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Method for producing 4-pentafluoride-sulfanyl-benzoylguanidines

An alkyl and compound technology, applied in organic chemistry, pharmaceutical formulations, in vivo radioactive preparations, etc., can solve the problems of huge technical complexity, low yield, unsuitable reagents and reaction conditions, etc.

Inactive Publication Date: 2012-04-25
SANOFI AVENTIS DEUT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the methods described therein for the preparation of these compounds have low yields, require reagents and reaction conditions that cause great technical complexity, or are not suitable for large-scale preparations

Method used

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  • Method for producing 4-pentafluoride-sulfanyl-benzoylguanidines
  • Method for producing 4-pentafluoride-sulfanyl-benzoylguanidines
  • Method for producing 4-pentafluoride-sulfanyl-benzoylguanidines

Examples

Experimental program
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Embodiment 1

[0152] a) 4-aminophenylsulfur pentafluoride

[0153]

[0154] A solution of tin(II) chloride (1465 g, 7.73 mol) in concentrated (32%) aqueous HCl was heated to 80 °C with stirring and then introduced into 4-nitrophenylpenta in 8 portions over 1 h under ice cooling. Sulfur fluoride (584 g, 2.344 mol). During this time, the internal temperature was kept below 100°C. Subsequently, the mixture was stirred at an internal temperature of 85 °C for 1.5 h, then cooled to 45 °C over a further 1 h. A mixture of ice (12 kg), NaOH (2 kg) and dichloromethane (1.5 L) was prepared and added to the reaction mixture with vigorous stirring. Separate the phases, extract the aqueous phase with dichloromethane 3 times, 1 L each time, combine the organic phases, and wash with Na 2 SO 4 Dry and evaporate in vacuo. 510 g (99%) of 4-aminophenylsulfur pentafluoride were obtained as pale yellow crystalline powder, m.p. Philip, D. Tetrahedron 2000, 56, 3399: 57-59°C).

[0155] 1 H-NMR 400MHz, C...

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Abstract

The invention relates to a method for producing 4-pentafluoride-sulfanyl-benzoylguanidines of formula (I) wherein groups from R1 to R4 correspond to meanings given in claims. The compounds of the formula (I) constitute NHE1 inhibitors and can be used for curing cardiovascular diseases.

Description

[0001] This application is a divisional application, the application number of the original application is 200480033480.6, the application date is November 3, 2004, and the title of the invention is "method for preparing 4-thiobenzoylguanidine pentafluoride". technical field [0002] The present invention relates to a process for the preparation of 4-pentafluorothiobenzoylguanidine of formula I. Compounds of formula I are NHE1 inhibitors and are useful, for example, in the treatment of cardiovascular disorders. Background technique [0003] German application 10222192 describes pentafluorothiobenzoylguanidines as NHE1 inhibitors. However, the methods described therein for the preparation of these compounds have low yields, require reagents and reaction conditions which cause great technical complexity or are not suitable for large-scale preparations. Contents of the invention [0004] It has now been found that a new and highly efficient synthetic method which avoids the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C381/00A61P9/00
CPCC07C381/00A61P9/00A61K51/0406
Inventor G·舒贝特H-W·克勒曼
Owner SANOFI AVENTIS DEUT GMBH
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