CN111372579B - 取代的苯基磺酰基苯基三唑硫酮和其用途 - Google Patents
取代的苯基磺酰基苯基三唑硫酮和其用途 Download PDFInfo
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- CN111372579B CN111372579B CN201880071304.3A CN201880071304A CN111372579B CN 111372579 B CN111372579 B CN 111372579B CN 201880071304 A CN201880071304 A CN 201880071304A CN 111372579 B CN111372579 B CN 111372579B
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- Prior art keywords
- compound
- alkyl
- pharmaceutically acceptable
- acceptable salt
- substituted
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- BHAVOZDSGFLVBI-UHFFFAOYSA-N 5-[2-(benzenesulfonyl)phenyl]triazole-4-thione Chemical class C1(=CC=CC=C1)S(=O)(=O)C1=C(C=CC=C1)C=1C(N=NN=1)=S BHAVOZDSGFLVBI-UHFFFAOYSA-N 0.000 title abstract 2
- 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims 38
- 150000003839 salts Chemical class 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 4
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 4
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 4
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- -1 Alkyl radicals Chemical class 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 238000010922 spray-dried dispersion Methods 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
- 108010010803 Gelatin Proteins 0.000 claims 1
- 229920000881 Modified starch Polymers 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 108010009736 Protein Hydrolysates Proteins 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 239000008121 dextrose Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229920000159 gelatin Polymers 0.000 claims 1
- 239000008273 gelatin Substances 0.000 claims 1
- 235000019322 gelatine Nutrition 0.000 claims 1
- 235000011852 gelatine desserts Nutrition 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 1
- 239000012985 polymerization agent Substances 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
-
- 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
- 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
- C07D403/10—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 carbon chain containing aromatic rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dispersion Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201762579070P | 2017-10-30 | 2017-10-30 | |
US62/579,070 | 2017-10-30 | ||
US201762584630P | 2017-11-10 | 2017-11-10 | |
US62/584,630 | 2017-11-10 | ||
PCT/US2018/058050 WO2019089478A1 (en) | 2017-10-30 | 2018-10-29 | Substituted phenyl sulfonyl phenyl triazole thiones and uses thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN111372579A CN111372579A (zh) | 2020-07-03 |
CN111372579B true CN111372579B (zh) | 2023-08-22 |
Family
ID=66333645
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201880071304.3A Active CN111372579B (zh) | 2017-10-30 | 2018-10-29 | 取代的苯基磺酰基苯基三唑硫酮和其用途 |
Country Status (12)
Country | Link |
---|---|
US (4) | US10501423B2 (en:Method) |
EP (1) | EP3703675A4 (en:Method) |
JP (2) | JP7277473B2 (en:Method) |
KR (1) | KR102639231B1 (en:Method) |
CN (1) | CN111372579B (en:Method) |
AU (1) | AU2018359224B2 (en:Method) |
BR (1) | BR112020008727A2 (en:Method) |
CA (1) | CA3080578A1 (en:Method) |
IL (1) | IL274010B2 (en:Method) |
MX (1) | MX2020004202A (en:Method) |
SG (1) | SG11202003879RA (en:Method) |
WO (1) | WO2019089478A1 (en:Method) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA3080578A1 (en) | 2017-10-30 | 2019-05-09 | Neuropore Therapies, Inc. | Substituted phenyl sulfonyl phenyl triazole thiones and uses thereof |
JP2021527692A (ja) * | 2018-06-20 | 2021-10-14 | ニューロポア セラピーズ インコーポレイテッド | Oat3の阻害剤を用いた神経変性に関連する状態の処置方法 |
CN117384029B (zh) * | 2023-12-12 | 2024-02-20 | 山东国邦药业有限公司 | 一种2,4,5-三氟苯乙酸的合成方法 |
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GB1476503A (en) | 1973-06-21 | 1977-06-16 | Sterling Drug Inc | 1-arylamino-and 1-arylimino-pyrroles and preparation thereof |
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DE3307506A1 (de) | 1983-03-03 | 1984-09-06 | Agfa-Gevaert Ag, 5090 Leverkusen | Fotografisches aufzeichnungsmaterial mit inhibitorvorlaeuferverbindungen |
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DE10123586A1 (de) * | 2001-05-08 | 2002-11-28 | Schering Ag | 3,5-Diamino-1,2,4-triazole als Kinase Inhibitoren |
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RU2223952C2 (ru) | 2001-06-04 | 2004-02-20 | Институт физиологически активных веществ РАН | Производные n,s-замещенных n'-1-[(гетеро)арил]-n'-[(гетеро)арил]метилизотиомочевин или их солей с фармакологически приемлемыми кислотами нх, способы получения их солей и оснований, фармацевтическая композиция, способ лечения и способ изучения глутаматэргической системы |
EP2168576A3 (en) | 2001-09-14 | 2010-05-26 | Shionogi & Co., Ltd. | Tricyclic compounds for treating dyslipidemia and arteriosclerotic diseases |
SE0301232D0 (sv) * | 2003-04-25 | 2003-04-25 | Astrazeneca Ab | Novel use |
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2018
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- 2018-10-29 BR BR112020008727-0A patent/BR112020008727A2/pt unknown
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2019
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US20200123116A1 (en) | 2020-04-23 |
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KR20200083545A (ko) | 2020-07-08 |
BR112020008727A2 (pt) | 2020-10-20 |
IL274010B1 (en) | 2023-03-01 |
IL274010A (en) | 2020-05-31 |
KR102639231B1 (ko) | 2024-02-22 |
WO2019089478A1 (en) | 2019-05-09 |
JP7277473B2 (ja) | 2023-05-19 |
JP2021501202A (ja) | 2021-01-14 |
AU2018359224B2 (en) | 2023-10-05 |
SG11202003879RA (en) | 2020-05-28 |
US20190292158A1 (en) | 2019-09-26 |
IL274010B2 (en) | 2023-07-01 |
AU2018359224A1 (en) | 2020-06-18 |
US20230391734A1 (en) | 2023-12-07 |
EP3703675A1 (en) | 2020-09-09 |
US10501423B2 (en) | 2019-12-10 |
EP3703675A4 (en) | 2021-06-16 |
CA3080578A1 (en) | 2019-05-09 |
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