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

Synthesis and uses of synephrine derivatives

A technology of reaction and compound, applied in the field of synthesis and application of synephrine derivatives, can solve problems such as death and side effects

Active Publication Date: 2007-06-20
SYNTECH SSPF INT
View PDF11 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The natural products ephedra, pseudoephedra and caffeine were once widely used in combination formulas as weight loss products, but they have side effects including causing death

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
  • Synthesis and uses of synephrine derivatives
  • Synthesis and uses of synephrine derivatives
  • Synthesis and uses of synephrine derivatives

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0155] Novel Synthesis of Novel Compound 2-Chloro-1-(4-Chloroacetoxyphenyl)-Ethanone (An Example of Formula III Where "X" Is Chloro)

[0156] This example provides the synthetic method of new intermediate 2-chloro-1-(4-chloroacetoxybenzene)-ethanone, its structure is as follows:

[0157]

[0158] 9.4 g of phenol was dissolved in 10 ml of dichloroethane, and the resulting solution was cooled with an ice bath. Then add 33.4 g of aluminum trichloride in portions while stirring, and remove the ice bath after adding. Then, a solution of 25.0 g of chloroacetyl chloride dissolved in 15 ml of dichloroethane was added dropwise to the above mixture, and the addition was completed in about 1 hour. There are many gases produced. After the reaction mixture was stirred and reacted at 25° C. for 5 hours, the reaction mixture was poured into dilute glacial hydrochloric acid water while stirring to fully hydrolyze it. The resulting solid suspension was filtered and washed with acid and...

example 2

[0159] Literature preparation of the known 2-chloro-1-(4-hydroxyphenyl)-ethanone (an example of formula VI where "X" is chloro)

[0160] This example provides the literature preparation method of 2-chloro-1-(4-hydroxyphenyl)-ethanone, whose structure is as follows:

[0161]

[0162] 9.4 g of phenol was dissolved in 10 ml of dichloroethane, and the resulting solution was cooled with an ice bath. Then add 33.4 g of aluminum trichloride in portions while stirring, and remove the ice bath after adding. Then, a solution of 17.0 g of chloroacetyl chloride dissolved in 15 ml of dichloroethane was added dropwise to the above mixture, and the addition was completed in about 1 hour. There are many gases produced. The reaction mixture was stirred at 65°C for 12 hours. The reaction mixture was poured into dilute glacial hydrochloric acid water, the insoluble viscous material was extracted with dichloromethane, the dichloromethane solution was dried over anhydrous sodium sulfate, f...

example 3

[0163] Novel preparation of the known 2-chloro-1-(4-hydroxyphenyl)-ethanone by hydrolysis (an example of formula VI where "X" is chloro)

[0164] This example provides a new preparation method of 2-chloro-1-(4-hydroxyphenyl)-ethanone, whose structural formula is as in example 2 above.

[0165] 10 g of 2-chloro-1-(4-chloroacetoxyphenyl)-ethanone prepared in Example 1 was suspended in 50 ml of methanol, and the suspension was cooled by an ice bath. 5% sodium hydroxide solution in equimolar ratio was added dropwise, and after the addition was completed, the mixture was stirred and reacted at room temperature for 0.5 hours. Then most of the solvent was distilled off, and the resulting residue was frozen and crystallized, and 5.9 g of crystals were obtained by filtration, with a yield of 85% and a melting point of 151-152°C.

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
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

The present invention discloses a novel syntheses of synephrine, its derivatives, and the salts of the foregoing, including their intermediates. One or more of the substituents of the nitrogen atom of the synephrine is / are modified to produce the derivatives. The synephrine derivatives and their salts are useful for treating animals for diseases, conditions, or disorders modulated by beta3-adrenergic receptor. They are preferably used as fat breakdown agents and / or weight loss agents.

Description

[0001] Summary [0002] The present invention provides novel syntheses of Synephrine, Synephrine Derivatives, Salts of Synephrine and Synephrine Derivatives, including their intermediates. One or two substituents on the nitrogen atom in the synephrine structure are modified to obtain synephrine derivatives. Synephrine derivatives for the treatment of animals caused by β 3 A disease, condition or disorder in which adrenergic receptors are regulated. Synephrine derivatives are more suitable for lipolysis and / or weight loss. Background technique [0001] Synthetic drugs Sibutramine and Orlistat are long-term drugs for the treatment of obesity that have been marketed in recent years. The natural products ephedra, pseudoephedra, and caffeine were once widely used in combination formulas as weight loss products, but they have side effects, including death. [0002] In recent years, Synephrine, another natural product extracted from the traditional Chinese medicine Citrus auranti...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/30C07D239/70C07C67/14C07C67/293C07C215/60C07D211/70C07D213/74C07D215/04C07D233/54C07D239/42C07D239/46C07D277/42C07D295/088
CPCC07D239/42C07D233/54C07C2101/08C07D213/74C07D215/04C07D277/42C07C2101/16C07D295/088C07C2101/04C07D211/70C07C215/60C07C67/14C07C67/293C07C2102/08C07D239/47C07C2601/04C07C2601/08C07C2601/16C07C2602/08C07C69/63
Inventor 陈建
Owner SYNTECH SSPF INT
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