HRP20220456T1 - Dihidropirimidinoizohinolinoni i njihove farmaceutske kompozicije za liječenje multiple skleroze - Google Patents
Dihidropirimidinoizohinolinoni i njihove farmaceutske kompozicije za liječenje multiple skleroze Download PDFInfo
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- HRP20220456T1 HRP20220456T1 HRP20220456TT HRP20220456T HRP20220456T1 HR P20220456 T1 HRP20220456 T1 HR P20220456T1 HR P20220456T T HRP20220456T T HR P20220456TT HR P20220456 T HRP20220456 T HR P20220456T HR P20220456 T1 HRP20220456 T1 HR P20220456T1
- Authority
- HR
- Croatia
- Prior art keywords
- ylmethoxy
- dihydro
- pyrimido
- isoquinolin
- dioxan
- Prior art date
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- 201000006417 multiple sclerosis Diseases 0.000 title claims 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 15
- 125000005842 heteroatom Chemical group 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 229910052717 sulfur Inorganic materials 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- -1 Methylamide 5-[2-([1,4]Dioxan-2-ylmethoxy)-4-oxo-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-9-yl]- pyridine-2-carboxylic acids Chemical class 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 1
- PVKCAQKXTLCSBC-UHFFFAOYSA-N 1h-isoquinolin-4-one Chemical compound C1=CC=C2C(=O)C=NCC2=C1 PVKCAQKXTLCSBC-UHFFFAOYSA-N 0.000 claims 1
- RFTGHRMNRSHWBL-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=CC=C3CCN2C(=O)N=C1OCC1COCCO1 RFTGHRMNRSHWBL-UHFFFAOYSA-N 0.000 claims 1
- FUKDWBZBOLZEPO-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(1,3-oxazol-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(OCC=4OC=CN=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 FUKDWBZBOLZEPO-UHFFFAOYSA-N 0.000 claims 1
- JRFGYWSBNKDLGZ-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(1-ethylpyrazol-4-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=NN(CC)C=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 JRFGYWSBNKDLGZ-UHFFFAOYSA-N 0.000 claims 1
- UFXFBYILWDOVNC-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(1-methylindol-5-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C=C2N(C)C=CC2=CC=1C(C=1)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 UFXFBYILWDOVNC-UHFFFAOYSA-N 0.000 claims 1
- JUURNCDFTFERJD-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(1-propylpyrazol-4-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=NN(CCC)C=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 JUURNCDFTFERJD-UHFFFAOYSA-N 0.000 claims 1
- GHTUWHMYNSQWBE-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(1h-indazol-5-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4C=C5C=NNC5=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 GHTUWHMYNSQWBE-UHFFFAOYSA-N 0.000 claims 1
- LXEDZWSAQCWVOW-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(1h-indol-2-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4NC5=CC=CC=C5C=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 LXEDZWSAQCWVOW-UHFFFAOYSA-N 0.000 claims 1
- NFUONRNKWZXWKG-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(1h-indol-5-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4C=C5C=CNC5=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 NFUONRNKWZXWKG-UHFFFAOYSA-N 0.000 claims 1
- UBAOKCMYALUHJA-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(1h-pyrazol-4-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C4=CNN=C4)C=C3CCN2C(=O)N=C1OCC1COCCO1 UBAOKCMYALUHJA-UHFFFAOYSA-N 0.000 claims 1
- IOEBVXSFJUYZAS-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-ethoxypyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound CCOC1=NC=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 IOEBVXSFJUYZAS-UHFFFAOYSA-N 0.000 claims 1
- IIOUXJJBJJESOH-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-methoxyphenyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound COC1=CC=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 IIOUXJJBJJESOH-UHFFFAOYSA-N 0.000 claims 1
- FOLJWRCFTUIJDT-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-methoxypyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound COC1=NC=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 FOLJWRCFTUIJDT-UHFFFAOYSA-N 0.000 claims 1
- VBOGBNPLAJEBNR-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-pyrazin-2-ylethyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(CCC=4N=CC=NC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 VBOGBNPLAJEBNR-UHFFFAOYSA-N 0.000 claims 1
- CMMVXNAUFZNASV-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-pyridin-2-ylethyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(CCC=4N=CC=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 CMMVXNAUFZNASV-UHFFFAOYSA-N 0.000 claims 1
- OJUGVILFVLNQIN-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-pyridin-2-ylethynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC=4N=CC=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 OJUGVILFVLNQIN-UHFFFAOYSA-N 0.000 claims 1
- HPNCYWFFYIFFCB-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-pyridin-3-ylethynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC=4C=NC=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 HPNCYWFFYIFFCB-UHFFFAOYSA-N 0.000 claims 1
- JWIVRAVRGYCFQU-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-pyridin-4-ylethynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC=4C=CN=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 JWIVRAVRGYCFQU-UHFFFAOYSA-N 0.000 claims 1
- RORQQZAQQRNVCC-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-pyrimidin-2-ylethynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC=4N=CC=CN=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 RORQQZAQQRNVCC-UHFFFAOYSA-N 0.000 claims 1
- UHBVJNATYAFKGG-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-pyrrolidin-1-ylpyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4C(=NC=CC=4)N4CCCC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 UHBVJNATYAFKGG-UHFFFAOYSA-N 0.000 claims 1
- OEPJEARHYWJBCU-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-ethyl-3-hydroxypent-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CC(O)(CC)CC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 OEPJEARHYWJBCU-UHFFFAOYSA-N 0.000 claims 1
- DJLCKRYRNSUXLI-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-hydroxy-3-methylbut-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CC(C)(O)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 DJLCKRYRNSUXLI-UHFFFAOYSA-N 0.000 claims 1
- YLALDPZXHDFNQM-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-hydroxy-3-phenylbut-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C=CC=CC=1C(O)(C)C#CC(C=1)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 YLALDPZXHDFNQM-UHFFFAOYSA-N 0.000 claims 1
- QOACGHRYBVFGBR-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-hydroxy-3-pyridin-3-ylprop-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C=CN=CC=1C(O)C#CC(C=1)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 QOACGHRYBVFGBR-UHFFFAOYSA-N 0.000 claims 1
- DKAOVRWVJAWHND-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-hydroxy-3-pyridin-3-ylpropyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C=CN=CC=1C(O)CCC(C=1)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 DKAOVRWVJAWHND-UHFFFAOYSA-N 0.000 claims 1
- FQYOAZIPVGMPMX-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-hydroxy-4-methylpent-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CC(O)C(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 FQYOAZIPVGMPMX-UHFFFAOYSA-N 0.000 claims 1
- XYEJBVUGGUZHMQ-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-hydroxy-5-methylhex-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CC(O)CC(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 XYEJBVUGGUZHMQ-UHFFFAOYSA-N 0.000 claims 1
- VUIPUKDNNNJULW-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-hydroxyhex-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CC(O)CCC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 VUIPUKDNNNJULW-UHFFFAOYSA-N 0.000 claims 1
- ZGJBNCCPCLGHNI-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-hydroxyprop-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CCO)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 ZGJBNCCPCLGHNI-UHFFFAOYSA-N 0.000 claims 1
- LQTVLMJGKMGMCX-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-imidazol-1-ylprop-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CCN4C=NC=C4)C=C3CCN2C(=O)N=C1OCC1COCCO1 LQTVLMJGKMGMCX-UHFFFAOYSA-N 0.000 claims 1
- AOYPYDSFTKKNAR-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-methoxyphenyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound COC1=CC=CC(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1 AOYPYDSFTKKNAR-UHFFFAOYSA-N 0.000 claims 1
- HLAQLEHDEDDXKD-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-methoxyprop-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CCOC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 HLAQLEHDEDDXKD-UHFFFAOYSA-N 0.000 claims 1
- GITIKJVOXNTBIV-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(4-hydroxybut-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CCCO)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 GITIKJVOXNTBIV-UHFFFAOYSA-N 0.000 claims 1
- KDECCZNQCUZKMM-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(4-methoxyphenyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=CC(OC)=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 KDECCZNQCUZKMM-UHFFFAOYSA-N 0.000 claims 1
- QKGNRHGIXBMVIU-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(4-morpholin-4-ylphenyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4C=CC(=CC=4)N4CCOCC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 QKGNRHGIXBMVIU-UHFFFAOYSA-N 0.000 claims 1
- MBCWUPQNTZIPCF-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(5-methoxypyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound COC1=CN=CC(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1 MBCWUPQNTZIPCF-UHFFFAOYSA-N 0.000 claims 1
- JFJQSOXFJBIMOJ-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(5-methylfuran-2-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound O1C(C)=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 JFJQSOXFJBIMOJ-UHFFFAOYSA-N 0.000 claims 1
- AXUGDRKDFNZHBY-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(6-ethoxypyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=NC(OCC)=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 AXUGDRKDFNZHBY-UHFFFAOYSA-N 0.000 claims 1
- YDYBKRUWQDWECH-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(6-methoxypyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 YDYBKRUWQDWECH-UHFFFAOYSA-N 0.000 claims 1
- FKDTXJMMDQIQOI-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(6-methylpyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=NC(C)=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 FKDTXJMMDQIQOI-UHFFFAOYSA-N 0.000 claims 1
- KWHDRSJRWXRARR-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(6-morpholin-4-ylpyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4C=NC(=CC=4)N4CCOCC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 KWHDRSJRWXRARR-UHFFFAOYSA-N 0.000 claims 1
- WDXDBZNLHDATCD-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(6-propan-2-yloxypyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=NC(OC(C)C)=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 WDXDBZNLHDATCD-UHFFFAOYSA-N 0.000 claims 1
- RTDPLTPARBVFOC-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(6-pyrrolidin-1-ylpyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4C=NC(=CC=4)N4CCCC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 RTDPLTPARBVFOC-UHFFFAOYSA-N 0.000 claims 1
- KEYIADWBIYGSQO-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(furan-2-ylmethylamino)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(NCC=4OC=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 KEYIADWBIYGSQO-UHFFFAOYSA-N 0.000 claims 1
- KSGKMLVYIUJQMZ-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(pyridin-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(OCC=4N=CC=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 KSGKMLVYIUJQMZ-UHFFFAOYSA-N 0.000 claims 1
- HYVQFMCVFHCARC-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[(1-methylpyrazol-3-yl)methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound CN1C=CC(COC=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=N1 HYVQFMCVFHCARC-UHFFFAOYSA-N 0.000 claims 1
- BSSVGTOJDBSHHZ-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[(3-methyl-1,2,4-oxadiazol-5-yl)methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound CC1=NOC(COC=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=N1 BSSVGTOJDBSHHZ-UHFFFAOYSA-N 0.000 claims 1
- LJIYHSOKPSIAOS-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[(3-methyl-1,2-oxazol-5-yl)methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound O1N=C(C)C=C1COC1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 LJIYHSOKPSIAOS-UHFFFAOYSA-N 0.000 claims 1
- XKTDLLOBRXQBKU-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[(5-ethyl-1,2,4-oxadiazol-3-yl)methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound O1C(CC)=NC(COC=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=N1 XKTDLLOBRXQBKU-UHFFFAOYSA-N 0.000 claims 1
- MZEXYPXWKJZIAA-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound O1C(C)=NC(COC=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=N1 MZEXYPXWKJZIAA-UHFFFAOYSA-N 0.000 claims 1
- QWVGYCGJYBKYSC-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[(5-phenyl-1,3-oxazol-2-yl)methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(OCC=4OC(=CN=4)C=4C=CC=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 QWVGYCGJYBKYSC-UHFFFAOYSA-N 0.000 claims 1
- NHIUBSCZOIMDJS-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[(5-propan-2-yl-1,2,4-oxadiazol-3-yl)methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound O1C(C(C)C)=NC(COC=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=N1 NHIUBSCZOIMDJS-UHFFFAOYSA-N 0.000 claims 1
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- MWUKVCCBFVEQTL-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[6-(trifluoromethyl)pyridin-3-yl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=NC(C(F)(F)F)=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 MWUKVCCBFVEQTL-UHFFFAOYSA-N 0.000 claims 1
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- KZBSTXQYMUCJLA-SFHVURJKSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(4-methoxybutyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCCCOC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 KZBSTXQYMUCJLA-SFHVURJKSA-N 0.000 claims 1
- FKTFVDHBAYCXFO-GGYWPGCISA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(oxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(OCC4OCCCC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 FKTFVDHBAYCXFO-GGYWPGCISA-N 0.000 claims 1
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- VBMLIXPOHJZPOV-IBGZPJMESA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(oxan-4-ylmethylamino)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(NCC4CCOCC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 VBMLIXPOHJZPOV-IBGZPJMESA-N 0.000 claims 1
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- MJIQIOIDMFDDBI-KRWDZBQOSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(oxetan-3-yloxymethyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(COC4COC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 MJIQIOIDMFDDBI-KRWDZBQOSA-N 0.000 claims 1
- VHYAHDGHXLDCRL-SFHVURJKSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-[(3-methyloxetan-3-yl)methoxymethyl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C=C(C=2N(C(N=C(OC[C@H]3OCCOC3)C=2)=O)CC2)C2=CC=1COCC1(C)COC1 VHYAHDGHXLDCRL-SFHVURJKSA-N 0.000 claims 1
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- XVEMVXXDOOBYHB-IBGZPJMESA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-[3-(2-methoxyethoxy)prop-1-ynyl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CCOCCOC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 XVEMVXXDOOBYHB-IBGZPJMESA-N 0.000 claims 1
- QPMSMEGRSPIYCY-UHFFFAOYSA-N 2-[[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]oxy]acetonitrile Chemical compound C1=C2C3=CC=C(OCC#N)C=C3CCN2C(=O)N=C1OCC1COCCO1 QPMSMEGRSPIYCY-UHFFFAOYSA-N 0.000 claims 1
- ZOPUGIAXQNDWQJ-UHFFFAOYSA-N 3-[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]-4-fluorobenzamide Chemical compound NC(=O)C1=CC=C(F)C(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1 ZOPUGIAXQNDWQJ-UHFFFAOYSA-N 0.000 claims 1
- XHQGJPXVKBSGHO-UHFFFAOYSA-N 3-[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]-5-fluorobenzamide Chemical compound NC(=O)C1=CC(F)=CC(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1 XHQGJPXVKBSGHO-UHFFFAOYSA-N 0.000 claims 1
- YDRDGVRBICOWFX-UHFFFAOYSA-N 3-[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1 YDRDGVRBICOWFX-UHFFFAOYSA-N 0.000 claims 1
- KXXDHPDMCWWMPD-UHFFFAOYSA-N 3-[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]benzonitrile Chemical compound C1=C2C3=CC=C(C=4C=C(C=CC=4)C#N)C=C3CCN2C(=O)N=C1OCC1COCCO1 KXXDHPDMCWWMPD-UHFFFAOYSA-N 0.000 claims 1
- YHYPVCLQMAAXSH-UHFFFAOYSA-N 3-[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]pyridine-4-carbonitrile Chemical compound C1=C2C3=CC=C(C=4C(=CC=NC=4)C#N)C=C3CCN2C(=O)N=C1OCC1COCCO1 YHYPVCLQMAAXSH-UHFFFAOYSA-N 0.000 claims 1
- LGNHTQPLDMLJSM-UHFFFAOYSA-N 4-[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 LGNHTQPLDMLJSM-UHFFFAOYSA-N 0.000 claims 1
- UCJBLOVGSXNIMZ-UHFFFAOYSA-N 4-[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]benzonitrile Chemical compound C1=C2C3=CC=C(C=4C=CC(=CC=4)C#N)C=C3CCN2C(=O)N=C1OCC1COCCO1 UCJBLOVGSXNIMZ-UHFFFAOYSA-N 0.000 claims 1
- MOTGLUMBOMRAEA-UHFFFAOYSA-N 4-[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]pyridine-3-carbonitrile Chemical compound C1=C2C3=CC=C(C=4C(=CN=CC=4)C#N)C=C3CCN2C(=O)N=C1OCC1COCCO1 MOTGLUMBOMRAEA-UHFFFAOYSA-N 0.000 claims 1
- KIMZPIYRCIUCII-UHFFFAOYSA-N 5-[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]-2-fluorobenzamide Chemical compound C1=C(F)C(C(=O)N)=CC(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1 KIMZPIYRCIUCII-UHFFFAOYSA-N 0.000 claims 1
- SJZKKRQYCSSGHV-UHFFFAOYSA-N 5-[2-(1,4-dioxan-2-ylmethoxy)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-9-yl]pent-4-ynenitrile Chemical compound C1=C2C3=CC=C(C#CCCC#N)C=C3CCN2C(=O)N=C1OCC1COCCO1 SJZKKRQYCSSGHV-UHFFFAOYSA-N 0.000 claims 1
- BGXQHNQYMRFIGL-SFHVURJKSA-N 9-(2,2-dimethylbutylamino)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(NCC(C)(C)CC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 BGXQHNQYMRFIGL-SFHVURJKSA-N 0.000 claims 1
- URZPEGGUMAIOJZ-KRWDZBQOSA-N 9-(2,2-dimethylpropoxy)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(OCC(C)(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 URZPEGGUMAIOJZ-KRWDZBQOSA-N 0.000 claims 1
- DFIYXVFBAYHFHF-SFHVURJKSA-N 9-(2,2-dimethylpropoxymethyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(COCC(C)(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 DFIYXVFBAYHFHF-SFHVURJKSA-N 0.000 claims 1
- NVXCVOSFBURWAP-UHFFFAOYSA-N 9-(2,3-dimethoxyphenyl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound COC1=CC=CC(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1OC NVXCVOSFBURWAP-UHFFFAOYSA-N 0.000 claims 1
- RYKVFDPZZFYMCH-UHFFFAOYSA-N 9-(2,5-dimethoxyphenyl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound COC1=CC=C(OC)C(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1 RYKVFDPZZFYMCH-UHFFFAOYSA-N 0.000 claims 1
- YWPOGCYNFZSDEW-UHFFFAOYSA-N 9-(2,6-dimethoxypyridin-3-yl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound COC1=NC(OC)=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 YWPOGCYNFZSDEW-UHFFFAOYSA-N 0.000 claims 1
- QKGNXXBOQFMEJH-UHFFFAOYSA-N 9-(2-chlorophenyl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound ClC1=CC=CC=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 QKGNXXBOQFMEJH-UHFFFAOYSA-N 0.000 claims 1
- GOABXHRYGPVPPU-UHFFFAOYSA-N 9-(2-cyclohexylethynyl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CCCCC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 GOABXHRYGPVPPU-UHFFFAOYSA-N 0.000 claims 1
- IRWVHUUXYLAIAL-UHFFFAOYSA-N 9-(2-cyclopentylethynyl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CCCC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 IRWVHUUXYLAIAL-UHFFFAOYSA-N 0.000 claims 1
- CGLMQSKTQZSXCH-GOSISDBHSA-N 9-(2-cyclopropylethyl)-2-[[(2r)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(CCC4CC4)C=C3CCN2C(=O)N=C1OC[C@H]1COCCO1 CGLMQSKTQZSXCH-GOSISDBHSA-N 0.000 claims 1
- CGLMQSKTQZSXCH-SFHVURJKSA-N 9-(2-cyclopropylethyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(CCC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 CGLMQSKTQZSXCH-SFHVURJKSA-N 0.000 claims 1
- IRBAWVGZNJIROV-UHFFFAOYSA-N 9-(2-cyclopropylethynyl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 IRBAWVGZNJIROV-UHFFFAOYSA-N 0.000 claims 1
- IRBAWVGZNJIROV-GOSISDBHSA-N 9-(2-cyclopropylethynyl)-2-[[(2r)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@H]1COCCO1 IRBAWVGZNJIROV-GOSISDBHSA-N 0.000 claims 1
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims 1
- XUUMONIOFNJCFP-UHFFFAOYSA-N 9-(3,3-dimethylbut-1-ynyl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CC(C)(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 XUUMONIOFNJCFP-UHFFFAOYSA-N 0.000 claims 1
- JYBKRGIWCQSOHN-UHFFFAOYSA-N 9-(3,5-dichlorophenyl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound ClC1=CC(Cl)=CC(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1 JYBKRGIWCQSOHN-UHFFFAOYSA-N 0.000 claims 1
- QYUIEQFTTNJTMS-UHFFFAOYSA-N 9-(3,5-dimethyl-1h-pyrazol-4-yl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound CC1=NNC(C)=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 QYUIEQFTTNJTMS-UHFFFAOYSA-N 0.000 claims 1
- LMVWRWNWERGULV-UHFFFAOYSA-N 9-(3,6-dihydro-2h-pyran-4-yl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4CCOCC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 LMVWRWNWERGULV-UHFFFAOYSA-N 0.000 claims 1
- YHSONAVIPVCZDX-UHFFFAOYSA-N 9-(3-anilinoprop-1-ynyl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CCNC=4C=CC=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 YHSONAVIPVCZDX-UHFFFAOYSA-N 0.000 claims 1
- LCNCDLIVLWJDTQ-QFIPXVFZSA-N 9-(3-anilinopropyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(CCCNC=4C=CC=CC=4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 LCNCDLIVLWJDTQ-QFIPXVFZSA-N 0.000 claims 1
- GKJJFXZUNPOFRS-UHFFFAOYSA-N 9-(3-chloro-2-methoxypyridin-4-yl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound COC1=NC=CC(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1Cl GKJJFXZUNPOFRS-UHFFFAOYSA-N 0.000 claims 1
- YKKXXDAPUOFZDC-LJQANCHMSA-N 9-(3-cyclopropylpropoxy)-2-[[(2r)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(OCCCC4CC4)C=C3CCN2C(=O)N=C1OC[C@H]1COCCO1 YKKXXDAPUOFZDC-LJQANCHMSA-N 0.000 claims 1
- YKKXXDAPUOFZDC-IBGZPJMESA-N 9-(3-cyclopropylpropoxy)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(OCCCC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 YKKXXDAPUOFZDC-IBGZPJMESA-N 0.000 claims 1
- BUJAVCYRADIVPH-IBGZPJMESA-N 9-(4,4-dimethylpentoxy)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(OCCCC(C)(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 BUJAVCYRADIVPH-IBGZPJMESA-N 0.000 claims 1
- HVVOJEOEPSKBIY-UHFFFAOYSA-N 9-(cyclohexen-1-yl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4CCCCC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 HVVOJEOEPSKBIY-UHFFFAOYSA-N 0.000 claims 1
- NOKFUPIFXYMEMG-FQEVSTJZSA-N 9-(cyclohexylmethylamino)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(NCC4CCCCC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 NOKFUPIFXYMEMG-FQEVSTJZSA-N 0.000 claims 1
- XIWIBKWGVWDVAZ-FQEVSTJZSA-N 9-(cyclohexyloxymethyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(COC4CCCCC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 XIWIBKWGVWDVAZ-FQEVSTJZSA-N 0.000 claims 1
- WKKMOSLPKTZYHE-FQEVSTJZSA-N 9-(cyclopentylmethoxymethyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(COCC4CCCC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 WKKMOSLPKTZYHE-FQEVSTJZSA-N 0.000 claims 1
- YJRYAOMRRMQDAV-UHFFFAOYSA-N 9-(cyclopentyloxymethyl)-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(COC4CCCC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 YJRYAOMRRMQDAV-UHFFFAOYSA-N 0.000 claims 1
- YJRYAOMRRMQDAV-LJQANCHMSA-N 9-(cyclopentyloxymethyl)-2-[[(2r)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(COC4CCCC4)C=C3CCN2C(=O)N=C1OC[C@H]1COCCO1 YJRYAOMRRMQDAV-LJQANCHMSA-N 0.000 claims 1
- XFWPJCXTBXFACX-KRWDZBQOSA-N 9-(cyclopropylmethoxy)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(OCC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 XFWPJCXTBXFACX-KRWDZBQOSA-N 0.000 claims 1
- ABVVTAOXKDJPMY-SFHVURJKSA-N 9-(cyclopropylmethoxymethyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(COCC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 ABVVTAOXKDJPMY-SFHVURJKSA-N 0.000 claims 1
- LDEXEZSXQFUIEE-UHFFFAOYSA-N 9-[(1,5-dimethylpyrazol-3-yl)methoxy]-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound CN1C(C)=CC(COC=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=N1 LDEXEZSXQFUIEE-UHFFFAOYSA-N 0.000 claims 1
- UWACCCXIIBRQDS-UHFFFAOYSA-N 9-[(5-cyclopropyl-1,2,4-oxadiazol-3-yl)methoxy]-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(OCC=4N=C(ON=4)C4CC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 UWACCCXIIBRQDS-UHFFFAOYSA-N 0.000 claims 1
- WVXXBOGIESBOAV-UHFFFAOYSA-N 9-[(5-tert-butyl-1,2,4-oxadiazol-3-yl)methoxy]-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound O1C(C(C)(C)C)=NC(COC=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=N1 WVXXBOGIESBOAV-UHFFFAOYSA-N 0.000 claims 1
- SVTUOYWRUDSQLS-UHFFFAOYSA-N 9-[(5-tert-butyl-1,3-oxazol-2-yl)methoxy]-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound O1C(C(C)(C)C)=CN=C1COC1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 SVTUOYWRUDSQLS-UHFFFAOYSA-N 0.000 claims 1
- RNGJWXRTLWVRTL-UHFFFAOYSA-N 9-[3-(benzylamino)prop-1-ynyl]-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CCNCC=4C=CC=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 RNGJWXRTLWVRTL-UHFFFAOYSA-N 0.000 claims 1
- OQPXEVMRXYMSCF-UHFFFAOYSA-N 9-[3-[benzyl(methyl)amino]prop-1-ynyl]-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C=CC=CC=1CN(C)CC#CC(C=1)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 OQPXEVMRXYMSCF-UHFFFAOYSA-N 0.000 claims 1
- DJFFTHUKYSGWTP-FQEVSTJZSA-N 9-[cyclohexyl(methyl)amino]-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C=C(C=2N(C(N=C(OC[C@H]3OCCOC3)C=2)=O)CC2)C2=CC=1N(C)C1CCCCC1 DJFFTHUKYSGWTP-FQEVSTJZSA-N 0.000 claims 1
- ZSYGTUKDHOKEBC-UHFFFAOYSA-N 9-cyclopropyl-2-(1,4-dioxan-2-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C4CC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 ZSYGTUKDHOKEBC-UHFFFAOYSA-N 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Classifications
-
- 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
-
- 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
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| US201161578979P | 2011-12-22 | 2011-12-22 | |
| EP17184834.4A EP3378862B1 (en) | 2011-12-22 | 2012-12-20 | Dihydropyrimidinoisoquinolinones and pharmaceutical compositions thereof for the treatment of multiple sclerosis |
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| HRP20220456T1 true HRP20220456T1 (hr) | 2022-05-27 |
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| HRP20171404TT HRP20171404T1 (hr) | 2011-12-22 | 2012-12-20 | Novi dihidropirimidinoizokinolinoni i njihovi farmaceutski pripravci, namijenjeni liječenju upalnih poremećaja |
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| EP2794627B1 (en) | 2011-12-22 | 2018-09-26 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| AR089284A1 (es) | 2011-12-22 | 2014-08-13 | Galapagos Nv | Dihidropirimidinoisoquinolinonas y composiciones farmaceuticas de las mismas para el tratamiento de trastornos inflamatorios |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| EP2935262B1 (en) | 2012-12-20 | 2017-03-15 | Galapagos NV | Novel dihydropyrimidinoisoquinolinones and pharmaceutical compositions thereof for the treatment of inflammatory disorders (gpr84 antagonists) |
| GB201319677D0 (en) * | 2013-11-07 | 2013-12-25 | Eth Z Rich | Cyclopropanation |
| GB201411241D0 (en) * | 2014-06-25 | 2014-08-06 | Galapagos Nv | Novel dihydropyridoisoquinolinones and pharmaceutical compositions thereof for the treatment of inflammatory disorders |
| GB201506894D0 (en) * | 2015-04-23 | 2015-06-10 | Galapagos Nv | Novel dihydropyridoisoquinolinones and pharmaceutical compositions thereof for the treatment of inflammatory disorders |
| JP6918957B2 (ja) * | 2017-03-06 | 2021-08-11 | 上海 インスティテュート オブ マテリア メディカ、チャイニーズ アカデミー オブ サイエンシーズＳｈａｎｇｈａｉ Ｉｎｓｔｉｔｕｔｅ Ｏｆ Ｍａｔｅｒｉａ Ｍｅｄｉｃａ， Ｃｈｉｎｅｓｅ Ａｃａｄｅｍｙ Ｏｆ Ｓｃｉｅｎｃｅｓ | Ｇｐｒ８４受容体拮抗剤およびその使用 |
| EP3403649A1 (en) | 2017-05-16 | 2018-11-21 | Bayer Pharma Aktiengesellschaft | Inhibitors and antagonists of gpr84 for the treatment of endometriosis |
| WO2019096944A1 (en) | 2017-11-15 | 2019-05-23 | Galapagos Nv | Compounds and pharmaceutical compositions thereof for use in the treatment of fibrotic diseases |
| JOP20220156A1 (ar) | 2019-12-19 | 2023-01-30 | Bayer Ag | مشتقات فوروإندازول |
| WO2021123394A1 (en) | 2019-12-20 | 2021-06-24 | University Of Copenhagen | G protein-coupled receptor modulators and a pharmaceutical composition |
| JP2023553295A (ja) | 2020-11-24 | 2023-12-21 | ガラパゴス・ナムローゼ・フェンノートシャップ | 線維性疾患の治療における使用のための化合物及び線維性疾患の治療方法 |
| CA3206499A1 (en) | 2021-02-02 | 2022-08-11 | Liminal Biosciences Limited | Gpr84 antagonists and uses thereof |
| WO2022179940A1 (en) | 2021-02-23 | 2022-09-01 | Bayer Aktiengesellschaft | Furoindazole derivatives as gpr84 antagonists |
| CN115109072A (zh) * | 2021-03-18 | 2022-09-27 | 武汉人福创新药物研发中心有限公司 | 一种gpr84拮抗剂及其制备方法和用途 |
| WO2022218372A1 (zh) * | 2021-04-14 | 2022-10-20 | 武汉人福创新药物研发中心有限公司 | 一种二氢嘧啶并异喹啉酮类衍生物及用途 |
| CA3218018A1 (en) | 2021-04-29 | 2022-11-03 | Bayer Aktiengesellschaft | Furoindazole derivatives as antagonists or inhibitors of gpr84 |
| US20250066335A1 (en) | 2021-06-18 | 2025-02-27 | University Of Copenhagen | Polysubstituted 4-hydroxypyridine and 4-hydroxyquinoline derivatives as gpr84 antagonists |
| EP4361151A4 (en) | 2021-06-21 | 2025-06-11 | Wuhan Humanwell Innovative Drug Research and Development Center Limited Company | Tricyclic compound as a GPR84 antagonist |
| CN115611944A (zh) | 2021-07-15 | 2023-01-17 | 中国科学院上海药物研究所 | 不对称gpr84拮抗剂及其用途 |
| WO2023076668A1 (en) * | 2021-10-29 | 2023-05-04 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Compositions and methods for treatment of cancer |
| GB202202297D0 (en) | 2022-02-21 | 2022-04-06 | Verona Pharma Plc | Formulation production process |
| WO2024083705A1 (en) | 2022-10-18 | 2024-04-25 | Bayer Aktiengesellschaft | Furoindazole derivatives for the treatment of pain |
| CN120569392A (zh) * | 2022-12-30 | 2025-08-29 | 广州市联瑞制药有限公司 | 三环类化合物及其制备方法和应用 |
| WO2024220480A2 (en) * | 2023-04-17 | 2024-10-24 | The Board Of Trustees Of The Leland Stanford Junior University | Method for detecting innate immune action in vivo using gpr84-pet |
| US12194045B1 (en) | 2023-06-26 | 2025-01-14 | Verona Pharma Plc | Particulate composition |
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| DE2720085A1 (de) | 1977-05-05 | 1978-11-16 | Hoechst Ag | Pyrimido(6,1-a)isochinolin-2-on- derivate |
| ATE311884T1 (de) * | 1997-07-12 | 2005-12-15 | Cancer Rec Tech Ltd | Cyclin-abhängige-kinase inhibierende purinderivate |
| EP1165556A1 (en) * | 1999-03-31 | 2002-01-02 | Vernalis Limited | Derivatives of pyrimido[6,1-a]isoquinolin-4-one |
| WO2005007092A2 (en) * | 2003-07-08 | 2005-01-27 | Smithkline Beecham Corporation | Novel chemical compounds |
| WO2005050225A2 (en) | 2003-10-31 | 2005-06-02 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with g protein-coupled receptor 84 (gpr84) |
| WO2007027661A2 (en) | 2005-09-02 | 2007-03-08 | Arena Pharmaceuticals, Inc. | Human g protein-coupled receptor and modulators thereof for the treatment of atherosclerosis and atherosclerotic disease and for the treatment of conditions related to mcp-1 expression |
| US7989461B2 (en) | 2005-12-23 | 2011-08-02 | Amgen Inc. | Substituted quinazolinamine compounds for the treatment of cancer |
| US8217177B2 (en) * | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| KR20110046514A (ko) | 2008-07-31 | 2011-05-04 | 제넨테크, 인크. | 피리미딘 화합물, 조성물 및 사용 방법 |
| JP2011088847A (ja) * | 2009-10-21 | 2011-05-06 | Takeda Chem Ind Ltd | 三環性化合物およびその用途 |
| CA2860192C (en) | 2011-12-22 | 2020-10-27 | Connexios Life Sciences Pvt. Ltd. | Derivatives of aza adamantane and uses thereof |
| CA2859764C (en) | 2011-12-22 | 2019-12-31 | Novartis Ag | Dihydro-benzo-oxazine and dihydro-pyrido-oxazine derivatives |
| KR102083040B1 (ko) | 2011-12-22 | 2020-02-28 | 커넥시오스 라이프 사이언시즈 피브이티. 리미티드 | 11-베타-하이드록시스테로이드 탈수소효소의 저해제로서 사이클릭 아마이드 유도체 및 이의 용도 |
| AR089284A1 (es) | 2011-12-22 | 2014-08-13 | Galapagos Nv | Dihidropirimidinoisoquinolinonas y composiciones farmaceuticas de las mismas para el tratamiento de trastornos inflamatorios |
| EP2935262B1 (en) | 2012-12-20 | 2017-03-15 | Galapagos NV | Novel dihydropyrimidinoisoquinolinones and pharmaceutical compositions thereof for the treatment of inflammatory disorders (gpr84 antagonists) |
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