CA2865709A1 - Improved analytical methods for analyzing and determining impurities in dianhydrogalactitol - Google Patents
Improved analytical methods for analyzing and determining impurities in dianhydrogalactitol Download PDFInfo
- Publication number
- CA2865709A1 CA2865709A1 CA2865709A CA2865709A CA2865709A1 CA 2865709 A1 CA2865709 A1 CA 2865709A1 CA 2865709 A CA2865709 A CA 2865709A CA 2865709 A CA2865709 A CA 2865709A CA 2865709 A1 CA2865709 A1 CA 2865709A1
- Authority
- CA
- Canada
- Prior art keywords
- analytical method
- dianhydrogalactitol
- ammonium
- preparation
- group
- 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
- AAFJXZWCNVJTMK-GUCUJZIJSA-N (1s,2r)-1-[(2s)-oxiran-2-yl]-2-[(2r)-oxiran-2-yl]ethane-1,2-diol Chemical compound C([C@@H]1[C@H](O)[C@H](O)[C@H]2OC2)O1 AAFJXZWCNVJTMK-GUCUJZIJSA-N 0.000 title claims abstract description 95
- 229950000758 dianhydrogalactitol Drugs 0.000 title claims abstract description 94
- 238000004458 analytical method Methods 0.000 title claims abstract description 64
- 239000012535 impurity Substances 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 claims abstract description 70
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 34
- 239000000126 substance Substances 0.000 claims abstract description 29
- 238000002953 preparative HPLC Methods 0.000 claims abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 96
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 claims description 48
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 32
- 239000005695 Ammonium acetate Substances 0.000 claims description 32
- 229940043376 ammonium acetate Drugs 0.000 claims description 32
- 235000019257 ammonium acetate Nutrition 0.000 claims description 32
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 30
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 30
- 239000000908 ammonium hydroxide Substances 0.000 claims description 30
- 238000010828 elution Methods 0.000 claims description 30
- 238000000105 evaporative light scattering detection Methods 0.000 claims description 30
- 150000003863 ammonium salts Chemical class 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000007857 degradation product Substances 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 238000004949 mass spectrometry Methods 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 230000003595 spectral effect Effects 0.000 claims description 9
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims description 8
- 239000000356 contaminant Substances 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 7
- 230000008020 evaporation Effects 0.000 claims description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 6
- 238000005481 NMR spectroscopy Methods 0.000 claims description 6
- 150000001793 charged compounds Chemical class 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 238000003109 Karl Fischer titration Methods 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 238000000921 elemental analysis Methods 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000001514 detection method Methods 0.000 abstract description 9
- 238000004885 tandem mass spectrometry Methods 0.000 abstract description 2
- 239000000523 sample Substances 0.000 description 26
- 239000008186 active pharmaceutical agent Substances 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 229940126534 drug product Drugs 0.000 description 6
- 238000010829 isocratic elution Methods 0.000 description 6
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000010354 integration Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 4
- 229940088679 drug related substance Drugs 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- 238000005349 anion exchange Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940126600 bulk drug product Drugs 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002663 nebulization Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001448 refractive index detection Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000012899 standard injection Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
- 206010014952 Eosinophilia myalgia syndrome Diseases 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- 239000012901 Milli-Q water Substances 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010062237 Renal impairment Diseases 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000003593 chromogenic compound Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical class OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000005977 kidney dysfunction Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 230000005976 liver dysfunction Effects 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000011003 system suitability test Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/47—Scattering, i.e. diffuse reflection
- G01N21/49—Scattering, i.e. diffuse reflection within a body or fluid
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
- G01N30/7233—Mass spectrometers interfaced to liquid or supercritical fluid chromatograph
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/15—Medicinal preparations ; Physical properties thereof, e.g. dissolubility
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/027—Liquid chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
- G01N2030/743—FTIR
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/8813—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample biological materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/8872—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample impurities
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
-
- 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
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
-
- 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
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/20—Oxygen containing
- Y10T436/203332—Hydroxyl containing
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
- Spectroscopy & Molecular Physics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261603464P | 2012-02-27 | 2012-02-27 | |
| US61/603,464 | 2012-02-27 | ||
| PCT/IB2013/000793 WO2013128285A2 (en) | 2012-02-27 | 2013-02-26 | Improved analytical methods for analyzing and determining impurities in dianhydrogalactitol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2865709A1 true CA2865709A1 (en) | 2013-09-06 |
Family
ID=49083394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2865709A Abandoned CA2865709A1 (en) | 2012-02-27 | 2013-02-26 | Improved analytical methods for analyzing and determining impurities in dianhydrogalactitol |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US10145824B2 (enExample) |
| EP (1) | EP2820408A4 (enExample) |
| JP (1) | JP6223364B2 (enExample) |
| KR (1) | KR20140129306A (enExample) |
| CN (1) | CN104428664B (enExample) |
| AU (1) | AU2013227353B2 (enExample) |
| BR (1) | BR112014021163A2 (enExample) |
| CA (1) | CA2865709A1 (enExample) |
| CL (1) | CL2014002276A1 (enExample) |
| HK (1) | HK1208528A1 (enExample) |
| MX (1) | MX2014010312A (enExample) |
| SG (1) | SG11201405249QA (enExample) |
| WO (1) | WO2013128285A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104428664B (zh) | 2012-02-27 | 2018-09-21 | 德玛医药 | 用于分析和测定在卫康醇中杂质的改良分析方法 |
| EP3071555A4 (en) * | 2013-11-18 | 2017-05-31 | Del Mar Pharmaceuticals | Hplc analysis of impurities in dianhydrogalactitol |
| MX379918B (es) * | 2015-11-25 | 2025-03-11 | Del Mar Pharmaceuticals Bc Ltd | Metodos para analisis y resolucion de preparaciones de dianhidrogalactitol y derivados o analogos del mismo. |
| US10927363B2 (en) | 2016-04-04 | 2021-02-23 | Mie University | DNA sequence and expression vector for alginate lyase |
| CN106596751B (zh) * | 2016-11-04 | 2020-05-19 | 天津大学 | 一种氯代消毒副产物二氯乙酰胺和三氯乙酰胺的高效液相色谱-电喷雾质谱检测方法 |
| JP6988158B2 (ja) * | 2017-05-11 | 2022-01-05 | 株式会社島津製作所 | 液体クロマトグラフ質量分析方法及び液体クロマトグラフ質量分析装置 |
| CN108827998B (zh) * | 2018-05-30 | 2021-06-22 | 中国计量科学研究院 | 一种采用定量核磁共振氢谱准确测量易挥发性物质纯度的方法 |
| EP4022668B1 (en) * | 2019-08-30 | 2023-11-29 | DH Technologies Development Pte. Ltd. | Method for mass spectrometry |
| EP4083620B1 (en) * | 2021-04-30 | 2025-03-05 | F. Hoffmann-La Roche AG | Lc system and method with column backflushing |
| US12295919B2 (en) | 2022-03-16 | 2025-05-13 | Mie University | Methods of treatment and prevention using 4-deoxy-L-erythro-5-hexoseulose uronic acid |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04297868A (ja) * | 1991-03-27 | 1992-10-21 | Tonen Corp | オリゴ糖の分析方法 |
| JPH09229920A (ja) * | 1996-02-26 | 1997-09-05 | Kao Corp | グラジェント液体クロマトグラフィー溶離液の処理方法 |
| US6060525A (en) | 1996-03-01 | 2000-05-09 | Dionix Corporation | Removal of borate in chromatography |
| US20030060434A1 (en) | 1997-02-18 | 2003-03-27 | Loretta Nielsen | Combined tumor suppressor gene therapy and chemotherapy in the treatment of neoplasms |
| CA2359337C (en) * | 1999-01-14 | 2005-09-13 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Process for the separation of sugars |
| US20020037328A1 (en) * | 2000-06-01 | 2002-03-28 | Brown Dennis M. | Hexitol compositions and uses thereof |
| US20060148732A1 (en) * | 2000-11-17 | 2006-07-06 | Gutterman Jordan U | Inhibition of NF-kappaB by triterpene compositions |
| US20030229237A1 (en) * | 2002-04-02 | 2003-12-11 | Haas Michael J. | In situ production of fatty acid alkyl esters |
| JP2004294384A (ja) * | 2003-03-28 | 2004-10-21 | National Agriculture & Bio-Oriented Research Organization | １−デオキシノジリマイシンの測定方法 |
| CA2819769C (en) * | 2003-07-18 | 2016-06-28 | Oakwood Laboratories, L.L.C. | Prevention of molecular weight reduction of the polymer, impurity formation and gelling in polymer compositions |
| EP1747457B1 (en) * | 2004-05-20 | 2011-11-30 | Novartis AG | Analysis of liquid chromatography eluates |
| JP2008076340A (ja) * | 2006-09-25 | 2008-04-03 | Toppan Printing Co Ltd | 高感度検出方法およびその検出装置 |
| US8772279B2 (en) * | 2010-01-29 | 2014-07-08 | Nerviano Medical Sciences S.R.L. | 6,7-dihydroimidazo[1,5-a]pyrazin-8(5H)-one derivatives as protein kinase modulators |
| AU2011292045B2 (en) * | 2010-08-18 | 2016-03-24 | Del Mar Pharmaceuticals | Method of synthesis of substituted hexitols such as dianhydrogalactitol |
| US9029164B2 (en) * | 2012-02-27 | 2015-05-12 | Del Mar Pharmaceuticals | Analytical methods for analyzing and determining impurities in dianhydrogalactitol |
| CN104428664B (zh) | 2012-02-27 | 2018-09-21 | 德玛医药 | 用于分析和测定在卫康醇中杂质的改良分析方法 |
-
2013
- 2013-02-26 CN CN201380022154.4A patent/CN104428664B/zh not_active Expired - Fee Related
- 2013-02-26 JP JP2014558224A patent/JP6223364B2/ja not_active Expired - Fee Related
- 2013-02-26 MX MX2014010312A patent/MX2014010312A/es unknown
- 2013-02-26 KR KR1020147027029A patent/KR20140129306A/ko not_active Ceased
- 2013-02-26 US US14/380,924 patent/US10145824B2/en active Active
- 2013-02-26 CA CA2865709A patent/CA2865709A1/en not_active Abandoned
- 2013-02-26 BR BR112014021163-9A patent/BR112014021163A2/pt not_active Application Discontinuation
- 2013-02-26 SG SG11201405249QA patent/SG11201405249QA/en unknown
- 2013-02-26 AU AU2013227353A patent/AU2013227353B2/en not_active Ceased
- 2013-02-26 HK HK15109084.1A patent/HK1208528A1/xx unknown
- 2013-02-26 WO PCT/IB2013/000793 patent/WO2013128285A2/en not_active Ceased
- 2013-02-26 EP EP13754722.0A patent/EP2820408A4/en not_active Withdrawn
- 2013-07-02 US US13/933,844 patent/US9759698B2/en not_active Expired - Fee Related
-
2014
- 2014-08-27 CL CL2014002276A patent/CL2014002276A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2013227353A1 (en) | 2014-09-25 |
| EP2820408A2 (en) | 2015-01-07 |
| JP6223364B2 (ja) | 2017-11-01 |
| SG11201405249QA (en) | 2014-10-30 |
| CN104428664A (zh) | 2015-03-18 |
| BR112014021163A2 (pt) | 2020-10-27 |
| WO2013128285A9 (en) | 2014-02-27 |
| KR20140129306A (ko) | 2014-11-06 |
| AU2013227353B2 (en) | 2016-06-09 |
| EP2820408A4 (en) | 2015-11-18 |
| WO2013128285A2 (en) | 2013-09-06 |
| JP2015508174A (ja) | 2015-03-16 |
| CN104428664B (zh) | 2018-09-21 |
| US10145824B2 (en) | 2018-12-04 |
| US9759698B2 (en) | 2017-09-12 |
| HK1208528A1 (en) | 2016-03-04 |
| MX2014010312A (es) | 2015-04-14 |
| US20140017798A1 (en) | 2014-01-16 |
| WO2013128285A3 (en) | 2013-12-27 |
| US20150027206A1 (en) | 2015-01-29 |
| CL2014002276A1 (es) | 2014-12-19 |
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