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US 9,751,884 B2Granted
N-aryl unsaturated fused ring tertiary amine compounds, preparation method and anti-tumor applications thereof
AssigneeInstitute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China
InventorsLan Xie, Xiaofeng Wang, Kuo-Hsiung Lee
Life of this patent
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Abstract
The present invention relates to a compound of Formula I or a pharmaceutically acceptable salt thereof, its preparation method, a pharmaceutical composition comprising the compound, and its use in manufacture of a medicament for treatment of a disease or disorder, wherein R1, R2, R5, R6, X, Y, Q, W, n1 and n2 are defined as those stated in the description.
Claims5
A compound of Formula I or a pharmaceutically acceptable salt thereof:
- wherein,
- X is —NR′—, and Y is —C(O)—, —CHOR′—, or —CR′R″—;
- wherein R′ and R″ each independently are H, C1-6 alkyl, C1-6 alkoxyl, C1-6 alkylamino, or hydroxyl;
- R1 represents 1 or 2 substituents optionally existing on the benzene ring, independently being C1-6 alkyl, C1-6 alkoxyl, halogen, hydroxyl, cyano, amino, or C1-6alkylamino;
- R2 is C1-6 alkyl, C1-6 alkoxyl, halogen, acyl, alkenyl, alkynyl, hydroxyl, cyano, alkylamino, dialkylamino, acylamino, alkylthio, cycloalkyl, cyano alkyl, heterocycloalkyl or aryl;
- Q and W each independently are N;
- R5 and R6 together with carbon atoms linked to them form 6-membered aromatic ring forming a conjugated system, wherein the aromatic ring is optionally substituted with 1 or 2 R3;
- R3 independently is H, C1-6 alkyl, C1-6 alkoxyl, fluorine, chlorine, bromine, iodine, acyl, hydroxyl, cyano, amino, C1-6 alkylamino, C1-6dialkylamino, acylamino, C1-6 alkylthio, or C3-6 cycloalkyl;
- n1=1;
- and
- n2=0.
8 more elements
A compound selected from the group consisting of:
- N1-[4-(2-chloro)quinazolinyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 1),
- N1-[4-(2-methyl)quinazolinyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 2),
- N1-[4-(2-methoxy)quinazolinyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 3),
- N1-[4-(2-methylamino)quinazolinyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 4),
- 2-methyl-4-(6-methoxy-7-fluoro-3,4-dihydroquinolin-1(2H)-yl)quinazoline (Compound 5),
- N1-[4-(2-methyl)quinazolinyl]-6-methyl-1,2,3,4-tetrahydroquinoline (Compound 6),
- N1-[4-(2-methyl)quinazolinyl]-6-bromo-1,2,3,4-tetrahydroquinoline (Compound 7),
- N2-[4-(2-methyl)quinazolinyl]-7-methoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepine (Compound 9),
- N1-[4-(2-chloro)quinazolinyl]-7-methoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine (Compound 10),
- N1-[4-(2-methyl)quinazolinyl]-4-hydroxyl-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 11),
- N1-[4-(2-chloro)quinazolinyl]-4-ethoxy-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 12),
- N4-[4-(2-chloro)quinazolinyl]-7-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazine (Compound 13),
- N4-[4-(2-methyl)quinazolinyl]-6-fluoro-7-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazine (Compound 14),
- 4-(2-chloroquinazolin-4-yl)-7-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazine (Compound 15),
- 4-(2-chloroquinazolin-4-yl)-7-methoxy-3,4-dihydro-2H-benzo[b][1,4]-1-oxythiazine (Compound 16),
- 4-(2-chloroquinazolin-4-yl)-7-methoxy-3,4-dihydro-2H-benzo[b][1,4]-1,1-dioxythiazine (Compound 17),
- N1-[4-(2-chloro)quinazolinyl]-6-methoxy-2,3-dihydroquinolin-4(1H)-one (Compound 18),
- N4-[4-(2-methyl)quinazolinyl]-7-methoxy-3,4-dihydroquinoxalin-2(1H)-one (Compound 19),
- 6-methoxy-2′-methyl-3,4-dihydro-2H-1,4′-biquinoline (Compound 20),
- 2-methyl-4-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)pyrido[2,3-d]pyrimidine (Compound 21),
- 2-methyl-4-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)pyrido[3,4-d]pyrimidine (Compound 22),
- 2-methyl-4-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)pyrido[4,3-d]pyrimidine (Compound 23),
- 2-methyl-4-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)pyrido[3,2-d]pyrimidine (Compound 24),
- 2-methyl-4-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)pteridine (Compound 25),
- N1-[(3-bromo-5-methoxycarbonyl)phenyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 26),
- N1-[(3-bromo-5-carboxyl)phenyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 27),
- N1-[(3-bromo-5-methylaminoacyl)phenyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 28),
- N1-[3-bromo-5-(N-cyclopropylaminoacyl)phenyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 29),
- N1-[4-(2-amino-6-chloro)pyrimidinyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (Compound 30),
- N1-methyl-N4-[4-(2-methyl)quinazolinyl]-7-methoxy-3,4-dihydroquinoxalin-2(1H)-one (Compound 31),
- 2-(N-methylmethylamino)-4-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)quinazoline (Compound 32),
- 2-cyclopropylamino-4-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)quinazoline (Compound 33),
- 2-cyclopentylamino-4-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)quinazoline (Compound 34),
- 2-(3-hydroxylpropylamino)-4-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)quinazoline (Compound 35),
- 4-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)quinazoline (Compound 36),
- 4-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)naphthalene (Compound 37),
- 4-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)quinoline (Compound 38),
- 1-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)isoquinoline (Compound 39),
- 4-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)isoquinoline (Compound 40),
- 8-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)quinoline (Compound 41),
- 6-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)purine (Compound 42),
- 2-fluoro-6-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)purine (Compound 43), and
- 2-amino-6-(6-methoxy-1,2,3,4-tetrahydro-1-quinolyl)purine (Compound 44);
- or
- a pharmaceutically acceptable salt thereof.
42 more elements
Dependencies are inferred from the claim text.