Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of buparvaquone

A technology of bupavaquinone and solvent is applied in the field of drug synthesis, which can solve the problems of low yield and the like, and achieve the effect of low cost

Inactive Publication Date: 2014-01-01
SHANDONG LUKANG SHELILE PHARMA
View PDF3 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Both of the above routes use the expensive catalyst AgNO 3 , and the yield is low

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
  • Preparation method of buparvaquone
  • Preparation method of buparvaquone
  • Preparation method of buparvaquone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Step 1: Condensation Reaction

[0028] Under argon protection, add 1.62g (0.01mol) of 1,4-benzopyrandione to a 50ml three-necked flask, slowly add 20ml of acetic acid solution of 1.82g (0.01mol) of p-tert-butylcyclohexylaldehyde, add 0.87ml (0.01mol) of isobutylamine was heated to 60°C for 4h.

[0029] Post-processing: Add 20ml of water dropwise to the reaction flask, solids are precipitated, filtered by suction, and recrystallized with 50ml of methyl tert-butyl ether to finally obtain a yellow solid product (formula intermediates shown).

[0030] Step 2: rearrangement reaction

[0031] Add the above product, 10ml of methanol, 10ml of 30% methanol solution of sodium methoxide (made now) into a 100ml single-necked bottle, and control the temperature at 20°C until the reaction is complete.

[0032] Post-processing: Filtration, adding 40ml of acetic acid to the filtrate to adjust the pH to 7-8, concentrating in vacuo until the solid precipitates, filtering with suction...

Embodiment 2

[0037] Step 1: Condensation Reaction

[0038] Under nitrogen protection, add 3.24g (0.02mol) of 1,4-benzopyrandione into a 100ml three-necked flask, slowly add 40ml of acetic acid solution of 7.28g (0.04mol) of p-tert-butylcyclohexylaldehyde, and add iso Butylamine 1.74ml (0.02mol), heated to 30°C for 10h.

[0039] Post-processing: drop 40ml of water into the reaction flask, solids are precipitated, filtered by suction, recrystallized with 100ml of ether, and finally obtain a yellow solid product (formula intermediates shown).

[0040] Step 2: rearrangement reaction

[0041] Add the above product, 20ml of methanol, and 20ml of 30% methanol solution of sodium methoxide (made now) into a 100ml single-necked bottle, and the reaction is completed at 20°C.

[0042] Post-processing: Filtration, adding 100ml acetic acid to the filtrate to adjust the pH to 7-8, concentrating in vacuo until the solid precipitates, filtering with suction, recrystallizing with 200ml of a mixed soluti...

Embodiment 3

[0044] Step 1: Condensation Reaction

[0045] Under argon protection, add 1.62g (0.01mol) of 1,4-benzopyrandione to a 50ml three-necked flask, slowly add 20ml of acetic acid solution of 1.82g (0.01mol) of p-tert-butylcyclohexylaldehyde, and add Morpholine 2.61ml (0.03mol), warmed up to 40°C for 4h.

[0046] Post-processing: Add 20ml of water dropwise to the reaction flask, solids are precipitated, filtered by suction, and recrystallized with 50ml of methyl tert-butyl ether to finally obtain a yellow solid product (formula intermediates shown).

[0047] Step 2: rearrangement reaction

[0048] Add the above product, 10ml of methanol, 10ml of 30% sodium ethoxide in ethanol (prepared now) into a 100ml single-necked bottle, and the reaction is completed at 20°C.

[0049] Post-treatment: filter, add 40ml of acetic acid to the filtrate to adjust the pH to 7~8, concentrate in vacuo until the solid precipitates, filter with suction, recrystallize with 100ml of methanol and water mi...

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
Melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a preparation method of buparvaquone and belongs to the field of medicine synthesis. The preparation method comprises the following step of: with 1,4-benzopyran diketone and p-tert-butylcyclohexyl acetaldehyde as raw materials, performing condensation and rearrangement to prepare pharmaceutical grade buparvaquone. According to the preparation method of buparvaquone, provided by the invention, use of an expensive catalyst AgNO3 is avoided, and a total synthesis yield is increased to about 65% as compared with the prior art. The route is green and environment-friendly, and easy to industrialize.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a preparation method of bupavaquinone. Background technique [0002] Buparvaquinone (2-[(4-tert-butylcyclohexyl)methyl]-3-hydroxy-1,4-naphthalenedione, CAS number: 88426-33-9, English name: Buparvaquone) is from Pitman-Moore Company A drug for the treatment of bovine theilesisis was developed in 1991 for the first time in some countries in Africa, the Middle East and the Far East, under the trade name Butalex. This product is the most effective drug for the treatment of theileriasis, and its effect exceeds that of the same drug - pavaquinone. Intramuscular injection of 2.5mg / kg dose to the affected cattle, medication 1-2 times, the effective rate can reach 92%. This product can also activate the immunity of cattle and improve animal production performance. [0003] There are mainly 2 routes in the prior art. [0004] Route 1 According to the patent EP 0077550, bupavaquinone is p...

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): C07C50/32C07C46/00
CPCC07C46/00C07D311/76
Inventor 马浩杰郭强颜丙春董坤彭欣桑艳丽
Owner SHANDONG LUKANG SHELILE PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com