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Heterocycles substituted pyridine derivatives and antifungal agent containing thereof

A technology of pyridine and pyridine ring, which is applied in antifungal agents, medical preparations containing active ingredients, organic chemistry, etc., can solve the problems of undisclosed antifungal effects and unrecorded compounds, and achieve excellent metabolic stability and safety excellent effect

Active Publication Date: 2012-09-05
EISIA R&D MANAGEMENT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] However, none of Patent Documents 3 to 5 describes the compound of the present invention, and the compounds disclosed in Patent Documents 3 to 5 are not disclosed at all against Candida, Aspergillus, Cryptococcus, etc., which are common bacterial species in human mycosis. fungal action

Method used

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  • Heterocycles substituted pyridine derivatives and antifungal agent containing thereof
  • Heterocycles substituted pyridine derivatives and antifungal agent containing thereof
  • Heterocycles substituted pyridine derivatives and antifungal agent containing thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0174] [Production method 1-1] Preparation method of compound (1a)

[0175]

[0176] [In the formula, ring A, R 1 , R 2 , R 3 and Z represent the same meanings as defined above. 〕

[0177] Compound (1b) may be used as it is from a commercial product, or may be prepared from a commercial product by a known method. In addition, it can also be prepared by the methods described in the preparation examples in the examples or [Production method 1-2-1] and the like.

[0178] Compound (1c) can be produced from commercially available products by known methods. Furthermore, it can also be prepared by the method described in the preparation example in an Example or [production method 1-3-1] etc.

[0179] [step 1]

[0180] This step is a step of reacting compound (1b) and compound (1c) in the presence of a base to obtain compound (1a). The solvent used for this reaction is not particularly limited as long as it can dissolve the starting material to a certain extent and does no...

Embodiment 1

[0728] [Example 1] 3-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine

[0729]

[0730]At 0°C, add the mixture of 4-benzyloxy-phenyl-acetohydroximoyl chloride (acetohydroximoyl chloride) (1.2g, 4.4mmol) and tetrahydrofuran (34mL) described in Preparation Example 1-1-3 to prepare 3-Ethynyl-pyridin-2-ylamine (260 mg, 2.2 mmol) and triethylamine (3.0 mL, 22 mmol) described in Example 1-2-3 were stirred at room temperature for 1 hour. At room temperature, water was added to the reaction mixture, followed by extraction with ethyl acetate-tetrahydrofuran (2:1). The organic layer was washed with saturated brine, and the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3) to obtain the title compound (240 mg, 15%).

[0731] 1 H-NMR spectrum (CDCl 3 )δ (ppm): 4.00 (2H, s), 5.05 (2H, s), 5.41 (2H, s), 6.24 (1H, s), 6.71 (1H, dd, J=4.9, 7.6Hz), 6.93- 6.97(2H, m), 7.18-7.22(2H, m), 7....

preparation example 1-1-1

[0733] [Preparation Example 1-1-1] 1-Benzyloxy-4-((E)-2-nitro-vinyl)-benzene

[0734]

[0735] At 0°C, nitromethane (330 μL, 6.1 mmol) and sodium methoxide (28% in methanol, 1.0 mL, 4.9 mmol), and stirred at room temperature for 10 minutes. The reaction mixture was cooled to 0°C, and 5N aqueous hydrochloric acid solution (20 mL) was added at the same temperature. The reaction mixture was stirred at room temperature for 15 minutes. The precipitated solid was obtained by filtration to obtain the title compound (1.2 g, 100%).

[0736] 1 H-NMR spectrum (DMSO-d 6 )δ (ppm): 5.20 (2H, s), 7.10-7.14 (2H, m), 7.32-7.48 (5H, m), 7.82-7.85 (2H, m), 8.12 (2H, dd, J = 13.5, 18.2Hz).

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PUM

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Abstract

A fungicide which has excellent antifungal activity and is excellent in properties, safety, and metabolic stability. Also provided is a compound represented by the following formula (I) or a salt thereof: [Chemical formula 1] (I) [wherein R<1> means hydrogen, halogeno, amino, C1-6 alkyl, C1-6 alkoxy, or (C1-6 alkoxy)C1-6 alkyl; R<2> means hydrogen, C1-6 alkyl, amino, or di(C1-6 alkyl)amino; one of X and Y means nitrogen and the other means nitrogen or oxygen; ring A means a 5- or 6-membered heteroaryl ring or benzene ring each optionally having one or two halogen atoms or C1-6 alkyl groups; Zmeans a single bond, methylene, ethylene, oxygen, sulfur, -CH2O-, -OCH2-, -NH-, -CH2NH-, -NHCH2-, -CH2S-, or -SCH2-; R<3> means hydrogen, halogeno, or C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl, 5- or 6-membered heteroaryl, or 5- or 6-membered nonaromatic heterocyclic group each optionally having one or two substituents selected from the substituent group (a); and R<4> means hydrogen or halogeno.

Description

technical field [0001] The present invention relates to novel heterocyclic substituted pyridine derivatives and antifungal agents containing the derivatives. Background technique [0002] In recent years, the number of patients with weakened immune function due to intensive chemotherapy or the like or the elderly has gradually increased, and countermeasures against opportunistic infections have become more and more important. The fact that opportunistic infections occur one after another due to different attenuated bacteria shows that as long as there are underlying diseases such as lowered patient resistance, the problem of infectious diseases will not be eliminated. Therefore, it is foreseeable that countermeasures against new infectious diseases including the problem of resistant bacteria will become one of the important issues in the coming aging society. [0003] In the field of antifungal agents, polyene amphotericin B or azole fluconazole, itraconazole, and voriconaz...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04A61K31/4439A61K31/444A61P31/10C07D401/14C07D413/04C07D413/14
Inventor 田中圭悟井上谕村井则夫松仓正幸中本和孝白鸟修司阿部信也
Owner EISIA R&D MANAGEMENT CO LTD
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