MXPA97002380A - New carboxamides with antifung activity - Google Patents

Abstract

The compounds of general formula I and their salts and solvates are antifungal agents and as such are useful in the treatment of various fungal infections. Pharmaceutical compositions including these compounds and methods for their preparation are also described.

Description

New carboxamides with antifungal activity Sector of the technique to which the invention relates The present invention relates to a new series of carboxamides of general formula I with a potent antifungal activity. The invention also relates to a process for their preparation, to pharmaceutical compositions containing them and to their use in the treatment of diseases caused by fungi. Description of the state of the art The compounds of the present invention are antifungal agents of the azole family, whose mechanism of action is based on the inhibition of the biosynthesis of ergosterol, the main sterol present in the membrane of fungi. Other antifungal agents that also possess this mechanism of action have been described in the literature. Patent applications EP 332387 and EP 617031 describe azo compounds containing an arylcarboxamide group. The compounds of the present invention are not only more potent antifungal agents than the compounds described in the two previous patents but also have a spectrum of antifungal activity that is broader because, unlike the compounds described therein, they are also active against filamentous fungi, included aspergillus. Description of the invention The present invention relates to the novel carboxamides of general formula I I in the form of racemates, mixtures of diastereomers or in the form of pure enantiomers, wherein: X represents N or CH; Ar represents phenyl or phenyl substituted by one or more halogen and / or trifluoromethyl groups; R1 is C1-C4 alkyl; R2 is hydrogen or C1-C4 alkyl; or else R \ together with R2 form a C2-C4 polymethylene chain; R3 is hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C4 alkyl, C1-C4 haloalkyl, phenyl-C? -C4 alkyl (wherein the phenyl group may be optionally substituted by 1, 2, 3 or 4 Rs groups, which may be the same or different), a group - (CH2) n-CH2? H, a group - (CH2) n- H2? Bn, a group - (CH2) n- H2NR6R7. a group - (CH2) n- H2COOR6, or a group - (CH2) n-CH2COOBn, in which case R4 is hydrogen; or R3 together with R4 and the remainder of said compound of formula I form an oxazolidine ring of formula I ' I 'or R3 together with R4 and the remainder of said compound of formula I form a morpholine ring of formula I " where D is O, in which case the dashed line represents a covalent bond, or D is hydroxy or hydrogen, in which case the dotted line is absent; A represents phenyl or a monocyclic or bicyclic heterocyclic group containing from 1 to 4 heteroatoms chosen from N, O and S and wherein each ring in the heterocyclic group consists of 5 or 6 atoms, where A may be unsubstituted or possess 1 , 2, 3 or 4 Rs groups; B represents a phenyl group which may be optionally substituted by 1, 2, 3 or 4 R9 groups, or B represents a monocyclic or bicyclic heterocyclic group containing from 1 to 4 heteroatoms chosen from N, O and S and wherein each ring in the heterocyclic group it is composed of 5 or 6 atoms, which may be optionally substituted by 1, 2, 3 or 4 R9 groups; R 5 represents C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or halogen; n represents 0, 1, 2 or 3; R and R7 independently represent hydrogen or C1-C4 alkyl; Rd represents C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, halogen, phenyl (optionally substituted by a halogen group, cyano, C1-C4 haloalkyl or C1-C4 haloalkoxy) , nitro, cyano, hydroxy, hydroxymethyl, a group -NR6R7, a group -CONR6R7 / a group -CORÓ, a group -COOR6, or a group -SOzR? O; R9 represents -C4 alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, 2-carboxy-2-propyl, halogen, nitro, cyano, hydroxy, benzyloxy, hydroxymethyl, a -CH2-OCO-R6 group, a -CO-R6 group, a -COO-Rβ group, a -SOzR group, or a -NR6R7 group, a -CONR6R7 group, a group -C (= NR6) NHRp, a group -C (= NRp) OR6, and in addition one of the groups R9 may also represent 1-pyrrolyl, 1-imidazolyl, lH-l, 2,4-triazol-l-yl, 5-tetrazolyl (optionally substituted by C1-C4 alkyl), 1-pyrrolidinyl, 4-morpholinyl, 4-morpholinyl-N-oxide, phenyl or phenoxy (both optionally substituted by a C1-C4 alkyl group, C1-C4 haloalkyl, C1 -C4 alkoxy, C1-C4 haloalkoxy, halogen, nitro or cyano), or a group of formula (i) - (iv) (i) (ii) Rio represents C1-C4 alkyl; z represents 0, 1 or 2; Rll represents hydrogen, -CONFb, -COMe, -CN, -SCbNHRó, -SO 2 R 10, -ORó, or -OCOR 6; Rl2 represents hydrogen or methyl; R13 represents hydrogen, isopropyl, cyclopentyl, cyclopropyl, 2-butyl, 3-pentyl, 3-hydroxy-2-butyl, or 2-hydroxy-3-pentyl; p represents 0 or 1; R 14 represents halogen, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, nitro, amino, cyano, or a group of formula (i); E represents -CH 2 - or -C (= 0) -; G represents NH or O; Y represents a simple bond, -S-, -SO-, -SO2-, -O- or -NR ^ -; m and q represent independently 0, 1 or 2; and its salts and solvates. The invention also provides a pharmaceutical composition comprising an effective amount of a compound of formula I or a pharmaceutically acceptable salt or solvate thereof in admixture with one or more pharmaceutically acceptable excipients. The invention further provides the use of a compound of formula I or a pharmaceutically acceptable salt or solvate thereof for the manufacture of a medicament for the treatment or prevention of fungal infections in animals, including humans. The invention also provides the use of a compound of formula I or a pharmaceutically acceptable salt or solvate thereof for the treatment or prevention of fungal infections in animals, including humans. The invention also provides a method of treating or preventing fungal infections in animals, including humans, which comprises administering to a patient in need thereof an effective amount of a compound of formula I or a pharmaceutically acceptable salt or solvate thereof. In addition to being useful for the treatment of infections caused by fungi in animals, the compounds of the present invention possess antifungal properties which may be useful for combating or preventing fungal infections in plants. Therefore, the invention also provides the use of a compound of formula I or a salt or solvate thereof for the treatment or prevention of fungal infections in plants.

The invention also provides an agrochemical composition comprising an effective amount of a compound of formula I or a salt or solvate thereof in admixture with one or more agrochemically acceptable excipients. The invention also provides a process for preparing a compound of formula I, which comprises: (a) reacting a compound of formula II p where X, Ri, R2, R3. R4 and Ar have the meaning defined above, with an acid of formula III m where A, B, Y, m and q have the meaning defined above, in the presence of a condensing agent, or with a reactive derivative of said acid III such as the acid chloride, anhydride or mixed anhydride in the presence of a proton-picking base; or (b) transforming in one or several steps a compound of formula I into another compound of formula I; and (c) if desired, after steps (a) or Cb), treating a compound of formula I with an acid to give the corresponding addition salt. In the above definitions, the term C1-C4 alkyl, as a group or as part of a group, means a straight or branched alkyl chain containing from 1 to 4 carbon atoms. Thus, it includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, and urea-butyl. A C2-C4 alkenyl group means a straight or branched alkyl chain containing from 2 to 4 carbon atoms and which also contains one or more double bonds. Examples include ethenyl, 1-propenyl, 2-propenyl, isopropenyl, -butenyl, 2-butenyl, 3-butenyl, and 1,3-butadienyl. A C2-C4 alkynyl group means a straight or branched alkyl chain containing from 2 to 4 carbon atoms and which also contains one or more triple bonds. Examples include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, and 3-butynyl. A chain of C2-C4 polymethylene means ethylene, propylene or butylene. A C1-C4 haloalkyl group means a group resulting from the substitution of one or more hydrogen atoms of a C1-C4 alkyl group by one or more halogen atoms (i.e., fluorine, chlorine, bromine or iodine), which may be same or different. Examples include trifluoromethyl, trichloromethyl, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, pentachloroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2, 2,2-trifluoroethyl, pentafluoroethyl, 3-chloropropyl, 3,3-dichloropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentachloropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3, 3,3-trifluoropropyl, 2,2,3,3-te rafluoropropyl, 2, 2, 3, 3,3-pentaf luoropropyl, heptafluoropropyl, 4-chlorobutyl, 4-fluorobutyl, 4-iodobutyl and 4-bromobutyl. The term C3-C6 cycloalkyl, as a group or as part of a group, represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. The abbreviation Bn represents benzyl. A C1-C4 alkoxy group means a group resulting from the attachment of a C1-C4 alkyl group to an ether oxygen atom. Examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy and fgrí-butoxy. A C1-C4 haloalkoxy group means a group resulting from the substitution of one or more hydrogen atoms of a C1-C4 alkoxy group by one or more halogen atoms, which may be the same or different. Examples include trifluoromethoxy, fluoromethoxy, 2-chloroethoxy, 2-fluoroethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 3-fluoropropoxy, 3-chloropropoxy, 2,2,3,3- tetrafluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 4-fluorobutoxy, and 4-chlorobutoxy. In the compounds of the present invention Ar represents a phenyl group or a phenyl group substituted by one or more halogen and / or trifluoromethyl groups. The halogen atoms may be fluorine, chlorine, bromine or iodine atoms, among which the fluorine and chlorine atoms are preferred. There may be one or more substituents in the phenyl group, and in case there is more than one, these may be identical or different. When the phenyl group is substituted, the substituents may be at any available position of the phenyl ring, but preferably they are at the 2 and / or 4 positions. Examples of substituted phenyl groups include 4- (trifluoromethyl) phenyl, 2-fluorophenyl, 4-fluorophenyl, 2-chloro-4-fluorophenyl, 4-chloro-2-fluorophenyl, 4-bromophenyl, 2-fluoro-4-iodophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 4-chlorophenyl and 2- fluoro-4- (trifluoromethyl) phenyl, of which 2-fluorophenyl, 4-fluorophenyl, 2-chloro-4-fluorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 4- (trifluoromethyl) phenyl and 4-chlorophenyl are preferred, and 2-fluorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 4- (trifluoromethyl) phenyl and 4-chlorophenyl are more preferred. In the compounds of the present invention R represents a C 1 -C 4 alkyl group, or together with R 2 forms a C 2 -C 4 polymethylene chain, but preferably Ri is C 1 -C 4 alkyl, and more preferably R is methyl. In the compounds wherein R2 is hydrogen or C1-C4 alkyl, or, in conjunction with Ri forms a C2-C4 polymethylene chain, those in which R2 is hydrogen or methyl are preferred, and those in which R2 is more preferred. It is hydrogen. Among the compounds in which R3 and R4 have no connection or can be linked to form an oxazolidine or morpholine cycle, those in which R3 and R4 are not connected (ie, R4 represents hydrogen) are preferred, and more preferred are those in which both R3 and R4 represent hydrogen. In the compounds of the present invention, groups A and B represent phenyl or a monocyclic or bicyclic heterocyclic group, wherein each ring in the heterocyclic group consists of 5 or 6 atoms and where 1 to 4 of the ring atoms that make up said heterocyclic group are heteroatoms selected from the group consisting of N, O and S. Both A and B can be unsubstituted or have 1, 2, 3 or 4 substituents Rs or R9 respectively, which can be found in any available position of any of the rings. When there is more than one substituent on ring A or B, these may be the same or different, with the aforementioned condition that for certain meanings of R9 there can not be more than one such group on ring B. Monocyclic heterocyclic groups A or B include thiophene, furan, pyran, pyrrole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, 1,2,4-triazole, 3,4-oxadiazole, 3,4-thiadiazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, pyridine, pyrazine, pyrimidine, pyridazine, furazane, pyrroline, imidazoline and pyrazoline. Examples of bicyclic heterocyclic A or B groups include, among others, benzimidazole, benzofuran, isobenzofuran, benzofurazan, indole, isoindole, indolizine, indazole, benzothiophene, benzothiazole, quinoline, isoquinoline, phthalazine, quinazoline, quinoxaline, cinnoline, imidazopyridine, imidazopyrimidine, imidazopyrazine, imidazopyridazine, pyrazolopyrazine, pyrazolopyridine and pyrazolopyrimidine. Of all the possible meanings of A, those where A represents phenyl or a 5- or 6-membered heterocyclic ring containing from 1 to 3 heteroatoms selected from N, O and S are preferred.; more preferred are those groups where A represents a 5- or 6-membered aromatic heterocyclic ring containing from 1 to 3 heteroatoms selected from N, O and S; even more preferred are those where A represents a ring of thiophene, furan, pyrrole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, 1,2,4-triazole, 1,3,4-oxadiazole, 1,3,4 -thiadiazole, 2,4-oxadiazole, or, 2,4-thiadiazole; and those where A represents thiophene, thiazole or pyrazole are especially preferred. All these groups A can be unsubstituted or have 1, 2, 3 or 4, preferably 1 or 2, groups Rs- Preferred Rs substituents include C1-4 alkyl, C1-4 haloalkyl, C1-4 haloalkoxy, halogen and amino , among which -4 alkyl and C1-4 haloalkyl are more preferred. As for B, those groups where B represents a phenyl group optionally substituted by 1, 2, 3 or 4 substituents R9 are preferred. Examples of substituted phenyls include, inter alia, 2-methylphenyl, 4-methylphenyl, 4-butylphenyl, 4- (2-carboxy-2-propyl) phenyl, 4-vinylphenyl, 4-fluorophenyl, 4-chlorophenyl, -bromophenyl, 4-iodophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 2,6-difluorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2-chlorophenyl, 2-chloro-4-fluorophenyl, 2,4,6-trifluorophenyl, 2,3,5, 6-tetrafluorophenyl, 2- (trifluoromethyl) phenyl, 3- (trifluoromethyl) phenyl, 4- (trifluoromethyl) phenyl, 4- (trichloromethyl) phenyl, 2-fluoro-5- (trifluoromethyl) -phenyl, 2-fluoro-4 - (trifluoromethyl) phenyl, 3-fluoro-4- (trifluoromethyl) phenyl, 4- (difluoromethoxy) phenyl, 4- (trifluoromethoxy) phenyl, 4- (2-fluoroethoxy) phenyl, 4- (2,2-difluoroexy) phenyl, 4- (2, 2,2-trifluoroe toxy) phenyl, 4- (2,2,3,3-tetrafluoropropoxy) phenyl, 3-nitrophenyl, 4-nitrophenyl, 2-fluoro-4-nitrophenyl, -cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 4- (4-cyanophenyl) phenyl, 4- (4-cyanophenoxy) phenyl, 2-methyl-4-cyanophenyl, 2-chloro-4-cyanophenyl, 2-cyano-4 - (trifluoromethyl) faith or it, 4- (metoxicarbonyl) phenyl, 2-methoxy-4- (trifluoromethyl) phenyl, 2-fluoro-4- (ethoxycarbonyl) phenyl, 4- (methylthio) phenyl, 4- (methylsulfinyl) phenyl, 4- (methylsulfonyl) phenyl, 4-aminophenyl, 4-dimethylamino phenyl and 4-carbamoylphenyl. Most preferred meanings for B are those where B represents phenyl substituted by 1 or 2 R9 groups, of which those in which one of the substituents R9 is in the para position are even more preferred. Preferred meanings for R9 include C1-C4 alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, 2-carboxy-2-propyl , halogen, nitro, cyano, hydroxy, benzyloxy, hydroxymethyl, a -CH2-OCO-R6 group, a -CO-R6 group, a -COO-R1 group, a -SOzRi0 group / a -NRR7 group, a group -CONR6R7, a group -C (= NR) NHRn or a group -C (= NRn) OR6. In the compounds in which Y represents a single bond, -S-, -SO-, -SO 2 -, - - or - Ré-ymyq independently represent 0, 1 or 2, those in which Y represents a single bond are preferred and m = q = 0, ie, those having ring B directly attached to ring A by a covalent bond. Preferred compounds of the present invention include those where, independently or in any compatible combination: X represents N; R1 represents C1-4 alkyl; R2 represents hydrogen; R4 represents hydrogen; Ar represents 2-fluorophenyl, 4-fluorophenyl, 2-chloro-4-fluorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 4- (trifluoromethyl) phenyl or 4-chlorophenyl; A represents phenyl or a 5- or 6-membered heterocyclic ring containing from 1 to 3 heteroatoms selected from N, O and S, where A may be unsubstituted or possess 1, 2, 3 or 4 Rs groups; B represents a phenyl group which may be optionally substituted by 1, 2, 3 or 4 substituents R9; the stereochemistry of the compounds is (R, R). Especially preferred compounds of the present invention include those where, independently or in any compatible combination: X represents N; R1 represents methyl; R2 represents hydrogen; R3 represents hydrogen; R4 represents hydrogen; Ar represents 2-fluorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 4- (trifluoromethyl) phenyl or 4-chlorophenyl; A represents a 5- or 6-membered aromatic heterocyclic ring containing from 1 to 3 heteroatoms selected from N, O and S, and which may be unsubstituted or possessing 1 or 2 Rs groups; B represents a phenyl group substituted by 1 or 2 R9 groups; Y represents a simple bond and m = q = 0; the stereochemistry of the compounds is (R, R). Thus, a preferred class of compounds of formula I is that wherein: X represents N; R1 represents C1-4 alkyl; R2 represents hydrogen; R4 represents hydrogen; Ar represents -fluorophenyl, 4-fluorophenyl, 2-chloro-4-fluorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 4- (trifluoromethyl) phenyl or 4-chlorophenyl; A represents nyl or a 5- or 6-membered heterocyclic ring containing from 1 to 3 hetaroatoms selected from N, O and S, where A may be unsubstituted or possess 1, 2, 3 or 4 Rs groups; B represents a phenyl group which may be optionally substituted by 1, 2, 3 or 4 R substituents, and the stereochemistry of the compounds is (R, R). A more preferred class of compounds of formula I is that where: X represents N; Rl represents motil; R2 represents hydrogen; R3 represents hydrogen; R4 represents hydrogen; Ar represents 2-fluorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 4- (trifluoromethyl) phenyl or 4-chlorophenyl; A represents a 5- or 6-membered aromatic heterocyclic ring containing from 1 to 3 heteroatoms selected from N, O and S, and which may be unsubstituted or possessing 1 or 2 Rs groups; / / B represents a phenyl group substituted by 1 or 2 R9 groups; Y represents a simple bond and m = q = 0; and the stereochemistry of the compounds is (R, R). An especially preferred class of compounds of formula I is that wherein: X represents N; R1 represents methyl; R2 represents hydrogen; R3 represents hydrogen; R4 represents hydrogen; Ar represents 2-fluorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 4- (trifluoromethyl) phenyl or 4-chlorophenyl; A represents thiophene, furan, pyrrole, imidazole, pyrazole, thiazoi, isothiazole, oxazole, isoxazole, 1,2,4-triazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,2,4- oxadiazole, or 1,2,4-thiadiazole, wherein A may be optionally substituted by one or two C1-4 alkyl or C1-4 haloalkyl groups; B represents a phenyl group substituted by 1 or 2 R9 groups; R9 represents C -C4 alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, 2-carboxy-2-propyl, halogen, nitro , cyano, hydroxy, benzyloxy, hydroxymethyl, a group -CH2-OCO-R6, a -CO-Ré group, a -COO-R ^ group, a -SOzR group, or a -NR6R7 group, a -CONR0R7 group, a -C (= NR1) NHRn group or a group -C (= NRn) OR6; Y represents a simple bond and m = q = 0; and the stereochemistry of the compounds is (R, R). The compounds of formula I contain one or more basic nitrogens atoms and can therefore form salts with acids, which also form part of the present invention. There is no limitation in the nature of these salts, assuming that when they are used for therapeutic purposes they are pharmaceutically acceptable, which, as is well known, means that they have no less activity (or unacceptably reduced activity) or greater toxicity ( or an unacceptably increased toxicity) than free compounds. Examples of these salts include: salts with an inorganic acid such as hydrochloric acid, hydrobromic acid, hydroiodic acid, nitric acid, perchloric acid, sulfuric acid or phosphoric acid; and salts with an organic acid, such as methanesulfonic acid, trifluoromethanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, fumaric acid, oxalic acid, maleic acid; and other mineral and carboxylic acids well known to those skilled in the art. The salts are prepared by treating the free base with a sufficient amount of the desired acid to give the salt in a conventional manner. The free bases and their salts differ in certain physical properties, such as solubility, but are equivalent for the purposes of the invention. Some compounds of the present invention may exist in solvated form, including hydrated forms. In general, solvated forms, with pharmaceutically acceptable solvents such as water, ethanol and the like, are equivalent to the unsolvated form for the purposes of the invention.

The compounds of formula I contain one or more asymmetric carbons and can therefore exist in the form of different stereoisomers. The present invention covers each of the individual stereoisomers as well as their mixtures. When R is C1-C4 alkyl and R2 is hydrogen, those compounds of formula I are preferred in which the absolute configuration of the carbon atoms to which the groups Ar and Ri are attached is (R, R), ie compounds of formula: The diastereoisomers can be separated by conventional techniques such as chromatography or fractional crystallization. The optical isomers can be solved by the use of conventional optical resolution techniques, to give the optically pure isomers. This resolution can be carried out on any synthesis intermediate that is chiral as well as on the products of general formula I. The optically pure isomers can also be obtained individually using enantiospecific syntheses. We have obtained the isomers (R, R) optically pure starting from the optically pure amine II, synthesized according to the general method described in J.Org.Chem, 1995, 60, 3000-3012. As already mentioned above, the present invention covers both the individual isomers and their mixtures (for example racemic mixtures), whether obtained by synthesis or by physically mixing them.

Some of the compounds of formula I may have tautomerism. For example, when the compounds of the present invention contain an amidino group of formula -C (= NRó) NHR? , the following tautomeric structures can exist in equilibrium: all of which are also encompassed in the present invention. The compounds of formula I can be prepared using the procedures described below. The precise method used for the preparation of a given compound may vary depending on its chemical structure. The compounds of formula I can be prepared by reaction of an amine of formula II with an acid of formula III in the presence of a suitable coupling agent, for example dicyclohexylcarbodiimide, alone or associated with 1-hydroxybenzotriazole, in a polar solvent, such as an amide substituted (for example N-methylpyrrolidone or dimethylformamide), an ether (for example tetrahydrofuran or dioxane) or diglyme, at a temperature preferably comprised between 0 ° C and 100 ° C. Alternatively, the compounds of formula I can be prepared by reaction of an amine II with a reactive derivative of an acid III, such as the acid chloride, the anhydride or the mixed anhydride. The reaction is carried out in the presence of a proton-trapping base, such as triethylamine or pyridine, in a suitable solvent such as dichloromethane or chloroform. Alternatively, the compounds of formula I where Y represents -O-, -S- or -NR? - and m is 0 can be prepared from the corresponding compound where A is substituted by a halogen atom, for example bromine, instead of the -Y (CH2) qB group by treatment with a salt of an alkali metal of the corresponding alcohol or thiol of formula HY (CH2) qB, for example the sodium salt, or by treatment with an amine of formula HNR (CH2) q-B in a suitable aprotic solvent such as N-methylpyrrolidone at a temperature between room temperature and the reflux temperature of the solvent. Likewise, some compounds of formula I can also be prepared by interconversion from another compound of formula I in one or several steps using known reactions in organic chemistry, such as M which are described below. These reactions are mentioned here only by way of example of the processes that can be used to interconvert compounds of the present invention and are not to be understood as limiting the scope of the preparation of the compounds of formula I. Thus, for example, the compounds of formula I wherein R3 together with R4 and the remainder of said compound of formula I form a morpholine ring of formula I ", where D is hydrogen and the dotted line is absent, can be prepared from the corresponding compound of formula I where R3 = - (CH2) 2H by treatment with diethylazadicarboxylate and tributylphosphine in a suitable solvent such as tetrahydrofuran The compounds of formula I wherein R3 together with R4 and the remainder of said compound of formula I form a morpholine ring of Formula I ", where D is hydroxy and the dotted line is absent, can be prepared from the corresponding compound of formula I where R3 = - (CH OH by oxidation for example by treatment with activated DMSO and a base, such as triethylamine, in a suitable solvent, such as dichloromethane or chloroform. The compounds of formula I wherein R3 together with R4 and the remainder of said compound of formula I form a morpholine ring of formula I ", where D is O and the broken line means a covalent bond, can be prepared from the corresponding compound of formula I wherein R3 = -CH2COOH using a suitable dehydrating agent or alternatively can be prepared from the corresponding compound of formula I wherein R3 = - (CH2) 2? H by scbreoxidation It is also possible to transform a group R3 into a compound of formula I in another group R3 using conventional methods of organic synthesis Thus, a benzyl ether can be converted into the corresponding alcohol by hydrogenation in the presence of a suitable catalyst such as Pd / C in a suitable solvent such as an alcohol to a hydrogen pressure between 1 and 5 atm An ester group can be hydrolyzed to the corresponding acid using conventional methods; if it is a benzyl ester, this transformation can be carried out by hydrogenation in the same experimental conditions mentioned above. An ester group can also be reduced by treatment with a suitable metal hydride such as sodium borohydride in a suitable solvent such as ethanol to give the corresponding alcohol. It is also possible to use a group B in a compound of formula I J5 to generate other groups B thus giving rise to other compounds of formula I. For example, a nitro group can be reduced to an amino group, for example by hydrogenation in the presence of a catalyst such as Pd / C in a suitable solvent such as an alcohol, for example ethanol, at a temperature between room temperature and the reflux temperature of the solvent and at a pressure preferably between atmospheric pressure and 10 atm. A thioether group can be oxidized to a sulfinyl or sulfonyl group by treatment with a suitable oxidizing agent. For example, a thioether group can be oxidized to a sulfonyl group by treatment with m-chloroperbenzoic acid in a suitable solvent such as a halogenated hydrocarbon at a temperature preferably comprised between 0 ° C and room temperature. Also, an amino group can be transformed into a group of formula (i) by treatment with phenyl chloroformate, subsequent reaction of the phenyl carbamate thus obtained with hydrazine and finally cyclization of the resulting semicarbazide with formamidine or acetamidine in a suitable solvent as dimethylformamide at a temperature between room temperature and the reflux temperature of the solvent. A nitrile group can be transformed into a tetrazole group by treatment with a suitable azide such as sodium azide or ammonium azide (which can be prepared in situ from sodium azide and ammonium chloride) in a suitable solvent as a polar solvent, for example dimethylformamide or N-methylpyrrolidone, at a temperature preferably between room temperature and that of refluxing the solvent. Another example of interconversion is the N-alkylation of a group of formula (i) or of a tetrazole by treatment with the corresponding alkyl halide in the presence of a base such as potassium or cesium carbonate in a suitable aprotic solvent. like dimethylformamide. A nitrile group can be hydrolyzed to a carbamoyl group by treatment with ammonium hydroxide in a suitable solvent such as tetrahydrofuran-reflux water mixtures. A nitrile group can be transformed to an alkylimidate group by bubbling HCl gas into an alcohol, such as methanol. An alkylimidate group can be transformed to an amino (imino) methyl group by reaction with an amine using the corresponding alkanol as the solvent. Also, a halogen atom, for example bromine or iodine, can be transformed into a phenyl group by a coupling reaction between the corresponding haloderivative and a boronic acid or ester of the formula (ROhB-76). phenyl (where R represents hydrogen or C 1-4 alkyl) in the presence of a palladium catalyst such as Pd (OAc) 2 or Pd (PPh 3) 4 in a suitable solvent such as dimethoxyethane at a temperature preferably comprised between temperature environmental and the reflux of the solvent. A halogen atom, for example a fluorine atom, can be converted into a C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, phenoxy, -SR 10, triazole or imidazole group by treatment with an alkali metal salt of the corresponding alcohol, thiol , triazole or imidazole, for example the sodium salt, in a suitable aprotic solvent such as N-methylpyrrolidone at a temperature between room temperature and the reflux temperature of the solvent; it can also be converted into an amine (-NR6R7, 1-pyrrolidine, morpholine, a group of formula (ii) or a group of formula (iii)) by treatment with the corresponding amine in a suitable aprotic solvent such as N -methylpyrrolidone at a temperature between room temperature and the reflux temperature of the solvent. Likewise, a compound of formula I wherein Y represents -SO- or -SO2- can be prepared from the corresponding compound I where Y is -S- by oxidation as described above in relation to group B. As will be evident to those skilled in the art, all these interconversion reactions can be applied both to the final products of formula I and to their synthesis intermediates. The amines of formula II can be prepared as described in J.Org.Chem, 1995, 60, 3000-3012, EP 332387 or EP 617031. Acids of formula I I I or derivatives thereof are commercially available, are widely described in the literature or can be synthesized according to methods analogous to those described in the literature. Thus, for example, the 5-substituted l-arylpyrazole-4-carboxylic acids can be obtained by reaction of the corresponding arylhydrazine with the product coming from the reaction of the corresponding ethyl acylacetate with the dimethyl acetal of the dimethylformamide, followed by a basic hydrolysis (KOH / EtOH-H2?), As described in /. Heterocyclic Chem. 1987, 24, 1669. L-arylpyrazole-4-carboxylic acids can be obtained by reaction of the arylhydrazine corresponding to the carbethoxymalonaldehyde, followed by an alkaline hydrolysis, as described in Gazz.Chim.Ital., 1946 , 76, 56. L-aryl-5-aminopyrazole-4-carboxylic acids can be obtained by reacting ethyl ethoxymethyleneacetate with the corresponding arylhydrazine, followed by basic hydrolysis, as described in Helv. Chim. Acta, 1959, 349. The 2-aryl-4-alkylthiazole-5-carboxylic acids can be obtained by reacting the corresponding thiobenzamide with the methyl acylchloroacetate in ethanol followed by an alkaline hydrolysis, as described in Eur.]. Med. Chem. 1976, 11, 567. 2-arylthiazole-4-carboxylic acids can be obtained by reaction of the corresponding thiobenzamides with ethyl bromopyruvate in ethanol followed by alkaline hydrolysis. The l-arylpyrrole-3-carboxylic acids can be obtained by reaction of the corresponding aniline with 2,5-dimethoxy-3-tetrahydrofurancarboxaldehyde in refluxing acetic acid, followed by oxidation with silver nitrate, as described in Org. . Prep. Procedure Int., 1995, 27, 236. 5-arylthiophene-2-carboxylic acids can be prepared by reaction of the corresponding acetophenone, dimethylformamide and ethyl thioglycolate in the presence of POCI3, followed by alkaline hydrolysis, as described in Tetrahedron Lett. ., 1968, 1317. 5-aryl-3-aminothiophen-2-carboxylic acids can be prepared by reaction of the corresponding β-chlorocinmonitrile with ethyl thioglycolate in the presence of a base, followed by an alkaline hydrolysis, as described in Synthesis , 1984, 275. The 5-aryl-l, 3,4-oxadiazole-2-carboxylic acids can be prepared according to the general method described in /. Prakt.Chem. 1985, 327, 109. The 3-aryl-l, 2,4-oxadiazole-5-carboxylic acids can be prepared according to the general method described in /. Med. Chem. 1995, 38, 1355. The 5-aryl-l, 2,4-oxadiazole-3-carboxylic acids can be prepared according to the general method described in Bull. Chem.Soc.Jpn. 1985, 53, 2519. The 3-aryl-l, 2,4-thiadiazole-5-carboxylic acids and 5-aryl-l, 2,4-thiadiazole-3-carboxylic acids can be prepared according to the general method described in /. Org.Che. 1977, 42, 1813. The present invention also provides compositions containing a compound of the present invention, together with an excipient and optionally other auxiliary agents, if necessary. The compounds of the present invention can be administered in the form of different pharmaceutical formulations, the exact nature of which will depend, as is well known, on the chosen administration route and on the nature of the pathology to be treated. Thus, solid compositions according to the present invention for oral administration include tablets, dispersible powders, granules and capsules. In tablets, the active ingredient is mixed with at least one inert diluent such as lactose, starch, mannitol, 1% cellulose microcrystalline or calcium phosphate; with binding and disintegrating agents such as starch, gelatin, microcrystalline cellulose or polyvinylpyrrolidone; and with lubricating agents, such as for example magnesium stearate, stearic acid or talc. The tablets can be coated by known techniques in order to delay their disintegration and absorption in the gastrointestinal tract and thus achieve a sustained action for a longer period of time. Tablets can be prepared with gastric or enteric coatings with sugar, gelatin, hydroxypropylcellulose, or acrylic resins. Sustained-release tablets may also be obtained using an excipient that produces regressive osmosis, such as galacturonic acid polymers. Preparations for oral use can also be presented as hard capsules of absorbable material, for example gelatin, in which the active ingredient is mixed with an inert solid diluent and lubricating agents, or paste materials, such as saturated ethoxylated glycerides. Also possible are soft gelatin capsules, in which the active ingredient is mixed with water or with an oily medium, for example arachis oil, liquid paraffin, or olive oil. The dispersible and granulated powders suitable for the preparation of suspensions by adding the water present the active ingredient mixed with a dispersing or wetting agent; a suspending agent, such as sodium carbonate, cellulose, hydroxypropylmethyl cellulose, sodium alginate, polyvinylpyrrolidine, tragacanth gum, xanthan gum, gum arabic, and one or more preservatives, such as the methyl or n-propyl p-hydroxybenzoate. Other excipients may also be added, for example sweeteners, flavors and colorants. Liquid forms for oral administration include emulsions, solutions, suspensions, syrups and elixirs containing commonly used inert diluents, such as distilled water, ethanol, sorbitol, glycerol or propylene glycol. Aqueous solutions can also be prepared using β-cyclodextrins, such as hydroxypropyl-β-cyclodextrin. Said compositions may also contain adjuvants such as wetting, suspending, sweetening, flavoring, perfuming, preservative and pH regulating agents. Other compositions for oral administration include aerosols, which can be prepared by known methods. These aerosols must contain a suitable propellant.

Injectable preparations, in accordance with the present invention, for parenteral administration comprise sterile aqueous or non-aqueous solutions, suspensions or emulsions, in a non-toxic parenterally acceptable solvent or diluent. Examples of aqueous solvents or suspending media are distilled water for injection, Ringer's solution and isotonic sodium chloride solution. Aqueous solutions can also be prepared using β-cyclodextrins, such as hydroxypropyl-β-cyclodextrin. As non-aqueous solvents or suspending media, propylene glycol, polyethylene glycol, vegetable oils such as olive oil, or alcohols such as ethanol can be used. These compositions may also contain adjuvants, such as humectants, preservatives, emulsifiers and dispersants. They could be sterilized by any of the known methods or prepared as sterile solid compositions which will be dissolved in sterile water or any other sterile injectable medium immediately before use. When all components are sterile, the injectables will maintain sterility if manufactured in a sterile environment. Preparations for vaginal administration in accordance with the present invention include tablets, capsules, soft gelatine capsules, ovules, creams, foams and douching. In vaginal tablets the active ingredient is mixed with lactose, microcrystalline cellulose, pregelatinized starch, polyvidone and magnesium stearate as typical excipients. Soft gelatin capsules (softgels) can be prepared by dispersing the active ingredient in an oily medium, for example liquid paraffin, dimethylpolysiloxane 1000 or hydrogenated soybean oil. The ovules can be prepared by mixing the active ingredient with a suitable synthetic or semisynthetic base (such as, for example, the Suppocire® or Novata® type). Glycerides of saturated fatty acids from Cs to Cp of low viscosity and colloidal silica are also added to improve the incorporation of the active ingredient and prevent its sedimentation. The vaginal creams can be prepared in the form of emulsions, which should have enough viscosity to maintain their integrity and adhere to the vaginal cavity. As an oily phase, neutral fats, fatty acids, waxes, mineral oils and fatty acid esters can be used. As water phase, water, glycerin, sorbitol solution or polyethylene glycol can be used. Nonionic emulsifying agents such as the polyethylene glycol ethers can also be used, and said formulations can also contain preservatives, pH regulators and thickeners. The foams can be prepared using a foaming agent that is capable of transforming a solution into a foam. Such systems may also include cosolvents, pH regulators, preservatives, foam stabilizers and perfumes in an aqueous vehicle. Douching can contain cosolvents, preservatives, pH regulators and perfumes in an aqueous solution rich in surfactants. A compound of the invention can also be administered rectally in the form of a suppository and topically in the form of creams, ointments, pastes, lotions, gels, sprays, foams, aerosols, solutions, suspensions or powders. Said preparations are prepared by conventional methods well known to a person skilled in the art. A compound of the invention can also be administered in the form of a shampoo for the hair or the body. These formulations can be prepared using suitable ionic and / or amphoteric surfactants such as sodium lauryl sulfate, triethanolamine lauryl sulfate, cocoamidopropyl betaine.; thickening agents such as cocamide DEA, carbomer, sodium chloride and polyethylene glycol 6000 distearate; and optionally, emollient agents, pH regulators, preservatives and perfumes. Dosage and frequency of doses may vary depending on the nature and severity of the fungal infection, symptoms, age and body weight of the patient, as well as depending on the route of administration used. In general, the compounds of the invention will be administered orally or parenterally at a dose of 0.01 mg / kg / day to 100 mg / kg / day, which can be administered as a single dose or as divided doses. Following are some representative formulations for tablets, capsules, syrups, aerosols and injectable preparations. They can be prepared by conventional methods and are useful in the treatment of fungal infections.

Tablets Compound of formula I 100 mg Calcium dibasic phosphate 125 mg Sodium glycolate starch 10 mg Talc 12.5 mg Magnesium stearate 2.5 mg 250. 0 mg 1 Hard gelatin capsules Compound of formula I 100 mg Lactose 197 mg Magnesium stearate 3 mg 300 mg Tarabe Compound of formula I 0.4 g Sucrose 45 g Flavoring agent 0.2 g Sweetener 0.1 g Water c.s.p. 100 mL Aerosol Compound of formula I 4 g Flavoring agent 0.2 g Propylene glycol c.s.p 100 mL Propellant suitable c.s.p. 1 unit Injectable 1 Compound of formula I 100 mg Benzyl alcohol 0.05 mL Propylene glycol 1 L Water c.s. 5 mL Injectable 2 Compound of formula I 100 mg Hydroxypropyl-β-cyclodextrin 1 g Sodium chloride 90 mg Water q.s. 10 m L The following examples illustrate, but do not limit, the scope of the present invention: REFERENCE EXAMPLE 1 l- (4-Chlorophemethyl) -l-pyrazole-4-carboxylic acid. (a) A solution of carbetoximalonaldehyde (0.8 g, 5.55 mmol, obtained according to Panizzi, L. Gazz.Chim.Ital., 1946, 76, 56) in ethanol (25 mL) was treated with 4-chlorophenylhydrazine hydrochloride (1.0 g, 5.55 mmol) at reflux for 5 h. The resulting reddish mixture was concentrated to give an oil which was purified by flash chromatography to give l- (4-chlorophenyl) -lH-pyrazole-4-carboxylic acid ethyl ester (0.68 g, 49%) as a white solid: mp 127 -128 ° C; TH NMR (80 MHz, CDC13) d (TMS) 8.37 (s, 1H, pyrazole), 8.09 (s, 1H, pyrazole), 7.67 (dt, Jt = 2, / d = 9, 2H, arom), 7.44 ( dt, / t = 2, Jd = 9, 2H, arom), 4.35 (q, / = 7, 2H, OCH2), 1.38 (t, / = 7, 3H, OCH2CH3). Analysis calculated for C 12 H 11 CIN 2 O 2: C 57.50; H 4.42; N 11.17. Found: C 57.49; H 4.46; N 11.16. (b) A solution of the above product (0.44 g, 1.75 mmol) in EtOH (25 mL) and H 2 O (4 mL) was treated with KOH (857 °, 0.81 g, 13 mmol) at reflux for 4 h. After this time, the reaction mixture was concentrated, partitioned between H2O and CHCl3 and the organic phase was discarded. The aqueous phase was brought to pH 1 with 6iV HCl and the formed precipitate was filtered, washed with water and dried to give the title compound as a white solid (0.32 g, 82%): mp 234-235 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 8.44 (s, 1H, pyrazole), 8.16 (s, 1H, pyrazole), 7.68 (dt, / t = 2, / d = 9, 2H, arom), 7.45 (dt, / t = 2, / d = 9, 2H, arom). Analysis calculated for C 10 H 7 CIN 2 O 2: C 53.95; H 3.17; N, 12.58 Found: C 53.31; H 3.30; N 12.60. REFERENCE EXAMPLE 2 l- (4-Chlorophenyl) -! 5-methyl-1-pyrazole-4-carboxylic acid. The synthesis of the following 5-substituted l-aryl-lH-pyrazole-4-carboxylic acids was carried out according to the general methodology described in Menozzi, G. et al. J. Heterocyclic Cheri. 1987, 24, 1669. The following example illustrates this methodology: (a) To a solution of ethyl acetylacetate (6 g, 46 mmol) in benzene (100 mL) a solution of dimethylformamide dimethylacetal (8.2 g, 69 mmol) was slowly added. ) in benzene (100 mL) at 25 ° C. After addition, the reddish mixture was refluxed for 1 h and concentrated to dryness to give ethyl 2-dimethylaminomethylene-3-oxobutanoate (8.66 g) as a reddish oil. This product (3.25 g, 17 mmol) was reacted with 4-chlorophenylhydrazine hydrochloride (3.14 g, 17 mmol) in EtOH (50 mL) under reflux for 8 h. The mixture was concentrated to dryness and the product was isolated by flash chromatography to give ethyl l- (4-chlorophenyl) -5-methyl-lH-pyrazole-4-carboxylate as a white solid (2.07 g, 46%): mp 55-56 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 8.02 (s, 1H, pyrazole), 7.50 (d, / = 9, 2H, arom), 7.34 (d, / = 9, 2H, arom), 4.33 (q , / = 7, 2H, OCH), 2.56 (s, 3H, Me-pyrazole), 1.37 (t, / = 7, 3H, OCH2CH3). Analysis calculated for C 13 H 13 CIN 2 O 2: C 58.99; H 4.95; N 10.58. Found: C 59.03; H 5.06; N 10.58. (b) A solution of the product obtained in section (a) (1.91 g, 7.21 mmol) in EtOH (50 mL) and H20 (10 mL) was treated with KOH (85%, 3.35 g, 50 mmol) at 60 ° C. C for 20 h. After this time, the reaction mixture was concentrated and partitioned between H20 and CHCl3. The organic phase was discarded and the aqueous phase was brought to pH 1 with 3N HCl. The precipitate formed was filtered, washed with water and dried to give the title compound as a white solid (1.42 g, 83%): mp 195-198 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 8.39 (s, 1 H, pyrazole), 7.50 (d, J = 9, 2 H, arom), 7.34 (d, / = 9, 2 H, arom), 2.59 (s) , 3H, Me-pyrazole). Analysis calculated for C 11 H 9 CIN 2 O 2: C 55.83; H 3.83; N, 11.84. Found: C 56.10; H 3.82; N 11.54. REFERENCE EXAMPLE 3 l- (4-Chlorophenyl) -5-isopropyl-1H-pyrazole-4-carboxylic acid (a) Following a methodology similar to that described in the section of reference example 2, l- (4-) chlorophenyl) -5-isopropyl-1H-pyrazole-4-carboxylic acid ethyl ester as a white solid: mp 86-87 ° C; l NMR (80 MHz, CDCl 3) d (TMS) 8.01 (s, 1H, pyrazole), 7.48 (dt, / = 2, / d = 9, 2H, arom), 7.28 (dt, / t = 2, / d = 9, 2H, arom), 4.33 (q, J = 7, 2H, OCH2), 3.28 (quint, J = 7, 1H, Me2CH), 1. 38 (t, J = 7, 3H, OCH2CH3), 1.35 (d, / = 7, 6H, Me2CH). Analysis calculated for C15H17CIN2O2: C 61.54; H 5.85; N 9.57. Found: C 61.23; H 5.94; N 9.42. (b) Following a procedure similar to that described in section b of reference example 2, the title compound was obtained as a white solid: mp 211-212 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 8.11 (s, 1H, pyrazole), 7. 48 (dt, / t = 2, / d = 9, 2H, arom), 7.30 (dt, / t = 2, / d = 9, 2H, arom), 3.29 (quint, / = 7, 1H, Me2CH) , 1.37 (t, / = 7, 6H, Me2CH). Analysis calculated for C 13 H 13 CIN 2 O 2: C 58.99; H 4.95; N 10.58. Found: C 59.23; H 4.93; N 10.47. REFERENCE EXAMPLE 4 5-feríbutil-l- (4-chlorophenyl) -LH-pyrazole-4-carboxylic acid (a) Following a similar to that described in paragraph 2 of reference example methodology pure 5-ferfbutil-l Ethyl (4-chlorophenyl) -lH-pyrazole-4-carboxylate as a white solid: mp 104-105 ° C; ! H NMR (80 MHz, CDCl 3) d (TMS) 7.96 (s, 1H, pyrazole), 7.43 (dt, / t = 2, / d = 9, 2H, arom), 7.24 (dt, / t = 2, / d = 9, 2H, arom), 4.31 (q,] = 7, 2H, OCH2), 1.37 (t, / = 7, 3H, OCH2CH3), 1.31 (s, 9H, Me_C). Analysis calculated for C 16 H 9 CIN 2 O 2: C 62.64; H 6.24; N 9.13. Found: C 62.67; H 6.28; N 9.12. "*" (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: NMR (80 MHz, CDCl 3) d (TMS) 8.09 (s, 1H, pyrazole), 7.45 (dt, / = 2, / d = 9, 2H, arom), 7.26 (dt, / t = 2, / d = 9, 2H, arom), 1.34 (s, 9H, Me3.? Analysis calculated for C14H15CIN2O2: C 60.33; H 5.42; N 10.05. Found: C 60.41; H 5.41; N 10.12. REFERENCE EXAMPLE 5 5-cyclopropyl-l- (4-chlorophenyl) -l_H-pyrazol-4-carboxüico (a) Following a similar to that described in section a of reference example 2 was obtained methodology-cyclopropyl- 5 1- (4-chlorophenyl) -lH-pyrazole-ethyl 4-carboxylate in the form of a white solid: mp 64-65 ° C; NMR (80 MHz, CDCl 3) d (TMS) 8.00 (s, 1H, pyrazole), 7.46 (s, 4H, arom), 4.33 (q, J = 7, 2H, OCH2), 2.2-1.8 (m, 1H, c-prop ), 1.37 (t, / = 7, 3H, OCH2CH3), 1.3-0.8 (m, 2H, c-prop), 0.8-0.5 (m, 2H, c-prop). Analysis calculated for C15H15CIN2O2: C 61.97; H 5.20; N 9.63. Found: C 61.64; H 5.26; N 9.65. 1 (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 186-187 ° C; ? NMR (80 MHz, CDCl 3) d (TMS) 8.09 (s, 1H, pyrazole), 7.46 (s, 4H, arom), 2.2-1.8 (m, 1H, c-prop), 1.3-0.8 (m, 2H, c-prop), 0.8-0.5 (m, 2H, c-prop). Analysis calculated for C 13 H 11 CIN 2 O 2: C 59.44; H 4.22; N 10.66. Found: C 2 0 59.37; H 4.17; N 10.46. REFERENCE EXAMPLE 6 5-metU-l- (4-trifluoromethylphenyl) -lh-pyrazole-4-carboxylic acid (a) Following a similar to that described in section a of reference example 2 was obtained methodology 5-methyl 1- (4-trifluoromethylphenyl) -lH-2-pyrazole-4-carboxylic acid ethyl ester in the form of a white solid: mp 60-61 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 8.05 (s, 1H, pyrazole), 7.79 (d,.) = 9, 2H, arom), 7.58 (d, J = 9, 2H, arom), 4.33 (q ,] = 7, 2H, OCH2), 2.62 (s, 3H, Me-pyrazole), 1.38 (t, / = 7, 3H, OCH2CH3). Analysis calculated for 4H13F3N2O2: C 56.38; H 4.39; N 9.39. Found: C 56.34; H 4.36; N 9.32. 3 0 (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 186-187 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 8.14 (s, 1H, pyrazole), 7.80 (d, / = 9, 2H, arom), 7.60 (d, / = 9, 2H, arom), 2.64 ( s, 3H, g-pyrazole). Analysis calculated for C 12 H 9 F 3 N 2 O 2: C 53.34; H 3.36; N 10.37. Found: C 53.68; H 3.38; N 10.22. REFERENCE EXAMPLE 3 May 7 L- (4-bromophenyl) -5-methyl-lH-pyrazole-4-carboxylic acid (a) Following a similar to that described in the section of • 'methodology - "Reference Example 2 was obtained ethyl l- (4-bromophenyl) -5-methyl-lH-pyrazole-4-carboxylate in the form of a dense oil: H NMR (80 MHz, CDCl 3) d (TMS) 8.02 (s, 1 H, pyrazole), 7.63 (dt, / t = 2, / d = 9, 2H, arom), 7.31 (dt, / t = 2, / d = 9, 2H, arom), 4.33 (q, / = 7, 2H, OCH2), 2.56 (s, 3H, Me-pyrazole), 1.37 (t, / = 7, 3H, 5 OCH2CH3) Analysis calculated for C? 3H? 3BrN2? 2: C 50.51; H 4.24; N 9.06. Found: C 50.34; H 4.57; N, 8.93. (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 213-214 ° C; ? NMR (80 MHz, CDCl 3) d (TMS) 8.10 (s, 1H, pyrazole), 7.65 (dt, /t1.5, 1 0 Jd = 9, 2H, arom), 7.31 (dt, Jt = 1.5, / d = 9, 2H, arom), 2.59 (s, 3H, Me-pyrazole). Analysis calculated for CpH9BrN2? 2: C 47.00; H 3.23; N 9.97. Found: C 47.01; H 3.21; N 9.99. REFERENCE EXAMPLE 8 5-Trifluoromethyl-1- (4-trifluoromethyl-phenyl) -lH-pyrazole-4-carboxylic acid 1 5 (a) Following a methodology similar to that described in section a of reference example 2, ethyl 5-trifluoromethyl-l- (4-trifluoromethyl-phenyl) -lH-pyrazole-4-carboxylate was obtained as a white solid : mp 45-46 ° C; * H NMR (80 MHz, CDCl 3) d (TMS) 8.14 (s, 1H, pyrazole), 7.90 (d, J = 9, 2H, arom), 7.56 (d, / = 9, 2H, arom), 4.38 ( q, 7 = 7, 2H, OCH2), 1.39 (t, 7 = 7, 3H, OCH2CH3). 2 0 Analysis calculated for Ci4H? 0F6N2? 2: C 47.74; H 2.86; N, 7.95. Found: C 47. 89; H 2.92; N, 7.95. (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 157-158 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 8.23 (s, 1H, pyrazole), 7.82 (d, 7 = 9, 2H, 2 5 arom), 7.58 (d, 7 = 9, 2H, arom). Analysis calculated for Ci2H6F6N2? 2: C 44.46 H 1. 87; N 8.64. Found: C 44.76; H 1.82; N, 8.50. REFERENCE EXAMPLE 9 l- (3,5-Dichlorophenyl) -5-methyl-1H-pyrazole-4-carboxylic acid (a) Following a methodology similar to that described in the section on Reference example 2 gave ethyl l- (3,5-dichlorophenyl) -5-methyl-lH-pyrazole-4-carboxylate as a slightly yellow solid: mp 85-86 ° C; * H NMR (80 MHz, CDCl 3) d (TMS) 8.02 (s, 1H, pyrazole), 7.5-7.3 (m, 3H, arom), 4.34 (q, 7 = 7, 2H, OCH2), 2.61 (s, 3H, e-pyrazole), 1.37 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C 13 H 12 Cl 2 2 O 2: C 52.19; H 4.04; N 9.36. Found: C 52.20; H 3 5 3.99; N 9.97. (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 229-230 ° C; 1 H NMR (300 MHz, CDC13) d (TMS) 7.98 (s, 1 H, pyrazole), 7.40 (t, 7 = 1 -8, 1H, arom), 7.33 (t, 7 = 1-8, 2H, arom. ), 2.54 (s, 3H, Vte-pyrazole). Analysis calculated for C 1 H 8 Cl 2 N 2 O 2: C 48.73; H 2.97; N 10.33. Found: C 48.92; H 2.89; N 10.40. REFERENCE EXAMPLE 10 A-cido l- (2,6-dichlorophenyl) -5-methyl-1H-pyrazole-4-carboxylic acid (a) Following a methodology similar to that described in section a of reference example 2, the ethyl l- (2,6-dichlorophenyl) -5-methyl-lH-pyrazole-4-carboxylate in the form of a colorless oil: ^ H NMR (80 MHz, CDCl 3) d (TMS) 8.12 (s, 1H, pyrazole) , 7.6-7.4 (m, 3H, arom), 4.34 (q, 7 = 7, 2H, OCH2), 2.36 (s, 3H, Me-pyrazole), 1.38 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C 13 H 12 Cl 2 N 2 O 2: C 52.19; H 4.04; N 9.36. Found: C 52.56; H 3.81; N 9.14. (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 180-182 ° C; l NMR (300 MHz, CDCl 3) d (TMS) 8.20 (s, 1H, pyrazole), 7.6-7.4 (m, 3H, arom), 2.40 (s, 3H, Me-pyrazole). Analysis calculated for C 11 H 8 Cl 2 N 2 O 2: C 48.73; H 2.97; N 10.33. Found: C 48.82; H 2.90; N 10.20. REFERENCE EXAMPLE 11 l- (2-Chlorophenyl) -5-methyl-L-pyrazole-4-carboxylic acid (a) Following a methodology similar to that described in section a of reference example 2, l- (2) ethyl chlorophenyl) -5-methyl-lH-pyrazole-4-carboxylate in the form of a colorless oil: * H NMR (300 MHz, CDCl 3) d (TMS) 8.05 (s, 1H, pyrazole), 7.6-7.4 (m , 4H, arom), 4.32 (q, 7 = 7, 2H, OCH2), 2.39 (s, 3H, Me-pyrazole), 1.37 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C 13 H 13 CIN 2 O 2: C 58.99. H 4.95; N 10.58. Found: C 59.20; H 4.91; N 10.38. (b) Following the procedure described in section b of reference example 2, < 1-title compound in the form of white solid: mp 150-151 ° C; 1 H NMR (300 MHz, CDCl 3) d (TMS) 8.14 (s, 1H, pyrazole), 7.6-7.4 (m, 4H, arom), 2.42 (s, 3H, < α-pyrazole). Analysis calculated for C 11 H 9 CIN 2 O 2: C 55.83; H 3.83; N, 11.84. Found: C 56.03; H 3.91; N 11.93. REFERENCE EXAMPLE 12 l- (4-Chlorophenyl) -3,5-dimethyl-li-pyrazole-4-carboxylic acid (a) Following a methodology similar to that described in section a of reference example 2 but reacting diacetylacetate of ethyl with 4-chlorophenylhydrazine hydrochloride was obtained directly l- (4-chlorophenyl) -3,5-dimethyl-lH-pyrazole-4-carboxylic acid ethyl ester as a white solid: mp 79-80 ° C; ] H NMR (80 MHz, CDCl 3) d (TMS) 7.47 (d, 7 = 9, 2H, arom), 7.32 (d, 7 = 9, 2H, arom), 4.32 (q, 7 = 7, 2H, OCH2 ), 2.51 (s, 3H, e-pyrazole), 2.49 (s, 3H, Me-pyrazole), 1.38 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C 14 H 15 CIN 2 O 2: C 60.33; H 5.42; N 10.05. Found: C 60.44; H 5.48; N 10.29. (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 220-223 ° C; l NMR (80 MHz, CDCl 3) d (TMS) 7.48 (d, 7 = 9, 2H, arom), 7.34 (d, 7 = 9, 2H, arom), 2.55 (s, 3H, Me-pyrazole), 2.52 (s, 3H, Mg-pyrazole). Analysis calculated for C 12 H 11 CIN 2 O 2: C 57.50; H 4.42; N 11.17. Found: C 57.60; H 4.43; N 11.19. REFERENCE EXAMPLE 13 5-Amino-1- (4-chlorophenyl) -lH-pyrazole-4-carboxylic acid (a) A solution of ethyl ethoxymethylene-acetic acid ethyl acetate (3 g, 17.7 mmol) and 4-chlorophenylhydrazine hydrochloride was heated to reflux ( 3.33 g, 18.6 mmol) in ethanol (60 mL) for 2 days, following the methodology described in Schmidt, P. et al. Helv.Chim.Acta, 1959, 349. After this time elapsed the reaction mixture was cooled to room temperature whereupon a precipitate appeared. Cold CHCl3 was added, the precipitate was filtered and washed with more CHCl3. The filtrate and washings were concentrated to dryness, precipitated with ether, filtered and dried to give ethyl 5-amino-l- (4-chlorophenyl) -lH-pyrazole-4-carboxylate (2.25 g, 48 g). %) in the form of white solid: mp 150-156 ° C; 1 NMR (80 MHz, CDCl 3) d (TMS) 7.77 (s, 1H, pyrazole), 7.48 (s, 4H, arom), 4.30 (q, 7 = 7, 2H, OCH 2), 1-36 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C12H12CIN3O2: C 54.25; H 4.55; N 15.81. Found: C 54.77; H 4.49; N 15.65. (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 169-171 ° C; ? NMR (80 MHz, CDCl 3 + MeOH-d 4) d (TMS) 7.78 (s, 1H, pyrazole), 7.50 (s, 4H, arom), 4.25 (broad s, NH 2, OH). Analysis calculated for C 10 H 8 CIN 3 O 2: C 50.54; H 3.39; N 17.68. Found: C 50.54; H 3.39; N 17.44. REFERENCE EXAMPLE 14 5-Amino-1- (4-trifluoromethyl-phenyl) -lH-pyrazole-4-carboxylic acid (a) Following the methodology described in reference example 13, 5-amino-1- (4-trifluoromethylphenyl) was obtained ) -lH-pyrazole-4-carboxylic acid ethyl ester in the form of amorphous white solid: TH NMR (80 MHz, CDCl 3) d (TMS) 7.76 (s, 1H, pyrazole), 7.90 (d, 7 = 9, 2H, arom. ), 7.56 (d, 7 = 9, 2H, arom), 4.31 (q, 7 = 7, 2H, OCH2), 1-35 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C 13 H 12 F 3 N 3 O 2: C 52.18; H 4.04; N 14.04. Found: C 52.13; H 4.22; N 14.02 u (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 169-171 ° C; 1 H NMR (80 MHz, CDCl 3 + MeOH-d 4) d (TMS) 7.78 (s, 1 H, pyrazole), 7.90 (d, -7 = 9, 2 H, arom), 7.56 (d, 7 = 9, 2 H, arom. ), 4.32 (s, NH2, OH). Analysis calculated for C 11 H 8 F 3 N 3 O 2: C 48.72; H 2.97; N 15.49. Found: C 48.52; H 3.18; N 15:28. REFERENCE EXAMPLE 15 5-Methyl-1- (3-trifluoromethylphenyl) -lH-pyrazole-4-carboxylic acid (a) Following a methodology similar to that described in section a of reference example 2, 5-methyl- Ethyl l- (3-trifluoromethylphenyl) -lH-pyrazole-4-carboxylate as a colorless oil: H NMR (80 MHz, CDCl 3) d (TMS) 8.05 (s, 1H, pyrazole), 7.8-7.5 (m, 4H, arom), 4.34 (q, 7 = 7, 2H, OCH2), 2.61 (s, 3H, Me-pyrazole), 1.38 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C 14 H 13 F 3 N 2 O 2: C 56.38; H 4.39; N 9.39. Found: C 56.42; H 4.67; N 9.13. (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 122-123 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 8.20 (s, 1H, pyrazole), 7.8-7.7 (m, 4H, arom), 2.69 (s, 3H, Me-pyrazole). Analysis calculated for C 12 H 9 F 3 N 2 O 2: C 53.34; H 3.36; N 10.37. Found: C 53.36; H 3.50; N 10.44. REFERENCE EXAMPLE 16 5-Methyl-1- (4-trifluoromethoxy-phenyl) -L-pyrazole-4-carboxylic acid (a) Following a methodology similar to that described in section a of reference example 2, 5-methyl- Ethyl l- (4-trifluoromethoxyphenyl) -lH-pyrazole-4-carboxylate as a colorless oil: H NMR (80 MHz, CDCl 3) d (TMS) 8.02 (s, 1 H, pyrazole), 7.52 (d, 7 = 9, 2H, arom), 7.32 (d, 7 = 9, 2H, arom), 4.33 (q, 7 = 7, 2H, OCH), 2.57 (s, 3H, Me-pyrazole), 1.38 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C 14 H 13 F 3 N 2 O 3: C 53.51; H 4.17; N, 8.91. Found: C 53.43; H 4.28; N 8.55. (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 176-178 ° C; ? NMR (300 MHz, CDCl 3) d (TMS) 8.46 (s, 1H, pyrazole), 7.55 (dt, 7t = 2.8, 7d = 8.8, 2H, arom), 7.43 (d, /=8.8, 2H, arom), 2.67 (s, 3H, Me-pyrazole). Analysis calculated for C 12 H 9 F 3 N 2 O 3: C 50.36; H 3.17; N 9.79. Found: C 50.52; H 3.13; N 9.76. REFERENCE EXAMPLE 17 5-Methyl-1- (4-methoxyphenyl) -lfi-pyrazole-4-carboxylic acid (a) Following a methodology similar to that described in section a of reference example 2, 5-methyl- Ethyl l- (4-methoxyphenyl) -lH-pyrazole-4-carboxylate in the form of a colorless oil: H NMR (300 MHz, CDCl 3) d (TMS) 7.99 (s, 1 H, pyrazole), 7.31 (d, 7 = 9, 2H, arom), 6.99 (d, 7 = 9, 2H, arom), 4.31 (q, -7 = 7, 2H, OCH2), 3.85 (s, 3H, OMe), 2.51 (s, 3H, Me -pirazol), 1.34 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C 14 H 16 N 2 O 3: C 64.60; H 6.20; N 10.76. Found: C 64.89; H 6.41; N 10.51. (b) Following the procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 212-213 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 8.08 (s, 1H, pyrazole), 7.33 (d, 7 = 8.8, 2H, arom), 7.01 (d, 7 = 8.8, 2H, arom), 3.87 ( s, 3H, OMe), 2.54 (s, 3H, Me-pyrazole). Analysis calculated for C 12 H 12 N 2 O 3: C 62.06; H 5.21; N 12.06. Found: C 62.23; H 2.13; N 12.06. REFERENCE EXAMPLE 18 2- (4-Chlorophenyl) thiazole-5-carboxylic acid (a) A solution of ethyl formylchloroacetate was heated to reflux (1.45 g, 9.6 mmol, obtained according to Panizzi, L. Gazz. Chim. Tal., 1946, 76, 56) and 4-chlorothiobenzamide (1.76 g, 9.6 mmol) in EtOH (50 mL) for 48 h. After this time, the reaction mixture was cooled to -20 ° C and the solid formed was filtered and dried to give ethyl 2- (4-chlorophenyl) thiazole-5-carboxylate (0.59 g, 23%): mp 144-145 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 8.40 (s, 1H, thiazole), 7.92 (dt, Jt = 1.8, 7 = 8.6, 2H, arom), 7.44 (dt, /t1.8, 7d = 8 -6, 2H, arom), 4.39 (q, 7 = 7, 2H, OCH2), 1-40 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C12H10CINO2S: C 53.84; H 3.76; N 5.23; S 11.97. Found: C 54.22; H 3.52; N 5.25; S 11.46. (b) Following the hydrolysis procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 233-234 ° C; ^ H NMR (300 MHz, CDCl 3 + MeOH-d 4) d (TMS) 8.31 (s, 1H, thiazole), 7.83 (dt, /t -1.8, /d=8.8, 2H, arom), 7.37 (dt, / t = 1.8, 7 = 8.8, 2H, arom). Analysis calculated for C10H 6CINO2S: C 50.11; H 2.52; N 5.84; S 13.38. Found: C 49.37; H 2.41; N 5.54; S 11.90. REFERENCE EXAMPLE 19 2-Phenyl-4-methylthiazole-5-carboxylic acid (a) A solution of methyl 2-chloroacetoacetate was heated to reflux. (1.86 g, 12.4 mmol) and benzothiamide (1.7 g, 12.4 mmol) in EtOH (50 mL) for 18 h. The mixture was concentrated to dryness and the oil obtained was purified by flash chromatography to give methyl 2-phenyl-4-methylthiazole-5-carboxylate (1.21 g, 42%) as a colorless oil: 1 H NMR (300 MHz, CDCl 3 ) d (TMS) 8.0-7.9 (m, 2H, arom), 7.5-7.4 (m, 3H, arom), 3.87 (s, 3H, OMe), 2.76 (s, 3H, Me-thiazole). Analysis calculated for C 12 H 11 NO 2 S: C 61.78; H 4.75; N 6.00; S 13.74. Found: C 61.56; H 4.71; N 5.82; S 14.61 (b) Following the hydrolysis procedure described in section b of reference example 2 but using MeOH as solvent and heating at 80 ° C for 4 h, the title compound was obtained as a white solid: mp 215-218 ° C; ] H NMR (300 MHz, CDCl 3 + MeOH-d 4) d (TMS) 7.9-7.8 (m, 2 H, arom), 7.4-7.3 (m, 3 H, arom), 2.66 (s, 3 H, Me-thiazole). Analysis calculated for C 11 H 9 NO 2 S: C 60.26 H 4.14; N 6.39; S 14.62. Found: C 60.37; H 4.07; N 6.14; S 14.91. REFERENCE EXAMPLE 20 2- (4-Chlorophenyl) -4-methylthiazole-5-carboxylic acid (a) Following the methodology described in the section of reference example 19, 2- (4-chlorophenyl) -4-methylthiazole- Methyl 5-carboxylate as a white solid: mp 132-133 ° C; H NMR (80 MHz, CDCI3) or (TMS) 7. 89 (dt, 7t = 1.8, 7d = 8.8, 2H, arom), 7.40 (dt, /t=1.8, 7d = 8-8, 2H, arom), 3.89 (s, 3H, OMe), 2.77 (s, 3H, Me-thiazole). Analysis calculated for C12H10CINO2S: C 53.84; H 3.76; N 5.23; S 11.97. Found: C 54.09; H 3.78; N 5.10; S 12.27. (b) Following the hydrolysis procedure described in section b of reference example 19, the title compound was obtained as a white solid: mp 256-253 ° C; ? NMR (300 MHz, CDCl 3 + MeOH-d 4) d (TMS) 7. 84 (dt, 7t = l-8, 7d = 8.8, H, arom), 7.40 (dt, /t=1.8, 7d = 8.8, 2H, arom), 2.70 (s, 3H, Me-thiazole). Analysis calculated for CpHßClNO? S: C 52.08; H 3.18; N 5.52; S 12.64. Found: C 49.38; H 2.93; N 5.15; S 11.20. EXAMPLE OF REFERENCE 21 2- (4-Bromophenyl) -4-methylthiazole-5-carboxylic acid (a) Following the methodology described in section a of reference example 19, 2- (4-bromophenyl) -4-methylthiazole was obtained Methyl carboxylate as a white solid: mp 144-146 ° C; * H NMR (80 MHz, CDCl 3) 5 (TMS) 7.84 (dt, / t = 2, 7d = 8.6, 2H, arom), 7.57 (dt, 7t = 2, 7d = 8-6, 2H, arom), 3.89 (s, 3H, OMe), 2.77 (s, 3H, Me-thiazole). Analysis calculated for Ci2H? OBrN? 2S: C 46.17; H 3.23; N 4.49; S 10.27. Found: C 45.95; H 3.27; N 4.52; S 10.34. (b) Following the hydrolysis procedure described in section b of reference example 19, the title compound was obtained as a white solid: mp 227 ° C (dec); * H NMR (80 MHz, CDCl 3 + MeOH-d) d (TMS) 7. 85 (dt, 7t = l-8, 7d = 8-8, 2H, arom), 7.40 (dt, 7t = 1.8, 7d = 8.8, 2H, arom), 2.79 (s, 3H, Me-thiazole). Analysis calculated for CnH8BrN? 2S: C 44.31; H 2.70; N 4.70; S 10.75. Found: C 44.02; H 3.09; N 4.45; S 10.36. REFERENCE EXAMPLE 22 4-Methyl-2- (4-trifluoromethoxyphenyl) thiazole-5-carboxylic acid (a) Following the methodology described in section a of reference example 19, 4-methyl-2- (4-trifluoromethoxyphenyl) was obtained ) methyl thiazole-5-carboxylate as a white solid: mp 76-77 ° C; * H NMR (80 MHz, CDCl 3) d (TMS) 8.00 (dt, 7t = 2, 7d = 8.8, 2H, arom), 7.30 (dt, / t = 2, 7d = 8-8, 2H, arom), 3.90 (s, 3H, OMe), 2.78 (s, 3H, Me-thiazole). Analysis calculated for C 13 H 10 F 3 NO 3 S: C 49.21; H 3.18; N 4.41; S 10.10. Found: C 49.23; H 3.40; N 4.36; S 10.37. (b) Following the hydrolysis procedure described in section b of reference example 19, the title compound was obtained as a white solid: mp 179-181 ° C; * H NMR (80 MHz, CDCl 3) d (TMS) 8.00 (dt, /t1.8, 7d = 8.8, 2H, arom), 7.30 (dt, /t1.8, 7d = 8.8, 2H, arom), 2.81 (s, 3H, Me-thiazole). Analysis calculated for C 12 H 8 F 3 NO 3 S: C 47.53; H 2.66; N 4.62; S 10.57.

Found: C 47.59; H 2.68; N 4.62; S 10.26. EXAMPLE OF REFERENCE 23 4-Methyl-2- [4- (2,2,3,3-tetrafluoropropoxy) phenyl] thiazole-5-carboxylic acid (a) Following the methodology described in section a of reference example 19, methyl 4-methyl-2- [4- (2,2,3,3-tetrafluoropropoxy) phenyl] thiazole-5-carboxylate as a white solid: mp 102-103 ° C; l NMR (80 MHz, CDCl 3) d (TMS) 7.95 (dt, / t = 2, /d=8.8, 2H, arom), 7.00 (dt, / = 2, 7d = 8-8, 2H, arom), 6.06 (tt, 7 = 4.6, 7 = 53, 1H, CHF2), 4.41 (tt, 7 = 1-5, /=11.8, 2H, CH2), 3.89 (s, 3H, OMe), 2.77 (s, 3H , Me-thiazole). Analysis calculated for C15H13F4NO3S: C 49.59; H 3.61; N 3.86; S 8.82. Found: C 49.76; H 3.73; N 3.89; S 8.66. (b) Following the hydrolysis procedure described in section b of reference example 19, the title compound was obtained as a white solid: mp 167-168 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 7.95 (dt, / t = 1.8, 7d = 8.8, 2H, arom), 7.00 (dt, 7t = 1.8, 7d = 8-8, 2H, arom), 6.05 (tt, 7 = 4.6, 7 = 53, 1H, CHF2), 4.41 (tt, 7 = 1.5, 7 = 11.8, 2H, CH2), 2.79 (s, 3H, Me-thiazole). Analysis calculated for C 14 H 11 F 4 NO 3 S: C 48.14; H 3.17; N 4.01; S 9.18. Found: C 48.20; H 3.19; N 3.71; S 8.72. REFERENCE EXAMPLE 24 2- (4-Cyanophenyl) -4-methylthiazole-5-carboxylic acid (a) A suspension of methyl 2-chloroacetoacetate (30 g, 0.19 mol) and 4-cyanobenzothiamide (21.5 g, 0.13 mol) in MeOH (250 mL) for 15 h. The reaction mixture was then cooled to 0 ° C, filtered after 20 h and washed with cooled MeOH (-20 ° C) and with ether. The resulting beige solid was dried to give methyl 2- (4-cyanophenyl) -4-methylthiazole-5-carboxylate (18.7 g, 55%). If desired, more product can be recovered by flash chromatography of the waters: mp 186-187 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 8.07 (dt, 7t = 1.6, /d=8.3, 2H, arom), 7.74 (dt, / t = l-6, 7d = 8-3, 2H, arom. ), 3.91 (s, 3H, OMe), 2.79 (s, 3H, Me-thiazole). Analysis calculated for C 13 H 10 N 2 O 2 S: C 60.45; H 3.90; N 10.85; S 12.41. Found: C 60.31; H 3.80; N 10.53; S 11.79. (b) The product obtained in section (a) (18.7 g, 72.4 mmol) was dissolved in a mixture of MeOH (0.6 L) and THF (0.3 L). Then a solution formed by LÍOH.H2O (15.2 g, 0.36 mol) in 60 mL of water was slowly added and the resulting reddish mixture was stirred at 30 ° C for 8 h. The mixture was concentrated to dryness, water was added to the residue, it was filtered on celite and acidified with 3 / V HCl until pH 1.0-1.2, which caused the appearance of an orange spongy mass. This product, difficult to filter, was centrifuged, washed with cold water and recentrifuged and dried to give the title compound as a yellowish solid (18 g, 100%): mp 235-250 ° C; NMR (300 MHz, CDCl 3) d (TMS) 8.15 (dt, / t = l-6, 7d = 8.3, 2H, arom), 7.84 (dt, / el .6, /d=8.3, 2H, arom), 2.74 (s, 3H, Me-thiazole). Analysis calculated for C 12 H 8 N 2 O 2 S: C 59.01; H 3.30; N 11.47; S 13.12. Found: C 59.31; H 3.18; N 11.68; S 13.01. REFERENCE EXAMPLE 25 2- [2- (4-Chlorophenyl) -4-methylthiazol-5-yl] -4-methylthiazole-5-carboxylic acid (a) A solution of 2- (4-chlorophenyl) -4-methylthiazole 5-carboxylic acid (0.78 g, 3 mmol, obtained in Reference Example 20) in thionyl chloride (10 mL) was heated to reflux for 4 h. The reaction mixture was concentrated to dryness and the resulting residue (0.93 g) was dissolved in THF (15 mL) and added slowly to a cooled (0 ° C) solution of 40% ammonium hydroxide. The volatiles were removed by concentration and the resulting aqueous residue was filtered and dried to give 2- (4-chlorophenyl) -4-methylthiazole-5-carboxamide (0.63 g, 79%) as a white solid: mp 236-237 ° C; ^ H NMR (300 MHz, CDCl 3 + MeOH-d 4) d (TMS) 7.80 (d, / = 8.4, 2H, arom), 7.36 (d, 7 = 8.4, 2H, arom), 2. 66 (s, 3H, Me-thiazole). (b) To a solution of the product obtained in section (a) (0.89 g, 3.52 mmol) in a mixture of toluene (15 mL) and THF (15 mL), Lawesson's reagent (0.85 g, 2.11 mmol) was added. and the resulting yellow solution was heated to reflux for 2 h. The reaction mixture was concentrated to dryness and the product formed (2- (4-chlorophenyl) -4-methylthiazole-5-carbothioamide, 2.19 g) was reacted with methyl 2-chloroacetoacetate in a manner similar to that described in a) of reference example 19. Flash chromatography isolated methyl 2- [2- (4-chlorophenyl) -4-methylthiazol-5-yl] -4-methylthiazole-5-carboxylate as a yellow solid ( 0.59 g, 46%): mp 174-175 ° C; * H NMR (300 MHz, CDC13 + MeOH-d4) d (TMS) 7.90 (d, / = 8.4, 2H, arom), 7.42 (d, 7 = 8.4, 2H, arom), 3.91 (s, 3H, OMe )), 2766 (s, 3H, Me-thiazole), 2761 (s, 3H, Me-thiazole). Analysis calculated for C? 6H? 3ClN2? 2S2: C 52.67; H 3.59; N 7.68; S 17.57. Found: C 52.53; H 3.87; N 7.29; S 17.01. (c) Following the hydrolysis procedure described in section b of reference example 2, the title compound was obtained as a somewhat yellowish solid: mp 265-268 ° C; * H NMR (300 MHz, CDCl 3) d (TMS) 8.15 (dt, 7t = 1.6, 7d = 8.3, 2H, arom), 7.84 (dt, / t = l -6, /d=8.3, 2H, arom) 2.74 (s, 6H, Me-thiazole). Analysis calculated for C15H11CIN2O2S2: C 51.35; H 3.16; N 7.98; S 18.28. Found: C 51.32; H 3.12; N 7.78; S 17.43. REFERENCE EXAMPLE 26 2- (4-Chlorophenyl) -4-trifluoromethylthiazole-5-carboxylic acid (a) Following the methodology described in section a of reference example 19 but using 2-chloro-4,4,4-trifluoroacetoacetate ethyl and 4-chlorophenylthiobenzamide ethyl 2- (4-chlorophenyl) -4-trifluoromethylthiazole-5-carboxylate was obtained as a white solid contaminated with some starting material: "? NMR (300 MHz, CDCl 3) d (TMS) ) 7.81 (dt, /t=2.4, /d=8.7, 2H, arom), 7.42 (dt, /t2.4, /d=8.7, 2H, arom), 4.3-4.2 (m, 2H, OCH2), 1.32 (t, / = 7, 3H, OCH2CH3). (b) Following the hydrolysis procedure described in section b of reference example 19, the title compound was obtained as a white solid: mp 235-250 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 7.95 (dt, 7t = 2.4, 7d = 8.7, 2H, arom), 7.43 (d, /=8.3, 2H, arom). Analysis calculated for C 11 H 5 ClF 3 NO 2 S: C 42.94; H 1.64; N 4.55; S 10.42. Found: C 43.34; H 1.66; N 4.48; S 9.93. REFERENCE EXAMPLE 27 4-Trifluoromethyl-2- (4-trifluoromethylphenyl) thiazole-5-carboxylic acid (a) Following the methodology described in section a of reference example 19 but using 2-chloro-4,4,4-trifluoroacetoacetate of ethyl and 4-trifluoromethylphenylthiobenzamide was obtained ethyl 4-trifluoromethyl-2- (4-trifluoromethylphenyl) thiazole-5-carboxylate as a white solid contaminated with some starting material: TH NMR (300 MHz, CDCl 3) d ( TMS) 8.01 (d, 7 = 8.1, 2H, arom), 7.71 (d, /=8.1, 2H, arom), 4.3-4.2 (m, 2H, OCH2), 1.34 (t, 7 = 7, 3H, OCH2CH3 ). (b) Following the hydrolysis procedure described in section b of reference example 19, the title compound was obtained as a white solid: mp 177-179 ° C; ] H NMR (300 MHz, CDCl 3) d (TMS) 8.14 (d, 7 = 8.2, 2H, arom), 7.75 (d, 7 = 8.2, 2H, arom). Analysis calculated for C 12 H 5 F 6 NO 2 S: C 42.24; H 1.48; N 4.10; S 9.40. Found: C 41.86; H 1.33; N 4.03; S 8.92. REFERENCE EXAMPLE 28 2- (4-Cyanophenyl) -4-trifluoromethylthiazole-5-carboxylic acid (a) Following the methodology described in section a of reference example 24 but using 2-chloro-4,4,4-trifluoroacetoacetate ethyl ethyl 2- (4-cyanophenyl) -4-trifluoromethylthiazole-5-carboxylate was obtained as a white solid contaminated with some starting material. (b) Following the hydrolysis procedure described in section b of reference example 24, the title compound was obtained as a white solid: mp 195-196 ° C; lH NMR (300 MHz, CDCl 3 + MeOH-d 4) d (TMS) 8.10 (d, 7 = 8.1, 2H, arom), 7.78 (d, 7 = 8.1, 2H, arom). Analysis calculated for C 12 H 5 F 3 N 2 O 2 S: C 48.33; H 1.69; N 9.39; S 10.75. Found: C 48.36; H 1.88; N 9.08; S 9.97. REFERENCE EXAMPLE 29 2 - [(4-Chlorophenoxy) methyl] -4-methylthiazole-5-carboxylic acid (a) Following the methodology described in section a of reference example 19, 2 - [(4-chlorophenoxy) was obtained methyl] -4-methylthiazole-5-carboxylic acid methyl ester as a white solid: mp 88-89 ° C; ? NMR (300 MHz, CDCl 3) d (TMS) 7.25 (dt, /t/2.1, /d=8.9, 2H, arom), 6.90 (dt, /t/2.1, /d=8.9, 2H, arom), 5.27 (s, 2H, CH2O), 3.86 (s, 3H, OMe), 2.73 (s, 3H, Me-thiazole). Analysis calculated for C 13 H 12 CINO 3 S: C 52.4 * H 4.06; N 4.70; S 10.77. Found: C 51.09; H 4.03; N . 18; S 10.19. (b) Following the hydrolysis procedure described in section b of reference example 24, but leaving the reaction overnight, the title compound was obtained as a white solid: mp 233-234 ° C; ^ H NMR (300 MHz, CDCl 3 + MeOH-d) d (TMS) 7.21 (dt, /t2.2, / d = 9, 2H, arom), 6. 88 (dt, /t2.2, / d = 9, 2H, arom), 5.22 (s, 2H, CH20), 2.66 (s, 3H, Me-thiazole). Analysis calculated for C12H 10CINO3S: C 50.80; H 3.55; N 4.94; S 11.30. Found: C 51.13; H 3.57; N 4.97; S 11.12. REFERENCE EXAMPLE 30 2- [N- (4-Chlorophenyl) amino] -4-methylthiazole-5-carboxylic acid (a) Following the methodology described in section a of reference example 19, but using 4-chlorophenylthiourea, obtained methyl 2- [N- (4-chlorophenyl) amino] -4-methylthiazole-5-carboxylate as a white solid: mp 172-173 ° C; ? NMR (300 MHz, CDCl 3 + MeOH-d 4) d (TMS) 7.43 (dt, 7t = 2.3, /d=8.9, 2H, arom), 7.34 (dt, /t/2.3, / = 8.9, 2H, arom) , 4.07 (broad s, 1H, NH), 3.83 (s, 3H, OMe), 2.64 (s, 3H, Me-thiazole). Analysis calculated for C 12 H 11 CIN 2 O 2 S: C 50.98; H 3.92; N 9.91; S 11.34. Found: C 51.21; H 3.80; N 9.81; S 10.11. (b) Following the hydrolysis procedure described in section b of reference example 2 but heating to reflux overnight the title compound was obtained as a white solid: mp >; 250 ° C; * H NMR (300 MHz, CDCl 3 + MeOH-d 4) d (TMS) 7.40 (dt, / t = 2.1, / d = 9, 2 H, arom), 7.30 (dt, / d = 9, 2 H, arom), 2.58 (s, 3H, Me-thiazole). Analysis calculated for C 11 H 9 CIN 2 O 2 S: C 49.17; H 3.38; N, 10.42; S 11.93. Found: C 49.29; H 3.31; N 10.32; S 11.32. REFERENCE EXAMPLE 31 2- (4-Chlorophenyl) thiazole-4-carboxylic acid (a) A solution of ethyl bromopyruvate (354 mg, 1.8 mmol) and 4-chlorobenzothiamide (283 g, 1.65 mmol) in EtOH was heated to reflux. (40 mL) for 3 h. The mixture was concentrated to dryness and the resulting oil was purified by flash chromatography to give ethyl 2- (4-chlorophenyl) thiazole-4-carboxylate as a colorless oil: ^ NMR (80 MHz, CDCl 3) d (TMS) 8.15 (s, 1H, thiazole), 7.95 (dt, 7t = 2, / = 8.5, 2H, arom), 7.42 (dt, / t = 2, /d=8.5, 2H, arom), 4.45 ( q, / = 7, 2H, OCH2), 1.43 (t, / = 7, 3H, OCH2CH3). Analysis calculated for Ci2H? OClN? 2S: C 53.84; H 3.76; N 5.23; S 11.97. Found: C 53.65; H 3.77; N 5.23; S 11.51. (b) Following the hydrolysis procedure described in section b of reference example 2 but heating the solution overnight, the title compound was obtained as a white solid: mp 189-190 ° C; * H NMR (80 MHz, CDCl 3) d (TMS) 8.29 (s, 1H, thiazole), 7.93 (dt, / = 2, /d=8.5, 2H, arom), 7.45 (dt, / t = 2, / d = 8.5, 2H, arom). Analysis calculated for C10H6CINO2S: C 50.11 H 2.52; N 5.84; S 13.35. Found: C 50.21; H 2.45; N 5.79; S 13.21. REFERENCE EXAMPLE 32 2- (4-Trifluoromethylphenyl) thiazole-4-carboxylic acid (a) Following the methodology described in section a of reference example 31, ethyl 2- (4-trifluoromethylphenyl) thiazole-4-carboxylate was obtained in the form of white solid: mp 102-103 ° C; * H NMR (80 MHz, CDCI3) d (TMS) 8. 21 (s, 1H, thiazole), 8.15 (d, 7 = 8.3, 2H, arom), 7.71 (d, 7 = 8.3, 2H, arom), 4.47 (q, 7 = 7, 2H, OCH2), 1-44 (t, 7 = 7, 3H, OCH2C H3). Analysis calculated for C 13 H 10 F 3 NO 2 S: C 51.83; H 3.35; N 4.65; S 10.64. Found: C 51.91; H 3.34; N 4.61; S 10.29. (b) Following the hydrolysis procedure described in section b of reference example 31, the title compound was obtained as a white solid: mp 188-189 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 8.37 (s, 1H, thiazole), 8.13 (d, 7 = 8.5, 2H, arom), 7.73 (d, 7 = 8.5, 2H, arom). Analysis calculated for C 11 H 6 F 3 NO 2 S: C 48.36 H 2.21; N 5.13; S 11.73. Found: C 48.46; H 2.22; N 5.17; S 11.75. REFERENCE EXAMPLE 33 2-Phenylthiazole-4-carboxylic acid (a) Following the methodology described in section a of reference example 31, ethyl 2-phenylthiazole-4-carboxylate was obtained as a colorless oil: H NMR (80 MHz, CDCI3) d (TMS) 8.14 (s, 1H, thiazole), 8.1-7.8 (m, 2H, arom), 7.6-7.2 (m, 3H, ar.om), 4.45 (q, 7 = 7, 2H, OCH2), 1.42 (t, / = 7, 3H, OCH2CH3). (b) Following the hydrolysis procedure described in section b of reference example 31, the title compound was obtained as an amorphous white solid: * H NMR (80 MHz, CDCl 3) d (TMS) 8.27 (s, 1H, thiazole ), 82-7.8 (m, 2H, arom), 7.6-7.4 (m, 3H, arom). REFERENCE EXAMPLE 34 2- [4- (2,2,3,3-Tetrafluoropropoxy) phenyl] thiazole-4-carboxylic acid (a) Following the methodology described in section a of reference example 31, 2- [ Ethyl 4- (2,2,3,3-tetrafluoropropoxy) phenyl] thiazole-4-carboxylate as a colorless oil:] H NMR (80 MHz, CDCl 3) d (TMS) 8.11 (s, 1H, thiazole), 7.98 (dt, / t = 2, /d=8.8, 2H, arom), 6.98 (dt, / t = 2, / d = 8-8, 2H, arom), 6.06 (tt, /=4.6 = 53, 1 H, CHF), 4.41 (tt, 7 = 1.5, = 11.8, 2H, CH2), 4.35 (q, 7 = 7, 2H, OCH2), 1-42 (t, 7 = 7, 3H, OCH2CH3). (b) Following the hydrolysis procedure described in section b of reference example 31, the title compound was obtained as a white solid: mp 170-173 ° C; 'H NMR (80 MHz, CDCl 3) d (TMS) 8.95 (s, 1H, thiazole), 8.70 (dt, / t = 2, /d=8.8, 2H, arom), 7.75 (dt, / t = 2, /d = 8.8, 2H, arom), 6.79 (tt, 7 = 4.6, 7 = 53, 1H, CHF2), 5.16 (tt, 7 = 1.5, 7 = 11.8, 2H, CH2). REFERENCE EXAMPLE 35 5- (4-Cyanophenyl) thiophene-2-carboxylic acid (a) Following the procedure described in Hauptmann et al, Tetrahedron Lett. 1968, 1317, ethyl 5- (4-cyanophenyl) thiophene-2-carboxylate was obtained as a white solid: mp 133-134 ° C; ^ H NMR (300 MHz, CDCl 3) d (TMS) 7.83 (d, 7 = 4, 1H, thiophene), 7.81 (dt, / t = 1.6, / d = 8-3, 2H, arom), 7.70 (dt) , 7t = 1.6, 7d = 8.3, 2H, arom), 7.43 (d, / = 4, 1H, thiophene), 4.44 (q, 7 = 7, 2H, OCH2), 1-45 (t, / = 7, 3H, OCH2CH3). Analysis calculated for C? 4 HnN02S: C 65.35; H 4.31; N 5.44; S 12.46. Found: C 64.92; H 4.19; N 5.34; S 12.19. (b) Following the hydrolysis procedure described in section b of reference example 24, the title compound was obtained as a white solid: mp > 300 ° C; NMR (300 MHz, DMSO-d6) d (TMS) 7.99 (d, 7 = 8.3, 2H, arom), 7.87 (d, 7 = 8.3, 2H, arom), 7.74 (s, 2H, thiophene). REFERENCE EXAMPLE 36 5- (4-Chlorophenyl) -3-methylthiophen-2-carboxylic acid (a) To a cooled solution (-78 ° C) of 3- (4-chlorophenyl) -3-chloro-aromolephine (2.0 g, 10.4 mmol, obtained as described in Hauptmann et al, Tetrahedron Lett, 1968, 1317) in anhydrous THF (30 mL) was added dropwise a 3M solution in THF of methylmagnesium bromide (3.47 mL, 10.4 mmol). After the addition was complete, the reaction mixture was stirred at -78 ° C for 0.5 h. Then a saturated aqueous solution of NH 4 Cl was added and the mixture was concentrated. The resulting aqueous residue was extracted with CHCl3, dried, filtered, concentrated and purified by flash chromatography to give 4- (4-chlorophenyl) -4-chloro-3-buten-2-ol (1.54 g, 71% ) in the form of a colorless oil: * H NMR (300 MHz, CDCl 3) d (TMS) 7.51 (dt, /t/2.6, /d=8.6, 2H, arom), 7. 33 (dt, /t/2.6, /d=8.6, 2H, arom), 6.18 (d, /=7.5, 1H, = CH), 4.93 (quint, 7 = 6.4, 1H, CHOH), 1.39 (d, 7 = 6.4, 3H, CHCH3). . (b) CH2Cl2 (160 mL), pyridine (14 mL, 0.175 mol) and Cr3 (8.76 g, 87 mmol) were placed in a flask. The resulting reddish solution was cooled to 0 ° C, stirred for 0.5 h and a solution of 4- (4-chlorophenyl) -4-chloro-3-buten-2-ol (2.8 g, 14.6 mmol, obtained in the previous section) in CH2CI2 (20 mL) dropwise. The reaction mixture was stirred at room temperature for 4 h, filtered over celite, washed, concentrated and purified by flash chromatography to give 4- (4-chlorophenyl) -4-chloro-3-buten-2-one in the form of a colorless oil (1.3 g, 45%): * H NMR (300 MHz, CDCl 3) d (TMS) 7.61 (dt,? = 2-6, /d = 8.6, 2H, arom), 7.39 (dt, J { = 2.6, / = 8.6, 2H, arom), 6.75 (s, 1H, = CH), 2.47 (s, 3H, Me). (c) Following the procedure described in the literature (see reference example 35), the compound obtained in section (b) was reacted with the sodium salt of ethyl mercaptoacetate to give 5- (4-chlorophenyl) -3- ethyl methylthiophen-2-carboxylate in the form of an amorphous solid: ^ H NMR (300 MHz, CDCI3) d (TMS) 7.54 (dt,? = 2.5, / d = 9, 2H, arom), 7.37 (dt, = 2-5, / d = 9, 2H, arom), 7.11 (s, 1H , thiophene), 4.35 (q, 7 = 7, 2H, OCH2), 2.57 (s, 3H, Me -thiophene), 1.40 (t, J-7, 3H, OCH2CH3). (d) Following the hydrolysis procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 245-246 ° C; H NMR (300 MHz, MeOH-d) d (MeOH) 7.63 (dt, / t = 2, / d = 8.6, 2 H, arom), 7.39 (dt, / t = 2, / d = 8.6, 2 H, arom. ), 7.25 (s, 1H, thiophene), 2.52 (s, 3H, Me-thiophene). Analysis calculated for 2H9CIO2S: C 57.03; H 3.59; S 12.69. Found: C 56.94; H 3.20; S 12.39. REFERENCE EXAMPLE 37 5- (4-Cyanophenyl) -3-methylthiophen-2-carboxylic acid (a) Following the procedure described in reference example 36a, 4- (4-cyanophenyl) -4-chloro-3- was obtained buten-2-ol as a colorless oil:? H NMR (300 MHz, CDCl 3) d (TMS) 7.70 (dt, /t/2.1, /d=8.7, 2H, arom), 7.64 (dt, /t = 2.1, fd = 8.7, 2H, arom), 6.33 (d, 7 = 7.5, 1H, = CH), 4.95 (quint, 7 = 6.5, 1H, CHOH), 1.41 (d, 7 = 6.5, 3H , CHCH3). (b) Following the procedure described in reference example 36b, 4- (4-cyanophenyl) -4-chloro-3-buten-2-one was obtained as a colorless oil: H NMR (300 MHz, CDCl 3) d (TMS) 7.79 (dt, 7t = 2.2, /d=8.7, 2H, afom), 7.71 (dt, /t2.2, Jd = 8.7, 2H, arom), 6.79 (s, 1H, = CH), 2.49 (s, 3H, Me). (c) Following the procedure described in reference example 36c, ethyl 5- (4-cyanophenyl) -3-methylthiophen-2-carboxylate was obtained as a white solid: mp 129-130 ° C; ] H NMR (300 MHz, CDCl 3) d (TMS) 7.68 (s, 4 H, arom), 7.19 (s, 1 H, thiophene), 4.35 (q, 7 = 7, 2 H, OCH 2), 2.57 (s, 3 H, Me-thiophene), 1.39 (t, 7 = 7, 3H, OCH2C-Í3) - (d) Following the hydrolysis procedure described in section b of reference example 24, the title compound was obtained as a white solid: mp 248-253 ° C; * H NMR (300 MHz, CDCl 3) d (TMS) 7.68 (d, 7 = 9, 2H, arom), 7.66 (d, / = 9, ZH, arom), 7.20 (s, 1H, thiophene), 2.53 ( s, 3H, Me-thiophene). Analysis calculated for C 13 H 9 N O 2 S: C 64.18; H 3.73; N 5.76; S 13.18. Found: C 64.18; H 3.71; N 5.60; S 13.00. REFERENCE EXAMPLE 38 2- (4-Chlorophenyl) -5-methyl-3H-imidazole-4-carboxylic acid (a) A solution of ethyl 2-oximinoacetoacetate (6 g, 38 mmol, obtained according to Org. Synth. 21, 67) in MeCN (75 mL) was treated with 4-chlorobenzylamine (5.6 g, 40 mmol) at reflux for 18 h. Then, the reaction mixture was allowed to cool and the yellow solid formed was separated by filtration to give ethyl 2- (4-chlorophenyl) -5-methyl-3H-imidazole-4-carboxylate as a white solid (4.1 g, 40%): mp 237-238 ° C; TH NMR (300 MHz, DMSO-d6) d (DMSO) 7.96 (d, / = 8, 2H, arom), 7.57 (d, 7 = 8, 2H, arom), 4.27 (q, 7 = 7, 2H, OCH2), 2.54 (s, 3H, Me-imidazole), 1.33 (t, 7 = 7, 3H, OCH2CH3). Analysis calculated for C 13 H 13 CIN 2 O 2: C 58.99; H 4.95; N 10.58. Found: C 59.20; H 4.95; N 10.59. (b) Following the hydrolysis procedure described in section b of reference example 2, the title compound was obtained as a white solid:? NMR (300 MHz, DMSO-d6) d (DMSO) 7.98 (s broad), 7.50 (d, 7 = 8.5, 2H, arom), 2.49 (s, 3H, Me-imidazole). EXAMPLE OF REFERENCE 39 Mixture of 2- (4-chlorophenyl) -3,5-dimethyl-3H-imidazole-4-carboxylic acid and 2- (4-chlorophenyl) -l, 5-dimethyl-lH-imidazole-4-carboxylic acid A solution of ethyl 2- (4-chlorophenyl) -5-methyl-3H-imidazole-4-carboxylate (2.7 g, 10 mmol, obtained in reference example 38) in DMF (50 mL) was treated with K2CO3 ( 1.4 g, 10 mmol) and Mel (0.95 mL, 15.3 mmol) at 60 ° C for 2 h. The mixture was concentrated to dryness and the resulting residue was partitioned between AcOEt and water. The organic phase was separated, dried over Na 2 SO 4, filtered and concentrated to give a mixture ca. 1: 1 N -methylimidazole derivatives. This mixture was then hydrolyzed as described above to give a mixture of N-methylated acids in the imidazole ring. This mixture was used directly in the next step as obtained. REFERENCE EXAMPLE 40 5- (4-Chlorophenyl) -l, 3,4-oxadiazole-2-carboxylic acid (a) This product was prepared by a modification of the general method described in Dost, J. et al. J.Prakt. Chem.19S5, 327, 109. To a cooled (0 ° C) solution of 4-chlorobenzhydrazide (crude, 5 g, 29 mmol) and triethylamine (7.4 mL, 51 mmol) in CH 2 Cl 2 (100 mL) was added dropwise ethyl oxalyl chloride (4 g, 29 mmol) and the mixture was stirred for 3 h. Then a saturated solution of NaHC 3 (50 mL) and CHCl 3 was added. The organic phase was dried over Na 2 S? 4 anhydrous, filtered and concentrated to give ethyl 4-chlorobenzoylhydrazinooxalate as a colorless oil which was purified by flash chromatography to give 1.1 g of a white solid. This compound was dissolved in POCI3 (30 mL) and heated at 100 ° C for 15 h. The reaction crude was concentrated to dryness and partitioned between a 10% aqueous solution of NaHC 3 and CHCl 3. The organic phase was decanted, dried over anhydrous Na 2 SO 4, filtered and concentrated. The residue was purified by flash chromatography to give ethyl 5- (4-chlorophenyl) -l, 3,4-oxadiazole-2-carboxylate as a white solid (450 mg): mp 117-118 ° C; "? NMR (300 MHz, CDC13) d (TMS) 8.11 (dt, /t/2.3, /d=8.6, 2H, arom), 7.54 (dt, /t/2.3, /d=8.6, 2H, arom) 4.56 (q, 7 = 7.1, 2H, OCH2), 1.49 (t, 7 = 7.1, 3H, OCH2CH3) Analysis calculated for C11H9CIN2O3: C 52.29; H 3.59; N 11.09 Found: C 52.70; H 3.42; N 10.89 (b) Following the hydrolysis procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 277-284 ° C; * H NMR (300 MHz, MeOH-d4) d (MeOH) 7.87 (d, / = 8.5, 2H, arom), 7.51 (d, 7 = 8.5, 2H, arom.) REFERENCE EXAMPLE 41 3- (4-Chlorophenyl) -l, 2,4-oxadiazole- 5-carboxylic acid (a) This compound was prepared by a modification of the general method described in Diana et al., J. Med.Chem, 1995, 38, 1355. A mixture of 4-chlorobenzonitrile (5 g, 36.34 mmol), EtOH ( 90 mL), hydroxylamine hydrochloride (2.52 g, 36.34 mmol) and K2CO3 (2.51 g, 18.17 mmol) was heated to reflux for 20 h. The reaction mixture was concentrated, cold water was added, filtered and dried to give 4-chlorobenzoamidoxime as a white solid (3.5 g, 56%). Then, this product (1.7 g, 10 mmol) was dissolved in pyridine (34 mL) and treated with ethyl oxalyl chloride (2.22 mL, 20 mmol) at 0 ° C. The reaction mixture was stirred for 1 h, poured into phosphate buffer pH 7, concentrated and partitioned between CHCl3 and water. The organic phase was washed with an aqueous solution of 10% NaHCO3, dried over Na2SO4, filtered, concentrated and purified by flash chromatography to give 3- (4-chlorophenyl) -l, 2.4- Oxadiazole-5-carboxylic acid ethyl ester in amorphous solid form (2.14 g, 85%): 1 H NMR (300 MHz, CDCl 3) d (TMS) 8.18 (dt, /t2.2, /d=8.6, 2H, arom), 7.56 (dt, /t2.2, /d=8.6, 2H, arom), 4.66 (q, 7 = 7.1, 2H, OCH2), 1.57 (t, 7 = 7.1, 3H, OCH2CH3). (b) This product was subjected to the hydrolysis procedure described in Reference Example 24 for 1 h to give the title compound as a white solid contaminated with some decarboxylation product: mp 43-44 ° C; * H NMR (300 MHz, CDCl 3 + MeOH-c U) d (TMS) 7.63 (d, 7 = 9, 2 H, arom), 7.50 (d, J = 9, 2 H, arom). REFERENCE EXAMPLE 42 5- (4-Chlorophenyl) -l, 2,4-oxadiazole-3-carboxylic acid (a) This compound was prepared by a modification of the general method described in Shimizu, T. et al. Bull.Chem.Soc.Jpn. 1985, 58, 2519. A mixture of 4-chlorobenzonitrile (1.7 g, 12.2 mmol), and diethyl nitromalonate (2.5 g, 12.2 mmol) in dodecane (20 mL) was heated at 150 ° C for 15 h. After the reaction was complete, the mixture was allowed to cool to room temperature and was concentrated by vacuum distillation. The residue was purified by flash chromatography to give ethyl 5- (4-chlorophenyl) -l, 2,4-oxadiazole-3-carboxylate as a light brown solid: mp 88-89 ° C; ] H NMR (300 MHz, CDC13) d (TMS) 8.15 (dt, 7t = 2.3, /d=8.7, 2H, arom), 7.54 (dt, /t/2.3, Jd = 8.7, 2H, arom), 4.55 (q, 7 = 7.1, 2H, OCH2), 1.47 (t, 7 = 7.1, 3H, OCH2CH3). (b) Following the hydrolysis procedure described in section b of reference example 2, the title compound was obtained as a white solid, contaminated with some decarboxylation product:] H NMR (300 MHz, CDCl 3 + MeOH-d) d (TMS) 8.11 (d, 7 = 9, 2H, arom), 7.51 (d, / = 9, 2H, arom). REFERENCE EXAMPLE 43 2- (4-Rert-butylphenyl) -4-methylthiazole-5-carboxylic acid (a) Following the methodology described in section a of reference example 19, 2- (4-ér-butylphenyl) was obtained. Methyl 4-methylthiazole-5-carboxylate as a colorless oil:] H NMR (300 MHz, CDCl 3) d (TMS) 7.89 (dt, /t2.2, /d=8.6, 2H, arom), 7.46 ( dt, /t/2.2, /d=8.6, 2H, arom), 3.89 (s, 3H, OMe), 2.78 (s, 3H, Me-thiazole), 1.35 (s, 9H, CMe3). (b) Following the hydrolysis procedure described in section b of reference example 2, the title compound was obtained as a white solid: mp 190-193 ° C; l H NMR (300 MHz, MeOH-d 4) d (MeOH) 7.89 (dt, /t2.2, /d=8.6, 2H, arom), 7.53 (dt, /t2.2, /d=8.6, 2H, arom. ), 2.72 (s, 3H, Me-thiazole), 1.36 (s, 9H, CMe3). Analysis calculated for C? 5Hi7N02S: C 65.43; H 6.22; N 5.09; S 11.64. Found: C 65.41; H 6.22; N 4.92; S 10.84. EXAMPLE 1 (l_R, 2_R) -l- (4-Chlorophenyl) -r- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -lH-pyrazole-4-carboxamide On a solution of (2R, 3R) -3-amino-2- (2,4-difluorophenyl) -l- (lH-1, 2,4-triazole -l-yl) -2-butanol (340 mg, 1.26 mmol, obtained as described in 7. Org. Chem., 199 5, 60, 3000-3012) in DMF (6 mL) was added 1-hydroxybenzotriazole (207 mg, 1.32 mmol). Subsequently, 1- (4-chlorophenyl) -lH-pyrazole-4-carboxylic acid (280 mg, 1.26 mmol, obtained in reference example 1) and DCC (272 mg, 1.32 mmol) were added and the mixture was stirred at room temperature. environment for 18 h. Then, the reaction mixture was cooled to 0 ° C and the dicyclohexylurea formed was filtered, washed with CHCl 3 and the remaining solution was concentrated to dryness and partitioned between a 10% aqueous solution of NaHCO 3 and CHCl 3. The phases were separated and the organic phase was dried over Na 2 SO 4, filtered and concentrated. The residue was purified by flash chromatography (hex: AcOEt 1: 1 then 1: 3) to give the title product, which was recrystallized from AcOEt: ether: hexane to give a white solid (560 mg, 94%): mp 212- 213 ° C; W NMR (80 MHz, CDCl 3) d (TMS) 8.39 (s, 1H, pyrazole), 8.02 (s, 1H, pyrazole), 7.9-7.2 (m, 7H, arom), 7.0-6.6 (m, 2H, arom. ), 6.43 (d wide, 7 = 9, 1H, NH), 5.35 (d, 7 = 1.3, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m) , 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 1.02 (d, 7 = 7, 3H, MeCH); [α] D = -106.3 ° (c 1, CHCl 3). Analysis calculated for C 22 H 19 ClF 2 N 6 O 2: C 55.88; H 4.05; N, 17.77. Found: C 55.96; H 4.06; N 17.55. EXAMPLE 2 (lR, 2_R) -l- (4-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (li-1, 2,4-triazole- 1-yl) propyl] -5-methyl-1H-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but using l- (4-chlorophenyl) -5-methyl-1H-pyrazole-4- carboxylic acid (reference example 2) the title compound was obtained as a white solid: mp 154-155 ° C; W NMR (80 MHz, CDCl 3) d (TMS) 7.90 (s, 1H, triazole), 7.79 (s, 2H, triazole, pyrazole), 7.6-7.2 (m, 5H, arom), 7.0-6.6 (m, 2H , arom), 6.37 (broad d, 7 = 9, 1H, NH), 5.35 (d, 7 = 1.3, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, / = 14.5, 1H, TrCH (H)), 2.61 (s, 3H, Me-pyrazole), 1.02 (d, 7 = 7, 3H, MeCH); [a] D = -91.4 ° (c 1, CHCl 3). Analysis calculated for C 23 H 2iClF 2 N 6 • 2: C 56.74; H 4.35; N 17.26. Found: C 56.79; H 4.62; N 17.15. EXAMPLE 3 (lR, 2_R) -l- (4-Chlorophenyl) -? V- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole -l-yl) propyl] -5-trifluoromethyl-lH-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but using l- (4-chlorophenyl) -5-trifluoromethyl-lH-pyrazole-4 -carboxylic compound was obtained as a white solid: mp 138-139 ° C; 1 NMR (80 MHz, CDCl 3) d (TMS) 7.98 (s, 1 H, triazole), 7.79 (s, 2 H, triazole, pyrazole), 7.6-7.2 (m, 5H, arom), 7.0-6.6 (m, 2H, arom), 6.48 (broad d, / = 9, 1H, NH), 5.31 (d, / = 1.3, 1H, OH), 5.05 (d, 7 = 14.5, 1 H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, / = 14.5, 1 H, TrCH (H)), 1.02 (d, 7 = 7, 3H, MeCH); [α] D = -103.6 ° (c 1, CHCl 3). Analysis calculated for C23H18CIF5N6O2: C 51.07; H 3.35; N 15.54. Found: C 50.66; H 3.41; N 15.39. EXAMPLE 4 (lR, 2_R) -l- (4-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- l-yl) propyl] -5-propyl-lH-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but using l- (4-chlorophenyl) -5-propyl-lH-pyrazole-4- The title compound was obtained as an amorphous solid: NMR (80 MHz, CDCl 3) d (TMS) 7.88 (s, 1H, triazole), 7.79 (s, 2H, triazole, pyrazole), 7.6-7.2 (m, 5H, arom), 7.0-6.6 (m, 2H, arom), 6.38 (broad d, / = 9, 1H, NH), 5.35 (d, 7 = 1.3, 1H, OH), 5.05 (d, 7 = 14.5 , 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 3.2-2.8 (m, 2H, Pr), 1.7-1.5 (m, 2H, Pr), 1.02 (d, / = 7, 3H, MeCH), 0.87 (t, 3H, Pr); [α] D = -79.5 ° (c 1, CHCl 3). Analysis calculated for C 25 H 25 ClF 2 N 6 O 2: C 58.31; H 4.89; N 16.32. Found: C 58.14; H 5.14; N 16.36. EXAMPLE 5 (lR, 2_R) -l- (4-Chlorophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -5-isopropyl-1H-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but using l- (4-chlorophenyl) -5-isopropyl-1H-pyrazole-4-acid carboxylic acid (reference example 3) the title compound was obtained as an amorphous solid: mp 85-92 ° C; NMR (80 MHz, CDCl 3) d (TMS) 7.83 (s, 1H, pyrazole), 7.79 (s, 2H, triazole), 7 6-7.2 (m, 5H, arom), 7.0-6.6 (m, 2H, arom. ), 6.41 (broad d, 7 = 10, 1H, NH), 5.32 (d, 7 = 1.3, 1H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m , 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 3.4-3.1 (m, 1H, CHMe2), 1-38 (d, 7 = 7, 6H, CHMe2), 1.02 ( d, 7 = 7, 3H, MeCH); [α] D = -82.5 ° (c 1, CHCl 3). Analysis calculated for C 25 H 2 IF2N6O2.I / 2H2O: C 57.30; H 5.00; N 16.04. Found: C 57.04; H 5.27; N 15.7.3. EXAMPLE 6 (lJR, 2K) -5-FerfButyl-1 - ('' -chlorophenyl) -IV- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2 , 4-triazol-l-yl)? Ropil] -lH-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but using the acid? -eributil-1 - (4-chlorophenyl) -l H-pyrazole 4-carboxylic acid (reference example 4) the title compound was obtained as a white solid: mp 191-192 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 7.80 (s, 2 H, triazole), 7.68 (s, 1 H, pyrazole), 7.6-7.2 (m, 5 H, arom), 7.0-6.6 (m, 2 H, arom. ), 6.45 (broad d, 7 = 10, 1H, NH), 5.31 (d, 7 = 1.3, 1 H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 1.31 (s, 9H, í-Bu), 1.02 (d, 7 = 7, 3H, MeCH); [α] D = -92.0 ° (c 1, CHCl 3). Analysis calculated for C 26 H 27 Cl 1 F 2 N 602: C 59.03; H 5.14; N 15.89. Found: C 59.36; H 5.66; N 15.87. EXAMPLE 7 (1R, 2) -5-Cyclopropyl-1- (4-chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2, 4-triazol-1-yl) propyl] -lH-pyrazole-4-carboxamide Following a procedure similar to that described in Example 1 but using 5-cyclopropyl-1- (4-chlorophenyl) -lH-pyrazole-4-acid carboxylic acid (reference example 5) the title compound was obtained as a white solid: mp 181-182 ° C; ? NMR (80 MHz, CDCl 3) d (TMS) 8.06 (s, 1H, pyrazole), 7.79 (s, 2H, triazole), 7.49 (s, 4H, arom), 7.6-7.2 (m, 1H, arom), 7.0 -6.6 (m, 3H, arom, NH), 5.33 (d, 7 = 1.3, 1H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe ), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 2.2-1.8 (m, 1H, c-prop), 1.3-1.0 (m, 2H, c-Pr), 1.04 (d, 7 = 7, 3H, MeCH), 0.8-0.5 (m, 2H, c-pr); [α] D = -112.6 ° (c 1, CHCl 3). Analysis calculated for C25H23CIF2N6O2: C 58.54; H 4.52; N 16.38. Found: C 58.90; H 4.87; N 16.27. EXAMPLE 8 (lR, 2_R) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (l-l, 2,4-triazol-l-yl) propyl] -5 methyl-l- (4-trifluoromethylphenyl) -l-H-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but using 5-methyl-1- (4-trifluoromethylphenyl) -lH-pyrazole-4-acid carboxylic (Reference example 6) the title compound was obtained as a white solid: mp 180-181 ° C; "? NMR (80 MHz, CDCl 3) d (TMS) 8.02 (s, 1H), 7.9-7.2 (m, arom), 7.0-6.6 (m, 2H, arom), 6.37 (broad d, 7 = 10, 1H , NH), 5.37 (d, 7 = 1.3, 1H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 2.69 (s, 3H, Me-pyrazole), 1.04 (d, 7 = 7, 3H, MeCH); [a] D = -90.8 ° (c 1, CHCI3). Analysis calculated for C 24 H 21 F 5 N 6 O 2: C 55.39; H 4.07; N 16.15. Found: C 55.57; H 4.27; N 16.01. EXAMPLE 9 (lK, 2_R) -l- (4-Bromophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -5-methyl-1H-pyrazole-4-carboxamide Following a procedure similar to that described in Example 1 but using l- (4-bromophenyl) -5-methyl-1H-pyrazole-4-acid carboxylic acid (reference example 7) the title compound was obtained as a white solid: mp 153-154 ° C; H NMR (300 MHz, CDCl 3)? (TMS) 7.91 (s, 1H, pyrazole), 7.81 (s, 1H, triazole), 7.80 (s, 1H, triazole), 7.66 (d, 7 = 8.7, 2H, arom), 7.4 (dt, / d = 6.5, /t = 8.8, 1H, arom), 7.32 (d, 7 = 8.7, 2H, arom), 6.8-6.6 (m, 2H, arom), 6.35 (broad d, 7 = 9.5, 1H, NH), 5.36 (d, 7 = 1.3, 1H, OH), 5.05 (d, 7 = 14.5, 1 H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.53 (d, 7 = 14.5, 1H , TrCH (H)), 2.63 (s, 3H, Me-pyrazole), 1.03 (d, 7 = 6.8, 3H, MeCH); MS 306 and 308 (ethylaminoacyl group, Ci3Hi3BrN'3?), 263 and 265 (acyl group, C?? H8BrN20), 224 (Tr-CH2COHAr, C? Or H8F2N3?); [α] D = -86.8 ° (c 1, CHCl 3). Analysis calculated for C23H2iBrF2N6? 2: C 51.99; H 3.98; N 15.82. Found: C 52.10; H 4.01; N 15.76.

EXAMPLE 10 (LR, 2R) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] -5 -trifluoromethyl-1- (4-trifluoromethylphenyl) -Lyphirazole-4-carboxamide Following a procedure similar to that described in example 1 but using 5-trifluoromethyl-1- (4-trifluoromethylphenyl) -lH-pyrazole-4-acid carboxylic acid (reference example 8) the title compound was obtained as a white solid: mp 141-143 ° C; * H NMR (80 MHz, CDC13) d (TMS) 8.02 (s, 1H), 7.9-7.2 (m, arom), 7.0-6.4 (m, 3H, arom, NH), 5.31 (d, 7 = 1- 3, 1H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 1.02 (d, 7 = 7, 3H, MeCH); [a] D = -86.3 ° (c 1, CHCl3). Analysis calculated for C24H? 8F8N6? 2: C 50.18; H 3.16; N 14.63. Found: C 49.75; H 3.20; N 14.45. EXAMPLE 11 (ljR, 2K) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl-1- (2,4-difluorophenyl) -5-methyl-1H-pyrazole-4-carboxamide Following a procedure similar to that described in Example 1 but using l- (2,4-difluorophenyl) -5-methyl-1H-pyrazole 4-carboxylic acid the title compound was obtained as a white solid: mp 208-209 ° C; ^ H NMR (80 MHz, CDCl 3) d (TMS) 7.93 (s, 1H, triazole), 7.78 (s, 2H, triazole, pyrazole), 7.6-7.0 (m, 3H, arom), 7.0-6.6 (m, 3H, arom), 6.35 (broad d, 7 = 9, 1H, NH), 5.34 (d, 7 = 1.3, 1 H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 5.1 -4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1 H, TrCH (H)), 2.49 (s, 3H, Me-pyrazole), 1.02 (d, 7 = 7, 3H, MeCH); [α] D = -89.6 ° (c 1, CHCl 3). Analysis calculated for C 23 H 20 F 4 N 6 O 2: C 56.56; H 4.13; N 17.21. Found: C 56.88; H 4.36; N, 16.83. EXAMPLE 12 (1α, 2K) -l- (3,5-Dichlorophenyl) -V- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2, 4-triazol-1-yl) propyl] -5-methyl-1H-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but using l- (3,5-dichlorophenyl) -5-methyl- The H-pyrazole-4-carboxylic acid (Reference example 9) gave the title compound as a white solid: mp 220-221 ° C; TH NMR (300 MHz, CDCl 3) d (TMS) 7.92 (s, 1H, pyrazole), 7. 81 (s, 1 H, triazole), 7.80 (s, 1 H, triazole), 7.5-7.3 (m, 4H, arom), 6.8-6.6 (m, 2H, arom), 6.36 (broad d, 7 = 9.5 , 1 H, NH), 5.36 (d, 7 = 1.3, 1H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 4.96 (fifth width, 7 = 7, 1 H, CHMe) , 4.53 (d, 7 = 14.5, 1H, TrCH (H)), 2.68 (s, 3H, Me-pyrazole), 1.03 (d, 7 = 6.8, 3H, MeCH); MS 296 and 298 (ethylaminoacyl group, C 13 H 12 Cl 2 N 3 O), 253 and 255 (acyl group, C 11 H 7 Cl 2 N 2 O), 224 (Tr-CH 2 COHAr, C 10 H 8 F 2 N 3 O); [α] D = -83.1 ° (c 1, CHCl 3). Analysis calculated for 23H20 I2F2N6O2: C 52.99; H 3.87; N 16.12. Found: C 53.58; H 4.08; N 15.90. EXAMPLE 13 (lE, 2R) -l- (2,6-Dichlorophenyl) -JV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1,2,4- triazol-1-yl) propyl] -5-methyl-L-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but Using the l- (2,6-dichlorophenyl) -5-methyl-1H-pyrazole-4-carboxylic acid (reference example 10) the title compound was obtained: mp 226-227 ° C; H NMR (300 MHz, CDC13) or (TMS) 8.03 (s, 1H, pyrazole), 7.81 (s, 2H, triazole), 7.6-7.3 (m, 4H, arom), 6.8-6.6 (m, 2H, arom. ), 6.42 (d wide, 7 = 9.5, 1H, NH), 5.38 (d, 7 = 1.3, 1H, OH), 5.07 (d, 7 = 14.5, 1 H, TrCH (H)), 4.97 (fifth width) , 7 = 7, 1H, CHMe), 4.57 (d, 7 = 14.5, 1H, TrCH (H)), 2.44 (s, 3H, Me-pyrazole), 1.04 (d, 7 = 6.8, 3H, MeCH); MS 296 and 298 (ethylaminoacyl group, C13H12CI2N3O), 253 and 255 (acyl group, C11H7Cl2N2O), 224 (Tr-CH2COHAr, C? Or H8F2N3?); [α] D = -80.3 ° (c 1, CHCl 3). Analysis calculated for C 23 H 20 Cl 2 F 2 N O 2: C 52.99; H 3.87; N 16.12. Found: C 53.29; H 3.91; N 15.93. EXAMPLE 14 (R, 2_R) -l- (2-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -5-methyl-1H-pyrazole-4-carboxamide Following a procedure similar to that described in Example 1 but using l- (2-chlorophenyl) -5-methyl-1H-pyrazole-4-acid carboxylic acid (reference example 11) the title compound was obtained as a white solid: mp 232-233 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 7.97 (s, 1H, pyrazole), 7.81 (s, 2H, triazole), 7.6-7.3 (m, 5H, arom), 6.8-6.6 (m, 2H, arom), 6.39 (d wide, /=9.5, 1H, NH), 5.38 (d, 7 = 1.5, 1 H, OH), 5.07 (d, 7 = 14.4, 1H, TrCH (H)), 4.97 (quint width, 7 = 7, 1H, CHMe), 4.57 (d, 7 = 14.4, 1 H, TrCH (H)), 2.48 (s, 3H, Me-pyrazole), 1.05 (d, 7 = 6.8, 3H, MeCH); [a = -85.2 ° (c 1, CHCl3). Analysis calculated for C 23 H 21 ClF 2 N 6 O 2: C 56.74; H 4.35; N 17.26. Found: C 56.87; H 4.56; N 17.03. EXAMPLE 15 (l_R, 2_R) -l- (4-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (li-1, 2,4-triazole- 1-yl) propyl] -3,5-dimethyl-1H-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but using l- (4-chlorophenyl) -3,5-dimethyl-1 H -pyrazole-4-carboxylic acid (reference example 12) the title compound was obtained: mp 144-145 ° C; * H NMR (80 MHz, CDCl 3) d (TMS) 7,978 (s, 2H, triazole), 7.6-7.2 (m, 5H, arom), 7.0-6.6 (m, 2H, arom), 6.28 (broad d, 7 = 10, 1H, NH), 5.35 (d, 7 = 1.3, 1H, OH), 5.07 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 ( d, 7 = 14.5, 1 H, TrCH (H)), 2.56 (s, 3H, Me-pyrazole), 2.54 (s, 3H, Me-pyrazole), 1.02 (d, 7 = 7, 3H, MeCH); [α] D = -93.9 ° (c 1, CHCl 3). Analysis calculated for C 24 H 23 ClF 2 N 6 O 2: C 57.55; H 4.63; N, 16.78. Found: C 57.91; H 4.80; N 16.53. EXAMPLE 16 (lR, 2R) -5-Amino-l- (4-chlorophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (L-1, 2, 4-triazol-1-yl) propyl] -lH-pyrazole-4-carboxamide Following a procedure similar to that described in Example 1 but using 5-amino-1- (4-chlorophenyl) -lH-pyrazole-4-acid carboxylic acid (reference example 13) the title compound was obtained as a white solid: mp 181-182 ° C; l NMR (80 MHz, CDCl 3) d (TMS) 7.78 (s, 2H, triazole), 7.69 (s, 1H, pyrazole), 7.50 (broad s, 4H, arom), 7.6-7.2 (m, 1H, arom) , 7.0-6.6 (m, 2H, arom), 6.15 (broad d, 7 = 9, 1H, NH), 5.55 (broad s, 2H, NH2), 5.36 (s, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 1.02 (d, 7 = 7, 3H, MeCH); [α] D = -86.7 ° (c 1, CHCl 3). Analysis calculated for C22H20CIF2N7O2: C 54.16; H 4.13; N 20.10. Found: C 54.28; H 4.35; N 19.76. EXAMPLE 17 (l_R, 2K) -5-Amino-iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] -l- (4-trifluoromethylphenyl) -lH-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but using 5-amino-1- (4-trifluoromethylphenyl) -lH-pyrazole-4-acid carboxyl (reference example 14) the title compound was obtained as a white solid: mp 208-210 ° C; ^ H NMR (80 MHz, CDCl 3) d (TMS) 7.76 (m, 7H, triazole, arom, pyrazole), 7.6-7.3 (m, 1H, arom), 7.0-6.6 (m, 2H, arom), 6.18 ( d wide, / = 9, 1H, NH), 5.6 (broad s, 2H, NH2), 5.37 (s, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 1.02 (d, / = 7, 3H, MeCH); [a] D = -69.6 ° (c 1, CHC1; ¡). Analysis calculated for C23H20F5N7 2.2H2O: C 49.55; H 4.34; N 17.59. Found: C 49.33; H 3.99; N 17.58. EXAMPLE 18 (l_R, 2_R) - / V- [2- (2,4-Diflu-D-phenyl) -2-hydroxy-l-methyl-3- (LH-1, 2,4-triazol-1-yl) propyl] - 5-methyl-1- (3-trifluoromethylphenyl) -Lyphirazole-4-carboxamide Following a procedure similar to that described in example 1 but using 5-rnethyl-1- (3-trifluoromethylphenyl) -lH-pyrazole-4 acid -carboxylic (reference example 15) the title compound was obtained as a white solid: mp 146-147 ° C; ] H NMR (300 MHz, CDCl 3) d (TMS) 7.95 (s, 1H, pyrazole), 7.82 (s, 2H, triazole), 7.6-7.5 (m, 4H, arom), 7.40 (dt, / d = 6.5 , /t = 8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.41 (broad d, 7 = 9.5, 1H, NH), 5.37 (d, 7 = 1.3, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 4.96 (fifth width, 7 = 7, 1H, CHMe), 4.53 (d, 7 = 14.5, 1H, TrCH (H)), 2.67 (s, 3H , Me-pyrazole), 1.03 (d, 7 = 6.8, 3H, MeCH); MS 296 (ethylaminoacyl group, C14H13F3N3O), 253 (acyl group, Ci2HsF3N2?), 224 (Tr-CH2COHAr, C10H8F2N3O); [a = -90.5 ° (c 1, CHCl3). Analysis calculated for C 24 H 21 F 5 N 6 O 2: C 55.39; H 4.07; N 16.15. Found: C 55.33; H 3.97; N 16.12. EXAMPLE 19 (LR, 2R) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl-5- methyl-l- (4-trifluoromethoxy-phenyl) -lH-pyrazole-4-carboxamide Following a procedure similar to that described in example 1 but using 5-methyl-1- (4-trifluoromethoxyphenyl) -lH-pyrazole-4-carboxylic acid (Reference example 16) the title compound was obtained as a white solid: mp 134-135 ° C; "? NMR (300 MHz, CDCl 3) d (TMS) 7.93 (s, 1H, pyrazole), 7,815 (s, 1H, triazole), 7,810 (s, 1H, triazole), 7.6-7.3 (m, 5H, arom) , 6.8-6.6 (m, 2H, arom), 6.38 (broad d, 7 = 9.5, 1H, NH), 5.37 (d, /=1.3, 1H, OH), 5.07 (d, /=14.5, 1H, TRCH (H)), 4.97 (fifth width, J = 7, 1H, CHMe), 4.54 (d, 7 = 14.5, 1H, TrCH (H)), 2.65 (s, 3H, M e-pyrazole), 1.04 (d , 7 = 6.8, 3H, M eCH); MS 312 (ethylaminoacyl group, C14H13F3N3O2), 269 (acyl group, 2H8F3N2O2), 224 (Tr- CH2COHAr, C10H8F2N3O); [a] D = -83.1 ° (c 1, CHCI3 Analysis calculated for 24H21F5N6O3: C 53.73, H 3.95, N 15.67, Found: C 53.99, H 3.94, N 15.46, EXAMPLE 20 (LR, 2_R) -N- [2- (2,4-Difluorophenyl) -2- hydroxy-l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] -5-methyl-l- (4-methoxyphenyl) -lH-pyrazole-4-carboxamide Following a procedure similar to described in example 1 but using 5-methyl-1- (4-methoxyphenyl) -lH-pyrazole-4-carboxylic acid (reference example 17) the title compound was obtained: mp 176-177 ° C; H NMR ( 300 MHz, CDCI3) d (TMS) 7.89 (s, 1H, pyrazole), 7.81 (s, 2H, triazole), 7.41 (dt, 7d = 6.5, /t8.8, 1H, arom), 7.33 (dt, /t2.5, /d6.6, 2H, arom) , 7.02 (dt, /t = 2.5, 7d = 6.6, 2H, arom), 6.8-6.6 (m, 2H, arom), 6.35 (broad d, 7 = 9.5, 1H, NH), 5.37 (d, 7 = 1.3, 1H, OH), 5.07 (d , 7 = 14.5, 1H, TrCH (H)), 4.97 (fifth width, 7 = 7, 1H, CHMe), 4.55 (d, 7 = 14.5, 1 H, TrCH (H)), 3.88 (s, 3H, OMe), 2.59 (s, 3H, Me-pyrazole), 1.04 (d, 7 = 6.8, 3H, M and CH); MS 258 (ethylaminoacyl group, C? 4H? 6N 3? 2), 215 (acyl group, Ci 2 H p N? 2). 224 (Tr-CH C OHA r, C 10 H 8 F 2 N 3 O); [α] D = -90.3 ° (c 1, CHCl 3). Analysis calculated for C 24 H 24 F 2 N 6 O 3: C 59.75; H 5.01; N 17.42. Found: C 59.88; H 4.91; N 17.30. EXAMPLE 21 (l_R, 2_R) -l- (4-Chlorophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (LH-1, 2,4-triazole- 1-yl) propyl] pyrrole-3-carboxamide Following a procedure similar to that described in example 1 but using l- (4-chlorophenyl) pyrrole-3-carboxylic acid (prepared as described in Fabis et al, Org. Prep. Int. Procedure 1995, 27, 236) the title compound was obtained as an amorphous solid: H NMR (80 MHz, CDCl 3) d (TMS) 7.79 (s, 2 H, triazole), 7.63 (t, / = 2, 1H, pyrrole), 7.6-7.3 (m, 5H, arom), 7.02 (t, / = 2, 1H, pyrrole), 7.0-6.6 (m, 2H, arom), 6.63 (t, / = 2, 1H, pyrrole), 6.35 (broad d, 1H, NH), 5.36 (d, / = 1.3, 1H, OH), 5.06 (d, 7 = 14.5, 1 H, TrCH (H)), 5.1-4.8 (m , 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 1.03 (d, / = 7, 3H, MeCH); [a] D = -95.2 ° (c 1, CHCl 3). Analysis calculated for C23H20CIF2N5O2: C 58.54; H 4.27; N 14.84. Found: C 58.42; H 4.26; N 14.65. EXAMPLE 22 (lR, 2_R) -2- (4-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] thiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-chlorophenyl) thiazole-5-carboxylic acid (reference example 18) the title compound was obtained as a white solid: mp 194-195 ° C; TH NMR (300 MHz, CDCl 3) d (TMS) 8.25 (s, 1H, thiazole), 7.93 (dt, / t = 2, / d = 9, 2H, arom), 7.81 (s, 1 H, triazole), 7.79 (s, 1H, triazole), 7.45 (dt, / t = 2, / d = 9, 2H, arom), 7.39 (dt, 7d = 6.5, /t=8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.55 (broad d, 7 = 9.3, 1H, NH), 5.40 (d, 7 = 1.6, 1H, OH), 5.03 (d, 7 = 14.5, 1H, TrCH (H)) , 4.95 (fifth width, 7 = 7, 1H, CHMe), 4.52 (d, 7 = 14.5, 1H, TrCH (H)), 1.04 (d, 7 = 6.8, 3H, MeCH); HPLC-MS 265 and 267 (ethylaminoacyl group, C12H10CIN2OS), 222 (acyl group, C10H5CINOS), 224 (Tr-CH2COHAr, C10H8F2N3O); [α] D = -105.6 ° (c 1, CHCl 3). Analysis calculated for C22H18CIF2N5O2S: C 53.94; H 3.70; N 14.29; S 6.54. Found: C 54.04; H 3.78; N 14.16; S 6.12. EXAMPLE 23 (LR, 2R) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] - 2-phenyl-4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2-phenyl-4-methylthiazole-5-carboxylic acid (reference example) 19) the title compound was obtained as an amorphous solid: H NMR (300 MHz, CDCl 3) d (TMS) 8.0-7.9 (m, 2H, arom), 7.81 (s, 1 H, triazole), 7.79 (s, 1H, triazole), 7.5-7.4 (m, 3H, arom), 7.38 (dt, 7 = 6.5, /t8.8, 1H, arom), 6.9-6.7 (m, 2H, arom), 6.40 (broad d , 7 = 9.5, 1H, NH), 5.38 (d, 7 = 1.3, 1H, OH), 5.05 (d, 7 = 14.2, 1H, TrCH (H)), 4.93 (fifth width, 7 = 7, 1H, CHMe), 4.53 (d, 7 = 14.2, 1 H, TrCH (H)), 2.82 (s, 3H, Me-thiazole), 1.03 (d, 7 = 6.8, 3H, MeCH); [α] D = -114.2 ° (c 1, CHCl 3). Analysis calculated for C23H2i F2N5? 2S: C 58.84; H 4.51; N 14.92; S 6.83. Found: C 58.59; H 4.78; N 15.02; S 6.50. EXAMPLE 24 (LR, 2) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] -4 -methyl-2- (4-trifluoromethylphenyl) thiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 4-methyl-2- (4-trifluoromethylphenyl) thiazole-5-carboxylic acid and recrystallizing the product obtained in DMF-H2O, the title compound was obtained as a white solid: mp 79-82 ° C; H NMR (80 MHz, CDCl 3) d (TMS) 8.1 (s, 1H, triazole), 8.03 (s, 1H, triazole), 7.78 (broad s, arom), 7.66 (s, arom), 7.6-7.2 (1H , arom), 7.0-6.6 (m, 2H, arom), 6.4 (broad d, 7 = 9, 1H, NH), 5.38 (d, 7 = 1.3, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 2.82 (s, 3H, Me-thiazole), 1.02 (d, 7 = 7, 3H, MeCH); [a] D = -103.2 ° (c 1, CHCl 3). Analysis calculated for C 24 H 20 F 5 N 5 O 2 S: C 53.63; H 3.75; N 13.03; S 5.96. Found: C 53.77; H 3.97; N 13.51; S 5.51. EXAMPLE 25 (lR, 2K) -2- (4-Chlorophenyl) -? V- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole -l-yl) propyl] -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-chlorophenyl) -4-methylthiazole-5-carboxylic acid (reference example 20) the title compound was obtained as a white solid: mp 159-160 ° C; ^ H NMR (80 MHz, CDCl 3) d (TMS) 8.0-7.8 (m, 4H, arom, triazole), 7.6-7.2 (m, 3H, arom), 7.0-6.6 (m, 2H, arom), 6.4 ( d wide, 7 = 10, 1H, NH), 5.37 (d, 7 = 1.3, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1 H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 2.80 (s, 3H, Me-thiazole), 1.02 (d, 7 = 7, 3H, MeCH); MS 281 and 283 (ethylaminoacyl group, C1 3 H 14C 1N 20S), 236 and 238 (acyl group, C 11 H 7 CINOS), 224 (Tr-CH 2 COHAr, C 10 H 8 F 2 3 O); [α] D = -117.1 ° (c 1, CHCl 3). Analysis calculated for C 23 H 20 ClF 2 N 5 O 2 S: C 54.82; H 4.00; N 13.90; S 6.36.

Found: C 55.13; H 3.93; 13.86; S 6.09. EXAMPLE 26 (l_R, 2K) -2- (4-Brom phenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4- triazol-1-yl) propyl] -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-bromophenyl) -4-methylthiazole-5-carboxylic acid (reference example 21 ) the title compound was obtained as a white solid: mp 165-166 ° C; ] H NMR (80 MHz, CDCl 3) d (TMS) 7.71 (d, 7 = 7.5, 2H, arom), 7.79 (s, 2H, triazole), 7.57 (d, 7 = 7.5, 2H, arom), 7.6- 7.2 (m, 1 H, arom), 7.0-6.6 (m, 2H, arom), 6.43 (broad d, 7 = 10, 1H, NH), 5.39 (d, 7 = 1.3, 1H, OH), 5.05 ( d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1 H, TrCH (H)), 2.80 (s, 3H, Me- thiazole), 1.02 (d, 7 = 7, 3H, M eCH); MS 323 and 325 (ethylaminoacyl group, C? 3Hi2BrN2OS), 280 and 282 (acyl group, CpH BrNOS), 224 (Tr-CH2COHAr, C? Or H 8F2N3?); [α] D = -108.7 ° (c 1, CHCl 3). Analysis calculated for C23H2? BrF2N5? 2S: C 50.37; H 3.68; N 12.77; S 5.85. Found: C 50.61; H 3.66; N 12.81; S 5.62. EXAMPLE 27 (.lR, 2_R) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (L-1, 2,4-triazol-1-yl) propyl] - 4-methyl-2- (4-trifluoromethoxyphenyl) thiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 4-methyl-2- (4-trifluoromethoxyphenyl) thiazole-5-carboxylic acid (reference example) 22) the title compound was obtained as an amorphous solid:? NMR (30C MHz, CDCl 3) d (TMS) 8.01 (dt, / t = 2, / d = 9, 2H, arom), 7.83 (s, 1H, triazole), 7.81 (s, 1H, triazole), 7.39 ( dt, / d = 6.5, /t = 8.8, 1H, arom), 7.32 (d, 7 = 9, 2H, arom), 6.8-6.6 (m, 2H, arom), 6.44 (broad d, 7 = 9.5 , 1H, NH), 5.40 (d, 7 = 1.3, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 4.95 (fifth width, 7 = 7, 1H, CHMe), 4.53 (d, 7 = 14.5, 1H, TrCH (H)), 2.83 (s, 3H, Me-thiazole), 1.04 (d, 7 = 6.8, 3H, MeCH); MS 329 (ethylaminoacyl group, C14H12F3N2O2S), 286 (acyl group, C12H7F3NO2S), 224 (Tr-CH2COHAr, C? 0H8F2N3O); [a] D = -105.4 ° (c 1, CHCl 3). Analysis calculated for C 24 H 20 F 5 N 5 O 3 S: C 52.08; H 3.64; N, 12.65; S 5.79. Found: C 52.27; H 3.88; N, 12.26; S 5.40. EXAMPLE 28 (lJ?, 2K) -N- [2- (2,4-Diflaorophenyl) -2-hydroxy-l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] - 4-methyl-2- [4- (2,2,3,3-tetrafluoropropoxy) phenyl] thiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 4-methyl-2- [4- (2,2,3,3-tetrafluoropropoxy) phenyl] thiazole-5-carboxylic acid (reference example 23) the title compound was obtained as an amorphous solid:] H NMR (300 MHz, CDCl 3) d (TMS) 7.95 ( dt, 7t = 2, 7d = 9, 2H, arom), 7.82 (s, 1 H, triazole), 7.80 (s, 1 H, triazole), 7.39 (dt, / d = 6.5, /t=8.8, 1H , arom), 7.02 (dt, / t = 2, 7d-9, 2H, arom), 6.8-6.6 (m, 2H, arom), 6.41 (broad d, 7 = 9.5, 1H, NH), 6.08 (tt , 7 = 4.7, 7 = 53, 1 H, CF2H), 5.39 (d, 7 = 1 -3, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 4.95 (quint wide) , 7 = 7, 1H, CHMe), 4.53 (d, 7 = 14.5, 1H, TrCH (H)), 4. 35 (tt, 7 = 1.3, 7 = 12, 2H, OCH2), 2.81 (s, 3H, Me-thiazole), 1.03 (d, 7 = 6.8, 3H, MeCH); MS 375 (ethylaminoacyl group, CI OH 15F4N 2O 2S), 332 (acyl group, C? 4H10F4N? 2S), 224 (Tr-CH2COHAr, C? 0H8F2N3O); [a] = -85.7 ° (c 1, CHCl3). Analysis calculated for C20H23F6. 5O3S: C 52.09; H 3.87; N 11.68; S 5.35. Found: C 52.23; H 3.60; N 11.62: S 5.24. EXAMPLE 29 (LR, 2_R) -2- (4-Cyanophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -4-methylthiazole-5-carboxamide Following a similar procedure to that described in example 1 but using 2- (4-cyanophenyl) -4-methylthiazole-5-carboxylic acid (reference example 24) obtained the title compound as a white solid: mp 109-111 ° C; ? NMR (300 MHz, CDC13) d (TMS) 8.07 (d, 7 = 8.3, 2H, arom), 7.81 (s, 1H, triazole), 7.79 (s, 1H, triazole), 7.75 (d, 7 = 8.3, 2H, arom), 7.37 (dt, / d = 6.5, 7t = 8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.46 (broad d, 7 = 9.5, 1H, NH), 5.40 ( s, 1H, OH), 5.03 (d, 7 = 14.5, 1H, TrCH (H)), 4.94 (fifth width, 7 = 7, 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H )), 2.83 (s, 3H, Me-thiazole), 1.02 (d, 7 = 6.8, 3H, MeCH); MS 270 (ethylaminoacyl group, C14H12N3OS), 227 (acyl group, C12H7N2OS), 224 (Tr-CH2COHAr, C10H8F2N3O); [α] D = -120.8 ° (c 1, CHCl 3). Analysis calculated for C 24 H 20 F 2 N 6 O 2 S: C 58.29; H 4.08; N, 16.99; S 6.48 Found: C 57.83; H 3.96; N 16.70; S 6.16. EXAMPLE 30 (lK, 2_R) -2- (4-Cyanophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -4-methylthiazole-5-carboxamide, oxalate To a solution of (lR, 2R) -2- (4-cyanophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy -l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] -4-methylthiazole-5-carboxamide (obtained in Example 29) in EtOH 2 equivalents of oxalic acid were added and of diethyl ether. The solution was cooled to -20 ° C and the obtained precipitate was filtered and dried to give the title compound as a white solid: mp 104-108 ° C; H NMR (300 MHz, MeOH-d4) d (TMS) 8.28 (s, 1H, triazole), 8.14 (d, 7 = 8.3, 2H, arom), 8.1-7.9 (m, 1H), 7.84 (d, 7) = 8.3, 2H, arom), 7.73 (s, 1H, triazole), 7.37 (dt, / d = 6.5, /t=8.8, 1H, arom), 7.0-6.9 (m, 1H, arom), (6.9- 6.8 (m, 1H, arom), 5.1-4.9 (m, 2H, TrCH (H), CHMe), 4.59 (d, 7 = 14.5, 1H, TrCH (H)), 2. 73 (s, 3H, Me-thiazole), 1.05 (d, 7 = 6.8, 3H, MeCH); [α] D = -72 ° (c 1, MeOH). Analysis calculated for C 24 H 20 F 2 N 6 O 2 S.C 2 H 4 O 2. I / 2 H 2 O: C 52.61; H 3.90; N 14.16; S 5.39. Found: C 52.74; H 3.80; N 13.88; S 5.01. EXAMPLE 31 (lR, 2_R) -2- (4-Cyanophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (l-l, 2,4-triazole- 1-yl) propyl] -4-methylthiazole-5-carboxamide, methanesulfonate To a solution of (1R, 2R) -2- (4-cyanophenyl) -N- [2- (2,4-difluorophenyl) -2- hydroxy-l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] -4-methylthiazole-5-carboxamide (obtained in Example 29) in MeOH were added 2 equivalents of diluted methanesulfonic acid in MeOH. The solution was cooled to 0 ° C and the formed precipitate was filtered and dried to give the title compound in the form of white needles: mp 126-138 ° C; * H NMR (300 MHz, DMSO-d6) d (DMSO) 8.55 (s, 1H, triazole), 8.15 (d, / = 9.2, 1 H, NH), 8.13 (d, 7 = 8.3, 2H, arom) , 7.98 (d, 7 = 8.3, 2H, arom), 7.87 (s, 1H, triazole), 7.30 (broad q, 7 = 8.5, 1H, arom), 7.20 (ddd, 7 = 2.4, 7 = 9.2, 7 = 11.8, 1H, arom), 6.92 (dt, / d = 2.4, /t = 8.5, 1H, arom), 4.9-4.8 (m, 2H, TrCH (H), CHMe), 4.54 (d, 7 = 14.5 , 1H, TrCH (H)), 2.68 (s, 3H, Me-thiazole), 2.38 (s, 3H, MeS03H), 0.93 (d, 7 = 6.8, 3H, MeCH); [a] D = -71 ° (c 1, DMF). Analysis calculated for C 24 H 20 F 2 N 6 O 2 S. CH 4 O 3 S.H 2 O: C 49.34; H 4.31; N 13.81; S 10.53. Found: C 49.35; H 4.11; N 13.72; S 10.30. EXAMPLE 32 (LR, 2R) -2- (4-Carbamoylphenyl) -V- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -4-methylthiazole-5-carboxamide To a solution of NH 4 OH in a mixture of H 2 O-THF was added (1R, 2R) -2- (4-cyanophenyl) -V- (2- (2 , 4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] -4-methylthiazole-5-carboxamide methanesulfonate (0.5 g, 0.84 mmol, obtained in Example 31.) The mixture was heated to reflux for 2 days, concentrated and the aqueous residue was extracted with CHCl 3, the organic phase was decanted, dried over Na 2 SO 4, filtered and the filtrate was concentrated to a solid. (0.0.53 g) This was purified by flash chromatography to give the title compound as a white solid: 133-135 ° C; l NMR (300 MHz, CDCl 3) d (TMS) 7.98 (d, 7 = 8.3, 2H , arom), 7.87 (d, 7 = 8.3, 2H, arom), 7.81 (s, 1H, triazole), 7.71 (s, 1H, triazole), 7.40 (dt, 7d = 6.5, /t=8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.57 (broad d, 7 = 9.5, 1H, NH), 6.27 (broad s, 2H, NH2), 5.63 (s, 1H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 4.98 (fifth width, 7 = 7, 1H, CHMe), 4.57 (d, 7 = 14.5, 1H, TrCH (H)), 2.81 (s, 3H, Me-thiazole), 1.05 (d, 7 = 6.8, 3H, MeCH); MS 288 and 289 (ethylaminoacyl group, Ci4H and 5 3? 2S), 245 (acyl group, C12H9N2O2S), 224 (Tr-CH2COHAr, C? Or H8F2N30); [α] D = -74.5 ° (c 1, MeOH). Analysis calculated for C 24 H 22 F 2 N 6 O 3 S: C 56.24; H 4.33; N 16.40; S 6.26. Found: C 55.90; H 4.64; N 15.29; S 5.62. EXAMPLE 33 (1 R, 2K) -2- [2- (4-Chlorophenyl) -4-methylthiazol-5-yl] -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3 - (lH-l, 2,4-triazol-l-yl) propyl] -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2- [2- (4-chlorophenyl)] -4-methylthiazol-5-yl] -4-methylthiazole-5-carboxylic acid (reference example 25) the title compound was obtained as a yellow solid: mp 110-114 ° C; * H NMR (300 MHz, CDCl 3) d (TMS) 7.92 (dt, 7t = 2, / d = 9, 2H, arom), 7.81 (s, 1H, tpazol), 7.79 (s, 1H, triazole), 7.39 (dt, 7d = 6.5, 7t = 8.8, 1H, arom), 7.32 (dt, 7t = 2, 7d = 9, 2H, arom), 6.8-6.6 (m, 2H, arom), 6.42 (broad d, 7 = 9.5, 1H, NH), 5.40 (d, 7 = 1.1, 1 H, OH), 5.05 (d, 7 = 14.3, 1H, TrCH (H)), 4.95 (fifth width, 7 = 7, 1H, CHMe ), 4.52 (d, 7 = 14.3, 1H, TrCH (H)), 2.80 (s, 3H, Me-thiazole), 2.78 (s, 3H, Me-thiazole), 1.03 (d, 7 = 6.8, 3H, MeCH); HPLC-MS 376 and 378 (ethylaminoacyl group, C17H 15C I N 3O S 2), 333 and 335 (acyl group, C15H10CIN2OS2), 224 (Tr-CH2COHAr, C? 0H8F2N3O); [a] D = -98 ° (c 1, CHCl 3). Analysis calculated for C27H23C1F2N602S2: C 53.95; H 3.86; N 13.98; S 10.67. Found: C 54.21; H 4.02; N 13.60; S 9.78. EXAMPLE 34 (l_R, 2K) -2- (4-Chlorophenyl) -? V- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (li-l, 2,4-triazole -l-yl) propyl] -4-trifluoromethylthiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-chlorophenyl) -4-trifluoromethylthiazole-5-carboxylic acid (reference example 26) , the title compound was obtained as a white solid: mp 78-79 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 7.91 (dt, / t = 2.5, / d = 8.5, 2 H, arom), 7.81 (s, 1 H, triazole), 7.79 (s, 1 H, triazole), 7.48. (dt, / d = 2.5, /t = 8.5, 2H, arom), 7.39 (dt, 7d = 6.5, /t = 8.8, 1H, arom), 6.87 (broad d, /=9.0, 1H, NH), 6.8-6.6 (m, 2H, arom), 5.38 (broad s, 1H, OH), 5.01 (d, 7 = 14.2, 1H, TrCH (H)), 4.91 (fifth width, 7 = 7, 1H, CHMe), 4.51 ( d, 7 = 14.2, 1H, TrCH (H)), 1.02 (d, 7 = 6.8, 3H, MeCH); [a] D = -88.8 ° (c 1, CHCl 3). Analysis calculated for C23H17CIF5N5O2S: C 49.51; H 3.07; N, 12.55; S 5.75. Found: C 49.86; H 3.08; N, 12.36; S 5.38. EXAMPLE 35 (LR, 2K) - - [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] -4- trifluoromethyl-2- (4-trifluoromethylphenyl) thiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 4-trifluoromethyl-2- (4-trifluoromethylphenyl) thiazole-5-carboxylic acid (reference example 27) , the title compound was obtained as a white solid: mp 83-86 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 8.12 (d, 7 = 8.1, 2 H, arom), 7.84 (s, 1 H, triazole), 7.80 (s, 1 H, triazole), 7.77 (d, 7 = 8.1 , 2H, arom), 7.38 (dt, / d = 6.5, /t = 8.8, 1H, arom), 6.95 (broad d, 7 = 9.0, 1H, NH), 6.8-6.6 (m, 2H, arom) , 5.42 (d, 7 = 1.6, 1H, OH), 5.03 (d, 7 = 14.2, 1H, TrCH (H)), 4.96 (fifth width, 7 = 7, 1H, CHMe), 4.51 (d, 7 = 14.2, 1H, TrCH (H)), 1.04 (d, 7 = 6.8, 3H, MeCH); [α] D = -79 ° (c 1, CHCl 3). Analysis calculated for C 24 H 17 F 8 N 5 2 2 S: C 48.74; H 2.90; N 11.84; S 5.42. Found: C 49.16; H 3.19; N 11.47; S 5.03. EXAMPLE 36 (LR, 2) -2- (4-Cyanophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -4-trifluoromethylthiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-cyanophenyl) -4-trifluoromethylthiazole-5-carboxylic acid (reference example 28), the title compound was obtained as a white solid: mp 101-108 ° C; * H NMR (300 MHz, CDC13) d (TMS) 8.13 (d, 7 = 8.1, 2H, arom) 7.86 (s, 1H, triazole), 7.83 (d, 7 = 8.1, 2H, arom), 7.83 (s) , 1H, triazole), 7.40 Cdt, 1H, arom), 6.98 (broad d, 7 = 9.0, 1H, NH), 6.8-6.6 (m, 2H, arom), 5.44 (d, 7 = 1.6, 1H, OH ), 5.05 (d, 7 = 14.2, 1H, TrCH (H)), 4.96 (fifth width, 7 = 7, 1H, CHMe), 4.55 (d, 7 = 14.2, 1H, TrCH (H)), 1.07 ( d, 7 = 6.8, 3H, MeCH); [α] D = -79.9 ° (c 1, CHCl 3). Analysis calculated for C 24 H 17 F 5 N 6 O 2 S: C 52.56; H 3.12; N 15.32; S 5.85. Found: C 51.98; H 3.51; N 11.29; S 5.16. EXAMPLE 37 (l_R, 2i?) - iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] -2- [4 - (lH-tetrazol-5-yl) phenyl] -4-trifluoromethylthiazole-5-carboxamide, hydrochloride The compound obtained in the previous example (400 mg, 0.73 mmol) was treated with sodium azide (143 mg, 2.18 mmol) and hydrochloride of triethylammonium (151 mg, 1.09 mmol) in NMP (5 mL) at 150 ° C for 2 h. The mixture was cooled to room temperature, H2O was added and acidified with 6N HCl. A creamy solid ("50 mg) was obtained, which was recrystallized from isopropanol to give the title compound as a creamy solid: mp >; 250 ° C; ] H NMR (300 MHz, MeOH-d 4) d (MeOH-d) 9.32 (s, 1 H, triazole), 8.39 (s, 1 H, triazole), 8.28 (d, 7 = 8-8, 2 H, arom), 8.24 (d, 7 = 8.8, 2H, arom), 7.36 (dt, / d = 6.5, /t = 8.8, 1H, arom), 7. 06 (ddd, 7 = 2.4, 7 = 8.7, 7 = 11.5, 1H, arom), 6.90 (dt, / d = 2.1, /t=8.0, 1H, arom), 5.13 (d, 7 = 14.3, 1H, TrCH (H)), 5.01 (q, 7 = 7, 1H, CHMe), 4.77 (d, 7 = 14-3, 1H, TrCH (H)), 1.10 (d, 7 = 7, 3H, MeCH); DIP / MS 367 (ethylaminoacyl group, C? 4H10F3N6OS), 324 (acyl group, C12H5F3N5OS), 224 (Tr-CH2COHAr, Q0H8F2 3O). Analysis calculated for C24H 13F5N9O2S. HCl. H2O: C 44.62; H 3.28; N 19.51; S 4.96.

Found: C 44.12; H 2.89; N 19.01; S 4.71. EXAMPLE 38 (lK, 2_R) -iV- [2- (2,4-Diflumphenyl) -2-hydroxy-l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] - 2- [4- (2-methyl-2H-tetrazol-5-yl) phenyl] -4-trifluoromethylthiazole-5-carboxamide The compound obtained in the previous example (162 mg, 0.27 mmol) was treated with methyl iodide (48). mg, 0.34 mmol) and K2CO3 (38 mg, 0.28 mmmol) in DMF (2 mL) at 25 ° C for 2 h. The reaction mixture was concentrated to dryness, and the residue was partitioned between H2O and CHCl3. The organic phase was decanted, dried and concentrated. The residue was subjected to flash chromatography to give mainly the title compound (38 mg) as a white solid: H NMR (300 MHz, CDCl 3) d (TMS) 8.29 (d, 7 = 8.3, 2H, arom), 8.13 (d, 7 = 8.3, 2H, arom), 7.84 (s, 1H, triazole), 7.81 (s, 1H, triazole), 7.39 (dt, 7d = 6.5,? = 8.8, 1H, arom), 6.91 (d width, 7 = 9.0, 1H, NH), 6.8-6.6 (m, 2H, arom), 5.41 (d, 7 = 1.6, 1H, OH), 5.05 (d, 7 = 14.2, 1H, TrCH (H)) , 4.94 (quint width, 7 = 7, 1H, CHMe), 4.55 (d, 7 = 14.2, 1 ?, TrC? (H)), 4.45 (s, 3? / Vfe-tetrazole), 1.05 (d, 7 = 6.8, 3H,? ECH); DIP / MS 381 (ethylaminoacyl group, C15H12F3N6OS), 338 (acyl group, C13H7F3N5OS), 224 (Tr-CH2COHAr, C10H8F2N3O). EXAMPLE 39 (l_R ^ _R) -2 - [(4-Chlorophenoxy) methyl] -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1-yl, 2,4 -triazol-1-yl) propyl] -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2 - [(4-chlorophenoxy) methyl] -4-methylthiazole-5-carboxylic acid ( reference example 29) the title compound was obtained as a white solid: mp 134-135 ° C; * H NMR (300 MHz, CDCl 3) d (TMS) 7.80 (s, 1H, triazole), 7.77 (s, 1H, triazole), 7.36 (dt, / d = 6.5, / = 8.8, 1H, arom), 7.28 (dt, / t = 2, / d = 9, 2H, arom), 6.93 (dt, / t = 2, / d = 9, 2H, arom), 6.8-6.6 (m, 2H, arom), 6.35 ( d wide, 7 = 9.5, 1H, NH), 5.34 (d, 7 = 1.3, 1H, OH), 5.30 (s, 2H, CH20), 5.02 (d, 7 = 14-3, 1H, TrCH (H)), 4.91 (quint wide, / = 7, 1H, CHMe), 4.48 (d, 7 = 14.3, 1H, TrCH (H)), 2.76 (s, 3H, Me-thiazole), 0.99 (d, 7 = 6.8, 3H, MeCH); GC / MS 309 and 310 (ethylaminoacyl group, C14H14CIN2O2S), 266 and 268 (acyl group, C12H9CINO2S), 224 (Tr-CH2COHAr, C10H8F2N3O); [ap = -94 ° (c 1, CHCl3). Analysis calculated for C 24 H 22 ClF 2 N 5 O 3 S: C 53.98; H 4.15; N 13.12; S 6.00 Found: C 54.04; H 4.48; N, 12.35; S 5.27. EXAMPLE 40 (lR, 2R) -2- [N- (4-Chlorophenyl) amino] -IV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2 , 4-triazol-1-yl) propyl] -4-methylthiazole-5-carboxamide Following a similar procedure to that described in Example 1 but using 2- [N- (4-chlorophenyl) amino] -4-methylthiazole- 5-carboxylic acid (reference example 30) the title compound was obtained as an amorphous white solid: HPLC-MS 295 and 267 (ethylaminoacyl group, C13H14CIN3OS), 251 and 253 (acyl group, CnH8ClN2OS), 224 (Tr-CH2COHAr, C? 0H8F2N3O). EXAMPLE 41 (l_R, 2-R) -2- (4-Chlorophenoxy) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (l-l, 2,4- triazol-1-yl) propyl] -4-methylthiazole-5-carboxamide (a) Following a procedure similar to that described in example 1 but using 2-bromo-4-methylthiazole-5-carboxylic acid (obtained as indicated in Singh, JMJ Med.Chem., 1969, 12, 1553), (lR, 2R) -2-bromo-N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- ( lH-1, 2,4-triazol-1-yl) propyl] -4-methylthiazole-5-carboxamide as a white solid: mp 155-163 ° C; TH NMR (300 MHz, CDC13) d (TMS) 7.81 (s, 1H, triazole), 7.78 (s, 1H, triazole), 7.35 (dt, 7 = 6.5, 7t = 8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.36 (broad d, 7 = 9.5, 1H, NH), 5.4 (broad s, 1H, OH), 5.00 (d, 7 = 14.2, 1H, TrCH (H)), 4.90 ( quint wide, 7 = 7, 1H, CHMe), 4.46 (d, 7 = 14.2, 1H, TrCH (H)), 2.74 (s, 3H, Me-thiazole), 0.99 (d, 7 = 6.8, 3H, MeCH ); [a] D = -97.8 ° (c 1, CHCl 3). Analysis calculated for Ci7H? 6BrF N5? 2S: C 43.23; H 3.41; N 14.83: S 6.79. Found: C 43.23; H 3.64; N 14.58; S 6.29. (b) To a solution of the product obtained in section (a) (375 mg, 0.79 mmol) in N-methylpyrrolidone (5 mL) was added 4-chlorophenol (117 mg, 0.91 mmol) and anhydrous K2CO3 (109 mg, 0.79). mmol). The mixture was stirred at 130 ° C for 18 h and after that time water and AcOEt were added. The organic phase was decanted and the aqueous residue was extracted with AcOEt. The combined organic phases were dried over Na 2 SO 4, concentrated and purified by flash chromatography to give the title compound as an amorphous solid (159 mg): H NMR (300 MHz, CDCl 3) d (TMS) 7.80 (s, 1H, triazole), 7.77 (s, 1H, triazole), 7.41 (d, 7 = 9, 2H, arom), 7.36 (dt, / d = 6.5, /t8.8, 1H, arom), 7.25 (d, 7 = 9, 2H, arom), 6.8-6.6 (m, 2H, arom), 6.20 (broad d, 7 = 9.5, 1H, NH), 5.33 (d, 7 = 1.5, 1H, OH), 5.00 (d, 7 = 14.2, 1H, TrCH (H)), 4.91 (fifth width, 7 = 7, 1H, CHMe), 4.46 (d, 7 = 14.2, 1H, TrCH (H)), 2.62 (s, 3H, Me-thiazole), 0.98 (d, 7 = 6.8, 3H, MeCH); GC-MS 295 and 297 (ethylaminoacyl group, C13H12CIN2O2S), 252 and 254 (acyl group, Cp H7ClN02S), 224 (Tr-CH COHAr, C? 0H8F2N3?); [a] D = -93 ° (c 1, CHCl 3). EXAMPLE 42 (lR, 2R) -2- (4-Chlorobenzenesulfonyl) - - [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole-1 -yl) propyl] -4-methylthiazole-5-carboxamide Following the procedure described in example 41 but using the sodium salt of 4-chlorobenzenesulfinic acid (obtained as indicated in Org.Synth.C0ll.V0l IV, 674, from of 4-chlorobenzenesulfonylchloride and sodium sulfite) in place of the mixture of 4-chlorophenol and 2CO3, the title compound was obtained as an amorphous white solid: H NMR (300 MHz, CDCl 3) d (TMS) 8.04 (dt, / t = 1.9, /d=8.7, 2H, arom), 7.81 (s, 1H, triazole), 7.76 (s, 1H, triazole), 7.56 (dt, / t = 1.9, /d=8.7, 2H, arom) , 7.34 (dt, / d = 6.5, /t = 8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.20 (broad d, 7 = 9.5, 1H, NH), 5.41 (d, 7 = 1.5, 1H, OH), 4.97 (d, 7 = 14.2, 1H, TrCH (H)), 4.86 (fifth width, 7 = 7, 1 H, CHMe), 4.42 (d, 7 = 14.2, 1H, TRCH (H)), 2.74 (s, 3H, Me-thiazole), 0.99 (d, 7 = 6.8, 3H, MeCH); GC-MS 343 and 345 (ethylaminoacyl group, Ci3HpClN2? 3S2), 300 and 302 (acyl group, C11H7CINO3S2), 224 (Tr-CH2COHAr, C? Or H8F2N3?). EXAMPLE 43 (l_R, 2_R) -5- (4-aorophenyl) -N- (2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (LH-1, 2,4-triazole- 1-yl) propyl-2-methyl-furan-3-carboxamide Following a procedure similar to that described in example 1 but using 5- (4-chlorophenyl) -2-methyl-furan-3-carboxylic acid, the title compound was obtained in the form of white solid: mp 189-190 ° C; TH NMR (300 MHz, CDCl 3) d (TMS) 7.80 (s, 1H, triazole), 7.79 (s, 1H, triazole), 7.59 (dt, 7t = 2, / d = 8.4, 2H, arom), 7.39 (dt, / d = 6.5, /t = 8.8, 1H, arom), 7.37 (dt, / t = 2, / d = 8-4, 2H, arom), 6.8- 6.6 (m, 2H, arom), 6.27 (s, 1H, furan), 6.29 (broad d, 7 = 9.5, 1H, NH), 5.35 (s, 1H, OH), 5.04 (d, 7 = 14.2, 1H , TrCH (H)), 4.93 (quint width, 7 = 7, 1H, CHMe), 4.51 (d, 7 = 14.2, 1H, TrCH (H)), 2.71 (s, 3H, Me-furan), 1.01 ( d, 7 = 6.8, 3H, MeCH); HPLC-MS 262 and 264 (ethylaminoacyl group, C? 4H? 3ClN? 2), 219 and 221 (acyl group, Ci2H8C102), 224 (Tr-CH2COHAr, C10H8F2N3O); a] D = -131.2 ° (c 1, CHCl 3) Analysis calculated for C 24 H 21 ClF 2 N 4 O 3: C 59.20, H 4.35, N 11.51.

Found: C 59.22; H 4.34; N 11.58. EXAMPLE 44 (l_R, 2_R) -5- (4-aorofenu) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-l, 2/4-triazole- 1-yl) propyl] -2-trifluoromethylfuran-3-carboxamide Following a procedure similar to that described in example 1 but using 5- (4-chlorophenyl) -2-trifluoromethyl-furan-3-carboxylic acid, the title compound was obtained in the form of amorphous white solid:] H NMR (300 MHz, CDCl 3) d (TMS) 7.81 (s, 1 H, triazole), 7.78 (s, 1 H, triazole), 7.66 (dt, / t = 2, 7d = 8.4, 2H , arom), 7.43 (dt, / t = 2, /d=8.4, 2H, arom), 7.36 (dt, / d = 6.5, /t=8.8, 1H, arom), 6.98 (s, 1H, furan) , 6.8-6.6 (m, 2H, arom), 6.60 (broad d, 7 = 9.3, 1 H, NH), . 34 (s, 1H, OH), 5.03 (d, 7 = 14.2, 1 H, TRCH (H)), 4.93 (fifth width, 7 = 7, 1H, CHMe), 4.50 (d, 7 = 14.2, 1H, TrCH (H)), 1.00 (d, 7 = 6.8, 3H, MeCH); GC / MS 316 and 318 (ethylaminoacyl group, C14H 10CIF3NO2), 273 and 275 (acyl group, C12H5CIF3O2), 224 (Tr-CH2COHAr, C10H8F2N3O); [a] D = -84.6 ° (c 1, CHCl 3). Analysis calculated for C24H? SClF5N4? 3: C 53.30; H 3.35; N 10.36. Found: C 53.12; H 3.82; N 10.36. EXAMPLE 45 (l_R, 2) -2- (4-Chlorophenyl) -V- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -4-methyloxazole-5-carboxamide A solution of N- (4-chlorobenzoyl) -alanine (1.46 g, 6.41 mmol) in benzene (35 mL) was treated with oxalyl chloride (0.55 mL, 6.41 mmol) at 45 ° C for 3 h. Then a solution of (2R, 3R) -3-amino-2- (2,4-difluorophenyl) -l- (lH-1, 2,4-triazol-1-yl) -2-butanol ( 1.72 g, 6.41 mmol) and triethylamine (2.2 mL) in CHCl2 (20 mL) and the reaction mixture was stirred at 0 ° C for 0.5 h. The reaction crude was added to cold water and extracted with CHCl3. The organic solution was dried over Na 2 SO 4, filtered and the filtrate was concentrated in vacuo to give a mixture of several substances (TLC) from which the title compound was isolated as a white solid by flash chromatography (140 mg): mp 89-93 ° C; * H NMR (300 MHz, CDCl 3) d (TMS) 8.04 (d, 7 = 8.5, 2H, arom), 7.79 (s, 1H, triazole), 7.78 (s, 1H, triazole), 7.49 (d, 7 = 8.5, 2H, arom), 7.37 (dt, / = 6.5, /t = 8.8, 1H, arom), 6.8-6.6 (m, 3H, arom, NH), 5.38 (d, 7 = 1.1, 1H, OH) , 5.04 (d, 7 = 14.3, 1H, TrCH (H)), 4.96 (fifth width, 7 = 7, 1H, CHMe), 4.53 (d, 7 = 14.3, 1H, TrCH (H)), 2.60 (s) , 3H, Me-oxazole), 1.04 (d, 7 = 6.8, 3H, MeCH); HPLC-MS 263 and 265 (ethylaminoacyl group, Ci3Hi2Cl t2? 2), 220 and 222 (acyl group, CpHtClN02), 224 (Tr-CH2COHAr, C10H8F2N3O); [a] D = -141 ° (c 0.5, CHCI3). Analysis calculated for C 23 H 20 ClF 2 N 5 O 3: C 56.62; H 4.13; N 14.35. Found: C 56.41; H 4.19; N 14.50. EXAMPLE 46 (l?, 2R) -2- (4-Chlorophenyl) - - [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (l-l, 2,4-triazole- 1-yl) propyl] thiazole-4-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-chlorophenyl) thiazole-4-carboxylic acid (reference example 31) the title compound was obtained as a white solid: mp 201-204 ° C; * H NMR (80 MHz, CDCl 3) d (TMS) 8.15 (s, 1H, thiazole), 8.0-7.7 (m, 4H, triazole, arom), 7.6-7.2 (3H, arom), 7.0-6.6 (m, 2H, arom), 5.33 (d, 7 = 1.3, 1 H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.5 (d, 7 = 14.5, 1H, TrCH (H)), 1.07 (d, 7 = 7, 3H, MeCH); [α] D = -130.7 ° (c 1, CHCl 3). Analysis calculated for C22H18CIF2N5O2S: C 53.94; H 3.70; N 14.29; S 6.54. Found: C 54.03; H 4.05; N, 13.85; S 6.51. EXAMPLE 47 (1K, 2K) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4-triazol-1-yl) propyl] -2 - (4-trifluoromethylphenyl) thiazole-4-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-trifluoromethylphenyl) thiazole-4-carboxylic acid (reference example 32), the title compound was obtained in the form of white solid: mp 167-168 ° C; ? NMR (80 MHz, CDCl 3) d (TMS) 8.21 (s), 8.16 (s), 8.07 (s), 8.1-7.6 (m, arom), 7.6-7.3 (1H, arom), 7.0-6.6 (m, 2H, arom), 5.34 (d, 7 = 1.3, 1H, OH), 5.06 (d, 7 = 14.5, 1 H, TrCH (H)), 5.1-4.8 (m, 1 H, CHMe), 4.5 (d , 7 = 14.5, 1H, TrCH (H)), 1.08 (d, 7 = 7, 3H, MeCH); [] D = -136.7 ° (c 1, CHCl 3). Analysis calculated for C 23 H 18 F 5 N 5 O 2 S: C 52.77; H 3.47; N 13.38; S 6.12. Found: C 52.92; H 3.47; N 13.42; S 6.08. EXAMPLE 48 (lR, 2) -iV- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] -2 phenylthiazole-4-carboxamide Following a procedure similar to that described in example 1 but using 2-phenylthiazole-4-carboxylic acid (reference example 33), the title compound was obtained as a white solid: mp 174-175 ° C; * H NMR (80 MHz, CDCI3) d (TMS) 8.15 (s), 8.1-7.9 (m, arom), 7.81 (s), 7.75 (s), 7.6-7.3 (m, 4H, arom), 7.0- 6.6 (m, 2H, arom), 5.35 (d, 7 = 1.3, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.5 (d, 7 = 14.5, 1H, TrCH (H)), 1.08 (d, 7 = 7, 3H, MeCH); [a] D = -145.5 ° (c 1, CHCl 3). Analysis calculated for C 22 H 19 F 2 N 5 O 2 S: C 58.01; H 4.20; N 15.38; S 7.04. Found: C 58.11; H 4.59; N 15.34; S 6.85. EXAMPLE 49 (LR, 2R) - - [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] -2- [4- (2,2,3,3-tetrafluoropropoxy) phenyl] thiazole-4-carboxamide Following a procedure similar to that described in example 1 but using 2- [4- (2,2,3,3-tetrafluoropropoxy ) phenyl] thiazole-4-carboxylic acid (reference example 34) the title compound was obtained as an amorphous solid: * H NMR (80 MHz, CDCl 3) d (TMS) 8.10 (s), 8.1-7.8 (m, arom. ), 7.6-7.4 (m, 1H, arom), 7.2-6.7 (m, 2 + 1/4 H, arom, CHF2), 6.07 (t, 7 = 4.3, 1 / 2H, CHF2), 5.41 (t, / = 4.3, 1 / 4H, CHF2), 5.34 (d, 7 = 1.3, 1H, OH), 5.06 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.5 (d, 7 = 14.5, 1H, TrCH (H)), 4.44 (tt, 7 = 0.8, 7 = 12, 2H, OCH2), 1.07 (d, 7 = 7, 3H, MeCH); [a] D = -123.8 ° (c 1, CHCl 3). Analysis calculated for C 25 H 21 F 6 N 5 O 3 S: C 51.28; H 3.62; N 11.96; S 5.48. Found: C 50.89; H 3. 90; N 11.34; S 5.34. EXAMPLE 50 (lK, 2) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] -2 - (3-pyridyl) thiazole-4-carboxamide Following a procedure similar to that described in example 1 but using 2- (3-pyridyl) thiazole-4-carboxylic acid, the title compound was obtained as a white solid: mp 182 -183 ° C; l NMR (80 MHz, CDCl 3) d (TMS) 9.23 (broad s, 1H, pyridine), 8.7 (broad s, 1H, pyridine), 8.34 (broad s, 1 / 2H, pyridine), 8.21 (s, 1.5H , thiazole, pyridine), 8.1-7.7 (m, triazole), 7.6-7.3 (m, 2H, arom, pyridine), 7.0-6.6 (m, 2H, arom), 5.34 (d, 7 = 1.3, 1H, OH ), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 1.08 (d, 7 = 7, 3H, MeCH); [a] D = -151.3 ° (c 1, CHCl 3). Analysis calculated for C 21 H 18 F 2 N 6 O 2 S: C 55.26; H 3.97; N 18.41; S 7.02 Found: C 55.14; H 3.93; N 18.41; S 6.81. EXAMPLE 51 (l_R, 2K) -5- (4-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] thiophene-2-carboxamide Following a procedure similar to that described in example 1 but using 5- (4-chlorophenyl) thiophene-2-carboxylic acid (prepared as described in Hauptmann et al, Tetrahedron Lett. 1968, 1317) the title compound was obtained as a white solid: mp 169-170 ° C; * H NMR (300 MHz, CDCl 3) d (TMS) 7.79 (s, 1 H, triazole), 7.78 (s, 1 H, triazole), 7.55 (dt, / t = 2.5, / = 6.6, 2 H, arom), 7.54. (d, 7 = 3.5, 1H, thiophene), 7.38 (dt, / d = 6.5, /t=8.8, 1H, arom), 7.38 (dt, 7t = 2.5, /d=6.6, 2H, arom), 7.25 (d, 7 = 3.5, 1H, thiophene), 6.8-6.6 (m, 2H, arom), 6.53 (broad d, 7 = 9.5, 1H, NH), 5.35 (d, 7 = 1.5, 1H, OH), 5.04 (d, 7 = 14.3, 1H, TrCH (H)), 4.93 (fifth width, 7 = 7, 1H, CHMe), 4.51 (d, /=14.3, 1 H, TrCH (H)), 1.02 (d) , 7 = 6.8, 3H, MeCH); MS 264 and 266 (ethylaminoacyl group, C13H11CINOS),221 and 223 (acyl group, CpH6C10S), 224 (Tr-CH2COHAr, 0H8F2N3O); [α] D = -101.0 ° (c 1, CHCl 3). Analysis calculated for C 23 H 19 ClF 2 N 4 O 2 S: C 56.50 H 3.92; N 11.46; S 6.56. Found: C 56.52; H 3.93; N 11.39; S 6.11. EXAMPLE 52 (l ^, 2) -5- (4-Cyanophenyl) -V- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole -l-yl) propyl] thiophen-2-carboxamide Following a procedure similar to that described in example 1 but using 5- (4-cyanophenyl) thiophene-2-carboxylic acid (reference example 35), the title compound was obtained in white solid form: mp 210-211 ° C; * H NMR (300 MHz, CDCl 3) d (TMS) 7.80 (s, 1 H, triazole), 7.79 (s, 1 H, triazole), 7.71. (d, 7 = 8, 2H, arom), 7.70 (d, 7 = 8, 2H, arom), 7.58 (d, 7 = 3.9, 1 H, thiophene), 7.41 (d, 7 = 3.9, 1H, thiophene ), 7.39 (dt, / = 6.5, /t = 8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.57 (broad d, 7 = 9.4, 1H, NH), 5.37 (d, 7) = 1.5, 1H, OH), 5.05 (d, 7 = 14.3, 1H, TrCH (H)), 4.94 (fifth width,] = 7, 1H, CHMe), 4.52 (d, 7 = 14.3, 1H, TrCH ( H)), 1.03 (d, 7 = 6.8, 3H, MeCH); HPLC-MS 212 (acyl group, C? 2H6NOS), 224 (Tr-CH2COHAr, C 1 0H 8 F 2 N 3 O); [α] D = -105.6 ° (c 1, CHCl 3). Analysis calculated for C 24 H 19 F 2 N 5 O 2 S: C 60.12 H 3.99; N 14.61; S 6.69. Found: C 58.98; H 3.90; N 14.26; S 6.28. EXAMPLE 53 (l_R, 2) -JV- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] -5 - (2-pyridyl) thiophene-2-carboxamide Following a procedure similar to that described in example 1 but using 5- (2-pyridyl) thiophene-2-carboxylic acid, the title compound was obtained as a white solid: mp 212 -213 ° C; TH NMR (80 MHz, CDCl 3) d (TMS) 8.60 (dt, 7t = 1, 7t = 5, 1H, arom), 7.9-7.5 (m, arom), 7.5-7.2 (m, arom), 6.9-6.5 (m, arom, NH), 5.34 (d, 7 = 1.3, 1H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 ( d, 7 = 14.5, 1H, TrCH (H)), 1.02 (d, 7 = 7, 3H, MeCH); [a] D = -116.8 ° (c-1, CHCl3). Analysis calculated for C 22 H 19 F 2 N 5 O 2 S: C 58.01; H 4.20; N 15.38; S 7.04. Found: C 58.20; H 4.55; N 15.82; S 6.85. EXAMPLE 54 (1 R, 2K) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4-triazol-1-yl) propyl] -5 - [l-Methyl-3-trifluoromethyl-lH-pyrazol-5-yl] thiophen-2-carboxamide Following a procedure similar to that described in example 1 but using 5- [l-methyl-3-trifluoromethyl-lH- pyrazol-5-yl] thiophene-2-carboxylic acid the title compound was obtained as a white solid: mp 106-110 ° C; 1 H NMR (300 MHz, CDCl 3) d (TMS) 7.79 (s, 1 H, triazole), 7.77 (s, 1H, triazole), 7.54 (d, 7 = 3.8, 1H, thiophene), 7.38 (dt, / d = 6.5, /t=8.8, 1H, arom), 7.30 (d, 7 = 3.8, 1H, thiophene), 6.84 (s, 1H, pyrazole), 6.8-6.6 (m, 2H, arom), 6.52 (broad d, 7 = 9.3, 1H, NH), 5.34 (d, 7 = 1 -5, 1H, OH), 5.03 (d, 7 = 14.3, 1H, TrCH (H)), 4.93 (fifth width, 7 = 7, 1H, CHMe), 4.52 (d, 7 = 14.3, 1H, TrCH ( H)), 4.03 (s, 3H, Me-pyrazole), 1.01 (d, 7 = 6.8, 3H, MeCH); MS 302 (ethylaminoacyl group, C12H11F3N3OS), 259 (acyl group, C? 0H6F3N2? S), 224 (Tr-CH2COHAr, C? Or H8F2N30); [a] D = -90.1 ° (c 1, CHCl3). Analysis calculated for C 22 H 19 F 5 N 6 O 2 S: C 50.19; H 3.64; N 15.96; S 6.09. Found: C 50.27; H 3.77; N 15.71; S 5.58. EXAMPLE 55 (lK, 2_R) -5- (4-Chlorophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -3-methylthiophen-2-carboxamide Following a procedure similar to that described in example 1 but using 5- (4-chlorophenyl) -3-methylthiophen-2-carboxylic acid (reference example 36) obtained the title compound as an amorphous solid: H NMR (300 MHz, CDCl 3) d (TMS) 7.84 (s, 1 H, triazole), 7.82 (s, 1 H, triazole), 7.56 (dt, / t, 2.5, 7d = 6-6, 2H, arom), 7.40 (dt, 7d = 6.5, 7t = 8.8, 1 H, arom), 7.39 (d, 7 = 7, 2H, arom), 7.14 (s, 1H, thiophene), 6.8-6.6 (m, 2H, arom), 6.42 (broad d, 7 = 9.3, 1H, NH), 5.38 (broad s, 1H, OH), 5.08 (d, 7 = 14.5, 1H, TrCH (H)) , 4.95 (fifth width, 7 = 7, 1H, CHMe), 4.55 (d, 7 = 14.5, 1H, TrCH (H)), 2.82 (s, 3H, Me-thiophene), 1.04 (d, 7 = 6.8, 3H, MeCH); MS 278 and 280 (ethylaminoacyl group, CHH? CINOS), 235 and 237 (acyl group, C? 2H8C10S), 224 (Tr-CH2COHAr, C10H8F2N3O); [α] D = -114.9 ° (c 1, CHCl 3). Analysis calculated for C 24 H 21 ClF 2 N 4 O 2 S: C 57.31 H 4.21; N 11.14; S 6.37. Found: C 57.39; H 4.21; N 11.21; S 6.59. 3 EXAMPLE 56 (lK, 2_R) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl-3 methyl-5- (4-trifluoromethylphenyl) thiophene-2-carboxamide Following a procedure similar to that described in example 1 but using 3-methyl-5- (4-trifluoromethylphenyl) thiophene-2-carboxylic acid (obtained by a similar procedure to that described in reference example 36) the title compound was obtained as an amorphous solid: MS 312 (ethylaminoacyl group, C15H13F3NOS), 269 (acyl group, C13H8F3OS), 224 (Tr-CH2COHAr, C10H8F2N3O); [a] D = -104.2 ° (c 1, CHCl 3). Analysis calculated for C 25 H 21 F 5 N 4 O 2 S: C 55.97 H 3.95; N, 10.44; S 5.98. Found: C 56.27; H 4.00; N, 10.58; S 5.77. EXAMPLE 57 (1 R, 2) -5- (4-Cyanophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1, 2, 4-triazole) 1-yl) propyl] -3-methylthiophen-2-carboxamide Following a procedure similar to that described in example 1 but using 5- (4-cyanophenyl) -3-methylthiophen-2-carboxylic acid (reference example 37) obtained the title compound as a white solid: mp 176-177 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 7.79 (s, 1 H, triazole), 7.78 (s, 1 H, triazole), 7.69 (s, 4 H, arom), 7.39 (dt, / d = 6.5, / t = 8.8, 1H, arom), 7.23 (s, 1H, thiophene), 6.9-6.6 (m, 2H, arom), 6.43 (d wide, 7 = 9.4, 1H, NH), 5.35 (d, 7 = 1.3, 1 HOUR, OH), 5.04 (d, 7 = 14.2, 1, TRCH (H)), 4.93 (fifth width, 7 = 7, 1H, CHMe), 4.52 (d, 7 = 14.2, 1H, TrCH (H)), 2.60 (s, 3H, Me-thiophene), 1.02 (d, 7 = 6.8, 3H, MeCH); GC / MS 269 (ethylaminoacyl group, C 15 H 1 3N 2OS), 226 (acyl group, C 13 H 8 NOS), 224 (Tr-CH 2 COHAr, C 10 H 8 F 2 N 3 O); [a] D = -116.3 ° (c 1, CHCl 3). Analysis calculated for C25H 21 F2N 5O2S: C 60.84 H 4.29; N 14.19; S 6.50.

Found: C 60.54; H 4.25; N 13.81; S 5.90. EXAMPLE 58 (1R, 2K) -3-Amino-5- (4-chlorophenyl) -xV- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2, 4-triazol-1-yl) propyl] thiophene-2-carboxamide Following a procedure similar to that described in example 1 but using 3-amino-5- (4-chlorophenyl) thiophene-2-carboxylic acid (obtained as described in Hartmann, Synthesis 1984, 275) the title compound was obtained as a yellow solid: mp 107-111 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 7.79 (s, 2H, triazole), 7.61 (dt, / t = 2, 7d = 9, 2H, arom), 7.39 (dt, 7d = 6.5, 7t = 8.8 , 1H, arom), 7.37 (dt, 7t = 2, 7d = 9, 2H, arom), 6.9-6.6 (m, 2H, arom), 6.78 (s, 1H, thiophene), 5.93 (broad d, 7 = 9.3, 1H, NH), 5.69 (broad s, 2H, NH2), 5.35 (d, 7 = 1.3, 1H, OH), 5.02 (d, 7 = 14.3, 1 H, TrCH (H)), 4.88 (quint width, 7 = 7, 1H, CHMe), 4.52 (d, 7 = 14.3, 1H, TrCH (H)), 1.01 (d, 7 = 6.8, 3H, MeCH); HPLC-MS 279 and 281 (ethylaminoacyl group, C13H12CIN2OS), 236 (acyl group, C11H7CINOS); [α] D = -137.8 ° (c 1, CHCl 3). Analysis calculated for C 23 H 20 ClF 2 N 5 O 2 S: C 54.82; H 4.00; N 13.90; S 6.36. Found: C 55.42; H 4.19; N 13.34; S 5.35. EXAMPLE 59 (1 R, 2 R) -3-Amino-4 - [(4-chlorophenyl) sulfonyl] -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1) , 2,4-triazol-l-yl) propyl] thiophen-2-carboxamide Following a procedure similar to that described in example 1 but using 3-amino-4 - [(4-chlorophenyl) sulfonyl] thiophen-2 acid The title compound was obtained in the form of a hygroscopic amorphous solid: * H NMR (80 MHz, CDCl 3) d (TMS) 8.1-7.7 (m, arom), 7.9-7.5 (m, arom), 7.6-7.3 (m, arom), 6.9-6.5 (m, arom, NH2), 6.00 (d wide, 7 = 9.5, 1H, NH), 5.31 (d, 7 = 1.5, 1H, OH), 4.95 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.44 (d, 7 = 14.5, 1H, TrCH (H)), 0.96 (d, 7 = 7, 3H, MeCH); [a] D = -59.2 ° (c 1, CHCl 3). Analysis calculated for C23H 20CIF2N 5O 4S2: C 48.64 H 3.55; N, 12.33; S 11.29. Found: C 48.27; H 3.91; N 12.60; S 10.65. EXAMPLE 60 (l_R, 2_R) -4 - [(4-Chlorophene) sulfonyl] -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2.4 -triazol-l-yl) propyl] -3-methylthiophen-2-carboxamide Following a procedure similar to that described in example 1 but using 4 - [(4-chlorophenyl) sulfonyl] -3-methylthiophen-2-carboxylic acid was obtained the title compound as an amorphous white solid: * H NMR (80 MHz, CDCl 3) d (TMS) 8.33 (s, 1H, thiophene), 7.85 (d, 7 = 8.8, 2H, arom), 7.78 (s, 1H, triazole), 7.75 (s, 1H, triazole), 7.50 (d, /=8.8, 2H, arom), 7.41 (dt, / d = 6.5, / t = 9, 1H, arom), 6.9-6.6 ( m, 2H, arom), 6.42 (broad d, 7 = 9.5, 1H, NH), 5.32 (d, 7 = 1.5, 1H, OH), 4.99 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.41 (d, 7 = 14.5, 1H, TrCH (H)), 2.54 (s, 3H, Me-thiophene), 0.98 (d, J = 7, 3H, MeCH); [α] D = -73.8 ° (c 1, CHCl 3). Analysis calculated for C 24 H 21 ClF 2 N 4 O 4 S 2: C 50.84 H 3.73; N 9.88; S 11.31. Found: C 51.23; H 4.12; N 9.67; S 10.62. EXAMPLE 61 (1 R, 2K) -2- (4-Chlorophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (li-1, 2,4-triazole- 1-yl) propyl] -5-methyl-3H-imidazole-4-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-chlorophenyl) -5-methyl-3H-imidazole-4-acid carboxylic acid (reference example 38) the title compound was obtained as a white solid: mp 165-166 ° C; ! H NMR (300 MHz, CDCI3) or (TMS) 9.48 (broad s, 1H, NH-imidazole), 7.81 (s, 1H, triazole), 7.78 (d, 7 = 8-8, 2H, arom), 7.75 (s, 1H, triazole), 7.71 (d, 7 = 9.6, 1H, NH) , 7.43 (dt, / d = 6.5, /t = 8.8, 1H, arom), 7.42 (d, 7 = 8.8, 2H, arom), 6.8-6.6 (m, 2H, arom), 5.38 (s, 1H, OH), 5.03 (d, 7 = 14.3, 1H, TrCH (H)), 4.85 (fifth width, 7 = 7, 1H, CHMe), 4.60 (d, 7 = 14.3, 1H, TrCH (H)), 2.68 (s, 3H, Me-imidazole), 1.07 (d, 7 = 6.8, 3H, MeCH); HPLC-MS 262 and 264 (ethylaminoacyl group, C13H13CIN3O), 219 (acyl group, CpH8ClN20); [α] D = -105.9 ° (c 1, MeOH). Analysis calculated for C23H2? ClF2N6? 2: C 56.74; H 4.35; N 17.26. Found: C 54.48; H 4.05; N 16.09. EXAMPLE 62 (l_R, 2_R) -2- (4-Chlorophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (U-1, 2,4-triazole- 1-yl) propyl] -3,5-dimethyl-3H-imidazole-4-carboxamide Following a procedure similar to that described in example 1 but using the mixture of acids obtained in reference example 39 (2- (4- chlorophenyl) -3,5-dimethyl-3H-imidazole-4-carboxylic acid and 2- (4-chlorophenyl) -l, 5-dimethyl-lH-imidazole-4-carboxylic acid) two products were obtained, which were easily separated by flash chromatography. The less polar product (TLC in AcOEt) was identified by NOE as the title compound and isolated as an amorphous white solid:? NMR (300 MHz, CDCl 3) d (TMS) 7.81 (s, 1 H, triazole), 7.78 (s, 1 H, triazole), 7.55 (d, 7 = 8.5, 2 H, arom), 7.45 (d, 7 = 8.5, 2H, arom), 7.40 (dt, / d = 6.5, /t=8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.39 (d, 7 = 9.5, 1H, NH), 5.37 ( d, 7 = 1.5, 1H, OH), 5.05 (d, 7 = 14.3, 1H, TrCH (H)), 4.96 (fifth width, 7 = 7, 1 H, CHMe), 4.53 (d, 7 = 14.3, 1H, TrCH (H)), 3.87 (s, 3H, N-Me), 2.61 (s, 3H, Me-imidazole), 1.03 (d, 7 = 6.8, 3H, MeCH); GC / MS 276 and 278 (ethylaminoacyl group, C? H? 5ClN3?), 198 and 200 (acyl group, C? 2H? 0N2?), 224 (Tr-CH2COHAr, C10H8F2N3O); [a] D = -71.4 ° (c 1, CHCl3). Analysis calculated for C24H23CIF2N6O2. H2O: C 55.55; H 4.86; N 16.19. Found: C 55.11; H 4.75; N . 93. EXAMPLE 63 (LR, 2K) -2- (4-Chlorophenyl) -V- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4- triazol-l-yl) propyl] -l, 5-dimethyl-lH-imidazole-4-carboxamide In the flash chromatography of the previous example, a second, more polar product eluted, which was identified by NOE as the title compound and which was also obtained in the form of amorphous white solid: * H NMR (300 MHz, CDCl 3) d (TMS) 7.81 (s, 1H, triazole), 7.73 (s, 1H, triazole), 7.68 (broad d, 7 = 9.4, 1H, NH ), 7.57 (d, 7 = 8.5, 2H, arom), 7.48 (d, 7 = 8.5, 2H, arom), 7.40 (dt, / d = 6.5, /t = 8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 5.36 (d, 7 = 1.5, 1H, OH), 5.03 (d, 7 = 14.3, 1H, TrCH (H)), 4.83 (fifth width, 7 = 7, 1 H, CHMe ), 4.56 (d, / = 14.3, 1H, TrCH (H)), 3.59 (s, 3H, N-Me), 2.68 (s, 3H, Me-imidazole), 1.04 (d, 7 = 6.8, 3H, MeCH); GC / MS 276 and 278 (ethylaminoacyl group, C14H 15CIN3O), 198 and 200 (acyl group, C12H10N2O), 224 (Tr-CH2COHAr, C? Or H8F2N3?); [α] D = -108.7 ° (c 1, CHCl 3). Analysis calculated for C 24 H 23 ClF 2 N 6 O 2 .H 2 O: C 55.55; H 4.86; N 16.19. Found: C 55.68; H 4.94; N 15.75. EXAMPLE 64 (l_R, 2K) -5- (4-Chlorophene) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -l, 3,4-oxadiazole-2-carboxamide, solvate with chloroform Following a procedure similar to that described in example 1 but using 5- (4-chlorophenyl) -l, 3,4- Oxadiazole-2-carboxylic acid (reference example 40) and recrystallization of the final product from CHCl3 gave the title compound as a white solid: mp 188-190 ° C; H NMR (300 MHz, MeOH-t) d (MeOH-d) 8.24 (s, 1H, triazole), 7.9-7.8 (m, 2H, arom), 7.68 (s, 1H, triazole), 7.52 (dt, / t = 2, /d=8.7, 2H, arom), 7.35 (dt, / d = 6.5, /t=8.8, 1H, arom), 6.95 (ddd, 7 = 2.4, 7 = 8.7, 7 = 11.5, 1 H, arom), 6.81 (dt, / d = 2.0, / t = 8.0, 1H, arom), 4.88 (d, 7 = 14.4, 1H, TrCH (H)), 4.82 (m, 1H, CHMe), 4.54 (d, 7 = 14.4, 1H, TrCH (H)), 0.99 (d, 7 = 6.8, 3H, M eCH); HPLC-MS 250 and 252 (ethylaminoacyl group, C11H9CIN3O2), 207 and 209 (acyl group, C9H4CIN2O2). 224 (Tr-CH2COHAr, C10H8F2N3O); [α] D = -66.5 ° (c 1, MeOH). EXAMPLE 65 (1 R, 21?) - 3- (4-Chlorophenyl) - - [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1-IF-1, 2,4-triazole- 1-yl) propyl] -l, 2,4-oxadiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 3- (4-chlorophenyl) -l, 2,4-oxadiazole-5- carboxylic acid (reference example 41) the title compound was obtained as a white solid: mp 170-172 ° C; ] H NMR (300 MHz, CDCl 3) d (TMS) 8.10 (dt, / t = 2, / d = 9, 2H, arom), 7. 81 (s, 1H, triazole), 7.79 (s, 1 H, triazole), 7.69 (broad d, 7 = 9.3, 1 H, NH), 7.52 (dt, 7t = 2, / d = 9, 2H, arom. ), 7.40 (dt, 7d = 6.5, /t=8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 5.46 (d, 7 = 1-5, 1H, OH), 5.02 (d, 7 = 14.2, 1H, TRCH (H)), 4.95 (fifth width, / = 7, 1H, CHMe), 4.52 (d, 7 = 14.2, 1 H, TRCH (H)), 1.07 (d, 7 = 6.8 , 3H, MeCH); HPLC-MS 250 and 252 (ethylaminoacyl group, Cp H9dN 3? 2), 207 and 209 (acyl group, C9H4CIN2O2), 224 (Tr-CH2COHAr, C? Or H8F2N3?); [a] = -81.8 ° (c 1, MeOH). EXAMPLE 66 (li, 2K) -5- (4-Chlorophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (LH-1, 2,4-triazole -l-yl) propyl] -l, 2,4-oxadiazole-3-carboxamide Following a procedure similar to that described in example 1 but using 5- (4-chlorophenyl) -l, 2,4-oxadiazole-3 acid -carboxylic (reference example 42) the title compound was obtained as a white solid: mp 79-83 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 8.16 (dt, / t = 1.8, / d = 8.6, 2 H, arom), 7.79 (broad s, 2 H, triazole), 7.60 (broad d, 7 = 9.3, 1H, NH), 7.56 (dt, /t/1.8, /d=8.6, 2H, arom), 7.40 (dt, / d = 6.5, /t=8.8, 1H, arom), 6.8-6.6 (m, 2H , arom), 5.38 (d, 7 = 1.5, 1H, OH), 5.04 (d, 7 = 14.4, 1H, TrCH (H)), 4.95 (fifth width, 7 = 7, 1H, CHMe), 4.53 (d , 7 = 14.4, 1H, TrCH (H)), 1.06 (d, 7 = 6.8, 3H, MeCH); HPLC-MS 250 and. 252 (ethylaminoacyl group, C1 1 H 9C IN 3O 2), 224 (Tr-CH 2 C O HA r, C 10 H 8 F 2 N 3 O); [α] D = -67.4 ° (c 1, MeOH). EXAMPLE 67 (1K, 2R) -3- (4-aorophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4-triazole- 1-yl) propyl] -l, 2,4-thiadiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 3- (4-chlorophenyl) -l, 2,4-thiadiazole-5- carboxylic acid (prepared as described in Howe et al, J.Org.Chem., 1977, 42, 1813) the title compound was obtained as a white solid: mp 215-220 ° C; l NMR (300 MHz, MeOH-d 4) d (MeOH-d 4) 8.45 (dt, / t = 2, / d = 7, 2 H, arom), 8.32 (s, 1 H, triazole), 7.75 (s, 1 H, triazole), 7.65 (dt, / t = 2, 7d = 7, 2H, arom), 7.50 (dt, / d = 6.5, 7t = 8.8, 1H, arom), 7.08 (ddd, 7 = 2.4, 7 = 8.7 , 7 = 11.5, 1H, arom), 6.94 (dt, / d = 2.0, 7t = 8.0, 1H, arom), 5.12 (q, 7 = 6.8, 1H, CHMe), 5.05 (d, 7 = 14.6, 1H , TrCH (H)), 4.70 (d, 7 = 14.6, 1H, TrCH (H)), 1.18 (d, 7 = 6.8, 3H, MeCH); HPLC-MS 266 and 268 (ethylaminoacyl group, C11H9CIN3OS), 223 and 225 (acyl group, C9H4CIN2OS), 224 (Tr-CH2COHAr, C10H8F2N3O); [α] D = -106.3 ° (c 1, CHCl 3). EXAMPLE 68 (lK, 2_R) -5- (4-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (L-1, 2,4-triazole -l-yl) propyl] -l, 2, '-thiadiazole-3-carboxamide Following a procedure similar to that described in Example 1 but using 5 - (4-chlorophenyl) -l, 2,4-thiadiazole- 3-carboxylic acid (prepared as described in Howe et al, J.Org.Chem 1977, 42, 1813) the title compound was obtained as a white solid: mp 186-187 ° C; l NMR (300 MHz, MeOH-d4) d (MeOH) 8.32 (s, 1H, triazole), 8.22 (dt, 7t = 2, /d=8.4, 2H, arom), 7.76 (s, 1H, triazole), 7.70 (dt, / t = 2, /d=8.4, 2H, arom), 7.49 (dt, / d = 6.5, /t=8.8, 1H, arom), 7.08 (ddd, 7 = 2.4, 7 = 8.7, 7 = 11-5, 1 H, arom), 6.94 (dt, / d = 2.0, /t=8.0, 1H, arom), 5.15 (q, 7 = 6.8, 1H, CHMe), 5.05 (d, 7 = 14.6, 1H, TrCH (H)), 4.70 (d, 7 = 14.6, 1 H, TrCH (H)), 1.17 (d, 7 = 6.8, 3H, MeCH); HPLC-MS 266 and 268 (ethylaminoacyl group, C11H9CIN3OS), 223 and 225 (acyl group, C9H4CIN2OS), 224 (Tr-CH2COHAr, 0H8F2N3O); [α] D = -80.8 ° (c 1, CHCl 3). EXAMPLE 69 (lK, 2) -3- (2-Chloro-6-fluorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-l-yl) propyl] -5-methylisoxazole-4-carboxamide Following a procedure similar to that described in example 1 but using 3- (2-chloro-6-fluorophenyl) -5-methylisoxazole 4-carboxylic acid the title compound was obtained as an amorphous solid: H NMR (80 MHz, CDC13) d (TMS) 7.77 (s, 1H, triazole), 7.70 (s, 1H, triazole), 7.6-7.0 ( m, 4H, arom), 6.9-6.5 (m, 2H, arom), 5.88 (broad d, 7 = 9, 1H, NH), 4.83 (d, 7 = 14.5, 1H, TrCH (H)), 5.1- 4.8 (m, 1H, CHMe), 4.17 (d, 7 = 14.5, 1H, TrCH (H)), 2.83 (s, 3H, Me-isoxazole), 0.74 (d, 7 = 6.6, 3H, MeCH); [α] D = -98.2 ° (c 1, CHCl 3). Analysis calculated for C 23 H 19 ClF 3 N 5 O 3: C 54.61; H 3.79; N 13.84. Found: C 55.38; H 4.02; N 13.76. EXAMPLE 70 (lR, 2JR) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (UI-1, 2,4-triazol-1-yl) propyl] -4 - (1,2,3-thiadiazol-4-yl) benzamide Following a procedure similar to that described in example 1 but using 4- (1, 2,3-thiadiazol-4-yl) benzoic acid, the title compound was obtained in the form of yellow solid: mp 196-198 ° C; NMR (80 MHz, CDCl 3) d CTMS) 8.76 (s, 1H, thiadiazole), 8.29 (d, 7 = 8, 2H, arom), 7.98 (d, 7 = 8, 2H, arom), 7.40 (dt, 7d = 6.5, 1H, arom), 7.79 (s, 2H, triazole), 6.9-6.5 (m, 3H, arom, NH), 5.37 (broad s, 1H, OH), 5.08 (d, 7 = 14.5, 1H, TrCH (H)), 5.1-4.8 (m, 1H, CHMe), 4.50 (d, 7 = 14.5, 1H, TrCH (H)), 1.06 (d, 7 = 7, 3H, MeCH); [a] D = -121.2 ° (c 1, CHCl3). Analysis calculated for C2iHi8F2N6? 2S: C 55.26; H 3.97; N 18.41; S 7.02. Found: C 55.65; H 4.11; N 19.05; S 7.39. EXAMPLE 71 (l ?, 2K) -5- (4-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole -l-yl) propyl] nicotinamide Following a procedure similar to that described in example 1 but using 5- (4-chlorophenyl) nicotinic acid, the title compound was obtained: mp 93-101 ° C; * H NMR (300 MHz, CDCl 3) d (TMS) 9.02 (d, 7 = 2.1, 1H, pyr), 8.96 (d, 7 = 2.2, 1H, pyr), 8.33 (t, 7 = 2.2, 1H, py ), 7.8 (s, 1H, triazole), 7.79 (s, 1H, triazole), 7.58 (dt, 7t = 2, 7d = 8-7, 2H, arom), 7.49 (dt, 7t = 2, 7d = 8 -7, 2H, arom), 7.39 (dt, / d = 6.5, 7t = 8.8, 1H, arom), 6.8-6.6 (m, 3H, arom, NH), 5.41 (d, 7 = 1.4, 1H, OH), 5.06 (d, 7 = 14.2, 1H, TrCH (H)) , 5.03 (quint width, 7 = 7, 1H, CHMe), 4.50 (d, 7 = 14.2, 1H, TrCH (H)), 1.06 (d, 7 = 6.8, 3H, MeCH); GC / MS 259 and 261 (ethylaminoacyl group, C14H12CIN2O), 216 and 218 (acyl group, C12H7CINO), 224 (Tr-CH2COHAr, C10H8F2N3O); [a] D = -96.6 ° (c 1, CHCl 3). EXAMPLE 72 (LR, 2K) -3- (4-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] benzamide Following a procedure similar to that described in example 1 but using 3- (4-chlorophenyl) benzoic acid, the title compound was obtained as a white solid: mp 90-91 ° C; ! H NMR (300 MHz, CDC13) d (TMS) 8.05 (t, 7 = 1.7, 1H, arom), 7.80 (dt, /t1.2, /d=8.3, 1H, arom), 7.79 (s, 2H , triazole), 7.72 (dt, 7t = 1.2, 7d = 8-3, 1H, arom), 7.56 (dt, / t = 2, /d=8.7, 2H, arom), 7.5-7.6 (m, 1H, arom), 7.44 (dt,? = 2, /d=8.7, 2H, arom), 7.39 (dt, / d = 6.5, /t =8.8, 1H, arom), 6.8-6.6 (m, 3H, arom, NH), 5.36 (d, /=1.2, 1H, OH), 5.08 (d, 7 = 14.2, 1H, TrCH (H)), 5.01 (fifth width, 7 = 7, 1H, CHMe), 4.50 (d, 7 = 14.2, 1H, TrCH (H)), 1.05 (d, 7 = 6.8, 3H, MeCH); GC / MS 258 and 260 (ethylaminoacyl group, C? 5H13ClNO), 224 (Tr-CH2COHAr, C10H8F2N3O), 215 and 217 (acyl group, C? 3H8C10); [a] D = -97.7 ° (c 1, CHCl 3). EXAMPLE 73 (! R, 2_R) -4- (4-Chlorophenyl) -V- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole -l-yl) propyl] benzamide Following a procedure similar to that described in example 1 but using 4- (4-chlorophenyl) benzoic acid, the title compound was obtained as a white solid: mp 173-174 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 7.93 (dt, 7t = l-7, 7d = 8.4, 2H, arom), 7.79 (s, 2H, triazole), 7.66 (dt, /t / 1.7, / d = 8.4, 2H, arom), 7.55 (dt, / t = 2, /d=8.6, 2H, arom), 7.44 (dt, / t = 2, / = 8.6, 2H, arom), 7.40 (dt, 7d = 6.5, 7t = 8.8, 1H, arom), 6.8-6.6 (m, 3H, arom, NH), 5.37 (broad s, 1H, OH), . 08 (d, 7 = 14.3, 1H, TrCH (H)), 5.00 (fifth width, 7 = 7, 1H, CHMe), 4.50 (d, 7 = 14.3, 1 H, TrCH (H)), 1.04 (d , 7 = 6.8, 3H, M eCH); GC / MS 258 and 260 (ethylaminoacyl group, C? 5H? 3ClNO), 224 (Tr-CH2COHAr, C10H8F2N3O), 215 and 217 (acyl group, C? 3H8C10); [α] D = -110.2 ° (c 1, CHCl 3). EXAMPLE 74 (1K, 2K) -2- (4-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4-triazole- 1-yl) propyl] -7-methylpyrazolo [1, 5-a] pyrimidine-6-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-chlorophenyl) -7-methylpyrazolo [1], 5-a] pyrimidine-6-carboxylic acid the title compound was obtained as a white solid: mp 227-228 ° C; ? NMR (300 MHz, CDCl 3) d (TMS) 8.61 (s, 1 H, arom), 7.99 (dt, / t = 2.0, / = 8.6, 2 H, arom), 7.83 (s, 2 H, triazole), 7.47 ( dt, /t=2.0, /d=8.6, 2H, arom), 7.39 (dt, 7d = 6.5, /t=8.8, 1H, arom), 7.03 (s, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.62 (broad d, 7 = 9-4, 1H, NH), 5.42 (s, 1 H, OH), 5.13 (d, 7 = 14.2, 1 H, TrCH (H)), 5.02 ( quint wide, 7 = 7, 1H, CHMe), 4.55 (d, 7 = 14.2, 1 H, TrCH (H)), 3.13 (s, 3H, Me-heterocycle), 1.09 (d, 7 = 6.8, 3H, MeCH); MS 313 and 315 (ethylaminoacyl group, C16H14CIN4O), 270 and 272 (acyl group, C14H9CIN3O), 224 (Tr-CH2COHAr, 10 C 10 H 8 F 2 N 3 O); [a] D = -93.8 ° (c 1, CHCl 3). Analysis calculated for C 26 H 22 ClF 2 N 7 O 2 S: C 58.05 H 4.12; N 18.23. Found: C 58.37; H 4.19; N 18.04. EXAMPLE 75 (l_R, 2R) -5- (4-Chlorophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] furan-2-carboxamide Following a procedure similar to that described in example 1 but using 5- (4-chlorophenyl) furan-2-carboxylic acid, the title compound was obtained as a white solid: mp 218 -219 ° C; * H NMR (300 MHz, CDCI3) or (TMS) 7.79 (s, 1H, triazole), 7.78 (s, 1H, triazole), 7.69 (dt, / t = 2, /d=8.4, 2H, arom), 7.42 (dt, 7t = 2, /d=8.4, 2H, arom), 7.39 (dt, / d = 6.5, /t=8.8, 1H, arom), 7.25 (d, 7 = 3.6, 1H, furan), 6.88 (broad d, 7 = 9.5, 1 H, NH), 6.8-6.6 (m, 2H, arom), 6.76 (d, 7 = 3.6, 1H, furan), 5.39 (broad s, 1H, OH), 5.04 (d, 7 = 14.2, 1H, TrCH (H)), 4.96 (fifth width, 7 = 7, 1H, CHMe), 4.53 (d, 7 = 14.2, 1H, TrCH (H)), 1.05 (d, 7 = 6.8, 3H, MeCH); GC-MS 248 and 250 (ethylaminoacyl group, C? 3HnClN? 2), 224 (Tr-CH2COHAr, C10H8F2N3O), 205 and 207 (acyl group, CnH6C102); [α] D = -173 ° (c 1, CHCl 3).

Analysis calculated for C 23 H 19 ClF 2 N 4 O 3: C 58.42; H 4.05; N, 11.85. Found: C 57.15; H 3.85; N 10.74. EXAMPLE 76 (R *, 2_R *) - 2- (4-Cyanophenyl) -N- [2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) -2- ( 4-trifluoromethylphenyl) propyl] -4-methylthiazole-5-carboxamide Following a similar procedure to that described in example 29 but using (2R *, 3R *) - 3-amino-1- (1H-1, 2, 4 triazol-l -yl) -2- (4-trifluoromethyl-phenyl) -2-butanol (obtained as described in EP 617031) the title compound was obtained as a white solid: mp 105-111 ° C; ] H NMR (300 MHz, CDCl 3) d (TMS) 8.08 (d, 7 = 8.2, 2 H, arom), 7.84 (s, 1 H, triazole), 7.76 (d, 7 = 8.2, 2H, arom), 7.64 (s, 1H, triazole), 7.57 (d, 7 = 8.4, 2H, arom), 7.47 (d, 7 = 8.4, 2H, arom), 6.45 (broad d, 7 = 9.2, 1H, NH), 5.46 (d, 7 = 1.0, 1H, OH), 4.75 (d, 7 = 14.2, 1H, TrCH (H)), 4.74 (fifth width, / = 7, 1H, CHMe) , 4.55 (d, 7 = 14.2, 1H, TrCH (H)), 2.83 (s, 3H, Me-thiazole), 1.03 (d, 7 = 6.8, 3H, MeCH); GC-MS 270 (ethylaminoacyl group, C 14H 12N 3OS), 256 (Tr-CH 2 COHAr, C1 1 H 9 F 3 N 3 O), 227 (acyl group, C12H7N2OS). EXAMPLE 77 (li, 2) -2- (4-Cyanophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (L-1, 2,4-triazole -l-yl) propyl] -? V-methyl-4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 29 but using (2R, 3R) -3- (iV-methylamino) -2- ( 2,4-difluorophenyl) -l- (lH-1, 2,4-triazol-1-yl) -2-butanol (obtained as described in EP 332,387) was obtained on 77 product mentioned as amorphous white solid: l NMR (300 MHz, CDCl 3) d (TMS) 8.04 (d, 7 = 8.4, 2H, arom), 7.9-7.7 (m, 4H, triazole, arom), 7.5-7.3 (m, 1H, arom), 6.9-6.7 (m, 2H, arom), 5.5-5.3 (m, 3H, OH, TrCH (H), CHMe), 4.37 (d, 7 = 14.2, 1H, TrCH (H )), 3.28 (s, 3H, NMe), 2.55 (s, 3H, Me-thiazole), 1.2-1.1 (m, 3H, MeCH); GC-MS 284 (ethylmethylaminoacyl group, C15H14N3OS), 227 (acyl group, C? 2H7N2OS), 224 (Tr-CH2COHAr, C? Or H8F2N3?); [α] D = -115.2 ° (cl ", CHCl3) Analysis calculated for C25H22F2N6O2S: C 59.05; H 4.36; N 16.53; S 6.30 Found: C 58.81; H 4.53; N 16.42; S 5.69 EXAMPLE 78 (lR , 2K) -2- (4-Cyanophenyl) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] -N- (2-benzyloxyethyl) -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 29 but using the (2R, 3R) -3 - [[2- (benzyloxy) ethyl] amino] -2- (2,4-difluorophenyl) -l- (lH-1, 2,4-triazol-1-yl) -2-butanol (obtained as described in EP 617031) the title compound was obtained as a solid amorphous white: l NMR (300 MHz, CDCl 3) d (TMS) 8.1-7.9 (m, arom), 7.76 (s), 7.74 (s), 7.7-7.5 (m, arom), 7.4-7.2 (m, arom), 6.9-6.7 (m , 2H, arom), 5.5 (broad m, 1H), 5.04 (d, 7 = 14.2, 1H, TrCH (H)), 4.7-4.5 (m, 4H, CH2OCH2), 4.40 (d, 7 = 14.2, 1H , TrCH (H)), 4.0-3.5 (m), 2.47 (s, 3H, Me-thiazole), 1.2-1.0 (m, 3H, MeCH); MS (DIP) 284 (ethylbenzyloxyethylamincacil group, C23H22N3O2S), 227 (acyl group, C12H7N2OS), 224 (Tr-CH2COHAr, C10H8F2 3O); [α] D = -69.7 ° (c 1, CHCl 3). EXAMPLE 79 (lK, 2) -2- (4-Cyanophenyl) -IV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -N- (ethoxycarbonylmethyl) -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 29 but using (2R, 3R) -3 - [(ethoxycarbonylmethyl) amino] -2- (2,4-difuorophenyl) -l- (lH-1, 2,4-triazol-1-yl) -2-bui anol (obtained as described in EP 617031) the title compound was obtained as an amorphous white solid :] H NMR (300 MHz, CDCl 3) d (TMS) 8.08 (m, 2 H, arom), 7.8 (m, 4 H, triazole, arom), 7.4-7.1 (m, 1 H, arom), 6.9-6.7 (m , 2H, arom), 5.5 (m, 1H, OH), 5.2-5.1 (m, 2H, CH2CO2EO, . 0-4.1 (m, 5H, TrCH2 / CHMe, CH3CH2O), 2.61 and 2.53 (broad s, 3H, Me-thiazole), 1.2-1.0 (m, 6H, MeCH, CH3CH2O); [α] D = -142.5 ° (c 1, CHCl 3). Analysis calculated for C28H26F2N6O S.I H2O: C 56.18; H 4.71; N 14.04; S 5.36. Found: C 56.19; H 4.50; N 14.00; S 5.17. EXAMPLE 80 (l_R, 2_R) -2- (4-Cyanophenyl) -? V- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-l, 2,4-triazole -l-yl) propyl] -? V- (benzyloxycarbonylmethyl) -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 29 but using the (2R, 3R) -3 - [(benzyloxycarbonylmethyl) amino] -2- (2,4-difluorophenyl) -l- (lH-1, 2,4-triazol-1-yl) -2-butanol (obtained as described in US Pat. EP 617031) the title compound was obtained as an amorphous white solid:] H NMR (300 MHz, CDC13) d (TMS) 8.0 (m, 2H, arom), 7.8-7.7 (m, 4H, triazole, arom), 7.4-7.1 (m, 6H, arom), 6.8-6.6 (m, 2H, arom), 5.5 (m, 1H, OH), 5.4-4.4 (m, 7H, CH2Ph, CH2C02Bn, TrCH2, CHMe), 2.5 ( s wide, 3H, Me-thiazole), 1.2-1.0 (m, 3H, MeCH); [a] D = -114.2 ° (c 0.2, CHCl3). EXAMPLE 81 (LR, 2J?) - 2- (4-Cyanophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole -l-yl) propyl] -JV- (carboxymethyl) -4-methylthiazole-5-carboxamide, trihydrate A mixture of the product obtained in the previous example (600 mg, 1 mmol), Pd / C was hydrogenated (1 atm) 5% (25 mg) and ethanol (25 mL) at room temperature for 6 h. The resulting crude was filtered over celite and the filtrate was concentrated to dryness to give the title compound as a white solid. (450 mg, 88%): mp 153-159 ° C; [α] D = -73.8 ° (c 0.2, MeOH). Analysis calculated for C 26 H 22 F 2 N 6 O 4 S.3H 2 O: C 51.48; H 4.65; N, 13.85; S 5.29. Found: C 51.85; H 4.40; N 13.60; S 4.61. EXAMPLE 82 (1 R, 2K) -2- (4-Cyanophenyl) -lV- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4-triazole- 1-yl) propyl] -IV- (2-hydroxyethyl) -4-methylthiazole-5-carboxamide To a solution of the product obtained in Example 79 (2.46 g, 4.23 mmol) in ethanol (25 mL) was slowly added NaBHt in 3 portions (0.48 mg, 12.7 mmol). The mixture was stirred at room temperature for 20 h, and then the reaction was stopped by the addition of a saturated aqueous solution of NH 4 Cl. The resulting mixture was concentrated and the concentrate was partitioned between water and CHCl3. The organic phase was decanted, dried over anhydrous Na 2 SO 4, filtered and concentrated to a residue. This was purified by flash chromatography to give the title compound as a white solid: mp 113-119 ° C; TH NMR (300 MHz, CDCl 3) d (TMS) 8.27 (broad s), 8.05 (broad m, 2H, arom), 7.75 (broad m, 4 H, triazole, arom), 7.36 (m, 1 H, arom), 6.9 -6.5 (m, 2H, arom), 5.71 (broad s, 1H, OH), 4.9-4.6 (m, 2H, TrCH (H), CHMe), 4.2-3.5 (m, 5H, NCH2CH2, TrCH (H) ), 2.54 and 2.46 (s, 3H, Me-thiazole), 1.3-1.1 (m, 3H, MeCH); GC-MS 314 (ethylhydroxyethylaminoacyl group, Ci 6H and 6N3? 2S), 271 (ethylaminoacyl group + 1, C14H12N3OS), 227 (acyl group, C12H7N2OS), 224 (Tr-CH2COHAr, C10H8F2N3O); [a] D = -76.5 ° (c 1, CHCl 3). EXAMPLE 83 (4R, 5K) -4- [5- [5- (2,4-difluorophenyl) -4-methyl-5 - [(1H-1, 2,4-triazol-1-yl) methyl] oxazo- Lidine-3-carbonyl] -4-methylthiazol-2-yl] benzonitrile Following a similar procedure to that described in Example 29 but using (4R, 5R) -5- (2,4-difluorophenyl) -4-methyl-5 - [(1H-l, 2,4-triazol-1-yl) methyl] oxazolidine (obtained as described in EP 332,387) the title compound was obtained as a white solid: mp 200-201 ° C; H NMR (300 MHz, CDC13) d (TMS) 8.08 (d, 7 = 8.1, 2H, arom), 7.77 (d, 7 = 8.1, 2H, arom), 7.77 (s, 1H, triazole), 7.72 (s) , 1H, triazole), 7.31 (dt, /d=6.6, /t=8.7, 1H, arom), 7.0-6.8 (m, 2H, arom), 5.43 (broad s, 1H, OCH (H) N), 5.31 (d, 7 = 4.5, 1H, OCH (H) N), 5.1-4.9 (broad s, 1H, CHMe), 4.58 (q AB,? V = 0.059, 7 = 14.7, 2H, TrCH2), 2.65 ( s, 3H, Me-thiazole), 1.04 (d, 7 = 6.6, 3H, MeCH); GC-MS 227 (acyl group, C 12 H 7 N 2 OS); [< x] D = + 17.5 ° (c 1, CHCl3). Analysis calculated for C 25 H 20 F 2 N 6 O 2 S: C 59.28; H 3.98; N 16.59; S 6.33. Found: C 59.29; H 3.83; N 16.16; S 6.06. EXAMPLE 84 (2i?, 3R) -4- [5- [2- (2,4-difluorophenyl) -3-methyl-2 - [(lH-1, 2,4-triazol-1-yl) methyl] morfo -lino-4-carbonyl] -4-methylthiazol-2-yl] benzonitrile A cooled solution (0 ° C) of (lR, 2R) -2- (4-cyanophenyl) -N- [2- (2, 4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] - - (2-hydroxyethyl) -4-methylthiazole-5-carboxamide ( 0.45 g, 0.83 mmol, obtained in Example 82) in THF (10 mL) with diethylazadicarboxylate (0.20 mL, 1.25 mmol) and tributylphosphine (0.31 mL, 1.25 mmol) for 20 h at room temperature. The mixture was evaporated to dryness and the residue was purified by flash chromatography to give the title compound as a white solid: mp 150-160 ° C; ^ H NMR (300 MHz, CDCl 3) d (TMS) 8.06 (d, 7 = 8.4, 2H, arom), 7.76 (s, 1H, triazole), 7.76 (d, 7 = 8.4, 2H, arom), 7.30 ( s, 1H, triazole), 7.4-7.2 (m, 1H, arom), 7-6.7 (m, 2H, arom), 5.53 (broad signal), 5.17 (d, 7 = 15.1, 1H, TrCH (H)), 4.7 (broad d, 1H), 4.6-4.4 (m, 1H), 4.0 (broad d), 3.6 (broad s), 2.57 (s, 3H, Me-thiazole), 1.13 (d, 7 = 6.8, 3H, MeC H); GC-MS 293 (M + -acyl, C 14 H 15 N 4 F 2 O), 227 (acyl group, C 12 H 7 N 2 OS); [α] D = -80.5 ° (c 1, CHCl 3). EXAMPLE 85 (2_R, 3R) -4- [5- [2- (2,4-difluorophenyl) -6-hydroxy-3-methyl-2 - [(lH-1, 2,4-triazol-1-yl) methyl] morpholine-4-carbonyl] -4-methylthiazol-2-yl] benzonitrile To a cooled solution (-78 ° C) of DMSO (0.29 mL, 4.17 mmol) in CH 2 Cl 2 (10 mL) was added a solution of trifluoroacetic anhydride (0.30 mL, 2.09 mmol) in CH 2 Cl 2 (1 mL) dropwise. Ten minutes later, a solution of (1 R, 2R) -2- (4-cyanophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H) was added. -l, 2,4-triazol-1-yl) propyl] -jV- (2-hydroxyethyl) -4-methylthiazole-5-carboxamide (0.9 g, 1.67 mmol, obtained in Example 82) in CH 2 Cl 2 (3 mL). The mixture was stirred for 1 h, and then triethylamine (1.1 mL, 8.3 mmol) was added. The reaction mixture was allowed to warm to -40 ° C and was stirred at this temperature for 1.5 h and then at -10 ° C for 30 min. An aqueous solution of 10% NaHC 3 3 was added, the organic phase was separated and the aqueous phase extracted with chloroform. The combined organic phases were washed with water, dried over anhydrous Na 2 SO 4, filtered and concentrated to give a crude reaction. Purification by flash chromatography gave the title compound as a white solid: mp 225-228 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 8.06 and 8.05 (d, 7 = 8.4, 2H, arom), 7.77 (s, 1H, triazole), 7.76 (d, 7 = 8.4, 2H, arom), 7.35 (dt, 7d = 6.5, /t = 8.8, 1H, arom), 7.30 (s, 1H, triazole), 7.0-6.7 (m, 2H, arom), 5.83 (m, 1H, OCHOH), 5.8-3.2 (several broad signals), 2.57 and 2.55 (s, 3H, Me-thiazole), 1.14 (d, 7 = 6.8, 3H, MeCH); [α] D = -79.8 ° (c 1, CHCl 3). Analysis calculated for C26H22F2N6O3S.I / 2H2O: C 57.24; H 4.21; N 15.40; S 5.86. Found: C 57.49; H 4.03; N 15.08; S 5.69. EXAMPLE 86 (2_R 3R) -4- [5- [2- (2,4-difluorophenyl) -3-methyl-6-oxo-2 - [(1H-1, 2,4-triazol-1-yl) methyl] ] morpholine-4-carbonyl] -4-methylthiazol-2-yl] benzonitrile From the first fractions of the above chromatography, the title compound was isolated as an amorphous white solid: GC-MS 227 (acyl group, C12H7N2OS). EXAMPLE 87 (lR, 2K) -2- (4-Cyanophenyl) -iV- [2- (2,4-dichlorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole- 1-yl) propyl] -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 29 but using the (2R, 3R) -3-amino-2- (2,4-dichlorophenyl) -l- ( lH-l, 2,4-triazol-l-yl) -2-butanol (obtained according to the general method described in / • Org Chem., 1995, 60, 3000-3012) the title compound was obtained as a solid white: mp 109-113 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 8.07 (dt, /t = 1.8, /d=6.9, 2H, arom), 7.83 (s, 1H, triazole), 7.81 (s, 1H, triazole), 7.76. (dt, /t=1.8, /d=6.9, 2H, arom), 7.51 (d, 7 = 8.4, 1H, arom), 7.35 (d, 7 = 2.1, 1H, arom), 7.12 (dd, 7 = 2.1, 7 = 8.7, 1H, arom), 6.50 (broad d, 7 = 9.2 , 1H, NH), 5.63 (d, 7 = 14.4, 1H, TrCH (H)), 5.51 (broad s, 1H, OH), 5.45 (m, 1H, CHMe), 4.45 (d, 7 = 14.4, 1H , TrCH (H)), 2.83 (s, 3H, Me-thiazole), 0.99 (d, 7 = 6.6, 3H, MeCH); GC-MS 270 (ethylaminoacyl group, C ^ Hp ^ OS), 256 and 258 (Tr-CH2COHAr, C10H8CI2N3O), 227 (acyl group, C? 2H7N2OS); [α] D = -106.3 ° (c 1, CHCl 3). Analysis calculated for C 24 H 20 Cl 2 N 6 O 2 S: C 54.75; H 3.83; N 15.97; S 6.08. Found: C 54.28; H 3.89; N 16.02; S 5.69.

EXAMPLE 88 (lJR, 2K) - - [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] -2- [4- [hydroxyamino (imino) methyl] phenyl] -4-methylthiazole-5-carboxamide To a solution of Na 2 C 3 (0.72 g, 6.77 mmol) in a mixture of H 2 O 5 mL) and THF (5 mL) was added (1R, 2R) -2- (4-cyanophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3 - '(1H-1, 2,4-triazole-1 -yl) propyl] -4-methylthiazole-5-carboxamide mesylate (0.5 g, 0.84 mmol, obtained in Example 31) and hydroxylamine hydrochloride (0.29 g, 4.23 mmol). The reaction mixture was stirred at room temperature overnight, and then concentrated and the aqueous residue was extracted with CHCl3. The organic phase was decanted, dried over Na 2 SO 4, filtered and the filtrate was concentrated to a solid. Purification by flash chromatography gave the title compound as a slightly yellow solid: mp 135-148 ° C; * H NMR (300 MHz, MeOH-d4) d (MeOH-d4) 8.24 (s, 1H, triazole), 8.03 (dt, 7t = 1.6, /d=8.5, 2H, arom), 7.78 (dt, / t = 1.6, 7d = 8-5, 2H, arom), 7.71 (s, 1H, triazole), 7.38 (dt, / d = 6.5, /,=8.8, 1H, arom), 6.97 (ddd, 7 = 2.4, 7 = 8.7, 7 = 11.5, 1H, arom), 6.84 (dt, 7d = 2.1, /t = 8.0, 1H, arom), 5.00 (q, / = 7, 1H, CHMe), 4.99 (d, 7 = 14.3, 1H, TrCH (H)), 4.58 (d, / = 14.3, 1 H, TrCH (H)), 2.74 (s, 3H, thiazole-Me), 1.05 (d, 7 = 7, 3H, MeCH); MS 496 (M ^ -NH2); [αD = -77.2 ° (c 1, MeOH). Analysis calculated for C 24 H 23 F 2 N 7 O 3 S.H 2 O: C 52.84; H 4.62; N 17.97; S 5.88 Found: C 53.48; H 4.61; N 17.19; S 5.34. EXAMPLE 89 (l_R, 2K) -2- [4- [Acetoxyamino (imino) methyl] phenyl] -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1 , 2,4-triazol-1-yl) propyl] -4-methylthiazole-5-carboxamide A solution of the product obtained in Example 88 (150 mg, 0.28 mmol) in CHCl 3 (10 mL) was treated with triethylamine (33 μL). , 0.33 mmol) and acetyl chloride (25 μL, 0.32 mmol) at 25 ° C for 18 h. Then an aqueous solution of 10% NaHC 3 3 was added and the phases were separated. The organic phase was washed with water, dried over Na 2 SO 4, filtered, concentrated and purified by flash chromatography to give the title compound as a white solid: mp 146-147 ° C; H NMR (300 MHz, CDCl 3) d (TMS) 8.01 (dt, / t = 1. 9, /d=8.7, 2H, arom), 7.81 (s, 1 H, triazole), 7.80 (dt, 7t = 1 -9, /d=8.7, 2H, arom), 7.79 (s, 1H, triazole) , 7.38 (dt, 7d = 6.5, / = 8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.43 (d wide, 7 = 9.5, 1 H, NH), 5.38 (s, 1 H , OH), 5.13 (broad s, 2H, NH), 5.05 (d, 7 = 14.5, 1 H, TrCH (H)), 4.94 (fifth width, 7 = 7, 1H, CHMe), 4.52 (d, 7 = 14.5, 1H, TrCH (H)), 2.82 (s, 3H, Me-thiazole), 2.27 (s, 3H, COMe), 1.02 (d, 7 = 6.8, 3H, MeCH); MS 327 (group IV-ethylheterocycle-H20, C16H16N4O2S), 284 (acyl group-H2O, C14H10N3O2S), 224 (Tr-CH2COHAr, C? 0H8F2NO); [α] D = -103.9 ° (c 1, MeOH).

Analysis calculated for C 26 H 25 F 2 N 7 O 4 S: C 54.83; H 4.42; N, 16.76; S 5.63 Found: C 53.97; H 4.38; N, 16.90; S 5.23. EXAMPLE 90 (1 R, 2K) -2- (4-Tert-butylphenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (U-1, 2,4- triazol-1-yl) propyl] -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-fer-1-butylphenyl) -4-methylthiazole-5-carboxylic acid (example reference 43) the title compound was obtained as a white solid: mp 85-91 ° C; l NMR (300 MHz, CDCl 3) d (TMS) 7.88 (dt, / t = 2, / d = 8.5, 2 H, arom), 7.81 (s, 1 H, triazole), 7.79 (s, 1 H, triazole), 7.47 (dt, / t = 2, /d=8.5, 2H, arom), 7.38 (dt, / d = 6.5, 7t = 8.8, 1H, arom), 6.8-6.6 (m, 2H, arom), 6.38 ( d wide, 7 = 9.5, 1H, NH), 5.37 (s, 1H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 4.93 (fifth width, 7 = 7, 1H, CHMe) , 4.53 (d, 7 = 14.5, 1H, TrCH (H)), 2.81 (s, 3H, Me-thiazole), 1.35 (s, 9H, CMe3), 1-02 (d, 7 = 6.8, 3H, MeCH ); GC-MS 301 (ethylaminoacyl group, C17H22N2OS), 258 (acyl group, C? 5H? 6NOS), 224 (Tr-CH2COHAr, C10H8F2N3O); [a] D = -105.9 ° (c 1, CHCI3). Analysis calculated for C 27 H 29 F 2 N 5 O 2 S: C 61.70; H 5.56; N 13.32; S 6.10. Found: C 61.70; H 6.20; N, 12.64; S 5.24. EXAMPLE 91 (l_R, 2_R) -2- (4-Cyanophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-imidazol-1-yl) propyl] -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-cyanophenyl) -4-methylthiazole-5-carboxylic acid (reference example 24) and (2R, 3R) - 3-amino-2- (2,4-difluorophenyl) -l- (lH-imidazol-1-yl) -2-butanol (75 mg, 0.28 mmol, obtained according to the general method described in J. Org. Chem., 1995, 60, 3000-3012) in DMF (5 mL) the title compound was obtained as a white solid: mp 126-128 ° C; * H NMR (300 MHz, CDCl 3) d (TMS) 8.05 (dt, 7t = 2, 7d = 8.4, 2H, arom), 7.50 (dt, / t = 2, /d=8.4, 2H, arom), 7.47 (dt, 7d = 6.5, /t = 8.8, 1H, arom), 7.24 (s, 1H, imidazole), 6.8-6.6 (m, 2H, arom), 6.52 (broad d, 7 = 9.5, 1H, NH) , 6.51 (s, 1H, imidazole), 6.32 (s, 1H, imidazole), 4.85 (fifth width, 7 = 7, 1H, CHMe), 4.68 (d, 7 = 14.5, 1H, ImCH (H)), 4.29 (d, 7 = 14.5, 1 H, ImCH (H)), 2.80 (s, 3H, Me-thiazole), 1.06 (d, 7 = 6.8, 3H, MeCH); MS 227 (acyl group, C12H7N2OS), 223 (Im-CH2COHAr, Cp H9F2N2?); [a] D = -20.4 ° (c 1, CHCl3). Analysis calculated for C 25 H 21 F 2 N 5 O 2 S: C 60.84; H 4.29; N 14.19; S 6.50 Found: C 60.85; H 4.31; N 13.75; S 6.18. EXAMPLE 92 (l_R, 2K) -2- (4-Cyanophenyl) -N- [2- (2-fluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole-1- il) propyl] -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 29 but using (2R, 3R) -3-amino-2- (2-fluorophenyl) -l- (lH-1, 2 , 4-triazol-1-yl) -2-butanol (obtained as described in / Org Chem., 1995, 60, 3000-3012) the title compound was obtained as a white solid: mp 107-114 ° C; H NMR (300 MHz, CDC13) d (TMS) 8.07 (dt, /t = 1.8, /d = 8.6, 2H, arom), 7.79 (s, 1H, triazole), 7.76 (dt, 7t = 1.8, / d = 8.6, 2H, arom), 7.75 (s, 1H, triazole), 7.36 (dt, /d=1.6, 7t = 7.8, 1H, arom), 7.3-7.3 (m, 1H, arom), 7.1-7.0 ( m, 2H, arom), 6.50 (broad d, 7 = 9.3, 1H, NH), 5.29 (d, 7 = 1-6, 1H, OH), 5.08 (d, 7 = 14.2, 1H, TrCH (H) ), 4.99 (fifth width, 7 = 7, 1H, CHMe), 4.52 (d, 7 = 14.2, 1H, TrCH (H)), 2.83 (s, 3H, Me-thiazole), 1.03 (d, 7 = 6.8 , 3H, MeCH); GC / MS 270 (ethylaminoacyl group, C14H 12N3OS), 227 (acyl group, C12H7N2OS), 206 (Tr-CH2COHAr, C10H9FN3O); [α] D = -115.6 ° (c 1, CHCl 3). Analysis calculated for C 24 H 21 FN 6 O 2 S.I / 2H 2 O: C 59.36; H 4.53; N 17.30; S 6.59. Found: C 59.63; H 4.73; N 16.68; S 6.15. EXAMPLE 93 (LR, 2K) -N- [2- (2,4-Difluorophenyl) -2-hydroxy-l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] -2 - (4-fluorophenyl) -4-methylthiazole-5-carboxamide Following a procedure similar to that described in example 1 but using 2- (4-fluorophenyl) -4-methylthiazole-5-carboxylic acid, the title compound was obtained in the form of amorphous white solid: * H NMR (300 MHz, CDCl 3) d (TMS) 7.96 (n, 2 H, arom), 7.81 (s, 1 H, triazole), 7.79 (s, 1 H, triazole), 7.37 (dt, 7d = 6.5, /t = 8.8, 1H, arom), 7.16 (tt, 7 = 2, 7 = 8.5, 2H, arom), 6.8-6.6 (m, 2H, arom), 6.40 (broad d , 7 = 9.5, 1 H, NH), 5.41 (s, 1 H, OH), 5.05 (d, 7 = 14.5, 1H, TrCH (H)), 4.94 (fifth width, 7 = 7, 1H, CHMe) , 4.52 (d, 7 = 14.5, 1 H, TrCH (H)), 2.80 (s, 3H, M e -thiazole), 1.02 (d, 7 = 6.8, 3H, M e CH); MS 263 (ethylaminoacyl group, C 13 H 2 FN 2 OS), 220 (acyl group, C 1 H 7 FNOS), 224 (Tr-CH 2 COHAr, C 10 H 8 F 2 N 3 O); [a] D = -113.5 ° (c 0.5, CHCI3). Analysis calculated for C 23 H 20 F 3 N 5 O 2 S: C 56.67; H 4.14; N 14.37; S 6.58 Found: C 56.87; H 4.19; N 14.00; S 6.29. EXAMPLE 94 In vitro activity In vitro activity was assessed against C. albicans, C. krusei, and Aspergillus fumigatus by the agar dilution method. The strains tested were of clinical origin or from the ATCC. Stock solutions of 800 μg / mL concentration were prepared by dissolving the products to be tested in 507o ethanol. The culture medium used was Kimmig agar (K.A., E. Merck) supplemented with 0.5% glycerin. Plates containing serial dilutions of the products to be tested were inoculated (80 to 0.025 μg / mL) 18 with 10 μL inoculum, whose concentration was 10 ^ colony forming units (cfu) / mL. Plates were incubated at 25 ° C for 48 h for Candida sp. and for 5 days for Apergillus fumigatus. At the end of the incubation, the MIC were determined (minimum inhibitory concentrations). The results are shown in the following table: IN VITRO ACTIVITIES (CMI in μg / mL) Na ETEMPLO C.albicans C.krusei Asp. fumigatus 2 0.15 2.5 10 3 0.07 5 5 8 0.15 1.25 10 10 0.63 2.5 10 15 0.15 2.5 5 19 0.15 5 2.5 22 <; 0.03 0.63 5 23 < 0.03 2.5 5 24 < 0.03 1.25 1.25 25 < 0.03 1.25 1.25 26 < 0.03 0.63 1.25 27 0.15 1.25 0.63 28 < 0.03 1.25 1.25 29 < 0.03 2.5 2.5 34 0.07 1.25 10 39 0.07 0.63 1.25 41 < 0.03 1.25 2.5 43 < 0.03 1.25 10 51 < 0.03 0.31 2.5 55 < 0.03 0.07 0.31 57 < 0.03 0.63 0.63 59 < 0.03 0.63 5 74 0.07 1.25 5 77 < 0.03 1.25 2.5 87 < 0.03 0.63 1.25 90 0.63 1.25 1.25 92 < 0.03 5 2.5 EXAMPLE 95 In Vivo Activity (Systemic Candidiasis) Groups of 10 male mice were inoculated intravenously with 0.2 mL of a suspension containing (2-8) x 107 cfu / mL of Candida albicans. The compounds were administered orally at 1 mg / kg at 1, 4 and 24 h after infection. Following this protocol, the animals treated with the products of examples 2, 3, 4, 7, 8, 9, 10, 15, 16, 18, 19, 21, 22, 24, 25, 26, 27, 28, 29 , 30, 31, 34, 36, 43, 44, 51, 52, 55, 56, 57, 62, 66, 73, 74, 77, 82, 83, 84, 85, 87 and 92 presented a 1007th protection on day when all the animals of the control group had died (days 2-4). EXAMPLE 96 In vivo activity (systemic aspergillosis) According to a similar in vivo model of systemic aspergillosis in mice, animals treated with the products of examples 3, 25, 26, 29, 51, and 57 (orally 20 mg / kg / day, 5 days) presented a 60-1007th protection on day 25 after infection. Mortality in the control group at day 25 was 907s.

Claims (18)

1. CLAIMS 1.- A compound of formula I:
2. I in the form of a racemate, a mixture of diastereomers or in the form of a pure enantiomer, characterized in that: X represents N or CH; Ar represents phenyl or phenyl substituted by one or more halogen and / or trifluoromethyl groups; R1 is C1-C4 alkyl; R2 is hydrogen or C1-C4 alkyl; or Ri together with R2 form a C2-C4 polymethylene chain; R3 is hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-Ci-C4 alkyl, C1-C4 haloalkyl, phenyl-C? -C4 alkyl (wherein the phenyl group may be optionally substituted by 1, 2 , 3 or 4 R5 groups, which may be the same or different), a group - (CH2) n-CH2? H, a group - (CH2) n -CH2? Bn, a group - (CH2) n- H2NR6R7, a group group - (CH2) n-CH2COOR6, or a group - (CH2) n-CH2COOBn, in which case R4 is hydrogen; or R3 together with R4 and the remainder of said compound of formula I form an oxazolidine ring of formula I ' or R3 together with R4 and the remainder of said compound of formula I form a morpholine ring of formula I "wherein D is O, in which case the dashed line represents a covalent bond, or D is hydroxy or hydrogen, in which if the dotted line is absent, A represents phenyl or a monocyclic or bicyclic heterocyclic group containing from 1 to 4 heteroatoms chosen from N, O and S and where each ring in the heterocyclic group consists of 5 or 6 atoms, where A may be unsubstituted or have 1, 2, 3 or 4 groups Re; B represents a phenyl group which may be optionally substituted by 1, 2, 3 or 4 R9 groups, or B represents a monocyclic or bicyclic heterocyclic group containing from 1 to 4 heteroatoms chosen from N, O and S and where each ring in the heterocyclic group consists of 5 or 6 atoms, which may be optionally substituted by 1, 2, 3 or 4 R9 groups; -C4 alkyl, C1-C4 haloalkyl or halogen or; n represents 0, ', 2 or 3; and R7 independently represent hydrogen or C1-C4 alkyl; Rd represents O-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, halogen, phenyl (optionally substituted by a halogen group, cyano, C1-C4 haloalkyl or C1-C4 haloalkoxy) , nitro, cyano, hydroxy, hydroxymethyl, a group -NRéR7, a group -CONR6R7, a group
3. -CORó, a group -COC R6, or a group -SOzR? O; R9 represents C1-C4 alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -C4 haloalkoxy, 2-carboxy-2-propyl, halogen, nitro, cyano, hydroxy, benzyloxy, hydroxymethyl, a group
4. -CH2-OCO-R6, a -CO-Ré group, a -COO-RÓ group, a -SOzR group, or a -NRéR7 group, a -CONR6R7 group, a -C (= NR6) NHRp group, a group - C (= NRp) OR6, and in addition one of the groups R9 may also represent 1-pyrrolyl, 1-imidazolyl, lH-l, 2,4-triazol-l-yl, 5-tetrazolyl (optionally substituted by C1-C4 alkyl) ), 1-pyrrolidinyl, 4-morpholinyl, 4-morpholinyl-N-oxide, phenyl or phenoxy (both optionally substituted by a C1-C4 alkyl group, C1-C4 haloalkyl, -C4 alkoxy, C1-C4 haloalkoxy, halogen, nitro or cyano), or a group of formula (i) - (iv) (i) (ii)
5. Rio represents C1-C4 alkyl; z represents 0, 1 or 2; Rll represents hydrogen, -CONH2, -COMe, -CN, -S02NHR6, -SO2R10, -O6, or -OCORe; Rl2 represents hydrogen or methyl; R13 represents hydrogen, isopropyl, cyclopentyl, cyclopropyl, 2-butyl, 3-pentyl, 3-hydroxy-2-butyl, or 2-hydroxy-3-pentyl; p represents 0 or 1; R 14 represents halogen, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, nitro, amino, cyano, or a group of formula (i); E represents -CH 2 - or -C (= 0) -; G represents NH or O; Y represents a simple bond, -S-, -SO-, -SO2-, -O- or -NR6-; m and q represent independently 0, 1 or 2; and its salts and solvates. 2. A compound as claimed in claim 1 characterized in that X represents N. 3. A compound as claimed in claims 1 or 2 characterized in that Ri represents C1-4 alkyl and R2 represents hydrogen. 4. A compound as claimed in claim 3 characterized in that R represents methyl. 5. A compound as claimed in any of claims 1 to 4 characterized in that R4 represents hydrogen.
6. 6. A compound as claimed in claim 5 characterized in that R3 represents hydrogen.
7. 7. A compound as claimed in any of claims 1 to 6 characterized in that Ar represents 2-fluorophenyl, 4-fluorophenyl, 2-chloro-4-fluorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 4- (trifluoromethyl) phenyl or 4-chlorophenyl.
8. 8. A compound as claimed in any of claims 1 to 7 characterized in that A represents phenyl or a 5- or 6-membered heterocyclic ring containing from 1 to 3 heteroatoms selected from N, O and S, where A may be not substituted or possessing 1, 2, 3 or 4 Rs groups.
9. 9. A compound as claimed in claim 8, characterized in that A represents a 5- or 6-membered aromatic heterocyclic ring containing from 1 to 3 heteroatoms selected from N, O and S, and which may be unsubstituted or possess 1. or 2 groups Rs-
10. 10.- A compound as claimed in any of claims 1 to 9 characterized in that B represents a phenyl group which may be optionally substituted by 1, 2, 3 or 4 substituents R9.
11. 11. A compound as claimed in any of claims 2 to 10, characterized in that the stereochemistry of the compounds is (R, R).
12. 12. A compound as claimed in claim 1 characterized in that: X represents N; R1 represents methyl; R2 represents hydrogen; R3 represents hydrogen; R4 represents hydrogen; Ar represents 2-fluorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 4- (trifluoromethyl) phenyl or 4-chlorophenyl; A represents thiophene, furan, pyrrole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, 1,2,4-triazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,2,4- oxadiazole, or 1,2,4-thiadiazole, wherein A may be optionally substituted by one or two C1-4 alkyl or C1-4 haloalkyl groups; B represents a phenyl group substituted by 1 or 2 R9 groups; R9 represents C1-C4 alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C cycloalkyl, C1-C4 haloalkyl, -C4 alkoxy, C? -C4 haloalkoxy, 2-carboxy-2-propyl, halogen, nitro , cyano, hydroxy, benzyloxy, hydroxymethyl, a -CH2-OCO-R6 group, a -CO-R6 group, a -COO-R6 group, a -SOzR group, or a -NR6R7 group, a -CONR6R7 group, a group -C (= NR¿) NHR? or a group -C (= NRi) OR6; Y represents a simple bond and m = q = 0; and the stereochemistry of the compounds is (R, R).
13. 13. A compound as claimed in claim 1 selected from: (a) (lR, 2R) -l- (4-chlorophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy- l-methyl-3- (lH-l, 2,4-triazol-l-yl) propyl] -5-methyl-lH-pyrazole-4-carboxamide; (b) (lR, 2R) -l- (4-chlorophenyl) -N- [2- (2,4-di-fluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole -l-yl) propyl] -5-trifluoromethyl-lH-pyrazole-4-carboxamide; (c) (1R, 2R) -l- (4-chlorophenyl) -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4-triazole -l-yl) propyl] -3,5-dimethyl-lH-pyrazole-4-carboxamide; (d) (lR, 2R) -N- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazol-1-yl) propyl] -4-methyl-2- (4-trifluoromethylphenyl) thiazole-5-carboxamide; (e) (1R, 2R) -2- (4-chlorophenyl) -jV- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4-triazole -l-yl) propyl] -4-methylthiazole-5-carboxamide; (f) (lR, 2R) -iV- [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole-li.l) propyl] - 4-methyl-2- (4-trifluoromethoxyphenyl) thiazole-5-carboxamide; (g) (1R, 2R) -2- (4-cyanophenyl) -N- [2- (2,4-di-fluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4-triazole -l-yl) propyl] -4-methylthiazole-5-carboxamide; (h) (1R, 2R) -5- (4-chlorophenyl) - / V- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4- triazol-1-yl) propyl] thiophene-2-carboxamide; (i) (1R, 2R) -5- (4-chlorophenyl) -N- [2- (2,4-di-fluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4-triazole -l-yl) propyl] -3-methylthiophen-2-carboxamide; (j) (lR, 2R) -5- (4-cyanophenyl) - - [2- (2,4-difluorophenyl) -2-hydroxy-l-methyl-3- (lH-1, 2,4-triazole -l-yl) propyl] -3-methylthiophen-2-carboxamide; (k) (1R, 2R) -2- (4-cyanophenyl) -N- [2- (2-puorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazole-1) -yl) propyl] -4-methylthiazole-5-carboxamide; (1) (1R, 2R) -N- [2- (2,4-difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1, 2,4-triazol-1-yl) propyl] - 2- (4-ñuorophenyl) -4-methylthiazole-5-carboxamide; or a salt or solvate thereof.
14. 14. A process for preparing a compound of formula I as defined in claim 1, characterized in that it comprises: (a) reacting a compound of formula II p where X, Ri, R2, R3, R4 and Ar have the meaning defined in claim 1, with an acid of formula III m where A, B, Y, myq have the meaning defined in claim 1, in the presence of a condensing agent, or with a reactive derivative of said acid III such as the acid chloride, anhydride or mixed anhydride in the presence of a scavenger base of protons; or (b) transforming a compound of formula I into another compound of formula I into ur.a or several steps; and (c) if desired, after steps (a) or (b), treating a compound of formula I with an acid to give the corresponding addition salt.
15. 15. A pharmaceutical composition characterized in that it comprises an effective amount of a compound of formula I as claimed in claim 1 or a pharmaceutically acceptable salt or solvate thereof mixed with one or more pharmaceutically acceptable excipients.
16. 16. The use of a compound of formula I as claimed in claim 1 or of a pharmaceutically acceptable salt or solvate thereof for the manufacture of a medicament for the treatment or prevention of fungal infections in animals, including humans.
17. 17. An agrochemical composition characterized in that it comprises an effective amount of a compound of formula I as claimed in claim 1 or a salt or solvate thereof mixed with one or more agrochemically acceptable excipients.
18. 18. The use of a compound of formula I as claimed in claim 1 or a salt or solvate thereof for the treatment or prevention of fungal infections in plants.