Preparation method of prulifloxacin

A technology of prulifloxacin and organic solvent, which is applied in the new preparation field of quinolone antibacterial drugs, can solve the problems of low reactivity, poor reactivity and effect, difficulty in source and storage, etc., and achieves high activity in the preparation process and is beneficial to The effect of industrial production and easy operation

Active Publication Date: 2012-10-10
SICHUAN KELUN PHARMA RES INST CO LTD
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Problems solved by technology

[0005] 4-Chloromethyl-5-methyl-1,3-dioxolone-X can be of the following chemical formula 4-chloromethyl-5-methyl-1,3-dioxole Diketone-Cl (DMDO-Cl), 4-Chloromethyl-5-methyl-1,3-dioxolepentane-Br (DMDO-Br), 4-Chloromethyl-5-methanol Any of the three substances o

Method used

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  • Preparation method of prulifloxacin
  • Preparation method of prulifloxacin
  • Preparation method of prulifloxacin

Examples

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experiment example 1

[0017] Experimental Example 1: Comparative Experiment

[0018] 1. Prepare prulifloxacin with reference to the method reported in the literature Chem.Pharm.Bull.43(11)1872-1877,1995

[0019] DMDO-Cl (2.26g, 15.2mmol) was dissolved in 5.5ml of DMF, sodium bromide (3.08g, 30.3mmol) was added, stirred at 303K for 1 hour, 11ml of acetone was added, the reaction was continued for 1 hour, the reaction liquid was filtered, and the filtrate was decompressed Acetone was removed, and this solution contained 14.1 mmol of DMDO-Br. Compound II (5.00g, 11.6mmol) was put into 32ml of DMF, the above DMDO-Br solution was added, potassium bicarbonate (2.69g, 26.9mmol) was added within 10 minutes, stirred at 304K for 3 hours, and then the reaction solution was poured into 120ml of ice water, Precipitate was precipitated, filtered, and vacuum-dried to obtain 4.80 g of crude prulifloxacin, with a yield of 89.7% and a purity of 89.9%.

[0020] 2. Reference Chem.Pharm.Bull.43 (11) 1872-1877, 1995 r...

Embodiment 1

[0033] DMDO-Cl (2.24g, 15.1mmol) was dissolved in 5.5ml of DMF, sodium iodide (3.28g, 22.0mmol) was added, stirred at 303K for 1 hour, 11ml of acetone was added, and stirring was continued for 1 hour. Add 32ml of DMF, compound II (5.00g, 11.6mmol), potassium bicarbonate (2.69g, 26.9mmol) to the reaction solution, stir at 293K for 3 hours, then pour the reaction solution into 120ml of ice water, precipitate out, filter, and dry in vacuo to obtain 4.93g prulifloxacin crude product, the yield is 92.1%, and the purity is 94.2%.

Embodiment 2

[0035]DMDO-Cl (6.44g, 43.4mmol) was dissolved in 16ml of DMF, sodium iodide (8.87g, 59.2mmol) was added, stirred at 303K for 1 hour, 30ml of acetone was added, and stirring was continued for 1 hour. Add 90ml DMF, compound II (15.00g, 34.8mmol) to the solution, add DIPEA (5.28g, 39.6mmol) dropwise within 10 minutes, stir at 304K for 1 hour, then pour the reaction solution into 120ml ice water, precipitate out, filter, vacuum Dry to obtain 14.83g of prulifloxacin crude product, the yield is 92.3%, and the purity is 94.3%.

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Abstract

The invention relates to a synthetic method of prulifloxacin, comprising the steps of: stirring DMDO-Cl and sodium iodide in an organic solvent, carrying out a one-pot reaction of the unseparated reaction liquid, a compound 2 and alkali substances to obtain the prulifloxacin. The synthetic method of the invention is advantaged in that the raw material DMDO-Cl used in the invention is cheap, easily available, and easily stored and transported, the prulifloxacin synthesized by the method has high yield, increased purity, and the operation is convenient.

Description

technical field [0001] The invention relates to a new preparation method of quinolone antibacterial drugs, in particular to a preparation method of prulifloxacin. Background technique [0002] Prulifloxacin is a fluoroquinolone antibacterial drug jointly developed by Nippon Shinyaku Co., Ltd. and Meiye Zhika Co., Ltd. It was first launched in Japan in 2002. This product has broad-spectrum antibacterial activity, the antibacterial activity against Staphylococcus aureus is similar to ofloxacin (ofloxacin), greater than ciprofloxacin (ciprofloxacin), the activity against streptococcus is 5 times greater than ofloxacin, and the activity against large intestine The activity of bacilli is equivalent to that of ciprofloxacin, and its antibacterial activity against Klebsiella pneumoniae, Serratia marcescens, and Pseudomonas aeruginosa is 2 to 3 times greater than that of ciprofloxacin and ofloxacin, and it can be used clinically to treat pneumonia , Acute and chronic bronchitis, ph...

Claims

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Application Information

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IPC IPC(8): C07D513/04
Inventor 张翔李明验黄耀宗
Owner SICHUAN KELUN PHARMA RES INST CO LTD
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