Halogenated 2-(a-hydroxyl pentyl) benzoate, production method and uses thereof

A technology of hydroxypentyl and benzoate, applied in the field of halogen-substituted 2-benzoate compounds and preparation thereof, can solve the problem of not involving the synthesis of halogenated 2-(a-hydroxypentyl)benzoate and Application and other issues, to achieve excellent anti-platelet aggregation effect, low toxicity, excellent protective effect

Active Publication Date: 2009-04-08
ZHEJIANG AUSUN PHARMA
View PDF4 Cites 44 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Chinese patent 200410048268.9 and Chinese patent 200610073077.7 respectively disclose the preparation and activity testing of the corresponding chiral 2-(a-hydroxypentyl) benzoate; Chinese patent 200710054215.1 discloses the halogenated 2-benzo[c] for the first time The synthesis and activity test of furanone compounds show that the activity of halogenated 2-benzo[c]furanone compounds is significantly better than that of butylphth

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Halogenated 2-(a-hydroxyl pentyl) benzoate, production method and uses thereof
  • Halogenated 2-(a-hydroxyl pentyl) benzoate, production method and uses thereof
  • Halogenated 2-(a-hydroxyl pentyl) benzoate, production method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: the preparation of the 2-(a-hydroxypentyl) benzoic acid of halogenation

[0038]

[0039] Add halo-3-n-butylisofuran-1(3H)-one (halogenated 3-n-butylphthalide) 50g methanol 100ml, NaOH 20g and water 30ml in the reaction flask, reflux for 6 hours, remove under reduced pressure After adding methanol, add 100ml of water and cool down. Under stirring, add hydrochloric acid with a concentration of 2M dropwise to adjust the pH to 2-3. Extracted with ether, the extract was washed with water, dried, filtered, and the ether was sucked dry under reduced pressure to obtain 100 g of white solid, yield: 90%.

Embodiment 2

[0040] Embodiment 2: the preparation of halogenated 2-(a-hydroxypentyl) benzoic acid sodium salt

[0041]

[0042] Add 2.0g (0.1mol) of NaOH, 30ml of methanol, and halogenated 2-(a-hydroxypentyl)benzoic acid (0.1mol) into the reaction flask, stir at room temperature for 2 hours, add 500ml of ether in batches, and precipitate a white oil , stirred for 2 hours and left to stand, the supernatant liquid was poured out, and the oil was evaporated to dryness under reduced pressure to obtain white halogenated 2-(a-hydroxypentyl)benzoic acid sodium salt.

Embodiment 3

[0043] Embodiment 3: the preparation of halogenated 2-(a-hydroxypentyl) potassium salt of benzoate

[0044]

[0045] Dissolve 10.7g KOH (0.19mol) in 60ml of methanol, then add halogenated 2-(a-hydroxypentyl)benzoic acid (0.48mol) in batches, and finish adding in 1 hour; after adding, continue to stir for 2 hours, then Slowly pour it into 2 liters of ether solution, a white solid precipitates out immediately, after the addition is complete, continue stirring for 2 hours, filter, and dry in vacuo to obtain 54 g of a white solid.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Diameteraaaaaaaaaa
Login to view more

Abstract

The invention discloses a halogen substituted 2-(a-hydroxyl amyl) benzoate compound, a preparation method and medicinal application thereof, which belong to the technical field of organic chemical synthesis. The structural formula of the compound which is showed as above has an antimer structure, wherein <R1> represents a halogen atom; n is equal to 1 to 3; and M represents a univalent metallic ion or a bivalent metallic ion or a trivalent metallic ion or an organic base. The compound has the advantages of better activity on preventing and treating cardio-cerebral ischemia diseases, improving cardio-cerebral circulation disturbance and resisting thrombus, and the like.

Description

technical field [0001] The present invention relates to a class of organic compounds, in particular to halogen-substituted 2-(a-hydroxypentyl) benzoate compounds and a preparation method thereof, and also relates to the use of such compounds in preventing and treating cardio-cerebral ischemic diseases and improving heart Cerebral circulation disorder, antithrombotic and other drugs. Background technique [0002] Acute ischemic stroke, coronary heart disease, and myocardial infarction are all ischemic injury diseases caused by thrombosis induced by various factors, which bring great pain and even life-threatening to patients. At present, research on this type of drug has always been the focus and frontier of drug research and development. [0003] Halogen chemistry is an important research field in medicinal chemistry. Halogen is an atom with greater electronegativity than carbon. When a halogen atom replaces a hydrogen atom, the electron cloud distribution of the original m...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07C65/03C07C51/09A61K31/192A61P9/10A61P7/02A61P25/28
Inventor 常俊标王威王强谢晶曦
Owner ZHEJIANG AUSUN PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products