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US 2012/0238571 A1Published application
Indazole derivatives as pi 3-kinase
AssigneeGlaxo Group Limited
InventorsIan Robert Baldwin, Kenneth David Down, Paul Faulder, Simon Gaines, Julie Nicole Hamblin, Katherine Louise Jones, Joelle Le, Christopher James Lunniss, Nigel James Parr, Timothy John Ritchie, John Edward Robinson, Christian Alan Paul Smethurst
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Abstract
The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds of formula (I): and salts thereof. The compounds of the invention are inhibitors of PI3-kinase activity.
Claims15
A compound of formula (I)
- wherein
- R1 is 9-membered bicyclic heteroaryl wherein the 9-membered bicyclic heteroaryl contains from one to three heteroatoms independently selected from oxygen and nitrogen and is optionally substituted by C1-6alkyl, halo or —CN;
- or phenyl fused to pyrrolidinyl wherein the pyrrolidinyl is substituted by oxo;
- R2 is 5-membered heteroaryl wherein the 5-membered heteroaryl contains one or two heteroatoms independently selected from oxygen, nitrogen and sulphur and is optionally substituted by one or two substituents independently selected from C1-6alkyl, —CO2R5 and —CH2NR6R7;
- or pyridinyl substituted by C1-6alkyl or —CH2NR8R9;
- R3 is hydrogen or fluoro;
- R4 is hydrogen or methyl;
- R5 is hydrogen or C1-6alkyl;
- R6 and R7, together with the nitrogen atom to which they are attached, are linked to form a 6-membered heterocyclyl wherein the 6-membered heterocyclyl optionally contains an oxygen atom and is optionally substituted by C1-6alkyl;
- and
- R8 and R9, together with the nitrogen atom to which they are attached, are linked to form a 6-membered heterocyclyl wherein the 6-membered heterocyclyl optionally contains a sulphur atom and is optionally substituted by one or two oxo substituents;
- or a salt thereof.
9 more elements
A compound which is:
- N-[6-(6-fluoro-1H-indol-4-yl)-1H-indazol-4-yl]-6-methyl-2-pyridinecarboxamide;
- N-[3-fluoro-6-(1H-indol-4-yl)-1H-indazol-4-yl]-6-methyl-2-pyridinecarboxamide;
- 2,5-dimethyl-N-[6-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-1,3-oxazole-4-carboxamide;
- 6-methyl-N-[6-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide;
- N-[6-(6-fluoro-1H-indol-4-yl)-1H-indazol-4-yl]-2,5-dimethyl-1,3-oxazole-4-carboxamide;
- 2,5-dimethyl-N-[6-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-indazol-4-yl]-1,3-oxazole-4-carboxamide;
- 6-methyl-N-[6-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide;
- N-[3-fluoro-6-(1H-indol-4-yl)-1H-indazol-4-yl]-3-(1-methylethyl)-2-pyridinecarboxamide;
- 3-(1-methylethyl)-N-[6-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide;
- N-[6-(6-fluoro-1H-indol-4-yl)-1H-indazol-4-yl]-3-(1-methylethyl)-2-pyridinecarboxamide;
- N-[3-fluoro-6-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-indazol-4-yl]-2,5-dimethyl-1,3-oxazole-4-carboxamide;
- N-[3-fluoro-6-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-indazol-4-yl]-3-(1-methylethyl)-2-pyridinecarboxamide;
- N-[3-fluoro-6-(6-fluoro-1H-indol-4-yl)-1H-indazol-4-yl]-2,5-dimethyl-1,3-oxazole-4-carboxamide;
- N-[3-fluoro-6-(1H-indol-4-yl)-1H-indazol-4-yl]-2,5-dimethyl-1,3-oxazole-4-carboxamide;
- N-[3-fluoro-6-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide;
- N-[6-(6-cyano-1H-indol-4-yl)-1H-indazol-4-yl]-1,4-dimethyl-1H-pyrazole-3-carboxamide;
- 2-methyl-N-[6-(2-oxo-2,3-dihydro-1H-indol-4-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide;
- N-[6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide;
- N-[6-(1H-benzimidazol-5-yl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide;
- 2-methyl-N-[6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide;
- N-1H,1′H-5,6′-biindazol-4′-yl-2-methyl-1,3-thiazole-4-carboxamide;
- 2-methyl-N-[6-(1H-pyrrolo[2,3-c]pyridin-3-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide;
- N-(6-imidazo[1,2-a]pyridin-6-yl-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide;
- 2-methyl-N-[1-methyl-6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide;
- N-(6-furo[3,2-b]pyridin-6-yl-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide;
- N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-1-(1-methylethyl)-1H-pyrazole-5-carboxamide;
- N-[6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-2-furancarboxamide;
- 1,1-dimethylethyl 4-({[6-(1H-indol-4-yl)-1H-indazol-4-yl]amino}carbonyl)-3-methyl-1H-pyrazole-1-carboxylate;
- 2-(1-piperidinylmethyl)-N-[6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide;
- 2-[(2-ethyl-4-morpholinyl)methyl]-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide;
- 6-[(1,1-dioxido-4-thiomorpholinyl)methyl]-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide;
- or
- a salt thereof.
30 more elements
10-12. (canceled)
Dependencies are inferred from the claim text.