Heterocyclic modulators of lipid synthesis
US-2024400552-A1 · Dec 5, 2024 · US
Indazole derivatives useful as ERK inhibitors
US9351965B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9351965-B2 |
| Application number | US-201113994224-A |
| Country | US |
| Kind code | B2 |
| Filing date | Dec 16, 2011 |
| Priority date | Dec 21, 2010 |
| Publication date | May 31, 2016 |
| Grant date | May 31, 2016 |
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- Title
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- Abstract
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Abstract
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The present invention provides a compound of the Formula I, or a pharmaceutically acceptable salt, solvate or ester thereof, wherein R, R 1 , R 2 , R 3 , m and are as defined herein. The compounds are ERK inhibitors. Also disclosed are pharmaceutical compositions that comprise the above compounds, and methods of treating cancer using the same.
First claim
Opening claim text (preview).
What is claimed is: 1. The compound selected from the group consisting of: N-[3-[(2-fluorophenyl)methyl]-3-hydroxycyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(hydroxymethyl)-3-phenoxycyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-amino-3-[(2-fluorophenyl)methyl]cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-[(2-fluorophenyl)methyl]-3-hydroxycyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(2-fluorophenoxy)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(2-fluorophenoxy)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(1H-imidazol-1-ylmethyl)cyclohexyl]-3-(2-methyl-2H-indazol-)-1H-indazole-5-carboxamide; N-[3-(2-chlorophenoxy)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(2,6-dimethylphenoxy)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(2,6-difluorophenoxy)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(aminocarbonyl)-3-(3-fluorophenoxy)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[cis-3-hydroxy-3-(1H-imidazol-1-ylmethyl)cyclohexyl]-3-(2-methyl-2H-indazol-)-1H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-(1H-imidazol-1-ylmethyl)cyclohexyl]-3-(2-methyl-2H-indazol-)-1H-indazole-5-carboxamide; N-[3-[(2-fluorophenyl)methyl]-3-(formylamino)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-[(2-fluorophenyl)methyl]-3-methoxycyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-[(2-fluorophenyl)methyl]-3-methoxycyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(2-fluorophenoxy)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(3-fluorophenoxy)-3-(hydroxymethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(1H-benzimidazol-1-ylmethyl)cyclohexyl]-3-(2-methyl-2H-indazol-)-1H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-(1H-pyrazol-1-ylmethyl)cyclohexyl]-3-(2-methyl-2H-indazol-)-1H-indazole-5-carboxamide; N-[cis-3-hydroxy-3-(1H-pyrazol-1-ylmethyl)cyclohexyl]-3-(2-methyl-2H-indazol-)-1H-indazole-5-carboxamide; N-[trans-3-(1H-benzimidazol-1-ylmethyl)-3-hydroxycyclohexyl]-3-(2-methyl-2H-indazol-)-1H-indazole-5-carboxamide; N-[cis-3-(1H-benzimidazol-1-ylmethyl)-3-hydroxycyclohexyl]-3-(2-methyl-2H-indazol-5-yl)-1H-indazole-5-carboxamide; N-[3-(difluorophenylmethyl)-3-hydroxycyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-hydroxy-3-(hydroxyphenylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; 3-imidazo[1,2-a]pyridin-6-yl-N-[3-(1H-pyrazol-1-ylmethyl)cyclohexyl]-1H-indazole-5-carboxamide; N-(3-benzoyl-3-hydroxycyclohexyl)-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-[(2,6-difluorophenyl)methyl]-3-hydroxycyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-(1H-1,2,4-triazol-1-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[cis-3-hydroxy-3-(1H-1,2,4-triazol-1-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; 3-imidazo[1,2-a]pyridin-6-yl-N-[3-(1H-1,2,4-triazol-1-ylmethyl)cyclohexyl]-1H-indazole-5-carboxamide; Ethyl-1-[(2-fluorophenyl)methyl]-3-[[[3-(2-methyl-4-pyridinyl)-1H-indazol-5-yl]carbonyl]amino]cyclohexanecarboxylate; N-[3-[(2-fluorophenyl)methyl]-3-(hydroxymethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(2-chlorophenoxy)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3 (R)-hydroxy-3-(1H-indazol-1-ylmethyl)-1(R)-cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3 (S)-hydroxy-3-(1H-indazol-1-ylmethyl)-1(R)-cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[trans-3-[(2-fluorophenyl)methyl]-3-hydroxycyclohexyl]-3-imidazo[1,2-a]pyridin-6-yl-1H-indazole-5-carboxamide; 3-(6-benzothiazolyl)-N-[3-[(2-fluorophenyl)methyl]-3-hydroxycyclohexyl]-1H-indazole-5-carboxamide; 1-[(2-fluorophenyl)methyl]-3-[[[3-(2-methyl-4-pyridinyl)-1H-indazol-5-yl]carbonyl]amino]cyclohexanecarboxylic acid; 3-(6-benzothiazolyl)-N-[3-[(2-fluorophenyl)methyl]-3-hydroxycyclohexyl]-1H-indazole-5-carboxamide; N-[3-[(2-methyl-1H-benzimidazol-1-yl)methyl]cyclohexyl]-3-(2-methyl-6-benzothiazolyl)-1H-indazole-5-carboxamide; N-[3-[(3-cyano-1H-indol-1-yl)methyl]cyclohexyl]-3-(2-methyl-6-benzothiazolyl)-1H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-[[2-(trifluoromethyl)-1H-benzimidazol-1-yl]methyl]cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[cis-3-hydroxy-3-[[2-(trifluoromethyl)-1H-benzimidazol-1-yl]methyl]cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(difluorophenylmethyl)-3-hydroxycyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-[(2-methyl-1H-benzimidazol-1-yl)methyl]cyclohexyl]-3-(2-methyl-4-pyridinyl)-H-indazole-5-carboxamide; N-[cis-3-hydroxy-3-[(2-methyl-1H-benzimidazol-1-yl)methyl]cyclohexyl]-3-(2-methyl-4-pyridinyl)-H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-(1H-imidazo[4,5-b]pyridin-1-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-(3H-imidazo[4,5-b]pyridin-3-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(2-chlorophenoxy)-1-piperidinyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-hydroxy-3-(hydroxyphenylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-hydroxy-3-(hydroxyphenylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(hydroxymethyl)-3-(phenylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-(3-benzoyl-3-hydroxycyclohexyl)-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-(2H-pyrazolo[3,4-b]pyridin-2-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-(1H-pyrazolo[3,4-c]pyridin-1-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-(2H-pyrazolo[3,4-c]pyridin-2-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[trans-3-hydroxy-3-[(2-methyl-1H-imidazo[4,5-c]pyridin-1-yl)methyl]cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-[(2-fluorophenyl)methyl]-3-(hydroxymethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(2,4-difluorophenoxy)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-(4-fluorophenoxy)-3-(hydroxymethyl)-1-piperidinyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-[(2,4-di fluorophenyl)methyl]-3-(hydroxymethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[3-[(4-fluorophenyl)methyl]-3-(hydroxymethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; 1-[(4-fluorophenyl)methyl]-3-[[[3-(2-methyl-4-pyridinyl)-1H-indazol-5-yl]carbonyl]amino]cyclohexanecarboxylic acid; N-[3(S)-[(2-fluorophenyl)methyl]-3-hydroxy-1(R)-cyclohexyl]-3-(2-methyl[1,2,4]triazolo[1,5-a]pyridiN-6-yl)-1H-indazole-5-carboxamide; N-[3(S)-[(2-fluorophenyl)methyl]-3-hydroxy-1(R)-cyclohexyl]-3-(2-methyl-6-benzothiazolyl)-1H-indazole-5-carboxamide; N-[3(S)-[(2-fluorophenyl)methyl]-3-hydroxy-1(R)-cyclohexyl]-3-imidazo[1,2-a]pyridin-6-yl-1H-indazole-5-carboxamide; N-[cis-3-hydroxy-3-(2H-pyrazolo[3,4-b]pyridin-2-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[cis-3-hydroxy-3-(1H-pyrazolo[3,4-b]pyridin-1-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[cis-3-hydroxy-3-(1H-pyrazolo[3,4-c]pyridin-1-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[cis-3-hydroxy-3-(1H-imidazo[4,5-b]pyridin-1-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; N-[cis-3-hydroxy-3-(3H-imidazo[4,5-b]pyridin-3-ylmethyl)cyclohexyl]-3-(2-methyl-4-pyridinyl)-1H-indazole-5-carboxamide; 3-(2-methy
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Ortho-condensed systems · CPC title
- A61K31/4439Primary
containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465) · CPC title
directly linked by a ring-member-to-ring-member bond · CPC title
containing three or more hetero rings · CPC title
containing three or more hetero rings · CPC title
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- What does patent US9351965B2 cover?
- The present invention provides a compound of the Formula I, or a pharmaceutically acceptable salt, solvate or ester thereof, wherein R, R 1 , R 2 , R 3 , m and are as defined herein. The compounds are ERK inhibitors. Also disclosed are pharmaceutical compositions that comprise the above compounds, and methods of treating cancer using the same.
- Who is the assignee on this patent?
- Shipps Jr Gerald W, Huang Xiaohua, Deng Yongqi, and 6 more
- What technology area does this patent fall under?
- Primary CPC classification A61K31/4439. Mapped technology areas include Human Necessities.
- When was this patent published?
- Publication date Tue May 31 2016 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).