JP2014500322A5 - - Google Patents
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- Publication number
- JP2014500322A5 JP2014500322A5 JP2013546262A JP2013546262A JP2014500322A5 JP 2014500322 A5 JP2014500322 A5 JP 2014500322A5 JP 2013546262 A JP2013546262 A JP 2013546262A JP 2013546262 A JP2013546262 A JP 2013546262A JP 2014500322 A5 JP2014500322 A5 JP 2014500322A5
- Authority
- JP
- Japan
- Prior art keywords
- benzofuran
- cyclopropyl
- fluorophenyl
- methanesulfonamide
- imidazol
- 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.)
- Granted
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 99
- -1 wherein Chemical group 0.000 claims 89
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 51
- 229910052736 halogen Inorganic materials 0.000 claims 47
- 150000002367 halogens Chemical class 0.000 claims 47
- 150000001875 compounds Chemical class 0.000 claims 43
- 229910052757 nitrogen Inorganic materials 0.000 claims 37
- 229910052739 hydrogen Inorganic materials 0.000 claims 33
- 239000001257 hydrogen Substances 0.000 claims 33
- 125000001424 substituent group Chemical group 0.000 claims 30
- 150000002431 hydrogen Chemical class 0.000 claims 24
- 229910052760 oxygen Inorganic materials 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 24
- 125000004043 oxo group Chemical group O=* 0.000 claims 23
- 229910052717 sulfur Inorganic materials 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 16
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 13
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 10
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 10
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 7
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 229920002477 rna polymer Polymers 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 241000700605 Viruses Species 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 claims 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000002808 molecular sieve Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- FZLBIQMUICKRDK-UHFFFAOYSA-N 2-[6-(2,5-dimethylpyrrol-1-yl)-2-phenyl-1-benzofuran-3-yl]-1h-imidazole Chemical compound CC1=CC=C(C)N1C1=CC=C(C(C=2NC=CN=2)=C(O2)C=3C=CC=CC=3)C2=C1 FZLBIQMUICKRDK-UHFFFAOYSA-N 0.000 claims 1
- NDRHOYIKEHEWAN-UHFFFAOYSA-N 3-[3-(1h-imidazol-2-yl)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-5-yl]-4-methyl-n-(1-phenylcyclopropyl)benzamide Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(=C2)C=3C(=CC=C(C=3)C(=O)NC3(CC3)C=3C=CC=CC=3)C)C2=C1C1=NC=CN1 NDRHOYIKEHEWAN-UHFFFAOYSA-N 0.000 claims 1
- AVUBUQNTEAIQGH-UHFFFAOYSA-N 3-[[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-methylsulfonylamino]-n-methylpropane-1-sulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCCS(=O)(=O)NC)S(C)(=O)=O)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 AVUBUQNTEAIQGH-UHFFFAOYSA-N 0.000 claims 1
- CRDBBGWKFXLNJC-UHFFFAOYSA-N 4-[[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-methylsulfonylamino]-n'-hydroxybutanimidamide Chemical compound C1=2C=C(C3CC3)C(N(CCC\C(N)=N\O)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 CRDBBGWKFXLNJC-UHFFFAOYSA-N 0.000 claims 1
- FSMIULIYKCFWGE-UHFFFAOYSA-N 4-[[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-methylsulfonylamino]-n-methylbutanamide Chemical compound C1=2C=C(C3CC3)C(N(CCCC(=O)NC)S(C)(=O)=O)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 FSMIULIYKCFWGE-UHFFFAOYSA-N 0.000 claims 1
- ZJKUSFXWFDSAGW-UHFFFAOYSA-N 4-[[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-methylsulfonylamino]butanoic acid Chemical compound C1=2C=C(C3CC3)C(N(CCCC(O)=O)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 ZJKUSFXWFDSAGW-UHFFFAOYSA-N 0.000 claims 1
- UPJUAAGYTXKNSD-UHFFFAOYSA-N 4-[[5-cyclopropyl-3-(2,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-methylsulfonylamino]butanoic acid Chemical compound C1=2C=C(C3CC3)C(N(CCCC(O)=O)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NOCN1 UPJUAAGYTXKNSD-UHFFFAOYSA-N 0.000 claims 1
- WXPPBIIVFIIMIP-UHFFFAOYSA-N 4-[[5-cyclopropyl-3-(5,6-dihydro-2h-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-methylsulfonylamino]-n'-hydroxybutanimidamide Chemical compound C1=2C=C(C3CC3)C(N(CCCC(=N)NO)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NOCCN1 WXPPBIIVFIIMIP-UHFFFAOYSA-N 0.000 claims 1
- UXMZTYOMHATDAW-UHFFFAOYSA-N 4-[[5-cyclopropyl-3-(5,6-dihydro-2h-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-methylsulfonylamino]butanoic acid Chemical compound C1=2C=C(C3CC3)C(N(CCCC(O)=O)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NOCCN1 UXMZTYOMHATDAW-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- LBKRPEDEYNCHAH-UHFFFAOYSA-N 5-[[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-methylsulfonylamino]pentanoic acid Chemical compound C1=2C=C(C3CC3)C(N(CCCCC(O)=O)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 LBKRPEDEYNCHAH-UHFFFAOYSA-N 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 229910003849 O-Si Inorganic materials 0.000 claims 1
- 229910003872 O—Si Inorganic materials 0.000 claims 1
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 claims 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 claims 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002912 morpholin-4-ylsulfonyl group Chemical group O1C([H])([H])C([H])([H])N(S(=O)(=O)[*])C([H])([H])C1([H])[H] 0.000 claims 1
- MYLUPBXSPOJRPM-UHFFFAOYSA-N n-(2-aminoethyl)-n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCN)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 MYLUPBXSPOJRPM-UHFFFAOYSA-N 0.000 claims 1
- ZOFPMEAEPQWWJW-UHFFFAOYSA-N n-(2-cyclohexylethyl)-n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide Chemical compound C=1C=2OC(C=3C=CC(F)=CC=3)=C(C=3NC=CN=3)C=2C=C(C2CC2)C=1N(S(=O)(=O)C)CCC1CCCCC1 ZOFPMEAEPQWWJW-UHFFFAOYSA-N 0.000 claims 1
- UMDKPEZPAXCNNB-UHFFFAOYSA-N n-(3-aminopropyl)-n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCCN)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 UMDKPEZPAXCNNB-UHFFFAOYSA-N 0.000 claims 1
- RQFLAZZZBNMSGJ-UHFFFAOYSA-N n-(3-cyanopropyl)-n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCCC#N)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 RQFLAZZZBNMSGJ-UHFFFAOYSA-N 0.000 claims 1
- CAUQQOUEDCRKLJ-UHFFFAOYSA-N n-(cyanomethyl)-n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CC#N)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 CAUQQOUEDCRKLJ-UHFFFAOYSA-N 0.000 claims 1
- JHCPWQHANUANAK-UHFFFAOYSA-N n-(cyclohexylmethyl)-n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide Chemical compound C=1C=2OC(C=3C=CC(F)=CC=3)=C(C=3NC=CN=3)C=2C=C(C2CC2)C=1N(S(=O)(=O)C)CC1CCCCC1 JHCPWQHANUANAK-UHFFFAOYSA-N 0.000 claims 1
- KWGYYWZXXLUCFC-UHFFFAOYSA-N n-(cyclopentylmethyl)-n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide Chemical compound C=1C=2OC(C=3C=CC(F)=CC=3)=C(C=3NC=CN=3)C=2C=C(C2CC2)C=1N(S(=O)(=O)C)CC1CCCC1 KWGYYWZXXLUCFC-UHFFFAOYSA-N 0.000 claims 1
- FUWRTEXLTFZWGF-UHFFFAOYSA-N n-[(2-bromo-1,3-thiazol-5-yl)methyl]-n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide Chemical compound C=1C=2OC(C=3C=CC(F)=CC=3)=C(C=3NC=CN=3)C=2C=C(C2CC2)C=1N(S(=O)(=O)C)CC1=CN=C(Br)S1 FUWRTEXLTFZWGF-UHFFFAOYSA-N 0.000 claims 1
- BFGJMDZSTJICKA-UHFFFAOYSA-N n-[2-(4-anilinophenyl)-5-cyclopropyl-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(3-methylbutyl)methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCC(C)C)S(C)(=O)=O)=CC=2OC(C=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1C1=NC=CN1 BFGJMDZSTJICKA-UHFFFAOYSA-N 0.000 claims 1
- RIKIJEFEHGUSIB-UHFFFAOYSA-N n-[2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-5-propan-2-yloxy-1-benzofuran-6-yl]-n-[(4-methoxyphenyl)methyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CN(S(C)(=O)=O)C(C(=C1)OC(C)C)=CC2=C1C(C=1NC=CN=1)=C(C=1C=CC(F)=CC=1)O2 RIKIJEFEHGUSIB-UHFFFAOYSA-N 0.000 claims 1
- CSOKSSVKVATETF-UHFFFAOYSA-N n-[3-(1h-imidazol-2-yl)-2-phenyl-1-benzofuran-6-yl]-n-(1-phenylethyl)methanesulfonamide Chemical compound C=1C=CC=CC=1C(C)N(S(C)(=O)=O)C(C=C1OC=2C=3C=CC=CC=3)=CC=C1C=2C1=NC=CN1 CSOKSSVKVATETF-UHFFFAOYSA-N 0.000 claims 1
- XAKADMFPZSTBFD-UHFFFAOYSA-N n-[3-(5-chloro-1h-imidazol-2-yl)-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl]methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(NS(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC(Cl)=CN1 XAKADMFPZSTBFD-UHFFFAOYSA-N 0.000 claims 1
- YJAKIGWKNQMVJC-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(2,3-dihydroxy-3-methylbutyl)methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CC(O)C(C)(O)C)S(C)(=O)=O)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 YJAKIGWKNQMVJC-UHFFFAOYSA-N 0.000 claims 1
- AEVUGNFPTSENSF-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(2-hydroxyethyl)methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCO)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 AEVUGNFPTSENSF-UHFFFAOYSA-N 0.000 claims 1
- MARQOJTUVDMPNG-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(2-hydroxypropyl)methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CC(O)C)S(C)(=O)=O)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 MARQOJTUVDMPNG-UHFFFAOYSA-N 0.000 claims 1
- WTCMXJSRGNXMOL-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(2-methoxyethyl)methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCOC)S(C)(=O)=O)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 WTCMXJSRGNXMOL-UHFFFAOYSA-N 0.000 claims 1
- USZWJLKTQGAXCJ-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(2-methylpropyl)methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CC(C)C)S(C)(=O)=O)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 USZWJLKTQGAXCJ-UHFFFAOYSA-N 0.000 claims 1
- SUGGGKHFWAZCSZ-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(2-phenoxyethyl)methanesulfonamide Chemical compound C=1C=2OC(C=3C=CC(F)=CC=3)=C(C=3NC=CN=3)C=2C=C(C2CC2)C=1N(S(=O)(=O)C)CCOC1=CC=CC=C1 SUGGGKHFWAZCSZ-UHFFFAOYSA-N 0.000 claims 1
- FYAZBEQVXGGLTG-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(2-phenylethyl)methanesulfonamide Chemical compound C=1C=2OC(C=3C=CC(F)=CC=3)=C(C=3NC=CN=3)C=2C=C(C2CC2)C=1N(S(=O)(=O)C)CCC1=CC=CC=C1 FYAZBEQVXGGLTG-UHFFFAOYSA-N 0.000 claims 1
- NJKJZDVEQNVQEJ-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(3,4-dihydroxy-4-methylpentyl)methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCC(O)C(C)(O)C)S(C)(=O)=O)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 NJKJZDVEQNVQEJ-UHFFFAOYSA-N 0.000 claims 1
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- SSUCZGSPTGOPLJ-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(4-hydroxybutyl)methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCCCO)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 SSUCZGSPTGOPLJ-UHFFFAOYSA-N 0.000 claims 1
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- RYZAYDNSPWCTNX-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(4-oxopentyl)methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCCC(=O)C)S(C)(=O)=O)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 RYZAYDNSPWCTNX-UHFFFAOYSA-N 0.000 claims 1
- SFCJAZJTGHYQPP-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(5-hydroxypentyl)methanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(CCCCCO)S(=O)(=O)C)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 SFCJAZJTGHYQPP-UHFFFAOYSA-N 0.000 claims 1
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- WECBDEKUMHMKSI-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-propan-2-ylmethanesulfonamide Chemical compound C1=2C=C(C3CC3)C(N(C(C)C)S(C)(=O)=O)=CC=2OC(C=2C=CC(F)=CC=2)=C1C1=NC=CN1 WECBDEKUMHMKSI-UHFFFAOYSA-N 0.000 claims 1
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| EP3043803B1 (en) | 2013-09-11 | 2022-04-27 | Emory University | Nucleotide and nucleoside compositions and their uses |
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2011
- 2011-12-16 WO PCT/US2011/065558 patent/WO2012087833A1/en not_active Ceased
- 2011-12-16 EP EP11808073.8A patent/EP2655362A1/en not_active Withdrawn
- 2011-12-16 CN CN201180068128.6A patent/CN103649079B/zh not_active Expired - Fee Related
- 2011-12-16 US US13/995,701 patent/US9173887B2/en active Active
- 2011-12-16 JP JP2013546262A patent/JP5918264B2/ja not_active Expired - Fee Related
- 2011-12-16 CN CN201610903761.7A patent/CN106986862A/zh active Pending
- 2011-12-16 CA CA2822357A patent/CA2822357A1/en not_active Abandoned
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2015
- 2015-09-14 US US14/852,984 patent/US9453007B2/en active Active
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2016
- 2016-08-18 US US15/240,753 patent/US9567355B2/en active Active