JP2006518370A5 - - Google Patents
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- Publication number
- JP2006518370A5 JP2006518370A5 JP2006502472A JP2006502472A JP2006518370A5 JP 2006518370 A5 JP2006518370 A5 JP 2006518370A5 JP 2006502472 A JP2006502472 A JP 2006502472A JP 2006502472 A JP2006502472 A JP 2006502472A JP 2006518370 A5 JP2006518370 A5 JP 2006518370A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- hydroxy
- cyclopentyl
- pyran
- triazolo
- 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 [1,2,4] triazolo [1,5-a] pyrimidyl Chemical group 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 7
- NGAVZHRDKFSJNM-UHFFFAOYSA-N 5-[(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-cyclopentyl-2-[2-(5-ethyl-4-hydroxy-2-methoxyphenyl)ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound C1=C(O)C(CC)=CC(CCC2(OC(=O)C(CC3=NN4C=C(Cl)C=NC4=N3)=C(O)C2)C2CCCC2)=C1OC NGAVZHRDKFSJNM-UHFFFAOYSA-N 0.000 claims 4
- 241000711549 Hepacivirus C Species 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- NPGGCRSEWDCBFP-UHFFFAOYSA-N 2-[4-[2-[2-cyclopentyl-5-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4,6-dioxooxan-2-yl]ethyl]-2-fluorophenyl]-2-methylpropanenitrile Chemical compound N=1N2C=C(C)C=NC2=NC=1CC(C(O1)=O)C(=O)CC1(C1CCCC1)CCC1=CC=C(C(C)(C)C#N)C(F)=C1 NPGGCRSEWDCBFP-UHFFFAOYSA-N 0.000 claims 3
- HOCQEMLXZVMLIA-UHFFFAOYSA-N 2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-[2-(5-ethyl-4-hydroxy-2-methoxyphenyl)ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound C1=C(O)C(CC)=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1OC HOCQEMLXZVMLIA-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- SGSKJWYJGCQGSG-UHFFFAOYSA-N 1-[4-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3h-pyran-2-yl]ethyl]-2-fluorophenyl]cyclopropane-1-carbonitrile Chemical compound N1=C2N=C(C)C=C(C)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC(C=C1F)=CC=C1C1(C#N)CC1 SGSKJWYJGCQGSG-UHFFFAOYSA-N 0.000 claims 2
- CKPQCJDUJDHMOH-UHFFFAOYSA-N 2-[2-(3-chloro-4-propan-2-yloxyphenyl)ethyl]-2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C(C)=CC(C)=NC3=N2)=C(O)C1 CKPQCJDUJDHMOH-UHFFFAOYSA-N 0.000 claims 2
- TZGFGNCLAGKSJH-UHFFFAOYSA-N 2-[2-(3-tert-butylphenyl)ethyl]-2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound N1=C2N=C(C)C=C(C)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC=CC(C(C)(C)C)=C1 TZGFGNCLAGKSJH-UHFFFAOYSA-N 0.000 claims 2
- VWRCELVMTVAQKW-UHFFFAOYSA-N 2-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-2-cyclopentyl-4-hydroxy-5-(imidazo[1,2-a]pyrimidin-2-ylmethyl)-3h-pyran-6-one Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1CCC1(C2CCCC2)OC(=O)C(CC=2N=C3N=CC=CN3C=2)=C(O)C1 VWRCELVMTVAQKW-UHFFFAOYSA-N 0.000 claims 2
- VVCIXSGSTPOQAC-UHFFFAOYSA-N 2-[4-[2-[2-cyclopentyl-4-hydroxy-5-[(1-methylindol-5-yl)methyl]-6-oxo-3h-pyran-2-yl]ethyl]-2-fluorophenyl]-2-methylpropanenitrile Chemical compound C=1C=C2N(C)C=CC2=CC=1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC=C(C(C)(C)C#N)C(F)=C1 VVCIXSGSTPOQAC-UHFFFAOYSA-N 0.000 claims 2
- XPRDGKCNHYYXEJ-UHFFFAOYSA-N 2-[4-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3h-pyran-2-yl]ethyl]-2-fluorophenyl]-2-methylpropanenitrile Chemical compound N1=C2N=C(C)C=C(C)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC=C(C(C)(C)C#N)C(F)=C1 XPRDGKCNHYYXEJ-UHFFFAOYSA-N 0.000 claims 2
- CLYTYUYJJROBBW-UHFFFAOYSA-N 2-cyclopentyl-2-[2-(3,5-dichloro-4-ethoxyphenyl)ethyl]-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound C1=C(Cl)C(OCC)=C(Cl)C=C1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C(C)=CC(C)=NC3=N2)=C(O)C1 CLYTYUYJJROBBW-UHFFFAOYSA-N 0.000 claims 2
- JKDXZVICJFGKRT-UHFFFAOYSA-N 2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-[2-(3-ethylphenyl)ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound CCC1=CC=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 JKDXZVICJFGKRT-UHFFFAOYSA-N 0.000 claims 2
- GHQUBVFTDXSBNL-UHFFFAOYSA-N 2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-[2-(3-fluoro-4-propan-2-yloxyphenyl)ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C(C)=CC(C)=NC3=N2)=C(O)C1 GHQUBVFTDXSBNL-UHFFFAOYSA-N 0.000 claims 2
- CAZMNUKVMHMZAD-UHFFFAOYSA-N 7-[[2-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-2-cyclopentyl-4-hydroxy-6-oxo-3h-pyran-5-yl]methyl]-3-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1CCC1(C2CCCC2)OC(=O)C(CC=2N=C3SC=C(C)N3C(=O)C=2)=C(O)C1 CAZMNUKVMHMZAD-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- KUIDQIZSCXAHTF-UHFFFAOYSA-N 1-[2-chloro-4-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3h-pyran-2-yl]ethyl]phenyl]cyclopropane-1-carbonitrile Chemical compound N1=C2N=C(C)C=C(C)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC(C=C1Cl)=CC=C1C1(C#N)CC1 KUIDQIZSCXAHTF-UHFFFAOYSA-N 0.000 claims 1
- FLBSVIOQWZTQGR-UHFFFAOYSA-N 1-[4-[2-[2-cyclopentyl-5-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4,6-dioxooxan-2-yl]ethyl]-2-fluorophenyl]cyclopropane-1-carbonitrile Chemical compound N=1N2C=C(C)C=NC2=NC=1CC(C(O1)=O)C(=O)CC1(C1CCCC1)CCC(C=C1F)=CC=C1C1(C#N)CC1 FLBSVIOQWZTQGR-UHFFFAOYSA-N 0.000 claims 1
- LWRKNHGYEUVPAT-UHFFFAOYSA-N 1-[4-[2-[5-[(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-cyclopentyl-4,6-dioxooxan-2-yl]ethyl]-2-fluorophenyl]cyclopropane-1-carbonitrile Chemical compound C=1C=C(C2(CC2)C#N)C(F)=CC=1CCC1(OC(=O)C(CC2=NN3C=C(Cl)C=NC3=N2)C(=O)C1)C1CCCC1 LWRKNHGYEUVPAT-UHFFFAOYSA-N 0.000 claims 1
- SBPQIILJPDJWAU-UHFFFAOYSA-N 2-[2-(3-chloro-4-hydroxyphenyl)ethyl]-2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound N1=C2N=C(C)C=C(C)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC=C(O)C(Cl)=C1 SBPQIILJPDJWAU-UHFFFAOYSA-N 0.000 claims 1
- OUZYDPGBHPOMKF-UHFFFAOYSA-N 2-[2-(3-chloro-5-ethyl-4-hydroxyphenyl)ethyl]-2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound ClC1=C(O)C(CC)=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 OUZYDPGBHPOMKF-UHFFFAOYSA-N 0.000 claims 1
- RCNNQIBXEMJNFX-UHFFFAOYSA-N 2-[2-(3-chloro-5-ethyl-4-methoxyphenyl)ethyl]-2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound ClC1=C(OC)C(CC)=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 RCNNQIBXEMJNFX-UHFFFAOYSA-N 0.000 claims 1
- MRJXONYVYVXDJG-UHFFFAOYSA-N 2-[2-(3-tert-butyl-4-hydroxyphenyl)ethyl]-2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound N1=C2N=C(C)C=C(C)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC=C(O)C(C(C)(C)C)=C1 MRJXONYVYVXDJG-UHFFFAOYSA-N 0.000 claims 1
- UNESVAYUOLKFAJ-UHFFFAOYSA-N 2-[2-chloro-4-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3h-pyran-2-yl]ethyl]phenyl]-2-methylpropanenitrile Chemical compound N1=C2N=C(C)C=C(C)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC=C(C(C)(C)C#N)C(Cl)=C1 UNESVAYUOLKFAJ-UHFFFAOYSA-N 0.000 claims 1
- TWDSJPZEAXRDOK-UHFFFAOYSA-N 2-[4-[2-[2-cyclopentyl-4,6-dioxo-5-([1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)oxan-2-yl]ethyl]-2-fluorophenyl]-2-methylpropanenitrile Chemical compound C1=C(F)C(C(C)(C#N)C)=CC=C1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C=CC=NC3=N2)C(=O)C1 TWDSJPZEAXRDOK-UHFFFAOYSA-N 0.000 claims 1
- URWAQHBJFIHLHY-UHFFFAOYSA-N 2-[4-[2-[2-cyclopentyl-4-hydroxy-5-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-6-oxo-3h-pyran-2-yl]ethyl]-2,6-difluorophenyl]-2-methylpropanenitrile Chemical compound N=1N2C=C(C)C=NC2=NC=1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC(F)=C(C(C)(C)C#N)C(F)=C1 URWAQHBJFIHLHY-UHFFFAOYSA-N 0.000 claims 1
- USZWVNBDYYFXBZ-UHFFFAOYSA-N 2-[4-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4,6-dioxooxan-2-yl]ethyl]-2-fluorophenyl]-2-ethylbutanenitrile Chemical compound C1=C(F)C(C(CC)(C#N)CC)=CC=C1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C(C)=CC(C)=NC3=N2)C(=O)C1 USZWVNBDYYFXBZ-UHFFFAOYSA-N 0.000 claims 1
- XOUBFQNJPMUSNW-UHFFFAOYSA-N 2-[4-[2-[5-[(4-chloro-1-methylpyrazol-3-yl)methyl]-2-cyclopentyl-4-hydroxy-6-oxo-3h-pyran-2-yl]ethyl]-2-fluorophenyl]-2-methylpropanenitrile Chemical compound CN1C=C(Cl)C(CC=2C(OC(CCC=3C=C(F)C(=CC=3)C(C)(C)C#N)(CC=2O)C2CCCC2)=O)=N1 XOUBFQNJPMUSNW-UHFFFAOYSA-N 0.000 claims 1
- WCVXLDLBIJYJDN-UHFFFAOYSA-N 2-[4-[2-[5-[(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-cyclopentyl-4,6-dioxooxan-2-yl]ethyl]-2-fluorophenyl]-2-methylpropanenitrile Chemical compound C1=C(F)C(C(C)(C#N)C)=CC=C1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C=C(Cl)C=NC3=N2)C(=O)C1 WCVXLDLBIJYJDN-UHFFFAOYSA-N 0.000 claims 1
- NJWQHGWIHBNKMN-UHFFFAOYSA-N 2-cyclopentyl-2-[2-(3-cyclopropyl-4-methoxyphenyl)ethyl]-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound C1=C(C2CC2)C(OC)=CC=C1CCC1(OC(=O)C(CC2=NN3C(C)=CC(C)=NC3=N2)=C(O)C1)C1CCCC1 NJWQHGWIHBNKMN-UHFFFAOYSA-N 0.000 claims 1
- TWCPTZLKZVTRQY-UHFFFAOYSA-N 2-cyclopentyl-2-[2-(3-ethyl-4-hydroxyphenyl)ethyl]-4-hydroxy-5-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-3h-pyran-6-one Chemical compound C1=C(O)C(CC)=CC(CCC2(OC(=O)C(CC3=NN4C=C(C)C=NC4=N3)=C(O)C2)C2CCCC2)=C1 TWCPTZLKZVTRQY-UHFFFAOYSA-N 0.000 claims 1
- MOIPRLHPYAWVEU-UHFFFAOYSA-N 2-cyclopentyl-5-[(5,7-diethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-[2-(3-ethyl-4-hydroxyphenyl)ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound N1=C2N=C(CC)C=C(CC)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC=C(O)C(CC)=C1 MOIPRLHPYAWVEU-UHFFFAOYSA-N 0.000 claims 1
- HAXCDOUQTIDWDJ-UHFFFAOYSA-N 2-cyclopentyl-5-[(5,7-diethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-2-[2-(4-hydroxy-3-propylphenyl)ethyl]-3h-pyran-6-one Chemical compound C1=C(O)C(CCC)=CC(CCC2(OC(=O)C(CC3=NN4C(CC)=CC(CC)=NC4=N3)=C(O)C2)C2CCCC2)=C1 HAXCDOUQTIDWDJ-UHFFFAOYSA-N 0.000 claims 1
- MSFZQOSJVAQTHS-UHFFFAOYSA-N 2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-[2-[3-ethyl-4-(2-hydroxyethoxy)phenyl]ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound C1=C(OCCO)C(CC)=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 MSFZQOSJVAQTHS-UHFFFAOYSA-N 0.000 claims 1
- RQOLVKUPSPRQFO-UHFFFAOYSA-N 5-[(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-cyclopentyl-2-[2-(3-ethyl-4-hydroxyphenyl)ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound C1=C(O)C(CC)=CC(CCC2(OC(=O)C(CC3=NN4C=C(Cl)C=NC4=N3)=C(O)C2)C2CCCC2)=C1 RQOLVKUPSPRQFO-UHFFFAOYSA-N 0.000 claims 1
- YZJFMXFFLQTHPW-UHFFFAOYSA-N 6-cyclopentyl-3-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-6-[2-(3-propan-2-ylphenyl)ethyl]oxane-2,4-dione Chemical compound CC(C)C1=CC=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)C(=O)C2)C2CCCC2)=C1 YZJFMXFFLQTHPW-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- HEEDAOMKXXXYRL-UHFFFAOYSA-N n-[2-[4-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3h-pyran-2-yl]ethyl]-2-ethylphenoxy]ethyl]acetamide Chemical compound C1=C(OCCNC(C)=O)C(CC)=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 HEEDAOMKXXXYRL-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 *C(Cc1ccccc1)C(*)(CC(O)=C1*)OC1=O Chemical compound *C(Cc1ccccc1)C(*)(CC(O)=C1*)OC1=O 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44908803P | 2003-02-21 | 2003-02-21 | |
| US47235503P | 2003-05-20 | 2003-05-20 | |
| PCT/IB2004/000493 WO2004074270A2 (en) | 2003-02-21 | 2004-02-09 | Inhibitors of hepatitis c virus rna-dependent rna polymerase, and compositions and treatments using the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006518370A JP2006518370A (ja) | 2006-08-10 |
| JP2006518370A5 true JP2006518370A5 (https=) | 2006-11-24 |
| JP3940430B2 JP3940430B2 (ja) | 2007-07-04 |
Family
ID=32912318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006502472A Expired - Fee Related JP3940430B2 (ja) | 2003-02-21 | 2004-02-09 | Ｃ型肝炎ウイルスｒｎａ依存ｒｎａポリメラーゼ阻害剤ならびにそれを用いた組成物および治療 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US7148226B2 (https=) |
| EP (1) | EP1597246A2 (https=) |
| JP (1) | JP3940430B2 (https=) |
| AR (1) | AR044749A1 (https=) |
| AU (1) | AU2004213247A1 (https=) |
| BR (1) | BRPI0407699A (https=) |
| CA (1) | CA2516235A1 (https=) |
| IS (1) | IS7896A (https=) |
| MX (1) | MXPA05007133A (https=) |
| NL (1) | NL1025544C2 (https=) |
| PA (1) | PA8596001A1 (https=) |
| PE (1) | PE20050289A1 (https=) |
| TW (1) | TW200426143A (https=) |
| UY (1) | UY28192A1 (https=) |
| WO (1) | WO2004074270A2 (https=) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60334781D1 (de) * | 2002-03-12 | 2010-12-16 | Merck Sharp & Dohme | Di-aryl-substituierte tetrazol-modulatoren des metabotropen glutamat-rezeptors-5 |
| NZ527142A (en) | 2003-07-23 | 2006-03-31 | Douglas Pharmaceuticals Ltd | A stable suspension formulation |
| UA88909C2 (ru) | 2004-08-18 | 2009-12-10 | Пфайзер Инк. | Ингибиторы рнк-зависимой рнк-полимеразы вируса гепатита с, фармацевтическая композиция на их основе и их применение |
| WO2006035061A1 (en) | 2004-09-30 | 2006-04-06 | Tibotec Pharmaceuticals Ltd. | Hcv inhibiting bi-cyclic pyrimidines |
| JP4521463B2 (ja) | 2005-03-17 | 2010-08-11 | ファイザー株式会社 | 疼痛の治療に有用なｎ−（ｎ−スルホニルアミノメチル）シクロプロパンカルボキサミド誘導体 |
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2003
- 2003-11-19 US US10/718,337 patent/US7148226B2/en not_active Expired - Fee Related
-
2004
- 2004-02-09 WO PCT/IB2004/000493 patent/WO2004074270A2/en not_active Ceased
- 2004-02-09 EP EP04709301A patent/EP1597246A2/en not_active Withdrawn
- 2004-02-09 MX MXPA05007133A patent/MXPA05007133A/es not_active Application Discontinuation
- 2004-02-09 BR BR0407699-0A patent/BRPI0407699A/pt not_active IP Right Cessation
- 2004-02-09 JP JP2006502472A patent/JP3940430B2/ja not_active Expired - Fee Related
- 2004-02-09 AU AU2004213247A patent/AU2004213247A1/en not_active Withdrawn
- 2004-02-09 CA CA002516235A patent/CA2516235A1/en not_active Abandoned
- 2004-02-17 PA PA20048596001A patent/PA8596001A1/es unknown
- 2004-02-17 US US10/783,117 patent/US20040224960A1/en not_active Abandoned
- 2004-02-18 UY UY28192A patent/UY28192A1/es not_active Application Discontinuation
- 2004-02-20 NL NL1025544A patent/NL1025544C2/nl not_active IP Right Cessation
- 2004-02-20 PE PE2004000179A patent/PE20050289A1/es not_active Application Discontinuation
- 2004-02-20 TW TW093104282A patent/TW200426143A/zh unknown
- 2004-02-20 AR ARP040100543A patent/AR044749A1/es unknown
-
2005
- 2005-06-16 IS IS7896A patent/IS7896A/is unknown
-
2006
- 2006-05-08 US US11/382,154 patent/US7473790B2/en not_active Expired - Fee Related
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