US 5,478,826 A · Orally active azole derivatives

Abstract

The present invention relates to new orally active azole derivatives with antifungal activity of formula I ##STR1## wherein: X is CH or N; Ar represents phenyl substituted with halogen and/or trifluoromethyl; Z is --C(=O)-- or --SO.sub.2 --; R.sub.1 is CN, CO.sub.2 H, CO.sub.2 R.sub.7, CONR.sub.8 R.sub.9 or CH.sub.2 Y and then R.sub.3 is hydrogen, or R.sub.1 together with R.sub.3 forms a ring of formula I' ##STR2## wherein B is O, hydroxy or hydrogen; R.sub.4 is C.sub.1-4 alkyl; R.sub.5, R.sub.6, R.sub.8 and R.sub.9 are hydrogen or C.sub.1-4 alkyl; Y is --OH, --OR.sub.7, --OC(=O)R.sub.7, --NR.sub.8 R.sub.9, --NHC(=O)OR.sub.7 ; R.sub.7 is C.sub.1 -C.sub.4 -alkyl, phenyl-C.sub.1 -C.sub.4 -alkyl or optionally substituted phenyl; when Z is --C(=O)--, R.sub.2 is optionally susbtituted phenyl, or naphtyl; when Z is --SO.sub.2 --, R.sub.2 is C.sub.1-4 alkyl, phenyl-C.sub.1-4 -alkyl or optionally susbtituted phenyl.

Claims29

Dependent claims

A compound of the formula ##STR110## as a racemate, a diastereoisomer mixture or as a homochiral compound wherein:

X is CH or N;
Ar represents phenyl or a phenyl ring substituted with one or more halogen and/or trifluoromethyl groups;
Z is --C (=O)-- or --SO.sub.2 --;
B is O, in which case the dotted line represents a covalent bond, or B is hydroxy, fluorine, hydrogen or 1-H-1,2,4-triazol-1-yl, in which case the dotted line is absent;
R.sub.4 is C.sub.1-4 alkyl;
R.sub.5, and R.sub.6, are independently hydrogen or C.sub.1-4 alkyl;
when Z is --C(=O)--, R.sub.2 is phenyl, phenyl substituted with one or more groups R.sub.10, or naphthyl;
when Z is --SO.sub.2 --, R.sub.2 is C.sub.1-4 -alkyl, phenyl--C.sub.1-4 -alkyl, phenyl or phenyl substituted with one or more groups R.sub.10 ;
R.sub.10 represents C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, halogen, nitro, cyano, hydroxy, benzyloxy, hydroxymethyl, a group of formula --CH.sub.2 --OCO--(C.sub.1-4 alkyl), a group of formula --CO-- (C.sub.1-4 alkyl), a group of formula --COO-- (C.sub.1-4 alkyl), a group of formula --SO.sub.2 (C.sub.1-4 Alkyl) wherein z is 0, 1 or 2, amino, mono- or dialkylamino wherein alkyl means C.sub.1 -C.sub.4 alkyl;
or
a salt or solvate thereof.

8 more elements

Dependencies are inferred from the claim text.

Orally active azole derivatives

Life of this patent

Orally active azole derivatives

Life of this patent

Abstract

Claims29