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A kind of method for preparing cetirizat

A technology for lixisenatide and compound, which is applied in the field of synthesizing cetilistatin products, can solve the problems of difficult reaction conditions, high cost, low yield and the like, and achieves the effects of simple post-processing, residual solution and high yield.

Inactive Publication Date: 2016-03-30
CHONGQING TOPTECH PHARMA TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The present invention solves the problems of low yield and high cost in the current method of preparing cetilistat (hexadecyloxy-6-methyl-4H-3,1-benzoxazin-4-one, cetilistat) , Reaction conditions are not easy for industrial production, etc., providing a new synthetic route and corresponding preparation method

Method used

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  • A kind of method for preparing cetirizat
  • A kind of method for preparing cetirizat
  • A kind of method for preparing cetirizat

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Put compound A (45.3g, 0.3mol) into a 1L reaction flask, add 500ml of methanol, add 30ml of concentrated sulfuric acid dropwise under stirring, stir overnight at room temperature, concentrate and recover most of the methanol, add 200ml of acetone, and stir in an ice bath for 2h. Suction filtration and drying gave 73.4 g of 2-amino-5-methylbenzoic acid methyl ester hydrogen sulfate, with a yield of 93%.

Embodiment 2

[0063] Put compound A hydrochloride (56.3g, 0.3mol) into a 1L reaction flask, add 600ml tetrahydrofuran and tert-butanol (26.7g, 0.36mol), add DCC (61.9g, 0.3mol) in batches under stirring, and Stir for 2h, then add DMPA (0.5g), stir overnight, concentrate and recover most of THF, add 600ml ethyl acetate and 30g sodium bicarbonate, stir for 1h, filter with suction, the filtrate is sequentially washed with 1% acetic acid solution, water and saturated saline Fully stirred, washed, separated, concentrated under reduced pressure to a slurry, added 500ml of petroleum ether, stirred for 2h in an ice bath, filtered with suction, and dried to obtain 55.9g of tert-butyl 2-amino-5-methylbenzoate. The yield was 90%.

Embodiment 3

[0065] Put compound A (45.3g, 0.3mol) into a 1L reaction flask, add 500ml of toluene and thionyl chloride (53.6g, 0.45mol), heat up to reflux, stir for 2h, cool down to room temperature, drop benzyl alcohol (43.2g , 0.4mol), stirred overnight at room temperature, concentrated most of the solvent under reduced pressure to form a slurry, stirred for 2h under ice bath, filtered with suction, and dried to obtain 79.2g of benzyl 2-amino-5-methylbenzoate hydrochloride , The yield is 95%.

[0066] Preparation of Compound C:

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Abstract

The invention discloses a method for preparing cetiristat, which belongs to the technical field of pharmaceutical preparation methods and is used to solve the problem of high "three wastes", low yield and high cost in the existing preparation method. The method comprises: (1) esterifying compound A (2-amino-5-methylbenzoic acid) or a salt thereof; (2) acylating the esterified product obtained in step 1 with n-hexadecyl chloroformate; (3) Deesterifying the compound obtained in step 2 to obtain 2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid; (4) cyclizing the compound obtained in step 3 to obtain the target product. By improving the production steps, a synthetic method is provided which is simple and efficient, convenient for industrial production and capable of obtaining high-quality cetiristat.

Description

technical field [0001] The invention belongs to the technical field of preparation methods of medicines, in particular, it is a method for synthesizing cetiristat product which is easy to operate, highly efficient and convenient for industrial production. Background technique [0002] Cetilistat (2-hexadecyloxy-6-methyl-4H-3,1-benzoxazin-4-one, cetilistat) is a long-acting and potent drug developed by Alizyme Specific gastrointestinal lipase inhibitors form covalent bonds with the active serine sites of gastric lipase and pancreatic lipase in the lumen of the stomach and small intestine to inactivate the enzymes, thereby achieving the therapeutic effect of reducing calorie intake and controlling body weight. The biggest advantage of this drug is that it does not act on the nervous system, does not affect other enzyme activities in the gastrointestinal tract, and is safer than the current similar drug orlistat. Its structural formula is as follows: [0003] [0004] In t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/26
CPCC07D265/26
Inventor 陈捷梁杰杜昌勇沈君伟叶健陈小勇
Owner CHONGQING TOPTECH PHARMA TECH
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