CN102101838A - 一种米格列奈钙的制备方法 - Google Patents
一种米格列奈钙的制备方法 Download PDFInfo
- Publication number
- CN102101838A CN102101838A CN 201010573666 CN201010573666A CN102101838A CN 102101838 A CN102101838 A CN 102101838A CN 201010573666 CN201010573666 CN 201010573666 CN 201010573666 A CN201010573666 A CN 201010573666A CN 102101838 A CN102101838 A CN 102101838A
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- Prior art keywords
- benzyl
- succinic acid
- hours
- acid
- synthesizing
- 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 25
- 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 description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 8
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims abstract description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims abstract description 4
- 239000001110 calcium chloride Substances 0.000 claims abstract description 4
- 229910001628 calcium chloride Inorganic materials 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- KYILORDWJFEQBS-UHFFFAOYSA-N 2-benzylidenebutanedioic acid Chemical compound OC(=O)CC(C(O)=O)=CC1=CC=CC=C1 KYILORDWJFEQBS-UHFFFAOYSA-N 0.000 claims description 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 16
- 230000002194 synthesizing effect Effects 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000000967 suction filtration Methods 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- GTOFKXZQQDSVFH-VIFPVBQESA-N (r)-2-benzylsuccinate Chemical compound OC(=O)C[C@@H](C(O)=O)CC1=CC=CC=C1 GTOFKXZQQDSVFH-VIFPVBQESA-N 0.000 claims description 8
- GTOFKXZQQDSVFH-UHFFFAOYSA-N 2-benzylsuccinic acid Chemical compound OC(=O)CC(C(O)=O)CC1=CC=CC=C1 GTOFKXZQQDSVFH-UHFFFAOYSA-N 0.000 claims description 8
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 8
- 235000019260 propionic acid Nutrition 0.000 claims description 8
- 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 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 6
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 6
- -1 phenyl aldehyde Chemical class 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical group C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- RUJHATQMIMUYKD-UHFFFAOYSA-N 2-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(CCN)=CC=CC2=C1 RUJHATQMIMUYKD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 230000006837 decompression Effects 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 239000001307 helium Substances 0.000 claims 1
- 229910052734 helium Inorganic materials 0.000 claims 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 2
- IFDLFCDWOFLKEB-JTQLQIEISA-N [(2s)-2-methylbutyl]benzene Chemical compound CC[C@H](C)CC1=CC=CC=C1 IFDLFCDWOFLKEB-JTQLQIEISA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000008065 acid anhydrides Chemical class 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 238000000926 separation method Methods 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- OTYHXTFOFQGPOV-UHFFFAOYSA-L calcium propanoate dihydrate Chemical compound O.O.C(CC)(=O)[O-].[Ca+2].C(CC)(=O)[O-] OTYHXTFOFQGPOV-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
- 229960000698 nateglinide Drugs 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 150000002993 phenylalanine derivatives Chemical class 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 239000003450 potassium channel blocker Substances 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 229960002354 repaglinide Drugs 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201010573666A CN102101838B (zh) | 2010-12-06 | 2010-12-06 | 一种米格列奈钙的制备方法 |
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CN201010573666A CN102101838B (zh) | 2010-12-06 | 2010-12-06 | 一种米格列奈钙的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN102101838A true CN102101838A (zh) | 2011-06-22 |
CN102101838B CN102101838B (zh) | 2012-09-12 |
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CN201010573666A Expired - Fee Related CN102101838B (zh) | 2010-12-06 | 2010-12-06 | 一种米格列奈钙的制备方法 |
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102659562A (zh) * | 2012-05-09 | 2012-09-12 | 山东铂源药业有限公司 | 一种米格列奈钙中间体的合成方法 |
CN102898348A (zh) * | 2012-06-27 | 2013-01-30 | 迪沙药业集团有限公司 | 一种米格列奈钙的制备方法 |
CN103450069A (zh) * | 2013-06-24 | 2013-12-18 | 山西大同大学 | 一种米格列奈钙的制备方法 |
CN103709092A (zh) * | 2013-11-04 | 2014-04-09 | 河北科技大学 | 高纯度米格列奈钙的制备方法 |
CN103864669A (zh) * | 2012-12-14 | 2014-06-18 | 南京长澳医药科技有限公司 | 一种米格列奈钙的新晶型及其制备方法 |
CN104311471A (zh) * | 2014-09-23 | 2015-01-28 | 山东省药学科学院 | 一种改进的米格列奈钙的工业化制备方法 |
CN105037244A (zh) * | 2015-07-20 | 2015-11-11 | 常州大学 | 一种米格列奈钙的制备方法 |
CN105152980A (zh) * | 2015-09-11 | 2015-12-16 | 浙江永宁药业股份有限公司 | N-叔丁氧羰基-(4s)-(对苯基苯基甲基)-4-氨基-(2r)-甲基丁酸的手性制备方法 |
CN105153012A (zh) * | 2015-07-20 | 2015-12-16 | 常州大学 | 一种米格列奈钙的制备新方法 |
CN105330585A (zh) * | 2015-11-05 | 2016-02-17 | 常州大学 | 一种米格列奈钙的制备新方法 |
CN106008312A (zh) * | 2016-08-15 | 2016-10-12 | 河南中医学院 | 一种降糖药物米格列奈钙的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1844096A (zh) * | 2006-05-24 | 2006-10-11 | 严洁 | 一种米格列奈钙的制备及质量控制方法 |
CN101270074A (zh) * | 2007-03-21 | 2008-09-24 | 北京德众万全药物技术开发有限公司 | 一种高纯度米格列奈钙的制备方法 |
-
2010
- 2010-12-06 CN CN201010573666A patent/CN102101838B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1844096A (zh) * | 2006-05-24 | 2006-10-11 | 严洁 | 一种米格列奈钙的制备及质量控制方法 |
CN101270074A (zh) * | 2007-03-21 | 2008-09-24 | 北京德众万全药物技术开发有限公司 | 一种高纯度米格列奈钙的制备方法 |
Non-Patent Citations (1)
Title |
---|
《化工时刊》 20070625 林伟 等 抗糖尿病新药米格列奈钙的合成 第25-26、29页 1-3 第21卷, 第6期 2 * |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102659562A (zh) * | 2012-05-09 | 2012-09-12 | 山东铂源药业有限公司 | 一种米格列奈钙中间体的合成方法 |
CN102898348B (zh) * | 2012-06-27 | 2015-09-02 | 迪沙药业集团有限公司 | 一种米格列奈钙的制备方法 |
CN102898348A (zh) * | 2012-06-27 | 2013-01-30 | 迪沙药业集团有限公司 | 一种米格列奈钙的制备方法 |
CN103864669A (zh) * | 2012-12-14 | 2014-06-18 | 南京长澳医药科技有限公司 | 一种米格列奈钙的新晶型及其制备方法 |
CN103450069A (zh) * | 2013-06-24 | 2013-12-18 | 山西大同大学 | 一种米格列奈钙的制备方法 |
CN103709092A (zh) * | 2013-11-04 | 2014-04-09 | 河北科技大学 | 高纯度米格列奈钙的制备方法 |
CN103709092B (zh) * | 2013-11-04 | 2016-07-06 | 河北科技大学 | 米格列奈钙的制备方法 |
CN104311471A (zh) * | 2014-09-23 | 2015-01-28 | 山东省药学科学院 | 一种改进的米格列奈钙的工业化制备方法 |
CN104311471B (zh) * | 2014-09-23 | 2017-05-17 | 山东省生物医药科学院 | 一种改进的米格列奈钙的工业化制备方法 |
CN105037244A (zh) * | 2015-07-20 | 2015-11-11 | 常州大学 | 一种米格列奈钙的制备方法 |
CN105153012A (zh) * | 2015-07-20 | 2015-12-16 | 常州大学 | 一种米格列奈钙的制备新方法 |
CN105153012B (zh) * | 2015-07-20 | 2018-01-02 | 常州大学 | 一种米格列奈钙的制备方法 |
CN105152980A (zh) * | 2015-09-11 | 2015-12-16 | 浙江永宁药业股份有限公司 | N-叔丁氧羰基-(4s)-(对苯基苯基甲基)-4-氨基-(2r)-甲基丁酸的手性制备方法 |
CN105330585A (zh) * | 2015-11-05 | 2016-02-17 | 常州大学 | 一种米格列奈钙的制备新方法 |
CN106008312A (zh) * | 2016-08-15 | 2016-10-12 | 河南中医学院 | 一种降糖药物米格列奈钙的制备方法 |
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