TWI476190B - Ｃ型肝炎病毒抑制劑 - Google Patents

Info

Publication number

TWI476190B

TWI476190B TW099108734A TW99108734A TWI476190B TW I476190 B TWI476190 B TW I476190B TW 099108734 A TW099108734 A TW 099108734A TW 99108734 A TW99108734 A TW 99108734A TW I476190 B TWI476190 B TW I476190B

Authority

TW

Taiwan

Prior art keywords

alkyl

group

imidazol

hydrogen

independently selected

Prior art date

2009-03-30

Links

• Espacenet
• Global Dossier
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• 241000711549 Hepacivirus C Species 0.000 title claims description 52
• 239000003112 inhibitor Substances 0.000 title 1
• 239000000203 mixture Substances 0.000 claims description 223
• 150000001875 compounds Chemical class 0.000 claims description 184
• 125000000217 alkyl group Chemical group 0.000 claims description 176
• 229910052739 hydrogen Inorganic materials 0.000 claims description 171
• 239000001257 hydrogen Substances 0.000 claims description 134
• -1 -NR a R b Chemical group 0.000 claims description 94
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 88
• 125000001424 substituent group Chemical group 0.000 claims description 84
• 125000003118 aryl group Chemical group 0.000 claims description 83
• 150000003839 salts Chemical class 0.000 claims description 76
• 150000002431 hydrogen Chemical class 0.000 claims description 74
• 125000000623 heterocyclic group Chemical group 0.000 claims description 63
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 58
• 125000001072 heteroaryl group Chemical group 0.000 claims description 55
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 39
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
• 229910052736 halogen Inorganic materials 0.000 claims description 35
• 150000002367 halogens Chemical class 0.000 claims description 35
• 125000005843 halogen group Chemical group 0.000 claims description 30
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
• 229910052760 oxygen Inorganic materials 0.000 claims description 29
• 239000001301 oxygen Substances 0.000 claims description 29
• 125000002619 bicyclic group Chemical group 0.000 claims description 26
• 125000001188 haloalkyl group Chemical group 0.000 claims description 26
• 229910052727 yttrium Inorganic materials 0.000 claims description 26
• 229910052717 sulfur Chemical group 0.000 claims description 25
• 125000005842 heteroatom Chemical group 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 19
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 239000011593 sulfur Chemical group 0.000 claims description 18
• 229930194542 Keto Natural products 0.000 claims description 17
• 125000000468 ketone group Chemical group 0.000 claims description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
• 239000003937 drug carrier Substances 0.000 claims description 9
• 208000015181 infectious disease Diseases 0.000 claims description 9
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• 239000003814 drug Substances 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
• 238000005452 bending Methods 0.000 claims description 2
• DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 2
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 16
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
• 125000000547 substituted alkyl group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 542
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 477
• 235000019439 ethyl acetate Nutrition 0.000 description 231
• 238000005481 NMR spectroscopy Methods 0.000 description 182
• 238000004458 analytical method Methods 0.000 description 159
• 239000000243 solution Substances 0.000 description 159
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 144
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 134
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 126
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 119
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 89
• 239000002904 solvent Substances 0.000 description 78
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
• 238000000034 method Methods 0.000 description 74
• 239000011541 reaction mixture Substances 0.000 description 74
• 239000007787 solid Substances 0.000 description 74
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 67
• 239000003921 oil Substances 0.000 description 56
• 235000019198 oils Nutrition 0.000 description 56
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
• 238000006243 chemical reaction Methods 0.000 description 48
• 239000012044 organic layer Substances 0.000 description 47
• 239000011734 sodium Substances 0.000 description 45
• 239000012267 brine Substances 0.000 description 44
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 44
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 41
• 239000013058 crude material Substances 0.000 description 40
• 238000000746 purification Methods 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
• 238000003756 stirring Methods 0.000 description 38
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
• 239000000047 product Substances 0.000 description 30
• 239000000725 suspension Substances 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
• 230000015572 biosynthetic process Effects 0.000 description 28
• 238000003818 flash chromatography Methods 0.000 description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
• 239000012074 organic phase Substances 0.000 description 26
• 239000012453 solvate Substances 0.000 description 26
• 239000000706 filtrate Substances 0.000 description 25
• 238000003786 synthesis reaction Methods 0.000 description 25
• 238000002360 preparation method Methods 0.000 description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
• 239000005909 Kieselgur Substances 0.000 description 21
• 238000001816 cooling Methods 0.000 description 21
• 239000000463 material Substances 0.000 description 21
• 230000002829 reductive effect Effects 0.000 description 21
• 238000011282 treatment Methods 0.000 description 20
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 19
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
• 239000002253 acid Substances 0.000 description 19
• 239000012043 crude product Substances 0.000 description 19
• 229920006395 saturated elastomer Polymers 0.000 description 19
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 17
• 239000002585 base Substances 0.000 description 17
• 239000006260 foam Substances 0.000 description 17
• 238000004128 high performance liquid chromatography Methods 0.000 description 17
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 16
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 16
• 239000010410 layer Substances 0.000 description 16
• 239000008194 pharmaceutical composition Substances 0.000 description 16
• 238000004007 reversed phase HPLC Methods 0.000 description 16
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
• 239000008346 aqueous phase Substances 0.000 description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
• 239000003039 volatile agent Substances 0.000 description 15
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 14
• 150000002148 esters Chemical class 0.000 description 13
• 238000009472 formulation Methods 0.000 description 13
• 239000005457 ice water Substances 0.000 description 13
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 13
• 239000000543 intermediate Substances 0.000 description 13
• 239000000843 powder Substances 0.000 description 13
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• 239000004480 active ingredient Substances 0.000 description 12
• 230000000694 effects Effects 0.000 description 12
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 12
• 239000012071 phase Substances 0.000 description 12
• 150000005331 phenylglycines Chemical class 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 238000000926 separation method Methods 0.000 description 12
• 239000007858 starting material Substances 0.000 description 12
• 238000002953 preparative HPLC Methods 0.000 description 11
• 230000002441 reversible effect Effects 0.000 description 11
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• 101800001014 Non-structural protein 5A Proteins 0.000 description 10
• 239000012230 colorless oil Substances 0.000 description 10
• YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 10
• 150000003840 hydrochlorides Chemical class 0.000 description 10
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• 239000007788 liquid Substances 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• 229910052799 carbon Inorganic materials 0.000 description 8
• 201000010099 disease Diseases 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
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• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
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• 235000001014 amino acid Nutrition 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
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• 229910004298 SiO 2 Inorganic materials 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
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• 229920002472 Starch Polymers 0.000 description 4
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