CN105175446A - 一种治疗骨质疏松的米诺膦酸的制备方法 - Google Patents
一种治疗骨质疏松的米诺膦酸的制备方法 Download PDFInfo
- Publication number
- CN105175446A CN105175446A CN201510677529.1A CN201510677529A CN105175446A CN 105175446 A CN105175446 A CN 105175446A CN 201510677529 A CN201510677529 A CN 201510677529A CN 105175446 A CN105175446 A CN 105175446A
- Authority
- CN
- China
- Prior art keywords
- formula
- reaction
- compound
- preparation
- compound shown
- 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
- VMMKGHQPQIEGSQ-UHFFFAOYSA-N minodronic acid Chemical compound C1=CC=CN2C(CC(O)(P(O)(O)=O)P(O)(O)=O)=CN=C21 VMMKGHQPQIEGSQ-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 229950011129 minodronic acid Drugs 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 36
- 208000001132 Osteoporosis Diseases 0.000 title abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 89
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000004471 Glycine Substances 0.000 claims abstract description 10
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims abstract description 10
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Chemical group 0.000 claims abstract description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims abstract description 4
- 229910001961 silver nitrate Inorganic materials 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000003756 stirring Methods 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 239000012046 mixed solvent Substances 0.000 claims description 21
- 230000001009 osteoporotic effect Effects 0.000 claims description 16
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 238000006366 phosphorylation reaction Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 230000026731 phosphorylation Effects 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 abstract description 9
- 238000000746 purification Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 abstract 2
- 235000004279 alanine Nutrition 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 230000000865 phosphorylative effect Effects 0.000 abstract 1
- 230000036632 reaction speed Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000012544 monitoring process Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- YRWKRIAFGJJDDX-UHFFFAOYSA-N bromomethyl 3-oxobutanoate Chemical compound C(CC(=O)C)(=O)OCBr YRWKRIAFGJJDDX-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 description 1
- 208000006386 Bone Resorption Diseases 0.000 description 1
- 206010065687 Bone loss Diseases 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000003076 Osteolysis Diseases 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229940062527 alendronate Drugs 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 208000029791 lytic metastatic bone lesion Diseases 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- WRUUGTRCQOWXEG-UHFFFAOYSA-N pamidronate Chemical compound NCCC(O)(P(O)(O)=O)P(O)(O)=O WRUUGTRCQOWXEG-UHFFFAOYSA-N 0.000 description 1
- 229960003978 pamidronic acid Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510677529.1A CN105175446B (zh) | 2015-10-17 | 2015-10-17 | 一种治疗骨质疏松的米诺膦酸的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510677529.1A CN105175446B (zh) | 2015-10-17 | 2015-10-17 | 一种治疗骨质疏松的米诺膦酸的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105175446A true CN105175446A (zh) | 2015-12-23 |
CN105175446B CN105175446B (zh) | 2017-03-22 |
Family
ID=54897954
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510677529.1A Active CN105175446B (zh) | 2015-10-17 | 2015-10-17 | 一种治疗骨质疏松的米诺膦酸的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105175446B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105837635A (zh) * | 2016-05-05 | 2016-08-10 | 青岛辰达生物科技有限公司 | 一种用于治疗骨质疏松的米诺膦酸的制备方法 |
CN107033187A (zh) * | 2017-04-28 | 2017-08-11 | 江苏笃诚医药科技股份有限公司 | 一种米诺膦酸的制备方法 |
CN107778313A (zh) * | 2016-08-29 | 2018-03-09 | 鲁南制药集团股份有限公司 | 一种米诺膦酸中间体咪唑并[1,2‑a]吡啶‑3‑乙酸的精制方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020042420A1 (en) * | 2000-08-16 | 2002-04-11 | Hans Briem | Beta-amyloid inhibitors, processes for preparing them, and their use in pharmaceutical compositions |
CN101973993A (zh) * | 2010-11-05 | 2011-02-16 | 天津药物研究院 | 一种制备2-[咪唑并(1,2-a)吡啶-3-基]乙酸的方法 |
CN102153585A (zh) * | 2011-02-24 | 2011-08-17 | 北京欧克兰医药技术开发中心 | 一种米诺膦酸中间体的合成方法及米诺膦酸的合成 |
CN104693240A (zh) * | 2015-03-02 | 2015-06-10 | 北京万全德众医药生物技术有限公司 | 一种米诺膦酸的制备方法 |
CN104945436A (zh) * | 2015-07-09 | 2015-09-30 | 山东罗欣药业集团股份有限公司 | 一种米诺膦酸的制备方法 |
-
2015
- 2015-10-17 CN CN201510677529.1A patent/CN105175446B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020042420A1 (en) * | 2000-08-16 | 2002-04-11 | Hans Briem | Beta-amyloid inhibitors, processes for preparing them, and their use in pharmaceutical compositions |
CN101973993A (zh) * | 2010-11-05 | 2011-02-16 | 天津药物研究院 | 一种制备2-[咪唑并(1,2-a)吡啶-3-基]乙酸的方法 |
CN102153585A (zh) * | 2011-02-24 | 2011-08-17 | 北京欧克兰医药技术开发中心 | 一种米诺膦酸中间体的合成方法及米诺膦酸的合成 |
CN104693240A (zh) * | 2015-03-02 | 2015-06-10 | 北京万全德众医药生物技术有限公司 | 一种米诺膦酸的制备方法 |
CN104945436A (zh) * | 2015-07-09 | 2015-09-30 | 山东罗欣药业集团股份有限公司 | 一种米诺膦酸的制备方法 |
Non-Patent Citations (2)
Title |
---|
THOMAS A. ENGLER ET AL.: "Substituted 3-Imidazo[1,2-a]pyridin-3-yl-4-(1,2,3,4-tetrahydro-[1,4]diazepino-[6,7,1-hi]indol-7-yl)pyrrole-2,5-diones as Highly Selective and Potent Inhibitors of Glycogen Synthase Kinase-3", 《J. MED. CHEM.》 * |
王伟等: "米诺膦酸的合成", 《中国医药工业杂志》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105837635A (zh) * | 2016-05-05 | 2016-08-10 | 青岛辰达生物科技有限公司 | 一种用于治疗骨质疏松的米诺膦酸的制备方法 |
CN105837635B (zh) * | 2016-05-05 | 2017-12-08 | 邱善晓 | 一种用于治疗骨质疏松的米诺膦酸的制备方法 |
CN107778313A (zh) * | 2016-08-29 | 2018-03-09 | 鲁南制药集团股份有限公司 | 一种米诺膦酸中间体咪唑并[1,2‑a]吡啶‑3‑乙酸的精制方法 |
CN107033187A (zh) * | 2017-04-28 | 2017-08-11 | 江苏笃诚医药科技股份有限公司 | 一种米诺膦酸的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN105175446B (zh) | 2017-03-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2010502667A (ja) | Snac(サルカプロザートナトリウム)の製造法 | |
CN104817593B (zh) | 半富马酸替诺福韦艾拉酚胺关键中间体的合成工艺 | |
KR20070119176A (ko) | L-α-글리세로포스포릴 콜린의 제조방법 | |
US20080275265A1 (en) | Process for the Preparation of (Aminoalkylamino)Alkyl Halides and Conversion to Amifostine | |
CA2646418A1 (en) | Process for manufacturing bisphosphonic acids | |
CN101389637A (zh) | 铂(ⅱ)配合物的制备 | |
CN105175446A (zh) | 一种治疗骨质疏松的米诺膦酸的制备方法 | |
CN104725422B (zh) | 一种米诺膦酸的制备方法 | |
CN102875602A (zh) | 一种米诺膦酸水合物的制备方法 | |
CN108586360B (zh) | 一种6-氯-3-甲基尿嘧啶的制备方法 | |
CN105153232A (zh) | 一种用于治疗骨质疏松的米诺膦酸的制备方法 | |
CN101528722B (zh) | 制备结晶3-o-烷基-抗坏血酸的方法 | |
KR20080007347A (ko) | 오염화인과 디엠에프로부터 부산물로서 옥시염화인의 생성및 빌스마이어-헥크 시약으로의 변환에 의한 염소화 반응에사용되는 옥시염화인의 용도 | |
KR101330814B1 (ko) | 콜린 알포세레이트의 제조방법 | |
CN104592337A (zh) | 一种9-β-D-阿拉伯呋喃糖基-2-氟代腺嘌呤-5’-磷酸酯的制备方法 | |
CN102344463A (zh) | 一种制备1-羟基-2-(咪唑并[1,2-a]吡啶-3-基)亚乙基-1,1-双膦酸化合物的方法 | |
EP2192126B1 (en) | Process for making zoledronic acid | |
JPH03109394A (ja) | リボフラビン―5′―リン酸もしくはそのモノナトリウム塩の製法 | |
CN107903263A (zh) | 一种帕布昔利布中间体的合成方法 | |
US7414151B2 (en) | Process for manufacture of 4-amino-hydroxybutylidene-1, 1-bisphosphonic acid and its salts | |
CN103030661B (zh) | 伊班膦酸钠的制备方法 | |
JPH03181493A (ja) | 純粋な環状リン酸ジアリールエステルの製造方法 | |
CN102796056B (zh) | 帕拉米韦中间体及类似物的制备方法 | |
CN102093416B (zh) | 一种合成伊班膦酸钠的方法 | |
CN105541910A (zh) | 对甲苯磺酰氧甲基膦酸二乙酯的合成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C41 | Transfer of patent application or patent right or utility model | ||
CB03 | Change of inventor or designer information |
Inventor after: Xia Changling Inventor after: Xu Shina Inventor after: Li Hongmei Inventor before: Chen Linghao |
|
COR | Change of bibliographic data | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20170113 Address after: 1 residential building, No. 443 Changjiang East Road, Huangdao District, Shandong, China, 1708, China, 266520 Applicant after: QINGDAO CHENDA BIOLOGICAL SCIENCE & TECHNOLOGY Co.,Ltd. Applicant after: Xia Changling Applicant after: Xu Shina Applicant after: Li Hongmei Address before: 1 residential building, No. 443 Changjiang East Road, Huangdao District, Shandong, China, 1708, China, 266520 Applicant before: QINGDAO CHENDA BIOLOGICAL SCIENCE & TECHNOLOGY Co.,Ltd. |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20191107 Address after: Room 2, west of the second floor, No. 355, Huanbei West Road, Weitang street, Jiashan County, Jiaxing City, Zhejiang Province Patentee after: Jiashan Weitang Asset Management Co.,Ltd. Address before: 1 residential building, No. 443 Changjiang East Road, Huangdao District, Shandong, China, 1708, China, 266520 Co-patentee before: Xia Changling Patentee before: QINGDAO CHENDA BIOLOGICAL SCIENCE & TECHNOLOGY Co.,Ltd. Co-patentee before: Xu Shina Co-patentee before: Li Hongmei |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A preparation method of minodronic acid for treating osteoporosis Effective date of registration: 20210531 Granted publication date: 20170322 Pledgee: Weitang sub branch of Zhejiang Jiashan Rural Commercial Bank Co.,Ltd. Pledgor: Jiashan Weitang Asset Management Co.,Ltd. Registration number: Y2021980004130 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20231018 Granted publication date: 20170322 Pledgee: Weitang sub branch of Zhejiang Jiashan Rural Commercial Bank Co.,Ltd. Pledgor: Jiashan Weitang Asset Management Co.,Ltd. Registration number: Y2021980004130 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A preparation method of minofloxacin for the treatment of osteoporosis Effective date of registration: 20231127 Granted publication date: 20170322 Pledgee: Weitang sub branch of Zhejiang Jiashan Rural Commercial Bank Co.,Ltd. Pledgor: Jiashan Weitang Asset Management Co.,Ltd. Registration number: Y2023330002807 |