JP2012522000A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012522000A5 JP2012522000A5 JP2012502245A JP2012502245A JP2012522000A5 JP 2012522000 A5 JP2012522000 A5 JP 2012522000A5 JP 2012502245 A JP2012502245 A JP 2012502245A JP 2012502245 A JP2012502245 A JP 2012502245A JP 2012522000 A5 JP2012522000 A5 JP 2012522000A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidin
- phenyl
- amino
- group
- alkyl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 207
- -1 C 3-8 carbocycle Chemical group 0.000 claims 152
- 229910052739 hydrogen Inorganic materials 0.000 claims 109
- 239000001257 hydrogen Substances 0.000 claims 108
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 106
- 150000002431 hydrogen Chemical class 0.000 claims 84
- 125000001424 substituent group Chemical group 0.000 claims 82
- 229910052757 nitrogen Inorganic materials 0.000 claims 64
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 61
- 229910052736 halogen Inorganic materials 0.000 claims 54
- 150000002367 halogens Chemical class 0.000 claims 54
- 125000005842 heteroatom Chemical group 0.000 claims 52
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 51
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 51
- 229910052760 oxygen Inorganic materials 0.000 claims 51
- 229910052717 sulfur Inorganic materials 0.000 claims 47
- 150000001875 compounds Chemical class 0.000 claims 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims 43
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 34
- 125000004432 carbon atom Chemical group C* 0.000 claims 31
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 28
- VFNZIDKTFVKAIA-YZNLSBJPSA-N tert-butyl N-[(1R)-2-[(2S)-2-[[4-[3-(4-methoxyphenyl)-5-[[2-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetyl]pyrrolidine-1-carbonyl]amino]-1H-indol-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1=CC(OC)=CC=C1C(C1=C2)=C(C=3C=CC(NC(=O)[C@H]4N(CCC4)C(=O)[C@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)=CC=3)NC1=CC=C2NC(=O)N1C(C(=O)[C@H](NC(=O)OC(C)(C)C)C=2C=CC=CC=2)CCC1 VFNZIDKTFVKAIA-YZNLSBJPSA-N 0.000 claims 28
- 125000003118 aryl group Chemical group 0.000 claims 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 24
- 229910052799 carbon Inorganic materials 0.000 claims 22
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 21
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 20
- 125000003627 8 membered carbocyclic group Chemical group 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 15
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 14
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 13
- 125000004076 pyridyl group Chemical group 0.000 claims 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 12
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 11
- 229910052731 fluorine Inorganic materials 0.000 claims 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 11
- 125000003386 piperidinyl group Chemical group 0.000 claims 11
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 10
- 239000011737 fluorine Substances 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 10
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 208000015181 infectious disease Diseases 0.000 claims 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229960002429 proline Drugs 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- AEDOURZAJMSKMP-HEVIKAOCSA-N (2s)-n-[4-[3-bromo-5-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]-1h-indol-2-yl]phenyl]-1-(2-phenylacetyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC2=CC=C3NC(=C(C3=C2)Br)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)CCN1C(=O)CC1=CC=CC=C1 AEDOURZAJMSKMP-HEVIKAOCSA-N 0.000 claims 3
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 3
- 125000003466 9 membered carbocyclic group Chemical group 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 2
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229940122604 HCV protease inhibitor Drugs 0.000 claims 2
- 229940124772 HCV-NS5B polymerase inhibitor Drugs 0.000 claims 2
- 241000700605 Viruses Species 0.000 claims 2
- 229960005475 antiinfective agent Drugs 0.000 claims 2
- 239000004599 antimicrobial Substances 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000002955 immunomodulating agent Substances 0.000 claims 2
- 229940121354 immunomodulator Drugs 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 230000029812 viral genome replication Effects 0.000 claims 2
- ONQDRMAAHQRIAT-ZTJXFJJRSA-N (2S)-1-[(2R)-2-(dimethylamino)-2-phenylacetyl]-N-[14-[[(2S)-1-[(2R)-2-(dimethylamino)-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]-18-azatetracyclo[9.7.0.02,7.012,17]octadeca-1(11),2(7),3,5,12(17),13,15-heptaen-5-yl]pyrrolidine-2-carboxamide Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C(=O)NC2=CC=C3NC=4C5=CC=C(C=C5CCCC=4C3=C2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 ONQDRMAAHQRIAT-ZTJXFJJRSA-N 0.000 claims 1
- RNNOPRADFYFTQD-URLMMPGGSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-(1h-indol-2-yl)phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@H](C(=O)N2[C@@H](CCC2)C=2NC(=CN=2)C=2C=CC(=CC=2)C=2NC3=CC=CC=C3C=2)N(C)C)=CC=CC=C1 RNNOPRADFYFTQD-URLMMPGGSA-N 0.000 claims 1
- RTMLENPULPASGH-PGSYEJHHSA-N (2s)-1-(2,3-diphenylpropanoyl)-n-[4-[5-[[(2s)-1-(2,3-diphenylpropanoyl)pyrrolidine-2-carbonyl]amino]-1h-indol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C=C(NC3=CC=2)C2=CC=C(C=C2)NC(=O)[C@H]2N(CCC2)C(=O)C(CC=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C(=O)C(C=1C=CC=CC=1)CC1=CC=CC=C1 RTMLENPULPASGH-PGSYEJHHSA-N 0.000 claims 1
- ZWGFJQBNRCTGIS-HEVIKAOCSA-N (2s)-1-(2-phenylacetyl)-n-[4-[5-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]-1h-pyrrolo[3,2-b]pyridin-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CCC1)C(=O)NC=1C=CC(=CC=1)C=1NC2=CC=C(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)N=C2C=1)C(=O)CC1=CC=CC=C1 ZWGFJQBNRCTGIS-HEVIKAOCSA-N 0.000 claims 1
- HPZMZHFCAWVHHF-BCRBLDSWSA-N (2s)-1-(2-phenylacetyl)-n-[8-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]-6,11-dihydro-5h-benzo[a]carbazol-3-yl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CCC1)C(=O)NC=1C=C2CCC=3C4=CC(NC(=O)[C@H]5N(CCC5)C(=O)CC=5C=CC=CC=5)=CC=C4NC=3C2=CC=1)C(=O)CC1=CC=CC=C1 HPZMZHFCAWVHHF-BCRBLDSWSA-N 0.000 claims 1
- FVUOFOYZBNADHI-XCIZVNRNSA-N (2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]-n-[4-[5-[[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]-1-benzofuran-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C(=O)NC=2C=C3C=C(OC3=CC=2)C2=CC=C(C=C2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 FVUOFOYZBNADHI-XCIZVNRNSA-N 0.000 claims 1
- UKJNYHDKMYFUSH-IYTFMMMVSA-N (2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]-n-[4-[5-[[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]-1h-indol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C(=O)NC=2C=C3C=C(NC3=CC=2)C2=CC=C(C=C2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 UKJNYHDKMYFUSH-IYTFMMMVSA-N 0.000 claims 1
- QUBSOKKEAIZSAQ-WPWPIJCXSA-N (2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]-n-[8-[[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]-6,11-dihydro-5h-benzo[a]carbazol-3-yl]pyrrolidine-2-carboxamide Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C(=O)NC2=CC=C3NC=4C5=CC=C(C=C5CCC=4C3=C2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 QUBSOKKEAIZSAQ-WPWPIJCXSA-N 0.000 claims 1
- ALOOORKLRZMRJL-LZCGGXSTSA-N (2s)-1-[(2r)-2-phenyl-2-piperidin-1-ylacetyl]-n-[4-[5-[[(2s)-1-[(2r)-2-phenyl-2-piperidin-1-ylacetyl]pyrrolidine-2-carbonyl]amino]-1h-indol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](C(=O)N2CCC[C@H]2C(=O)NC=2C=C3C=C(NC3=CC=2)C2=CC=C(C=C2)NC(=O)[C@H]2N(CCC2)C(=O)[C@H](N2CCCCC2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCCCC1 ALOOORKLRZMRJL-LZCGGXSTSA-N 0.000 claims 1
- LBXKXAKXTDJHJJ-IYTFMMMVSA-N (2s)-1-[(2r)-2-phenyl-2-pyrrolidin-1-ylacetyl]-n-[4-[5-[[(2s)-1-[(2r)-2-phenyl-2-pyrrolidin-1-ylacetyl]pyrrolidine-2-carbonyl]amino]-1h-indol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](C(=O)N2CCC[C@H]2C(=O)NC=2C=C3C=C(NC3=CC=2)C2=CC=C(C=C2)NC(=O)[C@H]2N(CCC2)C(=O)[C@H](N2CCCC2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCCC1 LBXKXAKXTDJHJJ-IYTFMMMVSA-N 0.000 claims 1
- ZUJFKHIYUQAGAT-SMCANUKXSA-N (2s)-n-(6,11-dihydro-5h-benzo[a]carbazol-3-yl)-1-[(2s)-2-(3,3-dimethylbutanoylamino)-2-phenylacetyl]pyrrolidine-2-carboxamide Chemical compound C1([C@@H](C(=O)N2[C@@H](CCC2)C(=O)NC=2C=C3CCC=4C5=CC=CC=C5NC=4C3=CC=2)NC(=O)CC(C)(C)C)=CC=CC=C1 ZUJFKHIYUQAGAT-SMCANUKXSA-N 0.000 claims 1
- CXUIFOXMAPEXRH-ACHIHNKUSA-N (2s)-n-[4-[3-chloro-5-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]-1h-pyrrolo[2,3-b]pyridin-2-yl]phenyl]-1-(2-phenylacetyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC2=CN=C3NC(=C(C3=C2)Cl)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)CCN1C(=O)CC1=CC=CC=C1 CXUIFOXMAPEXRH-ACHIHNKUSA-N 0.000 claims 1
- MGNATTMMCLVFMH-HEVIKAOCSA-N (2s)-n-[4-[3-fluoro-5-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]-1h-indol-2-yl]phenyl]-1-(2-phenylacetyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC2=CC=C3NC(=C(C3=C2)F)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)CCN1C(=O)CC1=CC=CC=C1 MGNATTMMCLVFMH-HEVIKAOCSA-N 0.000 claims 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- IKFWAKHUXARDDX-HEVIKAOCSA-N 5-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]-2-[4-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1h-indole-3-carboxamide Chemical compound C([C@H]1C(=O)NC2=CC=C3NC(=C(C3=C2)C(=O)N)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)CCN1C(=O)CC1=CC=CC=C1 IKFWAKHUXARDDX-HEVIKAOCSA-N 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- NJQLGSSKALZLQU-JPYDVTDNSA-N CC(C)(C)OC(=O)N[C@@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc(cc1)-c1nc2cc(NC(=O)[C@@H]3CCCN3C(=O)[C@H](NC(=O)OC(C)(C)C)c3ccccc3)ccc2[nH]1)c1ccccc1 Chemical compound CC(C)(C)OC(=O)N[C@@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc(cc1)-c1nc2cc(NC(=O)[C@@H]3CCCN3C(=O)[C@H](NC(=O)OC(C)(C)C)c3ccccc3)ccc2[nH]1)c1ccccc1 NJQLGSSKALZLQU-JPYDVTDNSA-N 0.000 claims 1
- NJQLGSSKALZLQU-YKKXUYLKSA-N CC(C)(C)OC(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc(cc1)-c1nc2cc(NC(=O)[C@@H]3CCCN3C(=O)[C@@H](NC(=O)OC(C)(C)C)c3ccccc3)ccc2[nH]1)c1ccccc1 Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc(cc1)-c1nc2cc(NC(=O)[C@@H]3CCCN3C(=O)[C@@H](NC(=O)OC(C)(C)C)c3ccccc3)ccc2[nH]1)c1ccccc1 NJQLGSSKALZLQU-YKKXUYLKSA-N 0.000 claims 1
- RZFPNUBKDXDHCW-JPYDVTDNSA-N CN[C@@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc2[nH]c(cc2c1)-c1ccc(cc1)-c1cnc([nH]1)[C@@H]1CCCN1C(=O)[C@H](NC)c1ccccc1)c1ccccc1 Chemical compound CN[C@@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc2[nH]c(cc2c1)-c1ccc(cc1)-c1cnc([nH]1)[C@@H]1CCCN1C(=O)[C@H](NC)c1ccccc1)c1ccccc1 RZFPNUBKDXDHCW-JPYDVTDNSA-N 0.000 claims 1
- RZFPNUBKDXDHCW-YKKXUYLKSA-N CN[C@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc2[nH]c(cc2c1)-c1ccc(cc1)-c1cnc([nH]1)[C@@H]1CCCN1C(=O)[C@@H](NC)c1ccccc1)c1ccccc1 Chemical compound CN[C@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc2[nH]c(cc2c1)-c1ccc(cc1)-c1cnc([nH]1)[C@@H]1CCCN1C(=O)[C@@H](NC)c1ccccc1)c1ccccc1 RZFPNUBKDXDHCW-YKKXUYLKSA-N 0.000 claims 1
- GXDIOGAPVJEFJL-UWXQCODUSA-N N1([C@@H](CCC1)C(=O)NC=1C=C2CCCC=3C4=CC(NC(=O)[C@H]5N(CCC5)C(=O)CC=5C=CC=CC=5)=CC=C4NC=3C2=CC=1)C(=O)CC1=CC=CC=C1 Chemical compound N1([C@@H](CCC1)C(=O)NC=1C=C2CCCC=3C4=CC(NC(=O)[C@H]5N(CCC5)C(=O)CC=5C=CC=CC=5)=CC=C4NC=3C2=CC=1)C(=O)CC1=CC=CC=C1 GXDIOGAPVJEFJL-UWXQCODUSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000005130 benzoxazines Chemical class 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- DIQKICKSJXHDFL-YZBUDRBASA-N benzyl (2s)-2-[5-[4-[5-[[(2s)-1-[(2r)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]-1h-indol-2-yl]phenyl]-1h-imidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound C([C@H]1C2=NC=C(N2)C2=CC=C(C=C2)C=2NC3=CC=C(C=C3C=2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](NC(=O)OC(C)(C)C)C=2C=CC=CC=2)CCN1C(=O)OCC1=CC=CC=C1 DIQKICKSJXHDFL-YZBUDRBASA-N 0.000 claims 1
- 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- HKKYCBGKXPTMPI-IOWSJCHKSA-N n-[4-[5-[5-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1,3,4-oxadiazol-2-yl]-1h-indol-2-yl]phenyl]acetamide Chemical compound O1C([C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=NN=C1C(C=C1C=2)=CC=C1NC=2C1=CC=C(NC(C)=O)C=C1 HKKYCBGKXPTMPI-IOWSJCHKSA-N 0.000 claims 1
- JIQHLXQULYNGBC-IYTFMMMVSA-N propan-2-yl N-[(1R)-2-oxo-1-phenyl-2-[(2S)-2-[2-[4-[5-[[(2S)-1-[(2R)-2-phenyl-2-(propan-2-yloxycarbonylamino)acetyl]pyrrolidine-2-carbonyl]amino]-1H-indol-2-yl]phenyl]-1H-imidazol-5-yl]pyrrolidin-1-yl]ethyl]carbamate Chemical compound C1([C@@H](NC(=O)OC(C)C)C(=O)N2CCC[C@H]2C2=CN=C(N2)C2=CC=C(C=C2)C=2NC3=CC=C(C=C3C=2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](NC(=O)OC(C)C)C=2C=CC=CC=2)=CC=CC=C1 JIQHLXQULYNGBC-IYTFMMMVSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- WEDWSADPODEZSW-ATUXXYJQSA-N tert-butyl N-[(1R)-2-[(2S)-2-[6-[5-[[(2S)-1-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]-1H-indol-2-yl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc2[nH]c(cc2c1)-c1ccc2[nH]c(nc2c1)[C@@H]1CCCN1C(=O)[C@H](NC(=O)OC(C)(C)C)c1ccccc1)c1ccccc1 WEDWSADPODEZSW-ATUXXYJQSA-N 0.000 claims 1
- DJHDQHHSWXTPOL-DUBDIQTKSA-N tert-butyl N-[(1R)-2-[(2S)-2-[[4-[3-(cyclopropylcarbamoyl)-5-[[(2S)-1-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]-1H-indol-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1([C@@H](NC(=O)OC(C)(C)C)C(=O)N2CCC[C@H]2C(=O)NC2=CC=C3NC(=C(C3=C2)C(=O)NC2CC2)C2=CC=C(C=C2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](NC(=O)OC(C)(C)C)C=2C=CC=CC=2)=CC=CC=C1 DJHDQHHSWXTPOL-DUBDIQTKSA-N 0.000 claims 1
- AJYSXMGBBDTTAW-SKQWTEPWSA-N tert-butyl n-[(1r)-2-[(2s)-2-[[2-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]-1h-indol-5-yl]carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1([C@@H](NC(=O)OC(C)(C)C)C(=O)N2CCC[C@H]2C(=O)NC=2C=C3C=C(NC3=CC=2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 AJYSXMGBBDTTAW-SKQWTEPWSA-N 0.000 claims 1
- WOXPSJXHTJZPDJ-ODTVBPJYSA-N tert-butyl n-[(1r)-2-[(2s)-2-[[2-[4-[[(2s)-1-acetylpyrrolidine-2-carbonyl]amino]phenyl]-3-fluoro-1h-indol-5-yl]carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound CC(=O)N1CCC[C@H]1C(=O)NC1=CC=C(C2=C(C3=CC(NC(=O)[C@H]4N(CCC4)C(=O)[C@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)=CC=C3N2)F)C=C1 WOXPSJXHTJZPDJ-ODTVBPJYSA-N 0.000 claims 1
- OOASIBIGISWJFA-GMCHKSTQSA-N tert-butyl n-[(1r)-2-[(2s)-2-[[3-fluoro-2-[4-(2-oxopyrrolidin-1-yl)phenyl]-1h-indol-5-yl]carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound O=C([C@@H]1CCCN1C(=O)[C@H](NC(=O)OC(C)(C)C)C=1C=CC=CC=1)NC(C=C1C=2F)=CC=C1NC=2C(C=C1)=CC=C1N1CCCC1=O OOASIBIGISWJFA-GMCHKSTQSA-N 0.000 claims 1
- XUIIRTRGXIYKBA-PHSYWDIOSA-N tert-butyl n-[(1r)-2-[(2s)-2-[[4-[3-(3-methylphenyl)-5-[[(2s)-1-[(2r)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]-1h-indol-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound CC1=CC=CC(C=2C3=CC(NC(=O)[C@H]4N(CCC4)C(=O)[C@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)=CC=C3NC=2C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@H](NC(=O)OC(C)(C)C)C=3C=CC=CC=3)=CC=2)=C1 XUIIRTRGXIYKBA-PHSYWDIOSA-N 0.000 claims 1
- ISVODORPOXOXSK-FIBWVYCGSA-N tert-butyl n-[(1s)-2-[(2s)-2-[[2-(4-acetamidophenyl)-3-chloro-1h-indol-5-yl]carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1=CC(NC(=O)C)=CC=C1C1=C(Cl)C2=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC(C)(C)C)C=3C=CC=CC=3)=CC=C2N1 ISVODORPOXOXSK-FIBWVYCGSA-N 0.000 claims 1
- XTZCHOMMYCPWKW-VMPREFPWSA-N tert-butyl n-[(1s)-2-[(2s)-2-[[4-(5-cyano-1h-indol-2-yl)phenyl]carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1([C@@H](C(=O)N2[C@@H](CCC2)C(=O)NC=2C=CC(=CC=2)C=2NC3=CC=C(C=C3C=2)C#N)NC(=O)OC(C)(C)C)=CC=CC=C1 XTZCHOMMYCPWKW-VMPREFPWSA-N 0.000 claims 1
- IKOODQHLWDYOCK-MXAOVZPPSA-N tert-butyl n-[(1s)-2-[(2s)-2-[[4-[3-fluoro-5-[[(2s)-1-[(2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]-1h-indol-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1([C@H](NC(=O)OC(C)(C)C)C(=O)N2CCC[C@H]2C(=O)NC2=CC=C3NC(=C(C3=C2)F)C2=CC=C(C=C2)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)OC(C)(C)C)C=2C=CC=CC=2)=CC=CC=C1 IKOODQHLWDYOCK-MXAOVZPPSA-N 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- 0 NC(*(CCC1)C1O)=O Chemical compound NC(*(CCC1)C1O)=O 0.000 description 14
- ZGMWGSBSLHOATG-UHFFFAOYSA-N CC1=CC(CN)=CCC1 Chemical compound CC1=CC(CN)=CCC1 ZGMWGSBSLHOATG-UHFFFAOYSA-N 0.000 description 1
- AIICVSNLYYSSLG-UHFFFAOYSA-O CC=C(C)OC([NH2+]C)=C Chemical compound CC=C(C)OC([NH2+]C)=C AIICVSNLYYSSLG-UHFFFAOYSA-O 0.000 description 1
- WXYDHDWIJKEYEB-UHFFFAOYSA-N CCC1N(C)C1 Chemical compound CCC1N(C)C1 WXYDHDWIJKEYEB-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16395809P | 2009-03-27 | 2009-03-27 | |
| US61/163,958 | 2009-03-27 | ||
| US24731809P | 2009-09-30 | 2009-09-30 | |
| US61/247,318 | 2009-09-30 | ||
| PCT/US2010/028653 WO2010111483A1 (en) | 2009-03-27 | 2010-03-25 | Inhibitors of hepatitis c virus replication |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014195016A Division JP5932929B2 (ja) | 2009-03-27 | 2014-09-25 | Ｃ型肝炎ウイルス複製の阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012522000A JP2012522000A (ja) | 2012-09-20 |
| JP2012522000A5 true JP2012522000A5 (OSRAM) | 2013-02-07 |
| JP5913091B2 JP5913091B2 (ja) | 2016-04-27 |
Family
ID=42781502
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012502245A Active JP5913091B2 (ja) | 2009-03-27 | 2010-03-25 | Ｃ型肝炎ウイルス複製の阻害剤 |
| JP2014195016A Active JP5932929B2 (ja) | 2009-03-27 | 2014-09-25 | Ｃ型肝炎ウイルス複製の阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014195016A Active JP5932929B2 (ja) | 2009-03-27 | 2014-09-25 | Ｃ型肝炎ウイルス複製の阻害剤 |
Country Status (40)
Families Citing this family (149)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010075380A1 (en) | 2008-12-23 | 2010-07-01 | Abbott Laboratories | Anti-viral compounds |
| WO2010075376A2 (en) | 2008-12-23 | 2010-07-01 | Abbott Laboratories | Anti-viral compounds |
| US8188132B2 (en) | 2009-02-17 | 2012-05-29 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| US8394968B2 (en) | 2009-02-17 | 2013-03-12 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8242156B2 (en) | 2009-02-17 | 2012-08-14 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| US8673954B2 (en) | 2009-02-27 | 2014-03-18 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US9765087B2 (en) | 2009-02-27 | 2017-09-19 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US8101643B2 (en) | 2009-02-27 | 2012-01-24 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US8507522B2 (en) | 2009-03-06 | 2013-08-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| CN102427729B (zh) | 2009-03-27 | 2014-09-03 | 默沙东公司 | 丙型肝炎病毒复制的抑制剂 |
| US20190127365A1 (en) | 2017-11-01 | 2019-05-02 | Merck Sharp & Dohme Corp. | Inhibitors of hepatitis c virus replication |
| US8796466B2 (en) | 2009-03-30 | 2014-08-05 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TW201038559A (en) | 2009-04-09 | 2010-11-01 | Bristol Myers Squibb Co | Hepatitis C virus inhibitors |
| US8143414B2 (en) | 2009-04-13 | 2012-03-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP2419404B1 (en) | 2009-04-15 | 2015-11-04 | AbbVie Inc. | Anti-viral compounds |
| US9139569B2 (en) | 2009-05-12 | 2015-09-22 | Merck Sharp & Dohme Corp. | Fused tricyclic aryl compounds useful for the treatment of viral diseases |
| RS56654B8 (sr) | 2009-05-13 | 2021-06-30 | Gilead Pharmasset Llc | Antiviralna jedinjenja |
| US8772505B2 (en) | 2009-05-29 | 2014-07-08 | Merck Sharp & Dohme Corp. | Antiviral compounds composed of three aligned aryl moieties to treat diseases such as hepatitis C |
| US8138215B2 (en) | 2009-05-29 | 2012-03-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CA2763140A1 (en) | 2009-05-29 | 2010-12-02 | Schering Corporation | Antiviral compounds composed of three linked aryl moieties to treat diseases such as hepatitis c |
| US8211928B2 (en) | 2009-05-29 | 2012-07-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8716454B2 (en) | 2009-06-11 | 2014-05-06 | Abbvie Inc. | Solid compositions |
| EA020031B1 (ru) | 2009-06-11 | 2014-08-29 | Эббви Бахамаз Лтд. | Противовирусные соединения |
| US8937150B2 (en) | 2009-06-11 | 2015-01-20 | Abbvie Inc. | Anti-viral compounds |
| US9394279B2 (en) | 2009-06-11 | 2016-07-19 | Abbvie Inc. | Anti-viral compounds |
| US8221737B2 (en) | 2009-06-16 | 2012-07-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8609648B2 (en) | 2009-07-02 | 2013-12-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| EP2454254A2 (en) | 2009-07-16 | 2012-05-23 | Vertex Pharmaceuticals Incorporated | Benzimidazole analogues for the treatment or prevention of flavivirus infections |
| EP2473056A4 (en) | 2009-09-04 | 2013-02-13 | Glaxosmithkline Llc | CHEMICAL COMPOUNDS |
| US8822700B2 (en) | 2009-09-11 | 2014-09-02 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US9156818B2 (en) | 2009-09-11 | 2015-10-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8759332B2 (en) | 2009-09-11 | 2014-06-24 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8815928B2 (en) | 2009-09-11 | 2014-08-26 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8927709B2 (en) | 2009-09-11 | 2015-01-06 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8703938B2 (en) | 2009-09-11 | 2014-04-22 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| RU2012116207A (ru) * | 2009-09-24 | 2013-10-27 | Ф.Хоффманн-Ля Рош Аг | Производные индола в качестве модуляторов crac |
| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20110269956A1 (en) | 2009-11-11 | 2011-11-03 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20110281910A1 (en) | 2009-11-12 | 2011-11-17 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US8653070B2 (en) | 2009-12-14 | 2014-02-18 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| CA2785488A1 (en) | 2009-12-22 | 2011-07-21 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds and methods of use thereof for the treatment of viral diseases |
| US8362020B2 (en) | 2009-12-30 | 2013-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CN102843909A (zh) | 2010-01-25 | 2012-12-26 | 埃南塔制药公司 | 丙型肝炎病毒抑制剂 |
| US8933110B2 (en) | 2010-01-25 | 2015-01-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8178531B2 (en) | 2010-02-23 | 2012-05-15 | Enanta Pharmaceuticals, Inc. | Antiviral agents |
| US8623814B2 (en) | 2010-02-23 | 2014-01-07 | Enanta Pharmaceuticals, Inc. | Antiviral agents |
| CN102858157A (zh) | 2010-03-04 | 2013-01-02 | 埃南塔制药公司 | 作为hcv复制的抑制剂的组合药物活性剂 |
| EP2545060B1 (en) * | 2010-03-09 | 2015-11-25 | Merck Sharp & Dohme Corp. | Fused tricyclic silyl compounds and methods of use thereof for the treatment of viral diseases |
| MX2012010918A (es) | 2010-03-24 | 2013-01-18 | Vertex Pharma | Analogos para el tratamiento o prevencion de infecciones por flavivirus. |
| WO2011127350A1 (en) | 2010-04-09 | 2011-10-13 | Enanta Pharmaceuticals, Inc. | Hepatitis c virus inhibitors |
| US9125904B1 (en) | 2010-05-11 | 2015-09-08 | Achillion Pharmaceuticals, Inc. | Biphenyl imidazoles and related compounds useful for treating HCV infections |
| US8778938B2 (en) | 2010-06-04 | 2014-07-15 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| NZ605440A (en) | 2010-06-10 | 2014-05-30 | Abbvie Bahamas Ltd | Solid compositions comprising an hcv inhibitor |
| EP2585447A2 (en) | 2010-06-28 | 2013-05-01 | Vertex Pharmaceuticals Incorporated | Compounds and methods for the treatment or prevention of flavivirus infections |
| JP2013531011A (ja) | 2010-06-28 | 2013-08-01 | バーテックス ファーマシューティカルズ インコーポレイテッド | フラビウイルス感染の処置または予防のための化合物および方法 |
| EP2603080A4 (en) | 2010-08-12 | 2014-01-22 | Enanta Pharm Inc | HEPATITIS C-VIRUS HEMMER |
| MX2013001869A (es) | 2010-08-17 | 2013-06-28 | Vertex Pharma | Compuestos y metodos para el tratamiento o prevencion de infecciones virales por flaviviridae. |
| EP2616461A4 (en) | 2010-08-26 | 2014-03-26 | Rfs Pharma Llc | POTENTIVE AND SELECTIVE INHIBITORS OF HEPATITIS C VIRUS |
| EP2621279B1 (en) * | 2010-09-29 | 2018-04-04 | Merck Sharp & Dohme Corp. | Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012040923A1 (en) * | 2010-09-29 | 2012-04-05 | Merck Sharp & Dohme Corp. | Tetracyclic indole derivatives and methods of use thereof for the treatment of viral diseases |
| BR112013007696A2 (pt) * | 2010-09-29 | 2019-09-24 | Merck Sharp & Dohme | composto, composição farmacêutica, usos do referido composto e da referida composição |
| US20130280214A1 (en) * | 2010-09-29 | 2013-10-24 | Merck Sharp & Dohme Corp. | Polycyclic heterocycle derivatives and methods of use thereof for the treatment of viral diseases |
| CN103459399A (zh) * | 2010-09-29 | 2013-12-18 | 默沙东公司 | 用于治疗丙型肝炎病毒感染的四环吲哚衍生物 |
| US20150158909A1 (en) * | 2010-12-15 | 2015-06-11 | Abbevie Inc. | Anti-viral compounds |
| WO2012087976A2 (en) * | 2010-12-21 | 2012-06-28 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| US8552047B2 (en) | 2011-02-07 | 2013-10-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2012122716A1 (en) | 2011-03-17 | 2012-09-20 | Merck Sharp & Dohme Corp. | Tetracyclic xanthene derivatives and methods of use thereof for treatment of viral diseases |
| US8835456B1 (en) | 2011-03-18 | 2014-09-16 | Achillion Pharmaceuticals, Inc. | NS5A inhibitors useful for treating HCV |
| US9156872B2 (en) | 2011-04-13 | 2015-10-13 | Merck Sharp & Dohme Corp. | 2′-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| EP2696681B1 (en) | 2011-04-13 | 2018-10-03 | Merck Sharp & Dohme Corp. | 2'-substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| US9546160B2 (en) | 2011-05-12 | 2017-01-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| EP2709455A4 (en) | 2011-05-18 | 2014-11-05 | Enanta Pharm Inc | PROCESSES FOR THE PREPARATION OF 5-AZASPIRO [2.4] HEPTANE-6-CARBOXYLIC ACID AND ITS DERIVATIVES |
| KR101931311B1 (ko) | 2011-05-27 | 2018-12-20 | 아칠리온 파르마세우티칼스 인코포레이티드 | Ｈｃｖ 감염 치료에 유용한 치환된 앨리팬, 시클로팬, 헤테라팬, 헤테로팬, 헤테로-헤테라팬 및 메탈로센 |
| CA2841095A1 (en) | 2011-07-09 | 2013-01-17 | Sunshine Lake Pharma Co., Ltd. | Spiro compounds as hepatitis c virus inhibitors |
| WO2013016499A1 (en) | 2011-07-26 | 2013-01-31 | Vertex Pharmaceuticals Incorporated | Methods for preparation of thiophene compounds |
| AU2012286853A1 (en) | 2011-07-26 | 2013-05-02 | Vertex Pharmaceuticals Incorporated | Thiophene compounds |
| WO2013030750A1 (en) | 2011-09-01 | 2013-03-07 | Lupin Limited | Antiviral compounds |
| SI2709613T2 (sl) | 2011-09-16 | 2020-12-31 | Gilead Pharmasset LLC c/o Gilead Sciences, Inc. | Postopki za zdravljenje HCV |
| KR101326828B1 (ko) | 2011-12-07 | 2013-11-11 | 현대자동차주식회사 | 클램핑 장치용 회전모듈 |
| US9133170B2 (en) * | 2011-12-16 | 2015-09-15 | Hoffmann-La Roche Inc. | Inhibitors of HCV NS5A |
| US9034832B2 (en) | 2011-12-29 | 2015-05-19 | Abbvie Inc. | Solid compositions |
| US9326973B2 (en) | 2012-01-13 | 2016-05-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| IN2014MN01547A (OSRAM) | 2012-02-10 | 2015-05-08 | Lupin Ltd | |
| EP2827876A4 (en) | 2012-03-22 | 2015-10-28 | Alios Biopharma Inc | PHARMACEUTICAL COMBINATIONS WITH A THIONUCLEOTIDE ANALOG |
| EP2887804B1 (en) | 2012-05-22 | 2021-01-27 | Trustees of Dartmouth College | Cycloalkanyl[b]indoles useful as glp-1 modulators |
| TWI610916B (zh) | 2012-08-03 | 2018-01-11 | 廣東東陽光藥業有限公司 | 作爲丙型肝炎抑制劑的橋環化合物及其在藥物中的應用 |
| EP2909210A4 (en) | 2012-10-17 | 2016-04-06 | Merck Sharp & Dohme | 2'-DISUBSTITUTED NUCLEOSIDE DERIVATIVES AND METHOD FOR THE USE THEREOF FOR THE TREATMENT OF VIRUS DISEASES |
| AR092959A1 (es) | 2012-10-17 | 2015-05-06 | Merck Sharp & Dohme | Derivados de nucleosidos 2-metil sustituidos y metodos de uso de los mismos para el tratamiento de enfermedades virales |
| WO2014059901A1 (en) | 2012-10-17 | 2014-04-24 | Merck Sharp & Dohme Corp. | 2'-cyano substituted nucleoside derivatives and methods of use thereof for treatment of viral diseases |
| EP2909172A1 (en) * | 2012-10-17 | 2015-08-26 | F. Hoffmann-La Roche AG | 6-aminoindole derivatives as trp channel antagonists |
| WO2014078463A1 (en) | 2012-11-19 | 2014-05-22 | Merck Sharp & Dohme Corp. | 2 -alkynyl substituted nucleoside derivatives for treating viral diseases |
| TWI585082B (zh) | 2012-11-29 | 2017-06-01 | 廣東東陽光藥業有限公司 | 作爲丙型肝炎抑制劑的螺環化合物、藥物組合物及它們的用途 |
| WO2014082380A1 (en) | 2012-11-29 | 2014-06-05 | Sunshine Lake Pharma Co., Ltd. | Fused ring compounds as hepatitis c virus inhibitors, pharmaceutical compositions and uses thereof |
| WO2014110687A1 (en) * | 2013-01-16 | 2014-07-24 | Merck Sharp & Dohme Corp. | Thiazolyl-substitued tetracyclic compounds and methods of use thereof for treatment of viral diseases |
| WO2014110688A1 (en) * | 2013-01-16 | 2014-07-24 | Merck Sharp & Dohme Corp. | Thiophene- sub stitued tetracyclic compounds and methods of use thereof for the treatment of viral diseases |
| NZ729172A (en) | 2013-01-31 | 2018-06-29 | Gilead Pharmasset Llc | Combination formulation of two antiviral compounds |
| WO2014121417A1 (en) * | 2013-02-07 | 2014-08-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c |
| WO2014121418A1 (en) * | 2013-02-07 | 2014-08-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c |
| TW201526899A (zh) | 2013-02-28 | 2015-07-16 | Alios Biopharma Inc | 醫藥組成物 |
| US11484534B2 (en) | 2013-03-14 | 2022-11-01 | Abbvie Inc. | Methods for treating HCV |
| JP6280573B2 (ja) | 2013-03-14 | 2018-02-14 | 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、（ナンバー２）、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ （Ｎｏ．２） Ｌｉｍｉｔｅｄ | ブロモドメイン阻害薬としてのフロピリジン |
| CN111116563B (zh) * | 2013-06-06 | 2023-07-04 | 上海爱博医药科技有限公司 | 抑制丙肝病毒的化合物、药物组合物及其应用 |
| WO2014205592A1 (en) | 2013-06-24 | 2014-12-31 | Merck Sharp & Dohme Corp. | Heterocyclic compounds and methods of use thereof for treatment of hepatitis c |
| US9717712B2 (en) | 2013-07-02 | 2017-08-01 | Bristol-Myers Squibb Company | Combinations comprising tricyclohexadecahexaene derivatives for use in the treatment of hepatitis C virus |
| US20150023913A1 (en) | 2013-07-02 | 2015-01-22 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| CN105530933B (zh) | 2013-07-17 | 2018-12-11 | 百时美施贵宝公司 | 用于治疗hcv的包含联苯衍生物的组合产品 |
| JP2016529293A (ja) | 2013-08-27 | 2016-09-23 | ギリアド ファーマセット エルエルシー | ２つの抗ウイルス化合物の組合せ製剤 |
| US10167298B2 (en) * | 2013-10-30 | 2019-01-01 | Merck Sharp & Dohme Corp. | Pseudopolymorphs of an HCV NS5A inhibitor and uses thereof |
| WO2015065821A1 (en) * | 2013-10-30 | 2015-05-07 | Merck Sharp & Dohme Corp. | Process for preparing tetracyclic heterocycle compounds |
| WO2015089810A1 (en) * | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Fused tetracyclic heterocyclic compounds and methods of use thereof for the treatment of viral diseases |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| US9738629B2 (en) | 2014-01-23 | 2017-08-22 | Sunshine Lake Pharma Co., Ltd. | Bridged ring compounds as Hepatitis C virus inhibitors, pharmaceutical compositions and uses thereof |
| CN107954997A (zh) * | 2014-02-21 | 2018-04-24 | 常州寅盛药业有限公司 | 作为丙肝病毒抑制剂的联环化合物 |
| WO2015179392A1 (en) * | 2014-05-21 | 2015-11-26 | Bristol-Myers Squibb Company | 2-(aryl- or heteroaryl-)phenyl (aza)benzofuran compounds for the treatment of hepatitis c |
| WO2015184644A1 (zh) * | 2014-06-06 | 2015-12-10 | 爱博新药研发(上海)有限公司 | 抑制丙肝病毒的化合物、药物组合物及其应用 |
| TWI721947B (zh) | 2014-06-11 | 2021-03-21 | 美商基利法瑪席特有限責任公司 | 抗病毒化合物的固態形式 |
| WO2016004899A1 (en) | 2014-07-11 | 2016-01-14 | Merck Sharp & Dohme Corp. | Process for making tetracyclic heterocycle compounds |
| WO2016105670A1 (en) * | 2014-12-22 | 2016-06-30 | Merck Sharp & Dohme Corp. | Solid dispersion formulations of antiviral compounds |
| WO2016126721A1 (en) | 2015-02-02 | 2016-08-11 | Forma Therapeutics, Inc. | 3-aryl-bicyclic [4,5,0] hydroxamic acids as hdac inhibitors |
| WO2016126726A1 (en) | 2015-02-02 | 2016-08-11 | Forma Therapeutics, Inc. | Bicyclic [4,6,0] hydroxamic acids as hdac6 inhibitors |
| US10457690B2 (en) | 2015-06-04 | 2019-10-29 | Merck Sharp & Dohme Corp. | Process for preparing substituted tetracyclic heterocycle compounds |
| WO2017023631A1 (en) | 2015-08-06 | 2017-02-09 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| WO2017076201A1 (zh) * | 2015-11-06 | 2017-05-11 | 江苏豪森药业集团有限公司 | Hcv抑制剂、其制备方法与应用 |
| IL286839B (en) * | 2016-02-19 | 2022-08-01 | Pmv Pharmaceuticals Inc | Propyne-indole compounds |
| WO2017181383A1 (en) | 2016-04-21 | 2017-10-26 | Merck Sharp & Dohme Corp. | Hepatitis c virus inhibitors |
| EP4483875A3 (en) | 2016-05-10 | 2025-04-02 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
| CN109562107A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的杂环降解决定子体 |
| EP3455219A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | AMINE-RELATED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| EP3472131B1 (en) | 2016-06-17 | 2020-02-19 | Forma Therapeutics, Inc. | 2-spiro-5- and 6-hydroxamic acid indanes as hdac inhibitors |
| WO2017223012A1 (en) | 2016-06-20 | 2017-12-28 | Merck Sharp & Dohme Corp. | Cyclic phosphate substituted nucleoside compounds and methods of use thereof for the treatment of viral diseases |
| EP3473639B1 (en) | 2016-06-21 | 2023-03-29 | Zhejiang Palo Alto Pharmaceuticals, Inc | Hepatitis c virus inhibitor and application |
| WO2018032468A1 (en) * | 2016-08-18 | 2018-02-22 | Merck Sharp & Dohme Corp. | Heterocycle-substitued tetracyclic compounds and methods of use thereof for treatment of viral diseases |
| WO2018032467A1 (en) | 2016-08-18 | 2018-02-22 | Merck Sharp & Dohme Corp. | Chromane-substitued tetracyclic compounds and uses thereof for treatment of viral diseases |
| KR101887969B1 (ko) * | 2016-08-30 | 2018-08-13 | 한국과학기술연구원 | 항바이러스 활성을 가지는 카르바졸 화합물 |
| CN109134600B (zh) * | 2017-06-19 | 2021-07-20 | 杭州国谋生物科技有限公司 | 作为丙型肝炎抑制剂的烷基及杂环化合物及其在药物中的应用 |
| EP3641762B1 (en) | 2017-06-20 | 2026-02-18 | C4 Therapeutics, Inc. | N/o-linked degrons and degronimers for protein degradation |
| CN109232612A (zh) * | 2017-07-11 | 2019-01-18 | 周龙兴 | 抑制丙肝病毒的化合物、药物组合物及其用途 |
| WO2019057946A1 (en) | 2017-09-25 | 2019-03-28 | F. Hoffmann-La Roche Ag | MULTI-CYCLIC AROMATIC COMPOUNDS AS D-FACTOR INHIBITORS |
| US12441762B2 (en) * | 2019-06-07 | 2025-10-14 | University Of Massachusetts | Hepatitis c virus NS3/4A protease inhibitors |
| SMT202500339T1 (it) | 2019-09-23 | 2025-11-10 | Pmv Pharmaceuticals Inc | Metodi e composti per ripristinare la funzione di p53 mutante |
| US12570645B2 (en) | 2020-06-22 | 2026-03-10 | Pmv Pharmaceuticals, Inc. | Uses of p53 x-ray co-crystal structures |
| WO2021262484A1 (en) | 2020-06-24 | 2021-12-30 | Pmv Pharmaceuticals, Inc. | Combination therapy for treatment of cancer |
| JP7725617B2 (ja) | 2021-05-21 | 2025-08-19 | ギリアード サイエンシーズ， インコーポレイテッド | ジカウイルス阻害剤としての五環式誘導体 |
| CA3219397A1 (en) | 2021-05-21 | 2022-11-24 | Gilead Sciences, Inc. | Tetracyclic compounds for the treatment of zika virus infection |
| EP4637749A2 (en) * | 2022-12-19 | 2025-10-29 | Nimbus Clio, Inc. | Cbl-b modulators and uses thereof |
| CN117362162A (zh) * | 2023-08-30 | 2024-01-09 | 中国科学院大连化学物理研究所 | 一种羰基类化合物的制备方法 |
| WO2025199211A1 (en) * | 2024-03-19 | 2025-09-25 | Yale University | Imidazopyridines and imidazopyrimidines, and methods of using same |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH478208A (de) * | 1965-08-05 | 1969-09-15 | Sandoz Ag | Verfahren zur Herstellung von Perinonfarbstoffen |
| JP3927630B2 (ja) | 1996-09-27 | 2007-06-13 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ウイルス感染症の予防・治療剤 |
| CA2422488A1 (en) | 2000-09-20 | 2002-03-28 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | 4-amino-quinazolines |
| EP2335700A1 (en) * | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis C virus polymerase inhibitors with a heterobicylic structure |
| RU2303595C2 (ru) | 2003-07-10 | 2007-07-27 | Пэредайм Терапьютикс Лтд. | Силиконовые соединения и их применение (варианты) |
| PT1719773E (pt) * | 2004-02-24 | 2009-06-03 | Japan Tobacco Inc | Compostos heterotetracíclicos fundidos e a sua utilização como inibidores da polimerase do hcv |
| US20070049593A1 (en) * | 2004-02-24 | 2007-03-01 | Japan Tobacco Inc. | Tetracyclic fused heterocyclic compound and use thereof as HCV polymerase inhibitor |
| WO2007084413A2 (en) | 2004-07-14 | 2007-07-26 | Ptc Therapeutics, Inc. | Methods for treating hepatitis c |
| US7153848B2 (en) | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| CA2585084A1 (en) | 2004-10-26 | 2006-05-04 | Immacolata Conte | Tetracyclic indole derivatives as antiviral agents |
| GB2438802A (en) | 2005-02-28 | 2007-12-05 | Univ Rockefeller | Structure of the hepatitis C virus NS5A protein |
| US7994360B2 (en) * | 2005-05-16 | 2011-08-09 | Xtl Biopharmaceuticals Ltd. | Benzofuran compounds |
| US20110104109A1 (en) | 2005-07-13 | 2011-05-05 | Frank Bennett | Tetracyclic indole derivatives and their use for treating or preventing viral infections |
| CA2612442A1 (en) * | 2005-07-14 | 2007-01-18 | Irm Llc | Heterotetracyclic compounds as tpo mimetics |
| US7473784B2 (en) * | 2005-08-01 | 2009-01-06 | Bristol-Myers Squibb Company | Benzothiazole and azabenzothiazole compounds useful as kinase inhibitors |
| FR2894963A1 (fr) | 2005-12-16 | 2007-06-22 | Inst Nat Sante Rech Med | Nouveaux composes interagissant avec pea-15 |
| US7745636B2 (en) | 2006-08-11 | 2010-06-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP2185554A1 (en) | 2007-08-09 | 2010-05-19 | Merck Sharp & Dohme Corp. | Silicon derivatives as histone deacetylase inhibitors |
| US7642251B2 (en) * | 2007-08-09 | 2010-01-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US20120121540A1 (en) | 2007-08-10 | 2012-05-17 | Franz Ulrich Schmitz | Certain Nitrogen Containing Bicyclic Chemical Entities For Treating Viral Infections |
| PL2242752T3 (pl) | 2008-02-13 | 2012-12-31 | Bristol Myers Squibb Co | Imidazolilobifenyloimidazole jako inhibitory wirusa zapalenia wątroby typu c |
| ME02024B (me) | 2008-07-22 | 2015-05-20 | Merck Sharp & Dohme | Makrociklična jedinjenja hinoksalina kao inhibitori hcv ns3 proteaze |
| JP5655568B2 (ja) * | 2008-10-09 | 2015-01-21 | コニカミノルタ株式会社 | 有機光電変換素子、太陽電池及び光センサアレイ |
| US8729077B2 (en) | 2008-11-28 | 2014-05-20 | Glaxosmithkline Llc | Anti-viral compounds, compositions, and methods of use |
| BRPI0922366B8 (pt) * | 2008-12-03 | 2021-05-25 | Presidio Pharmaceuticals Inc | composto, composição farmacêutica e uso de um composto |
| CN102427729B (zh) * | 2009-03-27 | 2014-09-03 | 默沙东公司 | 丙型肝炎病毒复制的抑制剂 |
| MX2011010132A (es) | 2009-03-27 | 2011-10-14 | Presidio Pharmaceuticals Inc | Inhibidores de anillo fusionado de hepatitis c. |
| US8772505B2 (en) | 2009-05-29 | 2014-07-08 | Merck Sharp & Dohme Corp. | Antiviral compounds composed of three aligned aryl moieties to treat diseases such as hepatitis C |
| US8221737B2 (en) | 2009-06-16 | 2012-07-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8377980B2 (en) | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CA2785488A1 (en) | 2009-12-22 | 2011-07-21 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds and methods of use thereof for the treatment of viral diseases |
| EP2545060B1 (en) | 2010-03-09 | 2015-11-25 | Merck Sharp & Dohme Corp. | Fused tricyclic silyl compounds and methods of use thereof for the treatment of viral diseases |
| WO2012018534A2 (en) | 2010-07-26 | 2012-02-09 | Schering Corporation | Substituted biphenylene compounds and methods of use thereof for the treatment of viral diseases |
| EP2621279B1 (en) | 2010-09-29 | 2018-04-04 | Merck Sharp & Dohme Corp. | Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases |
| US20130280214A1 (en) | 2010-09-29 | 2013-10-24 | Merck Sharp & Dohme Corp. | Polycyclic heterocycle derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012040923A1 (en) | 2010-09-29 | 2012-04-05 | Merck Sharp & Dohme Corp. | Tetracyclic indole derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012122716A1 (en) | 2011-03-17 | 2012-09-20 | Merck Sharp & Dohme Corp. | Tetracyclic xanthene derivatives and methods of use thereof for treatment of viral diseases |
-
2010
- 2010-03-25 CN CN201080021629.4A patent/CN102427729B/zh active Active
- 2010-03-25 SG SG10201402969QA patent/SG10201402969QA/en unknown
- 2010-03-25 HU HUE10756840A patent/HUE027755T2/en unknown
- 2010-03-25 KR KR1020137031213A patent/KR20130140219A/ko not_active Withdrawn
- 2010-03-25 EP EP10756840.4A patent/EP2410844B1/en active Active
- 2010-03-25 DK DK10756840.4T patent/DK2410844T3/en active
- 2010-03-25 PL PL10756840T patent/PL2410844T3/pl unknown
- 2010-03-25 CN CN201410127412.1A patent/CN103880862B/zh active Active
- 2010-03-25 CA CA2756172A patent/CA2756172C/en active Active
- 2010-03-25 MY MYPI2013004468A patent/MY169311A/en unknown
- 2010-03-25 RS RS20160286A patent/RS54713B1/sr unknown
- 2010-03-25 KR KR1020117025316A patent/KR101387274B1/ko not_active Expired - Fee Related
- 2010-03-25 UA UAA201112538A patent/UA108351C2/ru unknown
- 2010-03-25 HR HRP20160476TT patent/HRP20160476T1/hr unknown
- 2010-03-25 MA MA34270A patent/MA33209B1/fr unknown
- 2010-03-25 PE PE2011001718A patent/PE20120765A1/es active IP Right Grant
- 2010-03-25 BR BRPI1013394-1A patent/BRPI1013394B1/pt not_active IP Right Cessation
- 2010-03-25 AU AU2010229833A patent/AU2010229833B2/en not_active Ceased
- 2010-03-25 ME MEP-2016-84A patent/ME02418B/me unknown
- 2010-03-25 JP JP2012502245A patent/JP5913091B2/ja active Active
- 2010-03-25 NZ NZ595410A patent/NZ595410A/en not_active IP Right Cessation
- 2010-03-25 EA EA201171174A patent/EA020898B1/ru active Protection Beyond IP Right Term
- 2010-03-25 US US13/260,684 patent/US8871759B2/en active Active
- 2010-03-25 MX MX2011010084A patent/MX2011010084A/es active IP Right Grant
- 2010-03-25 SI SI201031173A patent/SI2410844T1/sl unknown
- 2010-03-25 CN CN201811052267.XA patent/CN109651342A/zh active Pending
- 2010-03-25 SG SG2011069887A patent/SG174929A1/en unknown
- 2010-03-25 WO PCT/US2010/028653 patent/WO2010111483A1/en not_active Ceased
- 2010-03-25 GE GEAP201012428A patent/GEP20146134B/en unknown
- 2010-03-25 ES ES10756840.4T patent/ES2573088T3/es active Active
-
2011
- 2011-09-11 IL IL215094A patent/IL215094A/en active IP Right Grant
- 2011-09-19 ZA ZA2011/06807A patent/ZA201106807B/en unknown
- 2011-09-21 TN TN2011000475A patent/TN2011000475A1/fr unknown
- 2011-09-23 NI NI201100172A patent/NI201100172A/es unknown
- 2011-09-23 CO CO11124967A patent/CO6420390A2/es active IP Right Grant
- 2011-09-26 DO DO2011000298A patent/DOP2011000298A/es unknown
- 2011-09-27 CR CR20110506A patent/CR20110506A/es unknown
- 2011-09-28 EC EC2011011357A patent/ECSP11011357A/es unknown
-
2013
- 2013-12-17 ZA ZA2013/09504A patent/ZA201309504B/en unknown
-
2014
- 2014-08-29 US US14/473,117 patent/US9090661B2/en active Active
- 2014-09-25 JP JP2014195016A patent/JP5932929B2/ja active Active
-
2015
- 2015-05-13 US US14/711,345 patent/US20150246917A1/en not_active Abandoned
-
2016
- 2016-09-22 US US15/272,669 patent/US20170008906A1/en not_active Abandoned
- 2016-12-26 FR FR16C1026C patent/FR16C1026I2/fr active Active
- 2016-12-29 LT LTPA2016048C patent/LTC2410844I2/lt unknown
- 2016-12-30 NL NL300858C patent/NL300858I2/nl unknown
-
2017
- 2017-01-03 LU LU00003C patent/LUC00003I2/fr unknown
- 2017-01-10 HU HUS1700002C patent/HUS1700002I1/hu unknown
- 2017-01-20 NO NO2017006C patent/NO2017006I2/no unknown
- 2017-01-20 CY CY2017004C patent/CY2017004I2/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7620649B2 (ja) | コロナウイルス、ピコルナウイルス及びノロウイルス感染を治療するための抗ウイルス化合物 | |
| KR101492672B1 (ko) | Ｃ형 간염 바이러스 억제제로서의 이미다졸릴 바이페닐 이미다졸 | |
| KR101475189B1 (ko) | Ｃ형 간염 바이러스 억제제 | |
| US8871759B2 (en) | Inhibitors of hepatitis C virus replication | |
| KR101730681B1 (ko) | Ｃ형 간염 바이러스 억제제 | |
| JP2013510853A5 (OSRAM) | ||
| JP2012518000A5 (OSRAM) | ||
| JP2010500413A5 (OSRAM) | ||
| ME02201B (me) | Pripravci u krutom stanju | |
| RU2010130095A (ru) | Активаторы глюкокиназы и фармацевтические композиции, содержащие их в качестве активного ингредиента | |
| RU2010109895A (ru) | Соединения индола в качестве ингибиторов клеточного некроза | |
| KR20100114924A (ko) | Ｃ형 간염 바이러스 억제제 | |
| JP2014506877A5 (OSRAM) | ||
| EP2398794A1 (en) | Hepatitis c virus inhibitors | |
| JP2014133739A5 (OSRAM) | ||
| CA2594667A1 (en) | Compositions and therapeutic methods utilizing a combination of a 5-ht1f inhibitor and an nsaid | |
| RU2013124814A (ru) | Гетероциклические производные диазенийдиолата | |
| JP2017527628A5 (OSRAM) | ||
| RU2007130706A (ru) | Замещенные 4-фенилтетрагидроизохинолины, способ их получения, их применение в качестве лекарственных средств, а также содержащие их лекарственные средства | |
| US11053243B2 (en) | Inhibitors of hepatitis C virus replication | |
| JP2025097322A5 (OSRAM) | ||
| EA050478B1 (ru) | Противовирусные соединения для лечения коронавирусной, пикорнавирусной и норовирусной инфекций | |
| AR065331A1 (es) | Derivados de bifenilil-1h-imidazol y bifenildiil-bis(1h-imidazol-4,2)diilo como inhibidores del virus de la hepatitis c, composiciones que los comprenden y su uso en el tratamiento de una infeccion de vhc. | |
| TH1801007388A (th) | สารประกอบอิมิดาโซโลนในฐานะที่เป็นตัวยับยั้งอีลาสเทสของนิวโทรฟิลมนุษย์ | |
| TH91886A (th) | การใช้สารต้าน cb1 ในการรักษาอาการข้างเคียงและอาการไม่พึงประสงค์ของภาวะจิตเภท |