Preparation method of saxagliptin intermediate

An intermediate, azabicyclic technology, applied in the field of medicinal chemistry, can solve the problems of high cost and low yield, and achieve the effect of simple operation, high selectivity and large-scale production
CN104628622AInactive Publication Date: 2015-05-20SHANGHAI INST OF TECH
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
SHANGHAI INST OF TECH
Publication Date
2015-05-20
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention provides a preparation method of a saxagliptin intermediate (1S, 3S, 5S)-3-(amino carbonyl)-2-azabicyalo[3.1.0]hexane-2-tert-butyl formate. According to the preparation method, L-pyroglutamic acid is taken as a raw material, and an esterification reaction, Boc protection, reduction, elimination, cyclopropylation, resolution, hydrolyzation, ammonolysis, Boc deprotection and ammonolysis are performed on L-pyroglutamic acid, and finally, the compound (1S, 3S, 5S)-3-(amino carbonyl)-2-azabicyalo[3.1.0]hexane-2-tert-Butyl formate is obtained. The preparation method of the saxagliptin intermediate is cheap and easily available in raw materials, reasonable in process, simple and convenient to operate, high in enantiomer selectivity and high in yield.
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Description

technical field

[0001] The invention belongs to the field of medicinal chemistry, in particular to a saxagliptin intermediate, specifically a saxagliptin intermediate (1S, 3S, 5S)-3-(aminocarbonyl)-2-azabicyclo [3.1.0] Preparation method of tert-butyl hexane-2-carboxylate. Background technique

[0002] Saxagliptin is the first hypoglycemic drug based on the mechanism of incretin jointly developed by two global pharmaceutical companies, Bristol-Myers Squibb and AstraZeneca. It was approved by the US Food and Drug Administration in July 2009. Approved for initial listing.

[0003] Saxagliptin is a high-efficiency dipeptidyl peptidase-4 (DPP-4) inhibitor with good tolerance and safety. It can be used as an adjuvant therapy with diet and exercise to improve the health status of adults with type 2 diabetes. Blood sugar control status. The drug has a unique mechanism of action. It selectively inhibits the DPP-4 enzyme, thereby promoting the secretion of insulin and reducing the...

Claims

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