Compounds

Inventors: Ian Robert Baldwin (Stevenage, GB); Kenneth David Down (Stevenage, GB); Paul Faulder (Stevenage, GB); Simon Gaines (Stevenage, GB); Joelle Le (Stevenage, GB); Nigel James Parr (Stevenage, GB); Timothy John Ritchie (Stevenage, GB); Juliet Kay Simpson (Stevenage, GB); Christian Alan Paul Smethurst (Harlow, GB)

Assignee: Glaxo Group Limited

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Quick Facts

Patent No.: US 8,536,169
App. No.: 12/994,254
Granted: Sep 17, 2013
Kind: B2

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Abstract

The invention is directed to certain novel compounds directed to compounds of formula (I) and salts thereof. The compounds of the invention are inhibitors of PI3-kinase activity.

Claims (56)

1. A compound of formula (I):

wherein

R 1 is 9- or 10-membered bicyclic heteroaryl wherein the 9- or 10-membered bicyclic heteroaryl contains from one to three heteroatoms independently selected from oxygen and nitrogen and is optionally substituted by C 1-6 alkyl, C 3-6 cycloalkyl, halo or —CN;

R 2 is —NHCOR 5 ,

R 3 is hydrogen or fluoro;

R 4 is hydrogen or methyl;

R 5 is phenyl optionally substituted by one or two substituents independently selected from C 1-6 alkyl, —OR 10 , halo, —NR 11 R 12 , and phenyl optionally substituted by halo;

R 11 and R 12 are each independently hydrogen or C 1-6 alkyl; and

R 10 is C 1-6 alkyl optionally substituted by from one to three fluoros;

or a salt thereof.

2. A compound according to claim 1 wherein R 1 is 9- or 10-membered bicyclic heteroaryl wherein the 9- or 10-membered bicyclic heteroaryl contains from one to three heteroatoms independently selected from oxygen and nitrogen.

3. A compound according to claim 1 wherein R 1 is indolyl.

4. A compound according to claim 1 wherein R 3 is hydrogen.

5. A compound according to claim 1 wherein R 4 is hydrogen.

6. A compound which is:

N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide;

2-fluoro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide;

2,3-difluoro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide;

2,5-difluoro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide;

N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-methylbenzamide;

2′-chloro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-biphenylcarboxamide;

2,4-difluoro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide;

2,6-difluoro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide;

N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-(methyloxy)benzamide;

2-[(difluoromethyl)oxy]-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide;

N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-4-methyl-2-(methyloxy)benzamide;

N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-5-methyl-2-(methyloxy)benzamide;

N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-3-methyl-2-(methyloxy)benzamide;

2-(ethyloxy)-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide;

N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-3-methylbenzamide;

3-(dimethylamino)-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide;

4-amino-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide;

a salt thereof.

7. A compound which is: