Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles
AssigneeJanssen Pharmaceutica NV
InventorsJan Heeres, Leo J. J. Backx, Joseph H. Mostmans
Life of this patent
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Abstract
Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles useful as anti-fungal and anti-bacterial agents.
Claims8
A chemical compound selected from the group consisting of an azole derivative having the formula:
- ##STR100## and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein:
- Q is CH;
- Ar is a member selected from the group consisting of phenyl and substituted phenyl, said substituted phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl and lower alkyloxy;
- and
- the radical Y is a member selected from the group consisting of:
- a 1H-1,2,4-triazol-1-yl radical of the formula ##STR101## wherein R.sub.6 is selected from the group consisting of hydrogen and lower alkylthio, and, R.sub.7 is selected from the group consisting of hydrogen, lower alkyl and phenyl;
- a 4H-1,2,4-triazol-4-yl radical of the formula ##STR102## wherein R.sub.8 is selected from the group consisting of hydrogen, lower alkyl, lower alkyloxy, lower alkylthio, lower alkylsulfinyl and lower alkylsulfonyl, and, R.sub.9 is selected from the group consisting of hydrogen and lower alkyl;
- a 2,3-dihydro-4H-1,2,4-triazol-4-yl radical of the formula ##STR103## wherein X is selected from the group consisting of O and S, and, R.sub.10 and R.sub.11 are each independently selected from the group consisting of hydrogen and lower alkyl, provided that when said X is S then said R.sub.11 is hydrogen;
- a 1H-1,2,3,4-tetrazol--yl radical of the formula ##STR104## a 4,5-dihydro-5-thioxo-1H-1,2,3,4-tetrazol-1-yl radical of the formula ##STR105##
A chemical compound selected from the group consisting of 1-{4-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylm ethoxy]phenyl}-1H-1,2,4-triazole and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof.
A chemical compound selected from the group consisting of cis-4-{4-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4 -ylmethoxy]phenyl}-3(propylthio)-4H-1,2,4-triazole and the pharmaceutically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of cis-4-{4-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4 -ylmethoxy]phenyl}-2,4-dihydro-2,5-dimethyl-3H-1,2,4-triazol-3-one and the pharmaceutically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of cis-4-{4-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4 -ylmethoxy]phenyl}-2-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one 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-imidazol-1-ylmethyl)-1,3-dioxolan-4 -ylmethoxy]phenyl}-1H-tetrazole and the pharmaceutically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of cis-4-{4-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4 -ylmethoxy]phenyl}-5-methyl-4H-1,2,4-triazole-3-thiol 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 amount of a compound selected from the group consisting of an azole derivative having the formula:
- ##STR106## and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein:
- Q is CH;
- Ar is a member selected from the group consisting of phenyl and substituted phenyl, said substituted phenyl having from 1 to 3 subtituents independently selected from the group consisting of halo, lower alkyl and lower alkyloxy;
- and
- the radical Y is a member selected from the group consisting of:
- a 1H-1,2,4-triazol-1-yl radical of the formula ##STR107## wherein R.sub.6 is selected from the group consisting of hydrogen and lower alkylthio, and, R.sub.7 is selected from the group consisting of hydrogen, lower alkyl and phenyl;
- a 4H-1,2,4-triazol-4-yl radical of the formula ##STR108## wherein R.sub.8 is selected from the group consisting of hydrogen, lower alkyl, lower alkyloxy, lower alkylthio, lower alkylsulfinyl and lower alkylsulfonyl, and, R.sub.9 is selected from the group consisting of hydrogen and lower alkyl;
- a 2,3-dihydro-4H-1,2,4-triazol-4-yl radical of the formula ##STR109## wherein X is selected from the group consisting of O and S, and, R.sub.10 and R.sub.11 are each independently selected from the group consisting of hydrogen and lower alkyl, provided that when said X is S then said R.sub.11 is hydrogen;
- a 1H-1,2,3,4-tetrazol-1-yl radical of the formula ##STR110## a 4,5-dihydro-5-thioxo-1H-1,2,3,4-triazol-1-yl radical of the formula ##STR111##
Dependencies are inferred from the claim text.