ES2643379T3 - Nuevas dihidropirimidinoisoquinolinonas y sus composiciones farmacéuticas para el tratamiento de trastornos inflamatorios - Google Patents

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Publication number

ES2643379T3

ES2643379T3 ES12812237.1T ES12812237T ES2643379T3 ES 2643379 T3 ES2643379 T3 ES 2643379T3 ES 12812237 T ES12812237 T ES 12812237T ES 2643379 T3 ES2643379 T3 ES 2643379T3

Authority

ES

Spain

Prior art keywords

ylmethoxy

dihydro

dioxan

isoquinolin

pyrimido

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 description 54
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 38
• 208000027866 inflammatory disease Diseases 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 633
• -1 --NO2 Chemical group 0.000 claims description 468
• 150000003839 salts Chemical class 0.000 claims description 126
• 125000005842 heteroatom Chemical group 0.000 claims description 110
• 229910052760 oxygen Inorganic materials 0.000 claims description 102
• 229910052717 sulfur Inorganic materials 0.000 claims description 100
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 61
• 125000005843 halogen group Chemical group 0.000 claims description 61
• 229910052757 nitrogen Inorganic materials 0.000 claims description 59
• 201000010099 disease Diseases 0.000 claims description 54
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 43
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 41
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 38
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 37
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 37
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 35
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 35
• 239000003814 drug Substances 0.000 claims description 31
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
• 230000004968 inflammatory condition Effects 0.000 claims description 27
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 26
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 25
• PVKCAQKXTLCSBC-UHFFFAOYSA-N 1h-isoquinolin-4-one Chemical compound C1=CC=C2C(=O)C=NCC2=C1 PVKCAQKXTLCSBC-UHFFFAOYSA-N 0.000 claims description 25
• 206010047115 Vasculitis Diseases 0.000 claims description 24
• 208000035473 Communicable disease Diseases 0.000 claims description 23
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 210000002865 immune cell Anatomy 0.000 claims description 23
• 208000023275 Autoimmune disease Diseases 0.000 claims description 22
• 230000002124 endocrine Effects 0.000 claims description 21
• 208000030172 endocrine system disease Diseases 0.000 claims description 20
• 208000030159 metabolic disease Diseases 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 19
• 230000002314 neuroinflammatory effect Effects 0.000 claims description 18
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 230000002265 prevention Effects 0.000 claims description 17
• 208000006673 asthma Diseases 0.000 claims description 16
• 239000012453 solvate Substances 0.000 claims description 16
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 14
• 230000003915 cell function Effects 0.000 claims description 13
• 229940124597 therapeutic agent Drugs 0.000 claims description 13
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 10
• 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
• 230000001771 impaired effect Effects 0.000 claims description 9
• ZKHKSLQAUALGNN-KRWDZBQOSA-N 2-[[(2s)-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-KRWDZBQOSA-N 0.000 claims description 8
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 description 7
• 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 7
• 201000004681 Psoriasis Diseases 0.000 claims description 7
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
• 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 5
• 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 5
• 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 5
• FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 230000001363 autoimmune Effects 0.000 claims description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• 125000004909 2,2-dimethylbutylamino group Chemical group CC(CN*)(CC)C 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 description 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 description 4
• 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 description 4
• 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 4
• 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 4
• NIDXRAREIYMXAW-UHFFFAOYSA-N 2-(1,4-dioxan-2-ylmethoxy)-9-[2-(4-methoxyphenyl)ethynyl]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=CC(OC)=CC=C1C#CC1=CC=C2C3=CC(OCC4OCCOC4)=NC(=O)N3CCC2=C1 NIDXRAREIYMXAW-UHFFFAOYSA-N 0.000 claims description 4
• 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 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
• 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 4
• 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 4
• 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 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
• 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 4
• 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 4
• 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 description 4
• 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 description 4
• 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 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 4
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