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2-phenyl-substituted imidazo-triazone used as phosphodiesterase inhibitor

A kind of phenyl substitution, imidazo technology, is applied in the application field of phosphodiesterase inhibitor, can solve the problem such as not requiring protection sulfonamido

Inactive Publication Date: 2004-06-30
BAYER IP GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The patent does not claim a compound with a sulfonylamino group at the 2-position aryl

Method used

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  • 2-phenyl-substituted imidazo-triazone used as phosphodiesterase inhibitor
  • 2-phenyl-substituted imidazo-triazone used as phosphodiesterase inhibitor
  • 2-phenyl-substituted imidazo-triazone used as phosphodiesterase inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1A

[0467] 2-Butyrylaminopropionic acid

[0468]

[0469] 22.27 g (250 mmol) of D, L-alanine and 55.66 g (550 mmol) of triethylamine were dissolved in 250 ml of dichloromethane, and the solution was cooled to 0°C. 59.75 g (550 mmol) of trimethylsilyl chloride were added dropwise, and the solution was stirred at room temperature for 1 hour and at 40° C. for 1 hour. After cooling to -10°C, 26.64 g (250 mmol) of butyryl chloride was added dropwise, and the resulting mixture was stirred at -10°C for 2 hours and at room temperature for 1 hour.

[0470] Under ice-cooling, 125 ml of water were added dropwise, and the reaction mixture was stirred at room temperature for 15 minutes. The aqueous phase was evaporated to dryness, the residue was triturated with acetone and the mother liquor was filtered. The solvent was removed and the residue was chromatographed. The resulting product was dissolved in 3 N aqueous sodium hydroxide solution, and the resulting solution was evaporated to d...

Embodiment 2A

[0474] 2-Butyrylaminobutyric acid

[0475]

[0476] 25.78 g of 2-aminobutyric acid (250 mmol) and 55.66 g (550 mmol) of triethylamine were dissolved in 250 ml of dichloromethane, and the solution was cooled to 0°C. 59.75 g (550 mmol) of trimethylsilyl chloride were added dropwise, and the solution was stirred at room temperature for 1 hour and at 40° C. for 1 hour. After cooling to -10°C, 26.64 g (250 mmol) of butyryl chloride was added dropwise, and the resulting mixture was stirred at -10°C for 2 hours and at room temperature for 1 hour.

[0477] Under ice-cooling, 125 ml of water were added dropwise, and the reaction mixture was stirred at room temperature for 15 minutes. The organic phase was mixed with aqueous sodium hydroxide solution, and the organic solvent was removed under reduced pressure. After acidification, the precipitated solid was stirred once with water and twice with petroleum ether, and dried under reduced pressure at 45°C. 29.1 g (67%) of a colorless...

Embodiment 3A

[0481] 2-Ethoxybenzonitrile

[0482]

[0483] 25 g (210 mmol) of 2-hydroxybenzonitrile were refluxed overnight in 500 ml of acetone with 87 g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide. The solid was filtered off, the solvent was removed under reduced pressure, and the residue was distilled under reduced pressure. 30.0 g (97%) of a colorless liquid were obtained.

[0484] 200MHz 1 H-NMR (DMSO-d6): 1.48, t, 3H; 4.15, quart., 2H; 6.99, dt, 2H; 7.51, dt,

[0485] 2H.

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Abstract

The 2-phenyl-substituted imidazotriazinones having short, unbranched alkyl radicals in the 9-position are prepared from the corresponding 2-phenyl-imidazotriazinones by chlorosulphonation and subsequent reaction with the amines. The compounds inhibit cGMP-metabolizing phosphodiesterases and are suitable for use as active compounds in pharmaceuticals, for the treatment of cardiovascular and cerebrovascular disorders and / or disorders of the urogenital system, in particular for the treatment of erectile dysfunction.

Description

[0001] This application is a divisional application of a patent application with a filing date of October 31, 1998 and an application number of 98811092.X (PCT / EP98 / 06910). technical field [0002] The present invention relates to 2-phenyl-substituted imidazotriazinones, their preparation methods, and their applications as medicines, especially as phosphodiesterase inhibitors for metabolizing cGMP. Background technique [0003] Laid-open specification DE 2811780 describes imidazotriazines as bronchodilators and discloses their antispasmodic activity and resistance to phosphodiesterases (cAMP-PDEs, named after Beavo: PDE-III and PDE-IV) inhibitory activity. Which does not disclose anti-phosphodiesterases (cGMP-PDEs) that cause cyclic guanylate metabolism (cGMP-PDEs, according to the nomenclature of Beavo and Reifsnyder ("Pharmacological Science Advances" (Trends in Pharmacol.Sci) 11, 150-155, 1990): PDE- I, PDE-II and PDE-V) inhibitory activity. This patent does not claim c...

Claims

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Application Information

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IPC IPC(8): A61K31/00A61K31/53A61K31/5375A61K31/5377A61K31/541A61K31/55A61K31/551A61K31/662A61P9/00A61P9/10A61P11/08A61P13/02A61P13/08A61P13/10A61P15/00A61P15/10A61P43/00C07DC07D487/04C07D491/113C07D519/00C07F9/6561
CPCC07D487/04C07F9/6561A61P11/08A61P13/00A61P13/02A61P13/08A61P13/10A61P15/00A61P15/10A61P43/00A61P9/00A61P9/06A61P9/08A61P9/10A61P9/12A61K31/53
Inventor U·尼维纳M·埃斯-萨耶德H·哈宁T·申克K·H·施莱默J·克尔德尼希E·比肖夫E·佩尔兹波恩K·德姆波夫斯基P·塞尔诺M·诺瓦科夫斯基
Owner BAYER IP GMBH
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