Pyridine ring-substituted alpha-hydroxycarboxylic acid derivatives, preparation method thereof and use thereof

A substituent, nitropyridine technology, applied in the application field of α-hydroxycarboxylic acid derivative corticosteroid selective endothelin receptor antagonist, preparation of antihypertensive drugs, can solve the problems of untimely treatment and lack of pulmonary arterial hypertension medications, etc.

Inactive Publication Date: 2010-07-07
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pulmonary hypertension is a disease that still plagues the medical field. If it is not treated in time, the

Method used

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  • Pyridine ring-substituted alpha-hydroxycarboxylic acid derivatives, preparation method thereof and use thereof
  • Pyridine ring-substituted alpha-hydroxycarboxylic acid derivatives, preparation method thereof and use thereof
  • Pyridine ring-substituted alpha-hydroxycarboxylic acid derivatives, preparation method thereof and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0070] Synthesis of embodiment 13-phenyl-3-(3-fluorophenyl)-2,3-epoxypropionic acid methyl ester

[0071]

[0072] Dissolve 42ml of 3-fluoro-benzophenone (29.646g, 0.148mmol, a type of VII) and methyl chloroacetate (a type of VI) in 40ml THF, and put it into a constant pressure funnel for use. Add 200ml THF to a 250ml three-neck flask, add sodium methoxide (24g, 0.444mmol) while stirring, cool to 0°C in an ice-salt bath, and add the above mixed solution dropwise, controlling the temperature not to exceed 10°C. After the addition, react at room temperature for 0.5 hours, add 150ml of water, extract with ethyl acetate (100ml×3), combine the organic phases, wash twice with saturated brine, dry with anhydrous sodium sulfate, filter, and distill under reduced pressure, the concentrate is 41.9g oily (a kind of V), yield 75%, ESI-MS: m / z 213[M-59], 241[M-31], 273[M+1], 295[M+23] are directly used in the following step response.

Embodiment 2-12

[0074] With reference to the synthetic operation of Example 1, different benzophenone derivatives were used to replace 3-fluoro-benzophenone (VII) in Example 1 to obtain different 3,3-diaryl-substituted-2,3 - Derivatives (V) of methyl glycidate.

[0075]

[0076]

Embodiment 163

[0077] Synthesis of Example 163-phenyl-3-(3-fluoro-phenyl)-2-hydroxyl-3-methoxypropionic acid methyl ester

[0078]

[0079] Dilute the product of Example 1 (a type of V) with 200ml of methanol (a type of IV), add p-benzenemethanesulfonic acid (0.65g, 3.42mmol) at room temperature, heat to reflux for 1h, concentrate under reduced pressure, and the residue dissolves In dichloromethane, washed with dilute sodium carbonate solution, the organic phase was dried and concentrated to give a light yellow viscous liquid as 3-phenyl-3-(3-fluoro-phenyl)-2-hydroxy-3-methoxy Methyl propionate (one of compound III), yield 80%, ESI-MS: m / z 245[M-59], 273[M-31], 305[M+1], 327[M+23 ].

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PUM

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Abstract

The invention relates to the fields of medicaments for treating blood pressure diseases and particularly relates to pyridine ring-substituted alpha-hydroxycarboxylic acid derivatives of a general formula I, preparation method thereof, medicinal compositions having the same and use thereof as an endothelin antagonist in the preparation of medicaments for treating hypertension and pulmonary hypertension, wherein groups are defined in the description.

Description

technical field [0001] The present invention relates to the field of drugs related to hypertension, in particular, the present invention relates to a pyridine ring substituted α-hydroxycarboxylic acid derivative corticosteroid selective endothelin receptor antagonist with hypotensive effect, its preparation method and Pharmaceutical composition, and its application in the preparation of antihypertensive drugs. Background technique [0002] Hypertension, pulmonary hypertension and other blood pressure diseases are more harmful diseases. Hypertension is a common disease with a high incidence rate, and usually requires long-term medication. It has always been an urgent desire for people to find safe and effective therapeutic drugs. Pulmonary hypertension is a disease that still plagues the medical field. If the disease is not treated in time, the survival time is only two to three years. There is still no effective treatment for pulmonary hypertension. [0003] Endothelin (ET...

Claims

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Application Information

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IPC IPC(8): C07D213/63A61K31/44A61P9/12
Inventor 张大同徐为人谭初兵汤立达邹美香王玉丽刘巍张士俊刘冰妮任晓文
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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