ES2610216T3 - Sólidos cristalinos de un inhibidor de METAP-2 y métodos para fabricar y usar los mismos - Google Patents
Sólidos cristalinos de un inhibidor de METAP-2 y métodos para fabricar y usar los mismos Download PDFInfo
- Publication number
- ES2610216T3 ES2610216T3 ES11788684.6T ES11788684T ES2610216T3 ES 2610216 T3 ES2610216 T3 ES 2610216T3 ES 11788684 T ES11788684 T ES 11788684T ES 2610216 T3 ES2610216 T3 ES 2610216T3
- Authority
- ES
- Spain
- Prior art keywords
- approximately
- crystalline
- dimethylaminoethoxy
- cinnamoyl
- fumagylol
- 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.)
- Active
Links
- 239000007787 solid Substances 0.000 title description 7
- 238000000034 method Methods 0.000 title description 5
- 239000003112 inhibitor Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 cinnamoyl Chemical group 0.000 abstract description 16
- 239000012458 free base Substances 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 5
- 238000002441 X-ray diffraction Methods 0.000 abstract description 3
- 239000000843 powder Substances 0.000 abstract description 2
- 239000000725 suspension Substances 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002178 crystalline material Substances 0.000 description 5
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000001907 polarising light microscopy Methods 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 229940028444 muse Drugs 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 101000979001 Homo sapiens Methionine aminopeptidase 2 Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 208000004554 Leishmaniasis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102100023174 Methionine aminopeptidase 2 Human genes 0.000 description 1
- 201000000090 Microsporidiosis Diseases 0.000 description 1
- MSHZHSPISPJWHW-UHFFFAOYSA-N O-(chloroacetylcarbamoyl)fumagillol Chemical class O1C(CC=C(C)C)C1(C)C1C(OC)C(OC(=O)NC(=O)CCl)CCC21CO2 MSHZHSPISPJWHW-UHFFFAOYSA-N 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- 108010026552 Proteome Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ZKEMUPZLDSXZCX-CEVDDVLHSA-N [(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] (E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]prop-2-enoate oxalic acid Chemical compound OC(=O)C(O)=O.C([C@H]([C@H]([C@@H]1[C@]2(C)[C@H](O2)CC=C(C)C)OC)OC(=O)\C=C\C=2C=CC(OCCN(C)C)=CC=2)C[C@@]21CO2.C([C@H]([C@H]([C@@H]1[C@]2(C)[C@H](O2)CC=C(C)C)OC)OC(=O)\C=C\C=2C=CC(OCCN(C)C)=CC=2)C[C@@]21CO2 ZKEMUPZLDSXZCX-CEVDDVLHSA-N 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 102000006602 glyceraldehyde-3-phosphate dehydrogenase Human genes 0.000 description 1
- 108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/336—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having three-membered rings, e.g. oxirane, fumagillin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41165510P | 2010-11-09 | 2010-11-09 | |
| US411655P | 2010-11-09 | ||
| PCT/US2011/059966 WO2012064838A1 (en) | 2010-11-09 | 2011-11-09 | Crystalline solids of a metap-2 inhibitor and methods of making and using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2610216T3 true ES2610216T3 (es) | 2017-04-26 |
Family
ID=45048246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11788684.6T Active ES2610216T3 (es) | 2010-11-09 | 2011-11-09 | Sólidos cristalinos de un inhibidor de METAP-2 y métodos para fabricar y usar los mismos |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US8349891B2 (enExample) |
| EP (1) | EP2638023B1 (enExample) |
| JP (1) | JP6239977B2 (enExample) |
| KR (1) | KR101892768B1 (enExample) |
| CN (2) | CN106905267A (enExample) |
| AU (1) | AU2011326566B2 (enExample) |
| BR (1) | BR112013011550A2 (enExample) |
| CA (1) | CA2817199C (enExample) |
| EA (1) | EA029941B1 (enExample) |
| ES (1) | ES2610216T3 (enExample) |
| IL (1) | IL226238B (enExample) |
| MX (1) | MX2013005208A (enExample) |
| MY (1) | MY177039A (enExample) |
| NZ (1) | NZ610569A (enExample) |
| PH (1) | PH12013500934A1 (enExample) |
| SG (1) | SG190688A1 (enExample) |
| UA (1) | UA111479C2 (enExample) |
| WO (1) | WO2012064838A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2731020A1 (en) * | 2008-07-18 | 2010-01-21 | Zafgen, Inc. | Use of antiangiogenic fumagillins in the treatment of obesity |
| US20120004162A1 (en) | 2008-12-04 | 2012-01-05 | Vath James E | Methods of Treating an Overweight or Obese Subject |
| WO2010065883A2 (en) | 2008-12-04 | 2010-06-10 | Zafgen Corporation | Method of treating an overweight or obese subject |
| KR20120083905A (ko) | 2009-10-09 | 2012-07-26 | 자프겐 코포레이션 | 비만의 치료에 사용하기 위한 설폰 화합물 |
| CA2786603C (en) | 2010-01-08 | 2018-02-20 | James E. Vath | Fumagillol type compounds and methods of making and using same |
| WO2011085198A1 (en) | 2010-01-08 | 2011-07-14 | Zafgen Corporation | Metap-2 inhibitor for use in treating benign prostatic hypertrophy (bph) |
| WO2011127304A2 (en) | 2010-04-07 | 2011-10-13 | Zafgen Corporation | Methods of treating an overweight subject |
| US9320805B2 (en) | 2010-05-25 | 2016-04-26 | Syndevrx, Inc. | Polymer-conjugated MetAP2 inhibitors, and therapeutic methods of use thereof |
| US9895449B2 (en) | 2010-05-25 | 2018-02-20 | Syndevrx, Inc. | Polymer-conjugated MetAP2 inhibitors, and therapeutic methods of use thereof |
| KR20130043207A (ko) | 2010-07-22 | 2013-04-29 | 자프겐 인크. | 트리시클릭 화합물 및 이의 제조 및 사용 방법 |
| PH12013500934A1 (en) | 2010-11-09 | 2022-10-24 | Zafgen Inc | Crystalline solids of a metap-2 inhibitor and methods of making and using same |
| CA2819251A1 (en) | 2010-11-29 | 2012-06-07 | Zafgen Corporation | Treatment of obesity using non-daily administration of 6 - 0 - (4 - dimethylaminoethoxy) cinnamoyl fumagillol |
| CA2825408A1 (en) | 2011-01-26 | 2012-08-02 | Zafgen, Inc. | Tetrazole compounds and methods of making and using same |
| KR101979039B1 (ko) | 2011-05-06 | 2019-05-15 | 자프겐 인크. | 부분 포화된 삼환식 화합물 및 그리고 그의 제조방법 및 그를 이용하는 방법 |
| BR112013028666A2 (pt) | 2011-05-06 | 2017-08-08 | Zafgen Inc | compostos de pirazolo sulfonamida tricícilos e métodos para fazer e usar o mesmo |
| BR112013028665A2 (pt) | 2011-05-06 | 2016-09-06 | Zafgen Inc | compostos de sulfonamida tricíclicos e métodos para fazer e usar os mesmos |
| EP2763671A2 (en) | 2011-10-03 | 2014-08-13 | Zafgen, Inc. | Methods of treating age related disorders |
| BR112014017673A8 (pt) | 2012-01-18 | 2017-07-11 | Zafgen Inc | Compostos de sulfonamida tricíclicos e métodos para fazer e usar os mesmos |
| EP2804856B1 (en) | 2012-01-18 | 2017-03-15 | Zafgen, Inc. | Tricyclic sulfone compounds and methods of making and using same |
| EP2847176A1 (en) | 2012-05-07 | 2015-03-18 | Zafgen, Inc. | Polymorphic salt of the oxalate salt of 6 - o - ( 4 - dimethylaminoethoxy) cinnarnoyl fumagillol and methods of making and using same |
| BR112014028041A2 (pt) | 2012-05-08 | 2017-06-27 | Zafgen Inc | tratamento de obesidade hipotalâmica com inibidores de metap2 |
| CA2873574A1 (en) | 2012-05-09 | 2013-11-14 | Zafgen, Inc. | Fumagillol type compounds and methods of making and using same |
| CN104918615B (zh) | 2012-11-05 | 2018-10-12 | 扎夫根股份有限公司 | 治疗肝病的方法 |
| BR112015010225A2 (pt) | 2012-11-05 | 2017-07-11 | Zafgen Inc | compostos tricíclicos e seus métodos de produção e utilização |
| US9868717B2 (en) | 2012-11-05 | 2018-01-16 | Zafgen, Inc. | Tricyclic sulphonamide compounds and methods of making and using same |
| WO2014118180A1 (en) * | 2013-01-30 | 2014-08-07 | Sandoz Ag | Crystalline form of linaclotide |
| PT2958916T (pt) * | 2013-02-21 | 2018-11-21 | Pfizer | Formas sólidas de um inibidor de cdk4/6 seletivo |
| AU2014236528A1 (en) | 2013-03-14 | 2015-09-24 | Zafgen, Inc. | Methods of treating renal disease and other disorders |
| BR112015025892A2 (pt) | 2013-04-10 | 2017-07-25 | Syndevrx Inc | inibidores de metap2 e métodos para tratar obesidade |
| AR101608A1 (es) * | 2014-08-22 | 2016-12-28 | Zafgen Inc | Formulaciones que contienen un inhibidor de metap-2 |
| CN106432255A (zh) | 2015-08-11 | 2017-02-22 | 扎夫根公司 | 烟曲霉素醇螺环化合物和制备和使用其的方法 |
| AR105671A1 (es) | 2015-08-11 | 2017-10-25 | Zafgen Inc | Compuestos heterocíclicos de fumagillol y sus métodos de elaboración y uso |
| KR102849342B1 (ko) | 2015-12-10 | 2025-08-21 | 신데브알엑스, 인크. | 푸마길롤 유도체 및 그의 다형체 |
| KR20180100663A (ko) | 2016-01-11 | 2018-09-11 | 신데브알엑스, 인크. | 대사 기능장애에 의하여 유도된 종양에 대한 치료 |
| JP2022512826A (ja) | 2018-10-26 | 2022-02-07 | シンデブルックス，インコーポレイティド | ＭｅｔＡＰ２阻害剤のバイオマーカーとその応用 |
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-
2010
- 2010-11-09 PH PH1/2013/500934A patent/PH12013500934A1/en unknown
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2011
- 2011-11-09 KR KR1020137014698A patent/KR101892768B1/ko not_active Expired - Fee Related
- 2011-11-09 MX MX2013005208A patent/MX2013005208A/es active IP Right Grant
- 2011-11-09 SG SG2013035225A patent/SG190688A1/en unknown
- 2011-11-09 BR BR112013011550A patent/BR112013011550A2/pt not_active Application Discontinuation
- 2011-11-09 JP JP2013538848A patent/JP6239977B2/ja not_active Expired - Fee Related
- 2011-11-09 UA UAA201307189A patent/UA111479C2/uk unknown
- 2011-11-09 ES ES11788684.6T patent/ES2610216T3/es active Active
- 2011-11-09 EP EP11788684.6A patent/EP2638023B1/en active Active
- 2011-11-09 AU AU2011326566A patent/AU2011326566B2/en not_active Ceased
- 2011-11-09 WO PCT/US2011/059966 patent/WO2012064838A1/en not_active Ceased
- 2011-11-09 EA EA201390675A patent/EA029941B1/ru not_active IP Right Cessation
- 2011-11-09 CN CN201710158431.4A patent/CN106905267A/zh active Pending
- 2011-11-09 NZ NZ610569A patent/NZ610569A/en not_active IP Right Cessation
- 2011-11-09 CN CN2011800600503A patent/CN103347870A/zh active Pending
- 2011-11-09 MY MYPI2013001644A patent/MY177039A/en unknown
- 2011-11-09 CA CA2817199A patent/CA2817199C/en not_active Expired - Fee Related
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2012
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- 2012-11-16 US US13/679,310 patent/US8735447B2/en not_active Expired - Fee Related
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2013
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2014
- 2014-02-12 US US14/178,788 patent/US9371312B2/en not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2638023A1 (en) | 2013-09-18 |
| AU2011326566A1 (en) | 2013-05-30 |
| IL226238A0 (en) | 2013-07-31 |
| KR101892768B1 (ko) | 2018-08-28 |
| CA2817199C (en) | 2019-01-15 |
| JP2013543867A (ja) | 2013-12-09 |
| EA029941B1 (ru) | 2018-06-29 |
| WO2012064838A1 (en) | 2012-05-18 |
| US8735447B2 (en) | 2014-05-27 |
| US8349891B2 (en) | 2013-01-08 |
| NZ610569A (en) | 2015-06-26 |
| US20170087119A1 (en) | 2017-03-30 |
| MX2013005208A (es) | 2013-08-01 |
| MY177039A (en) | 2020-09-03 |
| PH12013500934A1 (en) | 2022-10-24 |
| CN103347870A (zh) | 2013-10-09 |
| CA2817199A1 (en) | 2012-05-18 |
| US20150018413A1 (en) | 2015-01-15 |
| CN106905267A (zh) | 2017-06-30 |
| IL226238B (en) | 2019-02-28 |
| US20130197078A1 (en) | 2013-08-01 |
| EA201390675A1 (ru) | 2013-08-30 |
| JP6239977B2 (ja) | 2017-11-29 |
| EP2638023B1 (en) | 2016-09-07 |
| KR20140009994A (ko) | 2014-01-23 |
| UA111479C2 (uk) | 2016-05-10 |
| US20120316233A1 (en) | 2012-12-13 |
| SG190688A1 (en) | 2013-07-31 |
| US9827221B2 (en) | 2017-11-28 |
| BR112013011550A2 (pt) | 2017-10-24 |
| AU2011326566B2 (en) | 2016-12-01 |
| US9371312B2 (en) | 2016-06-21 |
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