AU2018231120B2 - Indole derivatives as efflux pump inhibitors - Google Patents

Indole derivatives as efflux pump inhibitors Download PDF

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Publication number
AU2018231120B2
AU2018231120B2 AU2018231120A AU2018231120A AU2018231120B2 AU 2018231120 B2 AU2018231120 B2 AU 2018231120B2 AU 2018231120 A AU2018231120 A AU 2018231120A AU 2018231120 A AU2018231120 A AU 2018231120A AU 2018231120 B2 AU2018231120 B2 AU 2018231120B2
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Australia
Prior art keywords
alkyl
carbocyclyl
hydrogen
aryl
halo
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AU2018231120A
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AU2018231120A1 (en
Inventor
Edmond J. Lavoie
Ajit Parhi
Yangsheng SUN
Yi Yuan
Yongzheng Zhang
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Rutgers, The State University of New Jersey
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Rutgers, The State University of New Jersey
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond

Landscapes

  • 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)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
AU2018231120A 2017-03-10 2018-03-09 Indole derivatives as efflux pump inhibitors Active AU2018231120B2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201762469987P 2017-03-10 2017-03-10
US62/469,987 2017-03-10
US201762523154P 2017-06-21 2017-06-21
US62/523,154 2017-06-21
PCT/US2018/021848 WO2018165611A1 (en) 2017-03-10 2018-03-09 Indole derivatives as efflux pump inhibitors

Publications (2)

Publication Number Publication Date
AU2018231120A1 AU2018231120A1 (en) 2019-10-31
AU2018231120B2 true AU2018231120B2 (en) 2022-06-23

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Application Number Title Priority Date Filing Date
AU2018231120A Active AU2018231120B2 (en) 2017-03-10 2018-03-09 Indole derivatives as efflux pump inhibitors

Country Status (12)

Country Link
US (1) US11993571B2 (enExample)
EP (1) EP3592736A1 (enExample)
JP (1) JP7323179B2 (enExample)
KR (1) KR102697360B1 (enExample)
CN (1) CN110770224B (enExample)
AU (1) AU2018231120B2 (enExample)
BR (1) BR112019018691A2 (enExample)
CA (1) CA3061238A1 (enExample)
IL (1) IL269210B2 (enExample)
MX (1) MX2019010717A (enExample)
SG (1) SG11201908351TA (enExample)
WO (1) WO2018165611A1 (enExample)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10556854B2 (en) 2016-02-24 2020-02-11 Rutgers, The State University Of New Jersey Bacterial efflux pump inhibitors
US10836706B2 (en) 2016-02-24 2020-11-17 Rutgers, The State University Of New Jersey Bacterial efflux pump inhibitors
WO2018165614A1 (en) 2017-03-10 2018-09-13 Rutgers, The State University Of New Jersey Bacterial efflux pump inhibitors
EP3592736A1 (en) 2017-03-10 2020-01-15 Rutgers, the State University of New Jersey Indole derivatives as efflux pump inhibitors
WO2018165612A1 (en) 2017-03-10 2018-09-13 Rutgers, The State University Of New Jersey Bacterial efflux pump inhibitors
CN111163774A (zh) 2017-05-26 2020-05-15 罗格斯新泽西州立大学 细菌外排泵抑制剂
US11458121B2 (en) 2017-06-26 2022-10-04 Rutgers, The State University Of New Jersey Therapeutic compounds and methods to treat infection
WO2019099402A1 (en) * 2017-11-14 2019-05-23 Rutgers, The State University Of New Jersey Therapeutic compounds and methods to treat infection
KR102704123B1 (ko) 2019-11-01 2024-09-06 에스엘 주식회사 차량용 램프
CN121695288A (zh) 2020-02-19 2026-03-20 Epizyme股份有限公司 Setd2抑制剂和相关方法和用途，包括组合疗法
EP4766445A1 (en) 2023-08-23 2026-07-01 Taxis Pharmaceuticals, Inc. BACTERIAL EFFLUX PUMP INHIBITORS
EP4770630A1 (en) * 2023-08-29 2026-07-08 Maze Therapeutics, Inc. Inhibitors of solute carrier family 6a member 19 (slc6a19) and methods of use thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003000657A1 (en) * 2001-06-20 2003-01-03 Daiichi Pharmaceutical Co., Ltd. Diamine derivatives
US20070155721A1 (en) * 2004-02-11 2007-07-05 Rene Hersperger Chemokine receptor antagonists
WO2007115231A2 (en) * 2006-03-30 2007-10-11 Chemocentryx, Inc. Cxcr4 modulators
WO2008012782A2 (en) * 2006-07-27 2008-01-31 Institut National De La Sante Et De La Recherche Medicale (Inserm) Labelled analogues of halobenzamides as radiopharmaceuticals
WO2009103552A1 (en) * 2008-02-22 2009-08-27 Grünenthal GmbH Substituted indole derivatives
WO2016040505A1 (en) * 2014-09-10 2016-03-17 Epizyme, Inc. Smyd inhibitors

Family Cites Families (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3238215A (en) * 1963-10-17 1966-03-01 Sterling Drug Inc 1-[(3-, 2-, and 1-indolyl)-lower-alkyl-, lower-alkenyl-, and lower-alkynyl]piperidines
US3465080A (en) * 1968-10-07 1969-09-02 American Cyanamid Co Therapeutic compositions containing morpholinoalkylene - indoles and methods of administering such in the treatment of depression
US3978224A (en) 1975-07-01 1976-08-31 Schering Corporation Antimicrobial halo-substituted-2-cyanoethylaminoalkyl-3-phenyl-indoles
US4910193A (en) * 1985-12-16 1990-03-20 Sandoz Ltd. Treatment of gastrointestinal disorders
US4938949A (en) 1988-09-12 1990-07-03 University Of New York Treatment of damaged bone marrow and dosage units therefor
AU8501291A (en) 1990-09-10 1992-03-30 Upjohn Company, The Cis-n-(2-aminocyclohexyl)benzamide and their enantiomers as anticonvulsants
US5864039A (en) * 1994-03-30 1999-01-26 Yoshitomi Pharmaceutical Industries, Ltd. Benzoic acid compounds and use thereof as medicaments
US5663152A (en) 1995-01-19 1997-09-02 Asahi Kasei Kogyo Kabushiki Kaisha Potentiators for aminoglycosides
US6506339B1 (en) * 1997-02-10 2003-01-14 Biomedical Design, Inc. Method of sterilization
AU2337599A (en) * 1998-01-23 1999-08-09 Microcide Pharmaceuticals, Inc. Efflux pump inhibitors
US6204279B1 (en) 1998-06-03 2001-03-20 Microcide Pharmaceuticals, Inc. Peptidomimetic efflux pump inhibitors
AU757777B2 (en) 1998-12-04 2003-03-06 Influx, Inc. Inhibitors of multidrug transporters
JP4831907B2 (ja) 1999-10-08 2011-12-07 アフィニアム・ファーマシューティカルズ・インコーポレイテッド ＦａｂＩ阻害剤
US6730684B1 (en) 1999-10-08 2004-05-04 Affinium Pharmaceuticals, Inc. Fab I inhibitors
US6555569B2 (en) 2000-03-07 2003-04-29 Pfizer Inc. Use of heteroaryl substituted N-(indole-2-carbonyl-) amides for treatment of infection
HUP0103986A2 (hu) * 2001-09-28 2003-06-28 Richter Gedeon Vegyészeti Gyár Rt. Új karbonsavamid szerkezetet tartalmazó piperidinil vegyületek, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények
EP1314733A1 (en) * 2001-11-22 2003-05-28 Aventis Pharma Deutschland GmbH Indole-2-carboxamides as factor Xa inhibitors
WO2004062674A2 (en) 2003-01-07 2004-07-29 Paratek Pharmaceuticals, Inc. Substituted polyamines as inhibitors of bacterial efflux pumps
US7994225B2 (en) 2004-03-17 2011-08-09 Rempex Pharmaceuticals, Inc. Bacterial efflux pump inhibitors for the treatment of ophthalmic and otic infections
EP1758920A1 (en) 2004-05-21 2007-03-07 Mpex Pharmaceuticals, Inc. Bacterial efflux pump inhibitors and methods of treating bacterial infections
EP1817025A2 (en) 2004-11-23 2007-08-15 PTC Therapeutics, Inc. Tetrahydrocarbazoles as active agents for inhibiting vegf production by translational control
US7855228B2 (en) 2005-02-10 2010-12-21 The Board Of Trustees Of The Leland Stamford Junior University Antibiotics targeting MreB
CA3144493A1 (en) 2006-10-03 2008-04-10 Arbutus Biopharma Corporation Lipid containing formulations
WO2009110002A1 (en) 2008-03-05 2009-09-11 Council Of Scientific & Industrial Research Novel efflux pump inhibitors
US20110237578A1 (en) 2008-09-18 2011-09-29 Zhi-Liang Wei Amide compounds, compositions and uses thereof
US8173636B2 (en) 2009-04-03 2012-05-08 Achillion Pharmaceuticals, Inc. Hydroxylthienoquinolones and related compounds as anti-infective agents
EP2536408A1 (en) 2010-02-16 2012-12-26 Wockhardt Research Centre Efflux pump inhibitors
EP2394653A1 (en) * 2010-05-26 2011-12-14 Almirall, S.A. Topical pharmaceutical compositions comprising mometasone furoate
FR2969150B1 (fr) 2010-12-20 2013-07-26 Centre Nat Rech Scient Nouvelles molecules indoliques demontrant des activites antibacteriennes dans une variete de bacteries a gram-negatif et positif dont des bacteries multidrogues-resistantes
BR112015004666B1 (pt) 2012-09-07 2022-04-26 Novartis Ag Derivados de indol carboxamida, seu uso, e composição farmacêutica
CA2890748A1 (en) 2012-11-13 2014-05-22 Memorial Sloan-Kettering Cancer Center Indole compounds and their use as antimicrobials
US20170044100A1 (en) * 2014-04-22 2017-02-16 The Johns Hopkins University Inhibitors of drug-resistant mycobacterium tuberculosis
US9926261B2 (en) 2015-03-10 2018-03-27 Rutgers, The State University Of New Jersey Bacterial efflux pump inhibitors
US9950993B2 (en) 2015-03-13 2018-04-24 Rutgers, The State University Of New Jersey Bacterial efflux pump inhibitors
CN107709314A (zh) 2015-06-11 2018-02-16 巴斯利尔药物国际股份公司 外排泵抑制剂及其治疗性用途
EP3331530A4 (en) 2015-08-03 2018-12-19 Raze Therapeutics Inc. Mthfd2 inhibitors and uses thereof
US10836706B2 (en) 2016-02-24 2020-11-17 Rutgers, The State University Of New Jersey Bacterial efflux pump inhibitors
US10556854B2 (en) 2016-02-24 2020-02-11 Rutgers, The State University Of New Jersey Bacterial efflux pump inhibitors
EP4306166A3 (en) 2016-12-23 2024-06-26 Aquinnah Pharmaceuticals Inc. Compounds, compositions and methods of use
WO2018165612A1 (en) 2017-03-10 2018-09-13 Rutgers, The State University Of New Jersey Bacterial efflux pump inhibitors
EP3592736A1 (en) 2017-03-10 2020-01-15 Rutgers, the State University of New Jersey Indole derivatives as efflux pump inhibitors
WO2018165614A1 (en) 2017-03-10 2018-09-13 Rutgers, The State University Of New Jersey Bacterial efflux pump inhibitors
CN111163774A (zh) 2017-05-26 2020-05-15 罗格斯新泽西州立大学 细菌外排泵抑制剂
US11458121B2 (en) * 2017-06-26 2022-10-04 Rutgers, The State University Of New Jersey Therapeutic compounds and methods to treat infection
US20190031624A1 (en) 2017-07-28 2019-01-31 Rutgers, The State University Of New Jersey Therapeutic compounds and methods to treat infection
WO2019099402A1 (en) * 2017-11-14 2019-05-23 Rutgers, The State University Of New Jersey Therapeutic compounds and methods to treat infection

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003000657A1 (en) * 2001-06-20 2003-01-03 Daiichi Pharmaceutical Co., Ltd. Diamine derivatives
US20070155721A1 (en) * 2004-02-11 2007-07-05 Rene Hersperger Chemokine receptor antagonists
WO2007115231A2 (en) * 2006-03-30 2007-10-11 Chemocentryx, Inc. Cxcr4 modulators
WO2008012782A2 (en) * 2006-07-27 2008-01-31 Institut National De La Sante Et De La Recherche Medicale (Inserm) Labelled analogues of halobenzamides as radiopharmaceuticals
WO2009103552A1 (en) * 2008-02-22 2009-08-27 Grünenthal GmbH Substituted indole derivatives
WO2016040505A1 (en) * 2014-09-10 2016-03-17 Epizyme, Inc. Smyd inhibitors

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
CAS Registry Number 1566604-70-3; Entry Date 2014-03-11; 1H-Indole-2-carboxamide, 4-chloro-N-[(3R,5S)-5-[(diethylamino)carbonyl]-1-methyl-3-pyrrolidinyl] *
CAS Registry Number 1626576-60-0; Entry Date 2014-09-26; 1H-Indole-2-carboxamide, 6-bromo-4-fluoro-N-(1-methyl-4-piperidinyl)-N-(2-methylpropyl) *
CAS Registry Number 1788589-70-7; Entry Date 2015-06-25; 1H-Indole-2-carboxamide, N-(2-aminopropyl)-4-fluoro-1-methyl *
CAS Registry Number 1957085-66-3; Entry Date 2016-07-21; 1H-Indole-2-carboxamide, N-(2-cyclopropyltetrahydro-2H-pyran-4-yl)-7-fluoro-4-methoxy *
CAS Registry Number 1978423-07-2; Entry Date 2016-08-24; N-[(1-aminocyclobutyl)methyl]-1H-Indole-2-carboxamide *
CAS Registry Number 2058714-02-4; Entry Date 2017-01-25; 1H-Indole-3-acetamide, 5-fluoro-2-methyl-N-[(3R,4R)-tetrahydro-4-(1-piperidinyl)-3-furanyl] *
NAGARAJAN, G. et al., "Effect of H4R antagonist N-(2-aminoethyl)-5-chloro-1H-indol-2-carboxamides and 5-chloro-2-(piperazin-1-ylmethyl)-1H-benzimidazole ..", Journal of Receptors and Signal Transduction, 2017, vol. 37, no. 3, p304–313 *
NAGARAJAN, G. et al., "Effect of H4R antagonist N-(2-aminoethyl)-5-chloro-1H-indol-2-carboxamides and 5-chloro-2-(piperazin-1-ylmethyl)-1H-benzimidazole on histamine and... ", JNL of Receptors and Signal Transduction, 2017, 37, 3, p304–13 *
NAGARAJAN, G. et al., Journal of Receptors and Signal Transduction, 2017 (published online 03-11-2016), vol. 37, no. 3, pages 304–313 *
NAGARAJAN, G. et al., Journal of Receptors and Signal Transduction, 2017, vol. 37, no. 3, pages 304–313 *
WENZLER, T. et al., "A new approach to chemotherapy: drug-induced differentiation kills African trypanosomes", Scientific Reports, 2016, vol. 6, no. 22451, pages 1–10 *

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Publication number Publication date
AU2018231120A1 (en) 2019-10-31
SG11201908351TA (en) 2019-10-30
IL269210A (en) 2019-11-28
JP2020510044A (ja) 2020-04-02
CN110770224B (zh) 2022-11-18
US20210094912A1 (en) 2021-04-01
BR112019018691A2 (pt) 2020-04-07
CN110770224A (zh) 2020-02-07
EP3592736A1 (en) 2020-01-15
JP7323179B2 (ja) 2023-08-08
KR20190138790A (ko) 2019-12-16
MX2019010717A (es) 2019-12-05
IL269210B2 (en) 2025-05-01
CA3061238A1 (en) 2018-09-13
WO2018165611A1 (en) 2018-09-13
US11993571B2 (en) 2024-05-28
IL269210B1 (en) 2025-01-01
KR102697360B1 (ko) 2024-08-20

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