CN101302244A - 一种桦木酸的生产方法 - Google Patents
一种桦木酸的生产方法 Download PDFInfo
- Publication number
- CN101302244A CN101302244A CNA2008100646757A CN200810064675A CN101302244A CN 101302244 A CN101302244 A CN 101302244A CN A2008100646757 A CNA2008100646757 A CN A2008100646757A CN 200810064675 A CN200810064675 A CN 200810064675A CN 101302244 A CN101302244 A CN 101302244A
- Authority
- CN
- China
- Prior art keywords
- betulinic acid
- crude product
- betulin
- betulinaldehyde
- milliliters
- 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
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 title claims abstract description 61
- QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 title claims abstract description 60
- CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 title claims abstract description 60
- DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 title claims abstract description 60
- PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 title claims abstract description 60
- MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 239000012043 crude product Substances 0.000 claims abstract description 47
- AKUYURNRLXSOLV-AYKZKCBTSA-N Betulinaldehyde Natural products C[C@H]1CC[C@@]2(C)[C@H](CC[C@@]3(C)[C@@H]4CC[C@]5(CC[C@H]([C@H]5[C@@H]4CC[C@@H]23)C(=C)C)C=C)C1(C)C AKUYURNRLXSOLV-AYKZKCBTSA-N 0.000 claims abstract description 25
- FELCJAPFJOPHSD-ROUWMTJPSA-N Lup-20(29)-en-28-al, 3beta-hydroxy- Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C FELCJAPFJOPHSD-ROUWMTJPSA-N 0.000 claims abstract description 25
- FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C FVWJYYTZTCVBKE-ROUWMTJPSA-N 0.000 claims abstract description 25
- MVIRREHRVZLANQ-UHFFFAOYSA-N betulin Natural products CC(=O)OC1CCC2(C)C(CCC3(C)C2CC=C4C5C(CCC5(CO)CCC34C)C(=C)C)C1(C)C MVIRREHRVZLANQ-UHFFFAOYSA-N 0.000 claims abstract description 25
- MHAVMNJPXLZEIG-UHFFFAOYSA-N betulinic aldehyde Natural products C1CC(=O)C(C)(C)C2CCC3(C)C4(C)CCC5(C=O)CCC(C(=C)C)C5C4CCC3C21C MHAVMNJPXLZEIG-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000000047 product Substances 0.000 claims abstract description 17
- 238000001953 recrystallisation Methods 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- JYDNKGUBLIKNAM-UHFFFAOYSA-N Oxyallobutulin Natural products C1CC(=O)C(C)(C)C2CCC3(C)C4(C)CCC5(CO)CCC(C(=C)C)C5C4CCC3C21C JYDNKGUBLIKNAM-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000012141 concentrate Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 229950009390 symclosene Drugs 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 11
- ZNUAKACHFYTNFX-UHFFFAOYSA-N Wallichenol Natural products CC12CCC(O)C(C)(C)C1CCC1(C)C2CCC2C3C(C(=C)CO)CCC3(C)CCC21C ZNUAKACHFYTNFX-UHFFFAOYSA-N 0.000 abstract 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 7
- 238000013019 agitation Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000011182 sodium carbonates Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- SLJTWDNVZKIDAU-CKURCAGRSA-N Betulonic acid Natural products CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O SLJTWDNVZKIDAU-CKURCAGRSA-N 0.000 description 1
- SLJTWDNVZKIDAU-SVAFSPIFSA-N Betulonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C SLJTWDNVZKIDAU-SVAFSPIFSA-N 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 238000006809 Jones oxidation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000024053 secondary metabolic process Effects 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Claims (5)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2008100646757A CN101302244B (zh) | 2008-06-06 | 2008-06-06 | 一种桦木酸的生产方法 |
PCT/CN2009/071271 WO2009146619A1 (zh) | 2008-06-06 | 2009-04-15 | 一种桦木酸的生产方法 |
CA2705902A CA2705902C (en) | 2008-06-06 | 2009-04-15 | A method for producing betulinic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2008100646757A CN101302244B (zh) | 2008-06-06 | 2008-06-06 | 一种桦木酸的生产方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101302244A true CN101302244A (zh) | 2008-11-12 |
CN101302244B CN101302244B (zh) | 2011-04-13 |
Family
ID=40112358
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2008100646757A Expired - Fee Related CN101302244B (zh) | 2008-06-06 | 2008-06-06 | 一种桦木酸的生产方法 |
Country Status (3)
Country | Link |
---|---|
CN (1) | CN101302244B (zh) |
CA (1) | CA2705902C (zh) |
WO (1) | WO2009146619A1 (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009146619A1 (zh) * | 2008-06-06 | 2009-12-10 | 东北林业大学 | 一种桦木酸的生产方法 |
CN102344482A (zh) * | 2011-07-29 | 2012-02-08 | 温州大学 | 桦木醇衍生物、制备方法及用途 |
CN103626827A (zh) * | 2012-08-29 | 2014-03-12 | 奇复康药物研发(苏州)有限公司 | 一种白桦酸标准品制备方法 |
CN112811995A (zh) * | 2021-01-14 | 2021-05-18 | 惠泽化学科技(濮阳)有限公司 | 一种4-取代基环己酮类液晶中间体的合成方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE536995C2 (sv) * | 2011-09-12 | 2014-11-25 | Stora Enso Oyj | Förfarande för derivatisering av en kemisk komponent i trä |
SE537100C2 (sv) * | 2011-09-12 | 2015-01-07 | Stora Enso Oyj | Förfarande för derivatisering av en kemisk komponent i trä |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5804575A (en) * | 1997-03-27 | 1998-09-08 | The Board Of Trustees Of The University Of Illinois | Methods of manufacturing betulinic acid |
US6232481B1 (en) * | 2000-01-11 | 2001-05-15 | Regents Of The University Of Minnesota | Method for manufacturing betulinic acid |
CA2603124A1 (en) * | 2005-03-29 | 2006-10-05 | Regents Of The University Of Minnesota | Selective oxidation of triterpenes employing tempo |
CN101302244B (zh) * | 2008-06-06 | 2011-04-13 | 东北林业大学 | 一种桦木酸的生产方法 |
-
2008
- 2008-06-06 CN CN2008100646757A patent/CN101302244B/zh not_active Expired - Fee Related
-
2009
- 2009-04-15 WO PCT/CN2009/071271 patent/WO2009146619A1/zh active Application Filing
- 2009-04-15 CA CA2705902A patent/CA2705902C/en not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009146619A1 (zh) * | 2008-06-06 | 2009-12-10 | 东北林业大学 | 一种桦木酸的生产方法 |
CN102344482A (zh) * | 2011-07-29 | 2012-02-08 | 温州大学 | 桦木醇衍生物、制备方法及用途 |
CN103626827A (zh) * | 2012-08-29 | 2014-03-12 | 奇复康药物研发(苏州)有限公司 | 一种白桦酸标准品制备方法 |
CN112811995A (zh) * | 2021-01-14 | 2021-05-18 | 惠泽化学科技(濮阳)有限公司 | 一种4-取代基环己酮类液晶中间体的合成方法 |
Also Published As
Publication number | Publication date |
---|---|
WO2009146619A1 (zh) | 2009-12-10 |
CA2705902A1 (en) | 2009-12-10 |
CA2705902C (en) | 2013-05-14 |
CN101302244B (zh) | 2011-04-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101302244B (zh) | 一种桦木酸的生产方法 | |
CN101987860A (zh) | 一种熊去氧胆酸的制备方法 | |
CN1325508C (zh) | 一锅法制备泼尼松龙衍生物 | |
CN101092421B (zh) | 一种芝麻素提取新工艺 | |
CN109369765B (zh) | 一种鼠胆酸的制备方法 | |
CN101824011A (zh) | 一种3-o-烷基抗坏血酸的制备方法 | |
CN102558280B (zh) | 一种30-卤代桦木酸的生产方法 | |
CN1544427A (zh) | 木犀草素的半合成方法 | |
CN103896930B (zh) | 卡格列净半水合物药用晶型的制备方法 | |
CN113185485B (zh) | 一种二氢槲皮素的半合成方法 | |
CN103360411A (zh) | 依维莫司结晶提纯方法 | |
WO2020182228A1 (zh) | 一种牛磺胆酸钠的精制方法 | |
CN112441932A (zh) | 一种富马酸比索洛尔杂质的制备方法 | |
CN102399255B (zh) | 一种桦木酸的制备方法 | |
KR20170029141A (ko) | 고순도 바제독시펜 아세테이트의 제조방법 | |
CN115716862A (zh) | 新型长效芸苔素内酯、合成方法及其应用 | |
CN1282647C (zh) | 阿昔莫司的制备方法 | |
CN101805389A (zh) | 一种科罗索酸的制备方法 | |
CN103664941B (zh) | 一种长春西汀类似物的制备方法 | |
CN109705016B (zh) | 一种吲达帕胺有关物质b的制备方法 | |
CN102746203A (zh) | 一种高含量玉米黄素的制备方法 | |
CN115785057B (zh) | 一种替卡格雷中间化合物及其盐的制备方法 | |
CN111087436B (zh) | 一种奥贝胆酸的制备方法 | |
CH449006A (de) | Verfahren zur Herstellung von Fusidinsäure- und Dihydrofusidinsäurederivaten | |
CN106892931B (zh) | 一种生物素中间体的提纯方法 |
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 | ||
ASS | Succession or assignment of patent right |
Owner name: HEILONGJIANG JIABAO BIO-TECHNOLOGY DEVELOPMENT CO. Free format text: FORMER OWNER: NORTHEAST FORESTRY UNIVERSITY Effective date: 20110629 |
|
C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 150040 NO. 26, HEXING ROAD, XIANGFANG DISTRICT, HARBIN CITY, HEILONGJIANG PROVINCE TO: 150028 NO. 2298, LONGXING ROAD, SONGBEI DISTRICT, HARBIN CITY |
|
TR01 | Transfer of patent right |
Effective date of registration: 20110629 Address after: 150028 Harbin city Songbei City Road No. 2298 Patentee after: Heilongjiang Province Jiabao Bio-technology Development Co.,Ltd. Address before: 150040 Xiangfang District, Heilongjiang, and Hing Road, No. 26, Harbin Patentee before: Northeast Forestry University |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Production process of betulinic acid Effective date of registration: 20120803 Granted publication date: 20110413 Pledgee: Harbin Enterprise Credit Guarantee Center Pledgor: Heilongjiang Province Jiabao Bio-technology Development Co.,Ltd. Registration number: 2012990000425 |
|
ASS | Succession or assignment of patent right |
Owner name: HARBIN BAODE BIOTECHNOLOGY DEVELOPMENT CO., LTD. Free format text: FORMER OWNER: HEILONGJIANG JIABAO BIO-TECHNOLOGY DEVELOPMENT CO., LTD. Effective date: 20140418 |
|
C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 150000 HARBIN, HEILONGJIANG PROVINCE TO: 150007 HARBIN, HEILONGJIANG PROVINCE |
|
TR01 | Transfer of patent right |
Effective date of registration: 20140418 Address after: 1102 room 235, Eastern Mansion, 150007 Garden Street, Nangang District, Heilongjiang, Harbin Patentee after: HARBIN BAODE BIOTECHNOLOGY Co.,Ltd. Address before: 150000 Heilongjiang city of Harbin province Songbei City Road No. 2298 Patentee before: Heilongjiang Province Jiabao Bio-technology Development Co.,Ltd. |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Production process of betulinic acid Effective date of registration: 20120803 Granted publication date: 20110413 Pledgee: Harbin Enterprise Credit Guarantee Center Pledgor: Heilongjiang Province Jiabao Bio-technology Development Co.,Ltd. Registration number: 2012990000425 |
|
PLDC | Enforcement, change and cancellation of contracts on pledge of patent right or utility model | ||
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: 1102 room 235, Eastern Mansion, 150007 Garden Street, Nangang District, Heilongjiang, Harbin Patentee after: HARBIN BAODE BIOTECHNOLOGY Co.,Ltd. Address before: 1102 room 235, Eastern Mansion, 150007 Garden Street, Nangang District, Heilongjiang, Harbin Patentee before: HARBIN BAODE BIOTECHNOLOGY Co.,Ltd. |
|
TR01 | Transfer of patent right |
Effective date of registration: 20150911 Address after: 150028 Heilongjiang city of Harbin province Songbei City Road No. 2298 Patentee after: Heilongjiang Province Jiabao Bio-technology Development Co.,Ltd. Address before: 1102 room 235, Eastern Mansion, 150007 Garden Street, Nangang District, Heilongjiang, Harbin Patentee before: HARBIN BAODE BIOTECHNOLOGY Co.,Ltd. |
|
DD01 | Delivery of document by public notice |
Addressee: Heilongjiang Province Jiabao Bio-technology Development Co.,Ltd. Document name: Notification of Passing Examination on Formalities |
|
PP01 | Preservation of patent right |
Effective date of registration: 20160413 Granted publication date: 20110413 |
|
RINS | Preservation of patent right or utility model and its discharge | ||
DD01 | Delivery of document by public notice |
Addressee: Heilongjiang Province Jiabao Bio-technology Development Co.,Ltd. Document name: Notice of preservation procedure |
|
PD01 | Discharge of preservation of patent | ||
PD01 | Discharge of preservation of patent |
Date of cancellation: 20170413 Granted publication date: 20110413 Date of cancellation: 20161013 Granted publication date: 20110413 |
|
PP01 | Preservation of patent right | ||
PP01 | Preservation of patent right |
Effective date of registration: 20161013 Granted publication date: 20110413 |
|
DD01 | Delivery of document by public notice | ||
DD01 | Delivery of document by public notice |
Addressee: Heilongjiang Province Jiabao Bio-technology Development Co.,Ltd. Document name: Notification of Termination of Patent Right |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20110413 Termination date: 20170606 |
|
CF01 | Termination of patent right due to non-payment of annual fee |