CN105732663A - 6-氨基青霉烷酸的制备方法 - Google Patents
6-氨基青霉烷酸的制备方法 Download PDFInfo
- Publication number
- CN105732663A CN105732663A CN201610182670.9A CN201610182670A CN105732663A CN 105732663 A CN105732663 A CN 105732663A CN 201610182670 A CN201610182670 A CN 201610182670A CN 105732663 A CN105732663 A CN 105732663A
- Authority
- CN
- China
- Prior art keywords
- amino
- penicillanic acid
- preparation
- acid
- penicillin
- 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.)
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- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 title claims abstract description 89
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 title claims abstract description 89
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 42
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 34
- 229930182555 Penicillin Natural products 0.000 claims description 32
- 229940049954 penicillin Drugs 0.000 claims description 30
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000011347 resin Substances 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 22
- 229960003424 phenylacetic acid Drugs 0.000 claims description 21
- 239000003279 phenylacetic acid Substances 0.000 claims description 21
- 239000012190 activator Substances 0.000 claims description 20
- 238000005336 cracking Methods 0.000 claims description 19
- 239000011259 mixed solution Substances 0.000 claims description 19
- 239000007864 aqueous solution Substances 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- 238000000855 fermentation Methods 0.000 claims description 16
- 230000004151 fermentation Effects 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- 239000012528 membrane Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 238000001728 nano-filtration Methods 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 8
- 238000000108 ultra-filtration Methods 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003463 adsorbent Substances 0.000 claims description 6
- 238000005516 engineering process Methods 0.000 claims description 6
- 238000001471 micro-filtration Methods 0.000 claims description 5
- 239000000919 ceramic Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229920002521 macromolecule Polymers 0.000 claims description 2
- 230000005611 electricity Effects 0.000 claims 1
- 229910052738 indium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 238000000034 method Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 108090000790 Enzymes Proteins 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 12
- 230000008569 process Effects 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 108010093096 Immobilized Enzymes Proteins 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N DMSO-d6 Substances [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000001427 coherent effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- 238000001896 rotating frame Overhauser effect spectroscopy Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000006166 lysate Substances 0.000 description 2
- 229930003658 monoterpene Natural products 0.000 description 2
- -1 monoterpenoid alkaloid Chemical class 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000682653 Corynanthe Species 0.000 description 1
- ITIONVBQFUNVJV-UHFFFAOYSA-N Etomidoline Chemical compound C12=CC=CC=C2C(=O)N(CC)C1NC(C=C1)=CC=C1OCCN1CCCCC1 ITIONVBQFUNVJV-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 229930195708 Penicillin V Natural products 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960003022 amoxicillin Drugs 0.000 description 1
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000011953 bioanalysis Methods 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 1
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 210000001822 immobilized cell Anatomy 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000010829 isocratic elution Methods 0.000 description 1
- RDOXTESZEPMUJZ-WBJZHHNVSA-N methoxybenzene Chemical group CO[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 RDOXTESZEPMUJZ-WBJZHHNVSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
- 229940056367 penicillin v Drugs 0.000 description 1
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940006198 sodium phenylacetate Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/42—Compounds with a free primary amino radical attached in position 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/04—Preparation
- C07D499/18—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P37/00—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin
- C12P37/06—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin by desacylation of the substituent in the 6 position
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
6-APA纯度 | 6-APA收率 | 裂解时间(min) | |
实施例1 | 99.6% | 99.6% | 36 |
实施例2 | 99.4% | 98.3% | 41 |
实施例3 | 99.5% | 98.2% | 45 |
实施例4 | 99.2% | 90.1% | 129 |
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201610182670.9A CN105732663B (zh) | 2016-03-28 | 2016-03-28 | 6‑氨基青霉烷酸的制备方法 |
Applications Claiming Priority (1)
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CN201610182670.9A CN105732663B (zh) | 2016-03-28 | 2016-03-28 | 6‑氨基青霉烷酸的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN105732663A true CN105732663A (zh) | 2016-07-06 |
CN105732663B CN105732663B (zh) | 2018-03-16 |
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Family Applications (1)
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CN201610182670.9A Active CN105732663B (zh) | 2016-03-28 | 2016-03-28 | 6‑氨基青霉烷酸的制备方法 |
Country Status (1)
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CN (1) | CN105732663B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107686490A (zh) * | 2017-10-25 | 2018-02-13 | 陈磊 | 一种提取利福霉素b的方法 |
CN108785728A (zh) * | 2017-05-05 | 2018-11-13 | 国家纳米科学中心 | 含药物中间体修饰的纳米金的抗菌敷料、其制备方法及应用 |
CN109535179A (zh) * | 2017-09-22 | 2019-03-29 | 联邦制药(内蒙古)有限公司 | 一种改进的6-apa提取方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998048039A1 (en) * | 1997-04-22 | 1998-10-29 | Dsm N.V. | Improved process for the fermentative production of penicillin |
CN101735243A (zh) * | 2008-11-11 | 2010-06-16 | 华北制药股份有限公司 | 一种直通式6-氨基青霉烷酸制备工艺 |
CN102925526A (zh) * | 2012-11-23 | 2013-02-13 | 华北制药河北华民药业有限责任公司 | 一种6-氨基青霉烷酸的制备方法 |
CN104004002A (zh) * | 2014-05-16 | 2014-08-27 | 河北天俱时生物科技有限公司 | 一种由青霉素发酵液直接制备6-氨基青霉烷酸的方法 |
-
2016
- 2016-03-28 CN CN201610182670.9A patent/CN105732663B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998048039A1 (en) * | 1997-04-22 | 1998-10-29 | Dsm N.V. | Improved process for the fermentative production of penicillin |
CN101735243A (zh) * | 2008-11-11 | 2010-06-16 | 华北制药股份有限公司 | 一种直通式6-氨基青霉烷酸制备工艺 |
CN102925526A (zh) * | 2012-11-23 | 2013-02-13 | 华北制药河北华民药业有限责任公司 | 一种6-氨基青霉烷酸的制备方法 |
CN104004002A (zh) * | 2014-05-16 | 2014-08-27 | 河北天俱时生物科技有限公司 | 一种由青霉素发酵液直接制备6-氨基青霉烷酸的方法 |
Non-Patent Citations (2)
Title |
---|
朱艳荣,等: "超声波协同酶激活剂法提取大蒜素的工艺研究", 《工业技术》 * |
禹邦超,刘德立: "《应用酶学导论》", 30 November 1995, 华中师范大学出版社 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108785728A (zh) * | 2017-05-05 | 2018-11-13 | 国家纳米科学中心 | 含药物中间体修饰的纳米金的抗菌敷料、其制备方法及应用 |
CN109535179A (zh) * | 2017-09-22 | 2019-03-29 | 联邦制药(内蒙古)有限公司 | 一种改进的6-apa提取方法 |
CN109535179B (zh) * | 2017-09-22 | 2020-05-22 | 联邦制药(内蒙古)有限公司 | 一种改进的6-apa提取方法 |
CN107686490A (zh) * | 2017-10-25 | 2018-02-13 | 陈磊 | 一种提取利福霉素b的方法 |
CN107686490B (zh) * | 2017-10-25 | 2020-02-07 | 南京久安源环保科技有限公司 | 一种提取利福霉素b的方法 |
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CN105732663B (zh) | 2018-03-16 |
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