BR112014015142B1 - Di-hidropirimidinoisoquinolinonas, seus usos, e composição farmacêutica - Google Patents

Info

Publication number

BR112014015142B1

BR112014015142B1 BR112014015142-3A BR112014015142A BR112014015142B1 BR 112014015142 B1 BR112014015142 B1 BR 112014015142B1 BR 112014015142 A BR112014015142 A BR 112014015142A BR 112014015142 B1 BR112014015142 B1 BR 112014015142B1

Authority

BR

Brazil

Prior art keywords

ylmethoxy

dioxan

pyrimido

isoquinolin

dihydro

Prior art date

2011-12-22

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 39
• 150000001875 compounds Chemical class 0.000 claims abstract description 677
• 238000011282 treatment Methods 0.000 claims abstract description 50
• 150000003839 salts Chemical class 0.000 claims description 125
• 125000005842 heteroatom Chemical group 0.000 claims description 111
• 229910052760 oxygen Inorganic materials 0.000 claims description 97
• 229910052717 sulfur Inorganic materials 0.000 claims description 95
• 239000000203 mixture Substances 0.000 claims description 87
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
• 125000005843 halogen group Chemical group 0.000 claims description 63
• 229910052757 nitrogen Inorganic materials 0.000 claims description 58
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 49
• -1 and OH Chemical group 0.000 claims description 49
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 43
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 40
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 39
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 38
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 38
• 239000003814 drug Substances 0.000 claims description 33
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 32
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 238000011321 prophylaxis Methods 0.000 claims description 19
• 239000012453 solvate Substances 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 229940124597 therapeutic agent Drugs 0.000 claims description 13
• 125000004450 alkenylene group Chemical group 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 125000004419 alkynylene group Chemical group 0.000 claims description 10
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
• 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 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 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 description 6
• FUQAHVVPRZZLSA-KRWDZBQOSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(3-hydroxy-3-methylbutyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCC(C)(O)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 FUQAHVVPRZZLSA-KRWDZBQOSA-N 0.000 claims description 6
• 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 description 6
• 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 description 6
• ZKGGBGUHHLWFKC-PKHIMPSTSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(3-methoxybutyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCC(C)OC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 ZKGGBGUHHLWFKC-PKHIMPSTSA-N 0.000 claims description 6
• NSCFDDAIAZZOIZ-SFHVURJKSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(4-hydroxy-4-methylpentyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCCC(C)(O)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 NSCFDDAIAZZOIZ-SFHVURJKSA-N 0.000 claims description 6
• 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 description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• PVKCAQKXTLCSBC-UHFFFAOYSA-N 1h-isoquinolin-4-one Chemical compound C1=CC=C2C(=O)C=NCC2=C1 PVKCAQKXTLCSBC-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 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 4
• 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 description 4
• 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 description 4
• ZKHKSLQAUALGNN-QGZVFWFLSA-N 2-[[(2r)-1,4-dioxan-2-yl]methoxy]-9-(3-methoxypropyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCCOC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@H]1COCCO1 ZKHKSLQAUALGNN-QGZVFWFLSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• DPDKIIHUMBDOHL-JRZJBTRGSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(3-hydroxybutyl)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCC(O)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 DPDKIIHUMBDOHL-JRZJBTRGSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• 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 description 3
• 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 description 3
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• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 3
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• 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 description 3
• 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 description 3
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• 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 description 3
• 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 description 3
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• RDXHLXPVIQVMJC-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-pyridin-4-yl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4C=CN=CC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 RDXHLXPVIQVMJC-UHFFFAOYSA-N 0.000 claims description 3
• GBEMSGJRHUHGQM-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-pyrimidin-5-yl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C=4C=NC=NC=4)C=C3CCN2C(=O)N=C1OCC1COCCO1 GBEMSGJRHUHGQM-UHFFFAOYSA-N 0.000 claims description 3
• YYMRQEAZLNSZOV-UHFFFAOYSA-N 2-[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 YYMRQEAZLNSZOV-UHFFFAOYSA-N 0.000 claims description 3
• YYMRQEAZLNSZOV-LJQANCHMSA-N 2-[2-[[(2r)-1,4-dioxan-2-yl]methoxy]-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=C1OC[C@H]1COCCO1 YYMRQEAZLNSZOV-LJQANCHMSA-N 0.000 claims description 3
• YYMRQEAZLNSZOV-IBGZPJMESA-N 2-[2-[[(2s)-1,4-dioxan-2-yl]methoxy]-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=C1OC[C@@H]1COCCO1 YYMRQEAZLNSZOV-IBGZPJMESA-N 0.000 claims description 3
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• FXENJTMDNMCZIQ-LJQANCHMSA-N 2-[[(2r)-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-LJQANCHMSA-N 0.000 claims description 3
• PXLDABOJDRUBRB-GOSISDBHSA-N 2-[[(2r)-1,4-dioxan-2-yl]methoxy]-9-pentyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(CCCCC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@H]1COCCO1 PXLDABOJDRUBRB-GOSISDBHSA-N 0.000 claims description 3
• 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 3
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• VFPRXDIPJDALBQ-INIZCTEOSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(2-methoxyethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(OCCOC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 VFPRXDIPJDALBQ-INIZCTEOSA-N 0.000 claims description 3
• WCHQRUYPBWMRFP-SFHVURJKSA-N 2-[[(2s)-1,4-dioxan-2-yl]methoxy]-9-(2-propan-2-yloxyethoxy)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(OCCOC(C)C)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC[C@@H]1COCCO1 WCHQRUYPBWMRFP-SFHVURJKSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• 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 description 3
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• 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 description 3
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