IP Library Granted Patent US 8,178,544
Granted Patent B2
US 8,178,544 · App. 12/601,124 · Granted May 15, 2012

2, 3-diamino-quinazolinone derivatives and their medical use

Assignee: Neurosearch A/S
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Quick Facts
Patent No.
US 8,178,544
App. No.
12/601,124
Granted
May 15, 2012
Kind
B2
Abstract

This invention provides 2,3-diamino-quinazolinone compounds of Formula (I) stereoisomers thereof, pharmaceutically-acceptable addition salts thereof, and N-oxides thereof, wherein the variables are as defined in the specification. The 2,3-diamino-quinazolinone compounds have medical utility. The 2,3-diamino-quinazolinone compounds can be used for the manufacture of medicaments, including pharmaceutical compositions. This invention also provides methods of treating disorders, diseases, or conditions which are responsive to activation of K v 7 channels.

Claims (131)

1. A 2,3-diamino-quinazolinone compound of Formula (I)

a stereoisomer or a mixture of its stereoisomers, or a pharmaceutically-acceptable addition salt thereof, or an N-oxide thereof, wherein

R 1 represents hydrogen, alkyl or halo; and R 2 represents hydrogen, alkyl, cycloalkyl, halo, haloalkyl, hydroxyalkyl, hydroxy, alkoxy, phenyl, phenyl-alkyl, amino, alkyl-carbonyl-amino, cyano or nitro; or R 1 and R 2 together with the carbon atom to which they are attached form a cycloalkyl (spiro) group; or R 1 represents hydrogen; and R 2 together with one of R 3 , R 4 and R 5 , attached in ortho-position on the aromatic ring, form a —(CH 2 ) n — bridge, wherein n is 1, 2 or 3;

R 3 , R 4 and R 5 , independently of each other, represent hydrogen, alkyl, cycloalkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, amino, alkyl-carbonyl-amino, alkyl-sulfanyl, alkyl-sulfonyl, phenyl, phenoxy, benzoyl, cyano or nitro; or two of R 3 , R 4 and R 5 , together form a methylenedioxy group; and the remaining of R 3 , R 4 and R 5 is as defined above; or two of R 3 , R 4 and R 5 , together with the phenyl ring to which they are attached, form a naphthyl group; and the remaining of R 3 , R 4 and R 5 is as defined above; or one of R 3 , R 4 and R 5 , attached in ortho-position on the aromatic ring, and together with R 2 form a —(CH 2 ) n — bridge, wherein n is 1, 2 or 3; and the remaining of R 3 , R 4 and R 5 , are as defined above;

R 6 and R 7 , independently of each other, represent hydrogen, alkyl, cycloalkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, amino, alkyl-carbonyl-amino, nitro, cyano or phenyl; and

R′ and R″, independently of each other, represent alkyl, hydroxy-alkyl, amino-alkyl, cycloalkyl, phenyl-alkyl, phenyl-hydroxyalkyl, N-alkyl-amino-alkyl, N,N-dialkyl-amino-alkyl, alkoxy-alkyl, piperidinyl, N-alkyl-piperidinyl, furanyl-alkyl, pyridinyl-alkyl, pyrazolyl-alkyl, imidazolyl-alkyl, pyrimidinyl, pyrimidinyl substituted with one or two substituents selected from N-alkyl-amino, N,N-dialkyl-amino and phenyl; or

R′ and R″, together with the nitrogen to which they are attached, form a heterocyclic ring selected from pyrrolidinyl, 2,5-dihydro-1H-pyrrol-1-yl, thiazolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl and homomorpholinyl,

which pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl and homomorpholinyl is optionally substituted one or more times with a substituent selected from the group consisting of alkyl, alkoxy, alkoxy-alkyl, alkyl-carbonyl-amino, cycloalkyl-carbonyl-amino, hydroxy-alkyl, hydroxy, amino, N-alkyl-amino, N,N-dialkyl-amino, amino-alkyl, N-alkyl-amino-alkyl, N,N-dialkyl-amino-alkyl, carbamoyl-alkyl, N-alkyl-carbamoyl-alkyl, N,N-dialkyl-carbamoyl-alkyl, N-hydroxy-alkyl-carbamoyl, N,N-dialkyl-amino-alkyl-carbamoyl, alkoxy-carbonyl, cyano-alkyl, pyrrolidinyl, pyrrolidinyl-alkyl, piperidinyl, piperidinyl-carbonyl, hydroxy-piperidinyl, hydroxy-piperidinyl-alkyl, hydroxy-piperidinyl-carbonyl, N-alkyl-piperidinyl, piperidinyl-alkyl, N-alkyl-piperidinyl-alkyl, morpholino-alkyl, morpholino-alkyl-carbamoyl, morpholino-carbonyl-alkyl, triazolyl-alkyl, piperazinyl, piperazinyl-alkyl, piperazinyl-carbonyl, N-alkyl-piperazinyl, N-alkyl-piperazinyl-alkyl, N-alkyl-piperazinyl-carbonyl, pyridinyl, pyridinyl-alkyl, and pyridinyl substituted once or twice with alkyl, trifluoromethyl and/or cyano.

2. The 2,3-diamino-quinazolinone compound of claim 1 , a stereoisomer or a mixture of its stereoisomers, or a pharmaceutically-acceptable addition salt thereof, or an N-oxide thereof, wherein R 1 represents hydrogen or alkyl; and R 2 represents hydrogen or alkyl.

3. The 2,3-diamino-quinazolinone compound of claim 1 , a stereoisomer or a mixture of its stereoisomers, or a pharmaceutically-acceptable addition salt thereof, or an N-oxide thereof, wherein R 3 , R 4 and R 5 , independently of each other, represent hydrogen, alkyl, halo, haloalkyl, hydroxy, alkoxy, alkyl-sulfanyl, alkyl-sulfonyl, phenyl or phenoxy.

4. The 2,3-diamino-quinazolinone compound of claim 1 , a stereoisomer or a mixture of its stereoisomers, or a pharmaceutically-acceptable addition salt thereof, or an N-oxide thereof, wherein R 6 and R 7 , independently of each other, represent hydrogen, halo, haloalkyl, hydroxy, alkoxy, or amino.

5. The 2,3-diamino-quinazolinone compound of claim 1 , a stereoisomer or a mixture of its stereoisomers, or a pharmaceutically-acceptable addition salt thereof, or an N-oxide thereof, wherein R′ and R″, independently of each other, represent alkyl, hydroxy-alkyl, cycloalkyl, or phenyl-alkyl.

6. The 2,3-diamino-quinazolinone compound of claim 1 , a stereoisomer or a mixture of its stereoisomers, or a pharmaceutically-acceptable addition salt thereof, or an N-oxide thereof, wherein R′ and R″, together with the nitrogen to which they are attached, form a heterocyclic ring selected from pyrrolidinyl, thiazolidinyl, piperidinyl, piperazinyl, homopiperazinyl and morpholinyl, which piperazinyl is optionally substituted one or more times with alkyl.

7. The 2,3-diamino-quinazolinone compound of claim 1 , which is:

2-(3,5-Difluoro-phenyl)-N-(4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(2-dimethylamino-4-oxo-4H-quinazolin-3-yl)-acetamide;

2-(4-Chloro-phenyl)-N-(2-diethylamino-4-oxo-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-[2-(ethyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-acetamide;

2-(3,5-Difluoro-phenyl)-N-(2-dimethylamino-4-oxo-7-trifluoromethyl-4H-quinazolin-3-yl)-propionamide;

N-(2-Diethylamino-4-oxo-4H-quinazolin-3-yl)-2-(4-methanesulfonyl-phenyl)-acetamide;

N-{2-[(2-Methoxy-ethyl)-methyl-amino]-4-oxo-4H-quinazolin-3-yl}-2-(4-trifluoromethyl-phenyl)-acetamide;

2-(4-Butoxy-phenyl)-N-{2-[(2-methoxy-ethyl)-methyl-amino]-4-oxo-4H-quinazolin-3-yl}-acetamide;

N-[2-(Benzyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-2-(4-methanesulfonyl-phenyl)-acetamide;

2-(4-Butoxy-phenyl)-N-(4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(4-oxo-2-thiazolidin-3-yl-4H-quinazolin-3-yl)-acetamide;

N-(2-Diethylamino-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

2-(3,5-Bis-trifluoromethyl-phenyl)-N-(4-oxo-2-thiazolidin-3-yl-4H-quinazolin-3-yl)-acetamide;

2-Benzo[1,3]dioxol-5-yl-N-(2-diethylamino-4-oxo-4H-quinazolin-3-yl)-acetamide;

N-(2-Diethylamino-4-oxo-4H-quinazolin-3-yl)-2-phenyl-acetamide; or

N-[2-(Ethyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-2-phenyl-acetamide; or a stereoisomer or a mixture of its stereoisomers, a pharmaceutically-acceptable addition salt thereof.

8. The 2,3-diamino-quinazolinone compound of claim 1 , which is:

2-(3-Fluoro-4-trifluoromethyl-phenyl)-N-(4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Bis-trifluoromethyl-phenyl)-N-{2-[(2-methoxy-ethyl)-methyl-amino]-4-oxo-4H-quinazolin-3-yl}-acetamide;

N-[2-(Benzyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-2-(3,4-difluoro-phenyl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(2-morpholin-4-yl-4-oxo-4H-quinazolin-3-yl)-acetamide;

2-(4-Chloro-phenyl)-N-{7-fluoro-2-[(2-methoxy-ethyl)-methyl-amino]-4-oxo-4H-quinazolin-3-yl}-acetamide;

2-(4-Chloro-phenyl)-N-(2-morpholin-4-yl-4-oxo-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-{7-fluoro-2-[(2-methoxy-ethyl)-methyl-amino]-4-oxo-4H-quinazolin-3-yl}-acetamide;

2-(4-Chloro-phenyl)-N-(2-dimethylamino-4-oxo-4H-quinazolin-3-yl)-acetamide;

N-(2-Diethylamino-6-fluoro-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

2-(4-Chloro-phenyl)-N-(2-diethylamino-6-fluoro-4-oxo-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-[2-(4-methyl-piperazin-1-yl)-4oxo-4H-quinazolin-3-yl]-acetamide;

N-(2-Diethylamino-6-fluoro-4-oxo-4H-quinazolin-3-yl)-2-(3-fluoro-5-trifluoromethyl-phenyl)-acetamide;

N-[2-(Benzyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-2-(3,5-difluoro-phenyl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-{2-[(2-methoxy-ethyl)-methyl-amino]-4-oxo-4H-quinazolin-3-yl}-acetamide;

2-(3-Fluoro-5-trifluoromethyl-phenyl)-N-(4-oxo-2-pyrrolidin-1-yl-7-trifluoromethyl-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(4-oxo-2-pyrrolidin-1-yl-7-trifluoromethyl-4H-quinazolin-3-yl)-acetamide;

2-(3-Fluoro-5-trifluoromethyl-phenyl)-N-{2-[(2-methoxy-ethyl)-methyl-amino]-4-oxo-7-trifluoromethyl-4H-quinazolin-3-yl}-acetamide;

2-(3,5-Difluoro-phenyl)-N-{2-[(2-methoxy-ethyl)-methyl-amino]-4-oxo-7-trifluoromethyl-4H-quinazolin-3-yl}-acetamide;

N-(6-Butoxy-2-morpholin-4-yl-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(5-Chloro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(5-Chloro-2-diethylamino-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(2-Diethylamino-7-fluoro-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(2-Diethylamino-5-fluoro-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(2-Diethylamino-4-oxo-7-trifluoromethyl-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(7-Chloro-2-diethylamino-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(7-Chloro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(6-Chloro-2-diethylamino-7-fluoro-4-oxo-4H-quinazolin-3yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(2-Diethylamino-5,7-difluoro-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(7-fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

N-(6-Chloro-7-fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(5,7-Difluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(5,7-Dichloro-2-diethylamino-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(2-Diethylamino-6,7-difluoro-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(6,7-Difluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

2-(3-Fluoro-4-trifluoromethyl-phenyl)-N-(2-morpholin-4-yl-4-oxo-4H-quinazolin-3-yl)-acetamide;

N-(2-Dimethylamino-4-oxo-4H-quinazolin-3-yl)-2-(3-fluoro-4-trifluoromethyl-phenyl)-acetamide;

N-(6-Chloro-2-diethylamino-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(2-Dimethylamino-6-fluoro-4-oxo-4H-quinazolin-3-yl)-2-(3-fluoro-4-trifluoromethyl-phenyl)-acetamide;

N-(6-Fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3-fluoro-4-trifluoromethyl-phenyl)-acetamide;

2-(4-Chloro-3-fluoro-phenyl)-N-(6-fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(6-fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(4-Chloro-3-fluoro-phenyl)-N-(2-dimethylamino-6-fluoro-4-oxo-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(2-dimethylamino-6-fluoro-4-oxo-4H-quinazolin-3-yl)-acetamide;

N-(5,7-Dichloro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(2-dimethylamino-5-fluoro-4-oxo-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(2-dimethylamino-7-fluoro-4-oxo-4H-quinazolin-3-yl)-acetamide;

N-(2-Dimethylamino-5-fluoro-4-oxo-4H-quinazolin-3-yl)-2-(3-fluoro-5-trifluoromethyl-phenyl)-acetamide;

N-(2-Dimethylamino-7-fluoro-4-oxo-4H-quinazolin-3-yl)-2-(3-fluoro-4-trifluoromethyl-phenyl)-acetamide;

2-(4-Chloro-phenyl)-N-(2-diethylamino-5,7-difluoro-4-oxo-4-quinazolin-3-yl)-acetamide;

2-(4-Chloro-phenyl)-N-(7-fluoro-4-oxo-2-pyrrolidin-1yl-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-[5-fluoro-2-(isopropyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-acetamide;

2-(3,5-Difluoro-phenyl)-N-[2-(ethyl-methyl-amino)-5-fluoro-4-oxo-4H-quinazolin-3-yl]-acetamide;

2-(3,5-Difluoro-phenyl)-N-[7-fluoro-2-(isopropyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-acetamide;

2-(3,5-Difluoro-phenyl)-N-[2-(ethyl-methyl-amino)-7-fluoro-4-oxo-4H-quinazolin-3-yl]-acetamide;

2-(4-Chloro-phenyl)-N-(7-fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-propionamide;

2-(4-Chloro-phenyl)-N-(4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-propionamide;

N-(2-Diethylamino-8-fluoro-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(8-fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-Naphthalen-2-yl-N-(4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

N-(5,7-Difluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3,4-difluoro-phenyl)-acetamide;

2-(3,4-Difluoro-phenyl)-N-[2-(ethyl-methyl-amino)-7-fluoro-4-oxo-4H-quinazolin-3-yl]-acetamide;

2-(4-Chloro-phenyl)-N-[2-(ethyl-methyl-amino)-7-fluoro-4-oxo-4H-quinazolin-3-yl]-acetamide;

2-Naphthalen-1-yl-N-(4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(4-Chloro-phenyl)-N-(5,7-difluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-[2-(ethyl-methyl-amino)-5,7-difluoro-4-oxo-4H-quinazolin-3-yl]-acetamide;

N-[5,7-Difluoro-2-(isopropyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-2-(3,4-difluoro-phenyl)-acetamide;

N-[5,7-Difluoro-2-(isopropyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-2-(3,5-difluoro-phenyl)-acetamide;

N-[2-(Ethyl-methyl-amino)-7-fluoro-4-oxo-4H-quinazolin-3-yl]-2-(4-methylsulfanyl-phenyl)-acetamide;

2-(4-Isobutyl-phenyl)-N-(4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-propionamide;

N-[2-(Ethyl-methyl-amino)-7-fluoro-4-oxo-4H-quinazolin-3-yl]-2-(4-methoxy-phenyl)-acetamide;

N-(7-Fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(4-phenoxy-phenyl)-acetamide;

2-Biphenyl-4-yl-N-(7-fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(4-Chloro-phenyl)-N-(4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(3,4-Difluoro-phenyl)-N-(4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

N-[2-(Ethyl-methyl-amino)-7-fluoro-4-oxo-4H-quinazolin-3-yl]-2-(4-isopropyl-phenyl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-[2-(isopropyl-methyl-amino)-4-oxo-4-quinazolin-3-yl]-acetamide;

2-(3,4-Difluoro-phenyl)-N-[2-(isopropyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-acetamide;

2-(3,4-Difluoro-phenyl)-N-(7-fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(3,4-Difluoro-phenyl)-N-(8-fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(3,4-Difluoro-phenyl)-N-[2-(isobutyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-acetamide;

2-(3,5-Difluoro-phenyl)-N-[2-(isobutyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-acetamide;

2-(3,4-Difluoro-phenyl)-N-[7-fluoro-2-(isopropyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-acetamide;

N-(7-Chloro-6-fluoro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(2-diisopropylamino-4-oxo-4H-quinazolin-3-yl)-acetamide;

N-[2-(Cyclopentyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-2-(3,5-difluoro-phenyl)-acetamide;

N-[2-(Cyclopentyl-methyl-amino)-4-oxo-4H-quinazolin-3-yl]-2-(3,4-difluoro-phenyl)-acetamide;

2-(3,4-Difluoro-phenyl)-N-(2-diisopropylamino-4-oxo-4H-quinazolin-3-yl)-acetamide;

2-(3,4-Difluoro-phenyl)-N-(4-oxo-2-piperidin-1-yl-4H-quinazolin-3-yl)-acetamide;

2-(3,5-Difluoro-phenyl)-N-(4-oxo-2-piperidin-1-yl-4H-quinazolin-3-yl)-acetamide;

N-(8-Chloro-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(2-Diethylamino-6-hydroxy-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(6,8-Dichloro-2-diethylamino-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(6-Amino-2-diethylamino-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(7-Amino-2-diethylamino-4-oxo-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide;

N-(7-Amino-4-oxo-2-pyrrolidin-1-yl-4H-quinazolin-3-yl)-2-(3,5-difluoro-phenyl)-acetamide; or

a stereoisomer or a mixture of its stereoisomers, a pharmaceutically-acceptable addition salt thereof.

9. A pharmaceutical composition comprising a therapeutically effective amount of the 2,3-diamino-quinazolinone compound of claim 1 , a stereoisomer or a mixture of its stereoisomers, or a pharmaceutically-acceptable addition salt thereof.

10. The 2,3-diamino-quinazolinone compound of claim 7 , which is:

2-(3,5-difluorophenyl)-N-(2-dimethylamino-4-oxo-7-trifluoromethyl-4H-quinazolin-3-yl )-propionamide; or

a stereoisomer or a mixture of its stereoisomers, or a pharmaceutically-acceptable addition salt thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2013
From: NEUROSEARCH A/S
To: ANIONA APS
Reel/Frame 030049/0894 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2010
From: JESSEN, CARSTEN; BROWN, WILLIAM DALBY; DEMNITZ, JOACHIM; STROBAEK, DORTE; KORSGAARD, MADS P.G.; CHRISTOPHERSEN, PALLE
To: NEUROSEARCH A/S
Reel/Frame 023879/0857 →
Priority Claims (1)
DK 2007 00756 · May 23, 2007 · national
Continuity (2)
Provisional Application 60939723 · May 23, 2007
Related Publication 20100160315A1 · Jun 24, 2010