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Dexibuprofen guaiacol ester and preparation method thereof

A technology of guaiacol and lignan ester, which is applied in the field of western medicine invention, can solve the problems of enantiomers having no drug effect and harmfulness, and achieve the effects of relieving pain, overcoming liver damage, and benefiting drug dosage

Inactive Publication Date: 2009-06-17
HUNAN JIUDIAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

An enantiomer of a beneficial isomer may be ineffective and may even be harmful

Method used

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  • Dexibuprofen guaiacol ester and preparation method thereof
  • Dexibuprofen guaiacol ester and preparation method thereof
  • Dexibuprofen guaiacol ester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 20.5g (0.1mol) of dextroibuprofen and 20ml of thionyl chloride into a 100ml dry single-necked bottle, heat (control the temperature at 60°C) and stir, and reflux until no hydrogen chloride gas is generated, then evaporate at normal pressure Excessive thionyl chloride gave 20.2 g (+) α-methyl-4-(2-methylpropyl) phenylacetyl chloride as a pale yellow liquid with a strong pungent odor. Add 18g (0.08mol) (+) α-methyl-4-(2-methylpropyl) phenylacetyl chloride and 9ml (0.08mol) guaiacol of the above-mentioned obtained liquid to a 100ml dry single-mouth bottle, add 60ml of dichloromethane was cooled in an ice-water bath and 10ml of triethylamine was added dropwise under strong mechanical stirring, and the raw material guaiacol basically reacted completely as detected by TLC. The reaction time is about 5 hours. The reaction system was washed with water until neutral, then dried by adding anhydrous sodium sulfate, the solvent was recovered under reduced pressure to obtain an...

Embodiment 2

[0034]Add 10g (0.049mol) dextroibuprofen and 10ml phosphorus trichloride to a 50ml dry single-necked bottle, heat (control the temperature at 30°C) and stir and reflux until no hydrogen chloride gas is generated, then evaporate excess trichloride under normal pressure Phosphate, to obtain light yellow liquid 8g (+) α-methyl-4-(2-methylpropyl) phenylacetyl chloride with a strong pungent odor. Then add 6g (0.027mol) (+) α-methyl-4-(2-methylpropyl) phenylacetyl chloride and 3ml (0.027mol) guaiacol of the above-mentioned obtained liquid into a 100ml dry single-necked bottle, add 30ml of acetone was cooled in an ice-water bath and 40ml of 5% sodium hydroxide solution was added dropwise under strong mechanical stirring, and the raw material guaiacol basically reacted completely as detected by TLC. The reaction time is about 4 hours. The reaction system was first washed with water until neutral, and finally dried by adding anhydrous sodium sulfate. The solvent was recovered under re...

Embodiment 3

[0036] Add 10g (0.049mol) of dextroibuprofen and 10ml of thionyl chloride to a 50ml dry single-necked bottle, control the temperature of the oil bath at 40°C, stir and reflux until no hydrogen chloride gas is produced (about 2.5 hours), then evaporate under reduced pressure The excess thionyl chloride was removed to obtain 10.5 g (96%) of (+) α-methyl-4-(2-methylpropyl)phenylacetyl chloride as a pale yellow liquid with a strong pungent odor. Add 10g (0.045mol) of the above-mentioned liquid (+) α-methyl-4-(2-methylpropyl) phenylacetyl chloride and 5ml (0.045mol) guaiacol to a 100ml dry single-necked bottle, add 40ml of toluene was cooled in an ice-water bath and 5ml of pyridine (1.2equ) was added dropwise under strong mechanical stirring, and the raw material guaiacol basically reacted completely as detected by TLC. The reaction time is about 6 hours. The reaction system was first washed with water until neutral, and finally dried by adding anhydrous sodium sulfate. The solven...

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Abstract

The invention relates to a novel optical isomer compound of a formula (1), in particular to a dextroisomer of ibuprofen guaiacol ester. The invention also discloses a method for preparing the compound, a drug composition taking the compound as an active ingredient and application of the compound and the drug composition to the preparation of drugs of diminishing inflammation, effectively alleviating various pain or having effects of relieving fever of adults and / or children.

Description

field of invention [0001] The invention belongs to the field of western medicine invention. It relates to a dextroisomer of a compound with structural formula (1), a preparation method of the compound, and a pharmaceutical composition containing the compound. The compound of the present invention has anti-inflammatory and analgesic effects, and can effectively relieve various pains. The medicine made by using the compound of the present invention can be used to relieve various pains, including acute attack of arthritis or persistent joint swelling and pain symptoms, and can also treat Various soft tissue rheumatic pains. The medicine prepared by using the compound of the present invention also has antipyretic effect on fever in adults and / or children. [0002] The novel compound discussed in the present invention is the dextroisomer of the compound ibuprofen guaiacol ester. Background technique [0003] Ibuprofen, as a non-steroidal anti-inflammatory analgesic, has been a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C69/612A61K31/216A61P29/00
Inventor 朱志宏郑良彬卜振军
Owner HUNAN JIUDIAN PHARMA
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