JP5635535B2 - 心血管疾患の予防および治療のための化合物 - Google Patents

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Publication number

JP5635535B2

JP5635535B2 JP2011544946A JP2011544946A JP5635535B2 JP 5635535 B2 JP5635535 B2 JP 5635535B2 JP 2011544946 A JP2011544946 A JP 2011544946A JP 2011544946 A JP2011544946 A JP 2011544946A JP 5635535 B2 JP5635535 B2 JP 5635535B2

Authority

JP

Japan

Prior art keywords

quinazolin

sec

butylphenyl

pharmaceutically acceptable

stereoisomer

Prior art date

2009-01-08

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.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 251
• 208000024172 Cardiovascular disease Diseases 0.000 title claims description 19
• 230000002265 prevention Effects 0.000 title claims description 9
• -1 is selected NMe 2 Chemical group 0.000 claims description 148
• 239000000203 mixture Substances 0.000 claims description 110
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 93
• 229910052739 hydrogen Inorganic materials 0.000 claims description 93
• 239000001257 hydrogen Substances 0.000 claims description 93
• 239000000460 chlorine Substances 0.000 claims description 88
• 150000003839 salts Chemical class 0.000 claims description 84
• 125000003118 aryl group Chemical group 0.000 claims description 71
• 150000002431 hydrogen Chemical class 0.000 claims description 60
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• 229910052731 fluorine Inorganic materials 0.000 claims description 47
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 40
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 39
• 108010059886 Apolipoprotein A-I Proteins 0.000 claims description 36
• 102000005666 Apolipoprotein A-I Human genes 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
• 201000010099 disease Diseases 0.000 claims description 32
• 229910052794 bromium Inorganic materials 0.000 claims description 29
• 229910052801 chlorine Inorganic materials 0.000 claims description 29
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 239000011737 fluorine Substances 0.000 claims description 28
• QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims description 24
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 235000012000 cholesterol Nutrition 0.000 claims description 18
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
• 229910005965 SO 2 Inorganic materials 0.000 claims description 17
• 150000002632 lipids Chemical class 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
• 238000004519 manufacturing process Methods 0.000 claims description 13
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
• 229910052740 iodine Inorganic materials 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 239000008280 blood Substances 0.000 claims description 9
• 210000004369 blood Anatomy 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• CMBCIGQSOTZAJG-UHFFFAOYSA-N 3-(4-aminophenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(N)=CC=2)=C1 CMBCIGQSOTZAJG-UHFFFAOYSA-N 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• LNSFWGANTMLKFH-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]pyrido[4,3-d]pyrimidin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CN=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 LNSFWGANTMLKFH-UHFFFAOYSA-N 0.000 claims description 5
• 230000003143 atherosclerotic effect Effects 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• OZUGFQKQFWHVPE-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CC(Br)=C1 OZUGFQKQFWHVPE-UHFFFAOYSA-N 0.000 claims description 4
• YCTVTSSLGLSZAR-UHFFFAOYSA-N 3-(4-bromophenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-8-methoxyquinazolin-4-one Chemical compound COC1=CC=CC(C(N2C=3C=CC(Br)=CC=3)=O)=C1N=C2C1=CC(C)=C(OCCO)C(C)=C1 YCTVTSSLGLSZAR-UHFFFAOYSA-N 0.000 claims description 4
• MAADFZNOPLSTHR-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-phenoxypyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C(C=N1)=CC=C1OC1=CC=CC=C1 MAADFZNOPLSTHR-UHFFFAOYSA-N 0.000 claims description 4
• QRQNMYJLPBKCGF-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 QRQNMYJLPBKCGF-UHFFFAOYSA-N 0.000 claims description 4
• HOKHPQSUTVJSDN-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-pyrimidin-5-ylquinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CN=C1 HOKHPQSUTVJSDN-UHFFFAOYSA-N 0.000 claims description 4
• KVZNCXGALLAQMW-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(1h-indol-4-yl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=CC2=C1C=CN2 KVZNCXGALLAQMW-UHFFFAOYSA-N 0.000 claims description 4
• ZYONEZWBPCJRII-UHFFFAOYSA-N 3-(4-cyclohexylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(=CC=2)C2CCCCC2)=C1 ZYONEZWBPCJRII-UHFFFAOYSA-N 0.000 claims description 4
• RPLJQAZHANXHFM-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(=CC=2)C(C)(C)C)=C1 RPLJQAZHANXHFM-UHFFFAOYSA-N 0.000 claims description 4
• RJFWYLQWEYURCM-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound C1=CC(N(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 RJFWYLQWEYURCM-UHFFFAOYSA-N 0.000 claims description 4
• 208000034826 Genetic Predisposition to Disease Diseases 0.000 claims description 4
• XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 4
• 230000003902 lesion Effects 0.000 claims description 4
• 230000037356 lipid metabolism Effects 0.000 claims description 4
• VAIACDKPQXPTID-UHFFFAOYSA-N n-[4-[2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-4-oxoquinazolin-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 VAIACDKPQXPTID-UHFFFAOYSA-N 0.000 claims description 4
• KQMYKFRYTCHDOI-UHFFFAOYSA-N n-[4-[2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-4-oxoquinazolin-3-yl]phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 KQMYKFRYTCHDOI-UHFFFAOYSA-N 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• FBQICEIXZHCUSF-UHFFFAOYSA-N 2-(1h-indol-5-yl)-3-(4-propan-2-ylphenyl)quinazolin-4-one Chemical compound C1=CC(C(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NC=C2)C2=C1 FBQICEIXZHCUSF-UHFFFAOYSA-N 0.000 claims description 3
• JWQKBRRBNLSXCT-UHFFFAOYSA-N 2-(1h-indol-5-yl)-3-[4-(trifluoromethoxy)phenyl]quinazolin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NC=C2)C2=C1 JWQKBRRBNLSXCT-UHFFFAOYSA-N 0.000 claims description 3
• DHFPRDLXYFACHV-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-3-(4-butan-2-ylphenyl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CC(Br)=C1 DHFPRDLXYFACHV-UHFFFAOYSA-N 0.000 claims description 3
• YHIZKXPNEDFRCG-UHFFFAOYSA-N 2-(6-bromopyridin-3-yl)-3-(4-butan-2-ylphenyl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(Br)N=C1 YHIZKXPNEDFRCG-UHFFFAOYSA-N 0.000 claims description 3
• DFPDROFHDIFMKK-UHFFFAOYSA-N 2-(6-bromopyridin-3-yl)-3-(4-chlorophenyl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(Br)N=C1 DFPDROFHDIFMKK-UHFFFAOYSA-N 0.000 claims description 3
• MSHZYSBUIBCCQR-UHFFFAOYSA-N 2-(6-methylpyridin-3-yl)-3-(4-methylsulfanylphenyl)quinazolin-4-one Chemical compound C1=CC(SC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C)N=C1 MSHZYSBUIBCCQR-UHFFFAOYSA-N 0.000 claims description 3
• UHBJGOGLEGXENZ-UHFFFAOYSA-N 2-(6-methylpyridin-3-yl)-3-(4-propan-2-ylphenyl)quinazolin-4-one Chemical compound C1=CC(C(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C)N=C1 UHBJGOGLEGXENZ-UHFFFAOYSA-N 0.000 claims description 3
• RKAJCRHQYCQUIJ-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3-(4-iodophenyl)quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(I)=CC=2)=C1 RKAJCRHQYCQUIJ-UHFFFAOYSA-N 0.000 claims description 3
• BCHCHJNQUJRDGT-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3-(4-morpholin-4-ylphenyl)quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(=CC=2)N2CCOCC2)=C1 BCHCHJNQUJRDGT-UHFFFAOYSA-N 0.000 claims description 3
• DBZKIEKURBHGOQ-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3-(4-propan-2-ylphenyl)quinazolin-4-one Chemical compound C1=CC(C(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 DBZKIEKURBHGOQ-UHFFFAOYSA-N 0.000 claims description 3
• KDNWYRLSNWUQHB-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3-[4-(trifluoromethyl)phenyl]quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 KDNWYRLSNWUQHB-UHFFFAOYSA-N 0.000 claims description 3
• AOUBRIJJTDSEFP-UHFFFAOYSA-N 3-(4-bromophenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-6-methoxyquinazolin-4-one Chemical compound C=1C=C(Br)C=CC=1N1C(=O)C2=CC(OC)=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 AOUBRIJJTDSEFP-UHFFFAOYSA-N 0.000 claims description 3
• MHHKKQCBXMYTBT-UHFFFAOYSA-N 3-(4-bromophenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(Br)=CC=2)=C1 MHHKKQCBXMYTBT-UHFFFAOYSA-N 0.000 claims description 3
• RMZSWYMBNQXQBT-UHFFFAOYSA-N 3-(4-bromophenyl)-2-[4-(2-hydroxyethoxy)-3-methylphenyl]quinazolin-4-one Chemical compound C1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(Br)=CC=2)=C1 RMZSWYMBNQXQBT-UHFFFAOYSA-N 0.000 claims description 3
• OPIXKJHACSNHAB-UHFFFAOYSA-N 3-(4-bromophenyl)-8-chloro-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC(Cl)=C3N=2)C=2C=CC(Br)=CC=2)=C1 OPIXKJHACSNHAB-UHFFFAOYSA-N 0.000 claims description 3
• OKRYXQFBDRWPGY-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(1h-indazol-5-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NN=C2)C2=C1 OKRYXQFBDRWPGY-UHFFFAOYSA-N 0.000 claims description 3
• VVNDNZSFPSYQEI-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(1h-indol-5-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NC=C2)C2=C1 VVNDNZSFPSYQEI-UHFFFAOYSA-N 0.000 claims description 3
• FIIGJZVHSNKSIU-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(1h-indol-7-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=CC2=C1NC=C2 FIIGJZVHSNKSIU-UHFFFAOYSA-N 0.000 claims description 3
• YKQANQSXCDWCKY-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(5-fluoropyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CC(F)=C1 YKQANQSXCDWCKY-UHFFFAOYSA-N 0.000 claims description 3
• CHJRJWBDMODIIS-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-chloropyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(Cl)N=C1 CHJRJWBDMODIIS-UHFFFAOYSA-N 0.000 claims description 3
• WHIOZSKENDJXSA-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-methoxypyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(OC)N=C1 WHIOZSKENDJXSA-UHFFFAOYSA-N 0.000 claims description 3
• MMHJYVUBDAYCHP-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-methylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C)N=C1 MMHJYVUBDAYCHP-UHFFFAOYSA-N 0.000 claims description 3
• NODCZFRSJFGEAB-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-morpholin-4-ylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(N2CCOCC2)N=C1 NODCZFRSJFGEAB-UHFFFAOYSA-N 0.000 claims description 3
• XEIBCRVYNCEUOP-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-piperidin-1-ylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(N2CCCCC2)N=C1 XEIBCRVYNCEUOP-UHFFFAOYSA-N 0.000 claims description 3
• UBJYLRRBBMGOJX-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[2-(hydroxymethyl)-3h-benzimidazol-5-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(N=C(CO)N2)C2=C1 UBJYLRRBBMGOJX-UHFFFAOYSA-N 0.000 claims description 3
• VSQCFAVZPFEZSL-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-6-methoxyquinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC(OC)=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 VSQCFAVZPFEZSL-UHFFFAOYSA-N 0.000 claims description 3
• LVQNHQOUQNMLEP-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-6-methylsulfonylquinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC(S(C)(=O)=O)=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 LVQNHQOUQNMLEP-UHFFFAOYSA-N 0.000 claims description 3
• VMENXQKOUGXXQB-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-7-methylsulfonylquinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=C(S(C)(=O)=O)C=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 VMENXQKOUGXXQB-UHFFFAOYSA-N 0.000 claims description 3
• INMSMJGRAMYTHH-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3-methylphenyl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(OCCO)C(C)=C1 INMSMJGRAMYTHH-UHFFFAOYSA-N 0.000 claims description 3
• QNAKGEGVMUTASP-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)phenyl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(OCCO)C=C1 QNAKGEGVMUTASP-UHFFFAOYSA-N 0.000 claims description 3
• NLLASDGHSCUILA-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[5-(diethylamino)pyridin-3-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CC(N(CC)CC)=C1 NLLASDGHSCUILA-UHFFFAOYSA-N 0.000 claims description 3
• SEJZRPRKEXKOKZ-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[6-(hydroxymethyl)pyridin-3-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(CO)N=C1 SEJZRPRKEXKOKZ-UHFFFAOYSA-N 0.000 claims description 3
• ZBSMUXWSTOCQNY-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[6-(trifluoromethyl)pyridin-3-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C(F)(F)F)N=C1 ZBSMUXWSTOCQNY-UHFFFAOYSA-N 0.000 claims description 3
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