CN101863862A - 一种工业半合成紫杉醇的方法 - Google Patents
一种工业半合成紫杉醇的方法 Download PDFInfo
- Publication number
- CN101863862A CN101863862A CN201010202911A CN201010202911A CN101863862A CN 101863862 A CN101863862 A CN 101863862A CN 201010202911 A CN201010202911 A CN 201010202911A CN 201010202911 A CN201010202911 A CN 201010202911A CN 101863862 A CN101863862 A CN 101863862A
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- Prior art keywords
- reaction
- phenyl
- baccatin iii
- doubly
- benzoyl
- 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
- 229930012538 Paclitaxel Natural products 0.000 title claims abstract description 48
- 229960001592 paclitaxel Drugs 0.000 title claims abstract description 47
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 14
- OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 claims abstract description 125
- 238000006243 chemical reaction Methods 0.000 claims abstract description 105
- 229930014667 baccatin III Natural products 0.000 claims abstract description 66
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 31
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000005886 esterification reaction Methods 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 61
- 239000000243 solution Substances 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- 230000004224 protection Effects 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- 238000001035 drying Methods 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000013019 agitation Methods 0.000 claims description 13
- YWLXLRUDGLRYDR-UHFFFAOYSA-N 10-deacetylbaccatin Chemical compound CC(=O)OC12COC1CC(O)C(C(C(O)C1=C(C)C(O)CC3(O)C1(C)C)=O)(C)C2C3OC(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 10
- 239000012266 salt solution Substances 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 8
- 238000001514 detection method Methods 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- 239000012043 crude product Substances 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 5
- 238000003379 elimination reaction Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 3
- 239000003518 caustics Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000035484 reaction time Effects 0.000 abstract description 6
- 239000011261 inert gas Substances 0.000 abstract description 2
- 230000000397 acetylating effect Effects 0.000 abstract 2
- 125000003834 baccatin III group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 230000000640 hydroxylating effect Effects 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 7
- -1 acetyl baccatin III Chemical compound 0.000 description 7
- 201000011510 cancer Diseases 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229960003668 docetaxel Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 230000008520 organization Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PSCJODZIMUSFCK-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazole-2-carboxylic acid Chemical class OC(=O)C1=NCCO1 PSCJODZIMUSFCK-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 241001149649 Taxus wallichiana var. chinensis Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 150000004200 baccatin III derivatives Chemical class 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000004579 taxol derivatives Chemical class 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
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CN2010102029114A CN101863862B (zh) | 2010-06-18 | 2010-06-18 | 一种工业半合成紫杉醇的方法 |
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CN2010102029114A CN101863862B (zh) | 2010-06-18 | 2010-06-18 | 一种工业半合成紫杉醇的方法 |
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CN101863862A true CN101863862A (zh) | 2010-10-20 |
CN101863862B CN101863862B (zh) | 2012-01-11 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102417491A (zh) * | 2011-10-31 | 2012-04-18 | 江苏红豆杉生物科技有限公司 | 以10-去乙酰基-巴卡丁iii为原料制备卡巴他赛的方法 |
CN103130753A (zh) * | 2013-03-14 | 2013-06-05 | 上海龙翔生物医药开发有限公司 | 抗肿瘤药物紫杉醇的半合成方法 |
CN103450118A (zh) * | 2013-09-18 | 2013-12-18 | 江苏红豆杉药业有限公司 | 一种半合成法制备紫杉醇的方法 |
CN108841888A (zh) * | 2018-07-31 | 2018-11-20 | 华南农业大学 | 乙酸酐作为酰基供体在参与dbat酶促反应中的应用 |
CN115260130A (zh) * | 2022-07-07 | 2022-11-01 | 上海卓鼎生物技术有限公司 | 一种10-脱乙酰基紫杉醇的制备方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102993137B (zh) * | 2012-12-13 | 2015-05-20 | 云南汉德生物技术有限公司 | 一种工业半合成多西紫杉醇的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5965739A (en) * | 1993-06-11 | 1999-10-12 | Pharmacia & Upjohn Company | Δ6,7 -taxols antineoplastic use and pharmaceutical compositions containing them |
CN101088994A (zh) * | 2006-06-12 | 2007-12-19 | 上海龙翔生物医药开发有限公司 | 一种紫杉醇和多西紫杉醇的合成方法 |
CN101468974A (zh) * | 2007-12-28 | 2009-07-01 | 上海百灵医药科技有限公司 | 多烯紫杉醇的半合成方法 |
-
2010
- 2010-06-18 CN CN2010102029114A patent/CN101863862B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5965739A (en) * | 1993-06-11 | 1999-10-12 | Pharmacia & Upjohn Company | Δ6,7 -taxols antineoplastic use and pharmaceutical compositions containing them |
CN101088994A (zh) * | 2006-06-12 | 2007-12-19 | 上海龙翔生物医药开发有限公司 | 一种紫杉醇和多西紫杉醇的合成方法 |
CN101468974A (zh) * | 2007-12-28 | 2009-07-01 | 上海百灵医药科技有限公司 | 多烯紫杉醇的半合成方法 |
Non-Patent Citations (4)
Title |
---|
《J Chem Soc Chem Commun》 19981231 Kanazawa A M,Denis J N,Greene A E. Direct,stereoselective synthesis of the proteced paclitaxel side chain and high yield transformation to paclitaxel. 2591-2592 1-6 第22卷, 2 * |
《Tetrahedron Lett》 19921231 Commercon A,Bezard D,Bernard F et al. Improved protection and esterification of a precursor of the TAXOTERE and taxol side chains 5185-5188 1-6 第33卷, 第5期 2 * |
《中国医药工业杂志》 20090228 李 鹏,李春香 多西他赛的合成 90-92 1-6 第40卷, 第2期 2 * |
《中国民族民间医药》 20100131 孙浩岩; 黄兴富; 唐艳梅; 王继良 具有实用价值紫杉醇半合成路线概述 , 第13期 2 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102417491A (zh) * | 2011-10-31 | 2012-04-18 | 江苏红豆杉生物科技有限公司 | 以10-去乙酰基-巴卡丁iii为原料制备卡巴他赛的方法 |
CN102417491B (zh) * | 2011-10-31 | 2013-11-06 | 江苏红豆杉生物科技有限公司 | 以10-去乙酰基-巴卡丁iii为原料制备卡巴他赛的方法 |
CN103130753A (zh) * | 2013-03-14 | 2013-06-05 | 上海龙翔生物医药开发有限公司 | 抗肿瘤药物紫杉醇的半合成方法 |
CN103130753B (zh) * | 2013-03-14 | 2015-09-02 | 上海龙翔生物医药开发有限公司 | 抗肿瘤药物紫杉醇的半合成方法 |
CN103450118A (zh) * | 2013-09-18 | 2013-12-18 | 江苏红豆杉药业有限公司 | 一种半合成法制备紫杉醇的方法 |
CN108841888A (zh) * | 2018-07-31 | 2018-11-20 | 华南农业大学 | 乙酸酐作为酰基供体在参与dbat酶促反应中的应用 |
CN108841888B (zh) * | 2018-07-31 | 2021-05-28 | 华南农业大学 | 乙酸酐作为酰基供体在参与dbat酶促反应中的应用 |
CN115260130A (zh) * | 2022-07-07 | 2022-11-01 | 上海卓鼎生物技术有限公司 | 一种10-脱乙酰基紫杉醇的制备方法 |
Also Published As
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CN101863862B (zh) | 2012-01-11 |
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