AU2008236872B2 - Substituted 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indoles, methods for the production and use thereof - Google Patents

Info

Publication number

AU2008236872B2

AU2008236872B2 AU2008236872A AU2008236872A AU2008236872B2 AU 2008236872 B2 AU2008236872 B2 AU 2008236872B2 AU 2008236872 A AU2008236872 A AU 2008236872A AU 2008236872 A AU2008236872 A AU 2008236872A AU 2008236872 B2 AU2008236872 B2 AU 2008236872B2

Authority

AU

Australia

Prior art keywords

pyrido

tetrahydro

indole

methyl

pyridin

Prior art date

2007-04-05

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.)

Ceased

Links

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• 238000000034 method Methods 0.000 title claims description 29
• 238000004519 manufacturing process Methods 0.000 title claims description 4
• 150000008591 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles Chemical class 0.000 title description 15
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 42
• -1 (pyridin-2-yl)ethyl Chemical group 0.000 claims description 144
• 150000001875 compounds Chemical class 0.000 claims description 94
• 150000003839 salts Chemical class 0.000 claims description 72
• 108091005435 5-HT6 receptors Proteins 0.000 claims description 70
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 67
• 125000001424 substituent group Chemical group 0.000 claims description 57
• 125000000217 alkyl group Chemical group 0.000 claims description 51
• 238000011282 treatment Methods 0.000 claims description 48
• 241001465754 Metazoa Species 0.000 claims description 45
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 43
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 42
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 37
• RDMFHRSPDKWERA-UHFFFAOYSA-N 5H-Pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=CC=C3NC2=C1 RDMFHRSPDKWERA-UHFFFAOYSA-N 0.000 claims description 36
• 229920002554 vinyl polymer Polymers 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 25
• 208000024827 Alzheimer disease Diseases 0.000 claims description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• 238000011321 prophylaxis Methods 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 208000010877 cognitive disease Diseases 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 230000003834 intracellular effect Effects 0.000 claims description 19
• 230000004770 neurodegeneration Effects 0.000 claims description 19
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
• 150000002475 indoles Chemical class 0.000 claims description 18
• 238000002347 injection Methods 0.000 claims description 17
• 239000007924 injection Substances 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 16
• 229940076279 serotonin Drugs 0.000 claims description 16
• 125000005504 styryl group Chemical group 0.000 claims description 16
• 239000003826 tablet Substances 0.000 claims description 16
• 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 description 15
• 239000004480 active ingredient Substances 0.000 claims description 15
• 239000002775 capsule Substances 0.000 claims description 15
• 230000001225 therapeutic effect Effects 0.000 claims description 15
• 208000023105 Huntington disease Diseases 0.000 claims description 14
• 201000000980 schizophrenia Diseases 0.000 claims description 14
• 208000028017 Psychotic disease Diseases 0.000 claims description 13
• 125000003277 amino group Chemical group 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 150000002500 ions Chemical class 0.000 claims description 11
• 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 description 10
• 208000019901 Anxiety disease Diseases 0.000 claims description 9
• 238000012856 packing Methods 0.000 claims description 9
• 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 description 8
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
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• 235000020824 obesity Nutrition 0.000 claims description 7
• 230000008506 pathogenesis Effects 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
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• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
• 230000001105 regulatory effect Effects 0.000 claims description 5
• 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 description 4
• 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 description 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• OORNIOGZQUYGRW-UHFFFAOYSA-N 8-fluoro-2-methyl-5-(2-pyridin-2-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2CCC1=CC=CC=N1 OORNIOGZQUYGRW-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• 230000003042 antagnostic effect Effects 0.000 claims description 4
• 208000029028 brain injury Diseases 0.000 claims description 4
• 208000028867 ischemia Diseases 0.000 claims description 4
• 230000000324 neuroprotective effect Effects 0.000 claims description 4
• YFRQBQCQMKJACD-UHFFFAOYSA-N 1-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Chemical compound FC1NCCC=2NC=3C=CC=CC3C21 YFRQBQCQMKJACD-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• LZUIBAORLZILET-FMIVXFBMSA-N 2,8-dimethyl-5-[(e)-2-[4-(trifluoromethyl)phenyl]ethenyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2\C=C\C1=CC=C(C(F)(F)F)C=C1 LZUIBAORLZILET-FMIVXFBMSA-N 0.000 claims description 3
• 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 description 3
• GDGRKDCFXHOMEX-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-3-ylethyl)-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=CN=C1 GDGRKDCFXHOMEX-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
• SLKYZAGABKKIDN-FMIVXFBMSA-N 5-[(e)-2-(4-fluorophenyl)ethenyl]-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2\C=C\C1=CC=C(F)C=C1 SLKYZAGABKKIDN-FMIVXFBMSA-N 0.000 claims description 3
• GXHZWDQDENWEIK-UHFFFAOYSA-N 5-[2-(2-methoxyphenyl)ethynyl]-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound COC1=CC=CC=C1C#CN1C2=CC=C(C)C=C2C2=C1CCN(C)C2 GXHZWDQDENWEIK-UHFFFAOYSA-N 0.000 claims description 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 description 3
• 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 description 3
• 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 description 3
• CZCOISNXSIJAAK-UHFFFAOYSA-N 8-fluoro-2-methyl-5-(2-pyridin-3-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2CCC1=CC=CN=C1 CZCOISNXSIJAAK-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• PRSVXRUERNSVCI-UHFFFAOYSA-N 8-fluoro-2-methyl-5-(2-pyridin-4-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2CCC1=CC=NC=C1 PRSVXRUERNSVCI-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
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• 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 description 2
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• 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 description 2
• ZLTIDZRETNUAHX-SDNWHVSQSA-N 2-methyl-5-[(e)-2-phenylethenyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2\C=C\C1=CC=CC=C1 ZLTIDZRETNUAHX-SDNWHVSQSA-N 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 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 description 2
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