CN103224541B - 吉西他滨α-异构体转化回收工艺 - Google Patents
吉西他滨α-异构体转化回收工艺 Download PDFInfo
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- CN103224541B CN103224541B CN201310154007.4A CN201310154007A CN103224541B CN 103224541 B CN103224541 B CN 103224541B CN 201310154007 A CN201310154007 A CN 201310154007A CN 103224541 B CN103224541 B CN 103224541B
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- Prior art keywords
- gemcitabine
- isomer
- alpha
- conversion
- recovery process
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 42
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 title claims abstract description 42
- 229960005277 gemcitabine Drugs 0.000 title claims abstract description 31
- 238000011084 recovery Methods 0.000 title claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims description 6
- 229940079593 drug Drugs 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 5
- 238000011160 research Methods 0.000 abstract description 4
- 239000002777 nucleoside Substances 0.000 abstract description 3
- 150000003833 nucleoside derivatives Chemical class 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 2
- 230000015556 catabolic process Effects 0.000 abstract description 2
- 238000006731 degradation reaction Methods 0.000 abstract description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 230000009897 systematic effect Effects 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 16
- 229960005144 gemcitabine hydrochloride Drugs 0.000 description 11
- 238000002156 mixing Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZAQJHHRNXZUBTE-NQXXGFSBSA-N D-ribulose Chemical compound OC[C@@H](O)[C@@H](O)C(=O)CO ZAQJHHRNXZUBTE-NQXXGFSBSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- ZAQJHHRNXZUBTE-UHFFFAOYSA-N D-threo-2-Pentulose Natural products OCC(O)C(O)C(=O)CO ZAQJHHRNXZUBTE-UHFFFAOYSA-N 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
转化量/mg | 转化收率/% | |
实施例一 | 5.6 | 49.2 |
实施例二 | 5.5 | 48.3 |
实施例三 | 5.0 | 43.9 |
实施例四 | 4.8 | 42.2 |
实施例五 | 4.5 | 39.5 |
实施例六 | 4.6 | 40.4 |
实施例七 | 5.0 | 43.9 |
对比例一 | 2.2 | 19.3 |
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201310154007.4A CN103224541B (zh) | 2013-04-27 | 2013-04-27 | 吉西他滨α-异构体转化回收工艺 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN201310154007.4A CN103224541B (zh) | 2013-04-27 | 2013-04-27 | 吉西他滨α-异构体转化回收工艺 |
Publications (2)
Publication Number | Publication Date |
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CN103224541A CN103224541A (zh) | 2013-07-31 |
CN103224541B true CN103224541B (zh) | 2015-07-01 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN201310154007.4A Active CN103224541B (zh) | 2013-04-27 | 2013-04-27 | 吉西他滨α-异构体转化回收工艺 |
Country Status (1)
Country | Link |
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CN (1) | CN103224541B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113583068B (zh) * | 2021-08-04 | 2023-10-20 | 上海兆维科技发展有限公司 | 一种利用强碱性阴离子交换树脂制备α-脱氧胞苷的方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5637688A (en) * | 1994-12-13 | 1997-06-10 | Eli Lilly And Company | Process for preparing 1-(2'-deoxy-2'-difluoro-d-ribofuranosyl)-4-aminopyrimidin-2-one hydrochloride |
CN101089010B (zh) * | 1998-02-25 | 2011-12-14 | 埃莫里大学 | 2'-氟代核苷 |
BRPI0514718A (pt) * | 2004-12-30 | 2008-07-01 | Hanmi Pharm Ind Co Ltd | método para a preparação de 2'-desoxi-2', 2'-diflúor-citidina |
EP1940859A1 (en) * | 2005-10-28 | 2008-07-09 | Arch Pharmalabs Limited | An improved process for preparation of gemcitabine hydrochloride |
CN101381387B (zh) * | 2007-09-06 | 2011-08-31 | 上海希迪制药有限公司 | 制备2'-脱氧-2',2'-二氟-β-胞苷盐酸盐的方法 |
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2013
- 2013-04-27 CN CN201310154007.4A patent/CN103224541B/zh active Active
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Address after: 222047 Lianyungang economic and Technological Development Zone, Jiangsu Patentee after: JIANGSU HANSOH PHARMACEUTICAL GROUP Co.,Ltd. Address before: 222047 Lianyungang economic and Technological Development Zone, Jiangsu Patentee before: Jiangsu best Pharmaceutical Co.,Ltd. Address after: 222047 Lianyungang economic and Technological Development Zone, Jiangsu Patentee after: Jiangsu best Pharmaceutical Co.,Ltd. Address before: 222047 Lianyungang economic and Technological Development Zone, Jiangsu Patentee before: JIANGSU HANSOH PHARMACEUTICAL Co.,Ltd. |