A kind of preparation method of icatibant acetate

A technology of icatibant acetate and amino acid, which is applied to the preparation method of peptide, chemical instrument and method, production of bulk chemicals, etc., can solve the problems of cumbersome process and low purity, and achieves simple preparation process, reduced aggregation, and reduced Effects of Deletion and Insertion Peptide Impurities
CN111944016BActive Publication Date: 2022-04-29台州吉诺生物科技有限公司
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
台州吉诺生物科技有限公司
Publication Date
2022-04-29

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Abstract

The invention discloses a preparation method of icatibant acetate, which belongs to the technical field of medicine synthesis. The preparation method comprises: using a solid-phase synthesis method, sequentially connecting amino acids and dipeptide fragments with protective groups at the N-terminal and side chains to a resin solid-phase carrier according to the sequence of icatibant acetate main chain peptides, to obtain resin peptides , in which the guanidine group of arginine is protected by nitro group, and the N-terminal of glycine is connected with 2,4-dimethoxybenzyl group; the resin peptide is cleaved by a cleavage reagent, the cleaved peptide chain is separated, and the nitration is catalyzed by palladium carbon base to obtain the crude product of icatibant, which was purified to obtain icatibant acetate. The present invention uses a nitro protecting group to protect the arginine residue, which greatly reduces the synthesis cost; during the synthesis process, dipeptide fragments and skeletons are used to modify the peptide at the corresponding amino acid position, reducing the impurities of missing peptides and inserted peptides, and the preparation process is simple. , stable and commercially viable.
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Description

technical field

[0001] The invention relates to the technical field of drug synthesis, in particular to a method for preparing icatibant acetate. Background technique

[0002] Icitibant is a selective competitive antagonist of the bradykinin B2 receptor with an affinity similar to that of bradykinin. Bradykinin, a vasodilator, is thought to be responsible for the typical hereditary angioedema symptoms of local swelling, inflammation, and pain. Icibant inhibits the binding of bradykinin to B2 receptors, thereby treating the clinical symptoms of acute attacks of hereditary angioedema. Icitibant is a synthetic decapeptide composed of five non-protein amino acids. In 2011, icatibant, developed by Shire Orphan Therapies, received preliminary approval in the United States as a subcutaneous injection.

[0003] Patent document US5648333A discloses icatibant and its preparation method.

[0004] Patent document CN107417770A discloses that by using a novel coupling reagent, such as...

Claims

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