Oxazolidin-2-one derivatives, preparation method therefor and th

Details Oxazolidin-2-one derivatives, preparation method therefor and th Oxazolidin-2-one derivatives, preparation method therefor and th

1998-04-13

1999-10-19

Higel, Floyd D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548225, 548229, 514374, C07D41304, C07D41314, A61K 3142

Patent

active

059691468

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/FR96/01511 filed Oct. 8, 1996.
The subject of the present invention is compounds derived from oxazolidin-2-one of general formula (I) ##STR2## in which: R.sub.1 represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, a fluoroalkyl group, a hydroxyfluoroalkyl group, a cyanoalkyl group, a phenyl group which is unsubstituted or substituted by a halogen atom or by an alkoxy, nitrile or nitro group, a phenylmethyl group which is unsubstituted or substituted by a halogen atom or by an alkoxy, nitrile or nitro group or an R.sub.3 A- group in which R.sub.3 is a is cycloalkyl or cyclooxyalkyl group which is unsubstituted or substituted by a hydroxyl group and A is a --CH.sub.2 or --CH.sub.2 --CH.sub.2 radical, is an alkyl group or a hydrogen atom and group,
In the context of the present invention, and except when otherwise indicated, the above terms have the following meanings: 1 to 5 carbon atoms, defined above, carbon atoms of which is substituted by one or a number of fluorine atoms, the carbon atoms of which is substituted by a hydroxyl group, 3 to 6 carbon atoms, carbon atoms of which is replaced by an oxygen atom as heteroatom; the perhydrofuranyl and perhydropyranyl groups are representative of such a cyclooxyalkyl group, carbon atoms of which is substituted by a nitrile group.
The compounds of formula (I) where R.sub.2 is a methyl group are preferred. Among the latter compounds, those where X represents an oxygen atom are very particularly preferred.
When X represents an oxygen atom, the R.sub.1 Z group advantageously represents: R.sub.1 chosen from a hydrogen atom, an alkyl group, a fluoroalkyl group, a hydroxyfluoroalkyl group, a cyanoalkyl group, an R.sub.3 A- group, a phenyl group which is unsubstituted or substituted by a halogen atom or a nitro, nitrile or alkoxy group and a phenylmethyl group which is unsubstituted or substituted by a halogen atom or a nitro, nitrile or alkoxy group. More preferentially, R.sub.a is a hydrogen atom or a phenylmethyl, butyl, 4,4,4-trifluorobutyl, 4,4,4-trifluoro-3-hydroxybutyl, 3,3,3-trifluoro-2-hydroxypropyl, 3-cyanopropyl, p-fluorophenylmethyl, cyclopropylmethyl or 2-(1-hydroxycyclopentyl)ethyl group. group and Re has one of the meanings of R.sub.1 chosen from a hydrogen atom or an alkyl group, a fluoroalkyl group, a hydroxyalkyl group, a hydroxyfluoroalkyl group, a phenyl group which is unsubstituted or substituted by a halogen atom or a nitro, nitrile or alkoxy group or a phenylmethyl group which is unsubstituted or substituted by a halogen atom or a nitro, nitrile or alkoxy group. More preferentially, R.sub.b Z is chosen from the ethenyl, 2-phenylethenyl, 2-phenylethyl, 5,5,5-trifluoropentyl, 5,5,5-trifluoropentenyl, 5,5,5-trifluoro-4-hydroxypentyl or 5,5,5-trifluoro-4-hydroxypentenyl group.
When X represents a sulphur atom, the R.sub.1 Z group advantageously represents an R.sub.c O group, where R, has one of the meanings of R.sub.1 chosen from an alkyl group, a hydroxyalkyl group, a fluoroalkyl group, a hydroxyfluoroalkyl group, a phenyl group which is unsubstituted or substituted by a halogen atom or a nitro, nitrile or alkoxy group or a phenylmethyl group which is unsubstituted or substituted by a halogen atom or by an alkoxy, nitrile or nitro group. According to a preferred aspect of the invention, R.sub.c is chosen from the group consisting of butyl, 4,4,4-trifluorobutyl, 4,4,4-trifluoro-3-hydroxybutyl and the phenylmethyl group.
When X represents an NR.sub.4 group, R.sub.4 is preferably a methyl group and the R.sub.1 Z group advantageously represents an R.sub.d O group, where R.sub.d has one of the meanings of R.sub.1 chosen from a fluoroalkyl group, a hydroxyfluoroalkyl group, a phenyl group which is unsubstituted or substituted by a halogen atom or a nitro, nitrile or alkoxy group or a phenylmethyl group which is unsubstituted or substituted by a halogen atom or a nitro, nitrile or alkoxy group. According to a preferred aspect of the invention, R.sub.d is chosen from the group consisting of 4,4,4-trifluorobutyl, 4

REFERENCES:
patent: 5783590 (1998-07-01), Booher et al.

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