JP2014513046A5 - - Google Patents
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- Publication number
- JP2014513046A5 JP2014513046A5 JP2013553647A JP2013553647A JP2014513046A5 JP 2014513046 A5 JP2014513046 A5 JP 2014513046A5 JP 2013553647 A JP2013553647 A JP 2013553647A JP 2013553647 A JP2013553647 A JP 2013553647A JP 2014513046 A5 JP2014513046 A5 JP 2014513046A5
- Authority
- JP
- Japan
- Prior art keywords
- deuterium
- alkyl
- cycloalkyl
- compound
- phenyl
- 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.)
- Pending
Links
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 45
- 229910052805 deuterium Inorganic materials 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 201000003631 narcolepsy Diseases 0.000 claims description 9
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 230000000422 nocturnal effect Effects 0.000 claims description 7
- 206010010904 Convulsion Diseases 0.000 claims description 6
- 208000001640 Fibromyalgia Diseases 0.000 claims description 6
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 6
- VWYANPOOORUCFJ-UHFFFAOYSA-N alpha-Fernenol Chemical compound CC1(C)C(O)CCC2(C)C3=CCC4(C)C5CCC(C(C)C)C5(C)CCC4(C)C3CCC21 VWYANPOOORUCFJ-UHFFFAOYSA-N 0.000 claims description 6
- 206010022437 insomnia Diseases 0.000 claims description 6
- 229960003928 sodium oxybate Drugs 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229940002612 prodrug Drugs 0.000 claims description 5
- 239000000651 prodrug Substances 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- GJJFMKBJSRMPLA-HIFRSBDPSA-N (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenyl-1-cyclopropanecarboxamide Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)N(CC)CC)C[C@@H]1CN GJJFMKBJSRMPLA-HIFRSBDPSA-N 0.000 claims description 4
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical group C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 claims description 4
- 108090000312 Calcium Channels Proteins 0.000 claims description 4
- 102000003922 Calcium Channels Human genes 0.000 claims description 4
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 claims description 4
- 230000005856 abnormality Effects 0.000 claims description 4
- 230000009977 dual effect Effects 0.000 claims description 4
- 229960002866 duloxetine Drugs 0.000 claims description 4
- 229960002870 gabapentin Drugs 0.000 claims description 4
- 229960000600 milnacipran Drugs 0.000 claims description 4
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims description 4
- 229960001233 pregabalin Drugs 0.000 claims description 4
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 claims description 4
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims description 4
- 229960004688 venlafaxine Drugs 0.000 claims description 4
- 208000007848 Alcoholism Diseases 0.000 claims description 3
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 3
- 206010013654 Drug abuse Diseases 0.000 claims description 3
- 208000004547 Hallucinations Diseases 0.000 claims description 3
- 206010019468 Hemiplegia Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010039897 Sedation Diseases 0.000 claims description 3
- 208000005439 Sleep paralysis Diseases 0.000 claims description 3
- 208000032140 Sleepiness Diseases 0.000 claims description 3
- 206010041349 Somnolence Diseases 0.000 claims description 3
- 201000007930 alcohol dependence Diseases 0.000 claims description 3
- 208000029650 alcohol withdrawal Diseases 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 201000006517 essential tremor Diseases 0.000 claims description 3
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 3
- 208000001797 obstructive sleep apnea Diseases 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 230000036280 sedation Effects 0.000 claims description 3
- 201000002859 sleep apnea Diseases 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 208000022925 sleep disturbance Diseases 0.000 claims description 3
- 230000037321 sleepiness Effects 0.000 claims description 3
- 208000011117 substance-related disease Diseases 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000002510 pyrogen Substances 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 208000032841 Bulimia Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
- 230000011514 reflex Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 230000000946 synaptic effect Effects 0.000 description 3
- 208000019505 Deglutition disease Diseases 0.000 description 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical class OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161442451P | 2011-02-14 | 2011-02-14 | |
| US61/442,451 | 2011-02-14 | ||
| US201161484296P | 2011-05-10 | 2011-05-10 | |
| US61/484,296 | 2011-05-10 | ||
| PCT/US2012/024974 WO2012112492A1 (en) | 2011-02-14 | 2012-02-14 | 4-hydroxybutyric acid deuterated analogs |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017083295A Division JP6692319B2 (ja) | 2011-02-14 | 2017-04-20 | ４−ヒドロキシ酪酸の重水素化類似体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014513046A JP2014513046A (ja) | 2014-05-29 |
| JP2014513046A5 true JP2014513046A5 (OSRAM) | 2015-04-02 |
Family
ID=46672903
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013553647A Pending JP2014513046A (ja) | 2011-02-14 | 2012-02-14 | ４−ヒドロキシ酪酸の重水素化類似体 |
| JP2017083295A Active JP6692319B2 (ja) | 2011-02-14 | 2017-04-20 | ４−ヒドロキシ酪酸の重水素化類似体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017083295A Active JP6692319B2 (ja) | 2011-02-14 | 2017-04-20 | ４−ヒドロキシ酪酸の重水素化類似体 |
Country Status (10)
| Country | Link |
|---|---|
| US (5) | US8759394B2 (OSRAM) |
| EP (1) | EP2675771B1 (OSRAM) |
| JP (2) | JP2014513046A (OSRAM) |
| KR (1) | KR101976218B1 (OSRAM) |
| CN (1) | CN103370289B (OSRAM) |
| BR (1) | BR112013020620A2 (OSRAM) |
| ES (1) | ES2804540T3 (OSRAM) |
| IL (1) | IL227754B (OSRAM) |
| MX (1) | MX355742B (OSRAM) |
| WO (1) | WO2012112492A1 (OSRAM) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2759251C (en) | 2009-04-23 | 2017-01-03 | Concert Pharmaceuticals, Inc. | 4-hydroxybutyric acid analogs |
| MX391660B (es) | 2010-03-24 | 2025-03-21 | Jazz Pharmaceuticals Inc | Formas de dosis de liberacion controlada para substancias de farmaco de alta dosis, solubles en agua e higroscopicas |
| US8759394B2 (en) * | 2011-02-14 | 2014-06-24 | Concert Pharmaceuticals, Inc. | 4-hydroxybutyric acid analogs |
| US10398662B1 (en) | 2015-02-18 | 2019-09-03 | Jazz Pharma Ireland Limited | GHB formulation and method for its manufacture |
| CA3207643A1 (en) * | 2015-09-23 | 2017-03-30 | XWPharma Ltd. | Prodrugs of gamma-hydroxybutyric acid, compositions and uses thereof |
| HK1258020A1 (zh) | 2015-11-19 | 2019-11-01 | 株式会社大塚制药工场 | 3-羟基异戊酸的一价阳离子盐的晶体及该晶体的制造方法 |
| AU2017282515A1 (en) | 2016-06-24 | 2019-01-17 | Otsuka Pharmaceutical Factory, Inc. | Crystal of β-hydroxy β-methylbutyric acid amino acid salt and production method therefor |
| US11602513B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12478604B1 (en) | 2016-07-22 | 2025-11-25 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11986451B1 (en) | 2016-07-22 | 2024-05-21 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| UY37341A (es) | 2016-07-22 | 2017-11-30 | Flamel Ireland Ltd | Formulaciones de gamma-hidroxibutirato de liberación modificada con farmacocinética mejorada |
| US11000498B2 (en) | 2016-07-22 | 2021-05-11 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12186296B1 (en) | 2016-07-22 | 2025-01-07 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11504347B1 (en) | 2016-07-22 | 2022-11-22 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US20180263936A1 (en) | 2017-03-17 | 2018-09-20 | Jazz Pharmaceuticals Ireland Limited | Gamma-hydroxybutyrate compositions and their use for the treatment of disorders |
| KR102378845B1 (ko) | 2017-03-30 | 2022-03-24 | 엑스더블유파마 리미티드 | 이환형 헤테로아릴 유도체 및 이의 제조 및 용도 |
| CA3093430A1 (en) * | 2018-03-23 | 2019-09-26 | Concert Pharmaceuticals, Inc. | Deuterated analogs of d-.beta.-hydroxybutyric acid and uses thereof |
| CN112004802B (zh) | 2018-09-30 | 2021-12-28 | 凯瑞康宁生物工程（武汉）有限公司 | 作为神经元组胺受体-3拮抗剂的化合物及其用途 |
| BR112021006027A2 (pt) | 2018-11-19 | 2021-06-29 | Jazz Pharmaceuticals Ireland Limited | formulações de fármaco resistente a álcool |
| AU2020231916B2 (en) | 2019-03-01 | 2025-08-28 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| CN115244028A (zh) | 2019-12-20 | 2022-10-25 | 凯瑞康宁生物工程有限公司 | 4-缬氨酰氧基丁酸的合成方法 |
| TW202139986A (zh) * | 2020-02-21 | 2021-11-01 | 愛爾蘭商爵士製藥愛爾蘭有限責任公司 | 治療原發性嗜睡症之方法 |
| AU2021292406B2 (en) | 2020-06-18 | 2024-03-14 | XWPharma Ltd. | Controlled release granulations of water-soluble active pharmaceutical ingredients |
| AU2021293941B2 (en) | 2020-06-18 | 2024-03-28 | XWPharma Ltd. | Pharmaceutical granulations of water-soluble active pharmaceutical ingredients |
| CN116261451A (zh) | 2020-07-24 | 2023-06-13 | 凯瑞康宁生物工程有限公司 | γ-羟基丁酸衍生物的药物组合物和药物动力学 |
| CN115666527B (zh) | 2020-10-05 | 2025-03-07 | 凯瑞康宁生物工程有限公司 | γ-羟基丁酸衍生物的修饰释放组合物 |
| TW202300139A (zh) | 2021-03-19 | 2023-01-01 | 凱瑞康寧生技股份有限公司 | γ-羟基丁酸衍生物的聯合釋放製劑的藥代動力學 |
| CN113200853A (zh) * | 2021-05-19 | 2021-08-03 | 宁波窦氏化学科技有限公司 | 一种制备丁二酸二醇酯的工艺方法 |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
| WO2025137671A1 (en) * | 2023-12-22 | 2025-06-26 | Temple University-Of The Commonwealth System Of Higher Education | Short chain fatty acid compounds and uses thereof |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA814854B (en) * | 1980-07-17 | 1982-07-28 | J Klosa | Nonhygroscopic salts of 4-hydroxybutryric acid, methods of their production and pharmaceutical preparations containing these salts |
| EP0044801B1 (de) | 1980-07-17 | 1984-02-15 | Josef Dr. Klosa | Nichthygroskopische Salze der 4-Hydroxybuttersäure, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Mittel |
| US4548716A (en) * | 1984-07-25 | 1985-10-22 | Lucas Boeve | Method of producing ultrapure, pyrogen-free water |
| US4738985A (en) | 1986-03-19 | 1988-04-19 | The University Of Toronto Innovations Foundations | Pharmaceutical composition and treatment |
| JP2727008B2 (ja) * | 1989-02-01 | 1998-03-11 | 日本酸素株式会社 | 静菌化水の製造方法 |
| DE4113984C2 (de) | 1991-04-29 | 2002-05-08 | Koehler Chemie Dr Franz | Salze der 4-Hydroxy-Buttersäure |
| IT1248588B (it) * | 1991-06-28 | 1995-01-19 | Gaetano Crepaldi | Composizioni farmaceutiche per la terapia dell'astinenza, del " craving", della dipendenza da sostanze stupefacenti, da sostanze psicoattive, da nicotina e dei disturbi alimentari. |
| US6221335B1 (en) | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| JP3696884B2 (ja) | 1994-03-25 | 2005-09-21 | アイソテクニカ、インコーポレーテッド | ジュウテリウム化による薬物の効能の増強 |
| US5840331A (en) | 1995-06-07 | 1998-11-24 | Arch Development Corporation | Use of γ-hydroxybutyrate for the stimulation of sleep-related secretion growth hormone and prolactin |
| JP4740426B2 (ja) | 1997-03-17 | 2011-08-03 | ビーティージー・インターナショナル・リミテッド | 治療用組成物 |
| US5990162A (en) | 1997-08-29 | 1999-11-23 | Orphan Medical, Inc. | Method for treatment of fibromyalgia and chronic fatigue syndrome |
| US6440710B1 (en) | 1998-12-10 | 2002-08-27 | The Scripps Research Institute | Antibody-catalyzed deuteration, tritiation, dedeuteration or detritiation of carbonyl compounds |
| DE60019435T2 (de) * | 1999-09-14 | 2006-02-23 | Tepha, Inc., Cambridge | Therapeutische anwendung von polymere die gamma-hydroxybutyrat enthalten |
| US6204245B1 (en) | 1999-09-17 | 2001-03-20 | The Regents Of The University Of California | Treatment of narcolepsy with immunosuppressants |
| EP1104760B1 (en) | 1999-12-03 | 2003-03-12 | Pfizer Products Inc. | Sulfamoylheteroaryl pyrazole compounds as anti-inflammatory/analgesic agents |
| CA2423358C (en) | 2000-09-22 | 2011-05-17 | Orphan Medical, Inc. | Gamma-hydroxybutyrate compositions containing carbohydrate, lipid or amino acid carriers |
| US7727549B2 (en) | 2002-07-15 | 2010-06-01 | Alcon, Inc. | Pharmaceutical compositions for otic use |
| TW200413273A (en) | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
| CA2624179A1 (en) | 2005-10-06 | 2007-04-12 | Auspex Pharmaceuticals, Inc. | Deuterated inhibitors of gastric h+, k+-atpase with enhanced therapeutic properties |
| US7750168B2 (en) | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
| JO2630B1 (en) | 2006-04-13 | 2012-06-17 | نوفارتيس ايه جي | Organic compounds |
| CA2661404A1 (en) | 2006-09-05 | 2008-03-13 | Schering Corporation | Pharmaceutical combinations for lipid management and in the treatment of atherosclerosis and hepatic steatosis |
| US20090082380A1 (en) * | 2007-09-25 | 2009-03-26 | Protia, Llc | Deuterium-enriched rosuvastatin |
| CN102216257B (zh) * | 2008-10-08 | 2015-11-25 | 凯飞药业公司 | Gaba偶联物及其使用方法 |
| CA2759251C (en) | 2009-04-23 | 2017-01-03 | Concert Pharmaceuticals, Inc. | 4-hydroxybutyric acid analogs |
| US8759394B2 (en) * | 2011-02-14 | 2014-06-24 | Concert Pharmaceuticals, Inc. | 4-hydroxybutyric acid analogs |
-
2012
- 2012-02-14 US US13/372,989 patent/US8759394B2/en active Active
- 2012-02-14 JP JP2013553647A patent/JP2014513046A/ja active Pending
- 2012-02-14 WO PCT/US2012/024974 patent/WO2012112492A1/en not_active Ceased
- 2012-02-14 EP EP12704646.4A patent/EP2675771B1/en active Active
- 2012-02-14 KR KR1020137024419A patent/KR101976218B1/ko active Active
- 2012-02-14 CN CN201280008737.7A patent/CN103370289B/zh active Active
- 2012-02-14 ES ES12704646T patent/ES2804540T3/es active Active
- 2012-02-14 MX MX2013009368A patent/MX355742B/es active IP Right Grant
- 2012-02-14 BR BR112013020620A patent/BR112013020620A2/pt not_active Application Discontinuation
-
2013
- 2013-08-01 IL IL227754A patent/IL227754B/en active IP Right Grant
-
2014
- 2014-04-17 US US14/255,331 patent/US9309182B2/en active Active
-
2016
- 2016-04-11 US US15/095,545 patent/US10040748B2/en active Active
-
2017
- 2017-04-20 JP JP2017083295A patent/JP6692319B2/ja active Active
-
2018
- 2018-08-06 US US16/055,407 patent/US20190100484A1/en not_active Abandoned
-
2021
- 2021-02-01 US US17/164,391 patent/US20210403407A1/en not_active Abandoned
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