JP2011506480A5 - - Google Patents
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- JP2011506480A5 JP2011506480A5 JP2010538205A JP2010538205A JP2011506480A5 JP 2011506480 A5 JP2011506480 A5 JP 2011506480A5 JP 2010538205 A JP2010538205 A JP 2010538205A JP 2010538205 A JP2010538205 A JP 2010538205A JP 2011506480 A5 JP2011506480 A5 JP 2011506480A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- piperidin
- carboxamide
- pyrido
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 347
- 150000001875 compounds Chemical class 0.000 claims description 116
- -1 Tetrahydro-2H-pyran-4-yl Chemical group 0.000 claims description 62
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 239000000651 prodrug Substances 0.000 claims description 17
- 229940002612 prodrug Drugs 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 150000003857 carboxamides Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 150000001204 N-oxides Chemical class 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 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 2
- 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
- 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 2
- 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 2
- 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 2
- OTGWQCQKDUIEOE-UHFFFAOYSA-N 2-[(4-carbamoylphenyl)methyl]-n-[1-[(4-carbamoylphenyl)methyl]piperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1CN1CCC(NC(=O)C=2C=C3C=4CN(CC=5C=CC(=CC=5)C(N)=O)CCC=4NC3=CC=2)CC1 OTGWQCQKDUIEOE-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- XLSJCVMIRMANEV-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound FC(C1=CC=C(CN2CC3=C(NC=4C=CC(=CC3=4)C(=O)N)CC2)C=C1)(F)F XLSJCVMIRMANEV-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
- 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 2
- 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 2
- 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 2
- 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 2
- LRWUVKQKCAKBSO-UHFFFAOYSA-N 4-[(4-benzylpiperazin-1-yl)methyl]-N-(1-benzylpiperidin-4-yl)benzamide N-(1-benzylpiperidin-4-yl)-4-[[4-(cyclohexylmethyl)piperazin-1-yl]methyl]benzamide Chemical compound O=C(NC1CCN(Cc2ccccc2)CC1)c1ccc(CN2CCN(CC3CCCCC3)CC2)cc1.O=C(NC1CCN(Cc2ccccc2)CC1)c1ccc(CN2CCN(Cc3ccccc3)CC2)cc1 LRWUVKQKCAKBSO-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 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
- 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 2
- 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 description 2
- 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 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 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 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 claims description 2
- NEVHNIWAXGKTBI-UHFFFAOYSA-N O=C(NC1CCN(Cc2ccccc2)CC1)c1ccc2cc(OC3CCN(Cc4ccc(cc4)C#N)CC3)ccc2c1.FC(F)(F)c1ccc(cc1)N1CCC(CC1)Oc1ccc2cc(ccc2c1)C(=O)NC1CCN(Cc2ccccc2)CC1 Chemical compound O=C(NC1CCN(Cc2ccccc2)CC1)c1ccc2cc(OC3CCN(Cc4ccc(cc4)C#N)CC3)ccc2c1.FC(F)(F)c1ccc(cc1)N1CCC(CC1)Oc1ccc2cc(ccc2c1)C(=O)NC1CCN(Cc2ccccc2)CC1 NEVHNIWAXGKTBI-UHFFFAOYSA-N 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 2
- CPBDISFQIOZKMH-UHFFFAOYSA-N benzyl 8-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]carbamoyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC(=O)C1=CC=C(NC2=C3CN(CC2)C(=O)OCC=2C=CC=CC=2)C3=C1 CPBDISFQIOZKMH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 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 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
- 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 2
- 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 2
- 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 2
- 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 2
- AVMQVXRALLUWAU-UHFFFAOYSA-N n-[1-(4-fluorophenyl)sulfonylpiperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CCC(NC(=O)C=2C=C3C=4CN(CC=5C=CC(=CC=5)C(F)(F)F)CCC=4NC3=CC=2)CC1 AVMQVXRALLUWAU-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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 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
- 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
- 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 2
- 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 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
- 230000037361 pathway Effects 0.000 claims description 2
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Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2079694B1 (en) | 2006-12-28 | 2017-03-01 | Rigel Pharmaceuticals, Inc. | N-substituted-heterocycloalkyloxybenzamide compounds and methods of use |
| KR101573091B1 (ko) | 2007-11-16 | 2015-11-30 | 리겔 파마슈티칼스, 인크. | 대사성 장애를 위한 카르복스아미드, 술폰아미드 및 아민 화합물 |
| ES2699627T3 (es) * | 2007-11-30 | 2019-02-12 | Siemens Healthcare Diagnostics Inc | Fragmentos de receptores de adiponectina y métodos de uso |
| CA2707047C (en) * | 2007-12-12 | 2017-11-28 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| CA2722139C (en) * | 2008-04-23 | 2017-04-11 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds for the treatment of metabolic disorders |
| NZ594556A (en) * | 2009-01-28 | 2013-11-29 | Rigel Pharmaceuticals Inc | Carboxamide compounds and methods for using the same |
| JP2012527474A (ja) | 2009-05-22 | 2012-11-08 | エクセリクシス， インク． | 増殖性疾患に対するベンゾキサゼピンベースのｐｉ３ｋ／ｍｔ０ｒ阻害剤 |
| GB0915892D0 (en) * | 2009-09-10 | 2009-10-14 | Smithkline Beecham Corp | Compounds |
| WO2011032320A1 (en) * | 2009-09-21 | 2011-03-24 | F. Hoffmann-La Roche Ag | Novel alkene oxindole derivatives |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2011123681A1 (en) | 2010-03-31 | 2011-10-06 | Rigel Pharmaceuticals, Inc. | Methods for using carboxamide, sulfonamide and amine compounds |
| TW201211053A (en) * | 2010-05-10 | 2012-03-16 | Nissan Chemical Ind Ltd | Spiro compound and drug for activating adiponectin receptor |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| UA112517C2 (uk) | 2010-07-06 | 2016-09-26 | Новартіс Аг | Тетрагідропіридопіримідинові похідні |
| CA2806341C (en) | 2010-07-29 | 2020-03-24 | Rigel Pharmaceuticals, Inc. | Ampk-activating heterocyclic compounds and methods for using the same |
| US9005909B2 (en) | 2011-01-06 | 2015-04-14 | Rigel Pharmaceuticals, Inc. | Whole blood assay for measuring AMPK activation |
| KR101624020B1 (ko) | 2011-03-07 | 2016-05-24 | 글락소스미스클라인 엘엘씨 | 퀴놀리논 유도체 |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013042782A1 (ja) | 2011-09-22 | 2013-03-28 | 武田薬品工業株式会社 | 縮合複素環化合物 |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9409884B2 (en) | 2012-02-01 | 2016-08-09 | Rigel Pharmaceuticals, Inc. | 5- or 6-substituted benzofuran-2-carboxamide compounds and methods for using them |
| WO2015046595A1 (ja) | 2013-09-30 | 2015-04-02 | 国立大学法人東京大学 | アディポネクチン受容体活性化化合物 |
| US20210238162A1 (en) * | 2015-12-17 | 2021-08-05 | Glaxosmithkline Intellectual Property Development Limited | Chemical compounds |
| RU2732075C1 (ru) * | 2019-07-24 | 2020-09-11 | Федеральное государственное бюджетное учреждение науки Институт аналитического приборостроения Российской академии наук | Способ предварительной сепарации потока заряженных частиц в источнике ионов с ионизацией при атмосферном давлении |
| AU2021275038A1 (en) | 2020-05-19 | 2022-12-22 | Kallyope, Inc. | AMPK activators |
| CA3183575A1 (en) | 2020-06-26 | 2021-12-30 | Iyassu Sebhat | Ampk activators |
Family Cites Families (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5028A (en) * | 1847-03-20 | monohot | ||
| EP0227640B1 (de) * | 1982-09-30 | 1993-05-26 | Ciba-Geigy Ag | Mit Bis-(polyalkylpiperidinyl-amino)-1,3,5-triazinen stabilisierte Polyolefine |
| GB8820115D0 (en) | 1988-08-24 | 1988-09-28 | Ici Plc | Insecticidal compounds |
| US5216156A (en) * | 1992-05-05 | 1993-06-01 | Ciba-Geigy Corporation | Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives |
| US6137002A (en) | 1993-07-22 | 2000-10-24 | Eli Lilly And Company | Glycoprotein IIb/IIIa antagonists |
| NZ331490A (en) | 1996-03-28 | 2000-06-23 | Glaxo Group Ltd | Pyrrolopyrrolone derivatives for the treatment or prophylaxis of inflammatory disease such as chronic bronchitis, obstructive pulmonary disease and asthma |
| GB9715584D0 (en) | 1997-07-23 | 1997-10-01 | Eisai Co Ltd | Compounds |
| DE19738615A1 (de) | 1997-09-04 | 1999-03-11 | Clariant Gmbh | Neue Lichtschutzmittel auf Basis von sterisch gehinderten Aminen |
| US6589954B1 (en) | 1998-05-22 | 2003-07-08 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| EP1107758A2 (en) | 1998-08-28 | 2001-06-20 | Scios Inc. | Use of piperidines and/or piperazines as inhibitors of p38-alpha kinase |
| US6953855B2 (en) | 1998-12-11 | 2005-10-11 | Targacept, Inc. | 3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof |
| DK1218380T3 (da) | 1999-10-08 | 2004-03-15 | Gruenenthal Gmbh | Bicykliske imidazo-3-yl-aminoderivater substitueret i seksledsringen |
| US6436965B1 (en) | 2000-03-02 | 2002-08-20 | Merck Frosst Canada & Co. | PDE IV inhibiting amides, compositions and methods of treatment |
| US7273868B2 (en) | 2000-04-28 | 2007-09-25 | Tanabe Seiyaku Co., Ltd. | Pyrazine derivatives |
| US6579328B2 (en) * | 2000-05-01 | 2003-06-17 | Ciba Specialty Chemicals Corporation | Transition-metal-catalyzed process for the preparation of sterically hindered N-substituted aryloxyamines |
| AU2001273040A1 (en) | 2000-06-27 | 2002-01-08 | Du Pont Pharmaceuticals Company | Factor xa inhibitors |
| DE10050663A1 (de) | 2000-10-13 | 2002-04-18 | Gruenenthal Gmbh | Verwendung von substituierten Imidazo[1,2-a]pyridin-, -pyrimidin- und pyrazin-3-yl-amin-Derivaten zur Herstellung von Medikamenten zur NOS-Inhibierung |
| HU230302B1 (hu) | 2000-10-20 | 2015-12-28 | Eisai R&D Management Co., Ltd. | Nitrogéntartalmú aromás származékok és ezeket tartalmazó gyógyászati készítmények |
| WO2002089749A2 (en) | 2001-05-10 | 2002-11-14 | Abbott Gmbh & Co.Kg | Arylsulfonamide ethers, and methods of use thereof |
| WO2002094796A2 (en) * | 2001-05-18 | 2002-11-28 | Axxima Pharmaceuticals Ag | Benzo[g]quinoxaline derivatives as effective compounds against infectious diseases |
| BR0212123A (pt) | 2001-08-24 | 2004-07-20 | Upjohn Co | 7-aza[2.2.1]biciclo-heptanos substituìdos com arila para o tratamento de doenças |
| EP1425286B1 (en) | 2001-09-12 | 2007-02-28 | Pharmacia & Upjohn Company LLC | Substituted 7-aza-[2.2.1]bicycloheptanes for the treatment of diseases |
| TW200407307A (en) * | 2001-11-26 | 2004-05-16 | Ciba Sc Holding Ag | Process for the synthesis of amine ethers from secondary amino oxides |
| CA2476681A1 (en) | 2002-02-19 | 2003-08-28 | Bruce N. Rogers | Fused bicyclic-n-bridged-heteroaromatic carboxamides for the treatment of disease |
| MXPA04007083A (es) | 2002-02-20 | 2004-10-29 | Upjohn Co | Compuestos azabiciclicos para el tratamiento de enfermedades. |
| AU2003245669A1 (en) | 2002-06-21 | 2004-01-06 | Cellular Genomics, Inc. | Certain aromatic monocycles as kinase modulators |
| EP1569646A2 (en) | 2002-12-13 | 2005-09-07 | Smithkline Beecham Corporation | Piperidine derivatives as ccr5 antagonists |
| US7208491B2 (en) | 2003-02-07 | 2007-04-24 | Hoffmann-La Roche Inc. | N-monoacylated o-phenylenediamines |
| GB2400101A (en) | 2003-03-28 | 2004-10-06 | Biofocus Discovery Ltd | Compounds capable of binding to the active site of protein kinases |
| GB0314054D0 (en) | 2003-06-17 | 2003-07-23 | Pfizer Ltd | Amide derivatives as selective serotonin re-uptake inhibitors |
| TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| EP1663204B1 (en) | 2003-08-29 | 2014-05-07 | Exelixis, Inc. | C-kit modulators and methods of use |
| JP2007516256A (ja) * | 2003-12-12 | 2007-06-21 | イーライ リリー アンド カンパニー | オピオイド受容体拮抗物質 |
| US7544803B2 (en) | 2004-01-23 | 2009-06-09 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| PE20060315A1 (es) | 2004-05-24 | 2006-05-15 | Irm Llc | Compuestos de tiazol como moduladores de ppar |
| CN1960727B (zh) | 2004-06-02 | 2011-02-16 | 霍夫曼-拉罗奇有限公司 | 用作组胺-3受体的配体的萘衍生物 |
| CN1972926B (zh) | 2004-06-21 | 2011-02-16 | 霍夫曼-拉罗奇有限公司 | 作为组胺受体拮抗剂的吲哚衍生物 |
| ATE517882T1 (de) | 2004-10-19 | 2011-08-15 | Hoffmann La Roche | Chinolinderivate |
| AU2005300150A1 (en) | 2004-10-29 | 2006-05-04 | Astrazeneca Ab | Novel sulphonamide derivatives as glucocorticoid receptor modulators for the treatment of inflammatory diseases |
| CN101098870B (zh) | 2004-11-08 | 2010-11-03 | 万有制药株式会社 | 新型稠环咪唑衍生物 |
| US20080125432A1 (en) | 2004-12-01 | 2008-05-29 | Devgen Nv | 5-Carboxamido Substituted Thiazole Derivatives that Interact With Ion Channels, In Particular With Ion Channels From the Kv Family |
| EP1838312A4 (en) | 2004-12-17 | 2010-01-20 | Smithkline Beecham Corp | CHEMICAL COMPOUNDS |
| BRPI0517211B8 (pt) | 2004-12-17 | 2021-05-25 | Glenmark Pharmaceuticals Sa | composto, composição farmacêutica e seu uso. |
| GB0428235D0 (en) | 2004-12-23 | 2005-01-26 | Glaxo Group Ltd | Novel compounds |
| EP1844023A1 (en) * | 2004-12-31 | 2007-10-17 | Sk Chemicals Co., Ltd. | Quinazoline derivatives for the treatment and prevention of diabetes and obesity |
| CA2599987A1 (en) | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | Fused heterocyclic compounds and their use as sirtuin modulators |
| US7893267B2 (en) | 2005-03-14 | 2011-02-22 | High Point Pharmaceuticals, Llc | Benzazole derivatives, compositions, and methods of use as β-secretase inhibitors |
| EP1863810A4 (en) | 2005-03-22 | 2010-03-31 | Astrazeneca Ab | NEW TETRAHYDRO-1H-PYRIDO [4,3-B] INDOLDERIVATE AS CB1 'RECEPTOR LIGANDS |
| GB0508472D0 (en) | 2005-04-26 | 2005-06-01 | Glaxo Group Ltd | Compounds |
| JP2009500419A (ja) | 2005-07-05 | 2009-01-08 | アリックス セラピューティクス、インコーポレイテッド | 立体異性体のピリジル及びピリドニル化合物並びに消化管障害及び中枢神経系障害の治療方法 |
| WO2007007688A1 (ja) * | 2005-07-08 | 2007-01-18 | Mochida Pharmaceutical Co., Ltd. | ３,５－ジアミノ－１,２,４－トリアゾール誘導体 |
| US20070032502A1 (en) * | 2005-07-15 | 2007-02-08 | Schering Corporation | Quinazoline derivatives useful in cancer treatment |
| KR101047204B1 (ko) | 2005-11-30 | 2011-07-06 | 에프. 호프만-라 로슈 아게 | Ｈ3 조절제로서 사용하기 위한1,1-다이옥소-싸이오모폴린일 인돌일 메탄온 유도체 |
| AU2006319916A1 (en) * | 2005-11-30 | 2007-06-07 | Astellas Pharma Inc. | 2-aminobenzamide derivative |
| ES2342979T3 (es) | 2005-11-30 | 2010-07-20 | F. Hoffmann-La Roche Ag | Derivados de indol-2-carboxamida sustituidos en 5. |
| CN101316840B (zh) | 2005-11-30 | 2012-08-08 | 霍夫曼-拉罗奇有限公司 | 1,5-取代的吲哚-2-基酰胺衍生物 |
| WO2007075688A2 (en) * | 2005-12-21 | 2007-07-05 | Schering Corporation | Substituted aniline derivatives useful as histamine h3 antagonists |
| JP2009524689A (ja) | 2006-01-25 | 2009-07-02 | スミスクライン ビーチャム コーポレーション | 化合物 |
| TW200738711A (en) | 2006-01-25 | 2007-10-16 | Smithkline Beecham Corp | Chemical compounds |
| WO2007098086A2 (en) * | 2006-02-17 | 2007-08-30 | Avalon Pharmaceuticals | Hydroxypiperidine derivatives and uses thereof |
| WO2007099423A1 (en) | 2006-03-02 | 2007-09-07 | Pfizer Products Inc. | 1-pyrrolidine indane derivatives as histamine-3 receptor antagonists |
| CN101421235A (zh) * | 2006-04-12 | 2009-04-29 | 霍夫曼-拉罗奇有限公司 | 5-酰氨基-2-酰胺吲哚 |
| NL2000581C2 (nl) | 2006-04-20 | 2008-01-03 | Pfizer Prod Inc | Aangecondenseerde fenylamidoheterocyclische verbindingen. |
| EP2032566A4 (en) | 2006-06-12 | 2009-07-08 | Merck Frosst Canada Ltd | AZETIDINE DERIVATIVES AS INHIBITORS OF STEAROYL-COENZYME-A-DELTA-9-DESATURASE |
| CA2654098A1 (en) | 2006-06-13 | 2007-12-21 | Merck Frosst Canada Ltd. | Azacyclopentane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| TW200821303A (en) | 2006-08-08 | 2008-05-16 | Speedel Experimenta Ag | Organic compounds |
| EP2079694B1 (en) | 2006-12-28 | 2017-03-01 | Rigel Pharmaceuticals, Inc. | N-substituted-heterocycloalkyloxybenzamide compounds and methods of use |
| JP2010527915A (ja) | 2007-04-26 | 2010-08-19 | アバロン ファーマシューティカルズ，インコーポレイテッド | 多重環化合物及びその用途 |
| NZ585137A (en) * | 2007-10-25 | 2012-07-27 | Exelixis Inc | Tropane compounds useful as hsp90 inhibitors |
| KR101573091B1 (ko) * | 2007-11-16 | 2015-11-30 | 리겔 파마슈티칼스, 인크. | 대사성 장애를 위한 카르복스아미드, 술폰아미드 및 아민 화합물 |
| CA2707047C (en) | 2007-12-12 | 2017-11-28 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| CA2722139C (en) * | 2008-04-23 | 2017-04-11 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds for the treatment of metabolic disorders |
-
2008
- 2008-12-12 CA CA2707047A patent/CA2707047C/en active Active
- 2008-12-12 ES ES08860063.0T patent/ES2553340T3/es active Active
- 2008-12-12 JP JP2010538205A patent/JP5650540B2/ja not_active Expired - Fee Related
- 2008-12-12 EP EP08860063.0A patent/EP2231666B1/en not_active Not-in-force
- 2008-12-12 WO PCT/US2008/086673 patent/WO2009076631A1/en not_active Ceased
- 2008-12-12 US US12/334,201 patent/US8129390B2/en active Active
-
2012
- 2012-01-11 US US13/348,384 patent/US8557822B2/en not_active Expired - Fee Related
-
2013
- 2013-10-14 US US14/053,328 patent/US8895578B2/en active Active
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