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A novel process for the preparation of n-(4-nitro-2-sulfamoyl-phenyl)-malonamic acid methyl ester and n-(4-amino-2-sulfamoyl-phenyl)-malonamic acid methyl ester

一种丙酰胺酸甲酯、甲磺酰基氨基的技术，应用在制备N-(4-硝基-2-氨磺酰基-苯基)-丙酰胺酸甲酯和N-(4-氨基-2-氨磺酰基-苯基)-丙酰胺酸甲酯的新领域，能够解决生色、颜色问题等问题

Inactive Publication Date: 2015-11-11
F HOFFMANN LA ROCHE & CO AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, in WO2010 / 42834, the production of the electron-rich diaminobenzene intermediate 2,5-diamino-benzenesulfonamide will cause color problems, and this problem needs to be reduced in the next intermediate, or it will lead to the final product (race Color issues in Poke Bouvet
In addition, the route of WO2010 / 42834 also leads to chlorine impurity (identified by LC / MS in the key intermediate N-(4-methylsulfonylamino-2-sulfamoyl-phenyl)-propionamic acid methyl ester)

Method used

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  • A novel process for the preparation of n-(4-nitro-2-sulfamoyl-phenyl)-malonamic acid methyl ester and n-(4-amino-2-sulfamoyl-phenyl)-malonamic acid methyl ester
  • A novel process for the preparation of n-(4-nitro-2-sulfamoyl-phenyl)-malonamic acid methyl ester and n-(4-amino-2-sulfamoyl-phenyl)-malonamic acid methyl ester
  • A novel process for the preparation of n-(4-nitro-2-sulfamoyl-phenyl)-malonamic acid methyl ester and n-(4-amino-2-sulfamoyl-phenyl)-malonamic acid methyl ester

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Embodiment Construction

[0023] The present invention relates to a new preparation method of the intermediate compound N-(4-methylsulfonylamino-2-sulfamoyl-phenyl)-propionamic acid methyl ester (V), which is used for the preparation of N-(3- {(1R,2S,7R,8S)-3-[(4-fluorophenyl)methyl]-6-hydroxy-4-oxo-3-azatricyclo[6.2.1.0 2,7 ]undec-5-en-5-yl}-1,1-dioxo-1,4-dihydro-1λ 6 ,2,4-Benzothiadiazin-7-yl)methanesulfonamide—trade name celtabvir—a compound used to treat hepatitis C. The present invention also relates to a new intermediate compound for the preparation of the intermediate compound N-(4-methylsulfonylamino-2-sulfamoyl-phenyl)-propionamic acid methyl ester (V), specifically N-(4 -Nitro-2-sulfamoyl-phenyl)-propionamic acid methyl ester (III) and N-(4-amino-2-sulfamoyl-phenyl)-propionamic acid methyl ester (IV).

[0024] The new method of the present invention has two main advantages over the approaches described in US7,939,524 and WO2010 / 42834. The first advantage is that the new route avoids the di...

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Abstract

The present invention provides a novel method for preparing compounds N-(4-nitro-2-sulfamoyl-phenyl)-malonamic acid methyl ester and N-(4-amino-2-sulfamoyl-phenyl)-malonamic acid methyl ester, which are novel intermediates for preparing a key intermediate N-(4-methanesulfonylamino-2-sulfamoyl-phenyl)-malonamic acid methyl ester, for the preparation of N-(3-{(1R,2S,7R,8S)-3-[(4-fluorophenyl)methyl]-6-hydroxy-4-oxo-3-azatricyclo[6.2.1.02,7]undec-5-en-5-yl}-1,1-dioxo-1,4-dihydro-1λ6,2,4-benzothiadiazin-7-yl)methanesulfonamide, also known commercially as Setrobuvir, a compound useful in treating hepatitis C.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Patent Application Serial No. 61 / 751,999, filed January 14, 2013, which is incorporated herein by reference in its entirety. technical field [0003] The present invention provides preparation compound N-(4-nitro-2-sulfamoyl-phenyl)-propionamic acid methyl ester and N-(4-amino-2-sulfamoyl-phenyl)-propionamic acid form A new method for esters, said compound is a new intermediate for the preparation of the key intermediate N-(4-methylsulfonylamino-2-sulfamoyl-phenyl)-propionamic acid methyl ester for the preparation of N- (3-{(1R,2S,7R,8S)-3-[(4-fluorophenyl)methyl]-6-hydroxy-4-oxo-3-azatricyclo[6.2.1.0 2,7 ]undec-5-en-5-yl}-1,1-dioxo-1,4-dihydro-1λ 6 ,2,4-benzothiadiazin-7-yl)methanesulfonamide, commercially known as Setrobuvir, is a compound used in the treatment of hepatitis C. [0004] The present invention also relates to novel intermediate compounds for the prepar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/46C07C311/39C07C303/38C07C303/40
CPCC07C303/40C07C303/38C07C311/46C07C311/39
Inventor J·朱
Owner F HOFFMANN LA ROCHE & CO AG