CN101880252B - 盐酸沃尼妙林的制备方法 - Google Patents
盐酸沃尼妙林的制备方法 Download PDFInfo
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- CN101880252B CN101880252B CN 201010213182 CN201010213182A CN101880252B CN 101880252 B CN101880252 B CN 101880252B CN 201010213182 CN201010213182 CN 201010213182 CN 201010213182 A CN201010213182 A CN 201010213182A CN 101880252 B CN101880252 B CN 101880252B
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- CN
- China
- Prior art keywords
- valnemulin
- preparation
- hydrochloride
- valnemulin hydrochloride
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- 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.)
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- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- MFBPRQKHDIVLOJ-AFFLPQGKSA-N 133868-46-9 Chemical compound Cl.CC(C)[C@@H](N)C(=O)NCC(C)(C)SCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 MFBPRQKHDIVLOJ-AFFLPQGKSA-N 0.000 title claims abstract description 16
- LLYYNOVSVPBRGV-MVNKZKPCSA-N valnemulin Chemical compound CC(C)[C@@H](N)C(=O)NCC(C)(C)SCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 LLYYNOVSVPBRGV-MVNKZKPCSA-N 0.000 claims abstract description 16
- 229950008166 valnemulin Drugs 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- ZRZNJUXESFHSIO-UHFFFAOYSA-N Pleuromutilin Natural products CC1C(O)C(C)(C=C)CC(OC(=O)CO)C2(C)C(C)CCC31C2C(=O)CC3 ZRZNJUXESFHSIO-UHFFFAOYSA-N 0.000 claims abstract description 11
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical compound C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 claims abstract description 11
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012043 crude product Substances 0.000 claims abstract description 9
- -1 sulphonic acid ester Chemical class 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 8
- MBPAUMHSIFBANF-UHFFFAOYSA-N 1-amino-2-methylpropane-2-thiol Chemical compound CC(C)(S)CN MBPAUMHSIFBANF-UHFFFAOYSA-N 0.000 claims description 4
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 13
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- FUAZTTPXPJFEJE-UHFFFAOYSA-N 6-(2-aminopropyl)-1-methylcyclohexa-2,4-diene-1-thiol Chemical compound SC1(C(CC(N)C)C=CC=C1)C FUAZTTPXPJFEJE-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 150000007970 thio esters Chemical class 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 244000000010 microbial pathogen Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 102000003916 Arrestin Human genes 0.000 description 1
- 108090000328 Arrestin Proteins 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 208000001572 Mycoplasma Pneumonia Diseases 0.000 description 1
- 201000008235 Mycoplasma pneumoniae pneumonia Diseases 0.000 description 1
- 108090000279 Peptidyltransferases Proteins 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229950003188 isovaleryl diethylamide Drugs 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000002114 valyl group Chemical group 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN 201010213182 CN101880252B (zh) | 2010-06-29 | 2010-06-29 | 盐酸沃尼妙林的制备方法 |
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CN 201010213182 CN101880252B (zh) | 2010-06-29 | 2010-06-29 | 盐酸沃尼妙林的制备方法 |
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CN101880252A CN101880252A (zh) | 2010-11-10 |
CN101880252B true CN101880252B (zh) | 2013-01-23 |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102225906B (zh) * | 2011-05-12 | 2014-07-30 | 浙江国邦药业有限公司 | 一种沃尼妙林盐酸盐的结晶方法 |
CN102344397B (zh) * | 2011-08-23 | 2013-09-04 | 浙江升华拜克生物股份有限公司 | 一种伐奈莫林盐酸盐的提纯方法 |
CN102424660B (zh) * | 2011-08-25 | 2013-11-27 | 浙江升华拜克生物股份有限公司 | 一种伐奈莫林盐酸盐的低温起泡干燥法及其干燥品 |
CN103382172A (zh) * | 2013-06-20 | 2013-11-06 | 中国农业科学院兰州畜牧与兽药研究所 | 一种盐酸沃尼妙林的合成方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4675330A (en) * | 1984-02-17 | 1987-06-23 | Sandoz Ltd. | Pleuromutilin derivatives process for their preparation and their use |
CN101735123A (zh) * | 2009-12-22 | 2010-06-16 | 山东胜利股份有限公司 | 一种盐酸沃尼妙林的合成方法 |
-
2010
- 2010-06-29 CN CN 201010213182 patent/CN101880252B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4675330A (en) * | 1984-02-17 | 1987-06-23 | Sandoz Ltd. | Pleuromutilin derivatives process for their preparation and their use |
CN101735123A (zh) * | 2009-12-22 | 2010-06-16 | 山东胜利股份有限公司 | 一种盐酸沃尼妙林的合成方法 |
Non-Patent Citations (2)
Title |
---|
沃尼妙林的研究进展;远立国等;《中国兽医科学》;20091231;第39卷(第12期);1124-1128 * |
远立国等.沃尼妙林的研究进展.《中国兽医科学》.2009,第39卷(第12期),1124-1128. |
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CN101880252A (zh) | 2010-11-10 |
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Denomination of invention: Preparation of vornimulin hydrochloride Effective date of registration: 20201228 Granted publication date: 20130123 Pledgee: INNER MONGOLIA BRANCH OF BANK OF COMMUNICATIONS Co.,Ltd. Pledgor: JINHE BIO-TECHNOLOGY Co.,Ltd. Registration number: Y2020150000082 |
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