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Compound for anesthetics

A technology of anesthetics and organic compounds, applied in the field of medicinal chemistry, can solve the problems of not showing strong oral activity, poor oral bioavailability, time cannot be used as a sedative/sleeping agent, etc.

Inactive Publication Date: 2012-10-03
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002]Naturally occurring neuroactive steroids are unsuitable as sedatives / hypnotics due to their poor oral bioavailability, presumably due to their rapid first-pass metabolism (Hogenkamp. D. J. et al., Journal of Medicinal Chemistry 40: 61-72 (1997))
Addition of 3?-substitutions resulted in neuroactive steroids that did not exhibit strong oral activity in animals, but they generally persisted too long to be useful sedatives / sleeping agents

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0017] Synthetic steps:

[0018] (1) Synthesis of 2-fluoro-4-bromo-benzyl bromide

[0019] Add 75.6g (0.4mol) of 2-fluoro-4 bromotoluene and 14.4g of benzoyl peroxide in the reaction flask equipped with mechanical stirring and reflux condenser, after stirring and heating to reflux, 71.2g (0.4mol) 2-Bromo-2,5-diketone pyrrole (NBS) was added to the reaction flask in batches within 20 minutes, heated to reflux for 2 hours, and the reaction yield was 65% (GC). The reaction solution was neutralized with sodium carbonate, concentrated, dissolved with industrial absolute ethanol (1g:1mL) under reflux, cooled to -15°C for recrystallization, the purity was about 90% (GC). Its purity was >99% after multiple recrystallizations.

[0020] (2) Synthesis of 4-triphenylamino formaldehyde

[0021] Under the protection of nitrogen, add 12.3g (0.05mol) triphenylamine and 100mL DMF to the reaction flask equipped with mechanical stirring and reflux condenser, cool to 5°C in an ice bath, slowly...

preparation Embodiment 2

[0033] The organic compound prepared in step (4) above was placed in a quartz ampoule. The prepared compound was vacuum dehydrated at a temperature of 100°C. The tube was disengaged and placed in a crystal growth furnace. Crystals were grown by the Bridgman method in a double furnace with an insulating film. Finally, colorless strip crystals were obtained. The crystal is subjected to single crystal X-ray diffraction crystallographic analysis, and its crystallographic parameters are as follows: it is an orthorhombic system, and its space group is P2 1 , a=6.30 ?, b=7.90 ?, c=9.10 ?, β=89.5°, V=452.9 ? 3 .

[0034] Biologically active examples:

Embodiment 1

[0036] Table 1 embodiment 1 compound and the biological activity comparison of embodiment 2 compound

[0037] compound TBPS IC 50 (nM) RR TD50 Oral (mg / kg) Duration of action (minutes) Example 1 46 31 >240 (3 / 8 pass) Example 2 44 15 >240 (0 / 8 passed)

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PUM

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Abstract

The invention provides an organic compound for anesthetics, functioning as sedative / hypnotic and used for anesthetization.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry and methods and methods of organic compounds for regulating brain stimulation. Background technique [0002] Naturally occurring neuroactive steroids are unsuitable as sedative / hypnotic agents because of their poor oral bioavailability, presumably due to their rapid first-pass metabolism (Hogenkamp. D. J. et al., Journal of Medicinal Chemistry 40: 61 -72 (1997)). Addition of 3?-substitutions resulted in neuroactive steroids that did not exhibit strong oral activity in animals, but they generally persisted for too long to be useful sedatives / hypnotics. Sedatives / hypnotics should have an elimination half-life in humans of <5 hours to avoid residual next-day effects and accumulation following continuous nightly dosing (Nicholson, A.N. Drugs 31:164-176 (1986)). However, we have found that 3?-methoxymethyl-substituted steroids, while maintaining the oral activity of other 3?-substituted ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/32A61K31/421A61P23/00
Inventor 阳慧林静
Owner WEST CHINA HOSPITAL SICHUAN UNIV