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Generated: September 25, 2017

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Title: Heterocyclic derivatives of (4-phenylpiperazin-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)methyl-1H-imidaz oles and 1H-1,2,4-triazoles
Abstract:Novel heterocyclic derivatives of (4-phenylpiperazin-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)methyl-1H-imidazol es and 1H-1,2,4-triazoles, useful as antifungal and antibacterial agents.
Inventor(s): Heeres; Jan (Vosselaar, BE), Backx; Leo J. J. (Arendonk, BE)
Assignee: Janssen Pharmaceutica, N.V. (Beerse, BE)
Application Number:06/020,383
Patent Claims: 1. A chemical compound selected from the group consisting of an azole derivative having the formula: ##STR68## and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein:

Q is a member selected from the group consisting of CH and N;

Ar is a member selected from the group consisting of phenyl, thienyl, halothienyl and substituted phenyl, said substituted phenyl having from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy and trifluoromethyl; and

the radical Y is a 2,3-dihydro-4H-1,2,4-triazol-4-yl radical of the formula ##STR69## wherein R.sup.15 is selected from the group consisting of lower alkyl and aryl lower alkyl and R.sup.16 is selected from the group consisting of hydrogen, lower alkyl, and aryl lower alkyl;

wherein said aryl as used in the foregoing definition is selected from the group consisting of phenyl and substituted phenyl, said substituted phenyl having from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy and trifluoromethyl.

2. A chemical compound selected from the group consisting of cis-4-{4-[4-{4-[2-(2,4-dichlorophenyl)-2-(1H -imidazol-1-yl-methyl)-1,3-dioxolan-4-ylmethoxy]phenyl}-1-piperazinyl]phen yl}-2,4-dihydro-2,5-dimethyl-3H-1,2,4-triazol-3-one and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof.

3. A chemical compound selected from the group consisting of cis-4-{4-[4-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3 -dioxolan-4-ylmethoxy]phenyl}-1-piperazinyl]phenyl}-2,4-dihydro-2,5-dimethy l-3H-1,2,4-triazol-3-one monohydrate and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof.

4. A chemical compound selected from the group consisting of cis-4-{4-[4-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3 -dioxolan-4-ylmethoxy]phenyl}-1-piperazinyl]-phenyl}-2-ethyl-2,4-dihydro-5- methyl-3H-1,2,4-triazol-3-one and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof.

5. A chemical compound selected from the group consisting of cis-4-{4-[4-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3 -dioxolan-4-ylmethoxy]phenyl}-1-piperazinyl]-phenyl}-2,4-dihydro-5-methyl-2 -propyl-3H-1,2,4-triazol-3-one monohydrate and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof.

6. A chemical compound selected from the group consisting of cis-4-{4-[4-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3 -dioxolan-4-ylmethoxy]phenyl}-1-piperazinyl]phenyl}-2-ethyl-2,4-dihydro-3H- 1,2,4-triazol-3-one and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof.

7. A composition for combatting the growth of a microorganism selected from the group consisting of fungus and bacterium comprising an inert carrier material and as an active ingredient an effective antifungal or antibacterial amount of a compound selected from the group consisting of an azole derivative having the formula ##STR70## and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein:

Q is a member selected from the group consisting of CH and N;

Ar is a member selected from the group consisting of phenyl, thienyl, halothienyl and substituted phenyl, said substituted phenyl having from 1 to 3 subtituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy and trifluoromethyl; and the radical Y is a 2,3-dihydro-4H-1,2,4-triazol-4-yl radical of the formula ##STR71## wherein R.sup.15 is selected from the group consisting of lower alkyl and aryl lower alkyl and R.sup.16 is selected from the group consisting of hydrogen, lower alkyl, and aryl lower alkyl;

wherein said aryl as used in the foregoing definition is selected from the group consisting of phenyl and substituted phenyl, said substituted phenyl having from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy and trifluoromethyl.
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