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Isoquinolinone derivatives

A technology for compounds and oxides, which can be used in drug combinations, active ingredients of heterocyclic compounds, digestive system, etc., and can solve problems such as unsatisfactory efficacy.

Inactive Publication Date: 2011-11-16
ASTRAZENECA AB
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although glucocorticoid therapy can yield important benefits, the efficacy of these drugs is often far from satisfactory, especially in the treatment of COPD

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0505] N-cyclopropyl-3-fluoro-5-[2-(3-hydroxy-2,2-dimethylpropyl)-1-oxo-4-(piperazin-1-ylmethyl)-1 , 2-Dihydroisoquinolin-6-yl]-4-methylbenzamide

[0506]

[0507] a) 4-Bromo-2-[(E)-2-(dimethylamino)vinyl]benzonitrile

[0508] A solution of 4-bromo-2-methylbenzonitrile (1.0 g) dissolved in 1-tert-butoxy-N, N, N', N'-tetramethylmethylenediamine (2.11 ml) was heated at 140 Stir for 2 hours at °C (flask opened to evaporate tert-butanol). The reaction mixture was diluted with water (250ml) and extracted with ethyl acetate (350ml). dry (MgSO 4 ) organics, filtered and evaporated to give crude product. The crude product was triturated with isohexane overnight to give the subtitle compound (0.75 g) as a solid.

[0509] 1 H NMRδ(CDCl 3 )7.50(s, 1H), 7.34(s, 1H), 7.05-6.96(m, 2H), 5.29(d, 1H), 2.94(s, 6H)

[0510] b) 6-bromoisoquinolin-1(2H)-one

[0511] Under nitrogen atmosphere, 4-bromo-2-[(E)-2-(dimethylamino)vinyl]benzonitrile (Example 1a, 1.0 g) was dissolved in 33% hy...

Embodiment 2

[0530] N-cyclopropyl-3-fluoro-5-{2-(3-hydroxy-2,2-dimethylpropyl)-4-[(4-methyl-1,4-diazepane -1-yl)methyl]-1-oxo-1,2-dihydroisoquinolin-6-yl}-4-methylbenzamide

[0531]

[0532] a) 6-bromo-2-(3-hydroxyl-2,2-dimethylpropyl)isoquinolin-1(2H)-one

[0533] A solution of 6-bromoisoquinolin-1(2H)-one (Example 1b, 2.5 g) in NMP (20 ml) was treated with cesium carbonate (7.27 g) and 3-bromo-2,2 under nitrogen atmosphere. - Treated with dimethylpropan-1-ol (2.75ml). The resulting mixture was stirred at 100°C for 8 hours. More cesium carbonate (1 equiv), 3-bromo-2,2-dimethylpropan-1-ol (1 equiv) and water (5 mL) were added, and the resulting mixture was stirred at 130° C. for 10 hours. The incomplete reaction mixture was diluted with water and extracted with ethyl acetate. dry (MgSO 4 ) organics, filtered and evaporated to give crude product. The crude product was dissolved in NMP (20ml) and treated with cesium carbonate (7.27g) and 3-bromo-2,2-dimethylpropan-1-ol (2.75ml) and ...

Embodiment 3

[0547] N-cyclopropyl-3-fluoro-5-(4-(((3S)-3-(hydroxymethyl)piperazin-1-yl)methyl)-2-(3-hydroxypropyl)-1 -Oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

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Abstract

The present invention relates to isoquinoline derivatives of formula (I): wherein are as herein defined; processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

Description

technical field [0001] The present invention relates to isoquinolinone derivatives, processes for their preparation, pharmaceutical compositions containing them and their use in therapy. Background technique [0002] The essential function of the lung requires a delicate structure to be exposed extensively to the environment including pollutants, microorganisms, allergens and carcinogens. Host factors arising from the interplay of lifestyle choices and genetic makeup influence the response to this exposure. Injury or infection to the lungs can produce a wide range of respiratory disorders (respiratory diseases). Many of these diseases are of enormous public health importance. Respiratory diseases include acute lung injury, acute respiratory distress syndrome (ARDS), occupational lung disease, lung cancer, tuberculosis, fibrosis, pneumoconiosis, pneumonia, emphysema, chronic obstructive pulmonary disease (COPD), and asthma. [0003] The most common respiratory disease is a...

Claims

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Application Information

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IPC IPC(8): C07D401/06A61K31/472A61K31/4725A61K31/496A61K31/55A61P11/06C07D217/24
CPCC07D217/24C07D401/06C07D401/12A61P1/00A61P1/04A61P1/18A61P11/00A61P11/02A61P11/06A61P11/08A61P11/16A61P13/00A61P13/02A61P13/10A61P17/00A61P17/04A61P17/06A61P17/14A61P19/00A61P19/02A61P19/06A61P19/08A61P19/10A61P21/00A61P25/04A61P25/28A61P27/02A61P31/04A61P31/08A61P31/12A61P31/16A61P31/18A61P35/00A61P35/02A61P3/06A61P37/00A61P37/06A61P43/00A61P9/00A61P9/10A61P3/10A61K31/4725
Inventor 斯蒂芬.J.布拉夫蒂莫西.J.卢克布赖恩.G.罗伯茨斯蒂芬.A.圣-加莱
Owner ASTRAZENECA AB
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