JP2006518370A5 - - Google Patents
Download PDFInfo
- 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
Links
- -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 |
|---|---|---|---|---|
| EP1485093B1 (en) * | 2002-03-12 | 2010-11-03 | Merck Sharp & Dohme Corp. | Di-aryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| NZ527142A (en) | 2003-07-23 | 2006-03-31 | Douglas Pharmaceuticals Ltd | A stable suspension formulation |
| AU2005273619B2 (en) | 2004-08-18 | 2009-05-28 | Pfizer Inc. | Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same |
| KR20070058602A (ko) | 2004-09-30 | 2007-06-08 | 티보텍 파마슈티칼즈 리미티드 | Ｈｃｖ 저해 바이-사이클릭 피리미딘 |
| EA200701745A1 (ru) | 2005-03-17 | 2008-06-30 | Пфайзер, Инк. | Циклопропанкарбоксамидные производные |
| US8030318B2 (en) | 2005-03-25 | 2011-10-04 | Tibotec Pharmaceuticals Ltd. | Fused bicyclic inhibitors of HCV |
| AR056347A1 (es) | 2005-05-12 | 2007-10-03 | Tibotec Pharm Ltd | Uso de compuestos de pteridina para fabricar medicamentos y composiciones farmaceuticas |
| TW200716631A (en) | 2005-05-12 | 2007-05-01 | Tibotec Pharm Ltd | Pyrido[2,3-d]pyrimidines useful as HCV inhibitors, and methods for the preparation thereof |
| WO2007010350A1 (en) * | 2005-07-19 | 2007-01-25 | Pfizer Products Inc. | Synthesis of therapeutic diphenyl ethers |
| WO2007023381A1 (en) | 2005-08-24 | 2007-03-01 | Pfizer Inc. | Methods for the preparation of hcv polymerase inhibitors |
| WO2007035816A2 (en) * | 2005-09-20 | 2007-03-29 | Dr. Reddy's Laboratories Ltd. | Paroxetine compositions |
| GB0608899D0 (en) * | 2006-05-05 | 2006-06-14 | Leuven K U Res & Dev | Novel viral replication inhibitors |
| EP2142215B1 (en) | 2007-05-04 | 2012-03-07 | Vertex Pharmceuticals Incorporated | Combination therapy for the treatment of hcv infection |
| EA200971025A1 (ru) | 2007-05-04 | 2010-04-30 | Кардиом Фарма Корп. | Пероральные композиции с регулируемым высвобождением соединений, модулирующих ионные каналы, и связанные с ними способы предупреждения аритмии |
| CA2695989A1 (en) * | 2007-08-10 | 2009-02-19 | Glaxosmithkline Llc | Certain nitrogen containing bicyclic chemical entities for treating viral infections |
| CN102083852A (zh) | 2008-06-06 | 2011-06-01 | 西尼克斯公司 | 环孢菌素类似物及其在治疗hcv感染中的应用 |
| BRPI0917458A2 (pt) | 2008-08-11 | 2015-12-01 | Glaxosmithkline Llc | composto, método de tratamento de doenças e condições, composição farmacêutica, método para tratar ou prevenir doença, e, uso de um composto |
| UA103195C2 (uk) | 2008-08-11 | 2013-09-25 | Глаксосмитклайн Ллк | Похідні пурину для застосування у лікуванні алергій, запальних та інфекційних захворювань |
| BRPI0917013A2 (pt) | 2008-08-11 | 2016-02-16 | Glaxosmithkline Llc | métodos para tratar doenças alérgicas e outras condições inflamatórias, e para tratar ou prevenir doença, composto, composição farmacêutica, e, uso de um composto |
| SG174214A1 (en) | 2009-03-25 | 2011-10-28 | Abbott Lab | Antiviral compounds and uses thereof |
| US8957254B2 (en) | 2009-07-06 | 2015-02-17 | Solvay Sa | Process for chemical synthesis from an alkenone made from a halogenated precursor |
| WO2011098451A1 (en) | 2010-02-10 | 2011-08-18 | Glaxosmithkline Llc | Purine derivatives and their pharmaceutical uses |
| DK2534149T3 (da) | 2010-02-10 | 2015-01-05 | Glaxosmithkline Llc | 6-amino-2-{ [ (1s)-1-methylbutyl]oxy}-9-[5-(1-piperidinyl)pentyl]-7,9-dihydro-8h-purin-8-on-maleat |
| WO2011159920A1 (en) * | 2010-06-17 | 2011-12-22 | Concert Pharmaceuticals, Inc. | [5,6]-dihydro-2h-pyran-2-one derivatives |
| ES2705027T3 (es) | 2010-08-19 | 2019-03-21 | Buck Institute For Age Res | Métodos de tratamiento del deterioro cognitivo leve (DCL) y trastornos relacionados |
| SG195100A1 (en) | 2011-07-01 | 2013-12-30 | Bayer Ip Gmbh | Hydroxymethylaryl-substituted pyrrolotriazines as alk1 inhibitors |
| EP2852575A1 (en) | 2012-05-22 | 2015-04-01 | Actelion Pharmaceuticals Ltd. | New process for the preparation of 2-cyclopentyl-6-methoxy-isonicotinic acid |
| LT3055315T (lt) * | 2013-10-11 | 2018-10-25 | F. Hoffmann-La Roche Ag | Tiazolpirimidinonai kaip nmda receptorių aktyvumo moduliatoriai |
| KR20160124157A (ko) | 2014-02-20 | 2016-10-26 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | 인간 인터페론의 유도인자로서의 피롤로[3,2]피리미딘 유도체 |
| MX2017006302A (es) | 2014-11-13 | 2018-02-16 | Glaxosmithkline Biologicals Sa | Derivados de adenina que son utiles en el tratamiento de enfermedades alergicas u otras afecciones inflamatorias. |
| RU2717665C2 (ru) | 2015-04-15 | 2020-03-24 | Ф. Хоффманн-Ля Рош Аг | Пиридопиримидиноны и их применение в качестве модуляторов рецептора n-метил-d-аспартата |
| EP3356343B1 (en) | 2015-09-28 | 2020-03-18 | Syngenta Participations AG | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| CN107849084B (zh) | 2015-12-03 | 2021-09-14 | 葛兰素史密斯克莱知识产权发展有限公司 | 作为sting调节剂的环状嘌呤二核苷酸 |
| SG11201804901WA (en) | 2015-12-22 | 2018-07-30 | SHY Therapeutics LLC | Compounds for the treatment of cancer and inflammatory disease |
| JP2019510802A (ja) | 2016-04-07 | 2019-04-18 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | タンパク質調節物質として有用な複素環アミド |
| PT3440076T (pt) | 2016-04-07 | 2022-07-29 | Glaxosmithkline Ip Dev Ltd | Amidas heterocíclicas úteis como modeladores de proteína |
| EA201992780A1 (ru) | 2017-06-21 | 2020-06-02 | ШАЙ ТЕРАПЬЮТИКС ЭлЭлСи | Соединения, которые взаимодействуют с суперсемейством ras, для лечения рака, воспалительных заболеваний, ras-опатий и фиброзного заболевания |
| AU2018344902B2 (en) | 2017-10-05 | 2021-06-03 | Glaxosmithkline Intellectual Property Development Limited | Modulators of stimulator of interferon genes (STING) useful in treating HIV |
| CA3077337A1 (en) | 2017-10-05 | 2019-04-11 | Glaxosmithkline Intellectual Property Development Limited | Modulators of stimulator of interferon genes (sting) |
| AU2019216531A1 (en) | 2018-02-02 | 2020-09-24 | Maverix Oncology, Inc. | Small molecule drug conjugates of gemcitabine monophosphate |
| CA3090272A1 (en) | 2018-02-02 | 2019-08-08 | Maverix Oncology, Inc. | Novel small molecule drug conjugates of gemcitabine derivatives |
| GB201807924D0 (en) | 2018-05-16 | 2018-06-27 | Ctxt Pty Ltd | Compounds |
| US12117453B2 (en) | 2018-12-07 | 2024-10-15 | Washington University | Predicting patient response to sodium channel blockers |
| US12391705B2 (en) | 2018-12-19 | 2025-08-19 | Shy Therapeutics, Llc | Compounds that interact with the Ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| WO2020232378A1 (en) | 2019-05-16 | 2020-11-19 | Silicon Swat, Inc. | Benzo[b][1,8]naphthyridine acetic acid derivatives and methods of use |
| US20220227761A1 (en) | 2019-05-16 | 2022-07-21 | Stingthera, Inc. | Oxoacridinyl acetic acid derivatives and methods of use |
| GB201910304D0 (en) | 2019-07-18 | 2019-09-04 | Ctxt Pty Ltd | Compounds |
| GB201910305D0 (en) | 2019-07-18 | 2019-09-04 | Ctxt Pty Ltd | Compounds |
| EP4077318B1 (en) | 2019-12-18 | 2025-10-15 | Ctxt Pty Ltd | Benzimidazole dimers as modulators of sting |
| CN114105745B (zh) * | 2020-08-28 | 2024-07-23 | 广东东阳光药业股份有限公司 | 辛波莫德中间体及其制备方法 |
| CN114234210A (zh) * | 2021-12-23 | 2022-03-25 | 南通万达锅炉有限公司 | 一种石油化工废液集成焚烧锅炉 |
| WO2024028169A1 (en) | 2022-08-01 | 2024-02-08 | Nerviano Medical Sciences S.R.L. | Novel specifically substituted thiophenolic compounds |
| CN115784977A (zh) * | 2023-02-06 | 2023-03-14 | 淄博新农基作物科学有限公司 | 2-氯-3-三氟甲基吡啶的合成工艺 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3786063A (en) * | 1971-05-24 | 1974-01-15 | Universal Oil Prod Co | Thiazolethiosulfonates |
| US3904667A (en) * | 1972-04-06 | 1975-09-09 | Du Pont | 4-Halo-2,5-dialkyl-benzeneacetonitriles |
| CA1140049A (en) * | 1977-12-22 | 1983-01-25 | Dke J.E. Helgstran | Pharmaceutical preparations from derivatives of hydroxycarbonylphosphonic acid |
| US4326058A (en) * | 1979-02-05 | 1982-04-20 | Sumitomo Chemical Company, Limited | Organo-phosphoric esters and their production and use |
| US4489077A (en) * | 1983-03-23 | 1984-12-18 | Warner-Lambert Company | 3-Isoxa-zolyl-2H-1,2-benzothiazine-3-carboxamide, 1,1-dioxides |
| US6174868B1 (en) * | 1992-09-10 | 2001-01-16 | Isis Pharmaceuticals, Inc. | Compositions and methods for treatment of hepatitis C virus-associated diseases |
| US5846964A (en) | 1993-07-19 | 1998-12-08 | Tokyo Tanabe Company Limited | Hepatitis C virus proliferation inhibitor |
| US5504104A (en) * | 1993-11-19 | 1996-04-02 | Warner-Lambert Company | Tricyclic pyrone derivatives as protease inhibitors and antiviral agents |
| RU2140917C1 (ru) | 1993-11-19 | 1999-11-10 | Парк, Дэвис энд Компани | Производные 5,6-дигидропирона и фармацевтическая композиция на их основе |
| FI962021A7 (fi) | 1993-11-19 | 1996-07-12 | Parke Davis & Co | 5,6-dihydropyronijohdannaiset proteaasi-inhibiittoreina ja antiviraali sina aineina |
| US5840751A (en) * | 1993-11-19 | 1998-11-24 | Warner-Lambert Company | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
| US6005103A (en) * | 1993-11-19 | 1999-12-21 | Warner-Lambert Company | Pyrone derivatives as protease inhibitors and antiviral agents |
| US5834506A (en) | 1996-11-01 | 1998-11-10 | Warner-Lambert Company | Dihydropyrones with improved antiviral activity |
| CA2339275A1 (en) * | 1998-09-11 | 2000-03-23 | Warner-Lambert Company | 5,6-dihydro-4-hydroxy-2-pyranones as hiv aspartyl protease inhibitors |
| DE19933767B4 (de) | 1999-07-19 | 2013-10-31 | Volkswagen Ag | Befestigungsanordnung für eine Scheibenwischeranlage an einer Fahrzeugkarosserie |
| US6512006B1 (en) * | 1999-12-09 | 2003-01-28 | Warner-Lambert Company | HIV protease inhibitors |
| EP1256628A3 (en) | 2001-05-10 | 2003-03-19 | Agouron Pharmaceuticals, Inc. | Hepatitis c virus (hcv) ns5b rna polymerase and mutants thereof |
| MXPA04009672A (es) * | 2002-04-01 | 2004-11-12 | Pfizer | Inhibidores de la rna polimerasa dependiente del rna del virus de la hepatitis c, y las composiciones y los tratamientos que usan los mismos. |
| DOP2003000641A (es) | 2002-05-10 | 2003-11-15 | Pfizer | Inhibidores de las arn polimerasa dependiente de arn del virus de las hepatitis c y composiciones y tratamiento que los usan |
-
2003
- 2003-11-19 US US10/718,337 patent/US7148226B2/en not_active Expired - Fee Related
-
2004
- 2004-02-09 AU AU2004213247A patent/AU2004213247A1/en not_active Withdrawn
- 2004-02-09 WO PCT/IB2004/000493 patent/WO2004074270A2/en not_active Ceased
- 2004-02-09 CA CA002516235A patent/CA2516235A1/en not_active Abandoned
- 2004-02-09 EP EP04709301A patent/EP1597246A2/en not_active Withdrawn
- 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 MX MXPA05007133A patent/MXPA05007133A/es not_active Application Discontinuation
- 2004-02-17 US US10/783,117 patent/US20040224960A1/en not_active Abandoned
- 2004-02-17 PA PA20048596001A patent/PA8596001A1/es unknown
- 2004-02-18 UY UY28192A patent/UY28192A1/es not_active Application Discontinuation
- 2004-02-20 PE PE2004000179A patent/PE20050289A1/es not_active Application Discontinuation
- 2004-02-20 AR ARP040100543A patent/AR044749A1/es unknown
- 2004-02-20 NL NL1025544A patent/NL1025544C2/nl not_active IP Right Cessation
- 2004-02-20 TW TW093104282A patent/TW200426143A/zh 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2006518370A5 (https=) | ||
| WO2004074270B1 (en) | Inhibitors of hepatitis c virus rna-dependent rna polymerase, and compositions and treatments using the same | |
| JP2020527560A5 (https=) | ||
| RU2417994C2 (ru) | Производные пиразина, полезные в качестве антагонистов аденозинового рецептора | |
| JP2013544873A5 (https=) | ||
| RU2006116466A (ru) | Сульфоксиминзамещенные пиримидины в качестве ингибиторов cdk и/или vegf, их получение и применение в качестве лекарственных средств | |
| DK2096919T3 (en) | SUBSTITUTED 2,3-DIHYDROIMIDAZO [1,2-C] QUINAZOLINE DERIVATIVES USED FOR TREATING HYPERPROLIFERATIVE DISORDERS AND DISEASES ASSOCIATED WITH ANGIOGENESIS | |
| JP2010523497A5 (https=) | ||
| JP2013519724A5 (https=) | ||
| JP2022502424A5 (https=) | ||
| JP2004534826A5 (https=) | ||
| JP2015502951A5 (https=) | ||
| JP2016520116A5 (https=) | ||
| JP2018507861A5 (https=) | ||
| HRP20210454T1 (hr) | 3-supstituirani 5-amino-6h-tiazolo[4,5-d]pirimidin-2,7-dion spojevi za liječenje i profilaksu virusne infekcije | |
| JP2007529484A5 (https=) | ||
| RU2018133391A (ru) | 1,5-дигидро-4н-пиразоло[3,4-d]пиримидин-4-оны и 1,5-дигидро-4н-пиразоло[4,3-c]пиридин-4-оны в качестве ингибиторов pde1 | |
| JP2015526472A5 (https=) | ||
| JP2014513134A5 (https=) | ||
| RU2001118284A (ru) | Новые соединения триазоло (4,5-D) пиримидина | |
| JP2010510319A5 (https=) | ||
| JP2007534687A5 (https=) | ||
| JP2018529731A5 (https=) | ||
| JP2005504080A5 (https=) | ||
| HRP20121022T1 (hr) | Kondenzirani bicikliäśki pirimidini |