CA2749101A1 - Novel forms of bendamustine free base - Google Patents
Novel forms of bendamustine free base Download PDFInfo
- Publication number
- CA2749101A1 CA2749101A1 CA2749101A CA2749101A CA2749101A1 CA 2749101 A1 CA2749101 A1 CA 2749101A1 CA 2749101 A CA2749101 A CA 2749101A CA 2749101 A CA2749101 A CA 2749101A CA 2749101 A1 CA2749101 A1 CA 2749101A1
- Authority
- CA
- Canada
- Prior art keywords
- free base
- bendamustine free
- crystalline form
- bendamustine
- diffraction pattern
- 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.)
- Abandoned
Links
- YTKUWDBFDASYHO-UHFFFAOYSA-N bendamustine Chemical compound ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(O)=O)=NC2=C1 YTKUWDBFDASYHO-UHFFFAOYSA-N 0.000 title claims abstract description 466
- 238000002360 preparation method Methods 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 98
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- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 4
- 239000012453 solvate Substances 0.000 abstract description 8
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- 239000002904 solvent Substances 0.000 description 35
- 239000007787 solid Substances 0.000 description 33
- 238000002441 X-ray diffraction Methods 0.000 description 31
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- 238000002474 experimental method Methods 0.000 description 29
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
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- 229960001215 bendamustine hydrochloride Drugs 0.000 description 4
- 235000021028 berry Nutrition 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
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- 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 3
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- 239000012043 crude product Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 229960002433 cysteine Drugs 0.000 description 1
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- GVLZDNWNOBSNEN-UHFFFAOYSA-N ethyl 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoate Chemical compound ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(=O)OCC)=NC2=C1 GVLZDNWNOBSNEN-UHFFFAOYSA-N 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
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- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
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- 230000036541 health Effects 0.000 description 1
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- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229940027278 hetastarch Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
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- 239000008101 lactose Substances 0.000 description 1
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- 239000006193 liquid solution Substances 0.000 description 1
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- 238000012792 lyophilization process Methods 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
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- 230000001766 physiological effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
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- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14484309P | 2009-01-15 | 2009-01-15 | |
| US61/144,843 | 2009-01-15 | ||
| PCT/US2010/020992 WO2010083276A1 (en) | 2009-01-15 | 2010-01-14 | Novel forms of bendamustine free base |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2749101A1 true CA2749101A1 (en) | 2010-07-22 |
Family
ID=42008533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2749101A Abandoned CA2749101A1 (en) | 2009-01-15 | 2010-01-14 | Novel forms of bendamustine free base |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8076366B2 (enExample) |
| EP (1) | EP2387400A1 (enExample) |
| JP (1) | JP2012515210A (enExample) |
| KR (1) | KR20110110293A (enExample) |
| CN (2) | CN103554030A (enExample) |
| AU (2) | AU2010204765A1 (enExample) |
| BR (1) | BRPI1004922A2 (enExample) |
| CA (1) | CA2749101A1 (enExample) |
| EA (1) | EA020767B1 (enExample) |
| IL (1) | IL213725A0 (enExample) |
| MX (1) | MX2011007557A (enExample) |
| NZ (1) | NZ594010A (enExample) |
| SG (1) | SG172810A1 (enExample) |
| UA (1) | UA109109C2 (enExample) |
| WO (1) | WO2010083276A1 (enExample) |
| ZA (1) | ZA201105099B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2516404A4 (en) * | 2009-12-23 | 2013-04-17 | Reddys Lab Ltd Dr | PREPARATION OF BENDAMUSTINE AND ITS SALTS |
| PL3158991T3 (pl) | 2010-01-28 | 2021-09-27 | Eagle Pharmaceuticals, Inc. | Preparaty bendamustyny |
| EP2720547A4 (en) * | 2011-06-20 | 2014-11-05 | Hetero Research Foundation | PROCESS FOR BENDAMUSTINE HYDROCHLORIDE |
| US20230241218A1 (en) * | 2012-07-10 | 2023-08-03 | Eagle Pharmaceuticals, Inc. | Formulations of bendamustine |
| EP2827863B1 (en) | 2012-03-20 | 2019-01-16 | Eagle Pharmaceuticals, Inc. | Liquid composition for use in a method of treating bendamustine-responsive conditions in patients requiring reduced volumes for administration |
| JP6250628B2 (ja) | 2012-03-20 | 2017-12-20 | イーグル・ファーマシューティカルズ・インコーポレーテッド | ベンダムスチンの製剤 |
| CA2904143A1 (en) | 2013-03-12 | 2014-10-09 | Cephalon, Inc. | Nanoparticulate and macroparticulate formulations |
| EP4218543A1 (en) | 2013-04-26 | 2023-08-02 | Genentech, Inc. | Contour integration perimetry vision test |
| US20240148696A1 (en) | 2022-10-25 | 2024-05-09 | Softkemo Pharma Inc. | Lyophilized bendamustine-cyclodextrin composition |
Family Cites Families (39)
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| DE80967C (enExample) | ||||
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| DD159289A1 (de) | 1981-06-01 | 1983-03-02 | Uwe Olthoff | Verfahren zur herstellung stabiler injektionsloesungen von n-lostverbindungen |
| DD159877A1 (de) * | 1981-06-12 | 1983-04-13 | Wolfgang Krueger | Verfahren zur herstellung von 4-[1-methyl-5-bis(2-chloraethyl)amino-benzimidazolyl-2]-buttersaeure |
| US5204335A (en) | 1986-10-31 | 1993-04-20 | Asta Pharma Aktiengesellschaft | Ifosfamide lyophilisate and process for its preparation |
| US5227373A (en) | 1991-10-23 | 1993-07-13 | Bristol-Myers Squibb Co. | Lyophilized ifosfamide compositions |
| DE122004000036I1 (de) | 1992-11-13 | 2005-07-07 | Biogen Idec Inc | Therapeutische Verwendung von chimerischen und markierten Antik¦rper gegen menschlichen B Lymphozyt beschr{nkter Differenzierung antigen f}r die Behandlung von B-Zell-Lymphoma. |
| US5595721A (en) | 1993-09-16 | 1997-01-21 | Coulter Pharmaceutical, Inc. | Radioimmunotherapy of lymphoma using anti-CD20 |
| WO1995011683A1 (en) | 1993-10-27 | 1995-05-04 | The Upjohn Company | Stabilized prostaglandin e¿1? |
| US5561121A (en) | 1993-11-09 | 1996-10-01 | American Cyanamid Company | Stable lyophilized thiotepa composition |
| US5955504A (en) | 1995-03-13 | 1999-09-21 | Loma Linda University Medical Center | Colorectal chemoprotective composition and method of preventing colorectal cancer |
| DE19529057B4 (de) | 1995-08-08 | 2007-12-13 | Baxter Healthcare S.A. | Ifosfamid-Lyophilisat-Zubereitungen |
| US20040072889A1 (en) | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
| US6034256A (en) | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
| US6077850A (en) | 1997-04-21 | 2000-06-20 | G.D. Searle & Co. | Substituted benzopyran analogs for the treatment of inflammation |
| AU767586B2 (en) | 1998-07-09 | 2003-11-20 | Cephalon, Inc. | Methods and compositions for the treatment of chronic lymphocytic leukemia |
| US5972912A (en) | 1998-12-17 | 1999-10-26 | S.P. Pharmaceuticals | Method for lyophilizing ifosfamide |
| US6569402B1 (en) | 1998-12-18 | 2003-05-27 | Bristol-Myers Squibb Pharma Company | Vitronectin receptor antagonist pharmaceuticals |
| US6380210B1 (en) | 1999-04-02 | 2002-04-30 | Neurogen Corporation | Heteroaryl fused aminoalkyl-imidazole derivatives: selective modulators of GABAa receptors |
| US6545034B1 (en) | 1999-07-23 | 2003-04-08 | The Regents Of The University Of California | Use of etodolac for the treatment of chronic lymphocytic leukemia |
| DE10016077A1 (de) | 2000-03-31 | 2001-12-13 | Cellcontrol Biomedical Lab Gmb | Verfahren und Vorrichtung zum automatischen Nachweisen einer Wirkung eines zellbeeinflussenden Mittels auf lebende Zellen |
| US20040152672A1 (en) | 2000-08-09 | 2004-08-05 | Carson Dennis A. | Indole compounds useful for the treatment of cancer |
| HUP0400683A2 (hu) | 2000-12-11 | 2004-06-28 | Takeda Chemical Industries, Ltd. | HER2 inhibitort tartalmazó fokozott felszívódású gyógyászati készítmény |
| CA2431319A1 (en) | 2000-12-11 | 2002-06-20 | Hiroto Bando | Pharmaceutical composition having an improved water solubility |
| BR0213279A (pt) | 2001-10-15 | 2004-10-26 | Hemoteq Gmbh | Revestimento de stents para impedir a restenose |
| US6613927B1 (en) | 2002-02-08 | 2003-09-02 | American Pharmaceutical Partners, Inc. | Sterile lyophilized ifosfamide and associated methods |
| DE10306724A1 (de) | 2002-02-28 | 2003-09-18 | G O T Therapeutics Gmbh | Vesikuläre Verkapselung von Bendamustin |
| AU2003221517B2 (en) | 2002-03-22 | 2010-02-18 | Christian Straka | Cytocapacity test |
| WO2003086470A2 (en) | 2002-04-17 | 2003-10-23 | Deutsches Krebsforschungszentrum | Smac-peptides as therapeutics against cancer and autoimmune diseases |
| EP1354952A1 (en) | 2002-04-17 | 2003-10-22 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Smac-peptides as therapeutics against cancer and autoimmune diseases |
| DE10393060D2 (de) | 2002-05-09 | 2005-05-04 | Hemoteq Gmbh | Reduktion der Schallemission von dünnwadigen Bauteilen in Magnetresonazgeräten |
| US20040096436A1 (en) | 2002-08-02 | 2004-05-20 | Regents Of The University Of California | Methods for inhibiting protein kinases in cancer cells |
| DE10304403A1 (de) | 2003-01-28 | 2004-08-05 | Röhm GmbH & Co. KG | Verfahren zur Herstellung einer oralen Arzneiform mit unmittelbarem Zerfall und Wirkstofffreisetzung |
| EP1444989A1 (en) | 2003-02-07 | 2004-08-11 | Giorgio Dr. Stassi | Sensitizing cells for apoptosis by selectively blocking cytokines |
| US7157551B2 (en) | 2003-02-14 | 2007-01-02 | Cephalon, Inc. | Compositions and methods for the detection and treatment of methylthioadenosine phosphorylase deficient cancers |
| WO2005011688A1 (en) | 2003-07-25 | 2005-02-10 | Wyeth | Cci-779 lyophilized formulations |
| US8436190B2 (en) | 2005-01-14 | 2013-05-07 | Cephalon, Inc. | Bendamustine pharmaceutical compositions |
| AU2009302493B2 (en) * | 2008-10-08 | 2015-04-09 | Cephalon Llc | Processes for the preparation of bendamustine |
-
2010
- 2010-01-14 AU AU2010204765A patent/AU2010204765A1/en not_active Abandoned
- 2010-01-14 KR KR1020117018325A patent/KR20110110293A/ko not_active Ceased
- 2010-01-14 UA UAA201109971A patent/UA109109C2/uk unknown
- 2010-01-14 MX MX2011007557A patent/MX2011007557A/es active IP Right Grant
- 2010-01-14 SG SG2011047875A patent/SG172810A1/en unknown
- 2010-01-14 NZ NZ594010A patent/NZ594010A/xx unknown
- 2010-01-14 CN CN201310425128.8A patent/CN103554030A/zh active Pending
- 2010-01-14 WO PCT/US2010/020992 patent/WO2010083276A1/en not_active Ceased
- 2010-01-14 CA CA2749101A patent/CA2749101A1/en not_active Abandoned
- 2010-01-14 EA EA201170934A patent/EA020767B1/ru not_active IP Right Cessation
- 2010-01-14 BR BRPI1004922A patent/BRPI1004922A2/pt not_active IP Right Cessation
- 2010-01-14 CN CN201080004743.6A patent/CN102281877B/zh not_active Expired - Fee Related
- 2010-01-14 JP JP2011546322A patent/JP2012515210A/ja active Pending
- 2010-01-14 US US12/687,398 patent/US8076366B2/en not_active Expired - Fee Related
- 2010-01-14 EP EP10701071A patent/EP2387400A1/en not_active Withdrawn
-
2011
- 2011-06-22 IL IL213725A patent/IL213725A0/en unknown
- 2011-07-11 ZA ZA2011/05099A patent/ZA201105099B/en unknown
-
2016
- 2016-07-13 AU AU2016204902A patent/AU2016204902A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR20110110293A (ko) | 2011-10-06 |
| WO2010083276A1 (en) | 2010-07-22 |
| ZA201105099B (en) | 2012-03-28 |
| IL213725A0 (en) | 2011-07-31 |
| AU2016204902A1 (en) | 2016-08-04 |
| EA020767B1 (ru) | 2015-01-30 |
| EA201170934A1 (ru) | 2011-12-30 |
| SG172810A1 (en) | 2011-08-29 |
| JP2012515210A (ja) | 2012-07-05 |
| BRPI1004922A2 (pt) | 2019-09-24 |
| US20100210701A1 (en) | 2010-08-19 |
| EP2387400A1 (en) | 2011-11-23 |
| CN102281877B (zh) | 2014-07-23 |
| US8076366B2 (en) | 2011-12-13 |
| NZ594010A (en) | 2013-08-30 |
| CN102281877A (zh) | 2011-12-14 |
| AU2010204765A1 (en) | 2011-07-28 |
| MX2011007557A (es) | 2011-08-12 |
| CN103554030A (zh) | 2014-02-05 |
| UA109109C2 (uk) | 2015-07-27 |
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| Date | Code | Title | Description |
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Effective date: 20160114 |