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AMPK activating compound and its use

A compound, mammalian technology, applied in the field of compounds to solve problems such as lactic acidosis

Inactive Publication Date: 2015-03-25
ENERGENESIS BIOMEDICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such AMPK activators have side effects including lactic acidosis, especially in patients with renal insufficiency

Method used

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  • AMPK activating compound and its use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] 2-Amino-6-(3-chlorobenzylamino)purine

[0047] After dissolving 4 mmol of 2-amino-6-chloropurine in 20 ml of butanol, 5 mmol of 3-chlorobenzylamine and 6 mmol of triethylamine were added. The mixture was reacted at 90°C for 4 hours. After cooling, the product was obtained by filtration, washed with water and butanol and crystallized from dimethylformamide or ethanol. HPLC: more than 98% purity. Productive rate 95%, the results are shown in Table 1.

[0048] Table 1 is produced by the compound of embodiment 1 method

[0049]

[0050]

Embodiment 2

[0052] 6-(3-Chlorobenzylamino)purine

[0053]After dissolving 4 mmol of 6-chloropurine in 20 ml of butanol, 5 mmol of 3-chlorobenzylamine and 6 mmol of triethylamine were added. The mixture was reacted at 90°C for 4 hours. After cooling, the product was obtained by filtration, washed with water and butanol and crystallized from dimethylformamide or ethanol. HPLC: more than 97% purity. Productive rate 94%, the results are shown in Table 2.

[0054] Table 2 is manufactured with the compound of embodiment 2 method

[0055]

[0056]

Embodiment 3

[0058] 2-Hydroxy-6-chloropurine

[0059] After dissolving 4 mmol of 2-amino-6-chloropurine in 35 ml of 50 wt% sulfuric acid, 5 mmol of sodium nitrate was added. The mixture was reacted at -10°C for 2 hours and then at 50°C for 1 hour. After cooling, the product was obtained by filtration, washed with water and butanol and crystallized from dimethylformamide or ethanol. HPLC: more than 98% purity. Yield 86%. MS(ESI)m / e170.88(M+H + );1H NMR(DMSO-d6):8.01(s,1H,=CH-N),13.26(s,2H,OH and NH).

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Abstract

The invention relates to an AMPK activating compound and its use in the preparation of drugs for preventing or treating diseases or physiological states which can be improved by an AMPK activator and comprise pre-diabetes, insulin resistance, type II diabetes, X-syndromes, metabolism syndromes and obesity. The compound reduces the blood plasma glucose amount by above 30wt%, reduces the triglyceride amount by above 35wt% and reduces the body weight by above 15%.

Description

technical field [0001] The present invention relates to compounds, especially a compound that activates AMPK (AMP-activated protein kinase) and its preparation for the treatment of diseases or physiological conditions that can be improved by AMPK activators to prevent or treat diseases, including pre-diabetes, insulin resistance, Use in medicine for type 2 diabetes, X-syndrome, metabolic syndrome and obesity. Background technique [0002] AMPK is clearly a sensor of cellular energy and a responder to energy demands. AMPK is a heteroternary body composed of catalytic α subunits, regulatory β and γ subunits, and all subunits are highly reserved in eukaryotes. AMPK is activated through its upstream kinases such as LKB1, calcium ion / calcitonin-dependent protein phosphokinase (Ca 2+ / Calmodulin dependent kinase) and TAK1 phosphorylate the α-subunit with a reserved 172th threonine residue, and the high AMP / ATP ratio caused by physiological or pathological stress also activates A...

Claims

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Application Information

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IPC IPC(8): C07D473/16C07D473/34C07D473/40C07D473/18A61K31/52A61K31/513A61P3/10A61P3/00A61P3/04A61P3/06A61P5/50
CPCC07D473/16C07D473/18C07D473/34C07D473/40
Inventor 邱壬乙陈翰民郭正宜林俊材黄纯芳
Owner ENERGENESIS BIOMEDICAL
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