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Preparation method of linezolid and preparation thereof

A technology for linezolid and preparations is applied in the field of preparation of linezolid and lyophilized powder injection preparations, which can solve the problems of inconvenient transportation of injections, easy freezing of injections, influence on stability, etc. Long shelf life and improved stability

Inactive Publication Date: 2011-01-19
符健
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, linezolid only has injections and tablets. Due to the vast territory of China, the injections are easy to freeze in winter, which affects its stability and brings about safety problems in drug use. The injections are inconvenient to transport and have a short storage period.
Therefore, it is very necessary to develop linezolid lyophilized powder injection. At present, there is no report of linezolid lyophilized powder injection.

Method used

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  • Preparation method of linezolid and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Step 1: Synthesis of 2(S)-1-amino-3-chloro-2-propanol hydrochloride: In a 100ml three-necked flask, add 10.07g benzaldehyde, 30ml ethanol, 10.26g 25% ammonia water, and then drop slowly Add 10.19g (S)-epichlorohydrin, stir at room temperature for 15h, concentrate, add 37% HCl 10.84g and 10ml water, stir at 35°C to 45°C for 2h, separate the water layer, concentrate, ethanol-petroleum ether crystallization, Suction filtration, washing, and drying yielded 3.67 g of white solid;

[0051] Step 2: Synthesis of (S)-N-[2-acetoxy-3-chloropropyl]acetamide: In a 50ml three-necked flask, add 2.08g of compound 2(S)-1-amino-3-chloro- 2-propanol hydrochloride, 10ml of CH 2 Cl 2 , 5.37 g of Ac 2 O, 2.61g of pyridine was dropped into it at 30°C. After the dropwise addition was completed, the reaction was kept for 15h; at 6°C, 5.27g of K was added slowly. 2 CO 3 20ml of aqueous solution, the organic layer was separated, and the aqueous layer was washed with CH 2 Cl 2 Extract, comb...

Embodiment 2

[0058] Step 1: Synthesis of 2(S)-1-amino-3-chloro-2-propanol hydrochloride

[0059] In a 100ml three-necked flask, add 19.98g benzaldehyde, 40ml ethanol, 19.94g 25% ammonia water, then slowly drop in 18.76g (S)-epichlorohydrin, stir at room temperature for 255h, concentrate, add 37% HCl19.34g and 20ml of water, stirred at 35°C-45°C for 4h, separated the water layer, concentrated, crystallized with ethanol-petroleum ether, filtered with suction, washed, dried to obtain 4.57g of white solid;

[0060] Step 2: Synthesis of (S)-N-[2-acetoxy-3-chloropropyl]acetamide

[0061] In a 50ml three-necked flask, add 4.03g compound 2(S)-1-amino-3-chloro-2-propanol hydrochloride, 20ml CH 2 Cl 2 , 14.49 g Ac 2 O, 6.73g of pyridine was dropped into it at 30°C. After the dropwise addition was completed, the reaction was kept for 25h; at 6°C, slowly added 9.96g of K 2 CO 3 40ml of aqueous solution, the organic layer was separated, and the aqueous layer was washed with CH 2 Cl 2 Extract, co...

Embodiment 3

[0070] Step 1: Synthesis of 2(S)-1-amino-3-chloro-2-propanol hydrochloride

[0071] In a 100ml three-necked flask, add 13.90g benzaldehyde, 35ml ethanol, 13.60g 25% ammonia water, then slowly drop 11.80g (S)-epichlorohydrin, stir at room temperature for 20h, concentrate, add 37% HCl19.10g and 18ml of water, stirred at 35°C to 45°C for 3h, separated the water layer, concentrated, crystallized with ethanol-petroleum ether, filtered with suction, washed, and dried to obtain 14.10g of white solid;

[0072] Step 2: Synthesis of (S)-N-[2-acetoxy-3-chloropropyl]acetamide

[0073] In a 50ml three-necked flask, add 5.00g compound 2(S)-1-amino-3-chloro-2-propanol hydrochloride, 18mlCH 2 Cl 2 , 8.00gAc 2 O, 3.40g of pyridine was dropped into it at 30°C, and the dropwise addition was completed, and the reaction was kept for 20h. At 6°C, slowly add 9.30gK 2 CO 3 30ml of aqueous solution, the organic layer was separated, and the aqueous layer was washed with CH 2 Cl 2 Extract, combi...

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Abstract

The invention relates to a preparation method of linezolid and a preparation thereof, in particular to a preparation method of a linezolid raw material and a freeze-dried powder injection thereof. The preparation method mainly comprises the following steps: (1) synthesizing 2(S)-1-amino-3-chloro-2-propanol hydrochloride; (2) synthesizing (S)-N-[2-acetoxyl-3-chloropropyl] acetamide; (3) synthesizing 3-fluoro-4-morpholinyl nitrobenzene; (4) synthesizing N-carbobenzoxy-3-fluoro-4-morpholinyl aniline; (5) synthesizing the linezolid; and (6) preparing the linezolid preparation. The freeze-dried powder injection of the linezolid for injection, which is prepared by the invention, effectively improves the stability of medicines so that the medicines have longer shelf life, can be transported more conveniently and are more favorable for clinical applications. Moreover, the method of the invention for preparing the raw material linezolid and the freeze-dried powder injection thereof is simple and effective and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a preparation method of linezolid and a freeze-dried powder preparation thereof. Background technique [0002] Linezolid (Linezolid) is also known as linezolid, morpholizodone, and its trade name is Zyvox. Its chemical name is (S)-N-((3-(3-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide. The molecular formula of linezolid is C 16 h 20 FN 3 o 4 , the molecular weight is 337.35, it is a white solid, the melting point is 181.5℃~182.5℃, and its structural formula is as follows: [0003] [0004] Linezolid is a new type of oxazolidinone antibacterial drug. It is the first class of antibiotics that prevent the protein synthesis of early Gram-positive bacteria. It has broad development prospects and is suitable for the treatment of skin and soft tissue infections, hospital and community acquired pneumonia and antibiotics Mycin-resistant enterococcal infections, including ...

Claims

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Application Information

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IPC IPC(8): C07D263/20A61K9/19A61K31/5377A61P31/04
Inventor 符健
Owner 符健
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