TWI755450B - 苯二氮平衍生物之選擇性磺化 - Google Patents

苯二氮平衍生物之選擇性磺化 Download PDF

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TWI755450B
TWI755450B TW106140599A TW106140599A TWI755450B TW I755450 B TWI755450 B TW I755450B TW 106140599 A TW106140599 A TW 106140599A TW 106140599 A TW106140599 A TW 106140599A TW I755450 B TWI755450 B TW I755450B
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cytotoxic agent
imine
represented
formula
alkyl
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TW106140599A
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TW201822819A (zh
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史考特 A 西得伯朗德
班傑明 M 胡金斯
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美商伊繆諾金公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/24—Oxygen atoms
    • C07D243/26—Preparation from compounds already containing the benzodiazepine skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/68035—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a pyrrolobenzodiazepine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6835—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site
    • A61K47/6849—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a receptor, a cell surface antigen or a cell surface determinant
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K16/00—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies
    • C07K16/18—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans
    • C07K16/28—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants
    • C07K16/2866—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants against receptors for cytokines, lymphokines, interferons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K16/00—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies
    • C07K16/18—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans
    • C07K16/28—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants
    • C07K16/2896—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants against molecules with a "CD"-designation, not provided for elsewhere
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K16/00—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies
    • C07K16/18—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans
    • C07K16/28—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants
    • C07K16/30—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants from tumour cells
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K2317/00—Immunoglobulins specific features
    • C07K2317/50—Immunoglobulins specific features characterized by immunoglobulin fragments
    • C07K2317/52—Constant or Fc region; Isotype
    • C07K2317/526—CH3 domain

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Cell Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
TW106140599A 2016-11-23 2017-11-22 苯二氮平衍生物之選擇性磺化 TWI755450B (zh)

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US201662425761P 2016-11-23 2016-11-23
US62/425,761 2016-11-23

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TW201822819A TW201822819A (zh) 2018-07-01
TWI755450B true TWI755450B (zh) 2022-02-21

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TW111103323A TWI845890B (zh) 2016-11-23 2017-11-22 苯二氮平衍生物之選擇性磺化

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US (5) US10287256B2 (https=)
EP (1) EP3544983A2 (https=)
JP (2) JP7203729B2 (https=)
KR (2) KR20230133935A (https=)
CN (2) CN116813690A (https=)
AU (2) AU2017363237B2 (https=)
CA (1) CA3044391A1 (https=)
IL (2) IL266743B (https=)
MA (1) MA46887A (https=)
TW (2) TWI755450B (https=)
WO (1) WO2018098258A2 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI845890B (zh) * 2016-11-23 2024-06-21 美商伊繆諾金公司 苯二氮平衍生物之選擇性磺化

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SMT202000614T1 (it) * 2015-06-29 2021-01-05 Immunogen Inc Coniugati di anticorpi ingegnerizzati con cisteina
AU2016285552B2 (en) * 2015-06-29 2022-10-13 Immunogen, Inc. Anti-CD123 antibodies and conjugates and derivatives thereof
MA54088A (fr) * 2018-10-30 2022-03-16 Immunogen Inc Procédés de traitement faisant appel à des immunoconjugués anti-cd123
WO2020092344A1 (en) * 2018-10-31 2020-05-07 Health Research, Inc. Combination treatment with anti-cd123 antibody drug conjugate and parp inhibitor
KR20220022112A (ko) 2019-03-21 2022-02-24 이뮤노젠 아이엔씨 세포-결합 제제-약물 콘쥬게이트를 준비하는 방법
KR20220004669A (ko) 2019-04-29 2022-01-11 이뮤노젠 아이엔씨 항-cd123 면역접합체를 포함하는 치료적 조합물
US20220306751A1 (en) 2019-09-13 2022-09-29 Mythic Therapeutics, Inc. Antigen-binding protein constructs and uses thereof
CN113189184B (zh) * 2021-04-28 2022-09-09 浙江大学 含有半胱氨酸的毛细管凝胶电泳样品缓冲液
EP4548932A1 (en) 2022-06-30 2025-05-07 Toray Industries, Inc. Pharmaceutical composition for treating and/or preventing cancer

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160106863A1 (en) * 2014-09-03 2016-04-21 Immunogen, Inc. Cytotoxic benzodiazepine derivatives
US20160207949A1 (en) * 2013-09-02 2016-07-21 Hangzhou Dac Biotech Co., Ltd Novel cytotoxic agents for conjugation to a cell binding molecule

Family Cites Families (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5208020A (en) 1989-10-25 1993-05-04 Immunogen Inc. Cytotoxic agents comprising maytansinoids and their therapeutic use
EP0563475B1 (en) 1992-03-25 2000-05-31 Immunogen Inc Cell binding agent conjugates of derivatives of CC-1065
GB9422383D0 (en) 1994-11-05 1995-01-04 Wellcome Found Antibodies
CA2388063C (en) 1999-11-24 2010-06-08 Immunogen, Inc. Cytotoxic agents comprising taxanes and their therapeutic use
US6441163B1 (en) 2001-05-31 2002-08-27 Immunogen, Inc. Methods for preparation of cytotoxic conjugates of maytansinoids and cell binding agents
US6716821B2 (en) 2001-12-21 2004-04-06 Immunogen Inc. Cytotoxic agents bearing a reactive polyethylene glycol moiety, cytotoxic conjugates comprising polyethylene glycol linking groups, and methods of making and using the same
US6756397B2 (en) 2002-04-05 2004-06-29 Immunogen, Inc. Prodrugs of CC-1065 analogs
BR0313197A (pt) 2002-08-02 2005-08-09 Immunogen Inc Agentes citotóxicos contendo potentes taxanos e seu uso terapêutico
DE60336149D1 (de) 2002-08-16 2011-04-07 Immunogen Inc Vernetzer mit hoher reaktivität und löslichkeit und ihre verwendung bei der herstellung von konjugaten für die gezielte abgabe von kleinmolekularen arzneimitteln
ZA200503075B (en) 2002-11-07 2006-09-27 Immunogen Inc Anti-CD33 antibodies and method for treatment of acute myeloid leukemia using the same
US8088387B2 (en) 2003-10-10 2012-01-03 Immunogen Inc. Method of targeting specific cell populations using cell-binding agent maytansinoid conjugates linked via a non-cleavable linker, said conjugates, and methods of making said conjugates
US7276497B2 (en) 2003-05-20 2007-10-02 Immunogen Inc. Cytotoxic agents comprising new maytansinoids
JP4942643B2 (ja) 2004-03-02 2012-05-30 シアトル ジェネティックス， インコーポレイテッド 部分的に付加された抗体およびそれらの結合体化方法
NZ579482A (en) 2004-06-01 2011-02-25 Genentech Inc Antibody drug conjugates and methods
DK1791565T3 (en) 2004-09-23 2016-08-01 Genentech Inc Cysteingensplejsede antibodies and conjugates
JP2008521828A (ja) 2004-11-29 2008-06-26 シアトル ジェネティックス， インコーポレイテッド 操作された抗体およびイムノコンジュゲート
US7612062B2 (en) 2005-04-21 2009-11-03 Spirogen Limited Pyrrolobenzodiazepines
US8008453B2 (en) 2005-08-12 2011-08-30 Amgen Inc. Modified Fc molecules
EP2032606B1 (en) 2006-05-30 2013-11-27 Genentech, Inc. Antibodies and immunoconjugates and uses therefor
ES2593484T3 (es) 2007-03-29 2016-12-09 Genmab A/S Anticuerpos biespecíficos y métodos de producción de los mismos
SI2019104T1 (sl) 2007-07-19 2013-12-31 Sanofi Citotoksična sredstva, ki obsegajo nove tomaimicinske derivate, in njihova terapevtska uporaba
NZ610239A (en) 2008-04-30 2014-11-28 Immunogen Inc Cross-linkers and their uses
SG189817A1 (en) 2008-04-30 2013-05-31 Immunogen Inc Potent conjugates and hydrophilic linkers
GB0819095D0 (en) 2008-10-17 2008-11-26 Spirogen Ltd Pyrrolobenzodiazepines
RU2683325C2 (ru) 2009-02-05 2019-03-28 Иммьюноджен, Инк. Новые производные бензодиазепина
EP2711018A1 (en) 2009-06-22 2014-03-26 MedImmune, LLC Engineered Fc regions for site-specific conjugation
WO2011092838A1 (ja) 2010-01-29 2011-08-04 株式会社フォーサイド・ドット・コム コンテンツ共有システム、およびコンテンツ共有方法
TWI622402B (zh) 2010-02-24 2018-05-01 免疫遺傳股份有限公司 葉酸受體１抗體類和免疫共軛物類及彼等之用途
SG10201501803YA (en) 2010-03-12 2015-05-28 Immunogen Inc Cd37-binding molecules and immunoconjugates thereof
JP5875083B2 (ja) 2010-04-15 2016-03-02 メディミューン リミテッド 増殖性疾患治療用ピロロベンゾジアゼピン
HRP20241208T1 (hr) 2010-04-20 2024-11-22 Genmab A/S Heterodimerni proteini koji sadrže fc fragment protutijela i postupci za njihovu proizvodnju
EA201390472A1 (ru) 2010-10-29 2014-02-28 Иммьюноджен, Инк. Новые молекулы, связывающиеся с egfr, и их иммуноконъюгаты
EA201390575A1 (ru) 2010-10-29 2014-01-30 Иммьюноджен, Инк. Неантагонистические egfr-связывающие молекулы и их иммуноконъюгаты
JP5826863B2 (ja) 2011-02-15 2015-12-02 イミュノジェン・インコーポレーテッド 細胞傷害性ベンゾジアゼピン誘導体
WO2013177481A1 (en) 2012-05-25 2013-11-28 Immunogen, Inc. Benzodiazepines and conjugates thereof
JP6423804B2 (ja) 2013-02-28 2018-11-14 イミュノジェン・インコーポレーテッド 細胞結合剤及び細胞毒性剤を含む複合体
EP3566750A3 (en) 2013-02-28 2020-04-08 ImmunoGen, Inc. Conjugates comprising cell-binding agents and cytotoxic agents
WO2014134457A2 (en) 2013-02-28 2014-09-04 Immunogen, Inc. Conjugates comprising cell-binding agents and cytotoxic agents
US9950077B2 (en) 2014-06-20 2018-04-24 Bioalliance C.V. Anti-folate receptor alpha (FRA) antibody-drug conjugates and methods of using thereof
SG11201610624WA (en) 2014-06-20 2017-01-27 Bioalliance Cv Anti-cd22 antibody-drug conjugates and methods of using thereof
SG11201701328XA (en) 2014-09-02 2017-03-30 Immunogen Inc Methods for formulating antibody drug conjugate compositions
AU2015311987B2 (en) 2014-09-03 2020-06-04 Immunogen, Inc. Cytotoxic benzodiazepine derivatives
MA41645A (fr) 2015-03-04 2018-01-09 Abbvie Stemcentrx Llc Anticorps issus de génie génétique spécifiques au site et méthodes d'utilisation
AU2016285552B2 (en) 2015-06-29 2022-10-13 Immunogen, Inc. Anti-CD123 antibodies and conjugates and derivatives thereof
SMT202000614T1 (it) 2015-06-29 2021-01-05 Immunogen Inc Coniugati di anticorpi ingegnerizzati con cisteina
EA201891723A1 (ru) 2016-02-05 2018-12-28 Милленниум Фармасьютикалз, Инк. Gcc-направленные конъюгаты антитело-лекарство
WO2018098258A2 (en) 2016-11-23 2018-05-31 Immunogen, Inc. Selective sulfonation of benzodiazepine derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160207949A1 (en) * 2013-09-02 2016-07-21 Hangzhou Dac Biotech Co., Ltd Novel cytotoxic agents for conjugation to a cell binding molecule
US20160106863A1 (en) * 2014-09-03 2016-04-21 Immunogen, Inc. Cytotoxic benzodiazepine derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI845890B (zh) * 2016-11-23 2024-06-21 美商伊繆諾金公司 苯二氮平衍生物之選擇性磺化

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TWI845890B (zh) 2024-06-21
IL266743B (en) 2022-04-01
US10287256B2 (en) 2019-05-14
AU2017363237B2 (en) 2022-03-17
US20230391733A1 (en) 2023-12-07
US10822313B2 (en) 2020-11-03
US11572349B2 (en) 2023-02-07
US20200157056A1 (en) 2020-05-21
CA3044391A1 (en) 2018-05-31
US10494348B2 (en) 2019-12-03
KR102576550B1 (ko) 2023-09-07
TW201822819A (zh) 2018-07-01
US20180208562A1 (en) 2018-07-26
WO2018098258A2 (en) 2018-05-31
KR20230133935A (ko) 2023-09-19
KR20190104995A (ko) 2019-09-11
RU2019118808A (ru) 2020-12-24
MA46887A (fr) 2019-10-02
RU2019118808A3 (https=) 2021-03-19
CN110392685A (zh) 2019-10-29
JP2020512276A (ja) 2020-04-23
AU2022204163B2 (en) 2024-05-02
AU2017363237A1 (en) 2019-06-27
WO2018098258A3 (en) 2018-10-04
AU2022204163A1 (en) 2022-07-21
IL266743A (en) 2019-07-31
IL291597A (en) 2022-05-01
CN110392685B (zh) 2023-07-04
US20210101871A1 (en) 2021-04-08
CN116813690A (zh) 2023-09-29
TW202235109A (zh) 2022-09-16
JP2023036842A (ja) 2023-03-14
US20190315699A1 (en) 2019-10-17
JP7203729B2 (ja) 2023-01-13
EP3544983A2 (en) 2019-10-02

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