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Synthetic technology for ofloxacin

A synthesis process, ofloxacin technology, applied in the field of ofloxacin synthesis process, can solve the problems of reduced yield, long chemical synthesis route, and reduced content of final products, so as to reduce the loss of intermediates and improve the condensation reaction Yield, the effect of reducing the discharge of three wastes

Inactive Publication Date: 2017-09-29
武汉励合生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Along with the wide use of ofloxacin, its demand grows rapidly, and in the processing route of prior art, because the chemical synthesis route is long, and the unreacted intermediate is easy to react with aminopropanol to generate impurities, and reduces the yield. rate, so that the final product content is reduced

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The present invention proposes a kind of synthetic technique of ofloxacin, comprises the steps:

[0021] S1. Choose (S)-(-)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7hydropyridine[1,2,3-de][1, 4) Benzazine-6-carboxylic acid, N-methylpiperazine, dimethyl sulfoxide as raw materials, and (S)-(-)-9,10-difluoro-2,3-dihydro-3 Molar mass of -methyl-7-oxo-7-hydropyridine[1,2,3-de][1,4]benzoperazine-6-carboxylic acid, N-methylpiperazine, dimethyl sulfoxide The ratio is 1:1:3, and sealed storage;

[0022] S2. Select the reactor as an auxiliary tool, and weigh (S)-(-)-9,10-difluoro-2,3-dihydro-3-methyl-7oxo-7hydropyridine in proportion [1 , 2,3-de] [1,4] benzoperazine-6-carboxylic acid, N-methylpiperazine, dimethyl sulfoxide as raw materials, and (S)-(-)-9,10- Difluoro-2,3-dihydro-3-methyl-7-oxo-7hydropyridinium[1,2,3-de][1,4]phenazine-6-carboxylic acid, N-methyl Piperazine and dimethyl sulfoxide were sequentially added to the reactor, heated and stirred for 4 hours under an e...

Embodiment 2

[0033] The present invention proposes a kind of synthetic technique of ofloxacin, comprises the steps:

[0034] S1. Choose (S)-(-)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7hydropyridine[1,2,3-de][1, 4) Benzazine-6-carboxylic acid, N-methylpiperazine, dimethyl sulfoxide as raw materials, and (S)-(-)-9,10-difluoro-2,3-dihydro-3 Molar mass of -methyl-7-oxo-7-hydropyridine[1,2,3-de][1,4]benzoperazine-6-carboxylic acid, N-methylpiperazine, dimethyl sulfoxide The ratio is 1:1:3, and sealed storage;

[0035] S2. Select the reactor as an auxiliary tool, and weigh (S)-(-)-9,10-difluoro-2,3-dihydro-3-methyl-7oxo-7hydropyridine in proportion [1 , 2,3-de] [1,4] benzoperazine-6-carboxylic acid, N-methylpiperazine, dimethyl sulfoxide as raw materials, and (S)-(-)-9,10- Difluoro-2,3-dihydro-3-methyl-7-oxo-7hydropyridinium[1,2,3-de][1,4]phenazine-6-carboxylic acid, N-methyl Piperazine and dimethyl sulfoxide were sequentially added to the reactor, heated and stirred for 5 hours under an e...

Embodiment 3

[0046] The present invention proposes a kind of synthetic technique of ofloxacin, comprises the steps:

[0047] S1. Choose (S)-(-)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7hydropyridine[1,2,3-de][1, 4) Benzazine-6-carboxylic acid, N-methylpiperazine, dimethyl sulfoxide as raw materials, and (S)-(-)-9,10-difluoro-2,3-dihydro-3 Molar mass of -methyl-7-oxo-7-hydropyridine[1,2,3-de][1,4]benzoperazine-6-carboxylic acid, N-methylpiperazine, dimethyl sulfoxide The ratio is 1:1:3, and sealed storage;

[0048] S2. Select the reactor as an auxiliary tool, and weigh (S)-(-)-9,10-difluoro-2,3-dihydro-3-methyl-7oxo-7hydropyridine in proportion [1 , 2,3-de] [1,4] benzoperazine-6-carboxylic acid, N-methylpiperazine, dimethyl sulfoxide as raw materials, and (S)-(-)-9,10- Difluoro-2,3-dihydro-3-methyl-7-oxo-7hydropyridinium[1,2,3-de][1,4]phenazine-6-carboxylic acid, N-methyl Piperazine and dimethyl sulfoxide were sequentially added to the reactor, heated and stirred for 7 hours under an e...

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Abstract

The invention discloses a synthetic technology for ofloxacin. The synthetic technology comprises the following steps: weighting (S)-(-)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7 hydrogen pyridine (1,2,3-de) (1,4) benzo oxazine-6 carboxylic acid, N-methyl piperazine and dimethyl sulfoxide at a ratio; adding into a reactor in turn; heating, stirring and reacting for 4-8h under the environment at 110-150 DEG C, thereby forming a mixed solution; filtering, adding an alkyl imidazole L-tartrate ionic solution, and heating, stirring and reacting for 30-45min under the environment at 60-80 DEG C; adding an organic solvent, mixing and stirring; reducing pressure and recycling dimethyl sulfoxide and excessive N-methyl piperazine; utilizing 90-95% ethyl alcohol to crystallize the residual solution; and performing hydrolysis reaction, thereby obtaining the ofloxacin. The invention can effectively reduce the happening of side reaction and can increase the yield of condensation reaction.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a synthesis process of ofloxacin. Background technique [0002] Ofloxacin, yellowish crystalline powder; odorless, bitter taste; gradually changing color when exposed to light. This product is slightly soluble in chloroform, slightly soluble in methanol, easily soluble in glacial acetic acid, slightly soluble in dilute acid and 0.1mol / L sodium hydroxide solution. The main component of ofloxacin hydrochloride is ofloxacin. Its chemical name is: (S)-(-)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H - Pyrido[1,2,3-de]-[1,4]benzoxazine-6-carboxylic acid hemihydrate. Molecular formula: C18H20FN3O4·1 / 2H2O, molecular weight: 370.38. [0003] Along with the wide use of ofloxacin, its demand grows rapidly, and in the processing route of prior art, because the chemical synthesis route is long, and the unreacted intermediate is easy to react with aminopro...

Claims

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Application Information

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IPC IPC(8): C07D498/06
CPCC07D498/06
Inventor 彭凡李娜田军叶杨欢叶志伟
Owner 武汉励合生物医药科技有限公司
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