CN1267436C - 硫酸头孢匹罗的合成方法 - Google Patents
硫酸头孢匹罗的合成方法 Download PDFInfo
- Publication number
- CN1267436C CN1267436C CN 200410069514 CN200410069514A CN1267436C CN 1267436 C CN1267436 C CN 1267436C CN 200410069514 CN200410069514 CN 200410069514 CN 200410069514 A CN200410069514 A CN 200410069514A CN 1267436 C CN1267436 C CN 1267436C
- Authority
- CN
- China
- Prior art keywords
- cefpirome
- cefpirome sulfate
- cooled
- washing
- water
- 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.)
- Expired - Fee Related
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- RKTNPKZEPLCLSF-GNERTXCBSA-N OS([O-])(=O)=O.N([C@@H]1C(N2C(=C(C[N+]=3C=4CCCC=4C=CC=3)CS[C@@H]21)C(O)=O)=O)C(=O)/C(=N/OC)C1=CSC(N)=N1 Chemical compound OS([O-])(=O)=O.N([C@@H]1C(N2C(=C(C[N+]=3C=4CCCC=4C=CC=3)CS[C@@H]21)C(O)=O)=O)C(=O)/C(=N/OC)C1=CSC(N)=N1 RKTNPKZEPLCLSF-GNERTXCBSA-N 0.000 title claims abstract description 21
- 229960002838 cefpirome sulfate Drugs 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 7
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- 229960000466 cefpirome Drugs 0.000 claims abstract description 14
- DKOQGJHPHLTOJR-WHRDSVKCSA-N cefpirome Chemical compound N([C@@H]1C(N2C(=C(C[N+]=3C=4CCCC=4C=CC=3)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 DKOQGJHPHLTOJR-WHRDSVKCSA-N 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 229960004261 cefotaxime Drugs 0.000 claims abstract description 6
- 238000007670 refining Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- -1 iodate hydrogen salt Chemical class 0.000 claims description 10
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 5
- 238000010189 synthetic method Methods 0.000 claims description 5
- 238000000247 postprecipitation Methods 0.000 claims description 4
- 239000003957 anion exchange resin Substances 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000013078 crystal Substances 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
- 238000011010 flushing procedure Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- 229960004839 potassium iodide Drugs 0.000 claims description 3
- 235000007715 potassium iodide Nutrition 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 238000011146 sterile filtration Methods 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 claims 1
- GPRBEKHLDVQUJE-VINNURBNSA-N cefotaxime Chemical compound N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C(O)=O)=O)C(=O)/C(=N/OC)C1=CSC(N)=N1 GPRBEKHLDVQUJE-VINNURBNSA-N 0.000 abstract description 5
- 238000003908 quality control method Methods 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
Landscapes
- Cephalosporin Compounds (AREA)
Abstract
Description
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410069514 CN1267436C (zh) | 2004-06-29 | 2004-06-29 | 硫酸头孢匹罗的合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410069514 CN1267436C (zh) | 2004-06-29 | 2004-06-29 | 硫酸头孢匹罗的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1587267A CN1587267A (zh) | 2005-03-02 |
CN1267436C true CN1267436C (zh) | 2006-08-02 |
Family
ID=34604359
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 200410069514 Expired - Fee Related CN1267436C (zh) | 2004-06-29 | 2004-06-29 | 硫酸头孢匹罗的合成方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1267436C (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100500671C (zh) * | 2007-04-20 | 2009-06-17 | 苏州中联化学制药有限公司 | 一种抗菌素硫酸头孢匹罗的合成方法 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101172982B (zh) * | 2006-11-03 | 2011-06-08 | 河北凯盛医药科技有限公司 | 一种硫酸头孢匹罗的制备方法 |
CN101104621A (zh) * | 2007-05-08 | 2008-01-16 | 深圳信立泰药业股份有限公司 | 制备高纯度硫酸头孢匹罗的工艺 |
CN101362770B (zh) * | 2007-08-10 | 2011-08-31 | 上海新先锋药业有限公司 | 硫酸头孢匹罗制备工艺 |
CN101284840B (zh) * | 2008-05-29 | 2012-07-04 | 管小明 | 硫酸头孢匹罗的合成方法 |
CN103044455B (zh) * | 2011-10-17 | 2015-04-01 | 苏州中联化学制药有限公司 | 硫酸头孢匹罗混粉的返工方法 |
CN103224505B (zh) * | 2013-05-27 | 2015-10-14 | 华北制药河北华民药业有限责任公司 | 一种硫酸头孢匹罗的制备方法 |
-
2004
- 2004-06-29 CN CN 200410069514 patent/CN1267436C/zh not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100500671C (zh) * | 2007-04-20 | 2009-06-17 | 苏州中联化学制药有限公司 | 一种抗菌素硫酸头孢匹罗的合成方法 |
Also Published As
Publication number | Publication date |
---|---|
CN1587267A (zh) | 2005-03-02 |
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Assignee: Suzhou Wanqing Pharmaceutical Co., Ltd. Assignor: Wei Xuewen|Wang Xiaoshu|Shen Jie Contract fulfillment period: 2006.12.1 to 2012.11.30 contract change Contract record no.: 2008320000107 Denomination of invention: Synthesis process of cefpirome sulfate as antibiotic Granted publication date: 20060802 License type: Exclusive license Record date: 2008.8.21 |
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Free format text: EXCLUSIVE LICENCE; TIME LIMIT OF IMPLEMENTING CONTACT: 2006.12.1 TO 2012.11.30 Name of requester: SUZHOU WANQING PHARMACEUTICAL CO., LTD. Effective date: 20080821 |
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Assignee: Hainan Chuntch Pharmaceutical Co., Ltd. Assignor: Wei Xuewen|Wang Xiaoshu|Shen Jie Contract fulfillment period: 2008.11.14 to 2013.11.13 contract change Contract record no.: 2008460000021 Denomination of invention: Synthesis process of cefpirome sulfate as antibiotic Granted publication date: 20060802 License type: Exclusive license Record date: 20081117 |
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TR01 | Transfer of patent right |
Effective date of registration: 20081219 Address after: Peace Avenue in Hainan city of Haikou province No. 30 Hui community building A0 zip code: 570208 Co-patentee after: Shen Jie Patentee after: Wei Xue Wen Address before: Haikou Longnan Medical Technology Development Co., Ltd., B2, 30 Heping Road, Hailin Island, Hainan, Haikou, China, zip code: 570206 Co-patentee before: Wang Xiaoshu Patentee before: Wei Xue Wen Co-patentee before: Shen Jie |
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LIC | Patent licence contract for exploitation submitted for record |
Free format text: EXCLUSIVE LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2008.11.14 TO 2013.11.13; CHANGE OF CONTRACT Name of requester: HAINAN ZHONGHUA LIANHE PHARMACEUTICAL INDUSTRIAL C Effective date: 20081117 |
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Addressee: Shen Jie Document name: Notification that Application Deemed not to be Proposed |
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ASS | Succession or assignment of patent right |
Owner name: HAINAN CHUNTCH PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: WEI XUEWEN Effective date: 20101228 Free format text: FORMER OWNER: SHEN JIE |
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Free format text: CORRECT: ADDRESS; FROM: 570208 BUILDING A0, HUILONG RESIDENTIAL QUARTER, NO.30, HEPING AVENUE, HAIKOU CITY, HAINAN PROVINCE TO: 570216 FACTORY BUILDING 6, FREE TRADE ZONE, HAIKOU CITY, HAINAN PROVINCE |
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Effective date of registration: 20101228 Address after: 570216 No. 6 workshop, Haikou Free Trade Zone, Hainan Patentee after: Hainan Chuntch Pharmaceutical Co., Ltd. Address before: Peace Avenue 570208 Hainan city of Haikou province No. 30 Hui community building A0 Co-patentee before: Shen Jie Patentee before: Wei Xuewen |
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