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New 3-([1,2,4]triazolo[4,3-a]pyridin-7-yl)benzamide derivatives

A technology of toluamide and pyridine, which is applied in the field of inhibitors of p38 mitogen-activated protein, can solve problems such as not showing

Inactive Publication Date: 2010-03-24
ALMIRALL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In contrast, p38β, γ and δ knockout (knock-out) mice did not show any developmental deficits (Beardmore et al., 2005; Sabio et al., 2005)

Method used

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  • New 3-([1,2,4]triazolo[4,3-a]pyridin-7-yl)benzamide derivatives
  • New 3-([1,2,4]triazolo[4,3-a]pyridin-7-yl)benzamide derivatives
  • New 3-([1,2,4]triazolo[4,3-a]pyridin-7-yl)benzamide derivatives

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preparation example Construction

[0201] Diluents are used in the preparation of the ingredients and include those liquid and solid diluents which are compatible with the active ingredients together with coloring or flavoring agents, if desired. Tablets or capsules may conveniently contain between 1-500 mg of active ingredient or an equivalent amount of a salt thereof.

[0202] Liquid compositions suitable for oral use may be in the form of solutions or suspensions. Solutions may be aqueous solutions of soluble salts or other derivatives of the active compound, combined with, for example, sucrose to form a syrup. Suspensions may contain an insoluble active compound of this invention or a pharmaceutically acceptable salt thereof, together with a suspending agent or flavoring agent, in combination with water.

[0203] Components suitable for parenteral injection may be prepared from soluble salts, which may or may not be lyophilized, and which may be dissolved in a pyrogen-free aqueous vehicle or other appropri...

Embodiment 1

[0488]

[0489] 3-(3-tert-butyl-[1,2,4]triazol[4,3-a]pyridin-7-yl)-N-cyclopropyl-4-methylbenzamide

[0490]A Schlenk tube was loaded with Intermediate 2 (1.07 g, 3.56 mmol), Intermediate 11 (1.26 g, 4.18 mmol), cesium carbonate (2M in water, 5 mL, 10.0 mmol) and dioxane (60 mL ). The mixture was submitted to three vacuum-argon cycles followed by [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (1:1) (168mg, 0.206mmol ) added, and removed in the same way. The reaction was stirred at 95°C under argon atmosphere for 17 hours. Next, pass the reacted raw material through the Siro to filter and wash with ethyl acetate. This organic phase was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated to give a light green oil. This oil was taken up in ethyl acetate and extracted with hydrochloric acid 2N (3 x 200 mL). The acidic aqueous phase was basified with sodium hydroxide 2N (620 mL) and extracted with dichlorometh...

Embodiment 2

[0494]

[0495] N-cyclopropyl-3-(3-isopropyl-[1,2,4]triazol[4,3-a]pyridin-7-yl)-4-methylbenzamide

[0496] From Intermediate 3 and Intermediate 11, a white solid (47%) was obtained according to the experimental procedure described in Synthesis Example 1.

[0497] LRMS (m / z): 335 (M+1) + .

[0498] 1 H-NMRδ(CDCl 3 ): 0.65(m, 2H), 0.88(m, 2H), 1.57(d, J=7.1Hz, 6H), 2.35(s, 3H), 2.93(m, 1H), 3.42(m, 1H), 6.51 (brs, 1H), 6.83(d, J=7.1Hz, 1H), 7.36(d, J=7.6Hz, 1H), 7.59(s, 1H), 7.70(m, 2H), 7.96(d, J= 7.6Hz, 1H).

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Abstract

This invention is directed to new inhibitors of the p38 mitogen-activated protein kinase having the general formula (I) to processes for their preparation; to pharmaceutical compositions comprising them; and to their use in therapy.

Description

technical field [0001] The present invention relates to novel inhibitors of p38 mitogen-activated protein. Background technique [0002] Mistogen-activated protein kinases (MAP kinases) are evolved conservation enzymes that translate membrane signals into gene expression responses. In mammals, four MAP kinase (MAPK) families can be distinguished: extracellular signal-related kinases (ERK1 / 2), Jun aminoterminal kinases (JNK1 / 2 / 3), p38 protein (alpha (alpha), beta (beta), gamma (gamma) and delta (delta)) and ERK5. The regulation of these proteins is represented by a three-tier cascade consisting of MAP kinases, MAP kinase kinases, and MAP kinase kinase kinases. [0003] p38MAP kinase is generally defined as a target of CSAIDs (Cytokine Inhibitory Anti-Inflammatory Drugs) with a central role in the signal transduction pathway leading to tumor necrosis factor-alpha (TNF-alpha) and other cytokines generated by (Lee et al., 1984). In response to stress and inflammatory stimuli...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/437A61P29/00
CPCC07D471/04A61P1/00A61P1/04A61P11/00A61P17/00A61P17/06A61P19/00A61P19/02A61P19/10A61P25/00A61P25/28A61P29/00A61P35/00A61P37/02A61P43/00A61P9/00A61P9/10A61K31/437
Inventor 伯纳特·维达尔胡安保罗罗伯特·伊斯特伍德雅各布·冈萨雷斯罗德里格斯克里斯蒂娜·伊斯特埃特里亚斯
Owner ALMIRALL
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