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Method for preparing broad-spectrum penicillin antibiotic ticarcillin sodium

A technology of ticarcillin disodium salt and disodium salt, which is applied in the field of preparation of broad-spectrum penicillin antibiotics, can solve the problems of complex salt formation process, low yield and purity, etc., achieve simple and convenient reaction route, reduce production cost, highly operable effect

Active Publication Date: 2012-01-18
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Aiming at the technical bias of carrying out carboxyl or amino protection to the starting material 6-APA (6-aminopenicillanic acid) or thienyl intermediate in the prior art, and then carrying out subsequent reactions, and the complexity of the salt-forming process, the yield and The deficiency of low purity; the present invention provides a kind of new synthesis method, only needs three steps, and reaction does not need to carry out amino group, carboxyl group protection, and the salt-forming refining method is easy and simple to operate, and raw material is cheap and easy to obtain, and obtains ticarcillin two from 6-APA The yield of sodium salt is over 60%, and the content reaches 98.5%.

Method used

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  • Method for preparing broad-spectrum penicillin antibiotic ticarcillin sodium
  • Method for preparing broad-spectrum penicillin antibiotic ticarcillin sodium
  • Method for preparing broad-spectrum penicillin antibiotic ticarcillin sodium

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Embodiment 1 3-thiophene malonic acid carries out chlorination reaction and prepares compound (II)

[0040] 9.3 grams of 3-thiophene malonate, 60ml of isopropyl ether, 0.2ml of DMF, 3.8ml of SOCl 2Add it to the round-necked bottle in turn, stir and heat up, control the temperature at 54°C to 56°C and reflux for 2 hours. After the reaction is complete, transfer the reaction solution to a rotary evaporator and distill to dryness at 30°C to obtain 9.45g of compound (II). Add 100ml of dichloromethane was used to obtain solution A for the next reaction with a yield of 92.5%.

Embodiment 2

[0041] Embodiment 2 3-thiophene malonic acid carries out chlorination reaction and prepares compound (II)

[0042] 12 grams of 3-thiophene malonate, 80ml of tetrahydrofuran, 0.5ml of DMF, 4ml of SOCl 2 Add it to the round-necked bottle in turn, stir and heat up, and control the temperature at 65°C to 68°C to reflux for 2.5 hours. After the reaction is complete, transfer the reaction solution to a rotary evaporator, and distill it to dryness under reduced pressure at 30°C to obtain 12.26g of compound (II). 100ml of dichloromethane was used to obtain solution A for the next reaction with a yield of 93%.

Embodiment 3

[0043] Embodiment 3 3-thiophene malonic acid carries out chlorination reaction and prepares compound (II)

[0044] Add 11 grams of 3-thiophenemalonic acid, 75ml of isopropyl ether, 0.6ml of triethylamine, and 3.9ml of phosphorus oxychloride into the round bottle in turn, stir and heat up, control the temperature at 54°C to 57°C and reflux for 2.5 hours, and the reaction is complete , the reaction solution was transferred to a rotary evaporator, and distilled to dryness under reduced pressure at 30°C to obtain 10.88g of compound (II), and 100ml of dichloromethane was added to obtain solution A for the next reaction, with a yield of 90%.

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Abstract

The invention relates to a novel method for preparing broad-spectrum penicillin antibiotic ticarcillin sodium. The method is characterized in that the method comprises the following steps of: (1) directly carrying out chlorination on 3-thiophenemalonic acid used as raw material and thionyl chloride in the presence of a catalyst, without protecting carboxyl, and chloridizing one carboxyl to obtiana compound (II); (2) carrying out condensation reaction with 6-aminopenicilanic acid (6-APA), controlling the reaction temperature and PH value, dripping the compound (II) and sodium bicarbonate solution, dispensing liquid after reaction, adjusting PH value to wash, adjusting pH value again to 2.0, extracting reaction solution, and drying to obtain a compound (IV); using sodium iso-octoate to salify, and refining crude products, to obtian the ticarcillin sodium salt.

Description

Technical field: [0001] The invention relates to a preparation method of broad-spectrum penicillin antibiotics, in particular to a new synthesis method of ticarcillin sodium salt. Background technique: [0002] Ticarcillin sodium (English name: Ticarcillin Disodium Chemical name: (2S, 5R, 6R)-3,3-Dimethyl-6-[2-carboxy-2-(2-thienyl) acetamido]-7- Oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt) is a broad-spectrum penicillin antibiotic, and its structural formula is: [0003] [0004] Ticarcillin sodium is a semi-synthetic penicillin drug created and developed by the British Beecham Company. So far, there have been many patents for ticarcillin sodium and its improved synthetic method, and there is no domestic method report for large-scale production of this product. Because ticarcillin sodium has poor stability and is sensitive to the temperature and pH of the environment, it has strict requirements on the production environment. At the same time, th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D499/72A61P31/04
Inventor 赵志全
Owner LUNAN PHARMA GROUP CORPORATION
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