JP2020502230A5 - - Google Patents
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- JP2020502230A5 JP2020502230A5 JP2019534197A JP2019534197A JP2020502230A5 JP 2020502230 A5 JP2020502230 A5 JP 2020502230A5 JP 2019534197 A JP2019534197 A JP 2019534197A JP 2019534197 A JP2019534197 A JP 2019534197A JP 2020502230 A5 JP2020502230 A5 JP 2020502230A5
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- JP
- Japan
- Prior art keywords
- methyl
- pyridyl
- amine
- isopropyl
- ethoxy
- 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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- -1 2-ethoxy-3-pyridyl Chemical group 0.000 claims 64
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 57
- LUCGBEPEAUHERV-UHFFFAOYSA-N pyridazin-4-amine Chemical compound NC1=CC=NN=C1 LUCGBEPEAUHERV-UHFFFAOYSA-N 0.000 claims 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- RXKFSWWPDUSPPI-UHFFFAOYSA-N 5-butan-2-yl-2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]imidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(CC)C)C)NCC1=NN(C=N1)C RXKFSWWPDUSPPI-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000014644 Brain disease Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000005793 Restless legs syndrome Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- KWHFOOUBIKZJGG-UHFFFAOYSA-N 1-methyl-3-[1-methyl-4-[(1-methyl-1,2,4-triazol-3-yl)methylamino]-3-propan-2-ylpyrazolo[3,4-b]pyridin-6-yl]pyridin-2-one Chemical compound C(C)(C)C1=NN(C2=NC(=CC(=C21)NCC1=NN(C=N1)C)C=1C(N(C=CC=1)C)=O)C KWHFOOUBIKZJGG-UHFFFAOYSA-N 0.000 claims 1
- ZAQZEKDEDSYQBE-UHFFFAOYSA-N 1-methyl-6-(2-methylthiophen-3-yl)-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C1=C(SC=C1)C)C ZAQZEKDEDSYQBE-UHFFFAOYSA-N 0.000 claims 1
- QRHQCJIVVZHYOW-UHFFFAOYSA-N 1-methyl-6-(4-methyl-1,3-oxazol-2-yl)-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C=1OC=C(N=1)C)C QRHQCJIVVZHYOW-UHFFFAOYSA-N 0.000 claims 1
- HSCRJYMGSBPNJH-UHFFFAOYSA-N 1-methyl-6-(4-methyl-1,3-thiazol-2-yl)-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C=1SC=C(N=1)C)C HSCRJYMGSBPNJH-UHFFFAOYSA-N 0.000 claims 1
- UWCWDWSFBBDRAA-UHFFFAOYSA-N 1-methyl-6-(4-methyl-1,3-thiazol-5-yl)-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C1=C(N=CS1)C)C UWCWDWSFBBDRAA-UHFFFAOYSA-N 0.000 claims 1
- BBARFKFCWUWRRB-UHFFFAOYSA-N 1-methyl-6-(5-methyl-1,3-thiazol-2-yl)-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C=1SC(=CN=1)C)C BBARFKFCWUWRRB-UHFFFAOYSA-N 0.000 claims 1
- WXTIDSSKTNFANV-UHFFFAOYSA-N 1-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-yl-6-(2-propoxypyridin-3-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C=1C(=NC=CC=1)OCCC)C WXTIDSSKTNFANV-UHFFFAOYSA-N 0.000 claims 1
- SZLBZKJVEXRMQK-UHFFFAOYSA-N 1-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-yl-6-(3-propoxypyridazin-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C1=C(N=NC=C1)OCCC)C SZLBZKJVEXRMQK-UHFFFAOYSA-N 0.000 claims 1
- XIVJQJYHOKNWIG-UHFFFAOYSA-N 1-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-yl-6-thiophen-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C=1SC=CC=1)C XIVJQJYHOKNWIG-UHFFFAOYSA-N 0.000 claims 1
- BNPSNWWWLRIQKN-UHFFFAOYSA-N 1-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-6-phenyl-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C1=CC=CC=C1)C BNPSNWWWLRIQKN-UHFFFAOYSA-N 0.000 claims 1
- BQWVEVJAUIPUIF-UHFFFAOYSA-N 1-methyl-N-[(1-methylimidazol-4-yl)methyl]-3-propan-2-yl-6-(2-propoxypyridin-3-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC=1N=CN(C=1)C)C=1C(=NC=CC=1)OCCC)C BQWVEVJAUIPUIF-UHFFFAOYSA-N 0.000 claims 1
- ALAXDBAQTHYEIO-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-3-propan-2-yl-N-(1H-pyrazol-4-ylmethyl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1C=NNC=1 ALAXDBAQTHYEIO-UHFFFAOYSA-N 0.000 claims 1
- XVFYUFDSYNHXPJ-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-3-propan-2-yl-N-(1H-pyrazol-5-ylmethyl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NNC=C1 XVFYUFDSYNHXPJ-UHFFFAOYSA-N 0.000 claims 1
- MLQPMZXVTOLORO-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-3-propan-2-yl-N-(pyridin-2-ylmethyl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NC=CC=C1 MLQPMZXVTOLORO-UHFFFAOYSA-N 0.000 claims 1
- HYJLLXCKLBOODZ-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-3-propan-2-yl-N-(pyrimidin-2-ylmethyl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NC=CC=N1 HYJLLXCKLBOODZ-UHFFFAOYSA-N 0.000 claims 1
- JWWIMQSUSRJCBX-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-3-propan-2-yl-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1C(=NC=CC=1)C(F)(F)F JWWIMQSUSRJCBX-UHFFFAOYSA-N 0.000 claims 1
- JRCKCGZGORHRPK-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NN(C=N1)C JRCKCGZGORHRPK-UHFFFAOYSA-N 0.000 claims 1
- FOVDMANDBXNDTK-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(1-methylimidazol-4-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1N=CN(C=1)C FOVDMANDBXNDTK-UHFFFAOYSA-N 0.000 claims 1
- CHHUNJYTBICHSR-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(1-methylpyrazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NN(C=C1)C CHHUNJYTBICHSR-UHFFFAOYSA-N 0.000 claims 1
- WWZHAOYZYKTTNL-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(1-methylpyrazol-4-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1C=NN(C=1)C WWZHAOYZYKTTNL-UHFFFAOYSA-N 0.000 claims 1
- SUBSKOWZVABHLO-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(1-methyltriazol-4-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1N=NN(C=1)C SUBSKOWZVABHLO-UHFFFAOYSA-N 0.000 claims 1
- WYHCKHHDBOXJTM-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(2-methyl-1,3-oxazol-4-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1N=C(OC=1)C WYHCKHHDBOXJTM-UHFFFAOYSA-N 0.000 claims 1
- LGLWUGOYVLYTIH-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(2-methyl-1,3-oxazol-5-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=CN=C(O1)C LGLWUGOYVLYTIH-UHFFFAOYSA-N 0.000 claims 1
- PFDOJBUVZPOWDD-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(2-methyl-1,3-thiazol-5-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=CN=C(S1)C PFDOJBUVZPOWDD-UHFFFAOYSA-N 0.000 claims 1
- UHUNWIYBXRPDQW-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(2-methyltetrazol-5-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1N=NN(N=1)C UHUNWIYBXRPDQW-UHFFFAOYSA-N 0.000 claims 1
- RJXGGVCAZKTLDK-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(2-methyltriazol-4-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NN(N=C1)C RJXGGVCAZKTLDK-UHFFFAOYSA-N 0.000 claims 1
- NPARRVPJZZVFOY-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NC(=NO1)C NPARRVPJZZVFOY-UHFFFAOYSA-N 0.000 claims 1
- APEKRDZVCNETFQ-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(4-methylpyrimidin-2-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NC=CC(=N1)C APEKRDZVCNETFQ-UHFFFAOYSA-N 0.000 claims 1
- UEPANVKGWPTNHX-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NOC(=N1)C UEPANVKGWPTNHX-UHFFFAOYSA-N 0.000 claims 1
- KYXAQYBPUXXOOB-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1OC(=NN=1)C KYXAQYBPUXXOOB-UHFFFAOYSA-N 0.000 claims 1
- JKBOBLRMRADSDW-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(5-methyl-1H-pyrazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NNC(=C1)C JKBOBLRMRADSDW-UHFFFAOYSA-N 0.000 claims 1
- JAZKAVZXVHLYEX-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(6-methylpyridin-2-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NC(=CC=C1)C JAZKAVZXVHLYEX-UHFFFAOYSA-N 0.000 claims 1
- DWBRWRRULZEDQN-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-N-[(2-methoxypyridin-4-yl)methyl]-1-methyl-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=CC(=NC=C1)OC DWBRWRRULZEDQN-UHFFFAOYSA-N 0.000 claims 1
- RHJDWKHUXITOMG-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-N-[(4-methoxypyridin-2-yl)methyl]-1-methyl-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NC=CC(=C1)OC RHJDWKHUXITOMG-UHFFFAOYSA-N 0.000 claims 1
- KBVLHQFNSGWKFE-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-N-[(5-methoxypyridin-3-yl)methyl]-1-methyl-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1C=NC=C(C=1)OC KBVLHQFNSGWKFE-UHFFFAOYSA-N 0.000 claims 1
- YQSMUCJTZVRTIO-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-N-[(6-methoxypyridin-2-yl)methyl]-1-methyl-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NC(=CC=C1)OC YQSMUCJTZVRTIO-UHFFFAOYSA-N 0.000 claims 1
- XQYKJVCSVMQFML-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-N-[(6-methoxypyridin-3-yl)methyl]-1-methyl-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1C=NC(=CC=1)OC XQYKJVCSVMQFML-UHFFFAOYSA-N 0.000 claims 1
- LVHVLTQXVAXWPP-UHFFFAOYSA-N 6-(2-methoxypyridin-3-yl)-1-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C=1C(=NC=CC=1)OC)C LVHVLTQXVAXWPP-UHFFFAOYSA-N 0.000 claims 1
- BXNZTRPFNUOKDZ-UHFFFAOYSA-N 6-(3-ethoxypyridazin-4-yl)-1-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC=1N=NC=CC=1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NN(C=N1)C BXNZTRPFNUOKDZ-UHFFFAOYSA-N 0.000 claims 1
- SKJAGQLVKJTFOB-UHFFFAOYSA-N 6-(3-ethoxypyridin-4-yl)-1-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC=1C=NC=CC=1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC1=NN(C=N1)C SKJAGQLVKJTFOB-UHFFFAOYSA-N 0.000 claims 1
- NUJLJUWNLVKKKJ-UHFFFAOYSA-N 6-(3-methoxypyrazin-2-yl)-1-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C1=NC=CN=C1OC)C NUJLJUWNLVKKKJ-UHFFFAOYSA-N 0.000 claims 1
- QQFKCMBRRMOQEB-UHFFFAOYSA-N 6-(4-methoxypyrimidin-5-yl)-1-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)(C)C1=NN(C=2N=C(C=C(C=21)NCC1=NN(C=N1)C)C=1C(=NC=NC=1)OC)C QQFKCMBRRMOQEB-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000005299 pyridinones Chemical group 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
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| US10034861B2 (en) | 2016-07-04 | 2018-07-31 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| JOP20190126A1 (ar) | 2016-12-22 | 2019-05-28 | H Lundbeck As | بيرازولو [3، 4-b] بيريدينات وإيميدازو [1، 5-b] بيريدازينات على هيئة مثبطات PDE1 |
| AR113926A1 (es) | 2017-12-14 | 2020-07-01 | H Lundbeck As | Derivados de 1h-pirazolo[4,3-b]piridinas |
| PT3723807T (pt) | 2017-12-14 | 2021-11-26 | H Lundbeck As | Tratamentos de associação que compreendem a administração de 1h-pirazolo[4,3-b]piridinas |
| CN117447475A (zh) | 2017-12-20 | 2024-01-26 | H.隆德贝克有限公司 | 作为PDE1抑制剂的吡唑并[4,3-b]吡啶和咪唑并[1,5-a]嘧啶 |
| TW201927784A (zh) | 2017-12-20 | 2019-07-16 | 丹麥商Ｈ 朗德貝克公司 | 作為pde1抑制劑之大環 |
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| CA3162047A1 (en) * | 2019-12-23 | 2021-07-01 | Anthony Pinkerton | Ectonucleotide pyrophosphatase/phosphodiesterase 1 (enpp1) modulators and uses thereof |
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| NZ579645A (en) | 2007-03-14 | 2012-01-12 | Ranbaxy Lab Ltd | Pyrazolo (3, 4-b) pyridine derivatives as phosphodiesterase inhibitors |
| WO2009067607A2 (en) * | 2007-11-20 | 2009-05-28 | Memory Pharmaceuticals Corporation | Combinations of pde4 inhibitors and antipsychotics for the treatment of psychotic disorders |
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| CN104379578B (zh) | 2012-03-19 | 2017-06-09 | 阿比德治疗公司 | 氨基甲酸酯化合物及其制备和使用方法 |
| TW201533043A (zh) * | 2013-04-18 | 2015-09-01 | Lundbeck & Co As H | 作爲ｌｒｒｋ２抑制劑的芳基吡咯并吡啶衍生化合物 |
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| WO2016147659A1 (en) | 2015-03-16 | 2016-09-22 | Sumitomo Dainippon Pharma Co., Ltd. | Bicyclic imidazolo derivative |
| TW201643167A (zh) * | 2015-04-22 | 2016-12-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之咪唑並三酮 |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| WO2017172795A1 (en) | 2016-03-28 | 2017-10-05 | Intra-Cellular Therapies, Inc. | Novel compositions and methods |
| US10034861B2 (en) | 2016-07-04 | 2018-07-31 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
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| TW201927784A (zh) | 2017-12-20 | 2019-07-16 | 丹麥商Ｈ 朗德貝克公司 | 作為pde1抑制劑之大環 |
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