- COMPOUNDS OF R-(-)-(E)-[4-(2,4-DICHLOROPHENYL)-1,3-DITHIOLAN-2-YLIDENE]-1 -IMIDAZOLYLACETONITRILE-HA (LULICONAZOLE-HA) AS ANTIFUNGALS
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The present invention refers to compound R-(-)-(E)-[4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-1-imidazolylacetonitrile HA, wherein HA is an acid; and to a process for their preparation. The present invention also refers to the use of compound R-(-)-(E)-[4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-1-imidazolylacetonitrile HA for the manufacturing of luliconazole and pharmaceutically acceptable salts or co-crystals thereof in high yield and purity. The present invention further is directed to this compound R-(-)-(E)-[4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-1-imidazolylacetonitrile HA in the treatment of fungal infections.
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Page/Page column 36
(2017/08/01)
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- Asymmetric chemoenzymatic synthesis of miconazole and econazole enantiomers. the importance of chirality in their biological evaluation
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A simple and novel chemoenzymatic route has been applied for the first time in the synthesis of miconazole and econazole single enantiomers. Lipases and oxidoreductases have been tested in stereoselective processes; the best results were attained with oxidoreductases for the introduction of chirality in an adequate intermediate. The behaviors of a series of ketones and racemic alcohols in bioreductions and acetylation procedures, respectively, have been investigated; the best results were found with alcohol dehydrogenases A and T, which allowed the production of (R)-2-chloro-1-(2,4-dichlorophenyl)ethanol in enantiopure form under very mild reaction conditions. Final chemical modifications have been performed in order to isolate the target fungicides miconazole and econazole both as racemates and as single enantiomers. Biological evaluation of the racemates and single enantiomers has shown remarkable differences against the growth of several microorganisms; while (R)-miconazole seemed to account for most of the biological activity of racemic miconazole on all the strains tested, both enantiomers of econazole showed considerable biological activities. In this manner, (R)-econazole showed higher values against Candida krusei, while higher values were observed for (S)-econazole against Cryptococcus neoformans, Penicillium chrysogenum, and Aspergillus niger.
- Mangas-Sanchez, Juan,Busto, Eduardo,Gotor-Fernandez, Vicente,Malpartida, Francisco,Gotor, Vicente
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experimental part
p. 2115 - 2122
(2011/05/19)
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- A switch in enantiomer preference between mitochondrial F1F 0-ATPase chemotypes
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The preferred absolute configuration of two series of F1F 0-ATP synthase inhibitors was determined. Although the configuration of the active enantiomer in each series is different, each series presents the same 'triaryl' pharmacophor
- Bisaha, Sharon N.,Malley, Mary F.,Pudzianowski, Andrew,Monshizadegan, Hossain,Wang, Paulina,Madsen, Cort S.,Gougoutas, Jack Z.,Stein, Philip D.
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p. 2749 - 2751
(2007/10/03)
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- Method for treating mycosis using imidazolylacetonitrile derivatives
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R-(+)-(E)-?4-(2-Chlorophenyl)-1,3-dithiolan-2-ylidene!-1-imidazolylacetonitrile, R-(-)-(E)-?4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene!-1-imidazolylacetonitrile, and pharmaceutically acceptable salts thereof which can be used as a pharmaceutical agent are disclosed. A process for producing them and a method for treating mycoses using them are also disclosed.
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