JP2008534496A5 - - Google Patents
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- 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
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- 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
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- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 1
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- 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)
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| 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 |
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| JP2008534496A JP2008534496A (ja) | 2008-08-28 |
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| JP (1) | JP2008534496A (https=) |
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| TW (1) | TW200716628A (https=) |
| UY (1) | UY29427A1 (https=) |
| WO (1) | WO2006101434A1 (https=) |
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| US20070117834A1 (en) * | 2005-10-04 | 2007-05-24 | David Hung | Methods and compositions for treating Huntington's disease |
| AR057959A1 (es) * | 2005-12-01 | 2007-12-26 | Elan Pharm Inc | 5-pirazolpiperidinas-(sustituidas) |
| 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 |
| 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 |
| NZ585298A (en) | 2007-11-16 | 2012-08-31 | Rigel Pharmaceuticals Inc | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| EP2231666B1 (en) | 2007-12-12 | 2015-07-29 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| 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 |
| 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 |
| BRPI0911681B8 (pt) | 2008-04-23 | 2021-05-25 | Rigel Pharmaceuticals Inc | composto, composição farmacêutica, e, método para ativar a via de proteína quinase ativada por 5'-amp em uma célula in vitro |
| 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 |
| US8575186B2 (en) | 2009-10-05 | 2013-11-05 | 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 |
| EP2668191A4 (en) | 2011-01-19 | 2014-08-20 | Albany Molecular Res Inc | BENZOFURO- [3,2-C-] PYRIDINES AND RELATED ANALOGS AS SEROTONIN-SUBTYPE-6 (5-HT6) MODULATORS FOR THE TREATMENT OF ADIPOSITAS, METABOLISM SYNDROME, COGNITION AND SCHIZOPHRENIA |
| US8791132B2 (en) | 2011-02-18 | 2014-07-29 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| 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 |
| UY35590A (es) * | 2013-05-28 | 2014-11-28 | Astrazeneca Ab | Nuevos compuestos para el tratamiento del cáncer |
| EP3640251B1 (en) | 2016-10-24 | 2021-12-08 | Astrazeneca AB | 6,7,8,9-tetrahydro-3h-pyrazolo[4,3-f]isoquinoline derivatives useful in the treatment of cancer |
| PL3494116T3 (pl) | 2017-01-30 | 2020-04-30 | Astrazeneca Ab | Modulatory receptora estrogenowego |
| MX2022013258A (es) | 2020-04-24 | 2022-11-14 | Astrazeneca Ab | Formulaciones farmaceuticas. |
| MX2022013391A (es) | 2020-04-24 | 2022-11-30 | Astrazeneca Ab | Pauta posologica para el tratamiento del 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 |
| JP2026508633A (ja) * | 2023-03-15 | 2026-03-11 | ニューロタージ・カンパニー・リミテッド | 新規なピリドインドール誘導体化合物を有効成分として含む退行性脳疾患の予防または治療用組成物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US62251A (en) * | 1867-02-19 | Improvement in machines foe burnishing plated ware | ||
| US4985422A (en) * | 1988-04-27 | 1991-01-15 | Glaxo Group Limited | Lactam derivatives |
| JPH02167280A (ja) * | 1988-08-15 | 1990-06-27 | Glaxo Group Ltd | ラクタム誘導体 |
| US6448257B1 (en) * | 1998-05-22 | 2002-09-10 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| WO2001058869A2 (en) * | 2000-02-11 | 2001-08-16 | Bristol-Myers Squibb Company | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators in 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 |
| AU2003231509A1 (en) * | 2002-05-16 | 2003-12-02 | Shionogi And 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 WO PCT/SE2006/000339 patent/WO2006101434A1/en not_active Ceased
- 2006-03-17 US US11/909,089 patent/US20100113502A1/en not_active Abandoned
- 2006-03-17 JP JP2008502944A patent/JP2008534496A/ja not_active Abandoned
- 2006-03-17 EP EP06717024A patent/EP1863810A4/en not_active Withdrawn
- 2006-03-17 CN CNA2006800168097A patent/CN101175754A/zh active Pending
- 2006-03-17 TW TW095109101A patent/TW200716628A/zh unknown
- 2006-03-17 CN CN2010105223008A patent/CN102030750A/zh active Pending
- 2006-03-20 UY UY29427A patent/UY29427A1/es not_active Application Discontinuation
- 2006-03-22 AR ARP060101132A patent/AR053699A1/es unknown
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