Phenylimidazolidines containing nitrooxy or carbonyloxy groups

Details Phenylimidazolidines containing nitrooxy or carbonyloxy groups Phenylimidazolidines containing nitrooxy or carbonyloxy groups

1998-09-28

2001-06-05

Higel, Floyd D. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C514S398000, C514S399000, C514S400000, C548S307100, C548S319100, C548S321100

Reexamination Certificate

active

06242611

ABSTRACT:

The present invention relates to new phenylimidazolidines containing in particular a nitrooxy or carbonyloxy radical, their preparation process, the new intermediates obtained, their use as medicaments, their new use and the pharmaceutical compositions containing them.
A subject of the present invention is the products of formula (I):
in which:
R
1
and R
2
, identical or different, are chosen from cyano, nitro, trifluoromethyl radicals and halogen atoms,
R
3
represents a linear or branched aryl, arylalkyl, alkyl, alkenyl or alkynyl radical containing at most 10 carbon atoms substituted by a radical chosen from the following radicals: nitrooxy, alkoxycarbonyloxy, cycloalkoxycarbonyloxy, carboxyalkoxy, hydroxyacyl, hydroxyacyloxy, alkoxyacyl and alkoxyacyloxy, in which the alkyl, alkoxy, acyl and acyloxy radicals are linear or branched, containing at most 10 carbon atoms, the cycloalkoxy radical contains 3 to 7 members, the carboxy radical is free, salified, esterified or amidified and the hydroxy radical is free, esterified, etherified or protected,
R
4
and R
5
are either identical or different and represent a linear or branched alkyl radical containing at most 4 carbon atoms and optionally substituted by a halogen atom, or form with the carbon atom to which they are linked a cyclic radical constituted by 3 to 7 members and optionally containing one or more identical or different heteroatoms, chosen from oxygen, sulphur or nitrogen atoms,
X and Y, identical or different, represent an oxygen or sulphur atom, said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomer forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).
In the products of formula (I) and in what follows:
the term halogen designates the fluorine, chlorine, bromine or iodine atoms.
The fluorine, chlorine or bromine atoms are preferred.
The term linear or branched alkyl radical designates the following radicals: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, isohexyl and also heptyl, octyl, nonyl and decyl as well as their linear or branched position isomers.
The alkyl radicals having at most 6 carbon atoms are preferred and in particular the methyl, ethyl, propyl, isopropyl, n-butyl, n-pentyl and n-hexyl radicals,
the term linear or branched alkenyl radical designates the vinyl, allyl, 1-propenyl, butenyl, 1-butenyl, pentenyl or hexenyl radical as well as their linear or branched position isomers.
Among the alkenyl radicals, the vinyl, allyl, n-butenyl or isobutenyl values are preferred,
the term alkynyl designates a linear or branched radical having at most 12 and preferably 4 carbon atoms such as for example ethynyl, propargyl, butynyl, pentynyl or hexynyl.
Among the alkynyl radicals, the propargyl radical is preferred.
The term linear or branched alkoxy radical designates the following radicals: methoxy, ethoxy, propoxy, isopropoxy, linear, secondary or tertiary butoxy, pentoxy or hexoxy as well as their linear or branched position isomers,
the term cyclic radical constituted by 3 to 7 members and optionally containing one or more identical or different heteroatoms, chosen from oxygen, sulphur or nitrogen atoms, designates on the one hand a cycloalkyl radical which itself designates in particular the cyclobutyl, cyclopentyl and cyclohexyl radicals and on the other hand a carbocyclic radical interrupted by one or more heteroatoms chosen from oxygen, nitrogen or sulphur atoms such as quite particularly the saturated monocyclic heterocyclic radicals. The following radicals can be mentioned for example: oxetannyl, oxolannyl, dioxanyl, dithiolane, thiooxolane, thiooxane, pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, azetidine, oxetane and thietane, and there can be indicated quite particularly:
the rings with 4 members containing at most 1 heteroatom, such as:
the rings with 5 members containing at most 1 heteroatom, such as:
the rings with 6 members containing at most 6 heteroatoms, such as:
The following radical can also be indicated:
in which W represents an alkyl or aryl radical as defined above,
the term cycloalkoxy radical represents in particular the cyclobutoxy, cyclopentoxy or cyclohexyloxy radicals,
the term acyl radical preferably designates the formyl, acetyl, propionyl, butyryl and benzoyl radicals, but also the valeryl, hexanoyl, acryloyl, crotonoyl and carbamoyl radicals,
the term acyloxy radical designates the radicals in whichthe acyl radicals have the meaning indicated above and for example the acetoxy or propionyloxy radicals,
the term aryl designates the carbocyclic aryl radicals such as phenyl or naphthyl and the monocyclic heterocyclic aryl radicals with 5 or 6 members or constituted by condensed rings, containing one or more heteroatoms preferably chosen from oxygen, sulphur and nitrogen. Among the heterocyclic aryls with 5 members, the following radicals can be mentioned: furyl, thienyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, thiadiazolyl, pyrazolyl, isoxazolyl, tetrazolyl.
Among the heterocyclic aryls with 6 members, the pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl radicals can be mentioned.
Among the condensed aryl radicals, the indolyl, benzofurannyl, benzothienyl, quinolinyl radicals can be mentioned. The phenyl, tetrazolyl and pyridyl radicals are preferred.
The term arylalkyl designates the radicals resulting from the combination of the alkyl radicals and the aryl radicals mentioned above.
The benzyl, phenylethyl, pyridylmethyl, pyridylethyl or tetrazolylmethyl radicals are preferred.
the terms alkoxy- and cycloalkoxy-carbonyloxy, carboxyalkoxy, hydroxy- and alkoxy-acyl and -acyloxy, represent the radicals in which the alkoxy, acyl and acyloxy radicals have the meanings indicated above: there can be mentioned for example and in a non-expaustive manner, the following radicals: isopropyloxycarbonyloxy, cyclopentyloxycarbonyloxy, cyclohexyloxycarbonyloxy, methoxycarbonyloxy, carboxybutyl, ethoxycarbonylbutyl, hydroxyacetyl, hydroxypropionyl or methoxybutyryl; hydroxyacetoxy or hydroxypropionyloxy; methoxy- or ethoxypropionyloxy.
By way of example and in a non-exhaustive manner, in addition to the values indicated above and to those given hereafter, in particular in the experimental part, R
3
can therefore in particular represent the isopropyloxy- or cyclohexyloxy or cyclopentyloxy -carbonyloxybutyl or the corresponding radicals in which the isopropyloxy remainder and the butyl remainder take the other values of the alkoxy and alkyl radicals mentioned above respectively such as, for example, pentoxy, butoxy, ethoxy, pentyl or isopropyl; such alkyl radicals can also be replaced by alkenyl or alkynyl remainders such as for example pentenyl, butenyl, propenyl, pentynyl, butynyl or allyl or also by aryl or arylalkyl remainders as defined above, such as, for example, phenyl, pyridyl, benzyl, phenethyl, pyridylmethyl or pyridylethyl. R
3
can also represent for example the following radicals: hydroxymethylcarbonylethyl, hydroxymethylcarbonylmethyl, hydroxy-1-difluoro-2,2-butyl, hydroxy-l-difluoro-2,2-propyl, hydroxyphenylmethyl, dihydroxyphenylmethyl, hydroxyphenyl or also hydroxymethylphenyl.
As particular examples of an alkyl radical substituted by a halogen atom, there can be mentioned the mono-fluoro-, chloro- or bromo-methyl, ethyl and -isopropyl radicals.
The carboxy radical or radicals of the products of formula (I) can be free, salified, esterified or amidified by various groups known to a man skilled in the art, amongst which there can be mentioned, for example:
among the salification compounds, mineral bases such as, for example, an equivalent of sodium, potassium, lithium, calcium, magnesium or ammonium or organic bases such as, for example, methylamine, propylamine, trimethylamine, diethylamine, triethylamine, N,N-dimethylethanolamine, tris (hydroxymethyl) amino methane, ethanolamine, pyridine, picoline, dicyclohexylamine, morpholine, benzylamine, procaine, lysine, arginine, histidine, N-

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