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Aryl pyridine compounds and medicament uses thereof

A compound and aryl technology, applied in the field of 6-aryl-3-substituted-pyridone derivatives and their preparation, can solve the problems of weakened signal transmission, decreased concentration of acetylcholine, disordered synthesis and secretion of acetylcholine, etc.

Inactive Publication Date: 2008-09-03
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the cholinergic model of AD, the main defect is the disorder of acetylcholine synthesis and secretion, and the catabolism of acetylcholine decomposing neurotransmitters is not affected, resulting in a large decrease in the concentration of acetylcholine in the cholinergic synaptic cleft, and to the cerebral cortex. The transmitted signal then weakens

Method used

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  • Aryl pyridine compounds and medicament uses thereof
  • Aryl pyridine compounds and medicament uses thereof
  • Aryl pyridine compounds and medicament uses thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0044] Preparation example 1: Preparation of starting compound IIa (p-methoxyacetophenone):

[0045] Compound IIa

[0046] Methoxybenzene (10.8 g, 0.1 mol) was dissolved in 150 ml of dichloromethane, then anhydrous zinc chloride powder (26.8 g, 0.20 mol) was added, and acetic anhydride (15.3 g, 0.15 moles); after the dropwise addition, the reaction was slowly raised to room temperature for 7 hours, then the reactant was carefully poured into 600 ml of ice water, and extracted 3 times with ethyl acetate; the organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated The crude product was obtained as a colorless oil, and the starting compound IIa (p-methoxyacetophenone) (13.1 g, yield 87%) was obtained by short silica gel column chromatography. White solid, melting point: 35-38°C. H NMR spectrum 1 H-NMR (400MHz, deuterated chloroform, δppm) 2.56 (single peak, 3H, COCH 3 ), 3.87 (single peak, 3H, OCH 3 ), 6.93 (doublet, 2H, J=8.4Hz, H-3,5), 7.94 (...

preparation example 2

[0047] Preparation example 2: Preparation of starting compound IIb (m-methoxyacetophenone):

[0048] Compound IIb

[0049] 3-Hydroxyacetophenone (13.6 grams, 0.1 moles) was dissolved in 150 milliliters of acetone, 20 grams of potassium carbonate (0.15 moles) and dimethyl sulfate (12.6 grams, 0.1 moles) were added; reflux reaction for 10 hours, TLC showed After the reaction was complete, filter, wash the filter cake with ethyl acetate, and concentrate to obtain a crude brown oil, which was subjected to short silica gel column chromatography to obtain Compound IIb (m-methoxyacetophenone), 12.1 g, with a yield of 81%. Colorless oil.

preparation example 3

[0050] Preparation example 3: Preparation of intermediate compound IIIa [3-cyano-6-(4-methoxyphenyl)-2H-pyridin-2-one]:

[0051] Compound IIIa

[0052] Sodium metal (2.76 g, 120 mmol) was added in 250 ml of ether, 1 ml of ethanol was added dropwise, compound IIa (p-methoxyacetophenone) (100 mmol) and ethyl formate ( 150 mmol) mixture, after the dropwise addition, the mixture was stirred for 15 minutes, then warmed up to room temperature and reacted for 1 hour, after diethyl ether was distilled off under reduced pressure, cyanoacetamide (12.6 grams, 150 mmol) and water (400 mmol) were added to the solid mixture. ml). After the mixture was refluxed for 8 hours, cooled, acidified with acetic acid, filtered to obtain a yellow solid, after drying, the initial product was recrystallized from ethanol to obtain intermediate compound IIIa[3-cyano-6-(4-methoxyphenyl) -2H-pyridin-2-one]: yield 56%, light yellow solid; melting point > 250 ° C; R f (Dichloromethane / methanol 20:1) 0....

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Abstract

The invention relates to medicinal chemistry field, more particularly, 6-aryl-3-substituted pyridone derivates with the structure represented by the formula (I) and the pharmaceutical salt thereof, and the invention further relates to a method for preparing the compounds with the structure of the formula I and the pharmaceutical use thereof. The compounds of the invention have the pharmaceutical uses for inhibiting the activity of acetylcholine esterase and preventing and curing senile dementia.

Description

technical field [0001] The invention belongs to the fields of organic chemistry, medicinal chemistry and pharmacology. Specifically, the invention relates to 6-aryl-3-substituted-pyridone derivatives capable of preventing and treating senile dementia, their preparation method and application. The pharmacological activity test shows that the compound has the activity of inhibiting acetylcholinesterase, and can be expected to be used as a medicine for preventing and treating senile dementia. Background technique [0002] Studies at home and abroad suggest that with the increase of age, the incidence of senile dementia will gradually increase, and the incidence of dementia in the elderly over 80 years old can reach 80%. Alzheimer's disease has become the fourth cause of death after heart disease, malignancy and stroke. At present, the elderly over 60 years old in my country has reached 120 million, and there are about 5 million senile dementia patients. Therefore, researching...

Claims

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Application Information

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IPC IPC(8): C07D213/82C07D401/06C07D491/10A61K31/5377A61K31/496A61K31/44A61P25/28
Inventor 李校堃阳应华敖雷蒋翔锐董盛谊韩方方黄可新郝小江赵昱白骅瞿佳
Owner WENZHOU MEDICAL UNIV
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