JP2016538574A - ジアンヒドロガラクチトール中の不純物のｈｐｌｃ分析 - Google Patents
ジアンヒドロガラクチトール中の不純物のｈｐｌｃ分析 Download PDFInfo
- Publication number
- JP2016538574A JP2016538574A JP2016554543A JP2016554543A JP2016538574A JP 2016538574 A JP2016538574 A JP 2016538574A JP 2016554543 A JP2016554543 A JP 2016554543A JP 2016554543 A JP2016554543 A JP 2016554543A JP 2016538574 A JP2016538574 A JP 2016538574A
- Authority
- JP
- Japan
- Prior art keywords
- dianhydrogalactitol
- dulcitol
- water
- minutes
- hplc
- 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.)
- Pending
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 107
- 229950000758 dianhydrogalactitol Drugs 0.000 title claims abstract description 102
- 239000012535 impurity Substances 0.000 title claims abstract description 92
- 238000004128 high performance liquid chromatography Methods 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 58
- 238000009472 formulation Methods 0.000 claims abstract description 55
- 238000004458 analytical method Methods 0.000 claims abstract description 32
- 238000000105 evaporative light scattering detection Methods 0.000 claims abstract description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 88
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 76
- 238000010828 elution Methods 0.000 claims description 44
- 239000000523 sample Substances 0.000 claims description 44
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 38
- 235000019253 formic acid Nutrition 0.000 claims description 38
- 239000007924 injection Substances 0.000 claims description 23
- 238000002347 injection Methods 0.000 claims description 23
- 239000007857 degradation product Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- 230000014759 maintenance of location Effects 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 230000035945 sensitivity Effects 0.000 claims description 9
- 239000000539 dimer Substances 0.000 claims description 8
- 238000012546 transfer Methods 0.000 claims description 8
- 239000000356 contaminant Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 239000003480 eluent Substances 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 239000006199 nebulizer Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000012925 reference material Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims description 4
- 239000002879 Lewis base Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 238000004811 liquid chromatography Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 19
- 238000002953 preparative HPLC Methods 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract description 4
- 238000004885 tandem mass spectrometry Methods 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 22
- 239000005695 Ammonium acetate Substances 0.000 description 22
- 229940043376 ammonium acetate Drugs 0.000 description 22
- 235000019257 ammonium acetate Nutrition 0.000 description 22
- 239000012086 standard solution Substances 0.000 description 22
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 20
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 19
- 239000000908 ammonium hydroxide Substances 0.000 description 19
- 150000003863 ammonium salts Chemical class 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000001514 detection method Methods 0.000 description 14
- 238000004949 mass spectrometry Methods 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000015556 catabolic process Effects 0.000 description 9
- 238000006731 degradation reaction Methods 0.000 description 9
- 239000008186 active pharmaceutical agent Substances 0.000 description 8
- 229940126534 drug product Drugs 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 7
- 230000003595 spectral effect Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000010829 isocratic elution Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 239000012490 blank solution Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940088679 drug related substance Drugs 0.000 description 4
- 230000010354 integration Effects 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000005349 anion exchange Methods 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000013480 data collection Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 238000001448 refractive index detection Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012899 standard injection Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 238000005406 washing Methods 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
- 241000206601 Carnobacterium mobile Species 0.000 description 1
- 206010014950 Eosinophilia Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000003109 Karl Fischer titration Methods 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
- 230000004075 alteration Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 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
- 238000004440 column chromatography Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011521 glass Substances 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
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000005977 kidney dysfunction Effects 0.000 description 1
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 description 1
- 239000000832 lactitol Substances 0.000 description 1
- 229960003451 lactitol Drugs 0.000 description 1
- 235000010448 lactitol Nutrition 0.000 description 1
- 238000012886 linear function Methods 0.000 description 1
- 239000007788 liquid Substances 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
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000005336 safety glass Substances 0.000 description 1
- 239000012898 sample dilution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
-
- 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
-
- 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
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
-
- 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
-
- 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
-
- 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
- G01N30/84—Preparation of the fraction to be distributed
- G01N2030/8447—Nebulising, aerosol formation or ionisation
- G01N2030/8494—Desolvation chambers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/083,135 US9029164B2 (en) | 2012-02-27 | 2013-11-18 | Analytical methods for analyzing and determining impurities in dianhydrogalactitol |
| US14/083,135 | 2013-11-18 | ||
| PCT/US2014/066087 WO2015074025A1 (en) | 2013-11-18 | 2014-11-18 | Hplc analysis of impurities in dianhydrogalactitol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016538574A true JP2016538574A (ja) | 2016-12-08 |
| JP2016538574A5 JP2016538574A5 (es) | 2017-12-28 |
Family
ID=53058168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016554543A Pending JP2016538574A (ja) | 2013-11-18 | 2014-11-18 | ジアンヒドロガラクチトール中の不純物のｈｐｌｃ分析 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP3071555A4 (es) |
| JP (1) | JP2016538574A (es) |
| KR (1) | KR20160108315A (es) |
| CN (1) | CN107529337B (es) |
| AU (1) | AU2014348232A1 (es) |
| CA (1) | CA2931088A1 (es) |
| CL (1) | CL2016001197A1 (es) |
| IL (1) | IL245713A0 (es) |
| MX (1) | MX2016006457A (es) |
| WO (1) | WO2015074025A1 (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106397360A (zh) * | 2015-07-29 | 2017-02-15 | 广西梧州制药（集团）股份有限公司 | 叔丁醇在去水卫矛醇或其组合物冷冻干燥过程中的应用 |
| EP3380462B1 (en) | 2015-11-25 | 2021-02-17 | Del Mar Pharmaceuticals (BC) Ltd. | Methods for analysis and resolution of preparations of dianhydrogalactitol and derivatives or analogs thereof |
| CN105445407B (zh) * | 2015-12-29 | 2017-04-19 | 成都普思生物科技股份有限公司 | 一种山桐子中脂肪酸和维生素e的检测方法 |
| WO2017175694A1 (ja) * | 2016-04-04 | 2017-10-12 | 国立大学法人三重大学 | アルギン酸リアーゼ及び当該酵素を用いる不飽和ウロン酸単糖の製造方法 |
| KR102270026B1 (ko) * | 2020-01-31 | 2021-06-28 | 현대약품 주식회사 | (3s)-3-(4-(3-(1,4-다이옥사스파이로[4,5]데스-7-엔-8-일)벤질옥시)페닐)헥스-4-이노익산의 품질 평가 방법 |
| CN114113352A (zh) * | 2020-08-28 | 2022-03-01 | 深圳波顿香料有限公司 | 发酵液中内酯型槐糖酯含量的测定方法 |
Citations (11)
| 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 |
| JP2000506969A (ja) * | 1996-03-01 | 2000-06-06 | ダイオネックス コーポレイション | クロマトグラフィーでのボレートの除去 |
| WO2000042225A1 (en) * | 1999-01-14 | 2000-07-20 | Board Of Supervisors Of Louisiana State Universityand Agricultural And Mechanical College | Process for the separation of sugars |
| JP2004517131A (ja) * | 2000-11-17 | 2004-06-10 | リサーチ ディベロップメント ファンデーション | トリテルペン組成物によるＮＦ−κＢの抑制 |
| 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 |
| JP2007538251A (ja) * | 2004-05-20 | 2007-12-27 | カイロン ソチエタ ア レスポンサビリタ リミタータ | 液体クロマトグラフィー溶出液の分析 |
| 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 |
| JP2008518881A (ja) * | 2003-07-18 | 2008-06-05 | オークウッド ラボラトリーズ，エル．エル．シー． | 高分子組成物中の高分子の分子量低下、不純物形成およびゲル化の防止 |
| WO2011092120A1 (en) * | 2010-01-29 | 2011-08-04 | Nerviano Medical Sciences S.R.L. | 6,7- dihydroimidazo [1,5-a] pyrazin-8 (5h) - one derivatives as protein kinase modulators |
| WO2012024368A2 (en) * | 2010-08-18 | 2012-02-23 | Del Mar Pharmaceuticals | Method of synthesis of substituted hexitols such as dianhydrogalactitol |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2010004493A (es) * | 2007-10-25 | 2010-06-11 | Exelixis Inc | Compuestos de tropano. |
| CN102008541B (zh) * | 2010-10-08 | 2012-07-04 | 广西中医学院 | 无糖型复方扶芳藤制剂中3种主要活性成分的同时检测方法 |
| EP2820408A4 (en) * | 2012-02-27 | 2015-11-18 | Del Mar Pharmaceuticals | IMPROVED ANALYTICAL METHODS FOR ANALYZING AND DETERMINING IMPURITIES IN DIANHYDROGALACTITOL |
| BE1020835A5 (nl) * | 2012-03-20 | 2014-06-03 | Maes Francis N V | Werkwijze voor het vervaardigen van een plantenextract, i.h.b. uit desmodium. |
-
2014
- 2014-11-18 MX MX2016006457A patent/MX2016006457A/es unknown
- 2014-11-18 JP JP2016554543A patent/JP2016538574A/ja active Pending
- 2014-11-18 KR KR1020167016274A patent/KR20160108315A/ko not_active Application Discontinuation
- 2014-11-18 CN CN201480073454.XA patent/CN107529337B/zh active Active
- 2014-11-18 AU AU2014348232A patent/AU2014348232A1/en not_active Abandoned
- 2014-11-18 CA CA2931088A patent/CA2931088A1/en not_active Abandoned
- 2014-11-18 EP EP14862051.1A patent/EP3071555A4/en not_active Withdrawn
- 2014-11-18 WO PCT/US2014/066087 patent/WO2015074025A1/en active Application Filing
-
2016
- 2016-05-18 CL CL2016001197A patent/CL2016001197A1/es unknown
- 2016-05-18 IL IL245713A patent/IL245713A0/en unknown
Patent Citations (13)
| 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 |
| JP2000506969A (ja) * | 1996-03-01 | 2000-06-06 | ダイオネックス コーポレイション | クロマトグラフィーでのボレートの除去 |
| WO2000042225A1 (en) * | 1999-01-14 | 2000-07-20 | Board Of Supervisors Of Louisiana State Universityand Agricultural And Mechanical College | Process for the separation of sugars |
| JP2004517131A (ja) * | 2000-11-17 | 2004-06-10 | リサーチ ディベロップメント ファンデーション | トリテルペン組成物によるＮＦ−κＢの抑制 |
| 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 |
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| JP2007538251A (ja) * | 2004-05-20 | 2007-12-27 | カイロン ソチエタ ア レスポンサビリタ リミタータ | 液体クロマトグラフィー溶出液の分析 |
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| JP2013518072A (ja) * | 2010-01-29 | 2013-05-20 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | タンパク質キナーゼモジュレーターとしての６，７−ジヒドロイミダゾ［１，５−ａ］ピラジン−８（５ｈ）−オン誘導体 |
| WO2012024368A2 (en) * | 2010-08-18 | 2012-02-23 | Del Mar Pharmaceuticals | Method of synthesis of substituted hexitols such as dianhydrogalactitol |
| JP2013534250A (ja) * | 2010-08-18 | 2013-09-02 | デル マー ファーマスーティカルズ | ジアンヒドロガラクチトール等の置換ヘキシトールの合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3071555A4 (en) | 2017-05-31 |
| WO2015074025A9 (en) | 2015-12-17 |
| WO2015074025A1 (en) | 2015-05-21 |
| KR20160108315A (ko) | 2016-09-19 |
| EP3071555A1 (en) | 2016-09-28 |
| AU2014348232A1 (en) | 2016-06-30 |
| IL245713A0 (en) | 2016-08-02 |
| CN107529337A (zh) | 2017-12-29 |
| CL2016001197A1 (es) | 2017-06-30 |
| CN107529337B (zh) | 2021-11-16 |
| MX2016006457A (es) | 2017-01-06 |
| CA2931088A1 (en) | 2015-05-21 |
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