TWI567073B - 用於治療發炎疾病之新穎二氫嘧啶異喹啉酮及醫藥組成物 - Google Patents

Info

Publication number

TWI567073B

TWI567073B TW101148765A TW101148765A TWI567073B TW I567073 B TWI567073 B TW I567073B TW 101148765 A TW101148765 A TW 101148765A TW 101148765 A TW101148765 A TW 101148765A TW I567073 B TWI567073 B TW I567073B

Authority

TW

Taiwan

Prior art keywords

ylmethoxy

dihydro

isoquinolin

dioxan

pyrimido

Prior art date

2011-12-22

Links

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• 239000008194 pharmaceutical composition Substances 0.000 title claims description 36
• 238000011282 treatment Methods 0.000 title claims description 30
• 208000027866 inflammatory disease Diseases 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 663
• PVKCAQKXTLCSBC-UHFFFAOYSA-N 1h-isoquinolin-4-one Chemical compound C1=CC=C2C(=O)C=NCC2=C1 PVKCAQKXTLCSBC-UHFFFAOYSA-N 0.000 claims description 152
• 150000003839 salts Chemical class 0.000 claims description 125
• 125000005842 heteroatom Chemical group 0.000 claims description 103
• 229910052739 hydrogen Inorganic materials 0.000 claims description 101
• 229910052760 oxygen Inorganic materials 0.000 claims description 101
• 229910052717 sulfur Inorganic materials 0.000 claims description 97
• 125000000217 alkyl group Chemical group 0.000 claims description 80
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
• -1 9-cyclopentyl Ethyl acetyl-2-([1,4]dioxan-2-ylmethoxy)-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one Chemical compound 0.000 claims description 64
• 125000005843 halogen group Chemical group 0.000 claims description 59
• 229910052757 nitrogen Inorganic materials 0.000 claims description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 55
• 125000003118 aryl group Chemical group 0.000 claims description 51
• 201000010099 disease Diseases 0.000 claims description 50
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 39
• 229910052799 carbon Inorganic materials 0.000 claims description 38
• 125000003545 alkoxy group Chemical group 0.000 claims description 37
• 239000003814 drug Substances 0.000 claims description 35
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 32
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 31
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 31
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 28
• 230000004968 inflammatory condition Effects 0.000 claims description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 208000015181 infectious disease Diseases 0.000 claims description 25
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 23
• 208000023275 Autoimmune disease Diseases 0.000 claims description 22
• 208000035473 Communicable disease Diseases 0.000 claims description 22
• 206010047115 Vasculitis Diseases 0.000 claims description 22
• 230000002124 endocrine Effects 0.000 claims description 22
• 210000002865 immune cell Anatomy 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 208000030159 metabolic disease Diseases 0.000 claims description 21
• 239000003795 chemical substances by application Substances 0.000 claims description 20
• 208000030172 endocrine system disease Diseases 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 20
• HETSDWRDICBRSQ-UHFFFAOYSA-N 3h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CC=NC2=C1 HETSDWRDICBRSQ-UHFFFAOYSA-N 0.000 claims description 19
• 230000003915 cell function Effects 0.000 claims description 19
• 230000001771 impaired effect Effects 0.000 claims description 19
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 18
• 208000006673 asthma Diseases 0.000 claims description 16
• 229940124597 therapeutic agent Drugs 0.000 claims description 15
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 13
• 208000017701 Endocrine disease Diseases 0.000 claims description 13
• 208000016097 disease of metabolism Diseases 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 12
• 230000002314 neuroinflammatory effect Effects 0.000 claims description 11
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• 201000004681 Psoriasis Diseases 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 7
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• QGFYFOHMBDMGBZ-UHFFFAOYSA-N 5-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol Chemical compound C1=C(O)C(CN(CC)CC)=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 QGFYFOHMBDMGBZ-UHFFFAOYSA-N 0.000 claims description 6
• 230000004060 metabolic process Effects 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 5
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 5
• 125000006650 (C2-C4) alkynyl group Chemical group 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
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 150000002013 dioxins Chemical class 0.000 claims description 4
• 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
• 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
• 208000011231 Crohn disease Diseases 0.000 claims description 3
• 206010009887 colitis Diseases 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 2
• 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 2
• 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 2
• 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 2
• 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 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
• 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 description 2
• 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 2
• 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 2
• 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 description 2
• 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 description 2
• 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 2
• 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 2
• 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 2
• 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 description 2
• 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 2
• 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 description 2
• 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 2
• 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 description 2
• 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 2
• 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 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
• 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 description 2
• 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 description 2
• 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 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
• PSEWMGKNBKQHTG-UHFFFAOYSA-N O1C(COCC1)OC1=NC(N2C(C3=CC=C(C=C3CC2)C=2C=NC(=CC2)N2CCOCC2)=C1)=O Chemical compound O1C(COCC1)OC1=NC(N2C(C3=CC=C(C=C3CC2)C=2C=NC(=CC2)N2CCOCC2)=C1)=O PSEWMGKNBKQHTG-UHFFFAOYSA-N 0.000 claims description 2
• 208000025865 Ulcer Diseases 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
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