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N-phenyl-n-quinoline carboxylic acid compound and its preparation method and medicinal use

The technology of a quinoline carboxylic acid and a compound is applied in the field of drugs related to the treatment of hyperuricemia and gout, and can solve the problems of liver and bone marrow toxicity and allergy, fulminant hepatitis, and limited clinical application.

Active Publication Date: 2022-03-15
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have different degrees of toxic and side effects, such as benzbromarone has the risk of causing fulminant hepatitis, allopurinol has adverse reactions such as liver and bone marrow toxicity and allergic reactions, probenecid and non-steroidal anti-inflammatory drugs, penicillin, etc. Drug interactions also limit its clinical application

Method used

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  • N-phenyl-n-quinoline carboxylic acid compound and its preparation method and medicinal use
  • N-phenyl-n-quinoline carboxylic acid compound and its preparation method and medicinal use
  • N-phenyl-n-quinoline carboxylic acid compound and its preparation method and medicinal use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047]

[0048] Reagents and conditions: a) potassium carbonate, potassium iodide, 80°C; b) palladium acetate, cesium carbonate, 4,5-bisdiphenylphosphine-9,9-dimethylxanthene, 110°C, N 2 ; c) sodium hydroxide, ethanol, 50 ℃

[0049] A. Synthesis of Compound IV-1

[0050] Dissolve compound II-1 (1.1g, 10mmol), compound III-1 (1.5g, 10mmol) in 20mL DMF, add potassium carbonate (2.8g, 20mmol), potassium iodide (332mg, 0.2mmol), react at 85°C for 10h . After the TLC monitoring reaction was complete, most of the DMF was evaporated, ethyl acetate and water were added for extraction, the organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated for column chromatography separation (petroleum ether-ethyl acetate 10:1-6: 1) to obtain compound IV-1, 1.44 g of light yellow oil, yield: 80%. HR-ESI-MS: m / z=179.0974[M+H]+, calculated for C 10 h 12 FN 2 :179.0979.

[0051] B. Synthesis of Compound VI-1

[0052] To compound IV-1 (128mg, 0.7mmol), compoun...

Embodiment 2～19

[0056] Examples 2-19 were prepared according to the synthesis method of Example 1.

Embodiment 2

[0057] Example 2: The synthesis method is similar to Example 1, except that in the first step, m-chloroaniline is used instead of m-fluoroaniline, and the yield is 70%.

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Abstract

The invention discloses N-phenyl-N-quinoline carboxylic acid compounds shown in the compound of formula I and physiologically acceptable salts thereof, pharmaceutical preparations containing the compounds, and preparations of the compounds for the prevention or treatment of high Application in uric acidemia and gout.

Description

technical field [0001] The invention relates to the field of drugs related to the treatment of hyperuricemia and gout. Specifically, the present invention relates to a novel N-phenyl-N-quinoline carboxylic acid compound having a therapeutic effect on hyperuricemia and gout, a preparation method, a pharmaceutical composition containing them and a medical application. Background technique [0002] It is estimated that there are more than 20 million gout patients worldwide. Gout is a chronic metabolic disease characterized by pain caused by hyperuricemia and deposition of monosodium urate (MSU) in joints and other parts. Studies have found that hyperuricemia is the most important biochemical basis for the pathogenesis of gout. Drugs currently used to treat gout include anti-inflammatory drugs for pain relief (such as colchicine, etc.), drugs that inhibit uric acid production (xanthine oxidase inhibitors represented by allopurinol and febuxostat), uric acid Excretion drugs (u...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/44A61K31/4706A61P19/06
CPCC07D215/44A61P19/06
Inventor 肖志艳杨颖杨亚军邵蒙杰叶菲田金英李雪晨
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI