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Method for preparing dipeptidyl peptidase-IV inhibitor

A compound, the technology of camphorsulfonic acid, applied in the field of compound preparation, can solve the problems of high product cost and expensive reagents

Inactive Publication Date: 2010-12-29
BEIJING HOPE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Both of the above-mentioned methods have the problems that the reagents are expensive and the cost of the product is high

Method used

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  • Method for preparing dipeptidyl peptidase-IV inhibitor
  • Method for preparing dipeptidyl peptidase-IV inhibitor
  • Method for preparing dipeptidyl peptidase-IV inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: 7-[3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-trifluoromethane Preparation of base-1,2,4-triazolo[4,3-a]pyrazine (III)

[0029] Add 10g of compound (II) and 110ml of methanol into the reaction kettle, heat up to about 40°C and stir to dissolve, add 2g of palladium carbon, pressurize and roughly estimate the hydrogen absorption according to the theoretical amount, about 6-8 hours, after the reaction is completed, filter out the palladium Carbon, 200ml isopropanol was added to the filtrate, stirred for 1 hour, and compound III was obtained by filtration.

Embodiment 2

[0030] Example 2: 7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3 -Preparation of trifluoromethyl-1,2,4-triazolo[4,3-a]pyrazine camphorsulfonate

[0031] Dissolve 10 g of compound III in 100 ml of toluene, add 6.2 g of D-camphorsulfonic acid monohydrate, heat and stir overnight. Cool, filter, and recrystallize the solid from toluene. Camphorsulfonate is obtained.

Embodiment 3

[0032] Example 3: 7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3 - Preparation of trifluoromethyl-1,2,4-triazolo[4,3-a]pyrazine tartrate

[0033] Dissolve 10 g of compound III in 100 ml of toluene, add 3.7 g of (-)-tartaric acid, and react at room temperature for 48 hours. A white solid precipitated out of the system, was filtered, and the solid was recrystallized from toluene. Get tartrate.

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PUM

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Abstract

The invention provides a method for preparing a dipeptidyl peptidase-IV inhibitor, and in particular relates to a method for preparing 7-[3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-trifluoromethyl-1,2,4-triazol[4,3-a]pyrazine raceme or an optically pure (R) or (S) compound thereof. The method comprises the following steps of: (1) performing hydrogenation reduction to obtain racemate; (2) reacting the racemate with camphorsulfonic acid or tartaric acid; and (3) converting a salt obtained in the step 2 into a corresponding alkali. The method has low cost and can be applied to industrial production.

Description

Field of invention: [0001] The present invention relates to a preparation method of a compound, especially optically pure 7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5 , The preparation method of 6,7,8-tetrahydro-3-trifluoromethyl-1,2,4-triazolo[4,3-a]pyrazine. Background technique: [0002] 7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-trifluoromethane Base-1,2,4-triazolo[4,3-a]pyrazine, or sitagliptin, is a potent inhibitor of dipeptidyl peptidase-IV for the treatment and prophylaxis of Diseases and conditions with base peptidase-IV inhibitors. [0003] There are several disclosed preparation methods of sitagliptin. WO2004085661 and WO20040876 describe the use of (s)-phenylglycineamide to obtain chiral compounds and further prepare sitagliptin; WO2005030127 and WO2006081151 describe the use of Asymmetric hydrogenation of transition metal precursors complexed with ferrocenyl diphosphine ligands. Both of the above-mentioned methods ...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07B57/00A61K31/4985A61P43/00
Inventor 王海军张勇刘长茹艾海马刘艳玲裴九宏
Owner BEIJING HOPE PHARMA
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