CN101654694A - 一种3-去乙酰基-7-氨基头孢烯酸的制备方法 - Google Patents
一种3-去乙酰基-7-氨基头孢烯酸的制备方法 Download PDFInfo
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- CN101654694A CN101654694A CN200810032127A CN200810032127A CN101654694A CN 101654694 A CN101654694 A CN 101654694A CN 200810032127 A CN200810032127 A CN 200810032127A CN 200810032127 A CN200810032127 A CN 200810032127A CN 101654694 A CN101654694 A CN 101654694A
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- immobilization
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- deacetylate
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- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 45
- 239000000758 substrate Substances 0.000 claims abstract description 20
- 102000004674 D-amino-acid oxidase Human genes 0.000 claims abstract description 18
- 108010003989 D-amino-acid oxidase Proteins 0.000 claims abstract description 18
- 108010034416 glutarylamidocephalosporanic acid acylase Proteins 0.000 claims abstract description 12
- 230000003647 oxidation Effects 0.000 claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 102000004190 Enzymes Human genes 0.000 claims description 30
- 108090000790 Enzymes Proteins 0.000 claims description 25
- 229940124587 cephalosporin Drugs 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 15
- 229930186147 Cephalosporin Natural products 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 150000001780 cephalosporins Chemical class 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 12
- 230000001590 oxidative effect Effects 0.000 claims description 12
- 238000005917 acylation reaction Methods 0.000 claims description 11
- 238000010931 ester hydrolysis Methods 0.000 claims description 10
- 108010013043 Acetylesterase Proteins 0.000 claims description 9
- 108090000371 Esterases Proteins 0.000 claims description 8
- IXUSDMGLUJZNFO-BXUZGUMPSA-N (7R)-7-(4-carboxybutanamido)cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCCC(O)=O)[C@@H]12 IXUSDMGLUJZNFO-BXUZGUMPSA-N 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 108010093096 Immobilized Enzymes Proteins 0.000 claims description 2
- 239000000243 solution Substances 0.000 abstract description 29
- 238000000034 method Methods 0.000 abstract description 21
- 230000008569 process Effects 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 230000002255 enzymatic effect Effects 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract 2
- 230000007613 environmental effect Effects 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000011259 mixed solution Substances 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 19
- 239000000843 powder Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 13
- URYAFVKLYSEINW-UHFFFAOYSA-N Chlorfenethol Chemical compound C=1C=C(Cl)C=CC=1C(O)(C)C1=CC=C(Cl)C=C1 URYAFVKLYSEINW-UHFFFAOYSA-N 0.000 description 11
- 239000003513 alkali Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 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 description 2
- -1 acetonyl ester ester Chemical class 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ZNVOUDVNEIRTGV-BBZZFXJRSA-N (6r)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-4-carboxylic acid Chemical compound S1C(C(O)=O)C=CN2C(=O)C(N)[C@H]21 ZNVOUDVNEIRTGV-BBZZFXJRSA-N 0.000 description 1
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960003328 benzoyl peroxide Drugs 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN2008100321276A CN101654694B (zh) | 2008-08-22 | 2008-08-22 | 一种3-去乙酰基-7-氨基头孢烯酸的制备方法 |
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CN2008100321276A CN101654694B (zh) | 2008-08-22 | 2008-08-22 | 一种3-去乙酰基-7-氨基头孢烯酸的制备方法 |
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CN101654694A true CN101654694A (zh) | 2010-02-24 |
CN101654694B CN101654694B (zh) | 2011-08-31 |
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CN2008100321276A Expired - Fee Related CN101654694B (zh) | 2008-08-22 | 2008-08-22 | 一种3-去乙酰基-7-氨基头孢烯酸的制备方法 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102827912A (zh) * | 2012-08-31 | 2012-12-19 | 山东鲁抗立科药业有限公司 | 两酶一步法制备医药中间体d-7-aca的工艺 |
CN103014083A (zh) * | 2012-12-31 | 2013-04-03 | 湖南宝利士生物技术有限公司 | 一种磷酸肌酸钠的制备方法 |
CN104480181B (zh) * | 2014-12-31 | 2018-07-20 | 华北制药河北莱欣药业有限公司 | 3-去乙酰基-7-氨基头孢烯酸的制备方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2165276B1 (es) * | 1999-06-18 | 2003-03-01 | Antibioticos Sau | Procedimiento biotecnologico para la produccion de acido 7-aminocefal osporanico (7-adca) y compuestos de sintesis intermedios particularmente penicilina n y desacetoxicefalosporina c (daoc) |
-
2008
- 2008-08-22 CN CN2008100321276A patent/CN101654694B/zh not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102827912A (zh) * | 2012-08-31 | 2012-12-19 | 山东鲁抗立科药业有限公司 | 两酶一步法制备医药中间体d-7-aca的工艺 |
CN102827912B (zh) * | 2012-08-31 | 2014-06-25 | 山东鲁抗立科药业有限公司 | 两酶一步法制备医药中间体d-7-aca的工艺 |
CN103014083A (zh) * | 2012-12-31 | 2013-04-03 | 湖南宝利士生物技术有限公司 | 一种磷酸肌酸钠的制备方法 |
CN104480181B (zh) * | 2014-12-31 | 2018-07-20 | 华北制药河北莱欣药业有限公司 | 3-去乙酰基-7-氨基头孢烯酸的制备方法 |
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Publication number | Publication date |
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CN101654694B (zh) | 2011-08-31 |
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Owner name: HU'NAN BAOLISHI BIOTECHNOLOGY CO., LTD. Free format text: FORMER OWNER: HU'NAN FULAIGE BIOLOGICAL TECHNOLOGY CO. LTD. Effective date: 20120807 |
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Effective date of registration: 20120807 Address after: 410329 Hunan biomedical park in Liuyang Zhiyuan Road No. 13 Patentee after: Hunan Baolishi Biotechnology Co., Ltd. Address before: 410100 Hunan province Changsha City Economic and Technological Development Zone Li Xiang West Road No. 7 Patentee before: Hu'nan Fulaige Biological Technology Co., Ltd. |
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Application publication date: 20100224 Assignee: Hunan Baolishi Biotechnology Co., Ltd. Assignor: Hu'nan Fulaige Biological Technology Co., Ltd. Contract record no.: 2012430000157 Denomination of invention: Preparation method of 3-deacetyl-7-amino-cephemcarboxylic acid Granted publication date: 20110831 License type: Exclusive License Record date: 20120726 |
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