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Felbinac acetaminopher ester and its preparation method

A technology of acetaminophen ester and felbinac, which is applied in the field of acetaminophen felbinac compound, can solve the problems affecting the popularization and use of drugs, low bioavailability, etc., and achieves simple and feasible synthesis process, good product purity, good analgesic effect

Inactive Publication Date: 2007-05-16
GUANGDONG ZHONGKE DRUG R&D
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, felbinac has serious gastrointestinal irritation and can only be used externally, which affects the popularization and use of this drug, and the bioavailability of external application is low, only about 20%.

Method used

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  • Felbinac acetaminopher ester and its preparation method
  • Felbinac acetaminopher ester and its preparation method
  • Felbinac acetaminopher ester and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: Preparation of paracetamol felbinac

[0028] Add 21.2g of felbinac and 120ml of DMF into a 500ml three-necked flask, add 11.9g of thionyl chloride dropwise under stirring, stir and reflux for 2 hours after the drop-in is complete, recover excess thionyl chloride under reduced pressure after the reaction is completed, and collect bp : 123-125°C fraction, 18.7g, yield 78%.

[0029] In a 250ml three-neck flask, add 9g of paracetamol, 2ml of pyridine, 100ml of acetone, add 50ml of ethyl acetate and 18.7g of biphenylacetamide under stirring, and stir for 3 hours at high temperature, fully cool in an ice bath, and precipitate by suction filtration The solid was washed with a small amount of cold absolute ethanol, and dried to obtain 23.5 g of white crude crystals. Yield 63%.

[0030] Put the above crude crystals in a 250ml round-bottomed flask, add 150ml of absolute ethanol and 0.5g of activated carbon, heat to reflux for 2min, decarburize by suction filtratio...

Embodiment 2

[0036] Embodiment 2: Preparation of paracetamol felbinac

[0037] Operation is by embodiment 1, feed intake is:

[0038] Felbinac: 21.2g

[0039] Thionyl chloride: 119g

[0040] Acetaminophen: 45g

[0041] 17.9 g of paracetamol felbinac was obtained, m.p.: 138.6-139.1° C., yield: 84.4%.

[0042] Embodiment 2: Preparation of paracetamol felbinac

[0043] Operation is by embodiment 1, feed intake is:

[0044] Felbinac: 21.2g

[0045] Thionyl chloride: 40g

[0046] Acetaminophen: 18g

[0047] 19.8 g of paracetamol felbinac was obtained, m.p.: 138.5-139.3°C, yield: 93.4%.

Embodiment 3

[0048] Embodiment 3: the preparation of paracetamol felbinac

[0049] In a 250ml three-neck flask, add 21.2g of felbinac and 150ml of acetone and drop in 40ml of thionyl chloride under stirring. After the drop is completed, reflux for 2 hours, recover excess thionyl chloride under reduced pressure, and collect bp: 123- The fraction at 125°C / 133Pa yielded 19.3g, with a yield of 80%.

[0050] In a 250ml three-necked flask, add 9.6g of acetaminophen, 2ml of pyridine, 120ml of acetone and 60ml of ethyl acetate, and drop in 19.3g of biphenylacetyl chloride under stirring, stir at high temperature for 3 hours after the dropping, and fully cool in the refrigerator After that, the solid was precipitated by suction filtration, washed and dried with a small amount of absolute ethanol to obtain 259 g of white crude crystals. Yield: 64.2%.

[0051]Put the above crude crystals in a 250ml round bottom flask, add 160ml of absolute ethanol and 0.5g of activated carbon, heat and reflux for 2...

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Abstract

The invention discloses a biphenyl acetate n-acetamido-phenolic ester compound and preparing method with active component as drug composition, which comprises the following steps: adopting biphenyl acetate and thionyl chloride as raw material to prepare biphenyl acetyl chloride; reacting biphenyl acetyl chloride and n-acetamido-phenolic ester to produce rough crystal of product; recrystallizing to obtain the product.

Description

Technical field: [0001] The invention belongs to the field of organic chemistry and relates to a felbinac acetaminophen ester compound. Background technique: [0002] Antipyretic and analgesic drugs commonly used in clinical practice mainly include paracetamol, aspirin, ibuprofen, felbinac, etc. Traditional antipyretic and analgesic drugs such as analgin, antipyrine, phenacetin, and aminopyrine Drugs have been withdrawn from the market due to their toxic side effects. Because of its toxicity, phenacetin is rarely used in developed countries, and aminopyrines are used less and less because of their damage to hematopoietic granulocytes. Acetaminophen has good antipyretic and analgesic effects, but it has no anti-inflammatory effect, and other anti-inflammatory drugs are usually added when using pyretaminophen. Aspirin has strong digestive system and anticoagulant side effects, and is not an ideal antipyretic and analgesic drug. [0003] As an anti-inflammatory and analgesic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/25C07C231/12A61K31/165A61P19/02A61P19/04A61P29/00
Inventor 陈文展王伟
Owner GUANGDONG ZHONGKE DRUG R&D
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