	US 7,329,664 B2
	Substituted (7-pyridyl-4-phenylamino-quinazolin-2-yl)-methanol analogues
Rajagopal Bakthavatchalam, Madison, Conn. (US); Charles A. Blum, Westbrook, Conn. (US); Harry Brielmann, Guilford, Conn. (US); Stéphane De Lombaert, Madison, Conn. (US); and Xiaozhang Zheng, Branford, Conn. (US)
Assigned to Neurogen Corporation, Branford, Conn. (US)
Filed on Jul. 16, 2004, as Appl. No. 10/892,741.
Claims priority of provisional application 60/488551, filed on Jul. 16, 2003.
Prior Publication US 2005/0215575 A1, Sep. 29, 2005
Int. Cl. A61K 31/517 (2006.01); A61K 31/519 (2006.01); C07D 401/04 (2006.01); C07D 405/14 (2006.01); C07D 487/04 (2006.01)

U.S. Cl. 514—266.21 [514/264.11; 544/279; 544/284]

39 Claims

1. A compound or a pharmaceutically acceptable salt thereof, wherein the compound is selected from:

(4-Cyclopropyl-phenyl)-[2-methoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-amine;

(4-Isopropyl-phenyl)-[2-(tetrahydro-pyran-4-yloxymethyl)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-amine;

(4-Isopropyl-phenyl)-[2-methoxymethyl-7-(3-methyl-pyridin-2-yl)-quinazolin-4yl]-amine;

(4-Isopropyl-phenyl)-[2-methoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-amine;

(4-tert-Butyl-phenyl)-[2-methoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-amine;

(4-Isopropyl-phenyl)-[7-(3-methyl-pyridin-2-yl)-2-(tetrahydro-pyran-4-yloxymethyl)-quinazolin-4-yl]-amine;

(4-tert-Butyl-phenyl)-[7-(3-chloro-pyridin-2-yl)-2-ethoxymethyl-quinazolin-4-yl]-amine;

(4-tert-Butyl-phenyl)-[7-(3-chloro-pyridin-2-yl)-2-methoxymethyl-quinazolin-4-yl]-amine;

[2-(Tetrahydro-pyran-4-yloxymethyl)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

[2-Benzyloxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-[4-(2,2,2-trifluoro-1-methyl-ethyl)-phenyl]-amine;

[2-Benzyloxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

[2-Benzyloxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-[4-(2-methoxy-1,1-dimethyl-ethyl)-phenyl]-amine;

[2-Benzyloxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-tert-butyl-phenyl)-amine;

[2-Ethoxymethyl-7-(3-methyl-pyridin-2-yl)-quinazolin-4-yl]-(4-isopropyl-phenyl)-amine;

[2-Ethoxymethyl-7-(3-methyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

[2-Ethoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

[2-Isopropoxymethyl-7-(3-methyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

[2-Isopropoxymethyl-7-(3-methyl-pyridin-2-yl)-quinazolin-4-yl]-(4-isopropyl-phenyl)-amine;

[2-Isopropoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

[2-Methoxymethyl-7-(3-methylpyridin-2-yl)-quinazolin-4-yl)-(4-trifluoromethylphenyl)-amine;

[2-Methoxyethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

[4-(2-Methoxy-1,1-dimethyl-ethyl)-phenyl]-[2-methoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-amine;

[4-(4-Isopropyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-yl]-methanol;

[4-(4-tert-Butyl-phenylamino)-7-(3-chloro-pyridin-2-yl)-quinazolin-2-yl]-methanol;

[4-(4-tert-Butyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-yl]-methanol;

[4-(4-Trifluoromethyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-yl]-methanol;

[7-(3-Chloro-pyridin-2-yl)-2-(tetrahydro-pyran-4-yloxymethyl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

[7-(3-Chloro-pyridin-2-yl)-2-(tetrahydro-pyran-4-yloxymethyl)-quinazolin-4-yl]-(4-isopropyl-phenyl)-amine;

[7-(3-Chloro-pyridin-2-yl)-2-ethoxymethyl-quinazolin-4-yl]-(4-isopropyl-phenyl)-amine;

[7-(3-Chloro-pyridin-2-yl)-2-ethoxymethyl-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

[7-(3-Chloro-pyridin-2-yl)-2-methoxymethyl-quinazolin-4-yl]-(4-isopropyl-phenyl)-amine;

[7-(3-Chloro-pyridin-2-yl)-2-methoxymethyl-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

[7-(3-Chloro-pyridin-2-yl)-4-(4-isopropyl-phenylamino)-quinazolin-2-yl]-methanol;

[7-(3-Methyl-pyridin-2-yl)-2-(tetrahydro-pyran-4-yloxymethyl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine;

2-{4-[2-Benzyloxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-ylamino]-phenyl}-2-methyl-propionitrile; and

2-{4-[2-Methoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-ylamino]-phenyl}-2-methyl-propionitrile.