JP2006521358A5 - - Google Patents
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- JP2006521358A5 JP2006521358A5 JP2006507424A JP2006507424A JP2006521358A5 JP 2006521358 A5 JP2006521358 A5 JP 2006521358A5 JP 2006507424 A JP2006507424 A JP 2006507424A JP 2006507424 A JP2006507424 A JP 2006507424A JP 2006521358 A5 JP2006521358 A5 JP 2006521358A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- carboxamide
- dihydro
- pyridine
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 27
- -1 benzimidazolonyl Chemical group 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 2
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 claims 2
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 241000534944 Thia Species 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000003943 azolyl group Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004623 carbolinyl group Chemical group 0.000 claims 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 2
- 125000005436 dihydrobenzothiophenyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims 2
- 125000005435 dihydrobenzoxazolyl group Chemical group O1C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 2
- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims 2
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 claims 2
- 125000005049 dihydrooxadiazolyl group Chemical group O1N(NC=C1)* 0.000 claims 2
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims 2
- 125000005051 dihydropyrazinyl group Chemical group N1(CC=NC=C1)* 0.000 claims 2
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims 2
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims 2
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims 2
- 125000005058 dihydrotriazolyl group Chemical group N1(NNC=C1)* 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000002708 enhancing effect Effects 0.000 claims 2
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- UFOUABRZSDGGAZ-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]-2-hydroxybenzamide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=C(Cl)C=C1CN1C(=O)C2=CC=CC=C2C1=O UFOUABRZSDGGAZ-UHFFFAOYSA-N 0.000 claims 2
- ZKYBTUSVWGDOKG-UHFFFAOYSA-N n-[[5-bromo-2-(pyridine-2-carbonylamino)phenyl]methyl]pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NCC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 ZKYBTUSVWGDOKG-UHFFFAOYSA-N 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000005545 phthalimidyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229930195712 glutamate Natural products 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- LYJAGGFAHZPMIQ-UHFFFAOYSA-N n-[(2-benzamido-5-bromophenyl)methyl]-n,3,5-trimethylbenzamide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C)CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=C1 LYJAGGFAHZPMIQ-UHFFFAOYSA-N 0.000 claims 1
- WUVLZNSKQMTNEG-UHFFFAOYSA-N n-[2-[(1,3-dioxoisoindol-2-yl)methyl]-3-fluorophenyl]-2-fluorobenzamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC=1C(F)=CC=CC=1NC(=O)C1=CC=CC=C1F WUVLZNSKQMTNEG-UHFFFAOYSA-N 0.000 claims 1
- GERLAVYIUACXNC-UHFFFAOYSA-N n-[2-[(1,3-dioxoisoindol-2-yl)methyl]-3-fluorophenyl]-2-hydroxybenzamide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC(F)=C1CN1C(=O)C2=CC=CC=C2C1=O GERLAVYIUACXNC-UHFFFAOYSA-N 0.000 claims 1
- QVZVAJPWBPGBLL-UHFFFAOYSA-N n-[2-[(1,3-dioxoisoindol-2-yl)methyl]-3-fluorophenyl]-3,5-difluorobenzamide Chemical compound FC1=CC(F)=CC(C(=O)NC=2C(=C(F)C=CC=2)CN2C(C3=CC=CC=C3C2=O)=O)=C1 QVZVAJPWBPGBLL-UHFFFAOYSA-N 0.000 claims 1
- JEHCNVSVMVZEBT-UHFFFAOYSA-N n-[2-[(1,3-dioxoisoindol-2-yl)methyl]-3-fluorophenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC=1C(F)=CC=CC=1NC(=O)C1=CC=CC=C1 JEHCNVSVMVZEBT-UHFFFAOYSA-N 0.000 claims 1
- KBUYPHYBNUWEIJ-UHFFFAOYSA-N n-[2-[(1,3-dioxoisoindol-2-yl)methyl]-4-methoxyphenyl]pyridine-2-carboxamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC(OC)=CC=C1NC(=O)C1=CC=CC=N1 KBUYPHYBNUWEIJ-UHFFFAOYSA-N 0.000 claims 1
- XGOOSXFYCRTVGG-UHFFFAOYSA-N n-[2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C=CC=C(CN2C(C3=CC=CC=C3C2=O)=O)C=1NC(=O)C1=CC=CC=N1 XGOOSXFYCRTVGG-UHFFFAOYSA-N 0.000 claims 1
- KEPIKEBSJNNFTQ-UHFFFAOYSA-N n-[2-[(4,6-dichloro-1,3-dioxoisoindol-2-yl)methyl]-4-fluorophenyl]pyridine-2-carboxamide Chemical compound O=C1C2=CC(Cl)=CC(Cl)=C2C(=O)N1CC1=CC(F)=CC=C1NC(=O)C1=CC=CC=N1 KEPIKEBSJNNFTQ-UHFFFAOYSA-N 0.000 claims 1
- SXYMBZYYIPCZNG-UHFFFAOYSA-N n-[2-[(5,6-dichloro-1,3-dioxoisoindol-2-yl)methyl]-4-fluorophenyl]pyridine-2-carboxamide Chemical compound O=C1C2=CC(Cl)=C(Cl)C=C2C(=O)N1CC1=CC(F)=CC=C1NC(=O)C1=CC=CC=N1 SXYMBZYYIPCZNG-UHFFFAOYSA-N 0.000 claims 1
- LHEXNEPHTRPWRP-UHFFFAOYSA-N n-[2-[[(4-butoxybenzoyl)-ethylamino]methyl]-4-chlorophenyl]pyridine-2-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1C(=O)N(CC)CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 LHEXNEPHTRPWRP-UHFFFAOYSA-N 0.000 claims 1
- ILUZEEKKNJMAEA-UHFFFAOYSA-N n-[2-[[(4-butoxybenzoyl)amino]methyl]-4-fluorophenyl]pyridine-2-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1C(=O)NCC1=CC(F)=CC=C1NC(=O)C1=CC=CC=N1 ILUZEEKKNJMAEA-UHFFFAOYSA-N 0.000 claims 1
- KRBXTRMWKLVWRS-UHFFFAOYSA-N n-[2-[[[3,5-bis(trifluoromethyl)benzoyl]-methylamino]methyl]-4-chlorophenyl]pyridine-2-carboxamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(=O)N(C)CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 KRBXTRMWKLVWRS-UHFFFAOYSA-N 0.000 claims 1
- AFTRJAHNDQZZOR-UHFFFAOYSA-N n-[4-bromo-2-[(4,6-dichloro-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C=2C(Cl)=CC(Cl)=CC=2C(=O)N1CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 AFTRJAHNDQZZOR-UHFFFAOYSA-N 0.000 claims 1
- HLGQBOQZDVJHKV-UHFFFAOYSA-N n-[4-bromo-2-[(4-fluoro-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C=2C(F)=CC=CC=2C(=O)N1CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 HLGQBOQZDVJHKV-UHFFFAOYSA-N 0.000 claims 1
- ITJDRUPTGGBFCK-UHFFFAOYSA-N n-[4-bromo-2-[(4-methyl-1,3-dioxo-5,6-dihydro-4h-cyclopenta[c]pyrrol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound CC1CCC(C2=O)=C1C(=O)N2CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 ITJDRUPTGGBFCK-UHFFFAOYSA-N 0.000 claims 1
- INILUHFLFKQYPV-UHFFFAOYSA-N n-[4-bromo-2-[(5,6-dichloro-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C=2C=C(Cl)C(Cl)=CC=2C(=O)N1CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 INILUHFLFKQYPV-UHFFFAOYSA-N 0.000 claims 1
- DQKUVCQNBYDJAW-UHFFFAOYSA-N n-[4-bromo-2-[(5-ethoxy-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C2=CC(OCC)=CC=C2C(=O)N1CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 DQKUVCQNBYDJAW-UHFFFAOYSA-N 0.000 claims 1
- IYPWCWQNVRQIKS-UHFFFAOYSA-N n-[4-bromo-2-[(5-fluoro-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C2=CC(F)=CC=C2C(=O)N1CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 IYPWCWQNVRQIKS-UHFFFAOYSA-N 0.000 claims 1
- HABBKKCXCKQVIA-UHFFFAOYSA-N n-[4-bromo-2-[[(2,4-difluorobenzoyl)-methylamino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C=C(F)C=C(F)C=1C(=O)N(C)CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 HABBKKCXCKQVIA-UHFFFAOYSA-N 0.000 claims 1
- PPMSJIUCBOVLKA-UHFFFAOYSA-N n-[4-bromo-2-[[(2-fluorobenzoyl)amino]methyl]phenyl]pyridine-2-carboxamide Chemical compound FC1=CC=CC=C1C(=O)NCC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 PPMSJIUCBOVLKA-UHFFFAOYSA-N 0.000 claims 1
- KKUJWDIQLCEKTM-UHFFFAOYSA-N n-[4-bromo-2-[[(3,4-dichlorobenzoyl)-methylamino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)N(C)CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 KKUJWDIQLCEKTM-UHFFFAOYSA-N 0.000 claims 1
- WEBSUSRUVQDKRQ-UHFFFAOYSA-N n-[4-bromo-2-[[(3,4-difluorobenzoyl)-methylamino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C=C(F)C(F)=CC=1C(=O)N(C)CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 WEBSUSRUVQDKRQ-UHFFFAOYSA-N 0.000 claims 1
- DXUZTWQZFRCOBQ-UHFFFAOYSA-N n-[4-bromo-2-[[(3,5-dichlorobenzoyl)-methylamino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(=O)N(C)CC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 DXUZTWQZFRCOBQ-UHFFFAOYSA-N 0.000 claims 1
- KQOVVZRIDHEVAK-UHFFFAOYSA-N n-[4-bromo-2-[[(3-methoxybenzoyl)-methylamino]methyl]phenyl]pyridine-2-carboxamide Chemical compound COC1=CC=CC(C(=O)N(C)CC=2C(=CC=C(Br)C=2)NC(=O)C=2N=CC=CC=2)=C1 KQOVVZRIDHEVAK-UHFFFAOYSA-N 0.000 claims 1
- XHICOKRZZFLUJA-UHFFFAOYSA-N n-[4-bromo-2-[[[2-(trifluoromethyl)benzoyl]amino]methyl]phenyl]pyridine-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)NCC1=CC(Br)=CC=C1NC(=O)C1=CC=CC=N1 XHICOKRZZFLUJA-UHFFFAOYSA-N 0.000 claims 1
- IETGCFRJUMBEJY-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]-1,2,5-thiadiazole-3-carboxamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C=1C=NSN=1 IETGCFRJUMBEJY-UHFFFAOYSA-N 0.000 claims 1
- LZCIHXJZKGVUBB-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]-1,3-thiazole-4-carboxamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=CSC=N1 LZCIHXJZKGVUBB-UHFFFAOYSA-N 0.000 claims 1
- RTCPGNXGDXKRBK-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]-1-methylimidazole-2-carboxamide Chemical compound CN1C=CN=C1C(=O)NC1=CC=C(Cl)C=C1CN1C(=O)C2=CC=CC=C2C1=O RTCPGNXGDXKRBK-UHFFFAOYSA-N 0.000 claims 1
- VUOLSIXUEZJCIP-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=C(Cl)C=C1CN1C(=O)C2=CC=CC=C2C1=O VUOLSIXUEZJCIP-UHFFFAOYSA-N 0.000 claims 1
- CIKGPUMGMDFOOC-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]-3-hydroxypyridine-2-carboxamide Chemical compound OC1=CC=CN=C1C(=O)NC1=CC=C(Cl)C=C1CN1C(=O)C2=CC=CC=C2C1=O CIKGPUMGMDFOOC-UHFFFAOYSA-N 0.000 claims 1
- URSPQVYFZHQLIN-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C(=CC(Cl)=CC=2)CN2C(C3=CC=CC=C3C2=O)=O)=C1 URSPQVYFZHQLIN-UHFFFAOYSA-N 0.000 claims 1
- YZDIYQCWDBEGQT-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC=2C(=CC(Cl)=CC=2)CN2C(C3=CC=CC=C3C2=O)=O)=N1 YZDIYQCWDBEGQT-UHFFFAOYSA-N 0.000 claims 1
- LWGKDNSBIOCANF-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]cyclohexanecarboxamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1CCCCC1 LWGKDNSBIOCANF-UHFFFAOYSA-N 0.000 claims 1
- PASZTKJWCDEAIE-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]furan-2-carboxamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CO1 PASZTKJWCDEAIE-UHFFFAOYSA-N 0.000 claims 1
- ORCGRLKKRDOYQI-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]imidazo[2,1-b][1,3]thiazole-6-carboxamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=CN(C=CS2)C2=N1 ORCGRLKKRDOYQI-UHFFFAOYSA-N 0.000 claims 1
- USYDGTLOPLIFMI-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 USYDGTLOPLIFMI-UHFFFAOYSA-N 0.000 claims 1
- DUGNCJWJJGAZFI-UHFFFAOYSA-N n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]pyrimidine-2-carboxamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=NC=CC=N1 DUGNCJWJJGAZFI-UHFFFAOYSA-N 0.000 claims 1
- ORCJGIAUEQWOBH-UHFFFAOYSA-N n-[4-chloro-2-[(2,5-dioxo-3-phenylpyrrol-1-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C=C(C=2C=CC=CC=2)C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 ORCJGIAUEQWOBH-UHFFFAOYSA-N 0.000 claims 1
- WBXKMHFMMCOTOK-UHFFFAOYSA-N n-[4-chloro-2-[(4-fluoro-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C=2C(F)=CC=CC=2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 WBXKMHFMMCOTOK-UHFFFAOYSA-N 0.000 claims 1
- YMDUTBCXGSCOQI-UHFFFAOYSA-N n-[4-chloro-2-[(5,6-dimethyl-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C=2C=C(C)C(C)=CC=2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 YMDUTBCXGSCOQI-UHFFFAOYSA-N 0.000 claims 1
- MFNLYFOKMBXZFR-UHFFFAOYSA-N n-[4-chloro-2-[(5-ethoxy-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C2=CC(OCC)=CC=C2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 MFNLYFOKMBXZFR-UHFFFAOYSA-N 0.000 claims 1
- YQBPEFYDKGHACA-UHFFFAOYSA-N n-[4-chloro-2-[(5-fluoro-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C2=CC(F)=CC=C2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 YQBPEFYDKGHACA-UHFFFAOYSA-N 0.000 claims 1
- HRSBHPKGNFMMLX-UHFFFAOYSA-N n-[4-chloro-2-[(5-hydroxy-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C2=CC(O)=CC=C2C(=O)N1CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 HRSBHPKGNFMMLX-UHFFFAOYSA-N 0.000 claims 1
- VZTQRKWQFHCAPP-UHFFFAOYSA-N n-[4-chloro-2-[[(3,4-dichlorobenzoyl)-methylamino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)N(C)CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 VZTQRKWQFHCAPP-UHFFFAOYSA-N 0.000 claims 1
- CBABSDKXEBXXLD-UHFFFAOYSA-N n-[4-chloro-2-[[(3,5-dichlorobenzoyl)-(2-methylpropyl)amino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(=O)N(CC(C)C)CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 CBABSDKXEBXXLD-UHFFFAOYSA-N 0.000 claims 1
- PUBHTMZIWJOLAV-UHFFFAOYSA-N n-[4-chloro-2-[[(3,5-dichlorobenzoyl)-[2-(dimethylamino)ethyl]amino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(=O)N(CCN(C)C)CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 PUBHTMZIWJOLAV-UHFFFAOYSA-N 0.000 claims 1
- JZKUQLOOJQQEOC-UHFFFAOYSA-N n-[4-chloro-2-[[(3,5-dichlorobenzoyl)-ethylamino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(=O)N(CC)CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 JZKUQLOOJQQEOC-UHFFFAOYSA-N 0.000 claims 1
- YOJHSDOFGNSSRQ-UHFFFAOYSA-N n-[4-chloro-2-[[(3,5-dichlorobenzoyl)-methylamino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(=O)N(C)CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 YOJHSDOFGNSSRQ-UHFFFAOYSA-N 0.000 claims 1
- CUKULHXSSDBCQK-UHFFFAOYSA-N n-[4-chloro-2-[[(3,5-dimethoxybenzoyl)-(2-methylpropyl)amino]methyl]phenyl]pyridine-2-carboxamide Chemical compound COC1=CC(OC)=CC(C(=O)N(CC(C)C)CC=2C(=CC=C(Cl)C=2)NC(=O)C=2N=CC=CC=2)=C1 CUKULHXSSDBCQK-UHFFFAOYSA-N 0.000 claims 1
- GNAILYLKTHOYJL-UHFFFAOYSA-N n-[4-chloro-2-[[(3,5-dimethoxybenzoyl)-ethylamino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C(OC)=CC(OC)=CC=1C(=O)N(CC)CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 GNAILYLKTHOYJL-UHFFFAOYSA-N 0.000 claims 1
- KCRMBWJGSAKJPS-UHFFFAOYSA-N n-[4-chloro-2-[[methyl-[2-(trifluoromethyl)benzoyl]amino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(=O)N(C)CC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=N1 KCRMBWJGSAKJPS-UHFFFAOYSA-N 0.000 claims 1
- QENKUXSIVHZOKM-UHFFFAOYSA-N n-[4-fluoro-2-[(5-nitro-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide Chemical compound O=C1C2=CC([N+](=O)[O-])=CC=C2C(=O)N1CC1=CC(F)=CC=C1NC(=O)C1=CC=CC=N1 QENKUXSIVHZOKM-UHFFFAOYSA-N 0.000 claims 1
- UXMZCQKEWDNWDG-UHFFFAOYSA-N n-[5-bromo-3-[(5,6-dichloro-1,3-dioxoisoindol-2-yl)methyl]pyridin-2-yl]pyridine-2-carboxamide Chemical compound O=C1C=2C=C(Cl)C(Cl)=CC=2C(=O)N1CC1=CC(Br)=CN=C1NC(=O)C1=CC=CC=N1 UXMZCQKEWDNWDG-UHFFFAOYSA-N 0.000 claims 1
- UKUOAARHLKXWBP-UHFFFAOYSA-N n-[5-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]cyclohexanecarboxamide Chemical compound C=1C(Cl)=CC=C(CN2C(C3=CC=CC=C3C2=O)=O)C=1NC(=O)C1CCCCC1 UKUOAARHLKXWBP-UHFFFAOYSA-N 0.000 claims 1
- CKCOUIYYKYXLEB-UHFFFAOYSA-N n-[[5-fluoro-2-(pyridine-2-carbonylamino)phenyl]methyl]quinoxaline-2-carboxamide Chemical compound C=1N=C2C=CC=CC2=NC=1C(=O)NCC1=CC(F)=CC=C1NC(=O)C1=CC=CC=N1 CKCOUIYYKYXLEB-UHFFFAOYSA-N 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45773403P | 2003-03-26 | 2003-03-26 | |
| PCT/US2004/008627 WO2004087048A2 (en) | 2003-03-26 | 2004-03-22 | Benzamide modulators of metabotropic glutamate receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006521358A JP2006521358A (ja) | 2006-09-21 |
| JP2006521358A5 true JP2006521358A5 (https=) | 2007-05-17 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006507424A Withdrawn JP2006521358A (ja) | 2003-03-26 | 2004-03-22 | 代謝調節型グルタミン酸受容体のベンズアミドモジュレータ |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7507836B2 (https=) |
| EP (1) | EP1611096A4 (https=) |
| JP (1) | JP2006521358A (https=) |
| CN (1) | CN100457731C (https=) |
| AU (1) | AU2004226450A1 (https=) |
| CA (1) | CA2519954A1 (https=) |
| WO (1) | WO2004087048A2 (https=) |
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|---|---|---|---|---|
| EP1667983A4 (en) * | 2003-09-23 | 2010-07-21 | Merck Sharp & Dohme | PYRAZOL MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS |
| GB0325956D0 (en) | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| TW200613272A (en) | 2004-08-13 | 2006-05-01 | Astrazeneca Ab | Isoindolone compounds and their use as metabotropic glutamate receptor potentiators |
| BRPI0606644A2 (pt) * | 2005-01-14 | 2009-07-14 | Hoffmann La Roche | derivados de 4-carboxamida tiazola |
| WO2006094639A1 (en) * | 2005-03-04 | 2006-09-14 | F.Hoffmann-La Roche Ag | Pyridine-2-carboxamide derivatives as mglur5 antagonists |
| GB0510142D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
| GB0510139D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B1 |
| GB0510140D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B2 |
| US7807706B2 (en) | 2005-08-12 | 2010-10-05 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
| WO2008131439A1 (en) * | 2007-04-23 | 2008-10-30 | House Ear Institute | Treatment and/or prevention of presbycusis by modulation of metabotropic glutamate receptor 7 |
| US8853392B2 (en) * | 2007-06-03 | 2014-10-07 | Vanderbilt University | Benzamide mGluR5 positive allosteric modulators and methods of making and using same |
| KR20100033981A (ko) * | 2007-06-03 | 2010-03-31 | 벤더르빌트 유니버시티 | 벤즈아미드 대사성 글루타민산염 수용체5 양성 알로스테릭 조절자 및 이의 제조 및 사용방법 |
| TWI417100B (zh) | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-８４２之用途 |
| GB0713686D0 (en) | 2007-07-13 | 2007-08-22 | Addex Pharmaceuticals Sa | New compounds 2 |
| US8034806B2 (en) * | 2007-11-02 | 2011-10-11 | Vanderbilt University | Bicyclic mGluR5 positive allosteric modulators and methods of making and using same |
| US8211882B2 (en) * | 2008-03-08 | 2012-07-03 | Richard Delarey Wood | Glutamate receptor modulators and therapeutic agents |
| US7790760B2 (en) | 2008-06-06 | 2010-09-07 | Astrazeneca Ab | Metabotropic glutamate receptor isoxazole ligands and their use as potentiators 286 |
| CA2737699A1 (en) * | 2008-09-16 | 2010-03-25 | Merck Sharp & Dohme Corp. | Phthalimide derivative metabotropic glutamate r4 ligands |
| WO2011034741A1 (en) * | 2009-09-15 | 2011-03-24 | Merck Sharp & Dohme Corp. | Imidazopyridin-2-one derivatives |
| WO2011035209A1 (en) * | 2009-09-17 | 2011-03-24 | Vanderbilt Universtiy | Substituted benzamide analogs as mglur5 negative allosteric modulators and methods of making and using the same |
| US8772301B2 (en) | 2009-12-18 | 2014-07-08 | Sunovion Pharmaceuticals, Inc. | Compounds for treating disorders mediated by metabotropic glutamate receptor 5, and methods of use thereof |
| CA2791672A1 (en) | 2010-03-04 | 2011-09-09 | Merck Sharp & Dohme Corp. | Positive allosteric modulators of mglur2 |
| GB201215033D0 (en) * | 2012-08-23 | 2012-10-10 | Novartis Ag | Diazepinone derivatives |
| GB201223308D0 (en) | 2012-12-21 | 2013-02-06 | Univ Sunderland | Enzyme inhibitors |
| AU2014353150A1 (en) | 2013-11-19 | 2016-07-07 | Vanderbilt University | Substituted imidazopyridine and triazolopyridine compounds as negative allosteric modulators of mGluR5 |
| US9533982B2 (en) | 2014-03-20 | 2017-01-03 | Vanderbilt University | Substituted bicyclic heteroaryl carboxamide analogs as mGluR5 negative allosteric modulators |
| US9550778B2 (en) | 2014-10-03 | 2017-01-24 | Vanderbilt University | Substituted 6-aryl-imidazopyridine and 6-aryl-triazolopyridine carboxamide analogs as negative allosteric modulators of mGluR5 |
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| EP1183238A1 (en) | 1999-05-17 | 2002-03-06 | Eli Lilly And Company | Metabotropic glutamate receptor antagonists |
| US6800651B2 (en) * | 2000-02-03 | 2004-10-05 | Eli Lilly And Company | Potentiators of glutamate receptors |
| WO2002046166A1 (en) | 2000-12-04 | 2002-06-13 | F. Hoffmann-La Roche Ag | Phenylethenyl or phenylethinyl derivatives as glutamate receptor antagonists |
| DK1397351T3 (da) * | 2001-06-01 | 2010-01-18 | Hoffmann La Roche | Pyrimidin-, triazin- og pyrazinderivater som glutamatreceptorer |
-
2004
- 2004-03-22 CA CA002519954A patent/CA2519954A1/en not_active Abandoned
- 2004-03-22 US US10/550,968 patent/US7507836B2/en not_active Expired - Fee Related
- 2004-03-22 JP JP2006507424A patent/JP2006521358A/ja not_active Withdrawn
- 2004-03-22 AU AU2004226450A patent/AU2004226450A1/en not_active Abandoned
- 2004-03-22 EP EP04758170A patent/EP1611096A4/en not_active Withdrawn
- 2004-03-22 CN CNB2004800140092A patent/CN100457731C/zh not_active Expired - Fee Related
- 2004-03-22 WO PCT/US2004/008627 patent/WO2004087048A2/en not_active Ceased
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