JP2010500413A5 - - Google Patents
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- Publication number
- JP2010500413A5 JP2010500413A5 JP2009524736A JP2009524736A JP2010500413A5 JP 2010500413 A5 JP2010500413 A5 JP 2010500413A5 JP 2009524736 A JP2009524736 A JP 2009524736A JP 2009524736 A JP2009524736 A JP 2009524736A JP 2010500413 A5 JP2010500413 A5 JP 2010500413A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidinyl
- imidazol
- biphenylyl
- oxo
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 899
- -1 carboxy, formyl Chemical group 0.000 claims 290
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 235
- 229910052757 nitrogen Inorganic materials 0.000 claims 84
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 77
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 67
- 150000003839 salts Chemical class 0.000 claims 42
- 150000001875 compounds Chemical class 0.000 claims 37
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 36
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 32
- 125000000217 alkyl group Chemical group 0.000 claims 31
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 26
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims 16
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 15
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 13
- BQKLBHZGHOKWSR-BTSKBWHGSA-N (2r)-2-morpholin-4-yl-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-oxolane-2-carbonyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound N1([C@@H](C(=O)N2[C@@H](CCC2)C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H]2OCCC2)C=2C=CC=CC=2)CCOCC1 BQKLBHZGHOKWSR-BTSKBWHGSA-N 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 9
- 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 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- PQJFJRGZSZKPTF-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O.COC(N)=O PQJFJRGZSZKPTF-UHFFFAOYSA-N 0.000 claims 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 6
- 108010047761 Interferon-alpha Proteins 0.000 claims 6
- 102000006992 Interferon-alpha Human genes 0.000 claims 6
- 108010050904 Interferons Proteins 0.000 claims 6
- 102000014150 Interferons Human genes 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 6
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 229940079322 interferon Drugs 0.000 claims 6
- 229940124597 therapeutic agent Drugs 0.000 claims 6
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 239000004202 carbamide Substances 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 229950003188 isovaleryl diethylamide Drugs 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 4
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 4
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 4
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 claims 4
- GXHAENUAJYZNOA-UHFFFAOYSA-N oxolane-2-carboxamide Chemical compound NC(=O)C1CCCO1 GXHAENUAJYZNOA-UHFFFAOYSA-N 0.000 claims 4
- 229960000329 ribavirin Drugs 0.000 claims 4
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- UMPWFNPLHSVRAN-UHFFFAOYSA-N 2-(diethylamino)-2-phenylacetaldehyde Chemical compound CCN(CC)C(C=O)C1=CC=CC=C1 UMPWFNPLHSVRAN-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229940049953 phenylacetate Drugs 0.000 claims 3
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 3
- NGACNFMXLHHFTI-JPYDVTDNSA-N (2r)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-oxolane-2-carbonyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenyl-2-piperidin-1-ylethanone Chemical compound N1([C@@H](C(=O)N2[C@@H](CCC2)C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H]2OCCC2)C=2C=CC=CC=2)CCCCC1 NGACNFMXLHHFTI-JPYDVTDNSA-N 0.000 claims 2
- XUXLCKDCNOQMOC-ATUXXYJQSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-2-(trifluoromethyl)phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C(=C2)C(F)(F)F)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 XUXLCKDCNOQMOC-ATUXXYJQSA-N 0.000 claims 2
- IUKDDNWJLHYBGC-ATUXXYJQSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)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 IUKDDNWJLHYBGC-ATUXXYJQSA-N 0.000 claims 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 2
- KXRRLLSJROBMBU-IIOWIJGZSA-N 2-(7-azabicyclo[2.2.1]heptan-7-yl)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[2-(7-azabicyclo[2.2.1]heptan-7-yl)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound N1([C@@H](CCC1)C=1NC(=CN=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1NC(=NC=1)[C@H]1N(CCC1)C(=O)C(N1C2CCC1CC2)C=1C=CC=CC=1)C(=O)C(N1C2CCC1CC2)C1=CC=CC=C1 KXRRLLSJROBMBU-IIOWIJGZSA-N 0.000 claims 2
- AOGFRXVTKLIGBI-UHFFFAOYSA-N 2-(dimethylamino)-2-phenylacetaldehyde Chemical compound CN(C)C(C=O)C1=CC=CC=C1 AOGFRXVTKLIGBI-UHFFFAOYSA-N 0.000 claims 2
- HVXUKFHYSAXUQR-KUKVWGSOSA-N 2-[(3s)-3-fluoropyrrolidin-1-yl]-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[2-[(3s)-3-fluoropyrrolidin-1-yl]-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1[C@@H](F)CCN1C(C=1C=CC=CC=1)C(=O)N1[C@H](C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)C(N2C[C@@H](F)CC2)C=2C=CC=CC=2)CCC1 HVXUKFHYSAXUQR-KUKVWGSOSA-N 0.000 claims 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 108020005544 Antisense RNA Proteins 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 229940124186 Dehydrogenase inhibitor Drugs 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- HAEJPQIATWHALX-KQYNXXCUSA-N ITP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(N=CNC2=O)=C2N=C1 HAEJPQIATWHALX-KQYNXXCUSA-N 0.000 claims 2
- 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims 2
- 102100040018 Interferon alpha-2 Human genes 0.000 claims 2
- 108010079944 Interferon-alpha2b Proteins 0.000 claims 2
- 102000013462 Interleukin-12 Human genes 0.000 claims 2
- 108010065805 Interleukin-12 Proteins 0.000 claims 2
- 102000000588 Interleukin-2 Human genes 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 102000004889 Interleukin-6 Human genes 0.000 claims 2
- 108090001005 Interleukin-6 Proteins 0.000 claims 2
- 102000005741 Metalloproteases Human genes 0.000 claims 2
- 108010006035 Metalloproteases Proteins 0.000 claims 2
- 108060004795 Methyltransferase Proteins 0.000 claims 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 102000012479 Serine Proteases Human genes 0.000 claims 2
- 108010022999 Serine Proteases Proteins 0.000 claims 2
- 230000005867 T cell response Effects 0.000 claims 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 2
- 229960003805 amantadine Drugs 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000003184 complementary RNA Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 2
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims 2
- 229960002751 imiquimod Drugs 0.000 claims 2
- 230000002452 interceptive effect Effects 0.000 claims 2
- 229940117681 interleukin-12 Drugs 0.000 claims 2
- 229940100601 interleukin-6 Drugs 0.000 claims 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 229960000888 rimantadine Drugs 0.000 claims 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- VSCSIVBMRODHIP-RRKGBCIJSA-N (2R)-2-hydroxy-1-(3-hydroxypyrrolidin-1-yl)-2-phenylethanone Chemical compound O=C([C@H](O)C=1C=CC=CC=1)N1CCC(O)C1 VSCSIVBMRODHIP-RRKGBCIJSA-N 0.000 claims 1
- CTRPRHJEFXXKTO-ACHIHNKUSA-N (2S)-2-[1-tert-butyl-5-[4-[4-[2-[(2S)-1-phenylmethoxycarbonylpyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]phenyl]-4-(trifluoromethyl)imidazol-2-yl]pyrrolidine-1-carboxylic acid Chemical compound CC(C)(C)N1C(=NC(=C1C2=CC=C(C=C2)C3=CC=C(C=C3)C4=CN=C(N4)[C@@H]5CCCN5C(=O)OCC6=CC=CC=C6)C(F)(F)F)[C@@H]7CCCN7C(=O)O CTRPRHJEFXXKTO-ACHIHNKUSA-N 0.000 claims 1
- NJGTUGMFRWNXBW-URXFXBBRSA-N (2S)-2-[5-[2-fluoro-4-[4-[2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]phenyl]-1H-imidazol-2-yl]pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCC[C@H]1C1=NC=C(C=2C(=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2NCCC2)F)N1 NJGTUGMFRWNXBW-URXFXBBRSA-N 0.000 claims 1
- NQMOHQHKXWEJAE-ZEQRLZLVSA-N (2S)-2-[5-[4-[4-[2-[(2S)-1-carboxypyrrolidin-2-yl]-1H-imidazol-5-yl]-3-fluorophenyl]-2-fluorophenyl]-1H-imidazol-2-yl]pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCC[C@H]1C1=NC=C(C=2C(=CC(=CC=2)C=2C=C(F)C(C=3NC(=NC=3)[C@H]3N(CCC3)C(O)=O)=CC=2)F)N1 NQMOHQHKXWEJAE-ZEQRLZLVSA-N 0.000 claims 1
- KPOOTHVUARHMTR-ZEQRLZLVSA-N (2S)-2-[5-[4-[4-[2-[(2S)-1-carboxypyrrolidin-2-yl]-1H-imidazol-5-yl]-3-fluorophenyl]phenyl]-1H-imidazol-2-yl]pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=C(F)C(C=3NC(=NC=3)[C@H]3N(CCC3)C(O)=O)=CC=2)N1 KPOOTHVUARHMTR-ZEQRLZLVSA-N 0.000 claims 1
- OEGGMPCANFOVSI-ZEQRLZLVSA-N (2S)-2-[5-[4-[4-[2-[(2S)-1-carboxypyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]phenyl]-1H-imidazol-2-yl]pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(O)=O)N1 OEGGMPCANFOVSI-ZEQRLZLVSA-N 0.000 claims 1
- KRSAYGSVMVDOPF-BTSKBWHGSA-N (2r)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-oxolane-2-carbonyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenyl-2-pyrrolidin-1-ylethanone Chemical compound N1([C@@H](C(=O)N2[C@@H](CCC2)C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H]2OCCC2)C=2C=CC=CC=2)CCCC1 KRSAYGSVMVDOPF-BTSKBWHGSA-N 0.000 claims 1
- VOCZDPISQHKZSQ-LZCGGXSTSA-N (2r)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-4,4-difluoro-1-[(2r)-2-phenyl-2-piperidin-1-ylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-4,4-difluoropyrrolidin-1-yl]-2-phenyl-2-piperidin-1-ylethanone Chemical compound N1([C@@H](C(=O)N2[C@@H](CC(C2)(F)F)C=2NC=C(N=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CC(F)(F)C2)C(=O)[C@H](N2CCCCC2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCCCC1 VOCZDPISQHKZSQ-LZCGGXSTSA-N 0.000 claims 1
- JCMKFTURXQEBOI-FTVGNFKQSA-N (2r)-1-[(2s,4s)-4-fluoro-2-[5-[4-[4-[2-[(2s,4s)-4-fluoro-1-[(2r)-2-phenyl-2-piperidin-1-ylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenyl-2-piperidin-1-ylethanone Chemical compound N1([C@@H](C(=O)N2[C@@H](C[C@@H](C2)F)C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(C[C@@H](F)C2)C(=O)[C@H](N2CCCCC2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCCCC1 JCMKFTURXQEBOI-FTVGNFKQSA-N 0.000 claims 1
- KCRKCIONJOJIJF-JRTLPCBOSA-N (2r)-2-(4-hydroxy-4-methylpiperidin-1-yl)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(4-hydroxy-4-methylpiperidin-1-yl)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1CC(C)(O)CCN1[C@H](C=1C=CC=CC=1)C(=O)N1[C@H](C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](N2CCC(C)(O)CC2)C=2C=CC=CC=2)CCC1 KCRKCIONJOJIJF-JRTLPCBOSA-N 0.000 claims 1
- QCYJEPFMDGAYSD-LZCGGXSTSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-2,5-difluorophenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=C(F)C=C(C(=C2)F)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 QCYJEPFMDGAYSD-LZCGGXSTSA-N 0.000 claims 1
- GXTKKFXXMWRHTJ-LZCGGXSTSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-3-fluorophenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2F)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 GXTKKFXXMWRHTJ-LZCGGXSTSA-N 0.000 claims 1
- UWAMWQMSHLVZIG-LZCGGXSTSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 UWAMWQMSHLVZIG-LZCGGXSTSA-N 0.000 claims 1
- RHJAPGNPPQBNKZ-JPYDVTDNSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)-3-methylbutanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-methylbutan-1-one Chemical compound CCN(CC)[C@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H](C(C)C)N(CC)CC)N1 RHJAPGNPPQBNKZ-JPYDVTDNSA-N 0.000 claims 1
- BIXCKKUISKNHQU-SFSFMBGESA-N (2r)-2-(diethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)propanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CCN(CC)[C@H](C)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H](C)N(CC)CC)N1 BIXCKKUISKNHQU-SFSFMBGESA-N 0.000 claims 1
- HENITQMDQHJFFP-MUPJHJRRSA-N (2r)-2-(diethylamino)-1-[(2s,4s)-2-[5-[4-[4-[2-[(2s,4s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]-4-hydroxypyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-4-hydroxypyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2C[C@@H](O)C[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2C[C@H](O)CN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 HENITQMDQHJFFP-MUPJHJRRSA-N 0.000 claims 1
- ZTVMKLVQIRLXRN-IYTFMMMVSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[4-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1-methylimidazol-4-yl]phenyl]phenyl]-1-methylimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C=2N(C)C=C(N=2)C2=CC=C(C=C2)C2=CC=C(C=C2)C=2N=C(N(C=2)C)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 ZTVMKLVQIRLXRN-IYTFMMMVSA-N 0.000 claims 1
- QQCXMZQNDLMMFL-ZTJXFJJRSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[3-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-4-methoxyphenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC(=CC=C2OC)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 QQCXMZQNDLMMFL-ZTJXFJJRSA-N 0.000 claims 1
- FGGHPRHSHSKDFY-WQNNDMHESA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-(2-naphthalen-1-ylacetyl)pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]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=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)CC=2C3=CC=CC=C3C=CC=2)N(C)C)=CC=CC=C1 FGGHPRHSHSKDFY-WQNNDMHESA-N 0.000 claims 1
- SZSNGJXSUGDHBS-IYTFMMMVSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-2-methylphenyl]-3-methylphenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C(=C2)C)C2=CC=C(C=C2C)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 SZSNGJXSUGDHBS-IYTFMMMVSA-N 0.000 claims 1
- FWSMGVFRTFQBND-SKQWTEPWSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-2-methylphenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C(=C2)C)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 FWSMGVFRTFQBND-SKQWTEPWSA-N 0.000 claims 1
- BDSIXINCAISMAK-IYTFMMMVSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-3-phenylpropanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-phenylpropan-1-one Chemical compound C([C@@H](N(C)C)C(=O)N1[C@@H](CCC1)C=1NC(=CN=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1NC(=NC=1)[C@H]1N(CCC1)C(=O)[C@@H](CC=1C=CC=CC=1)N(C)C)C1=CC=CC=C1 BDSIXINCAISMAK-IYTFMMMVSA-N 0.000 claims 1
- ZILFXIZLQOTHSA-DDADIKCBSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)propanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CN(C)[C@H](C)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H](C)N(C)C)N1 ZILFXIZLQOTHSA-DDADIKCBSA-N 0.000 claims 1
- FWGCYCKXNMGIBF-YZBUDRBASA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[4-(dimethylamino)benzoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C([C@H]1C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)CCN1C(=O)C1=CC=C(N(C)C)C=C1 FWGCYCKXNMGIBF-YZBUDRBASA-N 0.000 claims 1
- OSJQRQBAHSPLNB-XUTHUYCTSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[4-(hydroxymethyl)benzoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C([C@H]1C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)CCN1C(=O)C1=CC=C(CO)C=C1 OSJQRQBAHSPLNB-XUTHUYCTSA-N 0.000 claims 1
- ZQWPLEWGQJOEIG-ZZDDQDSOSA-N (2r)-2-(dimethylamino)-1-[(2s,4s)-2-[5-[4-[4-[2-[(2s,4s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]-4-hydroxypyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-4-hydroxypyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2C[C@@H](O)C[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2C[C@H](O)CN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 ZQWPLEWGQJOEIG-ZZDDQDSOSA-N 0.000 claims 1
- NWQCAAUPWUXELC-JPYDVTDNSA-N (2r)-2-(dimethylamino)-1-[(4r)-4-[5-[4-[4-[2-[(4r)-3-[(2r)-2-(dimethylamino)-2-phenylacetyl]-1,3-thiazolidin-4-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-1,3-thiazolidin-3-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CSC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CSCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 NWQCAAUPWUXELC-JPYDVTDNSA-N 0.000 claims 1
- LXAKRTGKWHMPJP-KWDKOVGYSA-N (2r)-2-(dimethylamino)-2-phenyl-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-(3-pyrrolidin-1-ylbenzoyl)pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound C([C@H]1C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)CCN1C(=O)C(C=1)=CC=CC=1N1CCCC1 LXAKRTGKWHMPJP-KWDKOVGYSA-N 0.000 claims 1
- QACMRPXUCTZBOA-IWJNXRQDSA-N (2r)-2-(dimethylamino)-2-phenyl-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-(5-phenylthiophene-2-carbonyl)pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound C([C@H]1C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)CCN1C(=O)C(S1)=CC=C1C1=CC=CC=C1 QACMRPXUCTZBOA-IWJNXRQDSA-N 0.000 claims 1
- WDBPQXUEJJCSSM-ZLBAHODBSA-N (2r)-2-(dipropylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(dipropylamino)propanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CCCN(CCC)[C@H](C)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H](C)N(CCC)CCC)N1 WDBPQXUEJJCSSM-ZLBAHODBSA-N 0.000 claims 1
- ASFUWJHTRWCQLF-IYTFMMMVSA-N (2r)-2-[ethyl(methyl)amino]-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-[ethyl(methyl)amino]-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)CC)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)CC)C=2C=CC=CC=2)=CC=CC=C1 ASFUWJHTRWCQLF-IYTFMMMVSA-N 0.000 claims 1
- UAGSIMCUMTVTNA-GASGPIRDSA-N (2r)-2-amino-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-methylbutan-1-one Chemical compound CC(C)[C@@H](N)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](N)C(C)C)N1 UAGSIMCUMTVTNA-GASGPIRDSA-N 0.000 claims 1
- HQDZRYUCSGSHCM-IZSXRKQISA-N (2r)-2-hydroxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-hydroxy-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-2-methylphenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2C)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 HQDZRYUCSGSHCM-IZSXRKQISA-N 0.000 claims 1
- BYPMSKJLHSBHJD-CDBYGCFJSA-N (2r)-2-hydroxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-hydroxy-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 BYPMSKJLHSBHJD-CDBYGCFJSA-N 0.000 claims 1
- IAHMCIMIFFMSLK-GASGPIRDSA-N (2r)-2-hydroxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-hydroxy-3-methylbutanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-methylbutan-1-one Chemical compound CC(C)[C@@H](O)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](O)C(C)C)N1 IAHMCIMIFFMSLK-GASGPIRDSA-N 0.000 claims 1
- SYMAFFKJYPWFHP-JPYDVTDNSA-N (2r)-2-hydroxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-hydroxy-3-phenylpropanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-phenylpropan-1-one Chemical compound C([C@@H](O)C(=O)N1[C@@H](CCC1)C=1NC(=CN=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1NC(=NC=1)[C@H]1N(CCC1)C(=O)[C@H](O)CC=1C=CC=CC=1)C1=CC=CC=C1 SYMAFFKJYPWFHP-JPYDVTDNSA-N 0.000 claims 1
- UFRPXKSFPYDVRA-SJWRPRNESA-N (2r)-2-hydroxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-hydroxypropanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound C[C@@H](O)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H](C)O)N1 UFRPXKSFPYDVRA-SJWRPRNESA-N 0.000 claims 1
- QCIHCVATPVOJKG-XJDCEBINSA-N (2r)-2-hydroxy-1-[(2s,4r)-4-hydroxy-2-[5-[4-[4-[2-[(2s,4r)-4-hydroxy-1-[(2r)-2-hydroxy-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2C[C@H](O)C[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2C[C@@H](O)CN2C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 QCIHCVATPVOJKG-XJDCEBINSA-N 0.000 claims 1
- UXBCVKLRKAKSSL-JPYDVTDNSA-N (2r)-2-methoxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-methoxy-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](OC)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](OC)C=2C=CC=CC=2)=CC=CC=C1 UXBCVKLRKAKSSL-JPYDVTDNSA-N 0.000 claims 1
- QFTOZIFOZMBEEH-LZCGGXSTSA-N (2r)-2-morpholin-4-yl-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-morpholin-4-yl-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound N1([C@@H](C(=O)N2[C@@H](CCC2)C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](N2CCOCC2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCOCC1 QFTOZIFOZMBEEH-LZCGGXSTSA-N 0.000 claims 1
- KTDHJRVKPDUSBY-JRTLPCBOSA-N (2r)-2-phenyl-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-phenyl-2-piperidin-1-ylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-piperidin-1-ylethanone Chemical compound N1([C@@H](C(=O)N2[C@@H](CCC2)C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](N2CCCCC2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCCCC1 KTDHJRVKPDUSBY-JRTLPCBOSA-N 0.000 claims 1
- BGWGLHJWKQZPKG-LZCGGXSTSA-N (2r)-2-phenyl-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-phenyl-2-pyrrolidin-1-ylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-pyrrolidin-1-ylethanone Chemical compound N1([C@@H](C(=O)N2[C@@H](CCC2)C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](N2CCCC2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCCC1 BGWGLHJWKQZPKG-LZCGGXSTSA-N 0.000 claims 1
- YOZBJKIABZDGPP-CBULZRFXSA-N (2r)-2-phenyl-2-piperidin-1-yl-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-(2-thiophen-2-ylacetyl)pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC(=CN=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1NC(=NC=1)[C@H]1N(CCC1)C(=O)[C@H](N1CCCCC1)C=1C=CC=CC=1)C(=O)CC1=CC=CS1 YOZBJKIABZDGPP-CBULZRFXSA-N 0.000 claims 1
- IUKDDNWJLHYBGC-IWWWZYECSA-N (2s)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@H](N(C)C)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)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 IUKDDNWJLHYBGC-IWWWZYECSA-N 0.000 claims 1
- ZILFXIZLQOTHSA-UDRQUUIHSA-N (2s)-2-(dimethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-(dimethylamino)propanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CN(C)[C@@H](C)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](C)N(C)C)N1 ZILFXIZLQOTHSA-UDRQUUIHSA-N 0.000 claims 1
- AEVJCQZIZSAJLH-OBMDHMNCSA-N (2s)-2-(methylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-(methylamino)propanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CN[C@@H](C)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](C)NC)N1 AEVJCQZIZSAJLH-OBMDHMNCSA-N 0.000 claims 1
- KYQGKPDXJAVBEQ-DYGKRUFJSA-N (2s)-2-[benzyl(methyl)amino]-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-[benzyl(methyl)amino]propanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CN([C@@H](C)C(=O)N1[C@@H](CCC1)C=1NC(=CN=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1NC(=NC=1)[C@H]1N(CCC1)C(=O)[C@H](C)N(C)CC=1C=CC=CC=1)CC1=CC=CC=C1 KYQGKPDXJAVBEQ-DYGKRUFJSA-N 0.000 claims 1
- NIBLWEFROMDHCM-ZQWQDMLBSA-N (2s)-2-cyclohexyl-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-cyclohexyl-2-hydroxyacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound C1([C@H](O)C(=O)N2[C@@H](CCC2)C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H](O)C2CCCCC2)CCCCC1 NIBLWEFROMDHCM-ZQWQDMLBSA-N 0.000 claims 1
- MIIUYAOLJFKCDB-SOAZDVDRSA-N (2s)-2-hydroxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-hydroxy-2-phenylpropanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylpropan-1-one Chemical compound C1([C@](C)(O)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@](O)(C)C=2C=CC=CC=2)=CC=CC=C1 MIIUYAOLJFKCDB-SOAZDVDRSA-N 0.000 claims 1
- IAHMCIMIFFMSLK-YDPTYEFTSA-N (2s)-2-hydroxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-hydroxy-3-methylbutanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-methylbutan-1-one Chemical compound CC(C)[C@H](O)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H](O)C(C)C)N1 IAHMCIMIFFMSLK-YDPTYEFTSA-N 0.000 claims 1
- WQQMZBVPBSKVPV-CUPIEXAXSA-N (2s)-2-hydroxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-hydroxy-4-methylpentanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-4-methylpentan-1-one Chemical compound CC(C)C[C@H](O)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H](O)CC(C)C)N1 WQQMZBVPBSKVPV-CUPIEXAXSA-N 0.000 claims 1
- AGGZMBJBJVDLHB-ATACATFBSA-N (4s)-4-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(4s)-2-oxo-1,3-oxazinane-4-carbonyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidine-1-carbonyl]-1,3-oxazinan-2-one Chemical compound N1([C@@H](CCC1)C=1NC(=CN=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1NC(=NC=1)[C@H]1N(CCC1)C(=O)[C@H]1NC(=O)OCC1)C(=O)[C@@H]1CCOC(=O)N1 AGGZMBJBJVDLHB-ATACATFBSA-N 0.000 claims 1
- HANJVUROINGYGL-MUVIMXQCSA-N (4s,5r)-5-methyl-4-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(4s,5r)-5-methyl-2-oxo-1,3-oxazolidine-4-carbonyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidine-1-carbonyl]-1,3-oxazolidin-2-one Chemical compound C[C@H]1OC(=O)N[C@@H]1C(=O)N1[C@H](C=2NC(=CN=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H]2[C@H](OC(=O)N2)C)CCC1 HANJVUROINGYGL-MUVIMXQCSA-N 0.000 claims 1
- SZPANMBAXSMUMO-GVYQIEHESA-N (5r)-5-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidine-1-carbonyl]pyrrolidin-2-one Chemical compound C([C@H]1C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)CCN1C(=O)[C@H]1CCC(=O)N1 SZPANMBAXSMUMO-GVYQIEHESA-N 0.000 claims 1
- QTLXNQVEHAWKMY-NOBGTIEJSA-N (5s)-5-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidine-1-carbonyl]pyrrolidin-2-one Chemical compound C([C@H]1C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)CCN1C(=O)[C@@H]1CCC(=O)N1 QTLXNQVEHAWKMY-NOBGTIEJSA-N 0.000 claims 1
- BVHLIRXEHAFUKM-SNLXXZSDSA-N 1-[(1r)-2-[(2s,4r)-4-hydroxy-2-[5-[4-[4-[2-[(2s,4r)-4-hydroxy-1-[(2r)-2-(methylcarbamoylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]-3-methylurea Chemical compound C1([C@@H](NC(=O)NC)C(=O)N2C[C@H](O)C[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2C[C@@H](O)CN2C(=O)[C@H](NC(=O)NC)C=2C=CC=CC=2)=CC=CC=C1 BVHLIRXEHAFUKM-SNLXXZSDSA-N 0.000 claims 1
- PGNCMSVERQPZBR-JRTLPCBOSA-N 1-[(1r)-2-oxo-1-phenyl-2-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-phenyl-2-(pyridin-3-ylcarbamoylamino)acetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]ethyl]-3-pyridin-3-ylurea Chemical compound N([C@@H](C(=O)N1CCC[C@H]1C1=NC=C(N1)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CN=C(N1)[C@@H]1CCCN1C(=O)[C@H](NC(=O)NC=1C=NC=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)NC1=CC=CN=C1 PGNCMSVERQPZBR-JRTLPCBOSA-N 0.000 claims 1
- GTXLDAQLCOVOIO-SIEKYESCSA-N 1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2,2-diphenylethanone Chemical compound C([C@H]1C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)CCN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 GTXLDAQLCOVOIO-SIEKYESCSA-N 0.000 claims 1
- CQSPWJTYUHEUGB-AQVMEVBTSA-N 1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-piperidin-1-ylpropan-1-one Chemical compound C([C@H]1C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)CCN1C(=O)CCN1CCCCC1 CQSPWJTYUHEUGB-AQVMEVBTSA-N 0.000 claims 1
- AGQUGDPUFVDBSQ-NSOVKSMOSA-N 1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-propanoylpyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CCC(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)CC)N1 AGQUGDPUFVDBSQ-NSOVKSMOSA-N 0.000 claims 1
- VSVACLHEKVUUAG-URLMMPGGSA-N 1-[4-[4-[2-[(2S)-1-[(2R)-2-(methoxycarbonylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]phenyl]imidazole-4-carboxylic acid Chemical compound COC(=O)N[C@@H](C(=O)N1[C@@H](CCC1)C=1NC(=CN=1)C1=CC=C(C=C1)C1=CC=C(C=C1)N1C=NC(=C1)C(=O)O)C1=CC=CC=C1 VSVACLHEKVUUAG-URLMMPGGSA-N 0.000 claims 1
- IMNIHXTVVDWOOR-JRTLPCBOSA-N 1-cyclopentyl-3-[(1r)-2-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(cyclopentylcarbamoylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound N([C@@H](C(=O)N1CCC[C@H]1C1=NC=C(N1)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CN=C(N1)[C@@H]1CCCN1C(=O)[C@H](NC(=O)NC1CCCC1)C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)NC1CCCC1 IMNIHXTVVDWOOR-JRTLPCBOSA-N 0.000 claims 1
- HPTJDALHSDQWKC-MPDHQVEESA-N 1-cyclopentyl-3-[(1r)-2-[(2s,4r)-2-[5-[4-[4-[2-[(2s,4r)-1-[(2r)-2-(cyclopentylcarbamoylamino)-2-phenylacetyl]-4-hydroxypyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-4-hydroxypyrrolidin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound N([C@@H](C(=O)N1[C@@H](C[C@H](C1)O)C=1NC(=CN=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1NC(=NC=1)[C@H]1N(C[C@H](O)C1)C(=O)[C@H](NC(=O)NC1CCCC1)C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)NC1CCCC1 HPTJDALHSDQWKC-MPDHQVEESA-N 0.000 claims 1
- RUJXBSVSFZKCEZ-ATUXXYJQSA-N 1-ethyl-3-[(1r)-2-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(ethylcarbamoylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1([C@@H](NC(=O)NCC)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](NC(=O)NCC)C=2C=CC=CC=2)=CC=CC=C1 RUJXBSVSFZKCEZ-ATUXXYJQSA-N 0.000 claims 1
- STZFHBJVOSTLJY-HEMKMFBASA-N 1-ethyl-3-[(1r)-2-[(2s,4r)-2-[5-[4-[4-[2-[(2s,4r)-1-[(2r)-2-(ethylcarbamoylamino)-2-phenylacetyl]-4-hydroxypyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-4-hydroxypyrrolidin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1([C@@H](NC(=O)NCC)C(=O)N2C[C@H](O)C[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2C[C@@H](O)CN2C(=O)[C@H](NC(=O)NCC)C=2C=CC=CC=2)=CC=CC=C1 STZFHBJVOSTLJY-HEMKMFBASA-N 0.000 claims 1
- NAVMQJJJBCMION-DNMDQSTESA-N 1-ethyl-3-[(1r)-2-oxo-2-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-oxolane-2-carbonyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-1-phenylethyl]urea Chemical compound C([C@H]1C=2NC=C(N=2)C2=CC=C(C=C2)C2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](NC(=O)NCC)C=2C=CC=CC=2)CCN1C(=O)[C@H]1CCCO1 NAVMQJJJBCMION-DNMDQSTESA-N 0.000 claims 1
- IZWNAILWAKQOER-JPYDVTDNSA-N 1-methyl-3-[(1r)-2-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(methylcarbamoylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1([C@@H](NC(=O)NC)C(=O)N2CCC[C@H]2C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](NC(=O)NC)C=2C=CC=CC=2)=CC=CC=C1 IZWNAILWAKQOER-JPYDVTDNSA-N 0.000 claims 1
- YLMQOWRZNAIITO-NCENMTFKSA-N 1-methyl-N-[(1R)-2-[(2S)-2-[5-[4-[4-[2-[(2S)-1-[(2R)-2-[(1-methylpyrrolidine-2-carbonyl)amino]-2-phenylacetyl]pyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]phenyl]-1H-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]pyrrolidine-2-carboxamide Chemical compound CN1C(CCC1)C(=O)N[C@@H](C(=O)N1[C@@H](CCC1)C=1NC(=CN=1)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CN=C(N1)[C@H]1N(CCC1)C([C@@H](C1=CC=CC=C1)NC(=O)C1N(CCC1)C)=O)C1=CC=CC=C1 YLMQOWRZNAIITO-NCENMTFKSA-N 0.000 claims 1
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- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
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- XRLZRYGYLZMQML-FDYONOINSA-N n-[(1r)-2-oxo-1-phenyl-2-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-phenyl-2-[(2-pyridin-3-ylacetyl)amino]acetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]ethyl]-2-pyridin-3-ylacetamide Chemical compound N([C@@H](C(=O)N1[C@@H](CCC1)C=1NC(=CN=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1NC(=NC=1)[C@H]1N(CCC1)C(=O)[C@H](NC(=O)CC=1C=NC=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)CC1=CC=CN=C1 XRLZRYGYLZMQML-FDYONOINSA-N 0.000 claims 1
- CCOQRFXJBJDNQV-DNMDQSTESA-N n-[(1r)-2-oxo-2-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-oxolane-2-carbonyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-1-phenylethyl]acetamide Chemical compound C([C@H]1C2=NC=C(N2)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](NC(=O)C)C=2C=CC=CC=2)CCN1C(=O)[C@H]1CCCO1 CCOQRFXJBJDNQV-DNMDQSTESA-N 0.000 claims 1
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- OVPLZYJGTGDFNB-UHFFFAOYSA-N propan-2-yl carbamate Chemical compound CC(C)OC(N)=O OVPLZYJGTGDFNB-UHFFFAOYSA-N 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (240)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5007235B2 (ja) | 2004-12-20 | 2012-08-22 | ジェネンテック， インコーポレイテッド | Ｉａｐのピロリジンインヒビター |
| US7745636B2 (en) | 2006-08-11 | 2010-06-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8329159B2 (en) | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7759495B2 (en) | 2006-08-11 | 2010-07-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8303944B2 (en) * | 2006-08-11 | 2012-11-06 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7659270B2 (en) | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20100055071A1 (en) * | 2006-11-21 | 2010-03-04 | Martin Robert Leivers | Anti-Viral Compounds |
| KR20100024923A (ko) * | 2007-04-30 | 2010-03-08 | 제넨테크, 인크. | Ｉａｐ의 억제제 |
| CN102872461A (zh) | 2007-05-04 | 2013-01-16 | 弗特克斯药品有限公司 | 用于治疗hcv感染的组合治疗 |
| US7741347B2 (en) | 2007-05-17 | 2010-06-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| ITMI20071012A1 (it) * | 2007-05-18 | 2008-11-19 | St Microelectronics Srl | Dispositivo di memoria migliorato a veloce programmazione |
| CN102015606B (zh) | 2007-06-08 | 2015-02-04 | 满康德股份有限公司 | IRE-1α抑制剂 |
| EP2170863B1 (en) * | 2007-07-05 | 2015-09-02 | Array Biopharma, Inc. | Pyrimido cyclopentanes useful for the treatment of inflammatory or hyperproliferative diseases |
| US8629171B2 (en) * | 2007-08-08 | 2014-01-14 | Bristol-Myers Squibb Company | Crystalline form of methyl ((1S)-1-((25)-2-(5-(4'-(2-((25)-1((2S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-2-pyrrolidinyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate dihydrochloride salt |
| US7728027B2 (en) * | 2007-08-08 | 2010-06-01 | Bristol-Myers Squibb Company | Process for synthesizing compounds useful for treating hepatitis C |
| CA2711957C (en) | 2007-10-11 | 2019-03-19 | The Regents Of The University Of California | Use of inhibitors of n-acylethanolamine-hydrolyzing acid amidase as anti-inflamatory medicaments |
| BRPI0907733A2 (pt) | 2008-02-12 | 2015-07-14 | Bristol Myers Squibb Co | Inibidores do vírus da hepatite c |
| JP5314053B2 (ja) * | 2008-02-12 | 2013-10-16 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ型肝炎ウイルス阻害剤 |
| US8147818B2 (en) | 2008-02-13 | 2012-04-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7704992B2 (en) | 2008-02-13 | 2010-04-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| NZ587557A (en) * | 2008-02-13 | 2012-04-27 | Bristol Myers Squibb Co | Imidazolyl biphenyl imidazoles as hepatitis c virus inhibitors |
| AU2009279924B2 (en) | 2008-08-02 | 2014-10-02 | Genentech, Inc. | Inhibitors of IAP |
| US7906655B2 (en) | 2008-08-07 | 2011-03-15 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8383094B2 (en) | 2008-10-01 | 2013-02-26 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TWI480272B (zh) * | 2008-10-09 | 2015-04-11 | Anadys Pharmaceuticals Inc | 藉由５，６－二氫－１ｈ－吡啶－２－酮與一或多種其他抗病毒化合物的組合物抑制ｃ型肝炎病毒的方法 |
| AU2009322387A1 (en) | 2008-12-03 | 2011-06-30 | Presidio Pharmaceuticals, Inc. | Inhibitors of HCV NS5A |
| EA024853B1 (ru) | 2008-12-03 | 2016-10-31 | Пресидио Фармасьютикалс, Инк. | Ингибиторы ns5a вгс |
| US8541424B2 (en) * | 2008-12-23 | 2013-09-24 | Abbott Laboratories | Anti-viral compounds |
| US8546405B2 (en) | 2008-12-23 | 2013-10-01 | Abbott Laboratories | Anti-viral compounds |
| EP2393359A4 (en) * | 2009-02-09 | 2012-10-03 | Enanta Pharm Inc | COMPOUND DIBENZIMIDAZOLE DERIVATIVES |
| US8420686B2 (en) | 2009-02-17 | 2013-04-16 | Enanta Pharmaceuticals, Inc. | Linked diimidazole antivirals |
| TWI438200B (zh) | 2009-02-17 | 2014-05-21 | 必治妥美雅史谷比公司 | Ｃ型肝炎病毒抑制劑 |
| 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 |
| US8188132B2 (en) | 2009-02-17 | 2012-05-29 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| US8637561B2 (en) | 2009-02-17 | 2014-01-28 | Enanta Pharmaceuticals, Inc. | Linked diimidazole derivatives |
| UY32462A (es) | 2009-02-23 | 2010-09-30 | Arrow Therapeutics Ltd | Derivados de bifenilo novedosos para el tratamiento de infección por virus de hepatitis c 644 |
| CA2753313A1 (en) * | 2009-02-23 | 2010-08-26 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| US8426458B2 (en) | 2009-02-27 | 2013-04-23 | Enanta Pharmaceuticals, Inc. | Hepatitis C Virus inhibitors |
| 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 |
| CN102427731B (zh) | 2009-02-27 | 2015-05-13 | 英安塔制药有限公司 | 丙型肝炎病毒抑制剂 |
| US8673954B2 (en) | 2009-02-27 | 2014-03-18 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US10752611B2 (en) | 2009-02-27 | 2020-08-25 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US8507522B2 (en) | 2009-03-06 | 2013-08-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| CN102427726B (zh) * | 2009-03-27 | 2014-10-08 | 普雷西迪奥制药公司 | 丙型肝炎的稠环抑制剂 |
| US8709999B2 (en) | 2009-03-27 | 2014-04-29 | Presidio Pharmaceuticals, Inc. | Substituted bicyclic HCV inhibitors |
| TWI476190B (zh) * | 2009-03-30 | 2015-03-11 | 必治妥美雅史谷比公司 | Ｃ型肝炎病毒抑制劑 |
| 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 |
| US20110182850A1 (en) | 2009-04-10 | 2011-07-28 | Trixi Brandl | Organic compounds and their uses |
| US8512690B2 (en) | 2009-04-10 | 2013-08-20 | Novartis Ag | Derivatised proline containing peptide compounds as protease inhibitors |
| US8143414B2 (en) | 2009-04-13 | 2012-03-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| RU2541571C2 (ru) * | 2009-04-15 | 2015-02-20 | Эббви Инк. | Противовирусные соединения |
| MX2011011136A (es) * | 2009-04-24 | 2011-11-18 | Tibotec Pharm Ltd | Eteres diarilicos. |
| WO2010132538A1 (en) * | 2009-05-12 | 2010-11-18 | Schering Corporation | Fused tricyclic aryl compounds useful for the treatment of viral diseases |
| AU2013202666B2 (en) * | 2009-05-13 | 2015-07-16 | Gilead Sciences, Inc. | Antiviral compounds |
| AU2014203349B2 (en) * | 2009-05-13 | 2014-11-27 | Gilead Sciences, Inc. | Antiviral compounds |
| EA027493B1 (ru) * | 2009-05-13 | 2017-07-31 | Джилид Фармассет Ллс | Промежуточные соединения для получения противовирусного соединения |
| US8211928B2 (en) | 2009-05-29 | 2012-07-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8138215B2 (en) * | 2009-05-29 | 2012-03-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| 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 |
| AU2010253791A1 (en) | 2009-05-29 | 2011-11-24 | Merck Sharp & Dohme Corp. | Antiviral compounds composed of three linked Aryl moieties to treat diseases such as Hepatitis C |
| US8716454B2 (en) | 2009-06-11 | 2014-05-06 | Abbvie Inc. | Solid compositions |
| US9394279B2 (en) | 2009-06-11 | 2016-07-19 | Abbvie Inc. | Anti-viral compounds |
| ES2414934T3 (es) | 2009-06-11 | 2013-07-23 | Abbvie Bahamas Limited | Inhibidores del virus de la Hepatitis C |
| AU2012203474B2 (en) * | 2009-06-11 | 2014-09-18 | Abbvie Ireland Unlimited Company | Anti-Viral Compounds |
| US8937150B2 (en) * | 2009-06-11 | 2015-01-20 | 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 |
| JP2012533569A (ja) | 2009-07-16 | 2012-12-27 | ヴァーテックス 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症を治療又は予防するためのベンゾイミダゾール類似体 |
| EP2462136A1 (en) | 2009-08-07 | 2012-06-13 | Janssen R&D Ireland | Phenyl ethynyl derivatives as hepatitis c virus inhibitors |
| US8623899B2 (en) | 2009-08-07 | 2014-01-07 | Janssen Research & Development Ireland | Bis-benzimidazole derivatives as hepatitis C virus inhibitors |
| WO2011026920A1 (en) | 2009-09-03 | 2011-03-10 | Tibotec Pharmaceuticals | Bis-benzimidazole derivatives |
| WO2011028596A1 (en) * | 2009-09-04 | 2011-03-10 | Glaxosmithkline Llc | Chemical compounds |
| US8927709B2 (en) * | 2009-09-11 | 2015-01-06 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| WO2011031934A1 (en) * | 2009-09-11 | 2011-03-17 | Enanta Pharmaceuticals, Inc. | Hepatitis c virus inhibitors |
| WO2011031904A1 (en) | 2009-09-11 | 2011-03-17 | Enanta Pharmaceuticals, Inc | Hepatitis c virus inhibitors |
| US8822700B2 (en) * | 2009-09-11 | 2014-09-02 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8703938B2 (en) * | 2009-09-11 | 2014-04-22 | 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 |
| US8415374B2 (en) | 2009-10-12 | 2013-04-09 | Bristol-Myers Squibb Company | Combinations of hepatitis C virus inhibitors |
| UA108211C2 (uk) * | 2009-11-04 | 2015-04-10 | Янссен Рід Айрленд | Бензімідазолімідазольні похідні |
| 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 |
| EP2503881B1 (en) | 2009-11-25 | 2015-05-13 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds and derivatives thereof useful for the treatment of viral diseases |
| US20110137633A1 (en) * | 2009-12-03 | 2011-06-09 | Abbott Laboratories | Anti-viral compounds and methods of identifying the same |
| MY179840A (en) * | 2009-12-04 | 2020-11-18 | National Health Res Inst | Proline derivatives |
| WO2011081918A1 (en) | 2009-12-14 | 2011-07-07 | Enanta Pharmaceuticals, Inc | Hepatitis c virus inhibitors |
| US8377980B2 (en) * | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CN104530079B (zh) * | 2009-12-18 | 2017-10-20 | 北京凯因科技股份有限公司 | C型肝炎病毒复制的新型抑制剂 |
| BR112012014899A2 (pt) | 2009-12-18 | 2017-03-14 | Idenix Pharmaceuticals Inc | composto, composição farmacêutica, método para tratar ou prevenir uma infecção por vírus de hepatite c em um sujeito, método para tratar , prevenir ou melhorar um ou mais sintomas de uma doença hepática ou distúrbio associado a uma infecção por vírus de hepatite c em um sujeito, método para inibir a replicação de um vírus em um hospedeiro, método para inibir a replicação de um vírus |
| KR20120116404A (ko) | 2009-12-18 | 2012-10-22 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｈｃｖ 병용 요법 |
| AU2010341537A1 (en) | 2009-12-22 | 2012-08-09 | Merck Sharp & Dohme Corp. | Fused Tricyclic Compounds and methods of use thereof for the treatment of viral diseases |
| EP2515902A1 (en) * | 2009-12-24 | 2012-10-31 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of flavivirus infections |
| US8362020B2 (en) | 2009-12-30 | 2013-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| JP2013518060A (ja) | 2010-01-25 | 2013-05-20 | エナンタ ファーマシューティカルズ インコーポレイテッド | Ｃ型肝炎ウイルス阻害剤 |
| US8933110B2 (en) | 2010-01-25 | 2015-01-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| EP2528926A4 (en) * | 2010-01-28 | 2013-06-19 | Boehringer Ingelheim Int | HEPATITIS C INHIBITOR COMPOUNDS |
| 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 |
| US8609635B2 (en) | 2010-03-09 | 2013-12-17 | Merck Sharp & Dohme Corp. | Fused tricyclic silyl compounds and methods of use thereof for the treatment of viral diseases |
| MX2012010919A (es) * | 2010-03-24 | 2013-02-01 | Vertex Pharma | Analogos para el tratamiento o prevencion de infecciones por flavivirus. |
| CA2794145A1 (en) | 2010-03-24 | 2011-09-29 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of flavivirus infections |
| WO2011119860A1 (en) * | 2010-03-24 | 2011-09-29 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of flavivirus infections |
| EP3290428B1 (en) | 2010-03-31 | 2021-10-13 | Gilead Pharmasset LLC | Tablet comprising crystalline (s)-isopropyl 2-(((s)-(((2r,3r,4r,5r)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2h)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate |
| US9127021B2 (en) | 2010-04-09 | 2015-09-08 | 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 |
| US20110312996A1 (en) * | 2010-05-17 | 2011-12-22 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| CA2800509A1 (en) * | 2010-05-24 | 2011-12-01 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| EP2575819A4 (en) | 2010-06-04 | 2013-11-27 | Enanta Pharm Inc | INHIBITORS OF HEPATITIS C VIRUS |
| NZ605440A (en) * | 2010-06-10 | 2014-05-30 | Abbvie Bahamas Ltd | Solid compositions comprising an hcv inhibitor |
| AR081691A1 (es) | 2010-06-28 | 2012-10-10 | Vertex Pharma | Derivados de tiofeno, metodos para su preparacion y su uso en el tratamiento o la prevencion de infecciones por flavivirus |
| EP2585448A1 (en) | 2010-06-28 | 2013-05-01 | Vertex Pharmaceuticals Incorporated | Compounds and methods for the treatment or prevention of flavivirus infections |
| WO2012009394A2 (en) * | 2010-07-16 | 2012-01-19 | Bristol-Myers Squibb Company | Methods to identify combinations of ns5a targeting compounds that act synergistically to inhibit hepatitis c virus replication |
| JP2013541499A (ja) | 2010-07-26 | 2013-11-14 | メルク・シャープ・エンド・ドーム・コーポレイション | 置換されたビフェニレン化合物およびウイルス性疾患の治療のためのその使用方法 |
| ES2504977T3 (es) | 2010-07-26 | 2014-10-09 | Janssen R&D Ireland | Derivados hetero-bicíclicos como inhibidores del VHC |
| US20120196794A1 (en) * | 2010-08-06 | 2012-08-02 | Bristol-Myers Squibb Company | Combinations of Hepatitis C Virus Inhibitors |
| EP2603080A4 (en) | 2010-08-12 | 2014-01-22 | Enanta Pharm Inc | HEPATITIS C-VIRUS HEMMER |
| US20120195857A1 (en) | 2010-08-12 | 2012-08-02 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| AR082619A1 (es) | 2010-08-13 | 2012-12-19 | Hoffmann La Roche | Inhibidores del virus de la hepatitis c |
| EP2606041A2 (en) | 2010-08-17 | 2013-06-26 | Vertex Pharmaceuticals Incorporated | Compounds and methods for the treatment or prevention of flaviviridae viral infections |
| EP2963034A1 (en) * | 2010-08-26 | 2016-01-06 | RFS Pharma, LLC. | Potent and selective inhibitors of hepatitis c virus |
| US8822520B2 (en) | 2010-09-22 | 2014-09-02 | Presidio Pharmaceuticals, Inc. | Substituted bicyclic HCV inhibitors |
| CN103249730A (zh) * | 2010-09-24 | 2013-08-14 | 百时美施贵宝公司 | 丙型肝炎病毒抑制剂 |
| AU2011314168A1 (en) | 2010-09-29 | 2013-04-04 | Merck Sharp & Dohme Corp. | Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012050918A2 (en) | 2010-09-29 | 2012-04-19 | Presidio Pharmaceutical, Inc. | Tricyclic fused ring inhibitors of hepatitis c |
| CN103179966B (zh) | 2010-10-08 | 2017-03-15 | 诺瓦提斯公司 | 磺酰胺ns3抑制剂的维生素e制剂 |
| AU2014203655B2 (en) * | 2010-10-13 | 2016-07-07 | Abbvie Ireland Unlimited Company | Anti-viral compounds |
| SI2692346T1 (sl) * | 2010-10-13 | 2016-03-31 | Abbvie Bahamas Limited | Antivirusni derivati 1-fenil-2,5-dibenzimidazol-5-il-pirolidina |
| WO2012048421A1 (en) * | 2010-10-14 | 2012-04-19 | Boehringer Ingelheim International Gmbh | Hepatitis c inhibitor compounds |
| EA025151B1 (ru) | 2010-10-26 | 2016-11-30 | Пресидио Фармасьютикалс, Инк. | Ингибиторы вируса гепатита с |
| CA2814534A1 (en) | 2010-11-04 | 2012-05-10 | Theravance, Inc. | Novel inhibitors of hepatitis c virus |
| WO2012068234A2 (en) | 2010-11-17 | 2012-05-24 | Gilead Sciences, Inc. | Antiviral compounds |
| EP2646453A1 (en) | 2010-11-30 | 2013-10-09 | Gilead Pharmasset LLC | Compounds |
| RU2452735C1 (ru) * | 2010-11-30 | 2012-06-10 | Александр Васильевич Иващенко | Замещенные азолы, противовирусный активный компонент, фармацевтическая композиция, способ получения и применения |
| US20150158909A1 (en) * | 2010-12-15 | 2015-06-11 | Abbevie Inc. | Anti-viral compounds |
| WO2012083061A2 (en) * | 2010-12-15 | 2012-06-21 | Abbott Laboratories | Anti-viral compounds |
| WO2012087976A2 (en) * | 2010-12-21 | 2012-06-28 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| WO2012087833A1 (en) | 2010-12-22 | 2012-06-28 | Abbott Laboratories | Hepatitis c inhibitors and uses thereof |
| US8552047B2 (en) * | 2011-02-07 | 2013-10-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2012123298A1 (en) | 2011-03-11 | 2012-09-20 | F. Hoffmann-La Roche Ag | Antiviral compounds |
| US8835456B1 (en) | 2011-03-18 | 2014-09-16 | Achillion Pharmaceuticals, Inc. | NS5A inhibitors useful for treating HCV |
| 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 |
| WO2012158861A2 (en) | 2011-05-18 | 2012-11-22 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of 5-azaspiro[2.4]heptane-6-carboxylic acid and its derivatives |
| SI2714036T1 (sl) | 2011-05-27 | 2016-10-28 | Achillion Pharmaceuticals, Inc. | Substituirani alifani, ciklofani, heterafani, heterofani, hetero-heterafani in metaloceni, uporabni pri zdravljenju okužb s HCV |
| US20120328565A1 (en) | 2011-06-24 | 2012-12-27 | Brinkman John A | Antiviral compounds |
| WO2013016501A1 (en) | 2011-07-26 | 2013-01-31 | Vertex Pharmaceuticals Incorporated | Formulations of thiophene compounds |
| WO2013016499A1 (en) | 2011-07-26 | 2013-01-31 | Vertex Pharmaceuticals Incorporated | Methods for preparation of thiophene compounds |
| EP2747569A4 (en) * | 2011-08-24 | 2015-07-08 | Glaxosmithkline Llc | COMBINATION TREATMENTS FOR HEPATITIS C |
| WO2013030750A1 (en) | 2011-09-01 | 2013-03-07 | Lupin Limited | Antiviral compounds |
| US20140378416A1 (en) | 2011-09-14 | 2014-12-25 | Michael P. Dwyer | Silyl-containing heterocyclic compounds and methods of use thereof for the treatment of viral diseases |
| PH12014500557A1 (en) | 2011-09-16 | 2014-05-26 | Gilead Pharmasset Llc | Methods for treating hcv |
| GB201116559D0 (en) * | 2011-09-26 | 2011-11-09 | Univ Leuven Kath | Novel viral replication inhibitors |
| US9180193B2 (en) | 2011-10-10 | 2015-11-10 | Hoffmann-La Roche Inc. | Antiviral compounds |
| US8466159B2 (en) | 2011-10-21 | 2013-06-18 | Abbvie Inc. | Methods for treating HCV |
| US8492386B2 (en) | 2011-10-21 | 2013-07-23 | Abbvie Inc. | Methods for treating HCV |
| PT107925A (pt) | 2011-10-21 | 2014-12-03 | Abbvie Inc | Tratamento de combinação de daa (eg. com abt-072 ou abt-333) para utilização no tratamento de hcv |
| BR112014006314A2 (pt) | 2011-10-21 | 2017-04-11 | Abbvie Inc | métodos para tratamento do vírus da hepatite c (hcv) compreendendo pelo menos dois agentes antivirais de atuação direta, ribavirina, sem interferon |
| RU2625787C2 (ru) * | 2011-11-03 | 2017-07-19 | ТЕРЕВАНС БАЙОФАРМА Ар энд Ди АйПи, ЭлЭлСи | Ингибиторы вируса гепатита с, имеющие жесткую вытянутую цепь и содержащие фрагмент { 2-[4-(бифенил-4-ил)-1н-имидазо-2-ил]пирролидин-1-карбонилметил} амина |
| PL2907816T3 (pl) | 2011-11-16 | 2019-03-29 | Gilead Pharmasset Llc | Skondensowane imidazolyloimidazole jako związki przeciwwirusowe |
| US9353075B2 (en) | 2011-11-22 | 2016-05-31 | The Regents Of The University Of California | Disubstituted beta-lactones as inhibitors of N-acylethanolamine acid amidase (NAAA) |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| CA2855574A1 (en) | 2011-12-16 | 2013-06-20 | F. Hoffmann-La Roche Ag | Inhibitors of hcv ns5a |
| UA111761C2 (uk) | 2011-12-20 | 2016-06-10 | Рібосаєнс Ллс | 2',4'-дифтор-2'-метилзаміщені нуклеозидні похідні як інгібітори реплікації phk вірусу гепатиту c |
| UA110428C2 (uk) | 2011-12-20 | 2015-12-25 | Riboscience Llc | 4'-азидо, 3'-фторзаміщені похідні нуклеозидів як інгібітори реплікації рнк вірусу гепатиту c |
| RU2621734C1 (ru) * | 2011-12-28 | 2017-06-07 | Янссен Сайенсиз Айрлэнд Юси | Гетеробициклические производные в качестве ингибиторов hcv |
| BR112014016007A8 (pt) | 2011-12-28 | 2017-07-04 | Janssen R&D Ireland | derivados de quinazolinona como inibidores de vhc |
| 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 |
| NZ628515A (en) | 2012-02-10 | 2016-06-24 | Lupin Ltd | Antiviral compounds with a dibenzooxaheterocycle moiety |
| CA2857262A1 (en) | 2012-02-24 | 2013-08-29 | F. Hoffmann-La Roche Ag | Antiviral compounds |
| US9012427B2 (en) | 2012-03-22 | 2015-04-21 | Alios Biopharma, Inc. | Pharmaceutical combinations comprising a thionucleotide analog |
| CA2869908C (en) | 2012-04-25 | 2018-02-20 | Theravance Biopharma R&D Ip, Llc | Hepatitis c virus inhibitors |
| ES2624846T3 (es) | 2012-04-25 | 2017-07-17 | Theravance Biopharma R&D Ip, Llc | Compuestos de piperazina-piperidina como inhibidores del virus de la hepatitis C |
| WO2013165796A1 (en) | 2012-05-03 | 2013-11-07 | Theravance, Inc. | Crystalline form of a pyridyl-piperazinyl hepatitis c virus inhibitor |
| US20130309196A1 (en) | 2012-05-16 | 2013-11-21 | Gilead Sciences, Inc. | Antiviral compounds |
| US20140010783A1 (en) | 2012-07-06 | 2014-01-09 | Hoffmann-La Roche Inc. | Antiviral compounds |
| US20150252028A1 (en) * | 2012-10-24 | 2015-09-10 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| JP6096324B2 (ja) | 2013-01-23 | 2017-03-15 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 抗ウイルス性トリアゾール誘導体 |
| SG11201506021XA (en) | 2013-01-31 | 2015-08-28 | Gilead Pharmasset Llc | Combination formulation of two antiviral compounds |
| RU2507201C1 (ru) | 2013-02-07 | 2014-02-20 | Александр Васильевич Иващенко | Алкил [(s)-1-((s)-2-{5-[4-(4-{2-[(s)-1-((s)-2-метоксикарбониламино-3-метил-бутирил)-пирролидин-2-ил]-3н-имидазол-4-ил}-бута-1,3-диинил)-фенил]-1н-имидазол-2-ил}-пирролидин-1-карбонил)-2-метил-пропил]-карбамат нафталин-1,5-дисульфонат, фармацевтическая композиция, лекарственное средство, способ лечения вирусных заболеваний |
| WO2014134251A1 (en) | 2013-02-28 | 2014-09-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions |
| MX2015011193A (es) | 2013-03-05 | 2015-11-13 | Hoffmann La Roche | Compuestos antivirales. |
| US11484534B2 (en) | 2013-03-14 | 2022-11-01 | Abbvie Inc. | Methods for treating HCV |
| WO2014144547A2 (en) | 2013-03-15 | 2014-09-18 | The Regents Of The University Of California | Amide derivatives of lactam based n-acylethanolamine acid amidase (naaa) inhibitors |
| WO2014144836A2 (en) | 2013-03-15 | 2014-09-18 | The Regents Of The University Of California | Carbamate derivatives of lactam based n-acylethanolamine acid amidase (naaa) inhibitors |
| WO2014175699A1 (ko) | 2013-04-26 | 2014-10-30 | 서울대학교 산학협력단 | 벤지딘 유도체, 이의 제조방법 및 이를 함유하는 c형 간염 바이러스에 의한 간질환 치료용 약학적 조성물. |
| US9895442B2 (en) | 2013-05-16 | 2018-02-20 | Riboscience Llc | 4′-fluoro-2′-methyl substituted nucleoside derivatives as inhibitors of HCV RNA replication |
| BR112015028765A2 (pt) | 2013-05-16 | 2017-07-25 | Riboscience Llc | derivados de nucleosídeo substituído 4'-azido, 3'-desoxi-3'-fluoro |
| US20180200280A1 (en) | 2013-05-16 | 2018-07-19 | Riboscience Llc | 4'-Fluoro-2'-Methyl Substituted Nucleoside Derivatives as Inhibitors of HCV RNA Replication |
| WO2015026454A1 (en) * | 2013-07-17 | 2015-02-26 | Bristol-Myers Squibb Company | Combinations comprising tricyclohexadecahexaene derivatives for use in the treatment of hepatitis c virus |
| 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 |
| CN105517574B (zh) * | 2013-07-09 | 2019-01-18 | 百时美施贵宝公司 | 丙型肝炎病毒抑制剂的组合产品 |
| US9775831B2 (en) | 2013-07-17 | 2017-10-03 | Bristol-Myers Squibb Company | Combinations comprising biphenyl derivatives for use in the treatment of HCV |
| EP3038601B1 (en) | 2013-08-27 | 2020-04-08 | Gilead Pharmasset LLC | Combination formulation of two antiviral compounds |
| KR101561964B1 (ko) | 2013-11-15 | 2015-10-20 | 한국과학기술연구원 | 옥사졸리디논 화합물 및 이를 포함하는 c형 간염 예방 또는 치료용 약학 조성물 |
| US20160311806A1 (en) * | 2013-12-11 | 2016-10-27 | Bristol-Myers Squibb Company | 4,4'-biphenyldiyl-bis-(1 h-imidazolyl) derivatives as hepatitis hcv inhibitors |
| 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 |
| WO2015154023A1 (en) | 2014-04-04 | 2015-10-08 | X-Rx Discovery, Inc. | Substituted spirocydic inhibitors of autotaxin |
| 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 |
| EP3166852B1 (en) | 2014-07-08 | 2018-03-28 | GIMA S.p.A. | Unit and method for filling containing elements of single-use capsules for extraction or infusion beverages. |
| WO2016075588A1 (en) * | 2014-11-11 | 2016-05-19 | Sun Pharmaceutical Industries Limited | Stable amorphous daclatasvir dihydrochloride |
| WO2016089814A1 (en) | 2014-12-02 | 2016-06-09 | Concert Pharmaceuticals, Inc. | Deuterated analogues of daclatasvir |
| CN105753944B (zh) * | 2014-12-19 | 2019-10-01 | 正大天晴药业集团股份有限公司 | 达卡他韦及其衍生物的制备中间体 |
| WO2016102979A1 (en) | 2014-12-26 | 2016-06-30 | Cipla Limited | Polymorphic forms of methyl((1s)-1-(((2s)-2-(5-(4'-(2-((2s)-1-((2s)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-2-pyrrolidinyl)-1h-imidazol-5-yl)-4-biphenylyl)-1h-imidazol-2-yl)-1-pyrrolidinyl) carbonyl)-2-methylpropyl)carbamate and salts thereof |
| CN106188015B (zh) * | 2015-05-06 | 2019-10-18 | 广东东阳光药业有限公司 | 一种制备达卡他韦的方法 |
| WO2016178250A1 (en) | 2015-05-07 | 2016-11-10 | Mylan Laboratories Limited | Process for the preparation of daclatasvir |
| CZ2015366A3 (cs) | 2015-05-29 | 2016-12-07 | Zentiva, K.S. | Pevné formy Daclatasviru |
| US20160375017A1 (en) | 2015-06-26 | 2016-12-29 | Abbvie Inc. | Solid Pharmaceutical Compositions for Treating HCV |
| WO2017023631A1 (en) | 2015-08-06 | 2017-02-09 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| WO2017076358A1 (zh) * | 2015-11-06 | 2017-05-11 | 苏州晶云药物科技有限公司 | 咪唑基联苯基化合物盐的新晶型及其制备方法 |
| GB2552919A (en) * | 2015-11-18 | 2018-02-21 | Azad Pharmaceutical Ingredients Ag | Stable amorphous form of daclatasvir |
| CN106083829B (zh) * | 2016-01-12 | 2019-01-22 | 深圳市塔吉瑞生物医药有限公司 | 一种丙型肝炎病毒抑制剂、药物组合物及其应用 |
| US11186541B2 (en) * | 2016-03-28 | 2021-11-30 | The University Of Toledo | Potent inhibitors of aspartate N-acetyl-transferase for the treatment of Canavan disease |
| SG10201900628RA (en) | 2016-04-07 | 2019-02-27 | Glaxosmithkline Ip Dev Ltd | Heterocyclic amides useful as protein modulators |
| WO2017189978A1 (en) | 2016-04-28 | 2017-11-02 | Emory University | Alkyne containing nucleotide and nucleoside therapeutic compositions and uses related thereto |
| WO2018007984A1 (en) | 2016-07-08 | 2018-01-11 | Lupin Limited | Crystalline forms of daclatasvir dihydrochloride |
| US20190337932A1 (en) * | 2016-07-18 | 2019-11-07 | Gienmark Pharmaceuticals Limited | Process for preparation of daclatasvir and salts |
| CN108069941A (zh) * | 2016-11-15 | 2018-05-25 | 广东东阳光药业有限公司 | 一种制备达卡他韦的方法 |
| RU2650610C1 (ru) | 2017-02-28 | 2018-04-16 | Васильевич Иващенко Александр | Противовирусная композиция и способ ее применения |
| US10392370B2 (en) * | 2017-03-13 | 2019-08-27 | Optimus Drugs Pvt Ltd | Process for the preparation of Daclatasvir dihydrochloride and its intermediates |
| WO2018171660A1 (zh) | 2017-03-22 | 2018-09-27 | 正大天晴药业集团股份有限公司 | 用于抗丙型肝炎病毒感染的含硅化合物 |
| CN109305962B (zh) * | 2017-07-28 | 2022-01-18 | 扬子江药业集团有限公司 | 一种盐酸达拉他韦的精制方法 |
| CN111194217B (zh) | 2017-09-21 | 2024-01-12 | 里伯赛恩斯有限责任公司 | 作为hcv rna复制抑制剂的4’-氟-2’-甲基取代的核苷衍生物 |
| EP3891508A1 (en) | 2018-12-04 | 2021-10-13 | Bristol-Myers Squibb Company | Methods of analysis using in-sample calibration curve by multiple isotopologue reaction monitoring |
| WO2020219808A1 (en) * | 2019-04-25 | 2020-10-29 | Beta Pharma, Inc. | Dicarbamate inhibitors of ns5a for treatment of hepatitis c virus infections and related diseases |
| EP4304586A4 (en) | 2021-03-10 | 2025-04-02 | Jnana Therapeutics Inc. | SMALL MOLECULE INHIBITORS OF MAMMALIAN SLC6A19 FUNCTION |
| CN117321059A (zh) | 2021-05-21 | 2023-12-29 | 吉利德科学公司 | 用于治疗寨卡病毒感染的四环化合物 |
| AU2022279234B2 (en) | 2021-05-21 | 2025-08-28 | Gilead Sciences, Inc. | Pentacyclic derivatives as zika virus inhibitors |
| EP4587021A1 (en) * | 2022-09-14 | 2025-07-23 | Jnana Therapeutics Inc. | Treating pku with correctors of mammalian slc6a19 function |
| WO2025122482A1 (en) * | 2023-12-04 | 2025-06-12 | Henry Ford Health System | Methods and compositions to inhibit tribbles 2 for cancer therapy |
| CN119707774A (zh) * | 2024-12-24 | 2025-03-28 | 浙江工业大学 | 一种微波辅助1,5,6,7-四氢-4h-吲哚-4-酮衍生物的溴化方法 |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994015909A1 (en) | 1993-01-14 | 1994-07-21 | Magainin Pharmaceuticals, Inc. | Amino acids and peptides having modified terminals |
| US5654451B1 (en) | 1993-01-14 | 2000-02-22 | Magainin Pharma | Amino acids and peptides having modified c-terminals and modified n-terminals |
| EP0946587A2 (en) * | 1996-12-16 | 1999-10-06 | Fujisawa Pharmaceutical Co., Ltd. | New amide compounds |
| US7244721B2 (en) * | 2000-07-21 | 2007-07-17 | Schering Corporation | Peptides as NS3-serine protease inhibitors of hepatitis C virus |
| US20030220386A1 (en) * | 2000-09-22 | 2003-11-27 | Andrew Plant | Delta 1-pyrrolines for use as pesticides |
| WO2004002940A1 (en) | 2002-07-01 | 2004-01-08 | Pharmacia & Upjohn Company | Inhibitors of hcv ns5b polymerase |
| EP1532118A2 (en) | 2002-07-05 | 2005-05-25 | Axxima Pharmaceuticals Aktiengesellschaft | Imidazole compounds for the treatment of hepatitis c virus infections |
| AU2003261434A1 (en) | 2002-08-12 | 2004-02-25 | Bristol-Myers Squibb Company | Iminothiazolidinones as inhibitors of hcv replication |
| DE10243939A1 (de) * | 2002-09-24 | 2004-04-01 | Bayer Cropscience Ag | Pyrroline |
| US7220745B2 (en) | 2003-05-15 | 2007-05-22 | Rigel Pharmaceuticals | Heterocyclic compounds useful to treat HCV |
| US20050119318A1 (en) | 2003-10-31 | 2005-06-02 | Hudyma Thomas W. | Inhibitors of HCV replication |
| GB0326168D0 (en) | 2003-11-10 | 2003-12-17 | Arrow Therapeutics Ltd | Chemical compounds |
| US7514434B2 (en) * | 2004-02-23 | 2009-04-07 | Rigel Pharmaceuticals, Inc. | Heterocyclic compounds having an oxadiazole moiety and hydro isomers thereof |
| KR20070011501A (ko) | 2004-04-28 | 2007-01-24 | 애로우 쎄라퓨틱스 리미티드 | 항바이러스제로서 유용한 모르폴리닐아닐리노퀴나졸린유도체 |
| MX2007001029A (es) * | 2004-07-26 | 2007-04-12 | Lilly Co Eli | Agentes del receptor de histamina h3, preparacion y usos terapeuticos. |
| WO2006022442A1 (ja) | 2004-08-24 | 2006-03-02 | Santen Pharmaceutical Co., Ltd. | ジヒドロオロテートデヒドロゲナーゼ阻害活性を有する新規複素環アミド誘導体 |
| US7894996B2 (en) | 2005-02-28 | 2011-02-22 | The Rockefeller University | Structure of the hepatitis C NS5A protein |
| US8143288B2 (en) | 2005-06-06 | 2012-03-27 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| KR20080050490A (ko) | 2005-09-16 | 2008-06-05 | 애로우 쎄라퓨틱스 리미티드 | 바이페닐 유도체, 및 ｃ형 간염 치료에 있어서의 그의 용도 |
| WO2007058384A1 (en) | 2005-11-17 | 2007-05-24 | Osaka University | Method of suppressing replication of hepatitis c virus, inhibitor of replication of the virus and method of screening for the same |
| WO2007081517A2 (en) | 2005-12-21 | 2007-07-19 | Abbott Laboratories | Anti-viral compounds |
| SG133452A1 (en) | 2005-12-30 | 2007-07-30 | Novartis Ag | Peptide deformylase inhibitors for treatment of mycobacterial and other parasitic diseases |
| JP2009523163A (ja) | 2006-01-11 | 2009-06-18 | アロー セラピューティクス リミテッド | 抗ウイルス剤として使用するためのトリアゾロアニリノピリミジン誘導体 |
| WO2007082554A1 (en) | 2006-01-23 | 2007-07-26 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | Modulators of hcv replication |
| WO2007138242A1 (en) | 2006-05-30 | 2007-12-06 | Arrow Therapeutics Limited | Biphenyl derivatives and their use in treating hepatitis c |
| US7759495B2 (en) * | 2006-08-11 | 2010-07-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8329159B2 (en) * | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7659270B2 (en) | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7745636B2 (en) * | 2006-08-11 | 2010-06-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8303944B2 (en) * | 2006-08-11 | 2012-11-06 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7741347B2 (en) * | 2007-05-17 | 2010-06-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8629171B2 (en) * | 2007-08-08 | 2014-01-14 | Bristol-Myers Squibb Company | Crystalline form of methyl ((1S)-1-((25)-2-(5-(4'-(2-((25)-1((2S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-2-pyrrolidinyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate dihydrochloride salt |
| US8181098B2 (en) * | 2008-06-11 | 2012-05-15 | Freescale Semiconductor, Inc. | Error correcting Viterbi decoder |
| TWI476190B (zh) * | 2009-03-30 | 2015-03-11 | 必治妥美雅史谷比公司 | Ｃ型肝炎病毒抑制劑 |
| US8138215B2 (en) * | 2009-05-29 | 2012-03-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8415374B2 (en) * | 2009-10-12 | 2013-04-09 | Bristol-Myers Squibb Company | Combinations of hepatitis C virus inhibitors |
| US8377980B2 (en) * | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20120196794A1 (en) * | 2010-08-06 | 2012-08-02 | Bristol-Myers Squibb Company | Combinations of Hepatitis C Virus Inhibitors |
| US8552047B2 (en) * | 2011-02-07 | 2013-10-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
-
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