Disclosed are novel compounds that are useful for regulating the expression of apolipoprotein A-I (ApoA-I), and their use for the treatment and prevention of cardiovascular disease and related disease states, including cholesterol- or lipid-related disorders, such as, for example, atherosclerosis. A
Disclosed are novel compounds that are useful for regulating the expression of apolipoprotein A-I (ApoA-I), and their use for the treatment and prevention of cardiovascular disease and related disease states, including cholesterol- or lipid-related disorders, such as, for example, atherosclerosis. Also disclosed are pharmaceutical compositions comprising the novel compounds. Formula (I)
대표청구항▼
1. A compound of Formula I: or a stereoisomer, tautomer, pharmaceutically acceptable salt, or hydrate thereof, wherein Y is carbon;W is nitrogen;Ra6 is selected from fluoride, hydrogen, C1-C3 alkoxy, cyclopropyloxy, SO2R3, SOR3, and SR3, wherein if Y is nitrogen then Ra6 is absent;Ra7 is selected f
1. A compound of Formula I: or a stereoisomer, tautomer, pharmaceutically acceptable salt, or hydrate thereof, wherein Y is carbon;W is nitrogen;Ra6 is selected from fluoride, hydrogen, C1-C3 alkoxy, cyclopropyloxy, SO2R3, SOR3, and SR3, wherein if Y is nitrogen then Ra6 is absent;Ra7 is selected from hydrogen, fluoride, SO2R3, SOR3, and SR3;Ra8 is selected from hydrogen, C1-C3 alkoxy, cyclopropyloxy, chloride, and bromide;AR is n is selected from 1, 2, or 3;D is selected from O, NH, NR1, S, or C;Rb3 and Rb5 are independently selected from hydrogen and C1-C3 alkyl;Rc3 and Rc5 are independently selected from hydrogen, C1-C3 alkyl, and cyclopropyl;Rc4 is selected from F, Cl, Br, I, CF3, C1-C6 alkyl, C3-C6 cycloalkyl, NHC(O)R4, NHSO2R4, C(O)OR4, and R1, R′1, R2 and R′2 are independently selected from hydrogen, fluoride, C1-C3 alkyl, and cyclopropyl, wherein R1 and R2 and/or R′1 and R′2 may be connected to form a 3-6 membered ring;R3 is selected from C1-C3 alkyl and cyclopropyl; andR4 is selected from hydrogen, C1-C4 alkyl, C3-C5 cycloalkyl, and aryl, provided that if Ra7 or Ra6 is fluoride, then Rc4 is not bromide. 2. The compound according to claim 1, wherein Rc4 is selected from F, Cl, Br, I, CF3, C1-C6 alkyl, cyclohexyl, —NHC(O)R4, —NHSO2R4, —C(O)OR4, and wherein R4 is selected from hydrogen, C1-C4 alkyl, and aryl; andR1 and R2 are independently selected from hydrogen and C1-C3 alkyl. 3. A compound of Formula II: or a tautomer, stereoisomer, pharmaceutically acceptable salt or hydrate thereof wherein: W is carbon or nitrogen;AR is T is carbon or nitrogen;Ra6, Ra7, and Ra8 are independently selected from hydrogen and fluoride;Rb4 is selected from hydrogen, Cl, Br, F, CF3, C1-C4 alkyl, C3-C5 cycloalkyl, C1-C4 alkoxy, C3-C5 cycloalkoxy, methoxy, -Oaryl, phenyl, CH2OH, —CH2morpholino, morpholino, piperidinyl, —CH2piperazino, —CH2(N-methylpiperazino), —NR1R2, and —CH2NR1R2;Rb5 is selected from hydrogen, Cl, Br, F, aryl, and —NR1R2, wherein Rb4 and Rb5 may be connected to form a ring;Rc4 is selected from Cl, Br, C2-C5 alkyl, C3-C5 cycloalkyl, —SR1, —NHSO2R1, —NR1R2; andR1 and R2 are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl wherein R1 and R2 may be connected to form a 3-6-membered ring, provided thatif Rb4 is fluoride, phenyl, methoxy, CH2OH, —CH2morpholino, morpholino, —CH2piperazino, or —CH2(N-methylpiperazino) then Rc4 is not chloride;if Ra7 or Ra6 is fluoride, then Rc4 is not bromide;if Rb5 is fluoride then Rc4 is not chloride;if Rc4 is chloride or bromide, then at least one of Rb2, Rb4, or Rb5 is not hydrogen;if T is N, then Rc4 is not halogen; andif AR is then Rc4 is not sec-butyl. 4. The compound according to claim 3, wherein Ra5, Ra7, and Ra8 are each hydrogen. 5. The compound according to claim 3, wherein Rb4 and Rb5 together to which the atoms they are bound form a phenyl ring. 6. A compound of Formula III: or a tautomer, stereoisomer, pharmaceutically acceptable salt, or hydrate thereof wherein: W is nitrogen;AR is selected from: T, U, and V are independently selected from carbon and nitrogen;R1 is selected from hydrogen, C1-C5 alkyl, C3-C5 cycloalkyl, and —SO2R3;R2 is selected from hydrogen, C1-C5 alkyl, C3-C5 cycloalkyl, and CH2OH;R3 is selected from hydrogen, C1-C5 alkyl, C3-C5 cycloalkyl, and optionally substituted aryl;R4 is selected from hydrogen, C1-C5 alkyl, and C3-C5 cycloalkyl;R5 is selected from hydrogen, C1-C5 alkyl, and C3-C5 cycloalkyl;Ra5, Ra6, Ra7, and Ra8 are independently selected from hydrogen and fluoride;Rb2 and Rb3 are independently selected from hydrogen, F, Cl, Br, C1-C3 alkyl, cyclopropyl, and C1-C3 alkoxy; andRc4 is selected from C2-C6 alkyl, C3-C6 cycloalkyl, F, Cl, Br, I, OCF3, and —NR4R5, provided thatif R1 is methyl, then Rc4 is not sec-butyl; andif R2 is CH2OH, then Rc4 is not Cl. 7. The compound according to claim 6, wherein T is nitrogen and U and V are both carbon. 8. The compound according to claim 6, wherein T is carbon and U and V are both carbon. 9. The compound according to claim 6, wherein T is carbon, U is carbon, and V is nitrogen. 10. A compound selected from the group consisting of: 3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)phenyl)quinazolin-4(3H)-one;3-(4-fluorophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one;2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-3-(4-iodophenyl)quinazolin-4(3H)-one;3-(4-bromophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-6-fluoro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one,3-(4-chlorophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-7-fluoro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one;2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-3-(4-(trifluoromethyl)phenyl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-7-(methylsulfonyl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-6-methoxyquinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-8-methoxyquinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)pyrido[4,3-d]pyrimidin-4(3H)-one;3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-6-(methylsulfonyl)quinazolin-4(3H)-one;3-(4-bromophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-6-methoxyquinazolin-4(3H)-one;3-(4-bromophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-8-methoxyquinazolin-4(3H)-one,2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-3-(4-isopropylphenyl)quinazolin-4(3H)-one;3-(4-bromophenyl)-2-(4-(2-hydroxyethoxy)-3-methylphenyl)quinazolin-4(3H)-one;3-(4-bromophenyl)-8-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one;2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-3-(4-morpholinophenyl)quinazolin-4(3H)-one;3-(4-tert-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one;N-(4-(2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-4-oxoquinazolin-3(4H)-yl)phenyl)acetamide;N-(4-(2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-4-oxoquinazolin-3(4H)-yl)phenyl)isobutyramide;Methyl 4-(2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-4-oxoquinazolin-3(4H)-yl)benzoate;3-(4-cyclohexylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one;N-(4-(2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-4-oxoquinazolin-3(4H)-yl)phenyl)formamide;3-(4-aminophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one;N-(4-(2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-4-oxoquinazolin-3(4H)-yl)phenyl)methanesulfonamide;N-(4-(2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-4-oxoquinazolin-3(4H)-yl)pN-(4-(2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-4-oxoquinazolin-3(4H)-yl)phenyl)propane-2-sulfonamide;3-(4-(dimethylamino)phenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3-methylphenyl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(4-(2-hydroxyethoxy)-3-methylphenyl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(pyridin-3-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(quinolin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(5-fluoropyridin-3-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(6-chloropyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(6-chloropyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(6-methoxypyridin-3-yl)quinazolin-4(3H)-one;2-(6-bromopyridin-3-yl)-3-(4-chlorophenyl)quinazolin-4(3H)-one;2-(6-bromopyridin-3-yl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(6-(diethylamino)pyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(6-(diethylamino)pyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(pyrimidin-5-yl)quinazolin-4(3H)-one,3-(4-sec-butylphenyl)-2-(6-methylpyridin-3-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(6-methylpyridin-3-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(6-(piperidin-1-yl)pyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(6-(piperidin-1-yl)pyridin-3-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(6-phenoxypyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(6-fluoropyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(6-phenoxypyridin-3-yl)quinazolin-4(3H)-one,3-(4-chlorophenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(6-phenylpyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(5-phenylpyridin-3-yl)quinazolin-4(3H)-one;2-(5-bromopyridin-3-yl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one;2-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(5-(diethylamino)pyridin-3-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(5-phenylpyridin-3-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(5-(diethylamino)pyridin-3-yl)quinazolin-4(3H)-one;3-(4-cyclopentylphenyl)-2-(6-methylpyridin-3-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(6-(hydroxymethyl)pyridin-3-yl)quinazolin-4(3H)-one;2-(6-methylpyridin-3-yl)-3-(4-(methylthio)phenyl)quinazolin-4(3H)-one;3-(4-isopropylphenyl)-2-(6-methylpyridin-3-yl)quinazolin-4(3H)-one;N-(4-(2-(6-methylpyridin-3-yl)-4-oxoquinazolin-3(4H)-yl)phenyl)methanesulfonamide;3-(4-sec-butylphenyl)-2-(6-(morpholinomethyl)pyridin-3-yl)quinazolin-4(3H)-one;3-(4-cyclopropylphenyl)-2-(6-methylpyridin-3-yl)quinazolin-4(3H)-one;3-(4-(dimethylamino)phenyl)-2-(6-methylpyridin-3-yl)quinazolin-4(3H)-one;2-(6-chloropyridin-3-yl)-3-(4-cyclopropylphenyl)quinazolin-4(3H)-one; and3-(4-sec-butylphenyl)-2-(6-morpholinopyridin-3-yl)quinazolin-4(3H)-one,3-(4-sec-butylphenyl)-2-(1H-indazol-5-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(2-(hydroxymethyl)-1H-benzo[d]imidazol-6-yl)quinazolin-4(3H)-one;2-(1H-indol-5-yl)-3-(4-(trifluoromethoxy)phenyl)quinazolin-4(3H)-one;2-(1H-indol-5-yl)-3-(4-isopropylphenyl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(1-(4-methoxyphenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(1-(4-fluorophenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)quinazolin-4(3H)-one;3-(4-(dimethylamino)phenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(2-(hydroxymethyl)-1H-indol-5-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(1-methyl-1H-indol-5-yl)quinazolin-4(3H)-one;3-(4-cyclopentylphenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(1H-indol-6-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(1H-indol-7-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(1H-indol-6-yl)quinazolin-4(3H)-one;3-(4-sec-butylphenyl)-2-(1H-indol-7-yl)quinazolin-4(3H)-one;3-(4-chlorophenyl)-2-(1H-indol-4-yl)quinazolin-4(3H)-one; and3-(4-sec-butylphenyl)-2-(1H-indol-4-yl)quinazolin-4(3H)-one, and pharmaceutically acceptable salts and hydrates thereof. 11. A pharmaceutical composition comprising a compound according to claim 1, 3, 6, or 10 and a pharmaceutically acceptable carrier. 12. A method of increasing the expression of ApoA-I in a subject, comprising administering a therapeutically effective amount of a compound according to claim 1, 3, 6, or 10. 13. The method of claim 12, wherein increasing the expression of ApoA-I in the subject treats a cardiovascular disease or a cholesterol-, or lipid-related disorder or reduces the risk of acquiring a cardiovascular disease or cholesterol-, or lipid-related disorder. 14. The method of claim 13, wherein the method comprises regression of arteriosclerosis lesions or reduction of the risk of acquiring arteriosclerosis lesions. 15. The method of claim 13, wherein the method comprises decreasing blood cholesterol levels. 16. The method of claim 12, wherein the subject has a genetic or non-genetic predisposition to a cardiovascular disease or cholesterol- or lipid related disorder.
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