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Ibuprofen end group-containing polyethylene glycol medicine macromonomer and synthesis method thereof

A polyethylene glycol and macromonomer technology, which is applied in the directions of drug combinations, pharmaceutical formulations, and medical preparations containing active ingredients, can solve the problems of high price of polyethylene glycol, difficult preparation, and gastrointestinal irritation, etc. Achieve the effect of not easily adhering to the blood vessel wall, mild operating conditions, and long half-life

Inactive Publication Date: 2011-02-16
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Activated polyethylene glycol is very expensive and difficult to prepare
The author is WANG Ru-long (WANG Ru-long) and Yuan Zhengping (YUAN Zheng-ping) in the book Pharmaceuticals published by Beijing Chemical Industry Press (Beijing: Chemical Industry Press, 4th Edition Edition 4, 2005: 352) Explain that ibuprofen is 2-(4-isobutylphenyl)propionic acid, which has anti-inflammatory, analgesic and antipyretic effects, and is excreted quickly. It needs to be taken 3 times a day, but ibuprofen and niacin Drugs with carboxyl groups are insoluble in water and have strong acidity. When administered orally, they can irritate the gastrointestinal tract

Method used

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  • Ibuprofen end group-containing polyethylene glycol medicine macromonomer and synthesis method thereof
  • Ibuprofen end group-containing polyethylene glycol medicine macromonomer and synthesis method thereof
  • Ibuprofen end group-containing polyethylene glycol medicine macromonomer and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0029] In the first step, the consumption of polyethylene glycol, solvent, ibuprofen acid chloride and catalyzer is respectively 9.6g, 13.2g, 2.25g and 0.8g, reacts 24 hours at room temperature, polyethylene glycol: solvent: ibuprofen Acyl chloride: the weight ratio of catalyzer is 1: 1.375: 0.234: 0.0833, and n is 89, and solvent is dichloromethane, and catalyzer is triethylamine; Ethylene glycol drug macromer is 9.56g, and the yield is 91.0%.

Embodiment 2

[0031] In the first step, the consumption of polyethylene glycol, solvent, ibuprofen acid chloride and catalyzer is respectively 9.6g, 8.79g, 2.25g and 2.54g, reacts 12 hours under 80 ℃, polyethylene glycol: solvent: ibuprofen Fenyl chloride: the weight ratio of catalyzer is 1: 0.916: 0.234: 0.265, and n is 136, and solvent is dichloromethane, and catalyzer is triethylamine; 7.64g of polyethylene glycol drug macromonomer, the yield is 72.7%.

Embodiment 3

[0033] In the first step, the consumption of polyethylene glycol, solvent, ibuprofen acid chloride and catalyzer is respectively 4.8g, 13.2g, 2.25g and 0.8g, reacts at room temperature for 36 hours, obtains the polyethylene glycol containing ibuprofen end group. The crude product of glycol drug macromer, polyethylene glycol: solvent: ibuprofen acid chloride: the weight ratio of catalyzer is 1: 2.75: 0.468: 0.167, and n is 45, and solvent is dichloromethane, and catalyzer is triethylamine; In the second step, 4.56 g of a white powdery product, i.e. polyethylene glycol drug macromonomer containing ibuprofen end groups, was obtained with a yield of 80%.

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Abstract

The invention relates to an ibuprofen end group-containing polyethylene glycol medicine macromonomer and a synthesis method thereof, belonging to the technical field of pharmaceutical chemistry and synthesis thereof. The macromonomer is white powder, is soluble in N,N-dimethylformamide, methylene dichloride, chloroform, dioxane, dimethyl sulfoxide, distilled water or phosphoric acid PBS buffer solution, is not soluble in petroleum ether or aether, and has a structure as shown in the specification, wherein n is an integral number in a interval of 45-224. Under the catalysis condition, polyethylene glycol reacts with ibuprofen acyl chloride to synthesize the crude macromonomer, and then the crude macromonomer is purified to obtain the finished macromonomer, wherein the raw material ibuprofen acyl chloride is synthesized by referencing the known literatures. The macromonomer has the advantages of long half-life period, good water-solubility, little dosage, low toxicity and small thrill on intestines and stomach, contains degradable ester bonds, and is especially suitable for being used as an active component of ibuprofen slow-release drugs.

Description

technical field [0001] The invention relates to a polyethylene glycol drug macromonomer containing ibuprofen end groups and a synthesis method thereof, belonging to the technical field of medicinal chemistry and synthesis thereof. Background technique [0002] Small-molecule drugs have disadvantages such as short half-life, fast metabolism, and large side effects. Clinical applications often require repeated administration, which increases toxicity and side effects; poor water solubility affects human absorption. In order to solve the above problems, the modification of small molecule drugs has become a research hotspot in recent years. Linking small drug molecules to macromolecules to achieve sustained release or targeting properties can effectively improve their transport and absorption in vivo. Polyethylene glycol is non-toxic, non-teratogenic, non-immunogenic, long half-life, various types, good water solubility and biocompatibility, small molecule drugs modified with i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/48A61K47/48A61P29/00C08G65/00A61K31/192A61K47/60
Inventor 张亮宋春梅常飞梁晟斌赵丹
Owner EAST CHINA NORMAL UNIV
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