CA2946754C - Optically active pde10 inhibitor - Google Patents

Optically active pde10 inhibitor Download PDF

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Publication number
CA2946754C
CA2946754C CA2946754A CA2946754A CA2946754C CA 2946754 C CA2946754 C CA 2946754C CA 2946754 A CA2946754 A CA 2946754A CA 2946754 A CA2946754 A CA 2946754A CA 2946754 C CA2946754 C CA 2946754C
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CA
Canada
Prior art keywords
disorders
compound
neurological disorder
disease
animal
Prior art date
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Active
Application number
CA2946754A
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English (en)
French (fr)
Other versions
CA2946754A1 (en
Inventor
Neil S. Cutshall
Kenneth M. Ferguson
Charles Prince ZUTA
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.)
Omeros Corp
Original Assignee
Omeros Medical Systems Inc
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Publication of CA2946754A1 publication Critical patent/CA2946754A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/433—Thidiazoles
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Epidemiology (AREA)
  • Anesthesiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2946754A 2014-04-28 2015-04-24 Optically active pde10 inhibitor Active CA2946754C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201461985381P 2014-04-28 2014-04-28
US61/985,381 2014-04-28
US201462047569P 2014-09-08 2014-09-08
US62/047,569 2014-09-08
PCT/US2015/027645 WO2015167968A1 (en) 2014-04-28 2015-04-24 Optically active pde10 inhibitor

Publications (2)

Publication Number Publication Date
CA2946754A1 CA2946754A1 (en) 2015-11-05
CA2946754C true CA2946754C (en) 2022-08-30

Family

ID=54359189

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2946754A Active CA2946754C (en) 2014-04-28 2015-04-24 Optically active pde10 inhibitor

Country Status (13)

Country Link
US (2) US9493447B2 (enExample)
EP (1) EP3137461B1 (enExample)
JP (1) JP2017513913A (enExample)
KR (1) KR102558505B1 (enExample)
CN (1) CN106255690B (enExample)
AU (1) AU2015253463B2 (enExample)
BR (1) BR112016024523B1 (enExample)
CA (1) CA2946754C (enExample)
ES (1) ES2895487T3 (enExample)
IL (1) IL248586B (enExample)
NZ (2) NZ716462A (enExample)
RU (1) RU2016146097A (enExample)
WO (1) WO2015167968A1 (enExample)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ601967A (en) * 2010-03-12 2015-03-27 Omeros Corp Pde10 inhibitors and related compositions and methods
NZ716462A (en) * 2014-04-28 2017-11-24 Omeros Corp Optically active pde10 inhibitor
NZ630810A (en) * 2014-04-28 2016-03-31 Omeros Corp Processes and intermediates for the preparation of a pde10 inhibitor
US20160284909A1 (en) * 2015-03-27 2016-09-29 Gabriel Harley Multi-diode solar cells
CA2980801A1 (en) * 2015-04-24 2016-10-27 Omeros Corporation Pde10 inhibitors and related compositions and methods
CA3003611C (en) 2015-11-04 2022-11-01 Omeros Corporation Solid state forms of a pde10 inhibitor

Family Cites Families (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK178590D0 (da) 1990-07-26 1990-07-26 Novo Nordisk As 1,4-disubstituerede piperaziner
PT100905A (pt) 1991-09-30 1994-02-28 Eisai Co Ltd Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem
DK0672031T3 (da) 1992-12-02 2003-06-10 Pfizer Catecholdiethere som selektive PDE IV-inhibitorer
DE4323192A1 (de) 1993-07-10 1995-01-12 Basf Ag Verfahren zur Herstellung von Homo- und Copolymerisaten von Alk-1-enen
DE4325846C1 (de) 1993-07-31 1995-01-19 Herberts Gmbh Verwendung von Furan-modifizierten aromatischen Pinakolderivaten als Initiatoren und Furan-modifizierte aromatische Pinakolderivate als solche
DE4343286A1 (de) 1993-12-17 1995-06-22 Hoechst Ag Heteroaromatische Verbindungen und ihre Verwendung in flüssigkristallinen Mischungen
DE4409501A1 (de) 1994-03-19 1995-09-21 Didier Werke Ag Verschleißfutter eines Schachtofens und Stein hierfür
JP3056788B2 (ja) 1994-06-24 2000-06-26 ユーロ−セルティーク，エス．エイ． ホスホジエステラーゼｉｖの阻害化合物および阻害方法
US5789434A (en) 1994-11-15 1998-08-04 Bayer Corporation Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors
TW332201B (en) 1995-04-06 1998-05-21 Janssen Pharmaceutica Nv 1,3-Dihydro-1-(phenylalkyl)-2H-imidazol-2-one derivatives
TW424087B (en) 1995-04-06 2001-03-01 Janssen Pharmaceutica Nv 1,3-dihydro-1-(phenylalkenyl)-2H-imidazol-2-one derivatives
US6037370A (en) 1995-06-08 2000-03-14 Vertex Pharmaceuticals Incorporated Methods and compositions for stimulating neurite growth
EP1170009B1 (en) 1996-01-22 2004-04-07 Fujisawa Pharmaceutical Co., Ltd. Thiazolybenzofuran derivatives and their use as SRS-A and leukotiene antagonists
AU4015497A (en) 1996-08-26 1998-03-19 Byk Gulden Lomberg Chemische Fabrik Gmbh Thiazole derivatives useful as selective inhibitors of pde-iv
JPH1087543A (ja) 1996-09-17 1998-04-07 Chisso Corp アルコキシベンゼン誘導体、液晶組成物および液晶表示素子
US6548490B1 (en) 1997-10-28 2003-04-15 Vivus, Inc. Transmucosal administration of phosphodiesterase inhibitors for the treatment of erectile dysfunction
WO1999045914A1 (en) 1998-03-13 1999-09-16 Maruho Kabushikikaisha Alkyl amine derivative and local anesthetic agent using the same
GB9807354D0 (en) * 1998-04-07 1998-06-03 Glaxo Group Ltd Antiviral compound
SE9804212D0 (sv) 1998-12-04 1998-12-04 Astra Pharma Prod Compounds
WO2000034251A1 (en) 1998-12-07 2000-06-15 Smithkline Beecham Corporation A method for quantitative determination of amino acids
TR200102817T2 (tr) 1999-03-12 2002-05-21 Boehringer Ingelheim Pharmaceuticals, Inc. Antiinflamatuar ajanlar olarak faydalı bileşikler
US7141593B1 (en) * 1999-06-04 2006-11-28 Abbott Laboratories Pharmaceutical formulations
GB9929552D0 (en) 1999-12-14 2000-02-09 Proteus Molecular Design Compounds
JP2004511434A (ja) 2000-06-15 2004-04-15 ファルマシア・コーポレーション インテグリン受容体アンタゴニストとしてのヘテロアリールアルカン酸
US20030032579A1 (en) 2001-04-20 2003-02-13 Pfizer Inc. Therapeutic use of selective PDE10 inhibitors
DE60209704T2 (de) * 2001-05-22 2006-11-16 Pfizer Products Inc., Groton Neue kristallforme von azithromycin
US6821502B2 (en) * 2002-06-12 2004-11-23 Chevron U.S.A. Inc. Method of making aluminum-containing zeolite with IFR structure
US20050272036A1 (en) 2002-07-27 2005-12-08 Barton Peter J Ketones
AU2003275493A1 (en) 2002-10-08 2004-05-04 The Scripps Research Institute Inhibitors of fatty acid amide hydrolase
AU2003288352A1 (en) 2002-10-30 2004-06-07 Centre National De La Recherche Scientifique (Cnrs) Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses
TW200410921A (en) 2002-11-25 2004-07-01 Hoffmann La Roche Mandelic acid derivatives
US20060040986A1 (en) 2002-12-06 2006-02-23 Kowa Co., Ltd. Erythropoietin production accelerator
BR0317600A (pt) 2002-12-20 2005-11-29 Pharmacia Corp ácidos heteroarilalcanóicos como derivados de antagonistas de receptor de integrina
WO2004071509A1 (ja) 2003-02-12 2004-08-26 Nippon Chemiphar Co., Ltd. オリゴデンドロサイト分化促進剤
US7226930B2 (en) 2003-04-18 2007-06-05 Memory Pharmaceutical Corporation Phosphodiesterase 4 inhibitors
AR047541A1 (es) * 2004-02-13 2006-01-25 Sandoz Ag Fosfato de 5-[[4-[2-metil-2-piridinil-amino-etoxi]fenil]metil]-2,4 tiazolidinadiona (rosiglitazona) y sus formas polimorficas
NZ550114A (en) 2004-04-20 2011-02-25 Transtech Pharma Inc Substituted thiazole and pyrimidine derivatives as melanocortin receptor modulators
MXPA06013250A (es) * 2004-05-14 2007-02-28 Abbott Lab Inhibidores de quinasa como agentes terapeuticos.
US7351833B2 (en) * 2004-07-23 2008-04-01 Abbott Laboratories (1S,5S)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane benzenesulfonate
US7449486B2 (en) * 2004-10-19 2008-11-11 Array Biopharma Inc. Mitotic kinesin inhibitors and methods of use thereof
US8436176B2 (en) * 2004-12-30 2013-05-07 Medicis Pharmaceutical Corporation Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine
WO2006072828A2 (en) 2005-01-07 2006-07-13 Pfizer Products Inc. Heteroaromatic quinoline compounds and their use as pde10 inhibitors
CN101384183B (zh) 2005-02-04 2012-07-04 西诺米克斯公司 包含连接有杂芳基部分的化合物及其作为用于食物组合物的新型鲜味调节剂、促味剂和味觉增强剂的应用
US20060252807A1 (en) 2005-04-22 2006-11-09 Kalypsys, Inc. Novel ortho-terphenyl inhibitors of p38 kinase and methods of treating inflammatory disorders
UA91546C2 (uk) * 2005-05-03 2010-08-10 Бьорінгер Інгельхайм Інтернаціональ Гмбх КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ
MY152185A (en) * 2005-06-10 2014-08-29 Novartis Ag Modified release 1-[(3-hydroxy-adamant-1-ylamino)-acetyl]-pyrrolidine-2(s)-carbonitrile formulation
CA2617788A1 (en) 2005-08-04 2007-02-15 Apogee Biotechnology Corporation Sphingosine kinase inhibitors and methods of their use
PT1924585E (pt) * 2005-08-29 2012-01-19 Sanofi Aventis Us Llc Nova forma cristalina de um derivado de piridazino[4,5-b]indole
DE602006019822D1 (de) * 2005-09-13 2011-03-10 Sicor Inc Reines rocuroniumbromid
TWI330639B (en) 2005-11-15 2010-09-21 Otsuka Pharma Co Ltd Oxazole compound and pharmaceutical composition
EP1968946A4 (en) 2005-12-23 2010-05-05 Astrazeneca Ab IMIDAZOLE AS MODULATORS OF THE GABA B RECEPTOR
JP2009535394A (ja) 2006-05-02 2009-10-01 ファイザー・プロダクツ・インク Ｐｄｅ１０阻害剤としての二環式ヘテロアリール化合物
US20080090834A1 (en) 2006-07-06 2008-04-17 Pfizer Inc Selective azole pde10a inhibitor compounds
JP2010502736A (ja) 2006-09-08 2010-01-28 オレ・ファーマシューティカルズ・インコーポレーテッド 消化管の炎症を低減または軽減するための方法
UA99600C2 (en) * 2006-09-25 2012-09-10 ПиТиСи ТЕРАПЬЮТИКС, ИНК. Crystalline forms of 3-[5-(2-fhjorophenyl)-[1,2,4]oxadiazol-3-yl]-benzoic acid
KR20090064400A (ko) * 2006-09-28 2009-06-18 머크 앤드 캄파니 인코포레이티드 Ｈｄａｃ 억제제 및 킬레이트화 가능한 금속 화합물 및 금속-ｈｄａｃ 억제제 킬레이트 착물의 약제학적 조성물
US20090253918A1 (en) 2006-10-02 2009-10-08 Janssen Pharmaceuticals, N.V. Novel intermediate for glyt1 inhibitor
US7837978B2 (en) * 2006-10-13 2010-11-23 Chevron U.S.A. Inc. Process for preparing aluminum-containing molecular sieve SSZ-26
US7786139B2 (en) 2006-11-21 2010-08-31 Omeros Corporation PDE10 inhibitors and related compositions and methods
EP2083819B1 (en) * 2006-11-21 2017-02-22 Omeros Corporation Pde10 inhibitors and related compositions and methods
PE20081506A1 (es) * 2006-12-12 2008-12-09 Infinity Discovery Inc Formulaciones de ansamicina
WO2009008906A2 (en) 2007-02-06 2009-01-15 The Trustees Of The University Of Pennsylvania Therapeutic compounds for blocking dna synthesis of pox viruses
EP2160394A1 (en) * 2007-05-22 2010-03-10 Ultimorphix Technologies B.v. Tenofovir disoproxil hemi-fumaric acid co-crystal
EP2017264A1 (de) 2007-07-16 2009-01-21 Bayer Cropscience Ag Substituierte Phenylpropargylverbindungen, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO2009049022A1 (en) 2007-10-10 2009-04-16 Ore Pharmaceuticals Inc. Method for treatment of pancreatitis
TW200944520A (en) * 2008-01-29 2009-11-01 Glaxo Group Ltd Spiro compounds as NPY Y5 receptor antagonists
WO2009143178A2 (en) 2008-05-20 2009-11-26 Omeros Corporation Pde10 inhibitors and related compositions and methods
TWI501965B (zh) 2008-06-20 2015-10-01 Lundbeck & Co As H 作為ｐｄｅ１０ａ酵素抑制劑之新穎苯基咪唑衍生物
EP2310016B1 (en) 2008-08-05 2017-10-04 Omeros Corporation Pde10 inhibitors and related compositions and methods
NZ601967A (en) * 2010-03-12 2015-03-27 Omeros Corp Pde10 inhibitors and related compositions and methods
NZ716462A (en) * 2014-04-28 2017-11-24 Omeros Corp Optically active pde10 inhibitor
NZ630810A (en) * 2014-04-28 2016-03-31 Omeros Corp Processes and intermediates for the preparation of a pde10 inhibitor

Also Published As

Publication number Publication date
US9850238B2 (en) 2017-12-26
WO2015167968A1 (en) 2015-11-05
US20170096420A1 (en) 2017-04-06
RU2016146097A3 (enExample) 2018-11-15
KR102558505B1 (ko) 2023-07-21
BR112016024523B1 (pt) 2022-10-11
EP3137461A4 (en) 2017-09-13
NZ630803A (en) 2016-03-31
JP2017513913A (ja) 2017-06-01
CN106255690B (zh) 2020-07-17
NZ716462A (en) 2017-11-24
ES2895487T3 (es) 2022-02-21
EP3137461A1 (en) 2017-03-08
IL248586A0 (en) 2016-12-29
BR112016024523A2 (pt) 2017-08-15
CN106255690A (zh) 2016-12-21
KR20160141845A (ko) 2016-12-09
EP3137461B1 (en) 2021-08-11
US20160024070A1 (en) 2016-01-28
RU2016146097A (ru) 2018-05-30
CA2946754A1 (en) 2015-11-05
AU2015253463A1 (en) 2016-11-03
US9493447B2 (en) 2016-11-15
IL248586B (en) 2019-09-26
AU2015253463B2 (en) 2018-12-06

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