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
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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

Method used

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  • 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.

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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

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Application Information

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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
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