CA2859578C - Dihydropyrimidinoisoquinolinones and pharmaceutical compositions thereof for the treatment of inflammatory disorders. - Google Patents

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Publication number

CA2859578C

CA2859578C CA2859578A CA2859578A CA2859578C CA 2859578 C CA2859578 C CA 2859578C CA 2859578 A CA2859578 A CA 2859578A CA 2859578 A CA2859578 A CA 2859578A CA 2859578 C CA2859578 C CA 2859578C

Authority

CA

Canada

Prior art keywords

ylmethoxy

dihydro

pyrimido

dioxan

isoquinolin

Prior art date

2011-12-22

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 238000011282 treatment Methods 0.000 title claims abstract description 59
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 38
• 208000027866 inflammatory disease Diseases 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 685
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims abstract description 38
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims abstract description 38
• 230000004968 inflammatory condition Effects 0.000 claims abstract description 35
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 28
• 206010047115 Vasculitis Diseases 0.000 claims abstract description 27
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 23
• 238000004519 manufacturing process Methods 0.000 claims abstract description 14
• 150000003839 salts Chemical class 0.000 claims description 127
• 125000005842 heteroatom Chemical group 0.000 claims description 108
• PVKCAQKXTLCSBC-UHFFFAOYSA-N 1h-isoquinolin-4-one Chemical compound C1=CC=C2C(=O)C=NCC2=C1 PVKCAQKXTLCSBC-UHFFFAOYSA-N 0.000 claims description 106
• 125000000217 alkyl group Chemical group 0.000 claims description 96
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
• 125000005843 halogen group Chemical group 0.000 claims description 59
• 229910052757 nitrogen Inorganic materials 0.000 claims description 59
• 229910052717 sulfur Inorganic materials 0.000 claims description 58
• 125000003118 aryl group Chemical group 0.000 claims description 51
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 38
• 239000003814 drug Substances 0.000 claims description 33
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 31
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 27
• 238000011321 prophylaxis Methods 0.000 claims description 21
• 208000006673 asthma Diseases 0.000 claims description 18
• 239000012453 solvate Substances 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 16
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 14
• 229940124597 therapeutic agent Drugs 0.000 claims description 14
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 11
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 9
• 201000004681 Psoriasis Diseases 0.000 claims description 9
• 125000002947 alkylene group Chemical group 0.000 claims description 9
• 125000004450 alkenylene group Chemical group 0.000 claims description 7
• 125000004419 alkynylene group Chemical group 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
• 208000011231 Crohn disease Diseases 0.000 claims description 5
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000001475 halogen functional group Chemical group 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• PEFSAXPTEDRHFK-KRWDZBQOSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(2-ethoxyethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(OCCOCC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 PEFSAXPTEDRHFK-KRWDZBQOSA-N 0.000 claims description 2
• FDBUJVHYUALRBC-FQEVSTJZSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(oxan-4-ylmethoxymethyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(COCC4CCOCC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 FDBUJVHYUALRBC-FQEVSTJZSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-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
• 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
• BCFJWOVDPHJBTF-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(2-methylpyridin-4-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=NC(C)=CC(C=2C=C3C(C=4N(C(N=C(OCC5OCCOC5)C=4)=O)CC3)=CC=2)=C1 BCFJWOVDPHJBTF-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
• 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
• 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
• 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
• FMUHXPKLGMHDNM-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-hydroxybut-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CC(O)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 FMUHXPKLGMHDNM-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
• QUXJSJPUEFPUAX-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-hydroxypent-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CC(O)CC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 QUXJSJPUEFPUAX-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
• RIDUIZFRYDXCCD-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-methoxy-4-methylpent-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CC(OC)C(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 RIDUIZFRYDXCCD-UHFFFAOYSA-N 0.000 claims 1
• DOHKQKMAJBATQH-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(3-methylbut-1-ynyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CC(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 DOHKQKMAJBATQH-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
• 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
• 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
• JACDZXYQWMDVHD-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-(6-piperidin-1-ylpyridin-3-yl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4C=NC(=CC=4)N4CCCCC4)C=C3CCN2C(=O)N=C1OCC1COCCO1 JACDZXYQWMDVHD-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
• WMUHITDTZXIXDX-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[(2-methylpropan-2-yl)oxymethyl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(COC(C)(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 WMUHITDTZXIXDX-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
• 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
• RJWYVPVVMDCLSE-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[1-(3-methylbutyl)pyrazol-4-yl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=NN(CCC(C)C)C=C1C1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 RJWYVPVVMDCLSE-UHFFFAOYSA-N 0.000 claims 1
• BPFWZVHBOZPPJX-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[2-(1-hydroxycyclopentyl)ethynyl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C=C(C=2N(C(N=C(OCC3OCCOC3)C=2)=O)CC2)C2=CC=1C#CC1(O)CCCC1 BPFWZVHBOZPPJX-UHFFFAOYSA-N 0.000 claims 1
• JZZYQXJKGTXYCE-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[2-(3-methylimidazol-4-yl)ethynyl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound CN1C=NC=C1C#CC1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 JZZYQXJKGTXYCE-UHFFFAOYSA-N 0.000 claims 1
• KDZIDRHAOFIRCJ-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[3-(pyridin-3-ylmethylamino)prop-1-ynyl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CCNCC=4C=NC=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 KDZIDRHAOFIRCJ-UHFFFAOYSA-N 0.000 claims 1
• 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
• UDEWBHZYVLSYNN-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-ethynyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#C)C=C3CCN2C(=O)N=C1OCC1COCCO1 UDEWBHZYVLSYNN-UHFFFAOYSA-N 0.000 claims 1
• FYDLWSDXHIOKMI-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-hex-1-ynyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CCCCC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 FYDLWSDXHIOKMI-UHFFFAOYSA-N 0.000 claims 1
• KFLOTFVSWTXWOA-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-methoxy-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(OC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 KFLOTFVSWTXWOA-UHFFFAOYSA-N 0.000 claims 1
• BDMWQQBSFVLOPB-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-pent-1-ynyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CCCC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OCC1COCCO1 BDMWQQBSFVLOPB-UHFFFAOYSA-N 0.000 claims 1
• UCKMDBYAIBGKDN-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-pyridin-3-yl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4C=NC=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 UCKMDBYAIBGKDN-UHFFFAOYSA-N 0.000 claims 1
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• XTFGTMPOQSBSFP-GOSISDBHSA-N 2-[[(2r)-1,4-dioxan-2-yl]methoxy]-9-(2-propoxyethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(OCCOCCC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@H]1COCCO1 XTFGTMPOQSBSFP-GOSISDBHSA-N 0.000 claims 1
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• CLGGBTXQLRICFB-LJQANCHMSA-N 2-[[(2r)-1,4-dioxan-2-yl]methoxy]-9-(oxan-4-yloxymethyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(COC4CCOCC4)C=C3CCN2C(=O)N=C1OC[C@H]1COCCO1 CLGGBTXQLRICFB-LJQANCHMSA-N 0.000 claims 1
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• LGDSFSUAFPMIIJ-LJQANCHMSA-N 2-[[(2r)-1,4-dioxan-2-yl]methoxy]-9-[2-(4-hydroxyoxan-4-yl)ethynyl]-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=1C#CC1(O)CCOCC1 LGDSFSUAFPMIIJ-LJQANCHMSA-N 0.000 claims 1
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• XTFGTMPOQSBSFP-SFHVURJKSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(2-propoxyethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(OCCOCCC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 XTFGTMPOQSBSFP-SFHVURJKSA-N 0.000 claims 1
• ZYKSMEXRFQZAAW-IBGZPJMESA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(3-ethyl-3-hydroxypentyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCC(O)(CC)CC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 ZYKSMEXRFQZAAW-IBGZPJMESA-N 0.000 claims 1
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• LACCZGDYHGONEM-YMXDCFFPSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(3-hydroxy-4,4-dimethylpentyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCC(O)C(C)(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 LACCZGDYHGONEM-YMXDCFFPSA-N 0.000 claims 1
• HXNYJZAEGHSVKR-YMXDCFFPSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(3-hydroxy-4-methylpentyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCC(O)C(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 HXNYJZAEGHSVKR-YMXDCFFPSA-N 0.000 claims 1
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• ARXUTZULCOVLEU-ZVAWYAOSSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(3-hydroxypentyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCC(O)CC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 ARXUTZULCOVLEU-ZVAWYAOSSA-N 0.000 claims 1
• FRYSOWASMQOUDH-YDNXMHBPSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(3-methoxy-4-methylpentyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCC(OC)C(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 FRYSOWASMQOUDH-YDNXMHBPSA-N 0.000 claims 1
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• VFYZBZNEAMFLHG-KRWDZBQOSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(4-hydroxybutyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCCCO)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 VFYZBZNEAMFLHG-KRWDZBQOSA-N 0.000 claims 1
• RUKXQQIDEBYETE-PKHIMPSTSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(4-hydroxypentyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCCC(O)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 RUKXQQIDEBYETE-PKHIMPSTSA-N 0.000 claims 1
• 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
• NWHHOSIUJNIWBU-IBGZPJMESA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(oxan-4-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(OCC4CCOCC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 NWHHOSIUJNIWBU-IBGZPJMESA-N 0.000 claims 1
• 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
• SUTVBPGMNVGUEY-KRWDZBQOSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(oxetan-3-ylmethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(OCC4COC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 SUTVBPGMNVGUEY-KRWDZBQOSA-N 0.000 claims 1
• 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
• FXENJTMDNMCZIQ-IBGZPJMESA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-[2-(1-hydroxycyclopentyl)ethyl]-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=1CCC1(O)CCCC1 FXENJTMDNMCZIQ-IBGZPJMESA-N 0.000 claims 1
• JYCHUBYLKOFCRG-FQEVSTJZSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-[3-(2-ethoxyethoxy)prop-1-ynyl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CCOCCOCC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 JYCHUBYLKOFCRG-FQEVSTJZSA-N 0.000 claims 1
• KPCFQZWDXFNIFC-SFHVURJKSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-[3-(2-fluoroethoxy)prop-1-ynyl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(C#CCOCCF)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 KPCFQZWDXFNIFC-SFHVURJKSA-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
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