MXPA97002504A - Derivatives of 1,2-difenil pirrol, its preparation and its therapeutic uses - Google Patents

Abstract

The compounds of the formula (I) and the formula (II) :( See Formula) [wherein R is hydrogen, halogen or alkyl, R1 is alkyl, amino or substituted amino, R2 is optionally substituted phenyl, R3 is hydrogen, halogen or optionally substituted alkyl, R 4 is hydrogen, optionally substituted alkyl, cycloalkyl, aryl or aralkyl], have valuable analgesic, anti-inflammatory, anti-pyretic and anti-allergic activities, and have the ability to inhibit the production of leukotrienes and to inhibit bone resorption. They are relatively free of side effects that are usually the result of the administration of compounds that have these kinds of activity

Description

DERIVATIVES OF 1, 2-DIFENILPIRROL, ITS PREPARATION AND ITS THERAPEUTIC USES BACKGROUND OF THE INVENTION The present invention relates to a series of new derivatives of 1,2-d? Phen? lpirrol which have valuable analgesic, anti-inflarnatopa, antipyretic and antialergic activities and which have the ability to inhibit the production of leukotpenes and to inhibit bone reabsorption; and that they are relatively free of collateral effects that are generally the result of the administration of compounds that have these kinds of activities. The invention also provides methods and compositions utilizing these novel compounds, as well as methods for their preparation. Non-eroidal anti-mflamatory drugs (FOINE) have been used extensively for clinical purposes in the treatment of inflammatory diseases, such as pyrexia, pain and edema. However, the adverse effects of these drugs, such as gastrointestinal alterations and renal alterations, present problems for any patient who turns the drug over a prolonged period of time, as well as for elderly patients. There are two main metabolic pathways that interact with arachidonic acids. These are: the trajectory that leads to the production of prostaglandins (PG) and the trajectory that leads to the production of le cotpenos (LD) It is believed that FftINE act to inhibit the action of PG-cyclooxygenase (COX) which is a crucial step in the production of PG from arachidonic acid. It has been discovered that two isozymes, called COX-1 and COX-2, are present in the COX. It has been discovered that COX-1 is normally present in the stomach, intestines, kidneys and other tissues, and it serves to produce PG, which functions physiologically, while COX-2 is induced by cytokines and endotoxins. inflammatory processes, such as IL-1, TNF_ and the like, and is specifically expressed in an inflammatory site to produce PG, which acts as a mediator of inflammatory reactions. With the discovery of these two isozrins, it was believed that the agents to ti-inflarnatopos that specifically inhibit COX-2 without inhibiting COX-I would be free from the side effects eß caused by conventional drugs, and that it could be? new type of anti-inflammatory agent. On the other hand, it is known that IL-1, TNF ", IL-6 and TL-8, the inflammatory cytokines, are produced in rhonocytes, rnacrophages and smovial cells as a result of various inflammatory stimulants and by the influence of various biological procedures, such as the production of PG, the expression of cell adhesion molecules, the production of conagenasa-prstease, the activation of osteoclasts, pyrexia, the production of acute phase proteins and the chirurgical activity of leukocytes. It is said that these cytokines are associated with the advancement of various diseases, such as chronic inflammatory diseases, which include chronic rheumatic arthritis. Thus, drugs that inhibit the actions of the cytokine are useful as a new type of anti-inflammatory agent. Recently it has been considered that prostaglandins, synthesized by osteoblast cells through induction by COX-2, activate osteoclast cells and, as such. way, they induce bone resorption. As a consequence, COX-2 inhibitors are expected to be useful for the treatment and prophylaxis of diseases that are accompanied by, or result from, bone resorption or destruction, such as osteoporosis, rheumatoid arthritis and osteoart pt is . The leucotpenes, on the other hand, have shown that they are strongly involved in inflammation, allergy and the formation of gastric ulcer. The inhibitors of the synthesis of LT and PG, therefore, are believed to be more convenient drugs for the treatment and prophylaxis of inflammatory diseases. Among the known 1,2-d? Feml? Irrol derivatives, which have analgesic and antiphlogistic actions, is a compound represented by the following formula, which is described in German Patent No. 193890 This compound is referred to below as "compound A". However, this compound is not active enough and thus, effective compounds would be desirable. A number of new compounds have been discovered which have the required activity, and which do not appear to exhibit the side effects of the known compounds. In addition, the compounds also surprisingly have the ability to inhibit the production of leucotropins and to inhibit bone resorption, and for both reasons they are of therapeutic and prophylactic value.

BRIEF DESCRIPTION OF THE INVENTION Therefore, it is an object of the present invention to provide a series of novel compounds which are useful for the treatment, prophylaxis and relief of pain and inflammation, and which inhibit the production of leukotriene and inhibit bone reabsorption. Additionally, it is a more specific objective of the present invention provide said compounds which, in general, are free from, or are relatively susceptible to, side effects such as gastrointestinal discomfort. Other objectives and advantages will be evident as the description proceeds. The compounds of the present invention are those compounds of the formula (I) and (II): wherein: R represents a hydrogen atom,? n halogen atom or an alkyl group having from 1 to 6 carbon atoms; Ri represents an alkyl group having one to six carbon atoms, an amino group or a group of the formula -NHR *, wherein R "represents an alkanoyl group having 25 carbon atoms, an alkoxycarbonyl group which has 1 carbon atoms in the alkoxy part, an aralkyloxycarbonyl group, wherein the aralkyl part is as further defined, an alkanoyloxymethyl group having from 1 to 6 carbon atoms in the alkanoyl part; an alkanoyloxy group having from 1 to 6 carbon atoms in the alkanoyl part; an alkoxycarbonyloxy methyl group having from 1 to 6 carbon atoms in the alkoxy part or a group (2-oxo-l, 3-d-oxolen-4-ylmethyl), which is unsubstituted or substituted in the position 5-d? Oxolene with an alkyl group having from 1 to 6 carbon atoms, or with an aryl group, as defined below: R2 represents a phenyl group which is unsubstituted or which is substituted by at least a substituent selected from the group consisting of the alpha substituents and beta substituents defined below: R3 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms, and which is not substituted or substituted with at least one substituent selected from the group consisting of alpha substituents, defined below, R * represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, and which is not replaced or that is replaced with at least one substitute? yente sel The group consists of the alpha substituents defined below, a cycloalkyl group having from 3 to 8 carbon atoms, an aplo group which is as defined below, or an aralkyl group which is as defined below.; said groups have 6 to 14 carbon atoms of ring in a carbocyclic ring, and they are unsubstituted or substituted with at least one of their substituents selected from the group consisting of alpha substituents and beta substituents defined below; said aralkyl groups and the aralkyl portions of said aralkyloxycarbonyl groups are alkyl groups having from 1 to 6 carbon atoms, which are substituted with at least one aplo group as defined above; the alpha substituents are selected from the group consisting of hydroxy groups, halogen atoms, alkoxy groups (having 6 carbon atoms and alkylthio groups having 1 to 6 carbon atoms), the beta substituents are selected from the group consists of alkyl groups having from 1 to 6 carbon atoines and which are unsubstituted or which are substituted by at least one substituent selected from the group consisting of the substituents alpha, defined above; alkanoyloxy groups having the 6 carbon atoms, rnercapto groups, alanoylthio groups having from 1 to 6 carbon atoms, alkylsulfiyl groups having 6 carbon atoms, cycloalkyloxy groups having from 1 to 8 carbon atoms , halogenoalkoxy groups having from 1 to 6 carbon atoms, and l-lelenedioxy groups having from the carbon atoms; and their pharmaceutically acceptable salts. The invention also provides a method for treating or alleviating pain or inflammation in a mammal, which can be human, which suffers from them, by administering an anti-mflarnatory and analgesic compound selected from the group consisting of compounds of the formula (I) and (II) and their pharmaceutical salts. typically acceptable. The invention also provides a method for inhibiting bone resorption in a mammal, which can be human, suffering from it by administering an active compound selected from the group consisting of the compounds of formula (I) and formula (II) , and its pharmaceutically acceptable salts. The invention also provides a method for inhibiting the production of leucotpene in a mammal, which can be human, by administering an active compound selected from the group consisting of compounds of formula (I) and (II) and their pharmaceutically acceptable salts.

DETAILED DESCRIPTION OF THE INVENTION In the compounds of the present invention, in which R represents a halogen atom, this may be a fluorine, chlorine, bromine or iodine atom, whereby the fluorine and chlorine atoms are preferred, and the fluorine volume is the most preferred. When R represents an alkyl group having from 1 to 6 carbon atoms, this may be a straight or branched chain group, and examples include the methyl, ethyl groups, propyl, isopropyl, butyl, isobutyl, secondary butyl, tertiary butyl, pentyl, isopentyl, neopentyl, 2-methy butyl, 1-et? iprop ?, 4-met? lpent? 3-methylpentyl, 2-methyl pentyl, 1-methylpentyl, 3,3-d? methytibyl, 2,2-di ethylbutyl, 1,1-di ethylbutyium, , 2-d? Met ibut? Lo, 1,3-dirnetilb? Tiio, 2,3-d? Met? Lbut? it, 2-butyl, hexyl and isohexyl. Preferred among them are those alkyl groups having from 1 to 4 carbon atoms, preferably the methyl, ethyl, propyl, isopropyl, butyl and isobutyl groups and, most preferably, the methyl group. Of the above groups and atoms, it is preferred that R represents a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group, of which the preferred one is the hydrogen atom. When R represents an alkyl group having 1 carbon atoms, this may be a straight or branched chain group, and examples include the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, tertiary butyl groups. , pentyl, isopentyl, neopentyl, 2-methyl-butyl, 1-etylpropyl, 4-rnet? I penti it, 3-met? lpent? it, 2-rnetilpentyl, 1-met? lpent? lo, 3,3-dimime + il butyl, 2,2-dirnetilbutyl, 1, 1-d? met? lbut? io, 1,2-d? met? lbut ? io, 1,3-dimetiibutilo, 2,3-d? met? lbut? io, 2-et? lbutyium, hexyl and isohexyl. Of these, those alkyl groups having from 1 to 4 carbon atoms, preferably the methyl, ethyl, propyl, isopropyl, butyl and isobutyl groups and, rnuy, are preferred. preferably, the methyl group. When R represents a group of the formula -NHR », and where R« represents an alkanoyl group, this is an alkanoi lamino group, which may be a straight or branched chain group, having from 1 to 25 carbon atoms better still, from 1 to 20 carbon atoms, still better still, from 1 to 6 carbon atoms and, preferably, from 1 to 4 carbon atoms. Examples of such alkanoylamino groups include the formylamino, acetylamino, propionylamino, butylamino, isobutylamino, pivaloylanno, valerylanno, isovalerylamino, hexanoyla, heptanoylammo, octanoylamino, nonanoylammo, decanoylamino, undecanoylamino, lauroylanno, tndecanoylamino, mipstoylammo, palrnitoylamino, stearoylamino , icosanolarnino, docosanoila mo and pentacosanoilar ino, of which the alkanoyla mo groups having 1 to 12 carbon atoms are preferred, and the most preferred is the acetyl cinnamino group. When it represents a group of the formula -NHR », and where R» represents an alkoxycarbonyl group having from 1 to 6 carbon atoms in the alkoxy part, this is an alkoxycarbonylamino group. The alkoxy part can be a straight or branched chain group, having 1 to 6 carbon atoms. Examples of such alkoxycarbonylamino groups include the nitrocarbonylamino group, ethoxy carbomamino, propoxycarbonylamino, and sopropoxycarbomlamino, butoxycarbonylamino, isobutoxycarbonylamino, secbutoxycarbomlammo, Terb? toxicarbom lamino, penti loxicarbomlarnmo, isopentiioxi-carbonylamino, neopentiloxicarboni lamino, 2-meth? lbutox? carbo-or lamino, 1 -et yl propox ica rbon i licked not -metí ipent i lox ica rbo-mlammo, 3-n d ? lpentiloxicarbonilarnino, 2-n d? lpent? lox? -carbonilammo, 1-n d lpent? lox? coal? lam? no, 3, 3-d? n d? l-butoxicarbo ylamino, 2, 2-d? met? ib? tox ?carbon? Lamino, 1,1-dimethylbutoxycarbonylammo, 1, -d? rnet? lbutox? carbonilarnmo, 1,3-d? Rnet? Ibutox? Carbon? Lar? No, 2,3-d? Met? Lbutox? Carbon? L-arnino, 2-e? Lbutox? Carbon? Lam? no, hexyloxy carboni lamino and isoxyhexyloxylamino. Of these groups it is preferred those alcoxicarbonilami or having 1 to 4 carbon atoms in the alkoxy part, preferably the ica rnetox groups rbon yl Arni, etoxicarbonila mo, propoxycarbonylamino, isopropoxicarbo-mlamino, lamino butoxicarbom, isobutoxy carbonilarnino, sec- butoxycarbilanilan and tert.-butoxycarbonylamino; and the most preferred, the groups rneto icarbonilarnmo or ethoxycarbomlammo. When R1 represents a group of the formula -NHR "and where R" represents an aralkyloxycarbomyl group, the part of that group is a carbocyclic aromatic group, preferably having 14 ring carbon atoms, better still, from 6 to 10 ring carbon atoms, and may be substituted or unsubstituted. If substituted, the substituents are preferably selected from the group consisting of the alpha substituents and the beta substituents, defined and exemplified above; and there is no particular restriction on the number of such substituents, except for that can be imposed by the number of substitutable positions (5 in the case of femlo groups and 7 in the case of naphthyl groups) and, possibly, by steric constraints. The examples of such anole groups are as given below, but unsubstituted groups, particularly the phenyl group, are preferred. The aralkyl group may contain from 1 to 3 of said aryl groups, preferably an aryl. The alkyl part of the aralkyl group can be any of the alkyl groups exemplified above, relative to R; but preferably it is one of said groups having from 1 to 4 carbon atoms, preferably the methyl, ethyl or propyl group and, most preferably, the methyl group. The most preferred aralkyl group is the benzyl group. Specific examples of the aralkyloxycarbonylamine groups that may be represented by R are the benzyloxycarbomamino, 1-naft? loxicarbonilamino, 2-naftiloxicarbonilamino, o-, m- and p-clorobenciloxicarbomlarnino and o-, m- and p-methy lamino lbenciloxicarboni, of which the most preferred is the carbonyl-amino group Loxi BENCI. When R represents a group of the formula -NHR »and where R * is an alkanoyloxy ethyl group, it has from 1 to 6 carbon atoms in the alkanoyl part. Examples of the alkanoyl groups are those alkanoyl groups having from 1 to 6 carbon atoms, and are included in the alkanoylamino groups exemplified further back. The examples specific groups to canoiloximetilammo include forrniloxirnetiiami and not hexanoiloxirnetilamino groups, aceto irnetilamino, propionyloxy -metilarnino, butiriloximetilammo, loximetilamino ísobutip, pivaloiloximetilarnmo, valeploximetilamino, ísovaleriioxi- etilammo, of which loe acetoximeti lamino groups, propioniloxinetiiarnino, butiploximetilamino and pivaloiloxirnet preferred ílarnino . When R represents a group of the formula -NHR * and when R * represents an alkoxycarbonyloxy methyl group having from 1 to 6 carbon atoms in the alkoxy part, the alkoxy part may be a straight or branched chain group. Examples of such groups include metoxicarbomloximetiiamino al.coxicarboniloximetilami.no groups, etoxicarbomloxirnetiiarní not propoxicarbomloximeti lamino, isopropoxicarboni loxirnetiiainmo, butoxicarboniloximetilanino, isobutoxy ílammo carboniloxirnet, sec-butoxicarbomloximetilamino, terbutoxicarbomloxirneti lamino, pentyloxy carboni loxunet ilarnmo, isopentyloxy carbonyloxymethyl, neopentyloxycarbonyloxy i-methylamino, 2-methybutoxycarbon? lox? met? larn? no, l-ethyl-propoxycarbonyloxyrnethylamine, 4-met? Ipent i lox ica rboni lox i -metí lamino, -me í 1 pent i lox i ca rbon 11 oxi rnet i lam ino, 2 -rne n-pentiloxicarbo iloximeti lamino, 1-met? Lpent? Lox? Carbon? Loxi-metí lam ino, 3,3-d? met? lbutox? carbon? lo? met? lam? no, 2,2-dimetilbutoxicarboni loxirnetiiami no, 1,1-d? rnet? l butoxicarboni 1-oxi etiiammo, 1 , 2-d? Rnet lbutoxicarboniloxirnetilarnino, 1,3-dinetiibuto icarboni lox irneti lamino, 2,3-d? Rnet? Ibutox? Carbon? L- oxirneti lamino, 2-etylbutoxycarbonyloxy, lamino, hexyl, i-carbonyloxymethylaryl and isohexyloxycarbonyloxymethyl lamino. Of these, alkoxycarbonyloxymethylamino groups having from 1 to 4 carbon atoms in the alkoxy part are preferred, preferably the methoxycarbonyloxymethyl lamino, ethoxycarbonyloxymethylamino, propoxylboxyethylamino, isopropoxycarbonyloxytrimethylamino, butoxycarbonyloxypnetamino, isobutoxycarbonyloxymethylamino groups. , sec-butoxicarbo iloxirneti lamino and terbutoxicarboniloxi ethylamino; and preferably, the methoxycarbonyloxyrneti lamino or ethoxycarbonyloxyrnetiiarnino group. When R represents a group of the formula -NHR », where R» represents a group (2-oxo-l, 3-d? Oxolen-4-? L) rnet ?, it is unsubstituted or substituted at the position 5-d? Oxolene with an alkyl group having from 1 to 6 carbon atoms, or with an aplo group. Examples of said alkyl groups include those exemplified above in relation to R; preferably the methyl, ethyl or terbutyl group. Examples of such aryl groups include those exemplified further in relation to R *, preferably the phenyl group. Specific examples of such groups (2-oxo-l, 3-d? Oxolen-4-? L) rnet? Lo include the groups (2-oxo-l, 3-d? Oxolen-4-? L) -methyl , (5-met ll -2-oxo-l, 3-d? Oxolen ~ 4-? L) -methyl, (5-et-1-2-oxo-1,3-d? Oxolen-4-? L) methyl, (5-te but? i ~ -oxo-l, 3-d? oxolen ~ 4-yl netyl and (5-phen? l-2-oxo-l, 3-d? oxolen-4-? 1) It is preferred from the above groups and atoms that R1 represents a methyl group, an ino group or a group acetylamines, of which the amino group and the acetylamins group are most preferred. When R2 represents a substituted femlo group, it may have from 1 to 5 substituents, preferably 1 to 3 constituents, better still, 1 or 2 constituents and, preferably, 1 substituent. When there is more than one substitute, these may be the same or different from each other. Substituents are selected from the group consisting of the alpha substituents and the beta substituents, previously defined and exemplified below, better still, of the alpha and beta listeners, defined and exemplified below; still better, of the alphai and beta2 substituents defined and exemplified further on. The substituents alpha 1 are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms and alkylthio groups having from 1 to 4 carbon atoms. Substituents beta1 are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 4 carbon atoms and which are substituted with at least one substituent selected from the group consisting of it consists of the substituents alpha1, rnercapto groups, alkanoylthio groups having from 1 to 4 carbon atoms, halogenoalkoxy groups having from 1 to 4 carbon atoms and alkylenedioxy groups having from 1 to 4 carbon atoms.

The beta2 substituents are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, halogenoalkyl groups having from 1 to 4 carbon atoms, mercapto groups, alkanoylthio groups having from 1 to 4 atoms of carbon, haiogenoalkoxy groups having from 1 to 4 carbon atoms and alkylene groups i having from 1 to 4 carbon atoms. When the alpha substituent or the substituent alpha 1 represents a halogen atom, this can be a fluorine, chlorine, bromine or iodine atom, of which the fluorine, chlorine and bromine atoms are preferred. When the alpha substituent or the substituent alpha1 represents an alkoxy group having from 1 to 6 (or 4) carbon atoms, it can be a straight or branched chain group, and examples include the methoxy, ethoxy, propoxy, isopropoxy groups, butoxy, isobutoxy, secondary butoxy, tertiary butoxy, pentyloxy, and sopentyloxy, neopentyloxy, 2-rnetii utoxy, 1-et? ipropox ?, 4-met? lpent? lox ?, 3-met? Ipenoxyloxy, 2-rnet-lpentyloxy, 1-rnet? L? Ent? Lox ?, 3,3? D? Rnet? Lb? Toxy, 2,2-di-ethylbutoxy, 1,1-dimethylbutoxy, 1,2-d? met? lbutox? , 1,3-dirnetiibutoxy, 2,3-d? Met? Oxy oxy, 2-et? Lbutox ?, hexyloxy and isohexyloxy. Preferred are alkoxy groups having from 1 to 4 carbon atoms, preferably the rnetoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, secondary butoxy and tertiary butoxy groups and, most preferably, the rnetoxy and ethoxy groups.

When the alpha substituent or substituent alpha1 represents an alkylthio group having 1 to 6 (or 4) carbon atoms, it can be a straight or branched chain group and examples include the rnetylthio, ethylthio, propylthio, isopropylthio groups, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentthylthio, isopentiitio, neopentylthio, 2-methyltbutyl, 1-ethylpropylthio, 4-met? ipent? it? o, 3-rnet? lpent? lt, 2- ethylpentylthio, 1-met? lpent? ítio, 3,3-d? met? lbut? uncle, 2,2-dirnethylbutylthio, 1,1-d? met? lbut? lt? o, 1, 2-d? rnet? lbut? lt? o, 1 , 3-dimethylbutylthio, 2,3-d? Met? l-butylthio, 2-et? lbutyl, hexylthio and isohexylthio. Preference is given to alkylthio groups having from 1 to 4 carbon atoms, preferably the methylthio, ethylthio, propylthio, isopropylthio, butyl + io, isobutylthio, sec-butylthio and tert-butyllium groups and, most preferably, the methylthio and ethylthio groups. When the beta substituent, the beta 1 substituent or the beta 2 substituent represents an alkyl group having from 1 to 6 (or 4) carbon atoms, this may be a straight or branched chain group, and the examples include the methyl, ethyl groups , propyl, isopropyl, butyl, isobutyl, secondary butyl, tertiary butyl, pentyl, and sopentyl, neopentyl, 2-rnet? lbutyl, 1-methylpropyl, 4-methylpent, 3-methylpent, 2-methylpentine, 1-methyl, 3, 3-methyl? ibutium, 2,2-dimethylbutyl, 1, 1-dibutyl, 1,2-dimethylbutyl, 1,3-dirnethylbutyl, 2,3-dimetylbutyl, 2 -butyl, hexyl and isohexyl. Of these, those alkyl groups are preferred they have from 1 to 4 carbon atoms, preferably the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl and tertiary butyl groups; and better still, the methyl and ethyl groups. Said groups can be unsubstituted or can be substituted with at least one of the alpha (or alpha1) substituents defined and exemplified above, in particular the halogen atoms. Specific examples of said haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-di-luoroethyl, 2,2,2-tri-fluoroethiio, 2,2-trichloroethyl, 3-fluoropropyl, -fluorobutyl, chloromethyl, trichloroethyl, iodomethyl and bromornetyl, of which the fluoromethyl, difluorometyl, tri-fluoromethyl, 2-fluoroethyl, 3-fluoro-yl, 4-fluorobutyl, chloroethyl, trichloroethyl and bromomethyl groups are preferred.; and fluorodileryl, difluoromethyl and trifluoromethyl groups are more preferred. In general, when the beta substituent, the beta 1 substituent or the beta 2 substituent represents a substituted alkyl group there is no particular restriction on the number of substituents, except those that may be imposed by the number of substitute positions by possible steric constraints. However, normally from 1 to 3 of said substituents are preferred. When the beta substituent represents an alanoyloxy group, it can be an alkanoylthio group, it can be a straight or branched chain group having from 1 to 6 (or 4) carbon. Specific examples of alkanoylthio groups include the formylthio, acetylthio, propionylthio, butypthio, isobutyrylthio, pivaloylthio, valepltio, isovalerylthio and hexanoylthio groups, of which those groups having 1 to 4 carbon atoms are preferred, and other groups are preferred. acetylium and propiomltio. When the beta substituent represents an alkylsulfinyl group having 6 carbon atoms, it may be a straight or branched chain group, and examples include the methylsulfinyl, ethyl-sulfinyl, propyl, finyl, isopropylsulinyl, butylsulfinyl groups, isobutylisulfinium, secbutylulphonyl, tert-butyl sulfimyl, pentiisylimide, isopentiisulinyl, neopentylsulfinyl, 2-methytisulfonyl, 1-et? lprop? ls? lf? nl, 4- Met? lpent? lsulf? mlo, 3,3-d? met? l-butilsulfinilo, 2, -d? met? lbut? lsulf? nor what, 1, 1-d? rnet? butyl-sufinyl, 1,2-d? met? ibut? isulf? l ?, 1,3-d? met? lbut? l sulf? n ?, 2, 3-d? met? lbut? lsulf? nor is it 2-ethylsulfonyl, isulin, and isohexylsulfimyl. Preference is given to alkylsulfinyl groups having 1 to 4 carbon atoms, preferably the methylisulfinyl, ethyl sulphimyl, propyl, trifluoromethyl, sulfonyl, butyl, and trifluoromethyl groups.; and what is most preferred, the rnetilsulfi and lo and etiisulfimlo groups. When the beta-constituent represents a cycloalkyloxy group, it preferably has from 3 to 8 carbon atoms in a single carbocyclic ring, and examples include the cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy and cyclooxyloxy groups, of which cyclopentyloxy and cyclohexyloxy groups are preferred; the cyclopentiioxy group being the most preferred. When the beta substituent, the beta 1 substituent or the beta 2 substituent represents a halogenoalkoxy group having from 1 to 6 (or 4) carbon atoms, it can be a straight or branched chain group, and the examples include the luoromethoxy, difluoro ethoxy groups , trifluoro ethoxy, 2-fluoroethoxy? , 2-chloroethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-tpchloroethoxy ?, 3-fluoropro-oxy, 4-fluorobutoxy, chloromethoxy, trichloromethoxy, iodomethoxy and bronometoxy, of which those groups having from 1 to 4 carbon atoms are preferred; and the fluoro-ethoxy, difluoromethoxy, tp fluorometho-, 2-fl uoroethoxy groups are more preferred, 2-chloroethoxy ?, 2-bromoethoxy? , 3-fluoropro? Ox ?, 4-fluorobutox? , chloromethoxy, trichloromethoxy and bromomethoxy; and most preferred are the fluoro-ethoxy, difluoromethoxy and tri-loromethoxy groups. When the beta substituent, the beta1 substituent or the beta2 substituent represent an alkylenedioxy group having from 1 to 6 (or 4) carbon atoms, it can be a straight or branched chain group, and examples include the methylenedioxy, ethylenedioxy groups , tri-ethylendioxy, tetra-ethylenedioxy, pentamethylenedioxy, hexaethylenedioxy and propylenedioxy, of which groups having 1 to 4 carbon atoms are preferred, and ethylenedioxy groups are more preferred; etiiendioxi. Specific examples of R 2 include phenyl group, phenyl groups having 1 to 3 substituents selected from halogen atoms, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, mercapto, alkanoylthio of 4 carbon atoms, alkyl isulfyl of 1 to 4 carbon atoms in the alkyl; such as the 4-fluorofemlo, 4-chlorofemlo, 4-brornofen groups? it, p-tolyl, 4-et-1-femlo, 4-rnetoxy-phenol, 4-ethoxyphenyl, 4-met? lt? ofem lo, 4-et? lt? ofen? lo, 4- etcaptophenyl, 4-acetyl ? lthiophenyl, 4-prop? on? l thiofemlo, 4-methylisulfinylphenyl, 4-et? lsulf? n? lfem lo, 3,4-d? fluorophen ?, 2,4-d? fluorophen ?, 3,4-d? chlorophen ?, 2, 4-d? chlorophen ?, 3,4-dimethylphenyl, 3 , 4-d? Methox? feni lo, 3-chloro-4-fluorophenol, 3-chloro-4-methox-femlo, 3-fluoro-4-rnetox? fen? 3-r-n-l-4-methoxyphenyl, 3,5-d-chloro-4-methoxy-phenol and 4-methoxy-3, 5-dinethylphenyl; Femlo groups substituted with tp f luoromet i lo, difluoromethoxy or tpfluoromethoxy, such as 4-trifluoromethylphenyl, 4-dLfluoromethoxy? feni lo and 4-tpfluorornetoxyphenyl; and phenyl groups substituted with rnetiiendioxy or ethylenedioxy, such as the 3,4-rnetiiendioxifemlo and 3,4-et? lend? ox? phenyl. In the compounds of formula (I) and (II), R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 carbon atoms or an alkyl group having 1 to 6 carbon atoms. carbon, and replaced with 01 at least one substituent selected from the group consisting of alpha substituents, and preferably, at least one selected from the group consisting of substituents alpha1, defined and exemplified further back, and better still, with at least one substituent. halogen atom. When R3 represents a halogen atom, it may be a fluorine, chlorine, bromine or iodine atom. When R3 represents an alkyl group having 1 to 6 carbon atoms, it can be a straight or branched chain group, and examples include the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, tertiary butyl groups, pentyl, isopentyl, neopentyl, 2-methylbutyl, 1-ethylene, 4-methylant, 3-rneti, pentyl, 2-netylpentyl, 1-methylpentyl, 3,3-dimethylbutyl , 2,2-dimethylbutyl, 1,1-dirnethibutyl, 1, -dimethylbutyl, 1,3-dimethylbutyl, 2,3-d? Methylbut? it, 2-ethylbutyl, hexyl and isohexyl. Of these, those alkyl groups having from 1 to 4 carbon atoms are preferred, preferably the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl and tertiary butyl groups and, most preferably, the methyl and ethyl groups. When R3 represents an alkyl group having 1 to 6 carbon atoms, it may be a straight or branched chain group, which is substituted with at least one substituent, selected from the group consisting of the alpha (or alpha1) substituents ), defined and exercised above, and particularly with a halogen atom. The examples of the alkyl part can be as those given above in relation to the unsubstituted groups. Examples of those halogenoalkyl groups include the fluoroethyl, difluoromethyl, trifluoromethyl, 2-fluoroetheio, 2,2-difluoroethyl, 2,2,2-tr? Fluoroetol, 2,2,2-tpchloroethoyl groups. , 3-fluoropropyl, 4-fluorobutyl, chloro-nitrene, t-chloro-deaceyl, ethyl-iodine and bromomethyl, of which the fluororethyl, difluorornethyl, tri-fluororyl, 2-fluorouroxy, 3-fluoropro , 4-fluorobutyl, iodomethyl, chloromethyl, t-chloromethyl, bro-ometiio, 2-chloroethanol and 3-chloroprOp-lo; and the preferred moieties are the groups fluoromethyl, difluoromethyl, trifluoroethyl, 2-fluoroetheio and 2-chloroethoyl. R3 preferably represents a hydrogen atom, a halogen atom (such as a fluorine, chlorine, bromine or iodine atom), a methyl group, an ethyl group, a fluorornetyl group, a difluoromethiium group, a 2- group fl uoroetium or a 2-chloroetyl group. In the compounds of formula (I) and (II), R * represents a hydrogen atom, an alkyl group having 5 carbon atoms, an alkyl group having 1 to 6 carbon atoms and substituted with minus one of the alpha substituents; a cycloalkyl group having from 3 to 8 carbon atoms, an aplo group having from 6 to 14 carbon atoms, an aryl group having from 6 to 14 carbon atoms and substituted with at least one of the alpha substituents or of the beta substituents (preferably at least one of the substituents alpha1, defined and exemplified above, or substituents beta3, defined later, and included in the groups exemplified above in relation to the beta substituents); an aralkyl group (having the carbon atom in the alkyl part and from 6 to 14 carbon atoms, preferably from 6 to 10 carbon atoms, in the aryl part) or an aralkyl group (having 6 to 10 carbon atoms); carbon atoms in the alkyl part and from 6 to 14 carbon atoms, preferably from 6 to 10 carbon atoms in the aplo part), substituted with at least one of the substituents alpha or the substituents beta (preferably at least one of substituents alpha1 or substituent beta3). Substituents beta3 include alkyl groups having from 1 to 6 carbon atoms, alkyl groups having from 1 to 6 carbon atoms and substituted with at least one of alpha substituents, and cycloalkilox groups having from 3 to 8 carbon atoms, all as defined and exemplified above. In particular it is preferred that it should represent hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkyl group having from 1 to 4 carbon atoms and substituted with at least one substituent selected from the group consisting of of the alpha2 substituents, defined below and included in the groups exemplified above in relation to the alpha substituents, a group cycloalkyl having 6 carbon atoms, an aplo group which is unsubstituted or substituted with the substituents alpha2 and substituents beta *, defined below, and included in the groups exemplified above, in relation to the beta substituents; an aralkyl group, which is unsubstituted or substituted with at least one of the substituents selected from the group consisting of the substituents alpha2 and loe its beta elements *. Alpha 2 substituents include hydroxy groups, halogen atoms and alkoxy groups having from 1 to 6 carbon atoms, all as defined and exemplified above. Beta substituents include those groups having 1 to 6 carbon atoms and which are unsubstituted or substituted with at least one halogen atom, and cycloalkyloxy groups having from 3 to 8 carbon atoms, all such as It was defined and exemplified before. When R * represents an alkyl group, it can be a straight or branched chain group, having from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, and examples include the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, tertiary butyl, pentyl, isopentium, neopentium, 2-rnet? ibutyl, 1-etiipropyl, 4-rnet? l? ent? what, 3-rnet? lpent? lo, 2-rnet? Ipentyl, 1-ethylpentyl, 3, 3-d? Met i lbutyl,?, 2-d? Rnet? Lyl ?, 1,1-dirnethylbutyl, 1,2-d? Methyl, l , 3-d? Rnet? Lbut? Io, 2,3- dirnetylbutyl, 2-butyl, hexyl and isohexyl. Of these, those alkyl groups having from 1 to 4 carbon atoms are preferred, preferably the methyl, ethyl, propyl, isopropyl and butyl groups and, most preferably, the methyl group. When R * represents a substituted alkyl group, it can be any of the alkyl groups exemplified above, in particular the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, tertiary butyl, pentyl or hexyl groups. Said groups are substituted with one or more of the alpha substituents defined and exemplified above, especially the hydroxy group, the alkoxy groups having from 1 to 4 carbon atoms and the halogen atoms, such as the fluorine, chlorine atoms, of bromine and iodine. There is no particular restriction on the number of said parties, except those that may be imposed by the number of substitutable positions and, possibly, by strict restrictions. However, in general, 1 to 3 substituents are preferred. In the case of substituents other than halogen atoms, a single substituent is more preferred. When R * represents a cycloalkyl group, it has from 3 to 8 carbon atoms, and examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl groups, of which cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl groups are preferred.; and the most preferred is the cyclopropyl group.

When R * represents an aryl group, it is a carbocyclic aromatic group, preferably having from carbon atoms, for example, a phenyl or naphthyl group (for example, 1- or 2-naphthyl). Said group may be substituted or unsubstituted and, if substituted, substituents are selected from the group consisting of the alpha substituents and beta substituents, defined and exemplified above. When R * represents an aralkyl group, it is an alkyl group (which may be as defined and exemplified above in relation to R), preferably having 1 to 4 carbon atoms, which is preferably substituted with 1 to 3 aryl groups (better still, 1), which can be as defined and exemplified above. This aralkyl group can be substituted or unsubstituted in the straight part and, if substituted, the substituents of the group consisting of alpha substituents and beta substituents defined and exemplified above are selected. Specific examples of the unsubstituted groups include the benzyl, phenethyl, 3-phenolyl, 4-phenol butyl, 1-naphthyl, and 2-naphthyl ether groups. When these aplo and aralkyl groups are substituted, there is no particular restriction on the number of such substituents, except those which may be imposed by the number of substitutable positions (5 in the case of the phenyl groups and 7 in the case of the groups). naphthyl) and possibly due to steric restrictions. Preferred examples of such substituents include: halogen atoms, such as the fluorine, chlorine, bromine and iodine atoms; alkyl groups having from 1 to 6 carbon atoms, such as the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl and tertiary butyl groups; halogenoalkyl groups having 1 carbon atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, t-chloroethyl, chlorocarbonyl, 2-fluoromethyl, 2-chloroetyl, 2-bromoet io, 2-iodoetyl, 3-fluoropropyl and 4-fluoropropyl; alkoxy groups having from 1 to 6 carbon atoms, such as the rnetoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, secondary butoxy and tertiary butoxy groups; and cycloalkyloxy groups having from 3 to 8 carbon atoms, such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyioxy groups. Preferred examples of groups which may be represented by R * include the hydrogen atom, the alkyl groups having from 1 to 4 carbon atoms, such as the methyl, ethyl, isopropyl, butyl and isobutyl groups; the ono-, di- or trihalogenoalkyl groups having from 1 to 4 carbon atoms, such as the groups fluoromethylo, di fluorornetyl, chlorodifloronet, brornodif luorornetyl, trifluoromethyl, 2-fluoroethio and 2.2, -tr? fl uorornet lio; the hydroxymethion group; the alkoxymethion groups that have 1 to 4 carbon atoms in the alkoxy part, such as the cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl groups; the phenyl group; the mono- or difluorofemlo groups, such as the 4-fl uorophenyl and 2,4-d? fluorophen groups? the; the mono- or dimethoxyphene groups, such as the 4-methox groups? phenyl and 3,4-dimethoxypheme; tolyl groups, such as p-tolyl and o-tolyl groups; cyclopentyloxy (rnetoxy) phenyl groups, such as the 3-c? clopent? lox? -4-methox? phenol group; the groups tp f luoromet 11 feni lo, such as the group 4-trifluoromet? l fem lo; the benzyl group; substituted benzyl groups, such as the 4-methoxybenzyl and 3-c? clopent? lox? -4-rnetoxy? benzyl groups; the phenethyl group, the naphthyl groups, such as the l-naphthyl and 2-naphthyl groups; and the naphthyl ether groups, such as the 1-naphthylmethyl and 2-naphthyl ether groups. Preferred classes of compounds of the invention are those compounds of formula (I) and (TT) and their salts, wherein: (0) R represents an atom of hydrogen, a halogen atom or an alkyl group having 1 to 4 carbon atoms; (B) R1 represents a methyl group, an arnino group or an acetyl lamium group; (C) R 2 represents a phenyl group or a phenyl group which is substituted with at least one substituent selected from the group consisting of the substituents alpha 1 and the substituent beta1, defined below: substituents alpha1 are selected from the group consisting of halogen atoms, alkoxy groups having 1 to 4 carbon atoms and alkylthio groups having 1 to 4 carbon atoms; and the beta1 substituents are selected from the group consisting of alkyl groups having 4 carbon atoms, alkyl groups having from 1 to 4 carbon atoms and substituted with the monkeys a substituent selected from the group consisting of substituents alpha1, mercapto groups, alkanoylthio groups having the 4 carbon atoms; halogenoalkoxy groups having from 1 to 4 carbon atoms and alkylenedioxy groups having from 1 to 4 carbon atoms. (D) R3 represents a hydrogen atom, a halogen atom an alkyl group having 1 to 4 carbon atoms or a substituted alkyl group having 4 carbon atoms and substituted with at least one substituent selected from the group it consists of its alpha1 listeners, defined below; The alpha1 substituents are selected from the group consisting of halogen atoms, alkoxy groups having 1 to 4 carbon atoms and alkylthio groups having from 1 to 4 carbon atoms. (E) R * represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkyl group substituted having 1 to 4 carbon atoms, and substituted with at least one substituent selected from the group consisting of the alpha substituents, defined above; a cycloalkyl group having from 3 to 6 carbon atoms, an aryl group having fi x 10 ring carbon atoms, and which is unsubstituted or substituted by at least one substituent selected from the group consisting of substituents alpha1 and the beta3 substituents defined below; an aralkyl group having from 1 to 4 carbon atoms in the alkyl part, and containing at least one aryl group as defined above; the substituents alpha1 are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms and alkylthio groups having from 1 to 4 carbon atoms; and the beta3 substituents include alkyl groups having from 1 to 6 carbon atoms, alkyl groups having from 1 to 6 carbon atoms and substituted with at least one of the alpha substituents, and cycloalkyloxy groups having from 3 to 8 atoms of carbon. Particularly preferred compounds of the present invention are those compounds of the formula (I) and their salts, in which R is as defined in (A) above; R is as defined in (B) above, R2 is as defined in (C) above, R3 is as defined in (D) above and R * is as defined in (E) above.

The most preferred classes of compounds of the present invention are those compounds of formula (I) and formula (II) and their salts, in which: (F) R represents a hydrogen atom, a fluorine atom,? n Chlorine atom or a methyl group. (G) R represents an ammo group or an acetylamino group. (H) R2 represents a phenyl group or a phenyl group which is substituted with at least one substituent selected from the group consisting of the substituents alpha1 and the euetituyentee beta2, defined below, and better still, with 1 to 3 of said substituents; the substituents alpha1 are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms and alkylthio groups having from 1 to 4 carbon atoms; and the beta2 substituents are selected from the group consisting of alkyl groups having from 4 carbon atoms, haloalkyl groups having from 1 to 4 carbon atoms, mercapto groups, alkanoylthio groups having from the 4 carbon atoms, halogenoalkoxy groups having 1 to 4 carbon atoms and alkylenedioxy groups having from 1 to 4 carbon atoms. (I) R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a halogenoalkyl group having 1 to 4 carbon atoms.

(J) R * represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms and substituted with at least one substituent selected from the group consisting of the alpha2 substituents, defined above; a cycloalkyl group having from 3 to 6 carbon atoms, an aryl group having from 6 to 10 carbon atoms and which is unsubstituted or substituted by at least one substituent selected from the group consisting of substituents alpha2 and substituents beta * defined below; an aralkyl group having 1 to 4 carbon atoms in the alkyl part and containing at least one aryl group such as those defined above; the alpha2 substituents include hydroxy groups, halogen atoms and alkoxy groups having from 1 to 6 carbon atoms; and substituents beta * include alkyl groups having from 1 to 6 carbon atoms and which are unsubstituted or substituted with at least one halogen atom, and cycloalkyloxy groups having from 3 to 8 carbon atoms. Particularly preferred compounds of the present invention are those compounds of formula (I) and (II) and their salts, in which R is as defined in (F) above; R1 is as previously defined in (G); R2 is as defined in (H) above; R3 is as defined in (I) above and R * is as defined defined in (3) above. The most preferred classes of compounds of the present invention are those in which: (K) R represents a hydrogen atom. Of these, particularly preferred compounds of the present invention are those compounds of formula (I) and (II) and their salts, in which R is as defined in (K) above; R1 is as defined in (G) above; R2 ee as defined in (H) above, R3 is as defined in (I) above and R * is as defined in (3) above. The compounds of the present invention can exist in the form of various stereoisomers, R and S isomers, depending on the presence of asymmetric carbon atoms. The present invention covers both the individual isomers and their mixtures, including the racemic mixtures. The compounds of the invention can be waterborne when they are exposed to the atmosphere to produce water or to produce a hydrate. The present invention covers said hydrates. Traditionally some other solvents can be absorbed by the comptetoe of the present invention, to produce solvates, which also form part of the present invention. The compounds of the present invention can form salts. Examples of such salts include: the salts horn alkali metals, such as sodium, potassium or lithium; the salts as an alkaline earth metal, such as barium or calcium; salts with another metal, such as magnesium or aluminum salts; ammonium salts, salts with an organic base, such as a salt with the sheet, direthylamine, triethyl amine, diisopropylamine, cyclohexylamine or dicyclohexyl ina; and salts like a basic amino acid, such as lysine or argimna. Specific examples of compounds of the present invention are those of formula (I) and (II) in which the groups thereof are as defined in a respective one of tables 1 (formula (I)) and (formula (ID). < p) In these tables, the following abbreviations are used: Ac acetyl Bu butyl and r buty ryl i Byr isobutyryl BZ benzyl Et ethyl For formyl I methyl Ph phenyl Piv pivaloyl cPn ciclopenti.lo Pr propyl cPr cyclopropyl iPr isopropyl Prn propionyl iVal isovaleryl Val valeryl TABLE I ADRO I (continued) TABLE I (continued) TABLE I (continued) TABLE I (continued) TABLE I (continued) 4 (5 TABLE II (continued) TABLE II (continued) TABLE II (continued) TABLE II (continued) TABLE II (continued) TABLE II (continued) TABLE II (continued) Of the compounds mentioned above, particularly preferred compounds are the following: (1) 3-met? L-2- (4-meth l phenyl) -1- (4-sul phenyl) phenyl) pyrrole. (2) 4-met? 1 -2- (4-met? Lfeml) -l- (4-sulo-pheoylphenol) (3) l- (4-fluorophen? 1) -2- (4-sul phenylphenol) pyrrolidone. ) l- (4-fluorophenyl) -4-meth? l-2- (4-sul-pheno? lfen? l) pyrrol. (5) 5-fluoro-l- (4-fluorophen? 1) -2- (4-rne? Lsul on? Lfeml) - pyrrole (6) 2- (4-rnetox? Phen? 1) -4-met? J -1 - (4-sul farnoi Item 1) - pyrrole. (7) 1- (4-methox? Phen?) -4-rne? .-? - (4-sul-famoylphenyl) -pyrrole. (8) 4-et? L-2- (4-rnetox? Phen? L) -l- (4-sul amo? J feniJ) - ?? rrol. (9) 2- (4-chlorophen? L) -4-met? L-l- (4-sul-famoyl phenyl) pyrrol. (10) 4-rnet? L-2- (4-rnet? Lt? Ofen? L) -l- (4-sulfamo? Lferul) -pyrrole. (11) 2- (4-ethoxy? In? J) -4 -rne ti 1 -J- (4-sul famoyl phen íl) pi ro! . (12) 2- (4-rnetox? -3-met? .l phenyl) -4-rnel 11-1- (4-sul famoyl-phenyl RIp. (13) 2- (3-fluoro-4-methox) FemJ) -4-met? lJ- (4-sul famoyl-phenyl) pyrrol. (14) 4-met? l-2-fem-l- (4-sulfamo? lfen? l) p rrol. ( 15) 2 - (3, - imet 11 f em 1) - 4 -me +? Ll- (4-sul f moi 1 phen 1) -pi ro! (16) 2- (3-cJoro-4-fnetox? fen? l) -4-rnet? ll- (4-sulfarno? l-phenyl) pi rl. (17) 4-met? L-l- (4-rne +? L +? Ofen? I) -2- (4-sulfamo? Lfen? L) -pyrrole. (18) 5-chloro-l- (4-methox? Phen? L) -2- (4-sulo-pheoylphenol). (19) 4-met? L-l- (3,4-d? Met lfenU) -2- (4-sulfamo? Lfen? L) -pyrrole. (20) 5-chloro-l- (4-ethoxy? Phen? L) -2- (4-sulfamo? Lfen? L) p? RroJ. (21) 5-Chloro-1- (4-methylt ofenyl) -2- (4-sulfamyl-1-yl) -pyrrole. (22) 1- (4-et? Lt? Ofen? L) -4-met? L-2- (4-sul-pheo-phen-U) -pyrrole. (23) 2- (3,5-d? Rnet? Lfen? L) -4-rnet? L-l- (4-sulfarno? Lfen? L) -pyrrole. (24) 1 - (4-rnercaptofen l) -4-met? L-2- (4-sul-phenoyl-phenyl-1) -pyrrole. (25) l- (4-acet? Lt? Ofen? 1) -4-met? L-2- (4-suJ famoyl phenyl) -pyrrole. (26) l- (4-acet? Larn? Nosul omlfen? L) -4-rnet? L-2- (4-rnetox? -phenyl) -pyrrole. (27) l- (4-acetyl-n-sulphonyl-1-ene) -4-rnet-l-2- (3,4-dimethyl-phenyl-pyrrolidone.) Of these are most preferred compounds. ), (6), (9), (10), (11), (12), (13), (15), (17), (26) and (27) and the most preferred are No. ( 11), (15), (17), (26) and (27) The compounds of the present invention can be prepared by a variety of well-known methods for the preparation of compounds of this type, by example, as those shown in the following methods A to L. The following methods A to E and K illustrate the preparation of the compounds of the formula (I).

METHOD A This illustrates the preparation of compounds of the formula (Ia), in which R3 is a hydrogen atom, an alkyl group or a substituted alkyl group having at least one substituent selected from the group consisting of the alpha substituents.

REACTION SCHEME A (1) (3) (6) (the) In the above formulas, R, Rl, R2 and RA are as defined above; and R3a represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a substituted alkyl group having 1 to 6 carbon atoms and having at least one substituent selected from the group consisting of alpha substituents, as defined and exemplified above.

Step Al In this step, an allyl compound of the formula (3) is prepared by condensation by dehydration of a benzaldehyde compound of the formula Ol), with an aniline compound of the formula (2) in an inert solvent. Normally and preferably the reaction is carried out in the presence of a solvent. There is no particular restriction on the nature of the solvent to be employed, provided that it has no adverse effects on the reaction or on the reagents involved, and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include: aliphatic hydrocarbons, such as hexane, heptane and petroleum tert; aromatic hydrocarbons, such as benzene, toluene and xylene; halogenated hydrocarbons, such as netylene chloride, chloroform, carbon tetrachloride, and diclorethane; the ethers, such as diethyl ether, d-opropyl ether, tetrahydrofuran and dioxane; alcohols, such as rnetanol, ethanol, propanol, isopropanol and butanol; and organic acids, such as acetic acid and propiomco acid. Alcohols are preferred from these solvents. The reaction can be carried out on a wide range of temperatures, and the precise reaction temperature is not critical to the invention. The preferred reaction temperature will depend on factors such as the nature of the solvent and the starting material or reagent used. However, in general, it is convenient to carry out the reaction at a temperature of 5 ° C to 200 ° C, even better, from room temperature to 150 ° C. The time required for the reaction can also vary widely, depending on many factors, mainly the temperature of the reaction and the nature of the reagents and solvent employed. However, provided that the reaction is carried out under the preferred conditions indicated above, a period of 10 minutes to 20 hours, preferably even 1 hour to 15 hours, will usually suffice. The reaction can be carried out while removing the water that is produced in the reaction; but normally the reaction will proceed sufficiently without any such procedure.

Step A2 In this step, an anilinonitoplo compound of the formula (4) is prepared by the addition of cyanide of hydrogen to the aldirnine compound of the formula (3), prepared as described in step AJ. The reaction can be carried out by reacting the aldiin compound of the formula (3) with tnmethylsilyl cyanide (TT1S-CN) in the presence of an acid Lewis, for example, aluminum chloride, tin chloride or zinc chloride. Normally and preferably the reaction is carried out in the presence of a solvent. There is no particular restriction on the nature of the solvent to be employed, provided that it has no adverse effects on the reaction or on the reagents involved, and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include: aromatic hydrocarbons, such as benzene, toluene and nitrobenzene; halogenated hydrocarbons, such as rnetylene chloride, chloroform, carbon tetrachloride and 1,2-d-chloroethane; and the ethers, such as diethyl ether, dusopropyl ether, tetrahydrofuran and dioxane. Those ethers are preferred. The reaction can be carried out on a wide range of temperatures, and the precise reaction temperature is not critical to the invention. The preferred reaction temperature will depend on factors such as the nature of the solvent and the starting material or reagent used. However, in general, it is convenient to carry out the reaction at a temperature of 5 ° C to 200 ° C, better still, from the room temperature up to J50 ° C. The time required for the reaction may also vary widely, depending on many factors, mainly the temperature of the reaction and the nature of the reagents and solvent employed. However, provided that the reaction is effected under the preferred conditions indicated above, a period of 30 minutes to 100 hours, preferably even from 1 hour to 30 hours, will suffice.

STEP A3 AND STEP A4 In these steps the desired compound of the formula (la) which is a compound of the present invention is prepared by reacting the anilinomtplo compound of the formula (4), prepared as described in step A2 , with an alpha, beta-unsaturated aldehyde or a ketone compound of the formula (5), to obtain a pyrrolidone compound of the formula (6), which is then dehydrated and then dehydrogenized in a modification of the method by VA Treibs and R. Derra CAnn. Chem., 589, J76 (1954) 1.

Step 3 The step is carried out in the presence of a base. There is no particular restriction on the nature of the bases used, and any base commonly used in reactions of this type can be used here as well. Examples of such bases include: alkaline metal hydroxides, such as lithium hydroxide, sodium hydroxide and potassium hydroxide; alkaline metal hydrides, such as lithium hydride, sodium hydride and potassium hydride; Alkali metal amides, such as lithium amide, sodium amide, potassium amide, lithium bis (tnmethylstil) arnide; and the alkali metal alkoxides, such as lithium ethoxide, sodium methoxide and sodium ethoxide and potassium terbutoxide. Preferred are lithium amides. Normally and preferably the reaction is carried out in the presence of a solvent. There is no particular restriction on the nature of the solvent to be employed, provided that it has no adverse effects on the reaction or on the reagents involved, and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include: aliphatic hydrocarbons, such as hexane and heptane; aromatic hydrocarbons, such as benzene, toluene and xylene; The ethers, such diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; and alcohols, such as methanol, ethanol, propane, isopropanol and butanol. The ethers are preferred from these solvents. The reaction can be carried out on a wide range of temperatures, and the precise reaction temperature is not critical to the invention. The preferred reaction temperature will depend on factors such as the nature of the solvent and the starting material or reagent used. Without 6J However, in general, it is convenient to carry out the reaction at a temperature of -7B ° C to J00 ° C, better still, from -78 ° C to room temperature. The time required for the reaction can also vary widely, depending on many factors, mainly the temperature of the reaction and the nature of the reagents and solvent employed. However, provided that the reaction is carried out under the preferred conditions indicated above, usually a period of JO minutes at 30 hours, better still, from 1 hour to 20 hours will suffice.

Step A4 In this step the desired compound of the formula (la), which is a compound of the present invention, is prepared by dehydrating and dehydrogenating a compound of the formula (6), prepared as described in Step A3. This can be achieved by heating the residue obtained by distilling off the solvent from the product of step A3, or by heating the material obtained, extracting that residue, washing it with water and expelling the solvent by distillation, at a temperature not lower than J00 ° C. , in the presence or absence of a solvent, after the reaction of step A3 is completed. The reaction proceeds sufficiently in the presence of a solvent; but when a solvent is used, preferably the solvent is inert and has a high boiling point.

Examples of suitable solvents include: toluene, xylene, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, diglyme and diphenyl ether.

METHOD B This is a modified method for preparing the compound of the formula (la), wherein 3 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a substituted alkyl group having 1 to 6 carbon atoms. carbon and having at least one substituent selected from the group consisting of the alpha substituents, as defined and exemplified above.

REACTION SCHEME B a-1) In the previous formulas: R, Rl, R2, R3 and «are as defined previously; each of R $ and R * represents an alkyl group having 1 to 4 carbon atoms or R5 and R6 together with the nitrogen atom to which they are attached represent a heterocyclic ring containing 6 or 6 ring atoms, of which one is said nitrogen atom; 0 or 1 is an additional heteroatom selected from the group consisting of nitrogen, oxygen and sulfur atoms, and the remaining atoms are carbon atoms; R7 represents a carboxy protecting group; and X »represents a chlorine, bromine or iodine atom. The term "carboxy protecting group", as used herein, means a protecting group capable of being decomposed by chemical means, such as hydrogenolysis, hydrolysis, electrolysis or photolysis. Examples of such carboxy protecting groups include: alkyl groups of 1 to 20 carbon atoms, preferably, from 1 to 6 carbon atoms, such as exemplified with respect to R and the higher alkyl groups, which are well known in the art, such as heptiio, octyl, nonyl, decyl, dodecyl, tridecyl, pentadecyl, octadecyl, nonadecyl and icosyl groups; but most preferably, the methyl, ethyl and tertbutyl groups; halogenated alkyl groups having from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, in the which alkyl part is as defined and exemplified with respect to the above alkyl groups; and the halogen atom is a chlorine, fluorine, bromine or iodine atom; for example: 2, 2, 2-trichloroethyl, 2-halogenoethyl (for example, 2-chloroethyl, 2-fluoroethyl, 2-brornoethyl or 2-iodoethyl), 2,2-dibro-ethyl and 2,2,2-tribromoethyl; cycloalkyl groups having from 3 to 8 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl groups; aralkyl groups, in which the alkyl part has 1 to 3 carbon atoms, and the aryl part is an aromatic carbocyclic group having from 6 to 14 carbon atoms, which may be substituted or unsubstituted and, if substituted, have at least one of the substituents alpha or the beta substituents defined and exemplified above; although unsubstituted groups are preferred; examples of such aralkyl groups include the benzyl, phenethyl, 1-phenylethyl, 3-phenylpropyl, 2-phenylpropyl, 1-naphthyl-phenyl, 2-naphthyl-phenyl, 2- (1-naphthylethyl, 2- (2-naphthyl) ethyl, benzhydryl groups. (ie, diphenylmethyl), triphenyl ether, bis (o-nitrophenyl) methyl, 9-anthrylmethyl, 2,4,6-trimethylbenzyl, 4-bromobenzyl, 2-nitrobenzyl, 4-nitrobenzyl, 3-nitrobenzyl, 4-methoxybenzyl and piperonyl alkenyl groups having from 2 to 6 carbon atoms, such as the groups vinyl, allyl, 2-methylallyl, 1-hydropenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1- pentenyl, 2-pentenlo, 3-? Enten? Lo, 4-penten? Lo, l-hexenilo, 2-hexen? Lo, 3-hexen? Lo, 4-hexen? Jo and 5-hexen? Lo, of which the groups vinyl, aillo, 2-rnet? lalo, 1-? penpelo, iopprope ilo and buteniJo are preferred; the aillo and 2-methylalo groups being more preferred; silylalkyl groups, in which the alkyl part is as defined and exemplified above; the silyl group has up to three substituents, selected from alkyl groups having from 1 to 6 carbon atoms and phenyl groups which are unsubstituted or which have at least one substituent selected from the alpha substituents and beta substituents defined and exemplified above, for example, a 2-tnmethylsilylethyl group; aplo groups having from 6 to 14 carbon atoms and optionally substituted with one or more substituents alpha or substituents beta, defined and exemplified above, for example, the groups femlo, alpha-naftilo, beta-naftilo, mdanilo and antrenilo, preferably the phenyl or mdanyl group and, better yet, the femlo group; any of these aplo groups may be unsubstituted or substituted and, if substituted, preferably has at least one alkyl group having 1 to 4 carbon atoms or the acyl group mo; examples of the substituted groups include the tolyl and benzarnidephenyl groups; phenacyl groups, which may be unsubstituted or have at least one of the alpha substituents or beta substituents defined and exemplified above, for example, the phenacyl group itself or the p-bromophenacyl group; and cyclic and acyclic terpene groups, for example, geranyl, neryl, linalyl, phytyl, menthyl (especially m- and p-menthyl), tujyl, caryl, pinanyl, bornyl, notcaryl, norpinanyl, norbornyl, entenyl, camphenyl and norbornenyl groups .

Step Bl In this step a 1,4-dioxo compound of the formula (9) is prepared by alkylating the beta position of the enamine compound of the formula (8) with a phenacyl halide compound of the formula (7). Normally and preferably the reaction is carried out in the presence of a solvent. There is no particular restriction on the nature of the solvent to be employed, provided that it has no adverse effects on the reaction or on the reagents involved, and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include: aliphatic hydrocarbons, such as hexane, heptane and petroleum ether; aromatic hydrocarbons, such as benzene, toluene and xylene; and the ethers, such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane. The ethers are preferred from these solvents.

The reaction can be carried out in the presence or absence of a base. There is also no particular restriction on the nature of the bases used, and any base commonly used in reactions of this type can also be used here. Examples of such bases include: pyridine, picoline, 4- (N, N-dimethylamino) pyridi, triethylamine, tributylamine, diisopropylethylamine and N-rneti piperidine. The reaction can be carried out on a wide range of temperatures, and the precise reaction temperature is not critical to the invention. The preferred reaction temperature will depend on factors such as the nature of the solvent and the starting material or reagent used. however, in general, it is convenient to carry out the reaction at a temperature of -30 ° C to 200 ° C, better still, from 0 ° C to 100 ° C. The time required for the reaction can also vary widely, depending on many factors, mainly the temperature of the reaction and the nature of the reagents and solvent employed. However, provided that the reaction is carried out under the preferred conditions indicated above, usually a period of 30 minutes to 30 hours, better still, of 1 hour to 20 hours will suffice. At the end of this reaction, the reaction mixture is acidified to prepare the 1,4-dioxo compound of the formula (9).

Step B2 In this step the desired compound of the formula (la) of the present invention is prepared by condensation by dehydration of the 1,4-dioxo compound of the formula (9), prepared as described in step Bl, and a aniline compound of the formula (10) for closing a ring. The reaction can be carried out under the same conditions as described in step Al of method A. However, it is preferred to carry out this step by heating to reflux in acetic acid for a period of 1 to 10 hours.

Step B3 In this step, a dioxoester compound of the formula (12) is prepared by alkylating the alpha position of the oxoester compound of the formula (11) with a phenacyl halide compound of the formula (7). The reaction is carried out in the presence of a base. There is no particular restriction on the nature of the bases used, and any base commonly used in reactions of this type can be used here as well. Examples of such bases include: the alkali metals, such as lithium, sodium and potassium; the alkali metal hydrides, such as lithium hydride, sodium hydride and potassium hydride; alkali metal amide, such as lithium amide, sodium amide and potassium amide; and the alkali metal alkoxides, talee as lithium ethoxide, sodium methoxide, ethoxide sodium and potassium terbutoxide. Alkaline metal alkoxides are preferred therefrom. Normally and preferably the reaction is carried out in the presence of a solvent. There is no particular restriction on the nature of the solvent to be employed, provided that it has no adverse effects on the reaction or on the reagents involved, and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include: aliphatic hydrocarbons, such as hexane and heptane; aromatic hydrocarbons, such as benzene, loluene and xylene; the ethers, such as diethyl ether, sodium ether, tetrahydrofuran and dioxane; the amides, such as dimethylformamide and dimethylacetarin; and alcohols, such as methanol, ethanol, propanol, isopropanol, butanol and tert-butanol. Ethers and alcohols are preferred from these solvents. The reaction can be carried out on a wide range of temperatures, and the precise reaction temperature is not e < z critical to the invention. The preferred reaction temperature will depend on such factors as the nature of the solvent and the starting material or reagent used. However, in general, it is convenient to carry out the reaction at a temperature of 5 ° C to 200 ° C, better still, from room temperature to J5Q ° C. The time required for the reaction can also vary widely, depending on many factors, mainly the temperature of the reaction and the nature of the reagents and the solvent used. However, provided that the reaction is carried out under the preferred conditions indicated above, usually a period of 20 minutes will be sufficient to 20 hours, even better, from 30 minutes to 15 hours.

Step B4 In this step, which is an alternative for step (J), prepare the 1,4-d-oxo compound of the f-ornule (9) by carrying out the decarboxylation of the dioxoester compound of the formula (12) , prepared as described in step B3; At the same time as the hydrolysis. The hydrolysis reaction can be carried out using any acid or lcali commonly used in organic synthesis chemistry for reactions of this type.

Step B5 This step can be carried out when R in the dioxoester compound of the formula (12) is a hydrogen atom. In this step the compound of the formula (Ia-1) is prepared by reacting the dioxoester compound of the formula (12), prepared as described in step B3, with an aniline compound of the formula (10). This reaction is essentially equal to, and may be carried out in the same manner as, that described in step B2.

Step B6 In this step, the compound of the formula (Ia) of the present invention is prepared by hydrolyzing the ester portion of the compound of the formula (Ia-1), prepared as described in Step B5, to obtain the acid corresponding carboxyl, which is then decarboxylated. The hydrolysis reaction can be carried out by conventional methods such as those mentioned above. The decarboxylation reaction can be carried out using an acid or an alkali, or with heating, as is well known in the field of organic synthetic chemistry. For example, the method described in Yakugaku Zasshi, 93 (5), 584 -598 (1973)].

Method C In this method a compound of the formula is prepared (Ib) in which R3 is a halogen atom, measure the halogenation of a corresponding compound, wherein R3 represents a hydrogen atom, as shown in the following reaction scheme.

REACTION SCHEME C (Ia-2) (Ib) In the above formulas, R, R1, R2 and RA are defined previously, and R3 * »represents a halogen atom, for example, a volume of fluorine, chlorine, bromine or iodine.

Step Cl In this step, the desired compound of the formula (Ib) of the present invention is prepared by compounding the compound of the formula (Ia-2) of the present invention, which may have been prepared, for example, as described above. described in method A or method B. Examples of suitable halogenating agents include: fluoridating agents, such as xenon difluoride, gilding agents, such as chlorine, sulfuryl chloride or N-chlorosuccinimide; the brightening agents, such as bromine or N-bromosuccimrnide; and iodinating agents, such as iodine or N-iodosuccimide. The reaction can be carried out according to the methods described in detail in The Chemistry of Heterocyclic Compounds, lathe 48, part 1, pages 348-395, published by John Uiley 8 Sons.

METHOD D This is a method for preparing a compound of the formula (Ic-1), (Ic-2) or (Ic-3), wherein R 3 represents a halogenoalkyl group having from 1 to 6 carbon atoms.

REACTION D SCHEME (Ic-2) In the above formulas: R, R1, R2 and * are as previously defined; Rβ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and X * > represents a halogen atom, for example pJo, a fluorine, chlorine, bromine or iodine atom.

Step DI In this step an acrylic compound of the formula (13) is prepared by acylating a compound of the formula (Ia-2) of the present invention, which may have been prepared, for example, as described in method A or in method B. In this step a compound of the formula (13) in which ß represents a hydrogen atom can be preparedby reacting a Viismeier reagent, such as phosphorus-dimethyl-formate oxychloride, phosphorus-dirnethylformarnide oxybromide or oxalyl-dimethylformamide chloride, with the compound of the formula (Ia-2). Normally and preferably the reaction is carried out in the presence of a solvent. There is no particular restriction on the nature of the solvent to be used, as long as it can dissolve the reagents, at least to some extent. Examples of suitable solvents include hydrocarbons, such as rnetylene chloride, chloroform, carbon tetrachloride and 1,2-dichloroethane; and the amides, such as dirne ilforrnarnida. The reaction can be carried out on a wide scale of temperatures, and the precise reaction temperature is not critical to the invention. The preferred reaction temperature will depend on factors such as the nature of the solvent and the starting material or reagent used. However, in general, it is convenient to carry out the reaction at a temperature of -10 ° C to J50 ° C, even better, from 0 ° C to 100 ° C. The time required for the reaction can also vary widely, depending on many factors, mainly the temperature of the reaction and the nature of the reactants and the solvent used. However, provided that the reaction is carried out under the preferred conditions indicated above, a period of 15 minutes to 20 hours, better still, from 30 minutes to 10 hours, will suffice. Those compounds of the formula (13), in which Rβ represents an alkyl group having from 1 to 6 carbon atoms, preferably from 1 to 3 carbon atoms, can be prepared by reacting an acid anhydride or an acid halide of the formula (R 8 * CO )2? or R8"C0X" (wherein X "is as defined above and Rβ" represents an alkyl group having from 1 to 6 carbon atoms, preferably from 1 to 3 carbon atoms) with the compound of the formula ( Ia-2) in the presence of a Lei acid (for example, aluminum chloride, tin chloride or zinc chloride). Normally and preferably the reaction is carried out in the presence of a solvent. There is no particular restriction about of the nature of the solvent to be used, provided that it has no adverse effects on the reaction or on the reagents involved, and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include: aromatic hydrocarbons, such as benzene, toluene and methobenzene; the hydrocarbons have been hydrogenated, such as rnetiHeno chloride, chloroform, carbon tetrachloride and 1,2-d-chloroethane. The reaction can be carried out on a wide range of temperatures, and the precise reaction temperature is not critical to the invention. The preferred reaction temperature will depend on factors such as the nature of the solvent and the starting material or reagent used. However, in general, it is convenient to carry out the reaction at a temperature of -10 ° C to 150 ° C, better still, from 0 ° C to 100 ° C. The time required for the reaction can also vary widely, depending on many factors, mainly the temperature of the reaction and the nature of the reagents and solvent used. However, provided that the reaction is effected under the preferred conditions indicated above, it will usually take a period of 10 minutes to 20 hours, better still, 30 minutes to 10 hours.

Step D2 In this step a hydroxy compound of the formula (14) reducing the acyl group of the acylpyrrole compound of the formula (13), prepared as described in step DI. The reaction can be carried out using a reducing reagent (for example, sodium borohydride, lithium borohydride, lithium aluminum hydride, dusobutylaluminum hydride or borane) or using catalytic reduction with hydrogen. These reactions are well known in the field of synthetic organic chemistry and can be carried out using well-known techniques, for example, as described in detail by 3. Dale C3. Org. Chem., 333385 (1968) 1, the description of which is incorporated herein by reference.

Step D3 In this step the desired compound of the formula (Ic-1), which is a compound of the present invention, is prepared by halogenating the hydroxy group of the hydroxy compound of the formula (14), prepared taJ as described in step D2.

Suitable halogenating agents include fluorinating agents, such as diurethane fluoride inoazu e (DAST); the gilding agents, such as thiomyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, and triphenylphos / carbon tetrachloride; brightening agents, such as hydrobromic acid, thionyl bromide, phosphorus pbromide or triphenylphosphine / carbon tetraborine; and iodinating agents, such as hydroiodic acid or phosphorus tpyduro. These reactions are well known in The field of synthetic organic chemistry can be carried out using well-known techniques, for example, such as those described in detail by U. J. Middieton C 3. Org.

Chern., 40, 574 (1975) 1 and C. R. Noller and R. Dmsmore [Qrg. Synth , II, 358 (1943) 3, whose descriptions are incorporated herein by reference.

Step D4 In this step the desired compound of the formula (Ic-2), which is a compound of the present invention, is prepared by gem-dihalogenation of the carbonyl group of the acylpyrrole compound of the formula (13), prepared as such or described in step DI, using a suitable halogenating agent. Suitable halogenating agents include: fluorinating agents, such as sulfur tetrafluoride and DAST; gilding agents, such as phosphorus pentachloride and thionyl chloride / dirnetiifornarnide; pranking agents, such as boro tribromine; and iodinating agents, such as t rimeti lysilyl iodide. These reactions are well known in the field of synthetic organic chemistry and can be effected using well-known techniques, for example, as described in detail by U. 3. Middleton. Org. Chern., 40, 574 (J975) 3 and M. E. Jung and co-authors Í3. Org. Chem., 43, 3698 (1978) 1, the descriptions of which are incorporated herein by reference.

Step D5 In this step prepare a carboxylic acid compound of the formula (15), oxidizing an acylpyrrole compound of the formula (13), wherein Rβ is a hydrogen atom, prepared as described in step DI . Examples of suitable oxidizing agents which can be used in this step include potassium perrnanganate, chromic acid, hydrogen peroxide, nitric acid, silver oxide (I) and silver (II) oxide. These reactions are well known in the field of synthetic organic chemistry and can be carried out using well known techniques, for example, as described in detail by C. D. Hurd and co-authors 13. Arn.

Chern. Soc., 55, 1082 (1933) 1.

Step D6 In this step the desired compound of the formula (Ic-3), which is a compound of the present invention, is prepared by converting the carboxy group of the carboxylic acid compound of the formula (15), prepared according to step Ü5, to a tri-luoromethyl group. This step can be carried out using sulfur tetrafluoride, according to the methods described by C.-L.3. Uang CKOrg. React., 34, 319 (1985) 1.

METHOD E This illustrates the preparation of compounds of the formula (Id-1), (Id-2), (Id-3) or (Id-4), wherein 4 represents a substituted alkyl group and R 3 represents a hydrogen atom or a halogen atom.

REACTION SCHEME E In the above formulas: R, Rl, 2, R3 * > , R7, x * and? & they are as defined further back; 3c represents a hydrogen atom or a halogen atom; R9 represents an alkyl group having from 1 to 6 carbon atoms; Ri ° represents a halogen atom or an alkoxy group having from 1 to 6 carbon atoms; and Y represents a cyano group or a group of the formula -CO2 Rf, where R? it is as defined above.

Step El In this step a phenacylaceto-nitnide compound of the formula (17) is prepared by alkylating the cyano compound of the formula (16) with a phenacyl halide compound of the formula (7). This reaction is essentially the same as, and can be carried out in the same way as, and using the same reagents and the same reaction conditions as in step B3 of method B.

Step E2 In this step, a mopyrrole compound of the formula (18) is prepared by reacting the frylacetyl ityl compound of the formula (17), prepared as described in step F.l, with an aniline compound of the formula (10). This step can be carried out in the presence of a catalytic amount of hydrogen chloride, according to the methods described by K. ti. H. Hilmy and E. B. Pedersen CLiebi? S Ann. Chem., (1989), 1145-11461.

Step E3 In this step, a mixture of the formula (19) is prepared, removing an ammonia group from the compound or amino acid of formula (1 8), prepared as described in Step E2. This can be achieved by reacting an alkyl nitrite (for example, methyl nitrite, ethyl nitropyl, propyl nitrite, butyl nitrite, terbutyl nitrite or isoamyl nitrite), with the ammopyrrole compound of the formula (18). Normally and preferably the reaction is carried out in the presence of a solvent. There is no particular restriction on the nature of the solvent to be employed, provided that it has no adverse effect on the reaction or on the reagents involved, and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include: aliphatic hydrocarbons, such as hexane or heptane, aromatic hydrocarbons, such as benzene, toluene or xylene; the ethers, such as diethyl ether, d sopropyl ether, rahydrofuran or dioxane; and the amides, such as dimethylformamide or dimethylacetamide. We prefer them ethers The reaction can be carried out within a wide range of temperatures, and the precise temperature of the reaction is not critical to the invention. The preferred reaction temperature will depend on factors such as the nature of the solvent and the starting material or reagent used. However, in general, it is convenient to carry out the reaction at a temperature of -10 ° C to 200 ° C, better still, from room temperature to J50 ° C. The time required for the reaction can also vary widely, depending on many factors, mainly the temperature of the reaction and the nature of the reagents and the solvent used. However, as long as the reaction is carried out under the preferred conditions indicated above, a period of JO minutes at 20 hours, usually from 30 minutes to 15 hours, will usually suffice.

Step E4 In this step a halogen-pyrrole compound of the formula (20) is prepared by halogenating the pyrrole compound of the formula (19), prepared as described in step F3. This reaction is essentially equal to, and can be effected in the same manner as, and using the same reagents and the same reaction conditions as, in step Cl of method C.

Step E5 and Step E5 In these steps, an ester compound of formula (21) is prepared from a compound of formula (19), prepared as described in step F3, or (20), prepared as as described in step E4, where Y represents a cyano group, converting the cyano group to a protected carboxy group. The steps can be carried out using, for example, the compound of formula (19) or (20), suitable alcohols and acids, such as hydrochloric acid, sulfuric acid or p-toluensulonic acid, using the methods described by R. Adarns and AF Thal fOrg. Synth , I, 270 (1941) 1.

Step E7 In this step a carboxylic acid compound of the formula (22) is prepared, by hydrolyzing the ester compound of the formula (21), prepared as described in step E5 or E6. This reaction is essentially the same as, and can be carried out in the same way as, and using the same reagents and the same reaction conditions as, in step E! 4 of method B.

Step E8 In this preparation the desired compound of the formula (Id-2) of the present invention is prepared, converting the carboxy group of the carboxylic acid compound of the formula (22), prepared as described in step E7, to a group tpf J? orornet i lo. This reaction is essentially the same as, and can be carried out in the same manner as, and using the same reactants and the same conditions as the reaction, step D6 of method D.

Step E9 and Step E10 These steps provide an alternative method for the preparation of the compounds (Ed-2) of the present invention from the ester compound of the formula (21), prepared as described in step E5 or E6. In step F9, the protected carboxy group of the ester compound of formula (21) is first converted to a p (alk? Tet) metal group. This tp (alkyl thio net ion) group is then converted to a t-fluoromethyl group by an oxidant fluorodesulphuration reaction in step E10. This method is described in detail by DP Matthews, 3. P. WhiUen and 3. R. ricCarthy [Tetrahedron Letfers, 27 (40), 4861-4864 (1986) 1, the description of which is incorporated herein by reference.

Step Eli In this step the corresponding aldehyde compound of the formula (24) is prepared by reducing the protected carboxy group of the ester compound of the formula (21), prepared as described in step E5 or E6. For example, you can Carry out this step using a reducing agent, such as Lithium aluminum hydride, sodium aluminum hydride, lithium hydride and t-butyl lithium, hydride diisobutylium, etc., according to the methods described in detail by LI Zakharfcm and TN Khorlma [Tetrahedron Lett. , (962), 6191, whose description is incorporated herein with reference.

Step 2 In this step the desired compound of the formula (Id-3) is prepared by ger-dihalogenation of the aldehyde compound of the formula (24), prepared as described in step Eli. This reaction is essentially equal to, and may be carried out in the same manner and using the same reactants and the same reaction conditions as in step D4 of method D.

Step El3 In this step a hydroxy inet.io compound of the formula (Id-1), a desired compound of the present invention, is prepared by reducing the protected carboxy group of the ester compound of the formula (21), prepared as described in step E5 or E6. For example, this step can be carried out using a reducing agent, such as lithium aluminum hydride, lithium borohydride or hydride of hydrotreamer, according to the methods described in detail by R. F-.

Nystrorn and co-authors [3. Arn. Chem. Soc. , 1, 3245 (1945) 1, whose 08 description is hereby incorporated as a reference. Step In this step, the halogenornetium compound or the alkoxykethethio compound of the formula (Td-4), which are compounds of the present invention, is prepared by halogenating or etherifying a hydroxymethylene compound of the formula (Td-1), prepared such as described in step F13. In this step, the halogenation reaction can be carried out in the same manner as, and using the same reagents and the same reaction conditions as in step D3 of method D. The reaction of etepfication can be carried out by reacting the hydroxymethyl compound of the formula (Id-1) with an alkyl halide. Normally and preferably the reaction is carried out in the presence of a solvent. There is no particular restriction on the nature of the solvent to be employed, provided that it has no adverse effect on the reaction or on the reagents involved, and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include: Aliphatic hydrocarbons, such as hexane, heptane and petroleum ether, aromatic hydrocarbons, such as benzene, toluene or xylene; the ether, such as diethyl ether, dusopropyl ether, tetrahydrofuran and dioxane; and the amides, such as dirnethylformamide or dimethylacetamide. The ethers and the amides are preferred.

The reaction is carried out in the presence of a base. There is also no particular restriction on the nature of the bases used, and any base commonly employed in the reactions of this type can also be used here. Examples of such bases include: alkali metal hydrides, such as lithium hydride, sodium hydride or potassium hydride; Alkaline metal alkoxides, such as sodium nitroxide, sodium ethoxide, potassium terbutoxide; and the tertiary amines, such as tpetilarní na, tributila ma, pipdina, picoline and 4- (N, N-d? met? iarn? no) ?? pdina From here, they prefer sodium hydride or potassium terbutoxide. The reaction can be carried out within a range of temperatures, and is not critical to the invention. The precise temperature of the reaction. The preferred reaction temperature will depend on such factors as the nature of the solvent and the starting material or reagent used. . However, in general, it is convenient to carry out the reaction at a temperature of -10 ° C to 200 ° C, better still, from 0 ° C to 150 ° C. The time required for the reaction can also vary widely, depending on many factors, mainly the temperature of the reaction and the nature of the reagents and solvent used. However, as long as the reaction under the preferred conditions indicated above is mild, a period of 30 minutes to 48 hours, better still, from 1 to 24, will usually suffice. hours, Step E15 In this step, compound of the formula (Id-1) is oxidized to give the compound of the formula (24). This can be carried out using an oxidizing agent, for example, chromic acid, manganese dioxide or dimethyl sulfoxide, according to the methods described in detail by S. Bartel and F. Bohlrnann [Tetrahedron Lett. (1985), 6851. The following methods F a 3 and L illustrate the preparation of compounds of the formula (II): METHOD F REACTION SCHEME F (27) (28) In the above formulas, R, R1, R2, R3 and R1 are such as was previously defined. The reactions of step Fl, step F2, step F3 and step F4 are essentially the same as those of step Al, step A2, step A3 and step A4, respectively, and can be carried out using the same reagents and Same reaction conditions.

METHOD G This illustrates the preparation of a compound of the formula (IIa-1), wherein R3 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a substituted alkyl group having from 1 to 6 atoms of carbon and having at least one of its constituents selected from the group consisting of substitutes is alpha, as they were defined and exemplified backwards.

REACTION SCHEME G In the formulas, R, R1, R2, R3 «, R *, RS, R6, R7 and Xa are t as defined above. Step Gl In this step a 1,4-d-oxo compound of the formula (33) is prepared by alkylating the beta position of an enarnine compound of the formula (32), using a phenacyl halogen compound of the formula ( 31). This reaction is essentially the same as, and can be effected in the same way and using the same reactants and the same reaction conditions as in step Bl of method B.

Step G2 In this step the compound of the for-rn? La (IIa-1), which is a compound of the present invention, is prepared by dehydration-condensation of the 1,4-d-oxo compound of the formula (33) , prepared as described in step Gl, and the aniline compound of formula (25) to close a ring. This reaction is essentially equal to, and can be effected substantially in the same manner as, using the same reagents and the same reaction conditions as in step B2 of method B.

Step G3 In this step a dioxoester compound of The formula (35) alkylating the alpha position of a compound of Formilic ester of the formula (34) with the phenacyl halide compound of the formula (31). This reaction is essentially equal to, and can be carried out in the same manner as, and using the same reagents and the same reaction conditions as, in step B3 of method B.

Step G4 In this step, the 1,4-d-oxo compound of the formula (33) is prepared by carrying out the decarboxylation of the dioxoester compound of the formula (35), prepared as described in step G3, Same time as Hydrolysis. This reaction is essentially the same as, and can be carried out in the same manner and using the same reactants and the same reaction conditions as in step B4 of the β-method.

METHOD H This illustrates the preparation of a compound of formula (Ilb), where R3 represents a halogen atom.

REACTION SCHEME H (Il) In the above formulas, R, R1, R2, R3 < > and R * are as defined before.

Step Hl In this step a mtropirrol compound of the formula (36) is prepared by nitrating the compound of the formula (TIa-2), which may have been prepared as described in the method G [a compound of the formula (IIa -1), where R3 * represents a volume of hydrogen! This step is carried out using a conventional nitrating agent, for example, nitric acid, fuming nitric acid or nitp acid with acetic anhydride, according to the methods described in detail in The Chernis ry of Heterocyclic Compounds, to 48, Part 1, pages 330-345, published by- 3ohn (Jiley R rons.

Step H2 In this step, an aninopyrrole compound of the formula (37) is prepared by reducing a nitro group of the nitropyrrole compound of the formula (36) prepared as described in step Hl. Methods for reducing nitro groups to ammo groups are well known in the field of synthetic organic chemistry, and any of the conventional methods can be used.

Step H3 In this step, a compound of arnmohalogenopyrrole of the formula (38) is prepared by halogenating the arninopyrrole compound of the formula (37), prepared as described in step H2. This reaction is essentially equal to, and can be carried out in the same manner as, and using the same reagents and the same reaction conditions as step Cl of method C.

Step H4 In this step the desired compound of the formula (Ilb) of the present invention is prepared, eliminating the amino group of the aminoharomopyrrole compound of the formula (38), prepared as described in step H3. This reaction is essentially equal to, and can be effected in the same manner and using the same reagents and reaction conditions as, in step E3 of method E.

METHOD I This method illustrates the preparation of a compound of the formula (IIc-1), (IIc-2), (IIc-3) or (IIc-4), wherein R * represents a substituted alkyl group having from J to 6 carbon atoms, and substituted with at least one of its substituents selected from the group consisting of the substituents alpha, and R3 represents a hydrogen atom or a halogen atom.

(Four. Five) REACTION SCHEME I (continued) i on In the above formulas, R, Rl, R2, 3 b t 3 c t 7 t R9 Ri o,? > t xb and Y are such or were defi two previously.

Step II In this step, a phenyacylacetonyl compound of the formula (40) is prepared by alkylating the cyano compound of the formula (16) with a phenacyl halide compound of the formula (39). This reaction is essentially equal to, and can be effected in the same manner as, and using the same reactants and reaction conditions as in, step El of method E.

Step 12 In this preparation, a novel arnide compound of the formula (41) is prepared by reacting the phenyacylacetonyl compound of the formula (40), prepared as described in step II, with the aniline compound of the formula (25). This reaction is essentially the same as, and can be carried out in the same manner as, and using the same reactants and the same reaction conditions as, in step E2 of method E.

Step 13 In this step prepare a compound composed of ainmohaloyeno of the formula (42), halogenating the aminopyrol compound of the formula (41), prepared as described in step 12. This reaction is essentially equal to that of, and can be carried out in the same manner and using the same reagents and the same reaction conditions as in step H3. of the method H.

Step 14 and step 15 In these steps a compound of the formula (43) and a compound of the formula (44) are prepared, respectively, by removing the ammo group of the aminopyrrole compound of the formula (41) and the arninohalogen compound of the formula (42); respectively. This reaction is essentially equal to that of, and can be carried out in the same manner as, and using the same reagents and the same reaction conditions as in, step H4 of the H method.

Step 16 and Step 17 In these steps an ester compound of the formula (45) is prepared from the pyrrole compounds of the formula (43) and (44), wherein Y represents a cyano group, converting the cyano group to? n protected carboxy group. This reaction is essentially identical to that of, and can be carried out in the same manner as, and using the reactive metals and the same reaction conditions as in steps E5 and E6 of method E.

Step 18 and Step 19 In these steps a compound is prepared triromethyl of the formula (IIc-2), the desired compound of the invention, from the ester compound of the formula (45), prepared as described in step 16 or 17, by means of a compound carboxylic acid of the formula (46). This reaction is essentially equal to that of, and can be carried out in the same manner as, and using the same reagents and the same reaction conditions as in steps E7 and E8 of method E.

Step 110 and Step 111 In these steps, a dihalogenomethyl compound of the formula (IIc-2) is prepared from the ester of the formula (45), prepared as described in step 16 or 17, by ? n compound tp (alkyl t? o) met? what of the formula (47). This reaction is essential as well as that of, and can be carried out in the same way as, and using the same reagents and the same reaction conditions as in steps E9 and E10 of method E.

Step 112 e 113 In these steps, a dihalogenornetium compound of the formula (IIc-3), a desired compound of the present invention, is prepared from the ester compound of the formula (45), prepared as described in step T6 or T7, by means of an aldehyde compound of the formula (48). This reaction is essentially equal to that of, and can be perform in the same manner as, and using the reactive metals and the same reaction conditions as in steps Eli and E12 of method E.

Step 114 and Step 115 In these steps the desired compound of the formula (TIc-4), which is a compound of the present invention, is prepared from the ester compound of the formula (45), prepared as described in step 16 or 17, by means of a hydroxymethyl compound of the formula (IIc-1), which is also a compound of the present invention. This reaction is essentially equal to that of, and can be carried out in the same manner and using the same reagents and the same reaction conditions as in steps 3 and E14 of method E. The aldehyde compound of the formula 24), in the method E, and the aldehyde compound of the formula (48), in the method I, the formulas (Td-1) and (IIc-1) can also be prepared from the corresponding compounds ), respectively, converting the hydroxy group to a formal group. The reaction in which a hydroxyrnethyl group is converted to a forrniium group can be carried out using an oxidizing agent, for example, chromic acid, manganese dioxide or dinethyl sulfoxide, according to the methods described in detail by B. Bartel and F. Bohl ann CTe rahedron Lett. , (1985), 6851.

METHOD 3 This is an alternative method to the G method, and prepares a compound of the formula (IIa-3), in which R3 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, or a substituted alkyl group , which is substituted with at least one suetuent selected from the group consisting of the alpha substituents, defined above, and * represents an alkyl group having 6 carbon atoms, a substituted alkyl group having from 1 to 6 atoms of carbon and which is substituted with at least one substituent selected from the group consisting of the alpha substituents, defined above, or an aralkyl group.

REACTION SCHEME 3 R2_ 0¿i_ R¿H-X¡ > CH R7) 2 - • R2-C- tCH-CH (COOR7) 2 Step Jl (31) (50) Hydrolysis Decarboxilation Step J3 R3a R4a -CH-H-CHO (55) (pa-3) In the previous formulas: R, Ri, R2, R3 », R7 and xa SOn as previously defined; and R4 * represents an alkyl group having from 1 to 6 carbon atoines, a substituted alkyl group having from 1 to 6 carbon atoms, which is substituted with at least one substituent selected from the group consisting of alpha substituents, defined above, or an aralq? i lo group.

Step 31 In this step a phenolic-alonic acid diester compound of the formula (50) is prepared by alkylation of a malonic acid diester compound of the formula (49) with a phenacyl halide of the formula (31) :: This reaction is essentially equal to La de, and can be made from The same way and using the same reagents and the same reaction conditions as in, step B3 of method B.

Step 32 In this step a compound of the for-rn? (52) by the addition of the fanacilrnalonic acid diester compound of the formula (50), prepared as described in step 31, with a halide compound of the formula (51). This reaction is essentially equal to that of, and can be carried out in the same way and using the same reagents and the same reaction conditions as in step B3 of method B.

Step 33 In this step a beta-ketoester compound of the formula (53) is prepared by hydrolysis of the compound of the formula (52), prepared as described in step 32, followed by the decarboxylation of the product. This reaction is essentially equal to that of, and can be carried out in the same way and using the same reagents and the same reaction conditions as in steps B4 and B6 of method B.

Step 34 In this step, a diol compound of the formula (54) is prepared by reduction of the ketone and ester parts of the beta-ketoester compound of the formula (53), prepared at as described in step 33. This reaction is essentially equal to that of, and can be effected in the same manner and using the same reagents and the same reaction conditions as in, step EJ3 of method E.

Step 35 In this step a ketoaldehyde compound of the formula (55) is prepared by oxidation of the two hydroxy groups of the diol compound of the formula (54), prepared as described in step 34. This reaction can be carried out by well-known methods, using an oxidizing agent (such as chromic acid, manganese dioxide or dimethyl sulfoxide), for example, as described by E. 3. Corey, G. Schmidt and co-authors CTetrahedron l.et. , (1979), 3991, whose description is incorporated herein with reference.

Step 36 In this step a compound of the formula (IIa-3), which is a compound of the present invention, is prepared by cyclizing the ketoaldehyde compound of the formula (55), prepared as described in step 35, and a aniline compound of the formula (25), ba or condensation and dehydration conditions. This reaction is essentially equal to that of, and can be carried out in the same manner and using the same reagents and the same reaction conditions as in step B2 of method B.

METHOD K In this method, a compound of the formula (Ie-1) or (Ie-2) are prepared, which are compounds of the formula (T), wherein R 2 represents a phenyl group substituted with a mercapto group, or with? n alkanoylthio group; and R3 represents a hydrogen atom, an alkyl group having 6 carbon atoms or a substituted alkyl group, having 6 carbon atoms, which is substituted with at least one constituent selected from the group consisting of of The alpha stents, previously defined.

REACTION SCHEME K R, 1, R 3 *, R * and Xa are such as defined above; and RII represents an alkanoyl group having from 7 to 5 carbon atoms.

Step Kl In this step, a compound of the formula (57) is prepared by dehydrating and condensing a benzaldehyde compound of the formula (1) with a dehydrated compound of do not aniline of the formula (56). This reaction is essentially the same as that of, and can be carried out in the same way and using the reactive metals and the same reaction conditions as in step A of the all method A.

Step K2 In this step, an anilinonityl disulfide compound of the formula (58) is prepared by the addition of hydrogen cyanide, also composed of the formula (5 /), prepared as described in step Kl. This reaction is essentially equal to that of, and can be carried out in the same way and using the same reagents and the same reaction conditions as in step A2 of method A.

Steps K3 and K4 In these steps, a pyrrole disulfide compound of the formula (60) is prepared by reacting an anilinonitopul disulfide compound of the formula (58), prepared as described in step K2, with an aldehyde or ketone compound to fa, beta-? of the formula (5), to give a pyrrolidine disulfide compound of the formula (59), which is then dehydrated and dehydrogenase. These reactions are essentially the same as those of, and can be carried out in the same way and using the reactive isms and the same reaction conditions as in steps A3 and A4 of method A.

Lll Step K5 In this step a compound of the formula (Te-L), which is a compound of the present invention, is prepared by reduction of a pyrrole disulfide compound of the formula (60), prepared as described in step K4 This reaction can be carried out by well known methods, using a reducing agent (such as sodium borohydride, lithium borohydride, lithium aluminum hydride, diisobutyl aluminum hydride or borane), for example, as described by 3. D'Arnico L ~ 3 Org. Chern. , 26, 3436 (1961) 1.

Step K6 In this step a compound of the formula (Te-2), which is also a compound of the present invention, is prepared by the canoi lation of the mercapto group of the compound of the formula (Te-1), which is a compound of the present invention, and which was prepared as described in step K5. This reaction can be carried out by conventional methods, using an alkanoyl halogen compound of the formula (61) or the corresponding acid anhydride compound of the formula (62).

METHOD L This method provides an alternative method to the method G for preparing a compound of the formula (33).

REACTION SCHEME L 1) Mg CH3 2) R2CN (65) or R2CO? A (66) or 2c? NOCH3 (67) Step L2 In the above formulas, X », R2, R3 R *? N such as was defined earlier.

Step Ll In this step a brornoacetal compound of the formula (64) is prepared by reacting an unsaturated aldehyde compound of the formula (63) with hydrogen bromide gas in ethylene glycol. The reaction can be carried out using the Taylor method and co-authors [3. Org. Chern., 48, 4852-4860) (1983) 1.

Step L2 In this step a ketoacetal compound of the formula (68) by reacting the bromoacetal compound of the formula (64), prepared as described in step Ll, with metallic magnesium, to prepare a Gngnard reagent and then reacting said Grignard reagent with a compound of mtplo of the formula (65), with an acyl halide compound of the formula (66) or with an amide compound of the formula (67). This reaction can be carried out by the method of Kruse and co-author [Hete rocy cies, 26, 3141-3151 (1987) 1.

Step L3 In this step a 1,4-d-oxo compound of the formula (33) is prepared by hydrolysis of the acetal portion of the ketoacetal compound of the formula (68), prepared as described in step L2. This can be done using any conventional method of hydrolysis, using an acid. Alternatively, the ketoacetal compound of the formula (68) can be used in step G2, instead of the compound of the formula (33). In all the above reactions, where R 1 represents an alkyl group having 6 carbon atoms, it is possible to use as a starting material a compound in which the alkylsulfonyl group (-SO 2 -alkyl) is replaced by a group alkylthio (-S- to chyle). In all those CASES, the reaction can be carried out as described, and The alkylthio group can then be oxidized by well known and conventional methods to an alkylsulphonyl group at any stage of the reaction sequence. For example, the oxidation of the alkylthio group to the alkylphosphonyl group can be carried out by reacting the alkylthio compound with two or more equivalents of an oxidizing agent. There is no particular restriction on the nature of the oxidizing agents used, and any oxidizing agent commonly used in reactions of this type can also be used here. Examples of those oxidizing agents include: peracids, such as peracet acid, perbenzoic acid or chloroperbenzoic acid; hydrogen peroxide, and alkali metal perhalogenates, such as sodium metaperchlorate, sodium metaperiodate or potassium rnetaperiodate. Preferred are peracids or hydrogen peroxide, particularly m-chloroperbenzoic acid. Normally and preferably the reaction is carried out in the presence of a solvent. There is no particular restriction-about the nature of the user to be employed, provided that it has no adverse effect on the reaction or on the reagents involved, and that it can dissolve the reagents, at least to some extent. . Examples of suitable solvents include: Aliphatic hydrocarbons, such as hexane, heptane or petroleum ether, aromatic hydrocarbons, such as benzene, toluene or xylene.; Halogenated hydrocarbons, such as rnetienene chloride, chloroform, carbon tetrachloride or dichloroethane; alcohols, such as methanol, ethane, propanol or butanol; the esters, such as ethyl acetate, propyl acetate, butyl acetate or ethyl propionate; The carboxylic acids, such as acetic acid or propiomo acid; water, or a mixture of two or more of these solvents. Halogenated hydrocarbons (in particular ethylene chloride, chloroform, dichloroethane) or carboxylic acids (in particular acetic acid) are preferred. The reaction can be carried out within a wide range of temperatures, and the precise temperature of the reaction is not critical to the invention. The preferred reaction temperature will depend on factors such as the nature of the solvent and the starting material or reagent used. However, in general, it is convenient to carry out the reaction at a temperature of -20 ° C to 150 ° C, better still, from 0 ° C to 100 ° C. The time required for the reaction can also vary widely, depending on many factors, mainly the temperature of the reaction and the nature of the reagents and solvent used. However, as long as the reaction is carried out under the indicated preferred conditions, usually a period of 10 minutes to 10 hours, better still, of 30 minutes to 5 hours will suffice. Furthermore, in all the above reactions it is possible to use a compound in which R represents a phenyl group substituted with an alkali group, and then convert this to a 11. 6 alkylsulfinyl group, at any stage of the reaction sequence, as described hereinabove. The reaction can be carried out as described above, but the amount of oxidizing agent is from 0.8 to 1.2 equivalents per equivalent of the alkyl thio compound.

BIOLOGICAL ACTIVITY The derivatives of 1,2-d? feni J? Role and its pharmacologically acceptable salts of the present invention act as selective inhibitory agents for cyclooxy-2-genase and / or as suppressive agents of inflammatory cytokine production, and are thus effective for prophylaxis and therapy. diseases mediated by c? cJoox? genasa-2 and / or by inflammatory cytokines .. Additionally, they have the ability to inhibit the production of Leucot rà © nos and to inhibit - 116 - Bone resorption. Consequently, these compounds can serve as analgesics, as anti-inflammatory agents, as antipyretics and / or as anti-allergic agents. Additionally, the compounds of the present invention may be used for the treatment or prophylaxis of diseases that involve, or are the result of, bone resorption, such as osteoporosis, reurnatoid arthritis, and osteoarthritis. These types of analgesics, anti-inflammatory and / or antipyretic agents exhibit effects not only on inflammatory diseases, such as pain, pyrexia and edema, but also on chronic inflammatory diseases, such as chronic rheumatoid arthritis and west-arthritis, allergic inflammatory diseases, such as asthma, sepsis, psoriasis, diversae autoimmune diseases, systemic lupus erythematosus, juvenile onset diabetes, autoimmune intestinal diseases (such as ulcerative colitis, Crohn's disease ), viral infection, tumors and glomerulonephritis. The biological activity of the compounds of the present invention is illustrated by the following experiments.

EXPERIMENT 1 INHIBITOR ACTIVITY ON CYCLOQXYGENASE-1 P FROM MICROSOMES OF SEMINAL CARNIVAL VESICULAR (RSVM) AND CYCLOOXYGENASE-2 HUMAN RECOMBINANT (IN VITRO TEST) In order to prepare cyclooxygenase-1 microsomes (COX-1), seminal sheep vesicles were blended by means of a blender. To prepare the cyclooxygenase-2 microsomes (COX-2), an expression vector containing the human COX-2 gene was introduced into COS cells. The cells were homogenized by sonic treatment after 66 hours of culture. Then the microsomes were prepared according to conventional methods. The enzymatic activity was analyzed in the following way.

The analysis mixture contained 10 μl of C0X-1 or C0X-2 microsomes (5 to 15 ug), 2 μl of sample dissolved in dimethyl sulfoxide, 50 μl of 200 mM Tris (pH 7.6), 10 μl of 20 Reduced glutathione M, 10 μl of 10 mM epinephrine and 15.5 μl of distilled water. After pre-incubation at 37 ° C for 15 minutes, 2.5 μl of 10 μM of arachidonic acid (dissolved in ethanol) (final volume of the mixture 100 μl) was added to the mixture and allowed to react at 37 ° C for 30 minutes . The final concentrations of dimethyl sulfoxide and ethanol were 2% and 2.5%, respectively. Then, 15 μl of 0.2 M HCl, cooled with ice, was added to the reaction mixture to stop the reaction; and the mixture was cooled to 4 ° C for 5 minutes. Then 15 μl of a 0.2 M aqueous solution of sodium hydroxide was added to neutralize the pH. The amount of PGE2 in the reaction mixture was measured using an ELISA (Cay an) kit available commercially. The IC 50 was calculated from the regression line determined by the inhibition rates of PGE 2 formation and the concentrations of the compound.

The results are shown in table 3 TABLE 3 Example Inhibitory effect Inhibitory effect Selectivity No. on COX-1 on COX-2 (C0X-1 / C0X-2) CCI50 (μM)] CCIso (μM) l 85 0.023 3696 38 > 100 0.023 > 4348 52 > 100 0.016 > 6250 56 > 100 0.018 > 5556 58 6.3 0.019 332 62 1.5 0.0097 153 65 13 0.015 867 73 3.0 0.025 120 80 25 0.011 2273 103 3.7 0.01 370 108 6.0 < 0.01 > 600 109 3.8 0.023 165 A > 100 > 100 Compound A is 5-methyl-2-phenyl-1- (4- sulo-phenyl) pyrrole, which is described in the German patent O:. 'K' No. 1,938,904, mentioned previously. In this test, the compound of the present invention exhibited excellent selective inhibitory effects for cyclooxygenase-2. 1. twenty EXPERIMENT 2 INHIBITOR EFFECT ON THE PRODUCTION OF CYTOCHINE IN HUMAN PERIPHERAL MONOCYTES (IN VITRO TEST) (1) Peripheral blood was collected from healthy human volunteers in the presence of heparin. After mixing it with an equal volume of phosphate buffered saline (PBS, Nissui Pharmaceutical), the mixture was layered on a Ficoll Paque medium (Pharmacia) at a rate of 2: 1 and centrifuged at 520 xg at 25 ° C. during 20 minutes. After centrifugation, the monocyte layer was centrifuged and suspended in RPMI 1640 (Nissui Pharmaceutical) containing 10% fetal calf serum (FCS). The monocytes were washed once with the same medium, placed in a plastic Petri dish, previously treated with human plasma and incubated for 2 hours in the presence of 5% CO2, to make them adhere to the disc. After incubation, the diethyl Petri was washed twice with PBS to remove the non-adherent cells. Subsequently, PBS containing 5% FCS and 0.2% EDTA was added to the Petri dish and the disc was left undisturbed for 15 minutes at 4 ° C. Monocytes were recovered from the disc by pipette. Then it was finally suspended in RPMI 1640 at a concentration of 1.25 x IOS cells / milliliter. (2) Culture of human monocytes.

A solution of 40 μl of the test compound and 40 μl of lipopolysaccharide (LPS, E. coli, 0.26.B6, Difco) adjusted to a final concentration of 10 μg / ml was added to 320 μl of a cell suspension. The resulting mixture was then cultivated for 20 hours in the presence of 5% CO2 and the supernatant was removed at the end of the culture to analyze IL-lß and TNFa. The test compound was dissolved in dinethyl sulfoxide and diluted to a factor of 100 with FCS to reach it times the final concentration (the final concentrations of dimethyl sulfoxide and FCS were 0.1% and 10%, respectively). (3) Measurement of cytokine in the supernatant medium. The amount of IL-lβ was measured with a commercially available ELISA (Cayman) kit, after diluting the supernatant by a factor of 15 or 30 with the ELISA regulator.

The amount of TNFa was measured similarly by a team ELISA (Genzyme) after diluting the supernatant by a factor of 2. The IC 50 was calculated from the regression line determined by the inhibition regimes and the concentrations of the test compound. The results are summarized in Tables 4 and 5. In this test, the compound of the present invention exhibited excellent inhibitory effects on the production of inflammatory cytokine (IL-lß and TNFa).

TABLE 4 Example No. Inhibition of IL-lß production (%) Dosage: 10 μM 7 42.6 41 51.2 90 62.2 A 24.2 TABLE 5 Example No. Inhibition of TNFa production (%) Dosage: 10 μM 49 40.9 54 54.7 68 42.6 81 46.1 105 41.8 123 43.6 A 13.9 EXPERIMENT 3 ANALGESIC EFFECT ON PAIN BY INFLAMMATION WITH YEAST IN RATS (RANDALL-SELITTO METHOD) (IN VIVO TEST) (1) The test compound The compound was suspended in 0.5% tragacanth and orally administered at a volume of 5 ml / kg. Only 0.5% tragacanth, as a vehicle, was administered to the control group. (2) Animals Uistar-Imamichi rats (males, 5 weeks of age, body weights: 80-100 g) were used in this test. (3) The test method The test was carried out according to the method of LJinter and Flataker Í3. Pharmacol. Exp. Ther. 150, 165-171 (1965)], which is a modification of the original method of Randall-Selitto CArch. Int. Phar acodyn. Ther. 111, 405-419 (1957)]. The rats were fasted for 16 hours before use. Inflammation was induced by subcutaneous injection of 0.1 ml of a 20% suspension of brewer's yeast (Sigma) in the right leg of the animal. After 4.5 hours, increasing pressure was applied to the inflamed leg, at a constant speed, using an Analgesy meter (registered trademark) (Ugo-Basile Co.). The pressure at which the animal exhibited a squealing reaction was measured and considered to be it was the level of pain (units: g). To the rats that exhibited a pain threshold of less than 200 g (average: 60 to 120 g), the compounds were administered immediately in oral form and the pain threshold values 0.5, 1 and 2 hours after administration were measured. . The average of the pain threshold values at each time point (0.5, 1 and 2 hours) in a control group was calculated first. If the pain threshold value exceeded twice the average control value at the same time point, even once in the drug-treated groups, then the animal was judged to indicate efficacy. Drug efficacy regimens were estimated using the Blake I3 evaluation method. Phar e. 19, 367-373, (1967) 1. The results are shown in table 6.

TABLE 6 ANALGESIC EFFECT ON PAIN BY INFLAMMATION BY YEAST IN RATS (RANDALL-SELITTO METHOD) Example Efficiency regime No. (No. of animals in which the drug was effective / No. of animals used in the test) Dosage: 12.5 mg / kg 7 5/5 18 5/5 19 5/5 52 5/5 62 5/5 65 5/5 66 5/5 67 5/5 69 5/5 71 5/5 77 5/5 78 5/5 79 5/5 82 5/5 83 5/5 84 5/5 85 5 / 5 86 5/5 87 5/5 88 5/5 97 5/5 100 5/5 101 5/5 129 5/5 130 5/5 A 1/5 EXPERIMENT 4 PROOF OF EDEMA IN PATA, INDUCED BY CARRAGENINA (IN VIVO TEST) The same test compounds that were tested in the Randall-Selitto test of experiment 3 were subjected. Rats? Istar-Imamichi (males, 6 weeks of age, body weights 110-120 g) were used in this test. The method of Uinter and coauthors was modified slightly [Proc. Soc. Exp. Biol. Med. 111, 544-547 (1962)] to perform the test [Sankyo Annual Research Report 39, 77-111 (1989)]. The rats were fasted for 16 hours before use. Inflammatory edema was induced by subcutaneous injection of 0.05 ml of a 1% solution of carrageenan (Viscarin 402) into the right forepaw of the animal. The test compounds were administered orally 30 minutes before the injection of carrageenan. The volume of the right leg was measured with? N Plethys ometer (registered trademark) (Ugo-Basile Co.), just before administration of the test compound and 3 hours after the injection of carrageenan, to determine the intensity of the edema [(volume of the right leg after 3 hours / volume of the right leg before injection) - 1], The inhibition rate (percent) at each dose was calculated and is shown in table 7.

TABLE 7 INHIBITOR EFFECT ON EDEMA IN PATA INDUCED BY CARRAGENINA, IN RATS Example No. Inhibition regime (%) Dosage: 50 mg / kg 7 56 17 67 18 53 19 65 41 60 52 65 62 55 64 60 67 64 69 55 73 72 75 57 76 56 78 66 82 78 83 70 84 66 85 73 86 64 88 61 90 64 96 60 97 63 98 55 99 57 100 57 103 56 104 69 105 68 108 58 109 77 120 62 121 59 129 62 130 73 A 14 EXPERIMENT 5 PROOF OF PAIN INDUCED BY ESCALATION (IN VIVO TEST) The test was carried out according to the method of Iizuka and Tanaka [3pn. 3. Pharmacol. 7_0, 697 (1967) 1. The test compound was administered in the same manner as in experiment 3. Amigo-istar-I male rats were used (4 to 5 weeks of age, body weights approximately 100 g). The right forepaw of the animal was immersed in hot water at 57 ° C for 6 seconds to induce scalding, under 1. 9 aneetesia with ether. Two hours later the climbing leg of the rat was irritated by immersing it in hot water at 40 ° C for 5 seconds, and the animal was returned to the cage. The behavior of the animal was observed for 30 seconds. Lifting the climbing leg or licking it without coming into contact with the metal cage were considered to be responses to pain. It was determined that the pain response time was the total time of the pain response during the 30-second observation period. After selecting those animals that exhibited a favorable response to pain two hours after the scalding was induced, the animals were given a test compound by oral administration.

The pain response time was re-measured 1 and 2 hours after dosing, and the mean value was determined. Using the mean values, the inhibition regimes were calculated with respect to the control group. The DIso was calculated from the regression line determined by the inhibition regimes and the dosies. The results are shown in table 8.

TABLE 8 ANALGESIC EFFECT OF PAIN INDUCED BY ROCK ESCALATION Example No. DIso (mg / kg) 52 1.1 67 1.6 EXPERIMENT 6 ANTIPREHETIC EFFECT ON YIELD-INDUCED FEVER (IN VIVO TEST) 5 The method of Roszkowski and co-authors was slightly modified [3. Pharmacol. Exp. Ther. 179, 114 (1971)] to carry out the test. The test compound was administered in the same manner as in experiment 3. It was used in the test Uistar-Imamichi male rats (6 weeks of age, body weights: approximately 120 g). It was suspended (brewer's yeast, Sigma) in physiological saline at a concentration of 25%, finely ground in an agate mortar and injected subcutaneously into the backs of the rats.

LS after anesthetizing them with ether at a volume of 2 l / rat.

The rats were left fasting after the yeast injection. The next day (19 hours after the injection of the yeast) a thermistor thermometer of the catheter type (3apan Koden, MGA III) 5 ml was inserted into the rectum to measure the temperature of the animals. Those animals that exhibited a fever of 1.5 ° C or more, compared to normal animals, were selected and grouped in such a way that the mean fever temperatures of each group were approximately equal. The temperatures were measured Rectal JC 1 and 2 hours after administration of the test compound and fever temperature was calculated by subtracting the Normal temperature of healthy animals, measured simultaneously. The inhibition rate of the group treated with the compound, with respect to the control group, was calculated using the mean value of 1 and 2 hours after the dosage. These results are shown in table 9.

TABLE 9 ANTIPREHETIC EFFECT ON YEAST INDUCED FEVER (IN VIVO TEST) 10 Example No. Inhibition regime (%) Dose: 0.4 mg / kg 52 82 67 78 15 84 64 EXPERIMENT 7 IRRITATING EFFECT ON THE GASTRIC MUCOSA (IN VIVO TEST) Experiments were carried out according to the method described by 3ahn and Adrián [Arzneim-Forsch, 19, 36, (1969) 1. Uistar male rats weighing approximately 120 g were fasted for 16 hours before the experiment. The drugs were administered orally to the rats as : > described in experiment 3. Three and a half hours after dosing the animals were sacrificed under anesthesia with ether and the stomachs were placed in 1% for alina. The stomach cutting along the greater curvature and the number and length of lesions were counted under a microscope (6.3 X 10). The ulcerogenicity of each animal was determined according to Hitchens and co-authors [Phar acologist 9_, 242 (1967)]. The incidence was determined as the regimen of rats with four or more ulcers of more than 0.5 mm in length, and the DU50 (doses producing an incidence of 50%) was calculated from the incidence, and by the probit method (= unit of probability). The results were summarized in table 10.

TABLE 10 IRRITATING EFFECT ON THE G STRICOSE MUCOSA Example No. DUso (mg / kg) 65 > 100 66 > 100 67 > 100 69 > 100 70 UOO 71 > 100 76 UOO 77 UOO 78 uoo 79 uoo 80 uoo 82 uoo 84 uoo 103 uoo 119 uoo 121 uoo EXPERIMENT B OSAS REBORSE ANALYSIS (IN VITRO TEST) Bone resorption analysis was carried out according to the method of Kitamura and co-authors [Bone 14, 829-834, (1993)]. The tibia and femur of ICR mice, from 18 to 20 days of age, were removed by scissors and shaken for 30 seconds in 10 ml of culture medium (D-MEM containing 10% FCS). The cell suspension remained for 2 minutes and the resulting supernatant was centrifuged at 800 rpm for 3 minutes to obtain a precipitate of unfractionated bone cells comprising osteoclasts and preosteoclasts. The precipitate suspended again in the medium was incubated in the presence of 5 x 10-8M rPTH (1-34) at 37 ° C in 5% CO2 incubator for 6 days. After incubation the cells were harvested with trypsin-EDTA, washed twice with the medium, adjusted to a density of 5 to 10 5 cells / ml and plated 200 μl / concavity in 96-well plates, each of which It contained a slice of ivory (6 mm in diameter, 0.15 mm thick). The slices were incubated in the presence of test compounds dissolved in dimethyl sulfoxide at 37 ° C, in a 5% CO2 incubator for 2 days. After scraping the cells, the slices were treated with hematoxylin-acid for 10 minutes to stain the formed stings and washed with water. The number of bites was counted under a light microscope and it was expressed the inhibitory activity of the compound on pitting as the percentage of the control value. In this analysis, the compound of the present invention exhibited excellent inhibition of bone resorption.

EXPERIMENT 9 EFFECT ON LOSS OF BONE IN OVARIETOMIZED RATS (IN VIVO TEST) Female eight-week-old Sprague-Dawley rats were purchased and ovarietated at 9 weeks of age. After surgery the animals received a daily oral administration of the test compound suspended in 5% tragacanth at a volume of 2 ml / kg for 2 weeks. The animals were euthanized the following day after administration and the bilateral femurs were removed to measure bone mineral density by means of a bone mineral analyzer using X-rays. For comparison, the rats were simulated (simulated) and ovarietized (OVX, received only 0.5% tragacanth and were subjected to the same measurements as the treatment group.The data will be expressed as the means ± SEM (normal error of the means.) In this experiment the compounds of the present invention exhibited excellent inhibition on the decrease in bone mineral density by OVX.

EXPERIMENT 10 INHIBITOR EFFECT ON THE PRODUCTION OF LTB * FROM HUMAN PERIPHERAL MONOCYTES (IN VITRO TEST) (1) Isolation of human peripheral monocytes Isolation of the monocytes as co or ee described in experiment 2- (1) was carried out. (2) Culture of human monocytes Cell culture was carried out as described in experiment 2- (2). (3) Measurement of LTB4 content in the monocyte culture medium. The supernatant of the culture medium was subjected after incubation to the ELISA (Cayman) analysis. The IC 50 values were calculated by the least square method from the regression line determined by the inhibition regimens and the doses. The results are shown in table 11.

TABLE II INHIBITOR EFFECT ON THE PRODUCTION OF LTBA FROM HUMAN PERIPHERAL MONOCYTES Example No. CIso (μM) 78 0.31 As can be seen from the above experiments, the compounds of the present invention have excellent analgesic, anti-inflammatory and antipyretic activities, and also reduce bone absorption. Therefore, they can be used in human and animal therapy. The 1,2-diphenylpyrrole derivatives of the present invention can be administered in any conventional form, for example in the form of tablets, capsules, granules, powders or syrups, or can be administered parenterally by injection, or as suppository, ointments, etc. . These pharmaceutical formulations can be prepared by mixing the compounds of the present invention with conventional additives, such as ordinary excipients, binders, disintegrating agents, lubricants, stabilizers, corrigents, using known methods. The dose of the compound of the present invention varies, depending on the condition, age and body weight of the patient, as well as the route of administration, the type of disease and other factors; but the compounds of the present invention can usually be administered in a daily dose ranging from 0.01 to 50 mg / kg of body weight, preferably from 0.1 to 10 mg / kg, in the case of adults, either as a single dose or as divided doses. The preparation of the compounds of the present invention is further illustrated by the following non-limiting examples.

EXAMPLE 1 l- (4-METOXYPENYL) -2- (4-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 1-33) Ki) 4-Methoxy-N- (4-methylsulfonylpencilidene) aniline 1.00 g (5.4 mmol) of 4-methylsulfonylbenzaldehyde and 0.67 g (5.4 mmol) of 4-methoxyaniline were dissolved in 15 ml of ethanol and the solution was heated to reflux for 1 hour. At the end of that time the reaction solution was cooled to room temperature and the crystals which precipitated were collected by filtration and washed with ethanol, to give 1.48 g (95% yield) of the title compound, as slightly yellow prismatic crystals. . Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 8.57 (1H, single band); 8.11-8.01 (4H, multiple bands) 7.33-7.26 (2H, multiple bands) 6.99-6.93 (2H, multiple bands) 3.85 (3H, single band); 3.09 (3H, single band). 1 (ii) a- (-methoxyanilino) -a- (4-methylsulfonylphenyl) acetoniyl 1.48 g (5.1 mmol) of 4-methoxy-N- (4-methylsulfonylbenzylidene) aniline [prepared as described in US Pat. step (i) above], in 15 ml of anhydrous tetrahydrofuran and 0.80 ml (6.0 mmoles) of 95% trimethylsilyl cyanide and 0.85 g (6.0 mmoles) of zinc chloride were added to the resulting suepeneium at 0 ° C. , while stirring. Then the temperature of the reaction mixture was allowed to return to room temperature and the mixture was stirred overnight. At the end of that time, water was added and the mixture was extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate, after which it was concentrated by evaporation under reduced pressure and the crystals which precipitated were collected, by filtration, to give 1.05 g (65% yield) of the compound of the title, like a slightly yellow powder. Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 8.04 (1H, double bands, 3 = 8 Hz); 7.84 (2H, double bands, 3 = 8 Hz); 6.84 (4H, single band); 6.45 (1H, double bands, 3 = 10 Hz); 6.10 (1H, double bands, 3 = 10 Hz); 3.67 (3H, single band); 3.25 (3H, single band). 1 (iii) 1- (Methoxyphenyl) -2- (4-methylsulfonylphenyl) pyrrole 1.00 g (3.2 mmoles) of a- (4-rhoethoxyanino) -α- (4-methylsulfonylphenyl) acetonitrile [prepared as described in step (ii) above] in 15 ml of anhydrous tetrahydrofuran and 0.24 ml (3.5 mmoles) of acrolein was added to the resulting suspension. Then 3.2 ml (3.2 mmol) of a 1.0M solution of lithium bis (trimethylsilyl) amide in tetrahydrofuran was added dropwise to the mixture at -60 ° C to -65 ° C while stirring. The mixture was stirred at the same temperature for one hour and then the temperature of the mixture was allowed to return to room temperature, and the mixture was stirred for another 1.5 hours. At the end of that time, a saturated aqueous solution of ammonium chloride was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was heated at 200 ° C for one hour. It was applied to silica gel chromatography column and eluted with a 1: 9 by volume mixture of hexane and methylene chloride to give 0.32 g (31% yield) of the title compound, as a pale yellow powder which melts 148-149 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.74 (2H, double bands, 3 = 8 Hz) 7.27 (2H, double bands, 3 = 8 Hz) 7.13-7.07 (2H, multiple bands) 6.95-6.85 (3H, multiple bands) 6.58-6.57 (1H, multiple bands) 6. 39-6.36 (1H, multiple bands); 3.84 (3H, single band), - 3.04 (3H, single band).

EXAMPLE 2 1- (4-CHLOROPHENYL) -2- (4-METHYLSULFONYLPHENYL) PYRROL (COMPOUND No. 1-35) Following a procedure similar to that described in the three steps of examples Ki), Kii) and Kiii), but using as starting material 4-chloroaniline instead of 4-methoxyaniline, the title compound was obtained as a pale yellow powder which melts at 1B4-188 ° C. The yield of the compound (pale yellow prismatic crystals) in the first stage was 94%, that of the second stage (white powder) was 93% and that of the third stage was 42%. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.78 (2H, double bands, 3 = 8 Hz); 7.37-7.26 (4H, multiple bands); 7.13-7.09 (2H, multiple bands); 6.97 (1H, single band); 6.58-6.57 (1H, multiple bands); 6.42-6.39 (1H, multiple bands); 3.05 (3H, single band).

EXAMPLE 3 1- (4-TRIFLUOROMETILPHENYL) -2- (-METILSULFONYLPHENYL) PIRROL (COMPOUND No. 1-45) Following a procedure similar to that described in the three steps of examples Ki), Kii) and Kiii), but using as starting material 4-trifluoromethylaniline instead of 4-methoxyaniline, the title compound was obtained as a white powder which melts at 187-190 ° C. The yield of the compound (pale yellow prismatic crystals) in the first stage was 64%, that of the second stage (white powder) was 95% and that of the third stage was 47%. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.80 (2H, double bands, 3 = 8 Hz); 6.64 (2H, double bands, 3 = 8 Hz); 7.28 (4H, double bands, 3 = 10 Hz); 7.02 (1H, single band); 6.61-6.60 (1H, multiple bands); 6.46-6.43 (1H, multiple bands); 3.06 (3H, single band).

EXAMPLE 4 1- (-TRIFLUOROMETOXYPHENYL) -2- (-METILSULFONYLPHENYL) PIRROL (COMPOUND No. 1-46) Following a procedure similar to that described in the three steps of examples Ki), Kii) and Kiii), but using as starting material 4-trifluoromethoxyaniline instead of 4-methoxyaniline, the title compound was obtained as a white powder which melts at 150-152 ° C. The yield of the compound (pale yellow prismatic crystals) in the first stage was 59%, that of the second stage (white powder) was 97% and that of the third stage was 52%. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.78 (2H, double bands, 3 = 8 Hz); 7.29-7.18 (6H, multiple bands); 6.98 (1H, single band); 6.59-6.58 (1H, multiple bands); 6.43-6.41 (1H, multiple bands); 3.05 (3H, single band).

EXAMPLE 5 1- (3-CHLORO-4-FLUOROFENIL) -2- (-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 1-39) Following a procedure similar to that described in three stages of the examples Ki), Kii) and Kiii), but using as starting material 3-chloro-4-fluoroaniline instead of 4-methoxyaniline, the title compound was obtained or a pale yellow powder which melts at 146-149 ° C. The yield of the compound (white powder) in the first stage was 93%, that of the second stage (white powder) was 96% and that of the third stage was 39%. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.80 (2H, double bands, 3 = 8 Hz); 7.33-6.95 (6H, multiple bands); 6.57 (1H, double bands, 3 = 2 Hz); 6.41-6.39 (1H, multiple bands); 3.05 (3H, single band).

EXAMPLE 6 1- (3,4-DIFLUOROPHENYL) -2- (-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 1-51) Following a procedure similar to that described in the three steps of examples Ki), Kii) and Kiii), but using 3,4-difluoroaniline as the starting material instead of 4-methoxyaniline, the title compound was obtained as a powder pale yellow that melts at 137-139 ° C. The yield of the compound (pale yellow prismatic crystals) in the first stage was 66%, that of the second stage (white powder) was 92% and that of the third stage was 46%. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.80 (2H, double bands, 3 = 8 Hz) 7.28 (2H, double bands, 3 = 8 Hz) 7.22-6.87 (6H, multiple bands) 6.58-6.56 (1H, multiple bands) 6.42-6.39 (1H, multiple bands) 3.06 (3H, single band).

EXAMPLE 7 1- (2, -DIFLUOROFENIL) -2-U-METILSULFONILFENIL) PIRROL (COMPOUND No. 1-53) Following a procedure similar to that described in the tree stages of examples Ki), Kii) and Kiii), but using as starting material 2,4-difluoroaniline instead of 4-methoxyaniline, the title compound was obtained as a powder white that melts at 122-125 ° C. The yield of the compound (white powder) in the first stage was 79%, that of the second stage (white powder) was 97% and that of the third stage was 10%. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.77 (2H, double bands, 3 = 8 Hz); 7.30-7.19 (3H, multiple bands); 6. 95-6.89 (3H, multiple bands); 6.60-6.59 (1H, multiple bands); 6.45-6.42 (1H, multiple bands); 3.04 (3H, single band).

EXAMPLE 8 1- (3, -DIMETHYLPHENYL) -2- (-METILSULFONYLPHENYL? PYROL (COMPOUND No. 1-55) Following a procedure similar to that described in the three steps of examples Ki), Kii) and Kiii), but using as starting material 3,4-dimethylaniline instead of 4-methoxyaniline, the title compound was obtained as a powder white that melts at 134-137 ° C. The yield of the compound (yellow prismatic crystals) in the first stage was 95%, that of the second stage (white powder) was 96% and that of the third stage was 23%. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.74 (2H, double bands, 3 = 8 Hz) 7.29 (2H, double bands, 3 = 8 Hz) 7.10-6.82 (4H, multiple bands) 6.57-6.55 (1H, multiple bands) 6.38-6.36 (1H, multiple bands) 3.03 (3H, single band); 2.29 (3H, individual band); 2. 24 (3H, single band).

EXAMPLE 9 1- (4-METHYLPHENYL) -2- (4-METHYLSULFONYLPHENYL) PYRROL (COMPOUND No. 1-37) Following a procedure similar to that described in the three steps of examples Ki), Kii) and Kiii), but using as starting material 4-methylaniline instead of 4-methoxyaniline, the title compound co or a yellow powder was obtained pale that melts at 112-114 ° C. The yield of the compound (white powder) in the first stage was 97%, that of the second stage (white powder) was 98% and that of the third stage was 19%. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.74 (2H, double bands, 3 = 8 Hz) 7.28 (2H, double bands, 3 = 9 Hz) 7.16 (2H, double bands, 3 = 8 Hz) 7.05 (2H, double bands, 3 = 8 Hz) 6.97 (1H, multiple bands); 6.57-6.56 (1H, multiple bands); 6.39-6.37 (1H, multiple bands); 3.03 (3H, single band); 2.39 (3H, single band).

EXAMPLE 10 1- (3, -DICLOROPHENYL) -2- (-METILSULFONYLPHENYL) PIRROL (COMPOUND No. 1-57) Following a procedure similar to that described in the three steps of examples Ki), Kii) and Kiii), but using 3,4-dichloroaniline as the starting material instead of 4-methoxyaniline, the title compound was obtained as a white powder that melts at 139-142 ° C. The yield of the compound (white powder) in the first stage was 91%, that of the second stage (white powder) was 93% and that of the third stage was 41%. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.83 (2H, double bands, 3 = 8 Hz) 7.43-7.26 (4H, multiple bands) 7.16 (2H, double bands, 3 = 8 Hz) 6.96-6.91 (4H, multiple bands) 6.58-6.57 (1H, multiple bands) 6.43-6.41 (1H, multiple bands) 3.06 (3H, single band).

EXAMPLE 11 1- (3, -METILENDIOXIFENIL) -2- (4-METILSULFONILFENIL) PYROL (COMPOUND No. 1-41) Following a procedure similar to that described in the three steps of examples Ki), Kii) and Kiii), but using as starting material 3,4-methylenedioxianiline instead of 4-methoxyaniline, the title compound was obtained as a yellow pale that melts at 172-175 ° C. The yield of the compound (pale yellow powder) in the first stage was 95%, that of the second stage (gray powder) was 91% and that of the third stage was 29%. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d pp: 7.77 (2H, double bands, 3 = 9 Hz); 7.31 (2H, double bands, 3 = 9 Hz); 6.93 (1H, single band); 6.78 (1H, double bands, 3 = 8 Hz); 6.66 (2H, double bands, 3 = 8 Hz); 6.55 (1H, single band); 6.37-6.35 (1H, multiple bands); 6.03 (2H, single band); 3.05 (3H, single band).

EXAMPLE 12 1- (-METOXYPHENYL) -4-METHYL-2- (4-METHYLSULFONYLPHENYL) PYRROL (COMPOUND No. 1-34) Following a procedure similar to that described in example Kiii), but using methacrolein in place of acrolein, the title compound was obtained as a pale yellow powder (21% yield), which melts at 154-160 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.72 (2H, double bands, 3 = 8 Hz) 7.25 (2H, double bands, 3 = 7 Hz) 7.09-7.03 (2H, multiple bands) 6.89-6.84 (2H, multiple bands) 6.73 (1H, single band); 6.41 (1H, double bands, 3 = 2 Hz); 3.83 (3H, single band); 3.03 (3H, single band); 2.18 (3H, single band).

EXAMPLE 13 2- (4-FLUOROFENIL) -l- (4-SULFAHOILFENIL) PIRROL (COMPOUND No. 2-62) 13 (i) N- (4-Luorobenzylidene) -4-sulfamoylamine Following a procedure similar to that described in Example Ki), but using 4-fluorobenzaldehyde and 4-sulfamoilaniline as starting materials, the title compound was obtained as a white powder (63% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated acetone) 6 ppm: 8.64 (1H, single band); 8.12-8.03 (2H, multiple bands); 7.93 (2H, double bands, 3 = 9 Hz); 7.40-7.28 (4H, multiple bands); 6.57 (2H, single band). 13 (ii) "- (-fluorophenyl) -a- (-β-sulphamoylanilino) acetonitrile Following a procedure similar to that described in example Kii), but using as starting materials N- (4-fluorobenzylidene) -4-sulfamoylaniline [prepared as described in step (i) above] and trimethylsilyl cyanide, the title compound was obtained as a white powder (95% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.75 (2H, double bands, 3 = 9 Hz) 7.66-7.55 (2H, multiple bands) 7.20-7.10 (2H, multiple bands) 6.81 (2H , double bands, 3 = 9 Hz) 6.71 (1H, double bands, 3 = 8 Hz) 6.35 (2H, single band); . 61 (1H, double bands, 3 = 8 Hz). 13 (iii) 2- (4-fluorophenyl) -1- (4-sulfamoylphenyl) pyrrole Following a procedure similar to that described in example Kiii), but using a- (4-fluorophenyl) -a- (4-sulfamoyl anilino) acetonitrile [prepared as described in step (ii) above] and acrolein as starting materials, the title compound was obtained as a brown powder (yield 11%), which melts at 198-199 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.88 (2H, double bands, 3 = 9 Hz) 7.26 (2H, double bands, 3 = 9 Hz) 7.14-7.04 (2H, multiple bands) 7.00-6.90 (3H, multiple bands) 6.95-6.97 (2H, multiple bands) 4.87 (2H, single band). Mass Spectrum (IE) m / z: 316 [M +].

EXAMPLE 14 2- (4-FLUOROPHENYL) -3-METHYL-1- (4-SULFATIOYLPHENYL) PYRROL (COMPOUND No. 2-64) Following a procedure similar to that described in Example 13 (iii), but using crotonaldehyde instead of acrolein, the title compound was obtained as a powder white (19% yield), which melts at 187-188 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.81 (2H, double bands, 3 = 9 Hz) 7.15 (2H, double bands, 3 = 9 Hz) 7.10-6.95 (2H, multiple bands) 6.90 (2H , double bands, 3 = 3 Hz) 6.29 (2H, double bands, 3 = 3 Hz) 4.78 (2H, single band); 2.14 (3H, single band). Mass spectrum (IE) m / z: 330 [M + l.

EXAMPLE 15 2- (-FLUOROPHENYL) -4-HETIL-l- (-SULFAMOYLPHENYL) PIRROL (COMPOUND No. 2-63) Following a procedure similar to that described in Example 13 (iii), but using methacrolein in place of acrolein, the title compound was obtained as a pale yellow powder (24% yield), which melts at 168-170 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.85 (2H, double bands, 3 = 9 Hz) 7.21 (2H, double bands, 3 = 9 Hz) 7.12-7.03 (2H, multiple bands) 7.00-6.89 (2H, multiple bands) 6. 74 (1H, single band); 6.27 (1H, single band); 4.82 (2H, single band), - 2.18 (3H, single band). Mass spectrum (IE) m / z: 330 [M + l.

EXAMPLE 16 2-U-METHYLPHENYL) -l- (4-SULFAHOYLPHENYL) PYRROL (COMPOUND No. 2-87) 16 (i) N- (4-methylbenzylidene) -4-sulicylaniline Following a procedure similar to that described in example Ki), but using 4-ethylbenzaldehyde and 4-sulfamoilaniline as starting materials, the title compound was obtained as a white powder (91% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 8.60 (1H, single band); 7.90-7.81 (4H, multiple bands); 7.42-7.32 (4H, multiple bands); 2.40 (3H, single band). 16 (ii) a- (Aethylphenyl) -ot- (4-sulfamoylanilino) acetonitrile Following a procedure similar to that described in example Kii), but using as starting materials N- (4-methylbenzylidene) -4-sulfamoylaniline [prepared how I know described in step (i) above] and trimethylsilyl cyanide, the title compound was obtained as a white powder (94% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.70 (2H, double bands, 3 = 9 Hz) 7.48 (2H, double bands, 3 = 9 Hz) 7.26 (2H, double bands, 3 = 9 Hz) 6.68 (1H, double bands, 3 = 8 Hz) 6.84 (2H, double bands, 3 = 9 Hz) 6.72 (2H, single band); 5.67 (1H, double bands, 3 = 8 Hz); 2.38 (3H, single band). 16 (iii) 2- (-methylphenyl) -1- (-sulfamoylphenyl) pyrrole FOLLOWING A procedure similar to that described in example Kiii), but using as starting materials a- (4-methyl phenyl) -a- (4- sulfamoylanilino) acetonitrile [prepared as described in step (ii) above] and acrolein, the title compound was obtained as a brown powder (yield 13%), which melts at 183-184 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.87 (2H, double bands, 3 = 9 Hz); 7.28 (2H, double bands, 3 = 9 Hz); 7.09-6.98 (4H, multiple bands); 6. 96-6.93 (1H, multiple bands); 6.44-6.38 (2H, multiple bands); 4.81 (2H, single band), - 2.33 (3H, single band). Mass spectrum (IE) m / z: 313 [(M + H) + l.

EXAMPLE 17 3-METHYL-2- (4-METHYLPHENYL) -l- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-88) Following a procedure similar to that described in example 16 (iii), but using crotonaldehyde instead of acrolein, the title compound was obtained as a brown amorphous material (33% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.79 (2H, double bands, 3 = 9 Hz) 7.16 (2H, double bands, 3 = 9 Hz) 7.09 (2H, double bands, 3 = 9 Hz) 6.97 (2H, double bands, 3 = 9 Hz) 6.89 (1H, double bands, 3 = 3 Hz) 6.28 (1H, double bands, 3 = 3 Hz) 4.83 (2H, single band); 2.34 (3H, single band); 2.15 (3H, single band). Mass spectrum (IE) m / z: 326 [l? +].

EXAMPLE 18 4-METHYL-2- (-METILPHENYL) -1- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-89) Following a procedure similar to that described in example 16 (iii), but using metacrolein instead of acrolein as starting materials, the title compound was obtained as a pale brown powder (yield 5%), which melts at 175-176 °. C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.84 (2H, double bands, 3 = 9 Hz) 7.23 (2H, double bands, 3 = 9 Hz) 7.08-6.97 (4H, multiple bands) 6.73 (1H , double bands, 3 = 2 Hz) 6.27 (1H, double bands, 3 = 2 Hz) 4.79 (2H, single band); 2.32 (2H, single band); 2.18 (2H, single band).

EXAMPLE 19 l- (4-FLUOROFENIL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-73) 19 (i) 4- luoro-N- (4-sulfamoylbenzylidene) aniline Following a procedure similar to that described in example i), but using 4-sulfamoylbenzaldehyde and 4- fluoroaniline as starting materials, the title compound was obtained as white prismatic crystals (25% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 8.74 (1H, single band); 8.11 (2H, double bands, 3 = 8 Hz); 7.96 (2H, double bands, 3 = 8 Hz); 7.50 (2H, single band); 7.43-7.25 (4H, multiple bands). 19 (ii) tt- (4-fluoroanilino) -ot- (4-sulfamoylphenyl) ketonitrile Following a procedure similar to that described in example Kii), but using as starting materials 4-fluoro-N- (4-sulfamoylbenzylidene) aniline [prepared as described in step (i) above], and tri-ethylsilyl cyanide as starting materials, the title compound was obtained as a slightly yellow powder (83% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.93 (2H, double bands, 3 = 8 Hz); 7.76 (2H, double bands, 3 = 8 Hz); 7.45 (2H, single band); 7.05 (2H, triple bands, 3 = 9 Hz); 6.73-6.85 (3H, multiple bands); 6.12 (1H, double bands, 3 = 10 Hz).

Mass spectrum (IE) m / z: 279 CM + 1. 19 (iii) l- (- luorophenyl) -2- (-sulfamoylphenyl) irrol Following a procedure similar to that described in example Kiii), but using a- (4-fluoroanilino) -a- (4-sulfamoylphenyl) acetonitrile [prepared as described in step (ii) above] and acrolein as starting materials, the title compound was obtained as a white powder (yield 48%), which melts at 160-161 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.67 (2H, double bands, 3 = 8 Hz); 7.32-7.22 (8H, multiple bands); 7.14 (1H, triple bands, 3 = 2 Hz); 6.59 (1H, double double bands, 3 = 4 to 2 Hz); 6.36 (1H, triple bands, 3 = 3 Hz). Mass spectrum (IE) m / z: 316 CM + 1.

EXAMPLE 20 1- (-FLUOROFENIL) -4-METHYL-2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-74) Following a procedure similar to that described in Example 19 (iii), but using methacrolein in place of acrolein, the title compound was obtained as a white powder (62% yield), which melts at 126-127 ° C. .1.60 Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.87 (2H, double bands, 3 = 9 Hz); 7.39-7.17 (6H, multiple bands); 6.87 (1H, single band); 6.53 (1H, single band); 4.93 (2H, single band); 2.31 (3H, single band). Mass spectrum (IE) m / z: 330 [M + l.

EXAMPLE 21 2- (4-FLUOROPHENYL) -3-METHYL-L- (4-METHYLSULFONYLPHENYL) PYRROL (COMPOUND No. 2-8) 21 (i) N- (4-fluoropencilidene) -4-w.ethylthioamine Following a procedure similar to that described in Example Ki), but using 4-fluorobenzaldehyde and 4-methylthioaniline as starting materials, the title compound was obtained as Needle-shaped crystals, light yellow in color (87% yield). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 8.43 (1H, single band); 7.94-7.86 (2H, multiple bands); 7.33-7.27 (2H, multiple bands); 7.21-7.12 (4H, multiple bands); 16. 1 2. 52 (3H, single band). 21 (ii) «- (4-fluorophenyl) -oc- (-methylthioanilino) acetonitrile Following a procedure similar to that described in example Kii), but using N- (4-fluorobenzylidene) -4-ethylthioaniline [prepared as described in Step (i) above] and trimethylsilyl cyanide as starting materials, the title compound was obtained as a pale yellow powder (96% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.63-7.54 (2H, multiple bands) 7.27 (2H, double bands, 3 = 9 Hz) 7.21-7.12 (2H, multiple bands) 6.73 (2H, double bands , 3 = 9 Hz) 5.40 (1H, double bands, 3 = 9 Hz) 4.01 (1H, double bands, 3 = 9 Hz) 2.45 (3H, single band). 21 (iii) 2- (4-fluorophenyl) -3-methyl-l- (-methylsulfonylphenyl) pyrro! A solution of 2.00 g (7.3 mmol) of a- (4-fluorophenyl) -a- (4-rethylthioanilino) acetonitrile [prepared as described in step (ii) was cooled to -78 ° C under a stream of nitrogen. ) above] in 15 ml of tetrahydrofuran, and 0.67 ml (8.1 mmol) of crotonaldehyde was added to the resulting solution.

Then 8.10 ml (8.1 mmol) of a 1.0M solution of lithium bistrimethylsilyamide was added dropwise to the mixture, and the resulting mixture was stirred at -78 ° C, after which the mixture was stirred overnight at the same time. that his temperature was allowed to rise naturally. The tetrahydrofuran was then removed by distillation under reduced pressure and the ethyl acetate was added to the residue. The resulting mixture was washed with a saturated aqueous solution of ammonium chloride with water and with a saturated aqueous solution of sodium chloride, in that order. The organic layer was separated and dried over anhydrous magnesium sulfate and the solvent was then removed by distillation under reduced pressure. The residue was dissolved in 20 ml of dichloroethane and 3.98 g (16.2 mmoles) of 70% m-chloroperbenzoic acid was added to the resulting solution in several portions while cooling with ice. The mixture was then stirred while cooling on ice for 30 minutes. At the end of that time the reaction mixture was diluted with methylene chloride and washed with a 10% w / v aqueous solution of sodium thiosulfate, and with a saturated aqueous solution of sodium bicarbonate, twice with each , in that order. Subsequently, the organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The residue was heated at 150 ° C for two hours, after which it was applied to a column of silica gel chromatography and eluted, using a 2: 1 by volume mixture of hexane and ethyl acetate as eluent, to give 0.36 g (yield 15%) of the title compound, as a white powder, which melts at 157-158 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.83 (2H, double bands, 3 = 9 Hz) 7.20 (2H, double bands, 3 = 9 Hz) 7.10-6.95 (4H, multiple bands) 6.91 (1H , double bands, 3 = 3 Hz) 6.30 (1H, double bands, 3 = 3 Hz) 3.06 (3H, single band); 2.14 (3H, single band). Mass spectrum (IE) m / z: 329 [M + l.

EXAMPLE 22 2- (4-FLUOROFENIL) -1- (-METILSULFONILFENIL) PIRROL (COMPOUND No. 2-3) Following a procedure similar to that described in example 21 (iii), but using acrolein instead of crotonaldehyde, the title compound was obtained as a white powder (yield 7%), which melts at 195-196 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.90 (2H, double bands, 3 = 9 Hz); 7.31 (2H, double bands, 3 = 9 Hz); 7. 13-7.05 (2H, multiple bands); 7.01-6.92 (3H, multiple bands); 6.46-6.40 (2H, multiple bands); 3.08 (3H, single band). Mass spectrum (IE) m / z: 315 [M + l.

EXAMPLE 23 2- (4-FLUOROPHENYL) -4-METHYL-L- (4-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 2-11) Following a procedure similar to that described in example 2 (iii), but using methacrolein instead of crotonaldehyde, the title compound was obtained as a white powder (36% yield), which melts at 151-154 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.87 (2H, double bands, 3 = 9 Hz) 7.26 (2H, double bands, 3 = 9 Hz) 7.12-7.03 (2H, multiple bands) 7.00-6.92 (2H, multiple bands) 6.76 (1H, double bands, 3 = 2 Hz) 6.28 (1H, double bands, 3 = 2 Hz) 3.08 (3H, single band); 2.18 (3H, single band). Mass spectrum (IE) m / z: 329 [M + l.

EXAMPLE 24 3-ETHYL-2- (-FLUQROFENIL) -1- (4-METILSULFQNILFENIL) PIRRQL (COMPOUND No. 2-9) Following a procedure similar to that described in example 21 (iii), but using 2-pentenal instead of crotonaldehyde, the title compound was obtained as a white powder (yield 15%), which melts at 107-108 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.82 (2H, double bands, 3 = 9 Hz); 7.21-6.93 (7H, multiple bands); 6.36 (1H, double bands, 3 = 3 Hz); 3.05 (3H, single band); 2.50 (2H, quad bands, 3 = 8 Hz); 1.19 (3H, triple bands, 3 = 8 Hz). Mass spectrum (IE) m / z: 343 CM + 1.

EXAMPLE 25 2- (-FLUOROPHENYL) -1- (-METILSULFONYLPHENYL? -3-PROPYLPIRROL (COMPOUND No. 2-10) Following a procedure similar to that described in example 21 (iii), but using 2-hexenal instead of crotonaldehyde, the title compound was obtained as white prismatic crystals (yield 20%), which melts 116-117 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.82 (2H, double bands, 3 = 9 Hz) 7.19 (2H, double bands, 3 = 9 Hz) 7.06-6.92 (5H, multiple bands) 6.33 (1H , double bands, 3 = 3 Hz) 3.05 (3H, single band); 2.44 (2H, triple bands, 3 = 8 Hz); 1.63-1.56 (2H, multiple bands); 0.92 (3H, triple bands, 3 = 7 Hz). Mass spectrum (IE) m / z: 357 [M +].

EXAMPLE 26 2- (4-CHLOROPHENYL) -l- (4-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 2-23) 26 (i) N- (4-chlorobenzylidene) -4-methylthioaniline Following a procedure similar to that described in example Ki), but using 4-chlorobenzaldehyde and 4-methylthioaniline as starting materials, the title compound was obtained as crystals in pale yellow needle shape (94% yield). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 8.43 (1H, single band); 7. 83 (2H, double bands, 3 = 9 Hz) 7.45 (2H, double bands, 3 = 9 Hz) 7.30 (2H, double bands, 3 = 9 Hz) 7.18 (2H, double bands, 3 = 9 Hz) 2.51 ( 3H, individual band). 26 (ii) tt- (4-chlorophenyl) -tt- (4-methylthioanilino) acetonitrile Following a procedure similar to that described in example Kii), but using as starting materials N- (4-chlorobenzylidene) -4-methylthioaniline [ prepared as described in step (i) above] and trimethylsilyl cyanide, the title compound was obtained as a pale yellow powder (yield 84%). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.55 (2H, double bands, 3 = 9 Hz) 7.44 (2H, double bands, 3 = 9 Hz) 7.27 (2H, double bands, 3 = 9 Hz) 6.72 (2H, double bands, 3 = 9 Hz) 5.40 (1H, double bands, 3 = 9 Hz) 4.02 (1H, double bands, 3 = 9 Hz) 2.45 (3H, single band). 26 (iii) 2- (-chloroenyl) -1- (-methylsulfonylphenyl) pyrrole Following a procedure similar to that described in example 21 (iii), but using a- (4-chlorophenyl) -a- (4- methylthioanilino) acetonitrile [prepared as described in step (ii) above] and acrolein as starting materials, the title compound was obtained as an orange powder (32% yield) melting at 203-205 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.91 (2H, double bands, 3 = 9 Hz) 7.32 (2H, double bands, 3 = 9 Hz) 7.23 (2H, double bands, 3 = 9 Hz) 7.05 (2H, double bands, 3 = 9 Hz) 7.00-6.97 (1H, multiple bands) 6.48-6.45 (1H, multiple bands) 6.44-6.40 (1H, multiple bands) 3.09 (3H, single band). Mass spectrum (IE) m / z: 331 [M +].

EXAMPLE 27 2- (4-CHLOROPHENYL) -3-METHYL-L- (4-METHYLSULFONYLPHENYL) PYRROL (COMPOUND No. 2-24) Following a procedure similar to that described in Example 26 (iii), but using crotonaldehyde in place of acrolein, the title compound was obtained as a pale yellow powder (21% yield), which melts at 173-174 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7. 84 (2H, double bands, 3 = 9 Hz) 7.27 (2H, double bands, 3 = 9 Hz) 7.21 (2H, double bands, 3 = 9 Hz) 7.01 (2H, double bands, 3 = 9 Hz) 6.92 ( 1H, double bands, 3 = 3 Hz) 6.30 (1H, double bands, 3 = 3 Hz) 3.07 (3H, single band); 2.15 (3H, single band). Mass spectrum (IE) m / z: 345 CM + 1.

EXAMPLE 28 2- (-METOXYPHENYL) -1- (-METILSULFONYLPHENYL) PIRROL (COMPOUND No. 2-20) 28 (i) N- (4-Methoxybenzylidene) -4-n > ethylthioamine Following a procedure similar to that described in example Ki), but using as starting materials 4-ethoxybenzaldehyde and 4-methylthioaniline, the title compound was obtained as a slightly yellow powder (100% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 8.39 (1H, single band); 7.84 (2H, double bands, 3 = 9 Hz) 7.29 (2H, double bands, 3 = 9 Hz) 7.16 (2H, double bands, 3 = 9 Hz) 6. 98 (2H, double bands, 3 = 9 Hz); 3.88 (3H, single band); 2.51 (3H, single band). 28 (ii) oc- (-methoxyphenyl) - "- (-methylthioanilino) acetoni ryl Following a procedure similar to that described in example Kii), but using as starting materials N- (4-methoxybenzylidene) -4-methylthioaniline Cpreparated as described in step (i) above] and tri-ethylsilyl cyanide, the title compound was obtained as a pale brown powder (yield 92%). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.47 (2H, double bands, 3 = 9 Hz) 7.27 (2H, double bands, 3 = 9 Hz) 6.97 (2H, double bands, 3 = 9 Hz) 6.73 (2H, double bands, 3 = 9 Hz) 5.34 (1H, double bands, 3 = 9 Hz) 3.97 (1H, double bands, 3 = 9 Hz) 3.84 (3H, single band); 2.45 (3H, single band). 28 (iii) 2- (-methoxyphenyl) -1- (-methylsulfonylphenyl) pyrrole Following a procedure similar to that described in Example 21 (iii), but using as starting materials a- (4-methoxy pheny1) -a- ( 4-methylthioanilino) acetonitrile [prepared 1. 7.1 As described in step (ii) above] and acrolein, the title compound was obtained as a white powder (yield 9%), which melts at 183-184 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.88 (2H, double bands, 3 = 9 Hz) 7.32 (2H, double bands, 3 = 9 Hz) 7.05 (2H, double bands, 3 = 9 Hz) 7.98-7.93 (1H, multiple bands) 6.80 (2H, double bands, 3 = 9 Hz) 6.43-6.37 (2H, multiple bands) 3.80 (3H, single band); 3.08 (3H, single band). Mass spectrum (IE) m / z: 327 CM +].

EXAMPLE 29 2- (4-METHYLPHENYL) -l- (4-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 2-25) 29 (i) N- (methyl ethyl en) -4-methylthioaniline Following a procedure similar to that described in example Ki), but using 4-methylbenzaldehyde and 4-methythoaniline as starting materials, the title compound was obtained as a slightly yellow powder (96% yield). Mass spectrum (IE) m / z: 241 [M +]. 29 (ii) tt- (-Methylphenyl) -oc- (-methylthioanilino) acetonitrile Following a procedure similar to that described in Example Kii), but using N- (4-methylbenzylidene) -4-methylthioaniline [prepared as described in step (i) above] and trimethylsilyl cyanide as starting materials, the title compound was obtained as a pale yellow powder (73% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.42 (2H, double bands, 3 = 9 Hz); 7.27 (4H, double bands, 3 = 9 Hz); 6.73 (2H, double bands, 3 = 9 Hz); 5.36 (1H, double bands, 3 = 8 Hz); 3.99 (1H, double bands, 3 = 8 Hz); 2.44 (3H, single band); 2.40 (3H, single band). 29 (iii) 2- (Methylphenyl) -1- (-roethyl-sulphonylphenyl) -yrol Following a procedure similar to that described in example 21 (iii), but using a- (4-methylphenyl) -a- (4-methylthioanilinoacetonitrile [ prepared as described in step (ii) above] and acrolein as starting materials, the title compound was obtained as a yellow powder (yield 16%), which melts at 186-1B7 ° C. Nuclear Magnetic Resonance Spectrum ( 270 MHz, CDCI3) d ppm: 7.88 (2H, double bands, 3 = 9 Hz) 7.32 (2H, double bands, 3 = 9 Hz) 7.10-6.94 (5H, multiple bands) 6.45-6.39 (2H, multiple bands) 3.08 (3H, single band) ); 2.33 (3H, single band). Mass spectrum (IE) m / z: 311 [M + l.

EXAMPLE 30 2- (4-METOXYPENYL) -3-METHYL-L- (-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 2-21) (i) «- (4-Methoxyphenyl) -o- (-methylsulfonylanilino) acetoniyl 6.41 g (20.3 m olee of a- (4-methoxy phenyl) -a- (4-methylthioamino) acetonitrile [prepared as described in example 28 (ii)], in 160 ml of dichloroethane, and 12.23 g (49.8 mmoles) of 70% m-chloroperbenzoic acid was added to the resulting solution in several portions, while cooling with ice. The mixture was stirred for 30 minutes, after which the reaction mixture was diluted with methylene chloride and washed once with a 10% w / v aqueous solution of sodium thiosulfate and once with a saturated aqueous solution of sodium thiosulfate. sodium bicarbonate, in that order, then the two washings were repeated in the same order, the organic layer was separated and dried over anhydrous magnesium sulfate and The solvent was removed by distillation under reduced pressure. The resulting residue was applied to a silica gel chromatography column and eluted with a 1: 2 by volume mixture of ethyl acetate and hexane, to give 3.65 g of the title compound, as a pale yellow powder (51% yield). ). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.83 (2H, double bands, 3 = 9 Hz) 7.50 (2H, double bands, 3 = 9 Hz) 6.99 (2H, double bands, 3 = 9 Hz) 6.83 (2H, double bands, 3 = 9 Hz) 5.43 (1H, double bands, 3 = 8 Hz) 4.56 (1H, double bands, 3 = 8 Hz) 3.85 (3H, single band); 3.03 (3H, single band). (ii) 2- (4-Methoxyphenyl) -3-methyl-1- (4-methylsulfonylphenyl) eneol Following a procedure similar to that described in example KIII), but using a- (4-methylphenyl) -a- (4 methylthioanilino) acetonitrile [prepared as described in step (i) above] and crotonaldehyde as starting materials, the title compound was obtained as an orange-colored powder (yield 40%), which melts at 131-132 °. C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.81 (2H, double bands, 3 = 9 Hz); 7. 21 (2H, double bands, 3 = 9 Hz) 7.01 (2H, double bands, 3 = 9 Hz) 6.89 (1H, double bands, 3 = 3 Hz) 6.84 (1H, double bands, 3 = 3 Hz) 6.29 ( 1H, double bands, 3 = 3 Hz) 3.81 (3H, single band); 3.05 (3H, single band); 2.14 (3H, single band). Mass spectrum (IE) m / z: 341 [M + l.

EXAMPLE 31 3-METHYL-2- (-METILPHENYL) -1- (-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 2-26) 31 (i) tt- (4-Methylphenyl) -tt- (4-methylsulfonylanilino) acetonitrile Following a procedure similar to that described in example 30 (i), but using a- (4-methylphenyl) -a- (4-methytioanilino) ) acetonitrile [prepared as described in Example 2 (ii)] and m-chlorobenzoic acid as starting materials, the title compound was obtained as a white powder (yield 93%). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.83 (2H, double bands, 3 = 9 Hz); 7.47 (2H, double bands, 3 = 9 Hz); 7.30 (2H, double bands, 3 = 9 Hz); 6. 84 (2H, double bands, 3 = 9 Hz) 5.45 (1H, double bands, 3 = 8 Hz) 4.55 (1H, double bands, 3 = 8 Hz) 3.03 (3H, single band); 2.41 (3H, single band). 31 (ii) 3-Methyl-2- (4-reethynyl) -l- (4-reethylsulfonyl enyl) iron. Following a procedure similar to that described in example Kiii), but using a- (4-methylphenyl) -a- (4-methylthioanilino) acetonitrile [prepared as described in step (i) above] and crotonaldehyde as starting materials, the title compound was obtained as a pale brown powder (yield 46%), which melts at 158-160 °. C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.81 (2H, double bands, 3 = 9 Hz) 7.21 (2H, double bands, 3 = 9 Hz) 7.10 (2H, double bands, 3 = 9 Hz) 6.97 (2H, double bands, 3 = 9 Hz) 6.90 (1H, double bands, 3 = 3 Hz) 6.29 (1H, double bands, 3 = 3 Hz) 3.05 (3H, single band); 2.35 (3H, single band); 2.15 (3H, single band). Mass spectrum (FAB) m / z: 326 C (M + H) +1. "FAB" means "Fast Atom Bombing" EXAMPLE 32 2- (-DIFLUOROMETOXYPHENYL) -3-METHYL-1- (4- METILSULFONYLPHENIDPIRROL (COMPOUND No. 2-37) 32 (i) tt- (-Difluoromethoxyphenyl) - «- (-methylthioanilino) acetonitrile Following a procedure similar to that described in example Ki), but using 4-difluoromethoxybenzaldehyde and 4-methylthioaniline as starting materials, N- (4 -difluoromethoxybenzylidene) -4-methylthioaniline in a yield of 91%. This compound of aniline and trimethylsilyl cyanide was then reacted with each other, in a manner similar to that described in Example Kii), to give the title compound as a slightly yellow powder (80% yield). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.61 (2H, double bands, 3 = 9 Hz); 7.27 (2H, double bands, 3 = 9 Hz); 7.22 (2H, double bands, 3 = 9 Hz); 6.73 (2H, double bands, 3 = 9 Hz); 6.56 (1H, triple bands, 3 = 73 Hz); 5.41 (1H, double bands, 3 = 9 Hz); 4.01 (1H, double bands, 3 = 9 Hz); 2.45 (3H, single band). 32 (ii) «- (4-Difluoromethoxyphenyl) -tt- (4-methylsulfonylanilino) acetonitrile Following a procedure similar to that described in Example 30 (i), but using a- (4-difluoromethoxyphenyl) -a- (4-methylthioanilino) ) acetonitrile [prepared as described in step (i) above] and m-chloroperbenzoic acid as starting materials, the title compound was obtained as a pale yellow powder (yield 89%). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d pp: 7.84 (2H, double bands, 3 = 9 Hz) 7.61 (2H, double bands, 3 = 9 Hz) 7.25 (2H, double bands, 3 = 9 Hz) 6.84 (2H, double bands, 3 = 9 Hz) 6.57 (1H, triple bands, 3 = 73 Hz); 5.51 (1H, double bands, 3 = 8 Hz); 4.60 (1H, double bands, 3 = 8 Hz); 3.03 (3H, single band). 32 (iii) 2- (4-Difluoromethoxy-phenyl) -3-methyl-1- (4-methylsulfonylphenyl) irrol Following a procedure similar to that described in example Kiii), but using a- (4-difluoromethoxyphenyl) -a- (4 -metiitioanilino) acetonitrile [prepared as described in step (ii) above] and crotonaldehyde as starting materials, the title compound was obtained as a white powder (yield 31%), which melts at 98-99 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.83 (2H, double bands, 3 = 9 Hz) 7.21 (2H, double bands, 3 = 9 Hz) 7.12-7.02 (4H, multiple bands) 6.91 (1H , double bands, 3 = 3 Hz) 6.54 (1H, triple bands, 3 = 74 Hz); 6.30 (1H, double bands, 3 = 3 Hz); 3.06 (3H, single band); 2.15 (3H, single band). Mass spectrum (IE) m / z: 377 [M +].

EXAMPLE 33 1- (4-FLUOROFENIL) -2- (-METILSULFONILFENIL) PIRROL (COMPOUND No. 1-3) 33 (i) tt- (4-Fluoroanilino) - "- (4-methylthiophenyl) acetonitrile Following a procedure similar to that described in example Ki), but using 4-methylthiobenzaldehyde and 4-fluoroanilino as starting materials, 4- was obtained fluoro-N- (4-methylthiobenzilidene) aniline in a yield of 89%. This compound of aniline and tri-ethylsilyl cyanide was reacted with each other, in a manner similar to that described in Example Kii), to give the title compound as a slightly yellow powder (yield 47%).

Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.50 (2H, double bands, 3 = 9 Hz); 7.31 (2H, double bands, 3 = 9 Hz); 6.98 (2H, triple bands, 3 = 9 Hz); 6.73 (2H, double double bands, 3 = 9 to 4 Hz); 5.33 (1H, double bands, 3 = 9 Hz); 3.92 (1H, double bands, 3 = 9 Hz); 2.51 (3H, single band). 10 33 (ii) 1- (-Fluoroenyl) -2- (4-methylsulfonylphenyl) pyrrole Following a procedure similar to that described in example 21 (iii), but using a- (4-difluoromethoxyphenyl) -a- (4-) methylthioanilino) acetonitrile [prepared as described in step (i) above] and acrolein as starting materials, the title compound was obtained as a yellow powder (yield 7%), which melts at 145-147 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 20 7.77 (2H, double bands, 3 = 9 Hz) 7.27 (2H, double bands, 3 = 9 Hz) 7.18-7.04 (4H, multiple bands) 6.96 ( 1H, double double bands, 3 = 3 at 2 Hz); 6.58 (1H, double double bands, 3 = 4 to 2 Hz); : > R 6.40 (1H, double double bands, 3 = 4 to 3 Hz); 3.04 (3H, single band).

Mass spectrum (IE) m / z: 315 [M +].

EXAMPLE 34 1- (4-FLUOROFENIL) -4-METHYL-2- (4-METHYLSULFONYLPHENYL) PIRRQL (COMPOUND No. 1-15) Following a procedure similar to that described in Example 33 (ii), but using methacrolein in place of acrolein, the title compound was obtained as a white powder (yield 4%), which melts at 127-130 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.75 (2H, double bands, 3 = 9 Hz) 7.24 (2H, double bands, 3 = 9 Hz) 7.15-7.03 (4H, multiple bands) 6.74 (1H , double bands, 3 = 2 Hz) 6.42 (1H, double bands, 3 = 2 Hz) 3.04 (3H, single band); 2.18 (3H, single band). Mass spectrum (IE) m / z: 329 [M + l.

EXAMPLE 35 5-BROMO-1- (-FLUOROPHENYL) -2- (-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 1-6) 0.32 g (1.0 mmol) of l- (4-fluorophenyl) was dissolved 2- (4-Methylsulfonylphenyl) pyrrole (prepared as described in example 33) in 10 ml of anhydrous tetrahydrofuran and 0.18 g (1.0 mmoles) of N-bromosuccinimide was added to the resulting solution while cooling with ice. The mixture was then stirred while cooling with ice for one hour, and then at room temperature for another hour. At the end of that time water was added to the mixture and the resulting mixture was extracted with methylene chloride. The organic extract was dried over anhydrous magnesium sulfate and then the solvent was removed by distillation under reduced pressure. The resulting residue was applied to a chromatography column on silica gel and eluted with a 1: 3 by volume mixture of ethyl acetate and hexane, to give 0.28 g of the title compound, as a white powder (yield 70% ), which melts at 174-176 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.73 (2H, double bands, 3 = 9 Hz) 7.23-7.09 (6H, multiple bands) 6.57 (1H, double bands, 3 = 4 Hz) 6.44 (1H , double bands, 3 = 4 Hz) 3.02 (3H, single band). Mass spectrum (IE) m / z: 393 [11 + 1.

EXAMPLE 36 5-BROMINE-1- (-FLUOROPHENYL) -4-METHYL-2- (4-METHYLSULFONYLPHENIDPYRROL (COMPOUND No. 1-18) Following a procedure similar to that described in Example 35, but using (4-fluorophenyl) -4-methyl-2- (4-ethylsulfonylphenyl) pyrrole (prepared as described in Example 34) and N-bromosuccinimide, as starting materials , the title compound was obtained, as a white powder (yield 30%), which melts at 158-159 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.71 (2H, double bands, 3 = 9 Hz); 7.19-7.11 (6H, multiple bands), - 6.49 (1H, single band); 3.02 (3H, single band); 2.15 (3H, single band). Mass spectrum (IE) m / z: 407 [M +].

EXAMPLE 37 5-CHLORO-l- (-FLUOROFENIL) -4-METHYL-2- (4- METILSULFONILFENIDPIRROL (COMPOUND No. 1-17) Following a procedure similar to that described in Example 35, but using N-chlorosuccinimide instead of N-bro-osuccinimide, the title compound was obtained, as? N White powder (58% yield), melting at 151-154 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.71 (2H, double bands, 3 = 9 Hz); 7.20-7.05 (6H, multiple bands); 6.44 (1H, single band); 3.02 (3H, single band). Mass spectrum (IE) m / z: 363 [M + l.

EXAMPLE 38 5-CHLORO-l- (-FLUOROFENIL) -4-METHYL-2- (SULFAMOYLPHENYL) PIRROL (COMPOUND No. 1-75) L- (4-fluorophenyl) -4-methyl-2- (4-sulfamoyl-phenyl) pyrrole (prepared as described in Example 20) was chlorinated in the same manner as described in Example 37, to give the compound of the title as white prismatic crystals (yield 67%), which melt at 119-120 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.63 (2H, double bands, 3 = 8 Hz); 7.33-7.17 (8H, multiple bands); 6.55 (1H, single band); 2.10 (3H, single band). Mass spectrum (IE) m / z: 364 [M +].

EXAMPLE 39 5-CHLORO-l- (-FLUOROFENIL) -2- (-METILSULFONILFENIL) PIRROL (COMPOUND No. 1-5) L- (4-fluorophenyl) -2- (4-methylsulfonyl-phenyDropyrrole (prepared as described in Example 33) was chlorinated in the same manner as described in Example 37, to give the title compound, as a powder white (86% yield), which melts at 180-182 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.73 (2H, double bands, 3 = 9 Hz); 7.23-7.09 (6H, multiple bands); 6.54 (1H, double bands, 3 = 4 Hz); 6.32 (1H, double bands, 3 = 4 Hz); 3.02 (3H, single band). Mass spectrum (IE) m / z: 349 [M + l.

EXAMPLE 40 1- (4-FLUOROPHENYL) -5-YODO-2- (4-METILSULFONYLPHENYL) PYRROL (COMPOUND NO. 1-7) Following a procedure similar to that described in example 35, but using N-iodosuccinimide instead of N-bro osuccinimide, the title compound was obtained as a yellow powder (51% yield), which melts at 174-176 ° C.

Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.73 (2H, double bands, 3 = 9 Hz); 7.22-7.12 (6H, multiple bands); 6.63 (1H, double bands, 3 = 4 Hz); 6.59 (1H, double bands, 3 = 4 Hz); 3.02 (3H, single band). Mass spectrum (IE) m / z: 441 CM + 1.

EXAMPLE 41 5-FLU0R0-1- (4-FLUOROFENIL) -2- (4-METILSULFONILFENIL) PIRROL (COMPOUND No. 1-4) 0.90 g (2.7 mmol) of l- (4-fluorophenyl) -2- (4-methylsulfonylphenyl) pyrrole (prepared as described in example 33) was dissolved in 10 ml of acetonitrile, in a reaction vessel made of polyethylene and to the resulting solution was added 0.46 g (2.7 mmol) of xenon difluoride, at 0 ° C, while stirring. The temperature of the reaction mixture was allowed to return to room temperature and the mixture was stirred at room temperature for 20 hours. At the end of that time 20 ml of a saturated aqueous solution of sodium carbonate was added to the mixture, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium carbonate and then with water, after which it was dried over magnesium sulfate. anhydrous. The solvent was removed by distillation under reduced pressure. The resulting residue was applied to a column of silica gel chromatography and eluted with a 3: 1 by volume mixture of hexane and ethyl acetate, to give 0.32 g of the title compound, as white prismatic crystals (34% yield). ), which melts at 140-141 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.74 (2H, double bands, 3 = 9 Hz); 10 7.26-7.15 (6H, multiple bands); 6.41 (1H, double double bands, 3 = 6 to 4 Hz); 5.76 (1H, triple bands, 3 = 4 Hz); 3.03 (3H, single band). Mass spectrum (IE) m / z: 333 [M + l. L5 EXAMPLE 42 5-FLUORO-l- (4-FLUOROFENIL) -4-METHYL-2- (4- METILSULFONILFENIDPIRROL (COMPOUND No. 1-16) 0 Following a procedure similar to that described in Example 41, but using l- (4-fluorophenyl) -4-methyl-2- (4-rnetylsul-fonyl-phenyl) -pyrrole (prepared as described in Example 34), the compound was obtained of the title as a white powder (yield 10%), which melts at 109-110 ° C. 5 Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7. 71 (2H, double bands, 3 = 9 Hz) 7.19-7.10 (6H, multiple bands) 6.30 (1H, double bands, 3 = 6 Hz) 3.02 (3H, single band); 2.08 (3H, single band). Mass spectrum (IE) m / z: 347 [M + l.

EXAMPLE 43 1- (4-FLUOROFENIL) -5-METHYL-2- (4-METHYLSULFONYLPHENYL) PYRROL (COMPOUND No. 1-8) 43 (i) Methyl 2- (4-methylthiophenacyl) acetoacetate 2.28 g (17.7 mmol) of methyl acetoacetate were dissolved in 40 ml of 2-methyl-2-propanol and 2.21 g (19.7 mmol) of potassium terbutoxide was added. to the resulting solution, under a nitrogen atmosphere. The mixture was then stirred at room temperature for one hour, after which 4.82 g (19.7 mmoles) of 4-methylthiophenacyl bromide in 30 ml of benzene was added dropwise to the resulting mixture. The mixture was then stirred at 60 ° C for three hours, after which it was cooled. It was poured into ice water and extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting residue was applied to a column of silica gel chromatography and eluted with a 1: 4 mixture by volume of ethyl acetate and hexane, to give 4.42 g (80% yield) of the title compound, as a slightly yellow powder. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.89 (2H, double bands, 3 = 9 Hz); 7.27 (2H, double bands, 3 = 9 Hz); 4.23 (1H, double double bands, 3 = 8 to 6 Hz); 3.78 (3H, single band), - 3.69 (1H, double double bands, 3 = 18 to 8 Hz); 3.48 (1H, double double bands, 3 = 18 to 6 Hz); 2.53 (3H, single band), - 2.44 (3H, single band). 43 (ii) Methyl 2- (4-methylsulfonylphenacyl) acetoacetate 4.42 g (15.8 mmol) of methyl 2- (4-methylthiophenazideacetoacetate [prepared as described in step (i) above] was dissolved in 150 ml of sodium chloride. methylene and 7.77 g (31.5 mmoles) of 70% m-chloroperbenzoic acid were added to the resulting solution while cooling with ice, then the mixture was stirred at room temperature for one hour and 30 ml of an aqueous solution was added. at 10% w / v sodium thiosulfate, and the mixture was shaken vigorously, after which it was separated to the liquid phases, the organic layer was separated and washed with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was applied to a column of silica gel chromatography and eluted with a 1: 1 by volume mixture of ethyl acetate and hexane, to give 3.65 g (yield 74%) of the title compound, as a slightly yellow powder . Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 8.16 (2H, double bands, 3 = 9 Hz); 8.07 (2H, double bands, 3 = 9 Hz); 4.26 (1H, double double bands, 3 = 8 6 Hz); 3.80 (3H, single band); 3.75 (1H, double double bands, 3 = 19 to 8 Hz); 3.52 (1H, double double bands, 3 = 19 to 6 Hz); 3.09 (3H, single band); 2.46 (3H, single band). 43 (iii) l- (4-Fluorophenyl) -4-methoxycarbonyl-5-methyl-2- (4-methylsulfonylphenyl) pyrrole 3.00 g (9.6 mmol) of methyl 2- (4-ethylsulfonylphenazideacetoacetate [prepared as described in step (ii) above] in 100 ml of acetic acid and 0.97 g (8.7 mmol) of 4-fluoroaniline was added to the resulting solution, then the resulting mixture was heated to reflux for 5 hours.

The solvent was distilled off under reduced pressure, a saturated aqueous solution of sodium bicarbonate was added to the residue and the mixture was extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was applied to a column of silica gel chromatography and eluted with a 1: 2 by volume mixture of ethyl acetate and hexane, to give 3.10g of the title compound, as a white powder (92% yield), which melts at 154-155 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.73 (2H, double bands, 3 = 9 Hz); 7.21-7.12 (6H, multiple bands); 6.94 (1H, single band); 3.87 (3H, single band); 3.02 (3H, single band); 2.41 (3H, single band). Mass spectrum (IE) m / z: 387 [M + l. 43 (iv) 1- (4-Fluorophenyl) -5-methyl-2- (4-methylsulfonylphenyl) ene 1.00 g (2.6 mmol) of l- (4-fluorophenyl) -4-methoxycarbonyl-5-methyl-2 was suspended. - (4-methylsulfonyl phenyl) -pyrrole [prepared as described in step (iii) above] in 20 ml of ethanol and added to the resulting suspension 2.5 ml of a 20% w / v aqueous solution of potassium hydroxide. The mixture was then heated at reflux for 15 hours. At the end of that time the mixture was cooled and diethyl ether was added. Then the mixture was shaken and the liquid phases separated. 3N aqueous hydrochloric acid was added to the aqueous layer to make it acid, and the layer was extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure, to give 0.92 g of a carboxylic acid, a hydrolyzed product. 0.92 g of this carboxylic acid was suspended in 12 ml of glycerol and the resulting suspension was stirred at 200 ° C for 30 minutes. At the end of that time the reaction mixture was poured into ice water and the resulting mixture was extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was applied to a column of silica gel chromatography and eluted with a 1: 4 by volume mixture of ethyl acetate and hexane, to give 0.55 g (yield 65%) of the title compound, as a white powder, that melts at 110-112 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) 6 ppm: 7.68 (2H, double bands, 3 = 9 Hz); 7. 20-7.08 (6H, multiple bands); 6.51 (1H, double bands, 3 = 4 Hz); 6.13 (1H, double bands, 3 = 4 Hz); 3.01 (3H, single band); 2.13 (3H, single band). Mass spectrum (IE) m / z: 329 [M + l.

EXAMPLE 44 5-TRIFLUOROMETHYL-l- (-FLUOROPHENYL) -2- (4-METILSULFONYLPHENIDPIRROL (COMPOUND No. 1-14) 44 (i) Ethyl 4,4,4-trifluoro-2- (4-methylthiophenacyl) acetoacetate Following a procedure similar to that described in example 43 (i), but using ethyl 4,4,4-trifluoroacetoacetate instead of methyl acetoacetate, the title compound was obtained as a slightly yellow powder (30% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.87 (2H, double bands, 3 = 9 Hz); 7.28 (2H, double bands, 3 = 9 Hz); 4.54 (1H, double double bands, 3 = 10 to 5 Hz); 4.26 (2H, quad bands, 3 = 7 Hz); 3.84 (1H, double double bands, 3 = 18 to 10 Hz); 3.68 (1H, double double bands, 3 = 18 to 5 Hz); 2. 53 (3H, single band); 1.29 (3H, triple bands, 3 = 7 Hz). 44 (ii) 5,5,5-Trifluoro-1- (-methylthiophenyl) pentane-1,4-dione 1.65 g (4.7 mmoles) of 4,4,4-trifluoro-2- (4-methylthiophenacyl) acetoacetate was dissolved. of ethyl [prepared as described in step fi) above], in 15 ml of dimethylformamide, and to the resulting solution was added 85 μl (4.7 mmoles) of water and 0.20 g (4.7 mmoles) of lithium chloride. The mixture was then stirred at 140 ° C for one hour, after which it was poured into ice water and the resulting mixture was extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was applied to a silica gel chromatography column with a 3: 1 by volume mixture of hexane and ethyl acetate, to give 0.26 g (20% yield) of the title compound, as a light yellow powder. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.89 (2H, double bands, 3 = 9 Hz); 7.28 (2H, double bands, 3 = 9 Hz); 3.38 (2H, triple bands, 3 = 6 Hz); 3.14 (2H, triple bands, 3 = 6 Hz). 4 (iii) 5-Trifluoromethyl-1- (4-fluorophenyl) -2- (-methylthio) pyrrole Following a procedure similar to that described in example 43 (iii), but using 5,5,5-trifluoro-l - (4-methylthiophenyl) pentane-1,4-dione [prepared as described in step (ii) above] and 4-fluoroaniline as starting materials, the title compound was obtained as a pale brown oily substance ( 42% yield). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.25 (8H, multiple bands); 6.76 (1H, double bands, 3 = 4 Hz); 6.36 (1H, double bands, 3 = 4 Hz); 2.44 (3H, single band). 44 (iv) 5-Trifluoromethyl-1- (4-fluorophenyl) -2- (4-methylsulfonyl-phenyl) -iron 5-Trifluoromethyl-1- (4-fluorophenyl) -2- (4-ethylsulfonylphenirapyrrol [prepared as described in step (iii) above] in the same manner as described in example 43 (ii), to give the title compound, as a white powder (69% yield), which melts at 136-139 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.87 (2H, double bands, 3 = 9 Hz), 7.30-7.22 (4H, multiple bands); 7. 15-7.06 (2H, multiple bands) 6.81 (1H, double bands, 3 = 4 Hz) 6.52 (1H, double bands, 3 = 4 Hz) 3.03 (3H, single band). Mass spectrum (IE) m / z: 383 [M + 1.

EXAMPLE 45 1-C4-FLUOROFENIL) - .5-DIMETHYL-2- (4-METHYLSULFONYLPHENYL) PYRROL (COMPOUND No. 1-20) 45 (i) Methyl 2-Methyl-2- (4-methylsulphenylphenidac-D-acetoacetate 0.65 g (2.1 mmol) of methyl 2- (4-methylsulfonylphenazideacetoacetate [prepared as described in example 43 (ii)] was dissolved in 20 ml of anhydrous tetrahydrofuran and to the resulting solution was added 92 mg (2.3 mmol) of sodium hydride (as a 60% w / w dispersion in mineral oil), while cooling with ice and under a nitrogen atmosphere. mixture for 10 minutes, after which 1.1 ml (2.5 mmol) of methyl iodide was added, while cooling with ice and the mixture was stirred for two hours.At the end of that time water was added to the mixture and then extracted with ethyl acetate, the organic extract was washed with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure.The residue was applied to a column from chromatography on silica gel and eluted with a 2: 3 by volume mixture of ethyl acetate and hexane to give 0.54 g (80% yield) of the title compound as a light yellow powder. 5 Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 8.14 (2H, double bands, 3 = 9 Hz); 8.06 (2H, double bands, 3 = 9 Hz); 3.77 (3H, single band); LO 3.69 (1H, double bands, 3 = 18 Hz); 3.58 (1H, double bands, 3 = 18 Hz); 3.08 (3H, single band), - 2.35 (3H, single band); 1.60 (3H, single band). L5 45 (ii) 1- (-Fluorophenyl) -, 5-dimethyl-2- (-methylsulfonyl- phenyDropyrol The hydrolysis and decarboxylation of methyl 2-methyl-2- (4-methylsulfonylphenacylacetoacetate [prepared as described in step (i) above], were carried out in the same manner as described in example 44 (ii), to give 3-rnethyl-1- (4-methylsulfonyl phenyl) pentane-1,4-dione. dione and 4-fluoroaniline were subjected to reaction in the same manner as described in Example 43 (iii) to give the title compound as a yellow powder (11% yield), which melts at 159-162 ° C.

Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.67 (2H, double bands, 3 = 9 Hz); 7.18-7.09 (6H, multiple bands); 6.41 (1H, single band); 3.01 (3H, single band); 2.12 (3H, single band); 2.04 (3H, single band). Mass spectrum (FAB) 344 [(M + H) + l. 0 EXAMPLE 46 l- (4-FLUOROFENIL) -4-HYDROXYMETHYL-2- (4-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 1-61) 46 (i) 2- (4-methylthiophenacydciacetic acid acetate) 5.70 g (57.6 mmol) of methyl cyanoacetate were dissolved in 150 ml of anhydrous tetrahydrofuran and 7.10 g (63.3 mmol) of potassium terbutoxide was added to the resulting solution, while it was cooled with ice, and then the mixture was stirred for 30 minutes.At the end of that time a solution of 14.11 g (57.6 mmoles) of 4-methylthiophenacyl bromide in 50 ml of tetrahydrofuran was slowly added dropwise to the mixture. While cooling with ice, the mixture was stirred while cooling with ice for two hours and then a saturated aqueous solution of ammonium chloride and ethyl acetate was added.The insolublee was filtered off.

Water was then added to the filtrate and the mixture was extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 1: 2 by volume mixture of ethyl acetate and hexane, to give 3.11 g (21% yield) of the title compound, as a slightly yellow powder . Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.87 (2H, double bands, 3 = 9 Hz); 7.27 (2H, double bands, 3 = 9 Hz); 4.16 (1H, double bands, 3 = 7 6 Hz); 3.83 (3H, single band); 3.74 (1H, double bands, 3 = 18 to 7 Hz); 3.53 (1H, double bands, 3 = 18 6 Hz); 2.54 (3H, single band). 46 (ii) 5-Amino-1- (4-fluoro-phenyl) -4-methoxycarbonyl-2- (4-ptethyl-sulphonylphenyl) pi rrol 3.11 g (11.8 mmoles) of 2- (4-methiithiophenazione cyanoacetate) was dissolved. of methyl [prepared as described in step (i) above] in 150 ml of methylene chloride and 5.83 g (23.6 mmoles) of 70% m-chloroperbenzoic acid was added to this mixture while cooling with ice. the resulting mixture was stirred at the temperature environment for one hour. At the end of that time, 50 ml of a 10% by weight aqueous solution (volume of sodium thiosulfate and the mixture was vigorously shaken, after which it was separated to the liquid phases) was washed into the mixture. a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure to give 3.15 g of sodium hydroxide. - (methyl 4-methyl-sulfonyl-phenazodciacetic acid acetate as a pale brown powder) 3.15 g of the powder thus obtained was dissolved in 100 ml of ethanol and 1.58 g (14.2 mmoles) of 4-fluoroaniline and 12 drops of acid were added to the resulting solution. concentrated aqueous hydrochloric acid, then the mixture was heated to reflux for three days, at the end of which time the reaction mixture was concentrated by evaporation under reduced pressure., methylene chloride was added to the residue and the insolubles were filtered off. The filtrate was concentrated by evaporation under reduced pressure and the residue was applied to a column of silica gel chromatography and eluted with a 1: 1 by volume mixture of ethyl acetate and hexane to give 2.10 g (46% yield) of the title compound, as? n white powder. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7. 68 (2H, double bands, 3 = 9 Hz); 7.26-7.11 (6H, multiple bands); 6.76 (1H, single band); 5.15 (2H, broad individual band); 3.85 (3H, single band); 3.01 (3H, single band). 46 (iii) 1- (4-Fluorophenyl) -4-methoxycarbonyl-2- (-methylsulfonyl-phenyDropyrol) 2.00 g (5.2 mmol) of 5-amino-1- (4-fluorophenyl) -4-methoxycarbonyl-2 was dissolved. (4-Methylsulfonylphenhydropyrrol [prepared as described in step (ii) above] in 50 ml of anhydrous tetrahydrofuran and 6.38 g (61.8 mmoles) of tert-butyl nitrite was added to the resulting solution at room temperature and under a nitrogen atmosphere. The mixture was then stirred at room temperature for 30 minutes, after which it was heated to reflux for two hours, then the solvent was removed by distillation under reduced pressure and the residue was applied to a column of silica gel chromatography. and eluted with a 2: 3 by volume mixture of ethyl acetate and hexane, to give 1.30 g (yield 68%) of the title compound, as a yellow powder, melting at 144-146 ° C.Magnetic Resonance Spectrum Nuclear (270 MHz, CDCl 3) d ppm: 7.95 (2 H, double bands, 3 = 9 Hz); 7. 56 (1H, double bands, 3 = 2 Hz) 7.27 (1H, double bands, 3 = 9 Hz) 7.21-7.06 (4H, multiple bands) 6.96 (1H, double bands, 3 = 2 Hz) 3.87 (3H, band individual); 3.05 (3H, single band). Mass spectrum (IE) m / z: 373 [M +]. 46 (iv) l- (4-Fluorophenyl) -4-hydroxymethyl-2- (4-methylsulfonyl-phenyl) pyrrole 0.15 g (4.0 mmol) of lithium aluminum hydride was suspended in 25 ml of diethyl ether and added to drops a solution of 0.98 g (2.6 mmol) of l- (4-fluorophenyl) -4-methoxycarbonyl-2- (4-methylsulfonylphenyl) pyrrole [prepared as described in step (iii) above] in 20 ml of sodium chloride methylene, to the suspension, while heating under reflux in a nitrogen atmosphere. The mixture was stirred at reflux for one hour and then 0.15 nl of water, 0.15 ml of a 15% w / v aqueous solution of sodium hydroxide and 0.45 ml of water were added to the mixture in that order. The mixture was then stirred at room temperature for 30 minutes. At the end of that time the mixture was dehydrated by adding anhydrous magnesium sulfate and filtered on a Celite filter aid (registered trademark). The solvent was removed from the filtrate by distillation under reduced pressure. The residue was applied to a gel chromatography column of silica, and eluted with a 2: 1 by volume mixture of ethyl acetate and hexane, to give 0.69 g (76% yield) of the title compound, as a white powder, which melts at 88-90 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.77 (2H, double bands, 3 = 9 Hz) 7.26 (2H, double bands, 3 = 9 Hz) 7.28-7.05 (4H, multiple bands) 6.97 (1H , double bands, 3 = 2 Hz) 6.60 (1H, double bands, 3 = 2 Hz) 4.65 (2H, double bands, 3 = 5 Hz) 3.04 (2H, single band).

EXAMPLE 47 l- (4-FLUOROFENIL) -4-HYDROXYMETHYL-5-METHYL-2- (4-METHYLSULFONYLPHENIDPYRROL (COMPOUND No. 1-62) L- (4-fluorophenyl) -4-methoxycarbonyl-5-methyl-2- (4-methylsulfonylphenyl) pyrrole [prepared as or described in Example 43 (iii)] was reduced in the same manner as described in Example 46 (iv), to give the title compound as a yellow powder (yield 84%), which melts at 140-142 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7. 69 (2H, double bands, 3 = 9 Hz); 7.20-7.12 (6H, multiple bands); 6.58 (1H, single band), - 4.63 (2H, double bands, 3 = 5 Hz); 5 3.01 (3H, single band); 2.13 (3H, single band). Mass spectrum (FAB) 360 [(M + H) + l.

EXAMPLE 48 10 5-DIFLUOROMETHYLL-L- (4-FLUOROFENIL) -2- (- METILSULFONYLPHENIDPIRROL (COMPOUND No. 1-13) 48 (i) 1- (-Fluorophenyl) -5-formyl-2- (4-methylsulfonylphenyl) pyrrole 1.67 g (5.3 mmol) of l- (4-fluorophenyl) -15- (4-methylsulfonylphenyl) pyrrole was dissolved. prepared as described in example 33) in 30 ml of dimethylformamide, 0.50 nrn (5.3 mmol) of phosphorus oxychloride was added to the resulting solution, and the mixture was stirred at 60 ° C. for two hours. At the end of that time, the reaction mixture was gradually added to ice water and the pH of the mixture was adjusted to a value of 8-9 by the addition of sodium carbonate. The mixture was then extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate, after which the solvent was distilled off under reduced pressure. HE "> K applied the residue to a silica gel chromatography column and eluted with a 5: 1 by volume mixture of hexane and ethyl acetate, to give 0.90 g (yield 50%) of the title compound, as a white powder, which melts at 135-137 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 9.55 (1H, single band); 7.80 (2H, double bands, 3 = 9 Hz) 7.32-7.19 (5H, multiple bands) 7.16-7.08 (2H, multiple bands) 6.64 (1H, double bands, 3 = 4 Hz) 3.04 (3H, single band). 48 (ii) 5-Di luoromethyl-1- (-fluorophenyl) -2- (-methylsulfonyl-phenyl) irol 3 ml of anhydrous diglyme 0.50 g (1.5 mmoles) of l- (4-fluorophenyl) -5-formyl was dissolved. -2- (4-methylsulfonyl-phenyl) pyrrole [prepared as described in step (i) above], and 0.17 ml (2.9 mmol) of diethylaminosulfur trifluoride was added to the resulting solution. The mixture was then stirred at 100 ° C for 6 hours. At the end of that time, water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The resulting residue was applied to a column of silica gel chromatography and eluted with a 7: 3 by volume mixture of hexane and ethyl acetate. ethyl to give 0.12 g (23% yield) of the title compound, as a slightly yellow powder, which melts at 111-112 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.76 (2H, double bands, 3 = 9 Hz) 7.27-7.21 (5H, multiple bands) 7.15-7.08 (2H, multiple bands) 6.71-6.69 (1H, multiple bands) 6.56-6.54 (1H, multiple bands) 6.42 (1H, triple bands, 3 = 54 Hz); 3.03 (3H, single band). Mass spectrum (IE) m / z: 365 CM + 1.

EXAMPLE 49 1- (4-FLUOROFENIL) -4-DIFLUOROMETHYL-2- (- METILSULFONILFENIDPIRROL (COMPOUND No. 1-29) 49 (i) 1- (4-Fluorophenyl) -4-formyl-2- (-methylsulfonylphenyl) eneol 0.58 g (1.7 mmol of l- (4-fluorophenyl) -4-hydroxymethyl-2- (4-methylsulfonylphenyl) was dissolved. pyrrole (prepared as described in example 46) in 30 ml of methylene chloride and 2.40 g of manganese dioxide was added to the resulting solution.The mixture was stirred at room temperature for 3 hours. the reaction mixture using a Celite filter material (brand recorded) and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was applied to a silica gel chromatography column and eluted with a 2: 3 by volume mixture of ethyl acetate and hexane, to give 0.52 g (90% yield) of the title compound, as a powder white, which melts at 169-171 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 9.89 (1H, single band), - 7.82 (2H, double bands, 3 = 9 Hz); 7.56 (1H, double bands, 3 = 2 Hz); 7.29 (2H, double bands, 3 = 9 Hz); 7.22-7.08 (4H, multiple bands); 6.99 (1H, double bands, 3 = 2 Hz); 3.06 (3H, single band). 49 (ii) l- (4-FluoropheniD-4-difluoromethyl-2- (4-methylsulfonyl-pheniDpyrrole) Following a procedure similar to that described in example 48 (ii), but using l- (4-fluorophenyl) -4-formyl -2- (4-methylsulfonylphenyl) pyrrole [prepared as described in step (i) above] and diethylaminosulfur trifluoride as starting materials, the title compound was obtained as a white powder (yield 16%), which melts 98-100 ° C Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7. 80 (2H, double bands, 3 = 9 Hz); 7.28 (2H, double bands, 3 = 9 Hz); 7.18-7.04 (5H, multiple bands); 6.74 (1H, triple bands, 3 = 57 Hz); 6.69 (1H, single band); 3.05 (3H, single band).

EXAMPLE 50 1- (4-FLUOROFENIL) -4-DIFLUOROMETHYL-5-METHYL-2- (4- METILSULFONYLPHENIDPIRROL (COMPOUND No. 1-30) 50 (i) l- (4-FluorofeniD-4-forn? Il-5-methyl-2- (4-Biethylsulfonyl-phenyDropyrol Following a procedure similar to that described in example 49 (i), but using l- (4- fluorophenyl) -4-hydroxymethyl-5-methyl-2- (4-methylsulfonylphenyl) pyrrole (prepared as described in Example 47) and manganese dioxide as starting materials, the title compound was obtained as a white powder ( 98% yield), which melts at 167-169 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 9.99 (1H, single band), 7.75 (2H, double bands, 3 = 9 Hz); 7.24 -7.16 (6H, multiple bands), 6.94 (1H, single band), 3.03 (3H, single band); 2. 42 (3H, single band). Mass spectrum (FAB) 358 C (M + H) +1. 50 (ii) 1- (4-Fluorophenyl) -4-difluoromethyl-5-methyl-2- (-methyl-sulfonylphenirapyrrol Following a procedure similar to that described in example 48 (ii), but using as starting materials 1- ( 4-fluorophenyl) -4-formyl-5-methyl-2- (4-methylsulfonylphenyl) pyrrole [prepared as described in step (i) above] and diethylaminosulfur trifluoride, the title compound was obtained as a white powder ( 70% yield), which melts at 136-138 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.72 (2H, double bands, 3 = 9 Hz); 7.22-7.08 (6H, multiple bands) 6.73 (1H, triple bands, 3 = 56 Hz), 6.66 (1H, single band), 3.02 (3H, single band), 2.18 (3H, single band), Mass spectrum (IE) m / z: 379 [ M + 1 EXAMPLE 51 2- (4-FLUOROFENIL) -4-PHENYL-1- (4-SULFAn? ILPHENYL) PYRROL (COMPOUND No. 2-69) 51 (i) 3- (4-Fluorobenzoyl) -2-phenylpropionaldehyde A 45% w / v solution of phenylacetoaldehyde in 4-diethyl phthalate containing 25.00 g (94 mmol) of phenylacetoaldehyde was dissolved in 50 ml of toluene and 7.96 g (94 mmol) of piperidine was added to the resulting solution. Then the mixture was heated to reflux while the produced water was removed, until the production of water stopped (approximately one hour). At that time the solvent was removed by distillation under reduced pressure to give 31.78 g of a mixture of β-piperidino styrene and diethyl phthalate, as an oily, red substance. 4.68 g of the mixture of β-piperidino styrene / diethyl phthalate was dissolved in 70 ml of anhydrous tetrahydrofuran and 1.01 g (10 mmol) of triethylamine was added to the resulting solution. Then 2.60 g (12 mmoles) of 4-fluorophenacyl bromide was added to the resulting mixture, and then stirred at room temperature for 3 hours. At the end of that time, 30 ml of IN aqueous hydrochloric acid was added to the reaction mixture and the mixture was stirred at room temperature for another hour. Then it was extracted with diethyl ether. The organic extract was washed with water and dried over anhydrous sodium sulfate. It was deleted then by distillation the solvent under reduced pressure and the residue was applied to a column of silica gel chromatography and eluted with a 95: 5 by volume mixture of hexane and ethyl acetate, to give 0.50 g of the title compound, as an oily, slightly yellow substance. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 9.80 (1H, single band); 8.03-7.98 (2H, multiple bands); 7.42-7.25 (5H, multiple bands); 7.16-7.10 (2H, multiple bands). Mass spectrum (FAB) 257 [(M + H) +]. 51 (ii) 2- (4-FluoropheniD-4-phenyl-1- (4-sulfamoylphenyl) pyrrole 0.32 g (1.25 mmoles) of 3- (4-fluorobenzoyl) -2-phenylpropionaldehyde was dissolved [prepared as described in step (i) above] and 0.26 g (1.5 mmol) of 4-sulfamoilaniline in 20 ml of acetic acid, and the mixture was heated at reflux for 4 hours, then the solvent was removed by distillation under reduced pressure and water was added to the residue, which was then extracted with ethyl acetate, the organic extract was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure and the residue was applied to a column of gel chromatography. of silica and eluted with a 3: 2 by volume mixture of hexane and ethyl acetate, to give 0.35 g (yield 60%) of the title compound, as a slightly yellow powder, melting at 192-194 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.91 (2H, double bands, 3 = 9 Hz) 7.58 (2H, double bands, 3 = 7 Hz) 7.39-7.22 (6H, multiple bands) 7.18-7.12 (2H, multiple bands) 6.99 (2H, triple bands, 3 = 9 Hz); 6.73 (1H, double bands, 3 = 2 Hz); 4.84 (2H, single band). Mass spectrum (IE) m / z: 392 [M +].

EXAMPLE 52 2- (-METOXYPHENYL) -4-METHYL-L- (SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-74) 52 (i) N- (4-Methoxybenzylidene) -4-sulfamoylaniline Following a similar procedure to that described in example Ki), but using 4-methoxybenzaldehyde and 4-sulfamoylaniline as starting materials, the title compound was obtained as a powder pale yellow (yield 95%). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 8.35 (1H, single band); 7. 94 (2H, double bands, 3 = 9 Hz); 7.86 (2H, double bands, 3 = 9 Hz); 7.23 (2H, double bands, 3 = 9 Hz); 7.00 (2H, double bands, 3 = 9 Hz); 5.98 (2H, single band); 3.90 (3H, single band). 52 (ii) tt- (4-Methoxyphenyl) -tt-sulfamoylamino) acetonitrile Following a procedure similar to that described in Example Kii), but using as starting materials N- (4-methoxybenzylidene) -4-sulfamoylaniline [prepared as described in step (i) above] and trimethylsilyl cyanide, the title compound was obtained as a pale yellow powder (yield 98%). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.74 (2H, double bands, 3 = 9 Hz) 7.51 (2H, double bands, 3 = 9 Hz) 6.97 (2H, double bands, 3 = 9 Hz) 6.82 (2H, double bands, 3 = 9 Hz) 6.60 (1H, double bands, 3 = 8 Hz) 6.41 (2H, single band); 5.54 (1H, double bands, 3 = 8 Hz); 3.84 (3H, single band). 52 (iii) 2- (-methoxyphenyl) -4-methyl-1- (4-sulfamoylphenyl) pyrrole Following a procedure similar to that described in example Kiii), but using as starting materials a- (4-rnetoxy phenyl) - a- (4-sulfaolanilino) acetonitrile [prepared as described in step (ii) above] and etacrolein, the title compound was obtained as a pale brown powder (yield 6%), which melts at 163-166 ° C . Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.84 (2H, double bands, 3 = 9 Hz) 7.23 (2H, double bands, 3 = 9 Hz) 7.03 (2H, double bands, 3 = 9 Hz) 6.79 (2H, double bands, 3 = 9 Hz) 6.73 (1H, single band) 6.23 (1H, single band) 4.78 (2H, single band) 3.79 (3H, single band) 2.18 (3H, single band) Mass spectrum (IE) m / z: 342 CM + 1.

EXAMPLE 53 1- (3, -DIMETOXYPENYL) -2- (-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 1-59) Following a procedure similar to that described in the three stages of the examples Ki), Kii) and Kiii), but using 3,4-dimethoxyaniline as starting material in place of 4-methoxyaniline, the title compound was obtained as a white powder, which melts at 124-126 ° C. The yield of the compound (yellow powder) in the first stage was 96%, in the second stage (brown prismatic crystals) it was 48% and in the third stage it was 15%. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.75 (2H, double bands, 3 = 7 Hz); 7.30 (2H, double bands, 3 = 7 Hz); 6.98 (1H, multiple bands), 6.84 (1H, double bands, 3 = 8 Hz); 6.74-6.70 (2H, multiple bands); 6.57 (1H, multiple bands); 6.39-6.37 (1H, multiple bands); 3.92 (3H, single band); 3.74 (3H, single band), - 3.03 (3H, single band). Mass spectrum (IE) m / z: 357 CM +].

EXAMPLE 54 1- (3-FLUORO-4-METOXYPENYL) -2- (-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 1-47) Following a procedure similar to that described in the three stages of the examples Ki), Kii) and Kiii), but using 3-fluoro-4-methoxyaniline as starting material in place of 4-methoxyaniline, the title compound was obtained as a white powder, which melts at 116-118 ° C. The yield of the compound (pale yellow powder) in the first stage was 94%, in the second stage (white powder) it was 87% and in the third stage it was 16%. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.77 (2H, double bands, 3 = 9 Hz) 7.29 (2H, double bands, 3 = 9 Hz) 7.00-6.84 (4H, multiple bands) 6.56-6.55 (1H, multiple bands) 6.39-6.37 (1H, multiple bands) 3.92 (3H, single band); 3.05 (3H, single band). Mass spectrum (IE) m / z: 345 [M + l.

EXAMPLE 55 l-PHENYL-2- (4-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 1-1) Following a procedure similar to that described in the three steps of examples Ki), Kii) and Kiii), but using as an aniline starting material instead of 4-methoxyaniline, the title compound was obtained as a crystal-white priematic, which melts at 140-142 ° C. The yield of the compound (pale yellow powder) in the first stage was 76%, in the second stage (pale yellow powder) was 95% and in the third stage it was 16%. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.74 (2H, double bands, 3 = 9 Hz) 7.40-7.33 (3H, multiple bands) 7.27 (2H, double bands, 3 = 8 Hz) 7.18-7.15 (2H, multiple bands) 7.00 (1H, multiple bands); 6.59-6.58 (1H, multiple bands); 6.41-6.39 (1H, multiple bands); 3.03 (3H, single band).

EXAMPLE 56 4-METHYL-L- (3. -DIMETHYLPHENYL) -2- (-METILSULFONYLPHENYL) PYRROL (COMPOUND No. 1-56) Following a procedure similar to that described in Example 8, but using methacrolein in place of acrolein in the third step, the title compound was obtained as a pale yellow powder (58% yield), which melts at 126-128 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.72 (2H, double bands, 3 = 9 Hz); 7.27-7.24 (2H, multiple bands); 7.08-7.05 (1H, multiple bands); 6. 96 (1H, single band); 6.83-6.79 (1H, multiple bands); 6.74 (1H, single band) 6.41 (1H, single band) 3.03 (3H, single band) 2.27 (3H, single band) 2.23 (3H, single band) 2.18 (3H, single band). Mass spectrum (IE) m / z: 339 [M + 1.

EXAMPLE 57 l- (4-METHYLPHENYL) -2- (4-SULPHAN? ILPHENYL) PYRROL (COMPOUND No. 1-99) 57 (i) N- (4-Sulfamoylbenzylidene) -4-methylaniline Following a procedure similar to that described in example Ki), but using 4-sulfamoylbenzaldehyde and 4-methylaniline as starting materials, the title compound was obtained as a powder yellow (82% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 8.56 (1H, single band); 8.01 (4H, single band); 7.27-7.12 (6H, multiple bands), - 2.38 (3H, single band). 57 (ii) «- (4-Hethylanilino) -ot- (-sulfamoylpheniDacetonitrile Following a similar procedure to that described in Example Kii), but using N- (4-sulfamoylbenzylidene) -4-ethylaniline [prepared as described in step (i) above] and trimethylsilyl cyanide as starting materials, the title compound was obtained as a pale yellow powder (yield 60%). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d pprn: 7.99 (2H, double bands, 3 = 8 Hz); 7.75 (2H, double bands, 3 = 8 Hz); 7.03 (2H, double bands, 3 = 8 Hz); 6.89 (2H, single band), - 6.69 (2H, double bands, 3 = 8 Hz); 5.70-5.55 (2H, multiple bands); 2.25 (3H, single band). 57 (iii) l- (4-Methylphenyl) -2- (4-sulfamoylphenyl) irrol Following a procedure similar to that described in example Kiii), but using a- (4-methylanilino) -a- (4-sulfamoylpheniDacetonitrile [prepared as described in step (ii) above] and acrolein as starting materials, the title compound was obtained as a pale brown powder (yield 28%), which melts at 131-134 ° C. Nuclear Magnetic Resonance Spectrum ( 270 MHz, CDCI3) d ppm: 7. 73 (2H, double bands, 3 = 8 Hz); 7.24 (2H, double bands, 3 = 8 Hz); 7.16 (2H, double bands, 3 = 8 Hz); 7.04 (2H, double bands, 3 = 8 Hz); 6.96 (1H, triple bands, 3 = 2 Hz); 6.55 (1H, double double bands, 3 = 3 at 2 Hz); 6.38 (1H, triple bands, 3 = 3 Hz); 4.74 (2H, single band); 2.38 (3H, single band). Mass spectrum (IE) m / z: 312 [M + l.

EXAMPLE 58 4-METHYL-L- (-METILPHENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-100) Following a procedure similar to that described in Example 57 (iii), but using methacrolein in place of acrolein, the title compound was obtained as a yellow powder (42% yield), which melts at 144-147 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.71 (2H, double bands, 3 = 8 Hz); 7.21 (2H, double bands, 3 = 8 Hz); 7.14 (2H, double bands, 3 = 8 Hz); 7.01 (2H, double bands, 3 = 8 Hz); 6.74 (1H, single band); 6. 39 (1H, single band); 4.71 (2H, single band); 2.37 (3H, single band); 2.18 (3H, single band). Mass spectrum (IE) m / z: 326 [M + l.

EXAMPLE 59 l- (4-CHLOROPHENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-96) 59 (i) 4-Chloro-N- (-sulfarooylbenzylidene) aniline Following a procedure similar to that described in example Ki), but using 4-sulfamoylbenzaldehyde and 4-chloroaniline as starting materials, the title compound was obtained as a powder pale yellow (72% yield): Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 8.52 (1H, single band); 8.02 (4H, single band), - 7.38 (2H, double bands, 3 = 9 Hz); 7.20 (2H, double bands, 3 = 9 Hz); 6.87 (2H, single band). 59 (ii) tt-f4-Chloroanilino) - «- (4-sulfamoylpheniaceacetonitrile Following a procedure similar to that described in example Kii), but using 4-chloro-N- (4- 9? sulfamoylbenzylidene) aniline [prepared as described in step (i) above] and trimethylsilyl cyanide as starting materials, the title compound was obtained as a white powder (yield 93%). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.99 (2H, double bands, 3 = 8 Hz); 7.74 (2H, double bands, 3 = 8 Hz); 7.14 (2H, double bands, 3 = 9 Hz); 7.12 (2H, single band); 6.74 (2H, double bands, 3 = 9 Hz); 6.52 (1H, double bands, 3 = 9 Hz); 5.69 (1H, double bands, 3 = 9 Hz). 59 (iii) 1- (Chlorophenyl) -2- (4-sulfamoyl enyl) iron. Following a procedure similar to that described in example Kiii), but using a- (4-chloroanilino) -a- (4-sulfamoyl) phenylacetonitrile [ prepared as described in step (ii) above] and acrolein as starting materials, the title compound was obtained as a pale yellow powder (38% yield), which melts at 179-181 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.77 (2H, double bands, 3 = 9 Hz) 7.34 (2H, double bands, 3 = 9 Hz) 7.23 (2H, double bands, 3 = 9 Hz) 7. 10 (2H, double bands, 3 = 9 Hz); 6.96 (1H, triple band, 3 = 2 Hz); 6.56 (1H, double double bands, 3 = 3 at 2 Hz); 6.40 (1H, triple bands, 3 = 3 Hz); 4.78 (2H, single band). Mass spectrum (IE) m / z: 332 [M + 1.

EXAMPLE 60 1- (4-CL0R0FENIL) -4-METHYL-2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-97) Following a procedure similar to that described in Example 59 (iii), but using methacrolein in place of acrolein, the title compound was obtained as a pale yellow powder (53% yield), which melts at 171-173 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.75 (2H, double bands, 3 = 8 Hz) 7.31 (2H, double bands, 3 = 8 Hz) 7.21 (2H, double bands, 3 = 8 Hz) 7.06 (2H, double bands, 3 = 8 Hz) 6.74 (1H, single band); 6.41 (1H, single band); 4.80 (2H, single band); 2.18 (3H, single band). Mass spectrum (IE) m / z: 346 CM *].

EXAMPLE 61 l- (4-METOXYPHENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-85) 61 (i) 4-Methoxy-N- (-sulfamoyl enylidene) aniline Following a procedure similar to that described in example Ki), but using 4-sulfamoylbenzaldehyde and 4-methoxyaniline as starting materials, the title compound was obtained, as a pale yellow powder (yield 85%).

Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 8.74 (1H, single band); 8.09 (2H, double bands, 3 = 8 Hz); 7.95 (2H, double bands, 3 = 8 Hz); 7.48 (2H, single band), - 7.37 (2H, double bands, 3 = 9 Hz); 7.01 (2H, double bands, 3 = 9 Hz); 3.80 (3H, single band). 61 (ii) o- (-methoxyanilino) - "- (-sului-1-phenylacetonitrile) Following a procedure similar to that described in example Kii), but using 4-methoxy-N- (4-sulfamoylbenzylidene) aniline [prepared as described in step (i) above] and trimethylsilyl cyanide as starting materials, the title compound was obtained as a powder white (68% yield). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) or ppm: 7.91 (2H, double bands, 3 = 8 Hz); 7.76 (2H, double bands, 3 = 8 Hz); 7.43 (2H, single band); 6.80 (4H, multiple bands); 6.40 (1H, double bands, 3 = 10 Hz); 6.03 (1H, double bands, 3 = 10 Hz); 3.67 (3H, single band). 61 (iii) l-C4-Methoxyphenyl) -2- (4-sulfamoylphenyl) pyrrole Following a procedure similar to that described in example Kiii), but using as starting materials a- (4-methoxyanilino) -a- (4- sulfamoylpheniDacetonitrile [prepared as described in step (ii) above] and acrolein, the title compound was obtained as a yellow powder (yield 8%), which melts at 112-114 ° C. Nuclear Magnetic Resonance Spectrum ( 270 MHz, CDCI3) d ppm: 7.78-7.68 (2H, multiple bands), 7.26-6.85 (7H, multiple bands), 6.53-6.51 (1H, multiple bands), 6.37-6.35 (1H, multiple bands), 5.07 ( 2H, single band), - 3.81 (3H, single band).

Mass spectrum (IE) m / z: 328 [M + l.

EXAMPLE 62 1- (4-METOXYPENYL) -4-METHYL-2- (SULPHANOYLPHENYL) PYRROL (COMPOUND No. 1-86) Following a procedure similar to that described in example 61 (iii), but using methacrolein instead of acrolein, the title compound was obtained as a pale yellow powder (35% yield), which melts at 63-64 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.69 (2H, double bands, 3 = 8 Hz) 7.18 (2H, double bands, 3 = 8 Hz) 7.05 (2H, double bands, 3 = 9 Hz) 6.85 (2H, double bands, 3 = 9 Hz) 6.72 (1H, single band) 6.38 (1H, single band) 5.04 (2H, single band) 3.80 (3H, single band) 2.18 (3H, single band). Mass spectrum (IE) m / z: 342 CM + 1.

EXAMPLE 63 4-BUTIL-1 - (-METOXYPHENYL) -2- (-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-87) Following a procedure similar to that described in example 61 (iii), but using 2-butylacrolein instead of acrolein, the title compound was obtained as a pale yellow powder (yield 85%), which melts at 115-117 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d pp: 7.70 (2H, double bands, 3 = 8 Hz); 7.26-7.19 (2H, multiple bands); 7.08-7.05 (2H, multiple bands); 6.88-6.87 (2H, multiple bands); 6.72 (1H, single band); 6.41-6.40 (1H, multiple bands); 4.89 (2H, single band); 3.82 (3H, single band); 2.53 (2H, triple bands, 3 = 8 Hz); 1.68-1.57 (2H, multiple bands); 1.49-1.36 (2H, multiple bands); 0.95 (3H, triple bands, 3 = 7 Hz). Mass spectrum (IE) m / z: 384 [M + l.

EXAMPLE 64 4-ETHYL-2- (4-METOXYPENYL) -1- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND NO 2-75) 6 (i) 1- (N, N-Diisopropylamino) -1-butene 6.25 ml (69.3 mmoles) of butyraldehyde and 19.44 ml (139 mmoles) of diisopropylamine in 30 ml of benzene were dissolved, and the mixture was heated to reflux while the produced water was eliminated, until the production of water stopped (approximately 15 hours). The solvent was then removed by distillation under reduced pressure and the residue was distilled at atmospheric pressure. Those fractions of the distillate having a boiling point of 140 to 160 ° C were collected, to give 6.95 g of the title compound, as a pale yellow oily substance (65% yield). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 5.94 (1H, double bands, 3 = 14 Hz); 4.05 (1H, double triple bands, 3 = 14 to 7 Hz); 3.50-3.34 (2H, multiple bands) 2.01-1.88 (2H, multiple bands) 1.03 (6H, double bands, 3 = 7 Hz) 0.91 (3H, triple bands, 3 = 7 Hz). 6 (ii) 2- (4-methoxy enac1) butyraldehyde It was dissolved in 10 ml of benzene 1.00 g (6.4 mmoles) of l- (N, N-diisopropylamino) -l-butene [prepared as described in step (i) above] and 0.98 g (4.3 mmoles) of 4-methoxy phenacyl bromide was added dropwise to the resulting solution, while stirring, and while cooling with ice. The reaction mixture was stirred while cooling with ice, for 15 minutes, and then at room temperature for 48 hours. At the end of that time, 9 ml of IN aqueous hydrochloric acid was added to the mixture and the mixture was stirred for 15 minutes. It was then neutralized by the addition of concentrated aqueous ammonia and extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was applied to a column of silica gel chromatography and eluted with a 4: 1 by volume mixture of hexane and ethyl acetate, to give 0.47 g (yield 49%) of the title compound, as an oily substance of pale yellow color. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 9.83 (1H, single band); 7.96 (2H, double bands, 3 = 9 Hz); 6.94 (2H, double bands, 3 = 9 Hz); 3.88 (3H, single band); 3.49-3.33 (1H, multiple bands); 3.09-2.93 (1H, multiple bands); 1. 92-1.74 (1H, multiple bands); 1.70-1.54 (1H, multiple bands); 1.01 (3H, triple bands, 3 = 7 Hz); 6 (iii) 4-Ethyl-2- (4-methoxyphenyl) -l- (-sulfamoylphenyl) pyrrole 0.47 g (2.1 mmol) of l- (4-methoxyphenacyl) butyraldehyde [prepared as above] was dissolved in 5 ml of acetic acid. described in step (ii) above] and 0.44 g (2.5 mmol) of 4-eulphamoylaniline; and the resulting solution was heated at reflux for two hours. At the end of that time the mixture was cooled to room temperature, concentrated aqueous ammonia was added to adjust its pH to a value of 8.0 and the mixture was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue was applied to a column of silica gel chromatography, eluted with a 3: 2 by volume mixture of hexane and ethyl acetate, to give 0.57 g (yield 76%) of the title compound, as a pale yellow powder, which melts at 154-156 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.84 (2H, double bands, 3 = 9 Hz) 7.24 (2H, double bands, 3 = 9 Hz) 7.04 (2H, double bands, 3 = 9 Hz) 6.79 (2H, double bands, 3 = 9 Hz) 6.74 (1H, single band); 6. 27 (1H, individual band); 4.78 (2H, single band); 3.79 (3H, single band); 2.57 (2H, quad bands, 3 = 8 Hz); 1.26 (3H, triple bands, 3 = 8 Hz).

EXAMPLE 65 2- (4-CHLOROPHENYL) -4-HETIL-l- (-SULFAMOYLPHENYL) PIRROL (COMPOUND No. 2-85) 65 (i) 1- (N, N-Diisobutylamino) -l-propene Following a procedure similar to that described in example 64 (i), but using propionaldehyde and diisobutylamine as starting materials, the title compound was obtained as a substance colorless oily (yield 29%), boiling at 63-66 ° C / 10 nrn Hg. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 5.89 (1H, double bands, 3 = 14 Hz); 3.92-3.79 (1H, multiple bands); 2.66 (2H, double bands, 3 = 7 Hz); 1.92-1.74 (2H, multiple bands); 1.54 (3H, double bands, 3 = 7 Hz); 0.80 (12H, double bands, 3 = 7 Hz). 65 (ii) 2- (4-Chlorophenacyl) propionaldehyde Following a procedure similar to that described in example 64 (ii), but using l- (N, N-diisobutylamino) -l-propene [prepared as described in step ( i) previous! and 4-chlorophenacyl bromide as starting materials, the title compound was obtained as a pale brown oily substance (39% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 9.79 (1H, single band); 7.92 (2H, double bands, 3 = 9 Hz); 7.45 (2H, double bands, 3 = 9 Hz); 3.47 (1H, double double bands, 3 = 18 to 7 Hz); 3.22-3.04 (1H, multiple bands), - 2.95 (1H, double double bands, 3 = 18 to 7 Hz); 1.25 (3H, double bands, 3 = 7 Hz). 65 (iii) 2- (4-Chloro-phenyl-4-γ-lyl-l- (4-sulfamoylphenyl) pyrrole Following a procedure similar to that described in Example 64 (iii), but using 2- (4-chlorophenazidepropionaldehyde [prepared as described in step (ii) above] and 4-sulfamoylaniline as starting materials, the title compound was obtained as a pale brown powder (yield 35%), which melts at 196-198 ° C. Nuclear Magnetic Resonance Spectrum ( 270 MHz, CDCI3) d ppm: 7. 85 (2H, double bands, 3 = 9 Hz) 7.36 (2H, double bands, 3 = 9 Hz) 7.22 (2H, double bands, 3 = 9 Hz) 7.03 (2H, double bands, 3 = 9 Hz) 6.75 ( 1H, individual band); 6.30 (1H, single band); 4.80 (2H, single band); 2.17 (3H, single band). Mass spectrum (IE) m / z: 342 CM + 1.

EXAMPLE 66 4-METHYL-2- (-METILTHOPHENYL) -1- (-SULFAMOYLFENI) PIRROL (COMPOUND No. 2-82) 66 (i) N- (4-Methylthiobenzylidene) -4-sulfamoylaniline Following a procedure similar to that described in Example Ki), but using 4-methylthiobenzaldehyde and 4-sul-famoilaniline as starting materials, the title compound was obtained as a yellow powder (88% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 8.46 (1H, single band); 7.90 (2H, double bands, 3 = 9 Hz) 7.84 (2H, double bands, 3 = 9 Hz) 7.33 (2H, double bands, 3 = 9 Hz) 7.27 (2H, double bands, 3 = 8 Hz) 7. 15 (2H, single band, wide), - 2.55 (3H, single band). 66 (ii) «- (4-Methylthiophenyl) -« - (4-sul to oilanilino) acetonitrile Following a procedure similar to that described in Example Kii), but using N- (4-methylthiobenzylidene) -4-sulfamoylaniline [prepared as described in step (i) above] and trimethylsilyl cyanide as starting materials, the title compound was obtained as a yellow powder (100% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.66 (2H, double bands, 3 = 9 Hz) 7.52 (2H, double bands, 3 = 8 Hz) 7.31 (2H, double bands, 3 = 8 Hz) 7.25-7.13 (1H, multiple bands) 6.90 (2H, single band, wide); 6.86 (2H, double bands, 3 = 9 Hz); 5.89-5.83 (1H, multiple bands); 2.50 (3H, single band). 66 (iii) 4-Methyl-2- (-methylthiophenyl) -1- (4-sulo famoyl phenyl) irol Following a procedure similar to that described in example Kiii), but using a- (4-methylthiophenyl) -a- ( 4-sulfamoylanilino) acetonitrile [prepared as described in step (ii) above] and methacrolein as the materials of Starting, the title compound was obtained as crystals in the form of exfoliation, pale brown (yield 31%), melting at 172-173 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.85 (2H, double bands, 3 = 9 Hz) 7.24 (2H, double bands, 3 = 9 Hz) 7.12 (2H, double bands, 3 = 9 Hz) 7.02 (2H, double bands, 3 = 8 Hz) 6.74 (1H, double bands, 3 = 2 Hz) 6.29 (1H, double bands, 3 = 2 Hz) 4.82 (2H, single band, wide); 2.47 (3H, single band). Mass spectrum (IE) m / z: 358 [M + l.

EXAMPLE 67 2- (4-ETOXYPENYL) -4-METHYL-L- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-78) 67 (i) N-C4-Ethoxybenzyl) en-4-sulfamoylaniline Following a procedure similar to that described in example Ki), but using 4-ethoxybenzaldehyde and 4-sulfamoylaniline as starting materials, the title compound was obtained as a powder pale yellow (76% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, sulfoxide hexadeuterated dimethyl) d ppm: 8.38 (1H, single band); 7.88 (2H, double bands, 3 = 9 Hz) 7.85 (2H, double bands, 3 = 9 Hz) 7.24 (2H, double bands, 3 = 9 Hz) 6.98 (2H, double bands, 3 = 9 Hz) 4.12 ( 2H, quad bands, 3 = 7 Hz); 1.45 (3H, triple bands, 3 = 7 Hz). 67 (ii) tt- (4-EthoxypheniD-oc- (-sulfamoylanilino) acetonitrile Following a procedure similar to that described in Example Kii), but using N- (4-ethoxybenzylidene) -4-eul-famoilaniline [prepared as described in Step (i) above] and trimethylsilyl cyanide as starting materials, the title compound was obtained as a slightly yellow powder (88% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.65 (2H, double bands, 3 = 8 Hz) 7.48 (2H, double bands, 3 = 8 Hz) 7.20-7.03 (1H, multiple bands) 6.99-6.80 (6H, multiple bands) 5.88-5.76 (1H, multiple bands) 4.04 (2H, quad bands, 3 = 7 Hz); 1.38 (3H, triple bands, 3 = 7 Hz). 67 (iii) 2- (4-Ethoxyphenyl) -4-wetyl-l- (-sulfamoylphenyl) irrol Following a procedure similar to that described in example Kiii), but using a- (4-ethoxyphenyl) -a- (4- sulfamoylanilino) acetonitrile [prepared as described in step (ii) above] and methacrolein as starting materials, the title compound was obtained as a brown powder (yield 3%), which melts at 135-139 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.83 (2H, double bands, 3 = 9 Hz) 7.22 (2H, double bands, 3 = 9 Hz) 7.02 (2H, double bands, 3 = 9 Hz) 6.77 (2H, double bands, 3 = 9 Hz) 6.72 (1H, single band, broad); 6.23 (1H, double bands, 3 = 2 Hz); 4.79 (2H, single band, broad); 4.03 (2H, quad bands, 3 = 7 Hz); 2.17 (3H, single band); 1.41 (3H, triple bands, 3 = 7 Hz). Mass spectrum (IE) m / z: 356 [M * 3.

EXAMPLE 68 4-METHYL-2- (4-PROPOXYPHENYL) -l- (4-SULFAHOYLPHENYL) PYRROL (COMPOUND No. 2-80) 68 (i) N-4-Propoxybenzylidene) -4-sulfamoylaniline Following a similar procedure to that described in example Ki), but using 4-propoxybenzaldehyde and 4-eulfa oilaniline as starting materials, el-238-title compound was obtained as a pale yellow powder (yield 84%). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dirnetyl sulfoxide) d ppm: 8.38 (1H, single band); 7.92 (2H, double bands, 3 = 9 Hz); 7.85 (2H, double bands, 3 = 9 H); 7.23 (2H, double bands, 3 = 8 Hz); 6.99 (2H, double bands, 3 = 8 Hr); 6.81 (2H, single band, broad); 4.01 (2H, triple bands, 3 = 6 Hz); L.91-J.78 (2H, multiple bands); 1.07 (3H, triple bands, 3-7 Hz). 68 (ii) tt- (4-Propoxyphenyl) -oc- (4-sulfamoylanilino) acetonitrile Following a procedure similar to that described in example l (??), but using N- (4-methylthobenzyl iden) - > \ -sul famoi Laní lina fpreparado as described f > n the step (i) above] and t-methylethyloyl cyanide as starting materials, the title compound was obtained as a pale yellow powder (yield 80%). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d pprn: 7.68 (2H, double bands, 3 = 9 Hz); 7.51 (2H, double bands, 3 = 8 Hz); 7.20-7.14 (IH, broad double bands, 3 = 8 Hz); 6.98 (2H, double bands, 3 = 9 H2), - 6.92 (2H, single band, broad); 6.88 (2H, double bands, 3 = 9 Hz); 5.83-5.80 (1H, broad double bands, 3 = 8 Hz); 3.96 (2H, triple bands, 3 = 6 Hz); 1.87-1.74 (2H, multiple bands); 1.04 (3H, triple bands, 3 = 7 Hz). 68 (iii) 4-Methyl-2- (4-propoxyphenyl) -l- (4-sulfamoylphenyl) pyrrole Following a procedure similar to that described in the example Km), but using a- (4-? Ropo? Phen? 1) -a- (4-sulphane? lan? no) aceton? tplo [prepared as described in step (n) above] and etacrolein co or starting materials, the title compound was obtained as? n pale brown powder (yield 5%), which melts at 142-145 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) 6 pprn: 7.83 (? H, double bands, 3 = 9 Hz); 7. 23 (2H, double bands, 3 = 9 Hz) 7.02 (2H, double bands, 3-9 Hz) 6.78 (2H, double bands, 3-9 Hz) 6.72 (1H, double bands, 3 = 2 Hz) 6.23 ( 1H, double bands, 3 = 2 Hz) 5.86 (2H, single band, broad); 3.90 (2H, triple bands, 3 =? Hz); 1.89-1.84 (2H, multiple bands); 1.03 (3H, triple bands, 3-7 Hz). Loop spectrum (IE) m / z: 370 fM + 1.

EXAMPLE 69 4-METHYL-2- (4-METQXI-3-METHYLPHENYL) -1- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-109) 69 (i) N- (4-Methoxy-3-methylbenzylidene) -4-sul-famoilaniline Following a procedure similar to that described in example l (?), But using 4-methoxy? -ethylbenzaldehyde and 4-s? Lfarnoylam As starting materials, the title compound was obtained as a yellow powder (92% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) 6 ppm: 8.85 to 8.31 (total: 1H, each individual band); 7.93 (IH, double bands, 3 = 8 Hz) 7.77-7.65 (2H, multiple bands) 7.26-7.23 (2H, multiple bands) 6. 91-6.86 (1H, multiple bands); 6.71-6.88 (1H, multiple bands); 4.77 to 4.14 (total: 1H, each individual band); 3.92 (3H, single band); 2.28 to 2.21 (total: 3H, each individual band). 69 (ii) «- (4-Methoxy-3-methylphenyl) -ce- (4-sulfamoylanilino) -acetonitrile Following a procedure similar to that described in Example Kn), but using N- (4-methox? -3- methybenzylidene) - 4-sulphinolamine J ina [prepared as described in step (i) above! and tp-ethylsilyl cyanide as starting materials, the title compound was obtained as a white powder (63% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated direthyl sulfoxide) d ppm: 7.62 (2H, double bands, 3-8 Hz); 7.39-7.34 (2H, multiple bands); 7.26 (1H, double bands, 3 = 9 Hz); 7.04-7.02 (3H, multiple bands); 6.90 (2H, double bands, 3 = 8 Hz); 5.97 (1H, double bands, 3 = 9 Hz); 3.81 (3H, single band); 3.33 (3H, single band). 69 (iii) 4-Methyl-2- (4-methoxy-3-methyl phenyl) -l- (4-sul-famoyl phenyl) -pyrrole Following a procedure similar to that described in example m), but using a- ( 4-methox? -3-met? Lfen? L) -a- (4-sulfamo? Lan? No) aceton? Tplo [prepared as described in step (n) above] and methacrolein as starting materials, the title compound was obtained as a pale yellow powder (yield 39%), which melts at 149-15 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.82 (2H, double bands, J ^ -g Hz); 7.26-7.20 (2H, multiple bands); 6.99 (1H, single band); 6.81-6.65 (3H, multiple bands); 6.22 (1H, single band); 4.90 (2H, single band); 3.79 (3H, single band); 2.17 (3H, single band); 2.14 (3H, single band). Mass spectrum (IE) rn / z: 332 CM +].

EXAMPLE 70 2- (3, 4-DICHLOROFENI) -4-METHYL-L- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-124) 70 (i) N- (3,4-Dichlorobenzylidene) -4-sulfamoylaniline Following a procedure similar to that described in example l (?), But using 3,4-d? Chlorobenzaldehyde and 4-sulfarnoylaniline as starting materials , the title compound was obtained as a white powder (52% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 8.49 (1H, single band); 8.09 (1H, double bands, 3 = 2 Hz); 7.94 (1H, double bands, J-9 Hz); 7.82 (1H, double double bands, 3 = 2 8 Hz); 7.63 (1H, double bands, 3 = 8 Hz); 7.30 (2H, double bands, 3 ^ -9 Hz); 7.10 (2H, single band, wide). 70 (ii) ot- (3,4-Dichloro phenyl) - < x- (4-sul-famoilanilino) acetonitrile Following a procedure similar to that described in example 1 (??), but using N- (3,4-d? chlorobenzyl) -k -sulfamellamine [prepared as It was described in step (i) above! and t nrnetilsyl lily cyanide as starting materials, the title compound was obtained as a white powder (91% yield).

Nuclear Magnetic Resonance Spectrum (270 MHz, sulfur dioxide hexadeuterated) ppm: 7.76 (1H, double bands, 3 = 2 Hz); 7.70 (2H, double bands, 3 = 9 Hz); 7.60 (1H, double bands, 3 = 8 Hz); 7.53 (1H, double double bands, 3 = 2 8 Hz); 7.24 (1H, broad double bands, 3 = 9 Hz); 6.84 (2H, single band, broad); 6.83 (2H, double bands, 3 = 9 Hz); 5.92 (1H, double bands, broad, 3 = 9 Hz). 70 (iii) 2- (3,4-DichloropheniD-4-methyl-1- (4-sulfamoylphenyl) pyrrole Following a similar procedure to that described in Example 1 (m), but using a- (3,4-d? chlorofen? l) -a- (4-sulfamo? lan?) aceton? tplo [prepared as described in step fu) above] and inetacrolein as starting materials, the title compound was obtained as? n Poi or pale coffee (yield 33%), which melts at 136-138 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDOL3) d ppm: 7.89 (2H, double bands, 3 = 9 Hz); 7.30 (IH, double bands, 3 = 3 Hz); 7.29 (1H, double bands, 3 = 9 Hz); 7.24 (2H, double bands, 3 = 9 Hz); 6.79 (1H, double double bands, 3 = 2 to g Hz); 6.76 (IH, double bands, 3 = 2 Hz); 6. 34 (1H, double bands, 3 = 2 Hz); 4.83 (2H, single band, broad); 2.17 (3H, single band). Mass spectrum (IE) rn / z: 380 TM + 1.

EXAMPLE 71 2- (3-FLUORO-4-METOXYPENYL) -4-METHYL-L- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-106) 71 (i) N- (3-Fluoro-4-methoxybenzylidene) -4-sulo familaniline Following a procedure similar to that described in example Ki), but using 3-fluoro-4-methox-benzaldehyde and 4-sulphonyl-naphine as starting materials, the title compound was obtained as a slightly yellow powder (yield 57%). Nuclear Magnetic Resonance Spectrum (270 MHz, sulfur dioxide hexadeuterated) pprn: 8.40 (1H, single band); 7.92 (2H, double bands, 3 = 9 Hz); 7.74 (IH, double double bands, 3 = 2 to 9 Hz); 7.62 (1H, double bands, 3 = 9 Hz); 7.25 (2H, double bands, 3 = 9 Hz); 7.12 (1H, triple bands, 3 = 8 Hz); 7.02 (2H, single band, broad); 3.97 (3H, single band). 71 (ii) «- (3-Fluoro-4-methoxy phenyl) -a- (4-sul-familannyl) -acetonitrile Following a procedure similar to that described in example l (??), but using N- (3-fluoro) -4-methox? Benc? L? Den) ~ 4-sulpholamino lina [prepared as described in step (i) above! and Tilmet and Isylyl cyanide as starting materials, the title compound was obtained as a slightly yellow powder (yield 98%). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated direthyl sulfoxide) d ppm: 7.69 (2H, double bands, 3 = 9 Hz); 7.37-7.33 (2H, multiple bands); 7.13-7.05 (IH, single band, broad); 7.12 (1H, triple bands, 3 = 9 Hz); 6.83 (2H, double bands, 3 = 9 Hz); 6.79 (2H, single band, broad); 5.77-5.73 (1H, multiple bands); 3.91 (3H, single band). 71 (iii) 2- (3-Fluoro-4-methoxypheni1) -4-methyl-1- (4-sulfamoyl-phenylDpyrrole Following a procedure similar to that described in the Km example), but using - (- fl uoro-4- me- »oxyphenyl) - < * - (4-sulfamo? Lan? L? No) aceton? r? lo [prepared as described in step (n) above! and methacrolein co or starting materials, the title compound co or a white powder was obtained (yield 28%), which melts at 170-173 ° C "Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.86 (2H, double bands, 3 = 9 H) 7.23 (2H, double bands, 3 = 9 Hz) 6.90-6.81 (3H, multiple bands) 6.79 (1H, double bands, 3 = 2 Hz) 6.74 (1H, double bands, 3 = 2 Hz) 4.82 (2H, single band, wide); 3.87 (3H, single band); 2.17 (3H, single band). Mass spectrum (IE) rn / z: 360 TM + 1.

EXAMPLE 72 2- (2,4-DIFLUOROPHENYL) -4-METHYL-1- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-115) 72 (i) N- (2,4-Difluorobenzylidene) -4-sulfamoylaniline Following a similar procedure to that described in example 1 (1), but using 2,4-d? Fluorobenzaldehyde and 4-sulfamoylaniline as starting materials, the title compound was obtained as a pale yellow powder (52% yield). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d pprn: 8.67 (1H, single band); 8. 20 (1H, double triple bands, 3 = 7 9 H .. '); 7.97 (2H, double double bands, 1 = 2 «7 Hz); 7.28 (2H, double double bands, 3 = 2 to 7 Hz); 7.05-6.98 (HI, multiple bands); 6.95-6.87 (1H, multiple bands); 4.88 (2H, single band, wide). 72 (ii) «- (2, 4-Dif luoro-enyl) -a- (4-sulpholinoylanilino) acetonitrile Following a procedure similar to that described in example l (??), but using N- (, 4-d? fluorobenzylidene) ~ 4 -sulfarnoilar lina [prepared as described in step (i) above! and trimethylsilyl cyanide as starting materials, the title compound was obtained as a pale yellow powder (88% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, dimer hexadeuterated ulfoxide) d ppm: 7.76 (H H, double bands, 3 = 9 H .. '); 7.71-7.65 (1H, multiple bands); 7.05-6.g2 (2H, multiple bands); 6.82 (2H, double bands, 3 = 9 Hz); 6.79 (1H, multiple bands); 6.37 (2H, single band, broad); 5.73 (IH, double bands, 3 = 9 Hz). 72 (iii) 2- (2,4-difluorophenyl) -4-methyl-1- (4-sul-famoyl phenyl) -pyrrole Following a procedure similar to that described in the Km example, but using a- (2.4 ~ d? fl? orofen? l) -a- (4-sulfarno? lan? no?) aceton? tplo [prepared as described in step (n) above] and etacrolein co or starting materials, the title compound was obtained as a pale brown powder (yield 32%), which melts at 170-1 2 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d pprn: 7.84 (2H, double bands, 3 = 9 Hz); 7.20 (2H, double bands, 3 = 9 Hz); 7.21-7.13 (1H, multiple bands); 6.87-6.67 (2H, bands rnuJti Leß); 6.80 (1H, single band, broad); 6.31 (LH, single band, broad); 4.85 (2H, single band, broad); 2.19 (3H, individual band). Spectrum of mass (IE) rn / z: 348 EM + 1.

EXAMPLE 73 2- (4-METOXYPENYL) -3-METHYL-L- (4-SULFAM0ILFENIL) PIRRQL (COMPOUND No. 2-76) Following a procedure similar to that described in example 52 (m), but using crotonaldehyde instead of rnetacrolein, the title compound was obtained as an amorphous coffee powder (21% yield). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d pprn: 7.79 (2H, double bands, 3 = 9 Hz) 7.16 (2H, double bands, 3 = 9 Hz) 7.01 (2H, double bands, 3 = 9 Hz) 6.88 (1H, bands dob Les, 3 = 3 Hz) 6.83 (2H, double bands, 3 = 9 Hz) 6.28 (1H, double bands, 3 = 3 Hz) 4.86 (2H, single band); 3.80 (3H, single band); 2.14 (3H, single band). Mass spectrum (IE) rn / z: 342 CM + 1.

EXAMPLE 74 2- (3, 4-DIFLUQROFENIL) -4-METHYL-L- (4-SULFAMQILFENIL) PIRROL (COMPOUND No. 2-112) 74 (i) N- (3,4-Dif luorobenzyl i den) -4-sulo familaniline Following a procedure similar to that described in Example Id), but using 3,4-d? FluorobenzaLdehyde and 4-sulfarnoylamine as starting materials, the title compound was obtained as a lightly yellow powder (67% yield). Spectrum of Nuclear Magnetic Resonance (270 MHz, its fox hexadeuterated dirnetiio) d pprn: 8.40 (IH, individual band); 7.96 (2H, double double bands, 3 = 7 to 2 Hz); 7.89-7.81 (1H, multiples bands); 7.67-7.62 (1H, multiple bands); 7.37-7.24 (1H, multiple bands); 7.25 (2H, double double bands, 3 = 7 2 Hz); 6.71 (2H, single band, wide). 74 (ii) tt- (3J4-DIFLUOROFENIL) -tt- (4-sulfamoylamino) acetonitrile Following a procedure similar to that described in example l (??), but using N- (3, 4-d? Fluorobenzyl? den) -4-sulfamoi ilin [prepared as described in step (i) above! and trirnethylsilyl cyanide as starting materials, the title compound was obtained as a slightly yellow powder (92% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dirnetium sulfoxide) d ppm: 7.76 (2H, double bands, 3 = 9 Hz); 7.52-7.24 (3H, multiple bands); 6.82-6.79 (3H, multiple bands); 6.28 (2H, single band, broad); 5.64 (1H, double bands, 3 = 8 Hz). 74 (iii) 2- (3,4-difluoro phenyl) -4-roethyl-1- (4-sul-famoyl phenyl) -pyrrole Following a procedure similar to that described in example m), but using or- (3) , 4-d? -fluoroferul) -a ~ (4-s? Lpno? Na? L? No?) Aceton? Tr? Lo [prepared as described in step (n) above] and mef acrolein as starting materials, obtained the title compound as a pale yellow powder (51% yield), which melts at 7-179 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.88 (2H, double double bands, 3 = 2 &7 H); 7.23 (2H, double double bands, 3 = 2 7 Hz); 7.08-6.8g (2H, multiple bands); 6.81-6.76 (1H, multiple bands); 6.74 (1H, double bands, 3 = 2 Hz); 6.29 (LH, double bands, 3 = 2 Hz); 4.99 (2H, single band, broad); 2.17 (3H, single band). Mass spectrum (IE) rn / z: 348 [M + 1.

EXAMPLE 75 1- (2,4-DIFLUORQFENIL) -4-METHYL-2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-122) 75 (i) 2,4-D fluoro-N- (4-sulfamylbenzylidene) aniline Following a procedure similar to that described in ei example l (?), but using 4-sul-phenylnobenzyl dehydrate and 2,4-difluoroamine as starting materials, the title compound was obtained as a white powder (yield 47%). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dineyl sulfoxide) d pprn: 8.79 (1H, single band); 8.12 (2H, double bands, 3 = 8 Hz); 7.97 (2H, double bands, 3 = 8 Hz); 7.58-7.34 (4H, multiple bands); 7.21-7.13 (1H, multiple bands). 75 (ii) «- (2,3-difluoroanilino) -ot- (4-sulfamoylphenyl) acetonitrile Following a procedure similar to that described in example Kn), but using 2,4-d? Fl? Oro-N- (4 -sulphame? lbenc? l? den) an? lma [prepared as described in step (i) above] and tprnethylsiyl cyanide as starting materials, the title compound was obtained as white powder (100% yield ). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.91 (2H, double bands, 3 = 8 H); 7.76 (2H, double bands, 3 = 8 Hz); 7.44 (2H, single band); 7.25-7.17 (1H, multiple bands); 6.97-6.94 (2H, multiple bands); 6.73 (1H, double bands, 3 = 10 Hz); 6. 17 (1H, double bands, J- LO Hz). 75 (iii) 1- (2, 4-Di luoro phenyl) -4-methyl-2- (4-sul famoyl phenyD-pyrrole Following a procedure similar to that described in the Km example), but using a- (2.4 -d? fluoroan? 1 i no) -cf- (4-s? lfarnoilfeniDacetomtrilo [prepared as described in step (n) above!) and methacrolein as starting materials, the title compound was obtained as a white powder ( 63% yield), which melts at 140-141 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d pprn: 7.75 (2H, double bands, 3 = 8 Hz); 7.23-7.16 (3H, multiple bands); 6.94-6.88 (2H, multiple bands); 6.69 (IH, single band); 6.43 (1H, single band); 4.99 (2H, single band); 2.20 (3H, single band); Mass spectrum (IE) rn / z: 348 l "M + l.

EXAMPLE 76 2- (4-METOXYPENYL) -l- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-73) Following a procedure similar to that described in example 52 (m), but using acrolein instead of rnetacrolei a, the title compound was obtained as a pale brown powder (yield 10%), which melts at 183-184 ° 0. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d pprn: 7.92-7.84 (2H, multiple bands) 7.39-7.23 (2H, multiple bands) 7..11-7.04 (2H, multiple bands) 6.95-6.93 (IH, multiple bands) 6.82-6.78 (2H, multiple bands) 6.39 (2H, multiple bands); 4.84 (2H, single band); 3.80 (3H, single band). Mass spectrum (IE) m / z: 342 [M + l.

EXAMPLE 77 4-METHYL-2-PHENYL-1- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-60) 77 (i) N-Benzylidene-4-sulfamoylaniline Following a procedure similar to that described in example l (?), But using benzaldehyde and 4-sulphinoylaniline as starting materials, the title compound was obtained as a yellow powder. solid (91% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated direthyl sulfoxide) d ppm: 8. 45 (1H, single band); 7.97-7.90 (2H, silent bands); 7.95 (2H, double bands, 3 = 9 Hz); 7.57-7.47 (3H, multiple bands); 7.25 (2H, double bands, 3 = 9 Hz); 6.74 (2H, single band, wide)., 77 (ii) o-Phenyl-tt- (4-sulfamoylanilino) acetonitrile Following a procedure similar to that described in Example Kn), but using N-benzyl J? Den ~ 4-sulfamoyl? Na [prepared as described in step (i) above] and trimethylsilyl cyanide as starting materials, the title compound was obtained as a slightly yellow powder (96% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, dimer hexadeuterated sulfoxide) & pprn: 7.78 (2H, double bands, 3 = 9 Hz); 7.64-7.61 (2H, multiple bands); 7.55-7.47 (3H, multiple bands); 6.85 (2H, double bands, 3 = 9 Hz); 6.52 (1H, broad double bands, 3 = 8 Hz); 6.24 (2H, single band, broad); 5.66 (1H, double bands, broad, 3 = 8 Hz). 77 (iii) 4-Methyl-2-phenyl-1- (4-sulfamoylphenyl) pyrrole Following a procedure similar to that described in eJ example Km), but using a-phenyl-a- (4-s? lfamo? lamlino) aceton? tr? lo [prepared as described in step (11) above! and netacrolein as starting materials, the title compound was obtained as a pale yellow powder (yield 47%), which melts at 165-168 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3)? ppm: 7.84 (2H, double double bands, 3 = 2 7 Hz); 7.23 (2H, double double bands, 3 = 2 to 7 Hz); 7.28-7.20 (3H, multiple bands); 7.12-7.09 (2H, multiple bands); 6.75 (1H, double bands, 3 = 2 Hz); 6.31 (1H, double bands, 3 = 2 Hz); 4.88 (2H, single band, broad); 2.18 (3H, single band). Mass spectrum (IE) m / z: 312 l "M + l.

EXAMPLE 78 4-METHYL-2- (3, 4-DIMETHYLPHENYL) -1- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-118) 78 (i) N- (3,4-dimethylbenzylidene) -4-sulfamoylaniline Following a procedure similar to that described in Example Ki), but using 3,4-dimethylbenzaldehyde and 4-sulfarnoylimide as starting materials, obtained the title compound as a pale yellow powder (yieldFour. Five%) . Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dirnetium sulfoxide) d ppm: 8.36 (1H, single band); 7.92 (2H, double bands, 3 = 9 Hz); 7.69 (1H, double bands, 3 = 2 Hz); 7.59 (1H, double double bands, 3 = 1 8 7 Hz); 7.26-7.08 (1H, multiple bands), - 7.22 (2H, double bands, 3 = 9 Hz); 6.46 (2H, single band, wide); 2.34 (6H, single band). 78 (ii) a- (3, 4-Dimethylphenyl!) - "- (4-sulfamoylanilino) acetonitrile Following a similar procedure to that described in Example Kn), but using N- (3,4-d? Rnet? Lbenc? l-den-4-sulfa oilaniline [prepared as described in the previous step (i) and triethyl cyanide 1, or as starting materials, the title compound was obtained as a slightly yellow powder (yield 91). %) Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethioxide oxide) d ppm: 7.72 (2H, double bands, 3 = 9 Hz), 7.34 (1H, single band), 7.30 (1H, double bands, 3 = 8 Hz), 7.20 (1H, double bands, 3 = 8 H), 6.82 (2H, double bands, 3 = 9 Hz); 6. 74-6.70 (HI, multiple, broad bands); 6.56 (2H, broad double bands, 3 = 8 Hz); 2.30 (3H, single band); 2.29 (3H, individual band). 78 (iii) 4-Methyl-2- (3,4-dimethylphenyl) -l- (-sulfamoylphenhydropyrrol Following a procedure similar to that described in example m), but using or- (3,4-d? Met? Lfen? l- (x- (4-sulfamoylolon) acetonylplo [prepared as described in step (ii) above) and rnetacrolein as starting materials, the title compound was obtained as a powder Amorphous slightly brown (69% yield) Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.83 (2H, double bands, 3 = 9 Hz), 7.22 (2H, double bands, 3 = 9 Hz), 6.98 -6.95 (2H, 1-foot inult bands), 6.75 (1H, multiple bands), 6.72 (1H, multiple, wide bands), 6.25 (1H, double bands, 3 = 2 Hz), 4.84 (2H, single band, wide) ), 2.23 (3H, single band), 2.Lg (3H, single band), 2.17 (3H, single band), Mass spectrum (IE) rn / z: 340 TM + 1.

EXAMPLE 79 2- (3-CHLORO-4-METOXYPENYL) -4-METHYL-L- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-100) 79 (i) N- (3-Chloro-4-methoxybenzylidene) -4-sul-famoilaniline Following a procedure similar to that described in example l (?), But using 3-chloro-4-? Netox? Benzaldehyde and 4- As a starting material, the title compound was obtained as a pale yellow powder (yield 72%). Nuclear Magnetic Resonance Spectrum (270 MHz, sulfur dioxide of hexadeuterated dimethylene) d ppm: 8.37 (1H, single band); 8.00 (1H, double bands, 3 = 2 Hz); 7.93 (2H, double bands, 3 = 9 Hz); 7.77 (1H, double double bands, J = 2 9 H); 7.24 (2H, double bands, 3 = 9 Hz); 7.09 (1H, double bands, 3 = 9 Hz); 6.90 (2H, double bands, broad, 3 = 5 H); 3.99 (3H, single band). 79 (ii) tt- (3-Chloro-4-methoxy phenyl) - "- (4-sul-familannyl) -acetonitrile Following a procedure similar to that described in example l (??), but using N- (3-chloro) -4-methox? Benc? 11 denk -s? Lepnoilanili na [prepared as described in step (i) previous! and tnrnetylsilyl cyanide as starting materials, the title compound was obtained as a slightly yellow powder (yield 64%). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.76-7.46 (4H, multiple bands); 7.02 (IH, double bands, 3 = 9 Hz); 6.80 (2H, double bands, 3 = 9 Hz); 6.71-6.58 (1H, multiple, broad bands); 6.44-6.27 (2H, multiple, broad bands); 5.57 (1H, broad double bands, 3 = 8 Hz); 3.94 (3H, single band). 79 (iii) 2- (3-Chloro-4-methoxy-pheni-1) -4-methyl-1- (4-sul-famoyl-phenyl) -pyrrole Following a procedure similar to that described in the example Km), but using a- (3-Chloro-4-methox? Phen? L-cf- (4-sulfarno? Lan? Not) aceton? Tr? Lo [prepared as described in step (ii) above] and etacrolein as starting materials , the title compound was obtained as a slightly yellow powder (37% yield) Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d pp: 7.86 (2H, double bands, 3 = 9 Hz); 7.23 (1H, bands doubles, 3 = 2 Hz), 7.23 (2H, double bands, J = 9 Hz); 6. 84 (1H, double double bands, 3 = 2 to 9 Hz); 6.78 (1H, double bands, 3 = 9 Hz); 6.73 (1H, multiple bands, broad); 6.25 (IH, double bands, 3 = 2 Hz); 4.83 (2H, single band, broad); 3.88 (3H, single band); 2.17 (3H, single band). Mass spectrum (IE) m / z: 376 ÍM + 1.

EXAMPLE 80 2- (4-METOXYPENYL) -4-METHYL-L- (4-METHYLSULFONYLPHENYL) PYRROL (COMPOUND No. 2-22) Following a procedure similar to that described in Example 28 (m), but using rnatacrolein instead of acrolein, 1 compound of the title was obtained or a white powder (yield 36%), which melts at 159-1 (51 °). C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.85 (2H, double bands, 3 = 9 Hz), 7.27 (2H, double bands, 3 = 9 Hz), 7.03 (2H, double bands, 3 = 9 Hz), 6.79 (2 H, double bands, 3 = 9 H), 6.84 (1 H, single band), 6.24 (1 H, single band), 3.80 (3 H, single band); 3. 07 (3H, individual band); 2.18 (3H, single band). Mass spectrum (FAB) 341 GM + 1.

EXAMPLE 81 4- (3-CICLOPENTILOXY-4-METOXIBENCIL) -2- (-METOXYPHENYL) -1- (4-SULFAMOILPHENIDPIRROL (COMPOUND No. 2-150) BKi) tt- (4-methoxyphenacyl) diethyl malonate 3.50 g (21.8 mmolee) of diethium malonate was dissolved in 60 ml of anhydrous tetrahydrofuran and to the resulting solution was added 2.70 g (24.0 mmoles) of potassium terbutoxide, while It cooled with ice. Then the mixture was stirred for an hour. At the end of that time, a solution of 5.00 g (21.8 mmoies) of 4-methoxyphenacyl bromide in 40 ml of anhydrous tetrahydro urane was slowly added dropwise to the mixture while cooling with ice. The mixture was stirred while cooling with ice for one hour, then a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. The residue thus obtained was applied to a column of silica gel chromatography and eluted with a 1: 4 by volume mixture of ethyl acetate and hexane, to give 4.87 g of the title compound, co or an oily substance, slightly yellow (73% yield): Nuclear Magnetic Resonance Spectrum (270 MHz, CDCJ3) d ppm: 7.97 (2H, double bands, 3 = 9 Hz); 6.94 (2H, double bands, 3 = 9 Hz); 4.25 (4H, double quad bands, 3 = 7 2 Hz); 4.04 (1H, triple bands, 3 = 7 Hz); 3.88 (3H, single band); 3.58 (2H, double bands, 3 = 7 Hz); 1.29 (6H, triple bands, 3 = 7 Hz). 81 (ii) «- (3-cyclopentyloxy-4-methoxybenzyl) -o- (4-methoxyphenacyl) -diethylmalonate 0.29 g (7.1 mmol) of sodium hydride (as a dispersion at 60% by weight) was added. weight in mineral oil) a 50 ml of anhydrous tetrahydrofuran, while cooling with ice, and then the mixture was stirred for 10 minutes. At the end of that time, a mixture of 2.00 g (6.5 mmol) of diethyl or- (4-methox-phenacyl) malonate [prepared as described in Example 1] was slowly added dropwise to the mixture while cooling with ice. step (1) above], in 20 ml of anhydrous tetrahydrofuran. Then the mixture was stirred for 30 minutes. A solution of 1.72 g was then added to the mixture. (7 .1 rnmoles) of 3-c chloride? clopen? lox? - 4 - Tocopherol in 20 ml of anhydrous fumaric acid and 0.97 g (6.5 mmol) of sodium iodide, and the resulting mixture was heated to reflux. during two hours. At the end of that time the mixture was cooled to room temperature and then acidified by the addition of 3N aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous magnesium sulfate and then the solvent was removed by distillation under reduced pressure. The residue thus obtained was applied to a column of silica gel chromatography and eluted with a 1: 4 by volume mixture of ethyl acetate and hexane, to give 2.45 g of the title compound, as an oily, pale yellow substance. . Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d pprn: 7.91 (2H, double bands, 3 = 9 Hz); 6.91 (2H, double bands, 3 = 9 Hz); 6.68 (1H, double bands, 3 = 8 Hz); 6.45 (IH, double double bands, 3 = 8 to 2 Hz); 6.36 (IH, double bands, 3 = 2 Hz); 4.31-4.22 (1H, multiple bands); 4.24 (4H, quad bands, 3 = 7 Hz); 3.86 (3H, single band); 3.77 (3H, single band); 3.49 (2H, single band); 3.44 (2H, single band); 1.72-1.45 (8H, multiple bands); 1.27 (6H, triple bands, 3 = 7 Hz). 81 (iii) ethyl tt- (3-Cyclopentyloxy-4-methoxybenzyl) -tt- (4-methoxy-phenacyl) ethyl acetate 2.43 g (4.7 mmoles) of a- (3-c? Clopent) was dissolved in 50 ml of benzene. ? lox? -4-methox? benc? l) -or- (4-methox? enale) -diethyl rnalonate [prepared as described in step (n) above] and 1.26 g (4.7 mmoles) of 18- crown-6; and 4.70 ml (4.7 rnmoles) of a 1.1M solution of potassium hydroxide in ethanol was added to the resulting solution. The mixture was stirred for 30 minutes, after which the ethanol was removed from the reaction mixture by distillation under reduced pressure. The remaining reaction solution was heated at reflux for 14 hours and then the reaction mixture was cooled to room temperature. The mixture was acidified by the addition of 3N aqueous hydrochloric acid and the resulting mixture was extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue thus obtained was applied to a column of gel chromatography. of silica and eluted with a 1: 4 mixture by volume of ethyl acetate and hexane to give J.68 g of the title compound as slightly yellow crystals (81% yield). Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d pprn: 7.92 (2H, double bands, 3 = 9 Hz); 6.00 (2H, double bands, 3 = 9 H); 6. 78 (1H, double bands, 3 = 8 Hz); 6.74-6.67 (2H, multiple bands); 4.76-4.67 (1H, multiple bands); 4.12 (2H, quad bands, 3 = 7 Hz); 3.86 (3H, single band); 3.82 (3H, single band); 3.39-3.22 (2H, multiple bands); 3.07-2.92 (2H, multiple bands); 2.83-2.72 (1H, multiple bands); 1.97-1.53 (8H, multiple bands); 1.19 (3H, triple bands, 3 = 7 Hz). 81 (iv) 4- (3-Cyclopentyloxy-4-methoxybenzDi-2- (4-methoxypheniD-l- (4-sulfamoylphenyl) pyrrolDDzGi + D 200 g (0.46 rnmoles) of a- (3-c? Clopent? lox? -4-methox? benc? l) - «- (4-methoxyethacryl) ethyl acetate Prepared as described in step (m) above], in 10 ml of anhydrous diethyl ether and added to the solution resulting in 20 rng (0.68 mmoles) of lithium aluminum hydride, while cooling with ice, the mixture was stirred for one hour while cooling with ice.At the end of that time 30 μl of water was added to the mixture. μl of a 15% w / v aqueous solution of sodium hydroxide and 80 μl of water, in that order, and the resulting mixture was stirred at room temperature for 10 minutes, then sulfate was added to the reaction mixture. anhydrous magnesium to dehydrate it and it filter the mixture using a Celite filter aid (registered trademark). The filtrate was then concentrated by evaporation under reduced pressure, to give 140 rng of a residue. The whole of this residue was dissolved in 20 ml of rnetienene chloride and 1.70 g was added to the resulting solution. (4.59 mmoles) of pipdinium dichromate, which is then stirred at room temperature overnight. The reaction mixture was filtered using a CeJite filter aid (registered trademark) and the filtrate was concentrated by evaporation under reduced pressure, to give a residue. The residue thus obtained was applied to a column of silica gel chromatography and eluted with a 4: 6 by volume mixture of ethyl acetate and hexane, to give 60 mg of a- (3-c? Clopent? Lox? 4-rnetox? Benzyl) -or- (4-rnetox? Fenac? L) acetaldehyde crude, as an oily, pale brown substance. The whole of this product thus obtained was dissolved in 3 ml of acetic acid and 26 mg (0.15 mol) of 4-sul farnoi Janilina was added to the resulting solution. The mixture was then heated at reflux for one hour, after which the acetic acid was distilled off under reduced pressure. Water was added to the residue and the mixture was neutralized with saturated aqueous solution with sodium bicarbonate. The mixture was then extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under reduced pressure to leave a residue.

The residue thus obtained was applied to a column of chromatography on silica gel and eluted with a 1: 2 mixture of ethyl acetate and hexane, to give 20 mg of the title compound, as a yellow powder (yield 9%), which melts at 81-84 ° C. . Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.82 (2H, double bands, 3 = 9 Hz); 7.20 (2H, double bands, 3 = 9 Hz); 7.02 (2H, double bands, 3 = 9 Hz); 6.87-6.72 (5H, multiple bands); 6.63 (1H, single band, broad); 6.24 (1H, double bands, 3 = 2 Hz); 4.84 (2H, single band, broad); 4.80-4.70 (1H, multiple bands); 3.83 (3H, single band); 3.80 (2H, single band); 3.78 (3H, single band); 1.95-1.53 (8H, multiple bands).

EXAMPLE 82 1- (4-ACETYLAMINOSULFONYLPHENYL) -2- (4-METOXYPENYL) -4-METHYLPYRROL (COMPOUND No. 2-148) 82 (i) 3- (4-Methoxybenzoyl) -2-methylpropionaldehyde was added dropwise under a stream of nitrogen 4. 36 g (75 mrnols) of propionaldehyde, to a solution of 6.46 and (50 mmoles) of diisopropylamine, 39 g of molecular sieves of 4fi and 10 rng of 2,6-d? -terbut? 1-4-methyl phenol in 50 nr of tetrahydrofurans, and the mixture was allowed to stand for three hours. At the end of that time, 5.73 g (25 rnmoles) of 4'-methoxy-2-bromoacetophenone was added to the mixture and the mixture was allowed to stand overnight at room temperature. The reaction mixture was then filtered and 55 ml of IN aqueous hydrochloric acid was added to the filtrate to separate it into phases. The aqueous layer was separated and extracted twice with ethyl acetate. The organic extracts were combined and washed with water and with a saturated aqueous solution of sodium chloride, in that order. The resulting solution was then dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue thus obtained was applied to a column of silica gel chromatography and eluted with a 2: 1 by volume mixture of hexane and ethyl acetate, yielding 2.82 g (yield 26%) of the title compound, as an oily pale yellow substance. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d pprn: 9.80 (1H, single band); 7.g6 (2H, double bands, 3 = 9 Hz); 6.94 (2H, double bands, 3 = 9 H); 3.88 (3H, single band), - 3.44 (1H, double double bands, 3 = 6 to J7 Hz); 3.17-3.03 (1H, multiple bands); 2. 97 (1H, double double bands, 3 = 6 17 Hz); 1.23 (3H, double bands, 3 = 7 Hz). 82 (ii) 1- (Acetylaminosul onylphenyl) -2- (methoxyphenyl) -4-methylpyrrole A solution of 2.82 g (12.8 mmoJes) of 3- (4-rnetoxy? Benzoyl) was heated under reflux for three hours. -2-rnetylpropionaldehyde [prepared as described in step (i) above] and 2.74 g (12.8 rnmoles) of 4-acetiJarninosulfoni laní 1 ina in 30 rnl of acetic acid; after which the acetic acid was removed by distillation under reduced pressure. The residue thus obtained was dissolved in chloroform and a saturated aqueous solution of sodium bicarbonate was added to the resulting solution to separate it into phases. The organic extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order, and dried over anhydrous magnesium sulfate, after which it was concentrated by evaporation under reduced pressure. The residue thus obtained was applied to a column of silica gel chromatography and eluted with a 2: 3 by volume mixture of hexane and ethyl acetate. It was then recrystallized from ethanol, to give 0.79 g (yield 16%) of the title compound, as a white powder, which melts at 215-217 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) 6 pprn: 8. 07-7.91 (1H, single band, broad); 7.95 (2H, double bands, 3 = 9 Hz) 7.24 (2H, double bands, 3 = 9 Hz) 7.03 (2H, double bands, 3 = 9 Hz) 6.79 (2H, double bands, 3 = 9 Hz) 6.73 (1H, single band); 6.23 (1H, single band); 3.80 (3H, single band); 2.17 (3H, single band); 2.og (3H, single band). Mass spectrum (FAB) 384 TM + l.

EXAMPLE 83 1- (4-ACETYLAMINOSULFONYLPHENYL) -2- (3, 4-DIMETHYLPHENYL) -4- METILPYRROL (COMPOUND No. 2-149) 83 (i) 3-Bromo-2-methylpropionaldehyde-ethylene acetal A 16.03 ml (0.12 mol) of tet raima was charged to a flask and 24.27 i (0.47 mol) of bromine was added dropwise while cooling with ice. The hydrogen bromide gas thus produced was bubbled through a tube to 55.21 ml (0.g9 moles) of ethanol, while cooling with ice. After 4 hours, 25 ml (0.30 ml) of meth acrolein was added dropwise to the mixture, and then stirred at room temperature for one hour. The reaction solution was extracted twice with pentane and the organic extract with a 5% aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, in that order. It was then dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue thus obtained was distilled under reduced pressure to give 29.81 g (51% yield) of the title compound, as a colorless oily substance with a boiling point of 65-68 ° C / 2 mm Hg. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) ppm: 4.83 (1H, double bands, 3 = 5 Hz); 4.03-3.84 (4H, multiple bands); 3.53 (1H, double double bands, 3 = 5 &10 Hz); 3.37 (IH, double double bands, 3 = 7 to 10 Hz); 2.18-2.01 (1H, multiple bands); 1.11 (3H, double bands, 3 = 7 H). 83 (ii) 3- C3,4-Dimethylbenzoyl) -2-methylpropionaldehyde-ethylene acetal 0.28 ml (3.4 rnmoles) of J, 2-d-bromoethane was added to a suspension of 1.66 g (68.1 mmol) of magnesium in 5 ml of anhydrous tetrahydrofuran, under a stream of nitrogen. Then 9.96 g (51.1 mmoles) of 3-bro-no-2-rnetiipropionaldehyde-ethiienacetal [prepared as described in step (1) above] was added dropwise, while cooling with ice, after which it was stirred for one hour Ja mix. HE A solution of 6.58 g (34.1 mmoles) of N-rnetox? -N-rnet? l-3,4-d? rnetilbenzam? da in 30 nl of tetrahydrofuran was added dropwise to the mixture, and the resulting mixture was stirred, while cooling with ice, for one hour. A saturated aqueous solution of ammonium chloride was added to the mixture and the resulting mixture was extracted twice with ethyl acetate. The organic extracts were combined and washed with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue thus obtained was applied to a column of silica gel chromatography and eluted with a 6: 1 by volume mixture of ethyl acetate and hexane to give 3.26 g (yield 39%) of the title compound as a substance. oily, colorless Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7..75 (1H, single band); 7.71 (1H, double bands, 3 = 8 Hz); 7.20 (1H, double bands, 3 = 8 Hz); 4.82 (1H, double bands, 3 = 4 Hz); 4.01-3.83 H, multiple bands); 3.18 (1H, double double bands, 3 = 5 &16 Hz); 2.76 (1H, double double bands, 3 = 9 &16 Hz); 2.62-2.47 (1H, multiple bands); 2.31 (6H, single band); L.02 (3H, double bands, 3 = 7 Hz) .. 83 (iii) l- (4-Acetylaminosulfonylphenyl) -2- (3,4-dimethylphenD-4-methyl pyrrole 3.26 (13.1 nmol ee) of 3- (3, -dirnethylbenzoyl) -2-methyprophenaldeh was dissolved ? do-et? lenacetal [prepared as described in step (n) above] and 2.81 g (13.1 rnmoles) of 4-acet? lam? sulfosilamylin, in a mixture of 52 rnL (52 mmoles) of aqueous hydrochloric acid IN and 16 rnl of tetrahydrofuran, and the mixture was heated at 70 ° C for one hour.At the end of this time the mixture was allowed to stand to allow it to cool, then the mixture was extracted three times with ethyl acetate. The organic extracts were washed with a saturated aqueous solution of sodium chloride, and the resulting solution was dried over anhydrous magnesium sulfate, after which it was concentrated by evaporation under reduced pressure. of silica gel chromatography and <The mixture was eluted with a 3: 2 by volume mixture of hexane and ethyl acetate and crystallized from dusopropyl ether to give 1.27 g (yield 25%) of the title compound as a white powder, which melted at room temperature. 192-193 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d pprn: 7.95 (2H, double bands, 3 = 9 H); 8.05-7.93 (1H, single band, broad); 7.25 (2H, double bands, 3 = 9 Hz); 6. 98 (1H, double bands, 3 = 8 Hz); 6.93 (1H, single band); 6.76 (1H, double bands, 3 = 8 Hz); 6.74 (1H, single band); 6.26 (1H, single band); 2.23 (3H, individual band); 2.17 (6H, single band); 2.08 (3H, single band). Mass spectrum (IE) rn / z: 382 TM + l.

EXAMPLE 84 4-METHYL-1- (4-METHYLTHEPHENYL) -2- (-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-164) B4 (i) 4-Methylthio-N- (4-sulfamoylbenzylidene) añiline Following a procedure similar to that described in example L (?), But using as starting materials 4-sulfarnoylbenzaldehyde and 4-met? lithioaniline, the title compound was obtained as a yellow powder (yield 95%). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethylsulphoxide) d ppm: 8.76 (1H, single band); 8.10 (2H, double bands, 3 = 8 Hz); 7.95 (2H, double bands, 3 = 8 Hz); 7.50 (2H, single band); 7.33 (4H, multiple bands); 2. 50 (3H, single band). 8 (ii) tt- (4-Methylthioanilino) -a- (4-sulfamoylphenyl) acetonitrile Following a procedure similar to that described in example Kn), but using 4-rnet? Lt? ON- (4-s? Lfamo? Lbenc ? ln) an? l? na [prepared as described in step (i) above] and t-phenyl ethyl eylyl cyanide as starting materials, the title compound was obtained as a yellow powder (100% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeu- ferated direthyl sulfoxide) d ppm: 7.92 (2H, double bands, 3 = 8 Hz); 7.75 (2H, double bands, 3 = 8 Hz); 7.45 (2H, single band); 7.18 (2H, double bands, 3 = 9 Hz) 6.92-6.78 (3H, multiple bands) 6.15 (1H, double bands, 3 = 9 Hz) 2.38 (3H, single band). 84 (iii) 4-Methyl-l- (4-methylthiopheniD-2- (4-sulphamoylphenyl) p rrol Following a procedure similar to that described in example m), but using co or starting materials w- (4- met? l? oan? l? no) -or- (4-sulfamo? lfeml) ace? t? lo [prepared as described in step (n) above] and methocrolein, the title compound was obtained as a slightly yellow powder (yield 33%), which melts at 194-196 ° C.

Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) 6 pprn: 7.54 (2H, double bands, 3 = 8 Hz) 7.29-7.20 (6H, multiple bands) 7.10 (2H, double bands, 3 = 9 Hz) 6.88 (1H, single band); 6.41 (1H, multiple bands); 2.48 (3H, single band); 2 . 1 0 (3H, dual i ndivi band). Mass spectrum (TE) rn / z: 358 CM + 1.

EXAMPLE 85 1- (4-ETHYLTHEPHENYL) -4-METHYL-2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-165) 85 (i) 4-Ethylthio-N- (4-sulfamoylbenzyl) en aniline Following a procedure similar to that described in Example Id), but using as starting materials 4-s-p-leno-benzyl-aldehyde and 4-ethyl-t-oan? lina, the title compound was obtained as a yellow powder (56% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated direthyl sulfoxide) d pprn: 8.76 (1H, single band); 8.10 (2H, double bands, 3 = 8 Hz); 7.95 (2H, double bands, 3 = 8 Hz); 7.50 (2H, single band); 7. 40-7.30 (4H, rnultipler bands, 3.01 (2H, quad bands, 3 = 7 Hz), 1.27-1.22 (3H, multiple bands). 85 (ii) «- (-Eththioanilino) -« - (4-etho famoyl phenyl) acetonitrile Following a procedure similar to that described in example l (??), but using as starting materials 4-et? Lt? ON- (4 ~ sulfarno? Lbenc? J? Den) an? Lma [prepared as described in step (i) above! and tri-ethylsilyl cyanide, the title compound was obtained as a yellow powder. (100% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dirne ilo sulfoxide) d ppm: 7.91 (2H, double bands, 3 = 8 Hz); 7.54 (2H, double bands, 3 = 8 Hz); 7.44 (2H, single band); 7.23 (2H, double bands, 3 = 8 Hz); 6.g3 (1H, double bands, 3 = g Hz); 6.80 (2H, double bands, 3 = 8 Hz); 6.14 (1H, double bands, 3 = g Hz); 2.79 (2H, quad bands, 3 = 7 Hz); 1.14 (3H, triple bands, 3 = 7 Hz). 85 (iii) l- (4-EthylthiopheniD-4-methyl-2- (4-sulo famoyl phenyl) irol Following a procedure similar to that described in the example Km), but using as starting materials or- (4-et? Lt? Oan? L? No) -or- (4-sulfamo? Lfen? L) aceton? Tp [prepared as described in step (11) above! and methacrolein, the title compound was obtained as a slightly yellow powder (69% yield), which melts at 139-141 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, hexadeuterated di-ethyl-sulfoxide) or ppm: 7.65 (2H, double bands, 3 = 8 Hz); 7.34-7.31 (4H, multiple bands); 7.21 (2H, double bands, 3 = 9 H); 7.10 (2H, double bands, 3 = 8 Hz); 6.90 (1H, single band); 6.42-6.41 (1H, multiple bands); 2.99 (2H, quad bands, 3 = 7 Hz); 2.10 (3H, single band); 1.24 (3H, triple bands, 3 = 7 Hz). Mass spectrum (IE) m / z: 372 CM + 1.

EXAMPLE 86 4-METHYL-L- (3, 4-DIMETHYLPHENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-160) 86 (i) 3, 4-Dimethyl-N- (4-sulfamoylbenzylidene) aniline Following a procedure similar to that described in example l (?), But using 4-sulfarno? Lbenzaldehyde and 3,4-dirnethylamine as the materials of Starting, the title compound was obtained as a yellow powder (60% yield).

Nuclear Magnetic Resonance Spectrum (270 MHz, dimethyloxyddehyde hexadeuterated) 6 pprn: 8.94 (2H, double bands, 3 = 8 Hz); 8.72 (1H, single band); 7.94 (2H, double bands, 3 = 8 Hz); 7.48 (2H, single band); 7.21-7.06 (3H, multiple bands); 2.27 (3H, single band); 2.24 (3H, single band). 86 (ii) tt- (3, 4-Dimethylanilino) -oc- (4-sulfamoylphenyl) acetonitrile Following a procedure similar to that described in example l (??), but using as starting materials 3,4-dirnethyl-N - (4-eul farnoi lbenc? L? Den) an? J i na [prepared as described in step (i) above] and tp ethylsilyl cyanide, the title compound was obtained, as a yellow powder (yield 100 %). Nuclear Magnetic Resonance Spectrum (270 MHz, sul fox of hexadeuterated dirnetyl) d ppm: 7.91 (2H, double bands, 3 = 8 Hz); 7.53 (2H, double bands, 3 = 8 Hz); 7.44 (2H, single band); 6.g3 (IH, double bands, 3 = 8 Hz); 6.66 (1H, multiple bands); 6.57-6.49 (3H, multiple bands); 6.07 (1H, double bands, 3 = 10 H. '); 2. 14 (3H, single band); 2.10 (3H, single band). 86 (iii) 4-Methyl-l- (3,4-dimethylpheniD -2- (4-sulfamoylphenhydropyrrol Following a procedure similar to that described in example Kiii), but using a- (3,4-dimethylanilino) -a as starting materials - (4-Sulfarnoylphenyl) acetonitrile [prepared as described in step (ii) above!) And methacrolein, the title compound was obtained as a slightly yellow powder (yield 43%), which melts at 118-120 ° C. Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.82 (2H, double bands, 3 = 8 Hz), 7.19 (2H, double bands, 3 = 8 Hz), 7.05 (1H, double bands, 3 = 8 Hz ), 6.97 (1H, single band), 6.79 (1H, double bands, 3 = 8 Hz), 6.73 (1H, single band), 6.38 (1H, single band), 5.02 (2H, single band),; 2.25 (3H, single band), 2.22 (3H, single band), 2.17 (3H, single band), Mass spectrum (IE) m / z: 340 [M + l.

EXAMPLE 87 4-METHYL-2- (3, 5-DIMETHYLPHENYL) -1- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-147) 87 (i) N- (3,5-Dimethylbenzylidene) -4-sulfamoylaniline Following a procedure similar to that described in example l (?), But using 3,5-d? Meth? Lbenzaldehyde and 4-sulfarnoylaniline as materials starting, the title compound was obtained as a pale yellow powder (59% yield). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 8.85 (1H, single band); 7.85 (2H, double bands, 3 = 8 Hz); 7.57 (2H, single band); 7.37 (4H, double bands, 3 = 8 Hz); 7., 22 (1H, single band); 2.35 (6H, single band). 87 (ii) «- (3,5-Dimethylphenyl) -« - (-sulfamoylanilino) acetonitrile Following a procedure similar to that described in example Kn), but using as starting materials N- (3,5-d? lbenc? l? den) -4-sulfamo? lan? lina [prepared as described in step (i) above] and trimethyl cyanide, the title compound was obtained as a pale yellow powder (yield 90%).

Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dirnetyl sulfoxide) or pprn: 7.61 (2H, double bands, 3 = 8 Hz); 7.29 (1H, double bands, 3 = 8 Hz); 7.16 (2H, single band); 7.04 (3H, single band); 6.89 (2H, double bands, 3 = 8 Hz); 6.00 (1H, double bands, 3 = 8 Hz); 2.30 (6H, single band). 87 (iii) 4-Methyl-2- (3, 5-dimethyl phenyl) -1- (4-sulo famoyl phenyl) pi rrol Following a procedure similar to that described in the example Km), but using as starting materials or- (3, 5-d? Rnet? I phenyl) -o * - (4-sul famoilanilinoJacetonitplo [prepared as described in step (n) above '] and rnetacrolein, the title compound was obtained as a slightly brown powder ( yield 28%), which melts at 163-166 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d pprn: 7.83 (2H, double bands, 3 = 9 Hz), 7.23 (2H, double bands, 3 = 9 Hz), 6.85 (IH, single band), 6.73 (3H, single band), 6.27 (1H, double bands, 3 = 2 Hz), 4.85 (2H, single band), 2.21 (6H, single band); 2 . 17 (3H, band i ndiv i dual). Spectrum of mass (IE) rn / z: 340 TM + 1.

EXAMPLE 88 3-METHYL-2- (4-METHYLTHEPHENYL) -1- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-83) Following a procedure similar to that described in example 66 (m), but using crotonaldehyde instead of methacrolein, the title compound was obtained as a pale yellow powder (24% yield), which melts at 132-134 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.8J (2H, double bands, 3 = 9 Hz); 7.18 (2H, double bands, 3 = 4 Hz); 7.15 (2H, double bands, 3 = 4 Hz); 7.00 (2H, double bands, 3 = 9 H); 6.89 (1H, double bands, 3 = 3 Hz); 6.26 (1H, double bands, 3 = 3 Hz); 4.78 (2H, single band); 2.48 (3H, single band); 2.15 (3H, single band). Mass spectrum (IE) rn / z: 358 [M + l.

EXAMPLE 89 1- (4-METOXYPENYL) -5-METHYL-2- (SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-88) Following a procedure similar to that described in example 6l (? I?), But using rnetyl vinyl ketone instead of acrolema, the title compound was obtained as a pale yellow powder (yield 39%), which melts at 196-197 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethylsulphoxide) d ppm: 7.56 (2H, double bands, 3 = 7 Hz); 7.22 (2H, single band); 7.16-7.13 (4H, multiple bands); 6.99 (2H, double bands, 3 = 7 Hz); 6.46-6.44 (1H, multiple bands); 6.07 (HI, multiple bands); 3.33 (3H, single band); 2.03 (3H, single band). Mass spectrum (IE) rn / z: 342 [M + l.

EXAMPLE 90 5-METHYL-L- (4-METHYLTHOPHENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-95) Following a procedure similar to the one described in Example 84 (m), but using methylimmo ketone instead of metacrolema, the title compound was obtained as a yellow powder (yield 65%), which melts at 139-141 ° C. Nuclear Magnetic Resonance Spectrum- (270 MHz, hexadeuterated di methyl sulfoxide) d pprn: 7.59 (2H, double bands, 3 = 8 Hz); 7.34-7.15 (8H, rn, 3 Hz); 6.48 (1H, double bands, 3 = 3 Hz); 6.10 (1H, double bands, 3 = 3 Hz); 2.50 (3H, single band); 2.07 (3H, individual band). Mass spec (IE) m / z: 358.

EXAMPLE 91 1- (-CLOROFENIL) -5-METHYL-2- (4-SULFAM0ILFENIL) PIRROL (COMPOUND No. 1-98) Following a procedure similar to that described in Example 59 (in), but using ethylvinyl ketone in place of acrolein, the title compound was obtained as a pale yellow powder (yield 44%), which melts at 152-154 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dirnetyl sulido oxide) d pprn: 7.61 (2H, double bands, 3 = 8 Hz); 7.53 (2H, double bands, 3 = 8 Hz); 7.28-7.20 (4H, multiple bands); 7.15 (2H, double bands, 3 = 8 Hz); 6. 49 (1H, double bands, 3 = 3 Hz); 6.12 (1H, double bands, 3 = 3 H), - 2.08 (3H, single band). Mass spectrum (IE) rn / z: 346 [M + l.

EXAMPLE 92 l- (4-METHYLTHEPHENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-93) Following a procedure similar to that described in example 84 (m), but using acrolein a in place of methacrolein, the title compound was obtained as a pale yellow powder (yield 15%), which melts at 159-l6lßC. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.75 (? H, double bands, 3-9 Hz); 7.26-7.21 (4H, multiple bands); 7.10-7.07 (2H, multiple bands); 6.97-6.95 (1H, multiple bands); 6.55 (1H, double double bands, 3 = 4 ft 2 Hz); 6.39 (IH, triple bands, 3 = 4 Hz); 4.82 (2H, single band); 2.50 (3H, single band). Mass spectrum (IE) m / z: 344 TM + l.

EXAMPLE 93 l- (2,4-DICHLOROPHENYL) -2- (4-SULFAHOYLPHENYL) PYRROL (COMPOUND No. 1-127) Following a procedure similar to that described in the three steps of examples 19 (?), 19 (n) and 19 (m), but using as starting material 2,4-d? Chloroan? Lna instead of 4 -fluoroamyl, the title compound was obtained as a white powder, which melts at 147-149 ° C. The total yield of the compound in the three stages was 15%. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d pprn: 7.79 (2H, double bands, 3 = 9 Hz); 7.42-7.36 (2H, multiple bands); 7.26-7.23 (2H, multiple bands); 6.96-6.90 (2H, multiple bands); 6.50 (1H, double double bands, 3 = 3 to 1 Hz); 6.40 (1H, triple bands, 3 = 3 Hz); 4.87 (2H, single band). Mass spectrum (TE) rn / z: 366 TM + 1.

EXAMPLE 94 l- (4-ETOXYPHENYL) -2- (4-SULFAMQILPHENYL) PYRROL (COMPOUND No. 1-89) Following a procedure similar to that described in « three stages of examples 19 (i), 19 (ii) and 19 (iii), but using 4-ethoxyaniline instead of 4-fl-oroanilma as the starting material, the title compound was obtained as? n white powder, which melts at 126-128 ° C. The total yield of the compound in the three stages was 16%. Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated di methyl sulfoxide) d ppm: 7.65 (2H, double bands, 3 = 8 Hz); 7.30-7.22 (4H, multiple bands); 7.14-7.06 (3H, multiple bands); 6.96 (2H, double bands, 3 = 9 H); 6.56 (1H, double double bands, 3 = 3 &1 Hz); 6.32 (1H, triple bands, 3 = 3 Hz); 4.04 (2H, quad bands, 3 = 7 Hz); 1.33 (3H, triple bands, 3 = 7 Hz).

EXAMPLE 95 4-METHYL-2- (-METILSULFINYLPHENYL) -1- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 2-151) 0.35 g (1.0 rnmoles) of 4-methyl-2- (4-ethylthiophenyl) -l- (4-sul-p-phenyl) p was dissolved. (prepared as described in Example 66) in 50 ml of chloroform and 0.27 g (1.1 rnmoles) of 70% rn-chloroperbenzoic acid was added to the resulting solution, in various portions, while cooling with ice, after which the mixture was stirred during a hour, while cooling with ice. The reaction mixture was then diluted with chloroform and washed with a 10% w / v aqueous solution of sodium thiosulfate and with a saturated aqueous solution of sodium bicarbonate, twice with each, in that order. The organic layer was then dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue thus obtained was applied to a silica gel chromatography column and eluted with a 95: 5 by volume mixture of rnetylene chloride and methanol, to give 0.23 g (63% yield) of the title compound as a powder. Pale orange color, which melts at 222-226 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.88 (2H, double bands, 3 = 9 Hz); 7.52 (2H, double bands, "1 = 8 Hz), 7.26 (2H, double bands, 3 = 3 Hz), 7.25 (2H, double bands, 3 = 3 Hz), 6.79 (1H, indiviual band), 6.39 (1H, double bands, 3 = 2 Hz), 4.90 (2H, single band), 2.74 (3H, single band), 2.22 (3H, single band), Mass spectrum (TE) rn / z: 374 [M +! .

EXAMPLE 96 4-METHYL-L- (4-METHYLSULFINYLPHENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-153) 4-Methyl-1- (4-methylthiophenyl) -2- (4-sul-phenoxy-1-phenypyrrole (prepared as described in Example 84) was oxidized, in the same manner as described in Example 95, to give the compound of the title as a white powder (yield 84%), which melts at 249-251 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.73-7.66 (4H, multiple bands); 7.37-7.31 (4H, multiple bands); 7.23 (2H, double bands, 3 = 8 Hz); 7.00 (1H, multiple bands); 6.46 (HI, multiple bands); 2.78 (3H, single band); 2.12 (3H, single band). Mass spectrum (IE) rn / z: 374 [M + l.

EXAMPLE 97 5-CHLORO-1- (4-METOXYPHENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-147) L- (4-rnetoxyphenyl) -2- (4-sulfamoylphenyl) pyrrole was chlorinated (prepared as described in example 61) thereof as described in example 37, to give the title compound as a pale yellow powder (yield 80%), which melts at 119-120 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d pprn: 7.69 (2H, double bands, 3-8 Hz) 7.17 C2H, double bands, 3 = 8 Hz) 7.11 (2H, double bands, 3 = 9 Hz) 6.92 (2H, double bands, 3 = 9 Hz) 6.50 (1H, double bands, 3 = 4 Hz) 6.29 (1H, double bands, 3 = 4 Hz) 4.82 (2H, single band); 3.85 (3H, single band). Mass spectrum (IE) rn / z: 362 GM + 1.

EXAMPLE 98 5-BR0M0-1- (4-METOXYPENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-148) It was brominated l- (4-rnetox? Feni 1) -2- (4-sul famoil eml Jpirrol (prepared as described in Example 61), in the same manner as described in Example 35, to give the title compound as a pale yellow powder (yield 76%), which melts at 121-123 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated 1-dimethyl sulfate) d ppm: 7. 62 (2H, double bands, 3 = 8 llz) 7.28-7.17 (6H, multiple bands) 7.02 (2H, double bands, 3 = 9 Hz) 6.63 (1H, double bands, 3 = 4 Hz) 6.48 (1H, bands double, 3 = 4 H) 3.80 (3H, single band). Mass spectrum (IE) rn / z: 406 TM + 1.

EXAMPLE 99 5-CHLORO-1- (4-METOXYPENYL) -4-METHYL-2- (4-SULFAMQYLPHENYL) PYRROL (COMPOUND NO 1-149) 1 - (4? -nuclex? Phen? L) -4-rnet il -2- (4-sulfamoylphenyl) pyrrole (prepared as described in Example 62) was chlorinated, in the same manner as described in Example 37, to give the title compound, as a pale yellow powder (yield 80%), which melts at 155-156 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.67 (2H, double bands, 3 = 9 Hz); 7.16-7.06 (4H, multiple bands); 6.90 (2H, double bands, 3 = 9 Hz); 6.40 (IH, individual band); 4.g4 (2H, single band); 3.84 (3H, single band); 2.14 (3H, single band).

Mass spectrum (IE) m / z: 376 TM + 1.

EXAMPLE 100 5-CHLORINE-1- (4-ETOXYPENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-151) L- (4-ethoxy? Phen? L) -2- (4-sulfarno? Lphenyl) p was chlorinated? rrol (prepared as described in Example 94), in the same manner as described in Example 37, to give the title compound, as a white powder (yield 93%), which melts 124-125 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.70 (2H, double bands, 3 = 9 Hz); 7.11-7.07 (4H, multiple bands); 6.90 (2H, double bands, 1-9 Hz); 6.50 (1H, double bands, 3 = 4 Hz); 6.29 (1H, double bands, 3 = 4 Hz); 4.75 (2H, single band); 4.06 (2H, quad bands, 3 = 7 Hz); 1.45 (3H, triple bands, 3 = 7 Hz). Mass spectrum (IE) rn / z: 376 TM + l.

EXAMPLE 101 5-CHLORO-1- (4-METHYLTHEPHENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-152) L- (4-methylthiophenyl) -2- (4-sulfamoylphenyl) pyrrole (prepared as described in Example 92) was chlorinated, in the same manner as described in Example 37, to give the title compound, as a white powder (yield 68%), which melts at 141-142 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.71 (2H, double bands, 3 = 9 Hz); 7.26-7.07 (6H, multiple bands); 6.50 (1H, double bands, 3 = 4 Hz); 6.31 (1H, double bands, 3 = 4 Hz); 4.78 (2H, single band); 2.52 (3H, single band). Mass spectrum (IE) rn / z: 378 [M + l.

EXAMPLE 102 5-CHLORO-1- (2,4-DICHLOROPHENYL) -2- (4-SULFAMOYLPHENYL) PYRROL (COMPOUND No. 1-155) L- (2,4-Dichlorophenyl) -2- (4-sulfamoyl-phenylDrug (prepared as described in Example 93) was chlorinated, The same way that was described in example 37, to give the compound of the title, as a white powder (yield 73%), which melts at 186-187 ° C. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCI3) d ppm: 7.78-7.67 (4H, multiple bands); 7.32-7.25 (5H, multiple bands); 6.63 (1H, double bands, 3 = 4 Hz); 6.48 (IH, double bands, 3 = 4 Hz). Mass spectrum (IE) rn / z: 400 EM + 1.

EXAMPLES 103-111 A procedure similar to that described in example 19, steps (1) and (11) was repeated, but using 4-sulfarnoylbenzaldehyde and various kinds of aniline as starting materials, to give the or-an? L? No-or- ( i -sul famoil fem l) aceton? tplo, corresponding, which were reacted in the same manner as described in example 18, to give the compounds having the following formula: where R2 has the different meanings shown in table 12. The abbreviations used in tables 12 and 13 for the groups s? stit? yentes are as previously given for tables 1 and 2 and the abbreviation "p.f." means "point of use." TABLE 3 Compues-Example to No. R2 Appearance? .f. (° C) 103 1-31 3,4-dlCl-Ph white powder 127-129 104 1-159 4-EtO-Ph yellow powder 122-123 p 105 105 1-113 3-F-4-MeO- yellow powder 116-117 Ph pale 106 1-109 3-Cl-4-MeO- light powder- 132-134 Green mind Compues Example to No, R2 Appearance pf (° C) 107 1-71 Ph white powder 91-93 108 1-103 3-C1-4-F- white powder 142-144 Ph 109 1-106 3,4-met? Ien- light powder- 147-149 dioxi-Ph cal ca. 110 1-146 2,4, 6-tpMe- yellow powder 125-126 pale Ph 111 1-150 4-Cl-2-F-Ph white powder 161-162 EXAMPLES 112-128 A procedure similar to that described in example 13, step (i) and (n) was repeated, using 4-sulfamo? Lan? L? and various kinds of benzaldehyde as starting materials, to give α-feml-or * - (4-sulfamo ?lam 1 ?not) aceton ?tplos, which were then reacted in the same manner as described in example 15, to give The compounds that have the following formula: where R has the various meanings shown in table 13, TABLE 4 Com¬ Sample to No. R2 Appearance p. f. (° C) 112 2-91 4-Et-Ph powder l igera121 - 126 mind coffee 113 • 93 4-? Pr-Ph light powder1 35- 139 mind ca fe Com¬ Sample to No. R2 Appearance p.f. , (° C) 114 2-102 4-CF3-Ph yellow powder 180--185 pale 115 2-95 3-Cl-4-F-Ph yellow powder 155--157 pale 116 2-103 4-CHF20-Ph white powder 137-- 140 grayish 117 2-104 4-CF3? -Ph white powder 188- 189 118 2-L21 2,4-dlCl-Ph light powder- 197--199 mind coffee 119 2-138 2,3-dlCl-Ph light powder167-170 mind coffee 120 2-137 4-MeC ~ 3,5-d ? Me- amorphous light¬ Green mind 121 2-139 3,5-dlCl-Ph light powder157-159 mind coffee Com¬ Sample to No. R2 Appearance p.f. (° C) 122 2-140 2,4,5-triMe-Ph color powder 114-115 orange 123 2-141 3-cPnC ~ 4-MeO-Ph light powder- 147-149 mind coffee 124 2-142 4-Cl-3- Light amorphous CF3-Ph light-brown coffee 125 2-143 3 -F-4-Me- Ph yellow powder 171-178 pale 126 2-144 4-Cl-3-Me-Ph yellow powder 166-J 68 pale 127 2 -145 2,4-d? Me-Ph yellow powder 178-182 128 2-146 4-OH-Ph amorphous c fé pal gone EXAMPLE 129 1- (4-MERCAPTOFENIL) -4-METHYL-2- (4-SULFAHOILFENIL) PYRROL (COMPOUND No. 1-156) 129 (i) Bis (4-aminophenyl) disulfide 7.42 g (40 rnrols) of 4-acetarn-dof lofenol were dissolved in 100 ml of methylene chloride and 40 nl (40 mmol) of the resulting solution were added. a 10% w / v aqueous solution of potassium bicarbonate, and 3.20 g (20 rnmoles) of bromine was added to the mixture, slowly, while stirring and cooling with ice. The mixture was stirred at room temperature for 15 minutes and then the resulting white precipitate was collected by filtration, and washed with water, to give the bis (4-acetamofenol) disulfide as a powder. White. The whole of this product was dissolved in 100 ml of ethanol and 50 ml of concentrated aqueous hydrochloric acid was added to the resulting solution. The mixture was then stirred at 80 ° C for six hours. At the end of that time, the reaction solution was evaporated under reduced pressure and the residue was dissolved in 200 ml of water. The pH of the mixture was then adjusted to a value of at least 9 by the addition of an aqueous solution IN by weight / volume of hydroxy or sodium. The resulting yellow precipitate was collected by filtration and washed with water to give 3.92 g (39% yield) of the title compound as a powderyellow that melts at 75-77 ° C. Mass spectrum (IE) rn / z: 248 [M + l .. 129 (ii) bisC4- (4-sulfamoyl encyl enamino) phenyl disulfide] Following a procedure similar to that described in example Id), but using bis (4-amidophenol) disulfide [prepared as described in step (i) above! and 4-sulfamoylbenzaldehyde as starting materials, the title compound was obtained as a slightly yellow powder (58% yield), which melts at 200-230 ° C. 129 (iii) BisC4 - ('- cyano-4-sulfamoylbenzylamino) -phenyl disulphide] Following a procedure similar to that described in Example J (??), but using b? S disulfide [4- (4 ~ sul phanoi J -benzylideneamino) pheni] [prepared as described in step (n) above] and trirnethylamyl cyanide, co or starting materials, the title compound was obtained as a yellow amorphous powder (yield 92%). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) d ppm: 7.95-7.91 (2H, multiple bands); 7.75 (2H, double bands, 3 = 8 Hz); 7.45 (2H, single band); 7.31 (2H, double bands, 3 = 8 Hz); 7.19 (1H, double bands, 3 = 9 Hz); 6. 82-6.79 (2H, multiple bands); 6.19 (1H, double bands, 3 = 9 Hz). Mass spectrum (FAB) in / z: 636 CM + 1. 129 (iv) Bis disulfide. { 4- [4-methyl-2- (4-sulfamoylphenyl) pyrrol-1-yl] phenyl} Following a procedure similar to that described in the example Km), but using b? S disulfide [4- (or-e? Ano-4-sulphanoylbenzylamino) phenylol [prepared as described in step (m) above! and methacrolein co or starting materials, the title compound was obtained as a pale yellow powder (42% yield), which melts at 251-255 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) ppm: 7.73 (4H, double bands, 3 = 9 Hz); 7.46 (4H, double bands, j-q Hz); 7.18 (4H, double bands, 3 = 9 Hz); 7.10 (4H, double bands, 3 = 9 Hz); 6.75 (2H, single band); 6.46 (4H, single band); 6.35 (2H, single band); 2.16 (6H, single band). Mass spectrum (FAS) m / z: 686 TM + 1. 129 (v) l- (4-Mercapto-phenyl) -4-methyl-2- (4-sulo-famo-phenyl-pyrrole) 1.00 g (1.5 rnmoles) of disulfide were dissolved.

Bis. { 4- [4-methy1-2- (4-sul-famoyl phenyl) pyrrol-1-yl phenyl} [prepared as described in step (iv) above!), in a mixture of 40 ml of tetrahydrofuran and 10 ml of methanol, and 55 mg (1.5 mmoles) of sodium borohydride was added to the resulting solution. The mixture was then stirred at room temperature for 15 minutes, after which 5% w / v aqueous sulfuric acid was added to acidify the mixture, and then 25 ml of water. The resulting mixture was extracted with ethyl acetate. The organic extract was extracted with water and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure to give 1.07 g (100% yield) of the title compound as a pale yellow amorphous powder. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d ppm: 7.74 (2H, double bands, 3 = 9 Hz); 7.24 (2H, double bands, 3 = 9 Hz); 7.21 (2H, double bands, 3 = 9 Hz); 6.98 (2H, double bands, 3 = 9 Hz); 6.73 (1H, single band); 6.40 (1H, single band); 4.76 (2H, single band); 3.50 (1H, single band); 2 . 17 (3H, dual i ndivi band). Mass spectrum (IE) rn / z: 344 CM + 1.

EXAMPLE 130 1- (4-ACETYLTHEPHENYL) -4-METHYL-2- (SULFAMOYLPHENYL) PIRROL (COMPOUND No. 1-157) 0.90 g (2.6 mmol) of l- (4-mercap ofem1) -4-methyl-1-2- (4-sulfamoylphenhydropyrrole (prepared as described in example 129) was dissolved in 15 ml of tetrahydrofuran and 0.27 ml (2.9 ml) was added. It was then added to the mixture 0.53 mmol (6.5 mmol) of pyridine, and then stirred at room temperature overnight.The reaction mixture was concentrated by evaporation under reduced pressure and A saturated aqueous solution of sodium bicarbonate was added to the residue, The resulting mixture was extracted with ethyl acetate, The organic extract was washed with water and dried over anhydrous magnesium sulfate., after which it was concentrated by evaporation under reduced pressure. The residue thus obtained was applied to a column of silica gel chromatography and eluted with a 3: 2 by volume mixture of hexane and ethyl acetate, to give 0.44 g (43% yield) of the title compound, as a powder white, melting at 149-152 ° C. Spectrum of Nuclear Magnetic Resonance (270 MHz, CDCI3) d pprn: 7.75 (2H, double bands, 3 = 9 Hz); 7.38 (2H, double bands, 3 = 9 Hz); 7.22 (2H, double bands, 3 = 9 Hz); 7. 16 (2H, double bands, 3 = 9 Hz); 6.80 (1H, single band); 6.41 (1H, single band); 4.78 (2H, single band); 2.44 (3H, single band); 2.18 (3H, single band). Mass spectrum (FAB) m / z: 386 [M + l.

Claims (3)

1. NOVELTY OF THE INVENTION CLAIMS Compounds of the formula (I) and (II) wherein: R represents a hydrogen atom, a halogen atom or an alkyl group having from 1 to 6 carbon atoms; R1 r-e represents an alkyl group having from 1 to 6 carbon atoms, an ammo group or a group of the formula -NHR », where R» represents an alkanoyl group having from 1 to 25 carbon atoms, an alkoxycarbonyl group having from 1 to 6 carbon atoms in the alkoxy part, an aralkyloxycarbonyl group in which the aralkyl part is as defined below, an alkanoyloxymethyl group having 1 to 5 carbon atoms in the alkanoyl part, an alkoxycarbonylsiloxirnetyl group having from 1 to 6 carbon-bearing lathes in the alkoxy couple or a group (2-oxo-l, 3-d-oxolen-4 ~? 1) rnet iio, which is not substituted or is substituted in position 5- dioxolene with an alkyl group having 1 to 6 carbon atoms or an aryl group as defined below; R 2 represents a phenyl group which is unsubstituted or substituted by at least one substituent selected from the group consisting of the a-substituents and the substituents defined below; R3 represents a hydrogen atom, a halogen atom or an alkyl group having from 1 to 6 carbon atoms, and which is unsubstituted or substituted by at least one substituent selected from the group consisting of substituents a, defined later; R * represents an atom of hydrogen, an alkyl group having from 1 to 6 carbon atoms, and which is unsubstituted or substituted with at least one substituent selected from the group consisting of the substituents defined below, a a cycloalkyl group having from 3 to 8 carbon atom, an aryl group which is as defined below or an aralkyl group which is as defined below; said aryl groups have from 6 to 14 carbon atoms in a carbocyclic ring and are unsubstituted or substituted by at least one substituent selected from the group consisting of substituents a and substituents | 3, defined below; the aralkyl groups and the aralkyl parts of the aralkyloxycarbonyl groups are alkyl groups having from 1 to 6 carbon atoms and which are substituted with at least one aryl group, such as defined above; the substituents or are selected from the group consisting of hydroxy groups, atoms of halogen, alkoxy groups having from 1 to 6 carbon atoms and alkylthio groups having from 1 to 6 carbon atoms; the β substituents are selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms and which are unsubstituted or substituted by at least one substituent selected from the group consisting of the s stituents defined above, alkanoyloxyl groups having from 1 to 6 carbon atoms, mercapto groups, alkanoylthio groups, having from 1 to 6 carbon atoms, alkylsulfinyl groups having from the 6 carbon atoms, cycloalkyl groups having from 3 to 8 carbon atoms, halogenoalkoxy groups having from 1 to 6 carbon atoms and alkylenedioxy groups having from 1 to 6 carbon atoms; and their pharmaceutically acceptable salts.
2. 2. The compounds according to claim 1, further characterized in that R represents an atom of hydrogen, a halogen atom or an alkyl group having 1 to 4 carbon atoms.
3. 3. The compounds according to claim 1, further characterized in that R rep resents a hydrogen atom, a fl uoride atom, a chloro atom or a methyl group. Four . - The compounds according to claim 1, further characterized in that R represents a hydrogen atom. 5 . - The compunds of conformity with the claim 1, further characterized in that R * r-e represents a methyl group, an arnino group or an acetiiammo group. 6. The compounds according to claim 1, characterized furthermore because R represents an arnino group or an acetylamino group. 7. The compounds according to claim 1, further characterized in that R2 represents a phenyl group or a phenyl group which is substituted with at least one substituent selected from the group consisting of the substituents ori and the subfl uents ß1, defined below: substituents a1 are selected from the group consisting of halogen atoms, alkoxy groups having 1 to 4 carbon atoms and alkylthio groups having 1 to 4 carbon atoms; and substituents ßi are selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, alkyl groups having 1 to 4 carbon atoms and which are substituted with at least one substituent selected from the group consisting of substituents a *, rnercapto groups, alkanoylthio groups having from 1 to 4 carbon atoms, halogenoalkoxy groups having from 1 to 4 carbon atoms and alkylenedioxy groups having from 1 to 4 carbon atoms. 8. The compounds according to claim 1, further characterized in that R2 represents a femlo group or a phenyl group that is substituted with at least one substituent selected from the group consisting of substituents a1 and substituents ß2, defined below, and better still, from 1 to 3 of said substituents; substituents are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms and alkylthio groups having from 1 to 4 carbon atoms; and the β2-substituents are selected from the group consisting of alkylthio groups having from 1 to 4 carbon atoms, halogenoalkyl groups having from 1 to 4 carbon atoms, mercapto groups, alkanoylthio groups having from 1 to 4. carbon atoms, halogenoalkoxy groups having from L to 4 carbon atoms and alkylenedioxy groups having from 1 to 4 carbon atoms. 9. The compounds according to claim 1, further characterized in that R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a substituted alkyl group having 1 to 4 carbon atoms. carbon atoms and substituted with at least one substituent selected from the group consisting of the substituents defined below: the substituents or are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms and alkylthio groups having from 1 to 4 carbon atoms. 10. The compounds according to claim 1, further characterized in that R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a halogenoalkyl group which has 1! to 4 carbon atoms. 11. The compounds according to claim 1, further characterized in that R * represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a substituted alkyl group having from 1 to 4 carbon atoms and substituted with at least one substituent selected from the group consisting of the substituents or, defined above, a cycloalkyl group having from 3 to 6 carbon atoms, an aplo group having from 6 to 10 ring carbon atoms and not is substituted or is substituted with at least one substituent selected from the group consisting of the substituents or and substituents ß 3, defined below, an aralkyl group having 4 carbon atoms in the alkyl part and containing less an aplo group as defined above; the substituents cf are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms, alkyl thio groups having from 1 to 4 carbon atoms; and β3 substituents include alkyl groups having from 1 to 6 carbon atoms, alkyl groups having from 1 to 6 carbon atoms and substituted with at least one of the α-substituents; and groups ci cloalqui loxi that have 3 to 8 carbon atoms. 12. The compounds according to claim 1, further characterized in that R * represents a hydrogen atom, an alkyl group having 1 to 4 atoms carbon, a substituted alkyl group having from 1 to 4 carbon atoms and substituted with at least one substituent selected from the group consisting of the substituents "1" defined above; a cycloalkyl group having from 3 to 6 carbon atoms, an aplo group having 6 to 10 ring carbon atoms and which is unsubstituted or substituted by at least one solvent selected from the group consisting of substituents a2 and the substituents ß *, defined below,? aralkyl group having from J to 4 carbon atoms in the alkyl part and containing at least one aplo group as defined above; substituents ot2 include hydroxy groups, halogen atoms and alkoxy groups having from 1 to 6 carbon atoms; and β4 substituents include alkyl groups having from 1 to 6 carbon atoms and which are unsubstituted or substituted by at least one halogen atom, and cycloalkyloxy groups having from 3 to 8 carbon atoms. 13. The compounds according to claim 1, further characterized in that: R represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms; R 1 represents a methyl group, an ammo group or an aceti lamino group; R 2 represents a phenyl group or a phenyl group which is substituted with at least one substituent selected from the group consisting of the substituents ori and substituents β, defined later; R3 represents a hydrogen atom, an atom of halogen, an alkyl group having 1 to 4 carbon atoms or a substituted alkyl group having 1 to 4 carbon atoms and substituted with at least one substituent selected from the group consisting of the s? stit? etents or. defined ahead; R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms and substituted with at least one substituent selected from the group consisting of the constituents or, defined above, a cycloalkyl group having from 3 to 6 carbon atoms, an aplo group having from 6 to 10 ring carbon atoms and which is unsubstituted or which is substituted by at least? n its selected ituent of the group consisting of the substituents or and substituents β3, defined below, an aralkyl group having 4 carbon atoms in the alkyl part and containing at least one aplo group as defined above; the sustituyenf.es or * are selected from the group consisting of halogen atoms, alkoxy groups having 1 to 4 carbon atoms, alkylthio groups having from 1 to 4 carbon atoms; and the substituents ß are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 4 carbon atoms and which are substituted with at least one selected substituent. consists of the substituents cri, groups ercapto, alkanoylthio groups that have the 4 carbon atoms, groups halogenoalkoxy having from 1 to 4 carbon atoms and alkylenedioxy groups having from 1 to 4 carbon atoms; and the β3 substituents include alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 6 carbon atoms and substituted with at least one of the substituents or ?; and cycloalkyloxy groups having from 3 to 8 carbon atoms. 14. The compounds according to claim 1, further characterized in that: R represents an atom of hydrogen, a fluorine atom, a chlorine atom, or a methyl group; R 1 represents an arnino group or an acetylamino group; R 2 represents a phenyl group or a phenyl group which is substituted with at least one substituent selected from the group consisting of the substituent ori and substituents β 2, defined below; R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a halogenoalkyl group having 1 to 4 carbon atoms; R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms and is substituted with at least one substituent selected from the group consisting of the following substituents: O2-defined ligands, a cycloalkyl group having from 3 to 6 carbon atoms, an alyl group having from 6 to 10 ring carbon atoms and which is unsubstituted or substituted by at least one etiomer selected from the group consisting of the substituents c * 2 and the substituents ß? , defined below, an aralkyl group having from 1 to 4 carbon atoms in the alkyl part and containing at least one aryl group as defined further back; the substituents selected from the group consisting of halogen atoms, alkoxy groups having 1 to 4 carbon atoms and alkylthio groups having 1 to 4 carbon atoms; substituents or 2 include hydroxy groups, halogen atoms and alkoxy groups having from 1 to 6 carbon atoms; the β 2 -ethan substituents selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, halogenoalkyl groups having from 4 carbon atoms, mercapto groups, alkanoylthio groups having from 1 to 4 carbon atoms, halogenoalkoxy groups having 1 to 4 carbon atoms and alkylenedioxy groups having 1 to 4 carbon atoms; and the β * substituents include alkyl groups having from 1 to 6 carbon atoms and which are unsubstituted or substituted by at least one halogen atom, and cycloalkyloxy groups having from 3 to 8 carbon atoms. 15. The compounds according to claim 1, further characterized in that: R represents a hydrogen atom; R1 represents an ammo group or an acetylamino group; R 2 represents a phenyl group or a femlo group which is substituted with at least one substituent selected from the group consisting of the substituents cri and the substituents β, defined; R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a halogenoalkyl group having 1 to 4 carbon atoms; R * represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a substituted alkyl group having from 1 to 4 carbon atoms and substituted with at least one substituent selected from the group consisting of substituents or * 2, defined above, a cycloalkyl group having from 3 to 6 carbon atoms, an aryl group having from 6 to 10 ring carbon atoms and which is unsubstituted or substituted with at least one selected substituent of the group consisting of substituents a2 and substituents ß *, defined below, an aralkyl group having 4 carbon atoms in the alkyl part and containing at least one aplo group as defined above; the substituents or are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms and alkyd groups having from 1 to 4 carbon atoms; and the substituyenf.es a2 include hydroxy groups, halogen atoms and alkoxy groups having from 1 to 6 carbon atoms; the β2 substituents are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, haloalkyl groups having from 1 to 4 carbon atoms, rnercapto groups, alkanoylthio groups having from 1 to 4 carbon atoms, groups halogenoalkoxy having 4 carbon atoms and alkyndiioxy groups having from J to 4 carbon atoms; and the substituents ß * include alkyl groups which have from 1 to 6 carbon atoms, and which are unsubstituted or substituted with at least one halogen atom; and cycloalkyloxy groups having from 3 to 8 carbon atoms. 16. The compound according to claim 1, further characterized in that it is 4-mef? L-2- (4-methylphenyl) -1- (4-sul fa oi lfeml) pyrrol. 17. The compound according to claim 1, further characterized in that it is 2- (4-rnetox i f em 1) -4-rnet? L-l- (4-sul f amo 11 f em J) ?? rrol. 18. The compound according to claim 1, further characterized in that it is 2- (4-chlorophene) -4-rnet? 1- 1- (4-sulphinoi-1-fe-pyrrole) 19.- The compound according to claim 1, further characterized in that 4-met? L-2- (4-methylthiophenyl) -l- (4- The compound according to claim 1, further characterized in that it is 2- (4-ethoxy-fe-1) -4-met-11-1- (4-sulfa ori-i-i-D-pyrrol. 21. The compound according to claim 1, further characterized in that it is 2- (4-rnetox? ~ 3-met? Lfeml) -4-met? Ll- (4-sul famoyl fem L) pyrrol. The composition according to claim 1, further characterized in that it is 2 - (3-fl uoro- -rnetox? Phen? L) -4-? Net? Ll- (4-sul famoi lphenyl) rr. The compound according to claim 1, further characterized in that it is 2 - (3, - dimet 11 fen 11) -4-met i ll- (4-sulphiolide 1) pyrol 1. 24.- The compound according to claim 1, further characterized because it is 4-rnet? ll- ( 4-Rethylthiophenyl) -2- (4-sulfarnαlphenyl) pyrrolidone. 25. The compound according to claim 1, further characterized in that it is l- (4-acetylaminosulfonylfem 1) -4-rnet? -2- (4-methox? Phen?) Pyrrol. 26. The compound according to claim 1, further characterized in that it is l- (4-acetyl lammosul foni lfeni 1) -4 -methyl-2- (3,4-d? Met? Lfe?) ?? rrol. 27. A method for treating or alleviating pain or inflammation in a mammal suffering from them, characterized in that an anti-inf larnatope and analgesic compound selected from the group consisting of the compounds of the formula (I) and ( II) and its pharmaceutically acceptable salts, as claimed in claim 1. 28.- The method according to claim 27, further characterized in that: R represents a hydrogen atom, a halogen atom or an alkyl group what has 1 to 4 carbon atoms; R 1 represents a methyl group, an a mo group or an acetyl amino group; R 2 represents a femlo group or a phenyl group which is substituted with at least one substituent selected from the group consisting of the ori substituents and the substituents β, defined hereafter; R3 represents a hydrogen atom, an atom of halogen, an alkyl group having 1 to 4 carbon atoms or a substituted alkyl group having 1 to 4 carbon atoms and substituted with at least one ester selected from the group consisting of the substituents defined hereinafter; R * represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a substituted alkyl group having from 1 to 4 carbon atoms and substituted with at least one substituent selected from the group consisting of s? stit? a, defined above,? n cycloalkyl group having from 3 to 6 carbon atoms, an aryl group having from 6 to 10 ring carbon atoms and which is unsubstituted or substituted by less is selected from the group consisting of substituents α and β3 substituents, defined below, an aralkyl group having from 1 to 4 carbon atoms in the alkyl part and containing at least one aplo group. as it was defined more © tras; the substituents "i" are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms, alkylthio groups having from 1 to 4 carbon atoms; and the substituents ßi are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 4 carbon atoms and which are substituted with at least one substituent selected from the group consisting of of the ring substituents, rnercapto groups, alkanoylthio groups having from 1 to 4 carbon atoms, groups halogenal or i having 1 to 4 carbon atoms and alkylenedioxy groups having 1 to 4 carbon atoms; and β3-substituents include alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 6 carbon atoms and substituted with at least one of the a-substituents; and cycloalkyloxy groups having from 3 to 8 carbon atoms. 29. The method according to claim 27, further characterized in that: R represents a hydrogen atom, a fluorine atom, a chlorine atom, or a methyl group; R1 represents an amino group or an acetylamino group; R 2 represents a phenyl group or a femlo group which is substituted with at least one substituent selected from the group consisting of substituents 0 * 1 and substituents β 2, defined below; R3 represents a hydrogen atom, a halogen atom, an alkyl group having from J to 4 carbon atoms or a halogenoalkyl group having from 1 to 4 carbon atoms; R4 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a substituted alkyl group having from 4 carbon atoms and is substituted with at least one substituent selected from the group consisting of substituents or * 2 defined above, a cycloalkyl group having from 3 to 6 carbon atoms, an aryl group having from 6 to 10 ring carbon atoms and which is unsubstituted or substituted by at least one substituent selected from the group consisting of of the substitutes yenfes a2 and substituents ß *, defined rnás further, an aralkyl group having 1 to 4 carbon atoms in the alkyl part and containing at least one aryl group such as is defined above; the cd substituents are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms and alkyl thio groups having from 1 to 4 carbon atoms; the s2 stituents a2 include hydroxy groups, halogen atoms and alkoxy groups having from 1 to 6 carbon atoms; the substituents β2 and β2 are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, halogenoalkyl groups having from 1 to 4 carbon atoms, mercapto groups, alkanoylthio groups having from 1 to 4 carbon atoms. carbon, halogenoalkoxy groups having 1 to 4 carbon atoms and alkylenedioxy groups having 1 to 4 carbon atoms; and the substituents * include alkyl groups having from 1 to 6 carbon atoms and which are unsubstituted or substituted by at least one halogen atom, and cycloalkyloxy groups having from 3 to 8 carbon atoms. The method according to claim 27, characterized in that the anti-inflammatory and analgesic composition is selected from the group consisting of: 4-rnetyl-2- (4-rnet? Ifen? L) -l- ( 4-sulo famoyl feni Dopropanol; 2- (4-methox? -fem D-4-met? Ll - (4-sulphenol phen ylpyrrole; 2- (4-chlorophemol) -4-met? Ll- ( 4-sul farnoi lfemDpi rrol; 4-met? L -2- (4-rnet? J thiofem J) -l- (4-sul famoyl femDpi rrol; 2- (4-ethox? Phen? L) -4-rnet ? li- (-s? l farnoi lphenyl) ?? rrol; 2- (4-methoxy? -3-rnet and LfeniL) -4-? net? l -1- - sulfamoylphenyl) pyrrolidone; 2- (3-fluoro-4-methoxy phenyl) -4-met? II- (4-sulphamoylphenyl) Jpyrrole; 2- (3,4-dimetho-phene-1) -4-rnet? II- (4-methoxy) famoil feniDpirrol; 4 - et? ll- (4-met? lt? ofen? l) -2- (4-sulfamoylphenyl) pyrro!; l- (4-acet? lar? nos? lfon? lfeml) -4-met L-2- (4-methoxyphenol) and 1- (4-acet? laminosul fonil fem 1) -4-rnet? l-2- (3,4-d? met? l) feni l) rrol 31. A method for inhibiting bone resorption in a mammal suffering from it, characterized in that an active compound selected from the group consisting of the compounds of formulas (I) and (II) is administered. ) and its pharmaceutically acceptable salts, as claimed in claim 1. 32.- The method according to claim 31, further characterized in that: R represents a hydrogen lance, a halogen atom or an alkyl group having 1 to 4 carbon atoms; R1 represents a methyl group, an arnino group or an acetyanino group; R2 represents a femlo group or a phenyl group which is substituted with at least one substituent selected from the group consisting of substituents ai and substituents ßi, defined later; R3 represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms or a substituted alkyl group having from 4 carbon atoms and substituted with at least one substituent selected from the group consisting of of the substitutes and yenf are defined later; It represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms and substituted with at least one solvent selected from the group consisting of substituents a, defined above, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 10 ring carbon atoms and which is unsubstituted or which is substituted with at least one substituent selected from the group consisting of substituents a and substituents ß3 , defined later on, an aralkyl group having from 1 to 4 carbon atoms in the alkyl part and containing at least one aryl group as defined above; the α-γ-γ-γ-γ-γ-γ-γ-α-γ-alkyl groups are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms, alkyl-thio groups having from 1 to 4 carbon atoms; and the substituents ßi are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 4 carbon atoms and which are substituted with at least one substituent selected from the group consisting of substituents ai, mercapto groups, alkanoylthio groups having from 1 to 4 carbon atoms, halogenoalkoxy groups having from 4 carbon atoms and alkyl endioxy groups having from 1 to 4 carbon atoms; and β3 substituents include alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 6 carbon atoms and substituted with at least one of substituents a; and cycloalkyloxy groups having from 3 to 8 carbon atoms. The method according to claim 31, further characterized in that: R represents a hydrogen atom, a fluorine atom, a chlorine atom, or a methyl group; R1 represents an a mo group or an acetylamino group; R 2 represents a phenyl group or a femlo group which is substituted with at least one substituent selected from the group consisting of substituents I and substituents β 2, defined below; R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a halogenoalkyl group having 1 to 4 carbon atoms; R * represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 4 carbon atoms and is substituted with at least one substituent selected from the group consisting of substitue a2 defined above, a cycloalkyl group having from 3 to 6 carbon atoms, an aryl group having from 6 to 12 ring carbon atoms and which is unsubstituted or substituted by at least one substituent selected from the group consisting of substituents .is a2 and the euet uentu *, defined below, an aralkyl group that has 4 carbon atoms in the alkyl part and which contains at least one aplo group as defined back; the substituents or are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms and alkylthio groups having from 1 to 4 carbon atoms; The a2 substituents include hydroxy groups, halogen atoms and alkoxy groups having from 1 to 6 carbon atoms; The β2 substituents are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, halogenoalkyl groups having from 1 to 4 carbon atoms, mercapto groups, alkanoyl groups having from 1 to 4 carbon atoms, groups halogenoalkoxy having 4 carbon atoms and alkylenedioxy groups having from J to 4 carbon atoms; and the β * substituents include alkyl groups having from 1 to 6 carbon atoms and which are unsubstituted or substituted by at least one halogen atom, and cycloalkyloxy groups having from 3 to 8 carbon atoms. 34.- The method according to claim 31, further characterized in that the active compound is selected from the group consisting of: 4-met? L -2- (4-rnet? Lfen? L) -l- (4 -sul famoyl phenyl? pyrrole;? - (4-methox? -phenol) -4-rnet 11-1- (4-sul famo 11 phene D p rrol; 2 - (4-cio ro feni 1) - 4 -meti 1 - 1 - (4-sulfamethylphenol) 4-met? L-2- (4-met? Lt? Ofen? L) -l- (4-sulo-pheoylphenol) 2- (4 -etox? phen?) -4-met? ll- (4-s?) famoyl feni Dp rrol; 2- (4-methox? ~ 3-met? 1 phenyl) -4-met? ll - (4- sulfinnoi lfem Dpi rrol; 2- (3-fl uoro-4-methox ifm D-4-me? 1-1- (4-s? famoyl femDpirrol; 2- (3,4-d? met? l in (l) -4-methyl-1- (4-sul phenyl) phenylpiol 4 -methyl-1- (4-rnetthylthiophenyl) -2- (4-sul phanole lfem Dp rrol; 1- (4 -acet?? n? noeulfon? l phenyl) -4-rnet? l- 2- (4-rnetox? phen? l) p? rrol; and 1-U-acet? lam? nosuifon? lfen? D -4 - met? l-2- (3,4-d? met? lfen? l) p? rrol. 35. A method for inhibiting the production of leucotpene in a mammal, characterized in that an active compound selected from the group consisting of compounds of the formula (I) and (II) and their pharmaceutically acceptable salts is administered, as claimed in claim 1. 36. The method according to claim 35, further characterized in that: R represents a hydrogen atom, a halogen atom or an alkyl group having from 1 to 4 carbon atoms; R 1 represents a methyl group, an ammo group or an acetyla mo group; R 2 represents a phenyl group or a femlo group which is substituted by at least one substituent selected from the group consisting of substituents α and substituents β, defined later; R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a substituted alkyl group having 4 carbon atoms and substituted with at least one substituent selected from the group consists of the substituents l defined as follows; R * represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a substituted alkyl group having from 1 to 4 carbon atoms and substituted with at least one substituent selected from the group consisting of substituents a , defined above, a cycloalkyl group having from 3 to 6 carbon atoms, a group aryl having from 6 to 10 ring carbon atoms and which is unsubstituted or substituted with at least one substituent selected from the group consisting of substituents l and substituents β3, defined below, an aralkyl group having 1 to 4 carbon atoms in the alkyl part and containing at least one aryl group as defined above; the substituents a are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms; and the ßi eethan substituents selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 4 carbon atoms and which are substituted with at least one substituent selected from the group consisting of substituents to the rnercapto groups, alkanoylthio groups having from 1 to 4 carbon atoms, halogenoalkoxy groups having from 4 carbon atoms and alkylenedioxy groups having from 1 to 4 carbon atoms; and the β3 substituents include alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 6 carbon atoms and substituted with at least one of the a substitutes; and cycloalkyloxy groups having from 3 to 8 carbon atoms. 37. The method according to claim 35, further characterized in that: R represents an atom of hydrogen, a fluorine atom, a chlorine atom, or a methyl group; R1 represents an arnin group or an acetyl amino group; R2 represents a phenyl group or a phenyl group which is substituted with at least one substituent selected from the group consisting of substituents α and β2 substituents, defined later; R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a halogenoalkyl group having 1 to 4 carbon atoms; R * represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a substituted alkyl group having from 4 carbon atoms and is substituted with at least one substituent selected from the group consisting of the substituents? a2 defined above, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 10 ring carbon atoms and which is unsubstituted or substituted with at least one substituent selected from the group consisting of of the α2 substituents and the βß substituents, defined below, an aralkyl group having from 1 to 4 carbon atoms in the alkyl part and containing at least one aplo group as defined further s; Substituents 1 are selected from the group consisting of halogen atoms, alkoxy groups having 1 to 4 carbon atoms, and alkyl thio groups having 1 to 4 carbon atoms; the a2 substituents include hydroxy groups, halogen atoms and alkoxy groups having from 1 to 6 carbon atoms; the β2 substituents are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, groups haloalkyl having 1 to 4 carbon atoms, mercapto groups, alkanoylthio groups having 1 to 4 carbon atoms, haloalkoxy groups having 1 to 4 carbon atoms and alkylenedioxy groups having 1 to 4 carbon atoms; and the β * substituents include alkyl groups having from 1 to 6 carbon atoms and which are unsubstituted or substituted by at least one halogen atom, and cycloalkyloxy groups having from 3 to 8 carbon atoms. 38.- The method according to claim 35, character- ized in addition because the active compound is selected from the group consisting of: 4-met? L-2- (4-methylphenyl) -1- (4-sul fainoi) 1 fem pi rrol; 2- (4-rnetox? -fen? L) -4-rneti l -i- (4-sul famoyl fen 11) pyrrol; 2- (4-chlorophen? 1) -4-rnet ? ll- (4-s? lfarno? lfeml) p? rrol; 4-met? l-2- (4-metlltiophenyl) -l- (4-sul famoil feml) pi rrol; 2- (4-ethoxy? fen? l) -4-rnet? ll- (4-sulicylpheni Doprol; 2- (4-metho? -3-met? lfen? 1) -4-? net? ll- (4-s? l farnoi lp Dm rrol, 2- (3-fluoro-4-rnetox? phen? 1) -4-met j J ~ l- (4 ~ sul fa oi 1 eni 1) rrol; 2 - (3, 4 - di eti 1 f eni 1) - 4 - met i 1 - 1 - (4 -sulfoylphenhydro) 4-rnet? J -l- (4-met? J uncle phenIl) -2- (4-sulfamoylfeml) p (4-acetylaminosulfonylphenyl) -4-methyl-2- (4-rnetoxy-phenol) pyrrolidone and l- (4-acetylansulfo-ilferul) - 4-rnet? L-2- (3,4-d? Rnet? Ifen? 1) r rrol 39. A method for selectively inhibiting the activity of COX-2 is a mammal, characterized by The mammal is administered an effective amount of an active compound selected from the group consisting of compounds of the formula (I) and (II) and their pharmaceutically acceptable salts, as claimed in claim 1. 40. The method according to claim 39, further characterized in that: R represents a hydrogen atom, an atom of halogen or an alkyl group having 1 to 4 carbon atoms; R represents a methyl group, an ammo group or an acetylamino group; R 2 represents a femlo group or a phenyl group which is substituted by at least one substituent selected from the group consisting of the substituents α and substituents β, defined later; R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a substituted alkyl group having from L to 4 carbon atoms and substituted with at least one substituent selected from the group consisting of from the substitutes to the defined future; R represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a substituted alkyl group < The atom has from 1 to 4 carbon atoms and is substituted with at least one substituent selected from the group consisting of the substituents a, defined above, a cycloalkyl group having from 3 to 6 carbon atoms, an aplo group having 6 carbon atoms. to 10 ring carbon atoms and which is unsubstituted or substituted by at least one substituent selected from the group consisting of substituents α and β3 substituents, defined below, an aralkyl group having from 1 to 4 atoms from carbon in the alkyl part and which therefore contains an aplo group as defined further back; the substituents I are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms, alkyl thio groups having from J to 4 carbon atoms; and the substituents ßi are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 4 carbon atoms and which are substituted with at least one substituent selected from the group consisting of of substituents al, mercapto group, alkanoylthio groups having from 4 carbon atoms, halogenoalkoxy groups having from 4 carbon atoms and alkylenedioxy groups having from 1 to 4 carbon atoms; and the β3 substituents include alkyl groups having from 1 to 4 carbon atoms, alkyl groups having from 1 to 6 carbon atoms and substituted with at least one of the substituents a; and cycloalkyl loxy groups having from 3 to 8 carbon atoms. 41. The method according to claim 39, further characterized in that: R represents a hydrogen atom, a fluorine atom, a chlorine atom, or a methyl group; Rl represents a group or a group aceti lamino; R2 represents a phenyl group or a phenyl group which is substituted with at least one substituent selected from the group consisting of the substituents α and substituents β, defined below; R3 represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 atoms of carbon or a halogenoalkyl group having from 1 to 4 carbon atoms; * represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms and is substituted with at least one substituent selected from the group consisting of substituents a2 defined above, a cycloalkyl group having from 3 to 6 carbon atoms, an aryl group having from 6 to 10 ring carbon atoms and which is unsubstituted or substituted by at least one substituent selected from the group consisting of substituents a2 and substituents ß *, defined below, an aralkyl group having 1 to 4 carbon atoms in the alkyl part and containing at least one aplo group as defined above; the sustituyent.es are selected from the group consisting of halogen atoms, alkoxy groups having from 1 to 4 carbon atoms and alkylthio groups having from J to 4 carbon lathes; The a2 substituents include hydroxy groups, halogen atoms and alkoxy groups having from J to 6 carbon atoms; The β2-substituents are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, halogenoalkyl groups having from 1 to 4 carbon atoms, mercapto groups, alkanoylthio groups having from 1 to 4 carbon atoms , halogenalkoxy groups having from 1 to 4 carbon atoms and alkylenedioxy groups having from J to 4 carbon atoms; and substituents ß * include alkyl groups that they have from 1 to 6 carbon atoms and are unsubstituted or substituted with at least one halogen atom, and cycloalkyloxy groups having from 3 to 8 carbon atoms. 42. The method according to claim 39, further characterized in that the active compound is selected from the group consisting of: 4-met? L-2- (4-met? Lfen? L) -l- (4-sulfar ? lfen? l) p? rrol; 2- (4-methox? -fen? 1) -4-rnet? L -l- (4-sulo famoyl fem Dp rrol; 2- (4-chlorophen? L) -4 -meth] -l- (4- sul famoil fen ll) pyrro 1; 4-rnet? l -2- (4-rnet? 1 uncle phen ll) -] - (4 -sulphennoylphenyl Jpyrrole; 2- (4-ethoxyphenol) -4 -met? ll- (4-sulfa oilphenyl Jpyrrole; 2- (4-methox? -3-met? lphenyl) -4 -rne 11-1- (4-sul phanole lfem Dp.pyrrol; - 4-methoxyphenyl) -4-met? Ll- (4-s? Lamoamoyl Dp rrol; 2- (3, 4-d? Met? Lfen? L) -4?? Net? L -l- ( 4-sulfamoylpheni D yrrol; 4 -methyl] -l- (4-methythoxyphenyl) -2- (4-sul phenylnoyl) pyrrolidone- (4-acetylamino-sulfonyl) -4-rnet α- 2- (4-rnetox-phenyl) p?-pyr;, yl ~ (4-acet-lam? nosul on? l in? L) -4-rnet? l-2- (3, 4-d? rnet? l phenyl) rrol.