CN107688069B - (1r,2r)-环己烷-1,2-二甲醇的检测方法 - Google Patents
(1r,2r)-环己烷-1,2-二甲醇的检测方法 Download PDFInfo
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- CN107688069B CN107688069B CN201710802972.6A CN201710802972A CN107688069B CN 107688069 B CN107688069 B CN 107688069B CN 201710802972 A CN201710802972 A CN 201710802972A CN 107688069 B CN107688069 B CN 107688069B
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- cyclohexane
- dimethanol
- benzoyl chloride
- derivatization
- hexane
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- XDODWINGEHBYRT-YUMQZZPRSA-N [(1r,2r)-2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@@H]1CCCC[C@H]1CO XDODWINGEHBYRT-YUMQZZPRSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 10
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- 238000001514 detection method Methods 0.000 claims abstract description 26
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 21
- 238000001212 derivatisation Methods 0.000 claims abstract description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000012490 blank solution Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000012085 test solution Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- BJTZQANDAMBQRV-UHFFFAOYSA-N hexane;propan-2-ol;2,2,2-trifluoroacetic acid Chemical compound CC(C)O.CCCCCC.OC(=O)C(F)(F)F BJTZQANDAMBQRV-UHFFFAOYSA-N 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000003908 quality control method Methods 0.000 abstract 1
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 description 25
- 238000004811 liquid chromatography Methods 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 18
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- 238000005406 washing Methods 0.000 description 14
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- 238000012544 monitoring process Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- NEKCRUIRPWNMLK-SCIYSFAVSA-N lurasidone hydrochloride Chemical compound Cl.C1=CC=C2C(N3CCN(CC3)C[C@@H]3CCCC[C@H]3CN3C(=O)[C@@H]4[C@H]5CC[C@H](C5)[C@@H]4C3=O)=NSC2=C1 NEKCRUIRPWNMLK-SCIYSFAVSA-N 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 229960002863 lurasidone hydrochloride Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229960001432 lurasidone Drugs 0.000 description 2
- PQXKDMSYBGKCJA-CVTJIBDQSA-N lurasidone Chemical compound C1=CC=C2C(N3CCN(CC3)C[C@@H]3CCCC[C@H]3CN3C(=O)[C@@H]4[C@H]5CC[C@H](C5)[C@@H]4C3=O)=NSC2=C1 PQXKDMSYBGKCJA-CVTJIBDQSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000004451 qualitative analysis Methods 0.000 description 2
- XDODWINGEHBYRT-OCAPTIKFSA-N [(1s,2r)-2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCCC[C@H]1CO XDODWINGEHBYRT-OCAPTIKFSA-N 0.000 description 1
- XDODWINGEHBYRT-HTQZYQBOSA-N [(1s,2s)-2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCCC[C@@H]1CO XDODWINGEHBYRT-HTQZYQBOSA-N 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- 229940127236 atypical antipsychotics Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229940036674 latuda Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000005220 pharmaceutical analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
Images
Classifications
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- 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
- G01N30/74—Optical detectors
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- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
Description
实施例 | (R)构型% | (S)构型% | e.e.% |
1-1 | 47.08 | 48.31 | -1.29 |
1-2 | 100 | 0 | 100 |
Claims (3)
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CN201710802972.6A CN107688069B (zh) | 2017-09-08 | 2017-09-08 | (1r,2r)-环己烷-1,2-二甲醇的检测方法 |
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CN201710802972.6A CN107688069B (zh) | 2017-09-08 | 2017-09-08 | (1r,2r)-环己烷-1,2-二甲醇的检测方法 |
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CN107688069A CN107688069A (zh) | 2018-02-13 |
CN107688069B true CN107688069B (zh) | 2020-11-03 |
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CN114200034A (zh) * | 2021-10-28 | 2022-03-18 | 上海旭东海普药业有限公司 | 一种维纳卡兰有关物质的分析方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102952001A (zh) * | 2011-08-19 | 2013-03-06 | 天津药物研究院 | 一种手性中间体环己烷二甲醇的制备方法 |
CN103207246A (zh) * | 2012-12-21 | 2013-07-17 | 北京万全德众医药生物技术有限公司 | 一种用液相色谱法分离测定鲁拉西酮及其光学异构体的方法 |
WO2013014665A8 (en) * | 2011-07-28 | 2014-01-23 | Mapi Pharma Ltd. | Intermediate compounds and process for the preparation of lurasidone and salts thereof |
CN103864774A (zh) * | 2012-12-14 | 2014-06-18 | 成都弘达药业有限公司 | 一种鲁拉西酮的制备方法 |
CN105467028A (zh) * | 2015-11-18 | 2016-04-06 | 北京万全德众医药生物技术有限公司 | 气相色谱法分离测定鲁拉西酮中间体光学异构体的方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7067291B2 (en) * | 2002-12-20 | 2006-06-27 | Pfizer Inc. | Biocatalytic preparation of enantiomerically enriched aminopentanenitrile |
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2017
- 2017-09-08 CN CN201710802972.6A patent/CN107688069B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013014665A8 (en) * | 2011-07-28 | 2014-01-23 | Mapi Pharma Ltd. | Intermediate compounds and process for the preparation of lurasidone and salts thereof |
CN102952001A (zh) * | 2011-08-19 | 2013-03-06 | 天津药物研究院 | 一种手性中间体环己烷二甲醇的制备方法 |
CN103864774A (zh) * | 2012-12-14 | 2014-06-18 | 成都弘达药业有限公司 | 一种鲁拉西酮的制备方法 |
CN103207246A (zh) * | 2012-12-21 | 2013-07-17 | 北京万全德众医药生物技术有限公司 | 一种用液相色谱法分离测定鲁拉西酮及其光学异构体的方法 |
CN105467028A (zh) * | 2015-11-18 | 2016-04-06 | 北京万全德众医药生物技术有限公司 | 气相色谱法分离测定鲁拉西酮中间体光学异构体的方法 |
Non-Patent Citations (5)
Title |
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Enantioselective Synthesis of ((1R,2R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate;Ganesh, K. Ravi; Pachore, Sharad S.; Pratap, T. V;《SYNTHETIC COMMUNICATIONS》;20150824;第45卷(第23期);2676-2682 * |
RESOLUTION OF ENANTIOMERS OF HYDROXYEICOSATETRAENOATE DERIVATIVES BY CHIRAL PHASE HIGH-PRESSURE LIQUID-CHROMATOGRAPHY;HAWKINS, DJ; KUHN, H; PETTY, EH;《ANALYTICAL BIOCHEMISTRY》;19980930;第173卷(第2期);456-462 * |
柱前紫外衍生-高效液相色谱法同时测定功能食品中八种糖醇和糖;刘亚攀;《四川大学学报(医学版)》;20141031;第45卷(第5期);831-835 * |
柱前衍生-反相高效液相色谱法测定人参中人参二醇;石李梁;《理化检验-化学分册》;20100531;第46卷(第5期);482-484 * |
高效液相色谱法测定1-三甲基硅基-1-炔-3-癸醇对映体纯度;阮源萍;《厦门大学学报( 自然科学版)》;20080731;第47卷(第4期);537-540 * |
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Effective date of registration: 20210929 Address after: 361000 unit 04, 4th floor, building B13, Xiamen biomedical industrial park, 2047 wengjiao West Road, Haicang District, Xiamen City, Fujian Province Patentee after: Xiamen Yixian Pharmaceutical Co.,Ltd. Patentee after: XIAMEN WEIYANG PHARMACEUTICAL Co.,Ltd. Address before: 361000 1101, technical service center, No. 120, Xinyuan Road, Haicang District, Xiamen City, Fujian Province Patentee before: Gu Shihai |