JP5650540B2 - 代謝障害のためのカルボキサミド、スルホンアミド、およびアミン化合物 - Google Patents

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Publication number

JP5650540B2

JP5650540B2 JP2010538205A JP2010538205A JP5650540B2 JP 5650540 B2 JP5650540 B2 JP 5650540B2 JP 2010538205 A JP2010538205 A JP 2010538205A JP 2010538205 A JP2010538205 A JP 2010538205A JP 5650540 B2 JP5650540 B2 JP 5650540B2

Authority

JP

Japan

Prior art keywords

alkyl

pyrido

piperidin

indole

carboxamide

Prior art date

2007-12-12

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.)

Expired - Fee Related

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• -1 amine compounds Chemical class 0.000 title claims description 219
• 150000003857 carboxamides Chemical class 0.000 title claims description 18
• 208000030159 metabolic disease Diseases 0.000 title description 4
• 229940124530 sulfonamide Drugs 0.000 title description 3
• 150000003456 sulfonamides Chemical class 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims description 663
• 150000001875 compounds Chemical class 0.000 claims description 372
• 125000003118 aryl group Chemical group 0.000 claims description 131
• 125000001072 heteroaryl group Chemical group 0.000 claims description 130
• 125000001188 haloalkyl group Chemical group 0.000 claims description 114
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 95
• 229910052799 carbon Inorganic materials 0.000 claims description 90
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 86
• 150000003839 salts Chemical class 0.000 claims description 57
• 229910052736 halogen Inorganic materials 0.000 claims description 55
• 125000004122 cyclic group Chemical group 0.000 claims description 54
• 239000000203 mixture Substances 0.000 claims description 51
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 41
• 150000001204 N-oxides Chemical class 0.000 claims description 35
• 125000005605 benzo group Chemical group 0.000 claims description 33
• 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 claims description 32
• 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• ZQCSYMFYGXRFIJ-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC=4C=NC=CC=4)CC3)=C2CC1 ZQCSYMFYGXRFIJ-UHFFFAOYSA-N 0.000 claims description 11
• 230000037361 pathway Effects 0.000 claims description 11
• 201000001320 Atherosclerosis Diseases 0.000 claims description 10
• YNQXJGXMYJSKIK-UHFFFAOYSA-N 2-benzyl-n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C=1C=C2NC=3CCN(CC=4C=CC=CC=4)CC=3C2=CC=1C(=O)NC(CC1)CCN1CC1=CC=C(C#N)C=C1 YNQXJGXMYJSKIK-UHFFFAOYSA-N 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 8
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 6
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
• 230000027455 binding Effects 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 6
• 230000003213 activating effect Effects 0.000 claims description 5
• BTAIFWSROFGMFY-UHFFFAOYSA-N 2-benzyl-n-[1-(pyridin-4-ylmethyl)piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C=1C=C2NC=3CCN(CC=4C=CC=CC=4)CC=3C2=CC=1C(=O)NC(CC1)CCN1CC1=CC=NC=C1 BTAIFWSROFGMFY-UHFFFAOYSA-N 0.000 claims description 4
• IGGLLQQALORMSZ-UHFFFAOYSA-N 5-methyl-n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C1C=2C3=CC(C(=O)NC4CCN(CC=5C=NC=CC=5)CC4)=CC=C3N(C)C=2CCN1CC1=CC=C(C(F)(F)F)C=C1 IGGLLQQALORMSZ-UHFFFAOYSA-N 0.000 claims description 4
• BCFVDNBHVMIRAB-UHFFFAOYSA-N n-[1-(4-cyanophenyl)sulfonylpiperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)S(=O)(=O)C=3C=CC(=CC=3)C#N)=C2CC1 BCFVDNBHVMIRAB-UHFFFAOYSA-N 0.000 claims description 4
• RCFJOZXVZXSWCF-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[1-(4-fluorophenyl)sulfonylpiperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(F)=CC=C1N1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)S(=O)(=O)C=3C=CC(F)=CC=3)=C2CC1 RCFJOZXVZXSWCF-UHFFFAOYSA-N 0.000 claims description 3
• CVBNRTBWRXYMNS-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[1-(pyridine-3-carbonyl)piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(F)=CC=C1N1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)C(=O)C=3C=NC=CC=3)=C2CC1 CVBNRTBWRXYMNS-UHFFFAOYSA-N 0.000 claims description 3
• HZRXZLQFFZLOCG-UHFFFAOYSA-N 2-[(4-carbamoylphenyl)methyl]-n-[1-(pyridin-4-ylmethyl)piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC=4C=CN=CC=4)CC3)=C2CC1 HZRXZLQFFZLOCG-UHFFFAOYSA-N 0.000 claims description 3
• NAMXHYMYXYEIIH-UHFFFAOYSA-N 2-[(4-carbamoylphenyl)methyl]-n-[1-(pyridine-4-carbonyl)piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)C(=O)C=3C=CN=CC=3)=C2CC1 NAMXHYMYXYEIIH-UHFFFAOYSA-N 0.000 claims description 3
• ORJZEXQGPICXJF-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]methyl]-n-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CCC(NC(=O)C=2C=C3C=4CN(CC=5C=CC(=CC=5)C(F)(F)F)CCC=4NC3=CC=2)CC1 ORJZEXQGPICXJF-UHFFFAOYSA-N 0.000 claims description 3
• PSAKFAMEEFCYHR-UHFFFAOYSA-N 2-benzyl-n-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CCC(NC(=O)C=2C=C3C=4CN(CC=5C=CC=CC=5)CCC=4NC3=CC=2)CC1 PSAKFAMEEFCYHR-UHFFFAOYSA-N 0.000 claims description 3
• NOEUVPVQVYUNNQ-UHFFFAOYSA-N 4-[(4-benzylpiperazin-1-yl)methyl]-n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]benzamide Chemical compound C=1C=C(CN2CCN(CC=3C=CC=CC=3)CC2)C=CC=1C(=O)NC(CC1)CCN1CC1=CC=CN=C1 NOEUVPVQVYUNNQ-UHFFFAOYSA-N 0.000 claims description 3
• YSWUPDVHCQKFEB-UHFFFAOYSA-N 4-[(4-benzylpiperazin-1-yl)methyl]-n-[1-(pyridin-4-ylmethyl)piperidin-4-yl]benzamide Chemical compound C=1C=C(CN2CCN(CC=3C=CC=CC=3)CC2)C=CC=1C(=O)NC(CC1)CCN1CC1=CC=NC=C1 YSWUPDVHCQKFEB-UHFFFAOYSA-N 0.000 claims description 3
• KGFAHANRXJLCME-UHFFFAOYSA-N 5-methyl-2-[[4-(trifluoromethyl)phenyl]methyl]-n-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C1C=2C3=CC(C(=O)NC4CCN(CC=5C=CC(=CC=5)C(F)(F)F)CC4)=CC=C3N(C)C=2CCN1CC1=CC=C(C(F)(F)F)C=C1 KGFAHANRXJLCME-UHFFFAOYSA-N 0.000 claims description 3
• YAJPXWSUYALXJQ-UHFFFAOYSA-N C=1C=CC=CC=1C(C)N(CC1)CCC1NC(=O)C(C=C1C=2C3)=CC=C1NC=2CCN3CC1=CC=C(C(F)(F)F)C=C1 Chemical compound C=1C=CC=CC=1C(C)N(CC1)CCC1NC(=O)C(C=C1C=2C3)=CC=C1NC=2CCN3CC1=CC=C(C(F)(F)F)C=C1 YAJPXWSUYALXJQ-UHFFFAOYSA-N 0.000 claims description 3
• OKBRVRYLWWQBQY-UHFFFAOYSA-N benzyl 8-[[1-[(4-cyanophenyl)methyl]piperidin-4-yl]carbamoyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carboxylate Chemical compound C1CC=2NC3=CC=C(C(=O)NC4CCN(CC=5C=CC(=CC=5)C#N)CC4)C=C3C=2CN1C(=O)OCC1=CC=CC=C1 OKBRVRYLWWQBQY-UHFFFAOYSA-N 0.000 claims description 3
• DQIKAHYIEHONKP-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]methyl]benzamide Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCN(CC=2C=CC(=CC=2)C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)CC1 DQIKAHYIEHONKP-UHFFFAOYSA-N 0.000 claims description 3
• WMIYKDUKJBRSAZ-UHFFFAOYSA-N n-(1-pyridin-3-ylsulfonylpiperidin-4-yl)-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)S(=O)(=O)C=3C=NC=CC=3)=C2CC1 WMIYKDUKJBRSAZ-UHFFFAOYSA-N 0.000 claims description 3
• IMRVWWJADBDGBL-UHFFFAOYSA-N n-[1-(1,3-oxazol-4-ylmethyl)piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC=4N=COC=4)CC3)=C2CC1 IMRVWWJADBDGBL-UHFFFAOYSA-N 0.000 claims description 3
• FZGINFUBHSEKDV-UHFFFAOYSA-N n-[1-(3-cyanophenyl)sulfonylpiperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)S(=O)(=O)C=3C=C(C=CC=3)C#N)=C2CC1 FZGINFUBHSEKDV-UHFFFAOYSA-N 0.000 claims description 3
• CDVFXBMESJKDMD-UHFFFAOYSA-N n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC=4C=NC=CC=4)CC3)=C2CC1 CDVFXBMESJKDMD-UHFFFAOYSA-N 0.000 claims description 3
• DGECFLNJVHGQCN-UHFFFAOYSA-N n-[1-(pyridin-4-ylmethyl)piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC=4C=CN=CC=4)CC3)=C2CC1 DGECFLNJVHGQCN-UHFFFAOYSA-N 0.000 claims description 3
• OGFRKPNRHFGFMY-UHFFFAOYSA-N n-[1-[(1-methylimidazol-4-yl)methyl]piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound CN1C=NC(CN2CCC(CC2)NC(=O)C=2C=C3C=4CN(CC=5C=CC(=CC=5)C(F)(F)F)CCC=4NC3=CC=2)=C1 OGFRKPNRHFGFMY-UHFFFAOYSA-N 0.000 claims description 3
• KKNPTVYJOMDBSC-UHFFFAOYSA-N n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-2-[4-(trifluoromethyl)phenyl]sulfonyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC=4C=CC(=CC=4)C#N)CC3)=C2CC1 KKNPTVYJOMDBSC-UHFFFAOYSA-N 0.000 claims description 3
• ROWAZKLYSMMAGD-UHFFFAOYSA-N n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-5-methyl-2-[[4-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C1C=2C3=CC(C(=O)NC4CCN(CC=5C=CC(=CC=5)C#N)CC4)=CC=C3N(C)C=2CCN1CC1=CC=C(C(F)(F)F)C=C1 ROWAZKLYSMMAGD-UHFFFAOYSA-N 0.000 claims description 3
• DUUPPYOMJAHZDS-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(F)=CC=C1N1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC=4C=NC=CC=4)CC3)=C2CC1 DUUPPYOMJAHZDS-UHFFFAOYSA-N 0.000 claims description 2
• NIKUVLNQFKYFIN-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-n-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC=4C=CC(=CC=4)C(F)(F)F)CC3)=C2CC1 NIKUVLNQFKYFIN-UHFFFAOYSA-N 0.000 claims description 2
• BKBLCVYZVFFSLX-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]methyl]-n-[1-[3-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)S(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)=C2CC1 BKBLCVYZVFFSLX-UHFFFAOYSA-N 0.000 claims description 2
• KOEFDTDROGKCAT-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]methyl]-n-[1-[4-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)S(=O)(=O)C=3C=CC(=CC=3)C(F)(F)F)=C2CC1 KOEFDTDROGKCAT-UHFFFAOYSA-N 0.000 claims description 2
• HNSWNILIGUSVRY-UHFFFAOYSA-N 4-[(4-benzylpiperazin-1-yl)methyl]-n-(1-benzylpiperidin-4-yl)benzamide Chemical compound C=1C=C(CN2CCN(CC=3C=CC=CC=3)CC2)C=CC=1C(=O)NC(CC1)CCN1CC1=CC=CC=C1 HNSWNILIGUSVRY-UHFFFAOYSA-N 0.000 claims description 2
• MRHVTROBWROWAO-UHFFFAOYSA-N 5-acetyl-n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-1h-pyrido[4,3-b]indole-8-carboxamide Chemical compound C1C=2C3=CC(C(=O)NC4CCN(CC=5C=NC=CC=5)CC4)=CC=C3N(C(=O)C)C=2CCN1CC1=CC=C(C(F)(F)F)C=C1 MRHVTROBWROWAO-UHFFFAOYSA-N 0.000 claims description 2
• KVBAIPOJGZVUES-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[[4-(cyclohexylmethyl)piperazin-1-yl]methyl]benzamide Chemical compound C=1C=C(CN2CCN(CC3CCCCC3)CC2)C=CC=1C(=O)NC(CC1)CCN1CC1=CC=CC=C1 KVBAIPOJGZVUES-UHFFFAOYSA-N 0.000 claims description 2
• VHZNWEPBTLBOJL-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-6-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxynaphthalene-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCC(OC=2C=C3C=CC(=CC3=CC=2)C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)CC1 VHZNWEPBTLBOJL-UHFFFAOYSA-N 0.000 claims description 2
• HDMYUOJFXJMKSY-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-6-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]oxynaphthalene-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CCC(OC=2C=C3C=CC(=CC3=CC=2)C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)CC1 HDMYUOJFXJMKSY-UHFFFAOYSA-N 0.000 claims description 2
• IKBHQVYRGCPXOB-UHFFFAOYSA-N n-[1-(pyridine-4-carbonyl)piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)C(=O)C=3C=CN=CC=3)=C2CC1 IKBHQVYRGCPXOB-UHFFFAOYSA-N 0.000 claims description 2
• MJZXWUSXZLKVPF-UHFFFAOYSA-N n-[1-[(3-fluorophenyl)carbamoyl]piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound FC1=CC=CC(NC(=O)N2CCC(CC2)NC(=O)C=2C=C3C=4CN(CC=5C=CC(=CC=5)C(F)(F)F)CCC=4NC3=CC=2)=C1 MJZXWUSXZLKVPF-UHFFFAOYSA-N 0.000 claims description 2
• CPMFDFYIVGIAOS-UHFFFAOYSA-N n-[1-[(4-cyanophenyl)carbamoyl]piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)C(=O)NC=3C=CC(=CC=3)C#N)=C2CC1 CPMFDFYIVGIAOS-UHFFFAOYSA-N 0.000 claims description 2
• VNYBAYCVTPQDHT-UHFFFAOYSA-N n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-2-(4-cyanophenyl)sulfonyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C=1C=C2NC=3CCN(S(=O)(=O)C=4C=CC(=CC=4)C#N)CC=3C2=CC=1C(=O)NC(CC1)CCN1CC1=CC=C(C#N)C=C1 VNYBAYCVTPQDHT-UHFFFAOYSA-N 0.000 claims description 2
• LCPUAANFKRLRTA-UHFFFAOYSA-N n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-2-pyridin-3-ylsulfonyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C=1C=C2NC=3CCN(S(=O)(=O)C=4C=NC=CC=4)CC=3C2=CC=1C(=O)NC(CC1)CCN1CC1=CC=C(C#N)C=C1 LCPUAANFKRLRTA-UHFFFAOYSA-N 0.000 claims description 2
• UTBCSRCIYLJRPJ-UHFFFAOYSA-N n-[1-[[4-(trifluoromethyl)phenyl]carbamoyl]piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)C(=O)NC=3C=CC(=CC=3)C(F)(F)F)=C2CC1 UTBCSRCIYLJRPJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• GYLSDHOBOCPBAT-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-6-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]oxynaphthalene-2-carboxamide Chemical compound C=1C=C2C=C(OC3CCN(CC=4C=CC(=CC=4)C#N)CC3)C=CC2=CC=1C(=O)NC(CC1)CCN1CC1=CC=CC=C1 GYLSDHOBOCPBAT-UHFFFAOYSA-N 0.000 claims 1
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