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Iguratimod crystalline form and composite thereof

A technology of crystal form and composition, applied in the field of autoimmune regulation drugs, to achieve the effect of easy production and high biological activity

Active Publication Date: 2010-11-24
TIANJIN INSTITUTE OF PHARMA RESEARCH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Regarding the crystalline form of iguratimod, there has been no literature report on the crystalline form so far

Method used

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  • Iguratimod crystalline form and composite thereof
  • Iguratimod crystalline form and composite thereof
  • Iguratimod crystalline form and composite thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] The following examples are further illustrative of the invention, not limiting.

[0080] Unless otherwise stated, herein, temperature refers to degrees Celsius (°C), and room temperature refers to about 18-23°C. The present inventors have identified several different forms of crystalline iguratimod, which have been characterized by several methods, typically XRD, DSC and IR.

[0081] According to Chem.Pharm.Bull.48131-139.2000. and Japanese Patent No97840, 4-chloro-3-nitroanisole is used as starting material to react with phenol to generate 4-phenoxy- 3-nitroanisole, iron powder reduction reaction to get 4-phenoxy-3-aminoanisole, acylation reaction with methanesulfonyl chloride to generate 3-methanesulfonamide-4-phenoxyanisole, and then Reaction with aminoacetonitrile hydrochloride, acylation, cyclization, and a total of 7 steps to prepare iguratimod. Reaction formula:

[0082]

[0083]

[0084] Alamode

[0085] Example 1. Preparation of Form 1: Take 10 grams ...

Embodiment 2

[0087] Example 2. Preparation of Form 2: Take 10 grams of Iguratimod and put it into a 1000 ml round bottom flask, add 500-1000 ml of analytically pure acetonitrile and activated carbon, heat, reflux, filter, and place the filtrate at room temperature for 24 hours, filter, filter The cake was washed and dried under reduced pressure at 50-60°C to obtain 9.5 g of Form 2. The melting point is 237-238°C.

[0088] Form 2 has an XRD pattern at about 24.48, about 22.60, about 21.76, about 19.52, about 10.84, about 18.08, about 17.56, about 16.92, about 11.20, about 9.36, about 8.64, about 7.48, about 6.84, about 6.52, and about 5.60 Peak, its DSC endothermic transition is at about 236-240 ° C; the IR (KBr, cm -1 ) at about 3342, 3276, 3123, 3065, 2869, 1687, 1621, 1531, 1489, 1425, 1358, 1264 and 1156 cm -1 There are characteristic bands, differential thermogram, and infrared spectrogram are the same as Form 1, see figure 2 -3.

Embodiment 3

[0089] Example 3. Preparation of Form 3: Take 10 grams of Iguratimod and put it into a 100 ml round-bottomed flask, add 20 ml of analytically pure dimethylformamide and activated carbon, heat, reflux, and filter, and place the filtrate in a refrigerator at room temperature for 18 hours. Filter, wash the filter cake, and dry under reduced pressure at 50-60°C to obtain 9.5 g of form 3. The melting point is 237-238°C.

[0090] The XRD pattern of Form 3 has peaks at about 27.28, about 25.68, about 25.24, about 24.40, about 24.04, about 23.08, about 20.16, about 17.52, about 10.56, and about 6.00, and its DSC endothermic transition is at about 236-240°C; IR (KBr, cm -1 ) at about 3342, 3276, 3123, 3065, 2869, 1687, 1621, 1531, 1489, 1425, 1358, 1264 and 1156 cm -1 There are characteristic bands, differential thermogram, and infrared spectrogram are the same as Form 1, see figure 2 -3.

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Abstract

The invention relates to a crystalline form (Iguratimod) of N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]-methyl sulfonamide. In addition, the invention further relates to application of the Iguratimod crystalline form in the medicine of treating rheumatoid arthritis, a pharmaceutical composition containing Iguratimod crystalline form and a method for preparing crystalline Iguratimod.

Description

technical field [0001] The invention belongs to the technical field of autoimmune regulation medicines, and more specifically, the invention relates to the crystal form of iguratimod, its preparation method and its application in the preparation of pharmaceutical preparations. Background technique [0002] Rheumatoid arthritis (RA) is a highly disabling systemic autoimmune disease. If it is not actively and effectively treated, joint erosions will generally occur within 1 to 2 years. Currently, RA treatment is divided into two categories of drugs, non-steroidal anti-inflammatory analgesics (NSAIDs) and disease-modifying antirheumatic drugs (DMARDs). The main function of NSAIDs is to relieve joint pain, swelling and improve joint function in RA patients, but it does not change the progress of the disease, nor prevent joint destruction, and its severe adverse reactions to the gastrointestinal tract limit its use. Compared with NSAIDs, DMARDs have a slower onset of action and ...

Claims

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Application Information

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IPC IPC(8): C07D311/22A61K31/352A61P19/02A61P29/00
Inventor 梅林雨梁忠信王杏林高晶
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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