SI3055308T1 - Diazacarbazole derivatives as tau-pet-ligands - Google Patents
Diazacarbazole derivatives as tau-pet-ligands Download PDFInfo
- Publication number
- SI3055308T1 SI3055308T1 SI201430549T SI201430549T SI3055308T1 SI 3055308 T1 SI3055308 T1 SI 3055308T1 SI 201430549 T SI201430549 T SI 201430549T SI 201430549 T SI201430549 T SI 201430549T SI 3055308 T1 SI3055308 T1 SI 3055308T1
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- Slovenia
- Prior art keywords
- compound
- formula
- aggregates
- pharmaceutically acceptable
- fluoro
- Prior art date
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- BZHCVCNZIJZMRN-UHFFFAOYSA-N 9h-pyridazino[3,4-b]indole Chemical class N1=CC=C2C3=CC=CC=C3NC2=N1 BZHCVCNZIJZMRN-UHFFFAOYSA-N 0.000 title claims 2
- 239000003446 ligand Substances 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract 25
- 238000003384 imaging method Methods 0.000 claims abstract 3
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims abstract 2
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims abstract 2
- 102000003802 alpha-Synuclein Human genes 0.000 claims abstract 2
- 108090000185 alpha-Synuclein Proteins 0.000 claims abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- -1 6-fluoro-pyridin-3-yl Chemical group 0.000 claims 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 5
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 102000013498 tau Proteins Human genes 0.000 claims 5
- 108010026424 tau Proteins Proteins 0.000 claims 5
- 229910052722 tritium Chemical group 0.000 claims 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims 2
- 102100027831 14-3-3 protein theta Human genes 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- 230000005587 bubbling Effects 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000002059 diagnostic imaging Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 claims 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
- 210000005171 mammalian brain Anatomy 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000010422 painting Methods 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 235000003270 potassium fluoride Nutrition 0.000 claims 1
- 239000011698 potassium fluoride Substances 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 239000013049 sediment Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000000527 sonication Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0455—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- 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
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2800/00—Detection or diagnosis of diseases
- G01N2800/28—Neurological disorders
- G01N2800/2814—Dementia; Cognitive disorders
- G01N2800/2821—Alzheimer
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Physics & Mathematics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Optics & Photonics (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Radiology & Medical Imaging (AREA)
- Microbiology (AREA)
- Cell Biology (AREA)
- Pathology (AREA)
- Food Science & Technology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13187764 | 2013-10-08 | ||
| PCT/EP2014/071283 WO2015052105A1 (en) | 2013-10-08 | 2014-10-06 | Diazacarbazole derivatives as tau-pet-ligands |
| EP14781169.9A EP3055308B1 (en) | 2013-10-08 | 2014-10-06 | Diazacarbazole derivatives as tau-pet-ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI3055308T1 true SI3055308T1 (en) | 2018-03-30 |
Family
ID=49301396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI201430549T SI3055308T1 (en) | 2013-10-08 | 2014-10-06 | Diazacarbazole derivatives as tau-pet-ligands |
Country Status (32)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100135235A (ko) | 2008-02-14 | 2010-12-24 | 지멘스 메디컬 솔루션즈 유에스에이, 인크. | 신경학적 기능이상을 검출하기 위한 조영제 |
| NO3055308T3 (enExample) | 2013-10-08 | 2018-04-21 | ||
| PT3143011T (pt) | 2014-05-13 | 2021-04-26 | Hoffmann La Roche | Compostos heterocíclicos deuterados e a sua utilização como agentes de imagiologia |
| ES2875734T3 (es) | 2015-02-02 | 2021-11-11 | UCB Biopharma SRL | Derivados de 9H-pirrolo-dipiridina |
| EP3118202A1 (en) | 2015-07-15 | 2017-01-18 | AC Immune S.A. | Dihydropyridopyrrole derivatives as tau-pet-ligands |
| WO2017009454A1 (en) | 2015-07-15 | 2017-01-19 | Ac Immune S.A. | Novel imaging compounds |
| MX386900B (es) | 2016-07-22 | 2025-03-19 | Ac Immune S A Star | Compuestos para formacion de imagenes de agregados de proteinas tau. |
| WO2018015546A1 (en) | 2016-07-22 | 2018-01-25 | Ac Immune S.A. | Compounds for imaging tau protein aggregates |
| WO2018024643A1 (en) | 2016-08-02 | 2018-02-08 | Ucb Biopharma Sprl | 9h-pyrrolo-dipyridine derivatives |
| WO2018024642A1 (en) | 2016-08-02 | 2018-02-08 | Ucb Biopharma Sprl | 9h-pyrrolo-dipyridine derivatives |
| MX375720B (es) | 2016-09-09 | 2025-03-04 | Hoffmann La Roche | Proceso para preparacion de 2-(6-nitropiridin-3-il)-9h-dipirido[2,3-beta;3',4'-d]pirrol. |
| JP7260552B2 (ja) * | 2018-01-24 | 2023-04-18 | エーシー・イミューン・エス・アー | Ｐｅｔ画像化のための診断用組成物、診断用組成物を製造するための方法及び診断におけるその使用 |
| KR20200113234A (ko) | 2018-01-24 | 2020-10-06 | 에이씨 이뮨 에스.에이. | 이미징 화합물을 제조하는 신규한 방법 |
| EP3743423A1 (en) | 2018-01-24 | 2020-12-02 | AC Immune SA | Gamma-carboline compounds for the detection of tau aggregates |
| EP3743426A1 (en) | 2018-01-24 | 2020-12-02 | AC Immune SA | Azacarboline compounds for the detection of tau aggregates |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100135235A (ko) | 2008-02-14 | 2010-12-24 | 지멘스 메디컬 솔루션즈 유에스에이, 인크. | 신경학적 기능이상을 검출하기 위한 조영제 |
| US8932557B2 (en) * | 2008-02-14 | 2015-01-13 | Eli Lilly And Company | Imaging agents for detecting neurological dysfunction |
| BRPI0909957A2 (pt) | 2008-06-11 | 2016-04-19 | Genentech Inc | "composto, composição farmacêutica, método de inibir o crescimento anormal de células ou de tratar um distúrbio hiperproliferativo em um mamífero, método de tratamento do câncer em um mamífero" |
| US8420052B2 (en) * | 2008-07-24 | 2013-04-16 | Siemens Medical Solutions Usa, Inc. | Imaging agents useful for identifying AD pathology |
| US8691187B2 (en) * | 2009-03-23 | 2014-04-08 | Eli Lilly And Company | Imaging agents for detecting neurological disorders |
| CN102438660A (zh) * | 2009-03-23 | 2012-05-02 | 美国西门子医疗解决公司 | 用于检测神经障碍的显像剂 |
| US20110183938A1 (en) | 2009-12-16 | 2011-07-28 | Genentech, Inc. | 1,7-diazacarbazoles and methods of use |
| US20150368244A1 (en) * | 2011-01-31 | 2015-12-24 | Genentech, Inc. | Diazacarbazoles and methods of use |
| NO3055308T3 (enExample) * | 2013-10-08 | 2018-04-21 |
-
2014
- 2014-10-06 NO NO14781169A patent/NO3055308T3/no unknown
- 2014-10-06 DK DK14781169.9T patent/DK3055308T3/en active
- 2014-10-06 AR ARP140103712A patent/AR097931A1/es active IP Right Grant
- 2014-10-06 SI SI201430549T patent/SI3055308T1/en unknown
- 2014-10-06 LT LTEP14781169.9T patent/LT3055308T/lt unknown
- 2014-10-06 TW TW103134795A patent/TWI513698B/zh active
- 2014-10-06 JP JP2016515518A patent/JP6194416B2/ja active Active
- 2014-10-06 PL PL14781169T patent/PL3055308T3/pl unknown
- 2014-10-06 EP EP14781169.9A patent/EP3055308B1/en active Active
- 2014-10-06 CA CA2917191A patent/CA2917191C/en active Active
- 2014-10-06 WO PCT/EP2014/071283 patent/WO2015052105A1/en not_active Ceased
- 2014-10-06 PT PT147811699T patent/PT3055308T/pt unknown
- 2014-10-06 UA UAA201604290A patent/UA116164C2/uk unknown
- 2014-10-06 RS RS20180058A patent/RS56777B1/sr unknown
- 2014-10-06 ES ES14781169.9T patent/ES2657121T3/es active Active
- 2014-10-06 EA EA201690515A patent/EA028483B1/ru not_active IP Right Cessation
- 2014-10-06 MY MYPI2016000604A patent/MY190196A/en unknown
- 2014-10-06 HU HUE14781169A patent/HUE035413T2/en unknown
- 2014-10-06 PE PE2015002706A patent/PE20160159A1/es active IP Right Grant
- 2014-10-06 MX MX2016002234A patent/MX373153B/es active IP Right Grant
- 2014-10-06 KR KR1020167008013A patent/KR101770531B1/ko active Active
- 2014-10-06 AU AU2014333996A patent/AU2014333996B2/en active Active
- 2014-10-06 CN CN201480037389.5A patent/CN105358558B/zh active Active
- 2014-10-06 SG SG11201602786UA patent/SG11201602786UA/en unknown
- 2014-10-06 HR HRP20180049TT patent/HRP20180049T1/hr unknown
-
2015
- 2015-12-10 ZA ZA2015/09013A patent/ZA201509013B/en unknown
- 2015-12-15 CR CR20150663A patent/CR20150663A/es unknown
- 2015-12-21 IL IL243249A patent/IL243249A0/en active IP Right Grant
-
2016
- 2016-02-04 PH PH12016500249A patent/PH12016500249B1/en unknown
- 2016-03-25 MA MA38935A patent/MA38935B1/fr unknown
- 2016-03-30 CL CL2016000728A patent/CL2016000728A1/es unknown
- 2016-04-07 US US15/093,366 patent/US10004817B2/en active Active
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2018
- 2018-05-15 US US15/980,080 patent/US11058781B2/en active Active
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