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Quinolyl amide derivative and its prepn process and use

A quinoline and amide technology, applied in the field of 4-hydroxy-quinoline-3-amide compounds, can solve problems such as treating symptoms but not root causes

Inactive Publication Date: 2006-10-18
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Immunodeficiency can induce autoimmunity through a variety of ways, among which persistent infection caused by inability to effectively clear antigens due to immunodeficiency is the most important reason, and various immunodeficiencies are directly related to autoimmune diseases. From this point of view, The use of immunosuppressants to treat autoimmune diseases is to treat the symptoms but not the root cause. Long-term use will have great side effects. Only by adjusting the imbalanced immune system to normal is the method to treat both the symptoms and the root causes of autoimmune diseases

Method used

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  • Quinolyl amide derivative and its prepn process and use
  • Quinolyl amide derivative and its prepn process and use
  • Quinolyl amide derivative and its prepn process and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0191] Embodiment 1: the synthesis of N-(3-chlorophenyl)-4-hydroxyl-7-chloro-quinoline-3-amide

[0192] 1.1 Synthesis of 3-chloroanilinodiethylmethylenemalonate: Mix 7.00 grams (0.055mol) of m-chloroaniline and 12.00 grams (0.056mol) of ethoxydiethylmethylenemalonate, add 50ml of toluene , heated to about 100°C, reacted for 5 hours, and evaporated the solvent under reduced pressure to obtain a white wax, white needle-like crystals recrystallized from petroleum ether, weighing 14.20 g, m.p.56-57°C, yield 87.0%.

[0193] 1.2 Synthesis of ethyl 4-hydroxy-7-chloro-quinoline-3-carboxylate: 14.20 grams (0.048mol) of diethyl 3-chloroanilinomethylidenemalonate was dissolved in 100ml of diphenyl ether and heated to React for 0.5 hours at about 250°C, stop heating, cool to room temperature, precipitate solid, filter the solid, wash with petroleum ether, absolute ethanol, and anhydrous ether to obtain a white solid weighing 10.50 g, m.p.>300°C, collected The rate is 87.5%.

[0194] 1.3...

Embodiment 2

[0195] Example 2: N-methyl-N-phenyl-4-hydroxyl-7-chloro-quinoline-3-amide

[0196] The compound was prepared according to the method 1.3 in Example 1, and the substituted amine used was N-methylaniline. m.p.276-278°C, yield 41.1%. 1 HNMR (DMSO-d 6 , δ): 11.91 (s, 1H, OH), 8.04 (d, 1H, J=5.9Hz), 7.96 (d, 1H, J=8.8Hz), 7.51 (d, 1H, J=1.7Hz), 7.20 -7.30 (m, 5H), 7.10 (t, 1H, J=7.0Hz), 3.37 (s, 3H).

Embodiment 3

[0197] Example 3: N-phenyl-4-hydroxy-7-chloro-quinoline-3-amide

[0198] The compound was prepared according to the method 1.3 in Example 1, and the amine used was aniline. m.p.>300°C, yield 88.7%. 1 HNMR (DMSO-d 6 , δ): 12.89(S, 1H), 12.29(S, 1H), 8.86(S, 1H), 8.34(d, 1H, J=8.7Hz), 7.3-7.8(m, 6H), 7.14(t, 1H, J=7.3Hz).

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Abstract

The present invention relates to quinolyl amide derivatives, their preparation process, medicine compositions and use in preparing medicines for treating and / or preventing chronic nephritis, rheumarthritis, insulin dependent diabetes mellitus, systemic lupus erythematous, multiple sclerosis and other diseases.

Description

technical field [0001] The present invention relates to 4-hydroxy-quinoline-3-amide compounds, their preparation methods, pharmaceutical compositions containing them and the preparation of said compounds for the treatment and / or prevention of chronic nephritis, rheumatoid arthritis, insulin-dependent diabetes mellitus, Use of drugs for diseases such as systemic lupus erythematosus and multiple sclerosis. Background technique [0002] Chronic nephritis is a class of diseases that seriously threaten human health, often leading to renal failure and endangering the lives of patients. At present, the pathogenesis of chronic nephritis is not very clear. It is generally believed to be related to immune dysfunction and belongs to autoimmune disease. There is no specific drug for its treatment. At present, hormonal drugs (cortisone, prednisone, corticosterone, cortisol, etc.) and immunosuppressive drugs (cyclosporin A, cyclophosphyl, FK506, etc.) The above-mentioned drugs need to b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/56A61K31/47A61K31/5355A61P3/10A61P13/12A61P19/02A61P29/00A61P37/02
Inventor 恽榴红贺俊峰杨日芳肖智勇周文霞程军平张永祥
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A