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Novel indazole derivatives and uses thereof

A compound, C4-C12 technology, applied in the field of indazole derivatives

Pending Publication Date: 2022-08-05
KOREA RES INST OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the indazole derivatives of the chemical formulas 1 and 2 of the present invention, their TRIB2 inhibitory activity or YAP inhibitory activity, and thus their usefulness in the treatment of cancer, narcolepsy and fasciitis have not been reported in the prior art. related content of

Method used

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  • Novel indazole derivatives and uses thereof
  • Novel indazole derivatives and uses thereof
  • Novel indazole derivatives and uses thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0133] Example 1. Synthesis of Indazole Derivatives and Confirmation of Physicochemical Properties

[0134] The synthetic procedures and physicochemical properties of the compounds 1 to 73 of the present invention are as follows.

[0135] Compound 1: tert-butyl 4-(5-(2-fluoropyridin-3-yl)-1H-indazole-3-carboxamido)piperidine-1-carboxylate

[0136] [Reaction 1]

[0137]

[0138] 1) Synthesis of 5-bromo-1H-indazole-3-carboxylic acid (5-bromo-1H-indazole-3-carboxylic acid)

[0139] A suspension of Indazole-3-carboxylic acid (500 mg, 3.08 mmol) in acetic acid (AcOH) (25 ml) was heated to 120°C to dissolve the starting material. The reaction mixture was cooled to 90°C, and the reaction mixture to which bromine (0.32 ml, 6.16 mmol) was added was stirred at 90°C for 18 hours. The reaction mixture was diluted with water (20 ml) and stirred for 1 hour. The solid formed in the reaction mixture was filtered and sucked dry to give compound 15-246 (550 mg, 2.28 mmol, 74%) as a white...

Embodiment 2

[0731] Example 2. Confirmation of TRIB2 or YAP inhibitory activity

[0732] Using the compounds 1 to 73 of the present invention synthesized from the above-mentioned Example 1, the TRIB2 kinase inhibitory activity and the cancer cell proliferation inhibitory activity were confirmed as shown in the following Table 1, and the YAP inhibitory activity was as follows figure 1 shown.

[0733] The TRIB2 kinase activity assay was commissioned by eurofins. The simple method is as follows: First, mix human TRIB2 enzyme with 8mM 3-morpholinopropanesulfonic acid (MOPS) (pH 7.0) , 0.2mM ethylenediaminetetraacetic acid (EDTA), 250μM substrate (RRRFRPASPLRGPPK), using 10mM Magnesium acetate (Magnesium acetate), 15μM microorganism γ-33P-ATP (gamma-33P-ATP), Different concentrations of test drugs were treated and allowed to react at room temperature for 120 minutes. Subsequently, the reaction was terminated by treatment with 0.5% phosphoric acid, and 10 μL of the reaction solution was droppe...

preparation example 1

[0741]

[0742] Mix 2 g of the present compound 17 (5-(2-fluoropyridin-3-yl)-N-(pyridin-4-yl)-1H-indazole-3-carboxamide), 1 g of lactose, and fill to gas The powder is prepared in a sealed bag.

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Abstract

The present invention relates to a novel indazole derivative and a use thereof, the indazole derivative having an excellent TRIB2 or YAP inhibitory activity and thus being useful as a pharmaceutical composition for preventing or treating cancer, hypersomnia, and fasciitis.

Description

technical field [0001] The present invention relates to a novel indazole derivative and use thereof, more particularly, to a novel indazole derivative with excellent Tribbles pseudokinase 2 (TRIB2) or Yes-associated protein (YAP) inhibitory activity, and a novel indazole derivative comprising the same The pharmaceutical composition for preventing or treating cancer, narcolepsy and fasciitis. Background technique [0002] Tribbles pseudokinase 2 (tribbles pseudokinases 2, TRIB2) is one of the proteins that facilitate molecular binding and is associated with various signal transduction pathways. In particular, TRIB2 is known to play an important role in properties related to cancer formation in various cancers, and has been found to be involved in androgen-independent studies through various in vitro and in vivo experiments and tissue studies of cancer patients. Proliferation / survival in prostate cancer, liver cancer, acute myeloid leukemia (AML), lung cancer, melanoma, antic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14A61K31/437A61K31/444A61K31/4725C07D401/04C07D471/04A61P21/00A61P25/00A61P29/00A61P35/00
CPCA61P21/00A61P25/00A61P29/00A61P35/00C07D401/04C07D401/14C07D471/04C07D401/12C07D405/14C07D409/14A61K9/145A61K9/2054A61K9/4866A61K9/205A61K9/0019A61K31/437A61K31/444A61K31/4725
Inventor 金珌虎金成桓
Owner KOREA RES INST OF CHEM TECH
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