SG11201909418WA - Small molecule inhibitors of bcl-2-associated death promoter (bad) phosphorylation - Google Patents

Small molecule inhibitors of bcl-2-associated death promoter (bad) phosphorylation

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Publication number
SG11201909418WA
SG11201909418WA SG11201909418WA SG11201909418WA SG 11201909418W A SG11201909418W A SG 11201909418WA SG 11201909418W A SG11201909418W A SG 11201909418WA SG 11201909418W A SG11201909418W A SG 11201909418WA
Authority
SG
Singapore
Prior art keywords
cancer
mysore
university
singapore
bangalore
Prior art date
Application number
Inventor
Peter Edward Lobie
Vijay Kumar Pandey
Subbegowda Rangappa Kanchugarakoppal
Bassappa Salundi
Dhananjaya Mohan Chakrabhavi
Shobith RANGAPPA
Srinivasa Venkatachalaiah
Original Assignee
Nat Univ Singapore
Univ Of Mysore
Bangalore Univ
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.)
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Application filed by Nat Univ Singapore, Univ Of Mysore, Bangalore Univ filed Critical Nat Univ Singapore
Publication of SG11201909418WA publication Critical patent/SG11201909418WA/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • 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
    • A61K31/495—Heterocyclic 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
    • 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
    • A61K31/495—Heterocyclic 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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic 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
    • C07D213/24—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • 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
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D471/06—Peri-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Management, Administration, Business Operations System, And Electronic Commerce (AREA)
  • Professional, Industrial, Or Sporting Protective Garments (AREA)

Abstract

INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 25 October 2018 (25.10.2018) WIPO I PCT omit VIII °nolo VIII VIII 11011111° oimIE (10) International Publication Number WO 2018/194520 Al (51) International Patent Classification: CO7D 211/06 (2006.01) A61K 31/496 (2006.01) CO7D 241/04 (2006.01) A61P 35/00 (2006.01) A61K 31/445 (2006.01) (21) International Application Number: PCT/SG2018/050194 (22) International Filing Date: Central College Campus, Palace Road, Bangalore 560001 (IN). (74) Agent: AMICA LAW LLC; 30 Raffles Place, #14-01 Chevron House, Singapore 048622 (SG). (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). Declarations under Rule 4.17: — of inventorship (Rule 4.17(iv)) Published: — with international search report (Art. 21(3)) — in black and white; the international application as filed contained color or greyscale and is available for download from PATENTSCOPE 18 April 2018 (18.04.2018) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 1706162.3 19 April 2017 (19.04.2017) GB (71) Applicants: NATIONAL UNIVERSITY OF SINGA- PORE [SG/SG]; 21 Lower Kent Ridge Road, Singa- pore 119077 (SG). UNIVERSITY OF MYSORE [IN/IN]; Manasagangotri, Mysore 570006 (IN). BANGALORE UNIVERSITY [IN/IN]; Central College Campus, Palace Road, Bangalore 560001 (IN). = (72) Inventors: LOBIE, Peter Edward; c/o National Uni- versity of Singapore, Cancer Science Institute of Sin- gapore, 21 Lower Kent Ridge Road, Singapore 119077 (SG). PANDEY, Vijay Kumar; c/o National Universi- ty of Singapore, Cancer Science Institute of Singapore, 21 Lower Kent Ridge Road, Singapore 119077 (SG). KANCHUGARAKOPPAL SUBBEGOWDA, Rangap- pa; c/o University of Mysore, Department of Stud- ies in Chemistry, Manasagangotri, Mysore 570006 (IN). SALUNDI, Bassappa; c/o Bangalore University, Depart- ment of Chemistry, Central College Campus, Palace Road, Bangalore 560001 (IN). CHAKRABHAVI DHANAN- JAYA, Mohan; c/o University of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570006 (IN). RANGAPPA, Shobith; c/o University of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570006 (IN). VENKATACHALAIAH, Srini- vasa; c/o Bangalore University, Department of Chemistry, W O 20 18/ 19 45 20 Al (54) Title: SMALL MOLECULE INHIBITORS OF BCL-2-ASSOCIATED DEATH PROMOTER (BAD) PHOSPHORYLATION Rza R2b (R 1 ) n (57) : The invention relates to compounds of general formula (I): wherein R 1 , n, R 2a , R 2b , and R 3 are as defined herein. The compounds are inhibitors of Bc1-2-associated death promoter (BAD) phosphorylation and have anti-apoptotic activity and are useful in the treatment of cancer, particularly breast cancer, endometrial cancer, ovarian cancer, liver cancer, colon cancer, prostate cancer or pancreatic cancer.
SG11201909418W 2017-04-19 2018-04-18 Small molecule inhibitors of bcl-2-associated death promoter (bad) phosphorylation SG11201909418WA (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB1706162.3A GB201706162D0 (en) 2017-04-19 2017-04-19 Compounds
PCT/SG2018/050194 WO2018194520A1 (en) 2017-04-19 2018-04-18 Small molecule inhibitors of bcl-2-associated death promoter (bad) phosphorylation

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SG11201909418WA true SG11201909418WA (en) 2019-11-28

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US (1) US11292773B2 (en)
EP (1) EP3612518A4 (en)
JP (1) JP7423010B2 (en)
KR (1) KR20200029384A (en)
CN (1) CN110719906B (en)
AU (1) AU2018256285B2 (en)
BR (1) BR112019022015A2 (en)
CA (1) CA3060939A1 (en)
GB (1) GB201706162D0 (en)
IL (1) IL270078B (en)
SG (1) SG11201909418WA (en)
WO (1) WO2018194520A1 (en)

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GB201706162D0 (en) * 2017-04-19 2017-05-31 Nat Univ Singapore Compounds
CN112481298A (en) * 2020-11-11 2021-03-12 清华-伯克利深圳学院筹备办公室 Recombinant plasmid and application thereof
CN115340527B (en) * 2021-05-13 2023-09-15 成都先导药物开发股份有限公司 BCL-XL inhibitor and preparation method and application thereof

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KR100578455B1 (en) 1998-06-25 2006-05-10 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 Process for the preparation of 3-aryl-benzofuranones
US6262066B1 (en) 1998-07-27 2001-07-17 Schering Corporation High affinity ligands for nociceptin receptor ORL-1
DE10348044A1 (en) 2003-10-15 2005-05-19 Imtm Gmbh Dual alanyl aminopeptidase and dipeptidyl peptidase IV inhibitors for the functional influence of different cells and for the treatment of immunological, inflammatory, neuronal and other diseases
US8252832B2 (en) * 2007-12-14 2012-08-28 Novartis Ag Kinesin inhibitors as cancer therapeutics
WO2010052448A2 (en) 2008-11-05 2010-05-14 Ucb Pharma S.A. Fused pyrazine derivatives as kinase inhibitors
US8916705B2 (en) * 2011-10-14 2014-12-23 The Board of Trustees of The University of Illilnois Procaspase-activating compounds and compositions
JP2017128541A (en) 2016-01-21 2017-07-27 学校法人東京女子医科大学 Apoptosis inducer
GB201706162D0 (en) * 2017-04-19 2017-05-31 Nat Univ Singapore Compounds

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JP2020517745A (en) 2020-06-18
RU2019135562A (en) 2021-05-19
RU2019135562A3 (en) 2021-07-21
KR20200029384A (en) 2020-03-18
CN110719906A (en) 2020-01-21
EP3612518A1 (en) 2020-02-26
JP7423010B2 (en) 2024-01-29
CN110719906B (en) 2023-07-28
WO2018194520A1 (en) 2018-10-25
AU2018256285A1 (en) 2019-11-07
WO2018194520A9 (en) 2019-10-17
CA3060939A1 (en) 2018-10-25
IL270078A (en) 2019-12-31
US11292773B2 (en) 2022-04-05
BR112019022015A2 (en) 2020-05-12
US20200131139A1 (en) 2020-04-30
EP3612518A4 (en) 2020-11-25
GB201706162D0 (en) 2017-05-31
AU2018256285B2 (en) 2022-08-04

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