JP2010523556A5 - - Google Patents
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- Publication number
- JP2010523556A5 JP2010523556A5 JP2010502052A JP2010502052A JP2010523556A5 JP 2010523556 A5 JP2010523556 A5 JP 2010523556A5 JP 2010502052 A JP2010502052 A JP 2010502052A JP 2010502052 A JP2010502052 A JP 2010502052A JP 2010523556 A5 JP2010523556 A5 JP 2010523556A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrido
- indole
- tetrahydro
- methyl
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 4-fluorostyryl Chemical group 0.000 claims 22
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 17
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 15
- 239000005557 antagonist Substances 0.000 claims 15
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 15
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 13
- 239000003814 drug Substances 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 150000004677 hydrates Chemical class 0.000 claims 11
- 230000002265 prevention Effects 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 8
- 239000011575 calcium Substances 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000005504 styryl group Chemical group 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 6
- 150000002500 ions Chemical class 0.000 claims 5
- 229940076279 serotonin Drugs 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 102000005962 receptors Human genes 0.000 claims 4
- 108020003175 receptors Proteins 0.000 claims 4
- 229920002554 vinyl polymer Polymers 0.000 claims 4
- XBVCLWSNUNVPNC-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-3-ylethynyl)-8-(trifluoromethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C(F)(F)F)=CC=C1N2C#CC1=CC=CN=C1 XBVCLWSNUNVPNC-UHFFFAOYSA-N 0.000 claims 3
- NESQBWDSPUMXBW-UHFFFAOYSA-N 5-ethyl-1,2,3,4-tetrahydropyrido[4,3-b]indole Chemical class C12=CC=CC=C2N(CC)C2=C1CNCC2 NESQBWDSPUMXBW-UHFFFAOYSA-N 0.000 claims 3
- YEXRDDBRPXWXJD-UHFFFAOYSA-N 5-ethynyl-1,2,3,4-tetrahydropyrido[4,3-b]indole Chemical class C12=CC=CC=C2N(C#C)C2=C1CNCC2 YEXRDDBRPXWXJD-UHFFFAOYSA-N 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000023105 Huntington disease Diseases 0.000 claims 3
- 230000003834 intracellular effect Effects 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 150000008591 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles Chemical class 0.000 claims 2
- IBUHDDLETPJVGP-UHFFFAOYSA-N 2,8-dimethyl-5-(2-phenylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=CC=C1 IBUHDDLETPJVGP-UHFFFAOYSA-N 0.000 claims 2
- NCRLGWIBMFMWHM-UHFFFAOYSA-N 2,8-dimethyl-5-(2-phenylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2C#CC1=CC=CC=C1 NCRLGWIBMFMWHM-UHFFFAOYSA-N 0.000 claims 2
- DUUHEGAGOHEODE-UHFFFAOYSA-N 2,8-dimethyl-5-(2-pyrazin-2-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CN=CC=N1 DUUHEGAGOHEODE-UHFFFAOYSA-N 0.000 claims 2
- DAZIZGHYHJVOSW-UHFFFAOYSA-N 2,8-dimethyl-5-(2-pyridin-2-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2C#CC1=CC=CC=N1 DAZIZGHYHJVOSW-UHFFFAOYSA-N 0.000 claims 2
- CTSIMNCXAXCWOY-UHFFFAOYSA-N 2,8-dimethyl-5-(2-pyridin-3-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2C#CC1=CC=CN=C1 CTSIMNCXAXCWOY-UHFFFAOYSA-N 0.000 claims 2
- OHKBLWVRXBNICP-UHFFFAOYSA-N 2,8-dimethyl-5-(2-pyridin-4-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=NC=C1 OHKBLWVRXBNICP-UHFFFAOYSA-N 0.000 claims 2
- SKLDPXZPHBQPFB-UHFFFAOYSA-N 2,8-dimethyl-5-(2-pyridin-4-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2C#CC1=CC=NC=C1 SKLDPXZPHBQPFB-UHFFFAOYSA-N 0.000 claims 2
- XQDRWCFJBHLWPR-JLHYYAGUSA-N 2,8-dimethyl-5-[(e)-2-phenylethenyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2\C=C\C1=CC=CC=C1 XQDRWCFJBHLWPR-JLHYYAGUSA-N 0.000 claims 2
- ZBNYHEVTJCAGAE-KPKJPENVSA-N 2,8-dimethyl-5-[(e)-2-pyridin-4-ylethenyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2\C=C\C1=CC=NC=C1 ZBNYHEVTJCAGAE-KPKJPENVSA-N 0.000 claims 2
- KPGWZRTZTASLIF-UHFFFAOYSA-N 2-methyl-5-(2-phenylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2CCC1=CC=CC=C1 KPGWZRTZTASLIF-UHFFFAOYSA-N 0.000 claims 2
- VATMTSNDTTWBHN-UHFFFAOYSA-N 2-methyl-5-(2-phenylethyl)-6-(trifluoromethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC(C(F)(F)F)=C1N2CCC1=CC=CC=C1 VATMTSNDTTWBHN-UHFFFAOYSA-N 0.000 claims 2
- VGJCKVYMMJXTIH-UHFFFAOYSA-N 2-methyl-5-(2-phenylethyl)-8-(trifluoromethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C(F)(F)F)=CC=C1N2CCC1=CC=CC=C1 VGJCKVYMMJXTIH-UHFFFAOYSA-N 0.000 claims 2
- XQOOIUOWFLBMEA-UHFFFAOYSA-N 2-methyl-5-(2-phenylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2C#CC1=CC=CC=C1 XQOOIUOWFLBMEA-UHFFFAOYSA-N 0.000 claims 2
- WTMKJZWIEBUUNH-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-2-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2CCC1=CC=CC=N1 WTMKJZWIEBUUNH-UHFFFAOYSA-N 0.000 claims 2
- MVNYSGODLSEWHS-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-3-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2C#CC1=CC=CN=C1 MVNYSGODLSEWHS-UHFFFAOYSA-N 0.000 claims 2
- BRMMBDRDSQRBHU-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-4-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2CCC1=CC=NC=C1 BRMMBDRDSQRBHU-UHFFFAOYSA-N 0.000 claims 2
- VATHEBDOZWAVRR-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-4-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2C#CC1=CC=NC=C1 VATHEBDOZWAVRR-UHFFFAOYSA-N 0.000 claims 2
- VXKWUCFGHPQDJE-UHFFFAOYSA-N 2-methyl-5-(2-pyrimidin-5-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2C#CC1=CN=CN=C1 VXKWUCFGHPQDJE-UHFFFAOYSA-N 0.000 claims 2
- LAOSTQCWEMLRTM-UKTHLTGXSA-N 2-methyl-5-[(e)-2-pyridin-2-ylethenyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2\C=C\C1=CC=CC=N1 LAOSTQCWEMLRTM-UKTHLTGXSA-N 0.000 claims 2
- HVJRMUTVOBWKJG-MDWZMJQESA-N 2-methyl-5-[(e)-2-pyridin-4-ylethenyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2\C=C\C1=CC=NC=C1 HVJRMUTVOBWKJG-MDWZMJQESA-N 0.000 claims 2
- UPLUVROGBHSYKI-UHFFFAOYSA-N 2-methyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2CCC1=CC=C(C)N=C1 UPLUVROGBHSYKI-UHFFFAOYSA-N 0.000 claims 2
- NBLGYQHUKBRDOI-UHFFFAOYSA-N 5-[2-(2-fluorophenyl)ethynyl]-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2C#CC1=CC=CC=C1F NBLGYQHUKBRDOI-UHFFFAOYSA-N 0.000 claims 2
- MZTCPDJFUXMOFR-UHFFFAOYSA-N 5-[2-(3-fluorophenyl)ethynyl]-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2C#CC1=CC=CC(F)=C1 MZTCPDJFUXMOFR-UHFFFAOYSA-N 0.000 claims 2
- WGZPAEUKXCKVDO-UHFFFAOYSA-N 5-[2-(4-methoxyphenyl)ethynyl]-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1=CC(OC)=CC=C1C#CN1C2=CC=C(C)C=C2C2=C1CCN(C)C2 WGZPAEUKXCKVDO-UHFFFAOYSA-N 0.000 claims 2
- KGWTUPZUHIAZPI-UHFFFAOYSA-N 5-ethenyl-1,2,3,4-tetrahydropyrido[4,3-b]indole Chemical class C12=CC=CC=C2N(C=C)C2=C1CNCC2 KGWTUPZUHIAZPI-UHFFFAOYSA-N 0.000 claims 2
- IAPCDZHOSMWPKV-UHFFFAOYSA-N 6-fluoro-2-methyl-5-(2-phenylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC(F)=C1N2CCC1=CC=CC=C1 IAPCDZHOSMWPKV-UHFFFAOYSA-N 0.000 claims 2
- IWEWIZBBORJKBV-UHFFFAOYSA-N 8-fluoro-2-methyl-5-(2-phenylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2CCC1=CC=CC=C1 IWEWIZBBORJKBV-UHFFFAOYSA-N 0.000 claims 2
- IJTHZGGGQZEMPL-UHFFFAOYSA-N 8-fluoro-2-methyl-5-(2-pyridin-2-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2C#CC1=CC=CC=N1 IJTHZGGGQZEMPL-UHFFFAOYSA-N 0.000 claims 2
- DPTCIIYSUBFZKY-UHFFFAOYSA-N 8-fluoro-2-methyl-5-(2-pyridin-3-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2C#CC1=CC=CN=C1 DPTCIIYSUBFZKY-UHFFFAOYSA-N 0.000 claims 2
- HCWWPLNFZNUYRH-UHFFFAOYSA-N 8-fluoro-2-methyl-5-(2-pyridin-4-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2C#CC1=CC=NC=C1 HCWWPLNFZNUYRH-UHFFFAOYSA-N 0.000 claims 2
- BGBNMDBTYCCSBL-FMIVXFBMSA-N 8-fluoro-2-methyl-5-[(e)-2-phenylethenyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2\C=C\C1=CC=CC=C1 BGBNMDBTYCCSBL-FMIVXFBMSA-N 0.000 claims 2
- JLCBMWGBAILPFS-YRNVUSSQSA-N 8-fluoro-2-methyl-5-[(e)-2-pyridin-2-ylethenyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2\C=C\C1=CC=CC=N1 JLCBMWGBAILPFS-YRNVUSSQSA-N 0.000 claims 2
- RZNJWVKDPLJHOA-IZZDOVSWSA-N 8-fluoro-2-methyl-5-[(e)-2-pyridin-4-ylethenyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2\C=C\C1=CC=NC=C1 RZNJWVKDPLJHOA-IZZDOVSWSA-N 0.000 claims 2
- ALOWJQCLRWGVOV-UHFFFAOYSA-N 8-fluoro-2-methyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2CCC1=CC=C(C)N=C1 ALOWJQCLRWGVOV-UHFFFAOYSA-N 0.000 claims 2
- XXLOLGBZLDQPQO-DHZHZOJOSA-N 8-fluoro-5-[(e)-2-(4-fluorophenyl)ethenyl]-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2\C=C\C1=CC=C(F)C=C1 XXLOLGBZLDQPQO-DHZHZOJOSA-N 0.000 claims 2
- BYXFJHQODHAJBJ-UHFFFAOYSA-N 8-fluoro-5-[2-(3-fluorophenyl)ethynyl]-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2C#CC1=CC=CC(F)=C1 BYXFJHQODHAJBJ-UHFFFAOYSA-N 0.000 claims 2
- RZJAPMAJSYCHTC-UHFFFAOYSA-N 8-fluoro-5-[2-(4-fluorophenyl)ethynyl]-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2C#CC1=CC=C(F)C=C1 RZJAPMAJSYCHTC-UHFFFAOYSA-N 0.000 claims 2
- QIFUPIGOSFZCEZ-UHFFFAOYSA-N 8-fluoro-5-[2-(4-methoxyphenyl)ethynyl]-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1=CC(OC)=CC=C1C#CN1C2=CC=C(F)C=C2C2=C1CCN(C)C2 QIFUPIGOSFZCEZ-UHFFFAOYSA-N 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 230000008506 pathogenesis Effects 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- ZRGIHRLCJVIUNZ-UHFFFAOYSA-N 2,3,4,4a-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound N1=C2C=CC=CC2=C2C1CCNC2 ZRGIHRLCJVIUNZ-UHFFFAOYSA-N 0.000 claims 1
- RPROHCOBMVQVIV-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CCNC2 RPROHCOBMVQVIV-UHFFFAOYSA-N 0.000 claims 1
- KDANPFZBGFTPQX-UHFFFAOYSA-N 2,7-dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=C(C)C=C1N2CCC1=CC=C(C)N=C1 KDANPFZBGFTPQX-UHFFFAOYSA-N 0.000 claims 1
- PMLYIGFXJXRZKK-UHFFFAOYSA-N 2,8-dimethyl-5-(2-pyridin-2-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=CC=N1 PMLYIGFXJXRZKK-UHFFFAOYSA-N 0.000 claims 1
- ZKAVOICTUKPVNY-UHFFFAOYSA-N 2,8-dimethyl-5-(2-pyridin-3-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=CN=C1 ZKAVOICTUKPVNY-UHFFFAOYSA-N 0.000 claims 1
- SMIWUMHLBZQUSR-UHFFFAOYSA-N 2-benzyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1=NC(C)=CC=C1CCN1C2=CC=CC=C2C(C2)=C1CCN2CC1=CC=CC=C1 SMIWUMHLBZQUSR-UHFFFAOYSA-N 0.000 claims 1
- CLKXVWCKERUWCO-UHFFFAOYSA-N 2-benzyl-8-chloro-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1=NC(C)=CC=C1CCN1C2=CC=C(Cl)C=C2C(C2)=C1CCN2CC1=CC=CC=C1 CLKXVWCKERUWCO-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- FAJHPHBADBLSHG-UHFFFAOYSA-N 2-methyl-2,3,4,5-tetrahydro-1h-1,4-benzodiazepin-9-amine Chemical group N1C(C)CNCC2=CC=CC(N)=C21 FAJHPHBADBLSHG-UHFFFAOYSA-N 0.000 claims 1
- ZHQFDMCLKMBYHW-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-2-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2C#CC1=CC=CC=N1 ZHQFDMCLKMBYHW-UHFFFAOYSA-N 0.000 claims 1
- DICDOOGFHQRKKL-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-3-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2CCC1=CC=CN=C1 DICDOOGFHQRKKL-UHFFFAOYSA-N 0.000 claims 1
- QZMJEAXRHNEGRT-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-3-ylethyl)-6-(trifluoromethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC(C(F)(F)F)=C1N2CCC1=CC=CN=C1 QZMJEAXRHNEGRT-UHFFFAOYSA-N 0.000 claims 1
- HJSAIEMTRYMFMF-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-4-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxylic acid Chemical compound C1N(C)CCC2=C1C1=CC(C(O)=O)=CC=C1N2CCC1=CC=NC=C1 HJSAIEMTRYMFMF-UHFFFAOYSA-N 0.000 claims 1
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| RU2334514C1 (ru) * | 2006-12-01 | 2008-09-27 | Институт физиологически активных веществ Российской Академии наук | СРЕДСТВО ДЛЯ УЛУЧШЕНИЯ КОГНИТИВНЫХ ФУНКЦИЙ И ПАМЯТИ НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО (4,3-b) ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| CN101868234A (zh) * | 2007-09-20 | 2010-10-20 | D2E有限公司 | 具有神经保护和认知增强特性的氢化吡啶并[4,3-b]吲哚的含氟衍生物,其制备方法及应用 |
| RU2007139634A (ru) * | 2007-10-25 | 2009-04-27 | Сергей Олегович Бачурин (RU) | Новые тиазол-, триазол- или оксадиазол-содержащие тетрациклические соединения |
| JP2011507835A (ja) * | 2007-12-21 | 2011-03-10 | アンドレイ・アレクサンドロビッチ・イワシェンコ | α−アドレナリン受容体、ドーパミン、ヒスタミン、イミダゾリン及びセロトニン受容体のリガンド並びにその使用 |
| CA2719412A1 (en) * | 2008-03-24 | 2009-10-01 | Medivation Technologies, Inc. | Pyrido[3,4-b]indoles and methods of use |
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2008
- 2008-04-01 CA CA2683453A patent/CA2683453C/en active Active
- 2008-04-01 US US12/594,453 patent/US8541437B2/en not_active Expired - Fee Related
- 2008-04-01 WO PCT/RU2008/000196 patent/WO2008123796A2/ru not_active Ceased
- 2008-04-01 EA EA200901253A patent/EA016234B1/ru not_active IP Right Cessation
- 2008-04-01 AU AU2008236872A patent/AU2008236872B2/en not_active Ceased
- 2008-04-01 KR KR1020097023171A patent/KR20090130105A/ko not_active Withdrawn
- 2008-04-01 UA UAA200910930A patent/UA98324C2/ru unknown
- 2008-04-01 JP JP2010502052A patent/JP5580731B2/ja active Active
- 2008-04-01 EP EP08753899.7A patent/EP2145887B1/en active Active
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2013
- 2013-03-16 US US13/844,825 patent/US20130217703A1/en not_active Abandoned
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2015
- 2015-07-03 US US14/791,280 patent/US9655886B2/en active Active
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