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Formation of N-protected bis-3,6-(4-aminobutyl)-2,5-diketopiperazine through cyclic alpha-N-protected amino ester

A technology of diketopiperazine and aminoalkyl, applied in the field of chemical synthesis, can solve the problems of changing active agents, unusable, poor stability, etc.

Active Publication Date: 2018-04-20
MANNKIND CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, broad-spectrum use of drug delivery systems has been prevented for a number of reasons including: (1) the system requires toxic amounts of adjuvants or inhibitors; (2) suitable low molecular weight carriers (i.e., active agents) are not available; ( 3) the system exhibits poor stability and insufficient shelf life; (4) the system is difficult to manufacture; (5) the system cannot protect the active agent (carrier); (6) the system negatively alters the active agent; or (7) the system cannot Allow or facilitate absorption of active agents

Method used

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  • Formation of N-protected bis-3,6-(4-aminobutyl)-2,5-diketopiperazine through cyclic alpha-N-protected amino ester
  • Formation of N-protected bis-3,6-(4-aminobutyl)-2,5-diketopiperazine through cyclic alpha-N-protected amino ester
  • Formation of N-protected bis-3,6-(4-aminobutyl)-2,5-diketopiperazine through cyclic alpha-N-protected amino ester

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Embodiment

[0077] figure 1 Active amino esters for protection by cyclic α-N- ( figure 1 The reaction scheme of CBz-Lys-NCA) to produce compound 11 is shown. CBz-Lys-NCA was synthesized according to the following procedure: triphosgene (26.49 g), CBz-Lys (50.00 g) and tetrahydrofuran (THF) (500 mL) were injected into a vacuum chamber equipped with nitrogen purge, mechanical stirrer, condenser and thermocouple 1L 4-neck round bottom flask. The reaction mixture was heated to 35-38 °C until clear. The reaction mixture was cooled to ambient temperature, and nitrogen gas was bubbled through the reaction mixture to remove any excess phosgene. The solvent was then removed in vacuo. The crude product was crystallized from THF (200 mL) and hexane (125 mL). The resulting white solid was isolated by filtration and dried in vacuo overnight. The yield of CBz-Lys-NCA was 48.6 g (89.02%).

[0078] Once CBz-Lys-NCA was obtained, it was used to generate compound 11 according to the following: benza...

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Abstract

A method for the synthesis of N-protected 3,6-aminoalkyl-2,5-diketopiperazines is provided. The method includes preparing cyclic a-N protected active amino ester and adding the cyclic a-N protected active amino ester to a mixture of an amine catalyst in an organic solvent.

Description

[0001] This application is filed on March 14, 2014, application number 201480015534.X, title of invention "Formation of N-protected bis-3,6-(4-aminobutyl) through cyclic α-N-protected amino ester -2,5-diketone piperazine" is a divisional application of the Chinese patent application. [0002] Related Application Cross Reference [0003] This nonprovisional patent application claims priority from US Provisional Application Serial No. 61 / 798,016, the contents of which are hereby incorporated by reference as if set forth in their entirety herein. technical field [0004] The present invention relates to compositions for the delivery of active agents, particularly bioactive agents. The disclosed embodiments are in the field of chemical synthesis, and more particularly relate to improved synthetic methods for the preparation of substituted piperazinediketones. Background technique [0005] Drug delivery is an ongoing problem in administering active agents to patients. Traditi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/08A61K47/22
CPCA61K47/22C07D241/08C07D241/10C07D241/04
Inventor J.J.弗里曼O.凡斯蒂尔W.E.贝K.S.克拉夫特
Owner MANNKIND CORP