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Method synthesizing arotinoid acid and arotinoid ethylester, and its pharmaceutical application

A technique of aromatic ethyl retinoic acid and a synthetic method, which is applied in the synthetic method and the application field in pharmacy, can solve problems such as not fully and specifically disclosing the application, and achieve the effects of cost reduction, good product quality, and shortened time

Inactive Publication Date: 2006-09-13
徐岩峰
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its pharmacological application has not been fully and specifically disclosed

Method used

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  • Method synthesizing arotinoid acid and arotinoid ethylester, and its pharmaceutical application
  • Method synthesizing arotinoid acid and arotinoid ethylester, and its pharmaceutical application
  • Method synthesizing arotinoid acid and arotinoid ethylester, and its pharmaceutical application

Examples

Experimental program
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Effect test

Embodiment 1

[0057] Example 1: Synthesis of aromatic ethyl retinoate, namely P-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) propenyl]-ethyl benzoate.

[0058] The first step, preparation [1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-ethyl]-triphenylphosphine bromide, its step as follows:

[0059] a, Preparation of 2,5-dimethylhexanedichloro-2,5

[0060] Add 365g of 2,5-dimethylhexanediol-2,5 into 2500ml of concentrated hydrochloric acid, let it stand at room temperature for 24 hours, separate the solid, wash it with water to remove the acid, wash it twice with methanol, and dry it The measured melting point is 64-65°C, which is 2,5-dimethylhexanedichloro-2,5;

[0061] b, preparation of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-naphthalene

[0062] Add 73.2g of 2,5-dimethylhexanedichloro-2,5 into 500ml of benzene, then add 10.5g of aluminum trichloride, heat to 60-80°C, reflux for 6 hours, remove benzene, collect 90 ~105℃ / -0.093MPa fraction, the measured refractive ...

Embodiment 2

[0079] Embodiment two. synthetic aromatic retinoic acid, its steps are as follows:

[0080] The aryl retinoic acid ethyl ester synthesized in Example 1, that is, P-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ) propenyl]-ethyl benzoate 50g was added in 1100 milliliters of ethanol, then 500 milliliters of 0.5N NaOH was added, and refluxed for 2.5 hours;

[0081] Use 0.5N sulfuric acid to adjust the pH value to 1-2, separate the solid, and wash it with water to remove the acidity;

[0082] Reflux with dichloromethane to dissolve, recover and remove most of the dichloromethane, add n-hexane to the remaining solution, and precipitate a solid, which is P-[(E)-2-(5,6,7,8-tetrahydro-5 , 5,8,8-tetramethyl-2-naphthyl)propenyl]-benzoic acid, referred to as aromatic retinoic acid or aromatic retinoic acid (Arotinoic acid), melting point 248 ~ 249 ° C.

Embodiment 3

[0083] Embodiment 3. Fragrant ethyl retinoic acid capsules, each containing 0.03 mg of aromatic ethyl retinoic acid and 200 mg of starch; combined with "8-methoxy psoralen long-wave ultraviolet photochemical therapy" for the treatment of psoriasis, "8 -Methoxypsoralen long-wave ultraviolet photochemical therapy" According to conventional treatment, the patient took the aromatic ethyl retinoate capsule once a day, 1 capsule each time.

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Abstract

A process for synthesizing aryltretinoin and aryltretinoin ethylester, used for preparing capsules to treat psoriasis, includes such steps as reaction between [1-(5,6,7,,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-ethyl]-phosphine triphenylbromide and p-ethoxycarbonyl benzaldehyde in isopropanol to obtain P-[(E)-2 -(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) propenyl]-ethyl benzoate, that is, aryltretinoin ethylester, and adding it to alcohol to synthesize P-[(E)-2 -(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) propenyl]-benzoate, that is, aryltretinoin.

Description

technical field [0001] The invention relates to a synthesis method of chemical substances and application of medicines, in particular to a synthesis method of aryl retinoic acid and aryl retinoic acid ethyl ester and their application in pharmacy. Background technique [0002] On July 4, 1979, the UK issued a patent application titled "stilbene derivatives" with application number No.7849418. This patent application discloses a method for preparing stilbene derivatives, and the applicant believes that hundreds or even thousands of derivatives can be prepared by this method. Since there are too many derivatives included, only a principled guidance is given for the preparation of a small amount of derivatives, so it is not detailed and specific enough for each specific derivative. Arylretinoic acid, P-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2 -Naphthyl)propenyl]-benzoic acid and ethyl aryretinoate, namely P-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl -2-naphthyl) ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/76C07C63/33A61K31/192A61K31/216A61K9/48A61P17/00
Inventor 张国威张明张青王作文
Owner 徐岩峰
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