CA2887896A1 - Pyrrolobenzodiazepine-anti-her2 antibody conjugates - Google Patents
Pyrrolobenzodiazepine-anti-her2 antibody conjugates Download PDFInfo
- Publication number
- CA2887896A1 CA2887896A1 CA2887896A CA2887896A CA2887896A1 CA 2887896 A1 CA2887896 A1 CA 2887896A1 CA 2887896 A CA2887896 A CA 2887896A CA 2887896 A CA2887896 A CA 2887896A CA 2887896 A1 CA2887896 A1 CA 2887896A1
- Authority
- CA
- Canada
- Prior art keywords
- conjugate according
- group
- antibody
- alkyl
- conjugate
- 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.)
- Abandoned
Links
- 229940127121 immunoconjugate Drugs 0.000 title description 3
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims abstract description 17
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims abstract description 17
- 239000000562 conjugate Substances 0.000 claims description 167
- -1 methoxy, ethoxy Chemical group 0.000 claims description 133
- 125000005647 linker group Chemical group 0.000 claims description 122
- 150000001875 compounds Chemical class 0.000 claims description 118
- 239000003814 drug Substances 0.000 claims description 87
- 125000003118 aryl group Chemical group 0.000 claims description 84
- 229940079593 drug Drugs 0.000 claims description 83
- 239000000203 mixture Substances 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 229940049595 antibody-drug conjugate Drugs 0.000 claims description 67
- 239000000611 antibody drug conjugate Substances 0.000 claims description 66
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 125000000623 heterocyclic group Chemical group 0.000 claims description 55
- 108010016626 Dipeptides Proteins 0.000 claims description 42
- 150000001413 amino acids Chemical class 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 206010028980 Neoplasm Diseases 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 238000011068 loading method Methods 0.000 claims description 20
- 201000011510 cancer Diseases 0.000 claims description 19
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- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
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- 229940022353 herceptin Drugs 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 47
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
- C07K16/18—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans
- C07K16/32—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against translation products of oncogenes
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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- 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
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- 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
- A61K47/6851—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 determinant of a tumour cell
- A61K47/6855—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 determinant of a tumour cell the tumour determinant being from breast cancer cell
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/505—Medicinal preparations containing antigens or antibodies comprising antibodies
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Cell Biology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Biomedical Technology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261712924P | 2012-10-12 | 2012-10-12 | |
| US201261712928P | 2012-10-12 | 2012-10-12 | |
| US61/712,928 | 2012-10-12 | ||
| US61/712,924 | 2012-10-12 | ||
| US201361784249P | 2013-03-14 | 2013-03-14 | |
| US201361784233P | 2013-03-14 | 2013-03-14 | |
| US201361784270P | 2013-03-14 | 2013-03-14 | |
| US61/784,233 | 2013-03-14 | ||
| US61/784,270 | 2013-03-14 | ||
| US61/784,249 | 2013-03-14 | ||
| PCT/EP2013/071343 WO2014057115A1 (en) | 2012-10-12 | 2013-10-11 | Pyrrolobenzodiazepine-anti-her2 antibody conjugates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2887896A1 true CA2887896A1 (en) | 2014-04-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2887896A Abandoned CA2887896A1 (en) | 2012-10-12 | 2013-10-11 | Pyrrolobenzodiazepine-anti-her2 antibody conjugates |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US20150273077A1 (enExample) |
| EP (1) | EP2906252B1 (enExample) |
| JP (1) | JP2016502504A (enExample) |
| KR (1) | KR20150083856A (enExample) |
| CN (1) | CN104955485B (enExample) |
| AU (1) | AU2013328621B2 (enExample) |
| BR (1) | BR112015008177A2 (enExample) |
| CA (1) | CA2887896A1 (enExample) |
| CY (1) | CY1119287T1 (enExample) |
| DK (1) | DK2906252T3 (enExample) |
| ES (1) | ES2640449T3 (enExample) |
| HR (1) | HRP20171264T1 (enExample) |
| HU (1) | HUE034505T2 (enExample) |
| LT (1) | LT2906252T (enExample) |
| MX (1) | MX2015004423A (enExample) |
| PL (1) | PL2906252T3 (enExample) |
| PT (1) | PT2906252T (enExample) |
| RS (1) | RS56222B1 (enExample) |
| SI (1) | SI2906252T1 (enExample) |
| SM (1) | SMT201700444T1 (enExample) |
| WO (1) | WO2014057115A1 (enExample) |
| ZA (1) | ZA201502267B (enExample) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0819095D0 (en) | 2008-10-17 | 2008-11-26 | Spirogen Ltd | Pyrrolobenzodiazepines |
| MX2012011900A (es) | 2010-04-15 | 2013-03-21 | Seattle Genetics Inc | Conjugados de pirrolobenzodiazepina diana. |
| EP2558475A1 (en) | 2010-04-15 | 2013-02-20 | Spirogen Sàrl | Pyrrolobenzodiazepines used to treat proliferative diseases |
| KR101860174B1 (ko) | 2011-09-20 | 2018-05-21 | 메디뮨 리미티드 | 표적 접합체 내의 내포를 위한 비대칭 이량체 pbd 화합물로서 피롤로벤조디아제핀 |
| 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 |
| CN103987384A (zh) | 2011-10-14 | 2014-08-13 | 西雅图基因公司 | 吡咯并苯并二氮杂卓和靶向结合物 |
| BR112014008888A2 (pt) | 2011-10-14 | 2017-04-18 | Seattle Genetics Inc | pirrolobenzodiazepinas |
| CN103997893B (zh) | 2011-10-14 | 2019-04-12 | 西雅图基因公司 | 吡咯并苯并二氮杂卓和靶向结合物 |
| CA2885340C (en) | 2012-10-12 | 2016-11-08 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| JP6367204B2 (ja) | 2012-10-12 | 2018-08-01 | メドイミューン・リミテッドＭｅｄＩｍｍｕｎｅ Ｌｉｍｉｔｅｄ | 結合用のピロロベンゾジアゼピン誘導体の合成および中間体 |
| PT3470086T (pt) | 2012-10-12 | 2021-02-01 | Medimmune Ltd | Pirrolobenzodiazepinas e conjugados das mesmas |
| BR112015014669B1 (pt) | 2012-12-21 | 2023-09-26 | Medimmune Limited | Compostos pirrolobenzodiazepinas, conjugados compreendendo os mesmos e uso destes para tratar uma doença proliferativa |
| AU2013366490B9 (en) | 2012-12-21 | 2018-02-01 | Medimmune Limited | Unsymmetrical pyrrolobenzodiazepines-dimers for use in the treatment of proliferative and autoimmune diseases |
| EA027910B1 (ru) | 2013-03-13 | 2017-09-29 | Медимьюн Лимитед | Пирролобензодиазепины и их конъюгаты |
| CN105142674B (zh) | 2013-03-13 | 2018-11-13 | 麦迪穆有限责任公司 | 吡咯并苯并二氮杂卓和其结合物 |
| GB201317982D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| EP3054985B1 (en) | 2013-10-11 | 2018-12-26 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| GB201317981D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| US10188746B2 (en) | 2014-09-10 | 2019-01-29 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| GB201416112D0 (en) | 2014-09-12 | 2014-10-29 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| ES2830385T3 (es) | 2014-09-12 | 2021-06-03 | Genentech Inc | Anticuerpos e inmunoconjugados anti-HER2 |
| HK1243629A1 (zh) * | 2014-09-17 | 2018-07-20 | 基因泰克公司 | 包含抗her2抗体和吡咯并苯并二氮杂䓬的免疫缀合物 |
| CA2968447A1 (en) | 2014-11-25 | 2016-06-02 | Adc Therapeutics Sa | Pyrrolobenzodiazepine-antibody conjugates and their use to treat neoplasms |
| US9504694B2 (en) * | 2015-03-19 | 2016-11-29 | Cellerant Therapeutics, Inc. | Isoquinolidinobenzodiazepines |
| GB201506389D0 (en) * | 2015-04-15 | 2015-05-27 | Berkel Patricius H C Van And Howard Philip W | Site-specific antibody-drug conjugates |
| GB201506411D0 (en) | 2015-04-15 | 2015-05-27 | Bergenbio As | Humanized anti-axl antibodies |
| GB201506394D0 (en) * | 2015-04-15 | 2015-05-27 | Berkel Patricius H C Van And Howard Philip W | Site-specific antibody-drug conjugates |
| MA43345A (fr) | 2015-10-02 | 2018-08-08 | Hoffmann La Roche | Conjugués anticorps-médicaments de pyrrolobenzodiazépine et méthodes d'utilisation |
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| WO2013177481A1 (en) * | 2012-05-25 | 2013-11-28 | Immunogen, Inc. | Benzodiazepines and conjugates thereof |
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2013
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- 2013-10-11 DK DK13788691.7T patent/DK2906252T3/en active
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- 2013-10-11 ES ES13788691.7T patent/ES2640449T3/es active Active
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- 2013-10-11 RS RS20170839A patent/RS56222B1/sr unknown
- 2013-10-11 MX MX2015004423A patent/MX2015004423A/es unknown
- 2013-10-11 EP EP13788691.7A patent/EP2906252B1/en active Active
- 2013-10-11 CA CA2887896A patent/CA2887896A1/en not_active Abandoned
- 2013-10-11 CN CN201380065413.1A patent/CN104955485B/zh not_active Expired - Fee Related
- 2013-10-11 WO PCT/EP2013/071343 patent/WO2014057115A1/en not_active Ceased
- 2013-10-11 PT PT137886917T patent/PT2906252T/pt unknown
- 2013-10-11 KR KR1020157012365A patent/KR20150083856A/ko not_active Withdrawn
- 2013-10-11 SM SM20170444T patent/SMT201700444T1/it unknown
- 2013-10-11 LT LTEP13788691.7T patent/LT2906252T/lt unknown
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- 2013-10-11 SI SI201330762T patent/SI2906252T1/sl unknown
- 2013-10-11 PL PL13788691T patent/PL2906252T3/pl unknown
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2015
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| BR112015008177A2 (pt) | 2017-09-19 |
| SMT201700444T1 (it) | 2017-11-15 |
| ZA201502267B (en) | 2017-09-27 |
| ES2640449T3 (es) | 2017-11-03 |
| CY1119287T1 (el) | 2018-02-14 |
| AU2013328621A1 (en) | 2015-04-23 |
| PT2906252T (pt) | 2017-09-19 |
| PL2906252T3 (pl) | 2017-11-30 |
| DK2906252T3 (en) | 2017-09-11 |
| RS56222B1 (sr) | 2017-11-30 |
| EP2906252B1 (en) | 2017-06-14 |
| KR20150083856A (ko) | 2015-07-20 |
| CN104955485B (zh) | 2018-01-30 |
| HUE034505T2 (en) | 2018-02-28 |
| JP2016502504A (ja) | 2016-01-28 |
| CN104955485A (zh) | 2015-09-30 |
| US20150273077A1 (en) | 2015-10-01 |
| SI2906252T1 (sl) | 2017-10-30 |
| WO2014057115A1 (en) | 2014-04-17 |
| EP2906252A1 (en) | 2015-08-19 |
| MX2015004423A (es) | 2015-10-29 |
| LT2906252T (lt) | 2017-09-11 |
| AU2013328621B2 (en) | 2016-12-01 |
| HRP20171264T1 (hr) | 2017-10-20 |
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