CN110568100A - mitiglinide calcium R-isomer detection method - Google Patents
mitiglinide calcium R-isomer detection method Download PDFInfo
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- CN110568100A CN110568100A CN201910862258.5A CN201910862258A CN110568100A CN 110568100 A CN110568100 A CN 110568100A CN 201910862258 A CN201910862258 A CN 201910862258A CN 110568100 A CN110568100 A CN 110568100A
- Authority
- CN
- China
- Prior art keywords
- mitiglinide calcium
- isomer
- mitiglinide
- preparation
- mobile phase
- 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.)
- Granted
Links
- 229960003365 mitiglinide Drugs 0.000 title claims abstract description 103
- PMRVFZXOCRHXFE-FMEJWYFOSA-L Kad 1229 Chemical compound [Ca+2].C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)[O-])C1=CC=CC=C1.C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)[O-])C1=CC=CC=C1 PMRVFZXOCRHXFE-FMEJWYFOSA-L 0.000 title claims abstract 29
- 238000001514 detection method Methods 0.000 title claims description 14
- 239000000243 solution Substances 0.000 claims abstract description 52
- 238000002360 preparation method Methods 0.000 claims abstract description 41
- 238000005303 weighing Methods 0.000 claims abstract description 34
- 239000013558 reference substance Substances 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000012085 test solution Substances 0.000 claims abstract description 18
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 239000012088 reference solution Substances 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 11
- 229940079593 drug Drugs 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 238000002347 injection Methods 0.000 claims abstract description 5
- 239000007924 injection Substances 0.000 claims abstract description 5
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 3
- 238000010606 normalization Methods 0.000 claims abstract description 3
- PMZXXNPJQYDFJX-UHFFFAOYSA-N acetonitrile;2,2,2-trifluoroacetic acid Chemical compound CC#N.OC(=O)C(F)(F)F PMZXXNPJQYDFJX-UHFFFAOYSA-N 0.000 claims description 10
- WPGGHFDDFPHPOB-BBWFWOEESA-N mitiglinide Chemical compound C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)O)C1=CC=CC=C1 WPGGHFDDFPHPOB-BBWFWOEESA-N 0.000 claims description 10
- QEVLNUAVAONTEW-UZYHXJQGSA-L calcium;(2s)-4-[(3as,7ar)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]-2-benzyl-4-oxobutanoate;dihydrate Chemical compound O.O.[Ca+2].C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)[O-])C1=CC=CC=C1.C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)[O-])C1=CC=CC=C1 QEVLNUAVAONTEW-UZYHXJQGSA-L 0.000 description 64
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 239000000523 sample Substances 0.000 description 11
- 238000000926 separation method Methods 0.000 description 10
- 238000012216 screening Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000012467 final product Substances 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- 230000003044 adaptive effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- GTOFKXZQQDSVFH-VIFPVBQESA-N (r)-2-benzylsuccinate Chemical group OC(=O)C[C@@H](C(O)=O)CC1=CC=CC=C1 GTOFKXZQQDSVFH-VIFPVBQESA-N 0.000 description 3
- KYILORDWJFEQBS-UHFFFAOYSA-N 2-benzylidenebutanedioic acid Chemical compound OC(=O)CC(C(O)=O)=CC1=CC=CC=C1 KYILORDWJFEQBS-UHFFFAOYSA-N 0.000 description 2
- GTOFKXZQQDSVFH-UHFFFAOYSA-N 2-benzylsuccinic acid Chemical compound OC(=O)CC(C(O)=O)CC1=CC=CC=C1 GTOFKXZQQDSVFH-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 230000003914 insulin secretion Effects 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- ODSNARDHJFFSRH-OCAPTIKFSA-N (3as,7ar)-2,3,3a,4,5,6,7,7a-octahydro-1h-isoindole Chemical compound C1CCC[C@@H]2CNC[C@@H]21 ODSNARDHJFFSRH-OCAPTIKFSA-N 0.000 description 1
- GTOFKXZQQDSVFH-SECBINFHSA-N (R)-2-benzylsuccinic acid Chemical compound OC(=O)C[C@H](C(O)=O)CC1=CC=CC=C1 GTOFKXZQQDSVFH-SECBINFHSA-N 0.000 description 1
- WVXPTHZHWXOLNK-UHFFFAOYSA-N 4-(2,3-dihydro-1h-isoindol-1-yl)butanoic acid Chemical compound C1=CC=C2C(CCCC(=O)O)NCC2=C1 WVXPTHZHWXOLNK-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- ARLZGEXVMUDUQZ-UHFFFAOYSA-N O.O.[Ca] Chemical compound O.O.[Ca] ARLZGEXVMUDUQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000009460 calcium influx Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003112 degranulating effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009207 exercise therapy Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- -1 mitiglinide benzyl ester Chemical class 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 239000003643 water by type Substances 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
-
- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N2030/042—Standards
- G01N2030/047—Standards external
Landscapes
- 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)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Diluent | ratio of | Degree of separation | Number of theoretical plates |
acetonitrile: trifluoroacetic acid | 100:0.05 | 1.50 | 2134 |
acetonitrile: trifluoroacetic acid | 100:0.1 | 2.63 | 2530 |
Acetonitrile: trifluoroacetic acid | 100:0.2 | 2.01 | 2076 |
Methanol: trifluoroacetic acid | 100:0.05 | 1.25 | 1965 |
Methanol: trifluoroacetic acid | 100:0.1 | 1.10 | 1852 |
Methanol: trifluoroacetic acid | 100:0.2 | 0.93 | 1869 |
Chromatographic column | Bonded phase | degree of separation |
Chiral chromatographic column | Ultimate Amy-SR | 2.37 |
Chiral chromatographic column | Ultimate Amy-DR | 2.65 |
Chiral chromatographic column | Sumichiral OA-3300 | 0.70 |
Chiral chromatographic column | Sumichiral OA-3100 | 1.03 |
Flow rate of flow | number of theoretical plate | Degree of separation |
0.3ml/min | 2170 | 2.45 |
0.5ml/min | 2480 | 2.63 |
0.8ml/min | 2010 | 2.60 |
Instrument for measuring the position of a moving object | Model number | Degree of separation |
Agilent high performance liquid chromatograph | 1260 | 2.60 |
Waters high performance liquid chromatograph | 2695 | 2.51 |
Type (B) | Degree of separation | number of theoretical plate |
the invention | 2.63 | 2639 |
National drug Standard YBH00192012 | 0.76 | 2315 |
National drug Standard YBH04122012 | 1.45 | 2473 |
Type (B) | Degree of separation | Number of theoretical plate |
Example 1 | 2.30 | 2159 |
Example 2 | 2.69 | 2487 |
example 3 | 2.53 | 2031 |
example 4 | 2.09 | 2028 |
Example 5 | 1.69 | 2003 |
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910862258.5A CN110568100B (en) | 2019-09-12 | 2019-09-12 | Mitiglinide calcium R-isomer detection method |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910862258.5A CN110568100B (en) | 2019-09-12 | 2019-09-12 | Mitiglinide calcium R-isomer detection method |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110568100A true CN110568100A (en) | 2019-12-13 |
CN110568100B CN110568100B (en) | 2022-05-31 |
Family
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Family Applications (1)
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CN201910862258.5A Active CN110568100B (en) | 2019-09-12 | 2019-09-12 | Mitiglinide calcium R-isomer detection method |
Country Status (1)
Country | Link |
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CN (1) | CN110568100B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112557566A (en) * | 2020-12-12 | 2021-03-26 | 江西济民可信药业有限公司 | Method for detecting corresponding isomer of mitiglinide calcium intermediate S-benzylsuccinic acid |
Citations (15)
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US20030203946A1 (en) * | 2000-11-17 | 2003-10-30 | Carsten Behrens | Glucagon antagonists/inverse agonists |
CN1742721A (en) * | 2005-09-29 | 2006-03-08 | 周卓和 | Mitiglinide preparation and preparing method |
CN1844096A (en) * | 2006-05-24 | 2006-10-11 | 严洁 | Preparation of mitiglinide calcium and its quality control method |
CN1843352A (en) * | 2006-05-24 | 2006-10-11 | 严洁 | Mitiglinide calcium formulation formula |
CN101464431A (en) * | 2007-12-19 | 2009-06-24 | 北京德众万全药物技术开发有限公司 | Method for analytical separation of Mitiglinide calcium intermediate body and its enantiomer by HPLC method |
CN101821264A (en) * | 2007-10-09 | 2010-09-01 | 默克专利有限公司 | Pyridine derivatives useful as glucokinase activators |
CN101959515A (en) * | 2008-02-25 | 2011-01-26 | 默克专利有限公司 | Glucokinase activators |
CN102911107A (en) * | 2012-09-28 | 2013-02-06 | 迪沙药业集团有限公司 | Preparation method of mitiglinide calcium |
CN103344733A (en) * | 2013-07-08 | 2013-10-09 | 江苏奥赛康药业股份有限公司 | High performance liquid chromatographic separation detection method for bortezomib enantiomers |
US20140045746A1 (en) * | 2012-08-02 | 2014-02-13 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
US20150344487A1 (en) * | 2008-11-13 | 2015-12-03 | Merck Sharp & Dohme Corp. | Aminotetrahydropyrans as dipeptidyl peptidase-iv inhibitors for the treatment of diabetes |
CN105560197A (en) * | 2015-12-30 | 2016-05-11 | 宜昌东阳光长江药业股份有限公司 | Rapid-dissolution mitiglinide preparation, and preparation method and detection method thereof |
CN108125917A (en) * | 2017-12-22 | 2018-06-08 | 江西济民可信药业有限公司 | A kind of method of the preparation of mitiglinide |
CN108982706A (en) * | 2018-09-14 | 2018-12-11 | 山东铂源药业有限公司 | The detection method of impurity cis-hexahydroisoindoline in a kind of Mitiglinide Calcium |
CN109580821A (en) * | 2018-12-21 | 2019-04-05 | 山东铂源药业有限公司 | The detection method of impurity succinic acid in a kind of S- benzyl succinic acid |
-
2019
- 2019-09-12 CN CN201910862258.5A patent/CN110568100B/en active Active
Patent Citations (15)
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US20030203946A1 (en) * | 2000-11-17 | 2003-10-30 | Carsten Behrens | Glucagon antagonists/inverse agonists |
CN1742721A (en) * | 2005-09-29 | 2006-03-08 | 周卓和 | Mitiglinide preparation and preparing method |
CN1844096A (en) * | 2006-05-24 | 2006-10-11 | 严洁 | Preparation of mitiglinide calcium and its quality control method |
CN1843352A (en) * | 2006-05-24 | 2006-10-11 | 严洁 | Mitiglinide calcium formulation formula |
CN101821264A (en) * | 2007-10-09 | 2010-09-01 | 默克专利有限公司 | Pyridine derivatives useful as glucokinase activators |
CN101464431A (en) * | 2007-12-19 | 2009-06-24 | 北京德众万全药物技术开发有限公司 | Method for analytical separation of Mitiglinide calcium intermediate body and its enantiomer by HPLC method |
CN101959515A (en) * | 2008-02-25 | 2011-01-26 | 默克专利有限公司 | Glucokinase activators |
US20150344487A1 (en) * | 2008-11-13 | 2015-12-03 | Merck Sharp & Dohme Corp. | Aminotetrahydropyrans as dipeptidyl peptidase-iv inhibitors for the treatment of diabetes |
US20140045746A1 (en) * | 2012-08-02 | 2014-02-13 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
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CN109580821A (en) * | 2018-12-21 | 2019-04-05 | 山东铂源药业有限公司 | The detection method of impurity succinic acid in a kind of S- benzyl succinic acid |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112557566A (en) * | 2020-12-12 | 2021-03-26 | 江西济民可信药业有限公司 | Method for detecting corresponding isomer of mitiglinide calcium intermediate S-benzylsuccinic acid |
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Address after: 336000 No. 888 hi tech seven road, hi tech Development Zone, Nanchang, Jiangxi. Applicant after: Jiangxi Jinshuibao Pharmaceutical Co.,Ltd. Applicant after: JIANGXI JIMINKEXIN PHARMACEUTICAL Co.,Ltd. Address before: 330096 Zhongxing Software Park, 688 Aixi Hubei Road, Nanchang High-tech Industrial Development Zone, Nanchang City, Jiangxi Province, 14 Applicant before: JIANGXI JIMINKEXIN JINSHUIBAO PHARMACEUTICAL Co.,Ltd. Applicant before: JIANGXI JIMINKEXIN PHARMACEUTICAL Co.,Ltd. |
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Inventor after: Chen Xiaomin Inventor after: Li Yibao Inventor after: Ma Lixiong Inventor after: Zhang Keqin Inventor after: Peng Changchun Inventor after: Yi Yaojiang Inventor before: Chen Xiaomin Inventor before: Zhang Keqin Inventor before: Zhao Youhong Inventor before: Peng Changchun Inventor before: Yi Yaojiang |
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Application publication date: 20191213 Assignee: JIANGXI JIMIN KEXIN MEDICINE Co.,Ltd. Assignor: JIANGXI JIMINKEXIN PHARMACEUTICAL Co.,Ltd. Contract record no.: X2023980053140 Denomination of invention: A Detection Method for R-Isomers of Migliflozine Calcium Granted publication date: 20220531 License type: Common License Record date: 20231219 |