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Synthesis method of barascamphor salicylatel isobaras camphor salicylate and its derivative

A kind of technology of camphenyl salicylate and isocamphenyl ester, which is applied in the synthesis field of camphenyl salicylate/isocamphenyl ester and derivatives thereof, and can solve problems such as adverse reactions, bone marrow toxicity and side effects, and reduction of adverse reactions.

Inactive Publication Date: 2003-04-16
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Subsequently, a number of other non-steroidal anti-inflammatory drugs came out one after another. In the 1950s, pyrazolone drugs such as phenylbutazone appeared, which have strong anti-inflammatory and analgesic effects, but have serious side effects on bone marrow; Indole acetic acid drugs such as indomethacin in the 1960s have strong anti-inflammatory, antipyretic and analgesic effects, but the drug has serious adverse reactions to the stomach, liver and kidney; since 70 years, ibuprofen as the representative Phenylpropionic acid drugs, phenylacetic acid drugs represented by diclofenac, phenate drugs represented by etofenamate, and benzothiazine drugs represented by piroxicam appeared one after another, and the adverse reactions decreased, but , there are still varying degrees of toxic side effects

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Synthesis of L-(-)-bornyl acetylsalicylate:

[0020] 153 grams (1 mole) of L-(-)-camphor was dissolved in 200 milliliters of ether solution, and 700 milliliters (1.12 moles) of 1.6 mole / liter n-butyllithium was added dropwise under cooling in an ice bath, and reacted for 10 minutes. Add to 198.5 g (1 mol) of acetylsalicylic acid chloride in 200 ml of ether and 10 ml (0.06 mol) of tetramethylethylenediamine solution. After 1 hour, wash with 2000 ml of 1mol / L hydrochloric acid, 2000 ml of saturated sodium bicarbonate solution, and 2000 ml of brine, and dry over anhydrous sodium sulfate. The solvent was distilled off, and diethyl ether and petroleum ether were used as eluents to separate on a silica gel column to obtain L-(-)bornyl acetylsalicylate.

Embodiment 2

[0022] Synthesis of D-(+)-bornyl propionylsalicylate:

[0023] 153 grams (1 mole) of D-(+)-camphor was dissolved in 400 milliliters of diethyl ether solution, and 750 milliliters (1.2 moles) of 1.6 mole / liter sec-butyllithium was added dropwise under cooling in an ice bath, and reacted for 20 minutes. Add to 233 g (1.1 mol) of propionylsalicylic acid chloride in 400 ml of ether and 20 ml (0.13 mol) of tetramethylethylenediamine solution. After 1 hour, wash with 1000 ml of 1mol / L hydrochloric acid, 2000 ml of saturated sodium bicarbonate solution, and 2000 ml of brine, and dry over anhydrous sodium sulfate. The solvent was evaporated, diethyl ether and petroleum ether were used as eluents, and silica gel column separation was performed to obtain D-(+)-camphoryl propionyl salicylate 1.

Embodiment 3

[0025] Synthesis of butyrylsalicylate L-(-)-isoborneol ester:

[0026] 153 grams (1 mole) of L-(-)-isoborneol was dissolved in 600 milliliters of diethyl ether solution, and 800 milliliters (1.28 moles) of 1.6 mole / liter tert-butyllithium was added dropwise under cooling in an ice bath, and reacted for 40 minutes. Added to a solution of 271.4 g (1.2 mol) of butyrylsalicylic acid chloride in 500 ml of ether and 50 ml (0.33 mol) of tetramethylethylenediamine. After 1.5 hours, wash with 2000 ml of 1mol / L hydrochloric acid, 2000 ml of saturated sodium bicarbonate solution, and 2000 ml of brine, and dry over anhydrous sodium sulfate. The solvent was evaporated, diethyl ether and petroleum ether were used as eluents, and silica gel column separation was performed to obtain L-(-)-isobornyl butyryl salicylate.

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Abstract

A process for synthesizing bornyl / isobornyl salicylate and its derivatives, which makes some anti-inflammatory agent have lower suppression to COX-1 but higher suppression to COX-2 for higher curative effect and lower toxic by-effect, includes the reaction of borneol / isoborneol on organolithium reagent to obtain bornyl lithium salt, and the nucleophilic reaction of negative ions borneol / isoborneol on the acid halide of salicylic acid derivative to obtain the compound containing borneol / isoborneol.

Description

technical field [0001] The invention belongs to the synthesis method of camphor / isocamyl salicylate and derivatives thereof. Background technique [0002] For inflammation not caused by the causative pathogen, the treatment means mainly rely on two classes of drugs. Steroidal anti-inflammatory drugs (SAIDs steroidal anti-inflammatory drugs) and non-steroidal anti-inflammatory drugs (NSAIDs non-steroidal anti-inflammatory drugs). [0003] Steroidal anti-inflammatory drugs refer to a class of hormone drugs with a steroid core as the basic structure. Clinically commonly used glucocorticoids (GCS), such as: cortisone, hydrocortisone, dexamethasone, prednisone and so on. Its basic mechanism of action is that after glucocorticoids combine with glucocorticoid receptors in the cytoplasm of target cells, they affect the transcription of some genes involved in inflammation and produce anti-inflammatory effects. Although the curative effect of glucocorticoids is positive, the side e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C69/76C07C69/84
Inventor 高连勋高照波邱雪鹏
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI