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Details for Patent: 4,368,200

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Details for Patent: 4,368,200

Title: Heterocyclic derivatives of (4-phenyl-piperazine-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)-methyl-1H-imi dazoles 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)
Filing Date:Jan 14, 1981
Application Number:06/224,992
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 isometric 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 member selected from the group consisting of

a 1H-pyrrol-1-yl radical of the formula ##STR69## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryl lower alkyl;

a 1H-pyrazol-1-yl radical of the formula ##STR70## wherein R.sup.5, R.sup.6 and R.sup.7 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryl lower alkyl;

a 1H-imidazol-1-yl radical of the formula ##STR71## wherein R.sup.8 is selected from the group consisting of hydrogen, lower alkyl, mercapto, lower alkylthio and aryl-lower alkylthio, and R.sup.9 and R.sup.10 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryl lower alkyl;

a 1H-1,2,4-triazol-1-yl radical of the formula ##STR72## wherein either of R.sup.11 and R.sup.12 is selected from the group consisting of hydrogen, hydroxy, mercapto, lower alkylthio and aryl-lower alkylthio, the remaining being selected from the group consisting of hydrogen, lower alkyl and aryl-lower alkyl;

a 4H-1,2,4-triazol-4-yl radical of the formula ##STR73## wherein R.sup.13 is selected from the group consisting of hydrogen, mercapto, hydroxy, lower alkylthio and aryl lower alkylthio, and R.sup.14 is selected from the group consisting of hydrogen, lower alkyl, aryl and aryl lower alkyl;

a 1H-1,2,3,4-tetrazol-1-yl radical of the formula ##STR74## wherein R.sup.17 is selected from the group consisting of hydrogen, mercapto, lower alkyl, aryl 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-1-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxo lan-4-ylmethoxy]phenyl}-4-[4-(1H-imidazol-1-yl)phenyl]piperazine and the pharmaceutically accetable acid addition salts and stereochemically isomeric forms thereof.

3. 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}-4-[4-(1H-1,2,4-triazol-1-yl)phenyl]piperazine and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof.

4. 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-[4-(1H-imidazol-1-yl)phenyl]piperazine and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof.

5. A chemical compound selected from the group consisting of cis-1-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-diox olan-4-ylmethoxy]phenyl}-4-{4-[3-(methylthio)-1H-1,2,4-triazol-1-yl]phenyl} piperazine and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof.

6. A chemical compound selected from the group consisting of cis-1-{4-[4-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxo lan-4-ylmethoxy]phenyl}-4-[4-(1H-tetrazol-1-yl)phenyl]piperazine 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 ##STR75## 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 member selected from the group consisting of

a 1H-pyrrol-1-yl radical of the formula ##STR76## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryl lower alkyl;

a 1H-pyrazol-1-yl radical of the formula ##STR77## wherein R.sup.5, R.sup.6 and R.sup.7 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryl lower alkyl;

a 1H-imidazol-1-yl radical of the formula ##STR78## wherein R.sup.8 is selected from the group consisting of hydrogen, mercapto, lower alkylthio and aryl lower alkylthio, and R.sup.9 and R.sup.10 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryl lower alkyl;

a 1H-1,2,4-triazol-1-yl radical of the formula ##STR79## wherein either of R.sup.11 and R.sup.12 is selected from the group consisting of hydrogen, hydroxy, mercapto, lower alkylthio and aryl-lower alkylthio, the remaining being selected from the group consisting of hydrogen, lower alkyl and aryl-lower alkyl;

a 4H-1,2,4-triazol-4-yl radical of the formula ##STR80## wherein R.sup.13 is selected from the group consisting of hydrogen, mercapto, hydroxy, lower alkylthio and aryl lower alkylthio, and R.sup.14 is selected from the group consisting of hydrogen, lower alkyl, aryl and arylllower alkyl;

a 1H-1,2,3,4-tetrazol-1-yl radical of the formula ##STR81## wherein R.sup.17 is selected from the group consisting of hydrogen, mercapto, lower alkyl, aryl 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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