Azole compounds, their production and use

Details Azole compounds, their production and use Azole compounds, their production and use

1996-10-17

2000-03-07

Morris, Patricia L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548252, C07D40314

Patent

active

06034248&

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to azole compounds useful as antifungal therapeutic agents, methods for producing the same and use thereof.


BACKGROUND ART

A variety of azole compounds have been reported exhibiting antifungal activity (see, for example, EP0122056A1, EP0332387A1, EP0122693A1 and EP0567982A).
None of these azole compounds, however, is satisfactory as a pharmaceutical agent in terms of its antifungal activity, antifungal spectrum, side effect and in vivo pharmacokinetics.
There has been a demand for a safer compound which exhibits better absorption in vivo and higher antifungal activity as an antifungal therapeutic agent.


DISCLOSURE OF INVENTION

The present invention provides ##STR2## wherein Ar is an optionally substituted phenyl group; R.sup.1 and R.sup.2, the same or different, are a hydrogen atom or a lower alkyl group, or R.sup.1 and R.sup.2 may combine together to form a lower alkylene group; R.sup.3 is a hydrogen atom or an acyl group; X is a nitrogen atom or a methine group; A is Y.dbd.Z (Y and Z, the same or different, are a nitrogen atom or a methine group optionally substituted with a lower alkyl group) or an ethylene group optionally substituted with a lower alkyl group; n is an integer from 0 to 2; and Az is an optionally substituted azolyl group, or a salt thereof, claim 1 or a salt thereof which comprises ##STR3## wherein the symbols have the same meanings as defined above; or a salt thereof ##STR4## wherein the symbols have the same meanings as defined above; or a salt thereof, and, if necessary, followed by an acylation; ##STR5## wherein the symbols have the same meanings as defined above; or a salt thereof ##STR6## wherein A" is --N.dbd.CH--, --CH.dbd.N-- or --CH.dbd.CH--; the symbols have the same meanings as defined above; or a salt thereof, and, if necessary, followed by an acylation; or ##STR7## wherein the symbols have the same meanings as defined above; or a salt thereof, and, if necessary, followed by an acylation, a compound represented by the above formula (I) or a salt thereof.
Examples of the substituents for "optionally substituted phenyl group" represented by Ar in the formula (I) include halogen atoms (e.g., fluorine, chlorine, bromide and iodine), lower (C.sub.1-4) haloalkyl, lower (C.sub.1-4) haloalkoxy, lower (C.sub.1-4) alkylsulfonyl, lower (C.sub.1-4) haloalkylsulfonyl and the like. Preferably, the substituent is halogen atoms (e.g., fluorine, chlorine, bromine and iodine), and more preferably it is fluorine. The number of the substituents is preferably from one to three, more preferably from one to two.
Examples of Ar include halophenyl, lower (C.sub.1-4) haloalkylphenyl, lower (C.sub.1-4) haloalkoxyphenyl, lower (C.sub.1-4) alkylsulfonylphenyl, lower (C.sub.1-4) haloalkylsulfonylphenyl and the like.
Examples of the halophenyl groups include 2,4-difluorophenyl, 2,4-dichlorophenyl, 4-chlorophenyl, 4-fluorophenyl, 2-chlorophenyl, 2-fluorophenyl, 2-fluoro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 2,4,6-trifluoropheny, 4-bromophenyl and the like.
Examples of the lower (C.sub.1-4) haloalkylphenyl groups include 4-trifluoromethylphenyl group and the like.
Examples of the lower (C.sub.1-4) haloalkoxyphenyl groups include 4-trifluoromethoxyphenyl, 4-(1,1,2,2-tetrafluoroethoxy)phenyl, 4-(2,2,2-trifluoroethoxy)phenyl, 4-(2,2,3,3-tetrafluoropropoxy)phenyl, 4-(2,2,3,3,3-pentafluoropropoxy)phenyl and the like.
Examples of the lower (C.sub.1-4) alkylsulfonylphenyl groups include 4-methanesulfonylphenyl and the like.
Examples of the lower (C.sub.1-4) haloalkylsulfonylphenyl groups include 4-(2,2,2-trifluoroethanesulfonyl)phenyl, 4-(2,2,3,3-tetrafluoropropanesulfonyl)phenyl, 4-(2,2,3,3,3-pentafluoropropanesulfonyl)phenyl and the like.
Specific examples of the phenyl groups of Ar are phenyl groups substituted with one to two halogen atoms such as 2,4-difluorophenyl, 2,4-dichlorophenyl, 4-chlorophenyl, 4-fluorophenyl, 2-chlorophenyl, 2-fluorophenyl, 2-fluoro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 4-bromophenyl and the like, among which phenyl groups su

REFERENCES:
patent: 5677464 (1997-10-01), Itoh et al.
patent: 5792780 (1998-08-01), Itoh et al.
Cram and Hammond, "Organic Chemistry", McGraw Hill Book Co., NY (1964) 2nd ed., pp. 565-567.

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