150802-97-4

Upstream product

• 99-33-2 3,5-dinitrobenoyl chloride 
• 212890-35-2 2-[(1R)-1-(3,4,5,6-Tetrahydro-2H-pyran-2-yl)oxyethyl]-2-(2,4-difluorophenyl)oxirane 
• 150802-96-3 (2S,3R)-3-(2,4-Difluorophenyl)-3,4-epoxy-2-butanol 

Downstream Products

• 126918-35-2 (1R)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 
• 188645-08-1 2-[(1S,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone 
• 155432-64-7 2-[(1S,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone 
• 126918-33-0 (1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 
• 135270-14-3 (R)-1-[(R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl methanesulfonate 
• 150802-87-2 (2S)-2-(2,4-difluorophenyl)-2-<(1R)-1-(2H-tetrazol-2-yl)ethyl>oxirane 
• 150802-88-3 (2S)-2-(2,4-difluorophenyl)-2-<(1R)-1-(1H-tetrazol-1-yl)ethyl>oxirane 
• 150802-85-0 <(1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethyl> benzoate 
• 155431-23-5 2-<(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl>-4-(4-fluorophenyl)-3(2H,4H)-1,2,4-triazolone 
• 155431-43-9 4-<(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl>-2-(4-fluorophenyl)-3(2H,4H)-1,2,4-triazolone 
• 155431-57-5 1-<(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl>-4-(4-fluorophenyl)-5(1H,4H)-tetrazolone 
• 155431-33-7 4-{(R)-1-[(S)-2-(2,4-Difluoro-phenyl)-oxiranyl]-ethyl}-2-(4-trifluoromethyl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one 
• 155431-31-5 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-(4-trifluoromethylphenyl)-3(2H,4H)-1,2,4-triazolone 
• 155431-50-8 1-{(R)-1-[(S)-2-(2,4-Difluoro-phenyl)-oxiranyl]-ethyl}-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one 

Relevant academic research and scientific papers

Azole compounds, their production and use

PCT No. PCT/JP96/00325 Sec. 371 Date Oct. 17, 1996 Sec. 102(e) Date Oct. 17, 1996 PCT Filed Feb. 15, 1996 PCT Pub. No. WO96/25410 PCT Pub. Date Aug. 20, 1996The present invention provides an azole compound represented by the formula (I): wherein Ar is an

Injectable composition and a method of producing the same

An injectable oil-in-water emulsion composition comprises an antifungal triazole compound of the following formula (I) STR1 wherein Ar represents a substituted phenyl group; R1 and R2 represent, independently, a hydrogen atom or a lo

Optically active antifungal azoles. VII. Synthesis and antifungal activity of stereoisomers of 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1- methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-[4-(2,2,3,3- tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (TAK-187)

2-[(1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4- triazol-1-yl)propyl]-4-[4-(2,2,3,3-tetrafluopropoxy)phenyl]-3(2H,4H)-1,2,4- triazolone [(1R,2R)-1: TAK-187] is a new antifungal agent selected as a candidate for clinical trials. The three stereoisomers [(1S,2S)-, (1R,2S)- and (1S,2R)-1] of this compound were prepared to clarify the relationship between the stereochemistry and the biological activities. In vitro and in vivo assays of antifungal activity revealed TAK-187 [(1R,2R)-1] is the most potent among the four stereoisomers. Furthermore, TAK-187 was found to exert a strong and selective inhibitory effect on the sterol synthesis in Candida albicans as compared with that in rat liver.

Optically active antifungal azoles. VI. Synthesis and antifungal activity of N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones

A new series of optically active antifungal azoles, N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones (1,2) and 5(1H,4H)-tetrazolones (3), were prepared from the triflate derivative of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (13) by an SN2 displacement reaction with the union of an azolone (17-19) and subsequent ring-opening reaction with 1H-1,2,4-triazole. The optically active oxiranylethanol 13 was synthesized from methyl (R)-lactate in a stereocontrolled manner. The azolones 1-3 prepared showed potent antifungal activities in vitro and in vivo.

Optically active tetrazole compounds, and fungicidal compositions thereof

An optically active azole compound of the formula (I): STR1 wherein R1 and R2 are independently a hydrogen atom, a halogen atom, a haloalkyl group, a haloalkoxy group or an optionally substituted nitrogen-containing heterocyclic group; R3 is a hydrogen atom or an acyl group; Q is CH or N; --NA is a nitrogen-containing aromatic five-membered heterocyclic group having at least two adjacent nitrogen atoms as the ring-constituting atoms which may be substituted, or an aromatic condensed heterocyclic group having two or more nitrogen atoms as the ring-constituting atoms which may be substituted; and (R) shows that the carbon atom marked with (R) has R-configuration; provided that either of R1 and R2 is an optionally substituted nitrogen-containing heterocyclic group when --NA is an 1H-1,2,4-triazol-1-yl group, or a salt thereof, which is useful as an antifungal agent.