MX2012010216A - Compuestos para el tratamiento de hepatitis c. - Google Patents
Compuestos para el tratamiento de hepatitis c.Info
- Publication number
- MX2012010216A MX2012010216A MX2012010216A MX2012010216A MX2012010216A MX 2012010216 A MX2012010216 A MX 2012010216A MX 2012010216 A MX2012010216 A MX 2012010216A MX 2012010216 A MX2012010216 A MX 2012010216A MX 2012010216 A MX2012010216 A MX 2012010216A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- fluoro
- phenyl
- hydrogen
- carboxamide
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 101
- 208000006454 hepatitis Diseases 0.000 title description 6
- 231100000283 hepatitis Toxicity 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- -1 hydroxyalkyloxy Chemical group 0.000 claims description 147
- 125000000217 alkyl group Chemical group 0.000 claims description 111
- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- 239000001257 hydrogen Substances 0.000 claims description 88
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 79
- 125000005843 halogen group Chemical group 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 38
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 37
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000002393 azetidinyl group Chemical group 0.000 claims description 16
- 125000002757 morpholinyl group Chemical group 0.000 claims description 16
- 125000004193 piperazinyl group Chemical group 0.000 claims description 16
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 16
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 15
- 125000003386 piperidinyl group Chemical group 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 14
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 14
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 14
- 125000005602 azabenzimidazolyl group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000005596 alkyl carboxamido group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
- 239000005977 Ethylene Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000005059 halophenyl group Chemical group 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- LIQVEXOTZPWBDF-UHFFFAOYSA-N 1-benzofuran-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=COC2=C1 LIQVEXOTZPWBDF-UHFFFAOYSA-N 0.000 claims description 6
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000005124 aminocycloalkyl group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- XFURMGJPAIPHLW-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,8-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3N=CC=CC3=CC=2)CC1 XFURMGJPAIPHLW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- MKCPKOUTBSNQHU-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,7-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=NC=CC3=CC=2)CC1 MKCPKOUTBSNQHU-UHFFFAOYSA-N 0.000 claims description 2
- NFWJVZCHHBVHHO-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,6-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=CN=CC3=CC=2)CC1 NFWJVZCHHBVHHO-UHFFFAOYSA-N 0.000 claims description 2
- IUDGYZRLNLWSFI-UHFFFAOYSA-N 4-fluoro-5-[3-fluoro-2-methyl-5-[[1-(1,5-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-2-(4-fluorophenyl)-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=C(F)C=1)C)=CC=1C(=O)NC1(C=2N=C3C=CC=NC3=CC=2)CC1 IUDGYZRLNLWSFI-UHFFFAOYSA-N 0.000 claims description 2
- ONWPMBHQPKIFRV-UHFFFAOYSA-N 4-fluoro-5-[3-fluoro-2-methyl-5-[[1-([1,3]oxazolo[4,5-c]pyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-2-(4-fluorophenyl)-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=C(F)C=1)C)=CC=1C(=O)NC1(C=2OC3=CC=NC=C3N=2)CC1 ONWPMBHQPKIFRV-UHFFFAOYSA-N 0.000 claims description 2
- DODKVWTYKYIFKH-UHFFFAOYSA-N 5-[2-(2-amino-2-oxoethoxy)-4-methoxy-5-[[1-(1,7-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-2-(4-fluorophenyl)-n-methyl-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)OCC(N)=O)=CC=1C(=O)NC1(C=2N=C3C=NC=CC3=CC=2)CC1 DODKVWTYKYIFKH-UHFFFAOYSA-N 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- USBRCLRFNGONSW-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[[1-([1,3]oxazolo[4,5-c]pyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2OC3=CC=NC=C3N=2)CC1 USBRCLRFNGONSW-UHFFFAOYSA-N 0.000 claims 1
- BTMVLRBLGJOLCL-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,5-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=CC=NC3=CC=2)CC1 BTMVLRBLGJOLCL-UHFFFAOYSA-N 0.000 claims 1
- FEGDRSNDNOWJMG-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,6-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=CN=CC3=CC=2)CC1 FEGDRSNDNOWJMG-UHFFFAOYSA-N 0.000 claims 1
- POUBHPCIAURQSZ-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[[1-(1,6-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2N=C3C=CN=CC3=CC=2)CC1 POUBHPCIAURQSZ-UHFFFAOYSA-N 0.000 claims 1
- KNHLOVDKCFESOW-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-5-[5-[[1-(7H-imidazo[4,5-c]pyridin-2-yl)cyclopropyl]carbamoyl]-4-methoxy-2-methylphenyl]-N-methyl-1-benzofuran-3-carboxamide Chemical compound CNC(=O)c1c(oc2ccc(c(F)c12)-c1cc(C(=O)NC2(CC2)C2=NC3=CN=CCC3=N2)c(OC)cc1C)-c1ccc(F)cc1 KNHLOVDKCFESOW-UHFFFAOYSA-N 0.000 claims 1
- WPNSUWPSDTWZLK-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,7-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=NC=CC3=CC=2)CC1 WPNSUWPSDTWZLK-UHFFFAOYSA-N 0.000 claims 1
- RXYMNVJZUGDQRS-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,8-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3N=CC=CC3=CC=2)CC1 RXYMNVJZUGDQRS-UHFFFAOYSA-N 0.000 claims 1
- XVGVBRGTAKDMON-UHFFFAOYSA-N 4-fluoro-5-[3-fluoro-2-methyl-5-[[1-(1,7-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-2-(4-fluorophenyl)-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=C(F)C=1)C)=CC=1C(=O)NC1(C=2N=C3C=NC=CC3=CC=2)CC1 XVGVBRGTAKDMON-UHFFFAOYSA-N 0.000 claims 1
- DRYPDNJBOFSJPB-UHFFFAOYSA-N CC(C(F)=CC(C(NC1(CC1)C1=NC(C=NC=C2)=C2O1)=O)=C1)=C1C1=CC=CC2=C1C(C(NC)=O)=C(C(C=C1)=CC=C1F)O2 Chemical compound CC(C(F)=CC(C(NC1(CC1)C1=NC(C=NC=C2)=C2O1)=O)=C1)=C1C1=CC=CC2=C1C(C(NC)=O)=C(C(C=C1)=CC=C1F)O2 DRYPDNJBOFSJPB-UHFFFAOYSA-N 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
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- 241000711549 Hepacivirus C Species 0.000 abstract description 74
- 238000000034 method Methods 0.000 abstract description 31
- 230000000694 effects Effects 0.000 abstract description 23
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- 238000004128 high performance liquid chromatography Methods 0.000 description 452
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 390
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- 239000002904 solvent Substances 0.000 description 94
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 82
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 80
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 80
- 239000001099 ammonium carbonate Substances 0.000 description 80
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- 229940043376 ammonium acetate Drugs 0.000 description 56
- 238000005481 NMR spectroscopy Methods 0.000 description 50
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000003161 ribonuclease inhibitor Substances 0.000 description 1
- 239000002336 ribonucleotide Substances 0.000 description 1
- 125000002652 ribonucleotide group Chemical group 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000013515 script Methods 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- MKIPOIJQGKXCFG-UHFFFAOYSA-N tert-butyl n-(1-acetylcyclopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1(C(=O)C)CC1 MKIPOIJQGKXCFG-UHFFFAOYSA-N 0.000 description 1
- QRCDHLUHNINTQN-UHFFFAOYSA-N tert-butyl n-(1-carbamimidoylcyclopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1(C(N)=N)CC1 QRCDHLUHNINTQN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31276810P | 2010-03-11 | 2010-03-11 | |
| US13/043,747 US8354410B2 (en) | 2010-03-11 | 2011-03-09 | Compounds for the treatment of hepatitis C |
| PCT/US2011/027823 WO2011112769A1 (en) | 2010-03-11 | 2011-03-10 | Compounds for the treatment of hepatitis c |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2012010216A true MX2012010216A (es) | 2012-10-03 |
Family
ID=43903118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2012010216A MX2012010216A (es) | 2010-03-11 | 2011-03-10 | Compuestos para el tratamiento de hepatitis c. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8354410B2 (enExample) |
| EP (1) | EP2545051B1 (enExample) |
| JP (1) | JP5735551B2 (enExample) |
| KR (1) | KR20130016263A (enExample) |
| CN (1) | CN102892767A (enExample) |
| AU (1) | AU2011224319A1 (enExample) |
| MX (1) | MX2012010216A (enExample) |
| WO (1) | WO2011112769A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103269586B (zh) | 2010-10-26 | 2015-07-15 | 普雷西迪奥制药公司 | 丙型肝炎病毒抑制剂 |
| US8507683B2 (en) * | 2010-12-09 | 2013-08-13 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US9303020B2 (en) | 2012-02-08 | 2016-04-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US9434738B2 (en) | 2013-01-10 | 2016-09-06 | Bristol-Myers Squibb Company | Macrocyclic benzofuran and azabenzofuran compounds for the treatment of hepatitis C |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| EP2961746B1 (en) | 2013-02-28 | 2018-01-03 | Bristol-Myers Squibb Company | Phenylpyrazole derivatives as potent rock1 and rock2 inhibitors |
| WO2014205594A1 (en) * | 2013-06-24 | 2014-12-31 | Merck Sharp & Dohme Corp. | Substituted benzofuran compounds and methods of use thereof for treatment of viral diseases |
| WO2014205592A1 (en) | 2013-06-24 | 2014-12-31 | Merck Sharp & Dohme Corp. | Heterocyclic compounds and methods of use thereof for treatment of hepatitis c |
| US9920036B2 (en) * | 2014-03-21 | 2018-03-20 | Bristol-Myers Squibb Company | Cyanoamino (aza)benzofuran compounds for the treatment of hepatitis C |
| CN105732602B (zh) * | 2015-09-23 | 2017-04-19 | 常州寅盛药业有限公司 | 作为ns4b抑制剂的苯并呋喃类似物 |
| CN114957110B (zh) * | 2021-02-26 | 2026-04-21 | 清华大学 | 一种抗病毒化合物及其制备方法和应用 |
| WO2023208171A1 (zh) * | 2022-04-29 | 2023-11-02 | 清华大学 | PLpro蛋白抑制剂及其制备方法和应用 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57123181A (en) | 1981-01-23 | 1982-07-31 | Mitsubishi Paper Mills Ltd | Preparation of pyrazolo (1,5-a) pyridine derivative |
| CZ20012350A3 (cs) * | 1998-12-24 | 2001-09-12 | Aventis Pharmaceuticals Products Inc. | Substituované (aminoiminomethyl nebo aminomethyl) benzoheteroarylové sloučeniny |
| PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| WO2002078701A1 (en) | 2001-03-30 | 2002-10-10 | Smithkline Beecham Corporation | Use of pyrazolopyridines as therapeutic compounds |
| US7265152B2 (en) | 2002-11-01 | 2007-09-04 | Viropharma Incorporated | Benzofuran compounds, compositions and methods for treatment and prophylaxis of hepatitis C viral infections and associated diseases |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| EP2134683A2 (en) * | 2007-02-12 | 2009-12-23 | Intermune, Inc. | Novel inhibitors hepatitis c virus replication |
| GB0707000D0 (en) | 2007-04-12 | 2007-05-30 | Istituto Di Ricerche D Biolog | Antiviral agents |
| ATE539070T1 (de) | 2008-02-14 | 2012-01-15 | Hoffmann La Roche | Heterozyklische antivirale verbindungen |
| WO2009137500A1 (en) | 2008-05-05 | 2009-11-12 | Wyeth | 6-substituted benzofuran compounds to treat infection with hepatitis c virus |
| WO2009137493A1 (en) | 2008-05-05 | 2009-11-12 | Wyeth | 2-substituted benzofuran compounds to treat infection with hepatitis c virus |
| US7994171B2 (en) * | 2008-09-11 | 2011-08-09 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8048887B2 (en) | 2008-09-11 | 2011-11-01 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8198449B2 (en) | 2008-09-11 | 2012-06-12 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| AR080185A1 (es) | 2010-02-19 | 2012-03-21 | Glaxo Group Ltd | Derivados de acido boronico y benzofurano, composiciones farmaceuticas que los contienen,y uso de los mismos en el tratamiento y/o prevencion de infecciones virales, en particular por el virus de hepatitis c(hcv). |
| DE112011100719B4 (de) | 2010-03-01 | 2015-02-26 | Plascoenergy Ip Holdings, S.L., Bilbao, Schaffhausen Branch | Laterales Transfersystem |
| WO2011106929A1 (en) | 2010-03-02 | 2011-09-09 | Merck Sharp & Dohme Corp. | Inhibitors of hepatitis c virus ns5b polymerase |
| TW201136919A (en) | 2010-03-02 | 2011-11-01 | Merck Sharp & Amp Dohme Corp | Inhibitors of hepatitis C virus NS5B polymerase |
-
2011
- 2011-03-09 US US13/043,747 patent/US8354410B2/en active Active
- 2011-03-10 WO PCT/US2011/027823 patent/WO2011112769A1/en not_active Ceased
- 2011-03-10 AU AU2011224319A patent/AU2011224319A1/en not_active Abandoned
- 2011-03-10 MX MX2012010216A patent/MX2012010216A/es active IP Right Grant
- 2011-03-10 KR KR1020127026466A patent/KR20130016263A/ko not_active Withdrawn
- 2011-03-10 EP EP11708667.8A patent/EP2545051B1/en not_active Not-in-force
- 2011-03-10 JP JP2012557233A patent/JP5735551B2/ja not_active Expired - Fee Related
- 2011-03-10 CN CN2011800236466A patent/CN102892767A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011112769A1 (en) | 2011-09-15 |
| EP2545051B1 (en) | 2017-04-19 |
| US20120059019A1 (en) | 2012-03-08 |
| AU2011224319A1 (en) | 2012-11-01 |
| CN102892767A (zh) | 2013-01-23 |
| KR20130016263A (ko) | 2013-02-14 |
| JP2013522224A (ja) | 2013-06-13 |
| JP5735551B2 (ja) | 2015-06-17 |
| EP2545051A1 (en) | 2013-01-16 |
| US8354410B2 (en) | 2013-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |