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Preparation method of ibudilast

A technology of ibudilast and step 2, applied in the preparation field of ibudilast, can solve the problems of difficult operation, low yield, inability to realize large-scale industrial production, etc., and achieves high product purity, high yield, and reduced types and the effect of the quantity used

Inactive Publication Date: 2012-08-01
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The present invention aims to solve the problem that the existing ibudilast method has difficult operation or low yield, which leads to the inability to realize industrialized large-scale production, and provides a preparation method of ibudilast

Method used

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  • Preparation method of ibudilast
  • Preparation method of ibudilast
  • Preparation method of ibudilast

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specific Embodiment approach 1

[0015] Specific embodiment one: present embodiment is a kind of preparation method of ibudilast, specifically completes according to the following steps:

[0016] 1. First, dissolve hydroxylamine oxysulfonic acid in the solvent, then add 2-picoline dropwise under ice-bath condition, after adding 2-picoline, raise the temperature to 50℃~90℃, and React at ~90°C for 0.5h~1h, then add inorganic base I, and stir at a stirring speed of 100r / min~300r / min until no bubbles are generated, then stir at a speed of 45r / min~90r / min and a temperature of 40 Rotary evaporation method at ℃~60℃ to constant weight, the obtained solid was washed 2 to 3 times with absolute ethanol, the filtrates obtained from the washing were combined, and the inorganic acid was added dropwise at the temperature of -15℃~-10℃ Or carry out acidification treatment with organic acid, the acidification treatment time is 0.5h~1h, and finally filter to obtain 1-amino-2-picoline acid compound;

[0017] 2. First, add 1-ami...

specific Embodiment approach 2

[0023] Specific embodiment two: the difference between this embodiment and specific embodiment one is: the solvent described in step one is selected from deionized water, methylene chloride, benzene, toluene and xylene. Others are the same as in the first embodiment.

specific Embodiment approach 3

[0024] Specific embodiment three: the difference between this embodiment and specific embodiment one or two is: the inorganic base I described in step one is potassium carbonate, sodium carbonate, sodium hydroxide or potassium hydroxide. Others are the same as in the first or second embodiment.

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Abstract

A preparation method of ibudilast relates to medicine compound compounding and aims at resolving the problem that the existing preparation method of the ibudilast is difficult to operate or low in yield and cannot achieve industrial production accordingly. The method includes 1 preparing 1-amino-2-picoline oxide and 2 adopting the 1-amino-2-picoline oxide to prepare the ibudilast. The method has the advantages that the preparation method is convenient in post-processing, the yield is 80% to 95%, and type and quantity of used solvent in industrialization are reduced; 2 medicine and agents used in the method are low in price, easy to obtain, high in yield and low in cost, thereby being suitable for industrialized production; and 3 a final product of the method is prepared by reduced pressure distillation and purification, and the purity can reach over 99%. The preparation method is mainly used in preparation of the ibudilast.

Description

technical field [0001] The invention relates to a synthesis of pharmaceutical compounds, in particular to a preparation method of ibudilast. Background technique [0002] 2-Methyl-1-[2-(1-methylethyl)-pyrazolo[1,5-a]pyrimidin-3-yl]-1-propanone (Ibudilast, generic drug name: IBUDILAST ) is an anti-allergic asthma drug, which can resist leukotrienes and platelet activating factors, promote the secretion of mucus in the airway, the function of airway cilia, enhance the effect of prostacyclin, increase cerebral blood flow, and improve brain metabolism. For the treatment of bronchial asthma, sequelae of cerebrovascular embolism, cerebral arteriosclerosis, etc. [0003] The preparation method of ibudilast mainly contains following two kinds: [0004] Method 1: (The Journal of Organic Chemistry, 1968, 33, 3766-3770) the synthetic route is as follows: [0005] [0006] This route uses 2-picoline as a raw material to obtain 1-amino-2-picoline iodide, and then reacts with pyrimi...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61P9/10A61P11/06
Inventor 张华史成阳鲁国明王阳李强迟帅苑兰兰
Owner HEILONGJIANG UNIV
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