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Isoalantolactone derivatives and their application in preparation of drugs for treating inflammatory bowel diseases

A technology of isocyanolide and inflammatory bowel disease, applied in the field of application of isocyanolide derivatives and their salts in the preparation of drugs for treating inflammatory bowel disease, can solve the problem of large gastrointestinal reactions, induced intestinal Perforation and inflammatory lesions and other problems, to achieve a significant effect of treatment

Inactive Publication Date: 2017-03-08
天承南运(天津)科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, non-steroidal anti-inflammatory drugs have large gastrointestinal reactions, which can induce clinical recessive enteropathy such as intestinal perforation and inflammatory lesions; long-term use of glucocorticoids can cause a series of immunosuppression and adrenal cortex suppression due to systemic absorption. side effect

Method used

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  • Isoalantolactone derivatives and their application in preparation of drugs for treating inflammatory bowel diseases
  • Isoalantolactone derivatives and their application in preparation of drugs for treating inflammatory bowel diseases
  • Isoalantolactone derivatives and their application in preparation of drugs for treating inflammatory bowel diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of compound (II)

[0028]

[0029] 1) Preparation of Compound (1.1)

[0030]

[0031] 1) Isoaurinolide (1.0g, 4.3mmol) was dissolved in dichloromethane (16mL), and peroxybenzoic acid (1.1g, 5.2mmol) was slowly added to the system in batches, reacted at room temperature for 3 hours, saturated The reaction was quenched with sodium thiosulfate (16 mL), extracted with dichloromethane (16 mL×3), the organic phase was washed with saturated aqueous sodium bicarbonate (16 mL), dried and concentrated, and purified by column chromatography (petroleum ether: ethyl acetate=20: 1) Obtain compound 1.2 (white solid, 984 mg, yield 92.0%).

[0032] 2) preparation of compound (I-II),

[0033]

[0034] Dissolve the compound 1.2 obtained in step 1) in dichloromethane (98mL), add potassium carbonate (16.4g, 118.9mmol) and dimethylamine hydrochloride (4.8g, 59.4mmol) to the system in turn, and stir the mixed system Reflux reaction for 3 hours, after the reaction, remo...

Embodiment 2

[0040] Preparation of compound (III)

[0041]

[0042] 1) Preparation of compound 1.3

[0043]

[0044] At 0°C, dissolve selenium dioxide (87.5mg, 0.75mmol) in dichloromethane (5mL), add tert-butanol peroxide (0.37mL), and stir for 30 minutes. , 2.15mmol) of dichloromethane (5mL) solution was slowly added to the above system, stirred at room temperature for 24 hours, quenched with saturated aqueous sodium thiosulfate (8mL), extracted with dichloromethane (8mL×3), dried Concentrate and purify by column chromatography (petroleum ether: ethyl acetate = 9:1 to 3:1) to obtain compound 1.23 (white solid, 350 mg, yield: 82.8%).

[0045] 2) Preparation of compound (I-III)

[0046]

[0047] The compound 1.3 obtained in the previous step was dissolved in dichloromethane (35mL), potassium carbonate (5.8g, 42.2mmol) and dimethylamine hydrochloride (1.7g, 21.1mmol) were added to the system successively, and the mixed system was stirred and refluxed Reacted for 3 hours. After th...

Embodiment 3

[0052] Preparation of Compound IV

[0053]

[0054] 1) Preparation of compound 1.4

[0055]

[0056] Compound 1.3 (112mg, 0.45mmol) was dissolved in dichloromethane (1mL), and a solution of peroxybenzoic acid (100mg, 0.60mmol) in dichloromethane (1mL) was slowly added dropwise to the above system, and reacted at room temperature for 2 hours , quenched the reaction with saturated sodium thiosulfate (2 mL), extracted with dichloromethane (2 mL×3), dried and concentrated, and purified by column chromatography (petroleum ether: ethyl acetate = 4:1 to 1:1) to obtain compound 1.4 ( White solid, 89 mg, yield: 74.5%).

[0057] 2) Preparation of compound (I-IV)

[0058]

[0059] The compound 1.4 obtained in the previous step was dissolved in dichloromethane (35mL), potassium carbonate (5.8g, 42.2mmol) and dimethylamine hydrochloride (1.7g, 21.1mmol) were added to the system successively, and the mixed system was stirred and refluxed Reacted for 3 hours. After the reaction, ...

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PUM

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Abstract

Isoalantolactone derivatives and their application in preparation of drugs for treating inflammatory bowel diseases are provided, and an isoalantolactone derivative shown as in formula (I) is provided; a salt-forming acid is an inorganic acid or organic acid, the inorganic acid is selected from hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid, bromic acid, seleninic acid, phosphomolybdic acid, phosphorus acid and sulfurous acid, and the organic acid is selected from citric acid, maleic acid, D-malic acid, L-malic acid, DL-malic acid, L-lactic acid, D-lactic acid, DL-acid, oxalic acid, methylsulfonic acid, pentanoic acid, oleic acid, lauric acid, p-methylbenzene sulfonic acid, 1-naphthalene sulfonic acid, 2-naphthalene sulfonic acid, phthalic acid, tartaric acid, malonic acid, succinic acid, fumaric acid, glycolic acid, mercapturic acid, glycine, creatine, sulfonic acid, nicotinic acid, picolimic acid, isonicotinic acid, and benzoic acid or substituted benzoic acid.

Description

[0001] Technical field: [0002] The present invention relates to inulin derivatives and their salts and their application and preparation. [0003] Background technique: [0004] Inula helenium is a plant of the genus Inula in the family Compositae, a perennial herb whose roots are used for medicinal purposes. It has the functions of invigorating the spleen and harmonizing the stomach, regulating qi and relieving depression, relieving pain and preventing miscarriage. It is used for chest and flank, abdominal distension and pain, vomiting and diarrhea, chest and flank contusion, pain in the chest and flank, restless fetal movement and other diseases. The volatile oil of inulin contains iso-inuricolide, iso-inuricolide and other components. Its chemical structure is similar to that of Sandonian, and it has anthelmintic effect on pigs, dogs, and cats. Its curative effect is better than that of Sandonian, and its toxicity is lower. Low. [0005] Isoacarina lactone (CAS: 470-17-7...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/365A61P1/00A61P1/04C07D307/92C07D493/10A61K9/50
CPCA61K31/365A61K9/5031A61K9/5036A61K9/5078C07D307/92C07D493/10
Inventor 杨光周红刚高晶晶尹春晓毕谆侯建楠张红丹
Owner 天承南运(天津)科技有限公司
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