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Glycogen phosphorylase inhibitor bile acid derivatives containing azo bond, preparation method and medical application thereof

A compound, pharmaceutical technology, applied in the field of glycogen phosphorylase inhibitor bile acid derivatives

Active Publication Date: 2015-10-21
CHENGDE MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the only azo-targeted prodrugs reported in the literature are prodrugs based on 5-aminosalicylic acid and azo polymer linkages.

Method used

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  • Glycogen phosphorylase inhibitor bile acid derivatives containing azo bond, preparation method and medical application thereof
  • Glycogen phosphorylase inhibitor bile acid derivatives containing azo bond, preparation method and medical application thereof
  • Glycogen phosphorylase inhibitor bile acid derivatives containing azo bond, preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (S)-2-tert-butoxycarbonylamino-3-(4-fluorophenyl)-1-(4-hydroxypiperidin-1-yl)acetone

[0043] Dissolve BOC-4-fluoro-L-phenylalanine (15.6g, 55.1mmol) in anhydrous dichloromethane (160mL), add HATU (25g, 66.1mmol) and DIPEA (8.54g, 66.1 mmol), stirred at room temperature for 10 minutes, then added 4-hydroxypiperidine (6.7 g, 66.1 mmol), stirred at room temperature overnight. The reaction solution was washed with saturated brine, anhydrous Na 2 SO 4 It was dried, filtered and concentrated, and the residue was separated by reverse phase HPLC to give a white solid (50mg, 29.8%). Flash column chromatography (petroleum ether / ethyl acetate 1 / 1, V / V) gave a white solid (19.7 g, 98%).

[0044] ESI-MS m / z: 367.2[M+H] + .

[0045] 1 H NMR (CDCl 3 , 400MHz): 7.14-7.18(m, 2H), 6.95-7.00(m, 2H), 5.47(dd, J=8.8, 14.8Hz, 1H), 4.83(dd, J=6.0, 13.6Hz, 1H), 3.81-4.01(m, 2H), 3.46-3.62(m, 1H), 3.15-3.33(m, 1H), 2.89-3.00(m, 2H), 1.73-1.83(m, 2H), 1.42-1.52(m , 2H), 1.40(s, 9H).

...

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Abstract

The invention relates to an azo bond contained glycogen phosphorylase inhibitor cholic acid derivative, a preparation method thereof and a pharmaceutical composition containing the same. The azo bond contained glycogen phosphorylase inhibitor cholic acid derivative is a liver-targeted pro-drug for glycogen phosphorylase; compared with a glycogen phosphorylase inhibitor, the concentration of the glycogen phosphorylase inhibitor in a liver can be increased after the glycogen phosphorylase inhibitor cholic acid derivative is taken orally, so that the glycogen phosphorylase inhibitor cholic acid derivative can serve as a preferred drug for lowering blood sugar, particularly for treating impaired fasting glucose. The compound can be used for preventing and treating diabetes and complications thereof, hyperlipidemia, obesity, high-glucagon disease, insulin resistance, impaired fasting glucose, hypertension and complications thereof, atherosclerosis, metabolic syndrome or tumor.

Description

technical field [0001] The invention relates to a class of bile acid derivatives containing azo bond-containing glycogen phosphorylase inhibitors, their preparation method and their drug combination. Glycogen phosphorylase inhibitors containing azo bonds Bile acid derivatives are liver-targeted prodrugs of glycogen phosphorylase, which can increase the level of glycogen phosphorylase after oral administration compared with glycogen phosphorylase inhibitors The concentration of the inhibitor in the liver can be used as a preferred drug for lowering blood sugar, especially fasting hyperglycemia. Such compounds can be used to prevent and treat diabetes and its complications, hyperlipidemia, obesity, hyperglucagonism, insulin resistance, fasting hyperglycemia, hypertension and its complications, atherosclerosis, metabolic Syndrome or tumor. Background technique [0002] Diabetes, especially type 2 diabetes, is the third chronic non-communicable disease that seriously threatens...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J43/00A61K31/58A61P3/10A61P3/06A61P3/04A61P5/50A61P9/12A61P9/10A61P3/00A61P35/00
CPCY02P20/55
Inventor 张丽颖
Owner CHENGDE MEDICAL UNIV
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