JP2008534496A

JP2008534496A - 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

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 Download PDF

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Publication number: JP2008534496A
Authority: JP; Japan
Prior art keywords: tetrahydro; pyrido; alkyl; indole; carbonyl
Prior art date: 2005-03-22
Legal status : Abandoned

Application number

JP2008502944A

Other languages

English (en)

Japanese (ja)

Other versions

JP2008534496A5 (https=

Inventor

ユン−シン・チェン

ミロスラウ・トーマシェウスキ

Current Assignee

AstraZeneca AB

Original Assignee

AstraZeneca AB

Priority date

2005-03-22

Filing date

2006-03-17

Publication date

2008-08-28

2006-03-17 Application filed by AstraZeneca AB filed Critical AstraZeneca AB

2008-08-28 Publication of JP2008534496A publication Critical patent/JP2008534496A/ja

2009-04-23 Publication of JP2008534496A5 publication Critical patent/JP2008534496A5/ja

Status Abandoned legal-status Critical Current

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239000003446 ligand Substances 0.000 title description 6
ZRGIHRLCJVIUNZ-UHFFFAOYSA-N 2,3,4,4a-tetrahydro-1h-pyrido[4,3-b]indole Chemical class N1=C2C=CC=CC2=C2C1CCNC2 ZRGIHRLCJVIUNZ-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 208
150000003839 salts Chemical class 0.000 claims abstract description 42
208000002193 Pain Diseases 0.000 claims abstract description 22
238000011282 treatment Methods 0.000 claims abstract description 20
230000036407 pain Effects 0.000 claims abstract description 16
-1 methoxy, ethoxy Chemical group 0.000 claims description 693
125000000217 alkyl group Chemical group 0.000 claims description 304
239000000203 mixture Substances 0.000 claims description 239
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 233
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 92
238000000034 method Methods 0.000 claims description 78
238000004519 manufacturing process Methods 0.000 claims description 77
229910052757 nitrogen Inorganic materials 0.000 claims description 59
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
125000000623 heterocyclic group Chemical group 0.000 claims description 43
125000003118 aryl group Chemical group 0.000 claims description 40
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 38
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 37
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 37
229910052736 halogen Inorganic materials 0.000 claims description 35
150000002367 halogens Chemical class 0.000 claims description 35
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
125000001072 heteroaryl group Chemical group 0.000 claims description 29
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 28
229910052799 carbon Inorganic materials 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 19
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 15
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 15
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 13
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 11
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
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 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 6
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 6
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 6
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 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
208000018522 Gastrointestinal disease Diseases 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000002757 morpholinyl group Chemical group 0.000 claims description 5
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
125000003386 piperidinyl group Chemical group 0.000 claims description 5
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
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 description 4
125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 4
YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
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 description 4
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 description 4
208000019901 Anxiety disease Diseases 0.000 claims description 4
208000018737 Parkinson disease Diseases 0.000 claims description 4
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
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 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
208000024172 Cardiovascular disease Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
206010028980 Neoplasm Diseases 0.000 claims description 3
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 description 3
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 description 3
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 description 3
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 description 3
201000011510 cancer Diseases 0.000 claims description 3
125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims description 3
PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
201000006417 multiple sclerosis Diseases 0.000 claims description 3
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 description 3
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 description 3
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 description 3
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
125000004673 propylcarbonyl group Chemical group 0.000 claims description 3
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
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 description 3
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 2
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 description 2
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 description 2
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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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
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
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
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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
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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
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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
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125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1