CN102827190A - Cefoselis sulfate intermediate and preparation method thereof - Google Patents
Cefoselis sulfate intermediate and preparation method thereof Download PDFInfo
- Publication number
- CN102827190A CN102827190A CN2012101749244A CN201210174924A CN102827190A CN 102827190 A CN102827190 A CN 102827190A CN 2012101749244 A CN2012101749244 A CN 2012101749244A CN 201210174924 A CN201210174924 A CN 201210174924A CN 102827190 A CN102827190 A CN 102827190A
- Authority
- CN
- China
- Prior art keywords
- preparation
- formula
- cefoselis sulfate
- reaction
- cefoselis
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 229950001580 cefoselis Drugs 0.000 title claims abstract description 16
- LZOLCSVRFKCSEM-ZQCAECPKSA-N cefoselis sulfate Chemical compound OS(O)(=O)=O.S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CN1C=CC(=N)N1CCO LZOLCSVRFKCSEM-ZQCAECPKSA-N 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 claims description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims 3
- 230000035484 reaction time Effects 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000001035 drying Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 methoxy benzyl ester Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 229930186147 Cephalosporin Natural products 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940124587 cephalosporin Drugs 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- KFCMZNUGNLCSJQ-NFBKMPQASA-N (4-methoxyphenyl)methyl (6r,7r)-3-(chloromethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)C1=C(CCl)CS[C@H]2N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1 KFCMZNUGNLCSJQ-NFBKMPQASA-N 0.000 description 1
- QIARZPLHXDREQO-UHFFFAOYSA-N 1-(3-amino-1h-pyrazol-5-yl)ethanol Chemical compound CC(O)C=1C=C(N)NN=1 QIARZPLHXDREQO-UHFFFAOYSA-N 0.000 description 1
- LYUPJHVGLFETDG-UHFFFAOYSA-N 1-phenylbutan-2-ol Chemical compound CCC(O)CC1=CC=CC=C1 LYUPJHVGLFETDG-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- 206010061977 Genital infection female Diseases 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ZINFAXPQMLDEEJ-GFVOIPPFSA-N cefoselis Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CN1C=CC(=N)N1CCO ZINFAXPQMLDEEJ-GFVOIPPFSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Abstract
The invention relates to a cefoselis sulfate intermediate and a preparation method for the cefoselis sulfate intermediate, in particular to the cefoselis sulfate intermediate and the preparation method for the cefoselis sulfate intermediate shown as a formula (II). The preparation method provided by the invention has a shorter reaction time, and a higher yield.
Description
Technical field
The present invention relates to a kind of new cefoselis sulfate midbody and preparation method thereof, especially cefoselis sulfate midbody and preparation method thereof shown in the formula (II).
Background technology
Cefoselis sulfate (Cefoselis sulfate) belong to the 4th generation cephalosporins; This medicine is developed by Japanese Fujisawa Pharmaceutical and U.S. Johnson company jointly; And at first went on the market in Japan in 1998; Its commodity are called FK-037, be the 4th generation cephalosporins typical case representative.At present, this medicine remarkable anti-microbial effect in external and animal infection modal is confirmed by worldwide a large amount of clinical experiment reports.Surgical infection, respiratory tract infection, obstetrics and gynecological infection and ophthalmology infection etc. have been successfully applied to both at home and abroad.
Up to the present; Wincef synthetic have with 7-tertbutyloxycarbonyl amido-3-chloromethyl-3-cephem-4-carboxylic acid benzhydryl ester, formula (I) compound promptly 7 beta-aminos-3-chloromethyl-3-cephem-4-carboxylic acid be raw material to methoxy benzyl ester etc.; Introduce 5-amino-1-hydroxyethyl pyrazole in C-3 ' position respectively, introduce 2-cis methoxy imino-2-(thiazolamine base-4)-ethanoyl in 7 β positions and realize.Wherein by in the process of formula (I) compound cefoselis sulfate usually with formyl radical as amino protecting group, make formula (III) midbody, but this midbody productive rate is not high, and soluble in water, be difficult to purification to be used for subsequent reactions.
CN101993450A discloses a kind of method for preparing cefoselis sulfate, and this method relates to the preparation of formula (II), but according to patented process; In the preparation process of formula (II), add the Boc2 reaction after 8 hours, raw material still has a large amount of residues; Usually need to continue reaction 12 hours; Raw material ability primitive reaction is complete, but simultaneously, the prolongation in reaction times causes reaction yield to reduce.
Summary of the invention
The object of the present invention is to provide the method for preparing midbody shown in the formula (II), this method by formula (I) compound and tert-Butyl dicarbonate react midbody shown in the formula (II).Preferably, this method is under the Tetrabutyl amonium bromide condition, to accomplish.
With respect to midbody shown in the formula (III), midbody provided by the present invention is easy to preparation, and is insoluble in water, is easy to purify to be used for subsequent reactions; Preparing method's productive rate that this invention provided is high, is fit to suitability for industrialized production.
With respect to the CN101993450A disclosed method, preparing method's reaction times of midbody formula provided by the invention (II) is shorter, and yield is higher.
Embodiment
For more detailed explanation the present invention, provide following embodiment, but scope of the present invention is not to be defined in this.Described ad hoc approach of those skilled in the art's easy to understand and result only are illustrative.
The preparation of reference example formula (I) compound
CH
2Cl
2(3L), PCl
5(374.4g) join successively in the reaction flask of 10L, stirring at normal temperature slowly drips pyridine (200mL) with about interior temperature drop to 0 ℃, the control rate of addition, and temperature is not above 5 ℃ in making.Continue to be cooled to-5 ℃ behind the reaction 1h, add GCLE (7-phenylacetamide-3-chloromethyl cephalosporin alkyl olefin(e) acid is to methoxy benzyl ester, and 584.4g), temperature continues reaction 3h in the control between-5 ℃ to 0 ℃ in batches.Fast cooling is to-30 ℃, and beginning slowly drips methyl alcohol (1500mL), continues at-30 ℃ of reaction 1h.Be warming up to-10 ℃, drip 1500mL water, controlled temperature-10 is to 0 ℃ of reaction 1h.At last, property adding 1500mL water stirs 5min again, and reaction solution is poured in the tool end opening filter flask, and standing demix is emitted organic phase, and water adds a small amount of CH
2Cl
2Extract, merge organic phase, SODIUM SULPHATE ANHYDROUS 99PCT (1000g) drying, suction filtration, filter cake are used a small amount of CH
2Cl
2Washing is added drop-wise to filtrating in the isopropyl ether (12L) stirred overnight.Next day, suction filtration, filter cake washs with a small amount of isopropyl ether, gets faint yellow solid, scrapes material, and drying under vacuum overnight gets product 456g.
The preparation of the embodiment same form (II) compound
Take by weighing reference example product (450g) and place the 5L reaction flask; Add 1; 4-dioxane (1L) adds sodium bicarbonate aqueous solution (1mol/L) 1100mL by amount and regulates pH value 7-7.5, then adds Tetrabutyl amonium bromide (10g); Stir the back and add tert-Butyl dicarbonate (450g), 20 ℃ of reaction 10h.After the TLC monitoring reaction is complete, adds ETHYLE ACETATE (1000mL) and extract, separatory, water layer add the 160mL ethyl acetate extraction again; Separatory merges organic phase, saturated common salt washing (250mL * 2), SODIUM SULPHATE ANHYDROUS 99PCT (200g) drying; Filter, concentrate, get oily matter, add 600mL ETHYLE ACETATE and fully dissolve the back to wherein dripping sherwood oil (2500ml) crystallization; Suction filtration behind the stirring 1h, filter cake normal temperature drying under vacuum overnight gets white powder solid 417g, yield 80.0%.
MS-ESI：491.33[M+Na]+
The preparation (with reference to CN101993450A) of embodiment two formulas (II) compound
Take by weighing reference example product (81.0g) and place the 2L reaction flask, add THF (400mL), triethylamine (24.3g) is cooled to 0-5 ℃; Drip tert-Butyl dicarbonate (48.0g), dropwise, return to stirring at room reaction 8 hours, TLC detects; Still have big content of starting materials formula (I) residue, continued stirring reaction about 12 hours, the raw material primitive reaction is complete, and reaction solution is concentrated into 150mL; Add ETHYLE ACETATE 500mL, use 1N hydrochloric acid 20mL successively, saturated aqueous common salt 200mL washing, organic phase is used anhydrous sodium sulfate drying; Filter, filtrating is concentrated into dried, adds sherwood oil (60-90 ℃) freezing and crystallizing, filters; Drying gets white solid 55.0g, yield 58.6%.
The preparation of embodiment three formulas (III) compound
The preparation method is with embodiment one, and difference is that the tert-Butyl dicarbonate among the embodiment one is become acetic formic anhydride, gets white powder solid 120g.
Claims (3)
1. the cefoselis sulfate intermediates preparation shown in the formula II,
2. cefoselis sulfate intermediates preparation according to claim 1, this method by formula I compound and tert-Butyl dicarbonate react midbody shown in the formula II,
3. cefoselis sulfate intermediates preparation according to claim 2, it is under the Tetrabutyl amonium bromide condition, to accomplish.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210174924.4A CN102827190B (en) | 2011-06-14 | 2012-05-30 | Cefoselis sulfate intermediate and preparation method thereof |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101586257 | 2011-06-14 | ||
| CN201110158625 | 2011-06-14 | ||
| CN201110158625.7 | 2011-06-14 | ||
| CN201210174924.4A CN102827190B (en) | 2011-06-14 | 2012-05-30 | Cefoselis sulfate intermediate and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102827190A true CN102827190A (en) | 2012-12-19 |
| CN102827190B CN102827190B (en) | 2015-10-21 |
Family
ID=47330525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210174924.4A Active CN102827190B (en) | 2011-06-14 | 2012-05-30 | Cefoselis sulfate intermediate and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102827190B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106317077A (en) * | 2015-06-24 | 2017-01-11 | 连云港恒运医药科技有限公司 | Novel efficient preparation method of ceftiofur sulfate intermediate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004058695A1 (en) * | 2002-12-26 | 2004-07-15 | Lupin Limited | Novel intermediates for synthesis of cephalosporins and process for preparation of such intermediates |
| CN1613860A (en) * | 2003-11-07 | 2005-05-11 | 天津药物研究院 | Cephaene onium salt compound and its preparation, and synthesis of cephapyrazde sulfate therefrom |
| CN101993450A (en) * | 2010-11-03 | 2011-03-30 | 湖南欧亚生物有限公司 | Preparation method of cefoselis sulfate |
-
2012
- 2012-05-30 CN CN201210174924.4A patent/CN102827190B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004058695A1 (en) * | 2002-12-26 | 2004-07-15 | Lupin Limited | Novel intermediates for synthesis of cephalosporins and process for preparation of such intermediates |
| CN1613860A (en) * | 2003-11-07 | 2005-05-11 | 天津药物研究院 | Cephaene onium salt compound and its preparation, and synthesis of cephapyrazde sulfate therefrom |
| CN101993450A (en) * | 2010-11-03 | 2011-03-30 | 湖南欧亚生物有限公司 | Preparation method of cefoselis sulfate |
Non-Patent Citations (2)
| Title |
|---|
| TOMOYASU ISHIKAWA ET AL.: ""Studies on Anti-MRSA Parenteral Cephalosporins III. Synthesis and Antibacterial Activity of 7β-[2-(5-Amino-l,2,4-thiadiazol-3-yl)-2(Z)-alkoxyiminoacetamido]-3-[(E)-2-(l-alkylimidazo[l,2-b]pyridazinium-6-yl)thiovinyl]-3-cephem-4-carboxylates……"", 《THE JOURNAL OF ANTIBIOTICS》, vol. 54, no. 3, 31 March 2001 (2001-03-31), pages 257 - 277, XP001056921 * |
| 黄朋勉 等: ""硫酸头孢噻利的合成研究进展"", 《精细化工中间体》, vol. 37, no. 1, 31 January 2007 (2007-01-31), pages 15 - 18 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106317077A (en) * | 2015-06-24 | 2017-01-11 | 连云港恒运医药科技有限公司 | Novel efficient preparation method of ceftiofur sulfate intermediate |
| CN106317077B (en) * | 2015-06-24 | 2020-07-17 | 连云港恒运药业有限公司 | Novel efficient preparation method of cefoselis sulfate intermediate |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102827190B (en) | 2015-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102603841B (en) | Preparation method of dehydroisoandrosterone | |
| CN101486706B (en) | Omeprazole sodium compound and method for synthesizing the same | |
| CN102134252B (en) | Preparation method of high-purity cefuroxime acid | |
| JP2016516693A (en) | Salt of treprostinil | |
| WO2012088607A1 (en) | Process for treprostinil salt preparation | |
| CN101490015B (en) | Rosuvastatin zinc salt | |
| CN106256824B (en) | Preparation method of high-purity delafloxacin meglumine salt | |
| CN102731605B (en) | A kind of purification process of Abiraterone acetate | |
| CN105330634A (en) | One-pot method for preparing 3-hydroxyphtalic anhydride | |
| CN102516261A (en) | Preparation method of cefdinir | |
| CN102827190A (en) | Cefoselis sulfate intermediate and preparation method thereof | |
| CN102304140A (en) | Preparation method of cefodizime sodium | |
| WO2020182228A1 (en) | Method of refining sodium taurocholate | |
| CN101928253B (en) | 2-[5-(2-hydroxyphenyl]-4H-1,2,4-triazole-3-thioether]-1-acetophenone compound or pharmaceutically acceptable salt and preparation and application thereof | |
| CN101993450B (en) | Preparation method of cefoselis sulfate | |
| PL104803B1 (en) | METHOD OF MANUFACTURING PHARMACY PERMISSIBLE, UNSOLVATED, ANHYDROUS NEW CRYSTALLINE FORM OF GAMMA SODIUM ACID 7- / D-ALPHA-FORMYLOOXY-ALPHA-PHENYLACETAMIDO / -3- / 1-THOMETHYL-THOMETRA -4 | |
| CN111471057A (en) | Process for preparing mezlocillin sodium by solvent crystallization | |
| CN104277053A (en) | High purity cefodizime and preparation method for intermediate cefodizime acid | |
| CN105315198A (en) | Crystal form of pirfenidone and preparation method of crystal form | |
| WO2018032586A1 (en) | Method for synthesizing 3-(difluoromethyl)-1-methyl-1h-pyrazole-4-carboxylic acid, and intermediates thereof | |
| CN102199132A (en) | Method for preparing 2-(2-amino-4-thiazole)-2(Z)-[[(tertbutyloxycarbonyl) methoxyl] imido] acetic acid and salt thereof | |
| CN103113294A (en) | Synthesizing method of rebamipide | |
| CN107892676A (en) | The preparation method of Cefdinir active thioester | |
| CN106317077B (en) | Novel efficient preparation method of cefoselis sulfate intermediate | |
| CN101016283B (en) | Preparation of yanhuning |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| ASS | Succession or assignment of patent right |
Owner name: LIANYUNGANG HENGYUN MEDICINE SCIENCE + TECHNOLOGY Free format text: FORMER OWNER: LIANYUNGANG HONGCHUANG PHARMACEUTICAL CO., LTD. OF JIANGSU HANSOH PHARMACEUTICAL GROUP Effective date: 20150629 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| C53 | Correction of patent of invention or patent application | ||
| CB02 | Change of applicant information |
Address after: 222006 Jiangsu province Lianyungang Kaitai Dapu Industrial Zone, economic and Technological Development Zone Road Applicant after: JIANGSU HANSOH PHARMACEUTICAL GROUP LIANYUNGANG HONGCHUANG PHARMACEUTICAL Co.,Ltd. Address before: 222006 Jiangsu province Lianyungang Kaitai Dapu Road Industrial Area Applicant before: JIANGSU HANSOH PHARMACEUTICAL GROUP LIANYUNGANG HONGCHUANG PHARMACEUTICAL Co.,Ltd. |
|
| TA01 | Transfer of patent application right |
Effective date of registration: 20150629 Address after: 222200, No. seven West Road, Lingang Industrial Zone, Guanyun County, Jiangsu, Lianyungang province 1 Applicant after: LIANYUNGANG HENGYUN MEDICAL TECHNOLOGY Co.,Ltd. Address before: 222006 Jiangsu province Lianyungang Kaitai Dapu Industrial Zone, economic and Technological Development Zone Road Applicant before: JIANGSU HANSOH PHARMACEUTICAL GROUP LIANYUNGANG HONGCHUANG PHARMACEUTICAL Co.,Ltd. |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CB03 | Change of inventor or designer information |
Inventor after: Zhang Qingjie Inventor after: Du Zuyin Inventor before: Du Zuyin |
|
| COR | Change of bibliographic data | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20170527 Address after: 222200 Guanyun City, Jiangsu province Lingang Industrial Zone, the south side of the weft Road, eight Patentee after: LIANYUNGANG HENGYUN MEDICAL TECHNOLOGY CO.,LTD. Address before: 222200, No. seven West Road, Lingang Industrial Zone, Guanyun County, Jiangsu, Lianyungang province 1 Patentee before: LIANYUNGANG HENGYUN MEDICAL TECHNOLOGY Co.,Ltd. |
|
| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 222200 Guanyun City, Jiangsu province Lingang Industrial Zone, the south side of the weft Road, eight Patentee after: LIANYUNGANG HENGYUN PHARMACEUTICAL Co.,Ltd. Address before: 222200 Guanyun City, Jiangsu province Lingang Industrial Zone, the south side of the weft Road, eight Patentee before: LIANYUNGANG HENGYUN MEDICAL TECHNOLOGY CO.,LTD. |