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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| EP2231600B1 (en) * | 2007-11-16 | 2015-07-29 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| EP2231666B1 (en) | 2007-12-12 | 2015-07-29 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| WO2009132136A1 (en) * | 2008-04-23 | 2009-10-29 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds for the treatment of metabolic disorders |
-
2008
- 2008-12-12 EP EP08860063.0A patent/EP2231666B1/en not_active Not-in-force
- 2008-12-12 CA CA2707047A patent/CA2707047C/en active Active
- 2008-12-12 WO PCT/US2008/086673 patent/WO2009076631A1/en not_active Ceased
- 2008-12-12 JP JP2010538205A patent/JP5650540B2/ja not_active Expired - Fee Related
- 2008-12-12 ES ES08860063.0T patent/ES2553340T3/es active Active
- 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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