IP Library Granted Patent US 7,410,963
Granted Patent B2
US 7,410,963 · App. 10/582,131 · Granted Aug 12, 2008

Benzo-1,4-diazepin-2-one derivatives as phosphodiesterase PDE2 inhibitors, preparation and therapeutic use thereof

Assignee: VIA Pharmaceuticals, Inc.
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Quick Facts
Patent No.
US 7,410,963
App. No.
10/582,131
Granted
Aug 12, 2008
Kind
B2
Abstract

The invention relates to compounds having PDE2 inhibitory activities, as well as therapeutic methods by administering said compounds, in particular for treating various diseases of the central or peripheral nervous system. It further deals with pharmaceutical compositions comprising said compounds and methods for preparing said compounds.

Claims (163)

1. A compound represented by formula (I):

wherein:

R 1 represents a member selected from the group consisting of hydrogen, (C 1 -C 6 ) alkyl, aryl, (C 1 -C 6 )alkylaryl, aryl(C 1 -C 6 )alkyl group, (C 3 -C 6 ) alkenyl, and (C 3 -C 6 ) alkenylaryl,

R 7 represents a substituted or unsubstituted aryl or heteroaryl group, wherein said heteroaryl group contains from 4 to 18 carbon atoms and one or more heteroatoms selected from N, O and S, wherein R 7 is a substituted aryl group, it is mono- or bis-substituted by the following groups: (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyloxy, (C 1 -C 6 )alkyloxy, (C 3 -C 6 )alkenyloxy, aryloxy, acyl, halogen, trifluoromethyl, difluoromethyl, cyano, nitro, hydroxy, carboxamide, amino, (C 1 -C 6 )aminoalkyl, (C 1 -C 6 )aminodialkyl, NCOR 12 where R 12 is selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylaryl, aryl, and —CONR 13 R 14 wherein R 13 and R 14 , independently from each other, are selected from the group consisting of hydrogen, (C 1 -C 6 )alkyl, (C 3 -C 6 )alkenyl, alkylaryl, alkenylaryl, and aryl, and wherein R 7 is a substituted heteroaryl group, it is substituted with one or two substituents independently selected from the group consisting of halogen, amino, aminoacyl, CONH 2 , (C 1 -C 6 )alkyl, aryloxy and (C 1 -C 6 )alkyloxy,

R 8 represents hydrogen or an OR 10 group, wherein R 10 is a selected from the group consisting of hydrogen, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )alkenyl, trifluoromethyl, difluoromethyl, (C 3 -C 6 )alkenylaryl, aryl, and a heterocyclic group, aromatic or not, having from 4 to 18 carbon atoms and 1 to 3 heteroatoms chosen from O, N and S,

when R 10 represents an aryl, it is mono- or bis-substituted by substituents selected from: hydrogen, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyloxy, (C 1 -C 6 )alkyloxy, (C 3 -C 6 )alkenyloxy, halogen, trifluoromethyl, difluoromethyl, cyano, nitro, hydroxy, carboxamide, amino, (C 1 -C 6 )aminoalkyl, (C 1 -C 6 )aminodialkyl NCOR 12 wherein R 12 is selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylaryl and aryl, and —CONR 13 R 14 wherein R 13 and R 14 , independently from each other, are selected from the group consisting of hydrogen, (C 1 -C 6 )alkyl, (C 3 -C 6 )alkenyl, alkylaryl, alkenylaryl, and aryl,

R X represents a member selected from the group consisting of hydrogen, halogen, methyl, methoxy, acetyl, trifluoromethyl, CN, COH and CONH 2 ,

R Y represents a member selected from the group consisting of hydrogen, halogen, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, aryl, arylalkyl, (C 3 -C 6 )cycloalkyloxy, COH, (C 1 -C 6 )alkyloxy, alkenyl, (C 3 -C 8 )alkenyloxy, alkynyl, alkynyloxy, acyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, cyano, nitro, hydroxy, carboxamide, amino, (C 1 -C 6 )aminoalkyl, (C 1 -C 6 )aminodialkyl, NHCOR 12 where R 12 is as defined above, and —CONR 13 R 14 wherein R 13 and R 14 are as defined above,

with the proviso that, when R 8 is hydrogen, then one or R X and R Y is other than hydrogen,

or a pharmaceutically acceptable salt thereof.

2. The compound of formula (I) according to claim 1 , wherein R 8 is hydrogen, alkoxy, or aryloxy.

3. The compound of formula (I) according to claim 1 , wherein at least one of R X and R Y is other than hydrogen.

4. The compound of formula (I) according to claim 1 , wherein R Y is an hydrogen atom and R X is other than hydrogen.

5. The compound of formula (I) according to claim 1 , wherein the one of R X and R Y , that is other than hydrogen, is on position 3 of the phenyl group represented in formula (I).

6. The compound of formula (I) according to claim 4 , wherein R X , is on position 3 of the phenyl group represented in formula (I).

7. The compound of formula (I) according to claim 1 , wherein R X represents CONH 2 , CN, or COCH 3 , and is on position 3 or 4 of the phenyl group represented in formula (I).

8. The compound of formula (I) according to claim 1 , wherein R Y is selected from the group consisting of hydrogen, halogen, CF 3 , (C 1 -C 6 )aminoalkyl, (C 1 -C 6 )aminodialkyl, —NHCOR 12 , —CONH 2 , (C 1 -C 3 alkyloxy and (C 1 -C 6 )alkyl.

9. The compound of formula (I) according to claim 1 , wherein R 1 represents hydrogen, alkyl, alkenyl, or arylalkyl.

10. The compound of formula (I) according to claim 1 , wherein R 7 represents a furanyl group.

11. The compound of formula (I) according to claim 1 , wherein R 7 represents an unsubstituted aryl group.

12. The compound of formula (I) according to claim 1 , wherein R 7 represents a substituted aryl or heteroaryl group.

13. The compound of formula (I) according to claim 1 , wherein R 7 represents an aryl or heteroaryl group substituted with one or two, substituents independently selected from the group consisting of halogen, amino, aminoacyl, CONH 2 , (C 1 -C 6 )alkyl, aryloxy and (C 1 -C 6 )alkyloxy.

14. The compound of formula (I) according to claim 1 , wherein R 7 is an aryl or heteroaryl group substituted with an alkoxy group.

15. The compound of formula (I) according to claim 1 , wherein R 7 is a phenyl group substituted by at least one group on the ortho position.

16. The compound of formula (I) according to claim 1 , wherein R 7 is a substituted phenyl group selected from the group consisting of 4-methoxy-phenyl, 4-fluoro-phenyl, 2-methoxy-phenyl, 2-chloro-phenyl, 4-chloro-phenyl, 3-chloro-phenyl, 3-methoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 4-carbamoyl-phenyl, 4-cyanophenyl, 2,4-dimethoxy-phenyl, 4-carboxamide-phenyl, 4-acetyl-phenyl, 2-isopropoxy-phenyl, 2-phenoxy-phenyl, and 3,4-dimethoxy-phenyl groups.

17. A compound of formula (I) in accordance with claim 1 , wherein said compound is selected from the group consisting of:

3-(8-Methoxy-1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile;

3-[7-(4-Fluoro-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[8-Methoxy-7-(2-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[8-Methoxy-7-(4-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(2-Chloro-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-1-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(3-Chloro-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(4-Chloro-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-(7-Furan-2-yl-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile;

3-(1-Methyl-2-oxo-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile

3-[8-Methoxy-7-(2-methoxy-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-(1-Methyl-2-oxo-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile;

3-[7-(2-Methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(3-Methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(4-Methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(2,5-Dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(2,6-Dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(2,4-Dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

8-Ethoxy-1-ethyl-5,7-diphenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

3-(8-Methoxy-1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide;

3-[7-(4-fluoro-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[8-Methoxy-7-(2-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[8-Methoxy-7-(4-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2-Chloro-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(3-Chloro-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(4-Chloro-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-(7-Furan-2-yl-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide;

3-(1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide;

3-[7-(2-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(3-methoxy-phenyl)-1-methyl-2-oxa-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(4-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2,5-Dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2,6-Dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2,4-Dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-(8-Methoxy-7-(4-benzamide)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide;

3-[1-Hexyl-8-methoxy-7-(2-methoxy-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[8-Methoxy-7-(2-methoxy-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[8-Methoxy-7-6-methoxy-phenyl)-2-oxo-1-propyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[8-Methoxy-7-(2-methoxy-phenyl)-2-oxo-1-phenethyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[1-Benzyl-8-methoxy-7-(2-methoxy-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

5-(3-Chloro-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(2-Chloro-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(4-Chloro-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

3-(8-Methoxy-1-methyl-2-oxo-7-(4-cyanophenyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile;

3-[1-Benzyl-8-methoxy-7-(2-methoxy-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[8-Methoxy-7-(2-methoxy-phenyl)-2-oxo-1-propyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[8-Methoxy-7-(2-methoxy-phenyl)-2-oxo-1-phenethyl-2,3-dihydro-1H-benzo[e][4]diazepin-5-yl]-benzamide;

3-[1-Hexyl-8-methoxy-7-(2-methoxy-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(4-Acetyl-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(4-Acetyl-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

5-(4-Methoxy-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(2-Methoxy-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

3-(7-Furan-2-yl-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile;

3-[7-(3,4-Dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(3,4-Dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

5-(3,5-Dichloro-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(3,4-Dichloro-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(4-Fluoro-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(3-Acetyl-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

1-Methyl-7-phenyl-5-(3-trifluoromethyl-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

1-Methyl-5-(4-methyl-3-nitro-phenyl)-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

1-Methyl-7-phenyl-5-(4-trifluoromethoxy-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(3-Bromo-phenyl)-8-methoxy-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

3-[7-(2-Isopropoxy-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

5-(3,4-Dimethoxy-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

1-Methyl-5-(3-nitro-phenyl)-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(3-Hex-1-ynyl-phenyl)-8-methoxy-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

{3-[3-(8-Methoxy-1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-phenyl]-prop-2-ynyl}-carbamic acid tert-butyl ester;

5-(3-Amino-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

3-(1-Methyl-2-oxo-8-phenoxy-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile;

3-[7-(2-Methoxy-phenyl)-1-methyl-2-oxo-8-phenoxy-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(2-Chloro-phenyl)-1-methyl-2-oxo-8-phenoxy-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-(1-Methyl-2-oxo-8-phenoxy-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide;

3-[7-(2-Chloro-phenyl)-1-methyl-2-oxo-8-phenoxy-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2-Methoxy-phenyl)-1-methyl-2-oxo-8-phenoxy-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

7-(2,6-Dimethoxy-phenyl)-5-(4-methoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

8-Methoxy-5-(4-methoxy-phenyl)-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-5-one;

7-(2,6-Dimethoxy-phenyl)-1-methyl-5-(4-methyl-3-nitro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

3-[7-(2-Isopropoxy-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

5-(3-Methoxy-phenyl)-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(3-Bromo-phenyl)-8-methoxy-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

3-[7-(2-Chloro-6-methoxy-phenyl)-2-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(5-Chloro-2-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(2-Chloro-6-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(5-Chloro-2-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-(2-Oxo-7-phenyl-8-trifluoromethoxy-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile;

3-(1-Methyl-2-oxo-7-phenyl-8-trifluoromethoxy-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile;

3-(1-Methyl-2-oxo-7-phenyl-8-trifluoromethoxy-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide;

3-[1-Methyl-2-oxo-7-(2-phenoxy-phenyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[7-(2,6-Dimethoxy-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[8-Methoxy-1-methyl-2-oxo-7-(2-phenoxy-phenyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile;

3-[1-Methyl-2-oxo-7-(2-phenoxy-phenyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2,6-Dimethoxy-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[8-Methoxy-1-methyl-2-oxo-7-(2-phenoxy-phenyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

8-Methoxy-1-methyl-7-phenyl-5-[3-(4-phenyl-butyl-phenyl]-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

8-Methoxy-5-[3-(3-methoxy-prop-1-ynyl)-phenyl]-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

{3-[4-(8-Methoxy-1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-phenyl]-prop-2-ynyl}carbamic acid tert-butyl ester;

8-Methoxy-1-methyl-7-phenyl-5-(4-phenylethynyl-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

8-Methoxy-5-[4-(3-methoxy-prop-1-ynyl)-phenyl]-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(3,4-Dichloro-phenyl)-7-(2,6-dimethoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

7-(2,6-Dimethoxy-phenyl)-5-(4-fluoro-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(3,4-Dimethoxy-phenyl)-7-(2,6-dimethoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(2-Bromo-phenyl)-8-methoxy-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

8-Methoxy-5-[3-(3-methoxy-propyl)-phenyl]-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(2-Bromo-phenyl)-8-methoxy-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(4-Hex-1-ynyl-phenyl)-8-methoxy-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

8-Methoxy-5-[4-(3-methoxy-propyl)-phenyl]-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

{3-[4-(8-Methoxy-1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-phenyl]-propyl}carbamic acid tert-butyl ester;

8-Methoxy-5-(4-methoxy-phenyl)-7-(2-methoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

7-(2,6-Dimethoxy-phenyl)-8-methoxy-5-(4-methoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

7-(2,5-Dimethoxy-phenyl)-8-methoxy-5-(4-methoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

7-(2-Fluoro-6-methoxy-phenyl)-8-methoxy-5-(4-methoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

8-Methoxy-5-(4-methoxy-phenyl)-1-methyl-7-(2-phenoxy-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(4-Bromo-phenyl)-8-methoxy-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

5-(4-Bromo-phenyl)-8-methoxy-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one; and

7-(2,6-Dimethoxy-phenyl)-1-methyl-5-m-tolyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one.

18. A compound of formula (I) in accordance with claim 1 , wherein said compound is selected from the group consisting of:

3-[7-(2,6-dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2,5-dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[8-methoxy-7-(4-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[8-methoxy-7-(2-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2-chloro-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-(8-methoxy-1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide;

7-(2,6-Dimethoxy-phenyl)-5-(4-methoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

3-[7-(2-Chloro-6-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2,6-Dimethoxy-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[8-Methoxy-1-methyl-2-oxo-7-(2-phenoxy-phenyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

5-(2,4-Dichloro-phenyl)-7-(2,6-dimethoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

7-(2,6-Dimethoxy-phenyl)-1-methyl-5-m-tolyl-1,3-dihydro-benzo[e][1,4]diazepin-5-one; and

7-(2,6-Dimethoxy-phenyl)-8-methoxy-5-(4-methoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one.

19. A compound of formula (I) in accordance with claim 1 , wherein said compound is selected from the group consisting of:

3-[7-(2,5-Dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2,6-Dimethoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

3-[7-(2,6-Dimethoxy-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzamide;

7-(2,6-Dimethoxy-phenyl)-5-(4-methoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one;

7-(2,6-Dimethoxy-phenyl)-5-(4-fluoro-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one; and

7-(2,6-Dimethoxy-phenyl)-8-methoxy-5-(4-methoxy-phenyl)-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one.

20. A pharmaceutical composition comprising at least one compound of formula (I) in accordance with claim 1 , and a pharmaceutically acceptable vehicle or support.

Assignments (4)
SECURITY AGREEMENT Recorded Mar 29, 2010
From: VIA PHARMACEUTICALS, INC.
To: BAY CITY CAPITAL LLC
Reel/Frame 024151/0196 →
COLLATERAL ASSIGNMENT OF PATENTS Recorded Mar 12, 2009
From: VIA PHARMACEUTICALS, INC.
To: BAY CITY CAPITAL LLC
Reel/Frame 022380/0518 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 7, 2008
From: NEURO3D
To: VIA PHARMACEUTICALS, INC.
Reel/Frame 021353/0751 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2006
From: ABARGHAZ, MUSTAPHA; BIONDI, STEFANO; DURANTON, JEROME; LIMANTON, EMMANUELLE; MONDADORI, CESARE; WAGNER, PATRICK
To: NEURO3D
Reel/Frame 018113/0344 →
Priority Claims (1)
EP 03293309 · Dec 23, 2003 · regional
Continuity (1)
Related Publication 20070123519A1 · May 31, 2007