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Benzonitrile derivatives as kinase inhibitors

A technology of compounds, mixtures, applied in techniques and procedures, capable of solving problems such as increased kinase expression, high protein kinase activity, increased kinase activity, etc.

Active Publication Date: 2014-07-16
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Aberrant activity involves: (1) expression in cells that do not normally express these protein kinases; (2) increased kinase expression, which leads to undesired cell proliferation such as cancer; (3) increased kinase activity, which leads to undesired Proliferation of cells such as cancer and / or lead to excessive activity of the corresponding protein kinase

Method used

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  • Benzonitrile derivatives as kinase inhibitors
  • Benzonitrile derivatives as kinase inhibitors
  • Benzonitrile derivatives as kinase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 105-117

[0766] Analytical method:

[0767] LCMS analysis:

[0768] Method A: A-0.1% TFA in H 2 O, B - 0.1% TFA in CAN: flow rate 2.0 ml / min.

[0769] Column: XBridge C8 (50 x 4.6mm, 3.5 μ)

[0770] Method B: A-10mM NH 4 HCO 3 , B: ACN; flow rate: 1.0 ml / min

[0771] Column: XBridge C8 (50x4.6mm, 3.5μ),

[0772] 1 H NMR:

[0773] Bruker 400 MHz

[0774] HPLC:

[0775] Method A:

[0776] Method: A-0.1% TFA in H 2 O, B-0.1% TFA in ACN: Flow rate – 2.0 ml / min.

[0777] Column: XBridge C8 (50 x 4.6 mm, 3.5 μ).

[0778] Synthesis of 5-bromo-2-cyclopropylmethoxybenzonitrile

[0779]

[0780] Sodium hydride, 60% suspended in oil (3.6 g, 0.09 mol) was added to a solution of cyclopropylmethanol (6.49 g, 0.09 mol) in dry DMF (200 ml) at 0 °C under nitrogen middle. After 30 min, 5-bromo-2-fluorobenzonitrile (12.0 g, 0.06 mol) in dry DMF (50 ml) was added at 0 °C and the reaction was stirred at 50 °C for 16 h. Ice water (200 ml) was added to the reaction mixture and extracted w...

Embodiment A

[0939] Example A: Injection Vials

[0940] A solution of 100 g of the active ingredient according to the invention and 5 g of disodium hydrogen phosphate in 3 liters of double distilled water is adjusted to pH 6.5 using 2 N hydrochloric acid, sterile filtered, filled into injection vials and lyophilized under sterile conditions And sealed under sterile conditions. Each injection vial contains 5 mg of active ingredient.

Embodiment B

[0941] Embodiment B: Suppository

[0942] A mixture of 20 g of active ingredient according to the invention with 100 g of soy lecithin and 1400 g of cocoa butter is melted, poured into molds and allowed to cool. Each suppository contains 20 mg of active ingredient.

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PUM

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Abstract

The invention relates to compounds of the formula (I), wherein R1, R2, X and Y have the meaning specified in claim 1, are inhibitors of TBK1 and IotaKappaKappaepsilon, and can be used, inter alia, for the treatment of cancer and inflammatory diseases.

Description

Background technique [0001] The object of the present invention was to find novel compounds having valuable properties, in particular those which can be used for the preparation of medicaments. [0002] The present invention relates to benzonitrile compounds capable of inhibiting one or more kinases. The compound is used in the treatment of a large number of diseases including cancer, septic shock, primary open angle glaucoma (POAG), hyperplasia, rheumatoid arthritis, psoriasis, atherosclerosis, retinopathy , osteoarthritis, endometriosis, chronic inflammatory and / or neurodegenerative diseases such as Alzheimer's disease. [0003] The present invention relates to compounds and uses of compounds that play a role in inhibiting, modulating and / or modulating the signal transduction of receptor kinases, as well as pharmaceutical compositions containing these compounds and the use of these compounds for treating kinase-induced diseases. [0004] Because protein kinases regulate al...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D401/14C07D405/14C07D413/14C07D417/14C07D471/04C07D491/10A61K31/506A61K31/4433
CPCC07D213/74C07D401/12C07D401/14C07D403/12C07D405/14C07D413/14C07D417/14C07D471/04C07D491/107C07D491/10A61K31/4439A61K31/444A61K31/4545A61K31/497A61K31/501A61K31/506A61K31/5377A61P1/00A61P11/00A61P15/00A61P17/02A61P17/06A61P19/00A61P19/02A61P21/00A61P25/00A61P25/28A61P27/00A61P27/02A61P27/06A61P29/00A61P3/00A61P3/04A61P31/00A61P35/00A61P37/02A61P37/06A61P43/00A61P5/50A61P7/00A61P9/00A61P9/10A61P3/10A61K45/06
Inventor G.赫尔策曼D.多施H-M.埃根魏勒
Owner MERCK PATENT GMBH
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