Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Silicon containing doai
Patent
1996-03-04
1998-01-13
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Silicon containing doai
548110, A61K 31695, C07F 718
Patent
active
057079765
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel substituted propane-2-ol derivatives, optical antipodes and racemates thereof, fungicidal compositions containing such compounds as well as to processes for preparing such compounds and compositions. Furthermore, the invention relates to a method of treating diseases caused by fungi, said method comprises administering one or more of the compounds of the present invention in a fungicidally effective amount to a mammal, by using a compound of the invention per se or in the form of a pharmaceutical composition.
The compounds of the present invention are characterized by the formula (I) ##STR3## wherein R.sup.1 is a C.sub.1-10 alkyl group, a phenyl group or a phenyl-C.sub.1-6 alkyl group, and the phenyl moiety of the two latter groups may carry at least one substituent selected from the group consisting of a halogen atom, C.sub.1-6 alkoxy group, phenyl group, phenoxy group and trifluoromethyl group; or phenyl group; ##STR4## and in this formulae Y.sup.1 and Y.sup.2 are, independently from each other, a --N.dbd. atom or a group of the formula --CH.dbd..
The compounds of the formula (I) carrying different substituents in positions 1 and 3 of the basic propane skeleton may exist in the form of optical antipodes. A 1:1 mixture of the antipodes forms a racemic mixture. If there is no reference to an individual antipode, it is self-evident that all the possible three forms are comprised by a reference to a compound of the formula (I). During the preparation process of the compounds of the formula (I) a racemic mixture thereof is formed. From this mixture the individual antipodes can be separated in a manner known per se, e.g. by selective crystallization of a diastereomeric salt pair formed with an optically active compound and then by liberation of the optically active compound of the formula (I).
GB patent specification No. 2,078,719 A relates to highly effective fungicidal compounds, possessing substantial plant growth regulating effect, too. These compounds are characterized by the formula ##STR5## if R is an alkyl, cycloalkyl, aryl or aralkyl, all these groups being optionally substituted by one or two halogen(s), or said aryl or aralkyl groups may carry alkoxy, phenyl, phenoxy or trifluoromethyl substituents; and Y.sup.1 and Y.sup.2 are as defined above.
According to the GB patent specification No. 2,099,818 A, 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propane-2-ol is used as a highly effective human fungicide. It is sold in the form of a human fungicidal pharmaceutical composition under the trade name fluconazole or diflucane.
In accordance with the GB patent specification No. 2,078,719 A the propane-2-ol derivatives of the formula (B) can be prepared by reacting a Grignard reagent of the formula R-Mg-halogen with dichloroacetone. A thus-obtained 1,3-dichloropropane-2-ol derivative of the formula ##STR6## is reacted with a salt, e.g. sodium salt, of imidazole or triazole, taken in an excess, in the presence of a protic or aprotic solvent, e.g. dimethyl formamide. The reaction can be also carried out with epoxy derivatives being prepared in situ through elimination of hydrogen chloride from the corresponding dihalogen compound with a base. The target compounds can be prepared by reacting the corresponding 1,3-bisimidazolyl- or 1,3-bis(1,2,4-triazol-1-yl)acetone with a Grignard reagent of the formula R-Mg-halogen, too. According to a further preparation method a compound of the formula ##STR7## is reacted with dimethyloxosulfoniummethylide, then a thus-obtained compound of the formula ##STR8## containing an R substituent in the place of R.sup.1, is reacted, similarly to the process described above, with the sodium salt of imidazole or triazole. The starting materials of the above processes can be prepared by known methods.
The process for the preparation of the active ingredient of fluconazole according to GB patent specification No. 2,099,818 A comprises the reaction of compounds of the formula (V) and compounds of the formula (IV) containing a substituent R in the place
REFERENCES:
patent: 4729986 (1988-03-01), Olson
patent: 5495024 (1996-02-01), Itoh et al.
Czibula Laszlo
Deutsch Ida nee Juhasz
Farkas Maria nee Kirjak
Hegedus Istvan
Kreidl Janos
Morris Patricia L.
Richter Gedeon Vegyeszeti Gyar Rt.
LandOfFree
Substituted propane-2-OL derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted propane-2-OL derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted propane-2-OL derivatives will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-326314