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A kind of medicine for treating thyroiditis and preparation method thereof

A technology of pharmacy and compounds, applied in the field of medicine, can solve problems such as restricting iodine intake

Inactive Publication Date: 2019-01-29
佳木斯大学附属第一医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(2) Limit iodine intake

Method used

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  • A kind of medicine for treating thyroiditis and preparation method thereof
  • A kind of medicine for treating thyroiditis and preparation method thereof
  • A kind of medicine for treating thyroiditis and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: 1-(2-methylthiazo[5,4-b]pyridin-5-yl)-3-(3-(1,2,3,4-tetrahydroacridin-9-ylamino) Propyl)urea (Compound 1)

[0060]

[0061] Heat the mixed solution of 4.34g of 9-chloro-1,2,3,4-tetrahydroacridine, 2.00g of 1,3-propylenediamine and 20ml of n-pentanol to 145°C to react under reflux 15h, cooled to room temperature, most of the solvent was removed by rotary evaporation, the residue was neutralized to weak alkalinity with saturated sodium bicarbonate solution and then washed with CH 2 Cl 2 Extract, combine the organic phases, wash the organic layer with water and saturated brine successively, dry over anhydrous sodium sulfate, filter and concentrate, the obtained residue is separated and purified by silica gel column chromatography (ethyl acetate:cyclohexane=1:1) to obtain the intermediate N 1 -(1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine 4.29g, yield 84.1%. ESI-MS[M+H] + = 256.17.

[0062] N under nitrogen 1 -(1,2,3,4-tetrahydroacridin-9-yl)propa...

Embodiment 2

[0066] Example 2: 1-(2-Butylbenzo[d]thiazol-6-yl)-3-(3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl) Urea (compound 2)

[0067]

[0068] N under nitrogen 1 -(1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine 2.55g was dissolved in 100ml of dichloromethane, stirred for 10 minutes, slowly added dropwise 2.29g of 2-butyl - A solution of 6-isocyanate benzo[d]thiazole dissolved in 100ml of dichloromethane, continue to stir for 20 minutes, slowly add dropwise a solution of 5ml triethylamine dissolved in 20ml of dichloromethane, after the dropwise addition, react at 30°C for 5h. The reaction solution was stirred with 200ml of water, the organic phase was washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and the concentrated solution was recrystallized with chloroform to obtain 3.82g of white crystals with a yield of 78.4%.

[0069] ESI-MS[M+H] + =488.24

[0070] Elemental analysis: theoretical value / measured value, C(68.96 / 68.89),...

Embodiment 3

[0072] Example 3: 1-(Benzo[d]thiazol-6-yl)-3-(3-(6-(pyrrolidin-1-yl)-1,2,3,4-tetrahydroacridine-9 -ylamino)propyl)urea (compound 3)

[0073]

[0074] Using a method similar to Example 1, replace 9-chloro-1,2,3,4-tetrahydroacridine with 6-(pyrrolidin-1-yl)-9-chloro-1,2,3,4-tetrahydroacridine Hydroacridine, substituting 6-isocyanate benzo[d]thiazole for 5-isocyanate-2-methylthiazo[5,4-b]pyridine afforded the title compound in 65.2% yield

[0075] ESI-MS[M+H] + =501.24[M+H] +

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PUM

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Abstract

The invention relates to a compound with a therapeutic effect for thyroiditis, a stereoisomer, prodrug or pharmaceutically acceptable salt, pharmaceutical composition, preparation method and application of the compound. Experimental results show that the compound provided by the invention can improve the situation that the weight of mice with hashimoto thyroiditis induced by the high-iodine waterdescends obviously, and thyroid peroxidase antibodies (TPOAb) and thyroglobulin antibodies (TGAb) increase greatly; and the experimental results show that the compound provided by the invention has good therapeutic effect on thyroiditis, particularly hashimoto thyroiditis. The therapeutic effect of the compound provided with the invention is even more remarkable compared with the therapeutic effect of a positive control dexamethasone. Therefore, the compound provided by the invention is suitable for being used as a medicine for treating thyroiditis, particularly hashimoto thyroiditis.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular, the present invention relates to a compound with therapeutic effect on thyroiditis, its stereoisomer, prodrug or pharmaceutically acceptable salt, its pharmaceutical composition, preparation method and application. Background technique [0002] Autoimmune thyroiditis (AIT), also known as Hashimoto's thyroiditis, or chronic lymphocytic thyroiditis, is the most common thyroid inflammatory disease and is one of the important causes of hypothyroidism. The clinical manifestations are diffuse lymphocytic infiltration, fibrosis, interstitial atrophy, and eosinophilic changes in acinar cells in the thyroid gland. It may be accompanied by hyperthyroidism or normal thyroid function in the early stage, and hypothyroidism in the later stage. It may also be accompanied by nodules, Those with thyroid cancer. The global incidence of AIT is 0.3-1.5 cases per 1000 people, and the incidenc...

Claims

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Application Information

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IPC IPC(8): C07D513/04C07D417/12A61K31/473A61P5/14A61P29/00
CPCC07D417/12C07D513/04
Inventor 曲义坤魏微微胡明刘隽东徐建博
Owner 佳木斯大学附属第一医院
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