CN1438237A - Echinocystic acid preparation, medicinal preparation and new use as medicine - Google Patents
Echinocystic acid preparation, medicinal preparation and new use as medicine Download PDFInfo
- Publication number
- CN1438237A CN1438237A CN 03100676 CN03100676A CN1438237A CN 1438237 A CN1438237 A CN 1438237A CN 03100676 CN03100676 CN 03100676 CN 03100676 A CN03100676 A CN 03100676A CN 1438237 A CN1438237 A CN 1438237A
- Authority
- CN
- China
- Prior art keywords
- ethanol
- filter
- echinocystic acid
- acid
- filtrate
- 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
- YKOPWPOFWMYZJZ-FMMUPTMQSA-N Echinocystic acid Natural products C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)C[C@H](O)[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C YKOPWPOFWMYZJZ-FMMUPTMQSA-N 0.000 title claims abstract description 72
- YKOPWPOFWMYZJZ-UHFFFAOYSA-N Echinocystsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CC(O)C5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C YKOPWPOFWMYZJZ-UHFFFAOYSA-N 0.000 title claims abstract description 72
- MCHWKJRTMPIHRA-UHFFFAOYSA-N n-(pyrrolidin-2-ylmethyl)aniline Chemical compound C1CCNC1CNC1=CC=CC=C1 MCHWKJRTMPIHRA-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 239000003814 drug Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 132
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000000463 material Substances 0.000 claims abstract description 17
- 210000004351 coronary vessel Anatomy 0.000 claims abstract description 11
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 10
- 208000029078 coronary artery disease Diseases 0.000 claims abstract description 8
- 238000000746 purification Methods 0.000 claims abstract description 5
- 239000011347 resin Substances 0.000 claims abstract description 5
- 229920005989 resin Polymers 0.000 claims abstract description 5
- 235000019441 ethanol Nutrition 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000000243 solution Substances 0.000 claims description 28
- 241000931143 Gleditsia sinensis Species 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- 239000000706 filtrate Substances 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 24
- 230000006837 decompression Effects 0.000 claims description 16
- 239000008367 deionised water Substances 0.000 claims description 16
- 229910021641 deionized water Inorganic materials 0.000 claims description 16
- 239000012065 filter cake Substances 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 16
- 208000031225 myocardial ischemia Diseases 0.000 claims description 15
- 230000007062 hydrolysis Effects 0.000 claims description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims description 12
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 12
- 229930182490 saponin Natural products 0.000 claims description 12
- 150000007949 saponins Chemical class 0.000 claims description 12
- 235000017709 saponins Nutrition 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000006187 pill Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000012141 concentrate Substances 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 235000013399 edible fruits Nutrition 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003463 adsorbent Substances 0.000 claims description 4
- 210000000481 breast Anatomy 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
- 239000000920 calcium hydroxide Substances 0.000 claims description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 4
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000292 calcium oxide Substances 0.000 claims description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- 239000000443 aerosol Substances 0.000 claims description 2
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000019634 flavors Nutrition 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 210000004165 myocardium Anatomy 0.000 abstract description 6
- 239000008280 blood Substances 0.000 abstract description 3
- 210000004369 blood Anatomy 0.000 abstract description 3
- 239000000284 extract Substances 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 229930182478 glucoside Natural products 0.000 abstract 1
- 150000008131 glucosides Chemical class 0.000 abstract 1
- 239000012264 purified product Substances 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 241000282472 Canis lupus familiaris Species 0.000 description 10
- 230000017531 blood circulation Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 6
- 206010061216 Infarction Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 230000007574 infarction Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000008899 fufang danshen Substances 0.000 description 4
- 210000002216 heart Anatomy 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000002183 duodenal effect Effects 0.000 description 3
- 210000001198 duodenum Anatomy 0.000 description 3
- 210000003516 pericardium Anatomy 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 206010008132 Cerebral thrombosis Diseases 0.000 description 2
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 210000003191 femoral vein Anatomy 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ZGZLYKUHYXFIIO-UHFFFAOYSA-N 5-nitro-2h-tetrazole Chemical compound [O-][N+](=O)C=1N=NNN=1 ZGZLYKUHYXFIIO-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000533849 Gleditsia Species 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229940126678 chinese medicines Drugs 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000009524 danshen dripping Substances 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000003601 intercostal effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TZBAVQKIEKDGFH-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-1-benzothiophene-2-carboxamide;hydrochloride Chemical compound [Cl-].C1=CC=C2SC(C(=O)NCC[NH+](CC)CC)=CC2=C1 TZBAVQKIEKDGFH-UHFFFAOYSA-N 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- -1 polyoxyethylene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000012109 statistical procedure Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000008130 triterpenoid saponins Chemical class 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 235000020985 whole grains Nutrition 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 03100676 CN1216896C (en) | 2003-01-21 | 2003-01-21 | Echinocystic acid preparation, medicinal preparation and new use as medicine |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 03100676 CN1216896C (en) | 2003-01-21 | 2003-01-21 | Echinocystic acid preparation, medicinal preparation and new use as medicine |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1438237A true CN1438237A (en) | 2003-08-27 |
CN1216896C CN1216896C (en) | 2005-08-31 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 03100676 Expired - Lifetime CN1216896C (en) | 2003-01-21 | 2003-01-21 | Echinocystic acid preparation, medicinal preparation and new use as medicine |
Country Status (1)
Country | Link |
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CN (1) | CN1216896C (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010130152A1 (en) * | 2009-05-15 | 2010-11-18 | 成都康弘制药有限公司 | Pharmaceutical composition for treating cardiovascular disorder and use thereof |
CN102240293A (en) * | 2010-05-11 | 2011-11-16 | 成都康弘制药有限公司 | Application of echinocystic acid in preparing medicament preventing and treating cardiovascular diseases |
CN101919901B (en) * | 2009-06-10 | 2012-01-11 | 赵全成 | Application of total aglycone of Gleditsia sinensis Lam in preparation of alpha-glucosidase inhibitor drugs |
CN102464698A (en) * | 2010-11-19 | 2012-05-23 | 苏州宝泽堂医药科技有限公司 | Method for preparing high-content echinocystic acid |
CN103145790A (en) * | 2013-03-18 | 2013-06-12 | 山东省中医药研究院 | Method for simultaneously preparing oleanolic acid and echinocystic acid from fructus gleditsiae |
WO2014063441A1 (en) * | 2012-10-22 | 2014-05-01 | 北京大学 | Triterpene derivative and its anti-influenza use |
CN106550942A (en) * | 2016-10-17 | 2017-04-05 | 徐州得铸生物科技有限公司 | A kind of bactericidal composition containing 1,8 cineoles |
CN110563792A (en) * | 2019-09-09 | 2019-12-13 | 南开大学 | G protein coupled bile acid receptor agonist and application thereof |
-
2003
- 2003-01-21 CN CN 03100676 patent/CN1216896C/en not_active Expired - Lifetime
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010130152A1 (en) * | 2009-05-15 | 2010-11-18 | 成都康弘制药有限公司 | Pharmaceutical composition for treating cardiovascular disorder and use thereof |
JP2012526730A (en) * | 2009-05-15 | 2012-11-01 | 成都康弘制薬有限公司 | Pharmaceutical composition for the treatment of cardiovascular disorders and use thereof |
CN101919901B (en) * | 2009-06-10 | 2012-01-11 | 赵全成 | Application of total aglycone of Gleditsia sinensis Lam in preparation of alpha-glucosidase inhibitor drugs |
CN102240293A (en) * | 2010-05-11 | 2011-11-16 | 成都康弘制药有限公司 | Application of echinocystic acid in preparing medicament preventing and treating cardiovascular diseases |
CN102240293B (en) * | 2010-05-11 | 2013-04-24 | 成都康弘制药有限公司 | Application of echinocystic acid in preparing medicament preventing and treating cardiovascular diseases |
CN102464698A (en) * | 2010-11-19 | 2012-05-23 | 苏州宝泽堂医药科技有限公司 | Method for preparing high-content echinocystic acid |
JP2015535222A (en) * | 2012-10-22 | 2015-12-10 | 北京大学 | Triterpene derivatives and their use for anti-influenza |
WO2014063441A1 (en) * | 2012-10-22 | 2014-05-01 | 北京大学 | Triterpene derivative and its anti-influenza use |
CN103768078A (en) * | 2012-10-22 | 2014-05-07 | 北京大学 | Triterpenoid derivatives and anti-influenza application thereof |
EP2910563A4 (en) * | 2012-10-22 | 2016-05-25 | Univ Beijing | Triterpene derivative and its anti-influenza use |
US9920088B2 (en) | 2012-10-22 | 2018-03-20 | University of Macao | Triterpene derivative and its anti-influenza use |
CN103768078B (en) * | 2012-10-22 | 2019-02-05 | 北京大学 | Tetraterpene derivatives and its anti influenza purposes |
CN103145790A (en) * | 2013-03-18 | 2013-06-12 | 山东省中医药研究院 | Method for simultaneously preparing oleanolic acid and echinocystic acid from fructus gleditsiae |
CN106550942A (en) * | 2016-10-17 | 2017-04-05 | 徐州得铸生物科技有限公司 | A kind of bactericidal composition containing 1,8 cineoles |
CN110563792A (en) * | 2019-09-09 | 2019-12-13 | 南开大学 | G protein coupled bile acid receptor agonist and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CN1216896C (en) | 2005-08-31 |
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Owner name: CHENGDU KANGHONG TECHNOLOGY INDUSTRIAL (GROUP) CO Free format text: FORMER OWNER: TIANYAO SCIENCE AND TECHNOLOGY CO LTD, JILIN Effective date: 20060317 |
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Owner name: CHENGDU KANGHONG PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: CHENGDU KANGHONG TECHNOLOGY INDUSTRIAL (GROUP) CO., LTD. Effective date: 20080912 |
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