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Triazopyridine formylglycine compound, and method and medicinal application thereof

A compound and pharmaceutical technology, which is applied in the field of triazole pyridine glycine compounds, can solve the problems that nutrition therapy is difficult to play a corresponding role, and achieve the effects of promoting EPO production and secretion, increasing EPO production and secretion, and strongly inhibiting activity

Active Publication Date: 2018-03-06
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when the anemia is caused by insufficient secretion of EPO, nutritional therapy alone cannot play a corresponding role, and erythropoiesis-stimulating agents (ESAs) should be given for treatment.

Method used

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  • Triazopyridine formylglycine compound, and method and medicinal application thereof
  • Triazopyridine formylglycine compound, and method and medicinal application thereof
  • Triazopyridine formylglycine compound, and method and medicinal application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] N-(5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-3-hydroxy-6-methylpicolyl)glycine

[0059] N-((5-(trimethylsilyl)ethynyl)-3-hydroxy-6-methylpicolyl)glycine methyl ester (200mg, 0.69mmol) was dissolved in 10mL of methanol, and 0.2mL of N,N- Diisopropylethylamine, 20mg cuprous iodide, 1mL TBAF and benzyl azide (110mg, 0.82mmol), conventionally heated to 80°C for 4h or microwaved to 120°C for 10min, the reaction was complete. After the reaction, cuprous iodide was removed by suction filtration, and after distillation under reduced pressure, the crude product was separated and purified by silica gel column chromatography (dichloromethane:methanol=100:1), and the white solid was dissolved in 10 mL of tetrahydrofuran, and 3 mL of 1M hydroxide was added to Lithium solution was heated to 30°C for 2 hours, and the reaction was complete. After the reaction, tetrahydrofuran in the reaction solution was distilled off under reduced pressure, and 3 mmol of dilute hydrochloric acid was added u...

Embodiment 2

[0061] N-(5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-6-chloro-3-hydroxypicolinate)glycine

[0062]N-((5-(trimethylsilyl)ethynyl)-6-chloro-3-hydroxypyridinecarboyl)glycine methyl ester (200mg, 0.69mmol) was dissolved in 10mL methanol, and 0.2mL N,N- Diisopropylethylamine, 20mg cuprous iodide, 1mL TBAF and benzyl azide (110mg, 0.82mmol), conventionally heated to 80°C for 4h or microwaved to 120°C for 10min, the reaction was complete. After the reaction, cuprous iodide was removed by suction filtration, and after distillation under reduced pressure, the crude product was separated and purified by silica gel column chromatography (dichloromethane:methanol=100:1), and the white solid was dissolved in 10 mL of tetrahydrofuran, and 3 mL of 1M hydroxide was added to Lithium solution was heated to 30°C for 2 hours, and the reaction was complete. After the reaction, tetrahydrofuran in the reaction solution was distilled off under reduced pressure, and 3 mmol of dilute hydrochloric acid was add...

Embodiment 3

[0064] N-(5-(1-(1-(4-chlorophenyl)cyclopropyl-1H-1,2,3-triazol-4-yl)-3-hydroxy-6-methylpicolinyl ) Glycine

[0065] N-((5-(trimethylsilyl)ethynyl)-3-hydroxy-6-methylpicolyl)glycine methyl ester (200mg, 0.69mmol) was dissolved in 10mL of methanol, and 0.2mL of N,N- Diisopropylethylamine, 20mg cuprous iodide, 1mL TBAF and 4-chlorophenylcyclopropyl azide (110mg, 0.82mmol), conventionally heated to 80°C for 4h or microwaved to 120°C for 10min, the reaction was complete. After the reaction, cuprous iodide was removed by suction filtration, and after distillation under reduced pressure, the crude product was separated and purified by silica gel column chromatography (dichloromethane:methanol=100:1), and the white solid was dissolved in 10 mL of tetrahydrofuran, and 3 mL of 1M hydroxide was added to Lithium solution was heated to 30°C for 2 hours, and the reaction was complete. After the reaction, tetrahydrofuran in the reaction solution was distilled off under reduced pressure, an...

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Abstract

The invention relates to the field of medicinal chemistry, in particular to a triazopyridine formylglycine compound (I). The compound has high prolyl hydroxylase inhibition activity, and can stabilizeintracellular hypoxia inducing factors, increase generation and secretion of erythropoietin and promote erythropoiesis. The invention also relates to a preparation method of the compound, a medicinalcomposition containing the compound or a pharmaceutically acceptable salt thereof, as well as application of the compound or the pharmaceutically acceptable salt thereof to preparation of medicines for inhibiting prolyl hydroxylase or preparation of medicines for promoting generation of the erythropoietin.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry. It specifically relates to a class of triazole pyridine glycine compounds, which have good prolyl hydroxylase inhibitory activity, can significantly increase the production and secretion of erythropoietin, thereby promoting red blood cell production, and can be used for treatment or prevention Anemia such as chronic renal anemia and ischemic diseases such as ischemic stroke, myocardial ischemia and other related diseases. Background technique [0002] Anemia generally refers to a disorder caused by abnormalities in hemoglobin, or red blood cells, that result in low oxygen levels in the blood. Anemia of chronic disease is one of the most common syndromes in medicine, such as chronic renal anemia. Renal anemia refers to anemia caused by relative or absolute deficiency of erythropoietin (EPO) caused by various kidney diseases (J Am Soc Nephrol19(2008) 7 1389-95), and some toxic substance...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D401/14C07D405/14C07D409/14A61K31/4439A61K31/444A61K31/506A61P7/06A61P13/12A61P29/00A61P19/02A61P1/00A61P9/10
CPCC07D401/04C07D401/14C07D405/14C07D409/14
Inventor 尤启冬张晓进蒋真盛伍悦李治红
Owner CHINA PHARM UNIV
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