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
- 239000011780 sodium chloride Substances 0.000 claims description 66
- 239000012453 solvate Substances 0.000 claims description 59
- -1 perhaloalkyl Chemical group 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 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
- 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
- DNSISZSEWVHGLH-UHFFFAOYSA-N Butyramide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 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
- 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
- 125000005589 carbonylalkylenealkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-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
- 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 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
- 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 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
- 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
- WDTMBTSDKCPDBW-UHFFFAOYSA-N CCC(CN1C2=C(CN(C)CC2)C2=CC(Cl)=CC=C12)C1=C(C)C=NC=C1 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
- 206010057668 Cognitive disease Diseases 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
- 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
- 201000010099 disease 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
- 230000000051 modifying Effects 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
- 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
- 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
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive Effects 0.000 description 1
- 125000005842 heteroatoms 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 (US07981874-20110719-C00313.png) | 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 (9)
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 |
JP5586577B2 (ja) * | 2008-03-24 | 2014-09-10 | メディベイション テクノロジーズ, インコーポレイテッド | 架橋複素環化合物およびその使用 |
PE20091717A1 (es) * | 2008-03-24 | 2009-11-25 | Medivation Technologies Inc | Pirido[3,4-b] indoles como moduladores de receptores de histamina |
AU2009308708B2 (en) * | 2008-10-31 | 2015-11-19 | Medivation Technologies, Inc. | Azepino [4, 5-b] indoles and methods of use |
US8907097B2 (en) | 2008-10-31 | 2014-12-09 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles containing rigid moieties |
US9962368B2 (en) | 2009-01-09 | 2018-05-08 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
US8362277B2 (en) | 2009-01-09 | 2013-01-29 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
WO2010081115A1 (en) | 2009-01-09 | 2010-07-15 | University Of Texas Southwestern Medical Center | Pro-neurogenic compounds |
US9162980B2 (en) | 2009-01-09 | 2015-10-20 | Board Of Regents Of The University Of Texas System | Anti-depression compounds |
JP2012517471A (ja) | 2009-02-11 | 2012-08-02 | スノビオン プハルマセウトイカルス インコーポレイテッド | ヒスタミンh3インバースアゴニスト及びアンタゴニスト、並びにその使用方法 |
EP2424366B1 (en) * | 2009-04-29 | 2016-02-17 | Medivation Technologies, Inc. | Pyrido [4, 3-b]indoles and methods of use |
US9255094B2 (en) | 2009-04-29 | 2016-02-09 | Medivation Technologies, Inc. | Pyrido[4,3-B]indoles and methods of use |
BR112012006640A2 (pt) | 2009-09-23 | 2019-09-24 | Medivation Technologies Inc | composto, composição farmacêutica, método de tratamento de um distúrbio cognitivo, distúrbiopsocótico, distúrbio mediado por neurotransmissor ou um distúrbio neuronal e kit |
BR112012006646A2 (pt) * | 2009-09-23 | 2019-09-24 | Medivation Technologies Inc | composto, composição farmacêutica, método de tratamento de um distùrbio cognitivo, distúrbio psicótico, distúrbio mediado por neurotransmissor ou um distúrbio neuronal e kit |
WO2011038164A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Bridged heterocyclic compounds and methods of use |
US9040519B2 (en) | 2010-02-18 | 2015-05-26 | Medivation Technologies, Inc. | Fused tetracyclic pyrido [4,3-B] indole and pyrido [3,4-B] indole derivatives and methods of use |
WO2011103460A1 (en) | 2010-02-18 | 2011-08-25 | Medivation Technologies, Inc. | Fused tetracyclic pyrido[4,3-b]indole and pyrido[3,4-b]ondole derivatives and methods of use |
US9034865B2 (en) | 2010-02-18 | 2015-05-19 | Medivation Technologies, Inc. | Pyrido [4,3-B] indole and pyrido [3,4-B] indole derivatives and methods of use |
WO2011103430A1 (en) | 2010-02-19 | 2011-08-25 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
WO2012006419A2 (en) * | 2010-07-07 | 2012-01-12 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
WO2012112964A2 (en) | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | PYRIDO[4,3-b]INDOLE AND PYRIDO[3,4-b]INDOLE DERIVATIVES AND METHODS OF USE |
BR112013021125A2 (pt) | 2011-02-18 | 2019-09-24 | Medivation Technologies Inc | método para regular os níveis de glicose no sangue, método para aumentar a secreção da insulina ou promover a liberação da insulina na corrente sanguínea, método para tratar uma doença ou condição, método para retardar o ínicio de uma doença ou condição de doença kit, composto de composição farmacêutica |
US9434747B2 (en) | 2011-02-18 | 2016-09-06 | Medivation Technologies, Inc. | Methods of treating diabetes |
US9199985B2 (en) | 2011-02-18 | 2015-12-01 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
EP2785720B1 (en) * | 2011-11-29 | 2017-08-09 | Nanjing Allgen Pharma Co. Ltd. | Heterocyclic amides compounds which are hdac6 inhibitors and used as anti-tumoral agents |
US20150315188A1 (en) * | 2012-08-22 | 2015-11-05 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
WO2014031986A1 (en) | 2012-08-24 | 2014-02-27 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
WO2015070234A2 (en) | 2013-11-11 | 2015-05-14 | Board Of Regents Of The University Of Texas System | Neuroprotective compounds and use thereof |
WO2015070237A1 (en) | 2013-11-11 | 2015-05-14 | Board Of Regents Of The University Of Texas System | Neuroprotective chemicals and methods for identifying and using same |
JP7286679B2 (ja) * | 2018-02-05 | 2023-06-05 | ザ ロックフェラー ユニバーシティー | 自己炎症性疾患を治療するためのcGASの2,3,4,5-テトラヒドロ-1H-ピリド[4,3-b]インドール阻害剤 |
JP2023543254A (ja) * | 2020-09-24 | 2023-10-13 | ベンタス・セラピューティクス・ユー・エス・インコーポレイテッド | ピリド[4,3-b]インドール誘導体およびその医薬としての使用 |
Family Cites Families (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3409628A (en) | 1966-05-12 | 1968-11-05 | Hoffmann La Roche | 5-(3-pyridylethyl)pyridoindole derivatives |
US3484449A (en) | 1966-05-12 | 1969-12-16 | Hoffmann La Roche | Certain substituted phenyl amino-ethylpyridine intermediates |
US3646045A (en) | 1968-09-10 | 1972-02-29 | Hoffmann La Roche | Intermediates for 5-(4-pyridylethyl)-pyridoindole derivatives |
US3502688A (en) | 1968-09-10 | 1970-03-24 | Hoffmann La Roche | 5-(4-pyridylethyl)-pyridoindole derivatives |
JPS5143863B2 (US07981874-20110719-C00313.png) | 1973-06-18 | 1976-11-25 | ||
US4754038A (en) | 1987-02-26 | 1988-06-28 | American Home Products Corporation | Carboline histamine H1 antagonists |
DK169922B1 (da) | 1988-08-02 | 1995-04-03 | Glaxo Group Ltd | Substituerede (imidazol-4-yl)methylpyrido-, og -azepino-, indolonderivater, fremgangsmåde til fremstilling deraf samt farmaceutiske præparater indeholdende derivaterne |
RU2140417C1 (ru) | 1995-10-17 | 1999-10-27 | Институт физиологически активных веществ РАН | Производные гидрированных пиридо(4,3-b)индолов, способы их получения, фармацевтическая композиция и способ лечения |
RU2106864C1 (ru) | 1995-10-23 | 1998-03-20 | Николай Серафимович Зефиров | Средство для лечения болезни альцгеймера |
DE10030375A1 (de) | 2000-06-21 | 2002-01-03 | Bayer Ag | Verwendung von MTP-Inhibitoren zur Senkung von ppTRL |
BR0211608A (pt) | 2001-08-08 | 2006-04-04 | Upjohn Co | 1h-pirido[4,3-b]indóis terapêuticos |
US7736889B2 (en) | 2003-06-10 | 2010-06-15 | The United States Of America As Represented By The Secretary Of The Navy | Fluidic force discrimination |
AP2334A (en) | 2004-12-17 | 2011-12-06 | Glenmark Pharmaceuticals Sa | Novel heterocyclic compounds useful for the treatment of inflamatory and allergic disorders. |
KR20080034171A (ko) | 2005-07-28 | 2008-04-18 | 브리스톨-마이어스 스큅 컴퍼니 | 세로토닌 수용체 효능제 및 길항제로서의 치환된테트라히드로-1h-피리도[4,3,b]인돌 |
CA2624731A1 (en) | 2005-10-04 | 2007-04-12 | Medivation, Inc. | Hydrogenated pyrido-indole compounds for the treatment of huntington's disease |
RU2338537C2 (ru) * | 2006-01-25 | 2008-11-20 | Сергей Олегович Бачурин | СРЕДСТВО ДЛЯ ЛЕЧЕНИЯ ШИЗОФРЕНИИ НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО(4,3-b)ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
JP2010504337A (ja) | 2006-09-20 | 2010-02-12 | メディベイション ニューロロジー, インコーポレイテッド | イヌの認知機能障害症候群の治療のためのディメボン(dimebon)などの水素化ピリド[4,3−b]インドール |
US20100099700A1 (en) | 2006-09-20 | 2010-04-22 | David Hung | Hydrogenated pyrido (4,3-b) indoles for treating amyotrophic lateral sclerosis (als) |
ATE549021T1 (de) | 2006-10-27 | 2012-03-15 | Medivation Neurology Inc | Kombinationstherapien zur behandlung von morbus alzheimer mit dimebon und donepezil |
RU2329044C1 (ru) | 2006-11-16 | 2008-07-20 | Андрей Александрович Иващенко | Лиганды 5-ht6 рецепторов, фармацевтическая композиция, способ ее получения и лекарственное средство |
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 |
RU2340342C2 (ru) | 2006-12-07 | 2008-12-10 | Сергей Олегович Бачурин | СРЕДСТВО ДЛЯ ЛЕЧЕНИЯ ОСТРЫХ И ХРОНИЧЕСКИХ НАРУШЕНИЙ МОЗГОВОГО КРОВООБРАЩЕНИЯ, В ТОМ ЧИСЛЕ ИНСУЛЬТА, НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО[4,3-b]ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
RU2338745C1 (ru) | 2007-03-21 | 2008-11-20 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ 2,3,4,5-ТЕТРАГИДРО-1Н-ПИРИДО[4,3-b]ИНДОЛЫ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
CA2683453C (en) * | 2007-04-05 | 2013-06-11 | Alla Chem, Llc | Substituted 2,3,4,5-tetrahydro-1h-pyrido[4,3-.beta.]indoles, methods for the production and use thereof |
RU2339637C1 (ru) | 2007-04-05 | 2008-11-27 | Андрей Александрович Иващенко | Блокаторы гистаминного рецептора для фармацевтических композиций, обладающих противоаллергическим и аутоиммунным действием |
EP2155196A1 (en) | 2007-05-25 | 2010-02-24 | Medivation Neurology, Inc. | Methods and compositions for stimulating cells |
RU2338533C1 (ru) | 2007-06-28 | 2008-11-20 | Сергей Олегович Бачурин | СРЕДСТВО, ОБЛАДАЮЩЕЕ АНКСИОЛИТИЧЕСКИМ ДЕЙСТВИЕМ, НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО(4,3-b)ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
CN101842010A (zh) | 2007-08-01 | 2010-09-22 | 梅迪维新神经学公司 | 使用抗精神病的组合治疗产品来治疗精神分裂症的方法和组合物 |
WO2009038764A1 (en) * | 2007-09-20 | 2009-03-26 | D2E, Llc | Fluoro-containing derivatives of hydrogented pyrido[4,3-b]indoles with neuroprotective and cognition enhancing properties, process for preparing, and use |
WO2009039420A1 (en) | 2007-09-21 | 2009-03-26 | Medivation Neurology, Inc. | Methods and compositions for treating neuronal death mediated ocular diseases |
RU2007139634A (ru) * | 2007-10-25 | 2009-04-27 | Сергей Олегович Бачурин (RU) | Новые тиазол-, триазол- или оксадиазол-содержащие тетрациклические соединения |
EP2236511A4 (en) | 2007-12-21 | 2011-04-13 | Alla Chem Llc | LIGANDS OF ALPHA ADRENOCEPTORS AND OF DOPAMINE, HISTAMIN, IMIDAZOLIN AND SEROTONIN RECEPTORS AND THEIR APPLICATION THEREOF |
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 |
WO2009111540A1 (en) | 2008-03-04 | 2009-09-11 | Medivation Neurology, Inc. | Methods for preparing pyridylethyl-substituted carbolines |
PE20091717A1 (es) | 2008-03-24 | 2009-11-25 | Medivation Technologies Inc | Pirido[3,4-b] indoles como moduladores de receptores de histamina |
JP5586577B2 (ja) | 2008-03-24 | 2014-09-10 | メディベイション テクノロジーズ, インコーポレイテッド | 架橋複素環化合物およびその使用 |
WO2009135091A1 (en) | 2008-04-30 | 2009-11-05 | Medivation Technologies, Inc. | Use of asenapine and related compounds for the treatment of neuronal or non-neuronal diseases or conditions |
CN101640878B (zh) | 2008-07-29 | 2011-08-31 | 华为技术有限公司 | 一种确定漫游用户终端移动性的方法及装置 |
WO2010014758A1 (en) | 2008-07-30 | 2010-02-04 | Edison Pharmaceuticals, Inc. | Use of hydrogenated pyrido[4,3-b] indoles for the treatment of oxidative stress |
AU2009308708B2 (en) | 2008-10-31 | 2015-11-19 | Medivation Technologies, Inc. | Azepino [4, 5-b] indoles and methods of use |
US8907097B2 (en) | 2008-10-31 | 2014-12-09 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles containing rigid moieties |
EP2424366B1 (en) | 2009-04-29 | 2016-02-17 | Medivation Technologies, Inc. | Pyrido [4, 3-b]indoles and methods of use |
US9255094B2 (en) * | 2009-04-29 | 2016-02-09 | Medivation Technologies, Inc. | Pyrido[4,3-B]indoles and methods of use |
WO2011014695A1 (en) | 2009-07-29 | 2011-02-03 | Medivation Technologies, Inc. | New 2,3,4,5-tetrahydro-1h-pyrido[4,3-b] indoles and methods of use |
WO2011038164A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Bridged heterocyclic compounds and methods of use |
BR112012006646A2 (pt) | 2009-09-23 | 2019-09-24 | Medivation Technologies Inc | composto, composição farmacêutica, método de tratamento de um distùrbio cognitivo, distúrbio psicótico, distúrbio mediado por neurotransmissor ou um distúrbio neuronal e kit |
WO2011038162A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Pyrido(3,4-b)indoles and methods of use |
BR112012006640A2 (pt) | 2009-09-23 | 2019-09-24 | Medivation Technologies Inc | composto, composição farmacêutica, método de tratamento de um distúrbio cognitivo, distúrbiopsocótico, distúrbio mediado por neurotransmissor ou um distúrbio neuronal e kit |
WO2011103460A1 (en) | 2010-02-18 | 2011-08-25 | Medivation Technologies, Inc. | Fused tetracyclic pyrido[4,3-b]indole and pyrido[3,4-b]ondole derivatives and methods of use |
WO2011103487A1 (en) | 2010-02-18 | 2011-08-25 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
US9040519B2 (en) | 2010-02-18 | 2015-05-26 | Medivation Technologies, Inc. | Fused tetracyclic pyrido [4,3-B] indole and pyrido [3,4-B] indole derivatives and methods of use |
US9034865B2 (en) | 2010-02-18 | 2015-05-19 | Medivation Technologies, Inc. | Pyrido [4,3-B] indole and pyrido [3,4-B] indole derivatives and methods of use |
WO2011103448A1 (en) | 2010-02-19 | 2011-08-25 | Medivation Technologies, Inc. | Methods and compositions for treating psychotic disorders using antipsychotic combination therapy |
WO2011103430A1 (en) | 2010-02-19 | 2011-08-25 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
WO2012112964A2 (en) | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | PYRIDO[4,3-b]INDOLE AND PYRIDO[3,4-b]INDOLE DERIVATIVES AND METHODS OF USE |
US9199985B2 (en) | 2011-02-18 | 2015-12-01 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
BR112013021125A2 (pt) | 2011-02-18 | 2019-09-24 | Medivation Technologies Inc | método para regular os níveis de glicose no sangue, método para aumentar a secreção da insulina ou promover a liberação da insulina na corrente sanguínea, método para tratar uma doença ou condição, método para retardar o ínicio de uma doença ou condição de doença kit, composto de composição farmacêutica |
US9434747B2 (en) | 2011-02-18 | 2016-09-06 | Medivation Technologies, Inc. | Methods of treating diabetes |
WO2014031170A1 (en) | 2012-08-22 | 2014-02-27 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
US20150315188A1 (en) | 2012-08-22 | 2015-11-05 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
-
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- 2010-04-29 JP JP2012508752A patent/JP5827943B2/ja not_active Expired - Fee Related
- 2010-04-29 BR BRPI1006608-0A patent/BRPI1006608A2/pt not_active IP Right Cessation
- 2010-04-29 CN CN201080029084.1A patent/CN102480956B/zh not_active Expired - Fee Related
- 2010-04-29 CA CA2760516A patent/CA2760516A1/en not_active Abandoned
- 2010-04-29 WO PCT/US2010/033055 patent/WO2011019417A1/en active Application Filing
- 2010-04-29 US US13/318,124 patent/US8741919B2/en not_active Expired - Fee Related
- 2010-04-29 AU AU2010282990A patent/AU2010282990B2/en not_active Ceased
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2012
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2013
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