AU2017269673A1 - Pyridine dicarboxamide derivatives as bromodomain inhibitors - Google Patents

Pyridine dicarboxamide derivatives as bromodomain inhibitors Download PDF

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Publication number
AU2017269673A1
AU2017269673A1 AU2017269673A AU2017269673A AU2017269673A1 AU 2017269673 A1 AU2017269673 A1 AU 2017269673A1 AU 2017269673 A AU2017269673 A AU 2017269673A AU 2017269673 A AU2017269673 A AU 2017269673A AU 2017269673 A1 AU2017269673 A1 AU 2017269673A1
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AU
Australia
Prior art keywords
bromodomain inhibitors
dicarboxamide derivatives
pyridine dicarboxamide
pyridine
derivatives
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
AU2017269673A
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English (en)
Inventor
Stephen John Atkinson
Emmanuel Hubert Demont
Lee Andrew Harrison
Etienne LEVERNIER
Alexander G. Preston
Jonathan Thomas Seal
Ian David Wall
Robert J. Watson
James Michael Woolven
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.)
GlaxoSmithKline Intellectual Property No 2 Ltd
Original Assignee
GlaxoSmithKline Intellectual Property No 2 Ltd
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
Priority claimed from GBGB1609096.1A external-priority patent/GB201609096D0/en
Priority claimed from GBGB1703274.9A external-priority patent/GB201703274D0/en
Application filed by GlaxoSmithKline Intellectual Property No 2 Ltd filed Critical GlaxoSmithKline Intellectual Property No 2 Ltd
Publication of AU2017269673A1 publication Critical patent/AU2017269673A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • 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
    • A61K31/435—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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • 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
    • 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
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Rheumatology (AREA)
  • Virology (AREA)
  • Pain & Pain Management (AREA)
  • Pulmonology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
AU2017269673A 2016-05-24 2017-05-22 Pyridine dicarboxamide derivatives as bromodomain inhibitors Abandoned AU2017269673A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB1609096.1 2016-05-24
GBGB1609096.1A GB201609096D0 (en) 2016-05-24 2016-05-24 Compounds
GBGB1703274.9A GB201703274D0 (en) 2017-03-01 2017-03-01 Compound
GB1703274.9 2017-03-01
PCT/EP2017/062208 WO2017202742A1 (en) 2016-05-24 2017-05-22 Pyridine dicarboxamide derivatives as bromodomain inhibitors

Publications (1)

Publication Number Publication Date
AU2017269673A1 true AU2017269673A1 (en) 2018-11-22

Family

ID=58739056

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2017269673A Abandoned AU2017269673A1 (en) 2016-05-24 2017-05-22 Pyridine dicarboxamide derivatives as bromodomain inhibitors

Country Status (10)

Country Link
US (1) US10844015B2 (enExample)
EP (1) EP3464242A1 (enExample)
JP (1) JP6885968B2 (enExample)
KR (1) KR20190006567A (enExample)
CN (1) CN109153646B (enExample)
AU (1) AU2017269673A1 (enExample)
BR (1) BR112018073524A2 (enExample)
CA (1) CA3023765A1 (enExample)
RU (1) RU2018142988A (enExample)
WO (1) WO2017202742A1 (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3344615A1 (en) 2015-09-02 2018-07-11 GlaxoSmithKline Intellectual Property (No. 2) Limited Pyridinone dicarboxamide for use as bromodomain inhibitors
KR20180052762A (ko) 2015-09-22 2018-05-18 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 브로모도메인 억제제로서 사용하기 위한 피리디논 디카르복스아미드
RU2018114705A (ru) 2015-10-05 2019-11-07 ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед Соединения 2-оксо-1,2-дигидропиридин-3,5-дикарбоксамида в качестве ингибиторов бромодомена
AU2017245641A1 (en) 2016-04-07 2018-09-13 Glaxosmithkline Intellectual Property (No.2) Limited Pyridyl derivatives as bromodomain inhibitors
CA3023765A1 (en) 2016-05-24 2017-11-30 Glaxosmithkline Intellectual Property (No. 2) Limited Pyridine dicarboxamide derivatives as bromodomain inhibitors
JOP20190192A1 (ar) 2017-03-01 2019-08-08 Glaxosmithkline Ip No 2 Ltd مشتقات بيرازول بوصفها مثبطات برومودومين
GB201703282D0 (en) * 2017-03-01 2017-04-12 Glaxosmithkline Intellectual Property (No 2) Ltd Compounds
US10800774B2 (en) 2017-08-17 2020-10-13 Board Of Regents, The University Of Texas System Heterocyclic inhibitors of ATR kinase
GB201814167D0 (en) 2018-08-31 2018-10-17 Glaxosmithkline Ip No 2 Ltd Compounds

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GB9004781D0 (en) 1990-03-02 1990-04-25 Glaxo Group Ltd Device
ATE438624T1 (de) 2000-12-28 2009-08-15 Shionogi & Co 2-pyridonderivate mit affinität für den cannabinoid-typ-2-rezeptor
DOP2002000332A (es) * 2001-02-14 2002-08-30 Warner Lambert Co Inhibidores de piridina de metaloproteinasas de la matriz
PT1477186E (pt) 2002-02-19 2010-02-11 Shionogi & Co Antipruriginosos
EP1551824B1 (en) * 2002-10-09 2007-12-12 Critical Outcome Technologies, Inc. Protein tyrosine kinase inhibitors
EP1433788A1 (en) 2002-12-23 2004-06-30 Aventis Pharma Deutschland GmbH Pyrazole-derivatives as factor Xa inhibitors
CN102028994B (zh) 2003-11-03 2013-04-24 葛兰素集团有限公司 流体分配装置
GB0919423D0 (en) 2009-11-05 2009-12-23 Glaxosmithkline Llc Novel compounds
GB0919434D0 (en) 2009-11-05 2009-12-23 Glaxosmithkline Llc Novel compounds
WO2012138734A1 (en) 2011-04-07 2012-10-11 Merck Sharp & Dohme Corp. C5-c6 oxacyclic-fused thiadiazine dioxide compounds as bace inhibitors, compositions, and their use
SG11201503397YA (en) * 2012-11-08 2015-05-28 Bristol Myers Squibb Co Heteroaryl substituted pyridyl compounds useful as kinase modulators
AU2013365926B9 (en) 2012-12-21 2019-01-17 Zenith Epigenetics Ltd. Novel heterocyclic compounds as bromodomain inhibitors
CN105593224B (zh) * 2013-07-31 2021-05-25 恒元生物医药科技(苏州)有限公司 作为溴结构域抑制剂的新型喹唑啉酮类化合物
EP3344615A1 (en) * 2015-09-02 2018-07-11 GlaxoSmithKline Intellectual Property (No. 2) Limited Pyridinone dicarboxamide for use as bromodomain inhibitors
KR20180052762A (ko) 2015-09-22 2018-05-18 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 브로모도메인 억제제로서 사용하기 위한 피리디논 디카르복스아미드
RU2018114705A (ru) * 2015-10-05 2019-11-07 ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед Соединения 2-оксо-1,2-дигидропиридин-3,5-дикарбоксамида в качестве ингибиторов бромодомена
AU2017245641A1 (en) 2016-04-07 2018-09-13 Glaxosmithkline Intellectual Property (No.2) Limited Pyridyl derivatives as bromodomain inhibitors
CA3023765A1 (en) 2016-05-24 2017-11-30 Glaxosmithkline Intellectual Property (No. 2) Limited Pyridine dicarboxamide derivatives as bromodomain inhibitors
GB201703282D0 (en) 2017-03-01 2017-04-12 Glaxosmithkline Intellectual Property (No 2) Ltd Compounds

Also Published As

Publication number Publication date
KR20190006567A (ko) 2019-01-18
CA3023765A1 (en) 2017-11-30
CN109153646A (zh) 2019-01-04
WO2017202742A1 (en) 2017-11-30
US10844015B2 (en) 2020-11-24
JP2019516761A (ja) 2019-06-20
EP3464242A1 (en) 2019-04-10
BR112018073524A2 (pt) 2019-05-28
RU2018142988A (ru) 2020-06-25
US20190202786A1 (en) 2019-07-04
JP6885968B2 (ja) 2021-06-16
CN109153646B (zh) 2022-08-02

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