KR102218323B1 - 효율적이고 상전이가 되지 않는 엠파글리플로진 무정형의 제조방법 - Google Patents
효율적이고 상전이가 되지 않는 엠파글리플로진 무정형의 제조방법 Download PDFInfo
- Publication number
- KR102218323B1 KR102218323B1 KR1020200115716A KR20200115716A KR102218323B1 KR 102218323 B1 KR102218323 B1 KR 102218323B1 KR 1020200115716 A KR1020200115716 A KR 1020200115716A KR 20200115716 A KR20200115716 A KR 20200115716A KR 102218323 B1 KR102218323 B1 KR 102218323B1
- Authority
- KR
- South Korea
- Prior art keywords
- amorphous
- empagliflozin
- crystallization
- manufacturing
- present
- 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.)
- Active
Links
- OBWASQILIWPZMG-QZMOQZSNSA-N empagliflozin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(O[C@@H]3COCC3)=CC=2)=C1 OBWASQILIWPZMG-QZMOQZSNSA-N 0.000 title claims abstract description 91
- 229960003345 empagliflozin Drugs 0.000 title claims abstract description 91
- 238000000034 method Methods 0.000 title claims abstract description 27
- 230000007704 transition Effects 0.000 title abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 55
- 238000002425 crystallisation Methods 0.000 claims abstract description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 230000008025 crystallization Effects 0.000 claims abstract description 23
- 238000007738 vacuum evaporation Methods 0.000 claims abstract description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007787 solid Substances 0.000 claims description 14
- 239000012296 anti-solvent Substances 0.000 claims description 11
- 239000013078 crystal Substances 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 238000000151 deposition Methods 0.000 claims description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000000634 powder X-ray diffraction Methods 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000001144 powder X-ray diffraction data Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005185 salting out Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 101710103228 Sodium/glucose cotransporter 2 Proteins 0.000 description 4
- 102100020888 Sodium/glucose cotransporter 2 Human genes 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000009102 absorption Effects 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 101710103121 Sodium/glucose cotransporter 1 Proteins 0.000 description 2
- 102100020885 Sodium/glucose cotransporter 1 Human genes 0.000 description 2
- 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108010078791 Carrier Proteins Proteins 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- CRRYCJOJLZQAFR-UHFFFAOYSA-N cyclohexane;pentane Chemical compound CCCCC.C1CCCCC1 CRRYCJOJLZQAFR-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000003168 generic drug Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
도 2은 본 발명의 실시예에 따라 제조된 엠파글리플로진 무정형의 분말 X선 회절(PXRD)패턴 결과를 보여준다.
도 3은 본 발명의 감압증발결정화 과정에서 생성된 100%의 엠파글리플로진 무정형 분말 X선 회절(PXRD)패턴 결과를 보여준다.
도 4는 국제공개특허공보 WO 2018/224957에서 실시예 9에 따라서 제조 된 엠파글리플로진 무정형의 분말 X선 회절(PXRD)패턴 결과 이다. 하지만 무정형이 아닌 무정형과 결정형의 혼합 결과로 나타났다.
도 5는 국제공개특허공보 WO 2017/203457에서 실시예 1에 따라서 제조 된 엠파글리플로진 무정형의 분말 X선 회절(PXRD)패턴 결과 이다. 하지만 무정형이 아닌 무정형과 결정형의 혼합 결과로 나타났다.
도 6는 국제공개특허공보 WO 2017/203457에서 실시예 2에 따라서 제조 된 엠파글리플로진 무정형의 분말 X선 회절(PXRD)패턴 결과 이다. 하지만 무정형이 아닌 무정형과 결정형의 혼합 결과로 나타났다.
도 7는 국제공개특허공보 WO 2017/203457에서 실시예 3에 따라서 제조 된 엠파글리플로진 무정형의 분말 X선 회절(PXRD)패턴 결과이다. 하지만 무정형이 아닌 결정형으로 나타났다.
도 8는 국제공개특허공보 WO 2017/203457에서 실시예 4에 따라서 제조 된 엠파글리플로진 무정형의 분말 X선 회절(PXRD)패턴 결과이다. 하지만 무정형이 아닌 무정형과 결정형의 혼합 결과로 나타났다.
도 9는 국제공개특허공보 WO 2017/203457에서 실시예 5에 따라서 제조 된 엠파글리플로진 무정형의 분말 X선 회절(PXRD)패턴 결과 이다. 하지만 무정형이 아닌 결정형으로 나타났다.
Claims (4)
- (a) 엠파글리플로진을 용매에 완전 용해시키는 단계;
(b) 상기 (a) 의 결과물을 감압증발 결정화를 통해 동시다발적으로 고체를 석출시키는 단계; 및
(c) 상기 (b) 의 결과물에 반용매를 투입하여 결정을 수득하는 단계를 포함하는 엠파글리플로진 무정형의 제조방법으로서, (a) 단계에서의 용매가 테트라하이드로퓨란이고, 엠파글리플로진 무정형의 수율이 80% 이상인 것을 특징으로 하는 제조방법. - 제 1 항에 있어서, (c) 단계에서의 반용매가 사이클로헥산인 것을 특징으로 하는 제조방법.
- 삭제
- 제 1 항 또는 제 2 항의 제조방법에 따라 제조된 엠파글리플로진 무정형.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020200115716A KR102218323B1 (ko) | 2020-09-09 | 2020-09-09 | 효율적이고 상전이가 되지 않는 엠파글리플로진 무정형의 제조방법 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020200115716A KR102218323B1 (ko) | 2020-09-09 | 2020-09-09 | 효율적이고 상전이가 되지 않는 엠파글리플로진 무정형의 제조방법 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR102218323B1 true KR102218323B1 (ko) | 2021-02-22 |
Family
ID=74687488
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020200115716A Active KR102218323B1 (ko) | 2020-09-09 | 2020-09-09 | 효율적이고 상전이가 되지 않는 엠파글리플로진 무정형의 제조방법 |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR102218323B1 (ko) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006117359A1 (en) | 2005-05-03 | 2006-11-09 | Boehringer Ingelheim International Gmbh | CRYSTALLINE FORM OF 1-CHLORO-4-(ß-D-GLUCOPYRANOS-1-YL)-2-[4-((S)-TETRAHYDROFURAN-3-YLOXY)-BENZYL]-BENZENE, A METHOD FOR ITS PREPARATION AND THE USE THEREOF FOR PREPARING MEDICAMENTS |
WO2011039107A1 (en) | 2009-09-30 | 2011-04-07 | Boehringer Ingelheim International Gmbh | Method for the preparation of a crystalline form of 1-chloro-4- (beta-d-glucopyranos-1-yl)-2-(4-((s)-tetrahydrofuran-3-yloxy)benzyl)benzene |
WO2016131431A1 (en) * | 2015-02-18 | 2016-08-25 | Zentiva, K.S. | Solid forms of empagliflozin |
WO2016169534A1 (en) * | 2015-04-24 | 2016-10-27 | Zentiva, K. S. | Solid forms of amorphous empagliflozin |
WO2017203457A1 (en) | 2016-05-26 | 2017-11-30 | Dr. Reddy's Laboratories Limited | Solid state forms of empagliflozin |
WO2018224957A1 (en) | 2017-06-05 | 2018-12-13 | Laurus Labs Limited | Novel process for preparation of empagliflozin or its co-crystals, solvates and their polymorphs thereof |
-
2020
- 2020-09-09 KR KR1020200115716A patent/KR102218323B1/ko active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006117359A1 (en) | 2005-05-03 | 2006-11-09 | Boehringer Ingelheim International Gmbh | CRYSTALLINE FORM OF 1-CHLORO-4-(ß-D-GLUCOPYRANOS-1-YL)-2-[4-((S)-TETRAHYDROFURAN-3-YLOXY)-BENZYL]-BENZENE, A METHOD FOR ITS PREPARATION AND THE USE THEREOF FOR PREPARING MEDICAMENTS |
WO2011039107A1 (en) | 2009-09-30 | 2011-04-07 | Boehringer Ingelheim International Gmbh | Method for the preparation of a crystalline form of 1-chloro-4- (beta-d-glucopyranos-1-yl)-2-(4-((s)-tetrahydrofuran-3-yloxy)benzyl)benzene |
WO2016131431A1 (en) * | 2015-02-18 | 2016-08-25 | Zentiva, K.S. | Solid forms of empagliflozin |
WO2016169534A1 (en) * | 2015-04-24 | 2016-10-27 | Zentiva, K. S. | Solid forms of amorphous empagliflozin |
WO2017203457A1 (en) | 2016-05-26 | 2017-11-30 | Dr. Reddy's Laboratories Limited | Solid state forms of empagliflozin |
WO2018224957A1 (en) | 2017-06-05 | 2018-12-13 | Laurus Labs Limited | Novel process for preparation of empagliflozin or its co-crystals, solvates and their polymorphs thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2012066565A2 (en) | Asenapine maleate amorphous and crystalline form and process for preparation thereof | |
CN104797580A (zh) | 阿哌沙班的晶型或无定形及其制备工艺 | |
CN105121434A (zh) | 坎格列净一水合物及其晶型、它们的制备方法和用途 | |
SK284935B6 (sk) | Forma I (-)-6-chlór-4-cyklopropyletynyl-4-tri-fluórmetyl-1,4- dihydro-2H-3,1-benzoxazín-2-ónu a spôsob jej kryštalizácie | |
CN105693734B (zh) | 一种特质ε-HNIW晶体及其制备方法 | |
KR102218323B1 (ko) | 효율적이고 상전이가 되지 않는 엠파글리플로진 무정형의 제조방법 | |
CN102875531A (zh) | 一种(r)-兰索拉唑无水晶型及其制备方法 | |
EP1673359B1 (en) | Process for the preparation of crystalline forms of orlistat | |
CN104151324B (zh) | 一种溶媒结晶法制备氨苄西林钠的方法 | |
EP3125869A1 (en) | Porous materials containing compounds including pharmaceutically active species | |
CN105859730B (zh) | 一种反溶剂稀释法制备小颗粒圆滑ε-HNIW晶体的方法 | |
CN112608238A (zh) | 十六烷基曲前列环素晶体和其制备方法 | |
CN115850169B (zh) | 苯磺顺阿曲库铵杂质及其中间体的制备方法 | |
EP1869015A1 (en) | An improved process for the manufacture of rabeprazole sodium | |
WO2020095316A1 (en) | Meloxicam co-crystals | |
CN105924447B (zh) | 一种反溶剂稀释加晶种诱导法制备大颗粒圆滑ε-HNIW晶体的方法 | |
KR102333167B1 (ko) | 효율적이고 대량생산이 가능한 미라베그론 무정형 제조방법 | |
KR102111247B1 (ko) | 다파글리플로진 무정형 형태의 공결정 또는 복합제 | |
WO2012171377A1 (zh) | 一类积雪草酸氨丁三醇盐晶型及其制备方法 | |
CN100387586C (zh) | 手性2-胺基-1-(6-氟-3,4-二氢苯并吡喃基)乙醇的合成方法 | |
EP3771718A1 (en) | Process for preparing the crystalline form ii of sotagliflozin | |
JP2021098689A (ja) | 超高純度トレプロスチニルを調製するための効率的な結晶化プロセス及びそれから調製された結晶 | |
KR102207319B1 (ko) | 새로운 엠파글리플로진의 공결정 | |
CN111217781A (zh) | 贝前列素-314d晶体和其制备方法 | |
CN113454084A (zh) | 醛糖还原酶抑制剂的盐及其制备方法和应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 20200909 |
|
PA0201 | Request for examination | ||
PA0302 | Request for accelerated examination |
Patent event date: 20200910 Patent event code: PA03022R01D Comment text: Request for Accelerated Examination Patent event date: 20200909 Patent event code: PA03021R01I Comment text: Patent Application |
|
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20210216 |
|
PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20210216 Patent event code: PR07011E01D |
|
PR1002 | Payment of registration fee |
Payment date: 20210216 End annual number: 3 Start annual number: 1 |
|
PG1601 | Publication of registration | ||
PR1001 | Payment of annual fee |
Payment date: 20240306 Start annual number: 4 End annual number: 4 |