CN105130955A - 富马酸沃诺拉赞的制备方法 - Google Patents
富马酸沃诺拉赞的制备方法 Download PDFInfo
- Publication number
- CN105130955A CN105130955A CN201510593001.6A CN201510593001A CN105130955A CN 105130955 A CN105130955 A CN 105130955A CN 201510593001 A CN201510593001 A CN 201510593001A CN 105130955 A CN105130955 A CN 105130955A
- Authority
- CN
- China
- Prior art keywords
- fumaric acid
- nuolazan
- preparation
- crude product
- pyridine
- 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 24
- ROGSHYHKHPCCJW-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]-n-methylmethanamine Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CN=CC=1S(=O)(=O)N1C=C(CNC)C=C1C1=CC=CC=C1F ROGSHYHKHPCCJW-WLHGVMLRSA-N 0.000 title abstract description 7
- 229950003825 vonoprazan Drugs 0.000 title abstract description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 145
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 73
- 239000001530 fumaric acid Substances 0.000 claims abstract description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000012043 crude product Substances 0.000 claims abstract description 29
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 25
- 230000002829 reductive effect Effects 0.000 claims abstract description 13
- 239000007787 solid Substances 0.000 claims abstract description 13
- 239000012046 mixed solvent Substances 0.000 claims abstract description 10
- 239000013078 crystal Substances 0.000 claims abstract description 8
- 238000000967 suction filtration Methods 0.000 claims abstract description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000002425 crystallisation Methods 0.000 claims abstract description 6
- 230000008025 crystallization Effects 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 238000004090 dissolution Methods 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 claims description 7
- 239000012321 sodium triacetoxyborohydride Substances 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 4
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 238000004128 high performance liquid chromatography Methods 0.000 abstract description 9
- 238000007670 refining Methods 0.000 abstract description 9
- 239000006227 byproduct Substances 0.000 abstract description 8
- 238000001035 drying Methods 0.000 abstract description 6
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract 2
- IXCSYEVJOAWXRH-UHFFFAOYSA-N 5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrole-3-carbaldehyde Chemical compound FC1=CC=CC=C1C1=CC(C=O)=CN1S(=O)(=O)C1=CC=CN=C1 IXCSYEVJOAWXRH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 238000001514 detection method Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000004519 grease Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102100021904 Potassium-transporting ATPase alpha chain 1 Human genes 0.000 description 2
- 108010083204 Proton Pumps Proteins 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000422 nocturnal effect Effects 0.000 description 2
- 229920000333 poly(propyleneimine) Polymers 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000036269 ulceration Effects 0.000 description 2
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
- CSYFJDLQTXTQER-UHFFFAOYSA-N CNCc(cc1-c(cccc2)c2F)c[n]1S(C(CC1)C=NC1O)(=O)=O Chemical compound CNCc(cc1-c(cccc2)c2F)c[n]1S(C(CC1)C=NC1O)(=O)=O CSYFJDLQTXTQER-UHFFFAOYSA-N 0.000 description 1
- QRENYOFWNSJPRB-UHFFFAOYSA-N CNCc(cc1-c(cccc2)c2F)c[n]1S(C1=CNCC=C1)(=O)=O Chemical compound CNCc(cc1-c(cccc2)c2F)c[n]1S(C1=CNCC=C1)(=O)=O QRENYOFWNSJPRB-UHFFFAOYSA-N 0.000 description 1
- SHVJLYSHYWPTCW-UHFFFAOYSA-N CNCc(cc1-c(cccc2)c2F)c[n]1S(C1C=NCCC1)(=O)=O Chemical compound CNCc(cc1-c(cccc2)c2F)c[n]1S(C1C=NCCC1)(=O)=O SHVJLYSHYWPTCW-UHFFFAOYSA-N 0.000 description 1
- 206010063655 Erosive oesophagitis Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010019375 Helicobacter infections Diseases 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
- 108091022875 Microtubule Proteins 0.000 description 1
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000006957 competitive inhibition Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229960003174 lansoprazole Drugs 0.000 description 1
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 210000001711 oxyntic cell Anatomy 0.000 description 1
- 229960005019 pantoprazole Drugs 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 229940125422 potassium channel blocker Drugs 0.000 description 1
- 239000003450 potassium channel blocker Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940126409 proton pump inhibitor Drugs 0.000 description 1
- 239000000612 proton pump inhibitor Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229960004157 rabeprazole Drugs 0.000 description 1
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
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CN201510593001.6A CN105130955B (zh) | 2015-09-16 | 2015-09-16 | 富马酸沃诺拉赞的制备方法 |
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CN201510593001.6A CN105130955B (zh) | 2015-09-16 | 2015-09-16 | 富马酸沃诺拉赞的制备方法 |
Publications (2)
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CN105130955A true CN105130955A (zh) | 2015-12-09 |
CN105130955B CN105130955B (zh) | 2018-06-12 |
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CN201510593001.6A Expired - Fee Related CN105130955B (zh) | 2015-09-16 | 2015-09-16 | 富马酸沃诺拉赞的制备方法 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106317020A (zh) * | 2016-08-03 | 2017-01-11 | 宜昌人福药业有限责任公司 | 富马酸沃诺拉赞晶型α及其制备方法 |
CN106478601A (zh) * | 2016-09-27 | 2017-03-08 | 海口南陆医药科技股份有限公司 | 一种富马酸沃诺拉赞新晶型及其制备方法 |
CN107941946A (zh) * | 2017-11-24 | 2018-04-20 | 中山奕安泰医药科技有限公司 | 一种富马酸沃诺拉赞的检测方法 |
CN108503621A (zh) * | 2017-12-25 | 2018-09-07 | 上海中拓医药科技有限公司 | 一种富马酸沃诺拉赞的制备方法 |
CN114380796A (zh) * | 2020-10-22 | 2022-04-22 | 杭州中美华东制药有限公司 | 一种富马酸沃诺拉赞的制备方法 |
CN114539219A (zh) * | 2022-03-17 | 2022-05-27 | 日照正济药业有限公司 | 一种富马酸伏诺拉生的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080139639A1 (en) * | 2004-09-30 | 2008-06-12 | Takeda Pharmaceutical Company Limited | Proton Pump Inhibitors |
CN101855206A (zh) * | 2007-06-22 | 2010-10-06 | 坎莫森特里克斯公司 | N-(2-(杂芳基)芳基)芳基磺酰胺类和n-(2-(杂芳基)杂芳基)芳基磺酰胺类 |
CN104860926A (zh) * | 2015-06-10 | 2015-08-26 | 浙江诚意药业股份有限公司 | 一种富马酸沃诺拉赞的制备方法 |
-
2015
- 2015-09-16 CN CN201510593001.6A patent/CN105130955B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080139639A1 (en) * | 2004-09-30 | 2008-06-12 | Takeda Pharmaceutical Company Limited | Proton Pump Inhibitors |
CN101855206A (zh) * | 2007-06-22 | 2010-10-06 | 坎莫森特里克斯公司 | N-(2-(杂芳基)芳基)芳基磺酰胺类和n-(2-(杂芳基)杂芳基)芳基磺酰胺类 |
CN104860926A (zh) * | 2015-06-10 | 2015-08-26 | 浙江诚意药业股份有限公司 | 一种富马酸沃诺拉赞的制备方法 |
Non-Patent Citations (1)
Title |
---|
丁巧灵等: "《醛/酮与胺还原烷基化反应的研究进展》", 《化工生产与技术》 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106317020A (zh) * | 2016-08-03 | 2017-01-11 | 宜昌人福药业有限责任公司 | 富马酸沃诺拉赞晶型α及其制备方法 |
CN106478601A (zh) * | 2016-09-27 | 2017-03-08 | 海口南陆医药科技股份有限公司 | 一种富马酸沃诺拉赞新晶型及其制备方法 |
CN107941946A (zh) * | 2017-11-24 | 2018-04-20 | 中山奕安泰医药科技有限公司 | 一种富马酸沃诺拉赞的检测方法 |
CN107941946B (zh) * | 2017-11-24 | 2021-03-16 | 中山奕安泰医药科技有限公司 | 一种富马酸沃诺拉赞的检测方法 |
CN108503621A (zh) * | 2017-12-25 | 2018-09-07 | 上海中拓医药科技有限公司 | 一种富马酸沃诺拉赞的制备方法 |
CN108503621B (zh) * | 2017-12-25 | 2021-09-14 | 上海中拓医药科技有限公司 | 一种富马酸沃诺拉赞的制备方法 |
CN114380796A (zh) * | 2020-10-22 | 2022-04-22 | 杭州中美华东制药有限公司 | 一种富马酸沃诺拉赞的制备方法 |
CN114539219A (zh) * | 2022-03-17 | 2022-05-27 | 日照正济药业有限公司 | 一种富马酸伏诺拉生的制备方法 |
Also Published As
Publication number | Publication date |
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CN105130955B (zh) | 2018-06-12 |
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Address after: Room 4, building B2, Nanhai Road, Xiuying District 570311 in Hainan city of Haikou province No. 266 Haikou national high tech Zone Business Incubator Center building A Applicant after: HAIKOU NAN LU PHARMACEUTICAL POLYTRON TECHNOLOGIES Inc. Address before: Room 4, building B2, Nanhai Road, Xiuying District 570311 in Hainan city of Haikou province No. 266 Haikou national high tech Zone Business Incubator Center building A Applicant before: HAIKOU NANLU PHARMACEUTICAL TECHNOLOGY CO.,LTD. |
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Address after: Room B2, 4 / F, building a, R & D center, Haikou national high tech Zone, 266 Nanhai Avenue, Haikou City, Hainan Province Patentee after: Hainan xinlai Pharmaceutical Technology Co.,Ltd. Address before: Room 4, building B2, Nanhai Road, Xiuying District 570311 in Hainan city of Haikou province No. 266 Haikou national high tech Zone Business Incubator Center building A Patentee before: HAIKOU NAN LU PHARMACEUTICAL POLYTRON TECHNOLOGIES Inc. |
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Denomination of invention: Preparation of vonolazan fumarate Effective date of registration: 20201201 Granted publication date: 20180612 Pledgee: Haikou national hi tech Zone Development Holding Co.,Ltd. Pledgor: Hainan xinlai Pharmaceutical Technology Co.,Ltd. Registration number: Y2020980008571 |
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Granted publication date: 20180612 Termination date: 20210916 |