EA027113B1 - Регуляторы пути комплемента и их применение - Google Patents

Info

Publication number

EA027113B1

EA027113B1 EA201492023A EA201492023A EA027113B1 EA 027113 B1 EA027113 B1 EA 027113B1 EA 201492023 A EA201492023 A EA 201492023A EA 201492023 A EA201492023 A EA 201492023A EA 027113 B1 EA027113 B1 EA 027113B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

indol

imidazole

benzo

carbonitrile

Prior art date

2012-05-04

Links

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• Global Dossier
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• 230000024203 complement activation Effects 0.000 title claims description 84
• 150000001875 compounds Chemical class 0.000 claims abstract description 323
• 238000000034 method Methods 0.000 claims abstract description 83
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
• 238000004519 manufacturing process Methods 0.000 claims abstract description 9
• -1 C1-C 6 alkyl Chemical group 0.000 claims description 763
• NWVGXXPWOYZODV-UHFFFAOYSA-N 1h-imidazole-5-carbonitrile Chemical compound N#CC1=CN=CN1 NWVGXXPWOYZODV-UHFFFAOYSA-N 0.000 claims description 446
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 217
• 201000010099 disease Diseases 0.000 claims description 130
• 150000003839 salts Chemical class 0.000 claims description 114
• 208000035475 disorder Diseases 0.000 claims description 87
• 230000001404 mediated effect Effects 0.000 claims description 75
• 230000004913 activation Effects 0.000 claims description 57
• 125000005605 benzo group Chemical group 0.000 claims description 55
• 208000002780 macular degeneration Diseases 0.000 claims description 52
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 51
• 239000000203 mixture Substances 0.000 claims description 51
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 50
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
• 230000000295 complement effect Effects 0.000 claims description 47
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 42
• 239000003814 drug Substances 0.000 claims description 42
• 125000005843 halogen group Chemical group 0.000 claims description 39
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 23
• 230000000694 effects Effects 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 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 8
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 229920002554 vinyl polymer Polymers 0.000 claims description 6
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
• 150000003536 tetrazoles Chemical class 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 2
• 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 2
• LYXTUXAZKMTXBE-UHFFFAOYSA-N difluoromethyl hypobromite Chemical group FC(F)OBr LYXTUXAZKMTXBE-UHFFFAOYSA-N 0.000 claims 1
• 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 1
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• 239000002904 solvent Substances 0.000 description 38
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• 230000010410 reperfusion Effects 0.000 description 34
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• 229940049920 malate Drugs 0.000 description 31
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 30
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
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• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 22
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