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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- ATHWWMWRXIYCJT-UHFFFAOYSA-N n-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1h-imidazol-2-yl)-1-benzofuran-6-yl]-n-(3-phenylpropyl)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)CCCC1=CC=CC=C1 ATHWWMWRXIYCJT-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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| JP2016522800A (ja) | 2013-04-12 | 2016-08-04 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 新規トリアゾリンチオン誘導体 |
| CN105308032B (zh) | 2013-04-12 | 2017-05-24 | 拜耳作物科学股份公司 | 新的三唑衍生物 |
| EA030024B1 (ru) | 2013-04-12 | 2018-06-29 | Байер Кропсайенс Акциенгезельшафт | Новые производные триазола для борьбы с фитопатогенными вредоносными грибами |
| DK3043803T3 (da) | 2013-09-11 | 2022-08-01 | Univ Emory | Nukleotid- og nucleosidsammensætninger og deres anvendelse |
| GB201321733D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| WO2016156294A1 (en) | 2015-04-02 | 2016-10-06 | Bayer Cropscience Aktiengesellschaft | Triazol derivatives as fungicides |
| JP2018516237A (ja) | 2015-04-02 | 2018-06-21 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 新規な５−置換イミダゾール誘導体 |
| JP7129703B2 (ja) | 2016-04-28 | 2022-09-02 | エモリー ユニバーシティー | アルキン含有ヌクレオチド及びヌクレオシド治療組成物並びにそれらに関連した使用 |
| CR20190128A (es) | 2016-09-13 | 2019-05-15 | Bayer Ag | Combinaciones de compuesto activo que comprenden un derivado de imidazol sustituido en la posición 5 |
| CN109983010A (zh) | 2016-09-29 | 2019-07-05 | 拜耳作物科学股份公司 | 作为用于作物保护的杀真菌剂的1-[2-(1-氯环丙基)-2-羟基-3-(3-苯基-1,2-噁唑-5-基)丙基]-1h-咪唑-5-甲腈衍生物及相关化合物 |
| US20190218188A1 (en) | 2016-09-29 | 2019-07-18 | Bayer Cropscience Aktiengesellschaft | Novel 5-substituted imidazole derivatives |
| EP3519391A1 (en) | 2016-09-29 | 2019-08-07 | Bayer CropScience Aktiengesellschaft | Novel 5-substituted imidazolylmethyl derivatives |
| SG11202002032SA (en) | 2017-09-22 | 2020-04-29 | Jubilant Epipad LLC | Heterocyclic compounds as pad inhibitors |
| CA3076476A1 (en) | 2017-10-18 | 2019-04-25 | Jubilant Epipad LLC | Imidazo-pyridine compounds as pad inhibitors |
| BR112020008851A2 (pt) | 2017-11-06 | 2020-10-20 | Jubilant Prodel LLC | composto da fórmula i, processo de preparação de compostos da fórmula i, composição farmacêutica, método para o tratamento e/ou prevenção de várias doenças, uso, método para o tratamento de câncer, método de tratamento de câncer e método para o tratamento e/ou prevenção de câncer e doenças infecciosas |
| BR112020009446A2 (pt) | 2017-11-13 | 2020-11-03 | Bayer Aktiengesellschaft | derivados de tetrazólio propila e seu uso como fungicida |
| PL3704120T3 (pl) | 2017-11-24 | 2024-09-16 | Jubilant Episcribe Llc | Związki heterocykliczne jako inhibitory prmt5 |
| SG11202008950PA (en) | 2018-03-13 | 2020-10-29 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
Family Cites Families (184)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3497597A (en) | 1967-08-01 | 1970-02-24 | American Cyanamid Co | Fungicidal composition and method containing 5-nitro-1,3,4-thiadiazoles |
| DE3208437A1 (de) | 1982-03-09 | 1983-09-15 | Bayer Ag, 5090 Leverkusen | Imidazothiadiazolalkencarbonsaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln |
| SE8704248D0 (sv) | 1987-10-30 | 1987-10-30 | Haessle Ab | Medical use |
| WO1991000092A1 (en) | 1989-06-13 | 1991-01-10 | Smithkline Beecham Corporation | Inhibition of interleukin-1 and tumor necrosis factor production by monocytes and/or macrophages |
| JP2778009B2 (ja) | 1989-09-12 | 1998-07-23 | 株式会社リコー | 電子写真感光体 |
| US5716964A (en) | 1989-12-04 | 1998-02-10 | G.D. Searle & Co. | Tetrazolyl substituted imidazo 1,2-a!pyridinylalkyl compounds for treatment of neurotoxic injury |
| KR910011852A (ko) | 1989-12-04 | 1991-08-07 | 폴 디. 매튜카이티스 | 신경독 장해 치료용 이미다조[1,2-a]피리디닐알킬 화합물 |
| AU8205991A (en) | 1990-06-12 | 1992-01-07 | Smithkline Beecham Corporation | Inhibition of 5-lipoxygenase and cyclooxygenase pathway mediated diseases |
| CA2092305C (en) | 1990-09-25 | 2003-02-11 | Alfred P. Spada | Compounds having antihypertensive and anti-ischemic properties |
| GB9026926D0 (en) | 1990-12-12 | 1991-01-30 | Smith Kline French Lab | Novel process |
| ZA919797B (en) | 1990-12-13 | 1992-10-28 | Smithkline Beecham Corp | Bicyclo-5,6-dihydro-7h-pyrrolo-1,20-imidazol-7-ols and 7-ones |
| WO1992010190A1 (en) | 1990-12-13 | 1992-06-25 | Smithkline Beecham Corporation | Novel csaids |
| US5240943A (en) | 1991-12-19 | 1993-08-31 | G. D. Searle & Co. | Benzopyran class iii antiarrhythmic agents |
| EP0644762B1 (en) | 1992-06-10 | 1997-12-17 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compounds for the treatment of anemia |
| RU2105005C1 (ru) | 1992-07-03 | 1998-02-20 | Кумиай Кемикал Индастри Ко., Лтд. | Конденсированное гетероциклическое производное, способ его получения и гербицидное средство |
| US5317028A (en) | 1992-09-08 | 1994-05-31 | Warner-Lambert Co. | 7-((substituted)amino)-8((substituted)carbonyl)-methylamino-1-oxaspiro(4,5)decanes useful in Parkinson's disease, dystonia, and other movement disorders |
| TW253885B (enExample) | 1992-12-15 | 1995-08-11 | Ishihara Sangyo Kaisha | |
| JPH08508030A (ja) | 1993-03-18 | 1996-08-27 | メルク シヤープ エンド ドーム リミテツド | ベンゾイミダゾール誘導体 |
| GB9316890D0 (en) | 1993-08-13 | 1993-09-29 | Pilkington Plc | Photochromic compounds |
| GB9408577D0 (en) | 1994-04-29 | 1994-06-22 | Fujisawa Pharmaceutical Co | New compound |
| JPH10513151A (ja) | 1994-12-22 | 1998-12-15 | バイオケム ファーマ インコーポレイテッド | トロンビン阻害剤としての複素環式ケトアルギニンペプチド |
| DE69622393T2 (de) | 1995-04-27 | 2002-11-28 | Fujisawa Pharmaceutical Co., Ltd. | Neue verwendung von pyrazolopyridinverbindungen |
| AU5348396A (en) | 1995-05-01 | 1996-11-21 | Fujisawa Pharmaceutical Co., Ltd. | Imidazo 1,2-a pyridine and imidazo 1,2-a pyridezine derivati ves and their use as bone resorption inhibitors |
| FR2735774B1 (fr) | 1995-06-21 | 1997-09-12 | Sanofi Sa | Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant |
| GB9519077D0 (en) | 1995-09-18 | 1995-11-15 | Fujisawa Pharmaceutical Co | New heterocyclic compounds |
| DE19547263C2 (de) | 1995-12-07 | 1999-04-29 | Cardiotec Inc | Amidinohydrazone vom Benzo[b]furan abgeleiteter Ketone, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| JP2000503984A (ja) | 1996-01-22 | 2000-04-04 | 藤沢薬品工業株式会社 | チアゾリルベンゾフラン誘導体およびその医薬組成物 |
| WO1997027205A1 (en) | 1996-01-23 | 1997-07-31 | The Regents Of The University Of Michigan | Imidazo[1,2-a]pyridine c-nucleosides as antiviral agents |
| US6121309A (en) | 1996-03-18 | 2000-09-19 | Eisai Co., Ltd. | Fused-ring carboxylic acid derivatives |
| AU2405697A (en) | 1996-04-25 | 1997-11-12 | Fujisawa Pharmaceutical Co., Ltd. | Preventives and remedies for ischemic intestinal lesion and ileus |
| GB9610813D0 (en) | 1996-05-23 | 1996-07-31 | Pharmacia Spa | Combinatorial solid phase synthesis of a library of benzufuran derivatives |
| NZ332859A (en) | 1996-06-17 | 2000-06-23 | American Home Prod | pyridinyl, pyrimidinyl or benzofuranyl methylamino substituted cyclobutene-3,4-dione derivatives |
| DE19624289A1 (de) | 1996-06-18 | 1998-01-02 | Merckle Gmbh | Pyrrolizin-Verbindungen und deren Verwendung |
| JP2002514162A (ja) | 1996-07-08 | 2002-05-14 | デュポン ファーマシューティカルズ カンパニー | Ｘａ因子阻害薬およびトロンビン阻害薬としてのアミジノインドール類、アミジノアゾール類、およびそれらの類似体 |
| US5990136A (en) | 1996-08-21 | 1999-11-23 | Pharmacia & Upjohn Company | Isoxazoline derivatives useful as antimicrobials |
| WO1998039342A1 (en) | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
| WO1998041237A1 (en) | 1997-03-18 | 1998-09-24 | Fujisawa Pharmaceutical Co., Ltd. | Preventives and remedies for hyperphosphatemia |
| US6255304B1 (en) | 1997-05-30 | 2001-07-03 | Pharmacia & Upjohn Company | Oxazolidinone antibacterial agents having a thiocarbonyl functionality |
| CN1138765C (zh) | 1997-05-30 | 2004-02-18 | 法玛西雅厄普约翰美国公司 | 带有硫代羰基功能基的噁唑烷酮抗菌剂 |
| EP0988289A2 (en) | 1997-06-05 | 2000-03-29 | Takeda Pharmaceutical Company Limited | Heterocyclic compounds, their production and use |
| US5998424A (en) | 1997-06-19 | 1999-12-07 | Dupont Pharmaceuticals Company | Inhibitors of factor Xa with a neutral P1 specificity group |
| GB9716244D0 (en) | 1997-07-31 | 1997-10-08 | Electrophoretics International | Pharmaceutical compounds |
| US6080773A (en) | 1997-10-14 | 2000-06-27 | Akzo Nobel, N.V. | Benzylamine derivatives which are useful in treating psychiatric disorders |
| US6630597B1 (en) | 1997-12-15 | 2003-10-07 | Transitions Optical, Inc. | Photochromic 6-aryl substituted 3H-naphtho(2,1-b)pyrans |
| US6262044B1 (en) | 1998-03-12 | 2001-07-17 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPASES) |
| KR20010034881A (ko) | 1998-05-21 | 2001-04-25 | 시오노 요시히코 | ｓＰＬＡ2 억제 효과를 갖는 피롤로[1,2-ｂ]피리다진 유도체 |
| CA2333947C (en) | 1998-06-01 | 2010-09-21 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compounds as adenosine a1 antagonist for male sterility |
| US6541669B1 (en) | 1998-06-08 | 2003-04-01 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US6410562B1 (en) | 1998-12-18 | 2002-06-25 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| JP2001057292A (ja) | 1999-08-20 | 2001-02-27 | Toray Ind Inc | 発光素子 |
| US6586638B1 (en) | 1999-10-19 | 2003-07-01 | Membrane Extraction Technology Limited | Process for removing and recovering of phenolic compounds from aqueous fluids |
| JP2001139575A (ja) | 1999-11-15 | 2001-05-22 | Fujisawa Pharmaceut Co Ltd | 新規ピラゾロピリジン誘導体 |
| US6461538B2 (en) | 1999-12-16 | 2002-10-08 | Fuji Photo Film Co., Ltd. | Production process for indolizine compounds and their use in organic light-emitting devices |
| AU2001252609A1 (en) | 2000-04-27 | 2001-11-12 | Imperial Cancer Research Technology Ltd. | Imidazopyridine derivatives |
| US6403588B1 (en) | 2000-04-27 | 2002-06-11 | Yamanouchi Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
| GB0017676D0 (en) * | 2000-07-19 | 2000-09-06 | Angeletti P Ist Richerche Bio | Inhibitors of viral polymerase |
| ATE301653T1 (de) | 2000-12-15 | 2005-08-15 | Glaxo Group Ltd | Pyrazolopyridine |
| DE10117183A1 (de) | 2001-04-05 | 2002-10-10 | Gruenenthal Gmbh | Verwendung von substituierten Imidazo[1,2-a]-pyridinverbindungen als Arzneimittel |
| CN100540538C (zh) | 2001-04-16 | 2009-09-16 | 田边三菱制药株式会社 | 高传导率钙-活化k通道开启剂 |
| WO2003004485A1 (fr) | 2001-07-05 | 2003-01-16 | Takeda Chemical Industries, Ltd. | Composes heterocycles a 5 chainons condenses avec un benzo, leur procede de preparation et leur utilisation |
| EP1427410A1 (en) | 2001-08-30 | 2004-06-16 | Merckle Gmbh | Use of annellated pyrrole compounds in the treatment of articular cartilage or subchondral bone degeneration |
| EP1447400B1 (en) | 2001-10-25 | 2008-09-17 | Asahi Kasei Pharma Corporation | Bicyclic compound |
| US20050113283A1 (en) | 2002-01-18 | 2005-05-26 | David Solow-Cordero | Methods of treating conditions associated with an EDG-4 receptor |
| TW200930291A (en) | 2002-04-29 | 2009-07-16 | Bayer Cropscience Ag | Pesticidal heterocycles |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| AU2003249477A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Heterobicylcic metalloproteinase inhibitors |
| US6828044B2 (en) | 2002-10-25 | 2004-12-07 | Eastman Kodak Company | Dopant in an electroluminescent device |
| UA79834C2 (en) | 2002-11-01 | 2007-07-25 | Viropharma Inc | Benzofuran compounds, compositions and methods for treatment and prophylaxis of hepatitis c viral infections and associated diseases |
| US7098231B2 (en) | 2003-01-22 | 2006-08-29 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| EP1599476B1 (en) | 2003-02-27 | 2009-10-14 | Neurosearch A/S | Novel diazabicyclic aryl derivatives |
| AU2004259012C1 (en) | 2003-07-23 | 2012-08-02 | Exelixis, Inc. | Anaplastic lymphoma kinase modulators and methods of use |
| DE602004030017D1 (de) | 2003-08-01 | 2010-12-23 | Chugai Pharmaceutical Co Ltd | Heterocyclische verbindungen als nützliche malonyl-coa decarboxylase-hemmer |
| WO2005014543A1 (ja) | 2003-08-06 | 2005-02-17 | Japan Tobacco Inc. | 縮合環化合物及びそのｈｃｖポリメラーゼ阻害剤としての利用 |
| US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| US7144907B2 (en) | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7351726B2 (en) | 2003-09-25 | 2008-04-01 | Wyeth | Substituted oxadiazolidinediones |
| WO2005027901A1 (en) | 2003-09-25 | 2005-03-31 | Tel Aviv University Future Technology Development L.P. | Compositions and methods using same for treating amyloid-associated diseases |
| US7288638B2 (en) | 2003-10-10 | 2007-10-30 | Bristol-Myers Squibb Company | Fully human antibodies against human 4-1BB |
| WO2005037223A2 (en) | 2003-10-15 | 2005-04-28 | Brigham And Women's Hospital, Inc. | Methods and compositions for immunomodulation |
| SE0303480D0 (sv) | 2003-12-19 | 2003-12-19 | Biovitrum Ab | Benzofuranes |
| WO2005066151A2 (en) | 2003-12-19 | 2005-07-21 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| US7229480B2 (en) | 2004-02-13 | 2007-06-12 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| US20050256150A1 (en) | 2004-02-20 | 2005-11-17 | Vladimir Birman | Enantioselective acyl transfer catalysts and their use in kinetic resolution of alcohols and desymmetrization of meso-diols |
| US7306631B2 (en) | 2004-03-30 | 2007-12-11 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| EP1746888A2 (en) | 2004-05-13 | 2007-01-31 | Viropharma Incorporated | Compounds, compositions and methods for treatment and prophylaxis of hepatitis c viral infections and associated diseases |
| TW200612923A (en) | 2004-07-29 | 2006-05-01 | Ferrer Int | Oxazolidinone compounds and compositions and methods related thereto |
| GB0420719D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| ES2306275T3 (es) | 2004-12-21 | 2008-11-01 | F. Hoffmann-La Roche Ag | Derivados de cromano y sus usos como ligandos dde receptores 5-ht. |
| US7666880B2 (en) | 2005-03-21 | 2010-02-23 | S*Bio Pte Ltd. | Imidazo[1,2-A]pyridine derivatives: preparation and pharmaceutical applications |
| DE102005019181A1 (de) | 2005-04-25 | 2006-10-26 | Novartis Ag | Peptid-Deformylase (PDF) Inhibitoren 1 |
| MY148644A (en) | 2005-07-18 | 2013-05-15 | Orion Corp | New pharmaceutical compounds |
| EP1945209B1 (en) | 2005-08-12 | 2018-05-30 | United States Government As Represented By The Secretary of The United States Army And The U.S. Army Medical Research & Materiel Command | Broad spectrum antibacterial compounds |
| US7399758B2 (en) | 2005-09-12 | 2008-07-15 | Meanwell Nicholas A | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7473688B2 (en) | 2005-09-13 | 2009-01-06 | Bristol-Myers Squibb Company | Indolobenzazepine HCV NS5B inhibitors |
| US7901793B2 (en) | 2005-09-23 | 2011-03-08 | Samsung Mobile Display Co., Ltd. | Organic light-emitting compound and organic light-emitting device containing the same |
| US7772183B2 (en) | 2005-10-12 | 2010-08-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7741281B2 (en) | 2005-11-03 | 2010-06-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CA2755268C (en) | 2005-11-15 | 2013-12-31 | Array Biopharma, Inc. | Erbb inhibitors |
| WO2007081630A2 (en) | 2005-12-21 | 2007-07-19 | Janssen Pharmaceutica, N.V. | Substituted pyrimidinyl kinase inhibitors |
| JP2009523729A (ja) * | 2006-01-13 | 2009-06-25 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｃ型肝炎の治療方法 |
| WO2007087548A2 (en) | 2006-01-25 | 2007-08-02 | Smithkline Beecham Corporation | Chemical compounds |
| US7456165B2 (en) | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
| MX2008012617A (es) | 2006-03-31 | 2008-10-10 | Novartis Ag | Compuestos organicos. |
| US7521443B2 (en) | 2006-05-17 | 2009-04-21 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7456166B2 (en) | 2006-05-17 | 2008-11-25 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7521441B2 (en) | 2006-05-22 | 2009-04-21 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| ES2343914T3 (es) | 2006-05-25 | 2010-08-12 | Bristol-Myers Squibb Company | Inhibidores de ns5b de hcv de indolobenzazepina condensada con ciclopropilo. |
| WO2007140200A2 (en) | 2006-05-25 | 2007-12-06 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine hcv ns5b inhibitors |
| US7585875B2 (en) | 2006-06-06 | 2009-09-08 | Avigen, Inc. | Substituted pyrazolo[1,5-a]pyridine compounds and their methods of use |
| US7452876B2 (en) | 2006-06-08 | 2008-11-18 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| EP2049474B1 (en) | 2006-07-11 | 2015-11-04 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2044083A1 (en) * | 2006-07-14 | 2009-04-08 | Genelabs Technologies, Inc. | Antiviral agents |
| WO2008014219A2 (en) | 2006-07-24 | 2008-01-31 | Smithkline Beecham Corporation | Thiozolidinedione derivatives as p13 kinase inhibitors |
| US20100158862A1 (en) | 2006-08-11 | 2010-06-24 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US7759495B2 (en) | 2006-08-11 | 2010-07-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8329159B2 (en) | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8303944B2 (en) | 2006-08-11 | 2012-11-06 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7659270B2 (en) | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7745636B2 (en) | 2006-08-11 | 2010-06-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| MX2009003650A (es) | 2006-10-06 | 2009-04-22 | Abbott Lab | Nuevos imidazotiazoles e imidazoxazoles. |
| US8343477B2 (en) | 2006-11-01 | 2013-01-01 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
| US20080107625A1 (en) | 2006-11-01 | 2008-05-08 | Bristol-Myers Squibb Company | Inhibitors of Hepatitis C Virus |
| US20080107623A1 (en) | 2006-11-01 | 2008-05-08 | Bristol-Myers Squibb Company | Inhibitors of Hepatitis C Virus |
| WO2008057855A2 (en) | 2006-11-01 | 2008-05-15 | Bristol-Myers Squibb Company | Heterocyclic compounds as modulators of glucocorticoid receptor, ap-i, and/or np-kappa-b activity |
| US7772180B2 (en) | 2006-11-09 | 2010-08-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7763584B2 (en) | 2006-11-16 | 2010-07-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8003604B2 (en) | 2006-11-16 | 2011-08-23 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7888464B2 (en) | 2006-11-16 | 2011-02-15 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CN101195597A (zh) | 2006-12-08 | 2008-06-11 | 中国科学院上海药物研究所 | 1-取代-4,4-二取代氨基硫脲类化合物、其制备方法以及其用途 |
| US7541351B2 (en) | 2007-01-11 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| CA2672290A1 (en) | 2007-01-15 | 2008-07-24 | The United States Of America, As Represented By The Secretary Of The Arm Y, On Behalf Of The U.S. Army Research Institute Of Infectious Diseases | Antiviral compounds and methods of using thereof |
| US7541352B2 (en) | 2007-02-02 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7517872B2 (en) | 2007-02-22 | 2009-04-14 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7998951B2 (en) | 2007-03-05 | 2011-08-16 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
| US7538102B2 (en) | 2007-03-14 | 2009-05-26 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US7541353B2 (en) | 2007-03-14 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| EP1972628A1 (en) | 2007-03-21 | 2008-09-24 | Schwarz Pharma Ag | Indolizines and aza-analog derivatives thereof as CNS active compounds |
| GB0707000D0 (en) | 2007-04-12 | 2007-05-30 | Istituto Di Ricerche D Biolog | Antiviral agents |
| WO2008134553A1 (en) | 2007-04-26 | 2008-11-06 | Xenon Pharmaceuticals Inc. | Methods of using bicyclic compounds in treating sodium channel-mediated diseases |
| US7741347B2 (en) | 2007-05-17 | 2010-06-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| BRPI0811065A2 (pt) | 2007-06-08 | 2014-12-02 | Abbott Lab | Indazóis 5-heteroaril substituídos como inibidores de quinase |
| WO2008153129A1 (ja) | 2007-06-14 | 2008-12-18 | Teijin Pharma Limited | 尿酸値低下剤 |
| US8143243B2 (en) | 2007-08-09 | 2012-03-27 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7652004B2 (en) | 2007-08-09 | 2010-01-26 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| EP2193133B1 (en) | 2007-09-27 | 2015-08-19 | Fundación Centro Nacional de Investigaciones Oncológicas Carlos III | Imidazolothiadiazoles for use as protein kinase inhibitors |
| US8124601B2 (en) | 2007-11-21 | 2012-02-28 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US8129367B2 (en) | 2007-11-21 | 2012-03-06 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| KR20100123717A (ko) | 2008-02-12 | 2010-11-24 | 브리스톨-마이어스 스큅 컴퍼니 | Ｃ형 간염 바이러스 억제제로서의 헤테로시클릭 유도체 |
| US8147818B2 (en) | 2008-02-13 | 2012-04-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7704992B2 (en) | 2008-02-13 | 2010-04-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| JP2011512341A (ja) | 2008-02-14 | 2011-04-21 | エフ．ホフマン−ラ ロシュ アーゲー | 抗ウイルス性複素環化合物 |
| KR100929642B1 (ko) | 2008-02-20 | 2009-12-03 | 주식회사 하이닉스반도체 | 반도체 소자 및 그의 제조방법 |
| JP2009203203A (ja) | 2008-02-29 | 2009-09-10 | Toyo Ink Mfg Co Ltd | アントラセン誘導体及びその用途 |
| AU2009233711B2 (en) | 2008-04-09 | 2015-02-12 | Infinity Pharmaceuticals, Inc | Inhibitors of fatty acid amide hydrolase |
| GB0806656D0 (en) | 2008-04-11 | 2008-05-14 | Karobio Ab | Novel estrogen receptor ligands |
| US8163921B2 (en) | 2008-04-16 | 2012-04-24 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP2110374A1 (en) | 2008-04-18 | 2009-10-21 | Merck Sante | Benzofurane, benzothiophene, benzothiazol derivatives as FXR modulators |
| EP2277881A4 (en) | 2008-04-18 | 2011-09-07 | Shionogi & Co | HETEROCYCLIC COMPOUND HAVING INHIBITORY ACTIVITY ON P13K |
| WO2009137500A1 (en) | 2008-05-05 | 2009-11-12 | Wyeth | 6-substituted benzofuran compounds to treat infection with hepatitis c virus |
| US8133884B2 (en) | 2008-05-06 | 2012-03-13 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US20090285774A1 (en) | 2008-05-15 | 2009-11-19 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20090285773A1 (en) | 2008-05-15 | 2009-11-19 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US8044023B2 (en) | 2008-05-29 | 2011-10-25 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7964560B2 (en) | 2008-05-29 | 2011-06-21 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| AR072008A1 (es) | 2008-06-13 | 2010-07-28 | Merck & Co Inc | Compuestos heterobiciclicos como agentes de inhibicion de quinasa p38 |
| EP2313102A2 (en) * | 2008-07-03 | 2011-04-27 | Biota Scientific Management | Bycyclic nucleosides and nucleotides as therapeutic agents |
| US7906655B2 (en) | 2008-08-07 | 2011-03-15 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8453322B2 (en) | 2008-08-14 | 2013-06-04 | Ddi Global Corp. | Manufacturing methods of multilayer printed circuit board having stacked via |
| US20100056491A1 (en) | 2008-08-29 | 2010-03-04 | Memory Pharmaceuticals Corporation | 4'-amino cyclic compounds having 5-ht6 receptor affinity |
| US8198449B2 (en) * | 2008-09-11 | 2012-06-12 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7994171B2 (en) | 2008-09-11 | 2011-08-09 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8293909B2 (en) | 2008-09-11 | 2012-10-23 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8048887B2 (en) | 2008-09-11 | 2011-11-01 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| WO2010033906A2 (en) | 2008-09-19 | 2010-03-25 | President And Fellows Of Harvard College | Efficient induction of pluripotent stem cells using small molecule compounds |
| US20100080770A1 (en) | 2008-09-29 | 2010-04-01 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US8563505B2 (en) | 2008-09-29 | 2013-10-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8044087B2 (en) | 2008-09-29 | 2011-10-25 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8383094B2 (en) | 2008-10-01 | 2013-02-26 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| JP5416944B2 (ja) | 2008-10-23 | 2014-02-12 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
| US8283310B2 (en) | 2008-12-15 | 2012-10-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20100204265A1 (en) | 2009-02-09 | 2010-08-12 | Genelabs Technologies, Inc. | Certain Nitrogen Containing Bicyclic Chemical Entities for Treating Viral Infections |
| TWI438200B (zh) | 2009-02-17 | 2014-05-21 | 必治妥美雅史谷比公司 | Ｃ型肝炎病毒抑制劑 |
| TWI476190B (zh) | 2009-03-30 | 2015-03-11 | 必治妥美雅史谷比公司 | Ｃ型肝炎病毒抑制劑 |
| TW201038559A (en) | 2009-04-09 | 2010-11-01 | Bristol Myers Squibb Co | Hepatitis C virus inhibitors |
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2011
- 2011-12-16 CN CN201610903761.7A patent/CN106986862A/zh active Pending
- 2011-12-16 WO PCT/US2011/065558 patent/WO2012087833A1/en not_active Ceased
- 2011-12-16 US US13/995,701 patent/US9173887B2/en active Active
- 2011-12-16 EP EP11808073.8A patent/EP2655362A1/en not_active Withdrawn
- 2011-12-16 CA CA2822357A patent/CA2822357A1/en not_active Abandoned
- 2011-12-16 CN CN201180068128.6A patent/CN103649079B/zh not_active Expired - Fee Related
- 2011-12-16 JP JP2013546262A patent/JP5918264B2/ja not_active Expired - Fee Related
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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