AU2017353315B2 - (1,2,4)triazolo(1,5-a)pyrimidine compounds as PDE2 inhibitors - Google Patents

(1,2,4)triazolo(1,5-a)pyrimidine compounds as PDE2 inhibitors Download PDF

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Publication number
AU2017353315B2
AU2017353315B2 AU2017353315A AU2017353315A AU2017353315B2 AU 2017353315 B2 AU2017353315 B2 AU 2017353315B2 AU 2017353315 A AU2017353315 A AU 2017353315A AU 2017353315 A AU2017353315 A AU 2017353315A AU 2017353315 B2 AU2017353315 B2 AU 2017353315B2
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disorder
disorders
dementia
disease
group
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AU2017353315A1 (en
Inventor
Peter Jacobus Johannes Antonius Buijnsters
Henricus Jacobus Maria Gijsen
Edgar Jacoby
Daniel Oehlrich
Gary Tresadern
Yves Emiel Maria Van Roosbroeck
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Janssen Pharmaceutica NV
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    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5355Non-condensed oxazines and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/08Antiepileptics; Anticonvulsants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/20Hypnotics; Sedatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/22Anxiolytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32Alcohol-abuse
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/34Tobacco-abuse
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36Opioid-abuse
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D451/00Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Epidemiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Psychology (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
AU2017353315A 2016-11-02 2017-10-31 (1,2,4)triazolo(1,5-a)pyrimidine compounds as PDE2 inhibitors Ceased AU2017353315B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP16196943.1 2016-11-02
EP16196943 2016-11-02
PCT/EP2017/077920 WO2018083103A1 (en) 2016-11-02 2017-10-31 [1,2,4]triazolo[1,5-a]pyrimidine compounds as pde2 inhibitors

Publications (2)

Publication Number Publication Date
AU2017353315A1 AU2017353315A1 (en) 2019-05-02
AU2017353315B2 true AU2017353315B2 (en) 2021-09-16

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AU2017353315A Ceased AU2017353315B2 (en) 2016-11-02 2017-10-31 (1,2,4)triazolo(1,5-a)pyrimidine compounds as PDE2 inhibitors

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US (1) US11053248B2 (enExample)
EP (1) EP3535269B1 (enExample)
JP (1) JP7021208B2 (enExample)
KR (1) KR20190071721A (enExample)
CN (1) CN109937202B (enExample)
AU (1) AU2017353315B2 (enExample)
BR (1) BR112019008163A2 (enExample)
CA (1) CA3038916A1 (enExample)
EA (1) EA039102B1 (enExample)
ES (1) ES2855032T3 (enExample)
MX (1) MX386174B (enExample)
WO (1) WO2018083103A1 (enExample)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HK1256751A1 (zh) 2015-11-02 2019-10-04 Janssen Pharmaceutica Nv [1,2,4]三唑并[1,5-a]嘧啶-7-基化合物
CN109937202B (zh) 2016-11-02 2022-12-30 詹森药业有限公司 作为pde2抑制剂的[1,2,4]三唑并[1,5-a]嘧啶化合物
MA46690A (fr) 2016-11-02 2019-09-11 Janssen Pharmaceutica Nv Composés de [1,2,4]triazolo [1,5-a]pyrimidine en tant qu'inhibiteurs de pde2
MY193511A (en) 2016-11-02 2022-10-17 Janssen Pharmaceutica Nv [1,2,4]triazolo[1,5-a]pyrimidine derivatives as pde2 inhibitors
CA3150878A1 (en) * 2019-09-12 2021-03-18 Jonathan Bentley Inhibitors of sarm1

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013000924A1 (en) * 2011-06-27 2013-01-03 Janssen Pharmaceutica Nv 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES
WO2015164508A1 (en) * 2014-04-23 2015-10-29 Dart Neuroscience, Llc Substituted [1,2,4] triazolo [1,5-a] pyrimidin-7-yl compounds as pde2 inhibitors

Family Cites Families (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036840A (en) * 1972-06-07 1977-07-19 Icn Pharmaceuticals 2-Substituted-s-triazolo[1,5a]pyrimidines
PT100639A (pt) 1991-06-27 1993-09-30 Univ Virginia Commonwealth Metodo para o tratamento terapeutico com compostos que sao ligandos ao receptor sigma e compostos ai utilizados, nomeadamente derivados fenilalquil-amina, aminotetralina,piperazina e piperidina
HUP0101810A3 (en) 1998-01-27 2002-05-28 Aventis Pharm Prod Inc Substituted oxoazaheterocyclyl factor xa inhibitors and pharmaceutical compositions containing them
US6194410B1 (en) 1998-03-11 2001-02-27 Hoffman-La Roche Inc. Pyrazolopyrimidine and pyrazolines and process for preparation thereof
US20040014744A1 (en) 2002-04-05 2004-01-22 Fortuna Haviv Substituted pyridines having antiangiogenic activity
EP1546103B1 (en) 2002-10-03 2009-03-18 Vertex Pharmaceuticals Incorporated Piperazine and piperidine derivatives for treatment of neurological diseases
US20070275961A1 (en) 2003-06-04 2007-11-29 Vernalis (Cambridge) Limited. Triazolo ' 1, 5-A ! Pyrimidines and Their Use in Medicine
CN100549014C (zh) 2003-07-16 2009-10-14 詹森药业有限公司 作为糖原合酶激酶3抑制剂的三唑并嘧啶衍生物
KR20060105872A (ko) 2003-12-29 2006-10-11 반유 세이야꾸 가부시끼가이샤 신규한 2-헤테로아릴 치환된 벤즈이미다졸 유도체
JP5149009B2 (ja) 2004-09-20 2013-02-20 ゼノン・ファーマシューティカルズ・インコーポレイテッド ヒトステアロイル−CoAデサチュラーゼを阻害するためのピリダジン誘導体
MX2007003325A (es) 2004-09-20 2007-06-05 Xenon Pharmaceuticals Inc Derivados heterociclicos y su uso como inhibidores estearoil-coa-desaturasa.
EP1812439B2 (en) 2004-10-15 2017-12-06 Takeda Pharmaceutical Company Limited Kinase inhibitors
US20100160349A1 (en) * 2005-01-14 2010-06-24 Christopher John Love Triazolopyrimidine derivatives as glycogen synthase kinase 3 inhibitors
US7507842B2 (en) 2005-08-12 2009-03-24 Radiorx, Inc. Cyclic nitro compounds, pharmaceutical compositions thereof and uses thereof
WO2007113136A1 (de) 2006-03-30 2007-10-11 Basf Aktiengesellschaft Verwendung von substituierten riazolopyrimidinen zur bekämpfung von phyto pathogenen schadpilzen
JP2007332061A (ja) 2006-06-14 2007-12-27 Nippon Kayaku Co Ltd 新規ピラゾロ[1,5−a]ピリミジン誘導体及びその用途
US8153803B2 (en) 2006-07-18 2012-04-10 The General Hospital Corporation Compositions and methods for modulating sirtuin activity
WO2008048914A1 (en) 2006-10-17 2008-04-24 Boehringer Ingelheim International Gmbh Polycyclic compounds which modulate the cb2 receptor
AU2008275927B8 (en) * 2007-07-18 2014-08-14 Janssen Pharmaceutica N.V. Sulfonamides as TRPM8 modulators
US8138168B1 (en) 2007-09-26 2012-03-20 Takeda Pharmaceutical Company Limited Renin inhibitors
GB0719803D0 (en) 2007-10-10 2007-11-21 Cancer Rec Tech Ltd Therapeutic compounds and their use
CN101560212B (zh) * 2009-05-26 2011-03-16 华中师范大学 1,2,4-三唑并[1,5-a]嘧啶-2-乙基硫醚双取代衍生物的制备及其应用
WO2012080729A2 (en) 2010-12-14 2012-06-21 Electrophoretics Limited CASEIN KINASE 1δ (CK1δ) INHIBITORS
AP2013007070A0 (en) 2011-02-23 2013-08-31 Pfizer Imidazo[5,1-f][1,2,4] triazines for the treatment of neurological disorders
CA2849726A1 (en) 2011-09-23 2013-03-28 Advinus Therapeutics Limited Amide compounds, compositions and applications thereof
CN103183675A (zh) * 2011-12-27 2013-07-03 山东轩竹医药科技有限公司 磷酸二酯酶-4抑制剂
US9034882B2 (en) 2012-03-05 2015-05-19 Bristol-Myers Squibb Company Inhibitors of human immunodeficiency virus replication
PL2834243T3 (pl) 2012-03-09 2018-09-28 Lexicon Pharmaceuticals, Inc. Związki na bazie pirazolo[1,5-a]pirymidyny, zawierające je kompozycje i sposoby ich zastosowania
US9193736B2 (en) * 2013-06-11 2015-11-24 Janssen Pharmaceutica, Nv PDE 10a inhibitors for the treatment of type II diabetes
US9328095B2 (en) * 2013-10-15 2016-05-03 Janssen Pharmaceutica Nv Heteroaryl linked quinolinyl modulators of RORgammat
WO2015130905A1 (en) 2014-02-27 2015-09-03 Merck Patent Gmbh Heterocyclic compounds as nav channel inhibitors and uses thereof
MX2016011784A (es) 2014-03-19 2016-12-02 Boehringer Ingelheim Int Nuevos heteroarilos y su uso como medicamentos.
CN105566321B (zh) 2014-10-29 2020-04-21 广东东阳光药业有限公司 杂芳化合物及其在药物中的应用
WO2016107602A1 (zh) 2015-01-01 2016-07-07 成都贝斯凯瑞生物科技有限公司 一类取代氮杂环衍生物及其应用
WO2016145614A1 (en) 2015-03-17 2016-09-22 Merck Sharp & Dohme Corp. Triazolyl pyrimidinone compounds as pde2 inhibitors
WO2017000276A1 (en) 2015-07-01 2017-01-05 Merck Sharp & Dohme Corp. Bicyclic heterocyclic compounds as pde2 inhibitors
WO2017000277A1 (en) 2015-07-01 2017-01-05 Merck Sharp & Dohme Corp. Substituted triazolo bicycliccompounds as pde2 inhibitors
WO2017066705A1 (en) 2015-10-14 2017-04-20 Aquinnah Pharmaceuticals, Inc. Compounds, compositions and methods of use against stress granules
HK1256751A1 (zh) 2015-11-02 2019-10-04 Janssen Pharmaceutica Nv [1,2,4]三唑并[1,5-a]嘧啶-7-基化合物
WO2017157882A1 (en) 2016-03-14 2017-09-21 Université Catholique de Louvain Serine biosynthetic pathway inhibitors
CN109937202B (zh) 2016-11-02 2022-12-30 詹森药业有限公司 作为pde2抑制剂的[1,2,4]三唑并[1,5-a]嘧啶化合物
MA46690A (fr) 2016-11-02 2019-09-11 Janssen Pharmaceutica Nv Composés de [1,2,4]triazolo [1,5-a]pyrimidine en tant qu'inhibiteurs de pde2
MY193511A (en) 2016-11-02 2022-10-17 Janssen Pharmaceutica Nv [1,2,4]triazolo[1,5-a]pyrimidine derivatives as pde2 inhibitors
AU2017378182A1 (en) 2016-12-16 2019-06-06 Janssen Pharmaceutica Nv Bicyclic OGA inhibitor compounds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013000924A1 (en) * 2011-06-27 2013-01-03 Janssen Pharmaceutica Nv 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES
WO2015164508A1 (en) * 2014-04-23 2015-10-29 Dart Neuroscience, Llc Substituted [1,2,4] triazolo [1,5-a] pyrimidin-7-yl compounds as pde2 inhibitors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Bioorganic & Medicinal Chemistry Letters, 2013, 23(24), 6522-27 *

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Publication number Publication date
BR112019008163A2 (pt) 2019-07-09
AU2017353315A1 (en) 2019-05-02
EP3535269B1 (en) 2020-12-09
JP7021208B2 (ja) 2022-02-16
US11053248B2 (en) 2021-07-06
MX386174B (es) 2025-03-18
EP3535269A1 (en) 2019-09-11
EA039102B1 (ru) 2021-12-03
EA201990973A1 (ru) 2019-09-30
MX2019005115A (es) 2019-06-20
ES2855032T3 (es) 2021-09-23
CN109937202B (zh) 2022-12-30
US20200048260A1 (en) 2020-02-13
JP2019532983A (ja) 2019-11-14
CN109937202A (zh) 2019-06-25
KR20190071721A (ko) 2019-06-24
WO2018083103A1 (en) 2018-05-11
CA3038916A1 (en) 2018-05-11

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