CN102584677B - 一种格列齐特的制备方法 - Google Patents
一种格列齐特的制备方法 Download PDFInfo
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- CN102584677B CN102584677B CN201210025914.4A CN201210025914A CN102584677B CN 102584677 B CN102584677 B CN 102584677B CN 201210025914 A CN201210025914 A CN 201210025914A CN 102584677 B CN102584677 B CN 102584677B
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- reaction
- cyclopentano
- gliclazide
- hydrogen
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- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 title claims abstract description 26
- 229960000346 gliclazide Drugs 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- 238000003756 stirring Methods 0.000 claims description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- 150000002148 esters Chemical class 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- 239000000243 solution Substances 0.000 claims description 22
- 238000004821 distillation Methods 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 14
- 239000012043 crude product Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 claims description 8
- VODBHXZOIQDDST-UHFFFAOYSA-N copper zinc oxygen(2-) Chemical compound [O--].[O--].[Cu++].[Zn++] VODBHXZOIQDDST-UHFFFAOYSA-N 0.000 claims description 8
- 239000011787 zinc oxide Substances 0.000 claims description 7
- SVDVKEBISAOWJT-UHFFFAOYSA-N n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1 SVDVKEBISAOWJT-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 235000015320 potassium carbonate Nutrition 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 150000003233 pyrroles Chemical class 0.000 claims description 4
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012267 brine Substances 0.000 claims description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract description 2
- 230000002829 reductive effect Effects 0.000 abstract description 2
- 238000007259 addition reaction Methods 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 7
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 239000003472 antidiabetic agent Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- 229940127003 anti-diabetic drug Drugs 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- -1 lithium aluminum hydride Chemical compound 0.000 description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
- UZHVXJZEHGSWQV-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole Chemical compound C1NCC2CCCC21 UZHVXJZEHGSWQV-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 229940126904 hypoglycaemic agent Drugs 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Abstract
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CN102584677A CN102584677A (zh) | 2012-07-18 |
CN102584677B true CN102584677B (zh) | 2014-01-08 |
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Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103833625B (zh) * | 2014-03-21 | 2016-06-08 | 华烁科技股份有限公司 | N-氨基-3-氮杂双环[3.3.0]辛烷盐酸盐的后处理方法 |
CN105061293B (zh) * | 2015-07-28 | 2017-11-07 | 江苏瑞科医药科技有限公司 | 一种格列齐特中间体氨基氮杂环盐酸盐的合成方法 |
CN105622438A (zh) * | 2016-03-01 | 2016-06-01 | 苏州艾缇克药物化学有限公司 | 一种酪胺盐酸盐的合成方法 |
CN106518747A (zh) * | 2016-10-19 | 2017-03-22 | 安徽金鼎医药股份有限公司 | 一种制备格列齐特中间体的新方法 |
CN106892856A (zh) * | 2017-02-06 | 2017-06-27 | 山东科源制药股份有限公司 | 一种格列齐特粗品重结晶的制备方法 |
CN106831536B (zh) * | 2017-02-21 | 2020-04-03 | 山东科源制药股份有限公司 | 一种格列齐特合成工艺的制备方法 |
CN108084080A (zh) * | 2018-01-22 | 2018-05-29 | 安徽金鼎医药股份有限公司 | 一种格列齐特中间体六氢环戊并[c]吡咯基-2-胺盐酸盐的制备方法 |
CN110372545B (zh) * | 2019-08-06 | 2022-01-04 | 山东海佑福瑞达制药有限公司 | 一种高纯度的格列齐特中间体对甲苯磺酰脲的制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101235011A (zh) * | 2008-03-11 | 2008-08-06 | 浙江大学 | N-氨基-1,2-环戊烷二甲酰亚胺及其制备方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH0565270A (ja) * | 1991-03-14 | 1993-03-19 | Honsyu Kagaku Kogyo Kk | N−アミノ−3−アザビシクロ〔3, 3, 0〕オクタンの製造方法 |
JPH0641073A (ja) * | 1992-07-20 | 1994-02-15 | Honsyu Kagaku Kogyo Kk | N−(4−メチルベンゼンスルホニル)−n’−(3−アザビシクロ(3, 3, 0)オクタ−3−イル)尿素又はその塩の製造方法 |
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Patent Citations (1)
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CN101235011A (zh) * | 2008-03-11 | 2008-08-06 | 浙江大学 | N-氨基-1,2-环戊烷二甲酰亚胺及其制备方法 |
Non-Patent Citations (4)
Title |
---|
JP平5-65270A 1993.03.19 |
JP平6-41073A 1994.02.15 |
格列齐特缩合反应的工艺改进;董海长等;《山东化工》;20111231;第40卷(第12期);第48,50页 * |
董海长等.格列齐特缩合反应的工艺改进.《山东化工》.2011,第40卷(第12期), |
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Address after: 247200, Chizhou, Anhui Province East County incense corner Chemical Industry Park Patentee after: ANHUI JINDING PHARMACEUTICAL CO.,LTD. Address before: 247200, Chizhou, Anhui Province East County incense corner Chemical Industry Park Patentee before: ANHUI JINDING PHARMACEUTICAL Co.,Ltd. |
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Denomination of invention: Method for preparing gliclazide Effective date of registration: 20190426 Granted publication date: 20140108 Pledgee: CITIC financing Company Limited by Guarantee in Dongzhi County Pledgor: ANHUI JINDING PHARMACEUTICAL CO.,LTD. Registration number: 2019340000217 |
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Date of cancellation: 20200508 Granted publication date: 20140108 Pledgee: CITIC financing Company Limited by Guarantee in Dongzhi County Pledgor: ANHUI JINDING PHARMACEUTICAL Co.,Ltd. Registration number: 2019340000217 |
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Denomination of invention: Method for preparing gliclazide Effective date of registration: 20200518 Granted publication date: 20140108 Pledgee: CITIC financing Company Limited by Guarantee in Dongzhi County Pledgor: ANHUI JINDING PHARMACEUTICAL Co.,Ltd. Registration number: Y2020980002272 |
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Date of cancellation: 20220329 Granted publication date: 20140108 Pledgee: CITIC financing Company Limited by Guarantee in Dongzhi County Pledgor: ANHUI JINDING PHARMACEUTICAL CO.,LTD. Registration number: Y2020980002272 |
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Denomination of invention: A Preparation Method of Gliclazide Effective date of registration: 20230925 Granted publication date: 20140108 Pledgee: Agricultural Bank of China Limited Dongzhi County Branch Pledgor: ANHUI JINDING PHARMACEUTICAL CO.,LTD. Registration number: Y2023980058738 |