[[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]- 1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles having anti-microbial properties

A composition for combatting microorganisms comprising an inert carrier material and as an active ingredient an antimicrobially effective amount of a compound having the formula ##STR20## a pharmaceutically acceptable acid-addition salt or a stereochemically isomeric form thereof, wherein

• Q is N or CH;
• Ar is aryl;
• R is hydrogen or C.sub.1-6 alkyl;
• and
• Y--R.sup.1 is a radical having the formula ##STR21## or a radical having the formula ##STR22## wherein R.sup.1 is tetrahydrofuranylC.sub.1-6 alkyl;
• or C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, arylC.sub.1-6 alkyl or (C.sub.3-6 cycloalkyl)C.sub.1-6 alkyl all substituted on the C.sub.1-6 alkyl and/or C.sub.3-6 cycloalkyl moiety with oxo, thioxo or with one or two radicals of formula --Z--R.sup.1-a ;
• said Z being O or S;
• said R.sup.1-a being hydrogen;
• C.sub.1-6 alkyl, aryl, C.sub.3-6 cycloalkyl or tetrahydro-2H-pyran-2-yl;
• or where R.sup.1 is substituted with two --Z--R.sup.1-a radicals, the two --R.sup.1-a radicals, taken together, may form a bivalent radical of formula --CH.sub.2 --, --CH(CH.sub.3)--, --C(CH.sub.3).sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH(CH.sub.3)--CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 --;
• X is O, S or NR.sup.2 ;
• said R.sup.2 being hydrogen or C.sub.1-6 alkyl;
• A is >C.dbd.O, NR.sup.3, methylene or methylene substituted with up to two radicals selected from the group consisting of C.sub.1-6 alkyl and aryl;
• said R.sup.3 being hydrogen or C.sub.1-6 alkyl;
• B is >C.dbd.O or methylene optionally substituted with up to two C.sub.1-6 alkyl radicals;
• or A and B, taken together, form a bivalent radical of formula
• --N.dbd.CH-- (c);
• A' and B' independently having the same meaning of A and B respectively, or A' and B', taken together, form a bivalent radical of formula
• --N.dbd.CH-- (c) or
• --CH.dbd.CH-- (d);
• wherein the nitrogen atom in the bivalent radical (c) is connected to NR.sup.1 ;
• wherein one hydrogen in said radical (c) and up to two hydrogens in radical (d) may be replaced by a C.sub.1-6 alkyl radical;
• provided that
• (i) when Y--R.sup.1 is a radical of formula (a) wherein --A--B-- is other than a bivalent radical of formula (c), then R.sup.1 is other than C.sub.1-6 alkyl substituted with C.sub.1-6 alkyloxy;
• (ii) when Y--R.sup.1 is a radical of formula (b) then R.sup.1 is other than C.sub.1-6 alkyl substituted with C.sub.1-6 alkyloxy;
• wherein aryl is phenyl or substituted phenyl, said substituted phenyl having from 1 to 3 substituents each independently selected from the group consisting of fluoro, chloro, bromo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, and trifluoromethyl.

A method of inhibiting and/or eliminating the development of fungi and bacteria in warm-blooded animals suffering from diseases caused by these fungi and/or bacteria by the systemic or topical a aministration of an antimicrobially effective amount of a compound having the formula ##STR23## a pharmaceutically acceptable acid-addition salt or a stereochemically isomeric form thereof, wherein

• Q is N or CH;
• Ar is aryl;
• R is hydrogen or C.sub.1-6 alkyl;
• and
• Y--R.sup.1 is a radical having the formula ##STR24## or a radical having the formula ##STR25## wherein R.sup.1 is tetrahydrofuranylC.sub.1-6 alkyl;
• or C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, arylC.sub.1-6 alkyl or (C.sub.3-6 cycloalkyl)C.sub.1-6 alkyl all substituted on the C.sub.1-6 alkyl and/or C.sub.3-6 cycloalkyl moiety with oxo, thioxo or with one or two radicals of formula --Z--R.sup.1-a ;
• said Z being O or S;
• said R.sup.1-a being hydrogen, C.sub.1-6 alkyl, aryl, C.sub.3-6 cycloalkyl or tetrahydro-2H-pyran-2-yl;
• or where R.sup.1 is substituted with two --Z--R.sup.1-a radicals, the two --R.sup.1-a radicals, taken together, may form a bivalent radical of formula --CH.sub.2 --, --CH(CH.sub.3)--, --C(CH.sub.3).sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH(CH.sub.3)--CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 --;
• X is O, S or NR.sup.2 ;
• said R.sup.2 being hydrogen or C.sub.1-6 alkyl;
• A is >C.dbd.O, NR.sup.3, methylene or methylene substituted with up to two radicals selected from the group consisting of C.sub.1-6 alkyl and aryl;
• said R.sup.3 being hydrogen or C.sub.1-6 alkyl;
• B is >C.dbd.O or methylene optionally substituted with up to two C.sub.1-6 alkyl radicals;
• or A and B, taken together, form a bivalent radical of formula
• --N.dbd.CH-- (c);
• A' and B' independently having the same meaning of A and B respectively, or A' and B', taken together, form a bivalent radical of formula
• --N.dbd.CH-- (c) or
• --CH.dbd.CH-- (d);
• wherein the nitrogen atom in the bivalent radical (c) is connected to NR.sup.1 ;
• wherein one hydrogen in said radical (c) and up to two hydrogens in radical (d) may be replaced by a C.sub.1-6 alkyl radical;
• provided that
• (i) when Y--R.sup.1 is a radical of formula (a) wherein --A--B-- is other than a bivalent radical of formula (c), then R.sup.1 is other than C.sub.1-6 alkyl substituted with C.sub.1-6 alkyloxy;
• (ii) when Y--R.sup.1 is a radical of formula (b) then R.sup.1 is other than C.sub.1-6 alkyl substituted with C.sub.1-6 alkyloxy;
• wherein aryl is phenyl or substituted phenyl, said substituted phenyl having from 1 to 3 substituents each independently selected from the group consisting of fluoro, chloro, bromo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, and trifluoromethyl.

A substituted phenol of the following formula (V):

• ##STR26## or a stereochemically isomeric form thereof, wherein R is hydrogen or C.sub.1-6 alkyl;
• and
• Y--R.sup.1 is a radical having the formula ##STR27## or a radical having the formula ##STR28## wherein R.sup.1 is tetrahydrofuranylC.sub.1-6 alkyl;
• or C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, arylC.sub.1-6 alkyl or (C.sub.3-6 cycloalkyl)C.sub.1-6 alkyl all substituted on the C.sub.1-6 alkyl and/or C.sub.3-6 cycloalkyl moiety with oxo, thioxo or with one or two radicals of formula --Z--R.sup.1-a ;
• said Z being O or S;
• said R.sup.1-a being hydrogen, C.sub.1-6 alkyl, aryl, C.sub.3-6 cycloalkyl or tetrahydro-2H-pyran-2-yl;
• or wherein R.sup.1 is substituted with two --Z--R.sup.1-a radicals, the two --R.sup.1-a radicals, taken together, may form a bivalent radical of formula --CH.sub.2 --, --CH(CH.sub.3)--, --C(CH.sub.3).sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH(CH.sub.3)--CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 --;
• X is O, S or NR.sup.2 ;
• said R.sup.2 being hydrogen or C.sub.1-6 alkyl;
• A is >C.dbd.O, NR.sup.3, methylene or methylene substituted with up to two radicals selected from the group consisting of C.sub.1-6 alkyl and aryl;
• said R.sup.3 being hydrogen or C.sub.1-6 alkyl;
• B is >C.dbd.O or methylene optionally substituted with up to two C.sub.1-6 alkyl radicals;
• or A and B, taken together, form a bivalent radical of formula
• --N.dbd.CH.dbd. (c);
• A' and B' independently having the same meaning of A and B respectively, or A' and B', taken together, form a bivalent radical of formula
• --N.dbd.CH-- (c) or
• --CH.dbd.CH-- (d);
• wherein the nitrogen atom in the bivalent radical (c) is connected to NR.sup.1 ;
• wherein one hydrogen in said radical (c) and up to two hydrogens in radical (d) may be replaced by a C.sub.1-6 alkyl radical;
• provided that
• (i) when Y--R.sup.1 is a radical of formula (a) wherein --A--B-- is other than a bivalent radical of formula (c), then R.sup.1 is other than C.sub.1-6 alkyl substituted with C.sub.1-6 alkyloxy;
• (ii) when Y--R.sup.1 is a radical of formula (b) then R.sup.1 is other than C.sub.1-6 alkyl substituted with C.sub.1-6 alkyloxy;
• wherein aryl is phenyl or substituted phenyl, said substituted phenyl having from 1 to 3 substituents each independently selected from the group consisting of fluoro, chloro, bromo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy and trifluoromethyl.