CN107304214B - 水溶性银杏内酯b氨基甲酸酯衍生物及其制备方法和用途 - Google Patents
水溶性银杏内酯b氨基甲酸酯衍生物及其制备方法和用途 Download PDFInfo
- Publication number
- CN107304214B CN107304214B CN201610240216.4A CN201610240216A CN107304214B CN 107304214 B CN107304214 B CN 107304214B CN 201610240216 A CN201610240216 A CN 201610240216A CN 107304214 B CN107304214 B CN 107304214B
- Authority
- CN
- China
- Prior art keywords
- ginkgolide
- carbamate
- isocyanate
- preparation
- carbamate derivative
- 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.)
- Active
Links
- SQOJOAFXDQDRGF-WJHVHIKBSA-N ginkgolide B Natural products O=C1[C@@H](C)[C@@]2(O)[C@@H]([C@H](O)[C@]34[C@@H]5OC(=O)[C@]23O[C@H]2OC(=O)[C@H](O)[C@@]42[C@H](C(C)(C)C)C5)O1 SQOJOAFXDQDRGF-WJHVHIKBSA-N 0.000 title claims abstract description 70
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- SQOJOAFXDQDRGF-MMQTXUMRSA-N ginkgolide-b Chemical compound O[C@H]([C@]12[C@H](C(C)(C)C)C[C@H]3OC4=O)C(=O)O[C@H]2O[C@]24[C@@]13[C@@H](O)[C@@H]1OC(=O)[C@@H](C)[C@]21O SQOJOAFXDQDRGF-MMQTXUMRSA-N 0.000 title claims abstract 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000012948 isocyanate Substances 0.000 claims abstract description 9
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 230000035484 reaction time Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims abstract 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- SQNBLZUUQXAIBW-UHFFFAOYSA-N (3-bromophenyl) carbamate Chemical compound NC(=O)OC1=CC=CC(Br)=C1 SQNBLZUUQXAIBW-UHFFFAOYSA-N 0.000 claims description 10
- AUELWJRRASQDKI-UHFFFAOYSA-N cyclohexyl carbamate Chemical compound NC(=O)OC1CCCCC1 AUELWJRRASQDKI-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- -1 ginkgolide B carbamate derivatives Chemical class 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- VQVBCZQTXSHJGF-UHFFFAOYSA-N 1-bromo-3-isocyanatobenzene Chemical group BrC1=CC=CC(N=C=O)=C1 VQVBCZQTXSHJGF-UHFFFAOYSA-N 0.000 claims description 3
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003146 anticoagulant agent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 229960004676 antithrombotic agent Drugs 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 6
- 238000004440 column chromatography Methods 0.000 abstract description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 238000011161 development Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 2
- 150000001555 benzenes Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001924 cycloalkanes Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- SQOJOAFXDQDRGF-ZMVGXLHTSA-N ginkgolide b Chemical compound O[C@H]([C@]12[C@H](C(C)(C)C)C[C@H]3OC4=O)C(=O)O[C@H]2O[C@]24[C@@]13[C@H](O)[C@@H]1OC(=O)[C@@H](C)[C@]21O SQOJOAFXDQDRGF-ZMVGXLHTSA-N 0.000 description 56
- 241000252212 Danio rerio Species 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- 229930063422 Bilobalide A Natural products 0.000 description 6
- 230000002785 anti-thrombosis Effects 0.000 description 6
- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 5
- 108010003541 Platelet Activating Factor Proteins 0.000 description 5
- 210000003050 axon Anatomy 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 230000002093 peripheral effect Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000011201 Ginkgo Nutrition 0.000 description 2
- 241000218628 Ginkgo Species 0.000 description 2
- 235000008100 Ginkgo biloba Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- MOLPUWBMSBJXER-YDGSQGCISA-N bilobalide Chemical compound O([C@H]1OC2=O)C(=O)[C@H](O)[C@@]11[C@@](C(C)(C)C)(O)C[C@H]3[C@@]21CC(=O)O3 MOLPUWBMSBJXER-YDGSQGCISA-N 0.000 description 2
- 229930004069 diterpene Natural products 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000001627 cerebral artery Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229930184727 ginkgolide Natural products 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000012151 immunohistochemical method Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000003848 thrombocyte activating factor antagonist Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
化合物 | 溶解度(mg/mL) |
银杏内酯B | <0.2 |
10-O-(间溴苯基氨基甲酸酯)银杏内酯B | 30-35 |
10-O-(环己基氨基甲酸酯)银杏内酯B | 55-60 |
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610240216.4A CN107304214B (zh) | 2016-04-18 | 2016-04-18 | 水溶性银杏内酯b氨基甲酸酯衍生物及其制备方法和用途 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610240216.4A CN107304214B (zh) | 2016-04-18 | 2016-04-18 | 水溶性银杏内酯b氨基甲酸酯衍生物及其制备方法和用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN107304214A CN107304214A (zh) | 2017-10-31 |
CN107304214B true CN107304214B (zh) | 2021-04-06 |
Family
ID=60152029
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610240216.4A Active CN107304214B (zh) | 2016-04-18 | 2016-04-18 | 水溶性银杏内酯b氨基甲酸酯衍生物及其制备方法和用途 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN107304214B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115109068B (zh) * | 2021-03-19 | 2024-05-24 | 澳门科技大学 | 用于预防或治疗心脑血管疾病的化合物及其制备方法和应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005021496A2 (en) * | 2003-08-27 | 2005-03-10 | The Trustees Of Columbia University In The City Of New York | Synthesis of derivatives of ginkgolide c |
CN1837212A (zh) * | 2006-04-26 | 2006-09-27 | 秦引林 | 银杏内酯b衍生物及其在制药中的应用 |
CN1837213A (zh) * | 2006-04-26 | 2006-09-27 | 秦引林 | 银杏内酯a衍生物及其在制药中的应用 |
CN104098584A (zh) * | 2013-04-03 | 2014-10-15 | 广东东阳光药业有限公司 | 银杏内酯b衍生物及其在药物中的应用 |
CN105367582A (zh) * | 2014-08-11 | 2016-03-02 | 广东东阳光药业有限公司 | 银杏内酯b衍生物及其在药物中的应用 |
-
2016
- 2016-04-18 CN CN201610240216.4A patent/CN107304214B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005021496A2 (en) * | 2003-08-27 | 2005-03-10 | The Trustees Of Columbia University In The City Of New York | Synthesis of derivatives of ginkgolide c |
CN1837212A (zh) * | 2006-04-26 | 2006-09-27 | 秦引林 | 银杏内酯b衍生物及其在制药中的应用 |
CN1837213A (zh) * | 2006-04-26 | 2006-09-27 | 秦引林 | 银杏内酯a衍生物及其在制药中的应用 |
CN104098584A (zh) * | 2013-04-03 | 2014-10-15 | 广东东阳光药业有限公司 | 银杏内酯b衍生物及其在药物中的应用 |
CN105367582A (zh) * | 2014-08-11 | 2016-03-02 | 广东东阳光药业有限公司 | 银杏内酯b衍生物及其在药物中的应用 |
Non-Patent Citations (1)
Title |
---|
银杏内酯类化合物的结构修饰与构效关系研究进展;常玉等;《中药材》;20130331;第36卷(第3期);第497-501页 * |
Also Published As
Publication number | Publication date |
---|---|
CN107304214A (zh) | 2017-10-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE60201890T2 (de) | Synthese von beta-lapachone und entsprechender zwischenprodukte | |
DE69530592T2 (de) | Verfahren zur herstellung von (+/-) calanolide a und zwischenprodukte dafür | |
JP2009545594A (ja) | 改善された効能、安定性および安全性を有する疑似塩基ベンゾ[c]フェナントリジン | |
EP0656353A1 (de) | Aminochinolin-Derivate mit einer Wirksamkeit gegen Malariaerreger | |
CN100358899C (zh) | 一类抗血小板活化因子化合物 | |
DE3623300A1 (de) | 7-acyloxy-6-aminoacyloxypolyoxylabdane, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
CN107304214B (zh) | 水溶性银杏内酯b氨基甲酸酯衍生物及其制备方法和用途 | |
DE2650845A1 (de) | Neue spiro-(1,3-dioxolan-4,3')- quinuclidine | |
DE2311131B2 (de) | Amidinopenicillansäureester, Verfahren zu deren Herstellung und pharmazeutische Mittel | |
DE60012750T2 (de) | Neue xanthon derivate, deren herstellung und verwendung als arzneimittel | |
EP0736535B1 (de) | Verfahren zur Herstellung von Dihydroartemisinin-hemisuccinat | |
DE1802162A1 (de) | Neue N-Pyridylmethyliden-homocystein-thiolacton-Verbindung und Verfahren zu ihrer Herstellung | |
US3366629A (en) | Alkaloids of mitragyna ciliata | |
CN104860847B (zh) | 利凡斯的明和咖啡酸、阿魏酸的二聚体,其制备方法及其药物组合物 | |
DE69819340T2 (de) | Optisch reine camptothecinanaloge, optisch reines synthese-zwischenprodukt und verfahren zu ihrer herstellung | |
DE3512629C2 (de) | s-Triazolo[1,5-a]pyrimidine und Verfahren zu ihrer Herstellung | |
CN101973938B (zh) | C环氢化青藤碱衍生物及其制备方法和应用 | |
DE3625738A1 (de) | 2-acyloxypropylamin-derivate, verfahren zu deren herstellung und deren verwendung | |
DE602005005308T2 (de) | Verfahren zur herstellung von 3-amino-8-(1-piperazinyl)-2h-1-benzopyran-2-on und seinen salzen und hydraten | |
DE60113278T2 (de) | Cumarin-derivate und ihre salze, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung | |
DE2748466A1 (de) | 4a-aryloctahydro-1h-2-pyrindine | |
DE60132981T2 (de) | Duale moleküle enthaltend ein peroxydderivat,deren synthese und deren verwendung als heilmittel | |
DE112020006237T5 (de) | Deuterierte Analoga von Selenophenochromenen, deren Synthese und Verfahren zur Verwendung dieser Mittel | |
CN107602518B (zh) | 香豆素-二硫代氨基甲酸酯衍生物及其合成方法 | |
CN1900082A (zh) | 抗血小板活化因子的药物化合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Water soluble ginkgolide B carbamate derivatives and their preparation methods and applications Effective date of registration: 20221024 Granted publication date: 20210406 Pledgee: Bank of China Limited Lanxi Sub-branch Pledgor: ZHEJIANG CONBA PHARMACEUTICAL Co.,Ltd. Registration number: Y2022980019363 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20210406 Pledgee: Bank of China Limited Lanxi Sub-branch Pledgor: ZHEJIANG CONBA PHARMACEUTICAL Co.,Ltd. Registration number: Y2022980019363 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right |