Antipyretic analgesic and anti-arthritis nonsteroidal compound and its pharmaceutical compositions

A compound and composition technology, applied in the field of new compounds and their preparation, can solve the problems of inability to block the generation of metabolic pathway products and the like

Active Publication Date: 2006-10-11
TIANJIN INSTITUTE OF PHARMA RESEARCH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The cyclooxygenase inhibitors that are currently on the market do not inhibit the 5-lipoxygenase that produces various leukotrienes at concentrations that can effectively inhibit cyclooxygenase activity, nor can they block the production of this metabolic pathway product

Method used

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  • Antipyretic analgesic and anti-arthritis nonsteroidal compound and its pharmaceutical compositions
  • Antipyretic analgesic and anti-arthritis nonsteroidal compound and its pharmaceutical compositions
  • Antipyretic analgesic and anti-arthritis nonsteroidal compound and its pharmaceutical compositions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Preparation of 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-pyrrolizine-5-bromobutyl acetate (v):

[0064] Put 50 milliliters of analytically pure methanol into a 250 milliliter four-neck reaction flask, stir and reflux, add 1.5 grams of sodium metal, reflux for 10 minutes, and cool down to room temperature; add 7.5 grams (0.02mol) of 6-(4-chlorophenyl) -2,2-Dimethyl-7-phenyl-2,3-dihydro-pyrrolizine-5-acetic acid (IV), reacted for 30 minutes; distilled to dryness under reduced pressure at 50-60°C, added 50 ml di Methylformamide and 12.9 g (0.06 mol) redistilled 1,4-dibromobutane were reacted at room temperature for 24 hours, then distilled to dryness under reduced pressure at 100°C to obtain an oil. Using 200-mesh silica gel column analysis, using n-hexane and diethyl ether at a ratio of 1:1 as the developing solvent, 7-8 grams of light yellow solid (v) was obtained with a yield of 60-70% and a melting point of 89-92°C.

[0065] HNMR (CDCl 3 )δ: 1.29 (6H, two ...

Embodiment 2

[0067] Preparation of 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-pyrrolizine-5-acetic acid butyl nitrate (II):

[0068] In a 250 ml four-neck reaction, 50 ml of tetrahydrofuran and 8 g (0.015 mol) of (v) were added at room temperature, and stirred to dissolve. 4 grams (0.023mol) of silver nitrate were dissolved in 30 milliliters of acetonitrile, and added to a 250 milliliter four-neck reaction flask. After reacting at room temperature for 24 hours, 1 gram (0.006mol) of silver nitrate was added to continue the reaction at room temperature for 24 hours, 50- Distilled to dryness under reduced pressure at 60°C to obtain oil. Using 200-mesh silica gel column analysis, using n-hexane and diethyl ether as a developing solvent at a ratio of 7:3, 4 g of (II) was obtained with a yield of 40% and a melting point of 105-107°C.

[0069] HNMR (CDCl 3 )δ: 1.30 (6H, two -CH at the 2-position of the pyrrolizine ring 3 Hydrogen), 1.76 (4H, two -CH in the 2'.3' position of butyl nit...

Embodiment 3

[0071] Preparation of 6-(4-bromophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-pyrrolizine-5-bromopropyl acetate (III):

[0072] Put 50 milliliters of analytically pure methanol into a 250 milliliter four-neck reaction flask, stir and reflux, add 1.5 grams of sodium metal, reflux for 10 minutes, and cool down to room temperature; add 8.5 grams (0.02mol) of 6-(4-bromophenyl) -2,2-Dimethyl-7-phenyl-2,3-dihydro-pyrrolizine-5-acetic acid (VI), reacted for 30 minutes; distilled to dryness under reduced pressure at 50-60°C, added 50 ml di Methylformamide and 12 g (0.06 mol) of redistilled 1,4-dibromopropane were reacted at room temperature for 24 hours, then distilled to dryness under reduced pressure at 100°C to obtain an oil. Using 200-mesh silica gel column analysis, using n-hexane and diethyl ether at a ratio of 1:1 as the developer, 6 g of a light yellow solid was obtained with a yield of 70%. The crude product was directly put into the next reaction without purification.

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PUM

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Abstract

The invention relates a group of compounds having formula (I) and their use as medicaments for non-steroidal analgesic analgesia, anti-arthritis, and protecting gastrointestinal tract mucous membrane. The invention also discloses the pharmaceutical compositions containing the compounds of formula (I), wherein R1, R2, R3 and X are defined in the specification.

Description

technical field [0001] The invention belongs to the technical field of autoimmune regulation drugs, more specifically, the invention relates to a new compound and its preparation method, as well as the pharmaceutical composition containing the compound and its application. Background technique [0002] For a long time, non-steroidal anti-inflammatory drugs such as aspirin have been widely used in antipyretic, analgesic and anti-rheumatoid treatments, but due to poor curative effect and common gastrointestinal and renal toxicity, the application of such drugs Restricted, especially for patients with diseases such as rheumatoid arthritis who need to take medicine for a long time. These pharmacological effects of non-steroidal anti-inflammatory drugs may be related to the blockage of cyclooxygenase in the biosynthesis of prostaglandins from arachidonic acid in the gastrointestinal tract and kidney tissue. Inhibition of cyclooxygenase is the main mechanism of action of most non...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/407A61P1/04A61P19/02A61P29/00
Inventor 梅林雨梁忠信王杏林高晶张俊伟刘昌孝王平保汤立达
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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