Heterocyclic derivatives of [4-(piperazin-1-yl-phenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazol es and 1H-1,2,4-triazoles
AssigneeJanssen Pharmaceutica NV
InventorsJan Heeres, Robert Hendrickx
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Abstract
Novel heterocyclic derivatives of [4-(piperazin-1-yl-phenloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazoles and 1H-1,2,4-triazoles, useful as antifungal and antibacterial agents.
Claims5
A chemical compound selected from the group consisting of an azole derivative having the formula:
- ##STR36## 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 an optionally substituted mono- or binuclear nitrogen-containing heteroaromatic radical selected from the group consisting of:
- a radical of formula ##STR37## wherein R.sup.1 is selected from the group consisting of hydrogen, lower alkylthio, aryl lower alkylthio and arylthio and R.sup.2 and R.sup.3 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryl lower alkyl;
- a radical of formula ##STR38## wherein each of R.sup.4 and R.sup.5 are independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryllower alkyl;
- a radical of formula ##STR39## wherein L is a member selected from the group consisting of S and N-R.sup.18, said R.sup.18 being selected from the group consisting of hydrogen, lower alkyl and aryllower alkyl, and R.sup.16 and R.sup.17 are each independently selected from the group consisting of hydrogen, lower alkyl, nitro and aryllower alkyl, or R.sup.16 and R.sup.17, when taken together, represent a radical of the formula --CH.dbd.CH--CH.dbd.CH--.
A chemical compound selected from the group consisting of cis-8-[4-{4-[2-(2,4-dichlorophenyl)-2-(1H-imidazol--ylmethyl)-1,3-dioxolan -4-ylmethoxy]phenyl}-1-piperazinyl]-7-ethyl-3,7-dihydro-1,3-dimethyl-1H-pur ine-2,6-dione and the pharmaceutically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of cis-1-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxo lan-4-ylmethoxy]phenyl}-4-(2-thiazolyl)piperazine and the pharmaceutically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of cis-1-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxo lan-4-ylmethoxy]-phenyl}-4-(1H-imidazol-1-yl)piperazine hemihydrate and the pharmaceutically acceptable acid addition salts thereof.
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:
- ##STR40## and the pharmaceutically acceptable 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 an optionally substituted mono- or binuclear nitrogen-containing heteroaromatic radical selected from the group consisting of:
- a radical of formula ##STR41## wherein R.sup.1 is selected from the group consisting of hydrogen, lower alkylthio, aryllower alkylthio and arylthio and R.sup.2 and R.sup.3 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryllower alkyl;
- a radical of formula ##STR42## wherein each of R.sup.4 and R.sup.5 are independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryllower alkyl;
- a radical of formula ##STR43## wherein L is a member selected from the group consisting of S and N-R.sup.18, said R.sup.18 being selected from the group consisting of hydrogen, lower alkyl and aryllower alkyl, and R.sup.16 and R.sup.17 are each independently selected from the group consisting of hydrogen, lower alkyl, nitro and aryllower alkyl, or R.sup.16 and R.sup.17, when taken together, represent a radical of the formula --CH.dbd.CH--CH.dbd.CH--.
Dependencies are inferred from the claim text.