CN102241724B - 一种齐墩果酸盐及其制备方法和晶体 - Google Patents
一种齐墩果酸盐及其制备方法和晶体 Download PDFInfo
- Publication number
- CN102241724B CN102241724B CN201010171882.XA CN201010171882A CN102241724B CN 102241724 B CN102241724 B CN 102241724B CN 201010171882 A CN201010171882 A CN 201010171882A CN 102241724 B CN102241724 B CN 102241724B
- Authority
- CN
- China
- Prior art keywords
- oleanolic acid
- solvent
- cooling
- ethylenediamine salt
- crystal seed
- 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
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 85
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 claims abstract description 129
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 claims abstract description 129
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 claims abstract description 129
- 229940100243 oleanolic acid Drugs 0.000 claims abstract description 129
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 claims abstract description 129
- -1 Oleanolic Acid ethylenediamine salt Chemical class 0.000 claims abstract description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000126 substance Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 80
- 238000001816 cooling Methods 0.000 claims description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 40
- 238000002425 crystallisation Methods 0.000 claims description 39
- 230000008025 crystallization Effects 0.000 claims description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- 239000012296 anti-solvent Substances 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 22
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 14
- 238000006386 neutralization reaction Methods 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 5
- 229940011051 isopropyl acetate Drugs 0.000 claims description 5
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 2
- 230000001143 conditioned effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 abstract description 13
- 238000004090 dissolution Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 18
- 239000003814 drug Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 238000001291 vacuum drying Methods 0.000 description 16
- 238000012360 testing method Methods 0.000 description 14
- 238000004088 simulation Methods 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 9
- 229940079593 drug Drugs 0.000 description 8
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 8
- 230000000968 intestinal effect Effects 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 210000004051 gastric juice Anatomy 0.000 description 4
- 230000006911 nucleation Effects 0.000 description 4
- 238000010899 nucleation Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229940079833 sodium oleanolate Drugs 0.000 description 4
- QNELTPKHJFMSNK-RLFONNADSA-M sodium;(4as,6ar,6as,6br,8ar,10s,12ar,14bs)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate Chemical compound [Na+].C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C([O-])=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C QNELTPKHJFMSNK-RLFONNADSA-M 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000003321 amplification Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003199 nucleic acid amplification method Methods 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000003028 elevating effect Effects 0.000 description 2
- 208000006454 hepatitis Diseases 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010583 slow cooling Methods 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000000935 solvent evaporation Methods 0.000 description 2
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 1
- 108010082126 Alanine transaminase Proteins 0.000 description 1
- 241000459479 Capsula Species 0.000 description 1
- 239000004381 Choline salt Substances 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 229910016860 FaSSIF Inorganic materials 0.000 description 1
- 229910005429 FeSSIF Inorganic materials 0.000 description 1
- 206010020852 Hypertonia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 231100000354 acute hepatitis Toxicity 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 125000001664 diethylamino group Chemical class [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 239000007919 dispersible tablet Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000753 hepatic injury Toxicity 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012067 mathematical method Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000011858 nanopowder Substances 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000006191 orally-disintegrating tablet Substances 0.000 description 1
- 150000002966 pentacyclic triterpenoids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000014860 sensory perception of taste Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201010171882.XA CN102241724B (zh) | 2010-05-11 | 2010-05-11 | 一种齐墩果酸盐及其制备方法和晶体 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201010171882.XA CN102241724B (zh) | 2010-05-11 | 2010-05-11 | 一种齐墩果酸盐及其制备方法和晶体 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102241724A CN102241724A (zh) | 2011-11-16 |
CN102241724B true CN102241724B (zh) | 2015-12-09 |
Family
ID=44959995
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201010171882.XA Expired - Fee Related CN102241724B (zh) | 2010-05-11 | 2010-05-11 | 一种齐墩果酸盐及其制备方法和晶体 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102241724B (zh) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1449372A (zh) * | 2000-08-08 | 2003-10-15 | 日清奥利友株式会社 | 齐墩果酸和/或山楂酸的制备方法 |
CN1911450A (zh) * | 2006-08-21 | 2007-02-14 | 沈阳药科大学 | 一种含d-半乳糖和甾醇或脂肪醇的肝靶向辅料及其制剂 |
US20090143279A1 (en) * | 2007-06-15 | 2009-06-04 | Vamsi Krishna Mootha | Methods and compositions for treating metabolic disorders |
-
2010
- 2010-05-11 CN CN201010171882.XA patent/CN102241724B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1449372A (zh) * | 2000-08-08 | 2003-10-15 | 日清奥利友株式会社 | 齐墩果酸和/或山楂酸的制备方法 |
CN1911450A (zh) * | 2006-08-21 | 2007-02-14 | 沈阳药科大学 | 一种含d-半乳糖和甾醇或脂肪醇的肝靶向辅料及其制剂 |
US20090143279A1 (en) * | 2007-06-15 | 2009-06-04 | Vamsi Krishna Mootha | Methods and compositions for treating metabolic disorders |
Also Published As
Publication number | Publication date |
---|---|
CN102241724A (zh) | 2011-11-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Sarode et al. | Supersaturation, nucleation, and crystal growth during single-and biphasic dissolution of amorphous solid dispersions: Polymer effects and implications for oral bioavailability enhancement of poorly water soluble drugs | |
CN104736526B (zh) | 沃替西汀盐及其晶体、它们的制备方法、药物组合物和用途 | |
Lu et al. | Maintaining supersaturation of active pharmaceutical ingredient solutions with biologically relevant bile salts | |
Thakuria et al. | Cocrystal dissociation under controlled humidity: a case study of caffeine–glutaric acid cocrystal polymorphs | |
Xiong et al. | Solid dispersions of telaprevir with improved solubility prepared by co-milling: formulation, physicochemical characterization, and cytotoxicity evaluation | |
CN105121434A (zh) | 坎格列净一水合物及其晶型、它们的制备方法和用途 | |
CN104017031A (zh) | 降血糖药物和组合物 | |
CN104031098A (zh) | 降糖药物 | |
Li et al. | Three-solvent spherical crystallization method with a model drug: Clopidogrel hydrogen sulfate | |
Chen et al. | Modified rivaroxaban microparticles for solid state properties improvement based on drug-protein/polymer supramolecular interactions | |
CN101987863B (zh) | 一种齐墩果酸哌嗪盐及其制备方法 | |
CN102234304B (zh) | 一种熊果酸盐、其制备方法及其晶体 | |
Yu et al. | Effect of natural polymer additives on crystal form and morphology of clozapine anhydrate and monohydrate | |
CN102241724B (zh) | 一种齐墩果酸盐及其制备方法和晶体 | |
CN104326970B (zh) | 左旋氨氯地平马来酸盐化合物及制备方法与含其药物制剂 | |
CN104448057B (zh) | 一种纳米级阿魏酸蔗渣木聚糖酯的制备方法 | |
CN102241723B (zh) | 一种熊果酸盐及其制备方法和晶体 | |
CN103724374A (zh) | 一种苯磷硫胺化合物及制备方法及其含有该化合物的药物组合物 | |
CN102442990B (zh) | 一种金雀异黄素烟酰胺共晶、其晶体及其制备方法 | |
Yu et al. | Cocrystallization of urea and succinic acid in “Nano-Crystallizer” | |
CN104540822A (zh) | 达拉菲尼甲磺酸盐的新晶型及其制备方法 | |
CN102442989B (zh) | 一种金雀异黄素盐、其晶体及其制备方法 | |
WO2008019053A2 (en) | Process for preparing clopidogrel bisulphate | |
CN102442991B (zh) | 一种金雀异黄素维生素b6共晶、其晶体及其制备方法 | |
CN102892749B (zh) | 阿戈美拉汀溴化氢水合物及其制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C41 | Transfer of patent application or patent right or utility model | ||
C56 | Change in the name or address of the patentee | ||
CP01 | Change in the name or title of a patent holder |
Address after: 201203 Shanghai City Harley Road, Zhangjiang hi tech Park No. 965 Room 303 Patentee after: SHANGHAI PHARMAEXPLORER Co.,Ltd. Address before: 201203 Shanghai City Harley Road, Zhangjiang hi tech Park No. 965 Room 303 Patentee before: Shanghai PharmaExplorer Co.,Ltd. |
|
TR01 | Transfer of patent right |
Effective date of registration: 20170110 Address after: 201203 Shanghai City Harley Road, Pudong New Area Zhangjiang hi tech Park No. 965, No. 3 building two floor Patentee after: SHANGHAI CHEMEXPLORER Co.,Ltd. Address before: 201203 Shanghai City Harley Road, Zhangjiang hi tech Park No. 965 Room 303 Patentee before: SHANGHAI PHARMAEXPLORER Co.,Ltd. |
|
TR01 | Transfer of patent right |
Effective date of registration: 20170612 Address after: 201203 Shanghai Zhangjiang High Tech Park of Pudong New Area Cailun Road No. 3 Building No. 302 room 720 Patentee after: XDCEXPLORER (SHANGHAI) Co.,Ltd. Address before: 201203 Shanghai City Harley Road, Pudong New Area Zhangjiang hi tech Park No. 965, No. 3 building two floor Patentee before: SHANGHAI CHEMEXPLORER Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20151209 |
|
CF01 | Termination of patent right due to non-payment of annual fee |