KR20190095301A - PDE1 저해제로서 피라졸로[3,4-b]피리딘 및 이미다조[1,5-b]피리다진 - Google Patents
PDE1 저해제로서 피라졸로[3,4-b]피리딘 및 이미다조[1,5-b]피리다진 Download PDFInfo
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- KR20190095301A KR20190095301A KR1020197017840A KR20197017840A KR20190095301A KR 20190095301 A KR20190095301 A KR 20190095301A KR 1020197017840 A KR1020197017840 A KR 1020197017840A KR 20197017840 A KR20197017840 A KR 20197017840A KR 20190095301 A KR20190095301 A KR 20190095301A
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- methyl
- isopropyl
- pyridyl
- amine
- ethoxy
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- 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 title description 19
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 title description 2
- AKJQYWFGJWOGKD-UHFFFAOYSA-N imidazo[1,5-b]pyridazine Chemical compound N1=CC=CC2=CN=CN21 AKJQYWFGJWOGKD-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 256
- 238000000034 method Methods 0.000 claims abstract description 52
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 23
- -1 oxdiazolyl Chemical group 0.000 claims description 174
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
- 229910052736 halogen Inorganic materials 0.000 claims description 68
- 150000002367 halogens Chemical group 0.000 claims description 68
- 125000003545 alkoxy group Chemical group 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 54
- 238000011282 treatment Methods 0.000 claims description 51
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 208000010877 cognitive disease Diseases 0.000 claims description 33
- LUCGBEPEAUHERV-UHFFFAOYSA-N pyridazin-4-amine Chemical class NC1=CC=NN=C1 LUCGBEPEAUHERV-UHFFFAOYSA-N 0.000 claims description 33
- 208000028698 Cognitive impairment Diseases 0.000 claims description 27
- 208000019901 Anxiety disease Diseases 0.000 claims description 26
- 230000036506 anxiety Effects 0.000 claims description 26
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 229960004979 fampridine Drugs 0.000 claims description 21
- 230000004770 neurodegeneration Effects 0.000 claims description 17
- 208000024827 Alzheimer disease Diseases 0.000 claims description 16
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 16
- 208000023105 Huntington disease Diseases 0.000 claims description 16
- 208000018737 Parkinson disease Diseases 0.000 claims description 16
- 201000003631 narcolepsy Diseases 0.000 claims description 16
- 201000000980 schizophrenia Diseases 0.000 claims description 16
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 13
- 208000014644 Brain disease Diseases 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 208000011580 syndromic disease Diseases 0.000 claims description 11
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
- 125000000335 thiazolyl group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000001425 triazolyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 5
- 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 description 5
- 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 description 5
- 125000003566 oxetanyl group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 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 description 4
- SIJOBWVHESJAGJ-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-7-methyl-N-(1,2,4-oxadiazol-3-ylmethyl)-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 SIJOBWVHESJAGJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 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 description 4
- 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 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 class 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 description 3
- 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 description 3
- 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 class 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 description 3
- 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 description 3
- 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 class 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 description 3
- 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 description 3
- 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 class 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 description 3
- 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 class 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 description 3
- 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 class 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 description 3
- 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 class 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 description 3
- 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 class 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 description 3
- 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 class 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 description 3
- 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 class 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 description 3
- RPGUWCCTZYIZDT-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-N-[(2-fluoropyridin-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)F RPGUWCCTZYIZDT-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- AMKJZWRXHVMIBK-UHFFFAOYSA-N 2-(2-ethoxypyridin-3-yl)-N-[(5-fluoropyrimidin-2-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=NC=C(C=N1)F AMKJZWRXHVMIBK-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- OYTNLXFIYGHFKR-UHFFFAOYSA-N 2-(3-ethoxypyridazin-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=1N=NC=CC=1C=1C=C(C=2N(N=1)C(=NC=2C(C)C)C)NCC=1C=NN(C=1)C OYTNLXFIYGHFKR-UHFFFAOYSA-N 0.000 claims description 3
- 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 class 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
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Classifications
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- 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
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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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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- 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
- 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
-
- 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
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- Engineering & Computer Science (AREA)
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- Biomedical Technology (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (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)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA201600784 | 2016-12-22 | ||
| DKPA201600784 | 2016-12-22 | ||
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20190095301A true KR20190095301A (ko) | 2019-08-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020197017840A Ceased KR20190095301A (ko) | 2016-12-22 | 2017-12-20 | PDE1 저해제로서 피라졸로[3,4-b]피리딘 및 이미다조[1,5-b]피리다진 |
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| AU (1) | AU2017384481A1 (enExample) |
| BR (1) | BR112018017067A2 (enExample) |
| CA (1) | CA3046588A1 (enExample) |
| CL (1) | CL2019001669A1 (enExample) |
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| CR (1) | CR20190302A (enExample) |
| DO (1) | DOP2019000169A (enExample) |
| EC (1) | ECSP19043790A (enExample) |
| ES (1) | ES2882335T3 (enExample) |
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| WO (1) | WO2018115067A1 (enExample) |
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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 |
| CN111465410B (zh) | 2017-12-14 | 2022-10-25 | H.隆德贝克有限公司 | 包括施用1h-吡唑并[4,3-b]吡啶的组合治疗 |
| US10766893B2 (en) | 2017-12-20 | 2020-09-08 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| 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 |
| JP7194738B2 (ja) | 2017-12-20 | 2022-12-22 | ハー・ルンドベック・アクチエゼルスカベット | PDE1阻害剤としてのピラゾロ[3,4-b]ピリジン及びイミダゾ[1,5-b]ピリダジン |
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| US20160311831A1 (en) | 2015-04-22 | 2016-10-27 | H. Lundbeck A/S | Imidazotriazinones 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 |
| 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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