Sodium salt compound of Iguratimod, preparation method thereof and pharmaceutical use thereof

A potassium compound and reaction technology, applied in the field of Iilamod's derivative compounds, can solve the problems of degradation, poor fluidity, and poor stability of Iilamod.

Inactive Publication Date: 2012-07-04
杨喜鸿
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] As a new type of high-efficiency non-steroidal anti-inflammatory drug, iguratimod also has deficiencies in drug preparation: one is that iguratimod is insoluble in water, and when administered orally, because of the poor insolubility of the drug in water, it contains In the common preparation composition of iguratimod, its active ingredient is not easy to wet and diffuse in water, and the oral dosage form prepared with conventional preparation auxiliary materials and dispersion system is easy to crystallize or precipitate out in gastrointestinal fluid and cannot be dissolved, which greatly Affecting the stripping and absorption utilization of medicines, there are unfavorable factors; the second is that the iguratimod compound is light in weight and prone to electrostatic interaction, which causes the iguratimod compound (crude drug) to gather into cotton wool, lacks brittleness, and is difficult to pulverize. The fluidity is very poor, and it is difficult to mix evenly with pharmaceutical excipients in the preparation of preparations, which brings great difficulties to the preparation of iguratimod preparations and the improvement of quality, and is not conducive to the needs of large-scale industrial production; the third is iguratimod Poor stability and degradation will occur, which will bring hidden dangers to the storage and quality safety of pharmaceutical preparations

Method used

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  • Sodium salt compound of Iguratimod, preparation method thereof and pharmaceutical use thereof
  • Sodium salt compound of Iguratimod, preparation method thereof and pharmaceutical use thereof
  • Sodium salt compound of Iguratimod, preparation method thereof and pharmaceutical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] Embodiment 1. iguratimod potassium and its preparation

[0113] Method 1. Add 1 g (about 2.67 mmol) of iguratimod to 400 ml of absolute ethanol, heat to reflux to dissolve, then add 150 mg of potassium hydroxide (about 2.67 mmol) in 10 ml of absolute ethanol, stir and mix at 80°C , reaction, if necessary, 280mg of activated carbon can be added, stirred and kept for decolorization and filtered out activated carbon, the filtrate is spin-dried with a rotary evaporator to remove the solvent, and the solid obtained is washed or rinsed repeatedly with cold ethanol or ether, the washing solvent is removed, and dried, to obtain Airamod Potassium. Molecular formula C 17 h 13 N 2 o 6 SK, elemental analysis results:

[0114] % Theoretical C: 49.50H: 3.18N: 6.79

[0115] % Found C: 49.56H: 3.22N: 6.81.

[0116] Method 2. Take 1g (about 2.67mmol) of iguratimod and add 80ml of distilled water to stir to make a suspension, and add 151mg of potassium hydroxide (about 2.7mmol) in...

Embodiment 2

[0126] Embodiment 2. iguratimod potassium and its preparation

[0127] Method 1. Take 1 g (about 2.67 mmol) of iguratimod and add 200 ml of acetonitrile, heat to reflux to dissolve, then add 151 mg of potassium hydroxide (about 2.7 mmol) in 10 ml of absolute ethanol, stir and mix at 70 ° C, Reaction, if necessary, add an appropriate amount of activated carbon, stir and keep warm for decolorization and filter out the activated carbon, spin the filtrate to remove the solvent with a rotary evaporator, and wash or rinse the solid matter repeatedly with cold ethanol or ether, remove the washing solvent, and dry to obtain Ai. Lamod Potassium.

[0128] Method 2. Take 1 g (about 2.67 mmol) of iguratimod and add 300 ml of absolute ethanol, heat to reflux to dissolve, then add a solution formed by 227 mg of potassium ethylate (about 2.7 mmol) in 17 ml of ethanol, mix and react at room temperature, add 0.15% (W / V) amount of activated carbon, heated and stirred at 55-90°C for 20 minutes,...

Embodiment 3

[0129] Embodiment 3. iguratimod potassium and its preparation

[0130] Take 1g of iguratimod (about 2.67mmol) and add 160ml of acetone to heat and reflux to dissolve, then add dropwise the solution formed by 150mg of potassium hydroxide (about 2.67mmol) in 2ml of distilled water, after adding it completely, keep warm and stir to mix and react until it drops to Suction filter at room temperature, wash the filter cake with acetone 2 to 4 times, and dry to obtain iguratimod potassium and its hydrate.

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Abstract

The invention relates to a sodium salt compound of Iguratimod and a hydrate or solvate thereof. The slat of the Iguratimod is far advantageous over the Iguratimod in water solubility, powder flowability and power stability. The compounds can be used in the preparation of medicaments for treating diseases such as rheumatoid arthritis, chronic infectious arthritis, osteoarthritis and ankylosing spondylitis and relieving pains caused by muscle or soft tissue damages and arthralgia. The invention also provides a preparation method of the sodium salt compound and the hydrate or solvate thereof, the use (medicinal compositions and medicinal composition preparation and use) of the compounds in medicaments, and the like.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a derivative compound of iguratimod, a preparation method thereof and its application in medicine. Background technique [0002] Iguratimod (Iguratimod, T-614), the chemical name is N-[3-(formamido)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]- Methanesulfonamide, English name: N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]-methanesulfonamide, the molecular structure is as follows: [0003] Molecular formula C 17 h 14 N 2 o 6 S, molecular weight 374.4. [0004] Iguratimod is a new non-steroidal anti-inflammatory drug that selectively inhibits cyclooxygenase-2. It has antipyretic, analgesic, anti-arthritis, and immunomodulatory effects. It is useful for the treatment of rheumatoid arthritis, rheumatoid Arthritis, osteoarthritis and ankylosing spondylitis have excellent curative effect, and can also relieve pain and joint pain caused by muscle and soft tissue damage. It c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/22A61K31/352A61P19/02A61P19/04A61P29/00A61P19/00A61P21/00
Inventor 杨喜鸿
Owner 杨喜鸿
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