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Substituted aryl methylene sulfonylated aza cyclo-pentanone compounds, its medicine compositions and its preparing process and use

A technology of arylmethylenesulfonyl nitrogen and heterocyclopentanone, which can be used in the field of medicine and can solve problems such as enzyme imbalance in the body and cardiovascular damage.

Inactive Publication Date: 2008-09-24
RADIOLOGY INST ACAD OF MILITARY MEDICINE SCI PLA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The prior art discloses that highly selective cox-2 inhibitors can cause enzyme imbalance in the body, although it can overcome gastrointestinal side effects, long-term use is likely to cause cardiovascular damage

Method used

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  • Substituted aryl methylene sulfonylated aza cyclo-pentanone compounds, its medicine compositions and its preparing process and use
  • Substituted aryl methylene sulfonylated aza cyclo-pentanone compounds, its medicine compositions and its preparing process and use
  • Substituted aryl methylene sulfonylated aza cyclo-pentanone compounds, its medicine compositions and its preparing process and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Preparation of (Z)-5-(3,5-di-tert-butyl-4-hydroxyphenylmethylene)-2-p-toluenesulfonimide-4-thiazolidinone (A1)

[0035] Add 2.34g (10mmol) 3,5-di-tert-butyl-4-hydroxybenzaldehyde, 1.16g (10mmol) 2-imino-4-thiazolidinone and 20ml water in a 50ml round-bottomed flask, and add 0.075 g (1 mmol) isopropanolamine. Reflux for 10 h, cool to room temperature, and filter with suction, wash the filter cake with cold water, and dry to obtain 2.69 g of yellow solid, mp 283-286°C, yield 81.0%. is (Z)-5-(3,5-di-tert-butyl-4-hydroxyphenylmethylene)-2-imino-4-thiazolidinone (intermediate A).

[0036] Dissolve 0.198g (0.6mmol) of the intermediate A in 10ml of dry tetrahydrofuran, and add 0.120g (1.2mmol) of triethylamine (1.2mmol) and 0.228g (1.2mmol) of p-toluenesulfonyl chloride while stirring. Reaction at 50°C for 12h, preparative thin layer separation, the developing solvent was dichloromethane:methanol=15:1, 0.102g of yellow solid was obtained, mp 264-267°C, yield 35.0%...

Embodiment 2

[0037] Example 2: Preparation of (Z)-5-(3,5-di-tert-butyl-4-hydroxyphenylmethylene)-2-benzenesulfonimide-4-thiazolidinone (A2)

[0038] Carry out by the method for embodiment 1.

[0039] The intermediate A is obtained first, the raw materials used in the condensation reaction are 3,5-di-tert-butyl-4-hydroxybenzaldehyde and 2-imino-4-thiazolidinone, and the catalyst is ethanolamine.

[0040] The reagent used in the sulfonylation process is benzenesulfonyl chloride, and the basic catalyst used is dimethylaminopyridine.

[0041] The product A2(Z)-5-(3,5-di-tert-butyl-4-hydroxyphenylmethylene)-2-benzenesulfonimido-4-thiazolidinone was obtained as a yellow solid, mp 252 -255°C, yield 18.9%.

Embodiment 3

[0042] Example 3: Preparation of (Z)-5-(4-hydroxyphenylmethylene)-2-benzenesulfonylimide-3-benzenesulfonyl-4-thiazolidinone (A3)

[0043] The same method as in Example 1 was used.

[0044] First synthesize (Z)-5-(4-hydroxyphenylmethylene)-2-imino-4-thiazolidinone, the raw materials used are 4-hydroxybenzaldehyde and 2-imino-4-thiazolidine Ketones, the catalyst is isopropanolamine. A yellow solid was obtained, mp > 300°C, and the yield was 82.4%.

[0045] The reagent used in the sulfonylation process is benzenesulfonyl chloride, and the basic catalyst used is pyridine.

[0046] The product A3 was obtained as light yellow solid, mp 222-226°C, yield 22.5%.

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Abstract

The present invention discloses substituted aryl methylene sulfonylated aza cyclopentanone compounds, their medicine compositions, and their preparation process and application in preparing antiphlogistic and analgetic medicines.

Description

Technical field [0001] The invention belongs to the field of medicine, and relates to a non-steroidal anti-inflammatory and analgesic drug, in particular to a class of substituted aryl methylenesulfonylated azacyclopentanone compounds (I), a preparation method thereof, and a general medicine containing an effective dose. A pharmaceutical composition of the compound of formula (I), and the application of the compound and the composition in the field of non-steroidal anti-inflammatory analgesia. Background technique [0002] Non-steroidal anti-inflammatory drugs (NSAIDs for short) are widely used in the prevention and treatment of various inflammatory diseases and pain due to their definite anti-inflammatory and analgesic effects. These ailments include migraine, biliary colic, bursitis, tenosynovitis, joint capsulitis, low back pain, gout, headache, toothache, neuralgia, joint pain, muscle pain, menstrual pain, fever, rheumatism, acute and chronic rheumatoid arthritis And rh...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/32C07D277/34C07D233/66C07D233/72A61K31/4166A61K31/427A61P29/00
Inventor 王林彭涛李鲁温晓雪刘靖刘力军
Owner RADIOLOGY INST ACAD OF MILITARY MEDICINE SCI PLA