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Benzofuran-[3,4-f] quinoline derivatives, combination containing the same and application thereof

A technology of drugs and compounds, applied in the field of inhibiting mammalian inflammation, immune and autoimmune diseases, and inflammatory diseases, and can solve problems such as no success

Inactive Publication Date: 2004-06-16
ABBOTT LAB INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Selective antagonists of the glucocorticoid receptor have been sought without success for decades

Method used

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  • Benzofuran-[3,4-f] quinoline derivatives, combination containing the same and application thereof
  • Benzofuran-[3,4-f] quinoline derivatives, combination containing the same and application thereof
  • Benzofuran-[3,4-f] quinoline derivatives, combination containing the same and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0434] 2,5-Dihydro-11-methoxy-5-phenyl-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinoline

Embodiment 1A

[0436] Methyl 2-hydroxy-3-methoxybenzoate (20.0 g, 110 mmol) in trifluoroacetic acid was treated with sodium nitrate (10.2 g, 121 mmol) in water (70 mL) over 45 minutes at 0°C (150ml) solution, stirred at 0°C for 30 minutes, and poured into ice (450ml). The precipitate was collected by filtration, washed with cold water, and dried in vacuo to give the designated compound.

[0437] MS (DCI / NH 3 )m / z 245(M+NH 4 ) + ;

[0438] 1 H NMR (300MHz, CDCl 3 )δ11.73(s, 1H), 8.45(d, J=7.8Hz, 1H), 7.87(d, J=8.2Hz, 1H), 4.04(s, 3H), 4.01(s, 3H).

Embodiment 1B

[0440] Example 1A (5.74 g, 25.3 mmol) in dichloromethane (100 ml) was treated with diisopropylethylamine (13.2 ml, 75.9 mmol) and freshly distilled trifluoroacetic anhydride ( 10.0g, 35.4mmol) was processed through the addition funnel for 30 minutes, stirred at -40°C for 15 minutes, when the initial phenol had reacted, stopped the reaction with water (30ml), stirred at 23°C until a uniform, two phase solution and treated with dichloromethane (65ml). The organic extract was washed successively with 5% hydrochloric acid, brine and saturated sodium bicarbonate, dried (sodium sulfate), filtered and concentrated. Recrystallization from hot hexanes afforded the desired compound. The residue was purified by flash chromatography using 15% ethyl acetate / hexanes to afford the desired compound, which could be stored indefinitely at -10°C under nitrogen without detectable decomposition.

[0441] mp84-86℃

[0442] MS (DCI / NH 3 )m / z377(M+NH4 ) + ;

[0443] 1 H NMR (300MHz, CDCl 3 )δ...

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PUM

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Abstract

Compounds having Formula (I) are useful for partially of fully antagonizing, repressing, agonizing, or modulating the glucocorticoid receptor in a mammal and treating immune, autoimmune and inflammatory diseases in a mammal. Also disclosed are pharmaceutical compositions comprising compounds of Formula (I) and methods of inhibiting immune or autoimmune diseases in a mammal.

Description

field of invention [0001] The present invention relates to glucocorticoid receptor selective benzopyrano[3,4-f]quinolines for the treatment of immune or autoimmune diseases, to pharmaceutical compositions containing these compounds, and to inhibitory Approaches to Inflammation, Inflammatory Diseases, Immunity and Autoimmune Diseases. Background of the invention [0002] Intracellular receptors (IR's) are a class of structurally related proteins involved in the regulation of gene expression. Steroid hormone receptors are a subtype of this superfamily, and their natural ligands generally consist of endogenous steroids such as estradiol, progesterone, and cortisol. Artificial ligands for these receptors play important roles in human health, and among these receptors the glucocorticoid receptor (GR) plays a crucial role in regulating human physiological and immune responses. Steroids that have been shown to interact with GR are potent anti-inflammatory agents. Despite these a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/4741A61P29/00A61P37/02A61P43/00C07D491/04C07D491/052
CPCC07D491/04A61P29/00A61P37/02A61P43/00
Inventor M·J·库格兰M·E·科尔特J·P·爱德华斯T·K·琼斯
Owner ABBOTT LAB INC