JP2012525430A5 - - Google Patents
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- JP2012525430A5 JP2012525430A5 JP2012508751A JP2012508751A JP2012525430A5 JP 2012525430 A5 JP2012525430 A5 JP 2012525430A5 JP 2012508751 A JP2012508751 A JP 2012508751A JP 2012508751 A JP2012508751 A JP 2012508751A JP 2012525430 A5 JP2012525430 A5 JP 2012525430A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrido
- indol
- dihydro
- methyl
- salt
- 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 101
- 150000003839 salts Chemical class 0.000 claims description 77
- -1 aminocarbonylamino, aminocarbonyloxy, aminosulfonyl Chemical group 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 36
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 16
- 102000000543 Histamine Receptors Human genes 0.000 claims description 12
- 108010002059 Histamine Receptors Proteins 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- ALALGYYKKWHHFT-UHFFFAOYSA-N 1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-ylpropan-2-ol Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(O)C1=CC=NC=C1 ALALGYYKKWHHFT-UHFFFAOYSA-N 0.000 claims description 4
- NHBJEVLRXOFTHJ-UHFFFAOYSA-N 1-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-(4-fluorophenyl)hexan-2-ol Chemical compound C1=2CCN(C)CC=2C2=CC(Cl)=CC=C2N1CC(O)(CCCC)C1=CC=C(F)C=C1 NHBJEVLRXOFTHJ-UHFFFAOYSA-N 0.000 claims description 4
- PXEPSGXCVODYGD-UHFFFAOYSA-N 2-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-pyridin-4-ylethanol Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(O)C1=CC=NC=C1 PXEPSGXCVODYGD-UHFFFAOYSA-N 0.000 claims description 4
- FFPDVUKDLHXYPS-UHFFFAOYSA-N 2-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-pyridin-4-ylethanol Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(O)C1=CC=NC=C1 FFPDVUKDLHXYPS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- MXLLWYGJUMMXIK-UHFFFAOYSA-N 1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-(4-methoxyphenyl)propan-2-ol Chemical compound C1=CC(OC)=CC=C1C(C)(O)CN1C2=CC=C(C)C=C2C2=C1CCN(C)C2 MXLLWYGJUMMXIK-UHFFFAOYSA-N 0.000 claims description 3
- IRLRNWRMIBNDMJ-UHFFFAOYSA-N 1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-pyrazin-2-ylpropan-2-ol Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(O)C1=CN=CC=N1 IRLRNWRMIBNDMJ-UHFFFAOYSA-N 0.000 claims description 3
- FHGOXDWNWJQYGK-UHFFFAOYSA-N 1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-pyrimidin-4-ylpropan-2-ol Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(O)C1=CC=NC=N1 FHGOXDWNWJQYGK-UHFFFAOYSA-N 0.000 claims description 3
- IDQXHUHLSUEWOD-UHFFFAOYSA-N 1-(2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-ylpropan-2-ol Chemical compound C1N(C)CCC2=C1C1=CC=CC=C1N2CC(C)(O)C1=CC=NC=C1 IDQXHUHLSUEWOD-UHFFFAOYSA-N 0.000 claims description 3
- UYCVKKGODKBIIQ-UHFFFAOYSA-N 1-(7,8-dichloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-ylpropan-2-ol Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=C(Cl)C=C1N2CC(C)(O)C1=CC=NC=C1 UYCVKKGODKBIIQ-UHFFFAOYSA-N 0.000 claims description 3
- GPDOQWMVEXTBOT-UHFFFAOYSA-N 1-(8,9-dichloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-ylpropan-2-ol Chemical compound C1N(C)CCC2=C1C1=C(Cl)C(Cl)=CC=C1N2CC(C)(O)C1=CC=NC=C1 GPDOQWMVEXTBOT-UHFFFAOYSA-N 0.000 claims description 3
- PTUZCMGIQGFPDX-UHFFFAOYSA-N 1-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-(3-fluoro-4-methoxyphenyl)propan-2-ol Chemical compound C1=C(F)C(OC)=CC=C1C(C)(O)CN1C2=CC=C(Cl)C=C2C2=C1CCN(C)C2 PTUZCMGIQGFPDX-UHFFFAOYSA-N 0.000 claims description 3
- LOLFYIWPYGTMJO-UHFFFAOYSA-N 2-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-(4-fluorophenyl)ethanol Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(O)C1=CC=C(F)C=C1 LOLFYIWPYGTMJO-UHFFFAOYSA-N 0.000 claims description 3
- FKAGVDSAIOJBEG-UHFFFAOYSA-N 4-[1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-hydroxypropan-2-yl]phenol Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(O)C1=CC=C(O)C=C1 FKAGVDSAIOJBEG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 3
- IPFQISBRAHCMTC-QFIPXVFZSA-N (2r)-1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-ylbutan-2-ol Chemical compound C1([C@@](O)(CN2C3=CC=C(C)C=C3C=3CN(C)CCC=32)CC)=CC=NC=C1 IPFQISBRAHCMTC-QFIPXVFZSA-N 0.000 claims description 2
- NHBJEVLRXOFTHJ-DEOSSOPVSA-N (2r)-1-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-(4-fluorophenyl)hexan-2-ol Chemical compound C1([C@@](O)(CN2C3=CC=C(Cl)C=C3C=3CN(C)CCC=32)CCCC)=CC=C(F)C=C1 NHBJEVLRXOFTHJ-DEOSSOPVSA-N 0.000 claims description 2
- IPFQISBRAHCMTC-JOCHJYFZSA-N (2s)-1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-ylbutan-2-ol Chemical compound C1([C@](O)(CN2C3=CC=C(C)C=C3C=3CN(C)CCC=32)CC)=CC=NC=C1 IPFQISBRAHCMTC-JOCHJYFZSA-N 0.000 claims description 2
- WMQWGFBKVULIPU-UHFFFAOYSA-N 1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-(4-fluorophenyl)butan-2-ol Chemical compound C1=2CCN(C)CC=2C2=CC(C)=CC=C2N1CC(O)(CC)C1=CC=C(F)C=C1 WMQWGFBKVULIPU-UHFFFAOYSA-N 0.000 claims description 2
- IPFQISBRAHCMTC-UHFFFAOYSA-N 1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-ylbutan-2-ol Chemical compound C1=2CCN(C)CC=2C2=CC(C)=CC=C2N1CC(O)(CC)C1=CC=NC=C1 IPFQISBRAHCMTC-UHFFFAOYSA-N 0.000 claims description 2
- IABZWPDEAGALDE-UHFFFAOYSA-N 1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-methyl-2-pyridin-4-ylbutan-2-ol Chemical compound C1=2CCN(C)CC=2C2=CC(C)=CC=C2N1CC(O)(C(C)C)C1=CC=NC=C1 IABZWPDEAGALDE-UHFFFAOYSA-N 0.000 claims description 2
- RAYAGSPPADIRJE-UHFFFAOYSA-N 1-(2-cyclopropyl-8-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-(2-methylpyridin-4-yl)propan-2-ol Chemical compound C1=2CCN(C3CC3)CC=2C2=CC(C)=CC=C2N1CC(C)(O)C1=CC=NC(C)=C1 RAYAGSPPADIRJE-UHFFFAOYSA-N 0.000 claims description 2
- JHNYSIBNEXURAE-UHFFFAOYSA-N 1-(2-ethyl-8-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-(4-fluorophenyl)propan-2-ol Chemical compound C1N(CC)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(O)C1=CC=C(F)C=C1 JHNYSIBNEXURAE-UHFFFAOYSA-N 0.000 claims description 2
- YJRGOONEJAQERR-UHFFFAOYSA-N 1-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-3-methyl-2-pyridin-4-ylbutan-2-ol Chemical compound C1=2CCN(C)CC=2C2=CC(Cl)=CC=C2N1CC(O)(C(C)C)C1=CC=NC=C1 YJRGOONEJAQERR-UHFFFAOYSA-N 0.000 claims description 2
- UEORSAWMQSHTKE-UHFFFAOYSA-N 1-[8-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]-2-pyridin-4-ylpropan-2-ol Chemical compound C1=2CCN(CC(F)(F)F)CC=2C2=CC(C)=CC=C2N1CC(C)(O)C1=CC=NC=C1 UEORSAWMQSHTKE-UHFFFAOYSA-N 0.000 claims description 2
- RWJZQZVBGBCVFN-UHFFFAOYSA-N 1-cyclohexyl-2-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-(4-fluorophenyl)ethanol Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(O)(C=1C=CC(F)=CC=1)C1CCCCC1 RWJZQZVBGBCVFN-UHFFFAOYSA-N 0.000 claims description 2
- KJZCUPMXUFTZLV-UHFFFAOYSA-N 2,3,8-trimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)C(C)CC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 KJZCUPMXUFTZLV-UHFFFAOYSA-N 0.000 claims description 2
- HMYDVYGSXLBJKK-UHFFFAOYSA-N 2,3,8-trimethyl-5-[2-(6-methylpyridin-3-yl)propyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1=2CC(C)N(C)CC=2C2=CC(C)=CC=C2N1CC(C)C1=CC=C(C)N=C1 HMYDVYGSXLBJKK-UHFFFAOYSA-N 0.000 claims description 2
- VDNUKKJGOKIGOK-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)propan-2-ol Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(C)(O)C1=CC=C(F)C=C1F VDNUKKJGOKIGOK-UHFFFAOYSA-N 0.000 claims description 2
- NSYXDDRZUMDVIW-UHFFFAOYSA-N 2-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-(4-fluorophenyl)ethanone Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(=O)C1=CC=C(F)C=C1 NSYXDDRZUMDVIW-UHFFFAOYSA-N 0.000 claims description 2
- FWIKWZGVKPJVNJ-UHFFFAOYSA-N 2-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-phenylethanone Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CC(=O)C1=CC=CC=C1 FWIKWZGVKPJVNJ-UHFFFAOYSA-N 0.000 claims description 2
- MKKXDTDAJBNQFR-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(8-chloro-2-propan-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)propan-2-ol Chemical compound C1N(C(C)C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(C)(O)C1=CC=C(Cl)C=C1 MKKXDTDAJBNQFR-UHFFFAOYSA-N 0.000 claims description 2
- VPYSJGVLDQLIDR-UHFFFAOYSA-N 2-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-(4-chlorophenyl)ethanone Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(=O)C1=CC=C(Cl)C=C1 VPYSJGVLDQLIDR-UHFFFAOYSA-N 0.000 claims description 2
- OVFFBWXBLFAZQI-UHFFFAOYSA-N 2-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-(4-fluorophenyl)ethanone Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(=O)C1=CC=C(F)C=C1 OVFFBWXBLFAZQI-UHFFFAOYSA-N 0.000 claims description 2
- KZSRTBKZNFOLNX-UHFFFAOYSA-N 2-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-cyclobutyl-1-(4-fluorophenyl)ethanol Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(O)(C=1C=CC(F)=CC=1)C1CCC1 KZSRTBKZNFOLNX-UHFFFAOYSA-N 0.000 claims description 2
- ZPVALAHVRBXBDR-UHFFFAOYSA-N 2-(8-chloro-2-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-1-phenylethanone Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CC(=O)C1=CC=CC=C1 ZPVALAHVRBXBDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- RWZMVPSBSUJAPW-UHFFFAOYSA-N 3-[5-[2-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)ethyl]pyridin-2-yl]propan-1-amine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(CCCN)N=C1 RWZMVPSBSUJAPW-UHFFFAOYSA-N 0.000 claims description 2
- CIFFOIBAEUIEQJ-UHFFFAOYSA-N 3-[8-methyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-2-yl]propan-1-ol Chemical compound C1=2CCN(CCCO)CC=2C2=CC(C)=CC=C2N1CCC1=CC=C(C)N=C1 CIFFOIBAEUIEQJ-UHFFFAOYSA-N 0.000 claims description 2
- MZWRHCBZOUSXRZ-UHFFFAOYSA-N 3-[8-methyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-2-yl]propanenitrile Chemical compound C1=2CCN(CCC#N)CC=2C2=CC(C)=CC=C2N1CCC1=CC=C(C)N=C1 MZWRHCBZOUSXRZ-UHFFFAOYSA-N 0.000 claims description 2
- XBVOPMXREOSTGO-UHFFFAOYSA-N 4-[8-methyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-2-yl]butan-1-ol Chemical compound C1=2CCN(CCCCO)CC=2C2=CC(C)=CC=C2N1CCC1=CC=C(C)N=C1 XBVOPMXREOSTGO-UHFFFAOYSA-N 0.000 claims description 2
- FJLRAIYQDBDRLE-UHFFFAOYSA-N 8-chloro-2,3-dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)C(C)CC2=C1C1=CC(Cl)=CC=C1N2CCC1=CC=C(C)N=C1 FJLRAIYQDBDRLE-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000005102 carbonylalkoxy group Chemical group 0.000 claims description 2
- 125000005589 carbonylalkylenealkoxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 230000019771 cognition Effects 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- WMQWGFBKVULIPU-HSZRJFAPSA-N (2s)-1-(2,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)-2-(4-fluorophenyl)butan-2-ol Chemical compound C1([C@](O)(CN2C3=CC=C(C)C=C3C=3CN(C)CCC=32)CC)=CC=C(F)C=C1 WMQWGFBKVULIPU-HSZRJFAPSA-N 0.000 claims 1
- LMOPRCLIZJULDB-UHFFFAOYSA-N 1-(2-fluorophenyl)hexan-2-ol Chemical compound CCCCC(O)CC1=CC=CC=C1F LMOPRCLIZJULDB-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 238000003556 assay Methods 0.000 description 12
- 102000015554 Dopamine receptor Human genes 0.000 description 10
- 108050004812 Dopamine receptor Proteins 0.000 description 10
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 8
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 8
- 108060003345 Adrenergic Receptor Proteins 0.000 description 6
- 102000017910 Adrenergic receptor Human genes 0.000 description 6
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| US9193728B2 (en) | 2010-02-18 | 2015-11-24 | Medivation Technologies, Inc. | Fused tetracyclic 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 |
| US9187471B2 (en) | 2010-02-19 | 2015-11-17 | 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 |
| US20140155384A1 (en) | 2011-02-18 | 2014-06-05 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| CA2829045A1 (en) | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| WO2012112965A1 (en) | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| WO2014031167A1 (en) | 2012-08-22 | 2014-02-27 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| 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 |
| WO2014031125A1 (en) | 2012-08-24 | 2014-02-27 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
-
2010
- 2010-04-29 WO PCT/US2010/033053 patent/WO2010127177A1/en not_active Ceased
- 2010-04-29 AU AU2010242910A patent/AU2010242910B2/en not_active Ceased
- 2010-04-29 JP JP2012508751A patent/JP5711725B2/ja not_active Expired - Fee Related
- 2010-04-29 BR BRPI1006602A patent/BRPI1006602A2/pt not_active IP Right Cessation
- 2010-04-29 CN CN201080028795.7A patent/CN102480955B/zh not_active Expired - Fee Related
- 2010-04-29 US US13/318,123 patent/US9255094B2/en not_active Expired - Fee Related
- 2010-04-29 EP EP10770380A patent/EP2424364A4/en not_active Withdrawn
- 2010-04-29 CA CA2760541A patent/CA2760541A1/en not_active Abandoned
-
2013
- 2013-03-08 US US13/791,796 patent/US20130190328A1/en not_active Abandoned
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