Preparation method of gemifloxacin side chain compound

A technology for gemifloxacin and a compound is applied in the field of preparation of gemifloxacin side chain compounds, can solve problems such as unfavorable industrial production, unfavorable industrial production, low yield and the like, and achieves the effects of low cost, easy realization and simple process

Active Publication Date: 2022-05-31
北京阳光诺和药物研究股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] This route includes 5 steps of chemical reactions. The starting material N-tert-butoxycarbonyl-4-cyano-3-pyrrolidone needs to be reduced by Raney nickel and palladium carbon in two steps. The reduction pressure is above 4Mpa, which is not conducive to industrial production.
[0015] In summary, the existing synthetic techniques all have the disadvantages of long routes, low yields, and unfavorable industrial production. It is urgent to develop a new route to solve this problem.

Method used

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  • Preparation method of gemifloxacin side chain compound
  • Preparation method of gemifloxacin side chain compound
  • Preparation method of gemifloxacin side chain compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

Each step is described as follows:

1. compound V obtains imine compound through palladium carbon catalytic hydrogenation, i.e. intermediate state 1, LC-Ms shows target chromatographic peak

The mass spectrum signal of 242 is the M+H peak of intermediate state 1, as shown in Figure 9;

2. after adding Boc acid anhydride, LC-Ms shows, and the chromatographic peak (15.192min) of intermediate state 1 is converted into the color of intermediate state 2

Spectral peak (11.560min), because the intermediate state 2 is not easy to ionize, its mass spectrum signal is not captured, as shown in Figure 10;

3. continue catalytic hydrogenation, intermediate state 2 is converted into target compound VI, and LC-Ms shows the mass spectrum signal of target chromatographic peak.

Number is 366, which is the M+Na peak of compound VI, as shown in Figure 2;

By this step-by-step feeding mode, reaction pressure can be reduced, the generation of side reaction impurities is avoided, and the purity ...

Embodiment 2

[0096] Temperature: 45 °C;

[0103]

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Abstract

The invention discloses a preparation method of gemifloxacin side chain compound. The preparation method comprises the following steps: S1, 1-N-tert-butoxycarbonyl-4-cyano-3-pyrrolidone reacts with methoxylamine hydrochloride to obtain the compound shown in formula (V); S2, in an inert In the atmosphere, at a temperature of 10-50°C and in the presence of palladium carbon, the compound shown in formula (Ⅴ) is subjected to a hydrogenation reduction reaction for 1-3 hours under a hydrogen atmosphere of 0.1-0.5Mpa; then Boc anhydride is added, and the Continue the hydrogenation reduction reaction at 10-50°C and 0.1-0.5Mpa for 4-8 hours to obtain the compound shown in formula (VI); S3, the compound shown in formula (VI) reacts with an acid to remove the protecting group to obtain Gemifloxacin side chain compound represented by formula (I). The preparation method of the present invention has simple process, very mild reaction conditions, and is easy to realize; (2) the raw material price is low, and the cost is low; (3) a new and effective synthesis process route of gemifloxacin side chain is created.

Description

Preparation method of gemifloxacin side chain compound technical field The present invention relates to a kind of preparation method of gemifloxacin side chain compound, belong to the technical field of pharmaceutical synthesis. Background technique Gemifloxacin is the 4th generation new fluoroquinolone antibacterial agent developed by Korea LG chemical company, as compound Shown in (III): 7-(4-aminomethyl-3-methoxyiminopyrrolidine-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4- Dihydro[1,8]naphthalene-3-carboxylic acid, trade name Factive, has the advantages of good curative effect and less toxic and side effects. [0003] Gemifloxacin was the first approved treatment for community-acquired disease caused by multidrug-resistant Streptococcus pneumoniae strains (MDRSP). Antibiotics for pneumonia. For the treatment of infections caused by Streptococcus pneumoniae, methicillin-resistant Staphylococcus aureus, Haemophilus influenzae, or Acute bronchitis, chronic bronchitis, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/22
CPCC07D207/22Y02P20/55
Inventor 刘宇晶马昂罗桓张文腾张强赵隋红孙跃军袁伟锋童元峰谌宗永
Owner 北京阳光诺和药物研究股份有限公司
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