Phthalide derivative as well as preparation method and application thereof

A technology of phthalides and derivatives, which is applied in the field of phthalide derivatives and their preparation, can solve problems such as not being able to meet the requirements for the treatment of stroke, and achieve good anti-platelet aggregation, stable chemical structure, and enhanced stability Effect

Active Publication Date: 2018-12-21
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the obvious chemical structure characteristics, the pharmacological activity of ligustilide is stronger than that of butylphthalide, but in terms of pharmaceutical effectiveness, safety and quality control, butylphthalide has pharmaceutical characteristics (stable chemical structure), so it is approved by SFDA Approved for marketing, but the current clinical response Due to its activity and side effects, clinicians have put forward a strong demand for further optimization and improvement of activity of butylphthalide, which cannot meet the clinical requirements for the treatment of stroke

Method used

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  • Phthalide derivative as well as preparation method and application thereof
  • Phthalide derivative as well as preparation method and application thereof
  • Phthalide derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: N-cyclopropyl-3-n-butyl-3- S - Synthesis of hydroxy-ligustilactam.

[0047]Ligustilide (1.900 g, 0.010 mol) was dissolved in 50 mL of tetrahydrofuran, and cyclopropylamine (0.684 g, 0.012 mol) was dissolved in 20 mL of tetrahydrofuran. The temperature of the water bath was controlled at 25 ° C. Under mechanical stirring, the ring The tetrahydrofuran solution of propylamine was added dropwise to the tetrahydrofuran solution of ligustilide, stirred and reacted for 4 h, the tetrahydrofuran and excess cyclopropylamine solution were recovered by rotary evaporation under reduced pressure, and 200 mL of petroleum ether was added to the above concentrate, mixed evenly, and placed The synthetic product was crystallized and washed out overnight, and suction filtered to obtain 1.976 g of crude product, with a reaction yield of 80%. The crude product was recrystallized with a mixed solvent of petroleum ether and acetone (5:1, V / V) to obtain a crystalline product of 0.97 ...

Embodiment 2

[0051] Example 2: Synthesis of N-cyclopropyl-3-n-butyl-3-hydroxy-phthalide.

[0052] Ligustilide (1.880 g, 0.010 mol) was dissolved in 50 mL of tetrahydrofuran, and cyclopropylamine (0.684 g, 0.012 mol) was dissolved in 20 mL of tetrahydrofuran. Under mechanical stirring at room temperature, the tetrahydrofuran solution of cyclopropylamine was added dropwise to into the tetrahydrofuran solution of ligustilide, stirred and reacted for 6 hours, recovered tetrahydrofuran and excess cyclopropylamine solution by rotary evaporation under reduced pressure, added 200 mL of petroleum ether to the above concentrate, mixed well, and left overnight until the crystallization of the synthesized product was washed. out, and suction filtered to obtain 2.083 g of crude product, with a reaction yield of 85%. The crude product was recrystallized with a mixed solvent of petroleum ether and acetone (10:1, V / V), to obtain 1.666 g of crystalline product, with a crystalline yield of 80%. %. Using th...

Embodiment 3

[0055] Embodiment 3: Using angelica volatile oil to carry out compound N-cyclopropanyl-3-n-butyl-3-hydroxyl-ligustilactam and compound N-cyclopropyl-3-n-butyl-3-hydroxyl-phthalide Synthesis of a mixture of amides

[0056] The prepared Angelica volatile oil was pre-separated by column chromatography with petroleum ether and ethyl acetate (3:1, V / V) as the eluent, and the Angelica volatile oil (3.000 g ,) was dissolved in 60 mL of tetrahydrofuran, cyclopropylamine (0.684 g, 0.012 mol) was dissolved in 30 mL of tetrahydrofuran, under mechanical stirring, the tetrahydrofuran solution of cyclopropylamine was added dropwise to the above tetrahydrofuran solution of angelica volatile oil, and the reaction was stirred After 10 h, the tetrahydrofuran and excess cyclopropylamine solution were recovered by rotary evaporation under reduced pressure, and 200 mL of petroleum ether was added to the above concentrate, mixed evenly, and left overnight until the crystals of the synthesized produ...

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Abstract

The invention discloses a phthalide derivative. The structure of the derivative is shown in the description. The invention also discloses a preparation method and application of the derivative. The phthalide derivative is obtained through structural modification, thereby enhancing the chemical stability and pharmacological activity of a phthalide compound, and improving the druggability of the type of compound.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, and relates to a phthalide derivative and a preparation method and application thereof. Background technique [0002] In nature, plants of the genus Angelica and Ligusticum in Umbelliferae contain phthalide compounds, such as angelica and chuanxiong. These compounds are the main components of plant volatile oils, and most of them have a strong aroma. It is rich in content, and there are many types of compound structures. These compounds are generally chemically unstable, and they are easily oxidized or degraded by light, heat and enzymes in the environment when they exist alone. However, such compounds generally have good pharmacological activities, such as anti-oxidation, anti-platelet aggregation, promotion of microcirculation, analgesia and anti-inflammation, central nervous system protection and anti-tumor and other significant pharmacological activities. Ligustilide is the main ph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/52C07D209/48A61P9/00A61P39/06
CPCA61P9/00A61P39/06C07D209/48C07D209/52C07B2200/07
Inventor 柳军玺张亚明
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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