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Method of preparing ketolide macrolide antibiotics

A technology for macrolides and antibiotics, applied in the field of preparation, can solve the problems of difficult removal, low yield, unstable structure of carbonylimidazole, etc., achieve good product purity, high reaction yield, and avoid the effect of impurity formation

Inactive Publication Date: 2017-07-07
上海启雁实业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the carbonylimidazole intermediate I is not very stable due to the carbonylimidazole structure, and some carbonylimidazole impurities (imp A) will be dropped when it is docked with the side chain. Since they all have a macrocyclic lactone structure, their properties are relatively close, and it is difficult to remove. and low yield

Method used

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  • Method of preparing ketolide macrolide antibiotics
  • Method of preparing ketolide macrolide antibiotics
  • Method of preparing ketolide macrolide antibiotics

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Embodiment Construction

[0028] The preferred embodiments of the present invention are given below in conjunction with the accompanying drawings to describe the technical solution of the present invention in detail.

[0029] Such as figure 1 Shown, the present invention prepares the method for ketolide macrolide antibiotics and comprises the following steps:

[0030] Step 1, the side chain is first reacted with triphosgene to generate isocyanate, namely compound III;

[0031] In step 2, the isocyanate obtained in step 1 is docked with intermediate IV, and cyclized to generate an oxazolone compound;

[0032] Step 3, removing the hydroxyl protecting group from the oxazolone compound obtained in Step 2 to obtain telithromycin.

[0033] Synthesis of Intermediate IV

[0034] In reaction bottle, add clarithromycin (50g, 0.067mol), triethylamine (18.75ml, 0.135mol, 2eq), ethyl acetate (350ml) stir and mix, add benzoic anhydride (22.5g, 0.1mol, 1.5eq), the addition was completed, and the reaction was stir...

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Abstract

The invention discloses a method of preparing ketolide macrolide antibiotics. The method of preparing ketolide macrolide antibiotics comprises the following steps: S1, performing a reaction on a side chain with triphosgene to generate isocyanate; S2, performing butt-joint of isocyanate obtained in the step 1 with isocyanate and performing cyclization to generate an oxazolone compound; and S3, removing a hydroxyl protective group from the oxazolone compound obtained in the step 2 to obtain telithromycin. The method disclosed by the invention does not use an unstable carbonyl imidazole intermediate, so that impurities of macrolide structures are prevented from being generated, and relatively high reaction yield and better product purity are obtained.

Description

technical field [0001] The invention relates to a preparation method, in particular to a method for preparing ketolide macrolide antibiotics. Background technique [0002] Macrolide antibiotics are an important class of antibacterial and anti-infective drugs. After structural modification of clarithromycin, it was found that ketolide derivatives such as telithromycin and solithromycin have better antibacterial activity and can Used in the treatment of acquired pneumonia and other diseases. [0003] According to industry experts' prediction: the next century will be the era of macrolide antibiotics. As a new class of drugs, ketolides are derived from macrolide antibiotics. A ketone group is introduced at the 3-position to replace the neutral sugar group, which improves the stability of the weak acid environment. Due to the change of structure, the antibacterial effect of this kind of drug is enhanced, especially the antibacterial activity of drug-resistant pathogenic bacter...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00
CPCC07H1/00C07H17/08Y02P20/55
Inventor 王奇
Owner 上海启雁实业有限公司
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