JP2014512405A5 - - Google Patents
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- JP2014512405A5 JP2014512405A5 JP2014506865A JP2014506865A JP2014512405A5 JP 2014512405 A5 JP2014512405 A5 JP 2014512405A5 JP 2014506865 A JP2014506865 A JP 2014506865A JP 2014506865 A JP2014506865 A JP 2014506865A JP 2014512405 A5 JP2014512405 A5 JP 2014512405A5
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- JP
- Japan
- Prior art keywords
- mmol
- vacuo
- residue
- disease
- dcm
- 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.)
- Granted
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 208000023275 Autoimmune disease Diseases 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SSICBAZNBPOZKX-UHFFFAOYSA-N 5-bromo-3-fluoro-n-(methoxymethyl)pyridine-2-carboxamide Chemical compound COCNC(=O)C1=NC=C(Br)C=C1F SSICBAZNBPOZKX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- 102000004127 Cytokines Human genes 0.000 description 2
- 108090000695 Cytokines Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007821 HATU Substances 0.000 description 2
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- 208000003456 Juvenile Arthritis Diseases 0.000 description 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- -1 4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl Chemical group 0.000 description 1
- PYATZGRLDQJZMG-UHFFFAOYSA-N 4-bromo-3-phenylpyrazolo[1,5-a]pyridin-2-amine Chemical compound NC1=NN2C=CC=C(Br)C2=C1C1=CC=CC=C1 PYATZGRLDQJZMG-UHFFFAOYSA-N 0.000 description 1
- IIQAVSXIOLXFAB-UHFFFAOYSA-N 5-bromo-3-fluoropyridine-2-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1=NC=C(Br)C=C1F IIQAVSXIOLXFAB-UHFFFAOYSA-N 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 208000009329 Graft vs Host Disease Diseases 0.000 description 1
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 229940116839 Janus kinase 1 inhibitor Drugs 0.000 description 1
- 229940121730 Janus kinase 2 inhibitor Drugs 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 230000002327 eosinophilic effect Effects 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000004068 intracellular signaling Effects 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- DWLOJDDYJICKFV-UHFFFAOYSA-N n-(4-bromo-3-phenylpyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide Chemical compound C=1C=CC=CC=1C1=C2C(Br)=CC=CN2N=C1NC(=O)C1CC1 DWLOJDDYJICKFV-UHFFFAOYSA-N 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161479956P | 2011-04-28 | 2011-04-28 | |
| US61/479,956 | 2011-04-28 | ||
| PCT/EP2012/057654 WO2012146659A1 (en) | 2011-04-28 | 2012-04-26 | Novel compound useful for the treatment of degenerative and inflammatory diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014512405A JP2014512405A (ja) | 2014-05-22 |
| JP2014512405A5 true JP2014512405A5 (enExample) | 2015-05-28 |
| JP5947372B2 JP5947372B2 (ja) | 2016-07-06 |
Family
ID=46017860
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014506865A Active JP5947372B2 (ja) | 2011-04-28 | 2012-04-26 | 変性疾患及び炎症性疾患の治療に有用な新規化合物 |
| JP2014506863A Active JP5947371B2 (ja) | 2011-04-28 | 2012-04-26 | 変性疾患及び炎症性疾患の治療に有用な新規化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014506863A Active JP5947371B2 (ja) | 2011-04-28 | 2012-04-26 | 変性疾患及び炎症性疾患の治療に有用な新規化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (5) | US8975406B2 (enExample) |
| EP (2) | EP2702059B1 (enExample) |
| JP (2) | JP5947372B2 (enExample) |
| KR (1) | KR101934707B1 (enExample) |
| CN (2) | CN103492385B (enExample) |
| AR (1) | AR086042A1 (enExample) |
| AU (2) | AU2012247484B2 (enExample) |
| BR (1) | BR112013027338A2 (enExample) |
| CA (2) | CA2833963C (enExample) |
| EA (1) | EA024743B1 (enExample) |
| IL (1) | IL228786A (enExample) |
| MX (2) | MX360697B (enExample) |
| SG (1) | SG194508A1 (enExample) |
| TW (1) | TWI536990B (enExample) |
| UY (1) | UY34037A (enExample) |
| WO (2) | WO2012146659A1 (enExample) |
| ZA (1) | ZA201307793B (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR086042A1 (es) * | 2011-04-28 | 2013-11-13 | Galapagos Nv | Compuesto util para el tratamiento de enfermedades degenerativas e inflamatorias y composicion farmaceutica |
| AU2014261539A1 (en) * | 2013-04-29 | 2015-12-10 | Sanofi Sa | Inhalable pharmaceutical compositions and the inhaler devices containing them |
| GB201321733D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| KR101690760B1 (ko) * | 2014-11-05 | 2016-12-30 | 조길래 | 피부자극완화, 탈모방지 및 발모촉진 효과를 나타내는 카페오일펜타펩타이드 및 이를 함유하는 탈모방지 및 발모촉진용 화장료 조성물 |
| TW201705961A (zh) * | 2015-06-11 | 2017-02-16 | 阿爾米雷爾有限公司 | 作為ｊａｋ抑制劑的２－（吡唑并吡啶－３－基）嘧啶衍生物 |
| ES2821049T3 (es) | 2015-06-18 | 2021-04-23 | 89Bio Ltd | Derivados de piperidina 1,4 sustituidos |
| MX379846B (es) | 2015-06-18 | 2025-03-11 | 89Bio Ltd | Derivados de 4-bencil y 4-benzoil piperidina sustituidos. |
| DK3322706T3 (da) | 2015-07-16 | 2021-02-01 | Array Biopharma Inc | Substituerede pyrazolo[1,5-a]pyridin-forbindelser som ret-kinaseinhibitorer |
| WO2017013270A1 (en) | 2015-07-23 | 2017-01-26 | Universite De Strasbourg | Use of leptin signaling inhibitor for protecting kidneys from patients having ciliopathy |
| DE102015215820A1 (de) * | 2015-08-19 | 2017-02-23 | Siemens Healthcare Gmbh | Steuern eines medizintechnischen Geräts |
| WO2018019223A1 (zh) | 2016-07-26 | 2018-02-01 | 张文燕 | 作为选择性jak抑制剂化合物，该化合物的盐类及其治疗用途 |
| JOP20190077A1 (ar) * | 2016-10-10 | 2019-04-09 | Array Biopharma Inc | مركبات بيرازولو [1، 5-a]بيريدين بها استبدال كمثبطات كيناز ret |
| TWI704148B (zh) * | 2016-10-10 | 2020-09-11 | 美商亞雷生物製藥股份有限公司 | 作為ｒｅｔ激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
| CA3049136C (en) | 2017-01-18 | 2022-06-14 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyrazine compounds as ret kinase inhibitors |
| JP6697631B2 (ja) * | 2017-03-09 | 2020-05-20 | 富士フイルム株式会社 | 音響レンズ用樹脂材料、音響レンズ、音響波プローブ、音響波測定装置、超音波診断装置、光音響波測定装置および超音波内視鏡 |
| EA037208B1 (ru) * | 2017-09-29 | 2021-02-19 | Эррей Биофарма Инк. | ЗАМЕЩЕННЫЕ ПИРАЗОЛО[1,5-а]ПИРИДИНОВЫЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ИНГИБИТОРОВ RET КИНАЗЫ |
| EA035568B1 (ru) * | 2017-09-29 | 2020-07-08 | Эррей Биофарма Инк. | ЗАМЕЩЕННЫЕ ПИРАЗОЛО[1,5-а]ПИРИДИНОВЫЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ИНГИБИТОРОВ RET КИНАЗЫ |
| TWI812649B (zh) | 2017-10-10 | 2023-08-21 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
| TWI783057B (zh) * | 2017-10-10 | 2022-11-11 | 美商絡速藥業公司 | 製備6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈的方法 |
| WO2019143994A1 (en) | 2018-01-18 | 2019-07-25 | Array Biopharma Inc. | Substituted pyrazolyl[4,3-c]pyridinecompounds as ret kinase inhibitors |
| CA3087354C (en) | 2018-01-18 | 2023-01-03 | Array Biopharma Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds as ret kinase inhibitors |
| CA3087578C (en) | 2018-01-18 | 2023-08-08 | Array Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| CN112996794A (zh) | 2018-09-10 | 2021-06-18 | 阿雷生物药品公司 | 作为ret激酶抑制剂的稠合杂环化合物 |
| WO2020064009A1 (zh) * | 2018-09-30 | 2020-04-02 | 北京志健金瑞生物医药科技有限公司 | 取代吡唑稠环类衍生物及其制备方法和应用 |
| JP7457709B2 (ja) * | 2018-12-07 | 2024-03-28 | サンシャイン・レイク・ファーマ・カンパニー・リミテッド | Ｒｅｔ阻害剤、医薬組成物、およびその使用 |
| JP7457708B2 (ja) | 2018-12-07 | 2024-03-28 | サンシャイン・レイク・ファーマ・カンパニー・リミテッド | Ｒｅｔ阻害剤、医薬組成物およびその使用 |
| US20230159523A1 (en) * | 2020-04-22 | 2023-05-25 | Shenzhen Zhongge Biological Technology Co., Ltd. | Pyrazolo[1,5-a]pyridine derivative, preparation method therefor, and composition and use thereof |
| CN113713083A (zh) * | 2020-05-25 | 2021-11-30 | 南京帝昌医药科技有限公司 | 一种用于治疗脱发的药物组合 |
| UY39401A (es) | 2020-09-01 | 2022-03-31 | Syngenta Crop Protection Ag | Derivados de isoindolin-1-ona o 7h-pirrolo[3,4-b]piridin-5-ona activos como plaguicidas con sustituyentes que contienen azufre |
| WO2022064459A1 (en) | 2020-09-28 | 2022-03-31 | 1ST Biotherapeutics, Inc. | Indazoles as hematopoietic progenitor kinase 1 (hpk1) inhibitors and methods of using same |
| WO2022165530A1 (en) * | 2021-02-01 | 2022-08-04 | Janssen Biotech, Inc. | Small molecule inhibitors of salt inducible kinases |
| US20240158392A1 (en) * | 2021-02-01 | 2024-05-16 | Janssen Biotech, Inc. | Small molecule inhibitors of salt inducible kinases |
| US20250145640A1 (en) | 2021-08-10 | 2025-05-08 | Syngenta Crop Protection Ag | 2,2-difluoro-5h-[1,3]dioxolo[4,5-f]isoindol-7-one derivatives as pesticides |
| CN114409675B (zh) * | 2022-01-07 | 2023-08-04 | 重庆医科大学 | 螺环异恶唑酮色满衍生物在制备用于治疗jak1介导的疾病药物中的用途 |
| WO2023187191A1 (en) | 2022-04-01 | 2023-10-05 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| CN120584105A (zh) | 2023-01-23 | 2025-09-02 | 先正达农作物保护股份公司 | 具有含硫取代基的杀有害生物活性的杂环衍生物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008503712A (ja) | 2004-06-21 | 2008-02-07 | ガラパゴス・ナムローゼ・フェンノートシャップ | 骨関節炎治療の方法及び手段 |
| CA2662074A1 (en) * | 2006-08-30 | 2008-03-06 | Cellzome Limited | Triazole derivatives as kinase inhibitors |
| WO2009017954A1 (en) * | 2007-08-01 | 2009-02-05 | Phenomix Corporation | Inhibitors of jak2 kinase |
| EP2288260A4 (en) * | 2008-06-20 | 2013-10-23 | Genentech Inc | TRIAZOLOPYRIDINE-JAK HEMMER COMPOUNDS AND METHOD |
| JO3041B1 (ar) * | 2008-07-25 | 2016-09-05 | Galapagos Nv | مركبات جديدة مفيدة لمعالجة الأمراض التنكسية والالتهابية |
| WO2010010186A1 (en) * | 2008-07-25 | 2010-01-28 | Galapagos Nv | Novel compounds useful for the treatment of degenerative and inflammatory diseases |
| TWI462920B (zh) * | 2009-06-26 | 2014-12-01 | 葛萊伯格有限公司 | 用於治療退化性及發炎疾病之新穎化合物 |
| AR086042A1 (es) * | 2011-04-28 | 2013-11-13 | Galapagos Nv | Compuesto util para el tratamiento de enfermedades degenerativas e inflamatorias y composicion farmaceutica |
-
2012
- 2012-04-24 AR ARP120101411A patent/AR086042A1/es unknown
- 2012-04-26 MX MX2013012282A patent/MX360697B/es active IP Right Grant
- 2012-04-26 EA EA201391584A patent/EA024743B1/ru not_active IP Right Cessation
- 2012-04-26 BR BR112013027338A patent/BR112013027338A2/pt not_active Application Discontinuation
- 2012-04-26 EP EP12717289.8A patent/EP2702059B1/en active Active
- 2012-04-26 SG SG2013077060A patent/SG194508A1/en unknown
- 2012-04-26 EP EP12717288.0A patent/EP2702058B1/en active Active
- 2012-04-26 CN CN201280020639.5A patent/CN103492385B/zh active Active
- 2012-04-26 CA CA2833963A patent/CA2833963C/en active Active
- 2012-04-26 AU AU2012247484A patent/AU2012247484B2/en not_active Ceased
- 2012-04-26 KR KR1020137029055A patent/KR101934707B1/ko not_active Expired - Fee Related
- 2012-04-26 TW TW101115010A patent/TWI536990B/zh not_active IP Right Cessation
- 2012-04-26 AU AU2012247482A patent/AU2012247482B2/en not_active Ceased
- 2012-04-26 WO PCT/EP2012/057654 patent/WO2012146659A1/en not_active Ceased
- 2012-04-26 UY UY0001034037A patent/UY34037A/es not_active Application Discontinuation
- 2012-04-26 CA CA2833942A patent/CA2833942A1/en not_active Abandoned
- 2012-04-26 JP JP2014506865A patent/JP5947372B2/ja active Active
- 2012-04-26 MX MX2013012281A patent/MX355653B/es active IP Right Grant
- 2012-04-26 WO PCT/EP2012/057652 patent/WO2012146657A1/en not_active Ceased
- 2012-04-26 US US14/114,218 patent/US8975406B2/en active Active
- 2012-04-26 CN CN201280020782.4A patent/CN103492386B/zh active Active
- 2012-04-26 JP JP2014506863A patent/JP5947371B2/ja active Active
- 2012-04-27 US US13/459,055 patent/US8802682B2/en active Active
-
2013
- 2013-10-08 IL IL228786A patent/IL228786A/en active IP Right Grant
- 2013-10-18 ZA ZA2013/07793A patent/ZA201307793B/en unknown
-
2014
- 2014-08-11 US US14/457,071 patent/US9241931B2/en active Active
-
2016
- 2016-01-25 US US15/005,442 patent/US9987272B2/en active Active
-
2017
- 2017-09-01 US US15/694,454 patent/US20180078547A1/en not_active Abandoned
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