Homochiral intermediates for preparation of orally active azole

Details Homochiral intermediates for preparation of orally active azole Homochiral intermediates for preparation of orally active azole

1997-04-24

1998-06-02

Higel, Floyd D.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

5483415, 549557, 514396, C07D24908, C07D23354, C07D23360, C07D30312, C07D30332

Patent

active

057602450

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(.dbd.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 formmula 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(.dbd.O)R.sub.7, --NR.sub.8 R.sub.9, --NHC(.dbd.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(.dbd.O)--, R.sub.2 is optionally substituted 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 substituted phenyl.

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