CA2895660A1 - Tricyclic compounds for inhibiting the cftr channel - Google Patents

Info

Publication number

CA2895660A1

CA2895660A1 CA2895660A CA2895660A CA2895660A1 CA 2895660 A1 CA2895660 A1 CA 2895660A1 CA 2895660 A CA2895660 A CA 2895660A CA 2895660 A CA2895660 A CA 2895660A CA 2895660 A1 CA2895660 A1 CA 2895660A1

Authority

CA

Canada

Prior art keywords

dione

pyrimido

dimethyl

pyrrolo

dihydro

Prior art date

2012-12-19

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 357
• 230000002401 inhibitory effect Effects 0.000 title description 8
• 150000003839 salts Chemical class 0.000 claims abstract description 59
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
• 238000000034 method Methods 0.000 claims description 281
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 142
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 68
• -1 pyridine-2-yl Chemical group 0.000 claims description 65
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
• 108010079245 Cystic Fibrosis Transmembrane Conductance Regulator Proteins 0.000 claims description 41
• 125000005843 halogen group Chemical group 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 34
• 239000003795 chemical substances by application Substances 0.000 claims description 33
• 201000010099 disease Diseases 0.000 claims description 32
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
• 206010012735 Diarrhoea Diseases 0.000 claims description 30
• 239000003814 drug Substances 0.000 claims description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
• 125000001424 substituent group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 20
• 125000003282 alkyl amino group Chemical group 0.000 claims description 18
• 208000030761 polycystic kidney disease Diseases 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 13
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 230000000694 effects Effects 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 9
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 4
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• OEKJILMMMNKMKL-UHFFFAOYSA-N 1,3,8,8-tetramethyl-9-(4-methyl-1,3-thiazol-2-yl)-5-phenyl-7,9-dihydropyrimido[4,5-a]pyrrolizine-2,4-dione Chemical compound CC1=CSC(C2C(CN3C2=C2C(C(N(C)C(=O)N2C)=O)=C3C=2C=CC=CC=2)(C)C)=N1 OEKJILMMMNKMKL-UHFFFAOYSA-N 0.000 claims 2
• OWDSPKZXDBSXBH-UHFFFAOYSA-N 1,3-dimethyl-10-(4-methyl-1,3-thiazol-2-yl)-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=CC=CC=3)CCS2)=N1 OWDSPKZXDBSXBH-UHFFFAOYSA-N 0.000 claims 2
• SFMJYXVKTHMZBI-UHFFFAOYSA-N 1,3-dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound O1C(C)=CC=C1C1C2=C(N(C)C(=O)N(C)C3=O)C3=C(C=3C=CC=CC=3)N2CCS1 SFMJYXVKTHMZBI-UHFFFAOYSA-N 0.000 claims 2
• ZVWHNWKIKAKMBA-UHFFFAOYSA-N 10-(3-chlorophenyl)-1,3-dimethyl-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3C=C(Cl)C=CC=3)SCCN2C=1C1=CC=CC=C1 ZVWHNWKIKAKMBA-UHFFFAOYSA-N 0.000 claims 2
• NODRNSUBQQBWEJ-UHFFFAOYSA-N 10-(4-chloro-1,3-thiazol-2-yl)-5-[4-(hydroxymethyl)-1,3-thiazol-2-yl]-1,3-dimethyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)SCCN2C=1C1=NC(CO)=CS1 NODRNSUBQQBWEJ-UHFFFAOYSA-N 0.000 claims 2
• PRBQGTHTOUQDAT-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(1-methylpyrazol-3-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CN1C=CC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SCCN32)=N1 PRBQGTHTOUQDAT-UHFFFAOYSA-N 0.000 claims 2
• IVAOJSCNZXBWCF-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(3-methylphenyl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=CC=CC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SCCN32)=C1 IVAOJSCNZXBWCF-UHFFFAOYSA-N 0.000 claims 2
• FMMKKYIEZSJODV-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(4-methyl-1,3-thiazol-2-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=CSC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SCCN32)=N1 FMMKKYIEZSJODV-UHFFFAOYSA-N 0.000 claims 2
• HODVQYQNLRXFNK-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound O1C(C)=NN=C1C1=C2C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SCCN21 HODVQYQNLRXFNK-UHFFFAOYSA-N 0.000 claims 2
• VYIFXMDXJZVGMQ-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SCCN2C=1C1=CC=CC=C1 VYIFXMDXJZVGMQ-UHFFFAOYSA-N 0.000 claims 2
• BBKGYGFXPBKJAB-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-5-(3-ethoxyphenyl)-1,3-dimethyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CCOC1=CC=CC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SCCN32)=C1 BBKGYGFXPBKJAB-UHFFFAOYSA-N 0.000 claims 2
• BSHCBORTLOSSJM-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-5-(3-methoxyphenyl)-1,3-dimethyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound COC1=CC=CC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SCCN32)=C1 BSHCBORTLOSSJM-UHFFFAOYSA-N 0.000 claims 2
• RVXYBSFWYANPGV-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-5-(cyclohexen-1-yl)-1,3-dimethyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SCCN2C=1C1=CCCCC1 RVXYBSFWYANPGV-UHFFFAOYSA-N 0.000 claims 2
• VFJLUGDGPPHZSJ-UHFFFAOYSA-N 3-[1,3,8,8-tetramethyl-9-(4-methyl-1,3-thiazol-2-yl)-2,4-dioxo-7,9-dihydropyrimido[4,5-a]pyrrolizin-5-yl]benzonitrile Chemical compound CC1=CSC(C2C(CN3C2=C2C(C(N(C)C(=O)N2C)=O)=C3C=2C=C(C=CC=2)C#N)(C)C)=N1 VFJLUGDGPPHZSJ-UHFFFAOYSA-N 0.000 claims 2
• RLKFROFNVRRLFT-UHFFFAOYSA-N 5-(3-fluorophenyl)-1,3,8,8-tetramethyl-9-(4-methyl-1,3-thiazol-2-yl)-7,9-dihydropyrimido[4,5-a]pyrrolizine-2,4-dione Chemical compound CC1=CSC(C2C(CN3C2=C2C(C(N(C)C(=O)N2C)=O)=C3C=2C=C(F)C=CC=2)(C)C)=N1 RLKFROFNVRRLFT-UHFFFAOYSA-N 0.000 claims 2
• WJHVFGZWIKTOIW-UHFFFAOYSA-N 9-(4-chloro-1,3-thiazol-2-yl)-1,3,8,8-tetramethyl-5-phenyl-7,9-dihydropyrimido[4,5-a]pyrrolizine-2,4-dione Chemical compound CC1(C)CN2C(C=3C=CC=CC=3)=C3C(=O)N(C)C(=O)N(C)C3=C2C1C1=NC(Cl)=CS1 WJHVFGZWIKTOIW-UHFFFAOYSA-N 0.000 claims 2
• JSNLQRXXLRDNTG-UHFFFAOYSA-N 9-(4-chloro-1,3-thiazol-2-yl)-5-(3-fluorophenyl)-1,3,8,8-tetramethyl-7,9-dihydropyrimido[4,5-a]pyrrolizine-2,4-dione Chemical compound CC1(C)CN2C(C=3C=C(F)C=CC=3)=C3C(=O)N(C)C(=O)N(C)C3=C2C1C1=NC(Cl)=CS1 JSNLQRXXLRDNTG-UHFFFAOYSA-N 0.000 claims 2
• SCWJMTRWNKOOKE-UHFFFAOYSA-N 1,3,8-trimethyl-10-(4-methyl-1,3-thiazol-2-yl)-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound S1C(C)CN(C(=C2C(=O)N(C)C(=O)N(C)C2=2)C=3C=CC=CC=3)C=2C1C1=NC(C)=CS1 SCWJMTRWNKOOKE-UHFFFAOYSA-N 0.000 claims 1
• FCDNVZVJKPOBNM-UHFFFAOYSA-N 1,3-dimethyl-10-(3-methylphenyl)-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=CC=CC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=CC=CC=3)CCS2)=C1 FCDNVZVJKPOBNM-UHFFFAOYSA-N 0.000 claims 1
• VEVARMXPPWZFND-UHFFFAOYSA-N 1,3-dimethyl-10-(4-methyl-1,3-thiazol-2-yl)-5-phenyl-7,8,9,10-tetrahydropyrimido[1,2]pyrrolo[4,5-b]pyridazine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=CC=CC=3)NCC2)=N1 VEVARMXPPWZFND-UHFFFAOYSA-N 0.000 claims 1
• HNVVHZKLSMTISP-UHFFFAOYSA-N 1,3-dimethyl-10-(4-methyl-1,3-thiazol-2-yl)-5-phenyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=CC=CC=3)CCC2)=N1 HNVVHZKLSMTISP-UHFFFAOYSA-N 0.000 claims 1
• OASYIEDNYIVIDV-UHFFFAOYSA-N 1,3-dimethyl-10-(4-methylthiophen-2-yl)-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=CC=CC=3)CCS2)=C1 OASYIEDNYIVIDV-UHFFFAOYSA-N 0.000 claims 1
• MXVHDCYTHBCVAX-UHFFFAOYSA-N 1,3-dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound O1C(C)=CC=C1C1C2=C(N(C)C(=O)N(C)C3=O)C3=C(C=3C=CC=CC=3)N2CCC1 MXVHDCYTHBCVAX-UHFFFAOYSA-N 0.000 claims 1
• CVDJAPNXRXWZNB-UHFFFAOYSA-N 1,3-dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-7-(triazol-2-ylmethyl)-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound O1C(C)=CC=C1C1C2=C(N(C)C(=O)N(C)C3=O)C3=C(C=3C=CC=CC=3)N2C(CN2N=CC=N2)CC1 CVDJAPNXRXWZNB-UHFFFAOYSA-N 0.000 claims 1
• OMKFKEYPKXLIDM-UHFFFAOYSA-N 1,3-dimethyl-10-(5-methylthiophen-2-yl)-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound S1C(C)=CC=C1C1C2=C(N(C)C(=O)N(C)C3=O)C3=C(C=3C=CC=CC=3)N2CCS1 OMKFKEYPKXLIDM-UHFFFAOYSA-N 0.000 claims 1
• KBXXSTGPDJDKPZ-UHFFFAOYSA-N 1,3-dimethyl-11-(4-methyl-1,3-thiazol-2-yl)-5-phenyl-8,9,10,11-tetrahydro-7h-pyrimido[1,2]pyrrolo[4,5-a]azepine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=CC=CC=3)CCCC2)=N1 KBXXSTGPDJDKPZ-UHFFFAOYSA-N 0.000 claims 1
• WNLWOYUQQHELJH-UHFFFAOYSA-N 1,3-dimethyl-5,10-bis(4-methyl-1,3-thiazol-2-yl)-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3SC=C(C)N=3)CCC2)=N1 WNLWOYUQQHELJH-UHFFFAOYSA-N 0.000 claims 1
• OZQVSGDSNMWOQA-UHFFFAOYSA-N 1,3-dimethyl-5-(3-methylphenyl)-10-(4-methyl-1,3-thiazol-2-yl)-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=C(C)C=CC=3)CCC2)=N1 OZQVSGDSNMWOQA-UHFFFAOYSA-N 0.000 claims 1
• PYTIQBNISILIGV-UHFFFAOYSA-N 1,3-dimethyl-5-(3-methylphenyl)-10-(4-methyl-1,3-thiazol-2-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=C(C)C=CC=3)CCS2)=N1 PYTIQBNISILIGV-UHFFFAOYSA-N 0.000 claims 1
• ZVPBNWABGHQZNI-UHFFFAOYSA-N 1,3-dimethyl-9-(4-methyl-1,3-thiazol-2-yl)-5-phenyl-8,9-dihydro-7h-pyrimido[4,5-a]pyrrolizine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=CC=CC=3)CC2)=N1 ZVPBNWABGHQZNI-UHFFFAOYSA-N 0.000 claims 1
• IEFQSGOKISPRQO-UHFFFAOYSA-N 1,3-dimethyl-9-(5-methylfuran-2-yl)-5-phenyl-8,9-dihydro-7h-pyrimido[4,5-a]pyrrolizine-2,4-dione Chemical compound O1C(C)=CC=C1C1C2=C(N(C)C(=O)N(C)C3=O)C3=C(C=3C=CC=CC=3)N2CC1 IEFQSGOKISPRQO-UHFFFAOYSA-N 0.000 claims 1
• VPZFSXVQZXOITQ-UHFFFAOYSA-N 10-(2,3-difluorophenyl)-1,3-dimethyl-5-phenyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3C(=C(F)C=CC=3)F)CCCN2C=1C1=CC=CC=C1 VPZFSXVQZXOITQ-UHFFFAOYSA-N 0.000 claims 1
• NLOPRZWYUAFUFX-UHFFFAOYSA-N 10-(2-chloro-1,3-thiazol-4-yl)-1,3-dimethyl-5-(1-methylpyrazol-3-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CN1C=CC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4N=C(Cl)SC=4)SCCN32)=N1 NLOPRZWYUAFUFX-UHFFFAOYSA-N 0.000 claims 1
• MXNCCALGQMGPNA-UHFFFAOYSA-N 10-(4-chloro-1,3-thiazol-2-yl)-1,3-dimethyl-5-(1-methylpyrazol-3-yl)-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound CN1C=CC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4SC=C(Cl)N=4)CCCN32)=N1 MXNCCALGQMGPNA-UHFFFAOYSA-N 0.000 claims 1
• UMTUTMRRDMOFOB-UHFFFAOYSA-N 10-(4-chloro-1,3-thiazol-2-yl)-1,3-dimethyl-5-(2-methyl-1,3-thiazol-4-yl)-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound S1C(C)=NC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4SC=C(Cl)N=4)CCCN32)=C1 UMTUTMRRDMOFOB-UHFFFAOYSA-N 0.000 claims 1
• JGYUXYKJPCDRTO-UHFFFAOYSA-N 10-(4-chloro-1,3-thiazol-2-yl)-1,3-dimethyl-5-(4-methyl-1,3-thiazol-2-yl)-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound CC1=CSC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4SC=C(Cl)N=4)CCCN32)=N1 JGYUXYKJPCDRTO-UHFFFAOYSA-N 0.000 claims 1
• UJMUZJRWCRZRMO-UHFFFAOYSA-N 10-(4-chloro-1,3-thiazol-2-yl)-5-(3-fluorophenyl)-8-(hydroxymethyl)-1,3-dimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)CC(CO)CN2C=1C1=CC=CC(F)=C1 UJMUZJRWCRZRMO-UHFFFAOYSA-N 0.000 claims 1
• YYMSODGVZHNXDE-UHFFFAOYSA-N 10-(4-chloro-1,3-thiazol-2-yl)-5-(3-fluorophenyl)-8-(hydroxymethyl)-1,3-dimethyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)SC(CO)CN2C=1C1=CC=CC(F)=C1 YYMSODGVZHNXDE-UHFFFAOYSA-N 0.000 claims 1
• QGKGPOZDMKIHPG-UHFFFAOYSA-N 10-(4-chloro-1,3-thiazol-2-yl)-5-[4-(hydroxymethyl)-1,3-thiazol-2-yl]-1,3-dimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)CCCN2C=1C1=NC(CO)=CS1 QGKGPOZDMKIHPG-UHFFFAOYSA-N 0.000 claims 1
• NJDHRJPRGCUZCW-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3,8-trimethyl-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound S1C(C)CN(C(=C2C(=O)N(C)C(=O)N(C)C2=2)C=3C=CC=CC=3)C=2C1C1=CC=C(Cl)O1 NJDHRJPRGCUZCW-UHFFFAOYSA-N 0.000 claims 1
• CTTIOMZLKYKEKX-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3-diethyl-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=12C(=O)N(CC)C(=O)N(CC)C2=C2C(C=3OC(Cl)=CC=3)SCCN2C=1C1=CC=CC=C1 CTTIOMZLKYKEKX-UHFFFAOYSA-N 0.000 claims 1
• JKYQAJRHBLIHNN-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(1-methylimidazol-4-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CN1C=NC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SCCN32)=C1 JKYQAJRHBLIHNN-UHFFFAOYSA-N 0.000 claims 1
• NRFUJNSPJPMOJX-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(1-methylpyrazol-4-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C1=NN(C)C=C1C1=C2C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SCCN21 NRFUJNSPJPMOJX-UHFFFAOYSA-N 0.000 claims 1
• JUUGCRVAKZXRJJ-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(4-methyl-1,3-oxazol-2-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=COC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SCCN32)=N1 JUUGCRVAKZXRJJ-UHFFFAOYSA-N 0.000 claims 1
• YILZNBNKEXAKMX-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(4-methyl-1,3-thiazol-2-yl)-8-[(2-oxo-1,3-oxazolidin-3-yl)methyl]-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=CSC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SC(CN4C(OCC4)=O)CN32)=N1 YILZNBNKEXAKMX-UHFFFAOYSA-N 0.000 claims 1
• QAAHSKKOMAHWBR-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-5-(3,5-difluorophenyl)-1,3-dimethyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SCCN2C=1C1=CC(F)=CC(F)=C1 QAAHSKKOMAHWBR-UHFFFAOYSA-N 0.000 claims 1
• TWGOCEGNFPCVSG-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-5-(3-fluorophenyl)-8-(hydroxymethyl)-1,3-dimethyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SC(CO)CN2C=1C1=CC=CC(F)=C1 TWGOCEGNFPCVSG-UHFFFAOYSA-N 0.000 claims 1
• LZVAAXNDLUJMFY-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-5-[4-(1-hydroxyethyl)-1,3-thiazol-2-yl]-1,3-dimethyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC(O)C1=CSC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SCCN32)=N1 LZVAAXNDLUJMFY-UHFFFAOYSA-N 0.000 claims 1
• HCSVUQJBRBZQSY-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-5-[4-(hydroxymethyl)-1,3-thiazol-2-yl]-1,3-dimethyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SCCN2C=1C1=NC(CO)=CS1 HCSVUQJBRBZQSY-UHFFFAOYSA-N 0.000 claims 1
• ULTQGYQOQUFXDC-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-5-(1-methylpyrazol-3-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CN1C=CC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SC(CO)CN32)=N1 ULTQGYQOQUFXDC-UHFFFAOYSA-N 0.000 claims 1
• HGIIJMBAUDLRQN-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-5-(2-methyl-1,3-thiazol-4-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound S1C(C)=NC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SC(CO)CN32)=C1 HGIIJMBAUDLRQN-UHFFFAOYSA-N 0.000 claims 1
• DBMBAPUQYZUKHG-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-5-(4-methyl-1,3-thiazol-2-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=CSC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SC(CO)CN32)=N1 DBMBAPUQYZUKHG-UHFFFAOYSA-N 0.000 claims 1
• KGBBKIRQNQXTLL-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SC(CO)CN2C=1C1=CC=CC=C1 KGBBKIRQNQXTLL-UHFFFAOYSA-N 0.000 claims 1
• QNTGLAAAZRVNMY-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-8-(imidazol-1-ylmethyl)-1,3-dimethyl-5-(4-methyl-1,3-thiazol-2-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=CSC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SC(CN4C=NC=C4)CN32)=N1 QNTGLAAAZRVNMY-UHFFFAOYSA-N 0.000 claims 1
• GGKFHMXFNJQQFD-UHFFFAOYSA-N 10-(5-chlorofuran-2-yl)-8-[(dimethylamino)methyl]-1,3-dimethyl-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound S1C(CN(C)C)CN(C(=C2C(=O)N(C)C(=O)N(C)C2=2)C=3C=CC=CC=3)C=2C1C1=CC=C(Cl)O1 GGKFHMXFNJQQFD-UHFFFAOYSA-N 0.000 claims 1
• AQBHPGUVTLTFHL-UHFFFAOYSA-N 11-(4-chloro-1,3-thiazol-2-yl)-1,3-dimethyl-5-phenyl-8,9,10,11-tetrahydro-7h-pyrimido[1,2]pyrrolo[4,5-a]azepine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)CCCCN2C=1C1=CC=CC=C1 AQBHPGUVTLTFHL-UHFFFAOYSA-N 0.000 claims 1
• ZGVYRUCPMUAXAH-UHFFFAOYSA-N 11-(4-chloro-1,3-thiazol-2-yl)-5-(3-fluorophenyl)-1,3-dimethyl-8,9,10,11-tetrahydro-7h-pyrimido[1,2]pyrrolo[4,5-a]azepine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)CCCCN2C=1C1=CC=CC(F)=C1 ZGVYRUCPMUAXAH-UHFFFAOYSA-N 0.000 claims 1
• PBKGPRDRZKKPET-UHFFFAOYSA-N 2-[10-(5-chlorofuran-2-yl)-1,3-dimethyl-2,4-dioxo-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazin-5-yl]-1,3-thiazole-4-carboxylic acid Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SCCN2C=1C1=NC(C(O)=O)=CS1 PBKGPRDRZKKPET-UHFFFAOYSA-N 0.000 claims 1
• ROUYJPQSSQQAHB-UHFFFAOYSA-N 3-(1,3-dimethyl-2,4-dioxo-5-phenyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizin-10-yl)benzonitrile Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3C=C(C=CC=3)C#N)CCCN2C=1C1=CC=CC=C1 ROUYJPQSSQQAHB-UHFFFAOYSA-N 0.000 claims 1
• CXLLNQHZWOYOAT-UHFFFAOYSA-N 3-[1,3-dimethyl-10-(4-methyl-1,3-thiazol-2-yl)-2,4-dioxo-7,8,9,10-tetrahydropyrimido[4,5-a]indolizin-5-yl]benzonitrile Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=C(C=CC=3)C#N)CCC2)=N1 CXLLNQHZWOYOAT-UHFFFAOYSA-N 0.000 claims 1
• QMJHFPIQCRMUCS-UHFFFAOYSA-N 3-[10-(4-chloro-1,3-thiazol-2-yl)-1,3-dimethyl-2,4-dioxo-7,8,9,10-tetrahydropyrimido[4,5-a]indolizin-5-yl]benzonitrile Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)CCCN2C=1C1=CC=CC(C#N)=C1 QMJHFPIQCRMUCS-UHFFFAOYSA-N 0.000 claims 1
• RLVZCPZUJUJJHR-UHFFFAOYSA-N 3-[10-(4-chloro-1,3-thiazol-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-2,4-dioxo-7,8,9,10-tetrahydropyrimido[4,5-a]indolizin-5-yl]benzonitrile Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)CC(CO)CN2C=1C1=CC=CC(C#N)=C1 RLVZCPZUJUJJHR-UHFFFAOYSA-N 0.000 claims 1
• PPVOWBPTODMVJM-UHFFFAOYSA-N 3-[10-(4-chloro-1,3-thiazol-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-2,4-dioxo-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazin-5-yl]benzonitrile Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)SC(CO)CN2C=1C1=CC=CC(C#N)=C1 PPVOWBPTODMVJM-UHFFFAOYSA-N 0.000 claims 1
• MPDQXBVRCZKRLB-UHFFFAOYSA-N 3-[10-(5-chlorofuran-2-yl)-1,3-dimethyl-2,4-dioxo-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazin-5-yl]benzonitrile Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SCCN2C=1C1=CC=CC(C#N)=C1 MPDQXBVRCZKRLB-UHFFFAOYSA-N 0.000 claims 1
• VQDOOCMMRPSYAI-UHFFFAOYSA-N 3-[10-(5-chlorofuran-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-2,4-dioxo-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazin-5-yl]benzonitrile Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SC(CO)CN2C=1C1=CC=CC(C#N)=C1 VQDOOCMMRPSYAI-UHFFFAOYSA-N 0.000 claims 1
• HWGPNMJPNDGBHY-UHFFFAOYSA-N 3-[11-(4-chloro-1,3-thiazol-2-yl)-1,3-dimethyl-2,4-dioxo-8,9,10,11-tetrahydro-7h-pyrimido[1,2]pyrrolo[4,5-a]azepin-5-yl]benzonitrile Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)CCCCN2C=1C1=CC=CC(C#N)=C1 HWGPNMJPNDGBHY-UHFFFAOYSA-N 0.000 claims 1
• WJPLFRUFLYZVBJ-UHFFFAOYSA-N 3-[9-(4-chloro-1,3-thiazol-2-yl)-1,3-dimethyl-2,4-dioxo-8,9-dihydro-7h-pyrimido[4,5-a]pyrrolizin-5-yl]benzonitrile Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)CCN2C=1C1=CC=CC(C#N)=C1 WJPLFRUFLYZVBJ-UHFFFAOYSA-N 0.000 claims 1
• PCJWLAMUOWWJEG-UHFFFAOYSA-N 3-[9-(4-chloro-1,3-thiazol-2-yl)-7-(hydroxymethyl)-1,3-dimethyl-2,4-dioxo-8,9-dihydro-7h-pyrimido[4,5-a]pyrrolizin-5-yl]benzonitrile Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)CC(CO)N2C=1C1=CC=CC(C#N)=C1 PCJWLAMUOWWJEG-UHFFFAOYSA-N 0.000 claims 1
• DDSJSTWPJIVJHW-UHFFFAOYSA-N 3-chloro-5-[10-(5-chlorofuran-2-yl)-1,3-dimethyl-2,4-dioxo-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazin-5-yl]benzonitrile Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3OC(Cl)=CC=3)SCCN2C=1C1=CC(Cl)=CC(C#N)=C1 DDSJSTWPJIVJHW-UHFFFAOYSA-N 0.000 claims 1
• WZBSYUDTBIEPPK-UHFFFAOYSA-N 5-(3-chlorophenyl)-1,3-dimethyl-10-(4-methyl-1,3-thiazol-2-yl)-7,8,9,10-tetrahydropyrimido[1,2]pyrrolo[4,5-b]pyridazine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=C(Cl)C=CC=3)NCC2)=N1 WZBSYUDTBIEPPK-UHFFFAOYSA-N 0.000 claims 1
• LBNQYWWRFSMODF-UHFFFAOYSA-N 5-(3-chlorophenyl)-10-(4-chloro-1,3-thiazol-2-yl)-1,3-dimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(C)C2=C2C(C=3SC=C(Cl)N=3)CCCN2C=1C1=CC=CC(Cl)=C1 LBNQYWWRFSMODF-UHFFFAOYSA-N 0.000 claims 1
• FJUCTSFLSKBGKB-UHFFFAOYSA-N 5-(3-fluorophenyl)-1,3,8-trimethyl-10-(5-methylfuran-2-yl)-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound C=1C=CC(F)=CC=1C1=C(C(N(C)C(=O)N2C)=O)C2=C2N1CC(C)CC2C1=CC=C(C)O1 FJUCTSFLSKBGKB-UHFFFAOYSA-N 0.000 claims 1
• HBEZYXMZZHFYLF-UHFFFAOYSA-N 5-(3-fluorophenyl)-1,3,9-trimethyl-10-(4-methyl-1,3-thiazol-2-yl)-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound CC1CCN(C(=C2C(=O)N(C)C(=O)N(C)C2=2)C=3C=C(F)C=CC=3)C=2C1C1=NC(C)=CS1 HBEZYXMZZHFYLF-UHFFFAOYSA-N 0.000 claims 1
• BPFFOGMPQUGGQQ-UHFFFAOYSA-N 5-(3-fluorophenyl)-1,3,9-trimethyl-10-(5-methylfuran-2-yl)-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound CC1CCN(C(=C2C(=O)N(C)C(=O)N(C)C2=2)C=3C=C(F)C=CC=3)C=2C1C1=CC=C(C)O1 BPFFOGMPQUGGQQ-UHFFFAOYSA-N 0.000 claims 1
• GQMRGCWPYIYAMA-UHFFFAOYSA-N 5-(3-fluorophenyl)-1,3-dimethyl-10-(5-methylfuran-2-yl)-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4-dione Chemical compound O1C(C)=CC=C1C1C2=C(N(C)C(=O)N(C)C3=O)C3=C(C=3C=C(F)C=CC=3)N2CCC1 GQMRGCWPYIYAMA-UHFFFAOYSA-N 0.000 claims 1
• QBGAXZVRZOOQSQ-UHFFFAOYSA-N 5-(3-methoxyphenyl)-1,3-dimethyl-10-(4-methyl-1,3-thiazol-2-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound COC1=CC=CC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4SC=C(C)N=4)SCCN32)=C1 QBGAXZVRZOOQSQ-UHFFFAOYSA-N 0.000 claims 1
• IIRDITKASGERQK-UHFFFAOYSA-N 7-(hydroxymethyl)-1,3-dimethyl-9-(4-methyl-1,3-thiazol-2-yl)-5-phenyl-8,9-dihydro-7h-pyrimido[4,5-a]pyrrolizine-2,4-dione Chemical compound CC1=CSC(C2C=3N(C(=C4C(=O)N(C)C(=O)N(C)C4=3)C=3C=CC=CC=3)C(CO)C2)=N1 IIRDITKASGERQK-UHFFFAOYSA-N 0.000 claims 1
• ZYILWZGTSMNONG-UHFFFAOYSA-N 7-[(dimethylamino)methyl]-1,3-dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound C=1C=CC=CC=1C1=C(C(N(C)C(=O)N2C)=O)C2=C2N1C(CN(C)C)CSC2C1=CC=C(C)O1 ZYILWZGTSMNONG-UHFFFAOYSA-N 0.000 claims 1
• ZDZJVAUPWBWYOE-UHFFFAOYSA-N 8-(aminomethyl)-10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(4-methyl-1,3-thiazol-2-yl)-8,10-dihydro-7h-pyrimido[1,2]pyrrolo[4,5-a][1,4]thiazine-2,4-dione Chemical compound CC1=CSC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4OC(Cl)=CC=4)SC(CN)CN32)=N1 ZDZJVAUPWBWYOE-UHFFFAOYSA-N 0.000 claims 1
• FVQJOVIQOBJYRA-UHFFFAOYSA-N 9,9-difluoro-5-(3-fluorophenyl)-1,3-dimethyl-10-(5-methylfuran-2-yl)-8,10-dihydro-7h-pyrimido[4,5-a]indolizine-2,4-dione Chemical compound O1C(C)=CC=C1C1C(F)(F)CCN2C1=C(N(C)C(=O)N(C)C1=O)C1=C2C1=CC=CC(F)=C1 FVQJOVIQOBJYRA-UHFFFAOYSA-N 0.000 claims 1
• XIILFYQBCGVPIG-UHFFFAOYSA-N 9-(4-chloro-1,3-thiazol-2-yl)-1,3-dimethyl-5-(4-methyl-1,3-thiazol-2-yl)-8,9-dihydro-7h-pyrimido[4,5-a]pyrrolizine-2,4-dione Chemical compound CC1=CSC(C2=C3C(=O)N(C)C(=O)N(C)C3=C3C(C=4SC=C(Cl)N=4)CCN32)=N1 XIILFYQBCGVPIG-UHFFFAOYSA-N 0.000 claims 1
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