RU2019116251A - Пиразоло[3,4-b]пиридины и имидазо[1,5-b]пиридазины в качестве ингибиторов pde1 - Google Patents
Пиразоло[3,4-b]пиридины и имидазо[1,5-b]пиридазины в качестве ингибиторов pde1 Download PDFInfo
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- RU2019116251A RU2019116251A RU2019116251A RU2019116251A RU2019116251A RU 2019116251 A RU2019116251 A RU 2019116251A RU 2019116251 A RU2019116251 A RU 2019116251A RU 2019116251 A RU2019116251 A RU 2019116251A RU 2019116251 A RU2019116251 A RU 2019116251A
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- methyl
- pyridyl
- amine
- isopropyl
- ethoxy
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- 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 title 1
- 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title 1
- 150000004892 pyridazines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- -1 (1-methyl-1H-1,2,4-triazol-3-yl) methyl Chemical group 0.000 claims 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- FNGPMGIWFZWLDM-UHFFFAOYSA-N 5-butan-2-yl-2-(2-ethoxypyridin-3-yl)-7-methyl-N-(1H-pyrazol-5-ylmethyl)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=NNC=C1 FNGPMGIWFZWLDM-UHFFFAOYSA-N 0.000 claims 2
- 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
- VDZUJWBMHWGEHF-UHFFFAOYSA-N 5-butan-2-yl-2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(1-methylpyrazol-4-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)NCC=1C=NN(C=1)C VDZUJWBMHWGEHF-UHFFFAOYSA-N 0.000 claims 2
- JZGITHYCPPKNND-UHFFFAOYSA-N 5-butan-2-yl-2-(2-ethoxypyridin-3-yl)-N-[(2-methoxypyridin-4-yl)methyl]-7-methylimidazo[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=CC(=NC=C1)OC JZGITHYCPPKNND-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease 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
- 238000000034 method Methods 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 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
- 150000005299 pyridinones Chemical group 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 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
- 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
- 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
- GPQAPIDIPLHUKX-UHFFFAOYSA-N 2-(1,3-benzoxazol-7-yl)-7-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound O1C=NC2=C1C(=CC=C2)C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=NN(C=N1)C GPQAPIDIPLHUKX-UHFFFAOYSA-N 0.000 claims 1
- HGQYXGMNDSLKAK-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-5-propan-2-yl-N-(1H-pyrazol-4-ylmethyl)imidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC=1C=NNC=1 HGQYXGMNDSLKAK-UHFFFAOYSA-N 0.000 claims 1
- GZIIKOSUOPMFBN-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-5-propan-2-yl-N-(1H-pyrazol-5-ylmethyl)imidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=NNC=C1 GZIIKOSUOPMFBN-UHFFFAOYSA-N 0.000 claims 1
- CSIIVTYLKGCZSL-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-5-propan-2-yl-N-(pyridin-2-ylmethyl)imidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=NC=CC=C1 CSIIVTYLKGCZSL-UHFFFAOYSA-N 0.000 claims 1
- GKPYPEMOOUITHU-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-5-propan-2-yl-N-(pyrimidin-2-ylmethyl)imidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=NC=CC=N1 GKPYPEMOOUITHU-UHFFFAOYSA-N 0.000 claims 1
- JEFFLSLDDQNQKB-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-5-propan-2-yl-N-[[2-(trifluoromethyl)pyridin-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(C)C)C)NCC=1C(=NC=CC=1)C(F)(F)F JEFFLSLDDQNQKB-UHFFFAOYSA-N 0.000 claims 1
- BMFZYHZGUOHQNG-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(1-methyl-1,2,4-triazol-3-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=NN(C=N1)C BMFZYHZGUOHQNG-UHFFFAOYSA-N 0.000 claims 1
- VTLYOTDVPMICIY-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(1-methylimidazol-4-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC=1N=CN(C=1)C VTLYOTDVPMICIY-UHFFFAOYSA-N 0.000 claims 1
- FAPQMRSFHIOJCJ-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(1-methylpyrazol-3-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=NN(C=C1)C FAPQMRSFHIOJCJ-UHFFFAOYSA-N 0.000 claims 1
- RJMKCZAZEIDVTF-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(1-methylpyrazol-4-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC=1C=NN(C=1)C RJMKCZAZEIDVTF-UHFFFAOYSA-N 0.000 claims 1
- WIBPYCKUGVEEPW-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(2-methyl-1,3-oxazol-4-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC=1N=C(OC=1)C WIBPYCKUGVEEPW-UHFFFAOYSA-N 0.000 claims 1
- KCQKYGDVZWPGLK-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(2-methyl-1,3-oxazol-5-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=CN=C(O1)C KCQKYGDVZWPGLK-UHFFFAOYSA-N 0.000 claims 1
- OFRYJGDTAAHRNZ-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(2-methyl-1,3-thiazol-5-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=CN=C(S1)C OFRYJGDTAAHRNZ-UHFFFAOYSA-N 0.000 claims 1
- HCRXVWMKOPRWDR-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(2-methyltetrazol-5-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC=1N=NN(N=1)C HCRXVWMKOPRWDR-UHFFFAOYSA-N 0.000 claims 1
- AJKPMQDASSUWHP-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(2-methyltriazol-4-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=NN(N=C1)C AJKPMQDASSUWHP-UHFFFAOYSA-N 0.000 claims 1
- WFHWENZYHXHCJW-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=NC(=NO1)C WFHWENZYHXHCJW-UHFFFAOYSA-N 0.000 claims 1
- PUMZQONTNXYATN-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=NOC(=N1)C PUMZQONTNXYATN-UHFFFAOYSA-N 0.000 claims 1
- FVVLBAMOQRYQPU-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC=1OC(=NN=1)C FVVLBAMOQRYQPU-UHFFFAOYSA-N 0.000 claims 1
- FNPAIIMMNTUEOV-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-[(5-methyl-1H-pyrazol-3-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=NNC(=C1)C FNPAIIMMNTUEOV-UHFFFAOYSA-N 0.000 claims 1
- UFMYTOVTLLJXOG-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-N-(imidazo[1,2-a]pyridin-5-ylmethyl)-7-methyl-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=CC=CC=2N1C=CN=2 UFMYTOVTLLJXOG-UHFFFAOYSA-N 0.000 claims 1
- LABOBNCXCXUMDC-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-N-(imidazo[1,5-a]pyridin-5-ylmethyl)-7-methyl-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=CC=CC=2N1C=NC=2 LABOBNCXCXUMDC-UHFFFAOYSA-N 0.000 claims 1
- ZYPDIQFNTLQCJN-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-N-[(2-methoxypyridin-3-yl)methyl]-7-methyl-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC=1C(=NC=CC=1)OC ZYPDIQFNTLQCJN-UHFFFAOYSA-N 0.000 claims 1
- LCCNKWNCXOSLKI-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-N-[(2-methoxypyridin-4-yl)methyl]-7-methyl-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC1=CC(=NC=C1)OC LCCNKWNCXOSLKI-UHFFFAOYSA-N 0.000 claims 1
- HOQBWECZUQEPSS-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-N-[(5-methoxypyridin-3-yl)methyl]-7-methyl-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC=1C=NC=C(C=1)OC HOQBWECZUQEPSS-UHFFFAOYSA-N 0.000 claims 1
- DEHXKVBXNSFYTR-UHFFFAOYSA-N 2-(3-ethoxypyridin-4-yl)-7-methyl-N-[(1-methylpyrazol-4-yl)methyl]-5-propan-2-ylimidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)OC=1C=NC=CC=1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC=1C=NN(C=1)C DEHXKVBXNSFYTR-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
- 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
- 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
- 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
- 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
- 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
- WGGOLWUIHCLTNX-UHFFFAOYSA-N 7-methyl-N-[(1-methylpyrazol-4-yl)methyl]-5-propan-2-yl-2-(2-propoxypyridin-3-yl)imidazo[1,5-b]pyridazin-4-amine Chemical compound C(C)(C)C=1N=C(N2N=C(C=C(C2=1)NCC=1C=NN(C=1)C)C=1C(=NC=CC=1)OCCC)C WGGOLWUIHCLTNX-UHFFFAOYSA-N 0.000 claims 1
- 230000003920 cognitive function Effects 0.000 claims 1
- 230000006735 deficit Effects 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
- GHVLUVWTSAIEOT-UHFFFAOYSA-N imidazo[1,5-b]pyridazin-4-amine Chemical compound N=1N2C(C(=CC=1)N)=CN=C2 GHVLUVWTSAIEOT-UHFFFAOYSA-N 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
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- LUCGBEPEAUHERV-UHFFFAOYSA-N pyridazin-4-amine Chemical compound NC1=CC=NN=C1 LUCGBEPEAUHERV-UHFFFAOYSA-N 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group 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
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/502—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with carbocyclic ring systems, e.g. cinnoline, phthalazine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
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| DKPA201700404 | 2017-07-06 | ||
| DKPA201700404 | 2017-07-06 | ||
| PCT/EP2017/083721 WO2018115067A1 (en) | 2016-12-22 | 2017-12-20 | Pyrazolo[3,4-b]pyridines and imidazo[1,5-b]pyridazines as pde1 inhibitors |
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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 |
| LT3723807T (lt) | 2017-12-14 | 2021-12-10 | H. Lundbeck A/S | Kombinuoti gydymai, apimantys 1h-pirazolo[4,3-b]piridinų vartojimą |
| AR113926A1 (es) | 2017-12-14 | 2020-07-01 | H Lundbeck As | Derivados de 1h-pirazolo[4,3-b]piridinas |
| 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 |
| US11535611B2 (en) | 2017-12-20 | 2022-12-27 | H. Lundbeck A/S | Pyrazolo[3,4-B]pyridines and imidazo[1,5-B]pyridazines as PDE1 inhibitors |
| US10766893B2 (en) | 2017-12-20 | 2020-09-08 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| CN115151550B (zh) * | 2019-12-23 | 2024-11-22 | 桑福德·伯纳姆·普雷比医学发现研究所 | 外核苷酸焦磷酸酶/磷酸二酯酶1(enpp1)调节剂及其用途 |
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| ATE430746T1 (de) | 2004-10-19 | 2009-05-15 | Smithkline Beecham Cork Ltd | Crf-rezeptor-antagonisten und zugehörige verfahren |
| EP2089034A4 (en) | 2006-12-05 | 2010-07-28 | Intra Cellular Therapies Inc | NEW USES |
| PT2124944E (pt) | 2007-03-14 | 2012-05-17 | Ranbaxy Lab Ltd | Derivados de pirazolo[3,4-b]piridina como inibidores de fosfodiesterase |
| WO2009067607A2 (en) * | 2007-11-20 | 2009-05-28 | Memory Pharmaceuticals Corporation | Combinations of pde4 inhibitors and antipsychotics for the treatment of psychotic disorders |
| BRPI0922700A2 (pt) * | 2008-12-06 | 2015-08-11 | Intracellular Therapies Inc | Compostos orgânicos |
| US9567302B2 (en) | 2012-03-19 | 2017-02-14 | Abide Therapeutics, Inc. | Carbamate compounds and of making and using same |
| 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 |
| US20160083400A1 (en) | 2014-09-18 | 2016-03-24 | Sunovion Pharmaceuticals Inc. | Tricyclic guanidine derivative |
| US20160083391A1 (en) | 2014-09-18 | 2016-03-24 | Sunovion Pharmaceuticals Inc. | Tricyclic piperazine derivative |
| WO2016042775A1 (en) | 2014-09-18 | 2016-03-24 | Sunovion Pharmaceuticals Inc. | Tricyclic derivative |
| TW201629064A (zh) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之三唑並吡酮 |
| US20180044343A1 (en) | 2015-03-16 | 2018-02-15 | Sumitomo Dainippon Pharma Co., Ltd. | Bicyclic imidazolo derivative |
| US20160311831A1 (en) | 2015-04-22 | 2016-10-27 | H. Lundbeck A/S | Imidazotriazinones as PDE1 Inhibitors |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| US10682354B2 (en) | 2016-03-28 | 2020-06-16 | Intra-Cellular Therapies, Inc. | Compositions and methods |
| 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 |
| 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 |
| US10766893B2 (en) | 2017-12-20 | 2020-09-08 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
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