Process for producing pyrrole compound

A compound and product technology, applied in the field of preparing pyrrole compounds, can solve problems such as desulfurization reaction of 2-mercaptopyrrole derivatives that have not been described

Active Publication Date: 2012-04-18
TAKEDA PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the desulfurization reaction of the res

Method used

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  • Process for producing pyrrole compound
  • Process for producing pyrrole compound
  • Process for producing pyrrole compound

Examples

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[0294] The preparation method of the present invention is described in detail below.

[0295] As the salts of compounds (I)-(XVII) in the reaction, there may be mentioned metal salts, ammonium salts, salts with organic bases, salts with inorganic bases, salts with organic acids, and alkali or Salts of acidic amino acids, etc. Examples of preferable metal salts include alkali metal salts such as sodium salts, potassium salts, etc., alkaline earth metal salts such as calcium salts, magnesium salts, barium salts, etc., aluminum salts, and the like. Examples of preferred salts with organic bases include trimethylamine, triethylamine, pyridine, picoline, 2,6-lutidine, ethanolamine, diethanolamine, triethanolamine, cyclohexylamine, dicyclohexylamine , N, N'-dibenzylethylenediamine and the like. Examples of preferable salts with inorganic acids include salts with hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid and the like. Examples of preferred sa...

Embodiment 1

[0469] 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile

[0470] 2-Chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile (5.0 g, 22.7 mmol), methanol (150 ml) and diisopropylethylamine (3.8 g, 29.5 mmol) were added to high pressure autoclave and purged the autoclave with nitrogen. 5% palladium on carbon (N.E. CHEMCAT, Standard, 0.5 g) was added. Then, the mixture was vigorously stirred at an internal temperature of 15-25° C. for about 4 hours under a hydrogen atmosphere (0.1 MPa). After purging with nitrogen, the catalyst was filtered off and washed with methanol (15ml). The organic layer was concentrated to about 13 g under reduced pressure. The amount of the contents was adjusted to about 28 g with ethanol. Water (40 ml) was added dropwise at an internal temperature of 15-25°C, and the mixture was stirred at the same temperature for 1 hr. The mixture was cooled to an internal temperature of 0-10°C and stirred for 1 hour. The precipitated crystals were collected by filtration...

Embodiment 2

[0477] 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile

[0478] Add 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile (25.0g, 113mmol), ethanol (350ml) and diisopropylethylamine (19.0g, 147mmol) into the autoclave , the autoclave was purged with nitrogen. A suspension of 5% palladium on carbon (N.E. CHEMCAT, Standard, 2.5 g) in ethanol (25 ml) was added. Under a hydrogen atmosphere, the mixture was stirred vigorously at an internal temperature of 15-25°C for about 7 hours. After purging with nitrogen, the catalyst was filtered off and washed with ethanol (75ml). The filtrates were combined and concentrated under reduced pressure to approximately 140 g. Water (200 ml) was added dropwise at an internal temperature of 20-30°C, and the mixture was stirred at the same temperature for 0.5 hr. The mixture was cooled to an internal temperature of 0-10°C and stirred for 1 hour. The precipitated crystals were collected by filtration, washed with a cold mixed solution of ethanol an...

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Abstract

A process for producing a sulfonylpyrrole compound useful as a medicine, a process for producing an intermediate for use in the process, and a novel intermediate. The process for producing a sulfonylpyrrole compound (VIII) comprises reducing a compound (III), subsequently hydrolyzing the compound to obtain a compound (IV), sulfonylating the compound (IV) to obtain a compound (VI), and aminating the compound (VI) to thereby produce the compound (VIII).

Description

technical field [0001] The present invention relates to a process for the preparation of pyrrole compounds useful as pharmaceuticals, especially acid secretion inhibitors, a process for the preparation of intermediates used in the process, novel intermediates and the like. Background of the invention [0002] Pyrrole compounds having a substituted sulfonyl group at the 1-position (hereinafter referred to as sulfonylpyrrole compounds) are useful as acid secretion inhibitors (proton pump inhibitors), therapeutic drugs for tumor diseases or autoimmune diseases (Patent Documents 1-3 ). [0003] For example, Patent Document 2 describes a compound having acid secretion inhibitory activity or a salt thereof represented by the following formula: [0004] [0005] Among them, r 1 is a monocyclic nitrogen-containing heterocyclic group optionally fused to a benzene ring or a heterocyclic ring, wherein the monocyclic nitrogen-containing heterocyclic group optionally fused to a benz...

Claims

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Application Information

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IPC IPC(8): C07D207/34C07D207/333C07D207/36C07D401/12
CPCC07D207/34C07D207/48C07D207/30C07D207/36C07D207/337C07D401/12C07C225/14C07D207/333
Inventor 池本朋己水船秀哉长田敏明瀬良美佐代福田直弘山崎健
Owner TAKEDA PHARMA CO LTD
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