IP Library Granted Patent US 7,592,357
Granted Patent B2
US 7,592,357 · App. 10/589,995 · Granted Sep 22, 2009

Compounds

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Quick Facts
Patent No.
US 7,592,357
App. No.
10/589,995
Granted
Sep 22, 2009
Kind
B2
Abstract

Novel Inhibitors of Rho-kinases are disclosed.

Claims (145)

1. A compound of formula (I)

or a pharmaceutically acceptable salt thereof wherein:

R 1 and R 2 , are, independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl;

R 3 is selected from the group consisting of phenyl optionally substituted with 1 to 3 substituents selected from the group consisting of F, Cl, trifluoromethyl, and phenyl; naphthyl; and quinolinyl;

R 4 is selected from the group consisting of hydrogen and methyl;

R 5 is C 1 -C 3 alkyl;

R 6 is selected from the group consisting of chlorine, fluorine and hydrogen; and

R 7 and R 8 , are, independently selected from the group consisting of hydrogen, halogen, and C 1 -C 3 alkyl.

2. A compound according to claim 1 having formula (II)

or a pharmaceutically acceptable salt thereof wherein:

R 5 is methyl;

R 6 is hydrogen; and

R 7 and R 8 are each hydrogen.

3. A compound or a pharmaceutically acceptable salt thereof, which compound is selected from the group consisting of

N-1H-Indazol-5-yl-2-methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Fluorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chlorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-1H-Indazol-5-yl-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Biphenylyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(3,4-Dichlorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Fluorophenyl)-N-1H-indazol-5-yl-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[2-Fluoro-4-(trifluoromethyl)phenyl]-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-1H-indazol-5-yl-2-methyl-6-oxo-4-(3-quinolinyl)-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-1H-indazol-5-yl)-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-N-(3-chloro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-1H-indazol-5-yl)-2-methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-1H-indazol-5-yl)-4-(4-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-N-(3-chloro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

2-Methyl-N-(3-methyl-1H-indazol-5-yl)-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Bromo-1H-indazol-5-yl)-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Ethyl-1H-indazol-5-yl)-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(7-Chloro-1H-indazol-5-yl)-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

2-Methyl-N-(7-methyl-1H-indazol-5-yl)-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl) phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Bromo-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl) phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[2-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-N-(3-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Ethyl-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl) phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1 H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl) phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[2-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-N-(7-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(7-Chloro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl) phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-2-methyl-N-(3-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Bromo-1H-indazol-5-yl)-4-(4-chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-N-(3-ethyl-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-2-methyl-N-(7-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-N-(7-chloro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Bromo-1H-indazol-5-yl)-2-methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

2-Methyl-N-(3-methyl-1H-indazol-5-yl)-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Ethyl-1H-indazol-5-yl)-2-methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

2-Methyl-N-(7-methyl-1H-indazol-5-yl)-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(7-Chloro-1H-indazol-5-yl)-2-methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-4-(4-chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chlorophenyl)-N-(6-fluoro-1 H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-1H-Indazol-5-yl-l ,2-dimethyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(3-Hydroxyphenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[4-(Aminosulfonyl)phenyl]-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Cyanophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl)phenyl]-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[2-Fluoro-4-(trifluoromethyl)phenyl]-1,2-dimethyl-N-(3-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl) phenyl]-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-1,2-dimethyl-N-(3-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-N-(3-chloro-1H-indazol-5-yl)-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-N-(6-fluoro-1H-indazol-5-yl)-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoro-methyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-4-(4-chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chlorophenyl)-2-methyl-N-(3-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Chloro-1H-indazol-5-yl)-4-(4-chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chlorophenyl)-N-1H-indazol-5-yl-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[2-Fluoro-4-(trifluoromethyl)phenyl]-N-1H-indazol-5-yl-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-N-1H-indazol-5-yl-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-1H-indazol-5-yl)-1,2-dimethyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-1,2-dimethyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chlorophenyl)-N-(6-fluoro-1H-indazol-5-yl)-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chlorophenyl)-1,2-dimethyl-N-(3-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-4-[2-fluoro-5-(methyloxy)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-4-[2-fluoro-3-(methyloxy)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(2-Fluoro-5-hydroxyphenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(2-Fluoro-3-hydroxyphenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[5-(Aminosulfonyl)-4-chloro-2-fluorophenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[3-(Aminosulfonyl)-4-chlorophenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[3-(Aminosulfonyl)phenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(2,3-Difluorophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(2,3-Difluorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(2,4-Difluorophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(2,4-Difluorophenyl)-N-(1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-4-(3-hydroxyphenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-2-methyl-4-{3-[(methylsulfonyl)amino]phenyl}-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-3-nitrophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(3-Amino-4-chlorophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-{4-Chloro-3-[(methylsulfonyl)amino]phenyl}-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-2-methyl-4-[3-nitro-4-(trifluoromethyl)phenyl]-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[3-Amino-4-(trifluoromethyl)phenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-2-methyl-4-[3-[(methylsulfonyl) amino]-4-(trifluoromethyl)phenyl]-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[3-[(Ethylsulfonyl)amino]-4-(trifluoromethyl)phenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-4-(2-fluoro-5-nitrophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-4-[4-fluoro-3-(trifluoro methyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[2,3-Difluoro-4-(trifluoromethyl)phenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-4-[3-fluoro-4-(trifluoromethyl) phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Cyanophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Biphenylyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-4-[4-(2-thienyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Bromophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(5-Cyano-2-fluorophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-4-[2-fluoro-4-(methyloxy)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-1H-indazol-5-yl)-4-[4-chloro-3-(methyloxy)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Bromo-1H-indazol-5-yl)-4-[4-chloro-3-(methyloxy)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[4-Chloro-3-(methyloxy)phenyl]-2-methyl-N-(3-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[4-Chloro-3-(methyloxy)phenyl]-N-(3-ethyl-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[4-Chloro-3-(methyloxy)phenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-3-hydroxyphenyl)-N-(3-chloro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Bromo-1H-indazol-5-yl)-4-(4-chloro-3-hydroxyphenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-3-hydroxyphenyl)-2-methyl-N-(3-methyl-1H-indazol-5-yl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-3-hydroxyphenyl)-N-(3-ethyl-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-3-hydroxyphenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(3-Chloro-1H-indazol-5-yl)-4-(4-chlorophenyl)-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-2-methyl-1-{[3-(methyloxy)phenyl]methyl}-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

1-Lthyl-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-(6-Fluoro-1H-indazol-5-yl)-2-methyl-1-(2-methylpropyl)-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide; and

1-[2-(Dimethylamino)-2-oxoethyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide.

4. A method of treating glaucoma comprising administering to a subject in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

5. A pharmaceutical composition comprising a compound according to claim 1 or a pharmaceutically acceptable salt thereof; and a suitable carrier.

6. A compound or a pharmaceutically acceptable salt thereof, which compound is selected from the group consisting of:

N-1H-Indazol-5-yl-2-methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Fluorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chloro-2-fluorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Chlorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

N-1H-Indazol-5-yl-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(4-Biphenylyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-(3,4-Dichlorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;

4-[2-Fluoro-4-(trifluoromethyl)phenyl]-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide; and

N-1H-Indazol-5-yl-2-methyl-6-oxo-4-(3-quinolinyl)-1,4,5,6-tetrahydro-3-pyridinecarboxamide.

7. The compound of claim 6 which is N-1H-Indazol-5-yl-2-methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide or a pharmaceutically acceptable salt thereof.

8. The compound of claim 6 which is 4-(4-Fluorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide or a pharmaceutically acceptable salt thereof.

9. The compound of claim 6 which is 4-(4-Chloro-2-fluorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide or a pharmaceutically acceptable salt thereof.

10. The compound of claim 6 which is 4-(4-Chlorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide or a pharmaceutically acceptable salt thereof.

11. The compound of claim 6 which is N-1H-Indazol-5-yl-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide or a pharmaceutically acceptable salt thereof.

12. The compound of claim 6 which is 4-(4-Biphenylyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide or a pharmaceutically acceptable salt thereof.

13. The compound of claim 6 which is 4-(3,4-Dichlorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide or a pharmaceutically acceptable salt thereof.

14. The compound of claim 6 which is 4-[2-Fluoro-4-(trifluoromethyl)phenyl]-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide or a pharmaceutically acceptable salt thereof.

15. The compound of claim 6 which is N-1H-Indazol-5-yl-2-methyl-6-oxo-4-(3-quinolinyl)-1,4,5,6-tetrahydro-3-pyridinecarboxamide or a pharmaceutically acceptable salt thereof.

16. A method of treating glaucoma comprising administering to a subject in need thereof a therapeutically effective amount of a compound according to claim 6 or a pharmaceutically acceptable salt thereof.

17. A pharmaceutical composition comprising a compound according to claim 6 or a pharmaceutically acceptable salt thereof and a suitable carrier.

Assignments (2)
CHANGE OF NAME Recorded Jan 6, 2010
From: SMITHKLINE BEECHAM CORPORATION
To: GLAXOSMITHKLINE LLC
Reel/Frame 023731/0761 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2009
From: LEE, DENNIS; GOODMAN, KRISTA B.
To: SMITHKLINE BEECHAM CORPORATION
Reel/Frame 022772/0445 →