CN106706818A - 一种依折麦布中间体光学纯度测定方法 - Google Patents
一种依折麦布中间体光学纯度测定方法 Download PDFInfo
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- CN106706818A CN106706818A CN201510782834.7A CN201510782834A CN106706818A CN 106706818 A CN106706818 A CN 106706818A CN 201510782834 A CN201510782834 A CN 201510782834A CN 106706818 A CN106706818 A CN 106706818A
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- ezetimibe
- optical purity
- ezetimibe intermediate
- mobile phase
- measuring
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- XXSSRSVXDNUAQX-QGZVFWFLSA-N 1-(4-fluorophenyl)-5-[(4s)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]pentane-1,5-dione Chemical compound C1=CC(F)=CC=C1C(=O)CCCC(=O)N1C(=O)OC[C@@H]1C1=CC=CC=C1 XXSSRSVXDNUAQX-QGZVFWFLSA-N 0.000 title claims abstract description 31
- 230000003287 optical effect Effects 0.000 title claims abstract description 22
- 238000000691 measurement method Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 16
- OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 claims abstract description 10
- 229960000815 ezetimibe Drugs 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 238000010606 normalization Methods 0.000 claims abstract description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- AVKAJIUWUFOCCN-UHFFFAOYSA-N dichloromethane;ethanol;hexane Chemical compound CCO.ClCCl.CCCCCC AVKAJIUWUFOCCN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000945 filler Substances 0.000 claims abstract description 3
- 238000000926 separation method Methods 0.000 claims abstract description 3
- PJTGFNAHESRDIO-UHFFFAOYSA-N (3-chloro-4-methylphenyl)carbamic acid Chemical compound CC1=CC=C(NC(O)=O)C=C1Cl PJTGFNAHESRDIO-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000741 silica gel Substances 0.000 claims abstract 2
- 229910002027 silica gel Inorganic materials 0.000 claims abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 14
- 150000007524 organic acids Chemical class 0.000 claims description 12
- 238000001514 detection method Methods 0.000 claims description 10
- 238000003556 assay Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 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 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims 1
- 239000012467 final product Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000007983 Tris buffer Substances 0.000 abstract 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 235000013305 food Nutrition 0.000 description 3
- 239000003814 drug Substances 0.000 description 2
- 235000006694 eating habits Nutrition 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- -1 chloro- 4- methyl phenyl carbamates Chemical class 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000000813 small intestine Anatomy 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
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- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (9)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510782834.7A CN106706818B (zh) | 2015-11-13 | 2015-11-13 | 一种依折麦布中间体光学纯度测定方法 |
PCT/CN2015/098886 WO2017080046A1 (zh) | 2015-11-13 | 2015-12-25 | 一种依折麦布中间体光学纯度测定方法 |
Applications Claiming Priority (1)
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CN201510782834.7A CN106706818B (zh) | 2015-11-13 | 2015-11-13 | 一种依折麦布中间体光学纯度测定方法 |
Publications (2)
Publication Number | Publication Date |
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CN106706818A true CN106706818A (zh) | 2017-05-24 |
CN106706818B CN106706818B (zh) | 2018-08-03 |
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CN201510782834.7A Expired - Fee Related CN106706818B (zh) | 2015-11-13 | 2015-11-13 | 一种依折麦布中间体光学纯度测定方法 |
Country Status (2)
Country | Link |
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CN (1) | CN106706818B (zh) |
WO (1) | WO2017080046A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107677753A (zh) * | 2017-11-24 | 2018-02-09 | 中山奕安泰医药科技有限公司 | 一种依替米贝中间体的检测方法 |
CN107764890A (zh) * | 2017-10-16 | 2018-03-06 | 杭州先导医药科技有限责任公司 | 一种依折麦布对映异构体的区分检测方法 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114236000B (zh) * | 2021-12-13 | 2023-03-17 | 山东省药学科学院 | 一种测定依折麦布中脱氟杂质的高效液相色谱方法 |
CN115389655B (zh) * | 2022-08-11 | 2024-04-09 | 唯智医药科技(北京)有限公司 | 6-甲醛基-2,2二甲基-1,3-二氧六环-4-乙酸叔丁酯异构体杂质检测 |
CN115453004B (zh) * | 2022-10-08 | 2023-10-13 | 南京科默生物医药有限公司 | 一种依折麦布阿托伐他汀钙片中有关物质的检测方法 |
Citations (6)
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---|---|---|---|---|
US20070049748A1 (en) * | 2005-08-26 | 2007-03-01 | Uppala Venkata Bhaskara R | Preparation of ezetimibe |
WO2008096372A2 (en) * | 2007-02-06 | 2008-08-14 | Ind-Swift Laboratories Limited | Process for preparing highly pure ezetimibe using novel intermediates |
CN103207248A (zh) * | 2012-12-21 | 2013-07-17 | 北京万全德众医药生物技术有限公司 | 一种用高效液相色谱法分离依折麦布中间体光学异构体的方法 |
CN103760281A (zh) * | 2014-01-14 | 2014-04-30 | 北京万全德众医药生物技术有限公司 | 一种液相方法分离依折麦布光学异构体的方法 |
CN104764825A (zh) * | 2015-04-11 | 2015-07-08 | 常州亚邦制药有限公司 | 依折麦布关键中间体的对映异构体的分离检测方法 |
CN104977368A (zh) * | 2014-04-02 | 2015-10-14 | 天津药物研究院 | 一种4-[(4-氟苯基亚胺)甲基]-苯酚的有关物质检测方法及其应用 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103760282A (zh) * | 2014-01-14 | 2014-04-30 | 北京万全德众医药生物技术有限公司 | 一种用液相色谱法分离测定依折麦布中间体有关物质的方法 |
-
2015
- 2015-11-13 CN CN201510782834.7A patent/CN106706818B/zh not_active Expired - Fee Related
- 2015-12-25 WO PCT/CN2015/098886 patent/WO2017080046A1/zh active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070049748A1 (en) * | 2005-08-26 | 2007-03-01 | Uppala Venkata Bhaskara R | Preparation of ezetimibe |
WO2008096372A2 (en) * | 2007-02-06 | 2008-08-14 | Ind-Swift Laboratories Limited | Process for preparing highly pure ezetimibe using novel intermediates |
CN103207248A (zh) * | 2012-12-21 | 2013-07-17 | 北京万全德众医药生物技术有限公司 | 一种用高效液相色谱法分离依折麦布中间体光学异构体的方法 |
CN103760281A (zh) * | 2014-01-14 | 2014-04-30 | 北京万全德众医药生物技术有限公司 | 一种液相方法分离依折麦布光学异构体的方法 |
CN104977368A (zh) * | 2014-04-02 | 2015-10-14 | 天津药物研究院 | 一种4-[(4-氟苯基亚胺)甲基]-苯酚的有关物质检测方法及其应用 |
CN104764825A (zh) * | 2015-04-11 | 2015-07-08 | 常州亚邦制药有限公司 | 依折麦布关键中间体的对映异构体的分离检测方法 |
Non-Patent Citations (4)
Title |
---|
KAMESWARA RAO CHIMALAKONDA ET AL.: "Development and Validation of Chiral HPLC Method for Identification and Quantification of (R)-Enantiomer in Ezetimibe", 《AMERICAN JOURNAL OF ANALYTICAL CHEMISTRY》 * |
大赛璐药物手性技术(上海)有限公司 WWW.DAICELCHIRALTECH.CN: "《"ChiralPakID-3, ChiralPakIE-3,CHIRALPAKIF-3色谱柱使用手册<正相模式>"》", 30 April 2014 * |
宋佳新 等: "HPLC手性固定相法检查苄基依折麦布中的异构体杂质", 《沈阳药科大学学报》 * |
金薇 等: "依折麦布及其R-对映体的超临界流体色谱手性拆分方法研究", 《中国药学杂志》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107764890A (zh) * | 2017-10-16 | 2018-03-06 | 杭州先导医药科技有限责任公司 | 一种依折麦布对映异构体的区分检测方法 |
CN107764890B (zh) * | 2017-10-16 | 2019-12-17 | 杭州先导医药科技有限责任公司 | 一种依折麦布对映异构体的区分检测方法 |
CN107677753A (zh) * | 2017-11-24 | 2018-02-09 | 中山奕安泰医药科技有限公司 | 一种依替米贝中间体的检测方法 |
CN107677753B (zh) * | 2017-11-24 | 2021-03-16 | 中山奕安泰医药科技有限公司 | 一种依替米贝中间体的检测方法 |
Also Published As
Publication number | Publication date |
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WO2017080046A1 (zh) | 2017-05-18 |
CN106706818B (zh) | 2018-08-03 |
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Effective date of registration: 20191009 Address after: 233000 Xianghe Home Floor No.9, Xinhuai Road, Dongsheng Street, Longzihu District, Bengbu City, Anhui Province Patentee after: Bengbu Qibang Science and Technology Information Consulting Co.,Ltd. Address before: Xinhua Road 512000 Guangdong city of Shaoguan province Wujiang District No. 32 Patentee before: GUANGZHOU JUNCY INTELLECTUAL PROPERTY MANAGEMENT CONSULTING Co.,Ltd. SHAOGUAN BRANCH |
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Effective date of registration: 20221228 Address after: No. 7100-2, Zhengyang Road, Zhoucun District, Zibo City, Shandong Province 255000 Patentee after: Zibo Youxin New Material Technology Co.,Ltd. Address before: 233000 No.9, 1st floor, Xianghe Jiayuan, Xinhuai Road, Dongsheng Street, Longzihu District, Bengbu City, Anhui Province Patentee before: Bengbu Qibang Science and Technology Information Consulting Co.,Ltd. |
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