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Aza (oxa)-cyclopentane-2- ketone (thione) compounds, medicine compositions thereof, preparation method and applications

A compound and cycloalkyl technology, applied in the field of pharmacy, can solve problems such as drug resistance, many side effects, and ineffective hypoglycemic effect

Active Publication Date: 2014-03-12
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the existing drugs and their corresponding targets have their shortcomings, such as high toxicity, many side effects, ineffective hypoglycemic effect, and easy drug resistance. Therefore, it is urgent to develop new drugs for the treatment of diabetes.

Method used

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  • Aza (oxa)-cyclopentane-2- ketone (thione) compounds, medicine compositions thereof, preparation method and applications
  • Aza (oxa)-cyclopentane-2- ketone (thione) compounds, medicine compositions thereof, preparation method and applications
  • Aza (oxa)-cyclopentane-2- ketone (thione) compounds, medicine compositions thereof, preparation method and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1: Preparation of important intermediate (S)-4(3,4-dimethoxybenzyl)oxazolidin-2-one

[0091]

[0092] Weigh levodopa 1a (purchased from Anaiji Chemical, 5.00g, 25.3mmol) and dissolve it in dioxane / water (50%, 80ml), add triethylamine (4.24ml, 30.4mmol), 0°C Di-tert-butyl dicarboxylate (6.64g, 30.4mmol) was added in batches, the reaction solution was stirred at this temperature for half an hour, and stirred at room temperature for 18h. After TLC detected that the reaction was complete, the solvent was vacuum-dried, and 30ml of water and 30ml of Ethyl acetate, acidified with 2M hydrochloric acid to pH = 1, separated, and extracted three times with ethyl acetate (20ml), combined organic phases, washed with saturated brine (3×20ml), dried over anhydrous sodium sulfate, filtered, vacuum The solvent was drained to give the crude product 2a. The crude product 2a was dissolved in acetone (50ml), potassium carbonate (12.25g, 88.0mmol) and dimethyl sulfate (8.15ml, 86...

Embodiment 2

[0095] Example 2: Preparation of (S)-4(3,4-dimethoxybenzyl)-3(3-methoxybenzyl)oxazolidin-2-one (yhhu3000)

[0096]

[0097] Weigh 5a (100mg, 0.42mmol) in a 10ml round bottom flask, add 3ml THF, slowly add 60% sodium hydride (34mg, 0.84mmol), add m-methoxybenzyl bromide (with m-methoxybenzaldehyde and boron Sodium hydride was reacted to obtain methoxybenzyl alcohol, which was then reacted with phosphorus tribromide, the same below) (93mg, 0.46mmol), reacted at room temperature overnight, and TLC detected that the reaction was complete, adding 3ml of water to extract it, and ethyl acetate ( 3×10ml) extraction, combined organic phases, dried over anhydrous sodium sulfate, dried the solvent under reduced pressure, column chromatography (petroleum ether / ethyl acetate=2:1), and obtained the target (S)-4(3,4 -dimethoxybenzyl)-3(3-methoxybenzyl)oxazolidin-2-one (112 mg, 75%). 1 H NMR (300MHz, CDCl 3 )δ7.25(dd,J=9.0,6.7Hz,1H),6.85-6.70(m,4H),6.60(d,J=8.1Hz,1H),6.49(s,1H),4.79(d,J ...

Embodiment 3

[0098] Example 3: Preparation of (S)-4(3,4-dimethoxybenzyl)-3(3-benzyloxybenzyl)oxazolidin-2-one (yhhu3001)

[0099]

[0100] In addition to replacing m-methoxybenzyl bromide with 3-benzyloxybenzyl bromide, compound (S)-4(3,4-dimethoxybenzyl)-3 was obtained according to a method similar to that shown in Example 2 (3-Benzyloxybenzyl)oxazolidin-2-one. 1 H NMR (300MHz, CDCl3) δ7.50–7.25(m,5H),6.93(d,J=8.5Hz,1H),6.90–6.80(m,2H),6.77(d,J=8.1Hz,1H) ,6.59(d,J=8.1Hz,1H),6.48(s,1H),5.05(s,2H),4.80(d,J=15.2Hz,1H),4.16-3.95(m,3H),3.84( s, 3H), 3.78 (s, 3H), 3.80–3.70 (m, 1H), 2.98 (dd, J=13.7, 5.0Hz, 1H), 2.55 (dd, J=13.9, 8.5Hz, 1H).

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Abstract

The invention belongs to the field of pharmacology, and relates to aza (oxa)-cyclopentane-2- ketone (thione) compounds shown in the formula I, medicine compositions thereof, a preparation method, applications in preparation of medicines treating diabetes and glucolipid metabolism, and especially applications in preparation of medicines treating II-type diabetes.

Description

technical field [0001] The invention belongs to the field of pharmacy, and specifically relates to a class of nitrogen (oxygen) oxolane-2-one (thione) compounds and pharmaceutically acceptable salts thereof, pharmaceutical compositions, preparation methods thereof, and their use in The use in the preparation of medicines for treating diabetes and glucose and lipid metabolism disorders, especially the preparation of medicines for treating type II diabetes. The above-mentioned compound has obvious functions of lowering blood sugar and regulating glucose and lipid metabolism activity. Background technique [0002] Compounds with oxazolidin-2-one and pyrrolidin-2-one as the core and their derivatives are an important class of synthons, which widely exist in a variety of reactions. However, there are only a small amount of literature and patent reports on the biological activity of this type of compound and its derivatives. According to the obtained literature reports, it can be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/24C07D413/06C07D263/56C07D263/57C07D263/16C07D207/27C07D405/06C07D403/06C07D207/24A61K31/421A61K31/422A61K31/5377A61K31/423A61K31/4015A61K31/4025A61K31/404A61P3/10
CPCC07D207/24C07D207/26C07D263/16C07D263/24C07D263/56C07D263/57C07D403/06C07D405/06C07D413/06
Inventor 胡有洪冷颖段书冬黄素玲
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI