RU2727805C2 - Аминопиразиновые соединения со свойствами антагониста a2a - Google Patents
Аминопиразиновые соединения со свойствами антагониста a2a Download PDFInfo
- Publication number
- RU2727805C2 RU2727805C2 RU2017120853A RU2017120853A RU2727805C2 RU 2727805 C2 RU2727805 C2 RU 2727805C2 RU 2017120853 A RU2017120853 A RU 2017120853A RU 2017120853 A RU2017120853 A RU 2017120853A RU 2727805 C2 RU2727805 C2 RU 2727805C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- amino
- carboxamide
- pyrazine
- oxazol
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
-
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462081262P | 2014-11-18 | 2014-11-18 | |
| US62/081,262 | 2014-11-18 | ||
| PCT/US2015/060509 WO2016081290A1 (en) | 2014-11-18 | 2015-11-13 | Aminopyrazine compounds with a2a antagonist properties |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2017120853A RU2017120853A (ru) | 2018-12-19 |
| RU2017120853A3 RU2017120853A3 (enExample) | 2019-06-17 |
| RU2727805C2 true RU2727805C2 (ru) | 2020-07-24 |
Family
ID=56014406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017120853A RU2727805C2 (ru) | 2014-11-18 | 2015-11-13 | Аминопиразиновые соединения со свойствами антагониста a2a |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10472347B2 (enExample) |
| EP (1) | EP3220910B1 (enExample) |
| JP (2) | JP6779204B2 (enExample) |
| KR (1) | KR20170083136A (enExample) |
| CN (1) | CN107106558A (enExample) |
| AU (1) | AU2015350315B2 (enExample) |
| BR (1) | BR112017010261A2 (enExample) |
| CA (1) | CA2967944C (enExample) |
| MX (1) | MX381180B (enExample) |
| RU (1) | RU2727805C2 (enExample) |
| WO (1) | WO2016081290A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3484856B1 (en) * | 2016-07-12 | 2023-11-15 | Revolution Medicines, Inc. | 2,5-disubstituted 3-methyl pyrazines and 2,5,6-trisubstituted 3-methyl pyrazines as allosteric shp2 inhibitors |
| RU2019126455A (ru) | 2017-01-23 | 2021-02-24 | Революшн Медсинз, Инк. | Пиридиновые соединения в качестве аллостерических ингибиторов shp2 |
| IL296456A (en) | 2017-01-23 | 2022-11-01 | Revolution Medicines Inc | Bicyclics as allosteric shp2 inhibitors |
| CN108570054B (zh) * | 2017-03-07 | 2021-07-16 | 广州再极医药科技有限公司 | 氨基嘧啶并五元杂环化合物、其中间体、制备方法、药物组合物及应用 |
| CA3070073A1 (en) | 2017-07-18 | 2019-01-24 | Nuvation Bio Inc. | 1,8-naphthyridinone compounds and uses thereof |
| US11028058B2 (en) | 2017-07-18 | 2021-06-08 | Nuvation Bio Inc. | Heterocyclic compounds as adenosine antagonists |
| CN111629728A (zh) | 2017-08-31 | 2020-09-04 | 科尔沃斯制药股份有限公司 | 用于调节腺苷a2b受体和腺苷a2a受体的化合物和方法 |
| SG11202002941WA (en) | 2017-10-12 | 2020-04-29 | Revolution Medicines Inc | Pyridine, pyrazine, and triazine compounds as allosteric shp2 inhibitors |
| EP3723754A4 (en) | 2017-12-13 | 2021-05-19 | Merck Sharp & Dohme Corp. | IMIDAZO [1,2-C] QUINAZOLINE-5-AMINE COMPOUNDS WITH PROPERTIES OF A2A ANTAGONIST |
| RU2020123241A (ru) | 2017-12-15 | 2022-01-17 | Революшн Медсинз, Инк. | Полициклические соединения в качестве аллостерических ингибиторов shp2 |
| CA3109778A1 (en) | 2018-08-16 | 2020-02-20 | Innate Tumor Immunity, Inc. | Substitued 4-amino-1h-imidazo[4,5-c]quinoline compounds and improved methods for their preparation |
| EP3616753A1 (en) * | 2018-08-31 | 2020-03-04 | Corvus Pharmaceuticals, Inc. | Compounds for modulating adenosine a2b receptor and adenosine a2a receptor |
| CN113015530A (zh) | 2018-11-20 | 2021-06-22 | 默沙东公司 | 取代的氨基三唑并嘧啶和氨基三唑并吡嗪腺苷受体拮抗剂、药物组合物及其用途 |
| EP3883576B1 (en) | 2018-11-20 | 2025-12-17 | Merck Sharp & Dohme LLC | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| US12263171B2 (en) | 2018-11-30 | 2025-04-01 | Merck Sharp & Dohme Llc | 7-, 8-, and 10-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use |
| TW202039496A (zh) | 2018-11-30 | 2020-11-01 | 美商默沙東藥廠 | 做為腺苷受體拮抗劑之9-經取代胺基三唑喹唑啉衍生物、醫藥組合物及其用途 |
| JP7625524B2 (ja) | 2019-01-11 | 2025-02-03 | オメロス コーポレーション | がんを処置するための方法および組成物 |
| AU2020208644A1 (en) | 2019-01-18 | 2021-08-26 | Nuvation Bio Inc. | Heterocyclic compounds as adenosine antagonists |
| WO2020150676A1 (en) | 2019-01-18 | 2020-07-23 | Nuvation Bio Inc. | 1,8-naphthyridinone compounds and uses thereof |
| TW202128650A (zh) * | 2019-10-11 | 2021-08-01 | 德商拜耳動物保健有限公司 | 作為殺蟲劑之新穎的雜芳基取代之吡𠯤衍生物 |
| CN111285798A (zh) * | 2020-04-09 | 2020-06-16 | 阿里生物新材料（常州）有限公司 | 一种（3-环丙基吡啶-2-基）甲胺盐酸盐的合成方法 |
| CN111423364A (zh) * | 2020-05-19 | 2020-07-17 | 阿里生物新材料（常州）有限公司 | 一种（3-环丙基吡啶-2-基）甲胺的合成方法 |
| EP3929189A1 (en) * | 2020-06-25 | 2021-12-29 | Bayer Animal Health GmbH | Novel heteroaryl-substituted pyrazine derivatives as pesticides |
| TW202304865A (zh) | 2021-03-23 | 2023-02-01 | 美商百愛及生物醫藥公司 | Nlrp3發炎體之抑制劑 |
| JP2025504008A (ja) | 2022-01-28 | 2025-02-06 | バイオエイジ ラブス， インコーポレイテッド | Ｎｌｒｐ３インフラマソームのｎ－オキシド阻害剤 |
| AU2023252914A1 (en) | 2022-04-13 | 2024-10-17 | Arcus Biosciences, Inc. | Combination therapy for treating trop-2 expressing cancers |
| US20250074870A1 (en) * | 2023-03-30 | 2025-03-06 | Brandeis University | Solid-solid phase change aromatic azo compounds, method of manufacture, and use for thermal energy storage and release |
| WO2025137640A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004111033A1 (en) * | 2003-06-18 | 2004-12-23 | Astrazeneca Ab | 2-substitued 5, 6-diaryl-pyrazine derivatives as cb1 modulator. |
| US20050113387A1 (en) * | 2003-10-27 | 2005-05-26 | Fujisawa Pharmaceutical Co. Ltd. | Pyrazine derivatives and pharmaceutical use thereof |
| US20090233944A1 (en) * | 2005-03-04 | 2009-09-17 | Georg Jaeschke | Pyrazine-2-carboxyamide derivatives |
| US20100075989A1 (en) * | 2002-12-17 | 2010-03-25 | Astrazeneca Ab | Novel Compounds Having Selective Inhibiting Effect at GSK3 |
| US20120065205A1 (en) * | 2009-06-01 | 2012-03-15 | Mercer Swati P | Pyrazine carboxamide orexin receptor antagonists |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1264901B1 (it) | 1993-06-29 | 1996-10-17 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(15-c)pirimidine ad attivita' antagonista per il recettore a2 dell'adenosina |
| ATE208199T1 (de) | 1993-07-27 | 2001-11-15 | Kyowa Hakko Kogyo Kk | Arzneimittel gegen parkinsonsche krankheit |
| IT1277392B1 (it) | 1995-07-28 | 1997-11-10 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(1,5-c]pirimidine ad attivita' antagonista per il recettore a2a dell'adenosina |
| IT1291372B1 (it) | 1997-05-21 | 1999-01-07 | Schering Plough S P A | Uso di analoghi eterociclici di 1,2,4-triazolo (1,5-c) pirimidine per la preparazione di medicamenti utili per il trattamento delle malattie |
| RU2315053C2 (ru) | 2000-05-26 | 2008-01-20 | Шеринг Корпорейшн | ПРОИЗВОДНЫЕ 5-АМИНО-ПИРАЗОЛО-[4,3-е]-1,2,4-ТРИАЗОЛО[1,5-с]ПИРИМИДИНА, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ИХ ОСНОВЕ, ПРИМЕНЕНИЕ И СПОСОБЫ ПОЛУЧЕНИЯ ПРОМЕЖУТОЧНЫХ СОЕДИНЕНИЙ |
| ES2270715B1 (es) * | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
-
2015
- 2015-11-13 BR BR112017010261-7A patent/BR112017010261A2/pt not_active IP Right Cessation
- 2015-11-13 US US15/525,788 patent/US10472347B2/en active Active
- 2015-11-13 WO PCT/US2015/060509 patent/WO2016081290A1/en not_active Ceased
- 2015-11-13 RU RU2017120853A patent/RU2727805C2/ru active
- 2015-11-13 EP EP15861650.8A patent/EP3220910B1/en active Active
- 2015-11-13 KR KR1020177016281A patent/KR20170083136A/ko not_active Withdrawn
- 2015-11-13 CN CN201580073488.3A patent/CN107106558A/zh active Pending
- 2015-11-13 JP JP2017526527A patent/JP6779204B2/ja not_active Expired - Fee Related
- 2015-11-13 MX MX2017006483A patent/MX381180B/es unknown
- 2015-11-13 AU AU2015350315A patent/AU2015350315B2/en not_active Ceased
- 2015-11-13 CA CA2967944A patent/CA2967944C/en not_active Expired - Fee Related
-
2020
- 2020-08-19 JP JP2020138418A patent/JP2020193211A/ja not_active Withdrawn
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100075989A1 (en) * | 2002-12-17 | 2010-03-25 | Astrazeneca Ab | Novel Compounds Having Selective Inhibiting Effect at GSK3 |
| WO2004111033A1 (en) * | 2003-06-18 | 2004-12-23 | Astrazeneca Ab | 2-substitued 5, 6-diaryl-pyrazine derivatives as cb1 modulator. |
| US20050113387A1 (en) * | 2003-10-27 | 2005-05-26 | Fujisawa Pharmaceutical Co. Ltd. | Pyrazine derivatives and pharmaceutical use thereof |
| US20090233944A1 (en) * | 2005-03-04 | 2009-09-17 | Georg Jaeschke | Pyrazine-2-carboxyamide derivatives |
| RU2407739C2 (ru) * | 2005-03-04 | 2010-12-27 | Ф. Хоффманн-Ля Рош Аг | ПРОИЗВОДНЫЕ ПИРАЗИН-2-КАРБОКСАМИДА В КАЧЕСТВЕ АНТАГОНИСТОВ mGluR5 |
| US20120065205A1 (en) * | 2009-06-01 | 2012-03-15 | Mercer Swati P | Pyrazine carboxamide orexin receptor antagonists |
Non-Patent Citations (2)
| Title |
|---|
| CELINE BONNEFOUS et al.: "Dipyridyl amides: potent metabotropic glutamate subtype 5 (mGlu5) receptor antagonists", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, vol.15, no.4, pages 1197-1200 * |
| CELINE BONNEFOUS et al.: "Dipyridyl amides: potent metabotropic glutamate subtype 5 (mGlu5) receptor antagonists", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, vol.15, no.4, pages 1197-1200. * |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2017006483A (es) | 2017-09-12 |
| AU2015350315A1 (en) | 2017-05-18 |
| RU2017120853A3 (enExample) | 2019-06-17 |
| KR20170083136A (ko) | 2017-07-17 |
| MX381180B (es) | 2025-03-12 |
| JP2017533946A (ja) | 2017-11-16 |
| CA2967944C (en) | 2020-11-17 |
| AU2015350315B2 (en) | 2020-06-25 |
| US10472347B2 (en) | 2019-11-12 |
| BR112017010261A2 (pt) | 2018-02-06 |
| JP6779204B2 (ja) | 2020-11-04 |
| EP3220910A4 (en) | 2018-04-25 |
| WO2016081290A1 (en) | 2016-05-26 |
| CA2967944A1 (en) | 2016-05-26 |
| EP3220910A1 (en) | 2017-09-27 |
| EP3220910B1 (en) | 2020-01-15 |
| CN107106558A (zh) | 2017-08-29 |
| RU2017120853A (ru) | 2018-12-19 |
| JP2020193211A (ja) | 2020-12-03 |
| US20180327385A1 (en) | 2018-11-15 |
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