A kind of method for preparing loxoprofen active metabolite

A technology of compound and chiral auxiliary agent, which is applied in the field of synthesis of trans-hydroxyl active metabolites, can solve the problems that are not suitable for large-scale production energy consumption, difficult to obtain reagents, harsh conditions and other problems, so as to achieve simple operation and avoid purification Steps, high safety effect
CN106045842BActive Publication Date: 2018-03-27NANJING HERON PHARMA SCI & TECH CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
NANJING HERON PHARMA SCI & TECH CO LTD
Publication Date
2018-03-27

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Abstract

The invention discloses a method for synthesizing the trans hydroxyl active metabolite of loxoprofen. The present invention uses 2-[p-(bromomethyl)phenyl]propionic acid as a raw material to obtain an intermediate compound of formula 3 through resolution and methyl esterification; starting with L-phenylalaninol to prepare a chiral auxiliary compound of formula 7 The compound of cyclopentanone and chiral auxiliary formula 7 first forms Schiff base formula 9, and then condenses with intermediate formula 3 to form intermediate formula 11; the compound of intermediate formula 11 undergoes acidic hydrolysis, and stereoselectively reduces cyclopentanone carbonyl to obtain Trans hydroxyl active metabolite formula TM compound. The raw materials of this synthesis route are easy to obtain, the operation is simple, the environment is friendly, the separation method of column chromatography is avoided, and the technical requirements of industrialized large-scale production are fully satisfied.
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Description

technical field

[0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for synthesizing a trans hydroxyl active metabolite of loxoprofen. Background technique

[0002] Loxoprofen is a precursor type of phenylpropionic acid non-steroidal anti-inflammatory drugs, which is less irritating to the gastrointestinal tract after oral administration. After absorption in the body, it is biotransformed into trans-hydroxyl active metabolites by the liver. It produces pharmacological effects by inhibiting the synthesis of prostaglandins and unsaturated fatty acids through competitive binding to cyclooxygenase. In 1986, Japan's Sankyo Co., Ltd. launched Loxolo tablets and granules in Japan under the trade name of "Loxonin", and entered the Chinese market in 1995. Loxoprofen has excellent antipyretic, analgesic and anti-inflammatory effects, and its analgesic effect is 10-20 times stronger than that of ketoprofen, indomethacin, and naproxe...

Claims

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