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Compound and application thereof in preparation of medicines for preventing/treating autoimmune diseases

An autoimmune, compound technology, applied in the field of medicine, can solve problems such as joint destruction, deformity, affecting the quality of life of patients

Inactive Publication Date: 2018-04-06
田甜
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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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  • Compound and application thereof in preparation of medicines for preventing/treating autoimmune diseases
  • Compound and application thereof in preparation of medicines for preventing/treating autoimmune diseases
  • Compound and application thereof in preparation of medicines for preventing/treating autoimmune diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of 2,4-Dichloro-6-(cyclohexyloxy)-3-methylpyridine

[0033]

[0034] To a solution of sodium hydride NaH (4.51g, 0.188mmol, 60wt% in mineral oil) in THF (200mL) at 0°C was added cyclohexanol (15.6mL, 0.15mol) dropwise. After stirring for 30 minutes at 0°C, a solution of 2,4,6-trichloro-3-methylpyridine (Compound 1) (26.52 g, 0.135 mol) in THF (40 mL) was added dropwise via a syringe. The reaction mixture was heated 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 terminate the reaction. The reaction mixture was allowed to warm to room temperature, diluted with ethyl acetate, and washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium thiosulfate solution. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered, and conce...

Embodiment 2

[0035] Example 2: 8-Benzyl-2-(4-chloro-6-(cyclohexyloxy)-3-methylpyridin-2-yl)-2,8-diazaspiro[4.5]decane synthesis:

[0036]

[0037] A 2L three-necked flask equipped with a mechanical stirrer, thermometer and dropping funnel was filled with ethanol (375mL), water (375mL) and 8-benzyl-2,8-diazaspiro[4.5]decane (34.55) g, 0.15 mol), cool the resulting solution (using an ice-salt bath) to about 0°C, and add a solution of compound 2 (33.37 g, 0.128 mol) in ethyl acetate (47.5 mL) dropwise in about 20 minutes. Keep the temperature below 10°C. The dropping funnel was rinsed twice with ethyl acetate (20 mL), and the rinse was transferred to the reaction mixture. Check the reaction by TLC to determine when the reaction is complete. After the reaction was completed, ice water (375 mL) was added and stirred for 30 minutes to complete the precipitation. The white solid was filtered out, washed 3 times with water (225mL each time), and dried under vacuum at 40-50°C until constant weight...

Embodiment 3

[0038] Example 3: 8-benzyl 2-(6-(cyclohexyloxy)-4-hydrazino-3-methylpyridin-2-yl)-2,8-diazaspiro[4.5]decane synthesis

[0039]

[0040] Under nitrogen purge, a suspension of compound 3 (50.00g, 0.110mol) synthesized in Example 2 and hydrazine monohydrate (7.51g, 0.15mol) in dioxane (255mL) was boiled and refluxed for 5.5 hour. Ice water (400 mL) was added to the reaction mixture and left to stand overnight. The resulting precipitate was filtered, washed 3 times with water (260 mL each time), and dried under vacuum at 40-50°C until constant weight to obtain 8-benzyl 2-(6-(cyclohexyloxy)-4-hydrazino -3-methylpyridin-2-yl)-2,8-diazaspiro[4.5]decane (compound 4), 35.61 g, yield 72%. 1 H-NMR (400 MHz, CDCl 3 ) δ: 1.08-1.37(m,9H), 1.53-1.69(m, 5H), 1.89(s, 1H), 1.94(m, 2H), 1.99(s, 1H), 2.20(s, 1H), 2.40 (s, 1H), 2.36-2.56(m, 4H), 3.44(t, 2H), 3.66(s, 2H), 3.69(s, 1H), 3.77(s,1H), 4.23(m, 1H), 5.21(s, 1H), 7.18-7.32(m, 5H). 13 C-NMR (125 MHz, CDCl 3 ) δ: 11.50, 24.60, 25.92, 30.44,...

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PUM

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Abstract

The invention discloses a compound formula (I), wherein R is selected from or. The compound formula (I) of the present invention can inhibit the production of IL-12 in vitro, has an inhibitory effect on the proliferation of HaCat cells, and exhibits excellent activity in the SD rat collagen-induced rheumatoid arthritis model. It shows that the compound formula (I) of the present invention can be used as a candidate drug for the prevention / treatment of autoimmune diseases for further research and development.

Description

Technical field [0001] The invention belongs to the field of medicine, and relates to a compound and its use in preparing medicines for treating autoimmune diseases. Background technique [0002] Autoimmune disease is a type of disease caused by the body's immune response to self-antigens and damage to its own tissues. At present, the research on IL-12 family at home and abroad mainly focuses on autoimmune diseases, such as multiple sclerosis (MS), inflammatory bowel disease (IBD), rheumatoid arthritis (Rheumatoid Arthritis, RA). ), psoriasis (psoriasis), etc. [0003] Rheumatoid arthritis is an autoimmune disease dominated by chronic inflammation of the synovial membrane of the joints, which can cause joint swelling and pain, which in turn leads to cartilage destruction, joint deformities, and eventually various degrees of disability. If proper treatment is not given, it usually leads to joint destruction and deformity, and affects the patient's quality of life. [0004] Psoriasi...

Claims

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Application Information

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IPC IPC(8): C07D471/10A61P37/02A61P1/00A61P29/00A61P19/02A61P17/06
CPCC07D471/10
Inventor 田甜陆超王灵玺
Owner 田甜
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