JP2008534496A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008534496A5 JP2008534496A5 JP2008502944A JP2008502944A JP2008534496A5 JP 2008534496 A5 JP2008534496 A5 JP 2008534496A5 JP 2008502944 A JP2008502944 A JP 2008502944A JP 2008502944 A JP2008502944 A JP 2008502944A JP 2008534496 A5 JP2008534496 A5 JP 2008534496A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- alkyl
- pyrido
- carbonyl
- indole
- 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.)
- Abandoned
Links
- 125000000217 alkyl group Chemical group 0.000 claims 235
- -1 methoxy, ethoxy Chemical group 0.000 claims 131
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 27
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 20
- 125000001072 heteroaryl group Chemical group 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 2
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 2
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- BAXKVCDKRUGYBB-UHFFFAOYSA-N (2-cyclobutyl-5-ethylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4-hydroxypiperidin-1-yl)methanone Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(C4CCC4)CC=3C2=CC=1C(=O)N1CCC(O)CC1 BAXKVCDKRUGYBB-UHFFFAOYSA-N 0.000 claims 1
- UZZMNKDKHIEBRE-UHFFFAOYSA-N (2-cyclobutyl-5-ethylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(C4CCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 UZZMNKDKHIEBRE-UHFFFAOYSA-N 0.000 claims 1
- HEFJJXPUDGTDOQ-UHFFFAOYSA-N (2-cyclobutyl-5-ethylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-[4-(hydroxymethyl)piperidin-1-yl]methanone Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(C4CCC4)CC=3C2=CC=1C(=O)N1CCC(CO)CC1 HEFJJXPUDGTDOQ-UHFFFAOYSA-N 0.000 claims 1
- CGCOYHXVKNETLI-UHFFFAOYSA-N (2-cyclobutyl-5-methylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCC2)S(C)(=O)=O)C3=C1 CGCOYHXVKNETLI-UHFFFAOYSA-N 0.000 claims 1
- NQVZYJPSQLRLKC-UHFFFAOYSA-N (2-cyclopentyl-1,3,4,5-tetrahydropyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(NC2=C3CN(CC2)C2CCCC2)C3=C1 NQVZYJPSQLRLKC-UHFFFAOYSA-N 0.000 claims 1
- TVKWKGUKDRRICW-UHFFFAOYSA-N (2-cyclopentyl-5-ethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(CC)C=3CCN(C4CCCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 TVKWKGUKDRRICW-UHFFFAOYSA-N 0.000 claims 1
- BZYPOSYJBZSSOY-UHFFFAOYSA-N (2-cyclopentyl-5-ethylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(C4CCCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 BZYPOSYJBZSSOY-UHFFFAOYSA-N 0.000 claims 1
- UCJRHXRUVGNGBQ-UHFFFAOYSA-N (2-cyclopentyl-5-imidazol-1-ylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCCC2)S(=O)(=O)N2C=NC=C2)C3=C1 UCJRHXRUVGNGBQ-UHFFFAOYSA-N 0.000 claims 1
- XDAZKNRNAJTBKN-UHFFFAOYSA-N (2-cyclopentyl-5-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4,4-difluoropiperidin-1-yl)methanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCCC4)CC=3C2=CC=1C(=O)N1CCC(F)(F)CC1 XDAZKNRNAJTBKN-UHFFFAOYSA-N 0.000 claims 1
- AMHQJYVBDKPZSA-UHFFFAOYSA-N (2-cyclopentyl-5-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C)C2=C3CN(CC2)C2CCCC2)C3=C1 AMHQJYVBDKPZSA-UHFFFAOYSA-N 0.000 claims 1
- MPUHRMVUUZAIMH-UHFFFAOYSA-N (2-cyclopentyl-5-methylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCCC2)S(C)(=O)=O)C3=C1 MPUHRMVUUZAIMH-UHFFFAOYSA-N 0.000 claims 1
- PUDOYHVREJTDBQ-UHFFFAOYSA-N (2-cyclopentyl-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(CCC)C=3CCN(C4CCCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 PUDOYHVREJTDBQ-UHFFFAOYSA-N 0.000 claims 1
- HWEKJGHXKXPACQ-UHFFFAOYSA-N (4,4-difluoropiperidin-1-yl)-[5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(F)(F)CC1 HWEKJGHXKXPACQ-UHFFFAOYSA-N 0.000 claims 1
- NSGOQJGVYWSOGC-UHFFFAOYSA-N (4,4-difluoropiperidin-1-yl)-[5-methyl-2-(oxolan-3-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(C)C=3CCN(C4COCC4)CC=3C2=CC=1C(=O)N1CCC(F)(F)CC1 NSGOQJGVYWSOGC-UHFFFAOYSA-N 0.000 claims 1
- AQBOFTWRMLZDBS-UHFFFAOYSA-N (4,4-dimethylpiperidin-1-yl)-[5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C)(C)CC1 AQBOFTWRMLZDBS-UHFFFAOYSA-N 0.000 claims 1
- LFQBUARMCBNNME-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(O)CC1 LFQBUARMCBNNME-UHFFFAOYSA-N 0.000 claims 1
- ORNLNZUOLVBBSU-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-(2-piperidin-4-yl-5-prop-2-enyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=C)C2=C3CN(CC2)C2CCNCC2)C3=C1 ORNLNZUOLVBBSU-UHFFFAOYSA-N 0.000 claims 1
- GENVWGFKMWRWGX-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-(2-propan-2-yl-1,3,4,5-tetrahydropyrido[4,3-b]indol-8-yl)methanone Chemical compound C1=C2C=3CN(C(C)C)CCC=3NC2=CC=C1C(=O)N1CCC(C)CC1 GENVWGFKMWRWGX-UHFFFAOYSA-N 0.000 claims 1
- QDCQXJDWHGCBHR-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-(2-propan-2-yl-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)methanone Chemical compound C=1C=C2N(CCC)C=3CCN(C(C)C)CC=3C2=CC=1C(=O)N1CCC(C)CC1 QDCQXJDWHGCBHR-UHFFFAOYSA-N 0.000 claims 1
- QEZXZSYRSPZABJ-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-(5-pentyl-2-propan-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)methanone Chemical compound C=1C=C2N(CCCCC)C=3CCN(C(C)C)CC=3C2=CC=1C(=O)N1CCC(C)CC1 QEZXZSYRSPZABJ-UHFFFAOYSA-N 0.000 claims 1
- XRNFCSLZGJJJPC-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-(5-propyl-2-pyridin-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)methanone Chemical compound C=1C=C2N(CCC)C=3CCN(C=4N=CC=CC=4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 XRNFCSLZGJJJPC-UHFFFAOYSA-N 0.000 claims 1
- WNCDFELRTFXLNY-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[2-(oxan-4-yl)-5-(pyridin-2-ylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=2N=CC=CC=2)C2=C3CN(CC2)C2CCOCC2)C3=C1 WNCDFELRTFXLNY-UHFFFAOYSA-N 0.000 claims 1
- JLYURUXNAAKJAD-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[2-(oxan-4-yl)-5-prop-2-enyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=C)C2=C3CN(CC2)C2CCOCC2)C3=C1 JLYURUXNAAKJAD-UHFFFAOYSA-N 0.000 claims 1
- XKSUFUUEUFNEJX-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[2-(oxan-4-yl)-5-propan-2-ylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(S(=O)(=O)C(C)C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 XKSUFUUEUFNEJX-UHFFFAOYSA-N 0.000 claims 1
- LEYYJOBTMJQHCX-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[2-(oxan-4-yl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(CCC)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 LEYYJOBTMJQHCX-UHFFFAOYSA-N 0.000 claims 1
- LCLHWAFOYICJIC-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[2-(oxan-4-yl)-5-propylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(S(=O)(=O)CCC)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 LCLHWAFOYICJIC-UHFFFAOYSA-N 0.000 claims 1
- KJGMABJBFGRVGD-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[2-(oxan-4-ylmethyl)-5-prop-2-enyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=C)C2=C3CN(CC4CCOCC4)CC2)C3=C1 KJGMABJBFGRVGD-UHFFFAOYSA-N 0.000 claims 1
- ZZNUMTXHWKDNJV-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[2-(oxolan-3-yl)-5-prop-2-enyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=C)C2=C3CN(CC2)C2COCC2)C3=C1 ZZNUMTXHWKDNJV-UHFFFAOYSA-N 0.000 claims 1
- WQKRVODUOZJARR-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[2-(oxolan-3-yl)-5-propylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(S(=O)(=O)CCC)C=3CCN(C4COCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 WQKRVODUOZJARR-UHFFFAOYSA-N 0.000 claims 1
- HSPRONAVKPLBTP-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[2-(oxolan-3-ylmethyl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCC)C=2CCN1CC1CCOC1 HSPRONAVKPLBTP-UHFFFAOYSA-N 0.000 claims 1
- MNJQTTGWERHCJH-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[5-(4-nitrophenyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCOCC2)C=2C=CC(=CC=2)[N+]([O-])=O)C3=C1 MNJQTTGWERHCJH-UHFFFAOYSA-N 0.000 claims 1
- GPBJSKKOWXKACF-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[5-(morpholine-4-carbonyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C(=O)N2CCOCC2)C2=C3CN(CC2)C2CCOCC2)C3=C1 GPBJSKKOWXKACF-UHFFFAOYSA-N 0.000 claims 1
- XUQWJBJECUXYDA-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[5-methylsulfonyl-2-(3,3,3-trifluoropropyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CCC(F)(F)F)CC2)S(C)(=O)=O)C3=C1 XUQWJBJECUXYDA-UHFFFAOYSA-N 0.000 claims 1
- GZBNSNLOUUIGBF-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[5-methylsulfonyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCOCC2)S(C)(=O)=O)C3=C1 GZBNSNLOUUIGBF-UHFFFAOYSA-N 0.000 claims 1
- JGBJMAXYYWJANQ-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[5-propyl-2-(2,3,4,5-tetrahydropyridin-6-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(CCC)C=3CCN(C=4CCCCN=4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 JGBJMAXYYWJANQ-UHFFFAOYSA-N 0.000 claims 1
- KGDCOHTYENZVQV-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[5-propyl-2-(3,3,3-trifluoropropyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(CCC)C=3CCN(CCC(F)(F)F)CC=3C2=CC=1C(=O)N1CCC(C)CC1 KGDCOHTYENZVQV-UHFFFAOYSA-N 0.000 claims 1
- KKQXADSDISBOJZ-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[5-propylsulfonyl-2-(3,3,3-trifluoropropyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(S(=O)(=O)CCC)C=3CCN(CCC(F)(F)F)CC=3C2=CC=1C(=O)N1CCC(C)CC1 KKQXADSDISBOJZ-UHFFFAOYSA-N 0.000 claims 1
- MSMSUUMPTDDUPS-UHFFFAOYSA-N (4-tert-butylpiperidin-1-yl)-[5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C(C)(C)C)CC1 MSMSUUMPTDDUPS-UHFFFAOYSA-N 0.000 claims 1
- XXTCWHWLUCBCRL-UHFFFAOYSA-N (5-benzyl-2-propan-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone Chemical compound C1N(C(C)C)CCC2=C1C1=CC(C(=O)N3CCC(C)CC3)=CC=C1N2CC1=CC=CC=C1 XXTCWHWLUCBCRL-UHFFFAOYSA-N 0.000 claims 1
- BMHIBCNWAACRRU-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decan-8-yl-[5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N(CC1)CCC21OCCO2 BMHIBCNWAACRRU-UHFFFAOYSA-N 0.000 claims 1
- ZBPSHEAJVGPDFK-UHFFFAOYSA-N 1-(2-cyclopentyl-5-propyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-8-yl)-3-ethylurea Chemical compound C1C2C3=CC(NC(=O)NCC)=CC=C3N(CCC)C2CCN1C1CCCC1 ZBPSHEAJVGPDFK-UHFFFAOYSA-N 0.000 claims 1
- QHQBQJWYZPQSBA-UHFFFAOYSA-N 1-(2-cyclopentyl-5-propyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-8-yl)-3-phenylurea Chemical compound C=1C=C2N(CCC)C3CCN(C4CCCC4)CC3C2=CC=1NC(=O)NC1=CC=CC=C1 QHQBQJWYZPQSBA-UHFFFAOYSA-N 0.000 claims 1
- JWOQQUODEBPMME-UHFFFAOYSA-N 1-[2-cyclobutyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]butan-1-one Chemical compound C=1C=C2N(C(=O)CCC)C=3CCN(C4CCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 JWOQQUODEBPMME-UHFFFAOYSA-N 0.000 claims 1
- DORYOPLPKBBLFQ-UHFFFAOYSA-N 1-[8-(4-methylpiperidine-1-carbonyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]butan-1-one Chemical compound C=1C=C2N(C(=O)CCC)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 DORYOPLPKBBLFQ-UHFFFAOYSA-N 0.000 claims 1
- CBRCWAVGAWOTCB-UHFFFAOYSA-N 1-cyclopentyl-3-(2-cyclopentyl-5-propyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-8-yl)urea Chemical compound C=1C=C2N(CCC)C3CCN(C4CCCC4)CC3C2=CC=1NC(=O)NC1CCCC1 CBRCWAVGAWOTCB-UHFFFAOYSA-N 0.000 claims 1
- UOSMIOCXTOYXOK-UHFFFAOYSA-N 2,2-difluoro-1-[8-(4-methylpiperidine-1-carbonyl)-5-prop-2-enyl-3,4-dihydro-1h-pyrido[4,3-b]indol-2-yl]propan-1-one Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=C)C2=C3CN(CC2)C(=O)C(C)(F)F)C3=C1 UOSMIOCXTOYXOK-UHFFFAOYSA-N 0.000 claims 1
- WOZOUJVEQDNDCB-UHFFFAOYSA-N 2,2-difluoro-1-[8-(4-methylpiperidine-1-carbonyl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-2-yl]propan-1-one Chemical compound C=1C=C2N(CCC)C=3CCN(C(=O)C(C)(F)F)CC=3C2=CC=1C(=O)N1CCC(C)CC1 WOZOUJVEQDNDCB-UHFFFAOYSA-N 0.000 claims 1
- FQGMRZAPDZONKL-UHFFFAOYSA-N 2-[2-cyclobutyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]-n,n-dimethylacetamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC(=O)N(C)C)C2=C3CN(CC2)C2CCC2)C3=C1 FQGMRZAPDZONKL-UHFFFAOYSA-N 0.000 claims 1
- XYVVKDQOILDYRL-UHFFFAOYSA-N 2-[2-cyclohexyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]-n,n-dimethylacetamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC(=O)N(C)C)C2=C3CN(CC2)C2CCCCC2)C3=C1 XYVVKDQOILDYRL-UHFFFAOYSA-N 0.000 claims 1
- IATFUJAKZIVKNY-UHFFFAOYSA-N 2-[2-cyclopentyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]-n,n-dimethylacetamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC(=O)N(C)C)C2=C3CN(CC2)C2CCCC2)C3=C1 IATFUJAKZIVKNY-UHFFFAOYSA-N 0.000 claims 1
- YVSNOWBNDCFRGB-UHFFFAOYSA-N 2-[2-cyclopentyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC(O)=O)C2=C3CN(CC2)C2CCCC2)C3=C1 YVSNOWBNDCFRGB-UHFFFAOYSA-N 0.000 claims 1
- WYRUYTRZZMGZQQ-UHFFFAOYSA-N 2-[[8-(4-methylpiperidine-1-carbonyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]sulfonyl]benzoic acid Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCOCC2)S(=O)(=O)C=2C(=CC=CC=2)C(O)=O)C3=C1 WYRUYTRZZMGZQQ-UHFFFAOYSA-N 0.000 claims 1
- LHRUBCPQJWSCDH-UHFFFAOYSA-N 2-cyclobutyl-n,n-dimethyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indole-5-carboxamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C(=O)N(C)C)C2=C3CN(CC2)C2CCC2)C3=C1 LHRUBCPQJWSCDH-UHFFFAOYSA-N 0.000 claims 1
- HBNFLNXIXRTYTC-UHFFFAOYSA-N 2-cyclopentyl-n,n-dimethyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indole-5-sulfonamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCCC2)S(=O)(=O)N(C)C)C3=C1 HBNFLNXIXRTYTC-UHFFFAOYSA-N 0.000 claims 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
- RUQMQGIXVFXBGL-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinolin-2-yl-[2-(1-methylpiperidin-4-yl)-5-propylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1C=2C3=CC(C(=O)N4CC5=CC=CC=C5CC4)=CC=C3N(S(=O)(=O)CCC)C=2CCN1C1CCN(C)CC1 RUQMQGIXVFXBGL-UHFFFAOYSA-N 0.000 claims 1
- BRXSGBLPIZRUMJ-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinolin-2-yl-[5-ethylsulfonyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1C=2C3=CC(C(=O)N4CC5=CC=CC=C5CC4)=CC=C3N(S(=O)(=O)CC)C=2CCN1C1CCOCC1 BRXSGBLPIZRUMJ-UHFFFAOYSA-N 0.000 claims 1
- KCSHFMUBPRUWTI-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinolin-2-yl-[5-ethylsulfonyl-2-(oxolan-2-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1C=2C3=CC(C(=O)N4CC5=CC=CC=C5CC4)=CC=C3N(S(=O)(=O)CC)C=2CCN1C1CCCO1 KCSHFMUBPRUWTI-UHFFFAOYSA-N 0.000 claims 1
- WXCRMQBQSUHIBE-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinolin-2-yl-[5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C1C=2C3=CC(C(=O)N4CC5=CC=CC=C5CC4)=CC=C3N(C)C=2CCN1C1CCOCC1 WXCRMQBQSUHIBE-UHFFFAOYSA-N 0.000 claims 1
- SGTCHVSZVLIDTQ-UHFFFAOYSA-N 5-[[2-cyclopentyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]methyl]furan-2-carboxylic acid Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=2OC(=CC=2)C(O)=O)C2=C3CN(CC2)C2CCCC2)C3=C1 SGTCHVSZVLIDTQ-UHFFFAOYSA-N 0.000 claims 1
- PYCWOQNHNUNSCO-UHFFFAOYSA-N 5-methyl-2-(oxan-4-yl)-n-(oxolan-2-ylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)NCC1CCCO1 PYCWOQNHNUNSCO-UHFFFAOYSA-N 0.000 claims 1
- QKPOUOPBYLWICG-UHFFFAOYSA-N 5-methyl-2-(oxan-4-yl)-n-phenyl-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)NC1=CC=CC=C1 QKPOUOPBYLWICG-UHFFFAOYSA-N 0.000 claims 1
- PVXROYBDZVXUHK-UHFFFAOYSA-N 5-methyl-n,2-bis(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)NC1CCOCC1 PVXROYBDZVXUHK-UHFFFAOYSA-N 0.000 claims 1
- PZVRJTKRUPRNFN-UHFFFAOYSA-N 5-methyl-n-(2-morpholin-4-ylethyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)NCCN1CCOCC1 PZVRJTKRUPRNFN-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- DUZZCRXFDYPJFU-UHFFFAOYSA-N [2-(2,2-difluoroethyl)-5-ethylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(CC(F)F)CC=3C2=CC=1C(=O)N1CCC(C)CC1 DUZZCRXFDYPJFU-UHFFFAOYSA-N 0.000 claims 1
- IOWBXOSMHOXQDB-UHFFFAOYSA-N [2-(2,2-difluoroethyl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(CCC)C=3CCN(CC(F)F)CC=3C2=CC=1C(=O)N1CCC(C)CC1 IOWBXOSMHOXQDB-UHFFFAOYSA-N 0.000 claims 1
- MTEYZEUVPQGYAB-UHFFFAOYSA-N [2-(3,4-dihydro-2h-pyrrol-5-yl)-5-[(4-ethoxyphenyl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1=CC(OCC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(C=1CCCN=1)C2 MTEYZEUVPQGYAB-UHFFFAOYSA-N 0.000 claims 1
- YVPLQCQGUWWNJU-UHFFFAOYSA-N [2-(3,4-dihydro-2h-pyrrol-5-yl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(CCC)C=3CCN(C=4CCCN=4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 YVPLQCQGUWWNJU-UHFFFAOYSA-N 0.000 claims 1
- RMUABMASIDBYLK-UHFFFAOYSA-N [2-(3,4-dihydro-2h-pyrrol-5-yl)-5-propylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(S(=O)(=O)CCC)C=3CCN(C=4CCCN=4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 RMUABMASIDBYLK-UHFFFAOYSA-N 0.000 claims 1
- XXLZMYGIMDUGFJ-UHFFFAOYSA-N [2-(cyclohex-3-en-1-ylmethyl)-5-(2-methoxyethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CC1CCC=CC1 XXLZMYGIMDUGFJ-UHFFFAOYSA-N 0.000 claims 1
- YHQGAWLEACLMCR-UHFFFAOYSA-N [2-(cyclopentylmethyl)-5-(2-methoxyethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CC1CCCC1 YHQGAWLEACLMCR-UHFFFAOYSA-N 0.000 claims 1
- VBJGLKTVMGKWFI-UHFFFAOYSA-N [2-(cyclopropylmethyl)-5-(2-methoxyethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CC1CC1 VBJGLKTVMGKWFI-UHFFFAOYSA-N 0.000 claims 1
- VAQRHCRTQRJWKH-UHFFFAOYSA-N [2-(cyclopropylmethyl)-5-(oxan-4-ylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC2CCOCC2)C2=C3CN(CC4CC4)CC2)C3=C1 VAQRHCRTQRJWKH-UHFFFAOYSA-N 0.000 claims 1
- BDSOSZNUEDOYNB-UHFFFAOYSA-N [2-(cyclopropylmethyl)-5-[(4-ethoxyphenyl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1=CC(OCC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C(C2)=C1CCN2CC1CC1 BDSOSZNUEDOYNB-UHFFFAOYSA-N 0.000 claims 1
- HFBGPIKGKKTFBM-UHFFFAOYSA-N [2-(cyclopropylmethyl)-5-ethylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(S(=O)(=O)CC)C=2CCN1CC1CC1 HFBGPIKGKKTFBM-UHFFFAOYSA-N 0.000 claims 1
- MVIUOIRYEBIYLG-UHFFFAOYSA-N [2-(cyclopropylmethyl)-5-methylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC4CC4)CC2)S(C)(=O)=O)C3=C1 MVIUOIRYEBIYLG-UHFFFAOYSA-N 0.000 claims 1
- ATFPKCCWKBNASV-UHFFFAOYSA-N [2-(cyclopropylmethyl)-5-prop-2-enyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=C)C2=C3CN(CC4CC4)CC2)C3=C1 ATFPKCCWKBNASV-UHFFFAOYSA-N 0.000 claims 1
- ZUNDGXRVRUQRJI-UHFFFAOYSA-N [2-butyl-5-(2-methoxyethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1N(CCCC)CCC(N(C2=CC=3)CCOC)=C1C2=CC=3C(=O)N1CCC(C)CC1 ZUNDGXRVRUQRJI-UHFFFAOYSA-N 0.000 claims 1
- KPIWYZKCJJXJPN-UHFFFAOYSA-N [2-cyclobutyl-5-(1-methylimidazol-4-yl)sulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCC2)S(=O)(=O)C=2N=CN(C)C=2)C3=C1 KPIWYZKCJJXJPN-UHFFFAOYSA-N 0.000 claims 1
- OGKIWQFBLNEINR-UHFFFAOYSA-N [2-cyclobutyl-5-[(4-ethoxyphenyl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1=CC(OCC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(C1CCC1)C2 OGKIWQFBLNEINR-UHFFFAOYSA-N 0.000 claims 1
- VJWLYZDNHBODEG-UHFFFAOYSA-N [2-cyclopentyl-5-(cyclopropylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC2CC2)C2=C3CN(CC2)C2CCCC2)C3=C1 VJWLYZDNHBODEG-UHFFFAOYSA-N 0.000 claims 1
- BJJMFHZGOXUYKR-UHFFFAOYSA-N [2-cyclopentyl-5-[(2-methyl-1,3-thiazol-4-yl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=2N=C(C)SC=2)C2=C3CN(CC2)C2CCCC2)C3=C1 BJJMFHZGOXUYKR-UHFFFAOYSA-N 0.000 claims 1
- SVKPGQVXHQUPDO-UHFFFAOYSA-N [2-cyclopentyl-5-[(4-methylsulfanylphenyl)methyl]-2-oxido-3,4-dihydro-1h-pyrido[4,3-b]indol-2-ium-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1=CC(SC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CC[N+]([O-])(C1CCCC1)C2 SVKPGQVXHQUPDO-UHFFFAOYSA-N 0.000 claims 1
- ZFURERTXCIPRLH-UHFFFAOYSA-N [2-cyclopentyl-5-[(4-methylsulfanylphenyl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1=CC(SC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(C1CCCC1)C2 ZFURERTXCIPRLH-UHFFFAOYSA-N 0.000 claims 1
- HTNYVWHHNPQKRS-UHFFFAOYSA-N [2-cyclopentyl-5-[(4-methylsulfonylphenyl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=2C=CC(=CC=2)S(C)(=O)=O)C2=C3CN(CC2)C2CCCC2)C3=C1 HTNYVWHHNPQKRS-UHFFFAOYSA-N 0.000 claims 1
- YNKLHYHLUVNZIK-UHFFFAOYSA-N [2-cyclopentyl-5-[(5-methyl-1,2-oxazol-4-yl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC2=C(ON=C2)C)C2=C3CN(CC2)C2CCCC2)C3=C1 YNKLHYHLUVNZIK-UHFFFAOYSA-N 0.000 claims 1
- UDIRIXGUGDFPAY-UHFFFAOYSA-N [2-ethanimidoyl-5-[(4-ethoxyphenyl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1=CC(OCC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(C(C)=N)C2 UDIRIXGUGDFPAY-UHFFFAOYSA-N 0.000 claims 1
- FWPFVGLCWNBZIF-UHFFFAOYSA-N [2-ethyl-5-(2-methoxyethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1N(CC)CCC(N(C2=CC=3)CCOC)=C1C2=CC=3C(=O)N1CCC(C)CC1 FWPFVGLCWNBZIF-UHFFFAOYSA-N 0.000 claims 1
- SAFSKHQXFTWUJK-UHFFFAOYSA-N [4-(hydroxymethyl)piperidin-1-yl]-[5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]methanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(CO)CC1 SAFSKHQXFTWUJK-UHFFFAOYSA-N 0.000 claims 1
- LTJVIJHEUMWHNQ-UHFFFAOYSA-N [5-(1-methylimidazol-4-yl)sulfonyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCOCC2)S(=O)(=O)C=2N=CN(C)C=2)C3=C1 LTJVIJHEUMWHNQ-UHFFFAOYSA-N 0.000 claims 1
- YBOVBIAZLZRDGP-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-(1,3-oxazol-2-ylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CC1=NC=CO1 YBOVBIAZLZRDGP-UHFFFAOYSA-N 0.000 claims 1
- KDKDNEZHXBKKNN-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-(1,3-oxazol-5-ylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CC1=CN=CO1 KDKDNEZHXBKKNN-UHFFFAOYSA-N 0.000 claims 1
- XACIQXDBFIHLJV-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-(2-phenylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CCC1=CC=CC=C1 XACIQXDBFIHLJV-UHFFFAOYSA-N 0.000 claims 1
- KSSSCUZZJNSZRZ-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-(3-methylbutyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(CCOC)C=3CCN(CCC(C)C)CC=3C2=CC=1C(=O)N1CCC(C)CC1 KSSSCUZZJNSZRZ-UHFFFAOYSA-N 0.000 claims 1
- QCOQITYVWOXUCU-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(CCOC)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 QCOQITYVWOXUCU-UHFFFAOYSA-N 0.000 claims 1
- YFLPKNCLBKTTPE-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-(oxolan-3-ylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CC1CCOC1 YFLPKNCLBKTTPE-UHFFFAOYSA-N 0.000 claims 1
- TWJOITXWBYBDFM-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-(pyridin-2-ylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CC1=CC=CC=N1 TWJOITXWBYBDFM-UHFFFAOYSA-N 0.000 claims 1
- IAVCVRKOGQTCMO-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-(pyridin-3-ylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CC1=CC=CN=C1 IAVCVRKOGQTCMO-UHFFFAOYSA-N 0.000 claims 1
- LVUOGTGREOXLGT-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-(pyridin-4-ylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CC1=CC=NC=C1 LVUOGTGREOXLGT-UHFFFAOYSA-N 0.000 claims 1
- KDZHTILKLKVWMZ-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-[(6-methylpyridin-2-yl)methyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CC1=CC=CC(C)=N1 KDZHTILKLKVWMZ-UHFFFAOYSA-N 0.000 claims 1
- VNHOGLXSCJDQLM-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-[2-(oxan-4-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1C=2C3=CC(C(=O)N4CCC(C)CC4)=CC=C3N(CCOC)C=2CCN1CCC1CCOCC1 VNHOGLXSCJDQLM-UHFFFAOYSA-N 0.000 claims 1
- ZQDOPMGIVQTNST-UHFFFAOYSA-N [5-(2-methoxyethyl)-2-pentyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1N(CCCCC)CCC(N(C2=CC=3)CCOC)=C1C2=CC=3C(=O)N1CCC(C)CC1 ZQDOPMGIVQTNST-UHFFFAOYSA-N 0.000 claims 1
- DVKUHMWHFDIMJO-UHFFFAOYSA-N [5-(benzenesulfonyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCOCC2)S(=O)(=O)C=2C=CC=CC=2)C3=C1 DVKUHMWHFDIMJO-UHFFFAOYSA-N 0.000 claims 1
- FSVUUMALPPRGGI-UHFFFAOYSA-N [5-(cyclobutylmethyl)-2-cyclopentyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC2CCC2)C2=C3CN(CC2)C2CCCC2)C3=C1 FSVUUMALPPRGGI-UHFFFAOYSA-N 0.000 claims 1
- CQBGJAUHLXXWJN-UHFFFAOYSA-N [5-[(2,6-difluorophenyl)methyl]-2-propan-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methoxypiperidin-1-yl)methanone Chemical compound C1CC(OC)CCN1C(=O)C1=CC=C(N(CC=2C(=CC=CC=2F)F)C2=C3CN(CC2)C(C)C)C3=C1 CQBGJAUHLXXWJN-UHFFFAOYSA-N 0.000 claims 1
- GATPKMYOJPZDNL-UHFFFAOYSA-N [5-[(4-ethoxyphenyl)methyl]-2-(2-methylpropyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1=CC(OCC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(CC(C)C)C2 GATPKMYOJPZDNL-UHFFFAOYSA-N 0.000 claims 1
- ZZPRUFQKSMSCLW-UHFFFAOYSA-N [5-[(4-ethoxyphenyl)methyl]-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1=CC(OCC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(C1CCOCC1)C2 ZZPRUFQKSMSCLW-UHFFFAOYSA-N 0.000 claims 1
- XCPQEHKBDTXLOB-UHFFFAOYSA-N [5-[(4-ethoxyphenyl)methyl]-2-propan-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-ethoxypiperidin-1-yl)methanone Chemical compound C1CC(OCC)CCN1C(=O)C1=CC=C(N(CC=2C=CC(OCC)=CC=2)C2=C3CN(CC2)C(C)C)C3=C1 XCPQEHKBDTXLOB-UHFFFAOYSA-N 0.000 claims 1
- AKLSVTVKVPYNHV-UHFFFAOYSA-N [5-[(4-ethoxyphenyl)methyl]-2-propan-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methoxypiperidin-1-yl)methanone Chemical compound C1=CC(OCC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(CC3)OC)C=C2C2=C1CCN(C(C)C)C2 AKLSVTVKVPYNHV-UHFFFAOYSA-N 0.000 claims 1
- MXSFGYZJQXJQCC-UHFFFAOYSA-N [5-[(4-ethoxyphenyl)methyl]-2-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1N(CCC)CCC2=C1C1=CC(C(=O)N3CCC(C)CC3)=CC=C1N2CC1=CC=C(OCC)C=C1 MXSFGYZJQXJQCC-UHFFFAOYSA-N 0.000 claims 1
- JCRXYOGVNHZBJI-UHFFFAOYSA-N [5-[(4-ethoxyphenyl)methyl]-2-pyrimidin-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1=CC(OCC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(C=1N=CC=CN=1)C2 JCRXYOGVNHZBJI-UHFFFAOYSA-N 0.000 claims 1
- LXSWSVZTCDAQKR-UHFFFAOYSA-N [5-[(4-methoxyphenyl)methyl]-2-propan-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1=CC(OC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(C(C)C)C2 LXSWSVZTCDAQKR-UHFFFAOYSA-N 0.000 claims 1
- XXAANGXTHDJWIZ-UHFFFAOYSA-N [5-[(5-methyl-1,2-oxazol-4-yl)sulfonyl]-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCOCC2)S(=O)(=O)C2=C(ON=C2)C)C3=C1 XXAANGXTHDJWIZ-UHFFFAOYSA-N 0.000 claims 1
- MNIPFNGXJLSGHK-UHFFFAOYSA-N [5-[(6-chloro-1,3-benzodioxol-5-yl)methyl]-2-propan-2-yl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methoxypiperidin-1-yl)methanone Chemical compound C1CC(OC)CCN1C(=O)C1=CC=C(N(CC=2C(=CC=3OCOC=3C=2)Cl)C2=C3CN(CC2)C(C)C)C3=C1 MNIPFNGXJLSGHK-UHFFFAOYSA-N 0.000 claims 1
- LWUVJNFMXIDOOI-UHFFFAOYSA-N [5-cyclopropylsulfonyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCOCC2)S(=O)(=O)C2CC2)C3=C1 LWUVJNFMXIDOOI-UHFFFAOYSA-N 0.000 claims 1
- NBPLAQPSYNGUKP-UHFFFAOYSA-N [5-ethyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(CC)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 NBPLAQPSYNGUKP-UHFFFAOYSA-N 0.000 claims 1
- KQAHDCSHFZPRLH-UHFFFAOYSA-N [5-ethylsulfonyl-2-(1-methylpiperidin-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(C4CCN(C)CC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 KQAHDCSHFZPRLH-UHFFFAOYSA-N 0.000 claims 1
- YJQLRPARZZLPEZ-UHFFFAOYSA-N [5-ethylsulfonyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methoxypiperidin-1-yl)methanone Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(OC)CC1 YJQLRPARZZLPEZ-UHFFFAOYSA-N 0.000 claims 1
- UCMNIYFDRVBMFV-UHFFFAOYSA-N [5-ethylsulfonyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 UCMNIYFDRVBMFV-UHFFFAOYSA-N 0.000 claims 1
- OINCQRGOMJVZHD-UHFFFAOYSA-N [5-ethylsulfonyl-2-(oxolan-3-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(C4COCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 OINCQRGOMJVZHD-UHFFFAOYSA-N 0.000 claims 1
- KQPJRFXWAWUUTE-UHFFFAOYSA-N [5-imidazol-1-ylsulfonyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCOCC2)S(=O)(=O)N2C=NC=C2)C3=C1 KQPJRFXWAWUUTE-UHFFFAOYSA-N 0.000 claims 1
- SRVUHZJXAYHXIN-UHFFFAOYSA-N [5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N(C)C2=C3CN(CC2)C2CCOCC2)C3=C1 SRVUHZJXAYHXIN-UHFFFAOYSA-N 0.000 claims 1
- IGBCISBWUNCTNY-UHFFFAOYSA-N [5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C)C2=C3CN(CC2)C2CCOCC2)C3=C1 IGBCISBWUNCTNY-UHFFFAOYSA-N 0.000 claims 1
- CIYIQMUKJDTYAJ-UHFFFAOYSA-N [5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-(4-phenylpiperidin-1-yl)methanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N(CC1)CCC1C1=CC=CC=C1 CIYIQMUKJDTYAJ-UHFFFAOYSA-N 0.000 claims 1
- OPYPOQONOBJLPD-UHFFFAOYSA-N [5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-[4-(trifluoromethyl)piperidin-1-yl]methanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C(F)(F)F)CC1 OPYPOQONOBJLPD-UHFFFAOYSA-N 0.000 claims 1
- VSHOWHRCWOIRAS-UHFFFAOYSA-N [5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCOCC1 VSHOWHRCWOIRAS-UHFFFAOYSA-N 0.000 claims 1
- AWPMNXJSXFCGSV-UHFFFAOYSA-N [5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-piperidin-1-ylmethanone Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCCCC1 AWPMNXJSXFCGSV-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims 1
- GUDSPOSQRRZORN-UHFFFAOYSA-N cyclobutyl-[5-[(4-ethoxyphenyl)methyl]-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-2-yl]methanone Chemical compound C1=CC(OCC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(C(=O)C1CCC1)C2 GUDSPOSQRRZORN-UHFFFAOYSA-N 0.000 claims 1
- TTXROTXBANFUIL-UHFFFAOYSA-N cyclobutyl-[8-(4-methylpiperidine-1-carbonyl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-2-yl]methanone Chemical compound C=1C=C2N(CCC)C=3CCN(C(=O)C4CCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 TTXROTXBANFUIL-UHFFFAOYSA-N 0.000 claims 1
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 1
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims 1
- KEQCRARZBQNJQJ-UHFFFAOYSA-N cyclopentyl-[8-(4-methylpiperidine-1-carbonyl)-5-prop-2-enyl-3,4-dihydro-1h-pyrido[4,3-b]indol-2-yl]methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=C)C2=C3CN(CC2)C(=O)C2CCCC2)C3=C1 KEQCRARZBQNJQJ-UHFFFAOYSA-N 0.000 claims 1
- KUKFQVOAHXOHNL-UHFFFAOYSA-N cyclopentyl-[8-(4-methylpiperidine-1-carbonyl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-2-yl]methanone Chemical compound C=1C=C2N(CCC)C=3CCN(C(=O)C4CCCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 KUKFQVOAHXOHNL-UHFFFAOYSA-N 0.000 claims 1
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
- YBBYEWHGGOBZTP-UHFFFAOYSA-N methyl 2-[2-cyclobutyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetate Chemical compound C=1C=C2N(CC(=O)OC)C=3CCN(C4CCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 YBBYEWHGGOBZTP-UHFFFAOYSA-N 0.000 claims 1
- NZLFMVRXBYBIPI-UHFFFAOYSA-N methyl 2-[2-cyclopentyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetate Chemical compound C=1C=C2N(CC(=O)OC)C=3CCN(C4CCCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 NZLFMVRXBYBIPI-UHFFFAOYSA-N 0.000 claims 1
- VSHCLFPRPOXBBF-UHFFFAOYSA-N methyl 2-[[8-(4-methylpiperidine-1-carbonyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]sulfonyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)N1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(C1CCOCC1)C2 VSHCLFPRPOXBBF-UHFFFAOYSA-N 0.000 claims 1
- DWSGEHPLNSEZOT-UHFFFAOYSA-N methyl 5-[[2-cyclopentyl-8-(4-methylpiperidine-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]methyl]furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC=C1CN1C2=CC=C(C(=O)N3CCC(C)CC3)C=C2C2=C1CCN(C1CCCC1)C2 DWSGEHPLNSEZOT-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- MTTQUXMMKJLVQI-UHFFFAOYSA-N n,n-dimethyl-8-(4-methylpiperidine-1-carbonyl)-2-(3,3,3-trifluoropropyl)-3,4-dihydro-1h-pyrido[4,3-b]indole-5-sulfonamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CCC(F)(F)F)CC2)S(=O)(=O)N(C)C)C3=C1 MTTQUXMMKJLVQI-UHFFFAOYSA-N 0.000 claims 1
- XSDISIAXSICJFF-UHFFFAOYSA-N n,n-dimethyl-8-(4-methylpiperidine-1-carbonyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indole-5-carboxamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C(=O)N(C)C)C2=C3CN(CC2)C2CCOCC2)C3=C1 XSDISIAXSICJFF-UHFFFAOYSA-N 0.000 claims 1
- IOBGWHNZXXNBCX-UHFFFAOYSA-N n,n-dimethyl-8-(4-methylpiperidine-1-carbonyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indole-5-sulfonamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCOCC2)S(=O)(=O)N(C)C)C3=C1 IOBGWHNZXXNBCX-UHFFFAOYSA-N 0.000 claims 1
- JGAUXIRUFFBYAM-UHFFFAOYSA-N n,n-dimethyl-8-(4-methylpiperidine-1-carbonyl)-2-(oxolan-3-yl)-3,4-dihydro-1h-pyrido[4,3-b]indole-5-sulfonamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2COCC2)S(=O)(=O)N(C)C)C3=C1 JGAUXIRUFFBYAM-UHFFFAOYSA-N 0.000 claims 1
- CTNUFTATIHKKSO-UHFFFAOYSA-N n-(2-cyclopentyl-5-propyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-8-yl)benzamide Chemical compound C=1C=C2N(CCC)C3CCN(C4CCCC4)CC3C2=CC=1NC(=O)C1=CC=CC=C1 CTNUFTATIHKKSO-UHFFFAOYSA-N 0.000 claims 1
- MKXCSIZMPVFGDY-UHFFFAOYSA-N n-(2-cyclopentyl-5-propyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-8-yl)benzenesulfonamide Chemical compound C=1C=C2N(CCC)C3CCN(C4CCCC4)CC3C2=CC=1NS(=O)(=O)C1=CC=CC=C1 MKXCSIZMPVFGDY-UHFFFAOYSA-N 0.000 claims 1
- LMTALNKYSCWTHC-UHFFFAOYSA-N n-(2-cyclopentyl-5-propyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-8-yl)cyclopentanecarboxamide Chemical compound C=1C=C2N(CCC)C3CCN(C4CCCC4)CC3C2=CC=1NC(=O)C1CCCC1 LMTALNKYSCWTHC-UHFFFAOYSA-N 0.000 claims 1
- FUWDLDCAGSELMV-UHFFFAOYSA-N n-(2-cyclopentyl-5-propyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-8-yl)cyclopropanecarboxamide Chemical compound C=1C=C2N(CCC)C3CCN(C4CCCC4)CC3C2=CC=1NC(=O)C1CC1 FUWDLDCAGSELMV-UHFFFAOYSA-N 0.000 claims 1
- DGSIRHNFMHTWRR-UHFFFAOYSA-N n-(2-cyclopentyl-5-propyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-8-yl)ethanesulfonamide Chemical compound C1C2C3=CC(NS(=O)(=O)CC)=CC=C3N(CCC)C2CCN1C1CCCC1 DGSIRHNFMHTWRR-UHFFFAOYSA-N 0.000 claims 1
- OHCNXSUCGCOZBE-UHFFFAOYSA-N n-(2-cyclopentyl-5-propyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-8-yl)propanamide Chemical compound C1C2C3=CC(NC(=O)CC)=CC=C3N(CCC)C2CCN1C1CCCC1 OHCNXSUCGCOZBE-UHFFFAOYSA-N 0.000 claims 1
- CPSQTBKLWRCGBX-UHFFFAOYSA-N n-(2-hydroxyethyl)-n,5-dimethyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C1C=2C3=CC(C(=O)N(CCO)C)=CC=C3N(C)C=2CCN1C1CCOCC1 CPSQTBKLWRCGBX-UHFFFAOYSA-N 0.000 claims 1
- OMORGSGQZVTEBA-UHFFFAOYSA-N n-(2-methoxyethyl)-5-methyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C1C=2C3=CC(C(=O)NCCOC)=CC=C3N(C)C=2CCN1C1CCOCC1 OMORGSGQZVTEBA-UHFFFAOYSA-N 0.000 claims 1
- QOQAZIKTQNXQFU-UHFFFAOYSA-N n-[2-(dimethylamino)-2-oxoethyl]-n,5-dimethyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C1C=2C3=CC(C(=O)N(C)CC(=O)N(C)C)=CC=C3N(C)C=2CCN1C1CCOCC1 QOQAZIKTQNXQFU-UHFFFAOYSA-N 0.000 claims 1
- IRISXNLIJVWQSO-UHFFFAOYSA-N n-[2-(oxan-4-yl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]cyclobutanecarboxamide Chemical compound C=1C=C2N(CCC)C=3CCN(C4CCOCC4)CC=3C2=CC=1NC(=O)C1CCC1 IRISXNLIJVWQSO-UHFFFAOYSA-N 0.000 claims 1
- CSVFPZZQZFQCBZ-UHFFFAOYSA-N n-[2-(oxan-4-yl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]cyclohexanecarboxamide Chemical compound C=1C=C2N(CCC)C=3CCN(C4CCOCC4)CC=3C2=CC=1NC(=O)C1CCCCC1 CSVFPZZQZFQCBZ-UHFFFAOYSA-N 0.000 claims 1
- BHMCZXLTPFVNMC-UHFFFAOYSA-N n-[2-(oxan-4-yl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]cyclopentanecarboxamide Chemical compound C=1C=C2N(CCC)C=3CCN(C4CCOCC4)CC=3C2=CC=1NC(=O)C1CCCC1 BHMCZXLTPFVNMC-UHFFFAOYSA-N 0.000 claims 1
- GWTOBOYCYQCJHL-UHFFFAOYSA-N n-[2-(oxan-4-yl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]oxane-4-carboxamide Chemical compound C=1C=C2N(CCC)C=3CCN(C4CCOCC4)CC=3C2=CC=1NC(=O)C1CCOCC1 GWTOBOYCYQCJHL-UHFFFAOYSA-N 0.000 claims 1
- WFEBRTGBKHHFBW-UHFFFAOYSA-N n-[2-(oxan-4-yl)-5-propyl-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]oxolane-2-carboxamide Chemical compound C=1C=C2N(CCC)C=3CCN(C4CCOCC4)CC=3C2=CC=1NC(=O)C1CCCO1 WFEBRTGBKHHFBW-UHFFFAOYSA-N 0.000 claims 1
- TZVMLNBCHPIZID-UHFFFAOYSA-N n-[4-[8-(4-methylpiperidine-1-carbonyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]phenyl]acetamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(C2=C3CN(CC2)C2CCOCC2)C=2C=CC(NC(C)=O)=CC=2)C3=C1 TZVMLNBCHPIZID-UHFFFAOYSA-N 0.000 claims 1
- FWADLSFMEAEECJ-UHFFFAOYSA-N n-[5-ethylsulfonyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]-1-methylimidazole-4-sulfonamide Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(C4CCOCC4)CC=3C2=CC=1NS(=O)(=O)C1=CN(C)C=N1 FWADLSFMEAEECJ-UHFFFAOYSA-N 0.000 claims 1
- NIYJRGMFSHSNMP-UHFFFAOYSA-N n-[5-ethylsulfonyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]pyrrolidine-1-carboxamide Chemical compound C=1C=C2N(S(=O)(=O)CC)C=3CCN(C4CCOCC4)CC=3C2=CC=1NC(=O)N1CCCC1 NIYJRGMFSHSNMP-UHFFFAOYSA-N 0.000 claims 1
- VMPPJORJEAPMIC-UHFFFAOYSA-N n-[5-methylsulfonyl-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indol-8-yl]cyclopentanecarboxamide Chemical compound C=1C=C2N(S(=O)(=O)C)C=3CCN(C4CCOCC4)CC=3C2=CC=1NC(=O)C1CCCC1 VMPPJORJEAPMIC-UHFFFAOYSA-N 0.000 claims 1
- KNFLDURHTRCKTJ-UHFFFAOYSA-N n-ethyl-5-methyl-2-(oxan-4-yl)-n-(pyridin-4-ylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C=1C=C2N(C)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N(CC)CC1=CC=NC=C1 KNFLDURHTRCKTJ-UHFFFAOYSA-N 0.000 claims 1
- JNRJINSDQQDNSH-UHFFFAOYSA-N n-ethyl-8-(4-methylpiperidine-1-carbonyl)-2-(oxan-4-yl)-3,4-dihydro-1h-pyrido[4,3-b]indole-5-sulfonamide Chemical compound C=1C=C2N(S(=O)(=O)NCC)C=3CCN(C4CCOCC4)CC=3C2=CC=1C(=O)N1CCC(C)CC1 JNRJINSDQQDNSH-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004673 propylcarbonyl group Chemical group 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 0 *c1ccc2[n](*)c(CCN(*)C3)c3c2c1 Chemical compound *c1ccc2[n](*)c(CCN(*)C3)c3c2c1 0.000 description 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0500654 | 2005-03-22 | ||
| PCT/SE2006/000339 WO2006101434A1 (en) | 2005-03-22 | 2006-03-17 | NOVEL TETRAHYDRO-1H-PYRIDO [4,3-b] INDOLE DERIVATIVES AS CB1’ RECEPTOR LIGANDS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008534496A JP2008534496A (ja) | 2008-08-28 |
| JP2008534496A5 true JP2008534496A5 (enExample) | 2009-04-23 |
Family
ID=37024033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008502944A Abandoned JP2008534496A (ja) | 2005-03-22 | 2006-03-17 | ＣＢ１’受容体リガンドとしての新規なテトラヒドロ−１Ｈ−ピリド［４，３−ｂ］インドール誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20100113502A1 (enExample) |
| EP (1) | EP1863810A4 (enExample) |
| JP (1) | JP2008534496A (enExample) |
| CN (2) | CN101175754A (enExample) |
| AR (1) | AR053699A1 (enExample) |
| TW (1) | TW200716628A (enExample) |
| UY (1) | UY29427A1 (enExample) |
| WO (1) | WO2006101434A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007041697A2 (en) * | 2005-10-04 | 2007-04-12 | Medivation, Inc. | Hydrogenated pyrido-indole compounds for the treatment of huntington ' s disease |
| KR20080073359A (ko) * | 2005-12-01 | 2008-08-08 | 엘란 파마슈티칼스, 인크. | 5(아릴설포닐)피라졸로피페리딘 |
| WO2008036022A1 (en) * | 2006-09-20 | 2008-03-27 | Astrazeneca Ab | Tetrahydro-lh-pyrido[3,4-b] indole derivatives as cb1 receptor ligands |
| WO2008036021A1 (en) * | 2006-09-20 | 2008-03-27 | Astrazeneca Ab | Tetrahydro-lh-pyrido [3,4 -b] indole derivatives as cbl receptor ligands |
| RU2329044C1 (ru) * | 2006-11-16 | 2008-07-20 | Андрей Александрович Иващенко | Лиганды 5-ht6 рецепторов, фармацевтическая композиция, способ ее получения и лекарственное средство |
| US20090062251A1 (en) * | 2007-08-17 | 2009-03-05 | Astrazeneca Ab | Novel Compounds 002 |
| CN101868234A (zh) | 2007-09-20 | 2010-10-20 | D2E有限公司 | 具有神经保护和认知增强特性的氢化吡啶并[4,3-b]吲哚的含氟衍生物,其制备方法及应用 |
| MX2010005298A (es) | 2007-11-16 | 2010-06-30 | Rigel Pharmaceuticals Inc | Compuestos de carboxamida, sulfonamida y amina para trastornos metabolicos. |
| EP2231666B1 (en) | 2007-12-12 | 2015-07-29 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| 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 |
| JP5666036B2 (ja) * | 2008-01-25 | 2015-02-04 | 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 | 新規２，３，４，５−テトラヒドロ−１Ｈ−ピリド［４，３−ｂ］インドール化合物およびその使用方法 |
| TWI498328B (zh) * | 2008-01-25 | 2015-09-01 | Medivation Technologies Inc | 新穎之２，３，４，５－四氫－１ｈ－吡啶并〔４，３－ｂ〕吲哚化合物及其使用方法 |
| AU2009240643B2 (en) | 2008-04-23 | 2014-03-06 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds for the treatment of metabolic disorders |
| CN102271508B (zh) * | 2008-10-31 | 2015-04-29 | 梅迪维新技术公司 | 含有刚性部分的吡啶并[4，3-b]吲哚类化合物 |
| EP2348847A4 (en) | 2008-10-31 | 2012-05-23 | Medivation Technologies Inc | AZEPINO [4, 5-B] INDOLE AND USE PROCESS |
| WO2011044134A1 (en) | 2009-10-05 | 2011-04-14 | Albany Molecular Research, Inc. | Epiminocycloalkyl(b)indole derivatives as serotonin sub-type 6 (5-ht6) modulators and uses thereof |
| CN102153549B (zh) * | 2010-12-14 | 2012-11-14 | 华东理工大学 | γ咔啉化合物、制备方法和用途 |
| AU2012207335A1 (en) | 2011-01-19 | 2013-07-25 | Albany Molecular Research, Inc. | Benzofuro[3,2-c] pyridines and related analogs as serotonin sub-type 6 (5-HT6) modulators for the treatment of obesity, metabolic syndrome, cognition and schizophrenia |
| CN103476416B (zh) | 2011-02-18 | 2016-09-21 | 梅迪维新技术公司 | 治疗高血压的化合物和方法 |
| CN103864779B (zh) * | 2012-12-07 | 2016-06-22 | 天津科技大学 | 一种1-(苯基)-2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚衍生物的制备及其在抗肿瘤药物中的应用 |
| CN103864781A (zh) * | 2012-12-13 | 2014-06-18 | 天津科技大学 | 一种新型1，9-二取代四氢咔啉类衍生物的制备及其抗肿瘤药物中的应用 |
| TN2015000516A1 (en) * | 2013-05-28 | 2017-04-06 | Astrazeneca Ab | Chemical compounds |
| PT3433256T (pt) | 2016-10-24 | 2019-10-31 | Astrazeneca | Derivados de 6,7,8,9-tetrahidro-3h-pirazolo[4,3-f]isoquinolina úteis no tratamento do cancro |
| KR102246668B1 (ko) | 2017-01-30 | 2021-04-29 | 아스트라제네카 아베 | 에스트로겐 수용체 조절인자 |
| PE20221838A1 (es) | 2020-04-24 | 2022-11-29 | Astrazeneca Ab | Formulaciones farmaceuticas |
| IL297216A (en) | 2020-04-24 | 2022-12-01 | Astrazeneca Ab | Dosage regimen for the treatment of cancer |
| CN116425670A (zh) * | 2022-07-15 | 2023-07-14 | 英矽智能科技(上海)有限公司 | 作为tead抑制剂的新型杂环化合物 |
| CN120917021A (zh) * | 2023-03-15 | 2025-11-07 | 纽脑泰智有限公司 | 用于预防或治疗神经退行性疾病的包含新型吡啶并吲哚衍生物化合物作为活性成分的组合物 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US62251A (en) * | 1867-02-19 | Improvement in machines foe burnishing plated ware | ||
| JPH0256485A (ja) * | 1988-04-27 | 1990-02-26 | Glaxo Group Ltd | ラクタム誘導体 |
| US5008272A (en) * | 1988-08-15 | 1991-04-16 | Glaxo Group Limited | Lactam derivatives |
| US6448257B1 (en) * | 1998-05-22 | 2002-09-10 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| US6653304B2 (en) * | 2000-02-11 | 2003-11-25 | Bristol-Myers Squibb Co. | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases |
| CO5300399A1 (es) * | 2000-02-25 | 2003-07-31 | Astrazeneca Ab | Heterocicliocs que contienen nitrogeno, proceso para su preparacion y composiciones farmaceuticas que los contienen |
| WO2003097598A1 (en) * | 2002-05-16 | 2003-11-27 | Shionogi & Co., Ltd. | Compound exhibiting pgd 2 receptor antagonism |
| TWI329111B (en) * | 2002-05-24 | 2010-08-21 | X Ceptor Therapeutics Inc | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| JP2005162657A (ja) * | 2003-12-02 | 2005-06-23 | Takeda Chem Ind Ltd | カンナビノイド受容体調節剤 |
| WO2008036022A1 (en) * | 2006-09-20 | 2008-03-27 | Astrazeneca Ab | Tetrahydro-lh-pyrido[3,4-b] indole derivatives as cb1 receptor ligands |
| WO2008036021A1 (en) * | 2006-09-20 | 2008-03-27 | Astrazeneca Ab | Tetrahydro-lh-pyrido [3,4 -b] indole derivatives as cbl receptor ligands |
-
2006
- 2006-03-17 EP EP06717024A patent/EP1863810A4/en not_active Withdrawn
- 2006-03-17 US US11/909,089 patent/US20100113502A1/en not_active Abandoned
- 2006-03-17 CN CNA2006800168097A patent/CN101175754A/zh active Pending
- 2006-03-17 CN CN2010105223008A patent/CN102030750A/zh active Pending
- 2006-03-17 WO PCT/SE2006/000339 patent/WO2006101434A1/en not_active Ceased
- 2006-03-17 JP JP2008502944A patent/JP2008534496A/ja not_active Abandoned
- 2006-03-17 TW TW095109101A patent/TW200716628A/zh unknown
- 2006-03-20 UY UY29427A patent/UY29427A1/es not_active Application Discontinuation
- 2006-03-22 AR ARP060101132A patent/AR053699A1/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008534496A5 (enExample) | ||
| DK3072886T3 (en) | Pyridine-2-amides for use as CB2 agonists | |
| KR101078505B1 (ko) | 질소 함유 복소환 유도체 및 이들을 유효 성분으로 하는약제 | |
| JP5970003B2 (ja) | アミノピラジン化合物 | |
| JP5206747B2 (ja) | 含窒素複素環化合物およびその医薬用途 | |
| JP2025113339A (ja) | メニン－ｍｌｌ相互作用の阻害剤 | |
| JP6626449B2 (ja) | ＰＤＥ２阻害剤としての置換［１，２，４］トリアゾロ［１，５−ａ］ピリミジン−７−イル化合物 | |
| US11098010B2 (en) | Substituted dihydroindene-4-carboxamides and analogs thereof, and methods using same | |
| RU2010102992A (ru) | Лиганды каннабиноидных рецепторов | |
| ES2609987T3 (es) | Piridinonas bicíclicas novedosas | |
| RU2013126657A (ru) | Ингибиторы nampt и rock | |
| CN108779116A (zh) | 多发性内分泌瘤蛋白-mll相互作用的抑制剂 | |
| JP2009523796A (ja) | 炎症性障害の処置のためのヒダントイン誘導体 | |
| JP2018530591A5 (enExample) | ||
| JP7766946B2 (ja) | ムスカリン性アセチルコリン受容体ｍ４の陽性アロステリック調節因子としての７－（ピペリジン－１－イル）－４ｈ－ピリミド［１，２－ｂ］ピリダジン－４－オン誘導体 | |
| EP1966162A2 (en) | Pyrimidine derivatives | |
| US20100113502A1 (en) | Novel Tetrahydro-1H-Pyrido[4,3-b] Indole Derivatives as CB1 Receptor Ligands | |
| KR20050059164A (ko) | 치환된 1,4-디-피페리딘-4-일-피페라진 유도체 및 뉴로키닌길항제로서의 그의 용도 | |
| CA2633624A1 (en) | 3,5-substituted piperidine compounds as renin inhibitors | |
| WO2022241265A1 (en) | Inhibitors of the menin-mll interaction | |
| JP4177895B2 (ja) | タキキニンアンタゴニストとしてのｎ―アシル―２―置換―４―（ベンゾイミダゾリル―またはイミダゾピリジニル―置換残基）―ピペリジン | |
| EA034904B1 (ru) | Производные 3-(карбоксиметил)-8-амино-2-оксо-1,3-диазаспиро-[4.5]-декана | |
| WO2020085234A1 (ja) | モルヒナン誘導体 | |
| MXPA04009088A (es) | 1,2-dihidropirazol-3-onas como mediadores de citocinas. | |
| RU2008148905A (ru) | Производные бензимидазола для применения в качестве антагонистов рецепторов св1 |