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

Method for separating nateglinide and its stereoisomers by high performance liquid chromatography

A technology of high performance liquid chromatography and stereoisomers, which is applied in the field of medicine, can solve the problems of high buffer concentration and short service life of chromatographic columns, and achieve high separation efficiency, guaranteed effectiveness and safety, and short separation time Effect

Active Publication Date: 2020-05-08
JIANGSU DEYUAN PHARMA
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Yang et al. reported a method for the separation of nateglinide and its L-isomer based on (R)-phenylglycic acid and 3,5-dinitroaniline-bonded silica chiral stationary phase, using Sumichiral OA- 3300 (250 × 4.6 mm, 5 µm) is a chromatographic column, and the methanol solution of ammonium acetate of 0.025mol / L is used as the mobile phase. This method has a higher buffer concentration and a shorter service life of the chromatographic column (Gengliang Yang et al., Chromatographia. (2002 ). 56(7): 515-518.)

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
  • Method for separating nateglinide and its stereoisomers by high performance liquid chromatography
  • Method for separating nateglinide and its stereoisomers by high performance liquid chromatography
  • Method for separating nateglinide and its stereoisomers by high performance liquid chromatography

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1, a method for simultaneous resolution of nateglinide and its cis-isomer and L-isomer by high-performance liquid chromatography: Weigh nateglinide, cis-isomer and L-isomer respectively An appropriate amount of isomer, dissolved and diluted with n-hexane: absolute ethanol (80:20) to make a mixed solution containing about 1 mg of nateglinide, 2 µg of cis-isomer and 2 µg of L-isomer per 1 mL ;Amylose-tris(3-chloro-5-methylphenylcarbamate) covalently bonded to the surface of silica gel as the stationary phase, and a mixed solution of n-hexane, absolute ethanol and trifluoroacetic acid as the mobile phase , using a high-performance liquid chromatography system to resolve nateglinide and its isomers; the surface is covalently bonded with amylose-tris(3-chloro-5-methylphenylcarbamate) type The chiral column is bonded chiral column CHIRALPAK IG. The flow rate of the mobile phase is 1 mL / min, the temperature of the chromatographic column is 30° C., and the detection wa...

Embodiment 2

[0029] Example 2, a method for simultaneous resolution of nateglinide and its cis-isomer and L-isomer by high-performance liquid chromatography: Weigh nateglinide, cis-isomer and L-isomer respectively An appropriate amount of isomers was dissolved and diluted with n-hexane: absolute ethanol (75:25) to make a mixed solution containing about 1 mg of nateglinide, 2 µg of cis-isomers and 2 µg of L-isomers per 1 mL ;Amylose-tris(3-chloro-5-methylphenylcarbamate) covalently bonded to the surface of silica gel as the stationary phase, and a mixed solution of n-hexane, absolute ethanol and trifluoroacetic acid as the mobile phase , using a high-performance liquid chromatography system to resolve nateglinide and its isomers; the surface is covalently bonded with amylose-tris(3-chloro-5-methylphenylcarbamate) type The chiral column is bonded chiral column CHIRALPAK IG. The flow rate of the mobile phase is 0.8mL / min, the temperature of the chromatographic column is 30°C, and the detecti...

Embodiment 3

[0030] Example 3, a method for simultaneous resolution of nateglinide and its cis-isomer and L-isomer by high-performance liquid chromatography: Weigh nateglinide, cis-isomer and L-isomer respectively An appropriate amount of isomer, dissolved and diluted with an appropriate amount of diluent to make a mixed solution containing about 1 mg of nateglinide, 2 µg of cis-isomer and 2 µg of L-isomer per 1 mL; Amylose-tris(3-chloro-5-methylphenylcarbamate) was used as the stationary phase, and a mixed solution of n-hexane, absolute ethanol and trifluoroacetic acid was used as the mobile phase, and a high-performance liquid chromatography system was used for resolution Nateglinide and its isomers; the diluent is n-hexane: absolute ethanol (75:25). The flow rate of the mobile phase is 0.8mL / min, the temperature of the chromatographic column is 30°C, and the detection wavelength is 220nm. The injection volume is 20 μL. In the mobile phase, by volume ratio, n-hexane: absolute ethanol: ...

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

No PUM Login to View More

Abstract

The invention discloses an HPLC (high performance liquid chromatography) resolution method for nateglinide and nateglinide stereoisomers. The method comprises the following steps: dissolving a mixed sample containing nateglinide as well as a cis-isomer and an L-isomer of nateglinide in a diluent until the concentration reaches 0.1-2 mg / mL; resolving nateglinide and the nateglinide stereoisomers with an HPLC system by taking silica gel with surface in covalent bonding with amylose-tris(3-chloro-methylphenyl carbamate) as a stationary phase. Nateglinide as well as the cis-isomer and the L-isomer of nateglinide can be resolved rapidly, efficiently and simultaneously with the method. The separation efficiency is high, the resolution time is short, the separation degree between the cis-isomer of nateglinide and nateglinide is 3.82, the separation degree between the L-isomer of nateglinide and nateglinide is 9.84, the method for simultaneously separating nateglinide from the cis-isomer and the L-isomer of nateglinide and determining nateglinide as well as the cis-isomer and the L-isomer of nateglinide is realized effectively, and effectiveness and safety of nateglinide products are guaranteed.

Description

technical field [0001] The invention relates to a method for resolving nateglinide and its isomers, belonging to the technical field of medicine. Background technique [0002] Nateglinide, chemical name N-(trans-4-isopropylcyclohexyl-1-formyl)-D-phenylalanine, is a non-sulfonylurea oral hypoglycemic It lowers blood sugar by stimulating the release of insulin, and has the characteristics of fast onset and short duration of action. [0003] There are cis-trans isomerism and optical isomerism in the three-dimensional structure of the nateglinide molecule, and the commercially available strong active substance is a trans-D configuration compound. It has been reported that oral administration of 1.6 mg / Kg nateglinide and oral administration of 100 mg / Kg L-isomer have comparable hypoglycemic effect (about 20%), while the cis-isomer has no hypoglycemic effect. In the production process, there are often a small amount of cis- and L-configuration isomers in nateglinide raw material...

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 Patents(China)
IPC IPC(8): G01N30/02
CPCG01N30/02
Inventor 杨汉跃董淑波陈学民闫显光吴广通陈勇叶德举王黎杜娜娜
Owner JIANGSU DEYUAN 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