Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1997-03-31
1999-03-30
Shah, Mukund J.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504263, 504265, 504266, 504269, 504270, 504271, 504272, 514361, 514363, 514364, 514365, 514372, 514374, 514378, 514383, 548125, 548128, 548136, 548143, 548204, 548214, 548236, 548239, 5482622, 5482674, C07D40312, C07D41712, C07D40914, A61K 3141
Patent
active
058889418
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to a new series of carboxamides of general formula I having potent antifungal activity. The invention also relates to a process for their preparation, to pharmaceutical compositions containing them and to their use for the treatment of fungal diseases.
DESCRIPTION OF THE PRIOR ART
The compounds of the present invention are antifungal agents belonging to the azole class, whose mechanism of action is based on the inhibition of the biosynthesis of ergosterol, the main sterol present in fungi membranes.
Other antifungal agents having this mechanism of action have been reported in the literature. Patent applications EP 332387 and EP 617031 describe azole derivatives containing an arylcarboxamide group. The compounds of the present invention are not only more potent antifungal agents than the compounds described in the above two patents but they also have a broader spectrum of antifungal activity since, unlike the compounds described therein, they are also effective against filamentous fungi, including aspergillus.
DESCRIPTION OF THE INVENTION
The present invention relates to new carboxamides of general formula I ##STR2## as racemates, diastereomer mixtures or as pure enantiomers, wherein: X represents N or CH; trifluoromethyl groups; chain; C.sub.3 -C.sub.6 cycloalkyl-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, phenyl-C.sub.1 -C.sub.4 alkyl (wherein the phenyl group can be optionally substituted with 1, 2, 3 or 4 groups R.sub.5, which can be the same or different), a group --(CH.sub.2).sub.n --CH.sub.2 OH, a group --(CH.sub.2).sub.n --CH.sub.2 OBn, a group --(CH.sub.2).sub.n --CH.sub.2 NR.sub.6 R.sub.7, a group --(CH.sub.2).sub.n --CH.sub.2 COOR.sub.6, or a group --(CH.sub.2).sub.n --CH.sub.2 COOB.sub.n, in which case R.sub.4 is hydrogen; formula I form an oxazolidine ring of formula I' ##STR3## or R.sub.3 together with R.sub.4 and the remainder of said compound of formula I form a morpholine ring of formula I" ##STR4## wherein D is O, in which case the dotted line represents a covalent bond, or D is hydroxy or hydrogen, in which case the dotted line is absent; containing from 1 to 4 heteroatoms selected from N, O and S and with each ring in the heterocyclic group being formed of 5 or 6 atoms, wherein A can be unsubstituted or have 1, 2, 3 or 4 groups R.sub.8 ; 3 or 4 groups R.sub.9, or B represents a monocyclic or bicyclic heterocyclic group containing from 1 to 4 heteroatoms selected from N, O and S and with each ring in the heterocyclic group being formed of 5 or 6 atoms, which can be optionally substituted with 1, 2, 3 or 4 groups R.sub.9 ; halogen; alkyl; C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, halogen, phenyl (optionally substituted with a group halogen, cyano, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 haloalkoxy), nitro, cyano, hydroxy, hydroxymethyl, a group --NR.sub.6 R.sub.7, a group --CONR.sub.6 R.sub.7, a group --COR.sub.6, a group --COOR.sub.6, or a group --SO.sub.z R.sub.10 ; C.sub.2 -C.sub.4 -alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, 2-carboxy-2-propyl, halogen, nitro, cyano, hydroxy, benzyloxy, hydroxymethyl, a group --CH.sub.2 --OCO--R.sub.6, a group --CO--R.sub.6, a group --COO--R.sub.6, a group --SO.sub.z R.sub.10, a group --NR.sub.6 R.sub.7, a group --CONR.sub.6 R.sub.7, a group --C(.dbd.NR.sub.6)NHR.sub.11, a group --C(.dbd.NR.sub.11)OR.sub.6, and additionally one of the groups R.sub.9 can also represent 1-pyrrolyl, 1-imidazolyl, 1H-1,2,4-triazol-1-yl, 5-tetrazolyl (optionally substituted with C.sub.1 -C.sub.4 alkyl), 1-pyrrolidinyl, 4-morpholinyl, 4-morpholinyl-N-oxide, phenyl or phenoxy (both optionally substituted with a group C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, halogen, nitro or cyano), or a group of formula (i)-(iv) ##STR5## R.sub.10 represents C.sub.1 -C.sub.4 alkyl; z represents 0, 1 or 2; NHR.sub.6, --SO.sub.2 R.sub.10, --OR
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Anguita Manuel
Bartroli Javier
Turmo Enric
J. Uriach & Cia. S.A.
Kifle Bruck
Shah Mukund J.
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