Sulphorous derivatives of imidazole and their use as medicaments

The present invention relates to new sulphurous derivatives of imidazole, 
their preparation process, the new intermediates obtained, their use as 
medicaments and the pharmaceutical compositions containing them. 
A subject of the present invention is the products of formula (I.sub.B): 
##STR4## 
in which: R.sub.1 represents an alkyl, alkenyl, alkynyl, or alkylkhio 
radical, each of these radicals being linear or branched and containing at 
most 10 carbon atoms, or a cycloalkyl radical containing 3 ko 7 carbon 
atoms, all khese radicals being optionally substituted by one or more 
identical or different radicals chosen from halogen atoms, and the 
following radicals, hydroxyl, alkoxy containing at most 6 carbon atoms, 
alkylthio, acyl, free, salified or esterified carboxy, cyano, nitro, amino 
optionally substituted by one or two identical or different alkyl radicals 
containing at most 6 carbon atoms, cycloalkyl containing 3 to 7 carbon 
atoms and aryl opkionally substituted by one or more identical or 
different radicals chosen from halogen atoms, and khe following radicals, 
hydroxyl, alkyl, alkenyl and alkoxy containing at most 6 carbon atoms, 
haloalkyl, alkylthio, haloalkylkhio, haloalkoxy, aryloxy, arylalkoxy. 
carbamoyl, acyl, acyloxy, free, salified or esterified carboxy, 
tetrazolyl, cyano, nitro, amino optionally substituted by one or two 
identical or different alkyl radicals containing at most 6 carbon atoms 
and phenyl optionally substituted by one or more radicals chosen from 
halogen atoms, and the following radicals, hydroxyl, alkyl and alkoxy 
containing at most 4 carbon atoms, trifluoromethyl, free, salified or 
esterified carboxy and tetrazolyl, 
R.sub.2B and R.sub.3B, identical or different, are chosen from: 
a) the hydrogen atom, the following radicals: mercapto, formyl, acyl, free, 
salified or esterified carboxy, nitro, cyano, --PO.sub.3 (R).sub.2 in 
which R represents a hydrogen atom, an alkyl or aryl radical, amino or 
carbamoyl radicals optionally substituted by one or two radicals chosen 
from the --(CH.sub.2).sub.m1 --S(O).sub.m2 --X--R.sub.10 group as defined 
below and alkyl and alkinyl radicals, having at most 4 carbon atoms, 
b) the radicals R.sub.4B, 
##STR5## 
in which: n represents the values 0, 1 or 2, 
X' represents an aryl radical optionally substituted by one or more 
identical or different radicals chosen from halogen atoms, the following 
radicals: hydroxyl, alkyl, alkenyl and alkoxy containing at most 6 carbon 
atoms, haloalkyl, alkylthio, haloalkylthio, haloalkoxy, aryloxy, 
arylalkoxy, carbamoyl, acyl, acyloxy, free, salified or esterified 
carboxy, tetrazolyl, cyano, nitro, amino optionally substituted by one or 
two identical or different alkyl radicals containing at most 6 carbon 
atoms and phenyl optionally substituted by one or more radicals chosen 
from halogen atoms, and the following radicals: hydroxyl, alkyl and alkoxy 
containing at most 4 carbon atoms, trifluoromethyl, free, salified or 
esterified carboxy and tetrazolyl, and either R.sub.4B represents a 
--(CH.sub.2).sub.m1 --S(O).sub.m2 --X--R.sub.10 radical in which ml 
represents an integer from 0 to 4, m2 represents an integer from 0 to 2, 
preferably 2, and either when ml is not 0, 
X--R.sub.10 represents an amino radical optionally substituted by one or 
two alkyl radicals containing at most 6 carbon atoms, 
or whatever the value of m1, 
X represents a single bond or the radicals --NH--, --NH--CO-- and 
--NH--CO--NH--, 
and R.sub.10 represents an alkyl, atkenyl or aryl radical, these radicals 
being optionally substituted by one or more different or identical 
radicals chosen from halogen atoms, and the following radicals: hydroxyl, 
alkoxy containing at most 6 carbon atoms, alkylthio, acyl, free, salified 
or esterified carboxy, cyano, nitro, amino optionally substituted by one 
or two identical or different alkyl radicals containing at most 6 carbon 
atoms, cycloalkyl containing 3 to 7 carbon atoms and aryl optionally 
substituted by one or more different or identical radicals chosen from 
halogen atoms, the radicals hydroxyl, alkyl, alkenyl and alkoxy containing 
at most 6 carbon atoms, haloalkyl, alkylthio, haloalkylthio, haloalkoxy, 
aryloxy, arylalkoxy, carbamoyl, acyl, acyloxy, free, salified or 
esterified carboxy, tetrazolyl, cyano, nitro, amino optionally substituted 
by one or two different or identical alkyl radicals containing at most 6 
carbon atoms and phenyl optionally substituted by one or more radicals 
chosen from halogen atoms, hydroxyl radicals, alkyl and alkoxy radicals 
containing at most 4 carbon atoms, trifluoromethyl radicals, free, 
salified or esterified carboxy radicals and tetrazolyl radicals, 
or R.sub.4B represents the hydrogen atom, or a radical chosen from alkyl, 
alkenyl, alkynyl and acyl, each of these radicals being linear or branched 
and containing at most 6 carbon atoms, and being optionally interrupted by 
one or more heteroatoms chosen from sulphur, oxygen or nitrogen atoms, or 
R.sub.4B represents an amino radical optionally substituted by one or two 
identical or different alkyl radicals containing at most 6 carbon atoms, a 
cycloalkyl radical containing 3 to 6 carbon atoms or an aryl radical, the 
alkyl alkenyl, cycloalkyl and aryl radicals being optionally substituted 
by one or more identical or different radicals chosen from: 
halogen atoms, 
hydroxyl, haloalkyl, alkylthio, alkenylthio, alkynylthio, mercapto, 
acylthio, haloalkylthio, haloalkoxy, cyano, azido, nitro radicals, 
the --O--Si(R.sub.5).sub.3 or --Si(R.sub.5).sub.3 radical in which R.sub.5 
represents an alkyl radical containing at most 4 carbon atoms, 
aryl, arylalkyl, arylalkenyl, arylthio, aryloxy and arylalkoxy radicals in 
which, if appropriate, the alkyl, alkenyl and alkoxy radicals contain at 
most 6 carbon atoms and the aryl radical is optionally substituted by one 
or more identical or different radicals chosen from halogen atoms, 
hydroxyl, alkyl, alkenyl and alkoxy radicals containing at most 6 carbon 
atoms, haloalkyl, alkylthio, haloalkylthio, haloalkoxy, aryloxy, 
arylalkoxy, carbamoyl, acyl, acyloxy, free, salified or esterified 
carboxy, tetrazolyl, cyano, nitro, amino optionally substituted by one or 
two identical or different alkyl radicals containing at most 6 carbon 
atoms and phenyl optionally substituted by one or more radicals chosen 
from halogen atoms, hydroxyl radicals, alkyl and alkoxy radicals 
containing at most 4 carbon atoms, trifluoromethyl radicals, free, 
salified or esterified carboxy radicals and tetrazolyl radicals, 
alkyl, alkenyl and alkoxy radicals containing at most 6 carbon atoms, free, 
salified or esterified carboxy radicals, tetrazolyl, acyl, formyl, 
acyloxy, and --SO.sub.3 H radicals, and 
the radicals 
##STR6## 
in which: either R.sub.6 and R.sub.7 or R.sub.8 and R.sub.9, identical or 
different, are chosen from: 
the hydrogen atom, 
amino acids, 
alkyl and alkenyl radicals containing at most 6 carbon atoms and optionally 
substituted by one or more identical or different radicals chosen from 
halogen atoms, the hydroxyl radical or alkoxy radicals containing at most 
6 carbon atoms, 
the aryl, arylalkyl and arylalkenyl radicals in which the linear or 
branched alkyl and alkenyl radicals contain at most 6 carbon atoms, these 
aryl, arylalkyl and arylalkenyl radicals being such that the aryl radical 
that they constitute or that they contain represents a monocyclic radical 
containing 5, 6 or 7 links or a radical constituted by condensed rings 
containing 8 to 14 links, these radicals containing optionally one or more 
heteroatoms chosen from oxygen, nitrogen and sulphur atoms, and being 
optionally substituted by one or more radicals chosen from halogen atoms, 
hydroxyl, nitro radicals, alkyl, alkenyl, haloalkyl, alkoxy and acyl 
radicals, these radicals containing at most 6 carbon atoms, amino radicals 
optionally substituted by one or two identical or different alkyl radicals 
containing at most 6 carbon atoms, free, salified or esterified carboxy 
radicals, tetrazolyl, aryl and arylalkyl radicals, the two latter radicals 
being optionally substituted by one or more radicals chosen from halogen 
atoms, hydroxyl, trifluoromethyl, nitro radicals, free, salified or 
esterified carboxy radicals and tetrazolyl radicals, 
a --(CH.sub.2).sub.m1 --S(O).sub.m2 --X--R.sub.10 radical as defined above, 
or R.sub.6 and R.sub.7 or R.sub.8 and R.sub.9 form respectively with the 
nitrogen atom to which they are linked a monocyclic radical containing 5, 
6 or 7 links or a radical constituted by condensed rings containing 8 to 
14 links, these identical or different radicals optionally containing one 
or more other heteroatoms chosen from oxygen, nitrogen and sulphur atoms, 
and being optionally substituted by one or more radicals chosen from 
halogen atoms, hydroxyl radicals, nitro, alkyl, alkenyl, haloalkyl, alkoxy 
and acyl radicals, these radicals containing at most 6 carbon atoms, amino 
radicals optionally substituted by one or two identical or different alkyl 
radicals containing at most 6 carbon atoms, free, salified or esterified 
carboxy radicals, tetrazolyl, aryl and arylalkyl radicals, these two 
latter radicals being optionally substituted by one or more radicals 
chosen from halogen atoms, hydroxyl radicals, trifluoromethyl, nitro 
radicals, free, salified or esterified carboxy radicals and tetrazolyl 
radicals, 
or R.sub.8 and R.sub.9, identical or different, represent an acyl radical 
or one of R.sub.8 or R.sub.9 represents a carbamoyl, alkoxycarbonyl or 
benzyloxycarbonyl radical or R.sub.8 and R.sub.9 form together with the 
nitrogen atom to which they are linked a phthalimido or succinimido 
radical, 
c) the --S--S--R.sub.4B, radical in which R.sub.4B, represents the values 
defined for R.sub.4B except for the amino and alkoxy radicals, it being 
understood that at least one of R.sub.2B and R.sub.3B represents the 
--OR.sub.4B radical or one of the radicals: 
##STR7## 
knowing that R.sub.2B and R.sub.3B cannot represent simultaneously the 
--S--S--R.sub.4B ' radical, 
m represents the value 0, 1 or 2, 
Y.sub.B represents the --Y.sub.1B --B--Y.sub.2B radical in which: 
Y.sub.1B represents a monocyclic aryl radical containing 5, 6 or 7 links or 
constituted by condensed rings containing 8 to 10 links, these radicals 
optionally containing one or more heteroatoms chosen from oxygen, nitrogen 
and sulphur atoms, and being optionally substituted by one or more 
radicals chosen from the radicals that can be represented by R.sub.2B and 
R.sub.3B, 
B represents: 
either a single bond between Y.sub.1B and Y.sub.2B, or one of the following 
divalent radicals: --CO--, --O--, --NH--CO--, --CO--NH-- or 
--O--(CH.sub.2).sub.p -- with p representing the values 1, 2 or 3, 
Y.sub.2B represents: 
either, whatever the value of B and Y.sub.2B being identical or different 
to Y.sub.1B, the values defined for Y.sub.1B, or, if B represents a single 
bond, a hydrogen atom, a cyano radical, a free, salified or esterified 
carboxy radical, the said products of formula (I.sub.B) 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 the said products of formula (I.sub.B). 
Also a subject of the present invention is the products of formula 
(I.sub.B) as defined above and corresponding to formula 
##STR8## 
in which: R.sub.1 represents an alkyl, alkenyl, alkynyl, alkylthio 
radical, each of these radicals being linear or branched and containing at 
most 10 carbon atoms, or a cycloalkyl radical containing 3 to 7 carbon 
atoms, all these radicals being optionally substituted by one or more 
identical or different radicals chosen from halogen atoms, hydroxyl, 
alkoxy radicals containing at most 6 carbon atoms, alkylthio, acyl 
radicals, free, salified or esterified carboxy radicals, cyano, nitro, 
amino radicals optionally substituted by one or two identical or different 
alkyl radicals containing at most 6 carbon atoms, cycloalkyl radicals 
containing 3 to 7 carbon atoms and aryl radicals optionally substituted by 
one or more identical or different radicals chosen from halogen atoms, 
hydroxyl radicals, alkyl, alkenyl and alkoxy radicals containing at most 6 
carbon atoms, haloalkyl, alkylthio, haloalkylthio, haloalkoxy, aryloxy, 
arylalkoxy, carbamoyl, acyl, acyloxy radicals, free, salified or 
esterified carboxy radicals, tetrazolyl, cyano, nitro, amino radicals 
optionally substituted by one or two identical or different alkyl radicals 
containing at most 6 carbon atoms and phenyl radicals optionally 
substituted by one or more radicals chosen from halogen atoms, hydroxyl 
radicals, alkyl and alkoxy radicals containing at most 4 carbon atoms, 
trifluoromethyl radicals, free, salified or esterified carboxy radicals 
and tetrazolyl radicals, 
R.sub.2 and R.sub.3, identical or different, are chosen from: 
a) the hydrogen atom, the following radicals: mercapto, formyl, acyl, free, 
salified or esterified carboxy, nitro, cyano, or --PO.sub.3 (R).sub.2 in 
which R represents a hydrogen atom, an alkyl or aryl radical, 
b) the radicals R.sub.4, 
##STR9## 
in which: n represents the values 0, 1 or 2, 
X' represents an aryl radical optionally substituted by one or more 
identical or different radicals chosen from halogen atoms, hydroxyl 
radicals, alkyl, alkenyl and alkoxy radicals containing at most 6 carbon 
atoms, haloalkyl, alkylthio, haloalkylthio, haloalkoxy, aryloxy, 
arylalkoxy, carbamoyl, acyl, acyloxy radicals, free, salified or 
esterified carboxy radicals tetrazolyl, cyano, nitro radicals, amino 
radicals optionally substituted by one or two identical or different alkyl 
radicals containing at most 6 carbon atoms and phenyl radicals optionally 
substituted by one or more radicals chosen from halogen atoms, hydroxyl 
radicals, alkyl and alkoxy radicals containing at most 4 carbon atoms, 
trifluoromethyl radicals, free, salified or esterified carboxy radicals 
and tetrazolyl radicals, 
R.sub.4 represents a hydrogen atom an alkyl, alkenyl, alkynyl, or acyl 
radical, each of these radicals being linear or branched and containing at 
most 6 carbon atoms, an amino radical optionally substituted by one or two 
identical or different alkyl radicals containing at most 6 carbon atoms, a 
cycloalkyl radical containing 3 to 6 carbon atoms or an aryl radical, the 
alkyl, alkenyl, cycloalkyl and aryl radicals being optionally substituted 
by one or more identical or different radicals chosen from: 
halogen atoms, 
hydroxyl, haloalkyl, alkylthio, mercapto, acylthio, haloalkylkhio, 
haloalkoxy, cyano, azido, nitro radicals, 
the --O--Si--(R.sub.5).sub.3 or --Si(R.sub.5).sub.3 radical in which 
R.sub.5 represents an alkyl radical containing at most 4 carbon atoms, 
aryl, arylalkyl, arylalkenyl, arylkhio, aryloxy and arylalkoxy radicals in 
which, if appropriate, the alkyl, alkenyl and alkoxy radicals contain at 
most 6 carbon atoms and the aryl radical is optionally substituted by one 
or more identical or different radicals chosen from halogen atoms, 
hydroxyl radicals, alkyl, alkenyl and alkoxy radicals containing at most 6 
carbon atoms, haloalkyl, alkylthio, haloalkylthio, haloalkoxy, aryloxy, 
arylalkoxy, carbamoyl, acyl, acyloxy radicals, free, salified or 
esterified carboxy radicals, tetrazolyl, cyano, nitro radicals, amino 
radicals optionally substituted by one or two identical or different alkyl 
radicals containing at most 6 carbon atoms and phenyl radicals optionally 
substituted by one or more radicals chosen from halogen atoms, hydroxyl 
radicals, alkyl and alkoxy radicals containing at most 4 carbon atoms, 
trifluoromethyl radicals, free, salified or esterified carboxy radicals 
and tetrazolyl radicals, 
alkyl, alkenyl and alkoxy radicals containing at most 6 carbon atoms, free, 
salified or esterified carboxy radicals, tetrazolyl, acyl, acyloxy 
radicals, --SO.sub.3 H radicals, and 
the radicals 
##STR10## 
in which: either R.sub.6 and R.sub.7 or R.sub.8 and R.sub.9, identical or 
different, are chosen from: 
the hydrogen atom, 
alkyl and alkenyl radicals containing at most 6 carbon atoms and optionally 
substituted by one or more identical or different radicals chosen from 
halogen atoms, the hydroxyl radical or alkoxy radicals containing at most 
6 carbon atoms, 
aryl, arylalkyl and arylalkenyl radicals in which the linear or branched 
alkyl and alkenyl radicals contain at most 6 carbon atoms, these aryl, 
arylalkyl and arylalkenyl radicals being such that the aryl radical that 
they constitute or that they contain represents a monocyclic radical 
containing 5, 6 or 7 links or a radical constituted by condensed rings 
containing 8 to 14 links, these radicals optionally containing one or more 
heteroatoms chosen from oxygen, nitrogen and sulphur atoms, and being 
optionally substituted by one or more radicals chosen from halogen atoms, 
hydroxyl, nitro radicals, alkyl, alkenyl, haloalkyl, alkoxy and acyl 
radicals, these radicals containing at most 6 carbon atoms, amino radicals 
optionally substituted by one or two identical or different alkyl radicals 
containing at most 6 carbon atoms, free, salified or esterified carboxy 
radicals, tetrazolyl radicals, aryl and arylalkyl radicals, these two 
latter radicals being optionally substituted by one 
or more radicals chosen from halogen atoms, hydroxyl radicals, 
trifluoromethyl, nitro radicals, free, salified or esterified carboxy 
radicals and tetrazolyl radicals, or R.sub.6 and R.sub.7 or R.sub.8 and 
R.sub.9 form respectively with the nitrogen atom to which they are linked 
a monocyclic radical containing 5, 6 or 7 links or a radical constituted 
by condensed rings containing 8 to 14 links, these identical or different 
radicals optionally containing one or more other heteroatoms chosen from 
oxygen, nitrogen and sulphur atoms, and being optionally substituted by 
one or more radicals chosen from halogen atoms, hydroxyl, nitro radicals, 
alkyl, alkenyl, haloalkyl, alkoxy and acyl radicals, these radicals 
containing at most 6 carbon atoms, amino radicals optionally substituted 
by one or two identical or different alkyl radicals containing at most 6 
carbon atoms, free, salified or esterified carboxy radicals, tetrazolyl 
radicals, aryl and arylalkyl radicals, these two latter radicals being 
optionally substituted by one or more radicals chosen from halogen atoms, 
hydroxyl radicals, trifluoromethyl, nitro radicals, free, salified or 
esterified carboxy radicals and tetrazolyl radicals, 
or R.sub.8 and R.sub.9, identical or different, represent an acyl radical 
or one of R.sub.8 or R.sub.9 represents a carbamoyl, alkoxycarbonyl or 
benzyloxycarbonyl radical or R.sub.8 and R.sub.9 form together with the 
nitrogen atom to which they are linked a phthalimido or succinimido 
radical,, 
c) the --S--S--R.sub.4, radical in which R.sub.4, represents the values 
defined for R.sub.4 except for the amino and alkoxy radicals, m represents 
the value 0, 1 or 2, 
Y represents the --Y.sub.1 --B--Y.sub.2 radical in which: 
Y.sub.1 represents a monocyclic aryl radical containing 5, 6 or 7 links or 
constituted by condensed rings containing 8 to 10 links, these radicals 
optionally containing one or more heteroatoms chosen from oxygen, nitrogen 
and sulphur atoms, and being optionally substituted by one or more 
radicals chosen from the radicals that can be represented by R.sub.2 and 
R.sub.3, 
B represents: 
either a single bond between Y.sub.1 and Y.sub.2, 
or one of the following divalent radicals: --CO--, --O--, --NH--CO--, 
--CO--NH-- or --O--(CH.sub.2).sub.p -- with p representing the values 1, 2 
for 3, 
Y.sub.2 represents: 
either, whatever the value of B and Y.sub.2 being identical or different to 
Y.sub.1, the values defined for Y.sub.1, 
or, if B represents a single bond, a hydrogen atom, a cyano radical, a 
free, salified or esterified carboxy radical, it being understood that at 
least one of R.sub.2 and R.sub.3 represents one of the radicals: 
##STR11## 
knowing that R.sub.2 and R.sub.3 cannot represent simultaneously the 
--S--S--R.sub.4 ' radical, the 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 the said products of formula (I). 
In the products of formulae (I.sub.B) and (I) and in what follows: 
the term linear or branched alkyl radical preferably designates methyl, 
ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl 
radicals but can also represent a pentyl or hexyl radical and in 
particular an isopentyl and isohexyl radical, 
the term linear or branched alkenyl radical preferably designates a vinyl, 
allyl, 1-propenyl, butenyl radical and particularly 1-butenyl or pentenyl 
radical, 
the term linear or branched alkynyl radical preferably designates an 
ethynyl, propargyl, butynyl or pentynyl radical. 
Among the alkyl radicals interrupted by one or more heteroatoms, there can 
be mentioned methoxymethyl, methoxyethoxymethyl, propylthiopropyl, 
propyloxypropyl, propylthioethyl, methylthiomethyl radicals, 
the term halogen atom preferably designates a chlorine atom, but can also 
represent a fluorine, bromine or iodine atom, 
the term linear or branched alkoxy radical preferably designates methoxy, 
ethoxy, propoxy or isopropoxy radicals, but can also represent a linear, 
secondary or tertiary butoxy radical, 
the term acyl radical preferably designates a radical having 1 to 6 carbon 
atoms such as for example the formyl, acetyl, propionyl, butyryl or 
benzoyl radical, but also the pentanoyl, hexanoyl, acryloyl, crotonoyl or 
carbamoyl radical, 
the term amino substituted by one or two alkyl radicals preferably 
designates radicals in which the alkyl radical or radicals are chosen from 
alkyl radicals as defined above such as for example for monoalkylamino in 
methylamino or ethylamino, or for example for dialkylamino in 
dimethylamino or also methylethylamino, 
the term acyloxy radical designates for example a radical in which the acyl 
radical has the values indicated above and preferably designates a 
formyloxy, acetyloxy, propionyloxy, butyryloxy or benzoyloxy radical, 
the term cycloalkyl radical preferably designates cyclopropyl, cyclobutyl, 
cyclopentyl or cyclohexyl radicals. 
the terms monocyclic radical and radical constituted by condensed rings 
designate saturated or unsaturated carbocyclic or heterocyclic radicals, 
it being understood that the heterocyclic radicals as defined above can 
contain one or more heteroatoms chosen from oxygen, nitrogen or sulphur 
atoms and that when these heterocyclic radicals contain more than one 
heteroatom, the heteroatoms of these heterocyclic radicals can be 
identical or different: 
the term monocyciic radical p eferabiy designates the radicals which 
contain 5 to 7 links: among the saturated carbocyclic monocyclic radicals 
there can be mentioned, for example, cyclohexyl and cyclopentyl radicals; 
among the unsaturated carbocyclic monocyclic radicals there can be 
mentioned, for example, cyclopentenyl, cyclohexenyl, cyclopentadienyl, 
cyclohexadienyl radicals and the carbocyclic aryl radicals such as the 
phenyl radical; among the saturated heterocyclic monocyclic radicals there 
can be mentioned for example pyrrolidinyl, imidazolidinyl, pyrazolidinyl, 
piperidyl, piperazinyl, morpholinyl, thiomorpholinyl, and azepinyl 
radicals, among the unsaturated heterocyclic monocyclic radicals there can 
be mentioned, for example, thienyl, furyl, pyrannyl, pyrrolyl, imidazolyl, 
pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, 
thiadiazolyl, oxazolyl, furazannyl, and pyrrolinyl radicals such as delta 
2-pyrrolinyl, imidazolinyl such a delta 2-imidazolinyl, pyrazolinyl such 
as delta 3-pyrazolinyl, as well as the isomers of position of the 
heteroatom or heteroatoms that can be contained by these radicals such as, 
for example, isothiazolyl or isoxazolyl radicals, 
the term radical constituted by condensed rings preferably designates 
radicals which contain 8 to 14 links: among the radicals constituted by 
saturated carbocyclic condensed rings there can be mentioned, for example, 
indanyl bicyclo-[4,4,0]decyl or bicyclo[4,4,1]undecyl radicals; among the 
radicals constituted by unsaturated carbocyclic condensed rings there can 
be mentioned aryl radicals, for example, naphthyl or phenanthryl, indenyl 
radicals; among the radicals constituted by saturated heterocyclic 
condensed rings there can be mentioned, for example, 
1-oxa-spiro[4,5]decyl, tetrahydropyrane-2-spirocyclohexyl, 
cyclohexanespiro-2'-(tetrahydrofuran) or 1,10-diaza-anthr-4-yl, among the 
radicals constituted by unsaturated heterocyclic condensed rings there 
canbe mentioned aryl radicals such as, for example, benzothienyl, 
naphtho[2,3-b]thienyl, indenyl, thianthrenyl, isobenzofurannyl, chromenyl, 
xanthenyl, phenoxathiinyl, indolizinyl, isoindolyl, 3H-indolyl, indolyl, 
indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, 
naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, 
carbazolyl, beta-carbolinyl, acridinyl, phenazinyl, phenothiazinyl, 
phenoxazinyl, indolinyl, isoindolinyl or also condensed polycyclic systems 
constituted by heterocyclic monocyclics as defined above, for example, 
such as for example furo-[2,3-b]-pyrrole or thieno-[2,3-b]-furane, 
the term aryl radical designates carbocyclic or heterocyclic unsaturated 
radicals, monocyclic or constituted by condensed rings, it being 
understood that the heterocyclic radicals can contain one or more 
heteroatoms chosen from oxygen, nitrogen or sulphur atoms and that when 
these heterocyclic radicals contain more than one heteroatom, the 
heteroatoms of these heterocyclic radicals can be identical or different: 
thus, these radicals that are designated by the term aryl radical can be 
chosen from the radicals as defined above. 
As examples of such aryl radicals, there can be mentioned the following 
radicals: phenyl, naphthyl, thienyl such as 2-thienyl and 3-thienyl, furyl 
such as 2-furyl, pyridyl such as 3-pyridyl, pyrimidyl, pyrrolyl, 
thiazolyl, isothiazolyl, diazolyl, triazolyl, tetrazolyl, thiadiazolyl, 
thiatriazolyl, oxazolyl, oxadiazolyl, 3- or 4-isoxazolyl; condensed 
heterocyclic groups containing at least one heteroatom chosen from 
sulphur, nitrogen and oxygen, for example benzothienyl such as 
3-benzothienyl, benzofuryl, benzopyrrolyl, benzimidazolyl, benzoxazolyl, 
thionaphthyl, indolyl or purinyl. 
the terms arylalkyl and arylalkenyl designate radicals in which the alkyl, 
alkenyl and aryl radicals respectively can take the values defined above 
for these radicals; as examples of such arylalkyl radicals there can be 
mentioned the following radicals: benzyl, diphenylmethyl, triphenylmethyl, 
naphthylmethyl, indenylmethyl, thienylmethyl such as 2-thienylmethyl, 
furylmethyl such as furfuryl, pyridylmethyl, pyrimidylmethyl or 
pyrrolylmethyl, it being understood that in the non-exhaustive list of 
examples of radicals as mentioned above, the alkyl radical can be 
represented quite as equally by ethyl, propyl or butyl radicals such as, 
for example, in the phenylethyl radical; 
as examples of arylalkenyl radicals, there can be mentioned the examples 
given above of arylalkyl radicals in which the alkyl radical is replaced 
by an alkenyl radical such as for example in phenylvinyl or phenylallyl 
radicals, it being understood that in these radicals the phenyl radical 
can be replaced quite as equally by a naphthyl or pyridyl radical or also 
for example one of the aryl radicals as defined above in the 
non-exhaustive list of aralkyl radicals, 
the term haloalkyl radical preferably designates radicals in which the 
alkyl radical is as defined above and is substituted by one or more 
halogen atoms as defined above such as for example in bromoethyl, 
trifluoromethyl, trifluoroethyl or also pentafluoroethyl, 
the term alkylthio radical preferably designates radicals in which the 
alkyl radical is as defined above such as for example in methylthio or 
ethylthio, 
the term haloalkylthio radical preferably designates radicals in which the 
alkyl radical is as defined above and is substituted by one or more 
halogen atoms as defined above such as for example in bromoethylthio, 
trifluoromethylthio, trifluoroethylthio or also pentafluoroethylthio, 
the term haloalkoxy radical preferably designates radicals in which the 
alkoxy radical is as defined above and is substituted by one or more 
halogen atoms as defined above such as for example in bromoethoxy, 
trifluoromethoxy, trifluoroethoxy or also pentafluoroethoxy, 
the term aryloxy radical preferably designates radicals in which the aryl 
radical is as defined above such as for example in phenoxy, 
the term arylalkoxy radical preferably designates radicals in which the 
aryl radical and the alkoxy radical represent radicals as defined above 
such as for example in benzyloxy, phenylethoxy or phenylisopropoxy, 
the term carbamoyl radical also designates substituted carbamoyl radicals, 
for example a carbamoyl lower N-monoalkyl group, such as 
N-methylcarbamoyl, N-ethylcarbamoyl, a lower N,N-dialkyl carbamoyl group, 
such as N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl; an N-(lower 
hydroxyalkyl) carbamoyl group, such as N-(hydroxymethyl) carbamoyl, 
N-(hydroxyethyl) carbamoyl, a lower carbamoylalkyl group, such as 
carbamoylmethyl, carbamoylethyl, 
the term acyloxy radical designates radicals in which the acyl radicals 
have the meaning indicated above and for example preferably acetoxy or 
propionyloxy radicals, 
the term arylthio radical preferably designates radicals in which the aryl 
radical represents radicals as defined above such as for example in 
phenylthio, 
the term aryl radical substituted by an alkylthio radical represents for 
example the benzylthio radical. 
In the products of formulae (I.sub.B) and (I) and in what follows, the 
alkyl, alkenyl, alkynyl, cycloalkyl and aryl radicals: 
that can be represented by R.sub.2 and R.sub.3, 
that can be contained by the radical --S(O).sub.n R.sub.4 that can be 
represented by R.sub.2 and R.sub.3, or - that can be carried by R.sub.2 
and R.sub.3, can take the values defined above for these radicals which 
can be or cannot be substituted by one or more identical or different 
substituents as defined above for these radicals. R.sub.2 and R.sub.3 can 
thus, for example, represent an alkylthio, arylthio, alkylsulphinyl, 
arylsulphinyl, alkylsulphonyl or arylsulphonyl radical but also a 
cycloalkylthio radical such as for example cyclohexylthio: 
the terms alkylthio, alkylsulphinyl and alkylsulphonyl radical designate 
radicals in which the linear or branched alkyl radical can represent, for 
example, the values indicated above for the alkyl radical; thus these 
radicals preferably represent methylthio, hydroxymethylthio, ethylthio, 
aminoethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, 
ethylsulphonyl radicals but can also represent a propylthio, 
isopropylthio, butylthio, sec-butylthio, tert-butylthio, isopentylthio or 
isohexylthio or those radicals in which the thio radical is oxidized into 
a sulphinyl or sulphonyl radical, 
the term arylthio, arylsulphinyl and arylsulphonyl radical designates 
radicals in which the aryl radical can represent, for example, the values 
indicated above for the aryl radical such as, for example, in phenylthio, 
pyridylthio or pyrimidylthio, imidazolylthio, N-methylimidazolylthio or 
those radicals in which the thio radical is oxidized into a sulphinyl or 
sulphonyl radical such as for example in phenylsulphinyl or 
phenylsulphonyl. 
As examples of alkyl radicals substituted by an aryl radical, there can be 
mentioned, for example, the following radicals: benzyl, diphenylmethyl, 
triphenylmethyl, naphthylmethyl, indenylmethyl, thienylmethyl such as 
2-thienylmethyl, furylmethyl such as furfuryl, pyridylmethyl, 
pyrimidylmethyl or pyrrolylmethyl, it being understood that. in the 
non-exhaustive list of examples of radicals as mentioned above, the alkyl 
radical can be represented quite as equally by ethyl, propyl or butyl 
radicals such as, for example, in the phenethyl radical. 
As examples of alkenyl radicals substituted by an aryl radical, there can 
be mentioned, for example, the examples given above of arylalkyl radicals 
in which the alkyl radical is replaced by an alkenyl radical such as for 
example in phenylvinyl or phenylallyl radicals, it being understood that 
in these radicals the phenyl radical can be replaced quite as equally by a 
naphthyl or pyridyl radical or also for example one of the aryl radicals 
as defined above. 
The carbocyclic or heterocyclic radicals as defined above preferably 
designate phenyl, benzyl, phenethyl, naphthyl, indolyl, indolinyl, 
thienyl, furyl, pyrrolyl, pyridyl, pyrrolidinyl, piperidino, morpholino, 
piperazinyl, these radicals being able to be substituted by one or more 
radicals as defined above such as for example in methylpiperazinyl, 
fluoromethylpiperazinyl, ethylpiperazinyl, propylpiperazinyl, 
phenylpiperazinyl or benzylpiperazinyl. 
The carbamoyl and amino radicals that can be represented by or carried by 
one or more of the optional substituents of the radicals defined in the 
products of formulae (I.sub.B) and (I) and in what follows and that can be 
represented, in particular, by: the radicals 
##STR12## 
designate radicals in which two identical or different radicals are linked 
to the nitrogen atom, chosen from the hydrogen atom to give the amino 
radical; alkyl radicals as defined above to give preferably monoalkyl- or 
dialkylamino radicals in which the linear or branched alkyl radicals 
contain 1 to 6 carbon atoms and in particular methyl, ethyl, isopropyl, 
methoxymethyl, methoxyethyl, ethoxyethyl radicals; carboxyclic or 
heterocyclic radicals that can be represented by R.sub.6, R.sub.7, R.sub.8 
and R.sub.9 can take the values defined above for these radicals and in 
particular phenyl, benzyl, phenethyl, naphthyl, indolyl, indolinyl, 
thienyl, furyl, pyrrolyl, pyridyl, pyrrolidinyl, piperidino, morpholino, 
piperazinyl, these radicals being able to be substituted by one or more 
radicals as defined above such as for example in methylpiperazinyl, 
fluoromethylpiperazinyl, ethylpiperazinyl, propylpiperazinyl, 
phenylpiperazinyl or benzylpiperazinyl. 
The expression amino acid preferably designates a derivative remainder of 
one of the natural amino acids such as glycine, alanine, valine or one of 
the other natural amino acids known to a man skilled in the art. 
When R.sub.6 and R.sub.7 on the one hand or R.sub.8 and R.sub.9 on the 
other hand form, together with the nitrogen atom to which they are linked, 
a heterocycle, it is, for example, one of the following rings: pyrrolyl, 
imidazolyl, pyrazinyl, indolyl, indolinyl, purinyl, pyrrolidinyl, 
piperidyl, piperidino, morpholino, piperazinyl, imidazolidinyl, 
pyrazolidinyl, thiomorpholinyl, azepine; these radicals can be optionally 
substituted by the substituents already mentioned previously and in 
particular by one or more radicals chosen from chlorine and fluorine 
atoms, methyl, ethyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, 
benzoyl, methoxycarbonyl, ethoxycarbonyl, such as for example in 
methylpiperazinyl, ethylpiperazinyl, propylpiperazinyl, phenylpiperazinyl 
or benzylpiperazinyl: in these two latter radicals, the phenyl and benzyl 
radicals can be substituted as indicated previously in the aryl, arylalkyl 
and arylalkenyl radicals, such as for example in chlorophenyl or 
trifluorophenyl. 
The heterocycle that can be formed by R.sub.6 and R.sub.7 on the one hand 
or R.sub.8 and R.sub.9 on the other hand respectively, with the nitrogen 
atom to which they are linked, preferably repcesents a saturated 
heterocycle. 
The acyl radicals that can be represented by R.sub.8 and R.sub.9 are as 
defined previously and can be chosen for example from acetyl, propionyl, 
butyryl, pentanoyl or carbamoyl radicals. 
In the case where one or both of R.sub.2 and R.sub.3, identical or 
different, contain a carbamoyl or amino radical, that is: 
##STR13## 
R.sub.6, R.sub.7, R.sub.8 and R.sub.9, identical or different, can 
represent all four of the aliphatic or cyclized chains or one or both of 
R.sub.6 and R.sub.7 on the one hand and R.sub.8 and R.sub.9 on the other 
hand can form, with the nitrogen atom to which they are linked, a 
heterocycle as defined above. The substituted carbamoyl 
##STR14## 
and substituted amino 
##STR15## 
radicals designate respectively the radicals in which the nitrogen atom 
can be substituted by one or two radicals chosen froin the radicals as 
defined previously: by way of example in a non-exhaustive manner, there 
can be mentioned as a substituted carbamoyl radical the lower N-monoalkyl 
carbamoyl group, for example, N-methylcarbamoyl, N-ethylcarbamoyl; the 
lower N,N-dialkyl carbamoyl group, for example, N,N-dimethylcarbamoyl, 
N,N-diethylcarbamoyl; the N-(lower hydroxyalkyl) carbamoyl group, for 
example, N-(hydroxymethyl) carbamoyl, N-(hydroxyethyl) carbamoyl; the 
lower carbamoylalkyl group, for example carbamoylmethyl, carbamoylethyl; 
phenylcarbamoyl; pyridylcarbamoyl; benzylcarbamoyl; N-methyl 
N-phenylcarbamoyl; pyridylmethylcarbamoyl. 
The substituted amino radical can be for example a monoalkyl- or 
dialkylamino radical in which the alkyl radical is chosen from methyl, 
ethyl or isopropyl radicals. 
Examples of such a substituted amino radical are given in the experimental 
part hereafter. 
When R.sub.8 or R.sub.9 represents an alkoxycarbonyl radical, this radical 
is preferably the tert-butyloxycarbonyl radical or the benzyloxycarbonyl 
radical. 
According to whether m represents the value 0, 1 or 2, the 
--(CH.sub.2).sub.m -- radical represents a single bond, a methylene 
radical or an ethylene radical. 
The radicals Y.sub.1 and Y.sub.2 can represent the values defined above for 
the aryl radicals, monocyclic or constituted by condensed rings, it being 
understood that in the case where B represents a single bond Y.sub.2 can 
also represent a hydrogen atom, a cyano radical or a free, salified or 
esterified carboxy radical. 
The radicals Y.sub.1 or Y.sub.2, identical or different, represent an aryl 
radical optionally substituted by one or more radicals preferably chosen 
from halogen atoms and the following radicals: hydroxyl, nitro, 
tetrazolyl, free, salified or esterified carboxy, alkyl, alkenyl, alkoxy 
and acyl, these radicals being as defined above. 
Among the preferred products of formula (I) are the products in which 
Y.sub.1 is not substituted and Y.sub.2 is substituted by a free or 
esterified carboxy radical or by a tetrazolyl radical. 
The carboxy radical or radicals of the products of formula (I) can be 
salified or esterified 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, ethaholamine, pyridine, picoline, 
dicyclohexylamine, morpholine, benzylamine, procaine, lysine, arginine, 
histidine, N-methylglucamine, 
among the esterification compounds, alkyl radicals in order to form alkoxy 
carbonyl groups such as, for example, methoxycarbonyl, ethoxycarbonyl, 
tert-butoxycarbonyl or benzyloxycarbonyl, these alkyl radicals being able 
to be substituted by radicals chosen for example from halogen atoms, 
hydroxyl, alkoxy, acyl, acyloxy, alkylthio, amino or aryl radicals such 
as, for example, in the chloromethyl, hydroxypropyl, methoxymethyl, 
propionyloxymethyl, methylthiomethyl, dimethylaminoethyl, benzyl or 
phenethyl groups. 
The addition salts with mineral or organic acids of the products of formula 
(I) can be, for example, the salts formed with the following acids: 
hydrochloric, hydrobromic, hydroiodic, nitric, sulphuric, phosphoric, 
propionic, acetic, formic, benzoic, maleic, fumaric, succinic, tartaric, 
citric, oxalic, glyoxylic, aspartic, ascorbic, alkylmonosulphonic such as 
for example methanesulphonic, ethanesulphonic, propanesulphonic, 
alkyldisulphonic such as for example methanedisulphonic, alpha, 
beta-ethanedisulphonic, arylmonosulphonic such as benzenesulphonic and 
aryldisulphonic. 
When R.sub.2 and R.sub.3 both represent a sulphurous group of formula 
--S(O).sub.n R.sub.4, R.sub.2 and R.sub.3 being identical or difference, 
the preferred products of the invention are in particular the products of 
formula (I) in which these sulphurous groups have the same degree of 
oxidation. 
Among the preferred products of the invention there are in particular the 
products of formula (I) in which one of R.sub.2 and R.sub.3 represents a 
sulphurous group optionally oxidized as defined above by --S(O)nR.sub.4 
and the other one of R.sub.2 and R.sub.3 represents an R.sub.4 radical as 
defined above and preferably an alkyl, alkenyl or aryl radical optionally 
substituted by one or more substituents as defined above. 
Among the preferred products of the invention, there are quite particularly 
the products of formula (I) in which R.sub.2 represents a sulphurous 
radical. 
In the case where R.sub.2 or R.sub.3 represents an --S(O).sub.n R.sub.4 
radical and R.sub.4 represents an amino radical, n is preferably equal to 
2. 
R.sub.2B and R.sub.3B can notably represent alkylthio, alkanylthio or 
alkynylthio radicals, optionally substituted by one or more radicals 
chosen from the following radicals: formyl; hydroxyl; alkoxy; acyloxy; 
free, salified or esterified carboxy; amino; substituted amino; carbamoyl; 
substituted carbamoyl; mercapto; alkylthio; acylthio such as acetylthio; 
arylthio such as phenylthio; sulpho, cycloalkyl such as cyclohexyl; 
pyridinyl; pyrimidinyl; phenyl. 
Among the substituents that can be carried by the radicals R.sub.2B and 
R.sub.3B, khe amino and carbamoyl radicals can notably be substituted by 
one or two radicals chosen from alkyl radicals and amino acids chosen from 
the 20 natural amino acids such as notably proline or for example glycine, 
alanine, leucine, isoleucine, valine or phenylalanine. 
The amino and carbamoyl radicals that can be carried by the radicals 
R.sub.2B and R.sub.3B can also constitute derivatives cyclized by the 
formation of a cyclic radical between the nitrogen atom and its 
substituents as indicated above and hereafter. 
R.sub.2B and R.sub.3B can thus notably represent alkylthio radicals, 
substituted by one or more halogen atoms such as chlorine and fluorine, 
such as for example the radicals: --S--CF.sub.3 ; --S--CHF.sub.2 ; 
--S--CH.sub.2 F; --S--CF.sub.2 --CHF.sub.2 ; --S--CF.sub.2 --CHFCl. 
The radicals R.sub.2B and R.sub.3B can thus represent the following 
radicals in which m, m1 and m2, identical or different, represent the 
values 0 to 6, 
##STR16## 
in which X.sub.1 represents H, OH, cyclohexyl, pyridyl, pyrimidyl, phenyl, 
naphthyl, CHO, COOH, NH.sub.2 or 
##STR17## 
The radicals R.sub.2B and R.sub.3B can also represent, particularly, the 
following radicals: 
##STR18## 
in all their isomer and cis-trans isomer forms. 
##STR19## 
X.sub.2 representing an alkyl or aryl radical. 
The radicals R.sub.2B and R.sub.3B can quite particularly represent the 
radical: 
##STR20## 
in which m3 represents the values 0 to 4 and AA represents a natural amino 
acid natural such as notably proline or glycine and the radical: 
##STR21## 
The products of formula (I.sub.B) therefore represent particularly the 
products in which R.sub.2B and R.sub.3B have the meanings indicated above 
and quite particularly the products in which R.sub.2B represents an 
optionally substituted alkylthio radical as defined above or an alkoxy 
radical such as for example mekhoxy and R.sub.3B represents a free, 
salified or esterified, or amidified carboxy radical, such as notably 
--COOH, --COO methyl, --CONH.sub.2 or 
##STR22## 
With these meanings indicated above for R.sub.2B and R.sub.3B in the 
products of formula (I.sub.B) are associated the values indicated above 
for Y.sub.B and notably the biphenyl radical substituted in the ortho 
position by a formyl, free, salified or esterified carboxy, cyano, or 
optionally substituted tetrazolyl radical or the --(CH.sub.2).sub.m1 
--SO.sub.2 --X--R.sub.10 radical as defined above and notably the radicals 
indicated below: 
##STR23## 
Notably a subject of the invention is the products of formula (I.sub.B) as 
defined above and corresponding to the formula (I.sub.C): 
##STR24## 
in which: R.sub.1a represents a linear or branched alkyl or alkenyl 
radical containing at most 4 carbon atoms, 
R.sub.2C and R.sub.3C, identical or different, are chosen from: 
a) the hydrogen atom; the mercapto radical; formyl radicals; free, salified 
or esterified carboxy radicals; halogen atoms; the hydroxyl radical; 
alkoxy radicals containing at most 6 carbon atoms; cyano; nitro; benzoyl; 
acyl radicals; 
b) the radicals R.sub.4C, --S(O).sub.n R.sub.4C such that n represents the 
value 0, 1 or 2, and --OR.sub.4C, in which R.sub.4C represents a linear or 
branched alkyl or alkenyl radical containing at most 6 carbon atoms, a 
cyclohexyl radical, a phenyl, pyridyl, pyrimidinyl or imidazolyl radical, 
all these radicals being optionally substituted by one or more identical 
or different radicals chosen from: 
halogen atoms, 
hydroxyl, mercapto, acylthio, trifluoromethyl, trifluoromethylthio, 
triftuoromethoxy, cyano, azido, nitro, formyl, sulpho radicals, 
phenyl, phenylthio, cycloalkyl, alkyl, alkylthio and alkoxy radicals 
containing at most 6 carbon atoms, these radicals being themselves 
optionally substituted by one or more radicals chosen from halogen atoms, 
the hydroxyl radical, alkoxy radicals containing at most 4 carbon atoms, 
phenyl and free, salified or esterified carboxy radicals, 
free, salified or esterified carboxy radicals, acyl, acyloxy radicals, 
isoxazolyl, pyrrolidinyl, pyrrolidinylcarbonyl pyridyl, pyrimidyl, 
thiazolyl, diazolyl, piperidinyl, tetrazolyl, tetrahydrofurannyl, all 
these radicals being optionally substituted by a methyl, ethyl or nitro 
radical, 
the radicals 
##STR25## 
in which: either R.sub.6a, R.sub.7a, R.sub.8a and R.sub.9a, identical or 
different, are chosen from the hydrogen atom, the hydroxyl radical, amino 
acids, alkyl, alkoxy, acyloxy or acyl radicals, these radicals containing 
at most 6 carbon atoms, free, salified or esterified carboxy radicals, 
phenyl, benzyl, phenethyl, azepine, piperidyl, morpholine, pyrrolidinyl, 
piperazinyl radicals, 
or on the one hand R.sub.6a and R.sub.7a and on the other hand R.sub.8a and 
R.sub.9a form respectively with the nitrogen atom to which they are 
linked, a heterocyclic radical, these identical or different radicals 
being chosen from the following radicals: imidazolyl, pyrrolyl, 
pyrrolinyl, pyrrolidinyl, pyridyl, piperidinyl, pyrimidinyl, pyridazinyl, 
pyrazinyl, piperazinyl, phenylpiperazinyl, piperidyl, oxazolyl, 
morpholinyl and thiomorpholinyl, azepine, indolyl, these radicals being 
optionally substituted by one or more identical or different radicals 
chosen from halogen atoms, hydroxyl radicals, nitro, cyano, acyl, 
trifluoromethyl, alkyl and alkoxy radicals, these radicals containing at 
most 6. carbon atoms, free, salified or esterified carboxy radicals, 
tetrazolyl, phenyl and oxazolyl radicals, Y.sub.C represents the 
--Y.sub.1C --Ba--Y.sub.2C radical in which: 
Y.sub.1C represents a phenyl radical, 
B.sub.a represents a single bond or the --CO--NH-- radical, 
Y.sub.2C is such that: 
either, if B.sub.a represents a single bond or a --CO--NH-- radical, 
Y.sub.2C represents a phenyl radical optionally substituted by one or more 
radicals chosen from free, salified or esterified carboxy radicals, the 
cyano radical, the tetrazolyl radical and the --(CH.sub.2).sub.p 
--SO.sub.2 --XC--R.sub.10C radical in which p represents the values 0 and 
1, X.sub.C represents the radicals --NH--, --NH--CO--, --NH--CO--NH-- or a 
single bond and R.sub.10C represents one of the following radicals: 
methyl, ethyl, propyl, vinyl, allyl, pyridyl, phenyl, benzyl, 
pyridylmethyl, pyridylethyl, pyrimidyl, tetrazolyl, thiazolyl, diazolyl, 
piperidinyl or tetrahydrofurannyl, all these radicals being optionally 
substituted by one cr more substituents chosen from halogen atoms, 
hydroxyl, alkyl and alkoxy radicals containing at most 4 carbon atoms, 
trifluoromethyl and nitro radicals, 
or, if B.sub.a represents a single bond, Y.sub.2C represents a cyano 
radical or free, salified or esterified carboxy radical or a tetrazolyl 
radical, the said products of formula (I.sub.C) 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 the said products of formula (I.sub.C). 
A particular subject of the invention is the products of formula (I.sub.B) 
as defined above, in which: 
R.sub.1 represents an alkyl radical containing at most 4 carbon atoms, 
R.sub.2B and R.sub.3B, identical or different, are chosen from: 
a hydrogen atom, 
a carboxy radical free, salified or esterified by an alkyl radical, 
formyl, acyloxy, sulpho, 
optionally substituted alkyl and alkoxy, 
phenylthio phenylsulphonyl phenylsulphinyl alkylthio, alkylsulphonyl and 
alkylsulphinyl, optionally substituted, as in all those radicals that can 
be represented by R.sub.2B and R.sub.3B, the alkyl and alkoxy radicals 
contain at most 6 carbon atoms, and the alkyl, alkoxy and phenyl radicals 
are optionally substituted by one or more radicals chosen from halogen 
atoms and hydroxyl radicals, trifluoromethyl, acyloxy, free, salified or 
esterified carboxy, phenyl, pyridyl, tetrazolyl, alkyl and alkoxy 
containing at most 4 carbon atoms and themselves optionally substituted by 
an alkoxy radical containing at most 4 carbon atoms, 
and Y.sub.B represents the --Y.sub.1B --B--Y.sub.2B radical in which YIB 
represents a phenyt radical, B represents a single carbon-carbon bond and 
Y.sub.2B represents a carboxy radical, free or esterified by a linear or 
branched alkyl radical containing at most 4 carbon atoms or a phenyl 
radical optionally substituted by a carboxy radical free or esterified by 
a linear or branched alkyl radical containing at most 4 carbon atoms, a 
cyano radical or an optionally salified tetrazolyl radical, the said 
products of formula (I.sub.B) 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 
the said products of formula (I.sub.B). 
A more particular subject of the invention is the products of formula 
(I.sub.B) as defined above and corresponding to the formula (I.sub.a): 
##STR26## 
in which: R.sub.1a represents a linear or branched alkyl or alkenyl 
radical containing at most 4 carbon atoms, 
R.sub.2a and R.sub.3a, identical or different, are chosen from: 
a) the hydrogen atom, the mcrcapto radical, the formyl radical, the free, 
salified or esterified carboxy radical, 
b) the radicals R.sub.4 a and --S(O).sub.n R.sub.4a such that n represents 
the value 0, 1 or 2, 
in which R.sub.4 a represents a linear or branched alkyl or alkenyl radical 
containing at most 4 carbon atoms, a cyclohexyl radical, a phenyl, 
pyridyl, pyrimidinyl or imidazolyl radical, all these radicals being 
optionally substituted by one or more identical or different radicals 
chosen from: 
halogen atoms, 
hydroxyl, mercapto, acylthio, trifluoromethyl, trifluoromethylthio, 
trifluoromethoxy, cyano, azido, or nitro radicals, 
the phenyl radical, 
alkyl and alkoxy radicals containing at most 4 carbon atoms, free, salified 
or esterified carboxy radicals, tetrazolyl, acyl, acyloxy radicals, and 
the radicals 
##STR27## 
in which: either R.sub.6a, R.sub.7a, R.sub.8a and R.sub.9a, identical or 
different, are chosen from the hydrogen atom, the hydroxyl radical, alkyl, 
alkoxy, acyloxy or acyl radicals, these radicals containing at most 6 
carbon atoms, free, salified or esterified carboxy radicals, phenyl, 
benzyl, phenethyl, azepine, piperidyl, morpholine, pyrrolidinyl, or 
piperazinyl radicals, 
or on the one hand R.sub.6a and R.sub.7a and on the other hand R.sub.8a and 
R.sub.9a form respectively, with the nitrogen atom to which they are 
linked, a radical, these identical or different radicals being chosen from 
the following radicals: imidazolyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, 
pyridyl, piperidinyl, pyrimidinyl, pyridazinyl, pyrazinyl, piperazinyl, 
phenylpiperazinyl, piperidyl, oxazolyl, morpholinyl and thiomorpholinyl, 
azepine, indolyl, these radicals being optionally substituted by one or 
more identical or different radicals chosen from halogen atoms, hydroxyl, 
trifluoromethyl, alkyl and alkoxy radicals, these radicals containing at 
most 6 carbon atoms, it being understood that at least one of R.sub.2a or 
R.sub.3a represents the --S(O)nR.sub.4 a radical, Y.sub.a represents the 
--Yla-Ba--Y.sub.2a radical in which: 
Y.sub.1a represents a phenyl radical, 
B.sub.a represents a single bond or the --CO--NH-- radical, 
Y.sub.2a is such that: 
either, if B.sub.a represents a single bond or a --CO--NH-- radical, 
Y.sub.2a represents a phenyl radical substituted in the ortho position by 
a free, salified or esterified carboxy radical or a tetrazolyl radical, 
or, if B.sub.a represents a single bond, Y.sub.2a represents a cyano 
radical or a free, sallfled or esterified carboxy radical or a tetrazolyl 
radical, the said products of formula (I.sub.a) 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 the said products of formula (I.sub.a). 
The --(CH.sub.2).sub.m1 --S(O).sub.m2 --X--R.sub.10 radical as defined 
above can represent for example the radicals in which (CH.sub.2).sub.m1 
represents the values of an alkylene radical such as, for example, 
methylene, ethylene, n-propylene or n-butylene and R.sub.10 can represent 
an alkyl or alkenyl radical chosen from the values defined above or an 
aryl radical also chosen from the values indicated above such as for 
example phenyl, biphenyl, naphthyl, tetrazolyl, the alkyl or alkenyl 
radical that can be represented by the R.sub.10 radical can optionally be 
substituted by an aryl radical chosen from the values defined above, to 
form an aralkyl or aralkenyl radical. 
These alkyl or alkenyl, aryl, aralkyl and arylalkenyl radicals can be 
substituted themselves as indicated above for these radicals. 
The following radicals can be mentioned for example and in a non-exhaustive 
manner: --SO.sub.2 --NH.sub.2, --SO.sub.2 --NH--CH.sub.3, --SO.sub.2 
--NH--CF.sub.3, --SO.sub.2 --NH--C.sub.6 H.sub.5, --SO.sub.2 
--NH--CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --SO.sub.2 --NH.sub.2, 
--CH.sub.2 --SO.sub.2 --NH--C.sub.6 H.sub.5, --SO.sub.2 
--NH--CO--NH--CH.sub.3, --SO.sub.2 --NH--CO--NH--C.sub.6 H.sub.5, 
--SO.sub.2 --H--CO--NH--CF.sub.3, --SO.sub.2 --NH--CO--NH--CH.sub.2 
--C.sub.6 H.sub.5, --SO.sub.2 --NH--CO--NH--D in which D represents a 
phenyl, pyridine or pyrimidine radical optionally substituted by a 
chlorine atom, 
##STR28## 
in which A and B, identical or different, are chosen from the hydrogen 
atom, the phenyl, pyridyl and pyrimidyl radicals, 
##STR29## 
with n=1 or 2 
The aryl radical that is represented by Y.sub.1B can be substituted by one 
or more radicals chosen from the values of R.sub.2B and R.sub.3B and in 
particular by the --NH--(CH.sub.2).sub.m1 --SO.sub.2 --X--R.sub.10 and 
--CO--NH--(CH.sub.2).sub.m1 --SO.sub.2 --X--R.sub.10 radicals in which the 
radical (CH.sub.2).sub.m1 --SO.sub.2 --X--R.sub.10 can take for example 
the values indicated above. 
There can be mentioned for example and in a nonexhaustive manner, the 
radicals: --NH--SO.sub.2 --CH.sub.3, --NH--SO.sub.2 --C.sub.6 H.sub.5, 
--NH--SO.sub.2 --CF.sub.3, --NH--CH.sub.2 --SO.sub.2 --NH--C.sub.6 
H.sub.5, --CO--NH--SO.sub.2 --C.sub.2 H.sub.5, --CO--NH--SO.sub.2 
--CH.sub.3, --CO--NH--SO.sub.2 --CH.sub.2 --C.sub.6 H.sub.5. 
A partlcular subject of the invention is the products of formula (I) as 
defined above in which: 
R.sub.1 represents an alkyl radical containing at most 4 carbon atoms, 
R.sub.2 and R.sub.3, identical or different, are chosen from the following 
radicals: 
carboxy free, salified or esterified by a linear or branched alkyl radical 
containing at most 4 carbon atoms, formyl, acyloxy, 
alkyl containing at most 4 carbon atoms optionally substituted by a 
hydroxyl radical 
phenylthio, phenylsulphonyl, phenylsUlphinyl, 
alkylthio, alkylsulphonyl and alkylsulphinyl, in which the alkyl radical 
contains at most 4 carbon atoms, and Y represents the --Y1-B--Y.sub.2 
radical in which Y.sub.1 represents a phenyl radical, B represents a 
single carbon-carbon bond and Y.sub.2 represents a carboxy radical, free 
or esterified by a linear or branched alkyl radical containing at most 4 
carbon atoms or a phenyl radical optionally substituted by a carboxy 
radical, free or esterified by a linear or branched alkyl radical 
containing at most 4 carbon atoms, the 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 the said products of formula (I). 
A quite particular subject of the invention is the products of formula 
(I.sub.B) corresponding to formula (I) as defined above, in which one of 
R.sub.2 or R.sub.3 represents an alkoxy, alkylthio or arylthio radical, 
these two latter radicals being optionally oxidized in the form of 
sulphoxide or sulphone and these three radicals being optionally 
substituted and the other represents a free, salified or esterified 
carboxy radical, the 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 the said products of formula (I). 
Among the substituents of the alkylthio, alkoxy, arylthio and aryloxy 
radicals, optionally oxidized, there can be mentioned for example the 
following radicals: hydroxyl, alkoxy, free, salified or esterified 
carboxy, acyl, acyloxy, alkyl, phenyl, and halogen atoms. 
Among the products which are a subject of the invention, there can be 
mentioned quite particularly the products of formula (I ) corresponding to 
the following formulae: 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(phenylthio)-1H-imid 
azole-5-carboxylic acid 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(methylthio)-1H-imid 
azole-5-carboxylic acid 
4'-[[2-butyl-4-(ethylthio)-5-(hydroxymethyl)-1H-imidazol-1-yl]-methyl]-(1,1 
'-biphenyl)-2-carboxylic acid 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(ethylsulphonyl)-1H- 
imidazole-5-carboxylic acid 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(ethylsulphinyl)-1H- 
imidazole-5-carboxylic acid 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(ethylthio)-1H-imida 
zole-5-carboxylic acid 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(phenylsulphonyl)-1H 
-imidazole-5-carboxylic acid 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(phenylsulphinyl)-1H 
-imidazole-5-carboxylic acid 
2-butyl-1-[[2'-tetrazolyl-(1,1'-biphenyl)-4-yl]-methyl]-4-(methylthio)-1H-i 
midazole-5-carboxylic acid. 
Also a subject of the invention is a process for the preparation of 
products of formula (I.sub.B) as defined above, characterized in that a 
compound of formula (II): 
##STR30## 
in which R.sub.1 ', R.sub.2B ' and R.sub.3B ' and have the meanings 
indicated above for R.sub.1, R.sub.2B and R.sub.3B respectively and in 
which the optional reactive functions are optionally protected by 
protective groups, is reacted with a compound of formula (III): 
EQU Z--(CH.sub.2).sub.m --Y.sub.B ' (III) 
in which Z represents a halogen atom or a sulphonate and Y.sub.B ' has the 
meaning indicated above for Y.sub.B in which the optional reactive 
functions are optionally protected by protective groups, in order to 
obtain a product of formula (IV): 
##STR31## 
in which R.sub.1 ', R.sub.2B ', R.sub.3B ' and Y.sub.B ' have the meanings 
indicated above, which product of formula (IV) is subjected, if necessary 
and if desired, to one or more of the following reactions, in any order: 
a) an elimination reaction of the protective groups that can be carried by 
the protected reactive functions, 
b) a salification reaction by a mineral or organic acid or by a base in 
order to obtain the corresponding salt, 
c) an esterification reaction of the acid function, 
d) a saponification reaction of the ester function into an acid function, 
e) a conversion reaction of the cyano function into an acid function, 
f) a reduction reaction of the carboxy function into an alcohol function, 
g) a conversion reaction of the alkoxy function into a hydroxyl function, 
h) an oxidation reaction of the alkylthio or arylthio group into a 
corresponding sulphoxide or sulphone, 
i) a conversion reaction of the sulphoxide or sulphone function into a 
corresponding sulphoximine function, 
j) an oxidation reaction of the alcohol function into an aldehyde or acid 
function, 
k) a conversion reaction of the nitrile function into tetrazole, 
l) a resolution reaction of the racemic forms into resolved products, 
m) a conversion reaction of the formyl radical into a carbamoyl radical, 
n) a conversion reaction of the carbamoyl radical into a nitrile radical, 
the said products of formula (I.sub.B) thus obtained being in all the 
possible racemic, enantiomeric and diastereoisomeric lsomer forms. 
In the preferred conditions for implementing the invention, the product of 
formula (IV) can be obtained by the addition of the product of formula 
(III) on to the free amine function of the imidazole of formula (II): in 
the product of formula (III), when Z represents a halogen atom, Z 
preferably represents a bromine atom but can also represent a chlorine or 
iodine atom; in the product of formula (III), Z can also represent a 
sulphonate of formula --O--SO.sub.2 -- in which A preferably represents an 
alkyl radical containing at most 4 carbon atoms such as for example methyl 
or an aryl radical such as for example phenyl optionally substituted for 
example by an alkyl radical containing at most 4 carbon atoms such as for 
example methyl: A can thus represent, for example, the methyl radical or 
also the tolyl radical to give for example a tosylate. 
The reaction of the product of formula (III) with the product of formula 
(II) can be achieved in a solvent such as for example dimethylformamide or 
also tetrahydrofuran, dimethoxyethane or dimethylsulphoxide under reflux 
of the solvent or at ambient temperature, preferably under agitation; the 
reaction is preferably carried out in the presence of a base such as for 
example sodium or potassium hydride or also sodium or potassium carbonate, 
sodium or potassium methylate or ethylate or tert-butylate. 
According to the values of R.sub.1 ', R.sub.2B ', R.sub.3B ' and Y.sub.B ', 
the products of formula (IV) constitute or do not constitute the products 
of formula (I.sub.B). 
The various reactive functions that can be carried by some of the compounds 
of the reactions defined above can, if necessary, be protected: they can 
be, for example, hydroxyl, acyl, free carboxy or also amino and 
monoalkylamino radicals which can be protected by the appropriate 
protective groups. 
The following non-exhaustive list of examples of protection of reactive 
functions can be mentioned: 
the hydroxyl groups can be protected for example by alkyl radicals such as 
tert-butyl, trimethylsilyl, tert-butyldimethylsilyl, methoxymethyl, 
tetrahydropyrannyl, benzyl or acetyl, 
the amino groups can be protected for example by acetyl, trityl, benzyl, 
tert-butoxycarbonyl, phthalimido radicals or other radicals known in the 
chemistry of the peptides, 
the acyl groups such as the formyl group can be protected for example in 
the form of cyclic or non-cyclic ketals such as dimethyl- or diethylketal 
or ethylene dioxyketal, 
the acid functions of the products described above can be, if desired, 
amidified by a primary or secondary amine for example in methylene 
chloride in the presence, for example, of 1-ethyl-3-(dimethylaminopropyl) 
carbodiimide hydrochloride at ambient temperature: 
the acid functions can be protected for example in the form of esters 
formed with easily cleavable esters such as benzyl or terbutyl esters or 
esters known in the chemistry of the peptides. 
The reactions to which the products of formula (IV) as defined above can be 
subjected, if desired or if necessary, can be carried out, for example, as 
indicated hereafter. 
a) The elimination of the protective groups such as for example those 
indicated above can be carried out in the usual conditions known to a man 
skilled in the art, notably by an acid hydrolysis carried out with an acid 
such as hydrochloric acid, benzene sulphonic or paratoluene sulphonic 
acid, formic or trifluoroacetic acid or also by a catalytic hydrogenation. 
The phthalimido group can be eliminated by hydrazine. 
A list of the various protective group which can be used will be found for 
example in the Patent BF 2,499,995. 
b) The products described above can, if desired, be subjected to 
salification reactions for example by a mineral or organic acid according 
to the usual methods known to a man skilled in the art. 
c) The products described above can, if desired, be subjected, on the 
optional carboxy functions, to salification reactions by a mineral or 
organic base or to esterification reactions: these esterification and 
salification reactions can be carried out according to the usual methods 
known to a man skilled in the art. 
d) The optional conversions of the ester functions into acid functions of 
the above-described products can be, if desired, carried out in the usual 
conditions known to a man skilled in the art, notably by alkaline or acid 
hydrolysis for example by soda or potash in an alcohol medium such as, for 
example, in methanol or also by hydrochloric or sulphuric acid. 
e) The optional cyano functions of the products described above can be, if 
desired, converted into an acid function in the usual conditions known to 
a man skilled in the art, for example by a double hydrolysis carried out 
in an acid medium such as for example in a sulphuric acid, glacial acetic 
acid and water mixture, these three compounds preferably being in equal 
proportions, or also in a mixture of soda, ethanol and water under reflux. 
f) The optional free or esterified carboxy functions of the above-described 
products can be, if desired, reduced to an alcohol function by methods 
known to a man skilled in the art: the optional esterified carboxy 
functions can be, if desired, reduced into an alcohol function by methods 
known to a man skilled in the art and notably by lithium-aluminium hydride 
in a solvent such as for example tetrahydrofuran or also dioxan or ethyl 
ether. 
The optional free carboxy functions of the above-described products can be, 
if desired, reduced to alcohol functions notably by boron hydride. 
g) The optional alkoxy functions, such as notably methoxy, of the 
above-described products can be, if desired, converted into a hydroxyl 
function in the usual conditions known to a man skilled in the art, for 
example by boron tribromide in a solvent such as for example methylene 
chloride, by pyridine hydrobromide or hydrochloride or also by hydrobromic 
or hydrochloric acid in water or acetic acid under reflux. 
h) The optional alkylthio or arylthio groups of the products described 
above can be, if desired, converted into corresponding sulphoxide or 
sulphone functions in the usual conditions known to a man skilled in the 
art, such as for example by peracids such as for example peracetic acid or 
metachloroperbenzoic acid or also by ozone, oxone, sodium periodate in a 
solvent such as for example methylene chloride or dioxane at ambient 
temperature. 
The obtaining of the sulphoxide function can be promoted by an equimolar 
mixture of the product containing an alkylthio or arylthio group and the 
reagent such as notably a peracid. 
The obtaining of the sulphone function can be promoted by a mixture of the 
product containing an alkylthio or arylthio group with an excess of the 
reagent such as notably a peracid. 
i) The optional sulphide, sulphoxide or sulphone functions of the 
above-described products can be, if desired, converted into the 
corresponding sulphoxime functions in order to prepare the products in 
which R.sub.2 or R.sub.3 represents a radical: 
##STR32## 
in the usual conditions known to a man skilled in the art: non-exhaustive 
examples of the preparation of products containing a sulphoximine function 
are described below. 
Thus for example for the preparation of compounds such as N-(arylsulphonyl) 
sulphoximines and for example in the case where the aryl group that is 
represented by X' is a toluene radical, the sulphoximine can be obtained 
by the action of paratoluenesulphonlc nitride on the corresponding 
sulphoxide, that being --S(O)CH.sub.3, preferably in the presence of 
copper as indicated for example in the following reference: J. A. C. S., 
95, pp. 4287 (1973) JOHNSON C.R. & coll. 
Another method also used consists of treating N-tosylsulphilimine, itself 
prepared from the sulphide by the action, for example, of chloramine "T", 
with an oxidizing agent such as for example sodium hypochlorite in phase 
transfer conditions as indicated, for example, in the following reference: 
J. Org. Chem., 49, pp. 2282 (1984) AKUTAGAWA K. & coll. 
j) The optional alcohol function of the products described above can be, if 
desired, converted into an aldehyde or acid function by oxidation in the 
usual conditions known to a man skilled in the art, such as for example by 
the action of manganese oxide to obtain the aldehydes or of Jones reagent 
to obhain the acids. 
k) The optional nitrile functions of the products described above can be, 
if desired, converted into tetrazole in the usual conditions known to a 
man skilled in the art, such as for example by the cycloaddition of a 
metallic azide such as for example a trialkyltin azide on to the nitrile 
function as indicated in the method described in the article referenced as 
follows: J. Organometallic Chemistry, 33, 337 (1971) KOZIMA S. & coll. 
l) The optional optically active forms of the products of formula (I.sub.B) 
can be prepared by resolution of the racemics according to the usual 
methods known to a man skilled in the art. 
The conversion reactions of the formyl radical into a carbamoyl radical and 
of the carbamoyl radical into a nitrile radical are carried out according 
to the usual conditions known to a man skilled in the art. These reactions 
as well as the conversion of the nitrile radical into tetrazole are 
carried out preferably when these substituents are carried in alpha 
position of the biphenyl substituent that can be represented by --Y.sub.B. 
The compounds of formula (I.sub.B) as defined above as well as their 
addition salts with acids have useful pharmacological properties. 
The products are endowed with antagonistic properties for the angiotensin 
II receptor and are thus notably inhibitors of the effects of angiotensin 
II, in particular of the vasoconstricting effect and also of the trophic 
effect at the level of the myocytes. 
These properties justify their use in therapeutics and also a subject of 
the invention is, as medicaments, the products as defined by formula 
(I.sub.B) above, the said products of formula (I.sub.B) being in all the 
possible racemic or optically active isomer forms, as well as the addition 
salts with pharmaceutically acceptable mineral or organic acids of the 
said products of formula (I.sub.B). 
A particular subject of the invention is, as medicaments, the products of 
formulae (I), (I.sub.C) and (I.sub.a) as defined above and the products of 
formula (I.sub.B) as defined above in which: 
R.sub.1 represents an alkyl radical containing at most 4 carbon atoms, 
R.sub.2 and R.sub.3, identical or different, are chosen from the following 
radicals: 
carboxy free, salified or esterified by a linear or branched alkyl radical 
containing at most 4 carbon atoms, formyl, acyloxy, alkyl containing at 
most 4 carbon atoms optionally substituted by a hydroxyl radical, 
phenylthio, phenylsulphonyl, phenylsulphinyl, alkylthio, alkylsulphonyl 
and alkylsulphinyl, in which the alkyl radical contains at most 4 carbon 
atoms, and Y represents the --Y.sub.1 --B--Y.sub.2 radical in which 
Y.sub.1 represents a phenyl radical, B represents a single carbon-carbon 
bond and Y.sub.2 represents a carboxy radical, free or esterified by a 
linear or branched alkyl radical containing at most 4 carbon atoms or a 
phenyl radical optionally substituted by a carboxy radical free or 
esterified by a linear or branched alkyl radical containing at most 4 
carbon atoms, the said products of formula (I.sub.B) 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 the said products of formula (I.sub.B). 
A quite particular subject of the invention is, as medicaments, the 
products of formula (I.sub.B) corresponding to formula (I.sub.a) as 
defined above, in which one of R.sub.2a or R.sub.3a represents an 
alkylthio or arylthio radical optionally oxidized in the form of 
sulphoxide or sulphone and optionally substituted as indicated above, and 
the other represents a free, salified or esterified carboxy radical, the 
said products of formula (I.sub.a) being in all the possible racemic, 
enantiomeric and diastereoisomeric isomer forms, as well as the addition 
salts with pharmaceutically acceptable mineral and organic acids or 
mineral and organic bases of the said products of formula (I.sub.a). 
A more particular subject of the invention is, as medicaments, the products 
described hereafter in the examples and notably the following products of 
formula (I): 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(phenylthio)-1H-imid 
azole-5-carboxylic acid 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(methylthio)-1H-imid 
azole-5-carboxylic acid 
4'-[[2-butyl-4-(ethylthio)-5-(hydroxymethyl)-1H-imidazol-1-yl]-methyl]-(1,1 
'-biphenyl)-2-carboxylic acid 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-sulphonyl)-1H-imidaz 
ole-5-carboxylic acid 
2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-ethylsulphonyl)-1H-i 
midazole-5-carboxylic acid 
2-butyl-1-[[2 
-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(ethylthio)-1H-imidazole-5-carbox 
ylic acid 
2-butyl-1-[[2 
-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(phenylsulphonyl)-1H-imidazole-5- 
carboxylic acid 
2-butyl-1-[[2 
-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(phenylsulphinyl)-1H-imidazole-5- 
carboxylic acid 
2-butyl-1-[[2 
-tetrazolyl-(1,1'-biphenyl)-4-yl]-methyl]-4-(methylthio)-1H-imidazole-5-ca 
rboxylic acid 
as well as their addition salts with pharmaceutically acceptable mineral or 
organic acids. 
The medicaments, which are a subject of the invention, can be used in the 
treatment of arterial hypertension, cardiac insufficiencies, renal 
insufficiencies and in the prevention of post-angioplasic reccurences of 
stenosis. 
They can also be used in the treatment of certain gastro-intestinal and 
gynaecological disorders, and in particular for a relaxing effect at the 
level of the uterus. 
The invention extends to pharmaceutical compositions containing as active 
ingredient at least one of the medicaments as defined above. 
These pharmaceutical compositions can be administered by buccal or rectal 
route, by parenteral route or by local route as a topical application on 
the skin and the mucous membranes. 
These compositions can be solid or liquid and can be presented in all the 
pharmaceutical forms currently used in human medicine such as, for 
example, plain or sugar-coated tablets, capsules, granules, suppositories, 
injectable preparations, ointments, creams, gels and aerosol preparations; 
they are prepared according to the usual methods. The active ingredient 
can be incorporated with the excipients usually employed in these 
pharmaceutical compositions, such as talc, gum arabic, lactose, starch, 
magnesium stearate, cocoa butter, aqueous or non-aqueous vehicles, fatty 
substances of animal or vegetable origin, paraffin derivatives, glycols, 
various wetting, dispersing or emulsifying agents and preservatives. 
The usual dose, variable according to the product used, the patient treated 
and the affection in question, can be, for example, 1 to 100 mg per day 
for an adult, by oral route. 
Some starting products of formula (II) are known and can be prepared for 
example as indicated in the European Patent EP 168,950. 
The starting products of formula (II) can in particular be prepared 
according to a new process and the present invention thus also relates to 
this new preparation process for the starting products of formula (II) as 
defined above, characterized in that a compound of formula (II.sub.a): 
##STR33## 
in which R.sub.2B ' has the meaning indicated above for R.sub.2B in which 
the optional reactive functions are optionally protected by protective 
groups, is subjected to the action of a reducing agent, in order to obtain 
the corresponding amine of formula (II.sub.b): 
##STR34## 
in which R.sub.2B ' has the meaning indicated previously, which is 
subjected to the action of a compound of formula (II.sub.c): 
##STR35## 
in which R.sub.1 ' has the meaning indicated above for R.sub.1 in which 
the optional reactive functions are optionally protected by protective 
groups and W represents a hydroxyl radical or a halogen atom, in order to 
obtain a product of formula (II.sub.d): 
##STR36## 
in which R.sub.1 ' and R.sub.2B ' have the meanings indicated previously, 
which is reacted with a compound of formula (II.sub.e): 
EQU R.sub.3B '--SH (II.sub.e) 
in which R.sub.3B ' has the meaning indicated above for R.sub.3B in which 
the optional reactive functions are optionally protected by protective 
groups, in order to obtain a product of formula (II.sub.f): 
##STR37## 
in which R.sub.1 ', R.sub.2B ' and R.sub.3B ' have the meanings indicated 
previously, which is subjected to a cyclization reaction in order to 
obtain a product of formula (II), which product of formula (II) is 
subjected, if desired and if necessary, to one or more of the following 
reactions, in any order: 
a) an elimination reaction of the protective groups that can be carried by 
the protected reactive functions, 
b) a salification reaction by a mineral or organic acid or by a base in 
order to obtain the corresponding salt, 
c) an esterification reaction of the acid function, 
d) a saponification reaction of the ester function into an acid function, 
e) a conversion reaction of the cyano function into an acid function, 
f) a reduction reaction of the carboxy function into an alcohol function, 
g) a conversion reaction of the alkoxy function into a hydroxyl function, 
h) an oxidation reaction of the alkylthio or arylthio group into a 
corresponding sulphoxide or sulphone, 
i) a conversion reaction of the sulphoxide or sulphone function into a 
corresponding sulphoximine function, 
j) an oxidation reaction of the alcohol function into an aldehyde or acid 
function, 
k) a conversion reaction of the nitrile function into tetrazole, 
l) a resolution reaction of the racemic forms into resolved products, 
m) a conversion reactLion of the formyl radical into a carbamoyl radical, 
n) a conversion reaction of the carbamoyl radical into a nitrile radical, 
the said products of formula (II) thus obtained being in all the possible 
racemic, enantiomeric and diastereoisomeric isomer forms. 
In the preferred conditions for implementing the invention, the above 
process is carried out in the following manner: 
the reduction of the oxime of formula (II.sub.a) to give the compound of 
formula (II.sub.b) can be carried out according to the usual methods known 
to a man skilled in the art such as for example by an aluminium amalgam 
prepared in the usual conditions such as for example by the action of 
mercuric chloride on aluminium: the reaction is carried out in a solvent 
such as for example tetrahydrofuran or toluene, preferably at a 
temperature of approximately 50.degree. C.; 
the addition of the product of formula (IIc), in which W preferably 
represents a chlorine atom but can also represent a bromine atom, on to 
the amine of formula (IIb) thus obtained can be carried out according to 
methods known to a man skilled in the art such as for example in the 
presence of a base such as for example pyridine or also triethylamine; the 
reaction is preferably carried out at a temperature of approximately 
0.degree. C., 
the addition of the sulphurous derivative of formula (II.sub.e) on to the 
amide of formula (II.sub.d) thus obtained in order to obtain the product 
of formula (II.sub.f) is carried out, for example, by solubilizing the 
amide of formula (II.sub.d) in a solvent such as for example an alcohol 
such as ethanol or methanol, then successive additions of a base such as 
for example triethylamine and the compound of formula (II.sub.e) 
preferably under agitation and at ambient temperature, 
the cyclization reaction of the compound of formula (II.sub.f) thus 
obtained into a product of formula (II) can be carried out in a solvent 
such as, for example, dichloromethane, dichloroethane or also chloroform: 
the reaction can be carried out for example in the presence of phosphorous 
pentachloride (PCl.sub.5) dissolved before.hand in dichoromethane at a 
temperature of approximately -78.degree. C. in the presence of a base such 
as for example pyridine or dimethylaminopyridine: the reaction can be 
carried out under agitation at ambient temperature. 
The product of formula (II) thus obtained can be subjected to one or more 
of the above-indicated reactions, these reactions being able to be carried 
out in the same conditions as those defined above for the products of 
formula (IV). 
The compound of formula (II.sub.a) can be, for example, 
ethylisonitrosocyanoacetate which can be found, for example, in the form 
of product commercially-available from LANCASTER under the reference 8930. 
The starting compounds of formula (III) may be commercially available or 
can be prepared according to the usual methods known to a man of the art. 
A preparation process for certain products of formula (III) as defined 
above, can consist of subjecting methyl iodobenzoate, for example, in the 
form of a product commercially available from JANSSEN, to the action of 
iodotoluene, for example, in the form of a product commercially available 
from FLUKA, the reaction being carried out for example in the presence of 
powdered copper at a temperature of approximately 100.degree. C. to 
300.degree. C., in order to obtain a product: 
##STR38## 
the esterified carboxy radical of which can, if desired, be released from 
the alkyl radical by standard methods known to a man skilled in the art or 
indicated above, for example acid or alkaline hydrolysis, which can be 
subjected to a bromination reaction on the methyl radical by standard 
methods known to a man skilled in the art, for example by the action of 
n-bromosuccinimide in carbon tetrachloride. 
Examples of the preparation of compounds of formula (III) are described in 
the literature and examples are given notably in the U.S. Pat. No. 
4,880,804 or for example in the reference Chemistry and Industry 7 
September 1987 HOWARD and COLQUHOUN pp. 612-617. 
Finally a subject of the present invention is as new industrial products 
and notably as intermediate products necessary for the preparation of the 
products of formula (I), the compounds of formula (II) in which R.sub.1 ' 
does not represent the methyl radical.