CA2857193A1 - Heterocyclic amides compounds which are hdac6 inhibitors and used as anti-tumoral agents - Google Patents

Heterocyclic amides compounds which are hdac6 inhibitors and used as anti-tumoral agents Download PDF

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Publication number
CA2857193A1
CA2857193A1 CA2857193A CA2857193A CA2857193A1 CA 2857193 A1 CA2857193 A1 CA 2857193A1 CA 2857193 A CA2857193 A CA 2857193A CA 2857193 A CA2857193 A CA 2857193A CA 2857193 A1 CA2857193 A1 CA 2857193A1
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CA
Canada
Prior art keywords
methyl
cndot
hydroxybenzamide
hydroxy
indol
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
Application number
CA2857193A
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English (en)
French (fr)
Inventor
Zhaoyin Wang
Lianhai Li
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NANJING ALLGEN PHARMA Co Ltd
Original Assignee
Beta Pharma Canada Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Beta Pharma Canada Inc filed Critical Beta Pharma Canada Inc
Publication of CA2857193A1 publication Critical patent/CA2857193A1/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00—Radiation therapy
    • A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Radiology & Medical Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2857193A 2011-11-29 2012-11-29 Heterocyclic amides compounds which are hdac6 inhibitors and used as anti-tumoral agents Abandoned CA2857193A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161629827P 2011-11-29 2011-11-29
US61/629,827 2011-11-29
PCT/CA2012/001101 WO2013078544A1 (en) 2011-11-29 2012-11-29 Heterocyclic amides compounds which are hdac6 inhibitors and used as anti-tumoral agents

Publications (1)

Publication Number Publication Date
CA2857193A1 true CA2857193A1 (en) 2013-06-06

Family

ID=48534555

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2857193A Abandoned CA2857193A1 (en) 2011-11-29 2012-11-29 Heterocyclic amides compounds which are hdac6 inhibitors and used as anti-tumoral agents

Country Status (6)

Country Link
US (1) US9345905B2 (enExample)
EP (1) EP2785720B1 (enExample)
JP (1) JP6272773B2 (enExample)
CN (1) CN103974956B (enExample)
CA (1) CA2857193A1 (enExample)
WO (1) WO2013078544A1 (enExample)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11524968B2 (en) 2017-10-18 2022-12-13 Hk Inno.N Corporation Heterocyclic compound as a protein kinase inhibitor
US12180185B2 (en) 2018-11-15 2024-12-31 Hk Inno.N Corporation Compound as protein kinase inhibitor, and pharmaceutical composition comprising thereof

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2451686C1 (ru) * 2010-12-27 2012-05-27 Александр Васильевич Иващенко ЗАМЕЩЕННЫЕ ГИДРИРОВАННЫЕ ТИЕНО-ПИРРОЛО [3,2-c] ПИРИДИНЫ, ЛИГАНДЫ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И СПОСОБ ИХ ПРИМЕНЕНИЯ
HRP20181965T1 (hr) * 2013-12-12 2019-02-08 Chong Kun Dang Pharmaceutical Corp. Novi derivati azaindola kao selektivni inhibitori histonske deacetilaze (hdac) i farmaceutski pripravci koji ih sadrže
KR101685639B1 (ko) * 2014-01-03 2016-12-12 주식회사 종근당 신규한 인돌 유도체 화합물 및 이를 포함하는 약제학적 조성물
US10533010B2 (en) 2014-03-27 2020-01-14 Vanderbilt University Substituted indole Mcl-1 inhibitors
US10106540B2 (en) 2014-08-04 2018-10-23 Universität Regensburg HDAC6 inhibitors and their uses
NZ739211A (en) 2015-07-27 2019-05-31 Chong Kun Dang Pharmaceutical Corp 1,3,4-oxadiazole amide derivative compound as histone deacetylase 6 inhibitor, and pharmaceutical composition containing same
BR112017027798B1 (pt) 2015-07-27 2023-12-19 Chong Kun Dang Pharmaceutical Corp Compostos de derivado de 1,3,4-oxadiazol sulfamida como inibidor de histona desacetilase 6 e a composição farmacêutica que compreende os mesmos
HRP20230052T1 (hr) 2015-07-27 2023-03-03 Chong Kun Dang Pharmaceutical Corp. Spojevi derivata 1,3,4-oksadiazol sulfonamida kao inhibitori histonske deacetilaze 6, i farmaceutski pripravak koji ih sadrži
HRP20220003T1 (hr) * 2015-08-04 2022-04-01 Chong Kun Dang Pharmaceutical Corp. Spojevi derivata 1,3,4-oksadiazola kao inhibitori histonske deacetilaze 6, i farmaceutski pripravak koji ih sadrži
FI3362445T3 (fi) 2015-10-12 2023-03-21 Chong Kun Dang Pharmaceutical Corp Oksadiatsoliamiinijohdannaisyhdisteitä histonideasetylaasi 6:n inhibiittoreina ja niitä käsittävä farmaseuttinen koostumus
JP7086395B2 (ja) 2016-03-04 2022-06-20 ヴァンダービルト ユニバーシティー 置換インドールＭｃｌ－１阻害剤
US11998546B2 (en) 2016-10-28 2024-06-04 Acetylon Pharmaceuticals, Inc. Pharmaceutical combinations comprising a histone deacetylase inhibitor and epothilone and methods of use thereof
JP7254028B2 (ja) 2017-05-16 2023-04-07 アンジー ファーマスーティカル シーオー．，エルティーディー． ヒストンデアセチラーゼ（ｈｄａｃｓ）阻害剤
KR102316234B1 (ko) 2018-07-26 2021-10-22 주식회사 종근당 히스톤 탈아세틸화효소 6 억제제로서의 1,3,4-옥사다이아졸 유도체 화합물 및 이를 포함하는 약제학적 조성물
CN113874369B (zh) 2019-05-31 2024-08-27 株式会社钟根堂 作为组蛋白脱乙酰酶6抑制剂的1,3,4-噁二唑高邻苯二甲酰亚胺衍生化合物及包含其的药物组合物
KR20220119653A (ko) 2019-12-20 2022-08-30 테나야 테라퓨틱스, 인코포레이티드 플루오로알킬-옥사디아졸 및 이의 용도
EP4326263A1 (en) 2021-04-23 2024-02-28 Tenaya Therapeutics, Inc. Hdac6 inhibitors for use in the treatment of dilated cardiomyopathy
US20240252502A1 (en) 2021-05-04 2024-08-01 Tenaya Therapeutics, Inc. Hdac6 inhibitors for treatment of metabolic disease and hfpef
CN113861193A (zh) * 2021-11-04 2021-12-31 西南大学 一种光引发自由基串联反应制备吲哚并四氢吡啶二酮及其衍生物的方法和产品
WO2025215092A1 (en) 2024-04-10 2025-10-16 Institut National de la Santé et de la Recherche Médicale Selective hdac6 inhibitors for use in the treatment of myotonic dystrophy type 1
CN121226371B (zh) * 2025-10-28 2026-07-14 百色学院 四氢吡嗪[1,2-a]吲哚类组蛋白去乙酰化酶抑制剂及其制备方法与应用

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006063294A2 (en) * 2004-12-09 2006-06-15 Kalypsys, Inc. Novel inhibitors of histone deacetylase for the treatment of disease
CA2597193A1 (en) * 2007-08-13 2009-02-13 De Montfort University Compounds and uses
JP2010536876A (ja) * 2007-08-21 2010-12-02 アークル インコーポレイテッド Ｈｄａｃインヒビター
BRPI0817897A2 (pt) * 2007-11-02 2019-09-24 Methylgene Inc composto, composição, e, métodos de inibição da atividade hdac, e de tratamento de uma doença responsiva a um inibidor de atividade hdac
WO2009073620A2 (en) * 2007-11-30 2009-06-11 Newlink Genetics Ido inhibitors
EP2254886B1 (en) * 2008-03-28 2016-05-25 Nerviano Medical Sciences S.r.l. 3,4-dihydro-2h-pyrazino[1,2-a]indol-1-one derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them
WO2011019417A1 (en) * 2009-04-29 2011-02-17 Medivation Technologies, Inc. Pyrido [4, 3-b] indoles and methods of use
WO2010127177A1 (en) * 2009-04-29 2010-11-04 Medivation Technologies, Inc. Pyrido [4,3-b] indoles and methods of use
JP5838157B2 (ja) * 2009-07-22 2015-12-24 ザ・ボード・オブ・トラスティーズ・オブ・ザ・ユニバーシティ・オブ・イリノイＴｈｅ Ｂｏａｒｄ Ｏｆ Ｔｒｕｓｔｅｅｓ Ｏｆ Ｔｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｉｌｌｉｎｏｉｓ Ｈｄａｃ阻害剤およびそれを用いる治療法
US20110053925A1 (en) * 2009-08-28 2011-03-03 Novartis Ag Hydroxamate-Based Inhibitors of Deacetylases
IT1396915B1 (it) * 2009-10-23 2012-12-20 Italfarmaco Spa Dietil-[6-(4-idrossicarbamoil-fenil-carbamoilossimetil)-naftalen-2-il-metil]-ammonio cloruro ed altri derivati della n-idrossi-benzammide per l'uso nel trattamento di infezioni da hiv.
WO2013062344A1 (en) * 2011-10-28 2013-05-02 Chong Kun Dang Pharmaceutical Corp. Hydroxamate derivatives for hdac inhibitor, and the pharmaceutical composition comprising thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11524968B2 (en) 2017-10-18 2022-12-13 Hk Inno.N Corporation Heterocyclic compound as a protein kinase inhibitor
US12180185B2 (en) 2018-11-15 2024-12-31 Hk Inno.N Corporation Compound as protein kinase inhibitor, and pharmaceutical composition comprising thereof

Also Published As

Publication number Publication date
CN103974956B (zh) 2016-07-06
EP2785720B1 (en) 2017-08-09
CN103974956A (zh) 2014-08-06
US20140322229A1 (en) 2014-10-30
JP6272773B2 (ja) 2018-01-31
WO2013078544A1 (en) 2013-06-06
US9345905B2 (en) 2016-05-24
EP2785720A4 (en) 2015-11-11
JP2014533734A (ja) 2014-12-15
EP2785720A1 (en) 2014-10-08

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FZDE Discontinued

Effective date: 20171129