JP2012525431A5 - - Google Patents
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- JP2012525431A5 JP2012525431A5 JP2012508752A JP2012508752A JP2012525431A5 JP 2012525431 A5 JP2012525431 A5 JP 2012525431A5 JP 2012508752 A JP2012508752 A JP 2012508752A JP 2012508752 A JP2012508752 A JP 2012508752A JP 2012525431 A5 JP2012525431 A5 JP 2012525431A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrido
- unsubstituted
- salt
- substituted
- 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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- 150000001875 compounds Chemical class 0.000 claims description 96
- 150000003839 salts Chemical class 0.000 claims description 66
- 239000012453 solvate Substances 0.000 claims description 59
- -1 perhaloalkyl Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 14
- 125000002971 oxazolyl group Chemical group 0.000 claims description 14
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 11
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000005102 carbonylalkoxy group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000005589 carbonylalkylenealkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- PXSYMVMGRYBTRY-UHFFFAOYSA-N 2,8-dimethyl-5-[(2-phenyl-1,3-dioxolan-2-yl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC1(C=2C=CC=CC=2)OCCO1 PXSYMVMGRYBTRY-UHFFFAOYSA-N 0.000 claims description 3
- KSHIBYPIOGCPDH-UHFFFAOYSA-N 2,8-dimethyl-5-[(2-pyridin-3-yl-1,3-dioxolan-2-yl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC1(C=2C=NC=CC=2)OCCO1 KSHIBYPIOGCPDH-UHFFFAOYSA-N 0.000 claims description 3
- WIFQQALACNYNTA-UHFFFAOYSA-N 5-[[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]methyl]-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC1(C=2C=CC(F)=CC=2)OCCO1 WIFQQALACNYNTA-UHFFFAOYSA-N 0.000 claims description 3
- NXUKGYHIRFZZSE-UHFFFAOYSA-N 8-chloro-2-methyl-5-[[2-(2-methylpyridin-4-yl)-1,3-dioxolan-2-yl]methyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC1(C=2C=C(C)N=CC=2)OCCO1 NXUKGYHIRFZZSE-UHFFFAOYSA-N 0.000 claims description 3
- XNSPQXHRNZQWTD-UHFFFAOYSA-N 8-chloro-2-methyl-5-[[2-(6-methylpyridin-3-yl)-1,3-dioxolan-2-yl]methyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC1(C=2C=NC(C)=CC=2)OCCO1 XNSPQXHRNZQWTD-UHFFFAOYSA-N 0.000 claims description 3
- VAVLJFSBBMYFKS-UHFFFAOYSA-N 8-chloro-5-[[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]methyl]-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC1(C=2C=CC(Cl)=CC=2)OCCO1 VAVLJFSBBMYFKS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- CEHPIEPEGHHJJZ-UHFFFAOYSA-N 2,8-dimethyl-5-[(2-pyrimidin-4-yl-1,3-dioxolan-2-yl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC1(C=2N=CN=CC=2)OCCO1 CEHPIEPEGHHJJZ-UHFFFAOYSA-N 0.000 claims description 2
- SDDGVYKUUGHLJD-UHFFFAOYSA-N 2-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-(4-fluorophenyl)-1-phenylethanol Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(O)(C=1C=CC(F)=CC=1)C1=CC=CC=C1 SDDGVYKUUGHLJD-UHFFFAOYSA-N 0.000 claims description 2
- UBFWYALTTULUDG-UHFFFAOYSA-N 2-cyclopropyl-5-[2-fluoro-2-(4-methoxyphenyl)propyl]-8-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1=CC(OC)=CC=C1C(C)(F)CN1C2=CC=C(C)C=C2C2=C1CCN(C1CC1)C2 UBFWYALTTULUDG-UHFFFAOYSA-N 0.000 claims description 2
- YYBJLIFFKRGEED-UHFFFAOYSA-N 2-ethyl-5-(2-fluoro-2-pyridin-3-ylpropyl)-8-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(CC)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(F)C1=CC=CN=C1 YYBJLIFFKRGEED-UHFFFAOYSA-N 0.000 claims description 2
- CRBBHOGWBDLVRA-UHFFFAOYSA-N 2-methyl-5-[(2-pyridin-4-yl-1,3-dioxolan-2-yl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2CC1(C=2C=CN=CC=2)OCCO1 CRBBHOGWBDLVRA-UHFFFAOYSA-N 0.000 claims description 2
- QXTAYFISWQSPRT-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-4-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)butanoic acid Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(CC(O)=O)C1=CC=C(F)C=C1F QXTAYFISWQSPRT-UHFFFAOYSA-N 0.000 claims description 2
- WXTVXXFBPXVBTO-UHFFFAOYSA-N 4-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-(2-fluorophenyl)-n-methylbutanamide Chemical compound C1=2CCN(C)CC=2C2=CC(C)=CC=C2N1CC(CC(=O)NC)C1=CC=CC=C1F WXTVXXFBPXVBTO-UHFFFAOYSA-N 0.000 claims description 2
- OPMKRVRPBZAAMY-UHFFFAOYSA-N 4-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-(2-fluorophenyl)butanoic acid Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(CC(O)=O)C1=CC=CC=C1F OPMKRVRPBZAAMY-UHFFFAOYSA-N 0.000 claims description 2
- CMBIIHJHLILBSO-UHFFFAOYSA-N 4-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-(4-fluorophenyl)-n-methylbutanamide Chemical compound C1=2CCN(C)CC=2C2=CC(C)=CC=C2N1CC(CC(=O)NC)C1=CC=C(F)C=C1 CMBIIHJHLILBSO-UHFFFAOYSA-N 0.000 claims description 2
- WPRCVURQRSQRDQ-UHFFFAOYSA-N 4-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-(4-fluorophenyl)butanoic acid Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(CC(O)=O)C1=CC=C(F)C=C1 WPRCVURQRSQRDQ-UHFFFAOYSA-N 0.000 claims description 2
- NLHAWMARHNLPJU-UHFFFAOYSA-N 4-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-pyridin-3-ylbutanoic acid Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(CC(O)=O)C1=CC=CN=C1 NLHAWMARHNLPJU-UHFFFAOYSA-N 0.000 claims description 2
- GFXZZEBQRNFDPE-UHFFFAOYSA-N 4-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-(4-chlorophenyl)-n-methylbutanamide Chemical compound C1=2CCN(C)CC=2C2=CC(Cl)=CC=C2N1CC(CC(=O)NC)C1=CC=C(Cl)C=C1 GFXZZEBQRNFDPE-UHFFFAOYSA-N 0.000 claims description 2
- HFYNOYFHGWDKRQ-UHFFFAOYSA-N 4-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-(4-chlorophenyl)butanoic acid Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(CC(O)=O)C1=CC=C(Cl)C=C1 HFYNOYFHGWDKRQ-UHFFFAOYSA-N 0.000 claims description 2
- QNTGEWKKHKULDO-UHFFFAOYSA-N 4-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-(4-methoxyphenyl)butanoic acid Chemical compound C1=CC(OC)=CC=C1C(CC(O)=O)CN1C2=CC=C(Cl)C=C2C2=C1CCN(C)C2 QNTGEWKKHKULDO-UHFFFAOYSA-N 0.000 claims description 2
- ZHAOCYAINPJTBG-UHFFFAOYSA-N 4-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-pyrimidin-4-ylbutanoic acid Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(CC(O)=O)C1=CC=NC=N1 ZHAOCYAINPJTBG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- JHTDVHAJMMAAIW-UHFFFAOYSA-N 5-(2-fluoro-2-pyridin-4-ylpropyl)-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(F)C1=CC=NC=C1 JHTDVHAJMMAAIW-UHFFFAOYSA-N 0.000 claims description 2
- GOVOMCQLELOXOH-UHFFFAOYSA-N 5-(2-fluoro-2-pyrimidin-4-ylpropyl)-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(F)C1=CC=NC=N1 GOVOMCQLELOXOH-UHFFFAOYSA-N 0.000 claims description 2
- YQQMLLFAAOPODD-UHFFFAOYSA-N 5-[2-(4-chlorophenyl)-2-fluoropropyl]-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(F)C1=CC=C(Cl)C=C1 YQQMLLFAAOPODD-UHFFFAOYSA-N 0.000 claims description 2
- MCXPOPAHXQJKEF-UHFFFAOYSA-N 5-[2-fluoro-2-(2-methylpyridin-4-yl)propyl]-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(F)C1=CC=NC(C)=C1 MCXPOPAHXQJKEF-UHFFFAOYSA-N 0.000 claims description 2
- RKPPXNINQHFRTD-UHFFFAOYSA-N 5-[2-fluoro-2-(4-fluorophenyl)propyl]-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(F)C1=CC=C(F)C=C1 RKPPXNINQHFRTD-UHFFFAOYSA-N 0.000 claims description 2
- WDTMBTSDKCPDBW-UHFFFAOYSA-N 8-chloro-2-methyl-5-[2-(3-methylpyridin-4-yl)butyl]-3,4-dihydro-1H-pyrido[4,3-b]indole Chemical compound CCC(CN1C2=C(CN(C)CC2)C2=CC(Cl)=CC=C12)C1=C(C)C=NC=C1 WDTMBTSDKCPDBW-UHFFFAOYSA-N 0.000 claims description 2
- FQGQMNNNLBPFDH-UHFFFAOYSA-N 8-chloro-2-methyl-5-[[2-(3-methylpyridin-4-yl)-1,3-dioxolan-2-yl]methyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC1(C=2C(=CN=CC=2)C)OCCO1 FQGQMNNNLBPFDH-UHFFFAOYSA-N 0.000 claims description 2
- ARAICNLSMVFMIA-UHFFFAOYSA-N 8-chloro-5-(2-fluoro-2-pyridin-3-ylpropyl)-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(C)(F)C1=CC=CN=C1 ARAICNLSMVFMIA-UHFFFAOYSA-N 0.000 claims description 2
- DVDZIMYMWCQZOA-UHFFFAOYSA-N 8-chloro-5-(2-fluoro-2-pyridin-4-ylpropyl)-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(C)(F)C1=CC=NC=C1 DVDZIMYMWCQZOA-UHFFFAOYSA-N 0.000 claims description 2
- ZVDZIWOYYUERJP-UHFFFAOYSA-N 8-chloro-5-[2-(2,4-difluorophenyl)-2-fluoropropyl]-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(C)(F)C1=CC=C(F)C=C1F ZVDZIWOYYUERJP-UHFFFAOYSA-N 0.000 claims description 2
- ZYCJYYFQJHKNMC-UHFFFAOYSA-N 8-chloro-5-[2-fluoro-2-(6-methylpyridin-3-yl)propyl]-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(C)(F)C1=CC=C(C)N=C1 ZYCJYYFQJHKNMC-UHFFFAOYSA-N 0.000 claims description 2
- VPCVVOOGNDRGFN-UHFFFAOYSA-N 8-chloro-5-[[2-(2-chlorophenyl)-1,3-dioxolan-2-yl]methyl]-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC1(C=2C(=CC=CC=2)Cl)OCCO1 VPCVVOOGNDRGFN-UHFFFAOYSA-N 0.000 claims description 2
- MQTGBDFTUKTJSY-UHFFFAOYSA-N CCC(CN1C2=C(CN(CC2)C)C3=C1C=CC(=C3)Cl)C4=CN=C(C=C4)C Chemical compound CCC(CN1C2=C(CN(CC2)C)C3=C1C=CC(=C3)Cl)C4=CN=C(C=C4)C MQTGBDFTUKTJSY-UHFFFAOYSA-N 0.000 claims description 2
- DQBINRGWLUXRHX-UHFFFAOYSA-N CCC(CN1C2=C(CN(CC2)CC)C3=C1C=CC(=C3)C)C4=CC(=NC=C4)C Chemical compound CCC(CN1C2=C(CN(CC2)CC)C3=C1C=CC(=C3)C)C4=CC(=NC=C4)C DQBINRGWLUXRHX-UHFFFAOYSA-N 0.000 claims description 2
- 102000000543 Histamine Receptors Human genes 0.000 claims description 2
- 108010002059 Histamine Receptors Proteins 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 230000019771 cognition Effects 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- NCKQTYFVEMJDIE-UHFFFAOYSA-N ethyl 4-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-(4-fluorophenyl)butanoate Chemical compound C1=2CCN(C)CC=2C2=CC(C)=CC=C2N1CC(CC(=O)OCC)C1=CC=C(F)C=C1 NCKQTYFVEMJDIE-UHFFFAOYSA-N 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
- OUNFKARXQGDBIP-UHFFFAOYSA-N 4-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-pyridin-4-ylbutanoic acid Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(CC(O)=O)C1=CC=NC=C1 OUNFKARXQGDBIP-UHFFFAOYSA-N 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 0 *C(*)(*)C[n]1c2ccc(*)cc2c2c1CCN(*)C2 Chemical compound *C(*)(*)C[n]1c2ccc(*)cc2c2c1CCN(*)C2 0.000 description 19
- NXUDRZAGTICPOO-UHFFFAOYSA-N 5-(2-fluoro-2-pyridin-4-ylethyl)-2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(F)C1=CC=NC=C1 NXUDRZAGTICPOO-UHFFFAOYSA-N 0.000 description 1
- QSWKMJOKNSYKKR-UHFFFAOYSA-N 8-chloro-5-[2-fluoro-2-(3-methylpyridin-4-yl)propyl]-2-propan-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C(C)C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(C)(F)C1=CC=NC=C1C QSWKMJOKNSYKKR-UHFFFAOYSA-N 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1135/NUM/2009 | 2009-04-29 | ||
| IN1135MU2009 | 2009-04-29 | ||
| US18125909P | 2009-05-26 | 2009-05-26 | |
| US61/181,259 | 2009-05-26 | ||
| PCT/US2010/033055 WO2011019417A1 (en) | 2009-04-29 | 2010-04-29 | Pyrido [4, 3-b] indoles and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012525431A JP2012525431A (ja) | 2012-10-22 |
| JP2012525431A5 true JP2012525431A5 (https=) | 2013-06-27 |
| JP5827943B2 JP5827943B2 (ja) | 2015-12-02 |
Family
ID=43586371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012508752A Expired - Fee Related JP5827943B2 (ja) | 2009-04-29 | 2010-04-29 | ピリド［４，３−ｂ］インドールおよびその使用方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8741919B2 (https=) |
| EP (1) | EP2424366B1 (https=) |
| JP (1) | JP5827943B2 (https=) |
| CN (1) | CN102480956B (https=) |
| AU (1) | AU2010282990B2 (https=) |
| BR (1) | BRPI1006608A2 (https=) |
| CA (1) | CA2760516A1 (https=) |
| WO (1) | WO2011019417A1 (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2007139634A (ru) | 2007-10-25 | 2009-04-27 | Сергей Олегович Бачурин (RU) | Новые тиазол-, триазол- или оксадиазол-содержащие тетрациклические соединения |
| RU2544856C2 (ru) | 2008-01-25 | 2015-03-20 | Сергей Олегович Бачурин | НОВЫЕ ПРОИЗВОДНЫЕ 2,3,4,5-ТЕТРАГИДРО-1-ПИРИДО[4,3-b]ИНДОЛА И СПОСОБЫ ИХ ПРИМЕНЕНИЯ |
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2010
- 2010-04-29 JP JP2012508752A patent/JP5827943B2/ja not_active Expired - Fee Related
- 2010-04-29 WO PCT/US2010/033055 patent/WO2011019417A1/en not_active Ceased
- 2010-04-29 EP EP10808471.6A patent/EP2424366B1/en not_active Not-in-force
- 2010-04-29 AU AU2010282990A patent/AU2010282990B2/en not_active Ceased
- 2010-04-29 US US13/318,124 patent/US8741919B2/en not_active Expired - Fee Related
- 2010-04-29 CN CN201080029084.1A patent/CN102480956B/zh not_active Expired - Fee Related
- 2010-04-29 BR BRPI1006608-0A patent/BRPI1006608A2/pt not_active IP Right Cessation
- 2010-04-29 CA CA2760516A patent/CA2760516A1/en not_active Abandoned
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2013
- 2013-03-08 US US13/791,862 patent/US8927571B2/en not_active Expired - Fee Related
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