CN111257491A - HPLC method for detecting cyclopropylamine in Levatinib mesylate - Google Patents
HPLC method for detecting cyclopropylamine in Levatinib mesylate Download PDFInfo
- Publication number
- CN111257491A CN111257491A CN201811458909.6A CN201811458909A CN111257491A CN 111257491 A CN111257491 A CN 111257491A CN 201811458909 A CN201811458909 A CN 201811458909A CN 111257491 A CN111257491 A CN 111257491A
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- CN
- China
- Prior art keywords
- cyclopropylamine
- derivatization
- acetonitrile
- solvent
- buffer solution
- 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
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000004128 high performance liquid chromatography Methods 0.000 title claims abstract description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title abstract description 22
- 238000001212 derivatisation Methods 0.000 claims abstract description 64
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 20
- 239000007853 buffer solution Substances 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 66
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 52
- 239000002904 solvent Substances 0.000 claims description 49
- 239000000243 solution Substances 0.000 claims description 41
- 238000001514 detection method Methods 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 claims description 26
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 229960001429 lenvatinib mesylate Drugs 0.000 claims description 4
- HWLFIUUAYLEFCT-UHFFFAOYSA-N lenvatinib mesylate Chemical compound CS(O)(=O)=O.C=12C=C(C(N)=O)C(OC)=CC2=NC=CC=1OC(C=C1Cl)=CC=C1NC(=O)NC1CC1 HWLFIUUAYLEFCT-UHFFFAOYSA-N 0.000 claims description 4
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- 239000008351 acetate buffer Substances 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- -1 p-nitrophenyl N-succinimidyl acetate Chemical compound 0.000 claims 1
- 238000004458 analytical method Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000003908 quality control method Methods 0.000 abstract description 2
- 239000000523 sample Substances 0.000 description 37
- 239000012535 impurity Substances 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 18
- 239000005695 Ammonium acetate Substances 0.000 description 18
- 229940043376 ammonium acetate Drugs 0.000 description 18
- 235000019257 ammonium acetate Nutrition 0.000 description 18
- 238000007865 diluting Methods 0.000 description 17
- 238000005303 weighing Methods 0.000 description 15
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 14
- 239000013558 reference substance Substances 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000007789 sealing Methods 0.000 description 11
- 238000005406 washing Methods 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 238000000926 separation method Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- 239000012488 sample solution Substances 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000012088 reference solution Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- YBADLXQNJCMBKR-UHFFFAOYSA-M (4-nitrophenyl)acetate Chemical compound [O-]C(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-M 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- ZSPLOATUDIRNAS-PPHPATTJSA-N levofloxacin mesylate Chemical compound CS(O)(=O)=O.C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 ZSPLOATUDIRNAS-PPHPATTJSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Images
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
- G01N30/89—Inverse chromatography
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- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Biological Materials (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
Claims (12)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811458909.6A CN111257491B (en) | 2018-11-30 | 2018-11-30 | HPLC method for detecting cyclopropylamine in lenvatinib mesylate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811458909.6A CN111257491B (en) | 2018-11-30 | 2018-11-30 | HPLC method for detecting cyclopropylamine in lenvatinib mesylate |
Publications (2)
Publication Number | Publication Date |
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CN111257491A true CN111257491A (en) | 2020-06-09 |
CN111257491B CN111257491B (en) | 2023-05-12 |
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Application Number | Title | Priority Date | Filing Date |
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CN201811458909.6A Active CN111257491B (en) | 2018-11-30 | 2018-11-30 | HPLC method for detecting cyclopropylamine in lenvatinib mesylate |
Country Status (1)
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CN (1) | CN111257491B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113122611A (en) * | 2019-12-30 | 2021-07-16 | 海南先声药业有限公司 | Method for checking microbial limit of montmorillonite powder |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105424822A (en) * | 2015-10-29 | 2016-03-23 | 成都百裕科技制药有限公司 | Method for detecting (1R,2S)-2-(3,4-diflurophenyl) cyclopropylamine in ticagrelor |
CN107305202A (en) * | 2016-04-22 | 2017-10-31 | 北京睿创康泰医药研究院有限公司 | The HPLC methods and impurity that analysis methanesulfonic acid pleasure is cut down for Buddhist nun and its preparation impurity make the purposes of reference standard |
-
2018
- 2018-11-30 CN CN201811458909.6A patent/CN111257491B/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105424822A (en) * | 2015-10-29 | 2016-03-23 | 成都百裕科技制药有限公司 | Method for detecting (1R,2S)-2-(3,4-diflurophenyl) cyclopropylamine in ticagrelor |
CN107305202A (en) * | 2016-04-22 | 2017-10-31 | 北京睿创康泰医药研究院有限公司 | The HPLC methods and impurity that analysis methanesulfonic acid pleasure is cut down for Buddhist nun and its preparation impurity make the purposes of reference standard |
Non-Patent Citations (2)
Title |
---|
PAVAN KUMAR S. R. KOTHAPALLI ET AL.: "Simple and Sensitive Stability-Indicating Ion Chromatography Method for the Determination of Cyclopropylamine in Nevirapine and Moxifloxacin Hydrochloride Drug Substances", 《SCIENTIA PHARMACEUTICA》 * |
张建礼等: "替格瑞洛原料药中有关物质的HPLC法测定", 《中国医药工业杂志》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113122611A (en) * | 2019-12-30 | 2021-07-16 | 海南先声药业有限公司 | Method for checking microbial limit of montmorillonite powder |
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Publication number | Publication date |
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CN111257491B (en) | 2023-05-12 |
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Address after: 210042 -18, Xuanwu Avenue, Xuanwu District, Jiangsu, Nanjing, 699 Applicant after: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. Applicant after: WUHU SIMCERE ZHONGREN PHARMACEUTICAL Co.,Ltd. Applicant after: SIMCERE PHARMACEUTICAL Co.,Ltd. Address before: 210042 -18, Xuanwu Avenue, Xuanwu District, Jiangsu, Nanjing, 699 Applicant before: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. Applicant before: WUHU SIMCERE ZHONGREN PHARMACEUTICAL Co.,Ltd. Applicant before: NANJING SIMCERE DONGYUAN PHARMACEUTICA Co.,Ltd. |
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Effective date of registration: 20230427 Address after: No. 20 Yaogu Yiheng Road, Xiuying District, Haikou City, Hainan Province, 570311 Applicant after: Xiansheng Zaiming Pharmaceutical Co.,Ltd. Address before: 210042 699 Xuanwu Road, Xuanwu District, Nanjing, Jiangsu -18 Applicant before: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. Applicant before: WUHU SIMCERE ZHONGREN PHARMACEUTICAL Co.,Ltd. Applicant before: SIMCERE PHARMACEUTICAL Co.,Ltd. |
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Address after: No. 20 Yaogu Yiheng Road, Xiuying District, Haikou City, Hainan Province, 570311 Patentee after: Hainan Xiansheng Zaiming Pharmaceutical Co.,Ltd. Country or region after: China Address before: No. 20 Yaogu Yiheng Road, Xiuying District, Haikou City, Hainan Province, 570311 Patentee before: Xiansheng Zaiming Pharmaceutical Co.,Ltd. Country or region before: China |
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