IP Library Granted Patent US 7,888,503
Granted Patent B2
US 7,888,503 · App. 11/577,444 · Granted Feb 15, 2011

Benzodiazepine derivatives that inhibit rock

Assignee: GlaxoSmithKline LLC
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Quick Facts
Patent No.
US 7,888,503
App. No.
11/577,444
Granted
Feb 15, 2011
Kind
B2
Abstract

The present invention relates to dihydrobenzodiazepine derivatives, compositions and medicaments containing the same, as well as processes for the preparation and use of such compounds, compositions and medicaments. Such dihydrobenzodiazepine derivatives are useful in the treatment of diseases associated with inappropriate ROCK kinase.

Claims (41)

1. A compound of Formula (I):

wherein

the dotted line represents a bond or is absent;

R 1 represents pyrazolyl, pyridinyl, pyrimidinyl optionally substituted by NH 2 , or indazolyl;

R 2 represents phenyl optionally substituted by one or more substituents selected from C 1-6 alkyl, CN, C 1-6 alkoxy, C 1-6 haloalkyl, C 1-6 haloalkoxy, NO 2 , halogen; or a 5-membered heteroaryl group containing one or more heteroatoms selected from O, N or S optionally substituted by a 5-membered heteroaryl group;

R 3 and R 4 independently represent H or C 1-6 alkyl;

or a salt thereof.

2. A compound selected from the group consisting of:

Structure

Name

5-(2-fluorophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4- benzodiazepine

5-(2-fluorophenyl)-7-(4-pyridinyl )-2,3,4,5-tetrahydro- 1H-1,4-benzodiazepine

(3S)-5-(2-fluorophenyl)-3-methyl-7-(4-pyridinyl)-2,3- dihydro-1H-1,4-benzodiazepine

7-(4-pyridinyl)-5-(3-thienyl)-2,3-dihydro-1H-1,4- benzodiazepine

5-(2,2′-bithien-5-yl)-7-(4-pyridinyl)-2,3-dihydro-1H- 1,4-benzodiazepine

7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepine

5-(3-nitrophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4- benzodiazepine

5-[3-(methyloxy)phenyl]-7-(4-pyridinyl)-2,3-dihydro- 1H-1,4-benzo-diazepine

5-phenyl-7-(4-pyridinyl)-2,3-dihydro-1H-1,4- benzodiazepine

7-(4-pyridinyl)-5-[2-(trifluoromethyl)phenyl]-2,3- dihydro-1H-1,4-benzodiazepine

5-(2-nitrophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4- benzodiazepine

-(5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-7-yl)-2- pyrimidinamine

5-phenyl-7-(1H-pyrazol-4-yl)-2,3-dihydro-1H-1,4- benzodiazepine

[2-fluoro-5-(1H-indazol-5- yl)phenyl](phenyl)methanone

4-[7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepin- 5-yl]benzonitrile

5-(4-chlorophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4- benzodiazepine

and salts thereof.

3. A compound of Formula (I):

wherein

the dotted line represents a bond or is absent;

R 1 represents pyrazolyl, pyridinyl optionally substituted by halo, pyrimidinyl optionally substituted by NH 2 , or indazolyl;

R 2 represents phenyl optionally substituted by one or more substituents selected from C 1-6 alkyl, CN, C 1-6 alkoxy, C 1-6 haloalkyl, C 1-6 haloalkoxy, NO 2 , halogen; or a 5-membered heteroaryl group containing one or more heteroatoms selected from O, N or S optionally substituted by a 5-membered heteroaryl group;

R 3 and R 4 independently represent H or C 1-6 alkyl;

or a salt or thereof.

4. The compound:

7-(3-fluoropyridin-4-yl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine

or a salt thereof.

5. A pharmaceutical composition comprising a therapeutically effective amount of a compound as claimed in claim 1 , or a salt thereof and one or more of pharmaceutically acceptable carriers, diluents and excipients.

6. A pharmaceutical composition comprising a therapeutically effective amount of a compound as claimed in claim 2 or a salt thereof and one or more of pharmaceutically acceptable carriers, diluents and excipients.

7. A pharmaceutical composition comprising a therapeutically effective amount of a compound as claimed in claim 3 or a salt thereof and one or more of pharmaceutically acceptable carriers, diluents and excipients.

8. A pharmaceutical composition comprising a therapeutically effective amount of a compound as claimed in claim 4 or a salt thereof and one or more of pharmaceutically acceptable carriers, diluents and excipients.

Assignments (1)
CHANGE OF NAME Recorded Jan 5, 2011
From: SMITHKLINE BEECHAM CORPORATION
To: GLAXOSMITHKLINE LLC
Reel/Frame 025586/0628 →
Continuity (2)
Provisional Application 60620189 · Oct 19, 2004
Related Publication 20090143366A1 · Jun 4, 2009