 | 2008-01-01 | Five Star Technologies, Inc. | Hydrodynamic cavitation crystallization device and process |
| WO2013009591A1 (en) * | 2011-07-08 | 2013-01-17 | Pfizer Limited | Process for the preparation of fluticasone propionate form 1 |
-
2012
- 2012-07-06 WO PCT/US2012/045660 patent/WO2013009591A1/en not_active Ceased
- 2012-07-06 CN CN201280034030.3A patent/CN103649104A/zh active Pending
- 2012-07-06 EP EP12811395.8A patent/EP2729480A4/en not_active Ceased
- 2012-07-06 KR KR1020147003035A patent/KR20140048237A/ko not_active Ceased
- 2012-07-06 US US14/131,407 patent/US10370402B2/en not_active Expired - Fee Related
- 2012-07-06 AU AU2012282936A patent/AU2012282936B2/en not_active Ceased
- 2012-07-06 MX MX2014000192A patent/MX376564B/es active IP Right Grant
- 2012-07-06 KR KR1020197026105A patent/KR102163368B1/ko not_active Expired - Fee Related
- 2012-07-06 KR KR1020207028182A patent/KR20200117056A/ko not_active Ceased
- 2012-07-06 JP JP2014520224A patent/JP2014520848A/ja active Pending
- 2012-07-06 CN CN201610951505.5A patent/CN106977575A/zh active Pending
- 2012-07-06 CA CA2840401A patent/CA2840401C/en not_active Expired - Fee Related
-
2013
- 2013-12-18 ZA ZA2013/09531A patent/ZA201309531B/en unknown
-
2014
- 2014-01-07 MX MX2020011330A patent/MX2020011330A/es unknown
-
2016
- 2016-08-25 JP JP2016164301A patent/JP2017031161A/ja active Pending
-
2019
- 2019-07-29 US US16/525,111 patent/US20200024298A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR20200117056A (ko) | 2020-10-13 |
| MX2014000192A (es) | 2014-04-25 |
| JP2017031161A (ja) | 2017-02-09 |
| ZA201309531B (en) | 2014-08-27 |
| US20140141247A1 (en) | 2014-05-22 |
| KR102163368B1 (ko) | 2020-10-08 |
| WO2013009591A1 (en) | 2013-01-17 |
| AU2012282936A1 (en) | 2014-01-16 |
| US10370402B2 (en) | 2019-08-06 |
| AU2012282936B2 (en) | 2016-11-10 |
| KR20190107165A (ko) | 2019-09-18 |
| CA2840401A1 (en) | 2013-01-17 |
| EP2729480A1 (en) | 2014-05-14 |
| CN106977575A (zh) | 2017-07-25 |
| MX2020011330A (es) | 2020-11-24 |
| US20200024298A1 (en) | 2020-01-23 |
| EP2729480A4 (en) | 2014-12-31 |
| KR20140048237A (ko) | 2014-04-23 |
| JP2014520848A (ja) | 2014-08-25 |
| CN103649104A (zh) | 2014-03-19 |
| MX376564B (es) | 2025-03-07 |
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