EA021260B1 - Ингибиторы вируса гепатита с - Google Patents

Info

Publication number

EA021260B1

EA021260B1 EA201101240A EA201101240A EA021260B1 EA 021260 B1 EA021260 B1 EA 021260B1 EA 201101240 A EA201101240 A EA 201101240A EA 201101240 A EA201101240 A EA 201101240A EA 021260 B1 EA021260 B1 EA 021260B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

cap

imidazol

mmol

pyrrolidinyl

Prior art date

2009-03-30

Links

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• Global Dossier
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• 241000711549 Hepacivirus C Species 0.000 title abstract description 4
• 239000003112 inhibitor Substances 0.000 title description 34
• 150000001875 compounds Chemical class 0.000 claims abstract description 290
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 11
• -1 O -O- -O Chemical class 0.000 claims description 152
• 150000003839 salts Chemical class 0.000 claims description 79
• 229910052739 hydrogen Inorganic materials 0.000 claims description 74
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 68
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 57
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 38
• 125000003118 aryl group Chemical group 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 7
• 150000002431 hydrogen Chemical group 0.000 claims description 7
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 229930195734 saturated hydrocarbon Natural products 0.000 claims description 6
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 5
• 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 description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 3
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 1
• 230000004853 protein function Effects 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 237
• 101800001014 Non-structural protein 5A Proteins 0.000 abstract 1
• 239000003443 antiviral agent Substances 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 506
• 238000004364 calculation method Methods 0.000 description 290
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 270
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 218
• 239000000243 solution Substances 0.000 description 169
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 142
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
• 239000011541 reaction mixture Substances 0.000 description 103
• 239000007787 solid Substances 0.000 description 100
• 238000000034 method Methods 0.000 description 83
• 239000002904 solvent Substances 0.000 description 82
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 70
• 239000003921 oil Substances 0.000 description 63
• 235000019198 oils Nutrition 0.000 description 61
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
• 239000012044 organic layer Substances 0.000 description 47
• 238000003756 stirring Methods 0.000 description 46
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
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• 238000000746 purification Methods 0.000 description 43
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
• 239000012267 brine Substances 0.000 description 42
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 42
• 239000013058 crude material Substances 0.000 description 41
• 239000000741 silica gel Substances 0.000 description 41
• 229910002027 silica gel Inorganic materials 0.000 description 41
• 238000010828 elution Methods 0.000 description 40
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
• 230000000840 anti-viral effect Effects 0.000 description 38
• 239000000725 suspension Substances 0.000 description 38
• 230000015572 biosynthetic process Effects 0.000 description 36
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• 239000000047 product Substances 0.000 description 33
• 238000003786 synthesis reaction Methods 0.000 description 31
• 239000000706 filtrate Substances 0.000 description 29
• 239000000126 substance Substances 0.000 description 28
• 239000012074 organic phase Substances 0.000 description 27
• 239000010410 layer Substances 0.000 description 26
• 239000011777 magnesium Substances 0.000 description 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• 238000006243 chemical reaction Methods 0.000 description 24
• 238000003818 flash chromatography Methods 0.000 description 24
• 239000006260 foam Substances 0.000 description 24
• 238000001816 cooling Methods 0.000 description 23
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 22
• 239000012071 phase Substances 0.000 description 20
• 230000002829 reductive effect Effects 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• 239000012043 crude product Substances 0.000 description 19
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
• 108010050904 Interferons Proteins 0.000 description 17
• 102000014150 Interferons Human genes 0.000 description 17
• 239000005909 Kieselgur Substances 0.000 description 17
• 239000002253 acid Substances 0.000 description 17
• 239000012230 colorless oil Substances 0.000 description 17
• 229940079322 interferon Drugs 0.000 description 17
• 238000004007 reversed phase HPLC Methods 0.000 description 17
• 239000008346 aqueous phase Substances 0.000 description 16
• 239000005457 ice water Substances 0.000 description 16
• 239000000543 intermediate Substances 0.000 description 16
• 229910052757 nitrogen Inorganic materials 0.000 description 16
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
• 229920006395 saturated elastomer Polymers 0.000 description 15
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
• 239000002585 base Substances 0.000 description 13
• 108010026228 mRNA guanylyltransferase Proteins 0.000 description 13
• 239000000843 powder Substances 0.000 description 13
• 238000002360 preparation method Methods 0.000 description 13
• 239000004480 active ingredient Substances 0.000 description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
• 150000002148 esters Chemical class 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
• 239000007858 starting material Substances 0.000 description 12
• 238000011282 treatment Methods 0.000 description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
• 239000000463 material Substances 0.000 description 11
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 11
• 238000000926 separation method Methods 0.000 description 11
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• 101100405319 Arabidopsis thaliana NSI gene Proteins 0.000 description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
• 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 description 10
• 101150016222 SNAT1 gene Proteins 0.000 description 10
• 101100500565 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) ECM8 gene Proteins 0.000 description 10
• 238000004128 high performance liquid chromatography Methods 0.000 description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
• 235000018102 proteins Nutrition 0.000 description 10
• 102000004169 proteins and genes Human genes 0.000 description 10
• 108090000623 proteins and genes Proteins 0.000 description 10
• 229960000329 ribavirin Drugs 0.000 description 10
• 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 description 10
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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• 125000000623 heterocyclic group Chemical group 0.000 description 8
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• 229960003444 immunosuppressant agent Drugs 0.000 description 4
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