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Improved Biapenem preparation method

A technology of biapenem and dihydrogen, which is applied in the field of preparation of biapenem, can solve the problems of low yield, need of column chromatography, and incapability of large-scale production, and achieve the effect of low-cost and high-efficiency synthesis method

Active Publication Date: 2009-06-10
NANJING SIMCERE DONGYUAN PHARM CO LTD +1
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Problems solved by technology

[0009] The present invention is by two (6,7-dihydro-5H-pyrazolo [1,2a] [1,2,4] triazolium salt-6-yl) disulfide dichloride and methanesulfonic acid After the reaction to obtain its mesylate, 6,7-dihydro-6-mercapto-5H-pyrazolo[1,2a][1,2,4]triazolium methanesulfonate can be obtained without column chromatography acid salt (i.e. side-chain mesylate), and the condensate produced by the reaction of side-chain mesylate and bicyclic parent nucleus, hydrogenation to prepare the final product can also obtain biapenem without column chromatography, solving In the prior art, the preparation of biapenem requires column chromatography, the yield is low, and it cannot be produced on a large scale, and a low-cost and high-efficiency synthesis method is provided

Method used

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Embodiment Construction

[0025] In the following section a preferred embodiment is illustrated by illustrating an example of the method of the invention. But it is in no way intended to limit the scope of the invention.

[0026] Preparation of Biapenem Example

[0027] Step 1 Preparation of bis(6,7-dihydro-5H-pyrazolo[1,2a][1,2,4]triazolium-6-yl)disulfide dimesylate

[0028]

[0029] Dissolve 8 g of bis(6,7-dihydro-5H-pyrazolo[1.2a][1.2.4]triazolium-6-yl)disulfide dichloride (II) in 20 ml of methanol, 5 ml of methanesulfonic acid was added under stirring at room temperature, and 7.5 ml of acetone was added to the residue concentrated under reduced pressure for crystallization to obtain 7.8 g of off-white solid.

[0030] Step 2 Preparation of 6,7-dihydro-6-mercapto-5H-pyrazolo[1,2a][1,2,4]triazolium mesylate

[0031]

[0032] The product in step 1 was off-white solid, bis(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-6-yl)disulfide disulfide Add 6g of mesylate (III), 30ml of tetrahydrofuran an...

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Abstract

The invention relates to a method for preparing biapenem. It comprises: carrying out salt precipitation with bi (6, 7- dihydro- 5H- pyrazole [1. 2a][1.2.4] triazole onium salt- 6- group ) dithioether bichloride and methanesulfonic acid, then getting the mesilate of 6, 7- dihydro- 5H- pyrazole [1. 2a][1.2.4] triazole onium salt- 6- group ) dithioether bichloride (side-chain mesilate)without column chromatography. The final product biapenem can be produced with mesilate which is produced by using side-chain mesilate and doublecyclic parent nucleus without column chromatography. The invention is characterized by reduced cost, temperate reaction condition, and suitability for industrial and large- scale production.

Description

technical field [0001] The invention relates to an improved preparation method of biapenem, which is low in cost, effective and capable of large-scale industrial production. Background technique [0002] Carbapenem antibiotics (Carbapenems) are atypical β-lactam antibiotics with a new structure. It is used to treat severe nosocomial infections, multidrug-resistant bacterial infections, and mixed infections. In recent years, Merck’s Imipenem (Imipenem) and Japan’s Sankyo’s Panipenem have been used clinically in my country. Panipenem and Meropenem from Sumitomo, Japan. [0003] Biapenem (Biapenem) is a new type of 1β-methyl carbapenem antibiotics. This product is a 1β-methyl carbapenem with a bicyclic triazole on the 2-position sulfur. It has a broad antibacterial spectrum and is effective against leather It has good bactericidal effect on gram-negative, gram-positive, aerobic and anaerobic bacteria; it is stable to human DHP-I, does not need to be combined with DHP-I inhibit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/06
Inventor 丁磊罗兴洪郭子维王光明殷晓进吴海峰
Owner NANJING SIMCERE DONGYUAN PHARM CO LTD
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