CA2757269A1 - Hepatitis c virus inhibitors - Google Patents

Info

Publication number

CA2757269A1

CA2757269A1 CA2757269A CA2757269A CA2757269A1 CA 2757269 A1 CA2757269 A1 CA 2757269A1 CA 2757269 A CA2757269 A CA 2757269A CA 2757269 A CA2757269 A CA 2757269A CA 2757269 A1 CA2757269 A1 CA 2757269A1

Authority

CA

Canada

Prior art keywords

imidazol

phenyl

alkyl

pyrrolidinyl

methyl

Prior art date

2009-03-30

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 241000711549 Hepacivirus C Species 0.000 title abstract description 54
• 239000003112 inhibitor Substances 0.000 title description 38
• 150000001875 compounds Chemical class 0.000 claims abstract description 150
• 239000000203 mixture Substances 0.000 claims abstract description 136
• 238000000034 method Methods 0.000 claims abstract description 94
• 229910052739 hydrogen Inorganic materials 0.000 claims description 158
• 125000000217 alkyl group Chemical group 0.000 claims description 143
• 239000001257 hydrogen Substances 0.000 claims description 119
• -1 carboxy, formyl Chemical group 0.000 claims description 87
• 125000003118 aryl group Chemical group 0.000 claims description 72
• 150000003839 salts Chemical class 0.000 claims description 72
• 150000002431 hydrogen Chemical group 0.000 claims description 60
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 229910052757 nitrogen Inorganic materials 0.000 claims description 47
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 44
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 44
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 36
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
• 125000001188 haloalkyl group Chemical group 0.000 claims description 34
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 125000001072 heteroaryl group Chemical group 0.000 claims description 30
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• 229910052717 sulfur Chemical group 0.000 claims description 19
• 125000005843 halogen group Chemical group 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 239000000126 substance Substances 0.000 claims description 16
• 125000002619 bicyclic group Chemical group 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 239000001301 oxygen Chemical group 0.000 claims description 13
• 239000011593 sulfur Chemical group 0.000 claims description 13
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
• 208000015181 infectious disease Diseases 0.000 claims description 7
• 125000005469 ethylenyl group Chemical group 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 229910052727 yttrium Inorganic materials 0.000 claims description 4
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• 229920002554 vinyl polymer Polymers 0.000 claims description 2
• 239000004202 carbamide Substances 0.000 claims 7
• PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims 6
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 3
• WNTJTJGNVDHXAD-ATUXXYJQSA-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]phenoxy]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C=2C=CC=C(C=2)OC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 WNTJTJGNVDHXAD-ATUXXYJQSA-N 0.000 claims 1
• DKEBEEQSQZZEHR-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]phenoxy]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C2=CC=C(C=C2)OC2=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 DKEBEEQSQZZEHR-ATUXXYJQSA-N 0.000 claims 1
• NNZZWCDLGUPTDG-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]phenoxy]methyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C2=CC=C(C=C2)OCC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 NNZZWCDLGUPTDG-SKQWTEPWSA-N 0.000 claims 1
• ZBGKKYUXZMMPHM-JPYDVTDNSA-N (2r)-2-hydroxy-1-[(2s)-2-[5-[4-[2-[4-[2-[(2s)-1-[(2r)-2-hydroxy-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]ethyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C2=CC=C(C=C2)CCC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 ZBGKKYUXZMMPHM-JPYDVTDNSA-N 0.000 claims 1
• HFGCNRSEJWSLOH-CDBYGCFJSA-N (2r)-2-hydroxy-1-[(2s)-2-[5-[4-[3-[2-[(2s)-1-[(2r)-2-hydroxy-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenoxy]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C=2C=CC=C(C=2)OC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 HFGCNRSEJWSLOH-CDBYGCFJSA-N 0.000 claims 1
• JTAAFITWZJSVSY-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]phenoxy]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C2=CC=C(C=C2)OC2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 JTAAFITWZJSVSY-CDBYGCFJSA-N 0.000 claims 1
• YLKPEGAEKOBUPL-JPYDVTDNSA-N (2r)-2-hydroxy-1-[(2s)-2-[5-[4-[[3-[2-[(2s)-1-[(2r)-2-hydroxy-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]methoxymethyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C=2C=CC=C(C=2)COCC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 YLKPEGAEKOBUPL-JPYDVTDNSA-N 0.000 claims 1
• HTRIYHGKDKIESH-JPYDVTDNSA-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]methoxymethyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C2=CC=C(C=C2)COCC2=CC=C(C=C2)C2=CN=C(N2)[C@@H]2CCCN2C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 HTRIYHGKDKIESH-JPYDVTDNSA-N 0.000 claims 1
• URBNHSPLMPSGPV-IYTFMMMVSA-N 1-ethyl-3-[(1R)-2-[(2S)-2-[5-[4-[2-[4-[2-[(2S)-1-[(2R)-2-(ethylcarbamoylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]ethyl]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]2C=2NC=C(N=2)C2=CC=C(C=C2)CCC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](NC(=O)NCC)C=2C=CC=CC=2)=CC=CC=C1 URBNHSPLMPSGPV-IYTFMMMVSA-N 0.000 claims 1
• YVEQPCMIMAWAQR-QCHLLITLSA-N methyl N-[(1S)-1-cyclobutyl-2-[(1R,3S,5R)-3-[5-[4-[2-[4-[2-[(1R,3S,5R)-2-[(2S)-2-cyclobutyl-2-(methoxycarbonylamino)acetyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1H-imidazol-5-yl]phenyl]ethynyl]phenyl]-1H-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@H]3C[C@H]32)C=2NC=C(N=2)C=2C=CC(=CC=2)C#CC=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N([C@@H]3C[C@@H]3C2)C(=O)[C@@H](NC(=O)OC)C2CCC2)CCC1 YVEQPCMIMAWAQR-QCHLLITLSA-N 0.000 claims 1
• VZSUSXHFERCFLP-CEYRAQRFSA-N methyl N-[(1S)-2-[(1R,3S,5R)-3-[5-[4-[(1R,2R)-2-[4-[2-[(1R,3S,5R)-2-[(2S)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1H-imidazol-5-yl]phenyl]cyclopropyl]phenyl]-1H-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-1-(oxan-4-yl)-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@H]3C[C@H]32)C=2NC=C(N=2)C=2C=CC(=CC=2)[C@H]2[C@@H](C2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N([C@@H]3C[C@@H]3C2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)CCOCC1 VZSUSXHFERCFLP-CEYRAQRFSA-N 0.000 claims 1
• VZSUSXHFERCFLP-SYBHSTCWSA-N methyl N-[(1S)-2-[(1R,3S,5R)-3-[5-[4-[(1S,2S)-2-[4-[2-[(1R,3S,5R)-2-[(2S)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1H-imidazol-5-yl]phenyl]cyclopropyl]phenyl]-1H-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-1-(oxan-4-yl)-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@H]3C[C@H]32)C=2NC=C(N=2)C=2C=CC(=CC=2)[C@@H]2[C@H](C2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N([C@@H]3C[C@@H]3C2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)CCOCC1 VZSUSXHFERCFLP-SYBHSTCWSA-N 0.000 claims 1
• RLYIICRCUIQRCJ-CSIWEQGYSA-N methyl N-[(1S)-2-[(1R,3S,5R)-3-[5-chloro-4-[4-[2-[4-[5-chloro-2-[(1R,3S,5R)-2-[(2S)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1H-imidazol-4-yl]phenyl]ethynyl]phenyl]-1H-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-1-(oxan-4-yl)-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@H]3C[C@H]32)C=2NC(=C(Cl)N=2)C=2C=CC(=CC=2)C#CC=2C=CC(=CC=2)C2=C(N=C(N2)[C@H]2N([C@@H]3C[C@@H]3C2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)Cl)CCOCC1 RLYIICRCUIQRCJ-CSIWEQGYSA-N 0.000 claims 1
• JHJJQCXJROWVGX-UIZYBZRTSA-N methyl N-[(1S)-2-[(1S,3S,5S)-3-[5-[4-[2-[4-[2-[(1S,3S,5S)-2-[(2S)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1H-imidazol-5-yl]phenyl]ethynyl]phenyl]-1H-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-1-(oxan-4-yl)-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@@H]3C[C@@H]32)C=2NC=C(N=2)C=2C=CC(=CC=2)C#CC=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N([C@H]3C[C@H]3C2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)CCOCC1 JHJJQCXJROWVGX-UIZYBZRTSA-N 0.000 claims 1
• HEIKUFLMXUCFJX-PGOVWKCYSA-N methyl N-[(1S)-2-[(2S,4S)-2-[5-[4-[(1S,2S)-2-[4-[2-[(2S,4S)-1-[(2S)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]-4-methylpyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]cyclopropyl]phenyl]-1H-imidazol-2-yl]-4-methylpyrrolidin-1-yl]-1-(oxan-4-yl)-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@H](C)C2)C=2NC=C(N=2)C=2C=CC(=CC=2)[C@@H]2[C@H](C2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(C[C@@H](C)C2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)CCOCC1 HEIKUFLMXUCFJX-PGOVWKCYSA-N 0.000 claims 1
• VBYSTLZGNHNONJ-VPGSQPSVSA-N methyl N-[(1S)-2-[(2S,4S)-2-[5-[4-[2-[4-[2-[(2S,4S)-1-[(2S)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]-4-methylpyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]ethynyl]phenyl]-1H-imidazol-2-yl]-4-methylpyrrolidin-1-yl]-1-(oxan-4-yl)-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@H](C)C2)C=2NC=C(N=2)C=2C=CC(=CC=2)C#CC=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(C[C@@H](C)C2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)CCOCC1 VBYSTLZGNHNONJ-VPGSQPSVSA-N 0.000 claims 1
• MYXMQLWOQGSSBI-RFGJTLQISA-N methyl N-[(1S)-2-[(2S,4S)-2-[5-chloro-4-[4-[2-[4-[5-chloro-2-[(2S,4S)-1-[(2S)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]-4-methylpyrrolidin-2-yl]-1H-imidazol-4-yl]phenyl]ethynyl]phenyl]-1H-imidazol-2-yl]-4-methylpyrrolidin-1-yl]-1-(oxan-4-yl)-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@H](C)C2)C=2NC(=C(Cl)N=2)C=2C=CC(=CC=2)C#CC=2C=CC(=CC=2)C2=C(N=C(N2)[C@H]2N(C[C@@H](C)C2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)Cl)CCOCC1 MYXMQLWOQGSSBI-RFGJTLQISA-N 0.000 claims 1
• NOGBIEKUCNIWKS-VPGSQPSVSA-N methyl N-[(1S)-2-[(2S,5S)-2-[5-[4-[2-[4-[2-[(2S,5S)-1-[(2S)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]-5-methylpyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]ethynyl]phenyl]-1H-imidazol-2-yl]-5-methylpyrrolidin-1-yl]-1-(oxan-4-yl)-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](CC[C@@H]2C)C=2NC=C(N=2)C=2C=CC(=CC=2)C#CC=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N([C@@H](C)CC2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)CCOCC1 NOGBIEKUCNIWKS-VPGSQPSVSA-N 0.000 claims 1
• LLHDGKLRGOULMV-MHCCPZGRSA-N methyl N-[(2S)-1-[(1R,3S,5R)-3-[5-[4-[2-[4-[2-[(1R,3S,5R)-2-[(2S)-2-(methoxycarbonylamino)butanoyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1H-imidazol-5-yl]phenyl]ethynyl]phenyl]-1H-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-1-oxobutan-2-yl]carbamate Chemical compound C=1NC([C@@H]2C[C@H]3C[C@H]3N2C(=O)[C@@H](NC(=O)OC)CC)=NC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C1=CNC([C@H]2N([C@@H]3C[C@@H]3C2)C(=O)[C@H](CC)NC(=O)OC)=N1 LLHDGKLRGOULMV-MHCCPZGRSA-N 0.000 claims 1
• HRCNRSKWMOQZML-CDBYGCFJSA-N methyl n-[(1r)-2-[(2s)-2-[5-[4-[2-[4-[2-[(2s)-4,4-difluoro-1-[(2r)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]ethynyl]phenyl]-1h-imidazol-2-yl]-4,4-difluoropyrrolidin-1-yl]-1-(oxan-4-yl)-2-oxoethyl]carbamate Chemical compound C1([C@@H](NC(=O)OC)C(=O)N2[C@@H](CC(F)(F)C2)C=2NC(=CN=2)C=2C=CC(=CC=2)C#CC=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CC(F)(F)C2)C(=O)[C@H](NC(=O)OC)C2CCOCC2)CCOCC1 HRCNRSKWMOQZML-CDBYGCFJSA-N 0.000 claims 1
• GPAPXRGLAKDUJT-JPYDVTDNSA-N methyl n-[(1r)-2-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(methoxycarbonylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenoxy]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1([C@@H](NC(=O)OC)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C2=CC=C(C=C2)OC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](NC(=O)OC)C=2C=CC=CC=2)=CC=CC=C1 GPAPXRGLAKDUJT-JPYDVTDNSA-N 0.000 claims 1
• GYHUDHSHRHODLZ-OLSWEDCXSA-N methyl n-[(1s)-2-[(1r,3s,5r)-3-[5-[3-[2-[3-[2-[(1r,3s,5r)-2-[(2s)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1h-imidazol-5-yl]phenyl]ethynyl]phenyl]-1h-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-1-(oxan-4-yl)-2-oxoethy Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@H]3C[C@H]32)C=2NC=C(N=2)C=2C=C(C=CC=2)C#CC=2C=C(C=CC=2)C=2N=C(NC=2)[C@H]2N([C@@H]3C[C@@H]3C2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)CCOCC1 GYHUDHSHRHODLZ-OLSWEDCXSA-N 0.000 claims 1
• JHJJQCXJROWVGX-OLSWEDCXSA-N methyl n-[(1s)-2-[(1r,3s,5r)-3-[5-[4-[2-[4-[2-[(1r,3s,5r)-2-[(2s)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1h-imidazol-5-yl]phenyl]ethynyl]phenyl]-1h-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-1-(oxan-4-yl)-2-oxoethy Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@H]3C[C@H]32)C=2NC=C(N=2)C=2C=CC(=CC=2)C#CC=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N([C@@H]3C[C@@H]3C2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)CCOCC1 JHJJQCXJROWVGX-OLSWEDCXSA-N 0.000 claims 1
• OSBVGXNAKWNPDF-YKKXUYLKSA-N methyl n-[(1s)-2-[(2s)-2-[5-[3-[2-[3-[2-[(2s)-1-[(2s)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]ethynyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-1-(oxan-4-yl)-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](CCC2)C=2NC=C(N=2)C=2C=C(C=CC=2)C#CC=2C=C(C=CC=2)C=2N=C(NC=2)[C@H]2N(CCC2)C(=O)[C@@H](NC(=O)OC)C2CCOCC2)CCOCC1 OSBVGXNAKWNPDF-YKKXUYLKSA-N 0.000 claims 1
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