KR20120034603A - Ｃ형 간염 바이러스 억제제 - Google Patents

Info

Publication number

KR20120034603A

KR20120034603A KR1020117025611A KR20117025611A KR20120034603A KR 20120034603 A KR20120034603 A KR 20120034603A KR 1020117025611 A KR1020117025611 A KR 1020117025611A KR 20117025611 A KR20117025611 A KR 20117025611A KR 20120034603 A KR20120034603 A KR 20120034603A

Authority

KR

South Korea

Prior art keywords

imidazol

phenyl

alkyl

methyl

pyrrolidinyl

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.)

Ceased

Links

• Espacenet
• Global Dossier
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• 241000711549 Hepacivirus C Species 0.000 title abstract description 47
• 239000003112 inhibitor Substances 0.000 title description 2
• 239000000203 mixture Substances 0.000 claims abstract description 182
• 150000001875 compounds Chemical class 0.000 claims abstract description 147
• 238000000034 method Methods 0.000 claims abstract description 128
• 229910052739 hydrogen Inorganic materials 0.000 claims description 198
• -1 carboxy, formyl Chemical group 0.000 claims description 156
• 239000001257 hydrogen Substances 0.000 claims description 122
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 111
• 125000000217 alkyl group Chemical group 0.000 claims description 106
• 125000003118 aryl group Chemical group 0.000 claims description 74
• 150000003839 salts Chemical class 0.000 claims description 67
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 65
• 229910052757 nitrogen Inorganic materials 0.000 claims description 61
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 60
• 150000002431 hydrogen Chemical group 0.000 claims description 60
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 44
• 125000001424 substituent group Chemical group 0.000 claims description 42
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 38
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
• 125000001188 haloalkyl group Chemical group 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 17
• 125000002619 bicyclic group Chemical group 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000004043 oxo group Chemical group O=* 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 229910052717 sulfur Chemical group 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
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 239000011593 sulfur Chemical group 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000005469 ethylenyl group Chemical group 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 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
• 125000004438 haloalkoxy 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
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 208000015181 infectious disease Diseases 0.000 claims description 4
• 125000005429 oxyalkyl group Chemical group 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 229910052727 yttrium Inorganic materials 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
• 229920002554 vinyl polymer Polymers 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
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 31
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 31
• 239000004202 carbamide Substances 0.000 claims 7
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 4
• 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
• 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
• JUJYNCPRVMVRCV-LURJTMIESA-N 2-[(2s)-pyrrolidin-2-yl]-1h-imidazole Chemical compound C1CCN[C@@H]1C1=NC=CN1 JUJYNCPRVMVRCV-LURJTMIESA-N 0.000 claims 1
• PCRFFXYXNNSCDH-UHFFFAOYSA-N 2-amino-2-phenylacetaldehyde Chemical compound O=CC(N)C1=CC=CC=C1 PCRFFXYXNNSCDH-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 13
• 101800001014 Non-structural protein 5A Proteins 0.000 abstract description 11
• 201000010099 disease Diseases 0.000 abstract description 8
• 230000002401 inhibitory effect Effects 0.000 abstract description 6
• 239000003443 antiviral agent Substances 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 618
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 368
• 239000002904 solvent Substances 0.000 description 187
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 173
• 239000000243 solution Substances 0.000 description 163
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 159
• 235000019439 ethyl acetate Nutrition 0.000 description 143
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 137
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 121
• 239000007787 solid Substances 0.000 description 113
• 239000011541 reaction mixture Substances 0.000 description 100
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 84
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 64
• 238000006243 chemical reaction Methods 0.000 description 64
• 238000002360 preparation method Methods 0.000 description 62
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
• 239000003921 oil Substances 0.000 description 54
• 235000019198 oils Nutrition 0.000 description 53
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 47
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