MXPA96002559A - New derivatives of piperidine with activityantagonist - Google Patents

Abstract

The present invention relates to compounds of general formula I and their salts and solvates are PAF antagonists and as such are useful in the treatment of various diseases or disorders mediated by PAF. Pharmaceutical compositions including these compounds and methods for their preparation are also described.

Description

New derivatives of piperidine with PAF antagonist activity. TECHNICAL FIELD OF THE INVENTION The present invention relates to novel piperidine derivatives which are potent antagonists of platelet activating factor (PAF). The invention also relates to a process for its preparation, to pharmaceutical compositions containing them and to their use in the treatment of diseases in which PAF is involved. Description of the state of the art Platelet activating factor (PAF) or (l-O-alkyl-2-acetyl-sp-0 giicepl-3-phosphorylcholine), also called acetylglyceryl ether phosphorylcholine '' (AGEPC) or PAF-acether, is a natural phospholipid synthesized by several cells (basophils, macrophages, neutrophils, platelets) and tissues (heart, lung and pion) of the organism. PAF was once described as a potent aggregation agent of platelets. Subsequently, it was demonstrated that it possesses other biological actions, such as peripheral vasodilatation, increased vascular permeability, induction of bronchial constriction and airway hyperreactivity. PAF also produces immediate hypotension followed by pulmonary and renal hypertension in rats, 0 guinea pigs, rabbits and dogs, and has been described as the most potent ulcerogenic agent described to date. Therefore, PAF is a mediator that is involved in a wide range of pathological processes such as asthma, septic shock, transplant rejection, thrombosis, ulceration, inflammation and renal diseases. The closest state of the art from the structural point of view is found in EP 441226, which describes pyridylcyanomethylpiperazines and piperidines with PAF antagonist activity, other than the compounds of the present invention. Description of the invention The present invention relates to the new piperidine derivatives of general formula I: I where: m represents 0, 1 or 2; a, b and c represent CR, wherein each R independently represents hydrogen or CM alkyl; R1 represents CM alkyl or C3.7 cycloalkyl; A represents -CO-, -SO2-, -NHCO- or -OCO-; B represents a group of formula (i), and when A represents -CO- or -SO2-, then B may also represent a group of formula (ii) or (iii) n represents 0, 1, 2 or 3; One of R2 or R3 represents C1.4 alkyl, C3.7 cycloalkyl or aryl, and the other represents hydrogen, C alkyl, C haloalkyl, C3.7 cycloalkyl, C1.4 alkoxy-C? 4 alkyl, aryl or aryl -Cμ alkyl; Z represents hydrogen, C1-4 alkyl, -CH2-OR4, -COOR4 or -CONR4R5, and when A represents -CO- or -SO2-, then Z can also be hydroxy, • 2 > -NR4R5, -NR * C (= 0) OR4, -NRC (= 0) R4, -NR ^ C (= O) NRR5, -N (OH) C (= 0) NR4R5 or -NR6SO2R4; or Z and R3 together form a C2.5 polymethylene chain in which case R2 represents C alkyl, C3.7 cycloaikyl or aryl; R4 represents hydrogen, alkyl, aryl or aryl-CM alkyl; R5 and R6 independently represent hydrogen or C alkyl; R7 represents CM alkyl, C3-7 cycloalkyl, aryl, aryl-CM alkyl or bisaryl-C1 alkyl; Y represents hydrogen, C1.4 alkyl, aryl, aryl-C? 4 alkyl, -C (= 0) OR4, -C (= 0) R4, -C (= 0) NR4R5, Ó -SChR4; Aryl, whenever it appears in the above definitions, represents phenyl or phenyl substituted by 1, 2, 3 or 4 groups independently chosen from halogen, C1.4 alkyl, C alkoxy, hydroxy, C haloalkyl, CM haloalkoxy, cyano, nitro , amino, C1. aiquilamino, C1. dialkylamino, C1.4 alkylcarbonyl, C) .4 alkylcarbonyloxy, C1.4 alkoxycarbonium, C1.4 alkylsulfonyl, C1.4 alkylsulfinyl, CM alkylthio, CM alkylcarbonylamino or alkoxycarbonyl; 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 and a pharmaceutically acceptable excipient. The invention also 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 1 0 diseases mediated by PAF. The use for the manufacture of a medicament for the treatment or prevention of ischemia and shock states such as septic shock, anaphylactic shock, hemorrhagic shock and myocardial ischemia is preferred; pancreatitis; and diseases related to allergy and inflammation such as asthma, dermatitis, 1 5 urticaria, arthritis and psoriasis. 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 diseases mediated by PAF. It is preferred to use for the treatment or prevention of ischemia states and of shock such as septic shock, anaphylactic shock, hemorrhagic shock and myocardial ischemia; pancreatitis; and diseases related to allergy _ and inflammation such as asthma, dermatitis, urticaria, arthritis and psoriasis. The invention further provides a method of treatment or prevention of diseases mediated by PAF in a mammal, which comprises administering to said mammal an effective amount of a compound of formula I or a pharmaceutically acceptable salt or solvate thereof. A method of treatment or prevention of ischemia and shock states such as septic shock, anaphylactic shock, hemorrhagic shock and myocardial ischemia is preferred; pancreatitis; and diseases 3 0 related to allergy and inflammation such as asthma, dermatitis, urticaria, arthritis and psoriasis in a mammal in need thereof, said method comprising administering to the mammal an effective amount of a compound of formula 1 or a pharmaceutically acceptable salt or solvate acceptable of it. The invention also provides a process for preparing a compound of formula I, comprising: (A) reacting a compound of formula II, wherein a, b, c, m and R1 have the meaning described above, with an acid of the formula BCOOH (III) or a suitable derivative thereof such as the acid chloride or the anhydride, a sulfonyl chloride of the formula BSO2CI (IV), a compound of formula BOC (= 0) G (V), a compound of formula 'BNHC (= 0) G (VI) or a compound of formula BN = C = 0 (VID, where B possesses 1 0 the meaning described above and G represents a good outgoing group! as chlorine or -OPh; or (B) transforming a compound of formula I into another compound of formula I in one or more steps; and (C) if desired, after steps A or B, reacting a compound of Formula I with an acid to give the corresponding addition salt. The invention also provides the new intermediates of formula p p where a, b, c, m and R 1 have the meaning described above for the compounds of formula I. The compounds of formula II are valuable intermediates in the preparation of the compounds of the present invention. The compounds of formula I may possess one or more chiral centers, which may give rise to stereoisomers. The present invention covers each of the individual stereoisomers as well as their mixtures. Likewise, some of the compounds of the present invention may present cis / trans isomerism. The present invention covers each of the geometric isomers as well as their mixtures. In the above definitions, the term C M alkyl, as a group or as part of a group, means a linear or branched alkyl group containing from one to four carbon atoms. Thus, it includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sfc-bualo, and ferf-butyl. The term "alkoxy CM", as a group or as part of a group, means a group resulting from the attachment of an alkyl group C as mentioned above to an oxygen atom of an ether functional group. Examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, and irf-butoxy. A halogen group or its abbreviation halo represent fluoro, chloro, bromo or iodo. A C3.7 cycloalkyl group represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl. A C2-5 polymethylene group represents ethylene, propylene, butylene and pentylene. A "haloalkyl" group means a group resulting from the substitution of one or more hydrogen atoms of an alkyl group by one or more halogen atoms (i.e., fluoro, chloro, bromo or iodo), which may be the same or different . Examples include trifluoromethyl, fluoromethyl, chloroethyl, fluoroethyl, iodoethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, fluoropropyl, chloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, fluorobutyl, and nonafluorobutyl. A "C Haloalkoxy" group means a group resulting from the substitution of one or more hydrogen atoms of an alkoxy CM group by one or more halogen atoms, which may be the same or different. Examples include trifluoromethoxy, fluoromethoxy, chloroethoxy, fluoroethoxy, iodoethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, fluoropropoxy, chloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, fluorobutoxy, and nonafluorobutoxy. A C M alkylamino or CM dialkylammo group represents a group resulting from the substitution of one or two hydrogen atoms, respectively, of an amino group by one or two alkyl CM groups, which may be the same or different. Examples include methylamino, dimethylamino, ethylamino, diethylamino, ethylmethylamino, propylamino, dipropylammon, isopropylamino and diisopropylamm. A C1-4 alkylcarbonyl group represents a group resulting from the attachment of a C alkyl group to a carbonyl group. Examples include acetyl, propanoyl, isopropanoyl, and butanoyl. A CM alkylcarbonyloxy group represents a group resulting from the attachment of a CM alkylcarbonyl group to an oxygen atom of an ether functional group. Examples include acetoxy, propanoxy, isopropanoxy, and butanoxy. A CM alkoxycarbonyl group represents a group resulting from the attachment of a C-alkoxy group to a carbonyl group. Examples include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl and tert-butoxycarbonyl. A CM alkylsulfonyl group represents a group resulting from the attachment of a C1.4 alkyl group to a sulfonyl group. Examples include methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, and tert-butylsulfonyl. A C1.4 alkylsulfinyl group represents a group resulting from the attachment of a C alkyl group to a sulfinyl group. Examples include rnetylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, and ftri-butylsulfinyl. A CM alkylthio group represents a group resulting from the attachment of a CM alkyl group to a sulfur atom of a thioether functional group. Examples include methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, s-butylthio, and butyl-butylthio. A CM alkylcarbonylamino group represents a group resulting from the substitution of a hydrogen atom of an amino group with a C 1 -4 alkylcarbonyl group. Examples include acetamido, propanamido and isopropanamido. A CM alkoxycarbonylamino group represents a group resulting from the substitution of a hydrogen atom of an amino group by a C 1 -4 alkoxycarbonyl group. Examples include n-methoxycarbonylamino, ethoxycarbonylamino, propoxycarbonylamino, isopropoxycarbonylamino, butoxycarbonylamino, isobutoxycarbonylamino, sec-butoxycarbonylamino and tt-butoxycarbonylamino. A CM alkoxyCM alkyl group represents a group resulting from the substitution of a hydrogen atom of an alkyl CM group by a group C 1 -4 alkoxy. Examples include among others methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, butoxymethyl, isobutoxymethyl, sec-butoxymethyl, / err-butoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2-isobutoxyethyl, 2 -sec-Butox? ethyl, 2-tert-butoxyethyl, 1 -metoxietilo, 1 -etoxietilo, 1 -propoxietilo, 1-isopropoxyethyl, 1-butoxyethyl, 1 -isobutoxietilo, 1-sec-butoxyethyl, and l-IERT-butoxyethyl. An aryl-Cj-4 alkyl group represents a group resulting from the substitution of a hydrogen atom of a C] -A alkyl group by an aryl group as defined above. Examples include among others, benzyl, -phenylethyl, 3-phenylpropyl, 2-phenylpropyl, 1 -fenilpropilo, 4-phenylbutyl, 3-phenylbutyl, 2-phenylbutyl and 1-phenylbutyl, wherein the phenyl groups may be substituted as has described above in the definition of an aryl group. A β-saryl-C? -4 alkyl group represents a group resulting from the substitution of two hydrogen atoms of an alkyl C group by two aryl groups as defined above, which may be the same or different. Examples include among others, diphenylmethyl, 2,2-diphenylethyl, 1,1-diphenylethyl, 2-diphenylethyl, 3,3-diphenylpropyl, 2,2-diphenylpropyl, 1,1 -difenilpropilo, 3,2-diphenylpropyl, 1, 3-diphenylpropyl, and 1,2-diphenylpropyl, wherein the phenyl groups may be substituted as described above in the definition of an aryl group. Preferred compounds include them where, independently or in any compatible combination: m represents 1 or 2; n represents 0, 1 or 2; A represents -CO- or -SO2-; A represents -NHCO- or -OCO-; B represents a group of formula (i); B represents a group of formula (ii); B represents a group of formula (iii); Z represents hydrogen, C alkyl, -CH2-OR4, -COOR4, or -CONR R5, and when A represents -CO- or -SO2-, Z can also represent hydroxy, -NR6C (= 0) OR4, -NR6C (= 0) R4 or -NR6SO2R4; Z and R3 together form a C2.5 polymethylene chain; R7 represents C alkyl, C3.7 cycloalkyl or aryl; Aryl represents phenyl or an alkyl substituted by 1, 2, 3 or 4 groups independently chosen from halogen, CM alkyl, CM alkoxy, hydroxy, CM haloalkyl, CM haloalkoxy or amino. Thus, a preferred class of compounds of formula I is that wherein: m represents 1 or 2; a, b and c represent CR, wherein each R independently represents hydrogen or Ci-t alkyl; R1 represents CM alkyl or C3-7 cycloalkyl; A represents -CO- or -SO2-; B represents a group of formula (i), (ii) or (iii) n represents 1 or 2; one of R2 or R3 represents C1.4 alkyl, C3-7 cycloalkyl or aryl, and the other represents hydrogen, CM alkyl, CM haloalkyl, C3.7 cycloalkyl, C alkoxy-C alkyl, aryl or aryl-CM alkyl; Z represents hydrogen, alkyl CM, -CH2-OR4, -COOR4, -CONR R5, hydroxy, -NRÍ ^ OJOR4, -NR * C (= 0) R4 or -NR6SO2R4; or Z and R3 together form a C2.5 polymethylene chain in which case R2 represents C alkyl, C3-7 cycloalkyl or aryl; R4 represents hydrogen, alkyl, aryl or aryl-CM alkyl; R5 v R6 independently represent hydrogen or CM alkyl; R7 represents C alkyl, C3-7 cycloalkyl or aryl; Y represents hydrogen, C alkyl, aryl, aryl-CM alkyl, -C (= 0) OR4, -C (= 0) R4, -C (= 0) NR4R5, or -SO2R4; and aryl in the above definitions represents phenyl or phenyl substituted by 1, 2, 3 or 4 groups independently chosen from halogen, alkyl CM, C alkoxy, hydroxy, CM haloalkyl, CM haloalkoxy or amino. A preferred group of compounds within this class is that wherein: B represents a group of formula (i) or (iii); one of R2 or R3 represents C 1.4 alkyl, C3.7 cycloalkyl or aryl, and the other represents hydrogen, C 1.4 alkyl, C haloalkyl, C3.7 cycloalkyl, C. .4 alkoxy-CM alkyl, aryl or aryl-C M alkyl; Z represents hydrogen, C alkyl, -CH2-OR4, -COOR4 or hydroxy; or Z and R3 together form a C2-5 polymethylene chain in which case R2 represents C alkyl, C3.7 cycloalkyl or aryl; R 4 represents hydrogen, C M alkyl, aryl or aryl-C 4,4 alkyl; R7 represents C1-4 alkyl, C3-7 cycloalkyl or aryl; and Y represents CM alkyl, aryl, or -5? 2R4- Another preferred group of compounds within this class is that wherein: B represents a group of formula (ii); and one of R2 or R3 represents CM alkyl or aryl, and the other represents hydrogen, C alkyl, CM alkoxy-CM alkyl, aryl or aryl-CM alkyl. Another preferred class of compounds of formula I is that wherein: m represents 1 or 2; a, b and c represent CR, wherein each R independently represents hydrogen or CM alkyl; R1 represents CM alkyl or C3-7 ocloaikyl; A represents -NHCO- or -OCO-, B represents a group of formula (i); (i) n represents 0 or 1; one of R2 or R3 represents C alkyl, C3.7 cycloalkyl or aryl, and the other represents hydrogen, CM alkyl, C M haloalkyl, C3.7 cycloalkyl, C 1-4 alkoxy-C? _4 alkyl, aryl or aryl-CM alkyl; Z represents hydrogen, C alkyl, -CH2-OR4, -COOR4, or -CONR R5; or Z and R3 together form a C2-5 polymethylene chain in which case R2 represents C M alkyl, C3.7 cycloalkyl or aryl; R4 represents hydrogen, alkyl, aryl or aryl-CM alkyl; R5 represents hydrogen or CM alkyl; and aryl in the above definitions represents phenyl or phenyl substituted by 1, 2, 3 or 4 groups independently chosen from halogen, C M alkyl, C alkoxy, hydroxy, C M haloalkyl, C haloalkoxy or ammo. Below are the formulas of some specific compounds, along with the number corresponding to the example where its preparation is described: NH, The compounds of formula I contain basic nitrogen atoms and, therefore, can form salts with. acids, which are also included in the present invention. There is no limitation on the nature of these salts, with the proviso that, when 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 unacceptably increased toxicity) compared to 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, citric acid, succinic acid, tartaric acid; and other mineral and carboxylic acids well known to those skilled in the art. The salts are prepared by reaction of 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. The compounds of the present invention can exist in unsolvated form as well as in solvated forms, 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. Some compounds of the present invention may exist in the form of diastereomeric vanes and / or optical isomers. The diastereoisomers can be separated by conventional techniques such as chromatography or fractional crystallization. The optical isomers can be resolved by using any of the 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. Optical resolution techniques include the separation by chromatography on a chiral phase or the formation of a diastereoisomeric pair, resolution and subsequent recovery of the two enantiomers. The optically pure isomers can also be obtained individually using enantiospecific synthesis. The present invention covers both the individual isomers and their mixtures (for example racemic mixtures), whether obtained by synthesis or by mixing them physically. Likewise, some of the compounds of the present invention may present cis / trans isomerism. Geometric isomers can be separated by conventional techniques such as chromatography or rectalization. Said separation can be carried out both on the products of formula I and on any of their synthesis intermediates. The individual isomers can also be obtained using stereospecific synthesis. The present invention covers each of the geometric isomers as well as their mixtures. The compounds of formula I can be prepared using the methods described below. As will be apparent to those skilled in the art, the precise method used for the preparation of a given compound may vary depending on its chemical structure. The reactions are carried out in an appropriate solvent for the reagents and materials used and that is suitable for the transformation that is being carried out. In addition, in some of the methods described below it will be desirable or necessary to protect the reactive or labile groups by conventional protecting groups, for example the groups described below. Both the nature of these protecting groups and the methods for their introduction and removal are well known in the art (see for example Greene T. W., "Protective Groups in Organic Synthesis", John Wiley & amp;; Sons, New York, 1981). The compounds of formula I can be obtained in general from the amines of formula II by reaction with an acid chloride of formula BCOCI (VIII), a sulfonyl chloride of the formula BSO2CI (IV), a compound of the formula BOC (= 0) G (V), a compound of the formula BNHC (= 0) C (VI) or a compound of the formula BN = C = 0 (VII): BCOCI (HIV) (ID where B, a, b, c, m and R1 have the meaning described above and G represents a good leaving group such as chlorine or -OPh. This reaction is carried out in the presence of a proton-binding amine such as rpetilamine or pyridine in a suitable solvent, or using the base as a solvent. Examples of suitable solvents include halogenated hydrocarbons, such as dichloromethane and chloroform; ethers, such as diethyl ether, tetrahydrofuran and dioxane; and aromatic hydrocarbons, such as benzene and toluene. The reaction is carried out at a temperature preferably between 0 ° C and the boiling point of the solvent. As an alternative to the acid chloride, the anhydride can be used. Isocyanates of formula VII can be prepared previously or can be generated in situ from the corresponding acid of formula BCO2 H (III) by known methods such as for example by treatment with diphenylphospholazide in the presence of tetylamine. As will be apparent to those skilled in the art, a compound of formula 1 wherein A represents -NHCO- can also be prepared by invoking the functionality of the reactive groups involved, ie by reacting an amine of formula BNH2 (IX) with a carbamate "' Reagent derived from amine II, for example its phenylcarbamate, which can be prepared from amine II by conventional methods such as, for example, by treatment with phenyl chloroformate under usual conditions, Alternatively, compounds of formula I wherein A represents -CO- can also be prepared by a dehydration process between the amines of formula II and a carboxylic acid of formula BCOOH (III). This process can be carried out using any conventional reaction of amide bond formation, such as for example the reaction of an amine with an acid in the presence of a suitable condemning agent such as a diimide, e.g. dicyclohexycarbodiimide, alone or in combination with 1-hydroxybenzotpazole. This reaction is carried out in an inert solvent such as a halogenated hydrocarbon, for example dichloromethane or chloroform; an ether, for example tetrahydrofuran or dioxane; acetonitrile; or dimethylformamide. The reaction is carried out at a temperature preferably comprised between 0 and 60 ° C during a reaction time preferably ranging from 6 to 24 hours. In addition, a compound of formula I can also be obtained by interconversion of another compound of formula I. Thus, for example, the compounds of formula I in which B represents a group of formula (i) wherein Z represents -NR6C (= 0 ) OR4, -NR6C (= 0) R4, -NR6C (= 0) NR4R5 or -R6SO2R4 or a group of formula (iii) where Y is other than hydrogen can be prepared from the corresponding compounds of formula I in which B represents a group of formula (i) wherein Z represents -NHR6 or a group of formula (iii) where Y = H, respectively, by conventional reactions, well known to those skilled in the art, as shown in the Scheme 1. Examples thereof include alkylations, acylations, formation of sulfonamides, carbamates and ureas. These reactions are widely described in the literature and are carried out under the usual conditions used in organic chemistry for this type of transformation. These compounds of formula I in which B represents a group of formula (i) wherein Z represents -NHR6 or a group of formula (iii) wherein Y = H can be prepared by the general procedures described above for the preparation of compounds I but starting from an acid of formula III (or the corresponding acid or anhydride chloride) or of a sulfonyl chloride of formula IV wherein the ammo group is protected by an amine protecting group (P), as shown in Scheme 1. As any amine protecting groups, any known amine protecting group, such as a tert-butoxycarbonium group, can be used. In this case, a subsequent step of removing the protecting group to obtain a compound of formula I will be necessary. The deprotection is carried out using conventional procedures, such as the procedures described below. p Scheme 1 where a, b, c, R1, R2, R3, R6, R7, m and n have the meaning described above; A represents -CO- or -SO2-; P represents an amine protecting group, such as a fer / -butoxycarbonyl group and Q represents a CO2H group (thus giving acids of formula III) or a SO2CI group (thus giving sulfonyl chlorides of formula IV). Another example of interconversions between compounds of formula I is the reduction of a nitro group in a compound of formula I to an amino group. This reduction can be carried out using any known aromatic nitros reducing agent that is compatible with the rest of the functional groups present in the molecule. Examples of suitable reducing agents include: Zn at different pH conditions within a suitable solvent such as ethanol-water mixtures at a temperature preferably between room temperature and that of the boiling point of the solvent, more preferably between 50 and 60 ° C; Na 2 S 2 γ 4 in a suitable solvent as mixtures of water and an organic solvent, for example tetrahydrofuran, ethanol or pyridine; SnCh at different pH conditions in a suitable organic solvent such as ethanol; Sn or Fe at different pH conditions; NaBRj in the presence of a suitable catalyst such as a salt of Sn, Co or Pd in a suitable organic solvent such as ethanol; and formic acid or ammonium formate in the presence of Pd / C. Alternatively, the reduction can be carried out by hydrogenation in the presence of a catalyst such as palladium on carbon in a suitable solvent such as an alcohol at a temperature preferably between room temperature and that of the boiling point of the solvent, at a pressure preferably between atmospheric pressure and 10 atmospheres and during a reaction time preferably between 1 and 48 h. As will be apparent to those skilled in the art, interconversions between substituents such as those described above can be performed both on the final compounds of formula I and on any of their synthesis intermediates. The salts of the compounds of formula I can be prepared by conventional methods by treatment for example with an acid such as hydrochloric acid, sulfuric acid, nitric acid, oxalic acid or fumaric acid.

The amines of formula I I can be prepared following the procedure described in Scheme 2, which is shown below: Scheme 2 where a, b, c, m and R1 have the meaning described above; P represents an amine protecting group such as a f? R / -butoxycarbonyl group and L represents halogen or C? -6 alkoxy. In a stepper stage (step A), a compound of formula X is reacted with a compound of formula XI in the presence of a proton-binding amine such as tetthylamine in a suitable solvent such as a halogenated hydrocarbon, for example chloroform, at a suitable temperature, preferably between room temperature and that of the boiling point of the solvent, to give a compound of formula XII. The reduction of a compound of formula XII (step B) leads to a compound of formula XIII. This reduction can be carried out by hydrogenation in the presence of a catalyst such as palladium on carbon in a suitable solvent such as an alcohol at a temperature preferably between room temperature and that of the boiling point of the solvent, at a pressure preferably between atmospheric pressure and 10 atmospheres and during a reaction time preferably between 1 and 48 h. Alternatively, this reduction can be carried out using a suitable reducing agent such as Na 2 S 2+ 4 in a suitable solvent such as mixtures of water and an organic solvent, for example tetrahydrofuran, ethanol or pyridine. In step C, a compound of formula XIII is reacted with a salt of an imino ether of formula R1C (= N H) OR8.HX (XV, where R1 has the meaning described above, R8 represents Ci-t, alkyl and X represents halogen) in a suitable solvent such as an alcohol, for example ethanol, to give a compound of formula XIV. This reaction is carried out at a temperature preferably between room temperature and that of the boiling point of the solvent, during a reaction time preferably between 6 and 48 h. Alternatively, instead of the imino ether it is possible to use a carboxylic acid of the formula R COOH (XVI), an acid halide of the formula R'COX (XVII), an anhydride of the formula (R'CO ^ O (XVIII) or a trialkylortoester of formula R! C (OR8) 3 (XIX), where R ', X and R8 have the meaning described above Finally, deprotection of the piperidine nitrogen atom of a compound of formula XIV (step D) leads to a compound of The agent employed for this deprotection as well as the reaction conditions used will depend on the nature of the protecting group employed.So, if the protecting group is an iver / -butoxycarbonyl group, the deprotection can be carried out by treatment with an acid (for example an inorganic acid such as hydrochloric acid, phosphoric acid, sulfuric acid or the like or an organic acid such as toluenesulfonic acid, methanesulfonic acid, acetic acid, or trifluoroacetic acid) in the breast of a suitable solvent such as water, an alcohol (eg. methanol), an ether (eg tetrahydrofuran or dioxane) or a halogenated hydrocarbon (eg dichloromethane), at a temperature preferably between 0 ° C and room temperature. The above reactions are all known per se and are carried out according to the described procedures. The acids of formula III and the sulfonyl chlorides of formula IV are commercial, are widely described in the literature or can be prepared by methods known to those skilled in the art, starting from commercial products or products that have already been described in the literature. . Examples of these refiners include alkylaones, alloys, conjugated additions to double bonds, Wittig reaction for the preparation of double bonds, preparation of sulfonamides, reductive aminations, and the like. All these reactions are known per se and are carried out in accordance with the conditions already described. The compounds of formulas BOC (= 0) G (V) and BNHC (= 0) G (VI) can be easily prepared from the corresponding alcohols and amines of the formulas BOH and BNH2, respectively, by conventional methods, for example by treatment with phenyl chloroformate. The isocyanates of the formula BN = C = 0 (VII) can be prepared from the acids of the formula BCOOH (III) by a sequence comprising the following steps: transformation of the acid to an acylazide by treatment for example with diphenylphosphorylazide; and subsequent Curtius rearrangement of said acylazide to give an isocyanate. This sequence for the synthesis of isocyanates from carboxylic acids is widely described in the literature and can be carried out under the conditions already described. The compounds of formulas X, XI, XV, XVI, XVII, XVIII and XIX, as well as the alcohols of formula BOH and the amines of formula BNH2 are commercial, are widely described in the literature or can be prepared by methods analogous to those described from commercially available products. The compounds of general formula I, being potent antagonists of the PAF, are useful as preventive and therapeutic agents for the treatment of circulatory diseases in which the PAF is involved, such as thrombosis, stroke (eg cerebral hemorrhage, cerebral thrombosis), angina pectoris, thrombotic phlebitis, thrombocytopenic purpura, nephritis (eg glomerulonephritis), diabetic nephrosis, pancreatitis; states of ischemia and shock (eg, septic shock observed after a severe infection or in a postoperative process, intravascular coagulation syndrome caused by endotoxin, anaphylactic shock, hemorrhagic shock, myocardial ischemia); diseases of the digestive system in which FAP is involved (eg gastric ulcer, inflammatory bowel disease); diseases related to allergy and inflammation (eg asthma, dermatitis, urticaria, arthritis, psoriasis); pneumonia; rejection due to an increase in PAF production after organ implantation; postoperative organic dysfunctions (eg in heart, liver and kidney) and any other disease in which PAF is involved. They could also be used for contraception in mammalian females by suppression of cell division and / or ovimplantation in the uterus, in the treatment of endometriosis and for the prevention or treatment of hyperendotelinemia caused by excessive secretion of endothelin. In accordance with the activity of the disclosed compounds, the present invention also provides compositions comprising a compound of the 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 route of administration chosen 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, microcrystalline cellulose or calcium phosphate; with binding agents and disintegrants such as, for example, 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 to delay their disintegration and absorption in the gastrointestinal tract and, thus, achieve a sustained action over a longer period. 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. Soft gelatine capsules are also possible, in which the active ingredient is mixed with water or with an oily medium, for example arachis oil, liquid paraffin or olive oil. In the dispersible and granulated powders suitable for the preparation of suspensions by the addition of water, the active principle is mixed with dispersing agents or wetting agents, suspending agents, such as the cavofilmible cel or sodium slab, me ti l ce slab, hydroxypropylmethylcellulose, sodium alginate, polyvinylpyrrolidine, gum tragacanth, xanthan gum, gum arabic, and one or more preservatives, such as methyl p-hydroxybenzoate or p-propyium. Additional excipients may also be present, for example sweeteners, flavorings and colorants. Liquid formulations for oral administration include emulsions, solutions, suspensions, syrups and elixirs containing inert diluents commonly used, such as distilled water, ethanol, sorbitol, glycerol or propylene glycol. Said compositions may also contain adjuvants such as wetting, suspending, sweetening, flavoring, perfuming, preservative and pH regulating agents. Other compositions for oral administration include sprays and aerosols, which can be prepared by known methods. These compositions, which can disperse the active principle in the form of drops of a solution or suspension or in the form of powders, must contain a suitable propellant agent. Injectable preparations, in accordance with the present invention, for parenteral administration in both bolus and continuous infusion form, include sterile aqueous or non-aqueous solutions, suspensions or emulsions, in a suitable 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. Examples of non-aqueous solvents or suspending media are propylene glycol, polyethylene glycol, vegetable oils such as olive oil, or alcohols such as ethanol. These compositions may also contain adjuvants, such as wetting agents, preservatives, emulsifiers and dispersants. They can be sterilized by any of the known methods or prepared as sterile solid compositions which can be dissolved in 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. A compound of the present invention can also be administered in the form of suppositories or enemas (including aqueous or oily solutions as well as suspensions and emulsions) for rectal administration of the drug. These compositions are prepared following conventional procedures; for example, suppositories can be prepared by mixing the active ingredient with a conventional suppository base such as cocoa butter or other glycerides. Compositions for topical administration of a compound of the present invention include creams, ointments, pastes, lotions, gels, sprays, foams, aerosols, solutions, suspensions or powders. Said compositions are conventional formulations and can be prepared according to procedures well known in the art. When the compounds of the invention are to be administered to the eyes, they can be formulated in the form of solutions or suspensions in suitable aqueous or non-aqueous sterile solvents. These compositions can also contain pH regulators and preservatives. Dosage and frequency of doses may vary depending on the symptoms, age and body weight of the patient, as well as depending on the route of administration, but, in general, the compounds of the invention can be administered orally at a daily dose of 1. -1000 mg for an adult, preferably a dose of 5-250 mg, which can be administered as a single dose or as a multiple dose. A preferred dosage for human patients is 0.005 to 20 mg / kg of body weight, more preferably 0.05 to 5 mg / kg of body weight. Formulations for topical administration will typically contain 0.5-10% by weight of a compound of formula I. Some representative formulations for tablets, capsules, syrups, aerosols, injectable preparations and creams are cited below. They can be prepared by conventional methods and are useful in the treatment of diseases mediated by PAF.

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 Hard gelatin capsules Compound of formula I 100 mg Lactose 197 mg Magnesium stearate 3 mg 300 mg laxate Compound of formula I 0.4 g Sucrose 45 g Flavoring agent 02 g Sweetener 0.1 g Water c.s.p. 100 m i Aerosol Compound of formula I 4 g Flavoring agent 02 g Propylene glycol c.s.p. 100 m i Propellant suitable c.s.p. 1 unit Injectable Compound of formula I 100 mg Benzyl alcohol 0.05 m i Propylene glycol 1 m i Water cs.p. 5 m i Cream Compound of formula I 2 g Dimethyl acetamide 2 g White paraffin 25 g Stearic alcohol 22 g Propylene glycol 12 g Sodium lauryl sulfate 1.5 g Methylparaben 03 g Purified water 31.6 g The following pharmacological tests explain the activity of the compounds of the present invention in more detail.

PHARMACOLOGICAL TEST 1 Inhibition of platelet aggregation induced by PAF Platelet aggregation studies were performed by the Bom method (Physwl, 1962, 162, 67). The blood was collected in 3.16% sodium citrate (1 volume per 9 volumes of blood) by cardiac puncture in male New Zealand rabbits (2-2.5 kg body weight). Platelet-rich plasma (PRP) was prepared by centrifugation of the blood at 250xg for 10 min at 4 ° C. The PRP was diluted with platelet poor plasma (PPP) obtained by additional centrifugation at 3000xg for 10 min. The number of platelets was adjusted to 3xl05 cells / mm3. Platelet aggregation was induced with Ciß-PAF (15 nM) and determined with a two-channel aggregometer Chrono-log 560. The activity was expressed as the IC 50 value, ie the concentration of the drug necessary to inhibit platelet aggregation in a fifty%. The results are shown in table 1 below. TABLE I Compound IC50 (μM) N ' 1 0.0076 16 0.0092 17a 0.018 17b 0.0050 21 0.0069 23 0.011 32 0.011 39 0.016 40 0.012 41 0.0067 44 0.019 47 0.036 50 0.013 59 0.017 60 0.017 61 0.0062 70 0.034 PHARMACOLOGICAL TEST 2 Inhibition of PAF-induced hypotension in normotensive rats. Male Sprague Dawley rats, weighing 180-220 g, were anesthetized with sodium pentobarbital (50 mg / Kg,? .p.). The artepal pressure was measured in the left carotid artery using a Statham pressure transducer coupled to a Beckman R6 1 polygraph. The left and right femoral veins were catheterized to inject the compounds to be tested and the PAF (0.5 μg / Kg). The tested compounds were administered by intravenous injection (1 mL / Kg, dissolved in physiological saline) 3 min. before the PAF. Blood pressure was monitored and the percent inhibition of PAF-induced hypotension was calculated with respect to the controls. The results were expressed as the ID 50 values, that is, the dose of compound tested to inhibit hypotension in a 50Tc. The results are shown in Table II. TABLE II Compound DI50 (mg / Kg) N D 1 0.0086 17a 0.029 17b 0.01-0.025 21 0.043 30 0.015 32 0.0079 40 0.033 41 0.012 47 0.013 50 0.017 59 0.021 60 0.019 70 0.014 The following examples illustrate, but do not limit, the scope of the present invention: REFERENCE EXAMPLE 1 l-ferf-Butoxycarbonyl-4- (aminomethyl) piperidine On a cooled (0 ° C) solution of 4- (am? Nomet? ) p? peridone (40 g, 0.35 moi) in CHCl3 (300 mL) was added a solution of di-tert-butyl dicarbonate (39.2 g, 0.17 mol) in CHCl3 (300 mL) and the mixture was stirred. reaction at room temperature for 18 h. The resulting solution was washed with H2O and the aqueous phase was reextracted with CHCl3. The combined organic phases were dried and concentrated to give a crude (54.1 g), which was used directly in the next step as obtained. ! H NMR (80 MHz, CDCl 3) d (TMS): 4.11 (broad d, J = 13.4 Hz, 2 H), 2.69 (m, 4 H), 1.45 (s, 9 H), 1.8-0.8 (complex signal, 7 H). REFERENCE EXAMPLE 2 4 - ((l- (r rf-Butoxycarbonyl) -4-piperidylmethylaminol-3-n? Ttopyridine On a cooled (0 ° C) solution of 4-chloro-3-n? Trop? Rid? Na ( 83.7 g, 0.53 mol) in CHCl3 (700 mL) was added a solution of the product obtained in the example of reierarena 1 (140 g, 0.65 mol) and Et 3 N (110 mL) in CHCl 3 (500 mL) and the mixture was heated to reflux during 18 h. It was concentrated, and the residue was partitioned between IN NaOH and AcOEt. The aqueous phase was reextracted twice with AcOEt, and the combined organic extracts were dried and concentrated to a total volume of 400 mL. After cooling (-20 ° C) overnight, a yellow solid was collected and dried (115 g, 64%). mp 131-138 ° C. ] H NMR (80 MHz, CDCI3) d (TMS): 9.20 (s, 1 H), 8.30 (d, J = 5.5 Hz, 1 H), 8.19 (m, 1 H), 6.72 (d, J = 5.5 Hz , 1 H), 4.18 (wide d, j = 13.4 Hz, 2H), 3.26 (t, J = 5.9Hz, 2H), 2.72 (wide t, j = 12.7Hz, 2H), 1.46 (s, 9H), 1.8-0.8 (complex signal, 5H). REFERENCE EXAMPLE 3 3-Amino-4 - ([1- (I-butoxycarbonyl) -4-piperidylmethylaminolpyridine A mixture of the product obtained in reference example 2 (26.2 g, 0.077 mol) and Pd / C 10% (3.83 g) ) in MeOH (500 mL) was hydrogenated at atmospheric pressure for 18 h, the catalyst was filtered and the filtrate was concentrated to give a crude (22.9 g, 96%), which was used directly in the next step as obtained Í H NMR (80MHz, CDCI3) d (TMS) 7 65 (d, J = 5.5Hz, 1 H), 7 64 (1H), 6.59 (d, J = . 5Hz, 1 H), 4 10 (wide d, J = 13 4 Hz, 2H), 3 9 (s 3H), 3.25 (d, 1 = 6.5Hz, 2H), 2.74 U wide, J = 12.0Hz, 2H), 1 46 (s, 9H), 1.8-0.8 (complex signal, 5H) Alternatively, the title compound was prepared as follows: On a solution of the product obtained in reference example 2 (82.2 g, 0.244 mol ) in pyridine (400 mL) was added a solution of Na2S2? '* (170 g, 0.976 mol) in H2O (500 mL). The mixture was stirred at room temperature for 24 h, and partitioned between AcOEt (800 mL) and 5N NaOH (450 mL). The organic phase was separated, dried and evaporated to give a yellow solid (101 g), which still contained pyridine. REFERENCE EXAMPLE 4 l- [. { l- (fírt-Butoxicarbonil) -4-piperidil] metill-lH-2-methylimidazo (4,5-clpiridine On a solution of the product obtained in reference example 3 (22.9 g, 0.07 mol) in EtOH (350 mL) was added ethyl acetimidate hydrochloride (9.2 g, 0.074 mol) and the mixture was heated at reflux for 4 h. A second equivalent of ethyl acetimidate hydrochloride (9.2 g, 0.074 mol) was added and heated to reflux for a further 18 h. Finally, a third was added ,, equivalent of ethyl acetimidate hydrochloride (9.2 g, 0.074 mol) and the mixture was heated for a further 4 h. The solvent was removed in vacuo and the residue was partitioned between CHCl3 and 0.5N NaOH. The organic phase was dried and concentrated to give a crude (30 g), which was purified by chromatography on silica gel (CHC: MeOH, 10%) to give the title compound as a yellow solid (23.4 g, 95%) . ! H NMR (80MHZ, CDCI3) d (TMS): 8.98 (1H), 8.38 (d, J = 5.5HZ, 1H), 7.22 (d, J = 5.5Hz, 1H), 4.10 (d) width, J = 13.4 Hz, 2H), 3.96 (d, J = 7.3Hz, 2H), 2.64 (wide t, J = 12.7Hz, 2H), 2.63 (s, 3H), 1.46 (s, 9H), 2.2 -1.0 (complex signal, 5H). REFERENCE EXAMPLE 5 l- | (4-Piperidyl) methyl) -l H-2-methylimidazo. { 4,5-Clpyridine A solution of dioxane / HClig) 6.5N was added dropwise to a cooled (0 ° C) solution of the product obtained in the example of reierarena 4 (23.1 g, 0.07 mol) in MeOH (200 mL). (44 mL). The mixture was stirred at room temperature for 2 h and evaporated to dryness. The residue was cooled (0 ° C), NaN NaOH was added and the resulting solution was extracted with CHCl3 (3x). The combined organic extracts were dried and concentrated to give a yellow solid (15.8 g, 98%). ] H NMR (80 MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), S.35 (d, j = 5.5 Hz, 1 H), 7.20 (d, J = . 5Hz, 1 H), 3.95 (d, J = 7.3Hz, 2H). 3.06 (d wide, J = 12.0 Hz, 2H), 2.61 (s 3H), 2.51 (t wide,) = 12.7Hz, 2H), 2.2-1 .0 (complex signal, 6H). REFERENCE EXAMPLE 6 l- (4-Piperidyl) -lH-2-methylimidazo (4,5-clpyridine, hydrochloride Following the procedure described above in reference examples 1-5, but starting from the 4-ammop? Perid? Na instead of 4- (amomethyl) p-peridin, the title compound (56%) was obtained] H NMR (80MHz, CD3OD) d (TMS) 9 32 (s 1 H) 8.82 (d, J = 5 5 Hz. 1 H) 8.62 (d j = 5.5 Hz, 1 H), 5 17 (s, 1 H), 3.9-2.2 (complex signal, 9H) REFERENCE EXAMPLE 7 Acid 3.3 -diphenyl-3-ethoxycarbonylpropanoic a) Ethyl diphenylacetate On a diphenylacetic acid solution (20 g, 0.094 mol) in EtOH (70 mL), toluene (70 mL) was added. Then, H2SO4 (3 mL) was added dropwise and the reaction mixture was heated at reflux for 18 h. H2O and AcOEt were then added, the phases were separated, and the organic phase was washed with saturated NaHC 3 solution (3x), dried and concentrated to give a white solid (23.2 g), which was used directly in the next stage as obtained. l H NMR (80 MHz, CDCl 3) d (TMS). 7.28 (m, 10H), 5.00 (s, 1 H), 4.19 (q, J = 7Hz, 2H), 1.22 (t, j = 7Hz, 3H). b) Ferf-butyl 3,3-diphenyl-3-ethoxycarbonylopropanoate To a solution of NaH (609 suspension in paraffin, 4.25 g) in DMF (100 mL), a solvaon of the product obtained in reference example 7a was added. (23.2 g, 0.965 mol) in DMF (50 mL) and the reaction mixture was stirred at room temperature for 1 h. Bitumen / ít / -butyl (13.5 mL) was added dropwise., 0.965 mol) and the mixture was stirred at 60 ° C for 18 h. The resulting solution was treated with H O (1 mL) and the solvents were removed. More H? 0 was added and extracted with AcOEt, at basic pH. The organic phase was dried and concentrated to give a dark oil] H NMR (80MHz, CDCl 3) d (TMS). 7.26 (s, 10H), 4.21 (q, j = 7.2Hz, 2H), 3.43 (s, 2H), 1.30 (s, 9H), 1.16 (t, J = 7.2Hz, 3H). c) Titrant compound On a cooled (0 ° C) solution of the product obtained in reference example 7b (6 g, 0.017 mol) in CH 2 Cl 2 (20 mL), trifluoroacetic acid (2.6 mL) was added dropwise and the mixture was shaken. mix at room temperature for 18 h. The title compound was then obtained by evaporation to dryness of the resulting solution (85%) H NMR (80 MHz, CDCl 3) d (TMS) 1 1.26 (broad s, 1 H), 7.25 (s, 10 H), 4.21 (q, J = 7. 1 Hz. 2H), 3 54 (s 2H), 1 .17 (t,] = 7 1 Hz, 3H) REFERENCE EXAMPLE 8 3-phenyl-3- (phenylamino) propanoic acid On an aniline hydrochloride solution (3.37 g, 26 mmol) and ethyl benzoylacetate (5 mL, 26 mmol) in MeOH (70 mL) was added. aBH ^ CN (1.75 g) and the mixture was stirred at room temperature for 18 h. The solvent was removed and the residue was partitioned between 0.5N HCl and Et2 ?. The aqueous phase was basified with 1 N NaOH and extracted with CHCl3. The organic phase was dried and concentrated, obtaining a crude. Purification by silica gel chromatography (hexane: AcOEt, 5%) afforded ethyl 3-phenyl-3- (phenallammo) propanoate (4.3 g, 62%). This compound was then hydrolyzed in basic medium to give the title compound as a white solid. pf-. pcM irc,] H NMR (80MHz, CDCl 3) d (TMS) 7.10 (m, 8H), 6.63 (m, 2H). 4.85 (t, J = 6.3 Hz, 1 H), 4.05 (m 2 H), 2.85 (d, J = 6.5 Hz. 2 H). REFERENCE EXAMPLE 9 3-Phenyl-3- (4-nitrophenyl) aminopropanoic acid A mixture of frans-cinnamic acid (2 g, 13 mmol) and HBr (30% solution in AcOH, 40 mL) was stirred at room temperature for 18 h and concentrated to dryness. The resulting solid was redissolved in 2-butanone (100 mL) and p-nitroaniline (5 g, 36 mmol) was added. The reaction mixture was heated at reflux for 18 h, allowed to cool and partitioned between CHCl3 and Hd IN. The organic phase was dried and concentrated, obtaining a crude. This was purified by chromatography on silica gel (hexane: AcOEt, 50%), to give the title compound as a yellow solid (0.78 g, 21%). 1 H NMR (80MHz, CDCl 3) d (TMS) 7 99 (d, J = 9.2 Hz, 2H). 7.33 (m, 5H), 6.56 (d, J = 9.2 Hz, 2H), 4.92 (t,] = 6.3Hz, 1 H), 3 44 (m, 2H), 2.82 (d, j = 6.5 Hz, 2H ). REFERENCE EXAMPLE 10a and 10b Cis- and rrans-3-phenyl-3- (4-nitrophenyl) propenoic acid On a cooled suspension (0 ° C) of 50% NaH (24.66 g, 0.51 mol) in THF (375 mL Ethyl iophonoacetate (88.2 mL, 0.44 mol) was added dropwise. The mixture was stirred for 45 m and 4-n-trobenzophenone (102 g, 0.45 mol) in THF (525 mL) was added. The resulting mixture was heated at reflux for 18 h under an argon atmosphere, and then allowed to cool and partitioned between H2O and AcOEt. The organic phase was dried and concentrated, obtaining a crude (115 g). This crude was dissolved in MeOH (600 mL), a solution of K? CO? (87.2 g) in H O (288 mL) and the mixture was heated under reflux for 4 h. The MeOH was removed, water was added and the solution was extracted with hexane. The aqueous solution was then brought to acid pH with 5N HCl and extracted with C HCl 3. Evaporation of the solvent gave a brown solid in the form of a cis / trans mixture.

The pure cis isomer (10a) can be obtained by acOEt reaistahzaaon (34 g, 30%). ? NMR (80MHz, CDCh) d (TMS): 8.23 (d, j = 8.0 Hz, 2H), 7.33 (m.7H), 6.70 (m), 6.44 (s, 1 H). The pure trans isomer (10b) can be obtained in the following way: A mixture of rasp-anamate of ethyl (4.4 g, 27 mmol), 4-bromonitrobenzene (6 g, 29.7 mol), t-phenylphosphine (0.26 g) was heated at reflux. , tributylamine (8 mL), and paiadium acetate (57 mg) in acetonitrile (20 mL) under an argon atmosphere for two days. The cooled mixture was partitioned between 0.5N NaOH and CHCl3, the organic phase was separated, dried and concentrated. The residue was purified by chromatography on silica gel (Hexane: AcOEt, 20%) to give a white solid (2.4 g, 31%). 'H NMR (80 MHz, CDCl 3) d (TMS): 8.18 (d, J = 8 0 Hz. 2 H), 7.33 i, 8 H), 6.39 (s, 1 H). REFERENCE EXAMPLE 11 3-Phenyl-3-hydroxy-3-trifluoromethylpropanoic acid On a cooled (0 ° C) solution of rc-butyl lithium (1.6M in hexanes, 40 mL) in anhydrous THF (90 mL), drop was added dropwise diisopropylamine (9.45 mL) and the mixture was stirred for 5 min. Maintaining the temperature at 0 ° C, AcOH (1.92 mL, 0.0336 mol) was added dropwise and the reaction mixture was stirred for 10 min. And then heated at 50 ° C for 30 min. The resulting solution was allowed to cool, a solution of 2,2,2-trifluoroacetoenone (4.76 mL (0.0336 mol) in anhydrous THF (15 mL) was added at 0 ° C and the resulting mixture was stirred at room temperature overnight. Finally, Et2 (150 mL) and H2O (50 mL) were added, the aqueous phase was separated, acidified with HCl and extracted with AcOEt (3x) The organic phase was dried and concentrated to give the title compound orange solid form (3.88 g, 49%). ] H NMR (80 MHz, CDCl 3) d (TMS): 9.0 (complex signal, 2H). 7.38 (m, 5H), 3.2 (s, 2H). REFERENCE EXAMPLE 12 3,3-Diphenylpropenoic acid Following a procedure similar to that described in the example of retention 10, but using benzotenone instead of 4-n-trobenzorenone, the title compound was obtained. ! H NMR (80 MHz, CDCh) d (TMS): 7.31 (m, 10 H), 6.33 (s, 1 H). 5 9 (m, 1 H). REFERENCE EXAMPLE 13 3- (4-Nitrophenyl) Butanoic Acid On cooled H2SO4 (0 ° C) (30 mL) was added 3-phenylbutypic acid (15 g, 91 mmol). Then, a cooled solution of HNO3 (5 mL) in H2SO4 (10 mL) was added dropwise and the mixture was stirred at 0 ° C for 30 min and at room temperature for a further 30 min. The mixture was poured onto ice and the resulting solution was allowed to precipitate in the refrigerator overnight. The pre-pad was filtered, washed with H2O and dried, to give a crude (28.3 g). This was purified by chromatography on silica gel (CHC: MeOH, 10%) to give the title compound (4.1 g, 21%). 'H NMR (80MHZ, CDC13 + CD30D) d (TMS): 8.14 (d, J = 8.7 Hz, 2H), 7.47 (d, J = 8.7 Hz, 2H), 4.77 (s, 1 H), 3.36 (quint , J = 7.6 Hz, 1 H), 2.61 (d, J = 7 4 Hz, 2H), 1.31 (d, J = 7.0 Hz, 3H). REFERENCE EXAMPLE 14 3-Ethoxycarbonyl-3- (4-nitrophenyl) propanoic acid Following a procedure similar to that described in reference example 7b, but starting with ethyl 4-n-trophoxylacetate in place of ethyl diphenylacetate, and then hydrolyzing the leff-butyl ester using p-toluenesulfonic acid in refluxing benzene instead of using rifluoroacetic acid, the title compound was obtained. 'H NMR (80MHz, CDCl 3) d (TMS): 9.61 (s, 1 H), 8.19 (d, J = 8.4 Hz. 2H), 7.49 (d, J = 8. 4 Hz, 2H), 4.16 (q, j = 7.3 Hz, 2H), 4.14 (m, 1 H), 3.30 (dd, j = 17.5 Hz, J = 9.0 Hz, l H), 2.76 (dd, J = 17.3 Hz, j = 6.1 Hz. 1 H), 1.20 (t, j = 7.3 Hz, 3H) REFERENCE EXAMPLE 15 3-Ethoxycarbonyl-3-phenylpropanoic acid Following a procedure similar to that described in the example of referena 14, but departing of ethyl phenylacetate, the title compound was obtained. * H NMR (80 MHz, CDCl 3) d (TMS): 9.49 (m, 1 H), 7.28 (s, 5 H), 4.13 (m, 3 H), 3.25 (dd, J = 17.2 Hz, J = 9.8 Hz, 1 H), 2.67 (dd, J = 17.1 Hz, J = 5.3 Hz, 1 H). 1.17 (t, J = 7.3 Hz, 3H). REFERENCE EXAMPLE 16 cis and fraps-3-phenyl-3- (3-nitrophenyl) propenoic acid Following the procedure described in reference example 10, but starting from 3-n-trobenzoenone, the title compound was obtained in the form of solid yellow. ? NMR (80MHz, CDCh) d (TMS): 8.1 1 (m, 2H), 7.25 (, 7H), 6.37 (s 0.67H), 6.34 (s, 0.33H), 6.12 (s, lH) REFERENCE EXAMPLE 17 3- [N- (Ethoxycarbonyl) am? No] -3- (4-nitrophenyl) propanoic acid Following the procedure described in reference example 13, but starting with 3- (N- (ethoxycarbonyl) am? no) -3-phenolpropane? co, the title compound was obtained. * H NMR (80MHz, CDCI3) d sMS): 9.66 (s, 1 H), 8.17 (d, J = 6.5 Hz, 2H), 7.50 (d, J = 6.5 Hz, 2H), 6.2 (m, 1 H) ), 5.22 (q, J = 7.5 Hz, 1 H), 4.11 (q, J = 7.1 Hz, 2H), 2.91 (d, J = 6.2 Hz, 2H), 1.20 (t, J = 7.1 Hz, 3H) . REFERENCE EXAMPLE 18 3-Hydroxy-3- (2-methylpropyl) -5-methylhexanoic acid Following the procedure described in reference example 11, but using 2,6-d ime t? In the case of 2, 2,2-trifluoroacetophenone, the title compound (56%) was obtained. l H NMR (80 MHz, CDCl 3) d (TMS): 6.8 (m, 2 H), 2.25 (s, 2 H). 1.7 (m, 2H), 0.95 (m, 16H). REFERENCE EXAMPLE 19 3-Phenyl-3-methylbutanoic acid a) 3-Phenyl-3-methylbutyronitrile A mixture of 1-chloro-2-phenyl-2-methylpropane (150 g, 0.889 mol) and NaCN (54.46 g) in DMSO (250 mL) was heated at 100 ° C for 3 weeks. The solution was concentrated to half the initial volume, H2O (400 mL) was added and extracted with Et2? (3x) The combined organic phases were dried and concentrated to give a crude (1 15.1 g), which was used directly in the next step as obtained b) Title compound On the product obtained in section a) H 2 O was added slowly (375) mL) and H2SO4 (300 mL), and the mixture was heated at reflux for 48 h. Then, H2O was added and the resulting solution was extracted with CHCl3. The organic phase was washed with 2N NaOH (3x), and the aqueous phase was acidified with 5N HCl and extracted with CHCl3. The combined organic phases were dried and concentrated to give the title compound. ] NMR (80 MHz, CDCh) d (TMS). 10.8 (m, 1 H). 7.29 (s, 5H), 2.61 (s, 2H). 1.43 (s, 6H). REFERENCE EXAMPLE 20 N-Phenyl-N-methylaminoacetic acid On a solution of N-phenylglycine (5 g, 33 mmol) and tormaldehyde (37% aqueous solution, 20 mL) in acetonitrile (100 mL) was added NaBH ^ CN J ~~ (6.8 g) and AcOH (2 mL) and the reaction mixture was stirred at room temperature overnight. The volatile solvents were removed in vacuo, the residue acidified to pH = 3- and extracted with CHCl3 several times. The combined organic phases were dried and concentrated to give a crude (5.73 g), which was purified by silica gel chromatography (AcOEt) to give the title compound (3.96 g, 73%). > H NMR (80 MHz, CDCl 3) d (TMS): 8.82 (s, 1 H), 7.38 (m, 2 H), 6.75 (m, 3 H), 4.05 (s 2 H), 3.03 (s, 3 H). REFERENCE EXAMPLE 21 3-Methyl-3- (4-nitrophenyl) butanoic acid Following the procedure described in reference example 13, but starting from the compound obtained in reference example 19, the title compound (47%) was obtained. 1 H NMR (80 MHz, CDCl 3) d (TMS): 8.16 (d, J = 6.5 Hz, 2 H), 7.55 (d, j = 6.5 Hz, 5 2 H), 3.5 (m, 1 H), 2.70 (s. 2H), 1.50 (s, 6H). REFERENCE EXAMPLE 22 cis and frans-3- (4-nitrophenyl) -2-butenoic acid Following the procedure described in reference example 10, but using 4-nitroacetophenone instead of 4-nitrobenzophenone, the title compound was obtained. ] NMR (80 MHz, CDCl 3) d (TMS): 8.8 (m, 1 H), 8.23 (d, j = 6 4 Hz, 2 H), 7.64 (d, J = 6.4 Hz, 2 H), 6.21 (d, J) = 1.3 Hz, 0.7H), 6.07 (d,) = 1.3 Hz. 0.3H), 2.62 (d, J = 1.3 Hz, 3H). REFERENCE EXAMPLE 23 5 N-Ethoxycarbonyl-N- (4-nitrophenyl) aminoacetic acid On a cooled (0 ° C) suspension of 4-n? Troanil? Na (10 g, 0.072 mol) and Et3N (10 mL) in CHCI3 (120 mL), ethyl chloroormate (6.9 mL) was added dropwise and the mixture was stirred under an argon atmosphere at room temperature overnight. CHCl3 was added and the resulting solution was washed with 1 HCl. The phases were separated, the aqueous phase was washed with CHCl 3 and the combined organic phases were dried and concentrated. The residue was chromatographed on silica gel (hexane: AcOEt, 30%) to give the? - (eto ?? carbonyl) -4-nitroaniline (1.7 g). This product was dissolved in THF (5 mL) and a cooled (0 ° C) suspension of NaH (0.48 g, 10 mmol) in anhydrous THF (10 mL) was added dropwise over 5. The mixture was stirred at room temperature for 30 min and ethyl bromoacetate (0.89 L, 8 mmol) was added. The reaction mixture was stirred at room temperature for 48 h and then heated to reflux for 24 h. The residue was dissolved in CHCl3 and phosphate buffer, and extracted with CHCl3 (2x). Evaporation of the solvent gave the title compound as ethyl ester (1.54 g). This product was dissolved in MeOH (35 mL), a solution of K2CO3 (1.33 g) in H2O (18 mL) and the mixture was heated at reflux for 3 h. The volatiles were removed in vacuo and the resulting solution was extracted with hexane. The aqueous phase was acidified and extracted with CHCl3. The combined organic phases were dried and concentrated to give the title compound. ] H NMR (80 MHz, CDCl 3) d (TMS): 8.21 (d, J = 6.5 Hz, 2 H), 7.50 (d,] = 6.5 Hz, 2 H), 5.89 (broad s, 1 H), 4.45 (s, 2H), 4.16 (q, J = 7 1 Hz, 2H), 1.26 (t, J = 7.1 Hz. 3H). REFERENCE EXAMPLE 24 Trans -3-phenyl-2-pentenoic acid Following the procedure described in reference example 10, but using propiophenone instead of 4-n-trobenzoenone, the title compound was obtained. > H NMR (80 MHz, CDCl 3) d (TMS): 10.68 (m, 1 H), 7.42 (m, 5 H), 6.05 (s, 1 H), 3.12 (q, J = 7.1 Hz, 2H), 1.09 (t, J = 7.1 Hz, 3H). REFERENCE EXEMPLE 25 2-Phenyl-2-methylpropylsulfonyl chloride Magnesium chips (0.8 g, 0.036 mol), anhydrous THF (10 mL) and a iodine buffer were placed in a flask under argon. Then, 1-chloro-2-phenol-2-methyl-lpropane (5 mL, 0.031 mol) in THF (15 mL) was added slowly and the reaction mixture was heated under reflux for 30 min. It was allowed to cool to room temperature and was finally cooled to -70 ° C and suifunlo chloride (2.5 mL) was added dropwise., 0.031 mol) in THF (10 mL). The temperature was allowed to rise to room temperature and was stirred at this temperature overnight. The resulting solution was poured over diluted phosphate buffer and extracted with AcOEt (3x). Evaporation of the solvent provided the title compound (4.6 g, 65%). ] H NMR (80MHz, CDCl?) D (TMS). 7.30 (m, 5H). 3.59 (s, 2H), 1 .39 (s, 6H) REFERENCE EXAMPLE 26 Acid [N -methyl-N- (2-methoxyfine lano-a) N- (2-methoxyphenyl) aminoacetic acid On a solution After cooling (0 ° C) of 2-methoxyane (13.2 g, 0.108 mol) in CHCl3 (100 mL), ethyl bromoacetate (b mL, 0.05 mol) was added and the mixture was stirred at room temperature overnight. . The resulting solution "*" "" was washed with 0.5N NaOH and the organic phase was concentrated, obtaining a crude. This was purified by chromatography on silica gel (hexane-AcOEt, 107c) to give ethyl N- (2-methoxyphenyl) amidoacetate (4.2 g, 40%). This compound was dissolved in MeOH (80 mL), a solution of K2CO3 (4.4 g) in H2O (50 mL) was added and the mixture was heated to reflux overnight. The MeOH was removed and the resulting aqueous solution was extracted with hexane. The aqueous phase was acidified with 5N HCl and extracted with CHCl3 (3x). Removal of the solvent gave the title compound. 'H NMR (80MHz, CDCl 3 + CD30D) d (TMS): 6.83 (m, 3H), 6.56 (m, 1H), 3.91 (s, 0 2H), 3.86 (s, 3H), 3.62 (s, 2H). b) Titrant compound Following the procedure described in reference example 20, but starting from the compound obtained in reference example 26a, the title compound (76%) was obtained. 5] H NMR (80MHz, CDCl 3) d (TMS): 8.78 (s broad, 1 H), 6.87 (m, 4H), 3.85 (s, 3H), 3. 71 (s, 2H), 2.88 (s, 1 H). REFERENCE EXAMPLE 27 Fraps-3-phenyl-3- (methoxymethyl) propenoic acid Following the procedure described in reference example 10, 0 but using 2-methoxyacetophenone instead of 4-n-trobenzophenone, the title compound was obtained (30%). 'H NMR (80 MHz, CDCl 3) d (TMS): 1 1.13 (broad s, 1 H), 7.23 (5 h), 6.49 (s, 1 H), 3. 66 (s, 3H), 3.52 (s, 2H). REFERENCE EXAMPLE 28 5 N-Isobutyl-N- (4-nitrophenylsulfonyl) aminoacetic acid a) N-Isobutyl-N- (4-nitrophenylsulfonyl) amine On a solution of isobutylamine (5 mL, 0.052 mol) in CH2Cl2 (100 mL) Et3N (5.07 mL) and 4-n-trobenzenesulonyl chloride (11.7 g, 0.052 mol) were added and the mixture was stirred at room temperature overnight. The resulting solution was washed with H2O (3x), dried and concentrated to give the desired product (9.41 g, 70%). 'H NMR (80 MHz, CDCh) d (TMS): 8.38 (d, J = 6.5 Hz, 2H), 08 08 (d, J = 6.5 Hz, 2H), 5.12 (t, J = 6 4 Hz, 1 H ), 2.83 (t J = 6 5 Hz, 2 H), 1.75 (hept, 1 = 0.5 Hz, 1 H), 0.89 (d, J = 6.5 Hz, 6H). B) Title compound Following a procedure similar to that described in reference example 26a, but starting from the compound obtained in a) "" - above, the title compound was obtained (3.20 g, 28%). ] H NMR (80 MHz, CDC13) d (TMS). 8.36 (d, J = 6.5 Hz, 2H), 8.03 (d,] = 6.5 Hz, 2H), 4.09 (s, 2H), 3.80 (s, 1 H), 3.10 (d, J = 7 4 Hz, 2H ), 1.87 (hept, J = 6.5 Hz, 1 H), 0.91 (d, j = 6.5 Hz, 6H). EXAMPLE 1 l- (ll- (3,3-Diphenylpropanoyl) -4-piperidylmethyl) -lH-2-methylimidazo (4,5-c) pyridine On a cooled mixture (0 ° C) of the product obtained in the example of Reference 5 (0.5 g, 2.17 mmol), 3,3-diphenylpropane? co (0.49 g, 2.17 mmol) and 1-hydroxybenzotristazole (0.26 g) in DMF (25 mL), was added under a 0 atmosphere of nitrogen dicyclohexylcarbodiimide (0 4 g) and the reaction mixture was stirred at room temperature for 18 h. The solvents were removed in vacuo, the resulting residue was stirred with AcOEt and the insoluble material was filtered. The organic solution was washed with saturated NaHC 3, H 2 O solution and saturated sodium chloride solution, dried and concentrated. Crude 5 (1.44 g) was purified by chromatography on silica gel (CHCh: MeOH, 10%) to give the title compound as a white solid (0.59 g, 62%). mp 79-84 ° C (C28H3oN4?); 'H NMR (80 MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), 8.35 (d, J = 5.5 Hz, 1 H), 7.23 (m, 11H), 4.66 (t, J = 7.3Hz, 1 H), 4.65 (m, 1 H), 3.83 (d, j = 7.2Hz, 2H), 3.81 (m, 1 H), 3.01 0 (dd, j = 7.8Hz, J = 3.2Hz, 2H), 2.57 (s, 3H), 3-0.5 (complex signal, 7); 13C NMR (20.15MHz, CDCI3) d (TMS): 169.25, 153.17, 143.78, 143.37, 140.85, 140.71. 139.84, 138.97, 127.93, 127.58, 127.19, 125.87, 104.74, 48.62. 47.11, 44.90, 40.88. 38.00, 36.32, 29.66, 29.03, 3.37 The t-hydrochloride was prepared by treating a solution of the product (0.28 g) in a mixture 1 1 of AcOEt and CH2Cl2 with a soluaon of HCl (g) in Et2 ?. The mixture was cooled for 1 h at -20 ° C and the solid was collected by filtration to give the desired salt (0.3 g, 85%). mp 128-134 ° C (C28H30N4O.3HCl). The hemifumarate was prepared by treatment of a solution of the product (0.87 g) in EtOH with a solution of fumápco acid (0.46 g) in EtOH. The mixture was cooled for 1 h at -20 ° C, the solid was collected by filtration and recrystallized from EtOH to give the desired salt (0.308 g, 30%) mp 190-194 ° C (C28H30N4O. C4H4O4, H20). EXAMPLE 2 l- (1- (3,3-Diphenylpropanoyl) -4-piperidyl-1 H-2-methylimidazo | 4,5-clpyridine Following the procedure described in Example 1, but starting with the compound obtained in example of retention 6, the title compound was obtained as a white solid (45%), mp: 95-100oC (C 7H2sN'4?);! H NMR (80MHz, CDC13) d (TMS): 8.97 (s) , 1 H), 8.33 (d, J = 5.3 Hz, 1 H), 7.29 (m, 10 H), 7.08 (d, J = 5.3 Hz, 1 H), 4.83 (m, 1 H), 4.74 (t, j = 7.5Hz, 1H), 4.30 (m, 2H), 3.10 (m, 3H), 2.61 (s, 3H), 3-1.5 (complex signal, 5H) EXAMPLE 3 l-Ill-l3-Phenyl- 3- (N- (methoxycarbonyl) amino) propanoyl] -4-piperidyl] methyl] -lH-2-methylimidazo (4,5-c] pyridine Following the procedure described in example 1, but using the 3-fenti-acid 3- (N- (methoxycarbonyl) amnolpropanoic instead of 3,3- diphenylpropanoic acid, the title compound was obtained as a white solid (51%) mp: 97-100 ° C (C24H29N5O3.I / 2H2O); 5] NMR (80 MHz, CDCl 3) d (TMS): 8.95 (s, 1 H), 8.35 (d, J = 5.5 Hz, 1 H), 7.30 (m, 6 H), 6.50 (m, 1 H), 5.08 (m, 1 H), 4.60 (m, 1 H), 3.87 (m, 3H), 3.63 (s, 3H). 2.58 (s, 3H), 3-0.5 (complex signal, 9H). EXAMPLE 4 l- (l-l3-Phenyl-3-lN- (methoxycarbonyl) aminolpropanoyl-4-piperidyl] -lH-2-0 methylimidazo. {4,5-c] pyridine Following the procedure described in example 1, but starting from the compound obtained in reference example 6 and 3-phenyl-3- [N- (methox? carbon? l) amnolpropanoic acid, the title compound was obtained as a white solid (56%). mp: 102-105 ° C (C23H27N5O3.H2O);] H NMR (80MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), 8.32 (d, J = 5.4Hz, 1 H), 7.36 (m , 5H), 7.08 (d, J = 5.4 Hz, 1 H), 6.30 (m, 1 H), 5.19 (m, 1 H), 4.87 (m, 1 H), 4.30 (m, 2 H), 3.66 ( s, 3H), 2.63 (s 3H), 3.3-1.6 (complex signal, 8H) EXAMPLE 5 0 l- (ll- | 3-Phenyl-3- [N- (i-ff-butoxycarbonyl) aminoJpropanoyl-4-piperidyl ) methyl) -lH-2-methylimidazo (4,5-c] pyridine Following the procedure described in Example 1, but using 3-phenyl? -3- [N- (frr / -butox? carbonyl) am. ? noipropane? co instead of the acid 3,3-difen? lpropane? co, the title compound was obtained as a white solid (407c)] H NMR (80 MHz, CDCh) d (TMS): 8.97 (s, 1 H), 8.38 (d,) = 5.5 Hz. 1 H), 7.30 (m, 6H), 6.30 (m.H.), 5.08 (m.H.), 4.60 (, 1 H), 3.87 (m.H3). 2.60 (s 3H), 3-0.5 (complete signal, 9H), 1.40 (s, 9H). EXAMPLE 6 1-K 1-13-1 N- (4-Aminobenzoyl-lamino] -3-phenylpropanoyl] -4-p-peridulmethyl 1-1 H-2-methylimidazoi-4,5-c] pyridine a) 1- (II) (3-Amino-3-phenupropanoyl) -4-piperidylmethyl] -lH-2-methylimidazo | 4,5-clpiridiru Following the procedure described in Reference Example 5, but starting from the compound obtained in Example 5, the desired product as a colorless oil.] H NMR (80 MHz, CDC13) d (TMS): 8.97 (s, 1 H), 8.38 (d, J = 5 Hz, 1 H), 7.31 (m, 6 H), 4.70 ( m, 1 H), 4.51 (t, J = 7.3 Hz, 1 H), 3.91 (m, 3 H), 2.60 (s 3 H), 3.0-0 7 (complex signal, 1 1 H). Following the procedure described in example 1, but starting from 4-aminobenzoic acid and the compound obtained in example 6a, the title compound was obtained as a white solid (757o). mp: 132-142 ° C (C29H32N O2.H2O); l H NMR (80 MHz, CDCl 3) d (TMS): 8.97 (s, 1 H), 8.45 (m, 1 H), 8.38 (d, j = 5.5 Hz, 1H), 7.72 (d, J = 8.3 Hz, 2H), 7.34 (m, 6H), 6.65 (d, j = 8.3 Hz, 2H), 5.50 (m, 1 H), 4.64 (m, 1 H), 3.80 (m, 5H), 2.57 (s, 3H), 3-0.5 (complex signal, 9H). EXAMPLE 7 l - ((1- (N- (Diphenylmethyl) aminoacetyl-4-piperidylmethyl] -lH-2-methylimidazo (4,5-clpyridine) Following the procedure described in Example 1, but using the acid (N- (difen ? lmet? Dam? no) acetic instead of 3,3-d? -entlpropane? co acid, the title compound was obtained as a white solid (6570) mp: 77-79 ° C (C28H31N5O.I / 2H20 H NMR (80 MHz, CDCl 3) d (TMS): 8.97 (s, 1 H), 8.38 (d, j = 5.5 Hz, 1 H), 7.29 (m, 11H), 4 84 (s, 1 H), 4.65 (m, 1 H), 3 94 (d,] = 7.2 Hz, 2H), 3.50 (m.IH), 3.36 (s, 2H), 2.60 (s) , 3H), 3.0-1 0 (complex signal, 8H). EXAMPLE 8 l- ( { L- (3,3-Diphenyl-3-hydrox? Propanoyl) -4-piperidylmethyl] -l H-2-metUimidazoí4,5-clpyridine Following the procedure described in Example 1, but using 3,3-d? phen? l-3-hydroxpropane? acid in place of the 3,3-d? ten? ipropane? acid, the title compound was obtained by white solid (61%). mp: 210-2110C (C 8 H? N? 2 1 / 2H20). l H NMR (80 MHz, CDCI 3) d (TMS): 9.20 (s, 1 H), 8.60 (d, J = 5.5 Hz, 1 H), 7.56 (m, 10 H), 7.38 (d, | = 5.5 Hz, 1 H), 6.79 (m, 1 H), 4.82 (, 1 H), 4.12 (d, J = 7.2H, 2H), 4.05 (m, 1 H), 3.42 (s, 2H), 2.81 (s, 3H), 3.3-1.0 (complex signal, 7H) EXAMPLE 9 l- [ll- (2-Amino-2,2-diphenylacetyl) -4-piperidylmethyl] -lH-2-methylimidazole4,5-cjpyridine Following the procedure described in Example 1, but using 2-amino-2,2-diphenylacetic acid instead of 3,3-diphenylpropanoic acid, the title compound was obtained as a white solid (887o). NMR (80 MHz, CDCl 3) d (TMS): 8.93 (s, 1 H), 8.36 (d, J = 5.5 Hz, 1 H), 7.34 (m, 10 H), 7.03 (d, J = 5.5 Hz, 1 H ), 4.29 (m, 2H), 3.75 (d, j = 7.2H, 2H), 2.49 (s, 3H), 2.8-1.0 (complex signal, 9H). EXAMPLE 10 l-III-L2- (N-acetylamino) -2 ^ -diphenylacetyl) -4-piperidyl] methyl I-lH-2-methylimidazo. { 4,5-cJpyridine A solution of the compound obtained in Example 9 (0.3 g, 0.68 mmol) in pyridine (3 mL) and A O (1 mL) was heated at 65 ° C for 18 h. The solvents were removed in vacuo and the residue was partitioned between CHCl3 and 0.5N NaOH. The organic phase was dried and concentrated to give a crude (0.38 g), which was purified by chromatography on silica gel (CHCh: 5% MeOH) to give the title compound (0.3 g, 9270). mp: 138-148 ° C (C29H31 N5O2); ^ H NMR (80MHz, CDCI3) d (TMS): 8.93 (s, 1 H), 8.35 (d, J = 5.5Hz, 1 H), 8.27 (s, 1 H), 7.60 (m, 4H), 7.30 (m, 6H), 7.00 (d, j = 5.5Hz, 1H), 4.45 (, 2H), 3.72 (d, J = 7.2Hz, 2H), 2.48 (s, 3H), 2.7-0.4 (complex signal , 7H), 1.69 (s, 3H). EXAMPLE 11 l - [[1- (3-Phenyl-3- (phen-amino) -propanoyl] -4-piperidyl] -netl-lH-2-methylimidazol-4,5-c] pyridine Following the procedure described in Example 1, but using the 3-phenyl-3- (phenylamino) propane? co acid (obtained in the reference example) 8) instead of 3,3-diphenylpropanoic acid, the title compound was obtained as a white solid (55%). mp: 82-91 ° C (C28H3? N? 0.1 / 2H20); H NMR (80 MHz, CDCl 3) d (TMS): 8.95 (s, 1 H), S.35 (d, J = 5.5 Hz, 1 H), 7.32 (m, 7 H), 7.06 (t, J = 8.0) Hz, 2H), 6.57 (t, 1 = 8.0Hz, 2H), 5.40 tm, 1 H), 4.77 (m, 2H), 3.77 (d,] = 7.1 H, 2H), 3.70 (m, 1 H) , 2.53 (s, 3H), 3.0-0.3 (complex signal, 9H). EXAMPLE 12 l-III- (3-Phenyl-3 - [(4-nitrophenyl) amino) propanoyl-4-piperidiUmetill-H-2-methylimidazo (4,5-c] pyridine Following the procedure described in Example 1 , but using the 3-phenyl-3- (4-n-trophenyl) am? nopropane? co acid (obtained in the reference example 9) instead of the 3,3-diphenylpropane? co acid, the title compound was obtained in white solid form (907o) mp: 230-232 ° C (C2sH3oN6? 3.1 / 2H0); 1 H NMR (80MHz, CDC13) d (TMS): 8.98 (s, 1 H), 8.38 (d, J = 5.5Hz, 1H), 7.97 (d, J = 9Hz, 2H), 7.35 (m, 5H), 7.12 (d, J = 5.5Hz, 1 H), 6.95 (m, 1 H), 6.42 (d, J = 9.0Hz, 2H), 4.76 (m, 2H), 3.75 (m, 3H), 2.58 (s, 3H), 3.0-0.3 (complex signal, 9H) EXAMPLE 13 l-lll-l 3-1 ( 4-Aminofenyl) amino] -3-phenylpropanoyl) -4-piperidyl) methyl-1H-2-methylimidazo [4, 5-Clpyridine To a solution of the product obtained in Example 12 (226 mg, 0.4 mmol) in EtOH (5 mL) and H 2 O (0.6 mL) was added a solution of CaCb (33.6 mg) in H 2 O (0.26 mL) and zinc powder (0.58 g). The resulting mixture was heated at 50 ° C for 45 mm, filtered through celite and the filtrate was concentrated. The residue was purified by silica gel chromatography (CHCh: MeOH 107c) to give the title compound as a white solid (0.17 g, 91%). 'H NMR (80 MHz, CDCh) d (TMS): 8.93 (s, 1 H), 8.34 (d, j = 5.5 Hz, 1 H), 7.31 (m, 6H), 6.44 (broad s, 4H), 4.62 (m, 2H), 3.80 (d, J = 7.0Hz, 2H), 3.52 (m, 4H), 2.55 (s, 3H), 3.0-0.5 (complex signal , 9H). A solution of the title compound in CHCl 3 was treated with a solution of HCKg) in Et?, To give the hydrochloride of the title compound. mp: 189-195 ° C (C28H32N60.4HCI.2H20). EXAMPLE 14 l - [[l- (2 ^ -Dyclohexylacetyl) -4-piperidyl] methyl] -lH-2-methylimidazo | 4,5-cJpyridine Following the procedure described in example 1, but using the acid 2,2- dicyclohexylacetic acid instead of 3,3-diphenylpropane? co acid, the title compound was obtained as a white solid (2370). mp: 161-164 ° C (C27H40N4O.3 / 4H2O); ? H NMR (80 MHz, CDCh) d (TMS): 8.97 (s, 1 H), 8.37 (d J = 5.5 Hz, 1 H), 7.19 (d, J = 5.5 Hz, 1 H), 4.82 (m, 1 H), 4.03 (m, 1 H), 3 98 (d, J = 7.2Hz, 2H), 2.62 (s, 3H), 3.0-0.5 (complex signal, 30H). EXAMPLE 15 l - ((1- (3,3-Diphenylpropenoyl) -4-piperidylmethyl-lH-2-methylimidazo (4,5-clpyridine) Following the procedure described in example 1, but using the 3,3-d acid When the propene is obtained (in the example of reterenase 12) instead of 3,3-d? phenolpropane? co, the title compound was obtained as a white solid (85%). 92 ° C (C28H28N4O.H2O), 5] H NMR (80MHz, CDCl 3) d (TMS): 8.95 (s, 1 H), 8.37 (d, J = 5.5Hz, 1 H), 7.32 (m, 10H) , 7.09 (d,] = 5.4 Hz, 1 H), 6.27 (s, 1 H), 4.65 (m, 1 H), 3.82 (m, 1 H), 3.77 (dd, J = 6.7 Hz, j = 2.2 Hz, 2H), 2.54 (s, 3H), 2.8-0.5 (complex signal, 7) EXAMPLE 16 cis and trans -l - [(l-l3-Phenyl-3- (4-nitrophenyl) propenoyl-4-piperidyl ) methyl] -lH-2-0 methylimidazo [4,5-c] pyridine Following the procedure described in example 1, but using a cis / trans mixture of 3-ten? -3- (4-n? trotenil) ) propene? co (obtained in reference example 10) instead of 3,3-d? phenolpropane? co acid, the title compound was obtained in white solid (857o). 5 mp: 106-1 2 ° C (C23H27N5O3.I / 2H2O); l H NMR (80MHz, CDCI3) d (TMS): 8.95 (s, 1 H), 8.37 (d,] = 5.5Hz, 1 H), 8.18 (dd, J = 8.6Hz, J = 3.2 Hz, 2H) , 7.37 (m, 8H), 6.49 (s, 0.5H), 6.40 (s 0.5H), 4.66 (m, 1H), 3.84 (m, 3H), 2.57 (s, 3H), 2.8-0.5 (signal complex, 7H). EXAMPLE 17a and 17b 0 a) cis -l- (H- (3- (4-Aminophenyl) -3-phenylpropenoyl-4-piperidylmethyl] -lH-2-methylimidazole4,5-cjpyridine b) trans-1 - ((1) 3- (4-Aminophenyl) -3-phenylpropenoyl) -4-piperidyl] methy1-lH-2- "" methylimidazo [4,5-c) pyridine Following the procedure described in the example of reierarena 3, but starting from of the compound obtained in Example 16, the title compound was obtained as a mixture of cis / trans isomers, which were separated by chromatography on silica gel (CHCh: MeOH, 107o) Isomer eluting slower, cis isomer (example 17a) ) (547o): mp: 121-135 ° C (C2sH29? 0.3 / 2H0); 0] H NMR (80MHz, CDCI3) d (TMS), 8.95 (s, 1 H), 8.36 (d,) = 5.5 Hz. 1 H), 7.29 (s, 5H), 7.07 (m, 3H), 6.65 (d, J = 6.5Hz, 2H), 6.07 (s, 1 H), 4.70 (m, 1 H), 3.82 (m 3H), 2.57 (s 3H) ), 2.8-0.5 (complex signal, 9H). Isomer that elutes faster, trans isomer (example 17b) (227c) mp: 223-224 ° C (C 8H2QN <0.1 2H2O). 5] H NMR (80 MHz, CDCh) d (TMS). 8 96 (s, 1 H), 8.38 (d, 1 = 5 5Hz, 1 H), 7.30 (s, 5H), 7.05 (m, 3H), 6.60 (d, | = 6.5Hz, 2H), 6.17 ( s, 1 H), 4.60 (, 1 H), 3.81 (m 3 H), 2.55 (s, 3 H), 2.8-0.5 (complex signal, 9 H) Following the same procedure described in example 16 but using acids of pure raps-3-phenyl-3- (4-pyrroenyl) propene? co (described in reference example 10a and 10b respectively) instead of a cis / trans mixture and reducing the resulting compounds following the above described procedure , the title compound was obtained in pure cis or trans form. Alternatively, the pure isomer was obtained in the following way: On a solution of SnCl2 -2H2? (21 g) in HCl (21 mL) was added a solution of c? S-1 - [[! - [3-phenyl-3- (4-n-troenyl) propenoyl] -4-p-peridyl) methyl] -l H-2-methylamine [4,5-c] pyridine (10 g , 20.7 mmol) in AcOH (35 mL). The mixture was stirred at room temperature overnight, and then basified with a cooled aqueous NaOH solution and extracted with CHCl 3 (3x), a solid precipitating in the organic phase. This solid was collected and the organic solution was dried and concentrated to give 8 g of the desired product. The first precipitate and the aqueous phase were combined and treated with more solution of NaOH and extracted with CHCl3 (3x). Evaporation of the solvent gave 1.73 g more of the title product. EXAMPLE 18 l-. { [1- (3,3-Dicyclohexyl-3-hydroxypropanoyl) -4-piperidyl] methyl) -lH-2-methylimidazo (4,5-c) pyridine Following the method described in Example 1, but using acid 3, 3-d? C? Clohex? L-3-hydroxyl? Propane? Co in 3,3-diphenylpropanoic acid, the title compound was obtained as a white solid (27%). mp: 75-81 ° C (C28H 2N4 2.5 4H2O); 1 H NMR (80 MHz, CDCl 3) d (TMS): 8.95 (s, H), 8.37 (d, J = 5.5 Hz, 1 H), 7.24 (d, J = 5.5 Hz, 1 H), 6.09 (s, 1 H), 4.69 (m, 1 H), 4.04 (d, j = 7.2 Hz, 2 H), 3.96 (m, 1 H), 2.64 (s, 3 H), 3.0-0.5 (complex signal, 31 H). EXAMPLE 19 l-. { (1-l3 ^ -Diphenyl-3- (ethoxycarbonyl) propanoyl-4-piperidylmethyl) -lH-2-methylimidazo (4,5-c] pyridine Following the procedure described in Example 1, but using the acid 3- The 3-ethoxycarbonylpropane (obtained in the reference example 7) was replaced by 3,3-d-phenolpropane-co, giving the title compound as a white solid. (607c) .pf: 79-89 ° C (C3? H34 OvH?); H NMR (80MHz, CDCh) d (TMS): 8.98 (s, 1 H), 8.38 (d, j = 5.5Hz, 1 H ), 7.28 (m, • "11H), 4.62 (m, 1 H), 4.22 (q, j = 7.3Hz, 2H), 3.85 (d,.}. = 7.2Hz, 2H), 3.81 (m, 1) H), 3.48 (m, 2H), 2.59 (s, 3H), 3-0.5 (complex signal, 7H), 1.17 (t, J = 7.2Hz, 3H) EXAMPLE 20 (R) -l - ([l - | 2-Phenyl-2- (methoxycarbonylamino) acetyl) -4-p? Peridylmethyl-lH-2-5 methylimidazo | 4,5-c] pyridine Following the method described in Example 1, but using the acid (R) -2-phenyl-2- (methoxycarbonylamino) acetic acid in place of 3,3-diphenylpropanoic acid, the title compound was obtained as a white solid (94%). 0 mp: 108-130 C (C2jH27N5? 3.1 / 2H20); l H NMR (80 MHz, CDCl 3) d (TMS): 8.95 (s, 1 H), 8.35 (d,) = 5.5 Hz. 1 H), 7.37 (m, 5 H), 7.01 (d, 1 = 5.5 Hz, l H), 6.28 (m, 1 H), 5.57 (m, 1 H), 4.70 (m 1 H), 3.80 ( m, 3H), 3.63 (s, 3H), 3-1 (complex signal, 10H). EXAMPLE 21 [11- (3-Phenyl-3-hydroxybutanoyl) -4-piperidyl] methyl] -lH-2-methylimidazo [4,5-cliplidine] Following the procedure described in example 1, but using the 3- phenyl-3-hydroxybutanoic instead of 3,3-diphenyipropanoic acid, the title compound was obtained as a white solid (4170). 0 mp: 199-200 ° C (C23H28N4O2 I / 4H2O); l H NMR (80 MHz, CDCl 3) d (TMS): 8.90 (s, 1 H), 8.38 (d, J = 5.5 Hz, 1 H), 7.22 (m, 6 H), 6.0 (m, 1 H), 4.60 (m, 1 H), 3.91 (m, 3H), 2.57 (s, 3H), 3-0.5 (complex signal, "9H), 1.59 (s, 3H) EXAMPLE 22 5 l-lIl- | 3- ( 4-N-prophenyl) butanoyl-4-piperidylmethyl] -lH-2-methylimidazo (4,5-clpyridine) Following the procedure described in example 1, but using 3- (4-n-trophenyl) butane-co-acid (obtained in reference example 13) instead of 3,3-diphen-ipropane-co-acid, the title compound was obtained in form 0 of white solid (537 °) mp: 75-77 ° C (C23H27N O. I / 2H 0 );] H NMR (80 MHz, CDCh) d (TMS): 8.92 («, 1 H), 8.36 (d, | = 5.5 Hz, 1 H), 8.28 (d, J = 9.5 Hz, 2 H), 7.42 (d, J = 9.5Hz, 2H), 7.12 (d, J = 5.5Hz, 1H), 4.60, 1H), 3.93 (m, 3H), 3.50 (m, IH), 2.61 (s, 3H). ), 3-0.5 (complex signal, 9H), 1.36 (d.1 = 6.9Hz, 3H) 5 EXAMPLE 23 l-lll-l 3- (4-Aminophenyl) butanoyl) -4-piperidyl] methyl 1-1 H -2-methylimidazol4, 5- cjpyridine Following the procedure described in the example of reference 3, but starting from the compound obtained in example 22, the title compound was obtained as a white solid (35% > ). mp: 116-n7 ° C (C23H29N5O.3 / 2H2O); 'H NMR (80MHz, CDC13 + CD30D) d (TMS): 8.88 (s, 1 H), 8.33 (d, j = 5.5Hz, 1 H), 7. 30 (d, J = 5.5Hz, 1 H), 7.02 (d, J = 9.0Hz, 2H), 6.67 (d, J = 9.0Hz, 2H), 4.64 (m, 1 H), 3.93 (m, 3H) ), 3.80 (m, 2H), 3.20 (m, 1 H), 2.63 (s, 3H), 3-0.5 (complex signal, 9H), 1. 31 (d, J = 6.9Hz, 3H). EXAMPLE 24 l - [(1- (2- (4-Nitrophenyl) propanoyl] -4-piperidyl] methyl-lH-2-methylimidazo. {4,5-cjpyridine Following the procedure described in example 1, but using 2- (4-n-troenyl) propane-co-acid instead of 3,3-diphen-lpropane-co-acid, the title compound was obtained as a white solid (127 °) mp: 82-87 ° C (C22H25N5O3.1 / 2H2O); l H NMR (80 MHz, CDCl 3) d (TMS): 8.94 (s, 1 H), 8.33 (d, j = 5.5 Hz, 1 H), 8.16 (d, J = 9.5 Hz, 2 H), 7.44 (d, J = 9.5Hz. 2H), 7.12 (m, 1H), 4.73 (m, 1 H), 4.0 (m, 4H), 2.55 (s, 3H), 3-0.5 (complex signal, 7H), 1.46 (d) , J = 6.9Hz, 3H). EXAMPLE 25 l - ((l- | 2- (4-Aminophenyl) propanoyl-4-piperidylmethyl] -lH-2-methylitnidazole 4,5-clpyridine Following the procedure described in reference example 3, but starting from the compound obtained in Example 24, the title compound was obtained as a white solid (34%), mp: 91-95 ° C (C22H27N? OH 0);] H NMR (80MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), 8.38 (d, j = 5.5Hz, 1 H), 7.05 (m, 1 H), 6.99 (d, J = 9.5Hz, 2H), 6.61 (d, J = 9.5Hz, 2H), 4.74 ( m, 1 H), 3.77 (m, 4H), 253 (s, 3H), 3-0.5 (complex signal, 9H), 1.37 (d, J = 6.9Hz, 3H) EXAMPLE 26 ll [l-l3- Ethoxycarbonyl-3- (4-nitrofenyl) propanoyl] -4-piperidyl] methyl 1-1 H-2-methylimidazole 4,5-c] pyridine Following the method described in Example 1, but using the acid 3-ethoxy? carbon? l-3- (4-n? troten? l) propane? co (obtained in the reference example 14) instead of the acid 3,3-difen? l-propane? co, the title compound was obtained in torma white solid (187c) .pf: 81-84 ° C (C25H2 O H2O); 'H NMR (80MHZ, C DCh) d (TMS): 8.95 (s, 1 H), 8.35 (d, 1 = 5.5 Hz. 1 H), 8.16 (d,) = '9.5Hz. 2H), 7.48 (d, J = 9.5Hz, 2H), 7.22 (m, 1 H), 4.63 (m, 1 H), 4.03 (m, 6H), 2.62 (s, 3H), 3.3-1 (signal complex, 9H), 1.19 (t, J = 6.5Hz, 3H). EXAMPLE 27 l-lll-l3- (4-Aminophenyl) -3-ethoxycarbonupropanoyl] -4-piperidyl) methyl] -lH-2-5 methylimidazo [4,5-c] pyridine Following the method descpto in reference example 3 , but starting from the compound obtained in Example 26, the title compound was obtained as a white solid (907o). mp: 204-205 ° C (C25H31N5? 3.H2?); 0 l H NMR (80 MHz, CDC13) d (TMS): 8.98 (s, 1 H), 8.41 (d,] = 5.5 Hz, 1 H), 7.26 (m, 1 H), 7.07 (d, J = 9.5 Hz, 2H), 6.62 (d, j = 9.5Hz, 2H), 4.65 (1H). 3.98 (m, 6H), 2.62 ^ (s, 3H), 3.3-1 (complex signal, 1 1 H), 1.19 (t, J = 6.5Hz, 3H) EXAMPLE 28 l-ll l- (3-Ethoxycarbonyl- 3-phenylpropanoyl) -4-piperidyl ether ethyl 1-1 H-2-5 methylimidazo [4,5-clpyridine Following the method described in Example 1, but using 3-ethoxycarbonyl-3-phenolpropane? (obtained in reference example 15) instead of 3,3-diphenylpropanoic acid, the title compound was obtained as a white solid (387o). 0 mp: 173-174 ° C (C25H30N4O3.H2O); TH NMR (80MHz, CDCI3) d (TMS): 8.99 (s, 1 H), 8.38 (d, j = 5.5Hz, 1 H), 7.30 (m, 6H), 4.66 (m, 1 H), 4.13 ( m, 6H), 2.62 (_, 3H), 3.5-1 (complex signal, 9H), 1.19 (t, J = 7.12Hz, 3H). EXAMPLE 29 5 ds and trans -ll (l- | 3-Phenyl-3- (3-nitrophenyl) propenoyl] -4-piperidyl) methyl] -lH-2-methylimidazo (4,5-clpyridine) Following the procedure described in Example 1, but using ace and fraps-3-phen? I-3- (3-n? troenyl) propene? co (obtained in reference example 16) instead of 3,3-diphen? -propane acid? co, the title compound was obtained as a white solid (957 °) .pf: 99-103 ° C (C28H 7N5O3.I / 2H20); * H NMR (80MHz. CDCh) d (TMS): 8 97 ( s, 1 H), 8.39 (d, J = 5.5Hz, 1 H), 8.27 (m, 2H), 7.30 (m, 8H), 6.54 (s, 0.66H), 6.39 (s, 0.34H), 4.62 (m 1 H), 3.98 m 3 H), 2.63 (s, 3 H), 3.1-0 7 (complex signal, T). EXAMPLE 30 as and trans -l - [[l- (3- (3-Aminophenyl) -3-phenupropenoyl] -4-piperidylmethyl-lH-2-methylimidazo | 4,5-c] pyridine Following the procedure described in Reference example 3, but starting from the compound obtained in Example 29, the title compound was obtained as a white solid (147c) mp: 122-133 ° C (C28H29N5O.H2O);] H NMR (80MHz, CDCl 3 ) d (TMS): 8.94 (s, 1 H), 8.33 (d, J = 5.5Hz, 1 H), 7.28 (m, 8H), 6.63 (m, 2H), 6.20 (s, 0.4H), 6.16 (s, 0.6H), 4.67 (m, 1 H), 3.78 (m, 3H), 2.54 (s, 3H), 2.8-0.1 (complex signal, 9H) EXAMPLE 31 l-lll-l3- (4- Aminophenyl) -3- | N- (ethoxycarbonyl) aminojpropanoyl] -4- piperidillmetip-lH-2-methylimidazo [4,5-c] pyridine Following the procedure described in example 1. but using the acid 3- [N- ( ethoxycarbonyl) amino] -3- (4-n-troenyl) propane-co (obtained in reference example 17), and hydrogenation of the compound thus obtained according to the procedure described in reference example 3, the title compound was obtained in white solid form (15%). mp: 113-116 ° C (C25H32N6? 3.1 / 2H2?); ? H NMR (80 MHz, CDCl 3) d (TMS): 8.94 (s, 1 H), 8.35 (d, J = 5.5 Hz, 1 H), 7.21 (d, J = 5.5 Hz, 1 H), 7.07 (d, J = 9.5Hz, 2H), 6.63 (m, 3H), 4.95 (m, 1H), 4.60 (m, 1 H), 4.06 (q, J = 7.2Hz, 2H), 3.88 (m, 3H), 2.59 (s, 3H), 3.6-0.5 (complex signal, 1 1 H), 1.19 (t,] = 7.2Hz, 3H). EXAMPLE 32 l - ([l- (3-Phenylhexanoyl) -4-piperidyl] methyl-lH-2-methylimidazo [4,5-clpyridine] Following the method described in Example 1, but using 3-phenylhexane acid co Instead of the 3,3-diphenolpropane-co-acid, the title compound was obtained as a white solid (517o) .pf: 39-55 ° C (C25H32N4O.I / 2H 0); 1 H NMR (80MHz, CDCl 3 ) d (TMS): 8.96 (s, 1 H), 8.36 (d, J = 5.5Hz, 1 H), 7.24 (m, 6H), 4.60 (m, 1 H), 3.84 (m, 3H), 3.18 (m, 1 H), 2.58 (s, 3H), 2.8-0.5 (complex signal, 13H), 0 97 (t,] = 6.9Hz, 3H) EXAMPLE 33 ll (l-l3-Hydroxy-3- ( 2-methylpropyl) -5-methylhexanoyl] -4-piperidyl) methyl-1H-2-methylimidazo (4,5-c) pyridine Following the procedure described in Example 1. but using 3-hydroxyl acid - 3- (2-methypropyl) -5-methylhexane? Co (obtained in reference example 18) instead of 3,3-diphenolpropane? Co acid, the title compound was obtained in white solid stock (25%,.) Mp: 38-51 ° C (C24H38N4O2 1 / 4H20); '"] H NMR (80MHz, CDCI3) d (TMS): 8.98 (1H), 8.38 (d, J = 5.5Hz, 1H), 7.21 (d, J = 5.5Hz, 1H), 4.98 (s, 1 H), 4.69 (m, 1 H), 4.01 (d, J = 7.2Hz, 2H), 3.85 (m, 1 H), 2.63 (s, 3H), 3.1-1.1 (complex signal, 15H ), 1.00 (broad s, 12H) EXAMPLE 34 l - ([l- [3- (N- (4-Aminobenzenesulfonyl) aminol-3-phenyropropanoyl-4-piperidyl] methyl] -lH-2-methylj-midazo [ 4,5-c) pyridine Following the procedure described in Example 1, but using the 3- (N- (4-nitrobenzenesulfonyl) amino] propanoic acid, and hydrogenation of the compound thus obtained according to the procedure described in Reference example 3, the title compound was obtained as a white solid (227 °). "mp: 126-1340C (C28H32N6? 3S.H20);] H NMR (80MHz, CDC13 + CD30D) d (TMS): 8.86 ( s, 1 H), 8.32 (d, J = 5.5 Hz, 1 H), 7.53 (d, J = 8.3 Hz, 2 H), 7.16 (m, 7 H), 6.86 (d,) = 8.3 Hz, 2 H), 4.65 (m, 1 H), 4.55 (m, 5 1 H), 4.00 (m, 5H), 2.61 (s, 3H), 3-0.5 (complex signal, 9H). Alternatively, the obtained compound was reacted or in Example 6a with 4-n-trobenzenesulfonyl chloride in the presence of triethylamine to give l - [[1 - [3- (N - (4-n'-trobenzenesulfonyl) ammon) -3- phenylpropane] - 4-p-peridyl] methyl] -1 H-2-methylimidazo [4,5-c] pyridine, which was hydrogenated according to the procedure described in reference example 3 to give the title compound. EXAMPLE 35 1-1 (1-1 (N-Ethoxycarbonyl-N-phenylamino) acetyl] -4-piperidylmethyl-1H-2-methylirnidazo [4,5-c] pyridine Following the procedure described in example 1, but using N-ethoxycarbonyl-N-phenylglycine (prepared from N-phenylglycine and ethyl chloroformate) in place of the 3,3-d-phenylpropane acid, the title compound was obtained as a white solid (417c). mp: 130-137 ^ (C 24 H 29 N 5 O 3 H 2 O); 0 ^ H NMR (80MHz, CDCI3) d (TMS): 8.96 (s, 1 H), 8.35 (d, J = 5.5Hz, 1 H), 7.31 (m, 6H), 4.43 (m, 1 H), 4.40 (m, 2H), 4.15 (q, J = 7.2Hz, 2H), 3.96 (d, J = 6.9Hz, 2H) 3.90 (m, 1 H), 2.61 (s, 3H), 3-1.2 (complex signal, 7H), 1.19 (t,) = 7.2Hz, 3H). EXAMPLE 36 (S) -ll [ll [N- (1-Ethoxycarbonyl-3-methylbutyl) amino-1 -carbonyl-4-piperidyl-1-methyl-5-lH-2-methylimidazole-4,5-clpyridine A solution of the compound obtained in the reaction mixture was heated to reflux. reference example 5 (0.5 g, 2.1 mmol) and the ethyl ester of N-en -oxocarbon lL-Leucine (078 g, 2.7 mmol, prepared from the ethyl ester of L-Leuana and chloroormate of phenyl) in pyridine (15 mL) for 18 h. The solvent was removed in vacuo and the residue was partitioned between CHCl3 and 0.5N NaOH. The organic phase was dried and concentrated to give crude (1.33 g), which was purified by chromatography on silica gel (CHCh: MeOH, 5% >) to give the title compound as a white solid (0.22 g, 44% ). mp: 60-63 ° C (C22H33N5O3.3 / 4H2O); l H NMR (80 MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), 8.36 (m, 1 H), 7.26 (d, J = 5.5 Hz, 1 H), 5.30 (d, J = 8.17 Hz, 1 H), 4.51 (q, j = 8.12 Hz, 1 H), 4.18 (q, J = 6.5 Hz, 2 H), 4.15 (m, 1 H), 4.00 (d, J = 7.3 Hz, 2 H), 2.70 (m, 3H), 2.62 (s, 3H), 2.1 -1.4 (complex signal, 8H), 1.27 ü, j = 6.5Hz, 3H), 0.93 (d, J = 5.5 Hz, 6H). EXAMPLE 37 (S) -l- [[l - [(N- (l-Ethoxycarbonyl-2- (4-nitrophenyl) etillaminolcarbonyl-4-piperidylmethyl] -l H-2-methylimidazo (4,5-c) pyridine Following The procedure described in Example 36, but using the ethyl ester of N-phenoxycarbonyl-4-n-tro-L-phenylalanine instead of the ethyl ester of N-phenoxycarbonyl-L-Leucine, was obtained title compound in the form of white solid (547 °) mp: 85-89 ° C (C25H3? N605.l / 2H 0); 1 H NMR (80 MHz, CDCl 3) d (TMS): 8.94 (1 H), 8.35 (d, j = 5.5Hz, 1 H), 8.1 (d,) = 9. 2Hz, 2H), 7.32 (d, J = 9.2Hz, 2H), 7.20 (d, J = 5.5Hz, 1H), 5.32 (d, J = 8.17Hz, 1H), 4.81 (q, j = 8.12 Hz, 1 H), 4.18 (q, J = 6.5Hz, 2H). 4.00 (m. 1 H), 3.98 (d,) = 7.3 Hz. 2H), 3.23 (d, J = 5.8Hz, 2H), 2.70 (m, 3H), 2.63 (s, 3H), 2.1 -1 4 (complex signal, 5H), 125 (t, J = 6.5Hz, 3H ). EXAMPLE 38 (Sr-1 - ((l - [(N- (2- (4-Aminophenyl) -l-ethoxycarbonylethyl] amino] carbonyl] -4-piperidylmethyl) -lH-2-methylimidazol-4,5-c] pyridine Following the procedure described in reference example 3, but starting from the compound obtained in example 37, the title compound was obtained as a white solid (947c) mp: 87-96 ° C (C25H32N6O.H2O); ] H NMR (80 MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), 8.36 (d, J = 5.5 Hz, 1 H), 7.20 (d, J = 5.5 Hz, 1 H), 6.88 (d) , \ = 9.2Hz, 2H), 6.57 (d,) = 9.2Hz, 2H), 4 97 (d,) = 8.1 Hz. 1 H), 4.65 (q, j = 8.12Hz, 1 H), 4.18 ( q, j = 6.5Hz, 2H), 4.00 (m, 1 H), 3.98 (d, ¡= 7.3Hz, 2H), 2.98 (d, J = 5.8Hz, 2H), 2.80 (m.5H), 2.61 (s, 3H), 2.1 -1 4 (complex signal, 5H), 1.25 (t, J = 6.5Hz, 3H) EXAMPLE 39 (S) -l- (ll-l [N- (l-Ethoxycarbonyl-l- Phenemethyl) aminolcarbonyl] -4-piperidyl) methyl] -lH-2-methylimidazole4,5-c) pyridine Following the procedure described in Example 36, but using the ethyl ester of N-phenoxycarbonyl-L-phenylglycine (prepared from of the ethyl ester of L-phenylglycine and phenyl chloroormate) in place of the ethyl ester of N-phenoxycarbonyl-L-Leuana, the title compound was obtained as a white solid (61%). mp: 153-154 ° C (C24H29N5O3.I / 2H20); l H NMR (80 MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), 8.37 (d, j = 5.5 Hz, 1 H), 7.33 (m, 5 H), 7.20 (d, J = 5.5 Hz, 1 HOUR). 5.51 (m, 2H), 4.18 (q, J = 6.5Hz, 2H), 4.00 (m, 1 H), 3.98 (d,] = 7.3Hz, 2H), 2.72 (m, 3H), 2.61 (s, 3H), 2.1 -1.4 (complex signal, 5H), 1.20 (t, j = 6.5Hz, 3H). EXAMPLE 40 l- [ll- (3-FenUbutaneU) -4-piperidU] metill-lH-2-methylimidazol4,5-clpiridir Following the method described in Example 1, but using 3-phenylbutanoic acid instead of acid 3, 3-diphenylpropanoic, the title compound was obtained as a white solid (387o). mp: 38-41 ° C (C 23 H 28 N 4 O.H 2 O); l H NMR (80 MHz, CDCl 3) d (TMS): 8.87 (s, 1 H), 8.28 (d, J = 5.5 Hz, 1 H). 7.16 (m, 6H). 4.60 (m, H), 3.76 (m, 3H), 3.30 (m, 1H), 2.50 (s, 3H), 3-0.5 (complex signal, 9H). 1.25 (d, J = 6.9Hz, 3H). EXAMPLE 41 l- (ll- (3-Phenyl-3-methylbutanoyl) -4-piperidyl) methyl-lH-2-methylimidazole4,5-cliplidine Following the procedure described in example 1, but using 3-phenyl-3 acid -methylbutane? co (obtained in reference example 19) instead of 3-diphenylpropane? co acid, the title compound was obtained as a white solid (587o). mp: 37-45 ° C (C24H3oN40.1 / 2H2O); ] H NMR (80 MHz, CDCl 3) d (TMS): 8.95 (s, 1 H), 8.38 (d, J = 5.5 Hz, 1 H), 7.26 (m, 6H), 4.65 (m 1 H), 3.86 (d,) = 7.1 Hz. 2H), 3.50 (m, 1 H), 2.58 (s, 3H), 3-0.5 (complex signal, 9H), 1.25 ( s, 6H) EXAMPLE 42-1-1-1 (N-Phenyl-N-ritylamino) acetyl] -4-piperidyl] methyl 1-1 H -2-methyl imidazo (4,5-cyphexidine Following the procedure described in example 1. but using the N-phenyl-N-methylaminoacetic acid (obtained in the reference example 20) instead of the 3,3-d? in? lpropane? co acid, the title compound was obtained as a white solid ( 397c) mp: 74-78 ° C (C22H27N O.H2O);] H NMR (80MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), 8.36 (d, J = 5.5Hz, 1 H) , 7.21 (m, 3H), 6.71 (m, 3H), 4.60 (m, 1 H), 4.05 (s, 2H), 3.92 (d, J = 7.1 Hz, 2H), 3.80 (m, 1 H), 2.99 (s, 3H), 2.59 (s, 3H), 3-1 (complex signal, 7H) EXAMPLE 43 l-lll-l3-Methyl-3- (4-nitrophenyl) butanoill-4-piperidyl] metill-lH -2- Methylimidazo (4,5-c) pyridine Following the procedure described in Example 1, but using 3-met? L-3- (4-n? Troenyl) butane? Co (obtained in the reference example) Inc 21) instead of the 3,3-diphenolpropane acid, the title compound was obtained as an oil (287o). 1 H NMR (80 MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), 8.37 (d, J = 5.5 Hz, 1 H), 8.1 1 (d, J = 8.4 Hz, 2 H), 7.51 (d , J = 8.4 Hz, 2H), 7.18 (d, J = 5.5Hz, 1 H), 4.55 (m, 1 H), 3.95 (d, J = 7. 1Hz. 2H), 3.83 (m, 1 H), 2.59 (s, 3H), 3-0.5 (complex signal, 9H), 1.50 (s, 6H). EXAMPLE 44 l-lll-l3- (4-Aminophenyl) -3-methylbutanoyl] -4-piperidyl) rnethyl] -lH-2-methylimidazo [4,5-c) pyridine Following the method described in reference example 3, but starting from the compound obtained in Example 43, the title compound was obtained as a white solid (5770) mp: 172-173 ° C (C24H31N5O.3 / 4H2O), H NMR (80MHz, CDCl3) d (TMS): 8.96 (s, 1 H), 8.38 (d, J = 5.5Hz, 1 H), 7.18 (m, 3H), 6.62 (d, J = 5.5Hz, 2H), 4.65 (, 1 H), 3.86 (d) ,] = 7.1 Hz, 2H), 3.63 (m, 2H), 3.50 (m, 1 H), 2.59 (s, 3H), 3-0.5 (complex signal, 9H), 1.25 (s, 6H). EXAMPLE 45 l-III-l [N- (Diphenylmethyl) aminolcarbonyl-4-piperidylmethyl] -lH-2-methylimidazo (4,5-c] pyridine Following the procedure described in Example 36, but using the N-phenoxycarbonyl -N- (diphenylmethyl) amine (prepared from the amino-diphenyl methane and phenyl chloroormate) in place of the ethyl ester of N-phenoxycarbonyl-L-Leucine, the title compound was obtained as a white solid ( 26%) mp: 212-218 ° C (C27H29N? O.H2?);? H NMR (80MHz, CDCI3) d (TMS): 8.96 (s, 1 H), 8.35 (d, J = 5.5Hz. H), 7.27 (m, 11H), 6.14 (d,) = 7.0Hz, 1H), 5.12 (d, J = 7.0Hz, 1H). 4.00 (m, 1 H). 3.96 (d, J = 7.3Hz, '"2H), 2.70 (m, 2H), 2.61 (s 3H), 2.1 -1 1 (complex signal, 6H) EXAMPLE 46 l-lll-l [N- (4 -Aminobenzoyl) -N-methylamino] acetyl) -4-piperidylmethyl-lH-2-methylimidazo [4,5-c] pyridine a) l- [ll-. {(N-methyI-N-rert-butoxycarbonyl? Nino ) acetill-4-piperidylmethyl-lH-2-methylimidazo | 4,5-clpyridine Following the procedure described in Example 1, but using N-methyl-N- (/ fr / -butox? carbonyl) am? no] acetic acid in place of 3,3-diphenylpropanoic acid, the desired product was obtained (63%) b) ll [l- [N-methylaminoacetill-4-piperidyl] methyl] -lH-2-methylimidazole4,5-c] p indina Following the procedure described in reference example 5, but starting from the compound obtained in section a), the desired product was prepared (quantitative yield) c) Titrant compound Following the procedure described in example 6b, but using the compound obtained in example 46b instead of the compound obtained in example 6a, the compound titu was obtained lar (327o). mp: 120-124 ° C (C23H28N6O2.H2O); H NMR (80 MHz, CDCl 3) d (TMS): 8.97 (s, 1 H), 8.38 (d, J = 5.5 Hz, 1 H), 7.25 (m, 3H), 6.61 (d, J = 9.0Hz, 2H), 4 64 (m, 1 H), 4.01 (m, 2H), 3.98 (d, j = 7.1 Hz, 2H), 3.10 (s, 3H), 2.62 (s 3H), 3.3-1 (complex signal, 10H). EXAMPLE 47 l-III- (3-Phenyl-3-hydroxy-3-trifluoromethylpropanoyl) -4-piperidylmethyl] -lH-2-5-methylimidazole-4,5-c) pyridine Following the procedure described in example 1, but using the acid 3-phenol-3-hydroxy-3-trifluoromethylpropane (obtained in reference example 11) instead of 3,3-diphenolpropane? Co acid, the title compound was obtained as a solid white (157o). 0 mp: 210-2n ° C (C23H25F3N4O2.I / 2H20); H NMR (80 MHz, CDCl 3) d (TMS): 8.90 (s, 1 H), 8.36 (d,] = 5.5 Hz, 1 H), 7.35 (m, 6 H), 4 68 (m, 1 H), 4 60 (.1 H), 3 94 (, 3H), 2.60 (s 3H), 3-0 5 (complex signal, 9H). EXAMPLE 48 5 trans-l-III- (3- (4-Arninofen.l) -2-butenoyl] -4-piperidylmethyl-lH-2-methylimidazole4,5-clpyridine Following the procedure described in example 1, but using the 3- (4-n-tetrenyl) -2-butene-co (obtained in reference example 22), and by hydrogenating the compound thus obtained according to the procedure described in example of reterenase 3, the title compound was obtained in white solid form (22%) mp: 106-n 0 ° C (C23H27N Ol / 2H2?); 1 H NMR (80MHz, CDC13) d (TMS): 8.98 (s, 1 H), 8.38 (d, J = 5.5Hz, 1H), 7.27 (m, 3H), 6.60 (d, J = 8.5Hz, 2H), 6.17 (s, 1 H), 4.67 (m, 1 H), 3.90 (d, J = 7.2 Hz, 2H), 3.81 (m, 1 H), 2.63 (s, 3H), 2.23 (s, 3H), 3.1 -0.5 (complex signal, 9H) EXAMPLE 49 l-ll ll (Phenylamino) acetyl-piperidyl] methyl] -l H-2-methylimidazo (4,5-c] pyridine Following the procedure described in example 1, but using the N- / t? Rf -butox? Carbonyl-N-phen? Lgl? C? Na instead of 3,3-diphenylpropane? Co acid, and subjecting the resulting compound to the procedure described in reference example 5, the titular compound in the form of a white solid (49%). mp: 219-220 ° C (C21 H25N5O.H2O); ? H NMR (80 MHz, CDCl 3) d (TMS): 9.00 (s, H), 8.40 (d, j = 5.5 Hz, 1 H), 7.20 (m, 4H), 6.66 (m, 2H), 4.72 (m, 2H), 3.89 (m, 5H), 2.63 (s, 3H), 3.2-1 (m, 7H). EXAMPLE 50 (R) -ll [11 (l-Phenylethylamino) carbonyl] -4-piperidillmetU) -lH-2-methylimidazole-4,5-clpyridine Following the procedure described in example 36, but using the (R) -N-phenoxy carbonyl-l-phenyl-lettylamine (prepared from (R) -l-phenylethylamine and phenyl chloroformate) in place of the ethyl ester of N-phenoxycarbonyl-L-Leucine, the title compound was obtained in the form of white solid (37%). mp: 80-84 ° C (C22H27N5O.I / 2H20); l H NMR (80 MHz, CDCl 3) d (TMS): 8.97 (s, 1 H), 8.38 (d, J = 5.5 Hz, 1 H), 7.30 (m, 5H), 7.20 (d, J = 5.5Hz, 1 H), 5.01 (quint, J = 6.8 Hz, 1 H), 4.70 (d wide, j = 7.1 Hz, 1 H), 4.02 (m, 1 H) , 3.97 (d, 1 = 7.3Hz, 2H), 2.68 (wide t, j = 12.7Hz, 2H), 2.62 (s, 3H), 1.48 (d,] = 6.5 Hz, 3H), 2.1-1.3 (m.6H). EXAMPLE 51 (S) -ll [lI (l-Phenylethylamino) carbonill-4-p? Peridylmethyl-II-2-methylimidazo | 4,5-cipyridine Following the procedure described in Example 36, but using the (S) -N -Nenox? carboni l-l -te? let? lam? na (prepared from (S) -l-eneethylethylamine and phenyl chlorotormiate) in place of the ethyl ester of N-inox? carbon? L-Leuana, the title compound was obtained as a white solid (417c). mp: 79-83 ° C (C22H27N O.I / 2H 0); H NMR (80 MHz, CDC13) d (TMS): 8.98 (s, 1 H), 8.38 (d, J = 5.5 Hz, 1 H), 7.26 (m, 5 H), 7.20 (d, J = 5.5 Hz, 1 H), 5.01 (quint, J = 6.8 Hz, 1 H), 4.68 (wide d, J = 7.1 Hz, 1H), 4.02 (m, 1 H), 3.97 (d,) = 7.3Hz, 2H), 2.68 (t wide,) = 12.7Hz. 2H), 2.62 (s, 3H), 1.48 (d, J = 6.5 Hz, 3H), 2.1-1.3 (m, 6H). EXAMPLE 52 l-III-L (N-Benzoyl-N-phenylamino) acetyl] -4-piperidyl) methyl) -lH-2-methylimidazo4,5-c] pyridine On a cooled solution (0 ° C) of the compound obtained in Example 49 (0.3 g, 0.824 mmol) and Et ^ (0.1 mL) in CH2Cl2 (6 mL), a soluaon of benzoyl chloride (0.09 mL) in CH2Cl2 (0.2 mL) was added dropwise and The mixture was stirred at room temperature overnight. The resulting solution was treated with 0.5N NaOH and extracted with CH2Cl2 (3x). The organic phase was dried and concentrated, obtaining a crude product which was purified by chromatography on silica gel (CHCh-MeOH, 8%) to give the title compound (70%) ? H NMR (80MHz, CDCl 3) d (TMS). 8.96 (m, 1 H), 8.38 (m, 1 H), 7.16 (m, 11 H), 4.68 (m, 3 H), 3.92 (m, 3 H), 2.60 (s, 3 H), 3.2-1.2 (m , 7H). The hydrochloride was prepared following the procedure described in example 13. mp: 145-152 ° C (C2sH2 N5O2.3HCl.H2O). EXAMPLE 53 l-ll l-ll N-methyl-N- (4-nitrobenzenesulfonyl) amino] acetill-4-piperidyl) methyl 1-1 H-2-methylimidazo [4,5-c] pyridine Following the procedure described in Example 52, but starting from the compound obtained in Example 46b) and using 4-nttrobenzenesulfonyl chloride in place of benzoyl chloride, the title compound was obtained as a white solid (487c). mp: 98-104 ° C (C22H2r.NeO5S.H2O); ] H NMR (80 MHz, CDCh) d (TMS): 8.99 (s, 1 H). 8.39 (d, 1 = 5.5 Hz, 1 H), 8.36 (d, | = 6.9 Hz, 2 H), 7 99 (d, 1 = 6 9 Hz, 2 H), 7.22 (d, J = 5.5 Hz, 1 H ). 4.52 (m.l H). 3.97 (m, 5H), 2.89 (s 3H). 2.64 ts. 3H), 3.2-1.3 (m, 7H) EXAMPLE 54 l-ll l-ll N-Etox? Carbonyl-N- (4-nitrophenyl) amino lacet il] -4-p? Peridyl Imethyl 1-1 H-2- methylimidazole4,5-clpyridine Following the procedure described in Example 1, but using the acid N-ethoxycarbon? N- (4-n? trofen? l) amno-acetic acid (obtained in reference example 23) in Place of 3,3-d? phen? lpropane? co acid. the title compound was obtained as a white solid (647 °). ] H NMR (80 MHz, CDC13) d (TMS): 8.96 (s, 1 H), 8.37 (d, J = 5.5 Hz, 1 H), 8.13 (d, J = 7.05 Hz, 2 H), 7.48 (d, J = 7.05Hz, 2H), 7.21 (d, J = 5.5Hz, 1 H), 4.65 (m, 1 H), 4.51 (d, J = 4.3 Hz, 2H), 4.22 (q, J = 7.1 Hz, 2H), 4.02 (d, J = 7.2 Hz, 2H), 3.80 (m, 1 H), 2.63 (s, 3H), 3.1-1.3 (m, 7H), 1.24 (t, j = 7.1 Hz, 3H) . L-lll-lfN- (4-Aminophenyl) -N-ethoxycarbonylamino] acetill-4-piperid II] methyl] -lH-2-methylimidazo (4,5-c] pyridine Following the procedure described in reference example 3 , but starting from the compound obtained in Example 54, the title compound was obtained as a white solid (747 °): mp: 137-138 ° C (C 24 H 30 N 6 O 3 H 2 O); H NMR (80 MHz, CDCl 3) d (TMS): 8.98 (s, 1 H), 8.40 (d, J = 5.5 Hz, 1 H), 7.20 (d, J = 5.5 Hz, 1 H), 7.10 (d, J = 7.05 Hz, 2 H), 6.60 (d, J = 7.05Hz, 2H), 4.65 (m, 1 H), 4.30 (m 2H), 4.10 (m, 4H), 3.80 (m, 3H), 2.62 (s, 3H), 3.1-1.3 (m, 7H) ), 1.17 (t, j = 6.9 Hz, 3H) EXAMPLE 56 trans-l-III- (3-phenyl-2-pentenoyl) -4-piperidyl] methyll-lH-2-methylimidazo [4,5- cipi idine Following the descpto procedure in example 1, but using the acid f raps-3-phen? L-2-pentene? Co (obtained in the reference example 24) instead of the 3,3-d? Phen? Lpropane acid? co, the title compound was obtained as a white solid (747 °) mp: 59-62 ° C (C24H28N4O.I / 2H20); N (80MHz, CDCI3) d (TMS): 8.99 (s, 1 H), 8.40 (d, J = 5.5Hz, 1 H), 7.36 (m, 5H), 7.20 (d, 1 = 5.5Hz, 1 H), 6.09 (s, 1 H), 4.75 (m, 1 H), 4.05 (m, 1 H), 4.01 (d, J = 7.1 Hz, 2H ), 2.72 (q, J = 7 4 Hz, 2H), 2.64 (s, 3H), 3.1 -1.3 (m, 7H), 1.02 (t, j = 7 4 Hz, 3H). EXAMPLE 57 l-ll l-ll N- (2-Methoxybenzyl) aminolcarbonyl-4-p-peridylmethyl 1-1 H-2-methylimidazole 4,5-clpyridine Following the procedure described in example 3, but using N-eneox? carbon? lN- (2-methox? benc? l) am? na (prepared from 2-methoxy-benahenamine and phenyl chloroormate) in place of the ethyl ester of N-phenoxycarbon? l-Leucine, obtained the title compound as a white solid (177o). mp: 76-85 ° C (C 22 H 27 N 5 O 2); H NMR (80MHz, CDCI3) d (TMS): 8.96 ts, 1 H), 8.35 (d, J = 5.5Hz. L H), 7.25 (m, 3H), 7.89 (t, J = 7.2Hz, 2H) , 5.14 (t, j = 5.3 Hz, 1 H), 4.40 (d, J = 5 6 Hz, 2 H), 3.91 (m 4 H), 3.82 (s, 3 H), 2.60 (s, 3 H), 2.8-1.3 (m, 7H). EXAMPLE 58 (R) -l-III-II (l-Ethoxycabonyl-l-phenyl) methylamino] carbonyl] -4-piperidyl) methyl] -lH-2-methylimidazo (4,5-cjpyridine Following the procedure described in the example 36, but using the ethyl ester of the (R) -N-phenoxycarbonyl-2-phenylgliana (prepared from the ethyl ester of the (R) -2-ene-glycol and phenyl chloroormate) instead of the ethyl ester of N-phenoxycarbonyl-L-Leucine, the title compound was obtained as a white solid (277 °) mp: 78-80 ° C (C24H29N5O3.I / 2H20); l H NMR (80 MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), 8.35 (d, J = 5.5 Hz, 1 H), 7.33 (s, 5 H), 7.19 (d, J = 5.5 Hz, 1 H), 5.52 (m, 2H), 4.13 (m, 6H), 2.71 (m 2H), 2.60 (s, 3H), 2.10 (m, 1 H), 1.45 (m, 4H), 1.19 (t, J = 7.1 Hz, 3H). EXAMPLE 59 l-III-l (l-Phenyl-l-cyclopropylamine) carbonill-4-piperidylmethyl) -lH-2-methylimidazo (4,5-c) pyridine On a solution of 1-phenyl-1-cyclopropanecarboxylic acid (1.62) g, 0.01 mol) and Et N (1.14 mL) in benzene (40 mL) was added dropwise diphenylphosphoplazide (2.14 mL) .The mixture was heated at 90 ° C for 2 h. The compound obtained in the example obtained was then added. reference 5 (1.6 g, 6. 8 mmol) and the mixture was heated at 90 ° C overnight. After cooling, 1N NaOH was added and extracted with AcOEt (3x). The organic phase was dried and concentrated, obtaining a crude product which was purified by chromatography on silica gel (CHCh-MeOH, 107) to give the title compound as a white solid (1.24 g, 47%). mp: 227-228 ° C (C23H27N5O); ^ H NMR (80MHz, CDCl 3) d (TMS): 8.98 (s, 1 H), 8.38 (d, J = 5 5Hz, IH), 7.23 (s, 6H), 5 44 (s 1 H), 4.02 (m, 2H), 3.97 (d, J = 8.0 Hz, 2H), 2.64 (m 2H), 2.62 (s 3H), 2.10 (m, 1 H), 1.55 (m, 4H), 1.22 (s) , 4H) EXAMPLE 60 (S) -ll (II (2-Ethoxy-1-phenylethylamino) carbonyl-4-piperidylmethyl-1H-2-methylimidazo | 4,5-clpyridine Following the procedure described in example 36, but using the Ethyl ether of (S) -N-phenoxycarbonyl-2-phenylglycol (prepared from the ethyl ether of 2-phenylglycanol and phenyl chloroormate) instead of the ethyl ester of N-phenoxycarbonyl-L-Leucine, the Titrant compound in the form of a white solid (247o), mp: 68-70 ° C (C24H31 N5O2);] H NMR (80MHz, CDCl 3) d (TMS): 8.97 (s, 1 H), 8.38 (d, J = 5.5Hz, 1 H), 7.29 (s, 5H), 7.21 (d,) = 5.5Hz, 1 H), 5.36 (d, J = 6.4 Hz, 1 H), 5.01 (q, J = 5.4 Hz, 1 H), 4.05 (m, 2H), 3.96 (d, J = 7.1 Hz, 2H), 3.54 (m, 4H), 2.75 (m, 2H), 2.61 (s, 3H), 2.10 (m, 1 H) , 1.45 (m, 4H), 1.15 (t,] = 6.9 Hz, 3H). EXAMPLE 61 ll [II (2-Phenyl-2-methylpropyl) sulfonyl-4-piperidyl] methyl) -lH-2-methylimidazole-4,5-clpyridine. On a solution of the compound obtained in reference example 5 (1 g, 4 mmol ) and E13N (0.6 mL) in CHCl3 (20 mL), 2-ferul-2-methylpropyl-sulfonyl chloride (2.32 g, 10 mmol, obtained in reference example 25) was added and the mixture was stirred at Room temperature during a night. The resulting solution was diluted with CHCl3, washed with 0.5N NaOH, dried and concentrated. The residue was purified by chromatography on silica gel (CHCl3-MeOH, 57o) to give a solid that was recrystallized from hot AcOEt. The title compound was obtained as a white solid (0.4 g, 25%). mp: 165-166 ° C (C 23 H 30 N 4 O 2 S); i H NMR (80 MHz, CDCl 3) d (TMS): 8.98 (s, 1 H), 8.38 (d, J = 5.5 Hz, 1 H), 7.32 (m, 5H), 7.17 (d, J = 5.5Hz, 1 H), 3.94 (d, J = 6.9 Hz, 2H), 3.65 (s, 2H), 2.60 (d wide, J = 12.0 Hz, 2H), 3.16 (s, 2H), s, 3H), 2.18 (broad t, J = 12.0 Hz, 2H), 1.58 (s, 6H), 1.48 (m, 5H). EXAMPLE 62 l-III- (3-Phenylpropanoyl) -4-piperidylmethyl-lH-2-methylimidazole-4,5-cyridine Following the procedure described in Example 1, but using 3-phenolpropane? Co acid instead of 3,3-diphenylpropanoic acid, the title compound was obtained as a white solid. mp: 52-58 ° C (C22H26N OJ / 4H2O); ] H NMR (80 MHz, CDCl 3) d (TMS). 8.96 (s, 1 H). 8.38 (d, j = 5.5Hz, 1 H). 7.23 (m, 6H), 4.71 (broad d, | = 13.6 Hz, 1 H), 3 94 (d, j = 7.21 Hz, 2H), 3.56 (wide d. | = 13.6 Hz, 1 H), 2.80 ( m, 2H), 2.62 (m, 2H), 2.61 (s, 3H), 2.7-0.8 (m.7H) EXAMPLE 63 l-III-III- (4-Nitrophenyl) ethylaminolcarbonyl-4-piperidyl] methyl) - lH-2-methylimidazole4,5-c] pyridine Following the procedure described in Example 59, but using 2- (4-n-troenyl) propane-co-acid instead of 1-phenyl? 1-Cyclopropanecarboxylic acid, the title compound was obtained as a white solid (577 °). ] H NMR (80 MHz, CDC13) d (TMS): 8.95 (s, 1 H), 8.35 (d, J = 5.5 Hz, 1 H), 8.22 (d,] = 9.1 Hz. 2 H), 7.45 (d, J = 9.1 Hz, 2H), 7.20 (d,) = 5.5Hz, 1H), 5.03 (m, 2H), 4.05 (m, 2H), 3.96 (d, J = 7.1 Hz, 2H), 2.71 (m , 2H), 2.62 (s, 3H), 1.48 (d, J = 6.6 Hz, 3H), 2-2-1.0 (m, 5H). EXAMPLE 64 L-III-III- (4-Aminophenyl) ethylamino] carbonyl] -4-piperidyl] methyl-lH-2-methylimidazo (4,5-c) pyridine A solution of the compound obtained in Example 63 (0.8 g, 1.89 mmol) and SnCl .2H2? (2.188 g, 9.4 mmol) in EtOH (25 mL) at 60 ° C and then a solution of NaBHj (0.035 g, 0.94 mmol) in EtOH (15 mL) was added dropwise. The reaction mixture was heated at 60 ° C for 1 h and then cooled to 10 ° C, basified and extracted with CHCl 3, washing with water. The organic phase was dried and concentrated, obtaining a crude product which was chromatographed on silica gel (CHCl3: MeOH: NH3, 60: 20: 0.2) to give the title compound (27 mg, 4%). mp: 122-128 ° C (C22H28N60.3 / 2H20); l H NMR (80 MHz, CDCl 3) d (TMS): 8.96 (s, 1 H), 8.36 (d, J = 5.5 Hz, 1 H), 7.18 (d, J = 5.5 Hz, 1 H), 7.1 1 (d , J = 8.3 Hz, 2H), 6.62 (d, J = 8.3 Hz, 2H), 4.90 (quint, J = 6.7 Hz, 1 H), 3.96 (d, J = 6.4 Hz, 1 H), 3.96 (m 4H), 2.64 (m, 2H), 2.61 (s, 3H), 2.10 (m, 1 H), 1.43 (d, 1 = 6.6 Hz, 3H), 1.26 (m, 6H). EXAMPLE 65 trans -1-1 (1-13- (4-Aminofenyl) propenoyl) -4-piperidylmethyl 1-1 H-2-methylimidazo (4,5-c) pyridine Following the method described in Example 1 , but using the ph-4-amynocinnamic acid hydrochloride in place of 3,3-diphenylpropanoic acid, the title compound was obtained as a white solid (71%) mp: 1 15-120 ° C (C22H 5N? 0.1 / 2H20); 'H NMR (80 MHz, CDCh) d (TMS): 8.99 (s, 1 H), 8.40 (d, J = 5.5 Hz, 1 H). 7.62 (d, 1 = 15.3 Hz, 1 H), 7.32 (d,) = 8 4 Hz, 2 H). 7.20 (d, J = 5.5 Hz, 1 H), 6.64 (d, J = 15.3 Hz, 1 H), 6.63 (d, 1 = 8 3 Hz, 2 H), 4.40 (m, 1 H). 4.00 (d, J = 7.3 Hz, 2H), 3 94 tm, 1 H), 2.80 (m, 2H), 2.64 (s, 3H), 2.4-1.2 (m, 7H). EXAMPLE 66 1-lll-lIN-Methyl-N- (2-methoxyphenU) ammo) acetill-4-piperidylmethyl-lH-2-methylimidazo [4,5-c] pyridine Following the procedure described in example 1, but using the [N-methyl-N- (2-methoxyphenyl) ammonoic acid (obtained in reference example 26) in place of 3,3-diphenylopropane acid, the title compound was obtained in the form of white solid (717o). mp: 59-64 ° C (C23H29N5O2.I / 2H20); H NMR (80 MHz, CDCl 3) d (TMS): 8.98 (s, 1 H), 8.38 (d, J = 5.5 Hz, 1 H), 7.20 (d, J = 5.5 Hz, 1 H), 7.06 (m, 3 H) ), 4.45 (m, 1 H), 4.42 (m, 1 H), 3.97 (m, 4H), 3.82 (s, 3H), 2.87 (s, 3H), 2.63 (m, 3H), 2.62 (s, 3H), 2.4- .2 (m, 5H) EXAMPLE 67 l-Ul-l (4- (Iert-butoxycarbonylamino) phenethylaminecarbonyl] -4- piperidu] methyl] -lH-2-methylimidazol-4,5-clpyridine Following the procedure described in Example 59, but using the 4- (N-ε-butoxycarbonylamino) phenylacetic acid in place of 1-phenyl-1-cyclopropanecarboxylic acid, the title compound was obtained as a white solid (947 °). -130 ° C (C26H 34 ^ 03! / 2H20);? H NMR (80MHz, CDCI3) d (TMS): 8.96 (s, 1 H), 8.36 (d, J = 5.5Hz, 1 H), 7.28 ( m, 5H), 6.90 (s, 1 H), 5.05 (m, 1 H), 4.31 (d, J = 5.2 Hz. 2H), 4.03 (m, 2H), 3.96 (d, J = 7.1 Hz. 2H), 2.62 (m, 2H), 2.60 (s, 3H), 2.1 -1.2 (m, 5H), 1.50 (s, 9H). EXAMPLE 68 l-III-l (4-Aminophenylmethylamino) carbonyl-4-piperidyl] methyl-lH-2-methylimidazo [4,5-c] pyridine Following the method described in reference example 5, but starting from the compound obtained in Example 67, the title compound was obtained as a white solid (707o). mp: 104-109 ° C (C2i H26N6O.H2); ] H NMR (80 MHz, CDCl 3) d (TMS): 8.92 (s, 1 H), 8.34 (d,) = 5.5 Hz, 1 H), 7.19 (d, J = 5.5 Hz, 1 H), 7.05 (d , J = 8.2 Hz, 2H), 6.58 (d, J = 8.2 Hz, 2H), 5.05 (m, 1 H), 4.26 (d, J = . 2 Hz. 2H), 4.08 (m, 2H), 3.96 (d, J = 7.1 Hz, 2H), 3.40 (m, 2H), 2.60 (m, 2H), 2.59 (s, 3H), 2.1 -1.2 ( m, 5H). EXAMPLE 69 l-ll l- (3- (2-Methoxy-enyl) -propanoyl-4-piperidylmethyl-1-1H-2-methyl imidazole 4,5-clpyridine Following the procedure described in example 1, but using the 3- (2-methox? Phenyl) propane? Co, in place of 3,3-d? In? Lpropane? Co, the title compound was obtained as a white solid (207 °) mp: 54-56 ° C (C23H28 4O2. I / 2H20);! H NMR (80MHz, CDCI3) d (TMS): 8.97 (s, 1 H), 8.37 (d, J = 5.5Hz, 1 H), 7.15 (m, 3H), 6.86 (m, 2H), 4.71 (d wide, J = 13.6 Hz, 1 H), 3.94 (d, J = 7.21 Hz, 2H), 3.81 (m, 1 H), 3.80 (s, 3H), 2.97 (m, 2H) , 2.62 (s, 3H), 2.61 (m, 4H), 2.3-0.8 (m, 5H) EXAMPLE 70 l-. {Ll-ll (l-Phenyl-l-cyclopropU) methoxy] carbonill-4-piperidylmethyl -lH-2-methylimidazole-4,5-c] pyridine Following the procedure described in example 36, but using the phenyl (l-phenyl-1-cyclopropyl) methyl carbonate (prepared from 1-phenyl-1-cyclopropanmethanol and phenyl chloroormate) in place of the ethyl ester of N-phenoxycarbonyl-L-Leuana, obtained the title compound as a white solid (237o). mp: 138-140 ° C (C24H28N4O2.I / 2H20); H NMR (80 MHz, CDCl 3) d (TMS): 8.97 (s, 1 H), 8.37 (d, J = 5.5 Hz, 1 H), 7.27 (s, 5 H), 7.19 (d,] = 5.5 Hz, 1 H), 4.16 (s, 2H), 4.15 (wide d, J = 13.6 Hz, 2H), 3.94 (d, J = 7.21 Hz, 2H), 2.60 (s, 3H), 2.60 (m, 2H), 2.3 -0.8 (m, 5H), 0.92 (s, 4H). EXAMPLE 71 frans-1 - ([1-13-Fenu-3- (methoxybutyl) propenoyl] -4-piperidulmethyl] -lH-2-methylimidazo (4,5-c] pyridine Following the procedure described in example 1, but using f-raps-3-phenyl-3- (methox? methyl) propene? co acid (obtained in reference example 27) instead of 3,3-diphenylpropane? co acid, the title compound was obtained as a solid white, mp: 63-67 ° C (C24H28N4O2.H2O); H NMR (80MHz, CDCI3) d (TMS): 8.98 (s.1 H), 8.40 (d, J = 5.5Hz, 1 H), 7.27 (m, 5H), 7.18 (d, J = 5.5Hz, 1 H), 6.39 (s, 1H), 4.60 (m, 1 H), 3.98 (m, 1 H), 3.96 (d, J = 7.2 Hz, 2H), 3.71 (s, 3H), 3.54 (d, J = 7.2 Hz, 2H), 2.60 (s, 3H), 3.1-1.3 (m, 7H). EXAMPLE 72 [1-N-N-Phenyl-N- (4-nitrophenylsulfonyl) amino] acetyl] -4-piperidyl) methyl] -lH-2-methylimidazo [4,5-clpyridine] On a solution of the compound obtained in Example 49 (2.5 g, 6.9 mmol) in pyridine was added the 4-n-trobenzenesultonyl chloride (1.54 g) and the resulting mixture was heated at 60 ° C for 18 h. The solvent was removed and the residue partitioned between 0.5N NaOH and CHCl3. The organism phase was dried and concentrated, obtaining a crude product which was chromatographed on silica gel (CHCl 3: MeOH, 10% -) to give the title compound as a yellow solid (2.93 g, 787 °). 115 ° C (C27H28N6O5S.I / 2H20); ] H NMR (80 MHz, CDCl 3) d (TMS): 9.00 (s, 1 H), 8.40 (d, J = 5.5 Hz, 1 H), 8.26 (d, J = 8. 8Hz, 2H), 7.84 (d, j = 8.8 Hz, 2H), 7.27 (m, 5H), 7.18 (d,) = 5.5Hz, 1H), 4.70 (m, 1H), 4.52 (s, 2H) , 4.00 (d, J = 7.2 Hz, 2H), 3.80 (m, 1H), 2.64 (s, 3H), 3.1 -1.3 (, 7H). EXAMPLE 73 L-ll l-ll N- (4-Aminophenylsulfonyl) -N-phenylaminolacetyl] -4-piperidyl] methyl 1-1 H-2-methylimidazol-4,5-c] pyridine Following the procedure described in reference example 3 , but starting from the compound obtained in Example 72, the title compound was obtained as a white solid (787o). ,. mp: 147-157 ° C (C27H30N O3S.H2O); ] H NMR (80 MHz, CDCl 3) d (TMS): 8.79 (s, 1 H), 8.38 (d, J = 5.5 Hz, 1 H), 7.45 (d, J = 8.8 Hz, 2 H), 7.26 (m, 6H), 6.94 (d, J = 8.8Hz, 2H), 4.36 (m, 1 H), 4.35 (s, 2H), 4.00 (d, J = 7.2 Hz. 2H), 3.98 (m, 1 H), 2.63 (s, 3H), 3.3-1.0 (m, 9H). EXAMPLE 74 l-. { 11-1 (2-Phenyl-2-methylpropylamino) carbonyl] -4-piperidylmethyl) -lH-2-methylimidazo (4,5-c] pyridine Following the procedure described in example 59, but using 3-phenyl- 3-methylbutane-co (obtained in reference example 19) instead of 1-phenyl-1-cyclopropanecarboxylic acid, the title compound was obtained as a white solid (36%) mp: 66-69 ° C (C24H31) N5O.I / 2H2O);] H NMR (80MHz, CDCl 3) d (TMS): 8.98 (s, 1 H), 8.39 (d, j = 5.5Hz, 1 H), 7.25 (m, 5H), 7.18 ( d, J = 5.5Hz, H), 4.08 (m, 1 H), 3 94 (d, J = 7.3 Hz, 2H), 3.78 (broad d, J = 16. 0 Hz, 2H), 3.43 (d, j = 5.7 Hz, 2H), 2.61 (s, 3H), 2.60 (m, 2H), 2.1-0.8 (m, 5H), 133 (s, 6H). EXAMPLE 75 l-lll-llN-Isobutyl-N- (4-nitrophenylsulphonyl) aminolacetyl) -4-piperidyl] methyl-lH-2-methylimidazole 4,5-clpyridine Following the procedure described in Example 1, but using the N- acid isobutyl-N- (4-n-trofen-lysulfonyl) ammonoacetic acid (obtained in reference example 28) instead of 3,3-d-phenylpropane-co-acid, the title compound was obtained in the form of solid white (7170). ] H NMR (80 MHz, CDCl 3) d (TMS): 8 98 (s, 1 H), 8.40 (d, J = 5.5 Hz, 1 H), 8.31 (d, j = 8.8 Hz, 2 H), 8.00 (d , j = 8.8 Hz, 2H), 7.21 (d, J = 5.5Hz, 1 H), 4.50 (m, 1 H), 4.16 (s, 2H), 4.01 (d, J = 7.2 Hz, 2H), 3.85 (m.1 H), 3.08 (d, J = 7 4 Hz, 2H), 2.63 (s, 3H), 3.1 -1.2 (m, 8H), 0.87 (d, 1 = 6.5 Hz, 6H). EXAMPLE 76 L-111-1-N- (4-Aminophenylsulfonyl) -N-isobutyl-minolacethyl-4-piperidyl] methyl-1H-2-methyl imidazo (4,5-c] pixidine Following the procedure described in reference example 3 , but starting from the compound obtained in Example 75, the title compound was obtained as a white solid (67%) mp: 112-116 ° C (C25H34N6O3S.3 / 2H2O); ^ H NMR (80MHz, CDCl3) d (TMS): 8.96 (s, 1H), 8.39 (d, J = 5.5Hz, 1H), 7.51 (d, J = 8.8 Hz, 2H), 7.20 (d, J = 5.5Hz, 1H), 6.63 (d , J = 8.8 Hz, 2H), 4.50 (m, 3H), 3.89 (m, 5H), 3.00 (m, 2H), 2.62 (s, 3H), 3.1-1.2 (m, 8H), 0.84 (d, ) = 6.5 Hz, 6H).

Claims (21)

1. CLAIMS 1.- A compound of formula I:
2. I characterized in that: m represents 0, 1 or 2; a, b and c represent CR, wherein each R independently represents hydrogen or C1-4 alkyl; R1 represents C alkyl or C3.7 cycloalkyl; A represents -CO-, -S? 2-, -NHCO- or -OCO-; B represents a group of formula (i), and when A represents -CO- or -SO2-, then B may also represent a group of formula (ii) or (iii) n represents 0, 1, 2 or 3; one of R2 or R3 represents C1.4 alkyl, C3.7 cycloalkyl or aryl, and the other represents hydrogen, C1.4 alkyl, .4 haloalkyl, C3.7 cycloalkyl, C1.4 alkoxy-C? -4 alkyl, aryl or aryl-C? 4 alkyl; Z represents hydrogen, C1.4 alkyl, -CH2-OR4, -COOR4 or -CONR R5, and when A represents -CO- or -SO2-, then Z can also be hydroxy, -NR R5, -NR * C (= 0) OR4, -NRí > C (= 0) R4, -NR * C (= O) NRR5, -N (OH) C (= 0) NR R5 or -NR6SO2R4; or Z and R3 together form a C2-5 polymethylene chain in which case R2 represents. alkyl, C3.7 cycloalkyl or aryl; R4 represents hydrogen, C1.4 alkyl, aryl or aryl-C4-4 alkyl; R5 and R6 independently represent hydrogen or Cj-4 alkyl; R7 represents C1. alkyl, C3-7 cycloalkyl, aryl, aryl-C? -4 alkyl or bisaryl-C? _4 alkyl; Y represents hydrogen, C1.4 alkyl, aryl, aryl-C? -4 alkyl, -C (= 0) OR4, -C (= 0) R4, -C (= 0) NR R5, OR -SO2R4; aryl, whenever it appears in the above definitions, represents phenyl or phenyl substituted by 1, 2, 3 or 4 groups independently chosen from halogen, C1-4 alkyl, C1-4 alkoxy, hydroxy, CM haloalkyl, CM haloalkoxy, cyano, nitro, amino, C1-4 alkylamino, C1-4 dialkylamino, C1.4 alkylcarbonyl, C1-4 alkylcarbonyloxy, C1.4 alkoxycarbonyl, C1-4 alkylsulfonyl, C1-4 alkylsulfinyl, C alkylthio, CM alkylcarbonylamino or CM alkoxycarbonylamino; and its salts and solvates. 2. A compound as claimed in claim 1, characterized in that m represents 1 or 2.
3. 3. A compound as claimed in claim 1 or 2, characterized in that A represents -CO- or -SO2-
4. 4.- A compound as claimed in claim 1 or 2, characterized in that A represents -NHCO- or -OCO-.
5. 5. A compound as claimed in any of claims 1 to 4, characterized in that B represents a group of formula (i).
6. 6. A compound as claimed in any of claims 1 to 5, characterized in that n represents 0, 1 or 2.
7. 7. A compound as claimed in any of claims 1 to 3, characterized in that B represents a group of formula (ii).
8. 8. A compound as claimed in any of claims 1 to 3, characterized in that B represents a group of formula (iii).
9. 9. A compound as claimed in any of claims 1 to 6, characterized in that Z represents hydrogen, C1-4 alkyl, -CH2-OR4, -COOR4 or -CONR4R5, and when A represents -CO- or -SO2- , then Z may also represent hydroxy, -NR * > C (= 0) OR4, -NR6C (= 0) R4 or -NR6S02R4; or Z and R3 together form a C2-5 polymethylene chain.
10. 10. A compound as claimed in any of claims 1, 2, 3 or 8, characterized in that R7 represents CM alkyl, C3.7 cycloalkyl or aryl.
11. 11. A compound as claimed in any of claims 1 to 10, characterized in that aryl represents phenyl or phenyl substituted by 1, 2, 3 or 4 groups independently chosen from halogen, C alkyl, alkoxy CM, hydroxy, C haloalkyl , CM haloalkoxy or amino.
12. 12. A compound as claimed in any of claims 1 or 2, characterized in that: A represents -CO- or -SO2-; B represents a group of formula (i), (ii) or (iii); n represents 1 or 2; one of R2 or R3 represents CM alkyl, C3.7 cycloalkyl or aryl, and the other represents hydrogen, C1-4 alkyl, C1-4 haloalkyl, C3.7 cycloalkyl, C1.4 alkoxy-CM alkyl, aryl or aryl-CM I rent; Z represents hydrogen, alkyl CM, -CH2-OR4, -COOR4, -CONR R5, hydroxy, -NRi >; C (= 0) OR4, -NR6C (= 0) R4 or -NR6S02R4; or Z and R3 together form a C2-5 polymethylene chain in which case R2 represents C alkyl, C3.7 cycloalkyl or aryl; R7 represents CM alkyl, C3-7 cycloalkyl or aryl; and aryl represents phenyl or phenyl substituted by 1, 2, 3 or 4 groups independently chosen from halogen, CM alkyl, CM alkoxy, hydroxy, C haloalkyl, CM haloalkoxy or amino.
13. 13. A compound as claimed in any of claims 1 or 2, characterized in that: A represents -NHCO- or -OCO-; B represents a group of formula (i); n represents 0 or 1; and aryl represents phenyl or phenyl substituted by 1, 2, 3 or 4 groups independently chosen from halogen, CM alkyl, akoxy CM, hydroxy, C haloalkyl, CM haloalkoxy or amino.
14. 14. A compound as claimed in claim 12, characterized in that: B represents a group of formula (i) or (iii); one of R2 or R3 represents CM alkyl, C3.7 cycloalkyl or aryl, and the other represents hydrogen, C alkyl, C1-4 haloalkyl, C3.7 cycloalkyl, .4 alkoxy-CM alkyl, aryl or aryl-CM alkyl; Z represents hydrogen, alkyl CM, -CH2-OR4, -COOR4 or hydrox; or Z and R3 together form a C2-5 polymethylene chain in which case R2 represents CM alkyl, C3.7 cycloalkyl or aryl; R 4 represents hydrogen, C alkyl, aryl or aryl-CM alkyl; R7 represents C M alkyl, C3.7 cycloalkyl, or aryl; and Y represents C alkyl, aplo or -S02R4
15. 15. A compound as claimed in claim 12, characterized in that: B represents a group of formula (ii); and one of R2 or R3 represents C 1.4 alkyl or aryl, and the other represents hydrogen, CM alkyl, C M alkoxy-C M alkyl, aryl or aryl-C? -4 alkyl.
16. 16. A compound according to claim 1 selected from: ll (1- (3-diphenylpropanoyl) -4-p? Peridyl) methyl] -l H-2-met? Lim? Dazol4,5-c] p ridiculous l - [[l-l3- (N- (4-am? nobenzoyl) am? no] -3-phenylpropanoyl] -4-p? peridyl] methyl] -l H-2-methylimidazo (4,5-c) pyridine; c? sl - [[1-13- (4-aminophenyl) -3-phenylpropenoyl] -4-piperidylmethyl-1 H-2-methylimdazo [4,5-c] pyridine; fraps-1 - ([ l- [3- (4-aminophenyl) -3-phenylpropenoyl] -4-piperidyl] methyl] -l H-2-methyl-imidazo (4,5-c] pyridine; l-III - (3-phenyl-3 -hydroxybutanoyl) -4-p? pepdillmethyl] -l H-2-methyl? midazo (4,5-c] -pyridine; l - [[l - [2- (4-aminophenyl) propanoyl) -4-p? peridyl] methyl] -l H-2-methylimidazole-4,5-c] -pyridine; ll [1- (3-phenylhexanoyl) -4-piperidyl] methyl] -l H-2-methylimidazo (4,5-c] pyridine; (S) -l-l [l- [. { N- (1-ethoxycarbonyl-1-phenylmethyl) amino] carbonill-4-p-peridyl] methyl] -lH-2-methylimidazo [4,5-c] pyridine; l- (ll - (3-phenylbutanoyl) -4-piperidyl] methyl] -l H-2-methylimidazol-4,5-cJpyridine; l-III- (3-phenyl-3-methylbutanoyl) -4-piperidyl] methyl] - l H-2-methylimidazo | 4,5-c] pyridine; 1-1 (1 - | 3- (4-aminophenyl) -3-methylbutanoyl-4-p? peridyl] methyl] -l H- 2-methylimidazo-l4-c] pyridine; l-ül- (3-phenyl-3-hydroxy-3-trifluoromethylpropanoyl) -4-p-peridyl] methyl] -l H-2-methylimidazo [4,5-c] pyridine; (R) -l- [[11 (l-phenylethylamino) carbonyl] -4-p-peridylmethyl] -l H-2-methylimidazo- [4-c] pyridine; l- (II - [(1-phenyl) -l-cyclopropylamide) carbonyl] -4-p-peridyl] methyl] -l H-2-methylimida-zo (4,5-c) pyridine; (S) -l - ([l - [(2- ethoxy-l-phenylethylamine) carbonyl] -4-p-peridyl] methyl] -l H-2-methylamide-dazol4-c) pyridine; l - ([l - [lN-methyl-N- (2-methoxyphenyl ) amino) acetyl] -4-p-peridyl) methyl] -l H-2-methyl-imidazo | 4,5-clpyridine; ll | l - [[(l-phenyl-l -c? clopropyl) methox ? lcarbonyl] -4-p? pepdillmet? l] -l H-2-methyl? mi-dazol4 -clpyridine; l - [ll - [[N- (4-am? nofen? lsulfonyl) -N-phen? lam ? nolacetill-4-p? peridillmethyl] -l H-2-methylimidazo (4,5-clp? ridine; l-l (l- (lN- (4-am? n-phenylsulfonyl) -N-isobutylamido) -acetyl-l-4-p-peridyl] -metill-l H-2-methylim? dazo [4,5-c] pyridine; or a salt or solvate thereof.
17. 17. A pharmaceutical composition characterized in that it comprises an effective amount of a compound of formula I as claimed in any of claims 1 to 16 or a pharmaceutically acceptable salt or solvate thereof and a pharmaceutically acceptable excipient.
18. 18. The use of a compound of formula I as claimed in any of claims 1 to 16 or a pharmaceutically acceptable salt or solvate thereof for the manufacture of a medicament for the treatment or prevention of diseases mediated by PAF.
19. 19. A process for preparing a compound of formula I according to claim 1, characterized in that it comprises: (A) reacting a compound of formula II, p wherein a, b, c, m and R1 have the meaning defined in claim 1, with an acid of the formula BCOOH (III) or a suitable derivative thereof such as the acid chloride or the anhydride, a sulfonyl chloride of the formula BS02C1 (IV), a compound of formula BOC (= 0) C (V), a compound of formula BNHC (= 0) G (VI) or a compound of formula BN = C = 0 (VII), where B has the meaning defined in claim 1 and G represents a good leaving group such as chloro or -OPh; or (B) transforming a compound of formula I into another compound of formula I in one or more steps; and (C) if desired, after steps A or B, reacting a compound of formula I with an acid to give the corresponding addition salt.
20. 20. A compound of formula II characterized in that a, b, c, m and R1 have the meaning defined in claim 1.
21. 21. A compound according to claim 20 characterized in that it is l - [(4-p ? peridyl) methyl] -l H-2-methylimidazo [4,5-c) pyridine.