AU2021226747A1 - Compounds and methods of use - Google Patents

Info

Publication number

AU2021226747A1

AU2021226747A1 AU2021226747A AU2021226747A AU2021226747A1 AU 2021226747 A1 AU2021226747 A1 AU 2021226747A1 AU 2021226747 A AU2021226747 A AU 2021226747A AU 2021226747 A AU2021226747 A AU 2021226747A AU 2021226747 A1 AU2021226747 A1 AU 2021226747A1

Authority

AU

Australia

Prior art keywords

carboxamide

naphthyridin

alkylene

oxy

alkyl

Prior art date

2020-02-24

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 286
• 238000000034 method Methods 0.000 title claims abstract description 62
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 12
• 108060006633 protein kinase Proteins 0.000 claims abstract description 12
• 230000001404 mediated effect Effects 0.000 claims abstract description 7
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 421
• 125000002947 alkylene group Chemical group 0.000 claims description 370
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 271
• 125000001424 substituent group Chemical group 0.000 claims description 194
• 125000001072 heteroaryl group Chemical group 0.000 claims description 162
• 150000003839 salts Chemical class 0.000 claims description 131
• -1 1H-pyrazol-3-yl Chemical group 0.000 claims description 129
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 122
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 98
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 97
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 96
• 125000005843 halogen group Chemical group 0.000 claims description 93
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 90
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 83
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 81
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 77
• 229910052702 rhenium Inorganic materials 0.000 claims description 72
• 125000004429 atom Chemical group 0.000 claims description 71
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 66
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 64
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 63
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 61
• 125000004432 carbon atom Chemical group C* 0.000 claims description 56
• 201000010099 disease Diseases 0.000 claims description 55
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 54
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 49
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 125000005842 heteroatom Chemical group 0.000 claims description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 208000035475 disorder Diseases 0.000 claims description 35
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 30
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 26
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 24
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
• 125000006239 protecting group Chemical group 0.000 claims description 20
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
• ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 238000001727 in vivo Methods 0.000 claims description 14
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 13
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 13
• 230000000694 effects Effects 0.000 claims description 13
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 12
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
• 229910017711 NHRa Inorganic materials 0.000 claims description 12
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
• 208000011580 syndromic disease Diseases 0.000 claims description 6
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 229920002554 vinyl polymer Polymers 0.000 claims description 4
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• JZMMZVZTTYZPKX-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=CC=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=CC=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O JZMMZVZTTYZPKX-UHFFFAOYSA-N 0.000 claims description 3
• QXKOHFSERWNKOJ-UHFFFAOYSA-N FC=1C=C(C=CC=1OC1=CC=NC2=CC(=CN=C12)OC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O Chemical compound FC=1C=C(C=CC=1OC1=CC=NC2=CC(=CN=C12)OC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O QXKOHFSERWNKOJ-UHFFFAOYSA-N 0.000 claims description 3
• YYGCNDALBLEAHC-UHFFFAOYSA-N FC=1C=C(C=CC=1OC1=CC=NC2=CC=C(N=C12)OC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O Chemical compound FC=1C=C(C=CC=1OC1=CC=NC2=CC=C(N=C12)OC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O YYGCNDALBLEAHC-UHFFFAOYSA-N 0.000 claims description 3
• VKLHKXQQQQLKFW-UHFFFAOYSA-N FC=1C=CC(=NC=1)N1C(C(=CC=C1C)C(=O)NC1=CC=C(C=C1)OC1=CC=NC2=CC(=CN=C12)OC)=O Chemical compound FC=1C=CC(=NC=1)N1C(C(=CC=C1C)C(=O)NC1=CC=C(C=C1)OC1=CC=NC2=CC(=CN=C12)OC)=O VKLHKXQQQQLKFW-UHFFFAOYSA-N 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 125000006352 iso-propylthiomethyl group Chemical group [H]C([H])([H])C([H])(SC([H])([H])*)C([H])([H])[H] 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
• 229910052701 rubidium Inorganic materials 0.000 claims description 2
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
• JRYYVMDEUJQWRO-UHFFFAOYSA-N 2-methylnicotinamide Chemical compound CC1=NC=CC=C1C(N)=O JRYYVMDEUJQWRO-UHFFFAOYSA-N 0.000 claims 1
• KCNQARIQPHGIDQ-UHFFFAOYSA-N 6-methyl-2-oxo-1h-pyridine-3-carboxamide Chemical compound CC1=CC=C(C(N)=O)C(=O)N1 KCNQARIQPHGIDQ-UHFFFAOYSA-N 0.000 claims 1
• WRRAGWMDUHXSGV-UHFFFAOYSA-N BrC=1C=C(C(N(C=1C)C1=NC=C(C=C1)F)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F Chemical compound BrC=1C=C(C(N(C=1C)C1=NC=C(C=C1)F)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F WRRAGWMDUHXSGV-UHFFFAOYSA-N 0.000 claims 1
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• BAUVLJGZLDHLJX-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C1=NC(=C(N=C1)C)C=1OC=CC=1)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C1=NC(=C(N=C1)C)C=1OC=CC=1)F BAUVLJGZLDHLJX-UHFFFAOYSA-N 0.000 claims 1
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• YCHBZBDEGJSENQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C1=NC=CN(C1=O)C1=NC=C(C=C1)F)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C1=NC=CN(C1=O)C1=NC=C(C=C1)F)F YCHBZBDEGJSENQ-UHFFFAOYSA-N 0.000 claims 1
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• RFRQTOXIHVPNHB-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=COC=C1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=COC=C1)C)C)F RFRQTOXIHVPNHB-UHFFFAOYSA-N 0.000 claims 1
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• ZYMPUZQVOUJIPC-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC(=CC=C1)C)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC(=CC=C1)C)C)COC)F ZYMPUZQVOUJIPC-UHFFFAOYSA-N 0.000 claims 1
• ZMTXBLJYWFUGGL-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=C(C=C1)F)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=C(C=C1)F)C)C)F ZMTXBLJYWFUGGL-UHFFFAOYSA-N 0.000 claims 1
• PMXLNVRCGZRRCI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=C(C=C1)F)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=C(C=C1)F)C)COC)F PMXLNVRCGZRRCI-UHFFFAOYSA-N 0.000 claims 1
• NRKPZVPSOAWZRK-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=CC=C1)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=CC=C1)C)COC)F NRKPZVPSOAWZRK-UHFFFAOYSA-N 0.000 claims 1
• XTXWWQATYWKIRG-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=CC=C1C)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=CC=C1C)C)COC)F XTXWWQATYWKIRG-UHFFFAOYSA-N 0.000 claims 1
• NZBULONFLIMTFF-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=C(C=1)C(F)(F)F)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=C(C=1)C(F)(F)F)C)C)C)F NZBULONFLIMTFF-UHFFFAOYSA-N 0.000 claims 1
• YAYPSEHENYFRMO-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=C(C=1)C)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=C(C=1)C)C)C)C)F YAYPSEHENYFRMO-UHFFFAOYSA-N 0.000 claims 1
• XHOLEZFIHKUXQM-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=CC=1)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=CC=1)C)C)C)F XHOLEZFIHKUXQM-UHFFFAOYSA-N 0.000 claims 1
• ZLILHVHPHQIFNH-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C(C)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C(C)C)C)C)F ZLILHVHPHQIFNH-UHFFFAOYSA-N 0.000 claims 1
• IDBDLBJTXXUNNF-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C)C)C)F IDBDLBJTXXUNNF-UHFFFAOYSA-N 0.000 claims 1
• NTUBTAFVRFOTKB-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C)C)COC)F NTUBTAFVRFOTKB-UHFFFAOYSA-N 0.000 claims 1
• WBWJWWLNCBKNEE-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)CC)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)CC)C)C)F WBWJWWLNCBKNEE-UHFFFAOYSA-N 0.000 claims 1
• YFIFHLLPPDAGOR-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC=CC=1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC=CC=1)C)C)F YFIFHLLPPDAGOR-UHFFFAOYSA-N 0.000 claims 1
• ACXICGZPGAFENQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC=CC=1)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC=CC=1)C)COC)F ACXICGZPGAFENQ-UHFFFAOYSA-N 0.000 claims 1
• FQDZTNLTAQVKMH-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC(=CC=1)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC(=CC=1)C)C)C)F FQDZTNLTAQVKMH-UHFFFAOYSA-N 0.000 claims 1
• AYVRNMNTNVVTAQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=C(C=1)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=C(C=1)C)C)C)F AYVRNMNTNVVTAQ-UHFFFAOYSA-N 0.000 claims 1
• SOXSIADXNGIVSR-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1)C)C)F SOXSIADXNGIVSR-UHFFFAOYSA-N 0.000 claims 1
• SAFRJKACTVWZNI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1)C)COC)F SAFRJKACTVWZNI-UHFFFAOYSA-N 0.000 claims 1
• XPPPAYILDZVWNR-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1C)C)C)F XPPPAYILDZVWNR-UHFFFAOYSA-N 0.000 claims 1
• PRHLPMRAYYNIQI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=COC=C1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=COC=C1)C)F PRHLPMRAYYNIQI-UHFFFAOYSA-N 0.000 claims 1
• KQVXJJAGJJAWKW-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=CSC=C1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=CSC=C1)C)F KQVXJJAGJJAWKW-UHFFFAOYSA-N 0.000 claims 1
• AJTPBFVCPCWIKT-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=C(C=C1)F)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=C(C=C1)F)C)F AJTPBFVCPCWIKT-UHFFFAOYSA-N 0.000 claims 1
• XQNLYFGQTVYCNK-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=C(C=C1C)F)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=C(C=C1C)F)C)F XQNLYFGQTVYCNK-UHFFFAOYSA-N 0.000 claims 1
• MACISLSDGXPVLR-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=CC=C1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=CC=C1)C)F MACISLSDGXPVLR-UHFFFAOYSA-N 0.000 claims 1
• SOSHSOQTLMUPAE-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1C=NC=CC=1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1C=NC=CC=1)C)F SOSHSOQTLMUPAE-UHFFFAOYSA-N 0.000 claims 1
• KPFRLPAHESBVNX-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1OC(=CC=1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1OC(=CC=1)C)C)F KPFRLPAHESBVNX-UHFFFAOYSA-N 0.000 claims 1
• LVGUAFKGPHSORA-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1OC(=CC=1)C=O)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1OC(=CC=1)C=O)C)F LVGUAFKGPHSORA-UHFFFAOYSA-N 0.000 claims 1
• SSWRSRRADIWLCR-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1OC=CC=1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1OC=CC=1)C)F SSWRSRRADIWLCR-UHFFFAOYSA-N 0.000 claims 1
• BVYAZPAJZZNVRK-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1SC(=CC=1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1SC(=CC=1)C)C)F BVYAZPAJZZNVRK-UHFFFAOYSA-N 0.000 claims 1
• HGFFFSGBARRSSB-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1SC=C(C=1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1SC=C(C=1)C)C)F HGFFFSGBARRSSB-UHFFFAOYSA-N 0.000 claims 1
• NMUKNJIKUPGQME-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1SC=CC=1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1SC=CC=1)C)F NMUKNJIKUPGQME-UHFFFAOYSA-N 0.000 claims 1
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• ZXLMDTVWFWHREN-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=C(N2C=1COCC2)C)C1=COC=C1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=C(N2C=1COCC2)C)C1=COC=C1)=O)F ZXLMDTVWFWHREN-UHFFFAOYSA-N 0.000 claims 1
• FROCIZYYIAXVOB-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=C(N2C=1COCC2)C)C1=CSC=C1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=C(N2C=1COCC2)C)C1=CSC=C1)=O)F FROCIZYYIAXVOB-UHFFFAOYSA-N 0.000 claims 1
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• MSPWLQMDDYRBAP-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=C(N2C=1COCC2)C)C=1SC=C(C=1)C)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=C(N2C=1COCC2)C)C=1SC=C(C=1)C)=O)F MSPWLQMDDYRBAP-UHFFFAOYSA-N 0.000 claims 1
• YWYJGDNFFGHQEK-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=C(N2C=1COCC2)C)C=1SC=CC=1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=C(N2C=1COCC2)C)C=1SC=CC=1)=O)F YWYJGDNFFGHQEK-UHFFFAOYSA-N 0.000 claims 1
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• JMHWFCZWTNTQRC-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C1=CSC=C1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C1=CSC=C1)=O)F JMHWFCZWTNTQRC-UHFFFAOYSA-N 0.000 claims 1
• LLXXBVQTLMYOIE-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1OC=CC=1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1OC=CC=1)=O)F LLXXBVQTLMYOIE-UHFFFAOYSA-N 0.000 claims 1
• UCVGDUJGIMWBTI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC(=CC=1)C)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC(=CC=1)C)=O)F UCVGDUJGIMWBTI-UHFFFAOYSA-N 0.000 claims 1
• ZTPPMOXJBDVHDZ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC=C(C=1)C)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC=C(C=1)C)=O)F ZTPPMOXJBDVHDZ-UHFFFAOYSA-N 0.000 claims 1
• JYCSPQOEJLFNRL-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC=CC=1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC=CC=1)=O)F JYCSPQOEJLFNRL-UHFFFAOYSA-N 0.000 claims 1
• FHGACBYGUZSSGN-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=C(C=NC=C1)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=C(C=NC=C1)F)=O)F FHGACBYGUZSSGN-UHFFFAOYSA-N 0.000 claims 1
• VLGRKRXTELZQMQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)C)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)C)=O)F VLGRKRXTELZQMQ-UHFFFAOYSA-N 0.000 claims 1
• TXBYEKNRJRLLEN-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)F)=O)F TXBYEKNRJRLLEN-UHFFFAOYSA-N 0.000 claims 1
• JXAVEKZMGZHAQX-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)O)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)O)=O)F JXAVEKZMGZHAQX-UHFFFAOYSA-N 0.000 claims 1
• AQNPSEJLYYRKFQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OC(C)C)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OC(C)C)=O)F AQNPSEJLYYRKFQ-UHFFFAOYSA-N 0.000 claims 1
• PQFBNURKUROABN-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OC)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OC)=O)F PQFBNURKUROABN-UHFFFAOYSA-N 0.000 claims 1
• YNHAHAOLJMMCDL-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OCCOCCOCC)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OCCOCCOCC)=O)F YNHAHAOLJMMCDL-UHFFFAOYSA-N 0.000 claims 1
• DULMLQKOCHQMDQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC=NC=C1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC=NC=C1)=O)F DULMLQKOCHQMDQ-UHFFFAOYSA-N 0.000 claims 1
• XTEAASMSMMAXJE-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC=[N+](C=C1)[O-])=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC=[N+](C=C1)[O-])=O)F XTEAASMSMMAXJE-UHFFFAOYSA-N 0.000 claims 1
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• BNMBIJKZZRAHCI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)OCC)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)OCC)=O)F BNMBIJKZZRAHCI-UHFFFAOYSA-N 0.000 claims 1
• FMTVXXZRSORBKW-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1C)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1C)F)=O)F FMTVXXZRSORBKW-UHFFFAOYSA-N 0.000 claims 1
• JVYUOHPIMNJQNE-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C=1C=NC=CC=1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C=1C=NC=CC=1)=O)F JVYUOHPIMNJQNE-UHFFFAOYSA-N 0.000 claims 1
• CUZNXKBGCZNZNP-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C=1N=NC=CC=1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C=1N=NC=CC=1)=O)F CUZNXKBGCZNZNP-UHFFFAOYSA-N 0.000 claims 1
• PLYDGFZRLONKPP-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC(=NC=C1)O)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC(=NC=C1)O)=O)F PLYDGFZRLONKPP-UHFFFAOYSA-N 0.000 claims 1
• REEHLFPGCWNRRS-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC=NC=C1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC=NC=C1)=O)F REEHLFPGCWNRRS-UHFFFAOYSA-N 0.000 claims 1
• CJMUTKWRGXBZMI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC=[N+](C=C1)[O-])=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC=[N+](C=C1)[O-])=O)F CJMUTKWRGXBZMI-UHFFFAOYSA-N 0.000 claims 1
• WXGRPEIXNHMYHY-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1OCC)C1=NC=C(C=C1)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1OCC)C1=NC=C(C=C1)F)=O)F WXGRPEIXNHMYHY-UHFFFAOYSA-N 0.000 claims 1
• NWOUOFPZTLZRBO-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=CN=CS1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=CN=CS1)C)F NWOUOFPZTLZRBO-UHFFFAOYSA-N 0.000 claims 1
• NEFMRZONQLCBLZ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=COC=C1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=COC=C1)C)F NEFMRZONQLCBLZ-UHFFFAOYSA-N 0.000 claims 1
• KVWOLBLGONMBMO-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=CSC=C1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=CSC=C1)C)F KVWOLBLGONMBMO-UHFFFAOYSA-N 0.000 claims 1
• XPNPZUCFVYALRK-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=NC=C(C=C1)F)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=NC=C(C=C1)F)C)F XPNPZUCFVYALRK-UHFFFAOYSA-N 0.000 claims 1
• AQBBFGCOJJASCG-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1C=NOC=1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1C=NOC=1)C)F AQBBFGCOJJASCG-UHFFFAOYSA-N 0.000 claims 1
• GXPYXVFGHQYIML-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N(N=C(C=1)C(F)(F)F)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N(N=C(C=1)C(F)(F)F)C)C)F GXPYXVFGHQYIML-UHFFFAOYSA-N 0.000 claims 1
• PMLHAPGDYAOKCH-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N(N=C(C=1)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N(N=C(C=1)C)C)C)F PMLHAPGDYAOKCH-UHFFFAOYSA-N 0.000 claims 1
• HAGJXHDZJYETIK-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N(N=CC=1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N(N=CC=1)C)C)F HAGJXHDZJYETIK-UHFFFAOYSA-N 0.000 claims 1
• ILMLBRHNNSVSCT-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N=CSC=1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N=CSC=1)C)F ILMLBRHNNSVSCT-UHFFFAOYSA-N 0.000 claims 1
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• DWRPNQLZTKLVSH-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1OC(=CC=1)C(C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1OC(=CC=1)C(C)C)C)F DWRPNQLZTKLVSH-UHFFFAOYSA-N 0.000 claims 1
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