JP2014518234A5 - - Google Patents
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- Publication number
- JP2014518234A5 JP2014518234A5 JP2014517667A JP2014517667A JP2014518234A5 JP 2014518234 A5 JP2014518234 A5 JP 2014518234A5 JP 2014517667 A JP2014517667 A JP 2014517667A JP 2014517667 A JP2014517667 A JP 2014517667A JP 2014518234 A5 JP2014518234 A5 JP 2014518234A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- triazolo
- quinoxaline
- chlorophenyl
- quinoxalin
- 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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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 12
- -1 pyridin-4-yloxy Chemical group 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- RBQZSOSIDAYTQQ-UHFFFAOYSA-N 4-[[1-[5-(2-methoxyethyl)pyridin-3-yl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]methyl]morpholine Chemical compound COCCC1=CN=CC(C=2N3C4=CC(CN5CCOCC5)=CC=C4N=C(C)C3=NN=2)=C1 RBQZSOSIDAYTQQ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- RFZHZDSZQMLWPM-UHFFFAOYSA-N (4-methyl-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)methanol Chemical compound N=1N=C2C(C)=NC3=CC=C(CO)C=C3N2C=1C1=CC=CC=C1 RFZHZDSZQMLWPM-UHFFFAOYSA-N 0.000 description 1
- PBXNICUZJRRAJG-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-4-methyl-n-(pyridin-2-ylmethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound N=1N=C2C(C)=NC3=CC=C(C(=O)NCC=4N=CC=CC=4)C=C3N2C=1C1=CC=C(Cl)C=C1Cl PBXNICUZJRRAJG-UHFFFAOYSA-N 0.000 description 1
- UFSFBTVVLZCSCY-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)-4-methyl-n-(pyridin-2-ylmethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound N=1N=C2C(C)=NC3=CC=C(C(=O)NCC=4N=CC=CC=4)C=C3N2C=1C1=CC(Cl)=CC=C1Cl UFSFBTVVLZCSCY-UHFFFAOYSA-N 0.000 description 1
- URLXPSUXGAGTAF-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-n-ethyl-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound N12C3=CC(C(=O)NCC)=CC=C3N=C(C)C2=NN=C1C1=C(Cl)C=CC=C1Cl URLXPSUXGAGTAF-UHFFFAOYSA-N 0.000 description 1
- DOKQEIRHEFIUMS-UHFFFAOYSA-N 1-(2-chloro-4-methoxyphenyl)-4-methyl-n-(pyridin-2-ylmethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=NN=C2N1C1=CC(C(=O)NCC=3N=CC=CC=3)=CC=C1N=C2C DOKQEIRHEFIUMS-UHFFFAOYSA-N 0.000 description 1
- ADXGWVHEMCWLBI-UHFFFAOYSA-N 1-(2-chloro-5-ethoxyphenyl)-4-methyl-8-(2-pyridin-3-ylethoxy)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCOC1=CC=C(Cl)C(C=2N3C4=CC(OCCC=5C=NC=CC=5)=CC=C4N=C(C)C3=NN=2)=C1 ADXGWVHEMCWLBI-UHFFFAOYSA-N 0.000 description 1
- RHGSISTUFNGCAI-UHFFFAOYSA-N 1-(2-chloro-5-ethoxyphenyl)-4-methyl-8-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCOC1=CC=C(Cl)C(C=2N3C4=CC(=CC=C4N=C(C)C3=NN=2)N2CCN(C)CC2)=C1 RHGSISTUFNGCAI-UHFFFAOYSA-N 0.000 description 1
- QPXNLQLXPDJMAK-UHFFFAOYSA-N 1-(2-chloro-5-ethoxyphenyl)-4-methyl-8-[(4-methylpiperazin-1-yl)methyl]-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCOC1=CC=C(Cl)C(C=2N3C4=CC(CN5CCN(C)CC5)=CC=C4N=C(C)C3=NN=2)=C1 QPXNLQLXPDJMAK-UHFFFAOYSA-N 0.000 description 1
- ICFQVFGTONAAIZ-UHFFFAOYSA-N 1-(2-chloro-5-ethoxyphenyl)-8-[(4-fluoropiperidin-1-yl)methyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCOC1=CC=C(Cl)C(C=2N3C4=CC(CN5CCC(F)CC5)=CC=C4N=C(C)C3=NN=2)=C1 ICFQVFGTONAAIZ-UHFFFAOYSA-N 0.000 description 1
- RXSACHXZPRTNLY-UHFFFAOYSA-N 1-(2-chloro-5-fluorophenyl)-4-methyl-n-(pyridin-2-ylmethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound N=1N=C2C(C)=NC3=CC=C(C(=O)NCC=4N=CC=CC=4)C=C3N2C=1C1=CC(F)=CC=C1Cl RXSACHXZPRTNLY-UHFFFAOYSA-N 0.000 description 1
- KSVZPHFVGCYJBQ-UHFFFAOYSA-N 1-(2-chloro-5-methoxyphenyl)-4-methyl-n-(pyridin-2-ylmethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound COC1=CC=C(Cl)C(C=2N3C4=CC(=CC=C4N=C(C)C3=NN=2)C(=O)NCC=2N=CC=CC=2)=C1 KSVZPHFVGCYJBQ-UHFFFAOYSA-N 0.000 description 1
- RFPHPZFQKKOGCW-UHFFFAOYSA-N 1-(2-chloro-5-methoxyphenyl)-8-[(4-fluoropiperidin-1-yl)methyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COC1=CC=C(Cl)C(C=2N3C4=CC(CN5CCC(F)CC5)=CC=C4N=C(C)C3=NN=2)=C1 RFPHPZFQKKOGCW-UHFFFAOYSA-N 0.000 description 1
- IZFCCDRZSRDTDB-UHFFFAOYSA-N 1-(2-chloro-5-methylphenyl)-4-methyl-n-(pyridin-2-ylmethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound CC1=CC=C(Cl)C(C=2N3C4=CC(=CC=C4N=C(C)C3=NN=2)C(=O)NCC=2N=CC=CC=2)=C1 IZFCCDRZSRDTDB-UHFFFAOYSA-N 0.000 description 1
- DXMWTQIHTKNDCL-UHFFFAOYSA-N 1-(2-chloro-5-propan-2-yloxyphenyl)-4-methyl-8-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CC(C)OC1=CC=C(Cl)C(C=2N3C4=CC(=CC=C4N=C(C)C3=NN=2)N2CCN(C)CC2)=C1 DXMWTQIHTKNDCL-UHFFFAOYSA-N 0.000 description 1
- DXRORSSYLRSSCH-UHFFFAOYSA-N 1-(2-chloro-5-propan-2-yloxyphenyl)-4-methyl-8-[(4-methylpiperazin-1-yl)methyl]-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CC(C)OC1=CC=C(Cl)C(C=2N3C4=CC(CN5CCN(C)CC5)=CC=C4N=C(C)C3=NN=2)=C1 DXRORSSYLRSSCH-UHFFFAOYSA-N 0.000 description 1
- SQCWLPYHEITKLZ-UHFFFAOYSA-N 1-(2-chloro-5-propan-2-yloxyphenyl)-8-[(4-fluoropiperidin-1-yl)methyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CC(C)OC1=CC=C(Cl)C(C=2N3C4=CC(CN5CCC(F)CC5)=CC=C4N=C(C)C3=NN=2)=C1 SQCWLPYHEITKLZ-UHFFFAOYSA-N 0.000 description 1
- KSLZFRSYFBPHNT-UHFFFAOYSA-N 1-(2-chloro-5-propoxyphenyl)-4-methyl-8-(2-pyridin-3-ylethoxy)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCOC1=CC=C(Cl)C(C=2N3C4=CC(OCCC=5C=NC=CC=5)=CC=C4N=C(C)C3=NN=2)=C1 KSLZFRSYFBPHNT-UHFFFAOYSA-N 0.000 description 1
- AJLATRGQTGOZDX-UHFFFAOYSA-N 1-(2-chloro-5-propoxyphenyl)-4-methyl-8-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCOC1=CC=C(Cl)C(C=2N3C4=CC(=CC=C4N=C(C)C3=NN=2)N2CCN(C)CC2)=C1 AJLATRGQTGOZDX-UHFFFAOYSA-N 0.000 description 1
- MWJHRMBPKCJYLL-UHFFFAOYSA-N 1-(2-chloro-5-propoxyphenyl)-4-methyl-8-[(4-methylpiperazin-1-yl)methyl]-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCOC1=CC=C(Cl)C(C=2N3C4=CC(CN5CCN(C)CC5)=CC=C4N=C(C)C3=NN=2)=C1 MWJHRMBPKCJYLL-UHFFFAOYSA-N 0.000 description 1
- ROZSPBVQXAQIAI-INIZCTEOSA-N 1-(2-chloro-5-propoxyphenyl)-4-methyl-8-[[(2s)-pyrrolidin-2-yl]methoxy]-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCOC1=CC=C(Cl)C(C=2N3C4=CC(OC[C@H]5NCCC5)=CC=C4N=C(C)C3=NN=2)=C1 ROZSPBVQXAQIAI-INIZCTEOSA-N 0.000 description 1
- YRVJDPUKLYCAAV-UHFFFAOYSA-N 1-(2-chloro-5-propoxyphenyl)-8-[(4-fluoropiperidin-1-yl)methyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCOC1=CC=C(Cl)C(C=2N3C4=CC(CN5CCC(F)CC5)=CC=C4N=C(C)C3=NN=2)=C1 YRVJDPUKLYCAAV-UHFFFAOYSA-N 0.000 description 1
- ADCUCKZPYWAEBQ-UHFFFAOYSA-N 1-(2-chloro-6-fluorophenyl)-8-ethenyl-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=C(C=C)C=C3N2C=1C1=C(F)C=CC=C1Cl ADCUCKZPYWAEBQ-UHFFFAOYSA-N 0.000 description 1
- FDJDXMSUDXBHSQ-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-7-(2-pyridin-2-ylethoxy)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C=1C=C2N3C(C=4C(=CC=CC=4)Cl)=NN=C3C(C)=NC2=CC=1OCCC1=CC=CC=N1 FDJDXMSUDXBHSQ-UHFFFAOYSA-N 0.000 description 1
- ZLNBADYTIGPAFU-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-7-(trifluoromethoxy)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC(OC(F)(F)F)=CC=C3N2C=1C1=CC=CC=C1Cl ZLNBADYTIGPAFU-UHFFFAOYSA-N 0.000 description 1
- RSAPMUKAYVUXCU-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-8-(2-pyridin-2-ylethoxy)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=C2N3C(C=4C(=CC=CC=4)Cl)=NN=C3C(C)=NC2=CC=C1OCCC1=CC=CC=N1 RSAPMUKAYVUXCU-UHFFFAOYSA-N 0.000 description 1
- PNYVWIGFSKFFAW-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-8-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1CN(C)CCN1C1=CC=C(N=C(C)C=2N3C(C=4C(=CC=CC=4)Cl)=NN=2)C3=C1 PNYVWIGFSKFFAW-UHFFFAOYSA-N 0.000 description 1
- MMWSLKUAHUNFRG-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-8-(trifluoromethoxy)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=C(OC(F)(F)F)C=C3N2C=1C1=CC=CC=C1Cl MMWSLKUAHUNFRG-UHFFFAOYSA-N 0.000 description 1
- QINZPNYWORORJH-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-8-[(4-methylpiperazin-1-yl)methyl]-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1CN(C)CCN1CC1=CC=C(N=C(C)C=2N3C(C=4C(=CC=CC=4)Cl)=NN=2)C3=C1 QINZPNYWORORJH-UHFFFAOYSA-N 0.000 description 1
- RNDRKGWDIXCGGN-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-8-amine Chemical compound N=1N=C2C(C)=NC3=CC=C(N)C=C3N2C=1C1=CC=CC=C1Cl RNDRKGWDIXCGGN-UHFFFAOYSA-N 0.000 description 1
- UQIZGVMJUBAZMQ-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-8-ol Chemical compound N=1N=C2C(C)=NC3=CC=C(O)C=C3N2C=1C1=CC=CC=C1Cl UQIZGVMJUBAZMQ-UHFFFAOYSA-N 0.000 description 1
- CTBSIWZADWNGPL-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=CC=CC=C1Cl CTBSIWZADWNGPL-UHFFFAOYSA-N 0.000 description 1
- BNSTYXVEOJNFJM-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxylic acid Chemical compound N=1N=C2C(C)=NC3=CC=C(C(O)=O)C=C3N2C=1C1=CC=CC=C1Cl BNSTYXVEOJNFJM-UHFFFAOYSA-N 0.000 description 1
- OKUUWEOFPDWWAJ-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-n-(1-methylpiperidin-4-yl)-[1,2,4]triazolo[4,3-a]quinoxalin-8-amine Chemical compound C1CN(C)CCC1NC1=CC=C(N=C(C)C=2N3C(C=4C(=CC=CC=4)Cl)=NN=2)C3=C1 OKUUWEOFPDWWAJ-UHFFFAOYSA-N 0.000 description 1
- FGXIRQDNKXCFIL-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-n-(1-methylpiperidin-4-yl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1=CC=C(N=C(C)C=2N3C(C=4C(=CC=CC=4)Cl)=NN=2)C3=C1 FGXIRQDNKXCFIL-UHFFFAOYSA-N 0.000 description 1
- LEZMGPUUKQUXJN-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-n-(2-morpholin-4-ylethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-8-amine Chemical compound C1=C2N3C(C=4C(=CC=CC=4)Cl)=NN=C3C(C)=NC2=CC=C1NCCN1CCOCC1 LEZMGPUUKQUXJN-UHFFFAOYSA-N 0.000 description 1
- IFWAHVQKYGJWGP-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-n-(2-morpholin-4-ylethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound N=1N=C2C(C)=NC3=CC=C(C(=O)NCCN4CCOCC4)C=C3N2C=1C1=CC=CC=C1Cl IFWAHVQKYGJWGP-UHFFFAOYSA-N 0.000 description 1
- XNYYCWIPILCSBL-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-n-(2-phenylethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound N=1N=C2C(C)=NC3=CC=C(C(=O)NCCC=4C=CC=CC=4)C=C3N2C=1C1=CC=CC=C1Cl XNYYCWIPILCSBL-UHFFFAOYSA-N 0.000 description 1
- RHFWGIGDAGTINL-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-n-(2-piperidin-1-ylethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound N=1N=C2C(C)=NC3=CC=C(C(=O)NCCN4CCCCC4)C=C3N2C=1C1=CC=CC=C1Cl RHFWGIGDAGTINL-UHFFFAOYSA-N 0.000 description 1
- YUYKNZMIAJIBOA-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-n-(2-pyridin-2-ylethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-8-amine Chemical compound C1=C2N3C(C=4C(=CC=CC=4)Cl)=NN=C3C(C)=NC2=CC=C1NCCC1=CC=CC=N1 YUYKNZMIAJIBOA-UHFFFAOYSA-N 0.000 description 1
- KTVOIZSPBSYWIC-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-n-(2-pyrrolidin-1-ylethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound N=1N=C2C(C)=NC3=CC=C(C(=O)NCCN4CCCC4)C=C3N2C=1C1=CC=CC=C1Cl KTVOIZSPBSYWIC-UHFFFAOYSA-N 0.000 description 1
- MGKVGJJPEDPCEQ-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-n-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)C=2C=C3N4C(C=5C(=CC=CC=5)Cl)=NN=C4C(C)=NC3=CC=2)=C1 MGKVGJJPEDPCEQ-UHFFFAOYSA-N 0.000 description 1
- AWMOIFLKHCCNSA-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-n-(pyridin-2-ylmethyl)-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound N=1N=C2C(C)=NC3=CC=C(C(=O)NCC=4N=CC=CC=4)C=C3N2C=1C1=CC=CC=C1Cl AWMOIFLKHCCNSA-UHFFFAOYSA-N 0.000 description 1
- VYUJHYUPDPKIJI-UHFFFAOYSA-N 1-(2-chlorophenyl)-8-(1,1-difluoroethoxy)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=C(OC(C)(F)F)C=C3N2C=1C1=CC=CC=C1Cl VYUJHYUPDPKIJI-UHFFFAOYSA-N 0.000 description 1
- KYFKQTJBDJLLCX-UHFFFAOYSA-N 1-(2-chlorophenyl)-8-[(3-methoxypiperidin-1-yl)methyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1C(OC)CCCN1CC1=CC=C(N=C(C)C=2N3C(C=4C(=CC=CC=4)Cl)=NN=2)C3=C1 KYFKQTJBDJLLCX-UHFFFAOYSA-N 0.000 description 1
- CPSWTJWDYWGXCK-UHFFFAOYSA-N 1-(2-chlorophenyl)-8-[(4-fluoropiperidin-1-yl)methyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=C2N3C(C=4C(=CC=CC=4)Cl)=NN=C3C(C)=NC2=CC=C1CN1CCC(F)CC1 CPSWTJWDYWGXCK-UHFFFAOYSA-N 0.000 description 1
- UZSLMTQHJNJZLV-UHFFFAOYSA-N 1-(2-chlorophenyl)-8-[(4-methoxypiperidin-1-yl)methyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1CC(OC)CCN1CC1=CC=C(N=C(C)C=2N3C(C=4C(=CC=CC=4)Cl)=NN=2)C3=C1 UZSLMTQHJNJZLV-UHFFFAOYSA-N 0.000 description 1
- KHYIRYRWPBUBTC-UHFFFAOYSA-N 1-(2-chlorophenyl)-8-[[3-(methoxymethyl)pyrrolidin-1-yl]methyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1C(COC)CCN1CC1=CC=C(N=C(C)C=2N3C(C=4C(=CC=CC=4)Cl)=NN=2)C3=C1 KHYIRYRWPBUBTC-UHFFFAOYSA-N 0.000 description 1
- WMIGIQZRGONALR-UHFFFAOYSA-N 1-(2-chlorophenyl)-8-ethenyl-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=C(C=C)C=C3N2C=1C1=CC=CC=C1Cl WMIGIQZRGONALR-UHFFFAOYSA-N 0.000 description 1
- IQFAUAIVCNIZMA-UHFFFAOYSA-N 1-(2-chlorophenyl)-8-methoxy-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N12C3=CC(OC)=CC=C3N=C(C)C2=NN=C1C1=CC=CC=C1Cl IQFAUAIVCNIZMA-UHFFFAOYSA-N 0.000 description 1
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| US9540379B2 (en) | 2011-01-31 | 2017-01-10 | Boehringer Ingelheim International Gmbh | (1,2,4)triazolo[4,3-A]quinoxaline derivatives as inhibitors of phosphodiesterases |
| WO2013000924A1 (en) | 2011-06-27 | 2013-01-03 | Janssen Pharmaceutica Nv | 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES |
| EP2763989A1 (en) * | 2011-09-09 | 2014-08-13 | H. Lundbeck A/S | Pyridine compounds and uses thereof |
| WO2014001314A1 (en) * | 2012-06-26 | 2014-01-03 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| US20140045856A1 (en) | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
| HK1210610A1 (en) * | 2013-01-31 | 2016-04-29 | 霍夫曼-拉罗奇有限公司 | Radiolabeled compounds |
| WO2014139983A1 (en) | 2013-03-13 | 2014-09-18 | H. Lundbeck A/S | [1,2,4]triazolo[4,3-a]quinoxalines as dual pde2/pde10 inhibitors |
| JP6696904B2 (ja) | 2014-01-08 | 2020-05-20 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 製剤および医薬組成物 |
| HUE057317T2 (hu) | 2014-04-23 | 2022-04-28 | Dart Neuroscience Llc | Helyettesített [1,2,4]triazolo[1,5-A]pirimidin-7-IL vegyületeket tartalmazó készítmények mint PDE2 inhibítorok |
| TWI568737B (zh) | 2014-11-05 | 2017-02-01 | 達特神經科學（開曼）有限責任公司 | 作為ｐｄｅ２抑制劑之經取代的５－甲基－［１，２，４］三唑并［１，５－ａ］嘧啶－２－胺化合物 |
| CA2969594A1 (en) | 2014-12-06 | 2016-06-09 | Intra-Cellular Therapies, Inc. | Pde2 inhibiting organic compounds |
| HK1244427A1 (zh) | 2014-12-06 | 2018-08-10 | Intra-Cellular Therapies, Inc. | 有机化合物 |
| WO2016145614A1 (en) | 2015-03-17 | 2016-09-22 | Merck Sharp & Dohme Corp. | Triazolyl pyrimidinone compounds as pde2 inhibitors |
| WO2016154081A1 (en) | 2015-03-26 | 2016-09-29 | Merck Sharp & Dohme Corp. | Pyrazolyl pyrimidinone compounds as pde2 inhibitors |
| WO2016179059A1 (en) | 2015-05-05 | 2016-11-10 | Merck Sharp & Dohme Corp. | Heteroaryl-pyrimidinone compounds as pde2 inhibitors |
| WO2016183741A1 (en) | 2015-05-15 | 2016-11-24 | Merck Sharp & Dohme Corp. | Pyrimidinone amide compounds as pde2 inhibitors |
| WO2016191935A1 (en) | 2015-05-29 | 2016-12-08 | Merck Sharp & Dohme Corp. | 6-alkyl dihydropyrazolopyrimidinone compounds as pde2 inhibitors |
| WO2016192083A1 (en) | 2015-06-04 | 2016-12-08 | Merck Sharp & Dohme Corp. | Dihydropyrazolopyrimidinone compounds as pde2 inhibitors |
| US10647727B2 (en) | 2015-06-25 | 2020-05-12 | Merck Sharp & Dohme Corp. | Substituted pyrazolo/imidazolo bicyclic compounds as PDE2 inhibitors |
| WO2017000276A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Bicyclic heterocyclic compounds as pde2 inhibitors |
| WO2017000277A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Substituted triazolo bicycliccompounds as pde2 inhibitors |
| EP3156405A1 (en) | 2015-10-13 | 2017-04-19 | Boehringer Ingelheim International GmbH | Spirocyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxamide |
| ES2765738T3 (es) * | 2015-11-02 | 2020-06-10 | Janssen Pharmaceutica Nv | Compuesto de [1,2,4]triazolo[1,5-a]pirimidin-7-ilo |
| US10166236B2 (en) | 2016-03-21 | 2019-01-01 | Perlara Pbc | Pharmaceutical formulations comprising substituted pyrazolo[5,1-c]pyrido[4,3-e][1,2,4]triazines for treating lysosomal storage disorders |
| AU2017353313C1 (en) | 2016-11-02 | 2022-06-09 | Janssen Pharmaceutica Nv | (1,2,4)triazolo(1,5-a)pyrimidine compounds as PDE2 inhibitors |
| CA3038916A1 (en) | 2016-11-02 | 2018-05-11 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidine compounds as pde2 inhibitors |
| MX385576B (es) | 2016-11-02 | 2025-03-18 | Janssen Pharmaceutica Nv | Derivados de [1,2,4]triazol[1,5-a]pirimidina como inhibidores de pde2 |
| CN107827828B (zh) * | 2017-11-21 | 2021-03-30 | 南京华漫新材料科技有限公司 | 含苯酰肼骨架的喹喔啉衍生物及其制备方法和在制备抗肿瘤药物中的应用 |
| AU2018371216B2 (en) | 2017-11-23 | 2024-09-19 | Oslo University Hospital Hf | Treatment of tachycardia |
Family Cites Families (214)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5584421A (en) | 1978-12-21 | 1980-06-25 | Mitsui Cokes Kogyo Kk | Method of making fibrous carbon |
| US4242513A (en) | 1979-03-05 | 1980-12-30 | Appleton Papers Inc. | Lactone compounds containing a heterocyclic radical |
| DE3666434D1 (de) | 1985-05-25 | 1989-11-23 | Yoshitomi Pharmaceutical | Oxodiazine compounds |
| JPH05503919A (ja) | 1989-06-13 | 1993-06-24 | スミスクライン・ビーチャム・コーポレイション | 単球および／またはマクロファージによるインターロイキン―１または腫瘍壊死因子生成の抑制 |
| KR920702606A (ko) | 1989-06-13 | 1992-10-06 | 스튜어트 알. 슈터 | 모노킨(Monokine)의 활성저해 |
| AU622330B2 (en) | 1989-06-23 | 1992-04-02 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides |
| KR910011852A (ko) | 1989-12-04 | 1991-08-07 | 폴 디. 매튜카이티스 | 신경독 장해 치료용 이미다조[1,2-a]피리디닐알킬 화합물 |
| AU8205991A (en) | 1990-06-12 | 1992-01-07 | Smithkline Beecham Corporation | Inhibition of 5-lipoxygenase and cyclooxygenase pathway mediated diseases |
| US5137876A (en) | 1990-10-12 | 1992-08-11 | Merck & Co., Inc. | Nucleoside antiviral and anti-inflammatory compounds and compositions and methods for using same |
| ZA919797B (en) | 1990-12-13 | 1992-10-28 | Smithkline Beecham Corp | Bicyclo-5,6-dihydro-7h-pyrrolo-1,20-imidazol-7-ols and 7-ones |
| AU9137591A (en) | 1990-12-13 | 1992-07-08 | Smithkline Beecham Corporation | Novel csaids |
| US5683998A (en) | 1991-04-23 | 1997-11-04 | Toray Industries, Inc. | Tricyclic triazolo derivatives, processes for producing the same and the uses of the same |
| CN1033327C (zh) | 1991-04-23 | 1996-11-20 | 东丽株式会社 | 三环三唑并衍生物的制造方法 |
| DK31093D0 (https=) | 1993-03-19 | 1993-03-19 | Novo Nordisk As | |
| US5486525A (en) | 1993-12-16 | 1996-01-23 | Abbott Laboratories | Platelet activating factor antagonists: imidazopyridine indoles |
| US5869486A (en) | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| JPH11505524A (ja) | 1995-05-01 | 1999-05-21 | 藤沢薬品工業株式会社 | イミダゾ１，２−ａピリジンおよびイミダゾ１，２−ａピリデジン誘導体、および骨吸収阻害剤としてのその用途 |
| US6992188B1 (en) | 1995-12-08 | 2006-01-31 | Pfizer, Inc. | Substituted heterocyclic derivatives |
| US20010007867A1 (en) | 1999-12-13 | 2001-07-12 | Yuhpyng L. Chen | Substituted 6,5-hetero-bicyclic derivatives |
| AU6279598A (en) | 1997-02-18 | 1998-09-08 | Neurocrine Biosciences, Inc. | Biazacyclic CRF antagonists |
| US6054587A (en) | 1997-03-07 | 2000-04-25 | Metabasis Therapeutics, Inc. | Indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
| US6245769B1 (en) | 1997-09-02 | 2001-06-12 | Dupont Pharmaceuticals Company | Heterocyclyl-substituted ring-fused pyridines and pyrimidines as corticotropin releasing hormone(CRH) antagonists, useful for treating CNS and stress-related disorders |
| WO2000001376A2 (en) | 1998-07-02 | 2000-01-13 | Eisai Co., Ltd | Pharmaceutical compositions and their uses for treatment of demyelinating disorders |
| US6248755B1 (en) | 1999-04-06 | 2001-06-19 | Merck & Co., Inc. | Pyrrolidine modulators of chemokine receptor activity |
| JP4032566B2 (ja) | 1999-06-21 | 2008-01-16 | 東レ株式会社 | 発光素子 |
| JP2001057292A (ja) | 1999-08-20 | 2001-02-27 | Toray Ind Inc | 発光素子 |
| GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| CO5271670A1 (es) | 1999-10-29 | 2003-04-30 | Pfizer Prod Inc | Antagonistas del factor de liberacion de corticitropina y composiciones relacionadas |
| AU2001232271A1 (en) | 2000-02-14 | 2001-08-20 | Japan Tobacco Inc. | Preventives/remedies for postoperative stress |
| EP1149583A3 (en) | 2000-04-13 | 2001-11-14 | Pfizer Products Inc. | Combinations of corticotropin releasing factor antagonists and growth hormone secretagogues |
| US6403588B1 (en) | 2000-04-27 | 2002-06-11 | Yamanouchi Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
| WO2002006286A2 (en) | 2000-07-14 | 2002-01-24 | Bristol-Myers Squibb Pharma Company | IMIDAZO[1,2-a]PYRAZINES FOR THE TREATMENT OF NEUROLOGICAL DISORDERS |
| AU2001295992A1 (en) | 2000-10-24 | 2002-05-06 | Sankyo Company Limited | Imidazopyridine derivatives |
| US20040058938A1 (en) | 2000-12-13 | 2004-03-25 | Oliver Cullmann | Use of substituted imidazoazines, novel imidazoazines, methods for the production thereof, and agents containing these compounds |
| SK286630B6 (sk) | 2001-01-22 | 2009-02-05 | Merck & Co., Inc. | Nukleozidové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie |
| TWI312347B (en) | 2001-02-08 | 2009-07-21 | Eisai R&D Man Co Ltd | Bicyclic nitrogen-containing condensed ring compounds |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| SE0100568D0 (sv) | 2001-02-20 | 2001-02-20 | Astrazeneca Ab | Compounds |
| ES2316546T3 (es) | 2001-02-20 | 2009-04-16 | Astrazeneca Ab | 2-arilamino-pirimidinas para el tratamiento de trastornos asociados a gsk3. |
| DE60204674T2 (de) | 2001-03-14 | 2006-05-18 | Eli Lilly And Co., Indianapolis | Retinoid x rezeptormodulatoren |
| US7074801B1 (en) | 2001-04-26 | 2006-07-11 | Eisai Co., Ltd. | Nitrogen-containing condensed cyclic compound having a pyrazolyl group as a substituent group and pharmaceutical composition thereof |
| WO2002096318A2 (en) | 2001-05-30 | 2002-12-05 | Alteon, Inc. | Method for treating glaucoma v |
| EP1406611A2 (en) | 2001-05-30 | 2004-04-14 | Alteon, Inc. | Method for treating fibrotic diseases or other indications |
| ATE337316T1 (de) | 2001-06-21 | 2006-09-15 | Smithkline Beecham Corp | Imidazo 1,2-aöpyridin-derivate zur prophylaxe und behandlung von herpes-infektionen |
| WO2003000682A1 (en) | 2001-06-25 | 2003-01-03 | Merck & Co., Inc. | (pyrimidyl)(phenyl)substituted fused heteroaryl p38 inhibiting and pkg kinase inhibiting compounds |
| IL159811A0 (en) | 2001-07-13 | 2004-06-20 | Neurogen Corp | Heteroaryl substituted fused bicyclic heteroaryl compounds as gabaa receptor ligands |
| EP1432712B1 (en) | 2001-10-05 | 2006-05-17 | SmithKline Beecham Corporation | Imidazo-pyridine derivatives for use in the treatment of herpes viral infection |
| AU2003207646C1 (en) | 2002-01-22 | 2008-09-18 | Vanderbilt University | Treating stress response with chemokine receptor CCR5 modulators |
| WO2003076442A1 (en) | 2002-03-05 | 2003-09-18 | Eli Lilly And Company | Purine derivatives as kinase inhibitors |
| JP2003313126A (ja) | 2002-04-23 | 2003-11-06 | Sankyo Co Ltd | イミダゾピリジン誘導体を有効成分とする医薬 |
| JP2004002826A (ja) | 2002-04-24 | 2004-01-08 | Sankyo Co Ltd | 高分子イミダゾピリジン誘導体 |
| JP2005530788A (ja) | 2002-05-13 | 2005-10-13 | メルク エンド カムパニー インコーポレーテッド | フェニル置換イミダゾピリジン類およびフェニル置換ベンズイミダゾール類 |
| WO2003099840A1 (en) | 2002-05-24 | 2003-12-04 | Isis Pharmaceuticals, Inc. | Oligonucleotides having modified nucleoside units |
| GB0217783D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Compounds |
| EP1539748A1 (en) | 2002-07-31 | 2005-06-15 | Smithkline Beecham Corporation | 2-phenylpyridin-4-yl derivatives as alk5 inhibitors |
| WO2004014900A1 (en) | 2002-08-09 | 2004-02-19 | Eli Lilly And Company | Benzimidazoles and benzothiazoles as inhibitors of map kinase |
| AU2003255845A1 (en) | 2002-08-22 | 2004-03-11 | Piramed Limited | Phosphadidylinositol 3,5-biphosphate inhibitors as anti-viral agents |
| UA80296C2 (en) | 2002-09-06 | 2007-09-10 | Biogen Inc | Imidazolopyridines and methods of making and using the same |
| AU2003270489A1 (en) | 2002-09-09 | 2004-03-29 | Cellular Genomics, Inc. | 6-ARYL-IMIDAZO(1,2-a)PYRAZIN-8-YLAMINES, METHOD OF MAKING, AND METHOD OF USE THEREOF |
| US7105533B2 (en) | 2002-09-13 | 2006-09-12 | Merck & Co., Inc. | Fused heterobicyclo substituted phenyl metabotropic glutamate-5 modulators |
| MY133311A (en) | 2002-09-19 | 2007-11-30 | Schering Corp | Novel imidazopyridines as cyclin dependent kinase inhibitors |
| US7576085B2 (en) | 2002-09-23 | 2009-08-18 | Schering Corporation | Imidazopyrazines as cyclin dependent kinase inhibitors |
| NZ538685A (en) | 2002-09-23 | 2008-02-29 | Schering Corp | Imidazopyrazines as cyclin dependent kinase inhibitors |
| NZ538686A (en) | 2002-09-23 | 2008-01-31 | Schering Corp | Novel imidazopyrazines as cyclin dependent kinase inhibitors |
| WO2004035579A1 (ja) | 2002-10-15 | 2004-04-29 | Takeda Pharmaceutical Company Limited | イミダゾピリジン誘導体、その製造法および用途 |
| LT1576138T (lt) | 2002-11-15 | 2017-06-26 | Idenix Pharmaceuticals Llc | 2`-šakoti nukleozidai derinyje su interferonu ir flaviviridae mutacija |
| US20070004736A1 (en) | 2002-11-22 | 2007-01-04 | Keiji Kubo | Imidazole derivative, process for producing the same, and use |
| EP1582516B1 (en) | 2003-01-10 | 2013-07-17 | Idemitsu Kosan Co., Ltd. | Nitrogenous heterocyclic derivative and organic electroluminescent element employing the same |
| WO2004072080A1 (en) | 2003-02-10 | 2004-08-26 | Cellular Genomics, Inc. | Certain 8-heteroaryl-6-phenyl-imidazo[1,2-a]pyrazines as modulators of hsp90 complex activity |
| US7186832B2 (en) | 2003-02-20 | 2007-03-06 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| WO2004075846A2 (en) | 2003-02-25 | 2004-09-10 | Bristol-Myers Squibb Company | Pyrazolopurine-based tricyclic compounds and pharmaceutical compositions comprising same |
| PA8595001A1 (es) | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
| US7041671B2 (en) | 2003-04-02 | 2006-05-09 | Pfizer Inc | Pyrrolo[1,2-b]pyridazine compounds and their uses |
| WO2004089416A2 (en) | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | Combination of an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent |
| US20060100235A1 (en) | 2003-04-11 | 2006-05-11 | Novo Nordisk A/S | Pharmaceutical use of substituted 1,2,4-triazoles |
| US20060094699A1 (en) | 2003-04-11 | 2006-05-04 | Kampen Gita Camilla T | Combination therapy using an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor and a glucocorticoid receptor agonist to minimize the side effects associated with glucocorticoid receptor agonist therapy |
| WO2004103991A1 (en) | 2003-05-20 | 2004-12-02 | 'chemical Diversity Research Institute', Ltd. | 2-substituted piperidines, focused library and a pharmaceutical compound |
| WO2005020885A2 (en) | 2003-05-21 | 2005-03-10 | Isis Pharmaceuticals, Inc. | Compositions and methods for the treatment of severe acute respiratory syndrome (sars) |
| EP1630152A4 (en) | 2003-05-30 | 2009-09-23 | Takeda Pharmaceutical | CONDENSED CYCLIC COMPOUND |
| US7405295B2 (en) | 2003-06-04 | 2008-07-29 | Cgi Pharmaceuticals, Inc. | Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds |
| WO2005005429A1 (en) | 2003-06-30 | 2005-01-20 | Cellular Genomics, Inc. | Certain heterocyclic substituted imidazo[1,2-a]pyrazin-8-ylamines and methods of inhibition of bruton’s tyrosine kinase by such compounds |
| RS20060018A (sr) | 2003-07-14 | 2007-12-31 | Arena Pharmaceuticals Inc., | Derivati spojenih arila i heteroarila kao modulatori metabolizma u profilaksi i lečenju sa njima povezanih stanja |
| US7259164B2 (en) | 2003-08-11 | 2007-08-21 | Cgi Pharmaceuticals, Inc. | Certain substituted imidazo[1,2-a]pyrazines, as modulators of kinase activity |
| KR100553752B1 (ko) | 2003-10-13 | 2006-02-20 | 삼성에스디아이 주식회사 | 이미다졸 고리 함유 화합물 및 이를 이용한 유기 전계발광 소자 |
| US7723324B2 (en) | 2003-10-28 | 2010-05-25 | Sepracor, Inc. | Imidazo[1,2-A]pyridine anxiolytics |
| WO2005047290A2 (en) | 2003-11-11 | 2005-05-26 | Cellular Genomics Inc. | Imidazo[1,2-a] pyrazin-8-ylamines as kinase inhibitors |
| EP1713784A1 (en) | 2004-02-12 | 2006-10-25 | Neurogen Corporation | Imidazo-pyridazines, triazolo-pyridazines and related benzodiazepine receptor ligands |
| US7306631B2 (en) | 2004-03-30 | 2007-12-11 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| JP2005343889A (ja) | 2004-05-06 | 2005-12-15 | Taisho Pharmaceut Co Ltd | イミダゾピリジン誘導体 |
| WO2005120513A1 (en) | 2004-06-09 | 2005-12-22 | Oncalis Ag | Protein kinase inhibitors |
| GB0413605D0 (en) | 2004-06-17 | 2004-07-21 | Addex Pharmaceuticals Sa | Novel compounds |
| AU2005278292B2 (en) | 2004-08-31 | 2011-09-08 | Msd K.K. | Novel substituted imidazole derivatives |
| AU2005295734A1 (en) | 2004-10-15 | 2006-04-27 | Biogen Idec Ma Inc. | Methods of treating vascular injuries |
| CA2583812A1 (en) | 2004-10-28 | 2006-05-11 | Irm Llc | Compounds and compositions as hedgehog pathway modulators |
| JP4935357B2 (ja) | 2004-11-08 | 2012-05-23 | Ｍｓｄ株式会社 | 新規縮環イミダゾール誘導体 |
| AU2005304473A1 (en) | 2004-11-10 | 2006-05-18 | Cgi Pharmaceuticals, Inc. | Imidazo[1 , 2-a] pyrazin-8-ylamines useful as modulators of kinase activity |
| JP2008524255A (ja) | 2004-12-17 | 2008-07-10 | スミスクライン ビーチャム コーポレーション | 化学物質 |
| WO2006070943A1 (ja) | 2004-12-28 | 2006-07-06 | Takeda Pharmaceutical Company Limited | 縮合イミダゾール化合物およびその用途 |
| WO2006094235A1 (en) | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | Fused heterocyclic compounds and their use as sirtuin modulators |
| EP1869049B1 (en) | 2005-03-21 | 2009-03-04 | Eli Lilly And Company | Imidazopyridazine compounds |
| US7666880B2 (en) | 2005-03-21 | 2010-02-23 | S*Bio Pte Ltd. | Imidazo[1,2-A]pyridine derivatives: preparation and pharmaceutical applications |
| WO2006100119A1 (en) | 2005-03-24 | 2006-09-28 | Glaxo Group Limited | Derivatives of imidazo (1,2-a) pyridine useful as medicaments for treating gastrointestinal diseases |
| US7557103B2 (en) | 2005-04-05 | 2009-07-07 | Eli Lilly And Company | Imidazopyridazine compounds |
| US7572807B2 (en) | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| GB0513423D0 (en) | 2005-06-30 | 2005-08-03 | Glaxo Group Ltd | Novel compounds |
| MX2008000463A (es) | 2005-07-11 | 2008-03-11 | Novartis Ag | Derivados de indolil-maleimida. |
| EP1910369A1 (en) | 2005-07-29 | 2008-04-16 | Astellas Pharma Inc. | Fused heterocycles as lck inhibitors |
| US20070185063A1 (en) | 2005-08-23 | 2007-08-09 | Idenix Pharmaceuticals, Inc. | Seven-membered ring nucleosides |
| US20070049591A1 (en) | 2005-08-25 | 2007-03-01 | Kalypsys, Inc. | Inhibitors of MAPK/Erk Kinase |
| JP2009507032A (ja) | 2005-09-02 | 2009-02-19 | アボット・ラボラトリーズ | 新規なイミダゾ系複素環 |
| US20070078136A1 (en) | 2005-09-22 | 2007-04-05 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| JP5048675B2 (ja) | 2005-09-27 | 2012-10-17 | エフ．ホフマン−ラ ロシュ アーゲー | ｍＧｌｕＲ２アンタゴニストとしてのオキサジアゾリルピラゾロ−ピリミジン類 |
| AR056556A1 (es) | 2005-09-30 | 2007-10-10 | Astrazeneca Ab | Imidazo(1,2-a)piridina con actividad antiproliferacion celular |
| JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
| TW200803863A (en) | 2005-11-10 | 2008-01-16 | Schering Corp | Method for inhibiting protein kinases |
| US20070117804A1 (en) | 2005-11-10 | 2007-05-24 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| WO2007078815A2 (en) | 2005-12-16 | 2007-07-12 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| EP2474546A1 (en) | 2006-01-23 | 2012-07-11 | Vertex Pharmaceuticals Inc. | Thiophene-carboxamides useful as inhibitors of protein kinases |
| 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 |
| JP2009528388A (ja) | 2006-03-02 | 2009-08-06 | スミスクライン・ビーチャム・コーポレイション | Ｐｉ３キナーゼ阻害物質として用いられるチアゾロン |
| EP2029605A1 (en) | 2006-06-06 | 2009-03-04 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| US20090175852A1 (en) | 2006-06-06 | 2009-07-09 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| ITVA20060041A1 (it) | 2006-07-05 | 2008-01-06 | Dialectica Srl | Uso di composti derivati amminotiazolici, di loro composizioni farmaceutiche, nel trattamento di malattie caratterizzate dalla anormale repressione della trascrizione genica, particolarmente il morbo di huntington |
| AU2007275221A1 (en) | 2006-07-20 | 2008-01-24 | Allen J. Borchardt | Benzothiophene inhibitors of RHO kinase |
| EP2046333A4 (en) | 2006-07-24 | 2010-09-15 | Glaxosmithkline Llc | THIOZOLIDINEDIONE DERIVATIVES AS INHIBITORS OF P13-KINASE |
| WO2008027812A2 (en) | 2006-08-28 | 2008-03-06 | Forest Laboratories Holdings Limited | Imidazopyridine and imidazopyrimidine derivatives |
| US8268809B2 (en) | 2006-09-05 | 2012-09-18 | Emory University | Kinase inhibitors for preventing or treating pathogen infection and method of use thereof |
| WO2008030795A2 (en) | 2006-09-05 | 2008-03-13 | Boards Of Regents, The University Of Texas System | Compositions and methods for inhibition of tyrosine kinases |
| CN101594909A (zh) | 2006-09-07 | 2009-12-02 | 比奥根艾迪克Ma公司 | 用于治疗炎性病症、细胞增殖性失调、免疫失调的irak调节剂 |
| EP2068869A4 (en) | 2006-10-06 | 2011-05-25 | Abbott Lab | NEW IMIDAZOTHIAZOLE AND IMIDAZOXAZOLE |
| WO2008053285A1 (en) | 2006-10-30 | 2008-05-08 | Draximage Limited | Methods for preparing 2-methoxyisobutylisonitrile and tetrakis(2-methoxyisobutylisonitrile)copper(i) tetrafluoroborate |
| WO2008057402A2 (en) | 2006-11-02 | 2008-05-15 | Cytovia, Inc. | N-aryl-isoxazolopyrimidin-4-amines and related compounds as activators of caspases and inducers of apoptosis and the use thereof |
| EP2079746A2 (en) | 2006-11-08 | 2009-07-22 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| CA2670044A1 (en) | 2006-11-20 | 2008-05-29 | Alantos Pharmaceuticals Holding, Inc. | Heterobicyclic matrix metalloprotease inhibitors |
| US7622584B2 (en) | 2006-11-24 | 2009-11-24 | Samsung Mobile Display Co., Ltd. | Imidazopyridine-based compound and organic light emitting diode including organic layer comprising the imidazopyridine-based compound |
| RU2469034C2 (ru) | 2006-12-04 | 2012-12-10 | Астразенека Аб | Химические соединения |
| US7977336B2 (en) | 2006-12-28 | 2011-07-12 | Banyu Pharmaceutical Co. Ltd | Aminopyrimidine derivatives as PLK1 inhibitors |
| AU2008205642B2 (en) | 2007-01-12 | 2013-06-06 | Msd K.K. | Spirochromanon derivatives |
| US20080242862A1 (en) | 2007-03-27 | 2008-10-02 | Calderwood David J | Novel imidazo based heterocycles |
| JP2010522765A (ja) | 2007-03-28 | 2010-07-08 | アレイ バイオファーマ、インコーポレイテッド | 受容体チロシンキナーゼとしてのイミダゾ［１，２−ａ］ピリジン化合物 |
| NZ580327A (en) | 2007-04-03 | 2012-02-24 | Array Biopharma Inc | IMIDAZO[1,2-a]PYRIDINE COMPOUNDS AS RECEPTOR TYROSINE KINASE INHIBITORS |
| WO2008124153A1 (en) | 2007-04-10 | 2008-10-16 | H. Lundbeck A/S | Heteroaryl amide analogues as p2x7 antagonists |
| WO2008133192A1 (ja) | 2007-04-19 | 2008-11-06 | Takeda Pharmaceutical Company Limited | 縮合イミダゾール化合物およびその用途 |
| WO2008134553A1 (en) | 2007-04-26 | 2008-11-06 | Xenon Pharmaceuticals Inc. | Methods of using bicyclic compounds in treating sodium channel-mediated diseases |
| AR066477A1 (es) | 2007-05-09 | 2009-08-19 | Novartis Ag | Imidazopiridazinas sustituidas como inhibidores de cinasa de lipido |
| HRP20120914T1 (hr) | 2007-05-10 | 2012-12-31 | Biocryst Pharmaceuticals, Inc. | Spojevi tetrahidrofuro[3,4-d]dioksolana, namijenjeni upotrebi u lijeäśenju virusnih infekcija i raka |
| CN101932580B (zh) | 2007-06-01 | 2013-05-22 | 葛兰素史密丝克莱恩有限责任公司 | 咪唑并吡啶激酶抑制剂 |
| CA2690557A1 (en) | 2007-06-14 | 2008-12-24 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| KR101030007B1 (ko) | 2007-06-15 | 2011-04-20 | 삼성모바일디스플레이주식회사 | 헤테로방향환 함유 화합물, 이의 제조 방법 및 이를 이용한유기 발광 소자 |
| CA2690192A1 (en) | 2007-06-26 | 2008-12-31 | Gilead Colorado, Inc. | Imidazopyridinyl thiazolyl histone deacetylase inhibitors |
| FR2918061B1 (fr) | 2007-06-28 | 2010-10-22 | Sanofi Aventis | Derives de 6-cycloamino-3-(pyridin-4-yl)imidazo°1,2-b!- pyridazine,leur preparation et leur application en therapeutique. |
| WO2009005675A1 (en) | 2007-06-28 | 2009-01-08 | Abbott Laboratories | Novel triazolopyridazines |
| FR2918986B1 (fr) | 2007-07-19 | 2009-09-04 | Sanofi Aventis Sa | Derives de 6-cycloamino-3-(pyridazin-4-yl)imidazo[1,2-b]- pyridazine, leur preparation et leur application en therapeutique |
| EP2185512B1 (en) | 2007-07-27 | 2010-12-29 | Actelion Pharmaceuticals Ltd. | Trans-3-aza-bicyclo[3.1.0]hexane derivatives |
| US20100249030A1 (en) | 2007-07-31 | 2010-09-30 | Schering Corporation | Anti-mitotic agent and aurora kinase inhibitor combination as anti-cancer treatment |
| CA2695989A1 (en) | 2007-08-10 | 2009-02-19 | Glaxosmithkline Llc | Certain nitrogen containing bicyclic chemical entities for treating viral infections |
| WO2009021990A1 (en) | 2007-08-14 | 2009-02-19 | Bayer Schering Pharma Aktiengesellschaft | Fused imidazoles for cancer treatment |
| JP5393677B2 (ja) | 2007-08-15 | 2014-01-22 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ５−ＨＴ２Ａセロトニン受容体に関連した障害の治療のための５−ＨＴ２Ａセロトニン受容体のモジュレーターとしてのイミダゾ［１，２−ａ］ピリジン誘導体 |
| GB0716292D0 (en) | 2007-08-21 | 2007-09-26 | Biofocus Dpi Ltd | Imidazopyrazine compounds |
| EP2217601A1 (en) | 2007-11-08 | 2010-08-18 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Imidazopyridazines for use as protein kinase inhibitors |
| EP2217069A4 (en) | 2007-11-09 | 2012-03-14 | Salk Inst For Biological Studi | INHIBITORS OF NON-NUCLEOSIDE INHIBITORS OF THE REVERSE TRANSCRIPTASE |
| KR20100110804A (ko) * | 2007-11-30 | 2010-10-13 | 와이어쓰 엘엘씨 | 포스포디에스테라제 10의 저해물질로서의 아릴 및 헤테로아릴 융합된 이미다조[1,5-ａ]피라진 |
| JP5643105B2 (ja) | 2007-12-14 | 2014-12-17 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 新規イミダゾ［１，２−ａ］ピリジン及びイミダゾ［１，２−ｂ］ピリダジン誘導体 |
| WO2009086130A1 (en) | 2007-12-21 | 2009-07-09 | Wyeth | Imidazo [1,2-b] pyridazine compounds as modulators of liver x receptors |
| EP2224510A1 (en) | 2007-12-21 | 2010-09-01 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| EP2231660A1 (en) | 2007-12-21 | 2010-09-29 | Wyeth LLC | Imidazo [1,2-a] pyridine compounds |
| FR2926556B1 (fr) | 2008-01-22 | 2010-02-19 | Sanofi Aventis | Derives de carboxamides n-azabicycliques, leur preparation et leur application en therapeutique |
| CA2710929A1 (en) | 2008-01-28 | 2009-08-06 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| ATE555116T1 (de) | 2008-02-26 | 2012-05-15 | Merck Sharp & Dohme | Ahcy-hydrolasehemmer zur behandlung von hyperhomocysteinämie |
| CA2716856C (en) | 2008-03-20 | 2013-02-19 | Amgen Inc. | Aurora kinase modulators and method of use |
| CA2721060A1 (en) | 2008-04-09 | 2009-10-15 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| DE102008017853A1 (de) | 2008-04-09 | 2009-10-15 | Merck Patent Gmbh | Thienopyrimidine |
| HUE025528T2 (en) | 2008-04-23 | 2016-05-30 | Gilead Sciences Inc | 1'-substituted carba-nucleoside analogs for antiviral treatment |
| WO2010036407A2 (en) | 2008-05-15 | 2010-04-01 | Biocryst Pharmaceuticals, Inc. | Antiviral nucleoside analogs |
| CA2724842A1 (en) | 2008-05-19 | 2009-11-26 | Sunovion Pharmaceuticals Inc. | Imidazo[1,2-a]pyridine compounds |
| WO2009146358A1 (en) | 2008-05-29 | 2009-12-03 | Sirtris Pharmaceuticals, Inc. | Imidazopyridine and related analogs as sirtuin modulators |
| AR072008A1 (es) | 2008-06-13 | 2010-07-28 | Merck & Co Inc | Compuestos heterobiciclicos como agentes de inhibicion de quinasa p38 |
| WO2010002985A1 (en) | 2008-07-01 | 2010-01-07 | Ptc Therapeutics, Inc. | Bmi-1 protein expression modulators |
| US8124764B2 (en) | 2008-07-14 | 2012-02-28 | Gilead Sciences, Inc. | Fused heterocyclyc inhibitor compounds |
| US8476430B2 (en) | 2008-07-24 | 2013-07-02 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| JP5576370B2 (ja) | 2008-08-06 | 2014-08-20 | ファイザー・インク | Ｃｈｋ−１阻害剤としての６置換２−ヘテロシクリルアミノピラジン化合物 |
| FR2934994B1 (fr) | 2008-08-12 | 2010-09-17 | Sanofi Aventis | Derives de 2-alkyl-6cycloamino-3-(pyridin-4-yl)imidaz°1,2-b! pyridazine, leur preparation et leur application en therapeutique |
| US8198449B2 (en) | 2008-09-11 | 2012-06-12 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US20120021519A1 (en) | 2008-09-19 | 2012-01-26 | Presidents And Fellows Of Harvard College | Efficient induction of pluripotent stem cells using small molecule compounds |
| WO2010048149A2 (en) | 2008-10-20 | 2010-04-29 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| JP5416944B2 (ja) | 2008-10-23 | 2014-02-12 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
| WO2010054253A1 (en) | 2008-11-07 | 2010-05-14 | Biotie Therapies Gmbh | Triazine derivatives as inhibitors of phosphodiesterases |
| WO2010059838A2 (en) | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Pde4 inhibitors selective for the long form of pde4 for treating inflammation and avoiding side effects |
| WO2010059836A1 (en) | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Substituted aza-bridged bicyclics for cardiovascular and cns disease |
| GB0822981D0 (en) | 2008-12-17 | 2009-01-21 | Summit Corp Plc | Compounds for treatment of duchenne muscular dystrophy |
| ES2397934T3 (es) * | 2008-12-17 | 2013-03-12 | Amgen Inc. | Compuestos de aminopiridina y carboxipiridina como inhibidores de fosfodiesterasa 10 |
| JP5210187B2 (ja) | 2009-01-22 | 2013-06-12 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
| EP2210891A1 (en) | 2009-01-26 | 2010-07-28 | Domain Therapeutics | New adenosine receptor ligands and uses thereof |
| WO2010088518A2 (en) | 2009-01-31 | 2010-08-05 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| EP2400991A1 (en) | 2009-02-24 | 2012-01-04 | Janssen Pharmaceutica, N.V. | Radiolabelled pde10 ligands |
| US8367222B2 (en) | 2009-02-27 | 2013-02-05 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| MX2011009314A (es) | 2009-03-05 | 2011-10-11 | Astellas Pharma Inc | Compuesto de quinoxalina. |
| JP2012521354A (ja) | 2009-03-20 | 2012-09-13 | アムジエン・インコーポレーテツド | Ｐｉ３キナーゼの阻害薬 |
| US8604466B2 (en) | 2009-03-24 | 2013-12-10 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element |
| BRPI1014572B8 (pt) | 2009-04-16 | 2022-07-19 | Fundacion Centro Nac De Investigaciones Oncologicas Carlos Iii | Imidazopirazinas para uso como inibidores de cinase |
| TW201111383A (en) * | 2009-05-29 | 2011-04-01 | Wyeth Llc | Substituted imidazo[1,5-a]quinoxalines as inhibitors of phosphodiesterase 10 |
| TW201107329A (en) | 2009-07-30 | 2011-03-01 | Oncotherapy Science Inc | Fused imidazole derivative having ttk inhibitory action |
| CN102482215B (zh) | 2009-08-19 | 2015-04-15 | 出光兴产株式会社 | 芳胺衍生物及使用该芳胺衍生物的有机电致发光元件 |
| KR101774035B1 (ko) | 2009-10-30 | 2017-09-01 | 얀센 파마슈티카 엔.브이. | 이미다조［１，２―ｂ］피리다진 유도체 및 ＰＤＥ１０ 저해제로서의 그의 용도 |
| TW201129546A (en) | 2009-11-16 | 2011-09-01 | Idemitsu Kosan Co | Aromatic amine derivative, and organic electroluminescent element comprising same |
| US9073927B2 (en) | 2010-01-22 | 2015-07-07 | Fundacion Centro Nacional De Investigaciones Oncologicas Carlos Iii | Inhibitors of PI3 kinase |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| US9540379B2 (en) | 2011-01-31 | 2017-01-10 | Boehringer Ingelheim International Gmbh | (1,2,4)triazolo[4,3-A]quinoxaline derivatives as inhibitors of phosphodiesterases |
| CA2833304A1 (en) | 2011-04-28 | 2012-11-01 | Janssen Pharmaceutica Nv | Salt of an inhibitor of phoshodiesterase 10 enzyme |
| WO2013000924A1 (en) | 2011-06-27 | 2013-01-03 | Janssen Pharmaceutica Nv | 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES |
| EP2763989A1 (en) | 2011-09-09 | 2014-08-13 | H. Lundbeck A/S | Pyridine compounds and uses thereof |
| WO2013034755A1 (en) | 2011-09-09 | 2013-03-14 | H. Lundbeck A/S | Triazolopyrazine derivatives and their use for treating neurological and psychiatric disorders |
| AU2013289284B2 (en) | 2012-07-09 | 2017-03-30 | Janssen Pharmaceutica Nv | Inhibitors of phosphodiesterase 10 enzyme |
-
2012
- 2012-06-26 WO PCT/EP2012/062381 patent/WO2013000924A1/en not_active Ceased
- 2012-06-26 US US14/128,835 patent/US10604523B2/en not_active Expired - Fee Related
- 2012-06-26 BR BR112013033375-8A patent/BR112013033375B1/pt not_active IP Right Cessation
- 2012-06-26 AU AU2012277912A patent/AU2012277912B2/en not_active Ceased
- 2012-06-26 CA CA2838645A patent/CA2838645C/en active Active
- 2012-06-26 CN CN201280031255.3A patent/CN103619846B/zh not_active Expired - Fee Related
- 2012-06-26 EA EA201490165A patent/EA027418B1/ru not_active IP Right Cessation
- 2012-06-26 JP JP2014517667A patent/JP6115962B2/ja not_active Expired - Fee Related
- 2012-06-26 ES ES12729637.4T patent/ES2575092T3/es active Active
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- 2012-06-26 MX MX2013015201A patent/MX344600B/es active IP Right Grant
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