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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Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| CL2009000725A1 (es) | 2008-03-24 | 2009-05-29 | Medivation Technologies Inc | Compuestos derivados de heterociclos con uniones puente sustituidos, moduladores de receptores adrenergicos, de serotonina, de dopamina y de histaminas; composicion farmaceutica; kit farmaceutico; y su uso en el tratamiento del trastorno cognitivo y trastorno psicotico. |
| WO2009120717A2 (en) | 2008-03-24 | 2009-10-01 | Medivation Technologies, Inc. | Pyrido [3, 4-b] indoles and methods of use |
| AU2009308708B2 (en) | 2008-10-31 | 2015-11-19 | Medivation Technologies, Inc. | Azepino [4, 5-b] indoles and methods of use |
| TWI477503B (zh) * | 2008-10-31 | 2015-03-21 | Medivation Technologies Inc | 含有剛性部分之吡啶并〔４，３－ｂ〕吲哚 |
| BRPI1008020A2 (pt) | 2009-02-11 | 2016-03-15 | Sunovion Pharmaceuticals Inc | antagonistas e agonistas inversos h3 da histamina e métodos de uso dos mesmos |
| EP2424366B1 (en) * | 2009-04-29 | 2016-02-17 | Medivation Technologies, Inc. | Pyrido [4, 3-b]indoles and methods of use |
| CA2760541A1 (en) | 2009-04-29 | 2010-11-04 | Medivation Technologies, Inc. | 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 |
| CA2775328A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles and methods of use |
| US9079904B2 (en) | 2009-09-23 | 2015-07-14 | Medivation Technologies, Inc. | Pyrido[3,4-B]indoles 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 |
| WO2011103433A1 (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 |
| 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 |
| 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 |
| US9056855B2 (en) * | 2010-10-28 | 2015-06-16 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| US9434747B2 (en) | 2011-02-18 | 2016-09-06 | Medivation Technologies, Inc. | Methods of treating diabetes |
| US8791132B2 (en) * | 2011-02-18 | 2014-07-29 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| 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 |
| WO2012112963A1 (en) | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| RU2490268C2 (ru) * | 2011-11-10 | 2013-08-20 | Федеральное Государственное Бюджетное Учреждение Науки Институт Физиологически Активных Веществ Российской Академии Наук (Ифав Ран) | ХЛОРГИДРАТЫ ФТОРСОДЕРЖАЩИХ ЗАМЕЩЕННЫХ 5-[2-(ПИРИД-3-ИЛ)-ЭТИЛ]-2,3,4,5-ТЕТРАГИДРО-1Н-ПИРИДО[4,3-b]ИНДОЛОВ, В КАЧЕСТВЕ СРЕДСТВ СНИЖЕНИЯ НЕКОНТРОЛИРУЕМОЙ АГРЕГАЦИИ БЕЛКОВ В НЕРВНОЙ СИСТЕМЕ, ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ИХ ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| WO2013078544A1 (en) * | 2011-11-29 | 2013-06-06 | Beta Pharma Canada Inc. | Heterocyclic amides compounds which are hdac6 inhibitors and used as anti-tumoral agents |
| 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 |
| WO2014031165A1 (en) * | 2012-08-22 | 2014-02-27 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| US10092550B2 (en) | 2014-10-21 | 2018-10-09 | Ions Pharmaceutical S.À R.L. | Therapeutic compositions containing curcumin, harmine, and isovanillin components, and methods of use thereof |
| US9907786B2 (en) | 2014-10-21 | 2018-03-06 | Ions Pharmaceutical S.À R.L. | Therapeutic compositions containing harmine and isovanillin components, and methods of use thereof |
| US12129265B2 (en) | 2020-07-21 | 2024-10-29 | Ankh Life Sciences Limited | Therapeutic agents and uses thereof |
| KR20230171634A (ko) * | 2022-06-14 | 2023-12-21 | 주식회사 레고켐 바이오사이언스 | 엑토뉴클레오티드 피로포스파타아제 포스포디에스터라아제-1 저해 화합물 및 이를 함유하는 약제학적 조성물 |
Family Cites Families (67)
| 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 |
| US3502688A (en) | 1968-09-10 | 1970-03-24 | Hoffmann La Roche | 5-(4-pyridylethyl)-pyridoindole derivatives |
| US3646045A (en) | 1968-09-10 | 1972-02-29 | Hoffmann La Roche | Intermediates for 5-(4-pyridylethyl)-pyridoindole derivatives |
| JPS5143863B2 (https=) | 1973-06-18 | 1976-11-25 | ||
| US4754038A (en) | 1987-02-26 | 1988-06-28 | American Home Products Corporation | Carboline histamine H1 antagonists |
| DE68926553T2 (de) | 1988-08-02 | 1996-10-17 | Glaxo Group Ltd., London | Lactamderivate |
| 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 |
| CA2453537A1 (en) * | 2001-08-08 | 2003-02-20 | Pharmacia & Upjohn Company | Therapeutic 1h-pyrido¬4,3-b|indoles |
| RU2283108C2 (ru) | 2003-12-08 | 2006-09-10 | Сергей Олегович Бачурин | ГЕРОПРОТЕКТОР НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО(4,3-b) ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| BRPI0517211B8 (pt) | 2004-12-17 | 2021-05-25 | Glenmark Pharmaceuticals Sa | composto, composição farmacêutica e seu uso. |
| KR20080034171A (ko) * | 2005-07-28 | 2008-04-18 | 브리스톨-마이어스 스큅 컴퍼니 | 세로토닌 수용체 효능제 및 길항제로서의 치환된테트라히드로-1ｈ-피리도[4,3,ｂ]인돌 |
| US20070117834A1 (en) | 2005-10-04 | 2007-05-24 | David Hung | Methods and compositions for treating 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 |
| EP2066322A2 (en) | 2006-09-20 | 2009-06-10 | Medivation Neurology, Inc. | Hydrogenated pyrido [4,3-b] indoles such as dimebon for treating canine cognitive dysfunction syndrome |
| JP2010504338A (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 | 筋萎縮性側索硬化症（ＡＬＳ）の治療のための水素化ピリド［４，３−ｂ］インドール |
| WO2008051599A2 (en) | 2006-10-27 | 2008-05-02 | Medivation Neurology, Inc. | Combination therapies for treating alzheimer's disease using i. a. dimebon and dolepezil |
| 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 |
| RU2339637C1 (ru) | 2007-04-05 | 2008-11-27 | Андрей Александрович Иващенко | Блокаторы гистаминного рецептора для фармацевтических композиций, обладающих противоаллергическим и аутоиммунным действием |
| UA98324C2 (ru) | 2007-04-05 | 2012-05-10 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ 2,3,4,5-ТЕТРАГИДРО-1H-ПИРИДО[4,3-b]ИНДОЛЫ, СПОСОБ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
| MX2009012788A (es) | 2007-05-25 | 2010-01-14 | Medivation Neurology Inc | Metodos y composiciones para estimular celulas. |
| 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 |
| MX2010001218A (es) * | 2007-08-01 | 2010-04-07 | Medivation Neurology Inc | Metodos y composiciones para tratamiento contra esquizofrenia mediante uso de terapia combinada de agentes antipsicoticos. |
| AU2008302751A1 (en) | 2007-09-20 | 2009-03-26 | D2E, Llc | Fluoro-containing derivatives of hydrogenated 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 |
| 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 |
| 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 |
| CL2009000725A1 (es) | 2008-03-24 | 2009-05-29 | Medivation Technologies Inc | Compuestos derivados de heterociclos con uniones puente sustituidos, moduladores de receptores adrenergicos, de serotonina, de dopamina y de histaminas; composicion farmaceutica; kit farmaceutico; y su uso en el tratamiento del trastorno cognitivo y trastorno psicotico. |
| WO2009120717A2 (en) | 2008-03-24 | 2009-10-01 | Medivation Technologies, Inc. | Pyrido [3, 4-b] indoles and methods of use |
| 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 |
| 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 |
| WO2010036998A2 (en) | 2008-09-29 | 2010-04-01 | Abbott Laboratories | Indole and indoline derivatives and methods of use thereof |
| US9625475B2 (en) | 2008-09-29 | 2017-04-18 | Abbvie Inc. | Indole and indoline derivatives and methods of use thereof |
| TWI477503B (zh) | 2008-10-31 | 2015-03-21 | Medivation Technologies Inc | 含有剛性部分之吡啶并〔４，３－ｂ〕吲哚 |
| AU2009308708B2 (en) | 2008-10-31 | 2015-11-19 | Medivation Technologies, Inc. | Azepino [4, 5-b] indoles and methods of use |
| 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 |
| CA2748813C (en) | 2009-01-09 | 2018-07-10 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| EP2424366B1 (en) | 2009-04-29 | 2016-02-17 | Medivation Technologies, Inc. | Pyrido [4, 3-b]indoles and methods of use |
| CA2760541A1 (en) | 2009-04-29 | 2010-11-04 | Medivation Technologies, Inc. | Pyrido[4,3-b] indoles and methods of use |
| WO2011008312A2 (en) | 2009-07-14 | 2011-01-20 | Abbott Laboratories | Indole and indoline derivatives and methods of use thereof |
| 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 |
| CN102711467A (zh) | 2009-09-23 | 2012-10-03 | 梅迪维新技术公司 | 吡啶并[3,4-b]吲哚类及使用方法 |
| WO2011038164A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Bridged heterocyclic compounds and methods of use |
| CA2775328A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles and methods of use |
| US9079904B2 (en) | 2009-09-23 | 2015-07-14 | Medivation Technologies, Inc. | Pyrido[3,4-B]indoles and methods of use |
| WO2011103433A1 (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 |
| 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 |
| 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 |
| 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 |
| WO2011103448A1 (en) | 2010-02-19 | 2011-08-25 | Medivation Technologies, Inc. | Methods and compositions for treating psychotic disorders using antipsychotic combination therapy |
| CA2804161A1 (en) | 2010-07-07 | 2012-01-12 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| WO2012112963A1 (en) | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| US9434747B2 (en) | 2011-02-18 | 2016-09-06 | Medivation Technologies, Inc. | Methods of treating diabetes |
| 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 |
| US8791132B2 (en) | 2011-02-18 | 2014-07-29 | 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 |
| WO2014031165A1 (en) | 2012-08-22 | 2014-02-27 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| CN108329253A (zh) | 2012-08-24 | 2018-07-27 | 得克萨斯州大学系统董事会 | 前神经原性化合物 |
-
2010
- 2010-04-29 CA CA2760541A patent/CA2760541A1/en not_active Abandoned
- 2010-04-29 AU AU2010242910A patent/AU2010242910B2/en not_active Ceased
- 2010-04-29 BR BRPI1006602A patent/BRPI1006602A2/pt not_active IP Right Cessation
- 2010-04-29 US US13/318,123 patent/US9255094B2/en not_active Expired - Fee Related
- 2010-04-29 JP JP2012508751A patent/JP5711725B2/ja not_active Expired - Fee Related
- 2010-04-29 CN CN201080028795.7A patent/CN102480955B/zh not_active Expired - Fee Related
- 2010-04-29 EP EP10770380A patent/EP2424364A4/en not_active Withdrawn
- 2010-04-29 WO PCT/US2010/033053 patent/WO2010127177A1/en not_active Ceased
-
2013
- 2013-03-08 US US13/791,796 patent/US20130190328A1/en not_active Abandoned
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