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A compound and its application in preparation of medicine for treating rheumatoid arthritis

A rheumatoid, compound technology, applied in the field of medicine, can solve problems such as affecting the quality of life of patients, joint destruction, deformity, etc.

Inactive Publication Date: 2018-11-13
THE AFFILIATED HOSPITAL OF QINGDAO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If not treated properly, often results in joint destruction and deformity and affects the patient's quality of life

Method used

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  • A compound and its application in preparation of medicine for treating rheumatoid arthritis
  • A compound and its application in preparation of medicine for treating rheumatoid arthritis
  • A compound and its application in preparation of medicine for treating rheumatoid arthritis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Synthesis of 2,4-dichloro-6-(cyclohexyloxy)-3-methylpyridine

[0030]

[0031] To a solution of sodium hydride NaH (4.51 g, 0.188 mmol, 60 wt % in mineral oil) in THF (200 mL) was added cyclohexanol (15.6 mL, 0.15 mol) dropwise at 0 °C. After stirring at 0°C for 30 minutes, a THF (40 mL) solution of 2,4,6-trichloro-3-methylpyridine (Compound 1) (26.52 g, 0.135 mol) was added dropwise via syringe. The reaction mixture was warmed to room temperature and stirred for 4 hours. The reaction was cooled to 0°C, and saturated aqueous ammonium chloride solution was slowly added to quench the reaction. The reaction mixture was allowed to warm to room temperature, diluted with ethyl acetate, and washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium thiosulfate. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. P...

Embodiment 2

[0032] Example 2: Synthesis of 4-chloro-6-(cyclohexyloxy)-3-methyl-2-(4-propylpiperazin-1-yl)pyridine

[0033]

[0034]Ethanol (375 mL), water (375 mL) and 4-propylpiperidine (19.08 g, 0.15 mol) were charged into a 2 L three-necked flask equipped with a mechanical stirrer, a thermometer and a dropping funnel, and the resulting solution was cooled (with ice-salt bath) to about 0°C, and a solution of 2,4-dichloro-6-(cyclohexyloxy)-3-methylpyridine (26.02g, 0.10mol) in ethyl acetate (37.5mL) was dissolved in about Add dropwise within 20 minutes, keeping the temperature below 10°C. The dropping funnel was rinsed twice with ethyl acetate (15 mL), and the rinses were transferred to the reaction mixture. The reaction was checked by TLC to determine when the reaction was complete. After the reaction, ice water (375 mL) was added and stirred for 30 minutes to complete the precipitation. The white solid was filtered off, washed 6 times with water (225 mL for each wash), and dried ...

Embodiment 3

[0035] Example 3: Synthesis of 6-(cyclohexyloxy)-4-hydrazino-3-methyl-2-(4-propylpiperazin-1-yl)pyridine

[0036]

[0037] Under nitrogen purging, the 4-chloro-6-(cyclohexyloxy)-3-methyl-2-(4-propylpiperazin-1-yl)pyridine (30.00g, 0.085mol) and hydrazine monohydrate (6.00g, 0.10mol) in dioxane (225mL) was boiled and refluxed for 5 hours. Ice water (400 mL) was added to the reaction mixture and left overnight. The resulting precipitate was filtered off, washed 3 times with water (260 mL each), and dried under vacuum at 40-50 °C until constant weight to give 6-(cyclohexyloxy)-4-hydrazino-3-methyl-2 -(4-Propylpiperazin-1-yl)pyridine, 18.26 g, 62% yield. 1 H-NMR (400 MHz, CDCl3)δ: 0.89(t, 3H), 1.13-1.41(m, 12H), 1.61-1.76(m, 7H), 1.90-1.98(m, 3H), 2.40(s, 3H) ), 3.20-3.30(m, 2H), 3.37-3.46(m, 2H),4.19(m, 1H), 5.21(s, 1H). 13 C-NMR(125 MHz, CDCl3) δ: 11.50, 14.20, 20.79, 24.60, 25.92, 30.44, 31.06, 35.70,36.20, 47.28, 76.82, 85.95, 109.94, 147.44, 164.IOS. ,ion) m / z: 347[M+...

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PUM

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Abstract

The invention discloses a compound shown in a formula (I) (described in the specification), wherein R is selected from two groups (described in the specification). The compound shown in the formula (I) can inhibit production of IL-12 in vitro and shows excellent activity in an SD rat collagen-induced rheumatoid arthritis model. Therefore, the compound shown in the formula (I) can be researched anddeveloped more deeply as a candidate drug for preparation of medicines used for preventing and / or treating rheumatoid arthritis.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a compound and its application in preparing medicine for treating rheumatoid arthritis. Background technique [0002] Rheumatoid arthritis is an autoimmune disease mainly characterized by chronic inflammation of the synovium of the joints, which can cause joint swelling and pain, and then lead to cartilage destruction, joint deformity, and eventually disability of varying degrees. If not treated properly, it often results in joint destruction and deformity, and affects the patient's quality of life. [0003] IL-12 is a cell inflammatory factor discovered in recent years. It is mainly produced by T, B lymphocytes and monocyte-macrophages. Synthesis of IL-11, etc., and is essential for TH 1 differentiation of TH precursor cells. IL-12 can also directly promote the proliferation and differentiation of B lymphocytes, secrete autoantibodies, and induce autoimmune diseases. IL-12 is a p70 heter...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04A61P19/02
CPCC07D401/04
Inventor 马进峰臧瓅娜吕江涛田甜陆超王灵玺
Owner THE AFFILIATED HOSPITAL OF QINGDAO UNIV
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