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 |
| BR112013033375B1 (pt) | 2011-06-27 | 2022-05-10 | Janssen Pharmaceutica N.V | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxa-lina, seu uso, composição farmacêutica que os compreende, processo de preparação dos mesmos, solução estéril e composto intermediário |
| JP2014526453A (ja) * | 2011-09-09 | 2014-10-06 | ハー・ルンドベック・アクチエゼルスカベット | ピリジン化合物およびそれらの使用 |
| HK1206250A1 (en) | 2012-06-26 | 2016-01-08 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 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 |
| BR112015017674A2 (pt) * | 2013-01-31 | 2017-07-11 | Hoffmann La Roche | compostos rádio marcados |
| 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 |
| EP3091983B1 (en) | 2014-01-08 | 2019-10-02 | Intra-Cellular Therapies, Inc. | Pharmaceutical compositions comprising a pde-1 inhibitor and a pde-2 inhibitor |
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-
2012
- 2012-06-26 BR BR112013033375-8A patent/BR112013033375B1/pt not_active IP Right Cessation
- 2012-06-26 US US14/128,835 patent/US10604523B2/en not_active Expired - Fee Related
- 2012-06-26 CN CN201280031255.3A patent/CN103619846B/zh not_active Expired - Fee Related
- 2012-06-26 MX MX2013015201A patent/MX344600B/es active IP Right Grant
- 2012-06-26 EP EP12729637.4A patent/EP2723744B1/en active Active
- 2012-06-26 JP JP2014517667A patent/JP6115962B2/ja not_active Expired - Fee Related
- 2012-06-26 AU AU2012277912A patent/AU2012277912B2/en not_active Ceased
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- 2012-06-26 EA EA201490165A patent/EA027418B1/ru not_active IP Right Cessation
- 2012-06-26 WO PCT/EP2012/062381 patent/WO2013000924A1/en not_active Ceased
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