Optionally substituted phenylimidazolidines, their preparation p

Details Optionally substituted phenylimidazolidines, their preparation p Optionally substituted phenylimidazolidines, their preparation p

1996-06-27

1998-05-12

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

5483185, 5483211, A01N 4350, C07D23340

Patent

active

057505535

DESCRIPTION:

BRIEF SUMMARY
This is a 371 application of PCT/FR 95/00004 filed on Jan. 4, 1995, published as WO95/18794 Jul. 13, 1995.
The present invention relates to new optionally substituted phenylimidazolidines, their preparation process and intermediates, their use as medicaments and the pharmaceutical compositions containing them.
In the Japanese Application J 48087030 3-phenyl 2-thiohydantoins are described which are presented as inhibiting the germination of certain plants.
In European Patent Applications 0,494,819 and 0,578,516 imidazolidines are described which are presented as possessing an anti-androgenic activity. The products of this Patent are however different from the products of the following Patent Application.
Therefore a subject of the present invention is the products of general formula (I): ##STR2## in which: Z.sub.1 and Z.sub.2, identical or different, represent a cyano, nitro radical, a halogen atom, a trifluoromethyl radical or an esterified, amidified or salified free carboxy radical, ##STR3## in which X represents an oxygen or sulphur atom, R.sub.3j represents R.sub.3 with the exception of the hydrogen value and R.sub.3 is chosen from the following radicals: carbon atoms, these radicals being optionally substituted by one or more substituents chosen from halogen atoms and the following radicals: optionally esterified, etherified or protected hydroxy, alkoxy, hydroxyalkyl, alkenyloxy, alkynyloxy, trifluoromethyl, mercapto, cyano, acyl, acyloxy, aryl, optionally substituted S-alkyl, S-aryl, in which the sulphur atom is optionally oxidized in the form of the sulphoxide or sulphone, free, esterified, amidified or salified carboxy, amino, mono- or dialkylamino, a cyclic radical containing 3 to 6 members and optionally containing one or more heteroatoms chosen from sulphur, oxygen or nitrogen atoms and the ##STR4## radical in which R.sub.7 represents an alkyl, hydroxy, alkoxy, aryl or aryloxy radical, the alkyl, alkenyl or alkynyl radicals moreover being optionally interrupted by one or more atoms of oxygen, nitrogen or sulphur optionally oxidized in the form of the sulphoxide or sulphone, the nitrogen atoms being optionally oxidized, alkyl, alkenyl or alkynyl, alkoxy, alkenyloxy, alkynyloxy or trifluoromethyl radical, Y represents an oxygen or sulphur atom or an NH radical, R.sub.4 and R.sub.5, identical or different, represent a hydrogen atom or an alkyl radical having 1 to 12 carbon atoms optionally substituted by one or more substituents chosen from halogen atoms, the ##STR5## radical as defined above, the optionally esterified, etherified or protected hydroxyl radical, linear or branched phenylthio and alkylthio radicals containing at most 8 carbon atoms, phenylthio and alkylthio radicals, in which the sulphur atom can be oxidized in the form of the sulphoxide or sulphone, themselves being optionally substituted by one or more radicals chosen from halogen atoms, the optionally esterified, etherified or protected hydroxyl radical, the free, esterified, amidified or salified carboxy radical, amino, mono- or dialkylamino radicals, with the exception of the products in which R.sub.4 and R.sub.5, identical or different, represent a hydrogen atom or an alkyl radical having 1 to 12 carbon atoms non-substituted or substituted by one or more halogen atoms, those in which one of R.sub.4 or R.sub.5 represents a methyl radical and the other represents a hydroxymethyl radical, Y represents an oxygen atom or an NH radical, the group --AB-- represents the radical ##STR6## Z.sub.1 in position 4 represents a nitro radical and Z.sub.2 in position 3 represents a trifluoromethyl radical, those in which Z.sub.1 and Z.sub.2 both represent a halogen atom and those in which one of Z.sub.1 and Z.sub.2 represents a halogen atom, one of R.sub.4 and R.sub.5 represents an alkyl radical substituted by the group --S--CH.sub.3 and R.sub.3 represents a hydrogen atom or an alkyl radical, ##STR7## in which Z.sub.3 represents a cyano or nitro radical, R.sub.3a represents a hydrogen atom or a linear or branched alkyl radical, containing at mo

REFERENCES:
patent: 5411981 (1995-05-01), Gaillard-Kelly et al.

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