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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US77139106P | 2006-02-08 | 2006-02-08 | |
| US60/771,391 | 2006-02-08 | ||
| PCT/US2007/061768 WO2007092888A2 (en) | 2006-02-08 | 2007-02-07 | Hcv ns5b inhibitors |
Publications (3)
| Publication Number | Publication Date |
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| JP2009526081A JP2009526081A (ja) | 2009-07-16 |
| JP2009526081A5 true JP2009526081A5 (https=) | 2010-04-02 |
| JP5147731B2 JP5147731B2 (ja) | 2013-02-20 |
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| JP2008554485A Expired - Fee Related JP5147731B2 (ja) | 2006-02-08 | 2007-02-07 | Ｈｃｖｎｓ５ｂ阻害剤 |
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| EP (1) | EP1987038B1 (https=) |
| JP (1) | JP5147731B2 (https=) |
| KR (1) | KR20080102161A (https=) |
| CN (1) | CN101379066B (https=) |
| AT (1) | ATE483712T1 (https=) |
| AU (1) | AU2007211988B2 (https=) |
| CY (1) | CY1111423T1 (https=) |
| DE (1) | DE602007009646D1 (https=) |
| DK (1) | DK1987038T3 (https=) |
| ES (1) | ES2352574T3 (https=) |
| HR (1) | HRP20100672T1 (https=) |
| NO (1) | NO20083513L (https=) |
| PL (1) | PL1987038T3 (https=) |
| PT (1) | PT1987038E (https=) |
| SI (1) | SI1987038T1 (https=) |
| WO (1) | WO2007092888A2 (https=) |
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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 |
| JP5205370B2 (ja) * | 2006-05-25 | 2013-06-05 | ブリストル−マイヤーズ スクイブ カンパニー | シクロプロピル縮合インドロベンゾアゼピンｈｃｖｎｓ５ｂ阻害剤 |
| WO2007140200A2 (en) * | 2006-05-25 | 2007-12-06 | 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 |
| 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 |
| 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 |
| US7538103B2 (en) * | 2007-03-15 | 2009-05-26 | 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 |
| US7652004B2 (en) * | 2007-08-09 | 2010-01-26 | 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 |
| 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 |
| EP2234977A4 (en) | 2007-12-19 | 2011-04-13 | Boehringer Ingelheim Int | VIRAL POLYMERASE INHIBITORS |
| WO2009120733A1 (en) * | 2008-03-27 | 2009-10-01 | Bristol-Myers Squibb Company | Pyrrolidine fused indolobenzadiazepine hcv ns5b inhibitors |
| JP2011515486A (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 | Ｃ型肝炎の治療用化合物 |
| KR20100124848A (ko) | 2008-03-27 | 2010-11-29 | 브리스톨-마이어스 스큅 컴퍼니 | 방향족 헤테로시클릭 융합된 인돌로벤자디아제핀 ｈｃｖ ｎｓ5ｂ 억제제 |
| US8138171B2 (en) * | 2008-03-27 | 2012-03-20 | Bristol-Myers Squibb Company | Dioxolane and dioxolanone fused indolobenzadiazepine HCV NS5B inhibitors |
| 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 |
| 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 |
| 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 |
| CA2822357A1 (en) | 2010-12-22 | 2012-06-28 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| KR20140003521A (ko) | 2010-12-30 | 2014-01-09 | 이난타 파마슈티칼스, 인코포레이티드 | 페난트리딘 매크로사이클릭 ｃ형 간염 세린 프로테아제 억제제 |
| EP2658859A4 (en) | 2010-12-30 | 2014-07-30 | Enanta Pharm Inc | MACROCYCLIC HEPATITIS C SERIN PROTEASE INHIBITORS |
| 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 |
| EP3089757A1 (en) | 2014-01-03 | 2016-11-09 | 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 |
| HRP20090250T1 (hr) | 2004-02-24 | 2009-06-30 | Japan Tobacco | Kondenzirani heterociklički spojevi i njihova upotreba kao inhibitora hcv polimeraze |
| 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 |
| US8097727B2 (en) | 2004-10-13 | 2012-01-17 | Merck Patent Gmbh | N,N′-diphenylurea derivatives which are suitable as kinase inhibitors |
| EP1807403A2 (en) | 2004-10-26 | 2007-07-18 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Tetracyclic indole derivatives as antiviral agents |
| 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
- 2007-02-06 US US11/671,753 patent/US7456165B2/en active Active
- 2007-02-07 EP EP07763294A patent/EP1987038B1/en not_active Not-in-force
- 2007-02-07 AU AU2007211988A patent/AU2007211988B2/en not_active Ceased
- 2007-02-07 PT PT07763294T patent/PT1987038E/pt unknown
- 2007-02-07 JP JP2008554485A patent/JP5147731B2/ja not_active Expired - Fee Related
- 2007-02-07 AT AT07763294T patent/ATE483712T1/de active
- 2007-02-07 WO PCT/US2007/061768 patent/WO2007092888A2/en not_active Ceased
- 2007-02-07 DK DK07763294.1T patent/DK1987038T3/da active
- 2007-02-07 DE DE602007009646T patent/DE602007009646D1/de active Active
- 2007-02-07 SI SI200730453T patent/SI1987038T1/sl unknown
- 2007-02-07 CN CN2007800049834A patent/CN101379066B/zh not_active Expired - Fee Related
- 2007-02-07 PL PL07763294T patent/PL1987038T3/pl unknown
- 2007-02-07 ES ES07763294T patent/ES2352574T3/es active Active
- 2007-02-07 KR KR1020087021812A patent/KR20080102161A/ko not_active Ceased
- 2007-02-07 HR HR20100672T patent/HRP20100672T1/hr 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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