SG10201811574YA - Biphenyl amides with modified ether groups as hsp90 inhibitors and hsp70 inducers - Google Patents

Biphenyl amides with modified ether groups as hsp90 inhibitors and hsp70 inducers

Info

Publication number
SG10201811574YA
SG10201811574YA SG10201811574YA SG10201811574YA SG10201811574YA SG 10201811574Y A SG10201811574Y A SG 10201811574YA SG 10201811574Y A SG10201811574Y A SG 10201811574YA SG 10201811574Y A SG10201811574Y A SG 10201811574YA SG 10201811574Y A SG10201811574Y A SG 10201811574YA
Authority
SG
Singapore
Prior art keywords
ether groups
hsp90 inhibitors
modified ether
hsp70 inducers
biphenyl amides
Prior art date
Application number
SG10201811574YA
Other languages
English (en)
Inventor
Brian Blagg
Rick Dobrowsky
Mercy Anyika
Original Assignee
Univ Kansas
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 Univ Kansas filed Critical Univ Kansas
Publication of SG10201811574YA publication Critical patent/SG10201811574YA/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
    • C07D309/10Oxygen atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/01Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
    • C07D307/20Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/16Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/203Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/06Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Epidemiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Rheumatology (AREA)
  • Vascular Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Obesity (AREA)
  • Emergency Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Endocrinology (AREA)
  • Psychiatry (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
SG10201811574YA 2014-06-24 2015-06-24 Biphenyl amides with modified ether groups as hsp90 inhibitors and hsp70 inducers SG10201811574YA (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US201462016473P 2014-06-24 2014-06-24

Publications (1)

Publication Number Publication Date
SG10201811574YA true SG10201811574YA (en) 2019-01-30

Family

ID=53525293

Family Applications (2)

Application Number Title Priority Date Filing Date
SG10201811574YA SG10201811574YA (en) 2014-06-24 2015-06-24 Biphenyl amides with modified ether groups as hsp90 inhibitors and hsp70 inducers
SG11201610677XA SG11201610677XA (en) 2014-06-24 2015-06-24 Biphenyl amides with modified ether groups as hsp90 inhibitors and hsp70 inducers

Family Applications After (1)

Application Number Title Priority Date Filing Date
SG11201610677XA SG11201610677XA (en) 2014-06-24 2015-06-24 Biphenyl amides with modified ether groups as hsp90 inhibitors and hsp70 inducers

Country Status (15)

Country Link
US (3) US10590065B2 (https=)
EP (2) EP4494702A3 (https=)
JP (2) JP6793640B2 (https=)
KR (1) KR102536408B1 (https=)
CN (1) CN106536498A (https=)
AU (2) AU2015279926B2 (https=)
CA (2) CA3289739A1 (https=)
CL (2) CL2016003276A1 (https=)
CO (1) CO2017000552A2 (https=)
EA (1) EA201790070A1 (https=)
IL (1) IL249712B (https=)
MX (2) MX388516B (https=)
NZ (1) NZ728482A (https=)
SG (2) SG10201811574YA (https=)
WO (1) WO2015200514A2 (https=)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SMT201900660T1 (it) 2012-02-09 2020-01-14 Univ Kansas Inibitori c-terminali di hsp90
CA2951270C (en) 2014-06-13 2023-07-04 The University Of Kansas Triazole modified coumarin and biphenyl amide-based hsp90 inhibitors
MX388516B (es) 2014-06-24 2025-03-20 Univ Kansas Bifenil amidas con grupos éter modificados como inhibidores de hsp90 e inductores de hsp70.
CN108478568B (zh) * 2018-02-01 2020-08-28 华中农业大学 一种香豆素类化合物在制备单胺氧化酶抑制剂中的用途
EP3749675B1 (en) 2018-02-07 2025-12-31 Reata Pharmaceuticals, Inc. CO-CRISTALLIN FORMS OF A NOVOBIOCIN AND PROLINE ANALOGUE
JP7508375B2 (ja) * 2018-05-14 2024-07-01 リアタ ファーマシューティカルズ インコーポレイテッド 熱ショックタンパク質経路に関連する疾患の治療のための、修飾された糖基を有するビアリールアミド
KR102175125B1 (ko) * 2018-12-28 2020-11-05 울산과학기술원 미토콘드리아 표적 Hsp90 억제제 기반 화합물 및 이를 포함하는 광역학 치료를 위한 약학적 조성물
AU2024265078A1 (en) 2023-05-04 2025-12-11 Revolution Medicines, Inc. Combination therapy for a ras related disease or disorder
IL326136A (en) 2023-08-07 2026-03-01 Revolution Medicines Inc RMC-6291 for use in the treatment of a disease or disorder associated with the RAS protein
US20250154171A1 (en) 2023-10-12 2025-05-15 Revolution Medicines, Inc. Ras inhibitors
WO2025171296A1 (en) 2024-02-09 2025-08-14 Revolution Medicines, Inc. Ras inhibitors
WO2025240847A1 (en) 2024-05-17 2025-11-20 Revolution Medicines, Inc. Ras inhibitors
US20250375445A1 (en) 2024-06-07 2025-12-11 Revolution Medicines, Inc. Methods of treating a ras protein-related disease or disorder
WO2025265060A1 (en) 2024-06-21 2025-12-26 Revolution Medicines, Inc. Therapeutic compositions and methods for managing treatment-related effects
WO2026006747A1 (en) 2024-06-28 2026-01-02 Revolution Medicines, Inc. Ras inhibitors
WO2026015825A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Use of ras inhibitor for treating pancreatic cancer
WO2026015796A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Methods of treating a ras related disease or disorder
WO2026015801A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Methods of treating a ras related disease or disorder
WO2026015790A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Methods of treating a ras related disease or disorder
WO2026050446A1 (en) 2024-08-29 2026-03-05 Revolution Medicines, Inc. Ras inhibitors
WO2026072904A2 (en) 2024-09-26 2026-04-02 Revolution Medicines, Inc. Compositions and methods for treating lung cancer

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AU2002223127A1 (en) 2000-11-30 2002-06-11 Kissei Pharmaceutical Co., Ltd. Intellectual Property Glucopyranosyloxybenzyl benzene derivatives, medicinal compositions containing the same and intermediates in the production thereof
WO2006050501A2 (en) 2004-11-03 2006-05-11 University Of Kansas Novobiocin analogues as anticancer agents
US8212012B2 (en) 2004-11-03 2012-07-03 University Of Kansas Novobiocin analogues having modified sugar moieties
US9120774B2 (en) 2004-11-03 2015-09-01 University Of Kansas Novobiocin analogues having modified sugar moieties
US7622451B2 (en) 2004-11-03 2009-11-24 University Of Kansas Novobiocin analogues as neuroprotective agents and in the treatment of autoimmune disorders
US8212011B2 (en) 2004-11-03 2012-07-03 University Of Kansas Novobiocin analogues
CA2620566A1 (en) 2005-08-30 2007-03-08 Boehringer Ingelheim International Gmbh Glucopyranosyl-substituted benzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
WO2008061108A2 (en) 2006-11-15 2008-05-22 Forest Laboratories Holdings Limited Phthalazine derivatives
JP5401329B2 (ja) 2007-03-20 2014-01-29 キュリス,インコーポレイテッド Hsp90インヒビターとしての縮合アミノピリジン
US7960353B2 (en) 2007-05-10 2011-06-14 University Of Kansas Novobiocin analogues as neuroprotective agents and in the treatment of autoimmune disorders
JP5766617B2 (ja) * 2009-02-20 2015-08-19 ユニバーシティ・オブ・カンザス 修飾された糖部分を有するノボビオシン類似体
US20110082098A1 (en) 2009-09-30 2011-04-07 University Of Kansas Novobiocin analogues and treatment of polycystic kidney disease
TW201216957A (en) 2010-07-13 2012-05-01 Dainippon Sumitomo Pharma Co Biarylamide derivative or a pharmaceutically acceptable salt thereof
ES2647889T3 (es) * 2011-04-05 2017-12-27 Sloan-Kettering Institute For Cancer Research Inhibidores de la Hsp90
US9056104B2 (en) 2011-05-20 2015-06-16 The University Of Kansas Dynamic inhibitors of heat shock protein 90
WO2012163054A1 (zh) 2011-11-16 2012-12-06 华为技术有限公司 一种微波预失真信号生成方法和装置
SMT201900660T1 (it) * 2012-02-09 2020-01-14 Univ Kansas Inibitori c-terminali di hsp90
MX388516B (es) 2014-06-24 2025-03-20 Univ Kansas Bifenil amidas con grupos éter modificados como inhibidores de hsp90 e inductores de hsp70.

Also Published As

Publication number Publication date
CO2017000552A2 (es) 2017-04-28
CN106536498A (zh) 2017-03-22
MX388516B (es) 2025-03-20
JP6793640B2 (ja) 2020-12-02
EP4494702A3 (en) 2025-02-26
CL2018002367A1 (es) 2018-10-12
US20180057446A1 (en) 2018-03-01
AU2015279926A1 (en) 2017-02-16
IL249712A0 (en) 2017-02-28
JP2021042217A (ja) 2021-03-18
WO2015200514A3 (en) 2016-02-25
KR20170035911A (ko) 2017-03-31
US20220041543A1 (en) 2022-02-10
CA3289739A1 (en) 2025-11-29
JP2017521496A (ja) 2017-08-03
AU2015279926B2 (en) 2020-12-24
MX2016017133A (es) 2018-01-12
US11098008B2 (en) 2021-08-24
IL249712B (en) 2021-04-29
CL2016003276A1 (es) 2017-05-26
NZ728482A (en) 2022-11-25
WO2015200514A2 (en) 2015-12-30
US20200270201A1 (en) 2020-08-27
US11708319B2 (en) 2023-07-25
KR102536408B1 (ko) 2023-05-23
BR112016029672A2 (pt) 2017-08-22
MX388515B (es) 2025-03-20
AU2021200969B2 (en) 2022-08-04
JP7105851B2 (ja) 2022-07-25
EP4494702A2 (en) 2025-01-22
SG11201610677XA (en) 2017-01-27
AU2021200969A1 (en) 2021-03-11
CA2952029C (en) 2026-04-07
US10590065B2 (en) 2020-03-17
EP3160977A2 (en) 2017-05-03
EA201790070A1 (ru) 2017-10-31
CA2952029A1 (en) 2015-12-30
MX2019015888A (es) 2020-02-07

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