KR20160108315A - 디안히드로갈락티톨 중의 불순물의 ｈｐｌｃ 분석 - Google Patents
디안히드로갈락티톨 중의 불순물의 ｈｐｌｃ 분석 Download PDFInfo
- Publication number
- KR20160108315A KR20160108315A KR1020167016274A KR20167016274A KR20160108315A KR 20160108315 A KR20160108315 A KR 20160108315A KR 1020167016274 A KR1020167016274 A KR 1020167016274A KR 20167016274 A KR20167016274 A KR 20167016274A KR 20160108315 A KR20160108315 A KR 20160108315A
- Authority
- KR
- South Korea
- Prior art keywords
- dianhydrogalactitol
- hplc
- water
- minutes
- formic acid
- 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.)
- Withdrawn
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 106
- 238000004128 high performance liquid chromatography Methods 0.000 title claims abstract description 101
- 239000012535 impurity Substances 0.000 title claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 88
- 238000000105 evaporative light scattering detection Methods 0.000 claims abstract description 46
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 238000009472 formulation Methods 0.000 claims abstract description 40
- 238000004458 analytical method Methods 0.000 claims abstract description 31
- 238000002360 preparation method Methods 0.000 claims abstract description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 86
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
- 238000010828 elution Methods 0.000 claims description 43
- 239000000523 sample Substances 0.000 claims description 40
- 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
- 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 26
- 239000007924 injection Substances 0.000 claims description 19
- 238000002347 injection Methods 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000539 dimer Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 230000035945 sensitivity Effects 0.000 claims description 8
- 239000000356 contaminant Substances 0.000 claims description 7
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims description 5
- 239000006199 nebulizer Substances 0.000 claims description 5
- 239000012925 reference material Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 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
- 238000003556 assay Methods 0.000 claims description 3
- 238000010494 dissociation reaction Methods 0.000 claims description 3
- 230000005593 dissociations Effects 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 238000004949 mass spectrometry Methods 0.000 abstract description 22
- 239000000463 material Substances 0.000 abstract description 13
- 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 21
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 20
- 239000000908 ammonium hydroxide Substances 0.000 description 20
- 150000003863 ammonium salts Chemical class 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 239000000126 substance Substances 0.000 description 16
- 238000000149 argon plasma sintering Methods 0.000 description 15
- 238000001514 detection 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
- 239000008186 active pharmaceutical agent Substances 0.000 description 9
- 239000007857 degradation product Substances 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 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
- 239000011550 stock solution Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000010829 isocratic elution Methods 0.000 description 6
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 5
- 239000012490 blank solution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000012488 sample solution Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940088679 drug related substance Drugs 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 238000005349 anion exchange Methods 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 238000001448 refractive index detection Methods 0.000 description 2
- 239000012899 standard injection Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 125000003944 tolyl group Chemical group 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
- 238000010268 HPLC based assay Methods 0.000 description 1
- 206010019663 Hepatic failure Diseases 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
- 208000001647 Renal Insufficiency 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
- 238000000889 atomisation Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000003593 chromogenic compound Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000023077 detection of light stimulus Effects 0.000 description 1
- 230000029087 digestion Effects 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
- 229930182830 galactose Natural products 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000012886 linear function Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000007903 liver failure Diseases 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000004252 protein component Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000005336 safety glass Substances 0.000 description 1
- 239000012898 sample dilution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Images
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 (1)
| Publication Number | Publication Date |
|---|---|
| KR20160108315A true KR20160108315A (ko) | 2016-09-19 |
Family
ID=53058168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167016274A Withdrawn KR20160108315A (ko) | 2013-11-18 | 2014-11-18 | 디안히드로갈락티톨 중의 불순물의 ｈｐｌｃ 분석 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP3071555A4 (enExample) |
| JP (1) | JP2016538574A (enExample) |
| KR (1) | KR20160108315A (enExample) |
| CN (1) | CN107529337B (enExample) |
| AU (1) | AU2014348232A1 (enExample) |
| CA (1) | CA2931088A1 (enExample) |
| CL (1) | CL2016001197A1 (enExample) |
| IL (1) | IL245713A0 (enExample) |
| MX (1) | MX2016006457A (enExample) |
| WO (1) | WO2015074025A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (7)
| 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 |
| 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. |
| 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 |
| US10927363B2 (en) | 2016-04-04 | 2021-02-23 | Mie University | DNA sequence and expression vector for alginate lyase |
| 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 |
| US12295919B2 (en) | 2022-03-16 | 2025-05-13 | Mie University | Methods of treatment and prevention using 4-deoxy-L-erythro-5-hexoseulose uronic acid |
| CN120741731B (zh) * | 2025-09-08 | 2025-11-14 | 天津中医药大学 | 一种基于uplc-qtrap-ms/ms检测扶芳藤或复方扶芳藤合剂中化学成分的方法 |
Family Cites Families (15)
| 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 |
| 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 |
| US20060148732A1 (en) * | 2000-11-17 | 2006-07-06 | Gutterman Jordan U | Inhibition of NF-kappaB by triterpene compositions |
| 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 |
| SI2074120T1 (sl) * | 2007-10-25 | 2010-06-30 | Exelixis Inc | Tropan spojine |
| 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 |
| 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 |
| 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 |
| 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 EP EP14862051.1A patent/EP3071555A4/en not_active Withdrawn
- 2014-11-18 JP JP2016554543A patent/JP2016538574A/ja active Pending
- 2014-11-18 WO PCT/US2014/066087 patent/WO2015074025A1/en not_active Ceased
- 2014-11-18 KR KR1020167016274A patent/KR20160108315A/ko not_active Withdrawn
- 2014-11-18 CN CN201480073454.XA patent/CN107529337B/zh not_active Expired - Fee Related
- 2014-11-18 CA CA2931088A patent/CA2931088A1/en not_active Abandoned
- 2014-11-18 AU AU2014348232A patent/AU2014348232A1/en not_active Abandoned
- 2014-11-18 MX MX2016006457A patent/MX2016006457A/es unknown
-
2016
- 2016-05-18 CL CL2016001197A patent/CL2016001197A1/es unknown
- 2016-05-18 IL IL245713A patent/IL245713A0/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2021154019A1 (ko) * | 2020-01-31 | 2021-08-05 | 주식회사 현대약품 | (3s)-3-(4-(3-(1,4-다이옥사스파이로[4,5]데스-7-엔-8-일)벤질옥시)페닐)헥스-4-이노익산의 품질 평가 방법 |
| CN115004024A (zh) * | 2020-01-31 | 2022-09-02 | 现代药品株式会社 | (3s)-3-(4-(3-(1,4-二氧杂螺环[4,5]癸-7-烯-8-基)苄氧基)苯基)己-4-炔酸的质量评价方法 |
| CN115004024B (zh) * | 2020-01-31 | 2024-04-26 | 现代药品株式会社 | (3s)-3-(4-(3-(1,4-二氧杂螺环[4,5]癸-7-烯-8-基)苄氧基)苯基)己-4-炔酸的质量评价方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CL2016001197A1 (es) | 2017-06-30 |
| IL245713A0 (en) | 2016-08-02 |
| AU2014348232A1 (en) | 2016-06-30 |
| CN107529337A (zh) | 2017-12-29 |
| JP2016538574A (ja) | 2016-12-08 |
| CN107529337B (zh) | 2021-11-16 |
| WO2015074025A1 (en) | 2015-05-21 |
| MX2016006457A (es) | 2017-01-06 |
| EP3071555A4 (en) | 2017-05-31 |
| CA2931088A1 (en) | 2015-05-21 |
| WO2015074025A9 (en) | 2015-12-17 |
| EP3071555A1 (en) | 2016-09-28 |
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