JP2011530531A5 - - Google Patents
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- Publication number
- JP2011530531A5 JP2011530531A5 JP2011522250A JP2011522250A JP2011530531A5 JP 2011530531 A5 JP2011530531 A5 JP 2011530531A5 JP 2011522250 A JP2011522250 A JP 2011522250A JP 2011522250 A JP2011522250 A JP 2011522250A JP 2011530531 A5 JP2011530531 A5 JP 2011530531A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidinyl
- benzimidazol
- benzimidazole
- ethynyl
- carbonyl
- 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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- -1 -NR a R b Chemical group 0.000 claims 56
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 19
- 239000011780 sodium chloride Substances 0.000 claims 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 15
- AKTZKFFAVIOFFB-WSZLSEGOSA-N (2R)-1-[(2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-1H-benzimidazol-4-yl]-1,3-oxazol-5-yl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-(dimethylamino)-2-phenylethanone Chemical compound C=1C=C2NC([C@@H]3CCCN3C(=O)[C@H](N(C)C)C=3C=CC=CC=3)=NC2=CC=1C(O1)=CN=C1C(C=1N=2)=CC=CC=1NC=2[C@@H]1CCCN1C(C)=O AKTZKFFAVIOFFB-WSZLSEGOSA-N 0.000 claims 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 11
- 108010050904 Interferons Proteins 0.000 claims 8
- 102000014150 Interferons Human genes 0.000 claims 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 229940079322 interferon Drugs 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 102100008763 IFNA2 Human genes 0.000 claims 4
- 108010047761 Interferon-alpha Proteins 0.000 claims 4
- 102000006992 Interferon-alpha Human genes 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
- 229960000329 Ribavirin Drugs 0.000 claims 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 4
- 201000009910 diseases by infectious agent Diseases 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 229920000160 (ribonucleotides)n+m Polymers 0.000 claims 2
- JCISRQNKHZNVHJ-UHFFFAOYSA-N 2-hydroxy-2-phenylacetaldehyde Chemical compound O=CC(O)C1=CC=CC=C1 JCISRQNKHZNVHJ-UHFFFAOYSA-N 0.000 claims 2
- 101710036216 ATEG_03556 Proteins 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
- 108020005544 Antisense RNA Proteins 0.000 claims 2
- 101700022936 IFNA2 Proteins 0.000 claims 2
- 101710034397 IMPDH1 Proteins 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
- HAEJPQIATWHALX-KQYNXXCUSA-N Inosine triphosphate 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
- 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
- 229940117681 Interleukin-12 Drugs 0.000 claims 2
- 102000000588 Interleukin-2 Human genes 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 229940100601 Interleukin-6 Drugs 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
- 101800001019 Non-structural protein 4B Proteins 0.000 claims 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims 2
- 101710003000 ORF1/ORF2 Proteins 0.000 claims 2
- 102000004316 Oxidoreductases Human genes 0.000 claims 2
- 108090000854 Oxidoreductases Proteins 0.000 claims 2
- 101700030467 Pol Proteins 0.000 claims 2
- UBCHPRBFMUDMNC-UHFFFAOYSA-N Rimantadine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 2
- 102000012479 Serine Proteases Human genes 0.000 claims 2
- 108010022999 Serine Proteases Proteins 0.000 claims 2
- 210000003283 T-Lymphocytes, Helper-Inducer Anatomy 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229920002847 antisense RNA Polymers 0.000 claims 2
- 239000003184 complementary RNA Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000002708 enhancing Effects 0.000 claims 2
- 101710004774 gua1 Proteins 0.000 claims 2
- 210000002443 helper T lymphocyte Anatomy 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229960002751 imiquimod Drugs 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 230000002452 interceptive Effects 0.000 claims 2
- 101700074809 mpaF Proteins 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 101710004466 rgy Proteins 0.000 claims 2
- 101710030364 rgy1 Proteins 0.000 claims 2
- 101710030359 rgy2 Proteins 0.000 claims 2
- 229960000888 rimantadine Drugs 0.000 claims 2
- UOHMTRVFNSOHES-XFCANUNOSA-N (2R)-1-[(2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-(dimethylamino)-2-phenylethanone Chemical compound C=1C=C2NC([C@@H]3CCCN3C(=O)[C@H](N(C)C)C=3C=CC=CC=3)=NC2=CC=1C#CC(C=C1N=2)=CC=C1NC=2[C@@H]1CCCN1C(C)=O UOHMTRVFNSOHES-XFCANUNOSA-N 0.000 claims 1
- HWRCWJVSZOYVND-CDBYGCFJSA-N (2R)-2-(dimethylamino)-1-[(2S)-2-[6-[2-[(2S)-1-[(2R)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-3H-benzimidazole-5-carbonyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C=2NC3=CC=C(C=C3N=2)C(=O)C=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 HWRCWJVSZOYVND-CDBYGCFJSA-N 0.000 claims 1
- BCEPLZVTQPBOPB-NUXXNWGHSA-N (2R)-2-(dimethylamino)-1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C([C@H]1C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)CCN1C(=O)[C@H]1CCCO1 BCEPLZVTQPBOPB-NUXXNWGHSA-N 0.000 claims 1
- TWJASYBMNHXFNV-VHYZKNOSSA-N (2R)-2-(dimethylamino)-2-phenyl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]-1,3-oxazol-5-yl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound C([C@H]1C=2NC3=CC=C(C=C3N=2)C2=NC=C(O2)C=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)CCN1C(=O)CC1=CC=CC=C1 TWJASYBMNHXFNV-VHYZKNOSSA-N 0.000 claims 1
- JDUFGXFCOQAJAB-CLLHQPRTSA-N (2R)-2-hydroxy-1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-2-hydroxy-2-phenylacetyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 JDUFGXFCOQAJAB-CLLHQPRTSA-N 0.000 claims 1
- IFGMSAKKDKYYAT-IYTFMMMVSA-N (2R)-2-morpholin-4-yl-1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-2-morpholin-4-yl-2-phenylacetyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound N1([C@@H](C(=O)N2[C@@H](CCC2)C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@H]2N(CCC2)C(=O)[C@H](N2CCOCC2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCOCC1 IFGMSAKKDKYYAT-IYTFMMMVSA-N 0.000 claims 1
- IIPYQQJWDWODRY-VVPILZOQSA-N (2R)-2-phenyl-1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-2-phenylpropanoyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound C1([C@@H](C)C(=O)N2CCC[C@H]2C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)[C@H](C)C=2C=CC=CC=2)=CC=CC=C1 IIPYQQJWDWODRY-VVPILZOQSA-N 0.000 claims 1
- NUQOFRGWKXFCIN-BZNWVNPFSA-N (2S)-2-hydroxy-1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2S)-2-hydroxy-2-phenylpropanoyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]-1,3-oxazol-5-yl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylpropan-1-one Chemical compound C1([C@](C)(O)C(=O)N2CCC[C@H]2C=2NC3=CC=C(C=C3N=2)C2=CN=C(O2)C2=CC=C3N=C(NC3=C2)[C@@H]2CCCN2C(=O)[C@](O)(C)C=2C=CC=CC=2)=CC=CC=C1 NUQOFRGWKXFCIN-BZNWVNPFSA-N 0.000 claims 1
- OQOUNIXDUUIUBM-YXRKCGNLSA-N (2S)-2-hydroxy-1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2S)-2-hydroxy-2-phenylpropanoyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylpropan-1-one Chemical compound C1([C@](C)(O)C(=O)N2CCC[C@H]2C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)[C@](O)(C)C=2C=CC=CC=2)=CC=CC=C1 OQOUNIXDUUIUBM-YXRKCGNLSA-N 0.000 claims 1
- CCUTXYHUYHBLPI-ACHIHNKUSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-ethylbenzoyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound CCC1=CC=CC=C1C(=O)N1[C@H](C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3NC(=NC3=CC=2)[C@H]2N(CCC2)C(C)=O)CCC1 CCUTXYHUYHBLPI-ACHIHNKUSA-N 0.000 claims 1
- MGAWDBUTHDOKBG-HEVIKAOCSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-oxo-2-phenylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethane-1,2-dione Chemical compound C([C@H]1C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)C(=O)C=2C=CC=CC=2)CCN1C(=O)C(=O)C1=CC=CC=C1 MGAWDBUTHDOKBG-HEVIKAOCSA-N 0.000 claims 1
- VCZOTKCXYDTOGQ-NSOVKSMOSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-(cyclobutanecarbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)C3CCC3)C=C2N1 VCZOTKCXYDTOGQ-NSOVKSMOSA-N 0.000 claims 1
- ATONGKHRLKENOH-SVBPBHIXSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-(cyclopropanecarbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)C3CC3)C=C2N1 ATONGKHRLKENOH-SVBPBHIXSA-N 0.000 claims 1
- WAIXPAADRONROY-NSOVKSMOSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-(morpholine-4-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)N3CCOCC3)C=C2N1 WAIXPAADRONROY-NSOVKSMOSA-N 0.000 claims 1
- LLFNHXVTTOYPLM-VMPREFPWSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-(pyridine-3-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)C=3C=NC=CC=3)C=C2N1 LLFNHXVTTOYPLM-VMPREFPWSA-N 0.000 claims 1
- KSVYUBDNIHAXPH-SVBPBHIXSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-(thiophene-2-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)C=3SC=CC=3)C=C2N1 KSVYUBDNIHAXPH-SVBPBHIXSA-N 0.000 claims 1
- QIJWNGOZDOAEHQ-XFCANUNOSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC(=CC=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)[C@@H]1OCCC1)C(=O)CC1=CC=CC=C1 QIJWNGOZDOAEHQ-XFCANUNOSA-N 0.000 claims 1
- CLDSFHBZZOWNJJ-OWHBQTKESA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-pyridin-2-ylethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC(=CC=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)[C@@H]1OCCC1)C(=O)CC1=CC=CC=N1 CLDSFHBZZOWNJJ-OWHBQTKESA-N 0.000 claims 1
- HXDXAKHUURNEJV-OWHBQTKESA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-pyridin-3-ylethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC(=CC=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)[C@@H]1OCCC1)C(=O)CC1=CC=CN=C1 HXDXAKHUURNEJV-OWHBQTKESA-N 0.000 claims 1
- PBNYNTAVERLUJO-RWSKJCERSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-thiophen-2-ylethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2NC(=NC2=CC=1)[C@H]1N(CCC1)C(=O)[C@@H]1OCCC1)C(=O)CC1=CC=CS1 PBNYNTAVERLUJO-RWSKJCERSA-N 0.000 claims 1
- BRSQAOTYXVQFNI-DHWXLLNHSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-3-phenoxypropan-1-one Chemical compound N1([C@@H](CCC1)C=1NC2=CC(=CC=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)[C@@H]1OCCC1)C(=O)CCOC1=CC=CC=C1 BRSQAOTYXVQFNI-DHWXLLNHSA-N 0.000 claims 1
- XWJLZQVUUFCLLF-HZFUHODCSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)[C@@H]3OCCC3)C=C2N1 XWJLZQVUUFCLLF-HZFUHODCSA-N 0.000 claims 1
- HWDUIHIXUKZUGH-HZFUHODCSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CCC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)[C@@H]3OCCC3)C=C2N1 HWDUIHIXUKZUGH-HZFUHODCSA-N 0.000 claims 1
- MERWCAZFKLGSJN-ACHIHNKUSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-(3-methoxyphenyl)ethanone Chemical compound COC1=CC=CC(CC(=O)N2[C@@H](CCC2)C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3NC(=NC3=CC=2)[C@H]2N(CCC2)C(C)=O)=C1 MERWCAZFKLGSJN-ACHIHNKUSA-N 0.000 claims 1
- RLBVPMDKEOKLEG-NSOVKSMOSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-cyclopropylethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)CC3CC3)C=C2N1 RLBVPMDKEOKLEG-NSOVKSMOSA-N 0.000 claims 1
- JIFHCIYSWMSLSH-CONSDPRKSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)C=C2N1 JIFHCIYSWMSLSH-CONSDPRKSA-N 0.000 claims 1
- JRTACNTYEOMOBX-KYJUHHDHSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-pyridin-2-ylethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)CC=3N=CC=CC=3)C=C2N1 JRTACNTYEOMOBX-KYJUHHDHSA-N 0.000 claims 1
- PYEMTPKLCISZMK-KYJUHHDHSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-pyridin-3-ylethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)CC=3C=NC=CC=3)C=C2N1 PYEMTPKLCISZMK-KYJUHHDHSA-N 0.000 claims 1
- IZJVINZHZRYQDU-VMPREFPWSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-thiophen-2-ylethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)CC=3SC=CC=3)C=C2N1 IZJVINZHZRYQDU-VMPREFPWSA-N 0.000 claims 1
- WUSHPSVNJPCKAS-UIOOFZCWSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(C)=O)C=C2N1 WUSHPSVNJPCKAS-UIOOFZCWSA-N 0.000 claims 1
- DXUMKEKSTHIWAU-UIOOFZCWSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CCC(=O)N1CCC[C@H]1C1=NC2=CC(C#CC=3C=C4NC(=NC4=CC=3)[C@H]3N(CCC3)C(C)=O)=CC=C2N1 DXUMKEKSTHIWAU-UIOOFZCWSA-N 0.000 claims 1
- RVPAZEUVMIVHET-KYJUHHDHSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-benzoylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)C=3C=CC=CC=3)C=C2N1 RVPAZEUVMIVHET-KYJUHHDHSA-N 0.000 claims 1
- DVEJDZVBGVMUDI-UIOOFZCWSA-N 1-[(2S)-2-[6-[2-[2-[(2S)-1-propanoylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CCC(=O)N1CCC[C@H]1C1=NC2=CC(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)CC)=CC=C2N1 DVEJDZVBGVMUDI-UIOOFZCWSA-N 0.000 claims 1
- RALBSRVEMPXONN-PQFLWIRSSA-N 1-[(2S,4R)-4-hydroxy-2-[6-[2-[2-[(2S,4R)-4-hydroxy-1-(2-phenylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound N1([C@@H](C[C@H](C1)O)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(C[C@H](O)C1)C(=O)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1 RALBSRVEMPXONN-PQFLWIRSSA-N 0.000 claims 1
- DRSAEFAATUYSKR-SOAZDVDRSA-N 1-[(2S,4S)-4-morpholin-4-yl-2-[6-[2-[2-[(2S,4S)-4-morpholin-4-yl-1-(2-phenylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound N1([C@@H](C[C@@H](C1)N1CCOCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(C[C@H](C1)N1CCOCC1)C(=O)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1 DRSAEFAATUYSKR-SOAZDVDRSA-N 0.000 claims 1
- AOGFRXVTKLIGBI-UHFFFAOYSA-N 2-(dimethylamino)-2-phenylacetaldehyde Chemical compound CN(C)C(C=O)C1=CC=CC=C1 AOGFRXVTKLIGBI-UHFFFAOYSA-N 0.000 claims 1
- MIBHBRWEVOCKOV-KYJUHHDHSA-N 2-cyclopropyl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-cyclopropylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2NC(=NC2=CC=1)[C@H]1N(CCC1)C(=O)CC1CC1)C(=O)CC1CC1 MIBHBRWEVOCKOV-KYJUHHDHSA-N 0.000 claims 1
- NLAXXAFZYYUYNP-OIFRRMEBSA-N 2-cyclopropyl-1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC(=CC=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)[C@@H]1OCCC1)C(=O)CC1CC1 NLAXXAFZYYUYNP-OIFRRMEBSA-N 0.000 claims 1
- KZFVERISEXZTRD-UHFFFAOYSA-N 2-dimethylarsanylethynyl(dimethyl)arsane Chemical compound C[As](C)C#C[As](C)C KZFVERISEXZTRD-UHFFFAOYSA-N 0.000 claims 1
- DJSCQCGHDWBAMG-UHFFFAOYSA-N 2-hydroxy-2-phenylpropanal Chemical compound O=CC(O)(C)C1=CC=CC=C1 DJSCQCGHDWBAMG-UHFFFAOYSA-N 0.000 claims 1
- CDPLEYHDFPHDHD-NSOVKSMOSA-N 2-methyl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-methylpropanoyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CC(C)C(=O)N1CCC[C@H]1C1=NC2=CC(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)C(C)C)=CC=C2N1 CDPLEYHDFPHDHD-NSOVKSMOSA-N 0.000 claims 1
- FISWFAPVJNDUGG-YTCPBCGMSA-N 2-methyl-1-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound CC(C)C(=O)N1CCC[C@H]1C1=NC2=CC=C(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)[C@@H]3OCCC3)C=C2N1 FISWFAPVJNDUGG-YTCPBCGMSA-N 0.000 claims 1
- HNSANIQTYGTRED-HEVIKAOCSA-N 2-phenyl-1-[(2S)-2-[4-[5-[2-[(2S)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]-1,3-oxazol-2-yl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C=1OC(=NC=1)C=1C=2N=C(NC=2C=CC=1)[C@H]1N(CCC1)C(=O)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1 HNSANIQTYGTRED-HEVIKAOCSA-N 0.000 claims 1
- BMVICXAUNDNFBI-HEVIKAOCSA-N 2-phenyl-1-[(2S)-2-[6-[2-[(2S)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1 BMVICXAUNDNFBI-HEVIKAOCSA-N 0.000 claims 1
- POCVGGOUYBWBFE-UWXQCODUSA-N 2-phenyl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-phenylacetyl)piperidin-2-yl]-3H-benzimidazol-5-yl]ethyl]-1H-benzimidazol-2-yl]piperidin-1-yl]ethanone Chemical compound N1([C@@H](CCCC1)C=1NC2=CC=C(CCC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCCC3)C(=O)CC=3C=CC=CC=3)C=C2N=1)C(=O)CC1=CC=CC=C1 POCVGGOUYBWBFE-UWXQCODUSA-N 0.000 claims 1
- IJODICVVCAZVOO-PXLJZGITSA-N 2-phenyl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]-1,3-oxazol-5-yl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C=1OC(=NC=1)C=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1 IJODICVVCAZVOO-PXLJZGITSA-N 0.000 claims 1
- MFRVVJNNGGBEFS-ZPGRZCPFSA-N 2-phenyl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(CCC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)C=C2N=1)C(=O)CC1=CC=CC=C1 MFRVVJNNGGBEFS-ZPGRZCPFSA-N 0.000 claims 1
- ICTCMYDEXITFNX-ZPGRZCPFSA-N 2-phenyl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1 ICTCMYDEXITFNX-ZPGRZCPFSA-N 0.000 claims 1
- ODLQZKAARXVVGM-UWXQCODUSA-N 2-phenyl-1-[(2S)-2-[6-[4-[2-[(2S)-1-(2-phenylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]buta-1,3-diynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1 ODLQZKAARXVVGM-UWXQCODUSA-N 0.000 claims 1
- GYQDNGNVRASWER-HEVIKAOCSA-N 2-pyridin-2-yl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-pyridin-2-ylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(CCC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)CC=3N=CC=CC=3)C=C2N=1)C(=O)CC1=CC=CC=N1 GYQDNGNVRASWER-HEVIKAOCSA-N 0.000 claims 1
- BIWGZVHZXZRSEZ-HEVIKAOCSA-N 2-pyridin-2-yl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-pyridin-2-ylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)CC=1N=CC=CC=1)C(=O)CC1=CC=CC=N1 BIWGZVHZXZRSEZ-HEVIKAOCSA-N 0.000 claims 1
- XGAGNXFQWBMQLV-HEVIKAOCSA-N 2-pyridin-3-yl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-pyridin-3-ylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(CCC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)CC=3C=NC=CC=3)C=C2N=1)C(=O)CC1=CC=CN=C1 XGAGNXFQWBMQLV-HEVIKAOCSA-N 0.000 claims 1
- RJULPLGZHOTUMQ-HEVIKAOCSA-N 2-pyridin-3-yl-1-[(2S)-2-[6-[2-[2-[(2S)-1-(2-pyridin-3-ylacetyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)CC=1C=NC=CC=1)C(=O)CC1=CC=CN=C1 RJULPLGZHOTUMQ-HEVIKAOCSA-N 0.000 claims 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N Bibenzyl Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N Isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 1
- AIDQCFHFXWPAFG-UHFFFAOYSA-N N-formylformamide Chemical compound O=CNC=O AIDQCFHFXWPAFG-UHFFFAOYSA-N 0.000 claims 1
- PDPQNBVKVGDPOZ-UIOOFZCWSA-N N-methyl-N-[(1S)-1-[6-[2-[2-[(1S)-1-[methyl-(2-phenylacetyl)amino]ethyl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]ethyl]-2-phenylacetamide Chemical compound CN([C@@H](C)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H](C)N(C)C(=O)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1 PDPQNBVKVGDPOZ-UIOOFZCWSA-N 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N Propanamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- UYEYMGLVUGXWRZ-RKAQNKOCSA-N [(2R)-oxolan-2-yl]-[(2S)-2-[6-[2-[2-[(2S)-1-(2-propoxybenzoyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]methanone Chemical compound CCCOC1=CC=CC=C1C(=O)N1[C@H](C=2NC3=CC(=CC=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@H]2N(CCC2)C(=O)[C@@H]2OCCC2)CCC1 UYEYMGLVUGXWRZ-RKAQNKOCSA-N 0.000 claims 1
- DMXLKIMVWRPUQM-RWSKJCERSA-N [(2R)-oxolan-2-yl]-[(2S)-2-[6-[2-[2-[(2S)-1-(pyridine-3-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2NC(=NC2=CC=1)[C@H]1N(CCC1)C(=O)C=1C=NC=CC=1)C(=O)[C@H]1CCCO1 DMXLKIMVWRPUQM-RWSKJCERSA-N 0.000 claims 1
- WWXNHYFHJULUMJ-YTCPBCGMSA-N [(2R)-oxolan-2-yl]-[(2S)-2-[6-[2-[2-[(2S)-1-(thiophene-2-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC(=CC=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)C=1SC=CC=1)C(=O)[C@H]1CCCO1 WWXNHYFHJULUMJ-YTCPBCGMSA-N 0.000 claims 1
- MIKZOSVZXJJNCL-KYJUHHDHSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(1-methylpyrrole-2-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-(1-methylpyrrol-2-yl)methanone Chemical compound CN1C=CC=C1C(=O)N1[C@H](C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@H]2N(CCC2)C(=O)C=2N(C=CC=2)C)CCC1 MIKZOSVZXJJNCL-KYJUHHDHSA-N 0.000 claims 1
- MIUGTZIWIROVJB-GSBZAIBZSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(1-methylpyrrole-2-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound CN1C=CC=C1C(=O)N1[C@H](C=2NC3=CC(=CC=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@H]2N(CCC2)C(=O)[C@@H]2OCCC2)CCC1 MIUGTZIWIROVJB-GSBZAIBZSA-N 0.000 claims 1
- LOEQBNGJZKSMCO-DHWXLLNHSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(2-ethylbenzoyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound CCC1=CC=CC=C1C(=O)N1[C@H](C=2NC3=CC(=CC=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@H]2N(CCC2)C(=O)[C@@H]2OCCC2)CCC1 LOEQBNGJZKSMCO-DHWXLLNHSA-N 0.000 claims 1
- WTCDFPBTTYWFAY-VDCPHJTRSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(2-methoxy-5-methylbenzoyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound COC1=CC=C(C)C=C1C(=O)N1[C@H](C=2NC3=CC(=CC=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@H]2N(CCC2)C(=O)[C@@H]2OCCC2)CCC1 WTCDFPBTTYWFAY-VDCPHJTRSA-N 0.000 claims 1
- ASOIUJBRVTUXQX-COCZKOEFSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(7-methoxyquinoline-2-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-(7-methoxyquinolin-2-yl)methanone Chemical compound C1=CC(OC)=CC2=NC(C(=O)N3CCC[C@H]3C=3NC4=CC=C(C=C4N=3)C#CC=3C=C4N=C(NC4=CC=3)[C@@H]3CCCN3C(=O)C=3C=CC4=CC=C(C=C4N=3)OC)=CC=C21 ASOIUJBRVTUXQX-COCZKOEFSA-N 0.000 claims 1
- NIHNTPFLMYPBPG-KYJUHHDHSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(cyclobutanecarbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-cyclobutylmethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2NC(=NC2=CC=1)[C@H]1N(CCC1)C(=O)C1CCC1)C(=O)C1CCC1 NIHNTPFLMYPBPG-KYJUHHDHSA-N 0.000 claims 1
- VAJUTEUDTKDFRQ-NSOVKSMOSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(cyclopropanecarbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-cyclopropylmethanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC(=CC=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)C1CC1)C(=O)C1CC1 VAJUTEUDTKDFRQ-NSOVKSMOSA-N 0.000 claims 1
- RTHRUQAMUTWAQZ-NSOVKSMOSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(furan-2-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-(furan-2-yl)methanone Chemical compound C([C@H]1C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)C=2OC=CC=2)CCN1C(=O)C1=CC=CO1 RTHRUQAMUTWAQZ-NSOVKSMOSA-N 0.000 claims 1
- STKVRBKRDJLCSY-TWLDFKIOSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(furan-2-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2NC(=NC2=CC=1)[C@H]1N(CCC1)C(=O)C=1OC=CC=1)C(=O)[C@H]1CCCO1 STKVRBKRDJLCSY-TWLDFKIOSA-N 0.000 claims 1
- ZIZWJHZFAQHLGO-KYJUHHDHSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(furan-3-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-(furan-3-yl)methanone Chemical compound C([C@H]1C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)C2=COC=C2)CCN1C(=O)C=1C=COC=1 ZIZWJHZFAQHLGO-KYJUHHDHSA-N 0.000 claims 1
- WJVAGBZITQIVJS-OIFRRMEBSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(furan-3-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2NC(=NC2=CC=1)[C@H]1N(CCC1)C(=O)C1=COC=C1)C(=O)[C@H]1CCCO1 WJVAGBZITQIVJS-OIFRRMEBSA-N 0.000 claims 1
- YHIIJRIYXRMTOT-IAHFNURPSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(oxolane-3-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-(oxolan-3-yl)methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)C1COCC1)C(=O)C1CCOC1 YHIIJRIYXRMTOT-IAHFNURPSA-N 0.000 claims 1
- SPUYITLICOIPDE-ACHIHNKUSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(pyridine-3-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-pyridin-3-ylmethanone Chemical compound C([C@H]1C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)C=2C=NC=CC=2)CCN1C(=O)C1=CC=CN=C1 SPUYITLICOIPDE-ACHIHNKUSA-N 0.000 claims 1
- SCFGRGXKFVKKOZ-NSOVKSMOSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(thiophene-2-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-thiophen-2-ylmethanone Chemical compound C([C@H]1C=2NC3=CC=C(C=C3N=2)CCC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)C=2SC=CC=2)CCN1C(=O)C1=CC=CS1 SCFGRGXKFVKKOZ-NSOVKSMOSA-N 0.000 claims 1
- OGGWHMCIYLYCGI-NSOVKSMOSA-N [(2S)-2-[6-[2-[2-[(2S)-1-(thiophene-2-carbonyl)pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-thiophen-2-ylmethanone Chemical compound C([C@H]1C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@@H]2CCCN2C(=O)C=2SC=CC=2)CCN1C(=O)C1=CC=CS1 OGGWHMCIYLYCGI-NSOVKSMOSA-N 0.000 claims 1
- NTUPARAGJBOPEU-VZNYXHRGSA-N [(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(CCC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)[C@@H]3OCCC3)C=C2N=1)C(=O)[C@H]1CCCO1 NTUPARAGJBOPEU-VZNYXHRGSA-N 0.000 claims 1
- LRJNFMXQIXYPEA-VZNYXHRGSA-N [(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)[C@@H]1OCCC1)C(=O)[C@H]1CCCO1 LRJNFMXQIXYPEA-VZNYXHRGSA-N 0.000 claims 1
- LRJNFMXQIXYPEA-KRCBVYEFSA-N [(2S)-2-[6-[2-[2-[(2S)-1-[(2S)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2S)-oxolan-2-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)[C@H]1OCCC1)C(=O)[C@@H]1CCCO1 LRJNFMXQIXYPEA-KRCBVYEFSA-N 0.000 claims 1
- UHDKHHCKRJKMCX-VDYROPKHSA-N [(2S)-2-[6-[2-[2-[(2S)-1-[2-(benzylamino)benzoyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)C=1C(=CC=CC=1)NCC=1C=CC=CC=1)C(=O)[C@H]1CCCO1 UHDKHHCKRJKMCX-VDYROPKHSA-N 0.000 claims 1
- WDARIWBMBIAKPD-XFCANUNOSA-N [(2S)-2-[6-[2-[2-[(2S)-1-[2-(methylamino)benzoyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound CNC1=CC=CC=C1C(=O)N1[C@H](C=2NC3=CC=C(C=C3N=2)C#CC=2C=C3N=C(NC3=CC=2)[C@H]2N(CCC2)C(=O)[C@@H]2OCCC2)CCC1 WDARIWBMBIAKPD-XFCANUNOSA-N 0.000 claims 1
- GFCVDZFDJIJVNJ-OWHBQTKESA-N [(2S)-2-[6-[2-[2-[(2S)-1-benzoylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2NC(=NC2=CC=1)[C@H]1N(CCC1)C(=O)C=1C=CC=CC=1)C(=O)[C@H]1CCCO1 GFCVDZFDJIJVNJ-OWHBQTKESA-N 0.000 claims 1
- XLBWRGJNPRJUNH-HEVIKAOCSA-N [(2S)-2-[6-[2-[2-[(2S)-1-benzoylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-phenylmethanone Chemical compound C([C@H]1C=2NC3=CC=C(C=C3N=2)C#CC2=CC=C3N=C(NC3=C2)[C@@H]2CCCN2C(=O)C=2C=CC=CC=2)CCN1C(=O)C1=CC=CC=C1 XLBWRGJNPRJUNH-HEVIKAOCSA-N 0.000 claims 1
- MKEIFBUWFBQSGR-XETGTQJKSA-N [(2S,4R)-4-hydroxy-2-[6-[2-[2-[(2S,4R)-4-hydroxy-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound N1([C@@H](C[C@H](C1)O)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(C[C@H](O)C1)C(=O)[C@@H]1OCCC1)C(=O)[C@H]1CCCO1 MKEIFBUWFBQSGR-XETGTQJKSA-N 0.000 claims 1
- CYUBKBRAFIRGNA-XGYOUSBVSA-N [(2S,4S)-4-(2-methylpropylamino)-2-[6-[2-[2-[(2S,4S)-4-(2-methylpropylamino)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound N1([C@@H](C[C@@H](C1)NCC(C)C)C=1NC2=CC=C(C=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(C[C@H](C1)NCC(C)C)C(=O)[C@@H]1OCCC1)C(=O)[C@H]1CCCO1 CYUBKBRAFIRGNA-XGYOUSBVSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 1
- BADMPYFSNVPXQS-CONSDPRKSA-N benzyl (2S)-2-[6-[2-[2-[(2S)-1-acetylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound CC(=O)N1CCC[C@H]1C1=NC2=CC(C#CC=3C=C4N=C(NC4=CC=3)[C@H]3N(CCC3)C(=O)OCC=3C=CC=CC=3)=CC=C2N1 BADMPYFSNVPXQS-CONSDPRKSA-N 0.000 claims 1
- HYNQIRCOFOQGGH-ZPGRZCPFSA-N benzyl (2S)-2-[6-[2-[2-[(2S)-1-phenylmethoxycarbonylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound N1([C@@H](CCC1)C=1NC2=CC(=CC=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)OCC=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 HYNQIRCOFOQGGH-ZPGRZCPFSA-N 0.000 claims 1
- PLVKRLFIJJHNCY-HEVIKAOCSA-N benzyl (5S)-2-oxo-5-[6-[2-[2-[(2S)-5-oxo-1-phenylmethoxycarbonylpyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethyl]-1H-benzimidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound C([C@H]1C=2NC3=CC=C(CCC=4C=C5NC(=NC5=CC=4)[C@H]4N(C(=O)CC4)C(=O)OCC=4C=CC=CC=4)C=C3N=2)CC(=O)N1C(=O)OCC1=CC=CC=C1 PLVKRLFIJJHNCY-HEVIKAOCSA-N 0.000 claims 1
- ZBWJQMSWJMMRDM-UHFFFAOYSA-N benzyl 2-[6-[2-[2-[1-phenylmethoxycarbonyl-4-(pyridine-4-carbonyl)piperazin-2-yl]-3H-benzimidazol-5-yl]ethyl]-1H-benzimidazol-2-yl]-4-(pyridine-4-carbonyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)C=2C=CN=CC=2)CC(C=2NC3=CC=C(CCC=4C=C5NC(=NC5=CC=4)C4N(CCN(C4)C(=O)C=4C=CN=CC=4)C(=O)OCC=4C=CC=CC=4)C=C3N=2)N1C(=O)OCC1=CC=CC=C1 ZBWJQMSWJMMRDM-UHFFFAOYSA-N 0.000 claims 1
- TYYWVWFLAAEVLV-UHFFFAOYSA-N benzyl 4-(cyclopropanecarbonyl)-2-[6-[2-[2-[4-(cyclopropanecarbonyl)-1-phenylmethoxycarbonylpiperazin-2-yl]-3H-benzimidazol-5-yl]ethyl]-1H-benzimidazol-2-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)C2CC2)CC(C=2NC3=CC(CCC=4C=C5N=C(NC5=CC=4)C4N(CCN(C4)C(=O)C4CC4)C(=O)OCC=4C=CC=CC=4)=CC=C3N=2)N1C(=O)OCC1=CC=CC=C1 TYYWVWFLAAEVLV-UHFFFAOYSA-N 0.000 claims 1
- XCWMRELWRCWOEM-UHFFFAOYSA-N benzyl 4-acetyl-2-[6-[2-[2-(4-acetyl-1-phenylmethoxycarbonylpiperazin-2-yl)-3H-benzimidazol-5-yl]ethyl]-1H-benzimidazol-2-yl]piperazine-1-carboxylate Chemical compound C1N(C(=O)C)CCN(C(=O)OCC=2C=CC=CC=2)C1C(NC1=C2)=NC1=CC=C2CCC(C=C1N=2)=CC=C1NC=2C1CN(C(C)=O)CCN1C(=O)OCC1=CC=CC=C1 XCWMRELWRCWOEM-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- MULJCOHZTVQQLK-OIFRRMEBSA-N cyclobutyl-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC(=CC=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)[C@@H]1OCCC1)C(=O)C1CCC1 MULJCOHZTVQQLK-OIFRRMEBSA-N 0.000 claims 1
- OLSDXODBNUIWOI-YTCPBCGMSA-N cyclopropyl-[(2S)-2-[6-[2-[2-[(2S)-1-[(2R)-oxolane-2-carbonyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]ethynyl]-1H-benzimidazol-2-yl]pyrrolidin-1-yl]methanone Chemical compound N1([C@@H](CCC1)C=1NC2=CC(=CC=C2N=1)C#CC=1C=C2N=C(NC2=CC=1)[C@H]1N(CCC1)C(=O)[C@@H]1OCCC1)C(=O)C1CC1 OLSDXODBNUIWOI-YTCPBCGMSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-M pyrrolidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-M 0.000 claims 1
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| EP2373167A4 (en) | 2008-12-03 | 2012-07-25 | Presidio Pharmaceuticals Inc | INHIBITORS OF HEPATITIS C VIRUS TYPE NS5A |
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| JP2012513409A (ja) * | 2008-12-23 | 2012-06-14 | アボット・ラボラトリーズ | 抗ウイルス化合物 |
| CN102245604A (zh) | 2008-12-23 | 2011-11-16 | 雅培制药有限公司 | 抗病毒化合物 |
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| US8314135B2 (en) * | 2009-02-09 | 2012-11-20 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole antivirals |
| 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 |
| US8420686B2 (en) | 2009-02-17 | 2013-04-16 | Enanta Pharmaceuticals, Inc. | Linked diimidazole antivirals |
| US8242156B2 (en) | 2009-02-17 | 2012-08-14 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| US8394968B2 (en) | 2009-02-17 | 2013-03-12 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| 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 |
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| 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 |
| US8507522B2 (en) | 2009-03-06 | 2013-08-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8796466B2 (en) | 2009-03-30 | 2014-08-05 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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