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Iloperidone impurity and its preparation method

A technology for iloperidone and impurities, which is applied in the testing of iloperidone and its impurities, the impurity of iloperidone and its preparation, and can solve the problems of low product purity and lack of single impurity control

Inactive Publication Date: 2013-03-06
CHONGQING PHARMA RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] Therefore, in the existing iloperidone preparation technology, there are deficiencies such as low product purity and lack of control of individual impurities.

Method used

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  • Iloperidone impurity and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Embodiment 1: the HPLC analysis method of iloperidone

[0079] Get an appropriate amount of iloperidone, add an appropriate amount of acetonitrile for sonication to dissolve, dilute with mobile phase to make a solution containing about 0.3 mg per 1 ml, as the test solution, according to the high performance liquid chromatography (Chinese Pharmacopoeia 2010 version two Appendix VD) Determination. Octadecylsilane bonded silica gel is used as filler, ammonium acetate solution (take 5.0g of ammonium acetate, add 1000ml of water to dissolve, shake well)-acetonitrile (volume ratio 50:50) as mobile phase, and the detection wavelength is 230nm. The number of theoretical plates should not be less than 2000 based on the calculation of iloperidone. Precisely measure 20 μl of the test solution, inject it into a liquid chromatograph, record the chromatogram to 6 times the retention time of the main peak, and calculate the purity of iloperidone with the area normalization method. I...

Embodiment 2

[0081] Embodiment 2: the preparation of formula I compound

[0082] Suspend 10g of iloperidone in 500mL of acetonitrile, add 5ml of 30% hydrogen peroxide dropwise, and react at room temperature for 24h. The reaction solution was extracted twice with dichloromethane, the combined dichloromethane layers were washed with water, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and the residue was purified with acetonitrile to obtain 1-(3-(4-acetyl- 2-methoxyphenoxy)propyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine-N-oxide (compound of formula I). HPLC purity 99.1%.

[0083] MH in mass spectrum [ESI-MS, m / z] ＋ Peak is 443.

[0084] 13C NMR (400MHz, DMSO) δ (ppm): 196.3, 164.6, 163.1, 160.7, 152.3, 148.6, 129.9, 123.6, 123.0, 117.0, 112.7, 111.8, 110.3, 97.5, 67.7, 67.0, 63.1, 55.5, 26.3, 24.6, 22.0;

[0085] 1H NMR (400MHz, DMSO) δ (ppm): 8.01-8.03 (1H,q), 7.70-7.73 (1H,dd), 7.61-7.63 (1H,dd), 7.45-7.46 (1H,d), 7.30- 7.34...

Embodiment 3-6

[0087] According to the method described in Example 2, different organic solvents and oxidizing agents were selected to obtain the compound of formula I, and the results are shown in Table 1 below:

[0088] Table 1

[0089] Numbering Organic solvents oxidizing agent HPLC purity of compound of formula Ⅰ Example 3 N,N-Dimethylformamide hydrogen peroxide 97.1％ Example 4 Acetonitrile tert-butyl hydroperoxide 98.3％ Example 5 Acetonitrile m-chloroperoxybenzoic acid 98.6％ Example 6 Acetonitrile peracetic acid 97.8％

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Abstract

The invention relates to an iloperidone impurity, its preparation method, its use as an iloperidone quality control reference standard substance, and an iloperidone and iloperidone impurity measurement method. The impurity is 1-(3-(4-acetyl-2-methoxyphenoxy)propyl)-4-(6-fluoro-1,2-benzisoxazole-3-yl)piperidine-N-oxide (a compound of formula I).

Description

technical field [0001] The invention belongs to the field of chemistry and analysis, and in particular relates to an impurity of iloperidone and a preparation method thereof, the use of the impurity as a reference standard for quality control of iloperidone, and a test method for iloperidone and the impurity thereof. Background technique [0002] Schizophrenia is the most common type of mental illness characterized by changes in basic personality, splits in thinking, emotion, and behavior, and incoordination between mental activities and the environment. According to the data of the World Health Organization, schizophrenia still has the highest prevalence among various severe mental illnesses, affecting 7‰ of adults in the world, mainly people aged 15-35. Schizophrenia seriously impairs the workforce and has profound adverse effects on personal development, family and society. Over the past ten years, the prevalence of schizophrenia in China has shown an upward trend. Accor...

Claims

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Application Information

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IPC IPC(8): C07D413/04G01N30/02
Inventor 谢峰姜芬龚恒源石瑞娜邓杰罗杰叶文润
Owner CHONGQING PHARMA RES INST
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