JP2017522357A5 - - Google Patents
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- JP2017522357A5 JP2017522357A5 JP2017505480A JP2017505480A JP2017522357A5 JP 2017522357 A5 JP2017522357 A5 JP 2017522357A5 JP 2017505480 A JP2017505480 A JP 2017505480A JP 2017505480 A JP2017505480 A JP 2017505480A JP 2017522357 A5 JP2017522357 A5 JP 2017522357A5
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- 150000001875 compounds Chemical class 0.000 claims 94
- 238000000034 method Methods 0.000 claims 37
- 238000004519 manufacturing process Methods 0.000 claims 20
- 239000000203 mixture Substances 0.000 claims 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 12
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 9
- 239000012442 inert solvent Substances 0.000 claims 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 5
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 5
- 230000003197 catalytic effect Effects 0.000 claims 5
- 238000005580 one pot reaction Methods 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 238000003756 stirring Methods 0.000 claims 4
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 3
- 229960000583 acetic acid Drugs 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 239000012362 glacial acetic acid Substances 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 0 C*c1c(C=C(C(C)=O)C(OCCC#N)=O)ccc(C#N)c1 Chemical compound C*c1c(C=C(C(C)=O)C(OCCC#N)=O)ccc(C#N)c1 0.000 description 1
- RFJLQSVKIAMLCX-NTEUORMPSA-N CC(/C(/C(OCCC#N)=O)=C\c(ccc(C#N)c1)c1OC)=O Chemical compound CC(/C(/C(OCCC#N)=O)=C\c(ccc(C#N)c1)c1OC)=O RFJLQSVKIAMLCX-NTEUORMPSA-N 0.000 description 1
- WWAABAWXHRNWCT-UHFFFAOYSA-N CC(C(C(I)=O)C(OC)=C1)C=C1[Zn] Chemical compound CC(C(C(I)=O)C(OC)=C1)C=C1[Zn] WWAABAWXHRNWCT-UHFFFAOYSA-N 0.000 description 1
- SMWPNASNQIIBDW-UHFFFAOYSA-N CC(C1=C2C(c(ccc(N)c3)c3OC)C(C(OCCN)=O)=C(C)N1)=CNC2=O Chemical compound CC(C1=C2C(c(ccc(N)c3)c3OC)C(C(OCCN)=O)=C(C)N1)=CNC2=O SMWPNASNQIIBDW-UHFFFAOYSA-N 0.000 description 1
- WUPRJMHPZJWLHY-YYBBLCMGSA-N CCOc1ncc(C)c2c1[C@H](C(/C(/OC)=C\C(\C#N)=C/C)=C)C(C(N)=O)=C(C)N2 Chemical compound CCOc1ncc(C)c2c1[C@H](C(/C(/OC)=C\C(\C#N)=C/C)=C)C(C(N)=O)=C(C)N2 WUPRJMHPZJWLHY-YYBBLCMGSA-N 0.000 description 1
- ZXENVSJZOHXCKL-UHFFFAOYSA-N COc1c(C=O)ccc(C#N)c1 Chemical compound COc1c(C=O)ccc(C#N)c1 ZXENVSJZOHXCKL-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14179544.3 | 2014-08-01 | ||
| EP14179544 | 2014-08-01 | ||
| PCT/EP2015/067340 WO2016016287A1 (de) | 2014-08-01 | 2015-07-29 | Verfahren zur herstellung von (4s)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carbox-amid und dessen aufreinigung für die verwendung als pharmazeutischer wirkstoff |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017522357A JP2017522357A (ja) | 2017-08-10 |
| JP2017522357A5 true JP2017522357A5 (cg-RX-API-DMAC7.html) | 2018-09-06 |
| JP6818674B2 JP6818674B2 (ja) | 2021-01-20 |
Family
ID=51260727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017505480A Active JP6818674B2 (ja) | 2014-08-01 | 2015-07-29 | （４ｓ）−４−（４−シアノ−２−メトキシフェニル）−５−エトキシ−２，８−ジメチル−１，４−ジヒドロ−１，６−ナフチリジン−３−カルボキサミドを調製するための方法および医薬品有効成分としての使用のためのその精製 |
Country Status (31)
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20250108757A (ko) * | 2014-08-01 | 2025-07-15 | 바이엘 파마 악티엔게젤샤프트 | (4s)-4-(4-시아노-2-메톡시페닐)-5-에톡시-2,8-디메틸-1,4-디히드로-1,6-나프티리딘-3-카르복스아미드의제조 방법 및 활성 제약 성분으로서 사용하기 위한 그의 정제 |
| HRP20191431T1 (hr) * | 2015-08-21 | 2019-11-01 | Bayer Pharma AG | Postupak za pripravu (4s)-4-(4-cijano-2-metoksifenil)-5-etoksi-2,8-dimetil-1,4-dihidro-1-6- naftiridin-3-karboksamida i njegovo pročišćavanje za uporabu kao aktivni farmaceutski pripravak |
| EP3560922A1 (de) | 2018-04-24 | 2019-10-30 | Bayer Aktiengesellschaft | Verfahren zur herstellung von (4s)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carbox-amid durch racemat-spaltung mittels diastereomerer weinsäureester |
| AU2020233169A1 (en) | 2019-03-05 | 2021-09-23 | Bayer Aktiengesellschaft | Process for preparing 4-amino-5-methylpyridone |
| AU2020230965A1 (en) | 2019-03-05 | 2021-09-23 | Bayer Aktiengesellschaft | Synthesis of 4-amino-5-methyl-1H-pyridin-2(1H)-on (intermediate compound for the synthesis of the MR antagonist finerenone) from 2-chloro-5-methyl-4-nitro-pyridine-1-oxide using the intermediate compound 2-chloro-5-methyl-4-pyridinamine |
| US20250270204A1 (en) * | 2019-10-17 | 2025-08-28 | Bayer Aktiengesellschaft | Process for the preparation of 2-cyanoethyl (4s)-4-(4-cyano-2-methoxy-phenyl)-5-hydroxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carboxylate by racemate separation by means of diastereomeric tartaric acid esters |
| CA3157823A1 (en) * | 2019-10-17 | 2021-04-22 | Bayer Aktiengesellschaft | Process for producing acyloxymethyl esters of (4s)-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carboxylic acid |
| PE20221420A1 (es) * | 2019-10-17 | 2022-09-20 | Bayer Ag | Procedimiento fotoquimico para la preparacion de (4r,4s)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida |
| KR20220084103A (ko) * | 2019-10-17 | 2022-06-21 | 바이엘 악티엔게젤샤프트 | 부분입체이성질체 타르타르산 에스테르를 사용한 라세미체 분해에 의한 2-시아노에틸 (4s)-4-(4-시아노-2-메톡시페닐)-5-에톡시-2,8-디메틸-1,4-디히드로-1,6-나프티리딘-3-카르복실레이트의 제조 방법 |
| JP2023523596A (ja) | 2020-04-22 | 2023-06-06 | バイエル アクチェンゲゼルシャフト | 心血管疾患および／または腎疾患を治療および／または予防するためのフィネレノンとｓｇｌｔ２阻害剤の組み合わせ |
| EP3900722A1 (en) | 2020-04-22 | 2021-10-27 | Bayer AG | Combination of finerenone and pecavaptan for the treatment and/or prevention of cardiovascular and/or renal diseases |
| TW202214624A (zh) | 2020-06-16 | 2022-04-16 | 德商拜耳廠股份有限公司 | 藉由催化不對稱漢斯（ｈａｎｔｚｓｃｈ）酯還原法進行之製備（４ｓ）－４－（４－氰基－２－甲氧基苯基）－５－乙氧基－２，８－二甲基－１，４－二氫－１，６－㖠啶－３－羧醯胺的方法 |
| CN112237573B (zh) * | 2020-10-29 | 2023-12-22 | 瑞阳制药股份有限公司 | 含finerenone的片剂及其制备方法 |
| WO2022214206A1 (en) | 2021-04-08 | 2022-10-13 | Bayer Aktiengesellschaft | Combination of finerenone and pecavaptan for the treatment and/or prevention of cardiovascular and/or renal diseases |
| CN114149427A (zh) * | 2021-12-18 | 2022-03-08 | 上海鼎雅药物化学科技有限公司 | 非奈利酮及其中间体的合成方法 |
| CN115340539B (zh) | 2022-01-19 | 2024-02-27 | 奥锐特药业股份有限公司 | 制备非奈利酮及其中间体的方法 |
| CN115340540A (zh) * | 2022-01-20 | 2022-11-15 | 奥锐特药业股份有限公司 | 制备非奈利酮及其中间体的方法 |
| CN114524812A (zh) * | 2022-03-18 | 2022-05-24 | 湖南凯铂生物药业有限公司 | 1,4-二氢-1,6-萘啶化合物的晶型制备以及合成方法 |
| WO2023205164A1 (en) | 2022-04-18 | 2023-10-26 | Teva Pharmaceuticals International Gmbh | Processes for the preparation of finerenone |
| EP4286368A1 (de) | 2022-05-31 | 2023-12-06 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 4-formyl-3-methoxybenzonitril |
| WO2024075139A1 (en) * | 2022-10-06 | 2024-04-11 | Maithri Drugs Private Limited | A process for preparation of finerenone and intermediates thereof |
| JP2025537211A (ja) | 2022-11-04 | 2025-11-14 | ナンジン ブイケア ファーマテック カンパニー リミテッド | ジアステレオマー酒石酸エステルによりラセミ体を分割することによりフィネレノンを調製する方法 |
| KR20250105629A (ko) * | 2022-11-23 | 2025-07-08 | 바이엘 악티엔게젤샤프트 | 유형 i 당뇨병에서의 만성 신장 질환의 치료 |
| EP4634179A1 (en) | 2022-12-16 | 2025-10-22 | Bayer Aktiengesellschaft | Sequential one-pot synthesis for preparing 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide |
| WO2024147053A1 (en) * | 2023-01-03 | 2024-07-11 | Optimus Drugs Pvt Ltd | Improved process for the preparation of finerenone |
| CN120731206A (zh) * | 2023-03-17 | 2025-09-30 | 江苏恒瑞医药股份有限公司 | 一种1,4-二氢-1,6-萘啶酰胺化合物的可药用盐、晶型及其制备方法 |
| WO2025104752A1 (en) * | 2023-11-18 | 2025-05-22 | Msn Laboratories Private Limited, R&D Center | Improved process for the preparation of (4s)4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide |
| CN120081840A (zh) * | 2023-12-01 | 2025-06-03 | 山东诚创蓝海医药科技有限公司 | 一种非奈利酮-马来酸共晶及其制备方法 |
| US20250313559A1 (en) | 2024-01-05 | 2025-10-09 | Bayer Aktiengesellschaft | Method of preventing or treating heart failure in a patient using (4s)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide |
| WO2025247801A1 (en) * | 2024-05-30 | 2025-12-04 | Bayer Aktiengesellschaft | Determination of a dosage of a nonsteroidal mineralocorticoid receptor antagonist |
| CN119462643A (zh) * | 2024-10-17 | 2025-02-18 | 河北国龙制药有限公司 | 一种非奈利酮单晶及其制备方法和应用 |
| CN119019395A (zh) * | 2024-10-29 | 2024-11-26 | 成都诺和晟欣生物医药有限公司 | 一种非奈利酮晶型ⅰ的制备方法 |
| CN119684288A (zh) * | 2024-12-18 | 2025-03-25 | 安徽先和医药研究有限公司 | 非奈利酮的制备方法 |
| CN119684289A (zh) * | 2024-12-18 | 2025-03-25 | 安徽先和医药研究有限公司 | 一种非奈利酮的制备方法 |
Family Cites Families (22)
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|---|---|---|---|---|
| IL75987A (en) * | 1984-08-25 | 1991-07-18 | Goedecke Ag | Tri-and tetrasubstituted-1,4-dihydro-1,6-naphthyridine-3-carboxylic acid derivatives,their preparation and pharmaceutical compositions containing them |
| US4895860A (en) * | 1989-04-21 | 1990-01-23 | American Home Products Corporation | Novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides useful as anthihyperglycemic agents |
| DE19834044A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Neue substituierte Pyrazolderivate |
| DE19834047A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Substituierte Pyrazolderivate |
| GB9914825D0 (en) | 1999-06-24 | 1999-08-25 | Smithkline Beecham Spa | Novel compounds |
| DE19943635A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943634A1 (de) | 1999-09-13 | 2001-04-12 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943636A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943639A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Dicarbonsäurederivate mit neuartigen pharmazeutischen Eigenschaften |
| AR031176A1 (es) | 2000-11-22 | 2003-09-10 | Bayer Ag | Nuevos derivados de pirazolpiridina sustituidos con piridina |
| DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
| DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| ES2357015T3 (es) * | 2004-10-15 | 2011-04-15 | Bayer Healthcare Llc | Preparación y uso de derivados bifenil-4-ilcarbonilaminoácido para el tratamiento de la obesidad. |
| EP1819684B1 (en) * | 2004-12-03 | 2013-08-07 | Intervet International B.V. | Substituted piperazines as cb1 antagonists |
| AU2006201739A1 (en) * | 2005-05-05 | 2006-11-23 | The University Of North Carolina At Chapel Hill | Synthesis and antiprotozoal activity of dicationic 3,5-diphenylisoxazoles |
| JP2009501199A (ja) | 2005-07-12 | 2009-01-15 | グラクソ グループ リミテッド | Ｇｐｒ３８アゴニストとしてのピペラジンヘテロアリール誘導体 |
| DE102006026583A1 (de) | 2006-06-07 | 2007-12-13 | Bayer Healthcare Aktiengesellschaft | Aryl-substituierte hetero-bicyclische Verbindungen und ihre Verwendung |
| DE102006044696A1 (de) | 2006-09-22 | 2008-03-27 | Bayer Healthcare Ag | 3-Cyano-5-thiazaheteroaryl-dihydropyridine und ihre Verwendung |
| DE102007009494A1 (de) | 2007-02-27 | 2008-08-28 | Bayer Healthcare Ag | Substituierte 4-Aryl-1, 4-dihydro-1,6-naphthyridinamide und ihre Verwendung |
| CN102020587A (zh) | 2010-11-25 | 2011-04-20 | 大连凯飞精细化工有限公司 | 2-甲氧基-4-氰基苯甲醛的合成方法 |
| KR20250108757A (ko) * | 2014-08-01 | 2025-07-15 | 바이엘 파마 악티엔게젤샤프트 | (4s)-4-(4-시아노-2-메톡시페닐)-5-에톡시-2,8-디메틸-1,4-디히드로-1,6-나프티리딘-3-카르복스아미드의제조 방법 및 활성 제약 성분으로서 사용하기 위한 그의 정제 |
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2015
- 2015-07-29 KR KR1020257022052A patent/KR20250108757A/ko active Pending
- 2015-07-29 DK DK15742306.2T patent/DK3174875T3/da active
- 2015-07-29 HR HRP20201800TT patent/HRP20201800T1/hr unknown
- 2015-07-29 CN CN202310620718.XA patent/CN116655630B/zh active Active
- 2015-07-29 RU RU2017106602A patent/RU2729998C9/ru active
- 2015-07-29 AU AU2015295376A patent/AU2015295376C1/en active Active
- 2015-07-29 SG SG11201700785UA patent/SG11201700785UA/en unknown
- 2015-07-29 EP EP19213735.4A patent/EP3660015A1/de not_active Withdrawn
- 2015-07-29 MY MYPI2017700334A patent/MY198066A/en unknown
- 2015-07-29 UA UAA201701875A patent/UA122773C2/uk unknown
- 2015-07-29 LT LTEP15742306.2T patent/LT3174875T/lt unknown
- 2015-07-29 HU HUE15742306A patent/HUE051350T2/hu unknown
- 2015-07-29 US US17/002,115 patent/USRE49575E1/en active Active
- 2015-07-29 CN CN202310619597.7A patent/CN116655629A/zh active Pending
- 2015-07-29 JP JP2017505480A patent/JP6818674B2/ja active Active
- 2015-07-29 PT PT157423062T patent/PT3174875T/pt unknown
- 2015-07-29 ES ES15742306T patent/ES2828704T3/es active Active
- 2015-07-29 KR KR1020237014295A patent/KR102830206B1/ko active Active
- 2015-07-29 KR KR1020177005278A patent/KR102527893B1/ko active Active
- 2015-07-29 MX MX2017001507A patent/MX369467B/es active IP Right Grant
- 2015-07-29 SI SI201531406T patent/SI3174875T1/sl unknown
- 2015-07-29 CN CN202310616268.7A patent/CN116655627A/zh active Pending
- 2015-07-29 US US15/329,043 patent/US10059707B2/en not_active Ceased
- 2015-07-29 RS RS20201213A patent/RS60921B1/sr unknown
- 2015-07-29 EP EP15742306.2A patent/EP3174875B1/de active Active
- 2015-07-29 WO PCT/EP2015/067340 patent/WO2016016287A1/de not_active Ceased
- 2015-07-29 CA CA3146285A patent/CA3146285C/en active Active
- 2015-07-29 PL PL15742306T patent/PL3174875T3/pl unknown
- 2015-07-29 BR BR112017001678-8A patent/BR112017001678B1/pt active IP Right Grant
- 2015-07-29 CN CN201580053456.7A patent/CN106795155B/zh active Active
- 2015-07-29 CA CA2956529A patent/CA2956529A1/en active Pending
- 2015-07-29 PE PE2017000143A patent/PE20170141A1/es unknown
- 2015-07-30 JO JOP/2015/0184A patent/JO3648B1/ar active
- 2015-07-30 TW TW104124689A patent/TWI684593B/zh active
- 2015-07-31 UY UY0001036251A patent/UY36251A/es not_active Application Discontinuation
- 2015-07-31 AR ARP150102475A patent/AR101403A1/es unknown
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2017
- 2017-01-23 IL IL250239A patent/IL250239B/en active IP Right Grant
- 2017-01-31 CL CL2017000263A patent/CL2017000263A1/es unknown
- 2017-01-31 CO CONC2017/0000886A patent/CO2017000886A2/es unknown
-
2018
- 2018-08-27 US US16/114,198 patent/US10399977B2/en not_active Ceased
-
2020
- 2020-11-03 US US17/087,659 patent/USRE49860E1/en active Active
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