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

Crystalline morphology of Iguratimod intermediate VI

A technology of crystal form and intermediate, applied in the field of crystal form and preparation of Ailamod intermediate VI

Inactive Publication Date: 2017-07-18
常州佳德医药科技有限公司
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the crystal form of this intermediate has not been reported so far

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
  • Crystalline morphology of Iguratimod intermediate VI
  • Crystalline morphology of Iguratimod intermediate VI
  • Crystalline morphology of Iguratimod intermediate VI

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056]In a 50mL four-necked reaction flask, add 25mL of acetonitrile, 5.27g of aluminum trichloride, 7.4g of Iguratimod intermediate V (α-formamidomethyl-2-methoxy-4-methanesulfonyl- 5-phenoxyacetophenone) and 4.72g sodium iodide, reacted at 50°C for 5h, lowered the temperature, added 74g of 1% (mass percentage) sodium sulfite solution, filtered, washed with water, and drained to obtain 7.0g of the product, with a weight yield of 94.59 %. The crystal form 1 of the pure iguratimod intermediate VI was obtained by refining with methanol, with a purity of 99.8% and a melting point of 172.6-173.7°C.

[0057] The XRD of Form 1 of Iguratimod Intermediate VI is as follows: figure 1 As shown, the graph shows that the 2θ angle has characteristic peaks at the following positions: about 5.373°, about 10.398°, about 12.923°, about 17.803°, about 18.721°, about 19.586°, about 20.160°, about 21.584°, about 21.876° , about 22.601°, about 25.048°, about 27.421°. Its differential thermal ana...

Embodiment 2

[0059] In a 50mL four-necked reaction flask, add 25mL of acetonitrile, 5.27g of aluminum trichloride, 7.4g of Ilamomod intermediate V (α-formamidomethyl-2-methoxy-4-methanesulfonamido- 5-phenoxyacetophenone) and 4.72g sodium iodide, reacted at 50°C for 5h, lowered the temperature, added 74g of 1% (mass percentage) sodium sulfite solution, filtered, washed with water, and drained to obtain 6.92g of the product, with a weight yield of 93.51 %. Purified with acetonitrile to obtain the crystalline form 2 of the pure iguratimod intermediate VI with a purity of 99.7% and a melting point of 191.0-192.3°C.

[0060] The XRD of Form 2 of Iguratimod Intermediate VI is as follows: figure 2 As shown, the spectrum shows that the 2θ angle has characteristic peaks at the following positions: about 5.408°, about 7.432°, about 11.006°, about 16.201°, about 18.808°, about 19.675°, about 21.621°. Its differential thermal analysis DSC diagram is as follows Figure 4 As shown, their endothermic...

Embodiment 3

[0062] Add 15mL of acetonitrile, 5.27g of aluminum trichloride, 7.4g of Alamod intermediate V (α-formamidomethyl-2-methoxy-4-methanesulfonamido-5 -phenoxyacetophenone) and 4.72g of sodium iodide were reacted at 50°C for 5h, cooled, and 74g of 1% sodium sulfite solution was added, filtered, washed with water, and drained to obtain 6.81g of the product, with a weight yield of 92.0%. Purified with methanol to obtain the crystalline form 1 of the pure iguratimod intermediate VI with a purity of 99.0% and a melting point of 172.2-173.3°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 invention belongs to the technical field of pharmaceutical chemical engineering, and relates to a crystalline morphology of an Iguratimod intermediate VI (alpha-formamido-2-hydroxy-4-methanesulfonamide-5-phenoxyacetophenone). In addition, the invention further relates to a preparation method for two types of crystalline morphologies of Iguratimod intermediates VI. The two different types of crystalline morphologies of Iguratimod intermediates VI provided by the invention have good melting point and quality, the yield by weight is 90 to 95 percent, and the purity is 99.0 to 99.9 percent.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and relates to the crystal form of Alamod intermediate VI (α-formamido-2-hydroxy-4-methanesulfonamido-5-phenoxyacetophenone) and its preparation method . Background technique [0002] Iguratimod (3-formamido-7-methanesulfonamido-6-phenoxy-4H-1-benzopyran-4-one) was jointly developed by Japan Toyama and Eisai Pharmaceutical Co., Ltd., and can be used for Treats rheumatoid arthritis and relieves osteoarthritis pain. [0003] Chinese patent CN1944420 A reports five crystal forms of iguratimod, and different crystal forms show excellent physical and chemical properties. And α-formamido-2-hydroxyl-4-methanesulfonamido-5-phenoxyacetophenone is used as an intermediate for the preparation of Alamod (Ailamod intermediate VI), in the synthesis of Alamod Maud played a very important role in the process. However, the crystal form of this intermediate has not been reported so far. ...

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): C07C311/08C07C303/40
CPCC07C311/08C07B2200/13C07C303/40
Inventor 赵金亮
Owner 常州佳德医药科技有限公司
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