JP2009526081A5 - - Google Patents
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- Publication number
- JP2009526081A5 JP2009526081A5 JP2008554485A JP2008554485A JP2009526081A5 JP 2009526081 A5 JP2009526081 A5 JP 2009526081A5 JP 2008554485 A JP2008554485 A JP 2008554485A JP 2008554485 A JP2008554485 A JP 2008554485A JP 2009526081 A5 JP2009526081 A5 JP 2009526081A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexyl
- indolo
- benzazepine
- carboxylic acid
- methyl
- 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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- -1 N-alkylpiperazinyl Chemical group 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 150000004702 methyl esters Chemical class 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 6
- 229940121649 protein inhibitor Drugs 0.000 claims 6
- 239000012268 protein inhibitor Substances 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 3
- OAQBOILMPKLGMA-UHFFFAOYSA-N 13-cyclohexyl-3-methoxy-6-[5-(3-morpholin-4-yl-3-oxopropyl)-1,3-oxazol-2-yl]-6,7-dihydro-5h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C12=CC=C(C(O)=O)C=C2N2CC(C=3OC(CCC(=O)N4CCOCC4)=CN=3)CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 OAQBOILMPKLGMA-UHFFFAOYSA-N 0.000 claims 2
- VHDRZIOZSVZFLW-UHFFFAOYSA-N 13-cyclohexyl-6-(2-oxo-3h-1,3,4-oxadiazol-5-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3OC(=O)NN=3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 VHDRZIOZSVZFLW-UHFFFAOYSA-N 0.000 claims 2
- AZPJUFRNELUFLN-UHFFFAOYSA-N 13-cyclohexyl-6-(3-methyl-1,2,4-oxadiazol-5-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound CC1=NOC(C=2CN3C4=CC(=CC=C4C(C4CCCCC4)=C3C3=CC=CC=C3C=2)C(O)=O)=N1 AZPJUFRNELUFLN-UHFFFAOYSA-N 0.000 claims 2
- GAPSCYRYTMBLBL-UHFFFAOYSA-N 13-cyclohexyl-6-[1-methyl-5-(oxan-4-ylmethyl)-1,2,4-triazol-3-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound CN1N=C(C=2CN3C4=CC(=CC=C4C(C4CCCCC4)=C3C3=CC=CC=C3C=2)C(O)=O)N=C1CC1CCOCC1 GAPSCYRYTMBLBL-UHFFFAOYSA-N 0.000 claims 2
- GOSFQGOWHCXBSJ-UHFFFAOYSA-N 13-cyclohexyl-6-[4-(oxan-4-ylmethyl)-5-oxo-1,3,4-oxadiazol-2-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3OC(=O)N(CC4CCOCC4)N=3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 GOSFQGOWHCXBSJ-UHFFFAOYSA-N 0.000 claims 2
- MWAKBTJMEQSBOT-UHFFFAOYSA-N 13-cyclohexyl-6-[5-(3-morpholin-4-yl-3-oxopropyl)-1,3-oxazol-2-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3OC(CCC(=O)N4CCOCC4)=CN=3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 MWAKBTJMEQSBOT-UHFFFAOYSA-N 0.000 claims 2
- YVCQNGFODIEXAM-UHFFFAOYSA-N 13-cyclohexyl-6-[5-(oxan-4-ylmethyl)-1,3,4-oxadiazol-2-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3OC(CC4CCOCC4)=NN=3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 YVCQNGFODIEXAM-UHFFFAOYSA-N 0.000 claims 2
- XMEUCBMBYSGEEX-UHFFFAOYSA-N 13-cyclohexyl-6-[5-(oxan-4-ylmethyl)-1h-1,2,4-triazol-3-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3N=C(CC4CCOCC4)NN=3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 XMEUCBMBYSGEEX-UHFFFAOYSA-N 0.000 claims 2
- HAWYOPSYYZDEIX-UHFFFAOYSA-N 13-cyclohexyl-6-[5-[(2-morpholin-4-ylacetyl)amino]-1,3,4-oxadiazol-2-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3OC(NC(=O)CN4CCOCC4)=NN=3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 HAWYOPSYYZDEIX-UHFFFAOYSA-N 0.000 claims 2
- NYMXQVVQMNBBPL-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-3-methoxy-6-[5-(3-morpholin-4-yl-3-oxopropyl)-1,3-oxazol-2-yl]-6,7-dihydro-5h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C12=CC=C(C(=O)NS(=O)(=O)N(C)C)C=C2N2CC(C=3OC(CCC(=O)N4CCOCC4)=CN=3)CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 NYMXQVVQMNBBPL-UHFFFAOYSA-N 0.000 claims 2
- JRBOPJICFCXBOU-UHFFFAOYSA-N 6-(5-amino-1,3,4-oxadiazol-2-yl)-13-cyclohexyl-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound O1C(N)=NN=C1C(CN1C2=CC(=CC=C22)C(O)=O)=CC3=CC=CC=C3C1=C2C1CCCCC1 JRBOPJICFCXBOU-UHFFFAOYSA-N 0.000 claims 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims 2
- 108010036949 Cyclosporine Proteins 0.000 claims 2
- 229940122750 HCV entry inhibitor Drugs 0.000 claims 2
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims 2
- 229940121759 Helicase inhibitor Drugs 0.000 claims 2
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- 102000015696 Interleukins Human genes 0.000 claims 2
- 108010063738 Interleukins Proteins 0.000 claims 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims 2
- 229940122055 Serine protease inhibitor Drugs 0.000 claims 2
- 101710102218 Serine protease inhibitor Proteins 0.000 claims 2
- 101000998548 Yersinia ruckeri Alkaline proteinase inhibitor Proteins 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 229960001265 ciclosporin Drugs 0.000 claims 2
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims 2
- 229930182912 cyclosporin Natural products 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims 2
- 229940079322 interferon Drugs 0.000 claims 2
- 239000003475 metalloproteinase inhibitor Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 239000003001 serine protease inhibitor Substances 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- WQQJWFQSSZEJMY-UHFFFAOYSA-N 13-cyclohexyl-3-methoxy-6-(1,3-oxazol-2-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C12=CC=C(C(O)=O)C=C2N2CC(C=3OC=CN=3)=CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 WQQJWFQSSZEJMY-UHFFFAOYSA-N 0.000 claims 1
- GGGUXVPVBSKNGO-UHFFFAOYSA-N 13-cyclohexyl-3-methoxy-6-[2-(oxan-4-ylmethyl)tetrazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C12=CC=C(C(O)=O)C=C2N2CC(C3=NN(CC4CCOCC4)N=N3)=CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 GGGUXVPVBSKNGO-UHFFFAOYSA-N 0.000 claims 1
- UFJOLAMGVIIIEO-UHFFFAOYSA-N 13-cyclohexyl-6-(2-ethyltetrazol-5-yl)-5h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound CCN1N=NC(C=2CC3=CC=CC=C3C=3N(C4=CC(=CC=C4C=3C3CCCCC3)C(O)=O)C=2)=N1 UFJOLAMGVIIIEO-UHFFFAOYSA-N 0.000 claims 1
- UVQAIFXSFFTSHK-UHFFFAOYSA-N 13-cyclohexyl-6-(2-ethyltetrazol-5-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound CCN1N=NC(C=2CN3C4=CC(=CC=C4C(C4CCCCC4)=C3C3=CC=CC=C3C=2)C(O)=O)=N1 UVQAIFXSFFTSHK-UHFFFAOYSA-N 0.000 claims 1
- DTQSHENDIALFEN-UHFFFAOYSA-N 13-cyclohexyl-6-(2h-tetrazol-5-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C3=NNN=N3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 DTQSHENDIALFEN-UHFFFAOYSA-N 0.000 claims 1
- YBCBRWFEXGMFFU-UHFFFAOYSA-N 13-cyclohexyl-6-(furan-3-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C3=COC=C3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 YBCBRWFEXGMFFU-UHFFFAOYSA-N 0.000 claims 1
- MIGPAWNSNSDOEF-UHFFFAOYSA-N 13-cyclohexyl-6-[1-(oxolan-2-ylmethyl)tetrazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3N(N=NN=3)CC3OCCC3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 MIGPAWNSNSDOEF-UHFFFAOYSA-N 0.000 claims 1
- XFQMEVHUWLJINP-UHFFFAOYSA-N 13-cyclohexyl-6-[2-(2-hydroxyethyl)tetrazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound OCCN1N=NC(C=2CN3C4=CC(=CC=C4C(C4CCCCC4)=C3C3=CC=CC=C3C=2)C(O)=O)=N1 XFQMEVHUWLJINP-UHFFFAOYSA-N 0.000 claims 1
- FTIBDKSPEPDGGR-UHFFFAOYSA-N 13-cyclohexyl-6-[2-(cyclopropylmethyl)tetrazol-5-yl]-5h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3CC(C3=NN(CC4CC4)N=N3)=CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 FTIBDKSPEPDGGR-UHFFFAOYSA-N 0.000 claims 1
- LSKZRFKDKYNRRV-UHFFFAOYSA-N 13-cyclohexyl-6-[2-(cyclopropylmethyl)tetrazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C3=NN(CC4CC4)N=N3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 LSKZRFKDKYNRRV-UHFFFAOYSA-N 0.000 claims 1
- QVBPXYCVAASVTD-UHFFFAOYSA-N 13-cyclohexyl-6-[2-(oxolan-2-ylmethyl)tetrazol-5-yl]-5h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3CC(C3=NN(CC4OCCC4)N=N3)=CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 QVBPXYCVAASVTD-UHFFFAOYSA-N 0.000 claims 1
- ULHQYOIEKKTUEJ-UHFFFAOYSA-N 13-cyclohexyl-6-[2-(oxolan-2-ylmethyl)tetrazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C3=NN(CC4OCCC4)N=N3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 ULHQYOIEKKTUEJ-UHFFFAOYSA-N 0.000 claims 1
- ATXFYGSNMDWVKB-UHFFFAOYSA-N 13-cyclohexyl-6-[3-(methylsulfonylmethyl)-1,2,4-oxadiazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound CS(=O)(=O)CC1=NOC(C=2CN3C4=CC(=CC=C4C(C4CCCCC4)=C3C3=CC=CC=C3C=2)C(O)=O)=N1 ATXFYGSNMDWVKB-UHFFFAOYSA-N 0.000 claims 1
- QYTBQTUEBKSLHQ-UHFFFAOYSA-N 13-cyclohexyl-6-[5-(3-methoxy-3-oxopropyl)-1,3-oxazol-2-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound O1C(CCC(=O)OC)=CN=C1C(CN1C2=CC(=CC=C22)C(O)=O)=CC3=CC=CC=C3C1=C2C1CCCCC1 QYTBQTUEBKSLHQ-UHFFFAOYSA-N 0.000 claims 1
- RZICPBVSRPKWNS-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-3-methoxy-6-(1,3-oxazol-2-yl)-6,7-dihydro-5h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C12=CC=C(C(=O)NS(=O)(=O)N(C)C)C=C2N2CC(C=3OC=CN=3)CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 RZICPBVSRPKWNS-UHFFFAOYSA-N 0.000 claims 1
- LBJOSUQXUZEPBC-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-3-methoxy-6-(1,3-oxazol-2-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C12=CC=C(C(=O)NS(=O)(=O)N(C)C)C=C2N2CC(C=3OC=CN=3)=CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 LBJOSUQXUZEPBC-UHFFFAOYSA-N 0.000 claims 1
- UYYCSKODCJTSOZ-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-3-methoxy-6-[2-(oxan-4-ylmethyl)tetrazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C12=CC=C(C(=O)NS(=O)(=O)N(C)C)C=C2N2CC(C3=NN(CC4CCOCC4)N=N3)=CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 UYYCSKODCJTSOZ-UHFFFAOYSA-N 0.000 claims 1
- MGGGCCZERFYBEM-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-6-(3-methyl-1,2,4-oxadiazol-5-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C=12C3=CC=CC=C3C=C(C=3ON=C(C)N=3)CN2C2=CC(C(=O)NS(=O)(=O)N(C)C)=CC=C2C=1C1CCCCC1 MGGGCCZERFYBEM-UHFFFAOYSA-N 0.000 claims 1
- NWJNBUZBXRSWBO-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-6-[1-methyl-5-(oxan-4-ylmethyl)-1,2,4-triazol-3-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C=12C3=CC=CC=C3C=C(C3=NN(C)C(CC4CCOCC4)=N3)CN2C2=CC(C(=O)NS(=O)(=O)N(C)C)=CC=C2C=1C1CCCCC1 NWJNBUZBXRSWBO-UHFFFAOYSA-N 0.000 claims 1
- GGTRDFOHRLUDLW-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-6-[2-(oxan-4-ylmethyl)tetrazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C=12C3=CC=CC=C3C=C(C3=NN(CC4CCOCC4)N=N3)CN2C2=CC(C(=O)NS(=O)(=O)N(C)C)=CC=C2C=1C1CCCCC1 GGTRDFOHRLUDLW-UHFFFAOYSA-N 0.000 claims 1
- CBLORMPCPISPBM-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-6-[3-(methylsulfonylmethyl)-1,2,4-oxadiazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C=12C3=CC=CC=C3C=C(C=3ON=C(CS(C)(=O)=O)N=3)CN2C2=CC(C(=O)NS(=O)(=O)N(C)C)=CC=C2C=1C1CCCCC1 CBLORMPCPISPBM-UHFFFAOYSA-N 0.000 claims 1
- CETZHOZHGXKTEB-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-6-[5-(3-morpholin-4-yl-3-oxopropyl)-1,3-oxazol-2-yl]-6,7-dihydro-5h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C=12C3=CC=CC=C3CC(C=3OC(CCC(=O)N4CCOCC4)=CN=3)CN2C2=CC(C(=O)NS(=O)(=O)N(C)C)=CC=C2C=1C1CCCCC1 CETZHOZHGXKTEB-UHFFFAOYSA-N 0.000 claims 1
- NYGKNSTZSBSKBD-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-6-[5-(3-morpholin-4-yl-3-oxopropyl)-1,3-oxazol-2-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C=12C3=CC=CC=C3C=C(C=3OC(CCC(=O)N4CCOCC4)=CN=3)CN2C2=CC(C(=O)NS(=O)(=O)N(C)C)=CC=C2C=1C1CCCCC1 NYGKNSTZSBSKBD-UHFFFAOYSA-N 0.000 claims 1
- WFBQIFSWUVAQMF-UHFFFAOYSA-N 6-[5-[(2-bromoacetyl)amino]-1,3,4-oxadiazol-2-yl]-13-cyclohexyl-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3OC(NC(=O)CBr)=NN=3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 WFBQIFSWUVAQMF-UHFFFAOYSA-N 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- OPHJWKWLYAFDEQ-UHFFFAOYSA-N N1(CCOCC1)C(CCC1=CN=C(O1)C1=CC=CC=2CCCN3C(C=21)=CC=1C=CC(=CC=13)C(=O)O)=O Chemical compound N1(CCOCC1)C(CCC1=CN=C(O1)C1=CC=CC=2CCCN3C(C=21)=CC=1C=CC(=CC=13)C(=O)O)=O OPHJWKWLYAFDEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- JMNCQOBGWWQJIA-UHFFFAOYSA-N methyl 13-cyclohexyl-3-methoxy-6-(1,3-oxazol-2-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxylate Chemical compound C=12C3=CC=C(OC)C=C3C=C(C=3OC=CN=3)CN2C2=CC(C(=O)OC)=CC=C2C=1C1CCCCC1 JMNCQOBGWWQJIA-UHFFFAOYSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 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
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| 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 |
| US7659263B2 (en) | 2004-11-12 | 2010-02-09 | Japan Tobacco Inc. | Thienopyrrole compound and use thereof as HCV polymerase inhibitor |
| US7399758B2 (en) * | 2005-09-12 | 2008-07-15 | Meanwell Nicholas A | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7456165B2 (en) | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
| 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 |
| EP2029606B1 (en) * | 2006-05-25 | 2010-05-26 | Brystol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine hcv ns5b inhibitors |
| US7521442B2 (en) * | 2006-05-25 | 2009-04-21 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7452876B2 (en) * | 2006-06-08 | 2008-11-18 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7541351B2 (en) * | 2007-01-11 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| 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 |
| US7541353B2 (en) * | 2007-03-14 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7521444B2 (en) * | 2007-03-14 | 2009-04-21 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7547690B2 (en) * | 2007-03-14 | 2009-06-16 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US7538102B2 (en) * | 2007-03-14 | 2009-05-26 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US7538103B2 (en) * | 2007-03-15 | 2009-05-26 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7642251B2 (en) * | 2007-08-09 | 2010-01-05 | 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 |
| US8143243B2 (en) * | 2007-08-09 | 2012-03-27 | 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 |
| US8124601B2 (en) | 2007-11-21 | 2012-02-28 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| AU2008338273B2 (en) | 2007-12-19 | 2014-10-02 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| JP2011515496A (ja) * | 2008-03-27 | 2011-05-19 | ブリストル−マイヤーズ スクイブ カンパニー | ジオキソランおよびジオキソラノン縮合インドロベンザジアゼピンｈｃｖｎｓ５ｂ阻害剤 |
| AU2009228451A1 (en) | 2008-03-27 | 2009-10-01 | Bristol-Myers Squibb Company | Aromatic heterocyclic fused indolobenzadiazepine HCV NS5B inhibitors |
| EP2280978B1 (en) * | 2008-03-27 | 2013-04-24 | Bristol-Myers Squibb Company | Pyrrolidine fused indolobenzadiazepine hcv ns5b inhibitors |
| EP2276764B1 (en) * | 2008-03-27 | 2013-07-24 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis c |
| US8133884B2 (en) * | 2008-05-06 | 2012-03-13 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
| CA2750227A1 (en) | 2009-01-07 | 2010-07-15 | Scynexis, Inc. | Cyclosporine derivative for use in the treatment of hcv and hiv infection |
| JP2012517468A (ja) * | 2009-02-11 | 2012-08-02 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ型肝炎治療のための化合物 |
| US8143244B2 (en) * | 2009-02-26 | 2012-03-27 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US20110027229A1 (en) | 2009-07-31 | 2011-02-03 | Medtronic, Inc. | Continuous subcutaneous administration of interferon-alpha to hepatitis c infected patients |
| US9173887B2 (en) | 2010-12-22 | 2015-11-03 | Abbvie Inc. | Hepatitis C inhibitors and uses thereof |
| EP2658859A4 (en) | 2010-12-30 | 2014-07-30 | Enanta Pharm Inc | MACROCYCLIC HEPATITIS C SERIN PROTEASE INHIBITORS |
| MX2013007698A (es) | 2010-12-30 | 2013-08-15 | Abbvie Inc | Inhibidores de serina proteasa de hepatitis c macrociclicos de fenantridina. |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| CN102276531A (zh) * | 2011-05-30 | 2011-12-14 | 扬子江药业集团广州海瑞药业有限公司 | 一种甲磺酸非诺多泮的制备方法 |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| CN104447952A (zh) * | 2014-12-11 | 2015-03-25 | 上海唐润医药科技有限公司 | 丙肝病毒蛋白酶抑制剂及其合成方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040138109A1 (en) * | 2002-09-30 | 2004-07-15 | Boehringer Ingelheim Pharmaceuticals, Inc. | Potent inhibitor of HCV serine protease |
| EP1636208B1 (en) * | 2003-04-11 | 2012-02-29 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| US20050119318A1 (en) * | 2003-10-31 | 2005-06-02 | Hudyma Thomas W. | Inhibitors of HCV replication |
| ATE428714T1 (de) | 2004-02-24 | 2009-05-15 | Japan Tobacco Inc | Kondensierte heterotetracyclische verbindungen und deren verwendung als hcv-polymerase-inhibitor |
| US7153848B2 (en) | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| US7348425B2 (en) | 2004-08-09 | 2008-03-25 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| ATE384723T1 (de) | 2004-10-13 | 2008-02-15 | Merck Patent Gmbh | Als kinaseinhibitoren geeignete derivate des n,n'-diphenylharnstoffs |
| BRPI0516972A (pt) | 2004-10-26 | 2008-09-30 | Angeletti P Ist Ricerche Bio | composto, uso do mesmo, composição farmacêutica, método para inibir a polimerase do vìrus da hepatite c e/ou de tratar ou prevenir uma doença devido ao vìrus da hepatite c, e, processo para preparar um composto |
| GB0518390D0 (en) | 2005-09-09 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic 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 |
| US7456165B2 (en) | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
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- 2007-02-07 AT AT07763294T patent/ATE483712T1/de active
- 2007-02-07 PT PT07763294T patent/PT1987038E/pt unknown
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- 2007-02-07 WO PCT/US2007/061768 patent/WO2007092888A2/en not_active Ceased
- 2007-02-07 EP EP07763294A patent/EP1987038B1/en active Active
- 2007-02-07 AU AU2007211988A patent/AU2007211988B2/en not_active Ceased
- 2007-02-07 JP JP2008554485A patent/JP5147731B2/ja not_active Expired - Fee Related
- 2007-02-07 ES ES07763294T patent/ES2352574T3/es active Active
- 2007-02-07 DE DE602007009646T patent/DE602007009646D1/de active Active
- 2007-02-07 PL PL07763294T patent/PL1987038T3/pl unknown
- 2007-02-07 HR HR20100672T patent/HRP20100672T1/hr unknown
- 2007-02-07 KR KR1020087021812A patent/KR20080102161A/ko not_active Ceased
- 2007-02-07 CN CN2007800049834A patent/CN101379066B/zh not_active Expired - Fee Related
- 2007-02-07 SI SI200730453T patent/SI1987038T1/sl unknown
-
2008
- 2008-08-13 NO NO20083513A patent/NO20083513L/no not_active Application Discontinuation
-
2011
- 2011-01-04 CY CY20111100016T patent/CY1111423T1/el unknown
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