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1/4 water cefmenoxime hydrochloride compound and pharmaceutical composition thereof

A technology of cefmenoxime hydrochloride and compound, which is applied in the field of 1/4 water cefmenoxime hydrochloride compound and its pharmaceutical composition, and can solve the problems of long synthetic process route, poor crystal form, excessive use of organic solvents and the like

Inactive Publication Date: 2018-12-28
HAINAN LINGKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the past, the synthesis process of cefmenoxime hydrochloride was long and complex, and the conversion rate of the organic solvent used was low. The solvent was not easy to recover, and other separation methods such as adsorption were required. Instead of using a single recrystallization method, the obtained crystal form was not good. , not easy to separate and dry
[0005] The present invention is committed to solving the problems of too long synthesis route, complex process, excessive use of organic solvents, etc., improving the conversion rate of the product, and preparing the cefmenoxime hydrochloride compound of single crystal form. The process route is simple, the synthesis yield is high, and the Production cost, the method of recrystallization is used to prepare crystals, which is suitable for industrial production

Method used

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  • 1/4 water cefmenoxime hydrochloride compound and pharmaceutical composition thereof
  • 1/4 water cefmenoxime hydrochloride compound and pharmaceutical composition thereof
  • 1/4 water cefmenoxime hydrochloride compound and pharmaceutical composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Preparation of 1 / 4 water cefmenoxime hydrochloride compound

[0032] Preparation Process

[0033] (1) Add 300ml of dichloromethane and 27.5g of 7-ACA to Reactor 1, raise the temperature to 35°C, and keep stirring, add 4.5ml of triethylamine, stir to dissolve, add 2-(2aminothiazole-4 -yl)-(cis)-2-methoxyimine acetylthiobenzothiazole active ester (MAEM) (42.2g) and N,N dimethylacetamide 1ml, stirred for 1h, then added 200ml of distilled water, Continue to stir for 15 minutes;

[0034] (2) After the above-mentioned reaction finishes, stand and separate layers, extract the organic phase with water, combine the water phases, wash with dichloromethane, then adjust the pH=3.1 of the water phase with 2mol / l hydrochloric acid solution, separate out white crystals, filter, filter The cake was washed with water and dried under vacuum to obtain off-white solid Ⅰ;

[0035] (3) Add 45.1g of white solid I to a 2000ml three-necked flask, then add 1000ml of distilled wa...

Embodiment 2

[0040] Embodiment 2: Preparation of 1 / 4 water cefmenoxime hydrochloride compound

[0041] Preparation Process

[0042] (1) Add 150ml of dichloromethane and 14g of 7-ACA to Reactor 1, raise the temperature to 40°C, and keep stirring, add 2.5ml of triethylamine, stir to dissolve, add 2-(2aminothiazole-4- base)-(cis)-2-methoxyimine acetylthiobenzothiazole active ester (MAEM) (21.2g) and N,N dimethylacetamide 0.5ml, stirred for 1.5h, then added distilled water 100ml , continue to stir for 15 minutes;

[0043] (2) After the above-mentioned reaction finishes, stand and separate layers, extract the organic phase with water, combine the water phases, wash with dichloromethane, then adjust the pH=3.1 of the water phase with 2mol / l hydrochloric acid solution, separate out white crystals, filter, filter The cake was washed with water and dried under vacuum to obtain off-white solid Ⅰ;

[0044] (3) Add 25.1g of white solid I into a 2000ml three-necked flask, then add 500ml of distilled...

Embodiment 3

[0049] Embodiment 3: Preparation of 1 / 4 water cefmenoxime hydrochloride compound

[0050] Preparation Process

[0051] (1) Add 450ml of dichloromethane and 42.2g of 7-ACA to Reactor 1, raise the temperature to 30°C, and keep stirring, add 7.5ml of triethylamine, stir to dissolve, add 2-(2aminothiazole-4 -yl)-(cis)-2-methoxyimine acetylthiobenzothiazole active ester (MAEM) (63.5g) and N,N dimethylacetamide 1.5ml, stirred for 2.0h, then added distilled water 300ml, continue stirring for 15min;

[0052] (2) After the above-mentioned reaction finishes, let the layers stand, extract the organic phase with water, combine the water phases, wash with dichloromethane, then adjust the pH=2.9 of the water phase with 2mol / l hydrochloric acid solution, separate out white crystals, filter, filter The cake was washed with water and dried under vacuum to obtain off-white solid Ⅰ;

[0053] (3) Add 75.2g of white solid I to a 5000ml three-necked flask, then add 1500ml of distilled water and ...

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Abstract

The invention discloses a 1 / 4 water cefmenoxime hydrochloride compound and a pharmaceutical composition thereof. Cefmenoxime hydrochloride per mole contains 1 / 4 mole of water. 7 amino cephalosporanicacid (7ACA) is taken as a starting raw material, is firstly reacted with 5-fluorenyl 1 methylol 1H-tetrazolium (MMT) at a C-3 position to form 3-(1-methyl-1-tetrazolium-5H-group) thiomethyl-7-aminocephalosporanic acid (7ACT), is reacted with MAEM in a C-7 position to synthesize cefmenoxime, and then is formed into salt with hydrochloric acid to obtain the 1 / 4 water cefmenoxime hydrochloride compound. The operation is simple, reactants are easily available, reaction conditions are mild, and the yield is high. The 1 / 4 water cefmenoxime hydrochloride compound has low moisture absorbing property,low impurity content, good fluidity, good thermodynamic stability and wide application prospect.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a 1 / 4 water cefmenoxime hydrochloride compound and a pharmaceutical composition thereof. Background technique [0002] Cefmenoxime (cefmenoxime) is the third-generation cephalosporin developed by Japan's Takeda in the 1970s. It was launched in Japan in 1983, and then in the United States, South Korea and other countries. With its broad-spectrum antibacterial activity and anti-β-endo Amidase has high stability and is widely used in the treatment of various infectious diseases caused by sensitive bacteria. [0003] Cefmenoxime is a cell wall synthesis inhibitor, which achieves bactericidal effect by inhibiting the biosynthesis of bacterial cell walls. This product is effective against both Gram-positive and Gram-negative bacteria. Among Gram-positive bacteria, the antibacterial effect on Streptococcus pyogenes and Pneumococcus is also strong. It also has a...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/06A61K31/546A61P31/04
CPCC07D501/06C07D501/36
Inventor 黄奋
Owner HAINAN LINGKANG PHARMA CO LTD
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