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Preparation method of loxoprofen

A new method and intermediate technology, applied in the field of preparation of loxoprofen, can solve the problems of long compound synthesis route, poor compound activity, low reaction conversion rate, etc., and achieve simple and easy-to-obtain starting materials, weak corrosiveness, color shallow effect

Active Publication Date: 2020-07-17
SHANGHAI INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the biggest problem of this route is that the activity of compound (Ⅵ) is poor, and its reaction conversion rate with compound (Ⅲ) is low, thereby causes the whole route yield to be very low
[0011] In addition, both route 1 and route 2 require the use of compound (Ⅲ) as a starting material, but compound (Ⅲ) has a long synthetic route and a cumbersome process

Method used

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  • Preparation method of loxoprofen
  • Preparation method of loxoprofen
  • Preparation method of loxoprofen

Examples

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Embodiment 1

[0039] This embodiment provides a kind of preparation method of loxoprofen, and concrete steps are as follows:

[0040] Step 1: Synthesis of intermediate (IX):

[0041] Add 55g of compound (Ⅷ), 300mL of dichloromethane and 70g of anhydrous aluminum trichloride to the reaction flask, control the internal temperature to about 0°C, and slowly dissolve 53.5g of compound (Ⅶ) prepared according to Example 4 into 50mL of dichloromethane Add the solution dropwise into the reaction flask; then rise to 40°C and stir for 12 hours until no obvious gas is released; after cooling, slowly add 750mL of 4N hydrochloric acid aqueous solution into the reaction system at a temperature of 0-5°C; then raise the temperature to 25°C, Continue to stir for 1 h; separate the organic phase; extract the aqueous phase once with 100 mL of dichloromethane, and combine the organic phases; wash the organic phase with 500 mL of saturated aqueous sodium bicarbonate solution and 500 mL of water successively, and ...

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Abstract

The invention discloses a novel preparation method of loxoprofen (I). The reaction process comprises the following steps: a compound (VII) and a compound (VIII) are subjected to a condensation reaction to obtain an intermediate (IX), the intermediate (IX) is subjected to a hydrogenation reduction reaction in a mixed solvent of acid and alcohol to obtain an intermediate (X), and the intermediate (X) is subjected to a hydrolysis reaction to obtain loxoprofen (I).

Description

technical field [0001] The present invention relates to a new method for preparing loxoprofen (I). Background technique [0002] Loxoprofen sodium (II, Loxoprofen Sodium), 2-[4-(2-oxocyclopentane-1-ylmethyl)phenyl]propionate sodium dihydrate, is a kind of non-phenylpropionic acid Steroidal anti-inflammatory drugs are used for pain relief and anti-inflammation of chronic rheumatoid arthritis, osteoarthritis, frozen shoulder and other diseases, as well as pain relief and anti-inflammation after tooth extraction or surgery. Developed by Japan Sankyo Co., Ltd. (currently Daiichi Sankyo Co., Ltd.). The trade name is Rifampicin. [0003] [0004] At present, the main industrialized preparation route of loxoprofen sodium is reported by Sankyo Co., Ltd. of Japan, and the following route is described in detail in the patent US4161538A and J.Med.Chem, 1984,27,212: [0005] Route 1: [0006] [0007] This route first forms compound (V) through the condensation reaction of com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C59/86C07C67/343C07C67/317C07C69/738
CPCC07C51/09C07C67/343C07C67/317C07C2601/08C07C69/738C07C59/86
Inventor 毛宇成潘仙华陈宇黎鸿艺
Owner SHANGHAI INST OF TECH
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