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Hydroxydecylbenzoquinone derivatives and uses thereof

A technology of medicine and composition, applied in the field of pharmaceutical use of 6--2,3-dimethoxy-5-methyl-1,4-benzoquinone, which can solve the problem of impaired cognitive function and unrelieved aging Effects of anesthesia and disorientation in surgical patients

Inactive Publication Date: 2015-09-16
北京三泉医药技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recovery from anesthesia with long-acting anesthetics often results in a state of marked disorientation and cognitive impairment for prolonged periods of time
Even newer short-acting anesthetics fail to alleviate postanesthesia effects in elderly surgical patients

Method used

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  • Hydroxydecylbenzoquinone derivatives and uses thereof
  • Hydroxydecylbenzoquinone derivatives and uses thereof
  • Hydroxydecylbenzoquinone derivatives and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0127] Embodiment 1: preparation compound of the present invention

[0128] The general reaction process of the present embodiment is as follows:

[0129]

[0130] (i), the preparation of 10-acetoxydecanoic acid (2)

[0131] In the reaction flask, add sodium hydroxide 115g (2.875mol), water 40ml, castor oil 150g and mixed cresol 45g, stir in 180~195 ℃ (reaction initial stage has frothing phenomenon, needs rapid stirring), reflux 3h. The volatile matter was removed by distillation, 1.5 L of water was added to the residue, the pH was adjusted to acidic with 50% sulfuric acid (containing Congo red), and heated to boiling. Separate the oil layer with a preheated separatory funnel, wash with ether, and dry over anhydrous sodium sulfate. Filtrate, recover the solvent from the filtrate, add 350ml of acetic anhydride to the residue, heat, stir and reflux for 5~6h, pour the reactant into an appropriate amount of ice, and place it overnight. Extracted several times with ether, c...

Embodiment 2

[0144] Embodiment 2: preparation compound of the present invention

[0145] Use embodiment 1 step (vi) gained product, carry out according to the method for embodiment 1 step (vii), difference is to use: 5mL dichloromethane is good solvent, 5mL sherwood oil is the first antisolvent, 15ml cyclohexane is Second anti-solvent; crystallization cooling rate is 0.05°C / min. The yield was 91.3%. mp54.5~55°C.

Embodiment 3

[0146] Embodiment 3: preparation compound of the present invention

[0147] Use embodiment 1 step (vi) gained product, carry out according to the method for embodiment 1 step (vii), difference is to use: 4mL dichloromethane is good solvent, 7mL n-pentane is the first anti-solvent, 13ml n-hexane is The second anti-solvent; the crystallization cooling rate is 0.5°C / min. The yield was 90.9%. mp54~54.5°C.

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Abstract

The invention relates to a hydroxydecyl benzoquinone derivative and application thereof. The invention specifically relates to a hydroxydecyl benzoquinone derivative shown as the following compound with a formula I, a pharmaceutical composition comprising the compound, a preparation method of the benzoquinone derivative as well as application of the derivatives in preparation of medicines for cerebrovascular diseases.

Description

technical field [0001] The invention relates to 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone. Specifically, the present invention relates to 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone with specific properties and its preparation method, and the 6- Pharmaceutical use of (10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone. Background technique [0002] Neuronal damage, neurodegenerative diseases and syndromes (Alzheimer's disease, multiple sclerosis, Friedrich's ataxia, brain and spinal cord injuries and neurotrauma, stroke, Parkinson's disease, alcoholism and narcolepsy, postoperative recovery syndrome and postanesthesia recovery syndrome) and many other conditions require effective treatment and prevention. [0003] Postoperative stroke and cognitive deficit (POSCD) syndrome is common, especially in older adults undergoing major surgical procedures such as heart surgery or hip replacement. In North America, more than 2.5 million such ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C50/28C07C46/10A61K31/122A61P9/00A61P25/00A61P25/18A61P9/10A61P25/22A61P25/24A61P25/28A61P7/02A61P39/06A61P25/32
Inventor 刘炜
Owner 北京三泉医药技术有限公司