JP2007505091A5 - - Google Patents
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- JP2007505091A5 JP2007505091A5 JP2006525884A JP2006525884A JP2007505091A5 JP 2007505091 A5 JP2007505091 A5 JP 2007505091A5 JP 2006525884 A JP2006525884 A JP 2006525884A JP 2006525884 A JP2006525884 A JP 2006525884A JP 2007505091 A5 JP2007505091 A5 JP 2007505091A5
- Authority
- JP
- Japan
- Prior art keywords
- thieno
- alkyl
- cyclohexyl
- pyrrole
- carboxylic acid
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 94
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 125000006413 ring segment Chemical group 0.000 claims description 30
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 239000011737 fluorine Substances 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 150000002431 hydrogen Chemical group 0.000 claims description 15
- -1 hydroxy, carboxy Chemical group 0.000 claims description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 10
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 150000001204 N-oxides Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- KGPQKNJSZNXOPV-UHFFFAOYSA-N moniliformin Chemical compound OC1=CC(=O)C1=O KGPQKNJSZNXOPV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims 4
- 241000711549 Hepacivirus C Species 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 claims 2
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- ZQWQDKJZNSFUNM-UHFFFAOYSA-N 3-[(benzylamino)methyl]-6-cyclohexyl-4-(methoxymethyl)-5-phenylthieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=C(CNCC=3C=CC=CC=3)C=2N(COC)C(C=2C=CC=CC=2)=C1C1CCCCC1 ZQWQDKJZNSFUNM-UHFFFAOYSA-N 0.000 claims 1
- JLZUJSKTVKGVEF-UHFFFAOYSA-N 3-[[benzyl(methyl)amino]methyl]-6-cyclohexyl-4-(methoxymethyl)-5-phenylthieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=C(CN(C)CC=3C=CC=CC=3)C=2N(COC)C(C=2C=CC=CC=2)=C1C1CCCCC1 JLZUJSKTVKGVEF-UHFFFAOYSA-N 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- PIJIZWLIYOYKMH-UHFFFAOYSA-N 4-benzyl-6-cyclohexyl-5-phenylthieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=CC=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)O)=CC=2N1CC1=CC=CC=C1 PIJIZWLIYOYKMH-UHFFFAOYSA-N 0.000 claims 1
- VLNRFOBEOKWKKS-UHFFFAOYSA-N 4-cyclohexyl-5-phenyl-6h-thieno[2,3-b]pyrrole-2-carboxylic acid Chemical compound C=1C=CC=CC=1C=1NC=2SC(C(=O)O)=CC=2C=1C1CCCCC1 VLNRFOBEOKWKKS-UHFFFAOYSA-N 0.000 claims 1
- OFQMOHBSPCNHAT-UHFFFAOYSA-N 4-cyclohexyl-6-[2-(dimethylamino)-2-oxoethyl]-5-phenylthieno[2,3-b]pyrrole-2-carboxylic acid Chemical compound C1=2C=C(C(O)=O)SC=2N(CC(=O)N(C)C)C(C=2C=CC=CC=2)=C1C1CCCCC1 OFQMOHBSPCNHAT-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- HZYUMMHNVWNXNV-UHFFFAOYSA-N 5-(3-chloro-4-methoxyphenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=C(Cl)C(OC)=CC=C1C(N(C=1C=C(SC=11)C(O)=O)CC(=O)N2CCOCC2)=C1C1CCCCC1 HZYUMMHNVWNXNV-UHFFFAOYSA-N 0.000 claims 1
- HOXZODAALGCXLC-UHFFFAOYSA-N 5-(3-chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)O)=CC=2N1CC(=O)N1CCOCC1 HOXZODAALGCXLC-UHFFFAOYSA-N 0.000 claims 1
- OVQKESNUSXTBDT-UHFFFAOYSA-N 5-(3-chlorophenyl)-6-cyclohexyl-4-[2-(dimethylamino)-2-oxoethyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=CC=2N(CC(=O)N(C)C)C(C=2C=C(Cl)C=CC=2)=C1C1CCCCC1 OVQKESNUSXTBDT-UHFFFAOYSA-N 0.000 claims 1
- VVRMCANIYITKHD-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-3-(1,3-dihydroisoindol-2-ylmethyl)-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C=1N(CC(=O)N2CCOCC2)C=2C(CN3CC4=CC=CC=C4C3)=C(C(=O)O)SC=2C=1C1CCCCC1 VVRMCANIYITKHD-UHFFFAOYSA-N 0.000 claims 1
- RFGZENZGVSWACO-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-3-(1,3-dihydroisoindol-2-ylmethyl)-4-methylthieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=C(CN3CC4=CC=CC=C4C3)C=2N(C)C(C=2C=CC(Cl)=CC=2)=C1C1CCCCC1 RFGZENZGVSWACO-UHFFFAOYSA-N 0.000 claims 1
- WVCIKFSHOZWUSM-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-3-[(2-methylpropylamino)methyl]-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C=1N(CC(=O)N2CCOCC2)C=2C(CNCC(C)C)=C(C(O)=O)SC=2C=1C1CCCCC1 WVCIKFSHOZWUSM-UHFFFAOYSA-N 0.000 claims 1
- XMIYIICEBQXOIQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-3-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=C(C(O)=O)SC2=C1N(CC(=O)N1CCOCC1)C(C=1C=CC(Cl)=CC=1)=C2C1CCCCC1 XMIYIICEBQXOIQ-UHFFFAOYSA-N 0.000 claims 1
- GPCJDWNZBAJPFP-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-3-[(dimethylamino)methyl]-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C=1N(CC(=O)N2CCOCC2)C=2C(CN(C)C)=C(C(O)=O)SC=2C=1C1CCCCC1 GPCJDWNZBAJPFP-UHFFFAOYSA-N 0.000 claims 1
- FFDSHANOHHBPKU-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-3-[(dimethylamino)methyl]-4-methylthieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C=1N(C)C=2C(CN(C)C)=C(C(O)=O)SC=2C=1C1CCCCC1 FFDSHANOHHBPKU-UHFFFAOYSA-N 0.000 claims 1
- AGTYRXITTZPBPH-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-3-(pyrrolidin-1-ylmethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C=1N(CC(=O)N2CCOCC2)C=2C(CN3CCCC3)=C(C(=O)O)SC=2C=1C1CCCCC1 AGTYRXITTZPBPH-UHFFFAOYSA-N 0.000 claims 1
- AVYXWNIRWFXLGM-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-3-[(propan-2-ylamino)methyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C=1N(CC(=O)N2CCOCC2)C=2C(CNC(C)C)=C(C(O)=O)SC=2C=1C1CCCCC1 AVYXWNIRWFXLGM-UHFFFAOYSA-N 0.000 claims 1
- QUOTYKIQXYAEFL-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)O)=CC=2N1CC(=O)N1CCOCC1 QUOTYKIQXYAEFL-UHFFFAOYSA-N 0.000 claims 1
- IOFCTOAWJQMYOD-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-[2-(dimethylamino)-2-oxoethyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=CC=2N(CC(=O)N(C)C)C(C=2C=CC(Cl)=CC=2)=C1C1CCCCC1 IOFCTOAWJQMYOD-UHFFFAOYSA-N 0.000 claims 1
- SMWMLRIKPDWMLY-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-[2-[2-[(dimethylamino)methyl]morpholin-4-yl]-2-oxoethyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1COC(CN(C)C)CN1C(=O)CN1C(C=C(S2)C(O)=O)=C2C(C2CCCCC2)=C1C1=CC=C(Cl)C=C1 SMWMLRIKPDWMLY-UHFFFAOYSA-N 0.000 claims 1
- KLLNDNYCXQKSDJ-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-[2-[methyl-(1-propan-2-ylpyrrolidin-3-yl)amino]-2-oxoethyl]-3-[(2-methylpropylamino)methyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C=1N(CC(=O)N(C)C2CN(CC2)C(C)C)C=2C(CNCC(C)C)=C(C(O)=O)SC=2C=1C1CCCCC1 KLLNDNYCXQKSDJ-UHFFFAOYSA-N 0.000 claims 1
- XRUROXFDVMPNED-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-[2-[methyl-(1-propan-2-ylpyrrolidin-3-yl)amino]-2-oxoethyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1N(C(C)C)CCC1N(C)C(=O)CN1C(C=C(S2)C(O)=O)=C2C(C2CCCCC2)=C1C1=CC=C(Cl)C=C1 XRUROXFDVMPNED-UHFFFAOYSA-N 0.000 claims 1
- XJVIDSGOGXOVQM-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-[2-[methyl-[(1-methylpiperidin-3-yl)methyl]amino]-2-oxoethyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C1=C(C2CCCCC2)C=2SC(C(O)=O)=CC=2N1CC(=O)N(C)CC1CCCN(C)C1 XJVIDSGOGXOVQM-UHFFFAOYSA-N 0.000 claims 1
- AIQPFNLAOFFFFL-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-[2-oxo-2-(4-pyrrolidin-1-ylpiperidin-1-yl)ethyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)O)=CC=2N1CC(=O)N(CC1)CCC1N1CCCC1 AIQPFNLAOFFFFL-UHFFFAOYSA-N 0.000 claims 1
- YCWQSHPHRHGDJC-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-methyl-3-(pyrrolidin-1-ylmethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=C(CN3CCCC3)C=2N(C)C(C=2C=CC(Cl)=CC=2)=C1C1CCCCC1 YCWQSHPHRHGDJC-UHFFFAOYSA-N 0.000 claims 1
- OPXYMXPJBCYOFV-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-methyl-3-[(4-methylpiperazin-1-yl)methyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1CN(C)CCN1CC1=C(C(O)=O)SC2=C1N(C)C(C=1C=CC(Cl)=CC=1)=C2C1CCCCC1 OPXYMXPJBCYOFV-UHFFFAOYSA-N 0.000 claims 1
- PBTULURDYPEQSS-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-methyl-3-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=C(CN3CCN(CC3)S(C)(=O)=O)C=2N(C)C(C=2C=CC(Cl)=CC=2)=C1C1CCCCC1 PBTULURDYPEQSS-UHFFFAOYSA-N 0.000 claims 1
- ADFBLMKUIZMZNV-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-4-methyl-3-[(pyridin-4-ylmethylamino)methyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=C(CNCC=3C=CN=CC=3)C=2N(C)C(C=2C=CC(Cl)=CC=2)=C1C1CCCCC1 ADFBLMKUIZMZNV-UHFFFAOYSA-N 0.000 claims 1
- ZOTDYFDFFOUTDU-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-n-ethylsulfonyl-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)NS(=O)(=O)CC)=CC=2N1CC(=O)N1CCOCC1 ZOTDYFDFFOUTDU-UHFFFAOYSA-N 0.000 claims 1
- RFILEOFRKQSWRQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclohexyl-n-methyl-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)NC)=CC=2N1CC(=O)N1CCOCC1 RFILEOFRKQSWRQ-UHFFFAOYSA-N 0.000 claims 1
- POUAVDPFIPNUCW-UHFFFAOYSA-N 6-cyclohexyl-3-[(dimethylamino)methyl]-5-phenyl-4h-thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=CC=CC=1C=1NC=2C(CN(C)C)=C(C(O)=O)SC=2C=1C1CCCCC1 POUAVDPFIPNUCW-UHFFFAOYSA-N 0.000 claims 1
- KAHHNLVHNLNJHI-UHFFFAOYSA-N 6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-5-(4-phenylmethoxyphenyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)O)=CC=2N1CC(=O)N1CCOCC1 KAHHNLVHNLNJHI-UHFFFAOYSA-N 0.000 claims 1
- YIJDUUFLVVHVJH-UHFFFAOYSA-N 6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-5-phenylthieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=CC=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)O)=CC=2N1CC(=O)N1CCOCC1 YIJDUUFLVVHVJH-UHFFFAOYSA-N 0.000 claims 1
- RKTFEWHUGWAZEB-UHFFFAOYSA-N 6-cyclohexyl-4-[2-(dimethylamino)-2-oxoethyl]-5-(3-formylphenyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=CC=2N(CC(=O)N(C)C)C(C=2C=C(C=O)C=CC=2)=C1C1CCCCC1 RKTFEWHUGWAZEB-UHFFFAOYSA-N 0.000 claims 1
- ZWCPYWFWUKADQO-UHFFFAOYSA-N 6-cyclohexyl-4-[2-(dimethylamino)-2-oxoethyl]-5-(3-methoxyphenyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound COC1=CC=CC(C=2N(C=3C=C(SC=3C=2C2CCCCC2)C(O)=O)CC(=O)N(C)C)=C1 ZWCPYWFWUKADQO-UHFFFAOYSA-N 0.000 claims 1
- IBORFVJNRXYVAS-UHFFFAOYSA-N 6-cyclohexyl-4-[2-(dimethylamino)-2-oxoethyl]-5-(4-formylphenyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=CC=2N(CC(=O)N(C)C)C(C=2C=CC(C=O)=CC=2)=C1C1CCCCC1 IBORFVJNRXYVAS-UHFFFAOYSA-N 0.000 claims 1
- PAIUXPOFNMYAMW-UHFFFAOYSA-N 6-cyclohexyl-4-[2-(dimethylamino)-2-oxoethyl]-5-(6-methoxypyridin-3-yl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=NC(OC)=CC=C1C(N(C=1C=C(SC=11)C(O)=O)CC(=O)N(C)C)=C1C1CCCCC1 PAIUXPOFNMYAMW-UHFFFAOYSA-N 0.000 claims 1
- LDQIMGHSERASIK-UHFFFAOYSA-N 6-cyclohexyl-4-[2-(dimethylamino)-2-oxoethyl]-5-(furan-3-yl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1CCCCC1C=1C=2SC(C(O)=O)=CC=2N(CC(=O)N(C)C)C=1C=1C=COC=1 LDQIMGHSERASIK-UHFFFAOYSA-N 0.000 claims 1
- MLNJWPGFXYKPAF-UHFFFAOYSA-N 6-cyclohexyl-4-[2-(dimethylamino)-2-oxoethyl]-5-phenylthieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=CC=2N(CC(=O)N(C)C)C(C=2C=CC=CC=2)=C1C1CCCCC1 MLNJWPGFXYKPAF-UHFFFAOYSA-N 0.000 claims 1
- JLWXGJRYHOLKSK-UHFFFAOYSA-N 6-cyclohexyl-4-methyl-5-(1,3-oxazol-5-yl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1CCCCC1C=1C=2SC(C(O)=O)=CC=2N(C)C=1C1=CN=CO1 JLWXGJRYHOLKSK-UHFFFAOYSA-N 0.000 claims 1
- BNIGSPMLDODEAJ-UHFFFAOYSA-N 6-cyclohexyl-4-methyl-5-phenylthieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(O)=O)=CC=2N(C)C(C=2C=CC=CC=2)=C1C1CCCCC1 BNIGSPMLDODEAJ-UHFFFAOYSA-N 0.000 claims 1
- ZBRHTWQOCJIYSW-UHFFFAOYSA-N 6-cyclohexyl-5-(4-fluorophenyl)-4-[2-oxo-2-(4-pyrrolidin-1-ylpiperidin-1-yl)ethyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)O)=CC=2N1CC(=O)N(CC1)CCC1N1CCCC1 ZBRHTWQOCJIYSW-UHFFFAOYSA-N 0.000 claims 1
- QKIQVHCJCYHOGU-UHFFFAOYSA-N 6-cyclohexyl-5-(4-formylphenyl)-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C=1C=C(C=O)C=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)O)=CC=2N1CC(=O)N1CCOCC1 QKIQVHCJCYHOGU-UHFFFAOYSA-N 0.000 claims 1
- UBYRXPDIILUWAZ-UHFFFAOYSA-N 6-cyclohexyl-5-(4-methoxyphenyl)-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(N(C=1C=C(SC=11)C(O)=O)CC(=O)N2CCOCC2)=C1C1CCCCC1 UBYRXPDIILUWAZ-UHFFFAOYSA-N 0.000 claims 1
- NNYCXADZGPOLRZ-UHFFFAOYSA-N 6-cyclohexyl-5-(4-methylphenyl)-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(N(C=1C=C(SC=11)C(O)=O)CC(=O)N2CCOCC2)=C1C1CCCCC1 NNYCXADZGPOLRZ-UHFFFAOYSA-N 0.000 claims 1
- GUJWSSYJMOQKIT-UHFFFAOYSA-N 6-cyclohexyl-5-[3-[(dimethylamino)methyl]phenyl]-4-[2-(dimethylamino)-2-oxoethyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound CN(C)CC1=CC=CC(C=2N(C=3C=C(SC=3C=2C2CCCCC2)C(O)=O)CC(=O)N(C)C)=C1 GUJWSSYJMOQKIT-UHFFFAOYSA-N 0.000 claims 1
- LJIYGIMFCMAMAI-UHFFFAOYSA-N 6-cyclohexyl-5-[4-[2-(dimethylamino)ethoxy]phenyl]-4-[2-(dimethylamino)-2-oxoethyl]thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=CC(OCCN(C)C)=CC=C1C(N(C=1C=C(SC=11)C(O)=O)CC(=O)N(C)C)=C1C1CCCCC1 LJIYGIMFCMAMAI-UHFFFAOYSA-N 0.000 claims 1
- IBPDPOIIZGXYEX-UHFFFAOYSA-N 6-cyclohexyl-5-phenyl-4-(2-pyrrolidin-1-ium-1-ylethyl)thieno[3,2-b]pyrrole-2-carboxylic acid;2,2,2-trifluoroacetate Chemical compound OC(=O)C(F)(F)F.C=1C=CC=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)O)=CC=2N1CCN1CCCC1 IBPDPOIIZGXYEX-UHFFFAOYSA-N 0.000 claims 1
- WPJMYSSUWNPXRV-UHFFFAOYSA-N 6-cyclohexyl-5-phenyl-4-(pyridin-1-ium-3-ylmethyl)thieno[3,2-b]pyrrole-2-carboxylic acid;2,2,2-trifluoroacetate Chemical compound OC(=O)C(F)(F)F.C=1C=CC=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)O)=CC=2N1CC1=CC=CN=C1 WPJMYSSUWNPXRV-UHFFFAOYSA-N 0.000 claims 1
- KWJJDJJGUBFGKF-UHFFFAOYSA-N 6-cyclohexyl-5-phenyl-4h-thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(=O)O)=CC=2NC(C=2C=CC=CC=2)=C1C1CCCCC1 KWJJDJJGUBFGKF-UHFFFAOYSA-N 0.000 claims 1
- MVKNSOMELSVNOY-UHFFFAOYSA-N 6-cyclopentyl-5-phenyl-4h-thieno[3,2-b]pyrrole-2-carboxylic acid Chemical compound C1=2SC(C(=O)O)=CC=2NC(C=2C=CC=CC=2)=C1C1CCCC1 MVKNSOMELSVNOY-UHFFFAOYSA-N 0.000 claims 1
- 102000006992 Interferon-alpha Human genes 0.000 claims 1
- 108010047761 Interferon-alpha Proteins 0.000 claims 1
- 102000003996 Interferon-beta Human genes 0.000 claims 1
- 108090000467 Interferon-beta Proteins 0.000 claims 1
- 102000008070 Interferon-gamma Human genes 0.000 claims 1
- 108010074328 Interferon-gamma Proteins 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229940044627 gamma-interferon Drugs 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- CQTRNSLAUNFUKJ-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)thieno[3,2-b]pyrrole-2-carboxylate Chemical compound C=1C=C(Cl)C=CC=1C1=C(C2CCCCC2)C=2SC(C(=O)OC)=CC=2N1CC(=O)N1CCOCC1 CQTRNSLAUNFUKJ-UHFFFAOYSA-N 0.000 claims 1
- MZANQBDSGYVDQA-UHFFFAOYSA-N methyl 6-benzyl-4-cyclohexyl-5-phenylthieno[2,3-b]pyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1C=1N(CC=2C=CC=CC=2)C=2SC(C(=O)OC)=CC=2C=1C1CCCCC1 MZANQBDSGYVDQA-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000004151 quinonyl group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
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| PCT/GB2004/003838 WO2005023819A1 (en) | 2003-09-09 | 2004-09-07 | Thienopyrroles as antiviral agents |
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| JP2007505091A JP2007505091A (ja) | 2007-03-08 |
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| ES (1) | ES2291933T3 (https=) |
| GB (1) | GB0321003D0 (https=) |
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| CA2534649A1 (en) | 2003-08-01 | 2005-02-10 | Genelabs Technologies, Inc. | Bicyclic imidazol derivatives against flaviviridae |
| WO2005049622A1 (ja) * | 2003-11-19 | 2005-06-02 | Japan Tobacco Inc. | ５－５員縮合複素環化合物及びそのｈｃｖポリメラーゼ阻害剤としての用途 |
| US20070049593A1 (en) | 2004-02-24 | 2007-03-01 | Japan Tobacco Inc. | Tetracyclic fused heterocyclic compound and use thereof as HCV polymerase inhibitor |
| GB0416396D0 (en) * | 2004-07-22 | 2004-08-25 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| US7659263B2 (en) | 2004-11-12 | 2010-02-09 | Japan Tobacco Inc. | Thienopyrrole compound and use thereof as HCV polymerase inhibitor |
| CA2606195C (en) | 2005-05-02 | 2015-03-31 | Merck And Co., Inc. | Hcv ns3 protease inhibitors |
| GB0509326D0 (en) * | 2005-05-09 | 2005-06-15 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| NZ565269A (en) | 2005-08-01 | 2010-03-26 | Merck & Co Inc | Macrocyclic peptides as HCV NS3 protease inhibitors |
| GB0609492D0 (en) | 2006-05-15 | 2006-06-21 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| GB0612423D0 (en) | 2006-06-23 | 2006-08-02 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| AU2007309546A1 (en) | 2006-10-24 | 2008-05-02 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | HCV NS3 protease inhibitors |
| CA2667146C (en) | 2006-10-24 | 2016-01-19 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| AU2007309488B2 (en) | 2006-10-24 | 2012-10-11 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| US8377874B2 (en) | 2006-10-27 | 2013-02-19 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| BRPI0718161A2 (pt) | 2006-10-27 | 2013-11-26 | Merck & Co Inc | Composto, composição farmacêutica, e, uso do composto. |
| GB0625349D0 (en) | 2006-12-20 | 2007-01-31 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| CA2672250C (en) | 2006-12-20 | 2013-04-30 | Ian Stansfield | Antiviral indoles |
| GB0625345D0 (en) | 2006-12-20 | 2007-01-31 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| JP2010533699A (ja) | 2007-07-17 | 2010-10-28 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー | Ｃ型肝炎感染症の治療のための大環状インドール誘導体 |
| AU2008277377B2 (en) | 2007-07-19 | 2013-08-01 | Msd Italia S.R.L. | Macrocyclic compounds as antiviral agents |
| EP2234977A4 (en) | 2007-12-19 | 2011-04-13 | Boehringer Ingelheim Int | VIRAL POLYMERASE INHIBITORS |
| WO2009134624A1 (en) | 2008-04-28 | 2009-11-05 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| US8126839B2 (en) * | 2008-06-19 | 2012-02-28 | Yahoo! Inc. | Methods and apparatuses for adapting a ranking function of a search engine for use with a specific domain |
| EA019327B1 (ru) | 2008-07-22 | 2014-02-28 | Мерк Шарп Энд Домэ Корп. | Макроциклическое хиноксалиновое соединение в качестве ингибитора протеазы вгс ns3 |
| CN102271699A (zh) | 2009-01-07 | 2011-12-07 | 西尼克斯公司 | 用于治疗hcv和hiv感染的环孢菌素衍生物 |
| US8828930B2 (en) | 2009-07-30 | 2014-09-09 | Merck Sharp & Dohme Corp. | Hepatitis C virus NS3 protease inhibitors |
| US20110152243A1 (en) * | 2009-12-23 | 2011-06-23 | Abbott Laboratories | Novel thienopyrrole compounds |
| CN105399697A (zh) * | 2014-09-12 | 2016-03-16 | 苏州旺山旺水生物医药有限公司 | 一种氨基磺酰基类化合物、其制备方法及用途 |
| EP3246330A1 (en) * | 2016-05-18 | 2017-11-22 | Istituto Europeo di Oncologia S.r.l. | Imidazoles as histone demethylase inhibitors |
| SG11202012616RA (en) * | 2018-08-21 | 2021-02-25 | Kyorin Pharmaceutical Co Ltd | Bicyclic heteroaromatic ring derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3706810A (en) * | 1970-09-15 | 1972-12-19 | American Cyanamid Co | N-morpholinoalkyl-thieno(3,2-b)pyrrole-5-carboxamides |
| SU367098A1 (ru) * | 1971-01-20 | 1973-01-23 | Способ получения производных 4,5-диоксотиено- - | |
| SU478833A1 (ru) * | 1972-12-29 | 1975-07-30 | Всесоюзный Научно-Исследовательский Химико-Фармацевтический Институт Им.С.Орджоникидзе | Способ получени производных тиено -(3,2-в)-пиррола |
| JPH04356029A (ja) | 1990-07-02 | 1992-12-09 | Japan Synthetic Rubber Co Ltd | 非線形光学素子 |
| JPH04179949A (ja) * | 1990-11-15 | 1992-06-26 | Fuji Photo Film Co Ltd | 新規な色素形成カプラーおよび該カプラーを用いたハロゲン化銀カラー写真感光材料 |
| US5340833A (en) * | 1992-05-01 | 1994-08-23 | Eisai Co., Ltd. | Urokinase inhibitors |
| EP1162196A4 (en) | 1999-12-27 | 2003-04-16 | Japan Tobacco Inc | COMPOUNDS WITH JOINED CYCLES AND THEIR USE AS MEDICAMENTS |
| US6448281B1 (en) | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| JP2003212846A (ja) * | 2001-06-26 | 2003-07-30 | Japan Tobacco Inc | 縮合環化合物及びｃ型肝炎治療剤 |
| AR035543A1 (es) | 2001-06-26 | 2004-06-16 | Japan Tobacco Inc | Agente terapeutico para la hepatitis c que comprende un compuesto de anillo condensado, compuesto de anillo condensado, composicion farmaceutica que lo comprende, compuestos de benzimidazol, tiazol y bifenilo utiles como intermediarios para producir dichos compuestos, uso del compuesto de anillo con |
| CA2448737C (en) | 2001-07-20 | 2010-06-01 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| EP2335700A1 (en) | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis C virus polymerase inhibitors with a heterobicylic structure |
| WO2003026587A2 (en) | 2001-09-26 | 2003-04-03 | Bristol-Myers Squibb Company | Compounds useful for treating hepatitus c virus |
| GB0222909D0 (en) * | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| BRPI0409465A (pt) * | 2003-04-17 | 2006-05-02 | Pfizer Prod Inc | derivados de carboxamida como agentes antidiabéticos |
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2003
- 2003-09-09 GB GBGB0321003.6A patent/GB0321003D0/en not_active Ceased
-
2004
- 2004-09-07 CN CNA2004800257994A patent/CN1849323A/zh active Pending
- 2004-09-07 CA CA002537545A patent/CA2537545A1/en not_active Abandoned
- 2004-09-07 AT AT04768385T patent/ATE373005T1/de not_active IP Right Cessation
- 2004-09-07 JP JP2006525884A patent/JP2007505091A/ja active Pending
- 2004-09-07 US US10/571,234 patent/US7781431B2/en not_active Expired - Fee Related
- 2004-09-07 ES ES04768385T patent/ES2291933T3/es not_active Expired - Lifetime
- 2004-09-07 EP EP04768385A patent/EP1664059B1/en not_active Expired - Lifetime
- 2004-09-07 WO PCT/GB2004/003838 patent/WO2005023819A1/en not_active Ceased
- 2004-09-07 DE DE602004008945T patent/DE602004008945T2/de not_active Expired - Lifetime
- 2004-09-07 AU AU2004270470A patent/AU2004270470A1/en not_active Abandoned
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