EA022624B1 - Ингибиторы вируса гепатита c - Google Patents

Info

Publication number

EA022624B1

EA022624B1 EA201391637A EA201391637A EA022624B1 EA 022624 B1 EA022624 B1 EA 022624B1 EA 201391637 A EA201391637 A EA 201391637A EA 201391637 A EA201391637 A EA 201391637A EA 022624 B1 EA022624 B1 EA 022624B1

Authority

EA

Eurasian Patent Office

Prior art keywords

pyrrolo

dimethyl

oxy

diazacyclopentadecin

carbamoyl

Prior art date

2011-05-05

Links

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• 239000003112 inhibitor Substances 0.000 title abstract description 38
• 241000711549 Hepacivirus C Species 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 490
• 238000000034 method Methods 0.000 claims abstract description 74
• -1 benzodioxanyl Chemical group 0.000 claims description 3343
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 843
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 521
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 317
• 150000003839 salts Chemical class 0.000 claims description 66
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 125000001188 haloalkyl group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 21
• 239000012634 fragment Substances 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 208000015181 infectious disease Diseases 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 125000005518 carboxamido group Chemical group 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 5
• VODXBRBCRGVVAQ-UHFFFAOYSA-N C1CCCCCCCCN2CCCC2CNC2(C(=O)N)CC21 Chemical compound C1CCCCCCCCN2CCCC2CNC2(C(=O)N)CC21 VODXBRBCRGVVAQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 125000002619 bicyclic group Chemical group 0.000 claims description 2
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 2
• 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
• 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
• MUSOFKWOKUJIRA-SAGIHDTNSA-N OC(NC1=CC=C/N=C\C2=CC=CN2CC=CC=CC=C1)=O Chemical compound OC(NC1=CC=C/N=C\C2=CC=CN2CC=CC=CC=C1)=O MUSOFKWOKUJIRA-SAGIHDTNSA-N 0.000 claims 108
• KSKFKKHQOWNOEZ-UHFFFAOYSA-N 1,2-diazacyclopentadeca-2,4,6,8,10,12,14-heptaen-6-ylcarbamic acid Chemical compound C1=CC=CC=C(C=CC=NNC=CC=C1)NC(=O)O KSKFKKHQOWNOEZ-UHFFFAOYSA-N 0.000 claims 14
• TZCCESVCSVECCN-AEJQTFAYSA-N C(C=CC=CC=CC=CC=C/N=C1)N2C/1=CC=C2 Chemical compound C(C=CC=CC=CC=CC=C/N=C1)N2C/1=CC=C2 TZCCESVCSVECCN-AEJQTFAYSA-N 0.000 claims 14
• MUSOFKWOKUJIRA-UHFFFAOYSA-N 1,13-diazabicyclo[13.3.0]octadeca-3,5,7,9,11,13,15,17-octaen-9-ylcarbamic acid Chemical compound C1C=CC=CC=CC(=CC=CN=CC2=CC=CN21)NC(=O)O MUSOFKWOKUJIRA-UHFFFAOYSA-N 0.000 claims 10
• MYPADSICVOFWBU-UHFFFAOYSA-N C1C(NC(=O)O)CCCCCCCC2CC2NC=C2CCCN21 Chemical compound C1C(NC(=O)O)CCCCCCCC2CC2NC=C2CCCN21 MYPADSICVOFWBU-UHFFFAOYSA-N 0.000 claims 8
• BQHFUZVWYNEZIQ-UHFFFAOYSA-N 2-ethylphthalazin-1-one Chemical compound C1=CC=C2C(=O)N(CC)N=CC2=C1 BQHFUZVWYNEZIQ-UHFFFAOYSA-N 0.000 claims 6
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 5
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 4
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
• XZNUJESLPUNSNO-UHFFFAOYSA-N 6-methoxyisoquinoline Chemical compound C1=NC=CC2=CC(OC)=CC=C21 XZNUJESLPUNSNO-UHFFFAOYSA-N 0.000 claims 3
• MIQQYZZSIXIFCI-UHFFFAOYSA-N 3-fluoropyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=C1F MIQQYZZSIXIFCI-UHFFFAOYSA-N 0.000 claims 2
• ZUNNSBIJBDFULW-UHFFFAOYSA-N 7-chloro-4-methoxyisoquinoline Chemical compound COC1=CN=CC2=CC(=CC=C12)Cl ZUNNSBIJBDFULW-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
• LUQVIGCZOGBWKB-UHFFFAOYSA-N 1,4-diazacyclopentadeca-2,4,6,8,10,12,14-heptaen-6-ylcarbamic acid Chemical compound C1=CC=CC=C(C=NC=CNC=CC=C1)NC(=O)O LUQVIGCZOGBWKB-UHFFFAOYSA-N 0.000 claims 1
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
• YCMAKRBTNQWRJM-UHFFFAOYSA-N 4-propoxyisoquinoline Chemical compound C(CC)OC1=CN=CC2=CC=CC=C12 YCMAKRBTNQWRJM-UHFFFAOYSA-N 0.000 claims 1
• DEHBGCXLSIYRIX-UHFFFAOYSA-N 7-fluoro-4-methoxyisoquinoline Chemical compound FC1=CC=C2C(OC)=CN=CC2=C1 DEHBGCXLSIYRIX-UHFFFAOYSA-N 0.000 claims 1
• CZBFZKZNECLWTB-UHFFFAOYSA-N 7-fluoro-6-methoxyisoquinoline Chemical compound C1=NC=C2C=C(F)C(OC)=CC2=C1 CZBFZKZNECLWTB-UHFFFAOYSA-N 0.000 claims 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
• 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims 1
• 125000003226 pyrazolyl group Chemical group 0.000 claims 1
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 88
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