KR20170102980A - 벤조디아제핀 이량체, 그의 접합체, 및 제조 및 사용 방법 - Google Patents

벤조디아제핀 이량체, 그의 접합체, 및 제조 및 사용 방법 Download PDF

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KR20170102980A
KR20170102980A KR1020177022244A KR20177022244A KR20170102980A KR 20170102980 A KR20170102980 A KR 20170102980A KR 1020177022244 A KR1020177022244 A KR 1020177022244A KR 20177022244 A KR20177022244 A KR 20177022244A KR 20170102980 A KR20170102980 A KR 20170102980A
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alkyl
substituted
mmol
independently
formula
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용 장
이바르 엠. 맥도널드
나이두 에스. 초우다리
트람 엔. 후인
로버트 엠. 보르질레리
산지브 강와르
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브리스톨-마이어스 스큅 컴퍼니
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50Medicinal 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
    • A61K47/51Medicinal 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
    • A61K47/68Medicinal 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
    • A61K47/6835Medicinal 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
    • A61K47/6843Medicinal 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 material from animals or humans
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50Medicinal 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
    • A61K47/51Medicinal 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
    • A61K47/68Medicinal 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
    • A61K47/6835Medicinal 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
    • A61K47/6849Medicinal 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D519/00Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K16/00Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
    • C07K16/18Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K16/00Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
    • C07K16/18Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans
    • C07K16/28Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K16/00Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
    • C07K16/18Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans
    • C07K16/28Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants
    • C07K16/30Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants from tumour cells
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • C07K5/06008Dipeptides with the first amino acid being neutral
    • C07K5/06017Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06052Val-amino acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K2317/00Immunoglobulins specific features
    • C07K2317/70Immunoglobulins specific features characterized by effect upon binding to a cell or to an antigen
    • C07K2317/76Antagonist effect on antigen, e.g. neutralization or inhibition of binding

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Immunology (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Cell Biology (AREA)
  • Zoology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
KR1020177022244A 2015-01-14 2016-01-13 벤조디아제핀 이량체, 그의 접합체, 및 제조 및 사용 방법 Ceased KR20170102980A (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201562103157P 2015-01-14 2015-01-14
US62/103,157 2015-01-14
US201562215928P 2015-09-09 2015-09-09
US62/215,928 2015-09-09
PCT/US2016/013136 WO2016115191A1 (en) 2015-01-14 2016-01-13 Benzodiazepine dimers, conjugates thereof, and methods of making and using

Publications (1)

Publication Number Publication Date
KR20170102980A true KR20170102980A (ko) 2017-09-12

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US (4) US9527871B2 (enExample)
EP (1) EP3245213B1 (enExample)
JP (1) JP6498773B2 (enExample)
KR (1) KR20170102980A (enExample)
CN (1) CN107428780B (enExample)
AU (1) AU2016206798A1 (enExample)
BR (1) BR112017014599A2 (enExample)
CA (1) CA2973354A1 (enExample)
CL (1) CL2017001824A1 (enExample)
CO (1) CO2017008078A2 (enExample)
EA (1) EA201791550A1 (enExample)
ES (1) ES2783624T3 (enExample)
IL (1) IL253402A0 (enExample)
MX (1) MX2017009145A (enExample)
PE (1) PE20171184A1 (enExample)
SG (1) SG11201705646XA (enExample)
TW (1) TW201632531A (enExample)
WO (1) WO2016115191A1 (enExample)
ZA (1) ZA201704738B (enExample)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6676058B2 (ja) * 2015-01-14 2020-04-08 ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company ヘテロアリーレン架橋したベンゾジアゼピン二量体、そのコンジュゲート、ならびに製造および使用方法
US9504694B2 (en) * 2015-03-19 2016-11-29 Cellerant Therapeutics, Inc. Isoquinolidinobenzodiazepines
WO2018048975A1 (en) 2016-09-09 2018-03-15 Bristol-Myers Squibb Company Use of an anti-pd-1 antibody in combination with an anti-mesothelin antibody in cancer treatment
WO2018053552A2 (en) * 2016-09-19 2018-03-22 Cellerant Therapeutics, Inc. Isoquinolidinobenzodiazepines
EP3522932A4 (en) * 2016-10-10 2020-06-24 Cellerant Therapeutics, Inc. ISOCHINOLIDINOBENZODIAZEPINE (IQB) -1 (CHLORMETHYL) -2,3-DIHYDRO-1-H-BENZO [E] INDOL (CBI) DIMERS
US10738338B2 (en) 2016-10-18 2020-08-11 The Research Foundation for the State University Method and composition for biocatalytic protein-oligonucleotide conjugation and protein-oligonucleotide conjugate
WO2018075842A1 (en) 2016-10-20 2018-04-26 Bristol-Myers Squibb Company Condensed benzodiazepine derivatives and conjugates made therefrom
CN110225904B (zh) * 2017-01-25 2023-10-27 伊缪诺金公司 制备细胞毒性苯二氮䓬衍生物的方法
WO2018195243A1 (en) * 2017-04-20 2018-10-25 Immunogen, Inc. Cytotoxic benzodiazepine derivatives and conjugates thereof
WO2019036433A2 (en) 2017-08-16 2019-02-21 Bristol-Myers Squibb Company ANTIBODIES IN THE FORM OF PRODRUGS, PRODRUGS BASED THEREON, THEIR METHODS OF USE AND PREPARATION
GB201714115D0 (en) 2017-09-04 2017-10-18 Femtogenix Ltd Cytotoxic agents
MX2020003125A (es) 2017-09-29 2020-10-01 Daiichi Sankyo Co Ltd Conjugado de anticuerpo-derivado de pirrolobenzodiazepina.
US11084801B2 (en) * 2018-05-29 2021-08-10 Intocell, Inc. Benzodiazepine derivatives and uses thereof
US12274898B2 (en) * 2018-10-31 2025-04-15 Intocell, Inc. Substituted benzodiazepines as antibody-drug conjugates
WO2020100954A1 (ja) 2018-11-14 2020-05-22 第一三共株式会社 抗cdh6抗体-ピロロベンゾジアゼピン誘導体コンジュゲート
HRP20230500T1 (hr) 2018-11-30 2023-07-21 Bristol-Myers Squibb Company Antitijelo koje sadrži c-terminalnu ekstenziju lakog lanca koja sadrži glutamin, njegovi konjugati, i postupci i primjene
KR20210102334A (ko) 2018-12-12 2021-08-19 브리스톨-마이어스 스큅 컴퍼니 트랜스글루타미나제 접합을 위해 변형된 항체, 그의 접합체, 및 방법 및 용도
GB201901197D0 (en) 2019-01-29 2019-03-20 Femtogenix Ltd G-A Crosslinking cytotoxic agents
TWI856078B (zh) 2019-03-25 2024-09-21 日商第一三共股份有限公司 抗體–吡咯并苯二氮呯衍生物結合物、其製造方法及其用途
KR20210141630A (ko) 2019-03-25 2021-11-23 다이이찌 산쿄 가부시키가이샤 항 her2 항체-피롤로벤조디아제핀 유도체 콘주게이트
CA3139180A1 (en) 2019-03-27 2020-10-01 Daiichi Sankyo Company, Limited Combination of antibody-pyrrolobenzodiazepine derivative conjugate and parp inhibitor
WO2020251878A1 (en) 2019-06-11 2020-12-17 Bristol-Myers Squibb Company Anti-ctla4 antibody prodruggable (probody) at a cdr position
US20240377413A1 (en) 2019-09-16 2024-11-14 Bristol-Myers Squibb Company Dual capture method for analysis of antibody-drug conjugates
KR20230146521A (ko) 2021-01-13 2023-10-19 메모리얼 슬로안 케터링 캔서 센터 항체-피롤로벤조디아제핀 유도체 접합체
CN113372245B (zh) * 2021-06-17 2023-01-13 仪征市海帆化工有限公司 一种n-苯甲酰基-o,o-对甲苯磺酰基-二乙醇胺的合成方法
WO2023037237A1 (en) * 2021-09-09 2023-03-16 Wavelength Enterprises Ltd Process for the preparation of remimazolam
WO2023054706A1 (ja) * 2021-09-30 2023-04-06 味の素株式会社 抗体および機能性物質のコンジュゲートまたはその塩、ならびにその製造に用いられる抗体誘導体および化合物またはそれらの塩
IL312728A (en) 2021-11-30 2024-07-01 Daiichi Sankyo Co Ltd Protease-cleavable masked antibodies
CA3251410A1 (en) 2022-02-09 2025-07-08 Daiichi Sankyo Co Ltd Masked antibody sensitive to the environment and its use
WO2025214466A1 (en) * 2024-04-12 2025-10-16 BeiGene Guangzhou Biologics Manufacturing Co., Ltd. Targeted pyrrolobenzodiazapine conjugates

Family Cites Families (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE320436T1 (de) 1998-08-27 2006-04-15 Spirogen Ltd Dimere pyrrolobenzodiazepine
ES2369542T3 (es) 2002-07-31 2011-12-01 Seattle Genetics, Inc. Conjugados de auristatina y su uso para tratar cáncer, una enfermedad autoinmune o una enfermedad infecciosa.
GB0226593D0 (en) 2002-11-14 2002-12-24 Consultants Ltd Compounds
GB0416511D0 (en) 2003-10-22 2004-08-25 Spirogen Ltd Pyrrolobenzodiazepines
GB0404578D0 (en) 2004-03-01 2004-04-07 Spirogen Ltd Pyrrolobenzodiazepines
PT2270010E (pt) 2004-03-01 2012-03-12 Spirogen Ltd Derivados de 11-hidroxi-5h-pirrolo[2,1-c][1,4]benzodiazepin- 5-ona como intermediários chave para a preparação de pirrolobenzodiazepinas substituídas em c2
GB0404577D0 (en) 2004-03-01 2004-04-07 Spirogen Ltd Pyrrolobenzodiazepines
WO2005085260A1 (en) 2004-03-09 2005-09-15 Spirogen Limited Pyrrolobenzodiazepines
PT1879901E (pt) 2005-04-21 2010-03-29 Spirogen Ltd Pirrolobenzodiazepinas
US8124738B2 (en) 2005-09-26 2012-02-28 Medarex, Inc. Human monoclonal antibodies to CD70
CN101356195B (zh) 2005-12-08 2013-04-03 米德列斯公司 抗岩藻糖基-gm1的人单克隆抗体及使用抗岩藻糖基-gm1抗体的方法
SI1813614T1 (sl) 2006-01-25 2012-01-31 Sanofi 174 Citotoksična sredstva, ki obsegajo nove tomajmicinske derivate
RS54624B1 (sr) 2007-07-17 2016-08-31 E. R. Squibb & Sons, L.L.C. Monoklonska antitela protiv glipikana-3
ES2435779T3 (es) 2007-07-19 2013-12-23 Sanofi Agentes citotóxicos que comprenden nuevos derivados de tomaimicina y su uso terapéutico
WO2009045957A1 (en) 2007-10-01 2009-04-09 Medarex, Inc. Human antibodies that bind mesothelin, and uses thereof
GB0813432D0 (en) 2008-07-22 2008-08-27 Spirogen Ltd Pyrrolobenzodiazepines
GB0819095D0 (en) 2008-10-17 2008-11-26 Spirogen Ltd Pyrrolobenzodiazepines
CN105198908B (zh) * 2009-02-05 2019-12-24 伊缪诺金公司 新型苯并二氮杂*衍生物
FR2949469A1 (fr) 2009-08-25 2011-03-04 Sanofi Aventis Derives anticancereux, leur preparation et leur application en therapeutique
ES2623057T3 (es) 2010-04-15 2017-07-10 Medimmune Limited Pirrolobenzodiazepinas usadas para tratar enfermedades proliferativas
CN102933236B (zh) 2010-04-15 2014-10-08 斯皮罗根有限公司 吡咯并苯二氮卓类及其结合物
CN103068405A (zh) 2010-04-15 2013-04-24 西雅图基因公司 靶向吡咯并苯并二氮杂卓结合物
FR2963007B1 (fr) 2010-07-26 2013-04-05 Sanofi Aventis Derives anticancereux, leur preparation et leur application therapeutique
PT2675480T (pt) * 2011-02-15 2019-04-15 Immunogen Inc Métodos para preparação de conjugados
CN103987718A (zh) 2011-09-20 2014-08-13 斯皮罗根有限公司 作为非对称二聚体pbd化合物用于内含在靶向结合物中的吡咯并苯并二氮杂卓
CN103998449A (zh) 2011-10-14 2014-08-20 斯皮罗根有限公司 吡咯并苯并二氮杂卓
CA2850373C (en) 2011-10-14 2019-07-16 Seattle Genetics, Inc. Pyrrolobenzodiazepines and targeted conjugates
WO2013055987A1 (en) 2011-10-14 2013-04-18 Spirogen Sàrl Pyrrolobenzodiazepines and conjugates thereof
CA2850375C (en) 2011-10-14 2019-07-02 Seattle Genetics, Inc. Pyrrolobenzodiazepines and targeted conjugates
CN103998450B (zh) 2011-10-14 2017-03-08 麦迪穆有限责任公司 吡咯并苯并二氮杂卓
WO2013177481A1 (en) * 2012-05-25 2013-11-28 Immunogen, Inc. Benzodiazepines and conjugates thereof
HK1211208A1 (zh) 2012-08-22 2016-05-20 Immunogen, Inc. 細胞毒性苯並二氮呯衍生物
CN104703630A (zh) 2012-10-12 2015-06-10 斯皮罗根有限公司 吡咯并苯并二氮杂卓及其结合物
RS58921B1 (sr) 2012-10-12 2019-08-30 Medimmune Ltd Pirolobenzodiazepini i njihovi konjugati
JP6133431B2 (ja) 2012-11-24 2017-05-24 ハンジョウ ディーエーシー バイオテック シーオー.,エルティディ.Hangzhou Dac Biotech Co.,Ltd. 親水性連結体及び薬物分子と細胞結合分子との共役反応における親水性連結体の使用
JP6527466B2 (ja) 2012-12-21 2019-06-05 メドイミューン・リミテッドMedImmune Limited 増殖性疾患および自己免疫疾患の治療に使用するための非対称ピロロベンゾジアゼピンニ量体
WO2014096368A1 (en) 2012-12-21 2014-06-26 Spirogen Sàrl Pyrrolobenzodiazepines and conjugates thereof
KR102066319B1 (ko) 2013-03-13 2020-01-14 메디뮨 리미티드 피롤로벤조디아제핀 및 그의 컨쥬게이트
WO2014159981A2 (en) 2013-03-13 2014-10-02 Spirogen Sarl Pyrrolobenzodiazepines and conjugates thereof
NZ710746A (en) 2013-03-13 2018-11-30 Medimmune Ltd Pyrrolobenzodiazepines and conjugates thereof
US20160106861A1 (en) 2013-04-26 2016-04-21 Spirogen Sarl Axl antibody-drug conjugate and its use for the treatment of cancer

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Publication number Publication date
EP3245213B1 (en) 2020-03-04
SG11201705646XA (en) 2017-08-30
IL253402A0 (en) 2017-09-28
US20180079781A1 (en) 2018-03-22
US10112975B2 (en) 2018-10-30
US20160200742A1 (en) 2016-07-14
US9527871B2 (en) 2016-12-27
US9676794B2 (en) 2017-06-13
JP2018503639A (ja) 2018-02-08
WO2016115191A1 (en) 2016-07-21
AU2016206798A1 (en) 2017-08-31
CO2017008078A2 (es) 2017-11-10
US9822144B2 (en) 2017-11-21
PE20171184A1 (es) 2017-08-22
CL2017001824A1 (es) 2018-02-09
ZA201704738B (en) 2019-02-27
CN107428780A (zh) 2017-12-01
CA2973354A1 (en) 2016-07-21
TW201632531A (zh) 2016-09-16
ES2783624T3 (es) 2020-09-17
MX2017009145A (es) 2017-11-22
BR112017014599A2 (pt) 2018-01-16
US20170233436A1 (en) 2017-08-17
EA201791550A1 (ru) 2017-11-30
JP6498773B2 (ja) 2019-04-10
EP3245213A1 (en) 2017-11-22
CN107428780B (zh) 2020-09-04
US20170073357A1 (en) 2017-03-16

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