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2,6-diisopropyl-4-fluorophenol or salt and crystal form thereof as well as preparation method and application thereof

A technology of diisopropyl and fluorophenol, which is applied in the field of medicine, can solve the problems of toxic side effects, easy oxidation, deterioration, etc., 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

AI Technical Summary

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-4-fluorophenol or salt and crystal form thereof as well as preparation method and application thereof
  • 2,6-diisopropyl-4-fluorophenol or salt and crystal form thereof as well as preparation method and application thereof
  • 2,6-diisopropyl-4-fluorophenol or salt and crystal form thereof as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1: Synthesis of 2,6-Diisopropyl-4-bromoanisole (Formula 3)

[0054] Add 15L of acetone, 1440g of 2,6-diisopropyl-4-bromophenol, 867g of methyl iodide, and 345g of potassium hydroxide to a 25L reaction flask, and heat to reflux. After TLC shows the reaction is complete, stop heating, filter, and concentrate ,Extract with n-hexane 2L×3, wash with water to neutral, anhydrous Na 2 SO 4 The organic phase was dried and concentrated to obtain 1500 g of a colorless oil, which was 2,6-diisopropyl-4-bromoanisole. Yield: 99%.

[0055] The structural characterization data of 2,6-diisopropyl-4-bromoanisole are as follows:

[0056] GC-MS: m / z=270(M + );272(M+2) + .

[0057] 1 H NMR(CDCl 3 ,δ / ppm): 1.21-1.23(d, 12H, -CH 3 );3.25-3.32(m, 2H, -CH-); 3.71(s, 3H, -OCH 3 ); 7.19(s, 2H, -ArH).

[0058] The above data confirms that the product obtained is 2,6-diisopropyl-4-bromoanisole.

Embodiment 2

[0059] Example 2: Synthesis of 2,6-Diisopropyl-4-bromoanisole (Formula 3)

[0060] Add 3L of 1,4-dioxane, 288g of 2,6-diisopropyl-4-bromophenol, 173g of methyl iodide, and 69g of potassium hydroxide to a 5L reaction flask. Heat to reflux. TLC shows that the reaction is complete. , Stop heating, filter, concentrate, extract with n-hexane 700mL × 3, wash with water to neutral, anhydrous Na 2 SO 4 The organic phase was dried and concentrated to obtain 182 g of a colorless oil, which was 2,6-diisopropyl-4-bromoanisole. Yield: 60%.

[0061] The characterization results of the product were the same as in Example 1.

Embodiment 3

[0062] Example 3: Synthesis of 2,6-Diisopropyl-4-bromoanisole (Formula 3)

[0063] Add 50g of 2,6-diisopropyl-4-bromophenol, 3.1g of tetrabutylammonium bromide, 280ml of dimethyl carbonate and 40g of potassium carbonate to a 500mL three-necked flask. Heat to reflux. TLC shows that the reaction is complete. , Stop heating, extract with n-hexane 400mL×3, wash with water to neutral, anhydrous Na 2 SO 4 The organic phase was dried and concentrated to obtain 20 g of a colorless oil. Yield: 38%.

[0064] The characterization results of the product were the same as in Example 1.

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Abstract

The invention discloses a preparation method of 2,6-diisopropyl-4-fluorophenol or a salt thereof, a crystal form of the 2,6-diisopropyl-4-fluorophenol, a medicine composition using the compound as an active ingredient, and an application thereof. The 2,6-diisopropyl-4-fluorophenol is prepared through phenolic hydroxyl group protection, ammoniation, fluorination and deprotection by using 2,6-diisopropyl-4-bromophenol as a starting raw material. The preparation method disclosed by the invention has the advantages of availability of the raw material, low cost, and simplicity in operation; and the 2,6-diisopropyl-4-fluorophenol is easily purified, a single crystal with high purity and the crystal form suitable for officinal application can be obtained. The 2,6-diisopropyl-4-fluorophenol or salt thereof has a valuable pharmacological property, and can be applied to preparation of central nervous system drugs.

Description

Technical field [0001] It belongs to the technical field of medicine, and specifically relates to a method for preparing the crystal form of 2,6-diisopropyl-4-fluorophenol or its salt and 2,6-diisopropyl-4-fluorophenol and the compound is Pharmaceutical compositions of active ingredients and their use in the preparation of drugs for the central nervous system. Background technique [0002] Propofol (Formula 7), also known as Propofol and Deprima, and its chemical name is 2,6-diisopropylphenol. It is a widely used general intravenous anesthetic. It has rapid onset of action, short action time, rapid 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 to dose Master and other excellent characteristics. But so far, the clinical use of propofol still has certain side effects, such as causing injection pain, l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/27C07C39/44C07C37/055C07C37/66A61K31/055A61P25/20A61P23/00A61P29/00A61P25/08A61P25/24A61P25/00
CPCA61K31/055C07B2200/13C07C37/055C07C37/66C07C39/27C07C41/16C07C41/22C07C213/02C07C39/44C07C43/225C07C217/84
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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