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New preparation process of 5-aminolevulinic acid (5-ALA) hydrochloride

A new technology of aminolevulinic acid hydrochloride, which is applied in the field of new preparation technology of aminolevulinic acid hydrochloride, can solve the problems of difficult separation of intermediate products, low reaction yield, high cost of 5-ALA preparation, etc.

Active Publication Date: 2012-08-29
上海泺安医药技术有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0030] According to the existing literature, the preparation cost of 5-ALA is relatively high, either because the raw materials are rare, or because the intermediate product is difficult to separate, or because the reaction yield is not high, thus limiting the production of 5-ALA and its derivatives. Application of things

Method used

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  • New preparation process of 5-aminolevulinic acid (5-ALA) hydrochloride
  • New preparation process of 5-aminolevulinic acid (5-ALA) hydrochloride
  • New preparation process of 5-aminolevulinic acid (5-ALA) hydrochloride

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Experimental program
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Embodiment

[0047] Preparation of epoxide 4-epoxyvalerate benzyl ester

[0048] In a 5000 milliliter flask, 155 grams of 4-alkene-pentanoic acid benzyl ester was dissolved in 1730 milliliters of dichloromethane, and 195 grams of m-chloroperoxybenzoic acid was added to maintain the reaction temperature from 30 to 35 degrees Celsius, and stirred for 24 hours. The reaction process A white solid precipitated out. TLC (developing solvent: cyclohexane-ethyl acetate 4:1) followed the reaction until the raw material 4-ene-pentanoic acid benzyl ester disappeared. Cool in a water bath, add 3% sulfurous acid solution, and test with potassium iodide starch test paper, the test paper does not show blue. Sodium bicarbonate solution was added to dissolve the solid, pH 7-8. Transfer to a separatory funnel and separate the layers. The organic matter was washed with 200 mL of brine. The organic layer was separated and dried over anhydrous sodium sulfate overnight. Suction filtration, concentration, an...

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Abstract

The invention relates to a new preparation process of 5-aminolevulinic acid (5-ALA) hydrochloride. The 5-ALA is a second-generation photosensitizer, and has a structure shown in the specification. The 5-ALA hydrochloride has been used for treating photosensitive keratosis in America. The 5-ALA hydrochloride is used for treating dermatological condyloma acuminatum in China. Indications related to the 5-ALA are also extended in clinical application. According to the new preparation process, 4-alkenylbenzyl valerate is used as a starting raw material and is subjected to oxidation, addition, oxidation and catalytic hydrogenation to successfully synthesize the 5-ALA.

Description

technical field [0001] The invention relates to a new preparation process of aminolevulinic acid hydrochloride (5-ALA). Photodynamic medicine is a field that has developed rapidly in the diagnosis and treatment of certain cancers and the treatment of skin diseases in recent years. Aminolevulinic acid hydrochloride, a second-generation photosensitizer, is now used in the United States for the treatment of actinic keratoses. It is used in China to treat genital warts, a skin venereal disease. The indications of 5-ALA are still expanding clinically. The invention uses benzyl 4-valerate as a starting material, and successfully synthesizes 5-ALA through oxidation, addition, oxidation and catalytic hydrogenation. technical background [0002] There are many reports on the synthesis of 5-ALA. CN101462974 discloses following route: [0003] [0004] NOTE: other reagents also tried, [0005] Reactants: 1, Reagents: 8, Solvents: 4, [0006] Steps: 1, Stages: 7 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/22C07C227/18C07D301/12C07D301/14C07D303/40
Inventor 何勇张俊杰
Owner 上海泺安医药技术有限公司
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