EA025884B1 - ПИПЕРАЗИНО[1,2-a]ИНДОЛ-1-ОНЫ И [1,4]ДИАЗЕПИНО[1,2-a]ИНДОЛ-1-ОН - Google Patents

Info

Publication number

EA025884B1

EA025884B1 EA201590125A EA201590125A EA025884B1 EA 025884 B1 EA025884 B1 EA 025884B1 EA 201590125 A EA201590125 A EA 201590125A EA 201590125 A EA201590125 A EA 201590125A EA 025884 B1 EA025884 B1 EA 025884B1

Authority

EA

Eurasian Patent Office

Prior art keywords

pyrazino

methyl

dihydro

indol

oxo

Prior art date

2012-08-06

Links

• Espacenet
• Global Dossier
• Discuss

• CVCSXBCKBNWYAB-UHFFFAOYSA-N [1,4]diazepino[1,2-a]indol-1-one Chemical compound O=C1N=CC=CN2C3=CC=CC=C3C=C12 CVCSXBCKBNWYAB-UHFFFAOYSA-N 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 398
• -1 benzo[1,3]dioxolyl Chemical group 0.000 claims abstract description 148
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 118
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 63
• 150000002367 halogens Chemical class 0.000 claims abstract description 63
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 40
• 239000000203 mixture Substances 0.000 claims abstract description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
• 239000001257 hydrogen Substances 0.000 claims abstract description 33
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 32
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
• 239000002253 acid Substances 0.000 claims abstract description 20
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims abstract description 14
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• 125000001424 substituent group Chemical group 0.000 claims abstract description 12
• 229940079593 drug Drugs 0.000 claims abstract description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
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• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims abstract description 7
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• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract description 5
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• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 22
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• 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
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• 238000004519 manufacturing process Methods 0.000 claims description 5
• POEUJTXBABFXJV-UHFFFAOYSA-N 1-oxo-7-pyridin-3-yl-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-9-carbonitrile Chemical compound O=C1NCCCN(C=23)C1=CC3=CC(C#N)=CC=2C1=CC=CN=C1 POEUJTXBABFXJV-UHFFFAOYSA-N 0.000 claims description 4
• AAOGBIVUHNMMNK-UHFFFAOYSA-N 11-methyl-7-(4-methylphenyl)-1-oxo-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-9-carbonitrile Chemical compound C1=C(C#N)C=C2C(C)=C3C(=O)NCCCN3C2=C1C1=CC=C(C)C=C1 AAOGBIVUHNMMNK-UHFFFAOYSA-N 0.000 claims description 4
• FKQYEUPDNPITME-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-8-fluoro-10-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one Chemical compound ClC=1C=C(C=CC1Cl)C1=CC(=CC=2C(=C3N(C12)CCNC3=O)C)F FKQYEUPDNPITME-UHFFFAOYSA-N 0.000 claims description 4
• RSRQQGGSSMMYAY-UHFFFAOYSA-N 6-(3,4-difluorophenyl)-8-fluoro-10-methyl-3,4-dihydro-2h-pyrazino[1,2-a]indol-1-one Chemical compound C1=C(F)C=C2C(C)=C3C(=O)NCCN3C2=C1C1=CC=C(F)C(F)=C1 RSRQQGGSSMMYAY-UHFFFAOYSA-N 0.000 claims description 4
• NZAXDZCQWPGJRR-UHFFFAOYSA-N 6-(4-cyanophenyl)-10-methyl-1-oxo-3,4-dihydro-2h-pyrazino[1,2-a]indole-8-carbonitrile Chemical compound C1=C(C#N)C=C2C(C)=C3C(=O)NCCN3C2=C1C1=CC=C(C#N)C=C1 NZAXDZCQWPGJRR-UHFFFAOYSA-N 0.000 claims description 4
• REFADPCLVBMMER-UHFFFAOYSA-N 6-(4-fluorophenyl)-1-oxo-3,4-dihydro-2h-pyrazino[1,2-a]indole-8-carbonitrile Chemical compound C1=CC(F)=CC=C1C1=CC(C#N)=CC2=C1N1CCNC(=O)C1=C2 REFADPCLVBMMER-UHFFFAOYSA-N 0.000 claims description 4
• DGEULJMOTKWIMT-UHFFFAOYSA-N 7-(3-chlorophenyl)-1-oxo-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-9-carbonitrile Chemical compound ClC1=CC=CC(C=2C=3N4CCCNC(=O)C4=CC=3C=C(C=2)C#N)=C1 DGEULJMOTKWIMT-UHFFFAOYSA-N 0.000 claims description 4
• LAHYYYCXGWERMS-UHFFFAOYSA-N 7-(4-chloro-2-fluorophenyl)-11-methyl-1-oxo-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-9-carbonitrile Chemical compound C1=C(C#N)C=C2C(C)=C3C(=O)NCCCN3C2=C1C1=CC=C(Cl)C=C1F LAHYYYCXGWERMS-UHFFFAOYSA-N 0.000 claims description 4
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• MQVDXEGVAONTPH-UHFFFAOYSA-N 8-chloro-10-methyl-6-pyrimidin-5-yl-3,4-dihydro-2h-pyrazino[1,2-a]indol-1-one Chemical compound C1=C(Cl)C=C2C(C)=C3C(=O)NCCN3C2=C1C1=CN=CN=C1 MQVDXEGVAONTPH-UHFFFAOYSA-N 0.000 claims description 4
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• LHJBTKJTUQMCBA-UHFFFAOYSA-N 1-oxo-7-(2,3,4-trifluorophenyl)-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-9-carbonitrile Chemical compound FC1=C(F)C(F)=CC=C1C1=CC(C#N)=CC2=C1N1CCCNC(=O)C1=C2 LHJBTKJTUQMCBA-UHFFFAOYSA-N 0.000 claims description 3
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