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Synthetic methods of ceftazidime intermediate and ceftazidime

A ceftazidime and synthetic method technology, applied in the field of drug synthesis, can solve the problems of low product purity and low process yield, and achieve the effects of less three waste discharge, high product purity, and simplified process flow

Active Publication Date: 2012-03-28
QILU ANTIBIOTICS PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the yield of this process is low, and the product purity is only 72% to 80%, so it cannot be used in the next step of reaction

Method used

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  • Synthetic methods of ceftazidime intermediate and ceftazidime
  • Synthetic methods of ceftazidime intermediate and ceftazidime
  • Synthetic methods of ceftazidime intermediate and ceftazidime

Examples

Experimental program
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Effect test

Embodiment 1

[0044] [embodiment 1] the synthesis of ceftazidime intermediate (formula 1, wherein HX is HCl) monohydrate:

[0045] 30g (0.11mol) of 7-aminocephalosporanic acid, 300ml of dichloromethane, and 35ml (0.16mol) of hexamethyldisilazane were placed in a reaction flask, heated to reflux for 8 hours, and N,N-diethyl Aniline 29ml (0.18mol), trimethylsilyl iodide 32g (0.16mol), react at room temperature for 3hr, add pyridine 18ml (0.22mol) under ice bath, and continue to react for 1hr;

[0046] Add 35ml of methanol dropwise, add 6ml of hydrogen peroxide (0.13mol), 80ml of concentrated hydrochloric acid, and 100ml of water, stir until all the solids are dissolved, let it stand for stratification, add 500ml of acetone to the water phase, add triethylamine to adjust the pH to 3.0, filter, and 100ml of acetone Washing, drying in vacuo to get light yellow solid 34.4g (91%), content 83.5%, purity > 98%, moisture: 5.5%, product detects through potentiometric titration that the chloride ion co...

Embodiment 2

[0047] [embodiment 2] the synthesis of ceftazidime intermediate (formula 1, wherein HX is HCl) monohydrate:

[0048] As described in Example 1, the difference is that the oxidant is replaced by FeCl 3 26g (0.16mol), after extraction, add 500ml of acetone to the water phase, add triethylamine to adjust the pH to 3.0, filter, wash with 100ml of acetone, and dry in vacuo to obtain 34.1g (90%) of a light yellow solid with a content of 83.9% and a purity of >98% , KF: 5.6%, chloride ion content: 10.84%, which is the monohydrochloride monohydrate of the ceftazidime intermediate (Formula 1, wherein HX is HCl).

Embodiment 3

[0049] [embodiment 3] the synthesis of ceftazidime intermediate (formula 1, wherein HX is HCl) monohydrate:

[0050] As described in Example 1, the difference is that the oxidizing agent is replaced by 12ml (0.08mol) of peracetic acid with a mass concentration of 20%. After extraction, 500ml of acetone is added to the water phase, and triethylamine is added to adjust the pH to 3.0, filtered, and washed with 100ml of acetone. , dried in vacuo to give light yellow solid 33.9g (90%), content 84.3%, purity > 98%, KF: 5.2%, chloride ion content: 10.2%, be ceftazidime intermediate (formula 1, wherein HX is HCl) single Hydrochloride monohydrate.

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Abstract

The invention relates to a synthetic method of ceftazidime intermediate; 7-amino cephalsporanic acid is used as a raw material; a silanization reaction, an iodination reaction, and a pyridine reaction are performed; the obtained product is added with an oxidant, and hydrochloric acid or is added into a mixed solvent of an organic solvent and water to prepare a halogen acid salt of the ceftazidimeintermediate (6R, 7R)-7-amino-3-pyridine methyl-ceph-3-ene-4-carboxylic acid. The invention also provides a method for preparing ceftazidime by using the obtained intermediate halogen acid salt. The ceftazidime intermediate and ceftazidime prepared by the methods have high yield, and low production cost; the operation is simple; the discharge of three wastes is less; treatment and recovery are easy, and the methods are applicable to industrial production.

Description

technical field [0001] The invention relates to a ceftazidime intermediate high-purity hydrohalide salt and a synthesis method of ceftazidime, belonging to the technical field of medicine synthesis. Background technique [0002] Cephalosporins are a series of semi-synthetic antibiotics obtained by modifying the side chain of cephalosporin C extracted from crown cephalosporin culture solution. Its advantages are: wide antibacterial spectrum, relatively stable to acid and β-lactamase produced by various bacteria. Since the 1970s, a variety of cephalosporins have been widely used in clinics, providing a good antibacterial treatment for bacterial infections, especially infections caused by strains resistant to penicillin and other antibiotics, nosocomial infections and infections in people allergic to penicillins. Variety. It not only has excellent pharmacological characteristics similar to penicillin, but also is more suitable for clinical needs. It is a class of antibiotics ...

Claims

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Application Information

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IPC IPC(8): C07D501/18C07D501/04C07D501/46
Inventor 李凤侠王晓艳王勇进贺俊华付景龙王立
Owner QILU ANTIBIOTICS PHARMA
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