CA3289739A1 - 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
CA3289739A1
CA3289739A1 CA3289739A CA3289739A CA3289739A1 CA 3289739 A1 CA3289739 A1 CA 3289739A1 CA 3289739 A CA3289739 A CA 3289739A CA 3289739 A CA3289739 A CA 3289739A CA 3289739 A1 CA3289739 A1 CA 3289739A1
Authority
CA
Canada
Prior art keywords
ether groups
hsp90 inhibitors
modified ether
hsp70 inducers
biphenyl amides
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.)
Pending
Application number
CA3289739A
Other languages
English (en)
Inventor
Brian S J Blagg
Rick T Dobrowsky
Mercy Anyika
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.)
University of Kansas
Original Assignee
University of 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 University of Kansas filed Critical University of Kansas
Publication of CA3289739A1 publication Critical patent/CA3289739A1/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic 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
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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
    • A61P9/10—Drugs 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic 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
    • C07C233/17—Carboxylic 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
    • C07C233/18—Carboxylic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic 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
    • C07D307/18—Heterocyclic 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
    • C07D307/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic 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
    • C07D309/08—Heterocyclic 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
    • C07D309/10—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic 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
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic 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
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/16—Benzo[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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • 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)
CA3289739A 2014-06-24 2015-06-24 Biphenyl amides with modified ether groups as hsp90 inhibitors and hsp70 inducers Pending CA3289739A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201462016473P 2014-06-24 2014-06-24
CA2952029A CA2952029C (en) 2014-06-24 2015-06-24 Biphenyl amides with modified ether groups as hsp90 inhibitors and hsp70 inducers

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2952029A Division CA2952029C (en) 2014-06-24 2015-06-24 Biphenyl amides with modified ether groups as hsp90 inhibitors and hsp70 inducers

Publications (1)

Publication Number Publication Date
CA3289739A1 true CA3289739A1 (en) 2025-11-29

Family

ID=53525293

Family Applications (2)

Application Number Title Priority Date Filing Date
CA3289739A Pending CA3289739A1 (en) 2014-06-24 2015-06-24 Biphenyl amides with modified ether groups as hsp90 inhibitors and hsp70 inducers
CA2952029A Active CA2952029C (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
CA2952029A Active CA2952029C (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
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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
SG10201811574YA (en) 2019-01-30
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
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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