JP3940430B2 - 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 - Google Patents
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 Download PDFInfo
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- JP3940430B2 JP3940430B2 JP2006502472A JP2006502472A JP3940430B2 JP 3940430 B2 JP3940430 B2 JP 3940430B2 JP 2006502472 A JP2006502472 A JP 2006502472A JP 2006502472 A JP2006502472 A JP 2006502472A JP 3940430 B2 JP3940430 B2 JP 3940430B2
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- Prior art keywords
- ethyl
- cyclopentyl
- pyran
- hydroxy
- phenyl
- 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.)
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- 241000711549 Hepacivirus C Species 0.000 title claims description 66
- 239000000203 mixture Substances 0.000 title description 119
- 238000011282 treatment Methods 0.000 title description 18
- 239000003730 rna directed rna polymerase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 489
- -1 [1,2,4] triazolo [1,5-a] pyrimidyl Chemical group 0.000 claims description 277
- 239000000460 chlorine Substances 0.000 claims description 99
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 56
- 125000005843 halogen group Chemical group 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 239000012453 solvate Substances 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 230000002401 inhibitory effect Effects 0.000 claims description 17
- 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 description 14
- 125000004429 atom Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 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 description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 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 description 9
- 239000003814 drug Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 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 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 6
- 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 description 6
- 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 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 2
- 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 description 2
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- 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 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 413
- 238000005481 NMR spectroscopy Methods 0.000 description 395
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 322
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 268
- 239000000243 solution Substances 0.000 description 194
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- 238000004458 analytical method Methods 0.000 description 120
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 81
- 239000007787 solid Substances 0.000 description 79
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 74
- 238000003818 flash chromatography Methods 0.000 description 73
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 71
- 239000012044 organic layer Substances 0.000 description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
- 238000000034 method Methods 0.000 description 62
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- 125000003118 aryl group Chemical group 0.000 description 58
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 56
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- CVWYKCQYEOJYHN-UHFFFAOYSA-N methyl 2-[4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-1,3-dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluorophenyl]-2-methylpropanoate Chemical compound C1=C(F)C(C(C)(C)C(=O)OC)=CC=C1C#CC(O)(C1CCCC1)CC1=CC(=O)OC(C)(C)O1 CVWYKCQYEOJYHN-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- YHXYRISRGHSPNV-UHFFFAOYSA-N methyl 3-(2-hydroxyphenyl)propanoate Chemical compound COC(=O)CCC1=CC=CC=C1O YHXYRISRGHSPNV-UHFFFAOYSA-N 0.000 description 1
- KVHBLGFFJQZLSA-UHFFFAOYSA-N methyl 5-[[2-cyclopentyl-2-[2-(3-fluoro-4-propan-2-yloxyphenyl)ethyl]-4-hydroxy-6-oxo-3h-pyran-5-yl]sulfanyl]-4-methyl-1,2,4-triazole-3-carboxylate Chemical compound CN1C(C(=O)OC)=NN=C1SC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC=C(OC(C)C)C(F)=C1 KVHBLGFFJQZLSA-UHFFFAOYSA-N 0.000 description 1
- KOCIGSXFNBEOHQ-UHFFFAOYSA-N methyl 6-[4-[2-(2-cyclopentyl-4,6-dioxooxan-2-yl)ethyl]-2-fluorophenoxy]-6-methyl-3,5-dioxoheptanoate Chemical compound C1=C(F)C(OC(C)(C)C(=O)CC(=O)CC(=O)OC)=CC=C1CCC1(C2CCCC2)OC(=O)CC(=O)C1 KOCIGSXFNBEOHQ-UHFFFAOYSA-N 0.000 description 1
- IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- KUPGEZYIBUYALR-UHFFFAOYSA-N n-(4-bromo-2-ethylphenyl)-n-methylmethanesulfonamide Chemical compound CCC1=CC(Br)=CC=C1N(C)S(C)(=O)=O KUPGEZYIBUYALR-UHFFFAOYSA-N 0.000 description 1
- GQVXCBNXSSNIAF-UHFFFAOYSA-N n-(4-bromo-2-ethylphenyl)methanesulfonamide Chemical compound CCC1=CC(Br)=CC=C1NS(C)(=O)=O GQVXCBNXSSNIAF-UHFFFAOYSA-N 0.000 description 1
- KKOIRAFXKFYZHQ-UHFFFAOYSA-N n-(4-bromophenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(Br)C=C1 KKOIRAFXKFYZHQ-UHFFFAOYSA-N 0.000 description 1
- OOXSHPNGCZCHMV-SECBINFHSA-N n-[(1r)-1-(4-bromophenyl)ethyl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC(Br)=CC=1)C(=O)C=1C=C(C)ON=1 OOXSHPNGCZCHMV-SECBINFHSA-N 0.000 description 1
- DRRCKKJEBGEBGR-SSDOTTSWSA-N n-[(1r)-1-(4-bromophenyl)ethyl]acetamide Chemical compound CC(=O)N[C@H](C)C1=CC=C(Br)C=C1 DRRCKKJEBGEBGR-SSDOTTSWSA-N 0.000 description 1
- OWMZZHQTGQTCTI-UHFFFAOYSA-N n-[1-[4-[2-(2-cyclopentyl-4,6-dioxooxan-2-yl)ethyl]phenyl]ethyl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound C=1C=C(CCC2(OC(=O)CC(=O)C2)C2CCCC2)C=CC=1C(C)NC(=O)C=1C=C(C)ON=1 OWMZZHQTGQTCTI-UHFFFAOYSA-N 0.000 description 1
- UQRIHERCVWFZON-UHFFFAOYSA-N n-[1-[4-[2-(2-cyclopentyl-4,6-dioxooxan-2-yl)ethyl]phenyl]ethyl]acetamide Chemical compound C1=CC(C(NC(C)=O)C)=CC=C1CCC1(C2CCCC2)OC(=O)CC(=O)C1 UQRIHERCVWFZON-UHFFFAOYSA-N 0.000 description 1
- VBGVBYKKIRNXSG-UHFFFAOYSA-N n-[1-[4-[2-(2-cyclopentyl-4,6-dioxooxan-2-yl)ethyl]phenyl]ethyl]methanesulfonamide Chemical compound C1=CC(C(NS(C)(=O)=O)C)=CC=C1CCC1(C2CCCC2)OC(=O)CC(=O)C1 VBGVBYKKIRNXSG-UHFFFAOYSA-N 0.000 description 1
- OUSDZTAXOPRYDK-UHFFFAOYSA-N n-[2-[3-[2-(2-cyclopentyl-4,6-dioxooxan-2-yl)ethyl]phenyl]-2-methylpropyl]-1h-pyrazole-5-carboxamide Chemical compound C=1C=CC(CCC2(OC(=O)CC(=O)C2)C2CCCC2)=CC=1C(C)(C)CNC(=O)C=1C=CNN=1 OUSDZTAXOPRYDK-UHFFFAOYSA-N 0.000 description 1
- OTZCBNXTACBBEX-UHFFFAOYSA-N n-[2-[3-[2-(2-cyclopentyl-4,6-dioxooxan-2-yl)ethyl]phenyl]-2-methylpropyl]-3-(furan-2-yl)propanamide Chemical compound C=1C=CC(CCC2(OC(=O)CC(=O)C2)C2CCCC2)=CC=1C(C)(C)CNC(=O)CCC1=CC=CO1 OTZCBNXTACBBEX-UHFFFAOYSA-N 0.000 description 1
- LVIMKTAOFADLLL-UHFFFAOYSA-N n-[2-[3-[2-(2-cyclopentyl-4,6-dioxooxan-2-yl)ethyl]phenyl]-2-methylpropyl]-4,5-dimethylfuran-2-carboxamide Chemical compound O1C(C)=C(C)C=C1C(=O)NCC(C)(C)C1=CC=CC(CCC2(OC(=O)CC(=O)C2)C2CCCC2)=C1 LVIMKTAOFADLLL-UHFFFAOYSA-N 0.000 description 1
- WTYYHMUEZOVGKG-UHFFFAOYSA-N n-[2-[3-[2-(2-cyclopentyl-4,6-dioxooxan-2-yl)ethyl]phenyl]-2-methylpropyl]-6-oxo-1h-pyrazine-3-carboxamide Chemical compound C=1C=CC(CCC2(OC(=O)CC(=O)C2)C2CCCC2)=CC=1C(C)(C)CNC(=O)C1=CN=C(O)C=N1 WTYYHMUEZOVGKG-UHFFFAOYSA-N 0.000 description 1
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- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
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- 229920001277 pectin Polymers 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
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- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
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- 239000008363 phosphate buffer Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical class [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 230000004853 protein function Effects 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
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- 230000002285 radioactive effect Effects 0.000 description 1
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- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- DXIAGEFOFLYATE-UHFFFAOYSA-N s-pyridin-2-yl 2-(5-methoxy-2,3-dihydro-1h-inden-1-yl)ethanethioate Chemical compound C1CC2=CC(OC)=CC=C2C1CC(=O)SC1=CC=CC=N1 DXIAGEFOFLYATE-UHFFFAOYSA-N 0.000 description 1
- PPVKUHRBHDJUMR-UHFFFAOYSA-N s-pyridin-2-yl 3-(4-methoxyphenyl)propanethioate Chemical compound C1=CC(OC)=CC=C1CCC(=O)SC1=CC=CC=N1 PPVKUHRBHDJUMR-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- 239000012047 saturated solution Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- 239000007790 solid phase Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
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- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- BZDQLMREXSQLLN-UHFFFAOYSA-N tert-butyl n-[2-(3-bromophenyl)-2-methylpropyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC(C)(C)C1=CC=CC(Br)=C1 BZDQLMREXSQLLN-UHFFFAOYSA-N 0.000 description 1
- IOFODOSKMQZDMG-UHFFFAOYSA-N tert-butyl n-[2-[3-[2-(2-cyclopentyl-4,6-dioxooxan-2-yl)ethyl]phenyl]-2-methylpropyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC(C)(C)C1=CC=CC(CCC2(OC(=O)CC(=O)C2)C2CCCC2)=C1 IOFODOSKMQZDMG-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- 125000001583 thiepanyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 201000001862 viral hepatitis Diseases 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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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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| WO2007010350A1 (en) * | 2005-07-19 | 2007-01-25 | Pfizer Products Inc. | Synthesis of therapeutic diphenyl ethers |
| CN102336758A (zh) | 2005-08-24 | 2012-02-01 | 辉瑞有限公司 | 作为hcv聚合酶抑制剂的化合物及组合物 |
| 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 |
| WO2008137778A2 (en) | 2007-05-04 | 2008-11-13 | Cardiome Pharma Corp. | Controlled release oral formulations of ion channel modulating compounds and related methods for preventing arrhythmia |
| ES2381410T3 (es) | 2007-05-04 | 2012-05-28 | Vertex Pharmceuticals Incorporated | Terapia de combinación paa el tratamiento de infecciones por VHC |
| WO2009023179A2 (en) * | 2007-08-10 | 2009-02-19 | Genelabs Technologies, Inc. | Nitrogen containing bicyclic chemical entities for treating viral infections |
| JP5820722B2 (ja) | 2008-06-06 | 2015-11-24 | スシネキス インク | シクロスポリン類似体及びhcv感染の治療におけるその使用 |
| SI2320905T1 (sl) | 2008-08-11 | 2017-10-30 | Glaxosmithkline Llc Corporation Service Company | Novi adeninski derivati |
| UA103195C2 (uk) | 2008-08-11 | 2013-09-25 | Глаксосмитклайн Ллк | Похідні пурину для застосування у лікуванні алергій, запальних та інфекційних захворювань |
| JP2011530562A (ja) | 2008-08-11 | 2011-12-22 | グラクソスミスクライン エルエルシー | アレルギー性、炎症性及び感染性疾患治療用のプリン誘導体 |
| MX2011010058A (es) * | 2009-03-25 | 2011-10-11 | Abbott Lab | Compuestos antivirales y usos de los mismos. |
| US8957254B2 (en) | 2009-07-06 | 2015-02-17 | Solvay Sa | Process for chemical synthesis from an alkenone made from a halogenated precursor |
| US8575340B2 (en) | 2010-02-10 | 2013-11-05 | Glaxosmithkline Llc | Purine derivatives and their pharmaceutical uses |
| EP2534149B1 (en) | 2010-02-10 | 2014-10-15 | GlaxoSmithKline LLC | 6-amino-2-{[(1s)-1-methylbutyl]oxy}-9-[5-(1-piperidinyl)pentyl]-7,9-dihydro-8h-purin-8-one maleate |
| WO2011159920A1 (en) * | 2010-06-17 | 2011-12-22 | Concert Pharmaceuticals, Inc. | [5,6]-dihydro-2h-pyran-2-one derivatives |
| JP6250394B2 (ja) | 2010-08-19 | 2017-12-20 | バック・インスティテュート・フォー・リサーチ・オン・エイジング | 軽度の認知障害(mci)および関連障害の処置方法 |
| PE20140570A1 (es) | 2011-07-01 | 2014-04-28 | Bayer Ip Gmbh | Pirrolotriazinas sustituidas con hidroximetilarilo y sus usos |
| US20150133669A1 (en) | 2012-05-22 | 2015-05-14 | Actelion Pharmaceuticals Ltd. | New process for the preparation of 2-cyclopentyl-6-methoxy-isonicotinic acid |
| MX2016004540A (es) * | 2013-10-11 | 2016-07-21 | Hoffmann La Roche | Tiazolopirimidinonas como moduladores de la actividad de receptores de n-metil-d-aspartato (nmda). |
| 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. |
| EP3283487B1 (en) | 2015-04-15 | 2019-10-16 | H. Hoffnabb-La Roche Ag | Pyridopyrimidinones and their use as nmda receptor modulators |
| CN108026074A (zh) | 2015-09-28 | 2018-05-11 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性杂环衍生物 |
| TWI704154B (zh) | 2015-12-03 | 2020-09-11 | 英商葛蘭素史克智慧財產發展有限公司 | 新穎化合物 |
| JP7114076B2 (ja) | 2015-12-22 | 2022-08-08 | シャイ・セラピューティクス・エルエルシー | がん及び炎症性疾患の処置のための化合物 |
| HRP20220936T1 (hr) | 2016-04-07 | 2022-10-28 | Glaxosmithkline Intellectual Property Development Limited | Heterociklički amidi korisni kao modulatori proteina |
| 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 |
| JP7514005B2 (ja) | 2017-06-21 | 2024-07-10 | シャイ・セラピューティクス・エルエルシー | がん、炎症性疾患、ラソパシー、及び線維性疾患の治療のためのrasスーパーファミリーと相互作用する化合物 |
| CA3077337A1 (en) | 2017-10-05 | 2019-04-11 | Glaxosmithkline Intellectual Property Development Limited | Modulators of stimulator of interferon genes (sting) |
| US20210238172A1 (en) | 2017-10-05 | 2021-08-05 | Glaxosmithkline Intellectual Property Development Limited | Heterocyclic amides useful as protein modulators and methods of using the same |
| US20210380626A1 (en) | 2018-02-02 | 2021-12-09 | Maverix Oncology, Inc. | Novel small molecule drug conjugates of gemcitabine derivatives |
| PE20210367A1 (es) | 2018-02-02 | 2021-02-26 | Maverix Oncology Inc | Conjugados de farmacos de molecula pequena de monofosfato de gemcitabina |
| 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 |
| JP7407461B2 (ja) | 2018-12-19 | 2024-01-04 | シャイ・セラピューティクス・エルエルシー | がん、炎症性疾患、ras病、及び線維性疾患の処置のためのrasスーパーファミリーと相互作用する化合物 |
| JP2022533194A (ja) | 2019-05-16 | 2022-07-21 | スティングセラ インコーポレイテッド | ベンゾ[b][1,8]ナフチリジン酢酸誘導体および使用方法 |
| US20220227761A1 (en) | 2019-05-16 | 2022-07-21 | Stingthera, Inc. | Oxoacridinyl acetic acid derivatives and methods of use |
| GB201910305D0 (en) | 2019-07-18 | 2019-09-04 | Ctxt Pty Ltd | Compounds |
| GB201910304D0 (en) | 2019-07-18 | 2019-09-04 | Ctxt Pty Ltd | Compounds |
| CN114981265B (zh) | 2019-12-18 | 2025-01-03 | Ctxt私人有限公司 | 化合物 |
| 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 |
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| 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 |
| CA1144937A (en) | 1977-12-22 | 1983-04-19 | Dke J.E. Helgstrand | Aromatic derivatives, pharmaceutical compositions and methods for combatting virus infections |
| 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 |
| WO1995003056A1 (en) | 1993-07-19 | 1995-02-02 | Tokyo Tanabe Company Limited | Hepatitis c virus proliferation inhibitor |
| SK283240B6 (sk) | 1993-11-19 | 2003-04-01 | Parke, Davis & Company | 5,6-Dihydropyrónové deriváty ako inhibítory proteázy a protivírusové činidlá a farmaceutická kompozícia obsahujúca tieto deriváty |
| US6005103A (en) | 1993-11-19 | 1999-12-21 | Warner-Lambert Company | Pyrone derivatives as protease inhibitors and antiviral agents |
| US5504104A (en) | 1993-11-19 | 1996-04-02 | Warner-Lambert Company | Tricyclic pyrone derivatives as protease inhibitors and antiviral agents |
| US5789440A (en) | 1993-11-19 | 1998-08-04 | Warner-Lambert Company | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
| DE69433705T2 (de) | 1993-11-19 | 2005-03-10 | Parke, Davis & Company | 5,6-Dihydropyronderivate als Proteaseinhibitoren und Antiviralmittel |
| US5834506A (en) | 1996-11-01 | 1998-11-10 | Warner-Lambert Company | Dihydropyrones with improved antiviral activity |
| KR20010085780A (ko) | 1998-09-11 | 2001-09-07 | 로즈 암스트롱, 크리스틴 에이. 트러트웨인 | Hiv 프로테아제 억제제 |
| 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 |
| ATE337309T1 (de) * | 2002-04-01 | 2006-09-15 | Pfizer | Pyranon- und pyrandioninhibitoren der rna- abhängigen rna-polymerase des hepatitis-c-virus |
| 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 |
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2003
- 2003-11-19 US US10/718,337 patent/US7148226B2/en not_active Expired - Fee Related
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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
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2005
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Also Published As
| Publication number | Publication date |
|---|---|
| MXPA05007133A (es) | 2005-08-29 |
| WO2004074270A2 (en) | 2004-09-02 |
| WO2004074270A3 (en) | 2004-12-23 |
| NL1025544A1 (nl) | 2004-08-24 |
| US7473790B2 (en) | 2009-01-06 |
| IS7896A (is) | 2005-06-16 |
| US20060189681A1 (en) | 2006-08-24 |
| US20040224960A1 (en) | 2004-11-11 |
| UY28192A1 (es) | 2004-09-30 |
| JP2006518370A (ja) | 2006-08-10 |
| CA2516235A1 (en) | 2004-09-02 |
| EP1597246A2 (en) | 2005-11-23 |
| PA8596001A1 (es) | 2004-09-16 |
| BRPI0407699A (pt) | 2006-02-07 |
| PE20050289A1 (es) | 2005-04-29 |
| US7148226B2 (en) | 2006-12-12 |
| AU2004213247A1 (en) | 2004-09-02 |
| TW200426143A (en) | 2004-12-01 |
| AR044749A1 (es) | 2005-10-05 |
| US20050176701A1 (en) | 2005-08-11 |
| NL1025544C2 (nl) | 2006-05-09 |
| WO2004074270B1 (en) | 2005-03-17 |
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