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Novel uracil compound having inhibitory activity on human deoxyuridine triphosphatase or salt thereof

A compound, uracil technology, applied in the field of new uracil compound or its salt with human deoxyuridine triphosphatase inhibitory activity, can solve the problem of insufficient dUTPase inhibitory activity and achieve excellent dUTPase inhibitory activity effect

Active Publication Date: 2011-05-11
TAIHO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, none of these inhibitors has sufficient inhibitory activity against dUTPase, and they are not compounds that can be used as pharmaceuticals

Method used

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  • Novel uracil compound having inhibitory activity on human deoxyuridine triphosphatase or salt thereof
  • Novel uracil compound having inhibitory activity on human deoxyuridine triphosphatase or salt thereof
  • Novel uracil compound having inhibitory activity on human deoxyuridine triphosphatase or salt thereof

Examples

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Embodiment

[0404] Reference examples, examples, and test examples are shown below, and the present invention will be described in more detail, but the present invention is not limited by these examples.

reference example 1

[0406] Synthesis of (3-(cyclopropylmethoxy)phenyl)methanamine

[0407]

[0408] Dissolve 3-cyanophenol (12.4g) in N,N-dimethylformamide (hereinafter referred to as DMF, 100mL), add potassium carbonate (30.5g), potassium iodide (1.74g), (chloromethyl) ring Propane (10.2 mL), stirred at 90°C for 4 hours. Water (130 mL) was added to the reaction liquid, followed by extraction with toluene (130 mL). The organic layer was washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (hereinafter referred to as THF, 60 mL), and a THF solution (2.4M, 68 mL) of lithium aluminum hydride (hereinafter referred to as LAH) was slowly added dropwise at 0°C, and the reaction solution was stirred at 45°C for 4 Hour. Water (10 mL), aqueous sodium hydroxide solution (1.0 M, 10 mL), and water (5.0 mL) were slowly added to the reaction solution at 0°C. The resulting precipitate was filtered o...

reference example 2

[0410] Synthesis of (3-cyclobutoxyphenyl)methanamine

[0411]

[0412] Dissolve 3-cyanophenol (1.25g), triphenylphosphine (2.9g) and cyclobutanol (1.2mL) in THF (15mL), and slowly add diethyl azodicarboxylate ( After a toluene solution (2.2 M, 50 mL), which is referred to as DEAD (hereinafter referred to as DEAD), was stirred at room temperature for 2 hours. After the reaction solution was concentrated under reduced pressure, ethyl acetate (20 mL) was added to the residue, and the organic layer was washed with aqueous sodium hydroxide solution (1.0 M, 5.0 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (40% ethyl acetate / hexane). The obtained compound was dissolved in THF (5.0 mL), and a THF solution (2.4 M, 5.3 mL) of LAH was slowly added dropwise at 0°C, followed by stirring at 45°C for 4 hours. Water (1.0 mL), aqueous sodium hydroxide solution (1.0 M, 1.0 mL), and water (5.0...

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Abstract

Disclosed is an uracil compound which has an excellent inhibitory activity on human dUTPase and is useful as an anti-tumor agent or the like or a salt of the uracil compound. Specifically disclosed is an uracil compound represented by general formula (I) or a salt thereof. [In general formula (I), n represents a number of 1 to 3; X represents a bond, an oxygen atom, a sulfur atom, or the like; Y represents a linear or branched alkylene group having 1 to 8 carbon atoms, or the like; Z represents -SO2NR1R2 or -NR3SO2-R4; R1 and R2 independently represent an alkyl group having 1 to 6 carbon atoms, an aralkyl group which may have a substituent, or the like; R3 represents an alkyl group having 1 to 6 carbon atoms, or the like; and R4 represents an aromatic hydrocarbon group, an unsaturated heterocyclic group, or the like].

Description

technical field [0001] The present invention relates to a novel uracil compound or a salt thereof which has excellent human deoxyuridine triphosphatase inhibitory activity and is useful as a therapeutic agent for diseases associated with deoxyuridine triphosphatase inhibitory activity, for example, as an antitumor agent. Background technique [0002] Deoxyuridine triphosphatase (hereinafter also referred to as dUTPase (EC3.6.1.23)) is a preventive DNA repair enzyme. It is an enzyme that specifically recognizes only deoxyuridine triphosphate (hereinafter referred to as dUTP) in natural nucleic acid triphosphates and decomposes it into deoxyuridine monophosphate (hereinafter referred to as dUMP) and pyrophosphate (non-patent document 1 ), it can be considered to undertake the following two reactions: (1) by reducing the amount of dUTP pool in the cell, avoiding uracil to replace thymine and mistakenly incorporated into DNA; (2) supplying the matrix dUMP of deoxythymidylate syn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/46A61K31/505A61K31/506A61P35/00A61P43/00C07D401/06C07D403/12C07D405/12C07D409/06C07D409/12
CPCC07D239/46C07D239/48C07D401/06C07D403/12C07D405/12C07D409/06C07D409/12A61P31/00A61P31/04A61P31/18A61P31/22A61P33/00A61P33/02A61P33/06A61P35/00A61P43/00
Inventor 福冈正哲横川达史宫原成司宫腰均矢野稚子田口淳子高尾弥生
Owner TAIHO PHARMA CO LTD
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