Amino thiazole derivative and preparation method and medical purpose thereof

A technology of aminothiazole and derivatives, applied in the field of medicine, can solve problems such as difficult to cure neurodegenerative diseases

Inactive Publication Date: 2012-02-15
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The drugs currently used in the treatment of AD are mostly symptom-improving

Method used

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  • Amino thiazole derivative and preparation method and medical purpose thereof
  • Amino thiazole derivative and preparation method and medical purpose thereof
  • Amino thiazole derivative and preparation method and medical purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 2-(Ethyl(4-(1,2,3,4-tetrahydro-acridin-9-amino)butyl)amino)-N-(4-phenylthiazol-2-yl)acetamide preparation of

[0043]

[0044] Reagents: 2-bromo-N-(4-phenylthiazol-2-yl)acetamide (0.4 g, 1.57 mmol), DMF (10 mL), potassium carbonate (0.26 g), potassium iodide (0.136 g), and N- (4-(Ethylamino)butyl)-1,2,3,4-tetrahydroacridin-9-amine (0.5 g, 1.57 mmol). Method: Take 2-chloro-N-(4-phenylthiazol-2-yl)acetamide and N-(4-(ethylamino)butyl)-1,2,3,4-tetrahydroacridine- 9-amine was dissolved in N,N-dimethylformamide, potassium carbonate was added, and the temperature was controlled at 70°C for 2 hours. Diluted with dichloromethane, washed with water and dried, then directly purified by silica gel column chromatography. Purification method: silica gel column chromatography using petroleum ether / ethyl acetate (2:1, 0.3% triethylamine) to obtain 0.51 g of light yellow oil with a yield of 55%. h 1 NMR results are: H 1 -NMR (CDCl 3 , 400MHz, δppm): 7.92(d, J=7.6Hz, 1H), 7.91...

Embodiment 1-1

[0046] N-(4-(4-chlorophenyl)thiazol-2-yl)-2-(ethyl(4-(1,2,3,4-tetrahydro-acridin-9-amino)butyl) Preparation of amino)acetamide

[0047]

[0048] Reagents: 2-bromo-N-((4-chlorophenyl)thiazol-2-yl)acetamide (0.34 g, 117 mmol), DMF (10 mL), potassium carbonate (0.2 g), potassium iodide (0.05 g), and N-(4-(Ethylamino)butyl)-1,2,3,4-tetrahydroacridin-9-amine (0.35 g, 1.17 mmol). Except for the reagents, the rest of the preparation and purification methods were the same as in Example 1 to obtain 0.6 g of a light brown oil with a yield of 85.7%. h 1 NMR results are: H 1 -NMR (CDCl 3 , 400MHz, δppm): 7.90(d, J=7.6Hz, 1H), 7.88(d, J=7.6Hz, 1H), 7.74(d, J=8.4Hz, 2H), 7.52(m, 2H), 7.33 (d, J=8.4Hz, 2H), 7.29(m, 1H), 7.11(s, 1H), 3.47(t, J=7.2Hz, 2H), 3.27(s, 2H), 3.03(t, J= 6.0Hz, 2H), 2.66(m, 4H), 2.59(m, 2H), 1.85(m, 4H), 1.69(m, 2H), 1.59(m, 2H), 1.08(t, J=7.2Hz, 3H).C 13 NMR results are: C 13 -NMR (CDCl 3 , 100MHz, δppm): 170.1, 158.3, 157.2, 150.5, 148.9, 147.2, 133.7, ...

Embodiment 1-2

[0050] N-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(ethyl(4-(1,2,3,4-tetrahydro-acridin-9-amino)butyl base) amino) acetamide preparation

[0051]

[0052] Reagents: 2-bromo-N-((4-methoxyphenyl)thiazol-2-yl)acetamide (0.43g, 1.5mmol), DMF (10mL), potassium carbonate (0.22g), potassium iodide (0.01h ), and N-(4-(ethylamino)butyl)-1,2,3,4-tetrahydroacridin-9-amine (0.45 g, 1.5 mmol). Except for the reagents, the rest of the preparation and purification methods were the same as in Example 1 to obtain 0.35 g of a light brown oil with a yield of 43.8%. h 1 NMR results are: H 1 -NMR (CDCl 3 , 400MHz, δppm): 7.95(d, J=7.6Hz, 1H), 7.93(d, J=7.6Hz, 1H), 7.75(d, J=8.8Hz, 2H), 7.55(m, 1H), 7.34 (m, 1H), 7.02(s, 1H), 6.92(d, 2H), 3.84(s, 3H), 3.52(t, J=7.2Hz, 2H), 3.29(s, 2H), 3.07(t, J=6.0Hz, 2H), 2.68(m, 4H), 2.61(t, J=7.2Hz, 2H), 1.88(m, 4H), 1.74(m, 2H), 1.62(m, 2H), 1.11( t,J=7.2Hz,3H).C 13 NMR results are: C 13 -NMR (CDCl 3 , 100MHz, δppm): 170.0, 159.5, 158.2, 156.9, 150.7, 1...

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Abstract

The invention provides an amino thiazole derivative compound, a tautomer thereof, a medicinal salt thereof and a preparation method thereof. The amino thiazole derivative compound, the tautomer thereof, or the medicinal salt thereof provided by the invention has effects of inhibiting acetylcholinesterase and senile plaque aggregated by beta- amyloid (A beta), and can be used for treating, improving or preventing cognitive decline related neurological diseases, such as Alzheimer disease, vascular dementia, slight cognitive impairment and other dementia with oxidative stress participation.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to an aminothiazole derivative, a preparation method and a medicine application. Background technique [0002] With the aging of the world's population, the incidence of neurological diseases related to cognitive decline, especially Alzheimer's disease (AD), has increased significantly. Alzheimer's disease is a neurodegenerative disease induced by multiple factors, and its exact pathogenesis is still unclear. For this reason, research on the pathogenesis and therapeutics of Alzheimer's disease has become the focus of attention. Alzheimer's disease is a degenerative disease of the central nervous system mainly characterized by progressive cognitive impairment and learning and memory impairment. . In recent years, the medical community has put forward a variety of etiological hypotheses, mainly including the hypothesis of cholinergic function decline, the hypothesis of amyloid deposition caus...

Claims

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Application Information

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IPC IPC(8): C07D417/12A61K31/473A61P25/28
Inventor 陈建国姜凤超王芳王悦江波黄超吴鹏飞王灿明周俊关鑫磊杨远坚曾建华
Owner HUAZHONG UNIV OF SCI & TECH
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