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2,6-diisopropyl-3-fluorophenol as well as preparation method and application thereof

A technology of diisopropyl and fluorophenol, which is applied in the field of medicine, can solve problems such as toxic side effects, deterioration, and easy oxidation, and achieve the effect of simple operation

Inactive Publication Date: 2014-07-02
SICHUAN HAISCO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, the clinical use of propofol still has certain side effects, such as causing injection pain, lipid metabolism disorders and hyperlipidemia, indigestion events, infection and side effects caused by cardiopulmonary function inhibition, etc. Judging from the actual use of propofol, it is easily oxidized in the air and deteriorates, etc.
These problems limit the use of 2,6-diisopropylphenol to a certain extent

Method used

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  • 2,6-diisopropyl-3-fluorophenol as well as preparation method and application thereof
  • 2,6-diisopropyl-3-fluorophenol as well as preparation method and application thereof
  • 2,6-diisopropyl-3-fluorophenol as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Synthesis of 2,6-diisopropylanisole (Formula 3)

[0047] Add 1.5L of acetone, 155g of methyl iodide, 176.4g of 2,6-diisopropylphenol, and 61.6g of potassium hydroxide into a 3L three-necked flask, and heat to reflux. After TLC shows that the reaction is complete, stop heating, filter, and concentrate the mother liquor Dry, extract with petroleum ether 600mL×3, wash with water until neutral, anhydrous Na 2 SO 4 The organic phase was dried and concentrated to obtain 190 g of light yellow liquid (yield: 100%). The following is the structural characterization data of 2,6-diisopropylanisole:

[0048] LC-MS: m / z=193, (M+H) + .

[0049] 1 H NMR (CDCl 3 , δ / ppm): 1.25-1.27 (d, 12H, -CH 3 ); 3.32-3.42 (m, 2H, -CH-); 3.76 (s, 3H, -OCH 3 ); 7.13 (s, 3H, -ArH).

[0050] The above data confirm that the product obtained is 2,6-diisopropylanisole.

Embodiment 2

[0051] Embodiment 2: Synthesis of 2,6-diisopropylanisole (formula 3)

[0052]Add 1.5L of 1,4-dioxane, 176.4g of 2,6-diisopropylphenol, 155g of methyl iodide, and 62g of potassium hydroxide into a 3L reaction flask, and heat to reflux. After TLC shows that the reaction is complete, stop heating , filtered, the mother liquor was concentrated to dryness, extracted with n-hexane 500mL×3, washed with water until neutral, anhydrous Na 2 SO 4 The organic phase was dried, concentrated and subjected to column chromatography to obtain 140 g of liquid (yield: 74%).

[0053] The characterization results of the product are the same as in Example 1.

Embodiment 3

[0054] Embodiment 3: the synthesis of 2,6-diisopropylanisole (formula 3)

[0055] Add 50g of 2,6-diisopropylphenol, 3.1g of tetrabutylammonium bromide, 280mL of dimethyl carbonate and 40g of potassium carbonate into a 500mL three-necked flask, and heat to reflux. After TLC shows that the reaction is complete, stop heating, and Extract with 500mL×3 alkane, wash with water until neutral, anhydrous Na 2 SO 4 The organic phase was dried, concentrated and subjected to column chromatography to obtain 32 g of the product (yield: 59%).

[0056] The characterization results of the product are the same as in Example 1.

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Abstract

The invention discloses 2,6-diisopropyl-3-fluorophenol and a preparation method thereof, a medicinal composition using the compound as an active ingredient and an application of 2,6-diisopropyl-3-fluorophenol in preparation of central nervous system medicaments. The 2,6-diisopropyl-3-fluorophenol is prepared by using 2,6-diisopropyl phenol as an initial raw material through phenolic hydroxyl protection, nitrification, reductive ammoniation, fluorination, deprotection and the like. The obtained compound can be used for preparing sedative hypnotic and anesthetic medicaments. The method disclosed by the invention has the advantages that the raw materials are readily available, the cost is low, the final finished product is easy in purification and the like. The 2,6-diisopropyl-3-fluorophenol has valuable pharmacological properties, and can be applied to the preparation of the central nervous system medicaments.

Description

technical field [0001] The present invention relates to the field of medicine, in particular to a 2,6-diisopropyl-3-fluorophenol having sedative, hypnotic and anesthetic effects, a preparation method thereof, a pharmaceutical composition containing the compound as an active ingredient, and its preparation method. Use in central nervous system medicines. Background technique [0002] Propofol (Propofol, formula 2), also known as Propofol and Diprivan, has a chemical name of 2,6-diisopropylphenol, and is a widely used systemic intravenous anesthetic. It has rapid onset, short action time, quick and complete recovery, low incidence of postoperative nausea and vomiting, small adverse reactions, no sequelae, wide application range (can be used for anesthesia induction, maintenance and auxiliary epidural anesthesia), easy dosage Master and other excellent characteristics. But so far, the clinical use of propofol still has certain side effects, such as causing injection pain, lip...

Claims

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Application Information

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IPC IPC(8): C07C39/27C07C37/055A61K31/055A61P25/20A61P23/00A61P29/00A61P25/08A61P25/24
CPCY02P20/55C07C39/27C07C37/055C07C41/16C07C41/22C07C201/08C07C213/02C07C43/225C07C217/84C07C205/37C07C43/205
Inventor 袁道义陈洪陈大峰赵雄李岳晏菊芳邹永
Owner SICHUAN HAISCO PHARMA CO LTD
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