Topical antifungal agent

A technology of alkyl and hydrogen atoms, applied in the field of 2-phenol derivatives or their pharmaceutically acceptable salts, can solve the compounds of 2-(1H-pyrazol-1-yl)phenol skeleton that are not suggested and disclosed Issues such as anti-trichophyton activity

Inactive Publication Date: 2013-10-02
MEIJI SEIKA KAISHA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In none of these prior art documents is it suggested or disclosed that compounds having a 2-(1H-pyrazol-1-yl)phenol skeleton are associated with anti-trichophyton activity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0197] Example 12-(3,5-Dimethyl-1H-pyrazol-1-yl)phenol

[0198] a) 1-(2-methoxyphenyl)-3,5-dimethyl-1H-pyrazole

[0199] Dissolve 3.50 g of 2-methoxyphenylhydrazine hydrochloride in 60 ml of ethanol, add 2.06 ml of acetylacetone, and heat to reflux for 1 hour. 150 ml of water was added to the reaction mixture, neutralized with saturated aqueous sodium carbonate solution, and extracted with 150 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=2:1) ​​to obtain 3.88 g of the title compound.

[0200] 1 H-NMR (CDCl 3 ): δ(ppm)2.08(3H,s),2.29(3H,s),3.78(3H,s),5.95(1H,s),6.98-7.03(2H,m),7.29-7.32(1H,m ),7.34-7.39(1H,m).

[0201] MS(ESI):m / z203(M+H) +

[0202] b) 2-(3,5-Dimethyl-1H-pyrazol-1-yl)phenol

[0203] Dissolve 3.88g of 1-(2-methoxyphenyl)-3,5-dimethyl-1H-pyrazole in 40ml of dichloromethane, add 32ml of 1M b...

Embodiment 2

[0206] Example 22-(3,5-Dimethyl-1H-pyrazol-1-yl)-4-fluorophenol

[0207] a) 2-amino-4-fluorophenol

[0208] 300 mg of 4-fluoro-2-nitrophenol was dissolved in 3 ml of ethanol, 120 mg of 10% palladium / carbon was added, and stirred at room temperature for 1 hour under a hydrogen atmosphere. After filtering the insoluble matter, the solvent was distilled off under reduced pressure to obtain 211 mg of the title compound.

[0209] 1 H-NMR (DMSO-d6): δ (ppm) 4.80 (2H, s), 6.09-6.14 (1H, m), 6.34-6.37 (1H, m), 6.53-6.57 (1H, m), 8.93 (1H ,s).

[0210] MS(FAB):m / z128(M+H) +

[0211] b) 2-(3,5-Dimethyl-1H-pyrazol-1-yl)-4-fluorophenol

[0212] 0.8 ml of 5N-hydrochloric acid was added to 100 mg of 2-amino-4-fluorophenol, and a solution of 65 mg of sodium nitrite dissolved in 0.2 ml of water was added dropwise at 0°C, followed by stirring for 30 minutes. Then, a solution of 249 mg of stannous chloride dissolved in 0.46 ml of 5N-hydrochloric acid was added dropwise at 0°C, stirred at 0...

Embodiment 32

[0215] Example 32-(1H-pyrazol-1-yl)phenol

[0216] a) 1-(2-methoxyphenyl)-1H-pyrazole

[0217] 200 mg of 2-methoxyphenylhydrazine hydrochloride was dissolved in 5 ml of ethanol, 189 μl of malondialdehyde dimethyl acetal was added, and heated to reflux for 2 hours. 50 ml of water was added to the reaction mixture, neutralized with saturated aqueous sodium carbonate solution, and extracted with 60 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 179.4 mg of the title compound.

[0218] 1 H-NMR (CDCl 3 ):δ(ppm)3.87(3H,s),6.42(1H,d,J=2.4Hz),7.02-7.07(2H,m),7.27-7.32(1H,m),7.68-7.72(2H,m ),8.01(1H,d,J=2.4Hz).

[0219] MS(FAB):m / z175(M+H) +

[0220] b) 2-(1H-pyrazol-1-yl)phenol

[0221] In the same manner as in Example 1b), 121 mg of the title compound was obtained from 178 mg of 1-(2-methoxyphenyl)-1H-pyrazole.

[0222] 1 H-NMR (CDCl 3 ):δ(ppm)6.49(1H,d,J=2.4Hz),6.88-6....

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Abstract

Provided is an anti-Trichophyton agent having as an active ingredient a compound having a 2-(1H-pyrazol-1-yl)phenol backbone represented by formula (I) or (II), or a salt of the compound.

Description

technical field [0001] The present invention relates to novel 2-(1H-pyrazol-1-yl)phenol derivatives or pharmaceutically acceptable salts thereof suitable as antitrichophyton agents, and antitrichophyton agents containing these compounds as active ingredients agent. Background technique [0002] Mycosis is a disease that results from the infection of humans or animals by fungi. Representative mycoses in humans include candidiasis caused by Candida, cryptococcosis caused by Cryptococcus, aspergillosis caused by Aspergillus, zygomycosis caused by Zygomycetes, and Cutaneous filamentous mycosis (tinea) caused by ringworm (pathogenic fungi and mycosis (Nanshantang, revised 2nd edition), p42-45; non-patent literature 1). [0003] Trichophyton is a dermatophyte fungus that causes white tinea, and has a property called keratolytic ability. Through this ability, it can invade the skin, nails, and hair to cause tinea alba (pathogenic fungi and mycosis (Nan Shantang, revised 2nd edit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12A61K31/415A61P17/00A61P31/10C07D231/14C07D231/22
CPCC07D231/12C07D231/14C07D231/22A61K31/415C07D207/32C07D207/34C07D207/36A61P17/00A61P31/10
Inventor 大山真田端祐二饭田真依子金田香织高畑祥
Owner MEIJI SEIKA KAISHA LTD
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