Selective ligands of human constitutive androstane receptor

Abstract

The present invention provides a structurally novel class of heterocyclic compounds of general formula I [Image disponible dans le document PDF, Image available in the PDF document] (I). The novel compounds are useful in the prevention or treatment of a condition which is mediated by the action, or by loss of action, of Constitutive androstane receptor (CAR) or its endogenous ligands. The present invention thus provides the novel compounds for medicinal use, as well as pharmaceutical composition containing said compounds.

Description

1 SELECTIVE LIGANDS OF HUMAN CONSTITUTIVE ANDROSTANE RECEPTOR Field of the Invention The present invention relates to novel heterocyclic compounds of formula (I) which are capable of highly selective modulation of human constitutive androstane receptor (CAR, NR1I3), and to use thereof in the treatment of metabolic or liver disorders, as well as to pharmaceutical compositions thereof. Background Art Constitutive androstane receptor (CAR, NR1I3) is a ligand-activated transcription factor belonging to the nuclear receptor subfamily NR1I. Nuclear receptors (NRs) are currently known as key transcriptional regulators of several key metabolic processes including hepatic glucose and lipid metabolism, bile acid and cholesterol homeostasis, and energy expenditure as well as inflammation, fibrosis, and cellular proliferation in the liver. Dysregulation of these processes contributes to the pathogenesis and progression of metabolic diseases, metabolic syndrome or nonalcoholic fatty liver disease (NAFLD). Some NRs provide strategies for research and treatment of metabolic disease and are already pharmacologically targeted in metabolic disorders such as hyperlipidemia (fibrates as ligands for peroxisomal proliferator-activated receptor <com:Math><semantics>α<annotation encoding="application / x-tex">\alpha< / annotation>< / semantics>< / com:Math>-PPAR<com:Math><semantics>α<annotation encoding="application / x-tex">\alpha< / annotation>< / semantics>< / com:Math>), and diabetes (glitazones as ligands for PPAR<com:Math><semantics>γ<annotation encoding="application / x-tex">\gamma< / annotation>< / semantics>< / com:Math>). But these groups of drugs suffer from numerous side effects and drawbacks. Nonalcoholic fatty liver disease (NAFLD) often progress to less common subtype, nonalcoholic steatohepatitis (NASH), which has the potential to progress to advanced liver damage or cancer. However, current treatment strategies focus only on lifestyle management of some risk factors, namely weight, and on the management of individual components of metabolic syndrome. No other therapeutic interventions are available at present (Dibba et al., 2018). Human CAR displays unique properties in comparison with other nuclear receptors including high constitutive activity, both direct (ligand-binding domain (LBD)-dependent) and LBD-independent activation, and spontaneous nuclear localization in tumor cell lines. CAR is dominantly expressed in parenchymal (hepatocyte) cells of the liver where CAR wild-type variant (WT) (348aa; NM_005122) and the low constitutive activity / highly inducible variant hCAR3 (a variant with 5 extra amino acids) are almost equally expressed (Chai et al., 2016a). Recent studies suggest that mouse CAR plays important roles in the metabolism of glucose, lipids, and fatty acids; in the endobiotic metabolism of bile acids, cholesterol and bilirubin. It has been proposed in several independent animal studies that CAR activation may ameliorate glucose homeostasis and insulin- sensibility in the treatment of type 2 diabetes by inhibition of gluconeogenetic genes expression (such as G6pc and Pck1) (Dong et al., 2009; Gao and Xie, 2012; Gao et al., 2015). CAR activation reduces levels of lipoproteins and inhibits the expression of lipogenic genes in mice what might be a promising therapeutic intervention in the treatment of steatohepatitis, obesity, dyslipidemia, and metabolic syndrome or prevention of atherosclerosis (Baskin-Bey et al., 2007; Dong et al., 2009; Mackowiak et al., 2018; Sberna et al., 2011b; Xu et al., 2018). CAR is also involved in cholesterol and bile acids homeostasis and its activation is supposed to have benefitial therapeutic activities in hypercholesterolemia, in cholesterol or bilirubin gallstone disease and cholestasis diseases (Cheng et al., 2017; Rezen et al., 2009; Sberna et al., 2011a). These activities of CAR ligands are of great interest since there is currently no medication to treat metabolic syndrome connected with diabetes mellitus type 2, steatosis, and nonalcoholic steatohepatitis or to reduce obesity at the level of anabolic metabolism inhibition (Fuchs et al., 2016; Pu et al., 2019). CAR up-regulates major xenobiotic- and endobiotic-metabolizing enzymes of cytochrome P450 such as CYP2B6, CYP3A4, and CYP2C9 in the hepatocytes or in enterocytes. In this way CAR activation may protect the liver and the whole body from toxic injury. However, the role of CAR in inducible regulation of CYP3A4 and CYP2C9 is quantitatively marginal in comparison with another nuclear receptor pregnane X receptor (PXR) and only CYP2B6 appears as a CAR target gene significantly regulated in human hepatocytes. Stimulation of endobiotic compounds (such as bilirubin) clearance by CAR activation is bennefitial in hyperbilirubinemia and jaundice, hyperthyreosis and in cytostatic prodrugs activation (Wagner et al., 2005; Wang et al., 2013). CAR activation has been recently shown as potential regenerative treatment after partial hepatectomy due to pro-proliferative effects on hepatocytes in mice (Tschuor et al., 2016). However, the putative pro- proliferative effect of human CAR activators is unlikely connected with liver tumors (Lake, 2018). No potent, specific (without cross reactivity to PXR receptor), high-affinity and drug-like (with suitable physicochemical and ADME properties) agonist of human CAR receptor has been discovered that can be used therapeutically or that can serve as a tool to address various diagnostic, biological or therapeutic functions of human CAR ligands to consider CAR as a therapeutic target (Chai et al., 2016b). The unique properties of human CAR, such as small hydrophobic cavity, high constitutive activity of CAR in hepatocytes but little expression in tumour-derived cell lines and crosstalk activation of similar nuclear receptor such as Pregnane X receptor (PXR) by known CAR ligands, make discovery of specific ligands difficult. This is highly important, since PXR activation has been reported to cause opposite effects in comparison with CAR activation on promotion of hepatic lipogenesis and steatosis or on plasma glucose levels (glycemia) (Hakkola et al., 2018; Mackowiak et al., 2018). Known to date is 6-(4-chlorophenyl)imidazo[2,1-b]thiazole-5-carbaldehyde <com:Math><semantics>O<annotation encoding="application / x-tex">O< / annotation>< / semantics>< / com:Math>-(3,4- dichlorobenzyl)oxime (CITCO) (Maglich et al., 2003), which is a potent human – but not mouse – CAR agonist. However, this highly lipophilic compound also significantly activates PXR. The potent mouse CAR ligand 1,4-bis[(3,5-dichloropyridine-2-yl)oxy]benzene (TCPOBOP) does not activate human or rat CAR. Phenobarbital, a nonspecific activator of CAR translocation widely used in experimental research of CAR is not a ligand of CAR and activates also PXR receptor (Chai et al., 2016b). Disclosure of the Invention This invention discloses novel compounds of formula I, and compositions comprising these compounds, as human constitutive androstane receptor (CAR, NR1I3) agonists or partial agonists. The present invention relates to a compound of general formula I [Image disponible dans le document PDF, Image available in the PDF document] (I), wherein L<com:Sub>1< / com:Sub> is a 5- or 6-membered N-heteroaryl, which optionally further includes 1 to 3 heteroatoms selected from N, O and S; L<com:Sub>2< / com:Sub> is selected from the group consisting of bivalent 5- or 6-membered heteroaryls containing 1-4 heteroatoms selected from N, O and S; 5- or 6-membered heterocycles including 1-3 heteroatoms selected from N, O and S; C6-C12 aryls; C3-C6 cycloalkyl; and C3-C6 cycloalkenyl; each of R<com:Sup>1< / com:Sup> and R<com:Sup>2< / com:Sup> is independently selected from the group consisting of halogen, pseudohalogen, amino, hydrocarbylamino, dihydrocarbylamino, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, acyl, alkylcarbamoyl, carbamoyl, alkylthiocarbamoyl, thiocarbamoyl, alkylsulfonyl, sulfonamido, N-alkylsulfonamido, N,N-dialkylsulfonamido, carboxyl, alkyloxycarbonyl, amide, N-alkylamide, N,N-dialkylamide, thioamide, N-alkylthioamide, N,N-dialkylthioamide, oxime, wherein each of these substituents may optionally be further substituted by one or more substitutents selected from the group consisting of halogen, pseudohalogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, hydrocarbylamino, dihydrocarbylamino; each of R<com:Sup>3< / com:Sup> and R<com:Sup>4< / com:Sup> is independently selected from the group consisting of H, OH, C1-C6 alkyl, C2-C6 alkenyl, wherein each of these substituents may optionally be further substituted by one or more substitutents selected from the group consisting of halogen, pseudohalogen, OH; or R<com:Sup>3< / com:Sup> and R<com:Sup>4< / com:Sup> together form a <com:Math><semantics>C1<annotation encoding="application / x-tex">C1< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>C4<annotation encoding="application / x-tex">C4< / annotation>< / semantics>< / com:Math> alkylidene or <com:Math><semantics>=0<annotation encoding="application / x-tex">=0< / annotation>< / semantics>< / com:Math>; each R<com:Sup>5< / com:Sup> is independently selected from the group consisting of halogen, pseudohalogen; each R<com:Sup>6< / com:Sup> is independently selected from the group consisting of <com:Sup>3< / com:Sup>H, halogen, pseudohalogen, OH; each X is independently selected from C or N; each Y is independently selected from C, O, S, N; wherein when Y is O or S, R<com:Sup>3< / com:Sup> and R<com:Sup>4< / com:Sup> are not present, and when Y is N, R<com:Sup>4< / com:Sup> is not present; m, n, o, q are independently selected from 0, 1 and 2; p is selected from 0, 1 and 2. In one aspect, the substituents in formula I are as follows: <com:Math><semantics>L1<annotation encoding="application / x-tex">L_1< / annotation>< / semantics>< / com:Math> is a 5- or 6-membered N-heteroaryl, which optionally further includes 1 to 3 heteroatoms selected from N, O and S; L<com:Sub>2< / com:Sub> is selected from the group consisting of bivalent 5- or 6-membered heteroaryls containing 1-4 heteroatoms selected from N, O and S; 5- or 6-membered heterocycles including 1-3 heteroatoms selected from N, O and S; and C6-C12 aryls; each of R<com:Sup>1< / com:Sup> and R<com:Sup>2< / com:Sup> is independently selected from the group consisting of halogen, pseudohalogen, amino, hydrocarbylamino, dihydrocarbylamino, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, acyl, alkylcarbamoyl, carbamoyl, alkylthiocarbamoyl, thiocarbamoyl, alkylsulfonyl, sulfonamido, N-alkylsulfonamido, N,N-dialkylsulfonamido, carboxyl, alkyloxycarbonyl, amide, N-alkylamide, N,N-dialkylamide, thioamide, N-alkylthioamide, N,N-dialkylthioamide, oxime, wherein each of these substituents may optionally be further substituted by one or more substitutents selected from the group consisting of halogen, pseudohalogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, hydrocarbylamino, dihydrocarbylamino; each of R<com:Sup>3< / com:Sup> and R<com:Sup>4< / com:Sup> is independently selected from the group consisting of H, C1-C6 alkyl, C2-C6 alkenyl, wherein each of these substituents may optionally be further substituted by one or more substitutents selected from the group consisting of halogen, pseudohalogen; or R<com:Sup>3< / com:Sup> and R<com:Sup>4< / com:Sup> together form a C1-C4 alkylidene; each R<com:Sup>5< / com:Sup> is independently selected from the group consisting of halogen, pseudohalogen; each R<com:Sup>6< / com:Sup> is independently selected from the group consisting of <com:Sup>3< / com:Sup>H, halogen, pseudohalogen; each X is independently selected from C or N; each Y is independently selected from C, O, S, N; wherein when Y is O or S, R<com:Sup>3< / com:Sup> and R<com:Sup>4< / com:Sup> are not present, and when Y is N, R<com:Sup>4< / com:Sup> is not present; m, n, o, q are independently selected from 0, 1 and 2; p is selected from 0, 1 and 2. Compounds of general formula I are intended to include all isomers, including geometric, tautomeric and optical forms, as well as mixtures of isomers, including racemic mixtures, and pharmaceutically acceptable derivatives, salts and solvates. Definitions: the term "aryl" refers to a group having 6 to 12 atoms and containing at least one aromatic ring. Aryl may contain one aromatic ring or two aromatic rings, preferably fused. Aryl is preferably selected from phenyl, naphthyl; the term "heteroaryl" refers to an aromatic cyclic group having 5 or 6 atoms and containing 1 to 4 heteroatoms (preferably 1 to 3 heteroatoms) selected from O, S, N, the remaining atoms being carbon atoms. The term "N-heteroaryl" refers to a heteroaryl containing at least one N as a heteroatom, and optionally containing further 1 to 3 (or preferably 1 to 2) heteratoms. Examples of heteroaryl include preferably selected are pyrrolyl, furanyl, thiophenyl, imidazolyl, thiazolyl, oxazolyl, indolyl, pyridinyl, pyrimidynyl, pyridazinyl, pyrazinyl, isothiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl; the term "heterocycle" refers to an aliphatic cyclic group having 5 or 6 atoms and containing 1 to 4 heteroatoms (preferably 1 to 3 heteroatoms) selected from O, S, N, the remaining atoms being carbon atoms; the term "alkyl" refers to a linear or branched saturated radical, typically containing one to six carbons. Alkyl is preferably selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert- butyl, amyl, t-amyl, n-pentyl, n-hexyl; the term "alkylidene" refers to a residue formed from an alkane by removal of two hydrogens from the same carbon atom. An example is a methylene; the term "haloalkyl" refers to alkyl as defined herein above, substituted by at least one halogen. Haloalkyl is preferably selected from perfluoro(C1-C6)alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, mono- or polyhalo substituted propyl, butyl, pentyl, hexyl; the term "alkenyl" refers to a linear radical containing at least one double bond, typically containing from two to six carbons. Alkyl is preferably selected from vinyl, allyl, 2-butenyl, 3-butenyl, 2-pentenyl, 3-pentanyl, 4-pentenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl and the like; the "alkenyl" group includes dienes and trienes of straight and branched chains; the term "cycloalkyl" refers to a saturated cyclic radical, typically containing three to six carbons. Cycloalkyl is preferably selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; the term "cycloalkenyl" refers to a saturated cyclic radical, typically containing three to six carbons and at least one double bond. Cycloalkenyl is preferably selected from cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl; the term "alkoxy" refers to a group alkyl-O-, wherein alkyl is as defined above. Alkoxy group is preferably selected from methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, pentyloxy, hexyloxy; the term "alkylthio" denotes a group alkyl-S-, wherein alkyl is as defined above. Alkylthio is preferably selected from methylthio, ethylthio; the term "amino" represents an -NH<com:Sub>2< / com:Sub> group; the term "hydrocarbylamino" represents an amino group substituted with one group selected from (C1-C6) alkyl, C6-C12 aryl. Examples include methylamine, ethylamine, n-propylamine, n-butylamine, n-pentylamine; _ the term "dihydrocarbylamino" used either alone or in combination with other radicals, represents an amino group substituted with two radicals that may be the same or different selected from (C1-C6) alkyl, C6-C12 aryl. Examples include dimethylamino, methylethylamino, diethylamino; the term "acyl" refers to a group of formula R<com:Sup>a< / com:Sup>C(=O)—, wherein R<com:Sup>a< / com:Sup> represents hydrogen or C1- C6 alkyl as defined above. Acyl is preferably selected from formyl, acetyl, propanoyl, butanoyl, iso- butanoyl, pentanoyl, hexanoyl, heptanoyl, benzoyl; the term "alkylcarbamoyl" represents a radical -NH-C(=O)-R<com:Sup>b< / com:Sup> wherein R<com:Sup>b< / com:Sup> is C1-C6 alkyl as defined above; the term "carbamoyl" denotes –NH-CHO; the term "alkylhiocarbamoyl" represents a radical -NH-C(=S)-R° wherein R° is C1-C6 alkyl as defined above; the term "thiocarbamoyl" represents –NH-CHS; - the term "alkylsulfonyl" represents a radical R<com:Sup>d< / com:Sup>SO<com:Sub>2< / com:Sub>-, wherein R<com:Sup>d< / com:Sup> is C1-C6 alkyl as defined above. Alkylsulfonyl is preferably selected from methylsulfonyl, ethylsulfonyl, propylsulfonyl; the term "sulfonamido" represents a radical –SO<com:Sub>2< / com:Sub>-NH<com:Sub>2< / com:Sub>; the term "N-alkylsulfonamido" represents a radical –SO<com:Sub>2< / com:Sub>-NHR<com:Sup>e< / com:Sup>, wherein R<com:Sup>e< / com:Sup> is C1-C6 alkyl as defined above; the term "N,N-dialkylsulfonamido" represents a radical -SO<com:Sub>2< / com:Sub>-N(R<com:Sup>f1< / com:Sup>)(R<com:Sup>f2< / com:Sup>), wherein each of R<com:Sup>f1< / com:Sup> and R<com:Sup>f2< / com:Sup> is independently C1-C6 alkyl as defined above, or R<com:Sup>f1< / com:Sup> and R<com:Sup>f2< / com:Sup> together form a C2-C5 alkylene or a 2- to 5-membered heteroalkylene containing one or more heteroatoms selected from O, S, N; the term "carboxyl" denotes –COOH group; the term "alkyloxycarbonyl" denotes –C(=O)O-R<com:Sup>g< / com:Sup> group, wherein R<com:Sup>g< / com:Sup> is C1-C6 alkyl as defined above. Examples of alkyloxycarbonyl include methoxycarbonyl, ethoxycarbonyl; the term "amide" represents an aminocarbonyl radical <com:Math><semantics>H2N−(C=O)−<annotation encoding="application / x-tex">H_2N-(C=O)-< / annotation>< / semantics>< / com:Math>; the term "N-alkylamide" represents an <com:Math><semantics>−C(=O)NH−Rh<annotation encoding="application / x-tex">-C(=O)NH-R^h< / annotation>< / semantics>< / com:Math> group wherein <com:Math><semantics>Rh<annotation encoding="application / x-tex">R^h< / annotation>< / semantics>< / com:Math> is C1-C6 alkyl or C1- C6 alkoxy. Examples of alkylamide include methyl amide, methoxy amide, ethyl amide; the term "N,N-dialkylamide" represents an <com:Math><semantics>−C(=O)N(Ri1)(Ri2)<annotation encoding="application / x-tex">-C(=O)N(R^{i1})(R^{i2})< / annotation>< / semantics>< / com:Math> group wherein <com:Math><semantics>Ri1<annotation encoding="application / x-tex">R^{i1}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Ri2<annotation encoding="application / x-tex">R^{i2}< / annotation>< / semantics>< / com:Math> are independently selected from C1-C6 alkyl, C1-C6 alkoxy; or R<com:Sup>i1< / com:Sup> and R<com:Sup>i2< / com:Sup> together form a C2-C5 alkylene or a 2- to 5-membered heteroalkylene containing one or more heteroatoms selected from O, S, N. Examples of dialkylamide include dimethyl amide, methylmethoxy amide, diethyl amide; the term "thioamide" represents an aminothiocarbonyl radical <com:Math><semantics>H2N−(C=S)−<annotation encoding="application / x-tex">H_2N-(C=S)-< / annotation>< / semantics>< / com:Math>; the term "N-alkylthioamide" represents an <com:Math><semantics>−C(=S)NH−Rj<annotation encoding="application / x-tex">-C(=S)NH-R^{j}< / annotation>< / semantics>< / com:Math> group wherein <com:Math><semantics>Rj<annotation encoding="application / x-tex">R^{j}< / annotation>< / semantics>< / com:Math> is C1-C6 alkyl or C1- C6 alkoxy. Examples of alkylamide include methyl amide, methoxy amide, ethyl amide; the term "N,N-dialkylthioamide" represents an <com:Math><semantics>−C(=S)N(Rk1)(Rk2)<annotation encoding="application / x-tex">-C(=S)N(R^{k1})(R^{k2})< / annotation>< / semantics>< / com:Math> group wherein <com:Math><semantics>Rk1<annotation encoding="application / x-tex">R^{k1}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Rk2<annotation encoding="application / x-tex">R^{k2}< / annotation>< / semantics>< / com:Math> are independently selected from C1-C6 alkyl, C1-C6 alkoxy; or R<com:Sup>k1< / com:Sup> and R<com:Sup>k2< / com:Sup> together form a C2-C5 alkylene or a 2- to 5-membered heteroalkylene containing one or more heteroatoms selected from O, S, N. Examples of dialkylamide include dimethyl amide, methylmethoxy amide, diethyl amide; _ the term "nitro" refers to <com:Math><semantics>−NO2<annotation encoding="application / x-tex">-NO_2< / annotation>< / semantics>< / com:Math>; the term "oxime" denotes a <com:Math><semantics>−C(Rx)=N−OH<annotation encoding="application / x-tex">-C(R^x)=N-OH< / annotation>< / semantics>< / com:Math> group wherein <com:Math><semantics>Rx<annotation encoding="application / x-tex">R^x< / annotation>< / semantics>< / com:Math> is hydrogen or C1-C6 alkyl; - the term "hydroxy" refers to –OH; the term "halogen" or "halide" includes -F, -Cl, -Br, and -I; - the term "pseudohalogen" includes cyanide, cyanate, thiocyanate, selenocyanate, trifluoromethyl, and azide. In preferred embodiments of the present invention, <com:Math><semantics>L1<annotation encoding="application / x-tex">L_1< / annotation>< / semantics>< / com:Math> is selected from pyridine, thiazole, pyrimidine, pyridazine, pyrazine. <com:Math><semantics>L2<annotation encoding="application / x-tex">L_2< / annotation>< / semantics>< / com:Math> is preferably selected from bivalent residues of pyridine, thiene, furane, oxazole, thiazole, isothiazole, isoxazole, oxadiazole, thiadiazole, triazole, tetrazole, imidazole, pyrrole, dihydropyrane, dihydrofurane, pyrimidine, triazine, tetrazine, benzene, cyclohexane, cyclohexene. Preferably, at least one R1 and / or R2 is present, wherein the said at least one R1 and / or R2 is independently selected from halogen, pseudohalogen and alkoxy. Further R1 and R2 substituents can be present, selected from the group defined above. Preferred embodiments of the invention are the compounds of general formula (I), selected from the group comprising: <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(3,4−dichlorobenzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> 6-(4-Chlorophenyl)-5-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[2,1-b]thiazole, <com:Math><semantics>5−(1−(3,4−Dimethoxybenzyl)−1H−1,2,3−triazol−4−yl)−6−phenylimidazo[2,1−b]thiazole,<annotation encoding="application / x-tex">5-(1-(3,4-Dimethoxybenzyl)-1H-1,2,3-triazol-4-yl)-6-phenylimidazo[2,1-b]thiazole,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>6−(4−Chlorophenyl)−5−(1−(4−methoxybenzyl)−1H−1,2,3−triazol−4−yl)imidazo[2,1−b]thiazole,<annotation encoding="application / x-tex">6-(4-Chlorophenyl)-5-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)imidazo[2,1-b]thiazole,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(3,4−dimethoxybenzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(3,4-dimethoxybenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(4−methoxybenzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>3−(1−Benzyl-1H−1,2,3−triazol-4−yl)−2−(4−chlorophenyl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">3-(1-\text{Benzyl-}1H-1,2,3-\text{triazol-}4-\text{yl})-2-(4-\text{chlorophenyl})\text{imidazo}[1,2-a]\text{pyridine},< / annotation>< / semantics>< / com:Math> <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(pyridin−2−ylmethyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>5−(1−Benzyl-1H−1,2,3−triazol-4−yl)−6−(4−chlorophenyl)imidazo[2,1−b]thiazole,<annotation encoding="application / x-tex">5-(1-\text{Benzyl-}1H-1,2,3-\text{triazol-}4-\text{yl})-6-(4-\text{chlorophenyl})\text{imidazo}[2,1-b]\text{thiazole},< / annotation>< / semantics>< / com:Math> 6-(4-Chlorophenyl)-5-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)imidazo[2,1-b]thiazole, <com:Math><semantics>3−(1−(4−Chlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(4−chlorophenyl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">3-(1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>5−(1−(4−Chlorobenzyl)−1H−1,2,3−triazol−4−yl)−6−(4−chlorophenyl)imidazo[2,1−b]thiazole,<annotation encoding="application / x-tex">5-(1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)-6-(4-chlorophenyl)imidazo[2,1-b]thiazole,< / annotation>< / semantics>< / com:Math> 6-Chloro-2-(4-chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-b]pyridazine, 3-Benzyl-5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)isoxazole, <com:Math><semantics>4−((4−(2−(4−Chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−yl)methyl)benzonitrile,<annotation encoding="application / x-tex">4-((4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzonitrile,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>4−((4−(6−(4−Chlorophenyl)imidazo[2,1−b]thiazol−5−yl)−1H−1,2,3−triazol−1−yl)methyl)benzonitrile,<annotation encoding="application / x-tex">4-((4-(6-(4-Chlorophenyl)imidazo[2,1-b]thiazol-5-yl)-1H-1,2,3-triazol-1-yl)methyl)benzonitrile,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(3,4−dichlorobenzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−b]pyridazine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-b]pyridazine,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(3,4−dichlorophenyl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(3,4-dichlorophenyl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>5−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−6−(3,4−dichlorophenyl)imidazo[2,1−b]thiazole,<annotation encoding="application / x-tex">5-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-6-(3,4-\text{dichlorophenyl})\text{imidazo}[2,1-b]\text{thiazole},< / annotation>< / semantics>< / com:Math> 6-Chloro-3-(1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-chlorophenyl)imidazo[1,2-b]pyridazine, <com:Math><semantics>3−(1−Benzyl−1H−1,2,3−triazol−4−yl)−6−chloro−2−(4−chlorophenyl)imidazo[1,2−b]pyridazine,<annotation encoding="application / x-tex">3-(1-Benzyl-1H-1,2,3-triazol-4-yl)-6-chloro-2-(4-chlorophenyl)imidazo[1,2-b]pyridazine,< / annotation>< / semantics>< / com:Math> 5-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-3-(3,4-dichlorobenzyl)-1,2,4-oxadiazole, 2-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-5-(3,4-dichlorobenzyl)-1,3,4-oxadiazole, 5-(6-(4-Chlorophenyl)imidazo[2,1-b]thiazol-5-yl)-3-(3,4-dichlorobenzyl)-1,2,4-oxadiazole, <com:Math><semantics>2−(4−Chlorophenyl)−3−(5−(3,4−dichlorobenzyl)−1H−1,2,4−triazol−3−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(5-(3,4-dichlorobenzyl)-1H-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> 6-(4-Chlorophenyl)-5-(2-(3,4-dichlorobenzyl)thiazol-4-yl)imidazo[2,1-b]thiazole, 4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-2-(3,4-dichlorobenzyl)thiazole, 2-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-5-(3,4-dichlorobenzyl)-1,3,4-thiadiazole, <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(p−tolyl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-yl)-2-(p-tolyl)\text{imidazo}[1,2-a]\text{pyridine},< / annotation>< / semantics>< / com:Math> <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(2,4−dichlorophenyl)imidazo[1,2−a]<annotation encoding="application / x-tex">3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-2-(2,4-\text{dichlorophenyl})\text{imidazo}[1,2-a]< / annotation>< / semantics>< / com:Math>pyridine, <com:Math><semantics>4−(3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]<annotation encoding="application / x-tex">4-(3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]< / annotation>< / semantics>< / com:Math>pyridin-2-yl)benzonitrile, <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol-4−yl)−2−(4−methoxyphenyl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol-}4-\text{yl})-2-(4-\text{methoxyphenyl})\text{imidazo}[1,2-a]\text{pyridine},< / annotation>< / semantics>< / com:Math> <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(4−(trifluoromethyl)phenyl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-2-(4-(\text{trifluoromethyl})\text{phenyl})\text{imidazo}[1,2-a]\text{pyridine},< / annotation>< / semantics>< / com:Math> <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(4−fluorophenyl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-2-(4-\text{fluorophenyl})\text{imidazo}[1,2-a]\text{pyridine},< / annotation>< / semantics>< / com:Math> 9 <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(4−ethylphenyl)imidazo[1,2−a]<annotation encoding="application / x-tex">3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-2-(4-\text{ethylphenyl})\text{imidazo}[1,2-a]< / annotation>< / semantics>< / com:Math>pyridine, Methyl 2-chloro-5-<com:Math><semantics>((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−<annotation encoding="application / x-tex">((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-< / annotation>< / semantics>< / com:Math> yl)methyl)benzoate, <com:Math><semantics>(2−Chloro−5−((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−<annotation encoding="application / x-tex">(2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-< / annotation>< / semantics>< / com:Math> yl)methyl)phenyl)methanol <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(3,4−dichlorophenyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> 2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine, 2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-pyrrol-2-yl)imidazo[1,2-a]pyridine, <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(3,4−dichlorophenethyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(3,4-dichlorophenethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> 2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide, 2-Chloro-5-<com:Math><semantics>((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−yl)methyl)−N,N−<annotation encoding="application / x-tex">((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-N,N-< / annotation>< / semantics>< / com:Math> dimethylbenzamide, 2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzoic acid, 2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-N- methoxy-N-methylbenzamide, <com:Math><semantics>1−(2−Chloro−5−((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−<annotation encoding="application / x-tex">1-(2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-< / annotation>< / semantics>< / com:Math> yl)methyl)phenyl)ethan-1-one, 2-Chloro-5-<com:Math><semantics>((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−yl)methyl)−N−1<annotation encoding="application / x-tex">((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-N-1< / annotation>< / semantics>< / com:Math> methylbenzamide, <com:Math><semantics>1−(2−Chloro−5−((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−<annotation encoding="application / x-tex">1-(2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-< / annotation>< / semantics>< / com:Math> yl)methyl)phenyl)propan-1-one, 2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)-N,N- dimethylbenzamide, 2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)-N,N- dimethylbenzothioamide, 2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-oxadiazol-2-yl)methyl)-N- methylbenzothioamide, 2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-oxadiazol-2-yl)methyl)-N- methylbenzamide, 2-(4-Chlorophenyl)-3-(1-(4-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2- a]pyridine, <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(4−(methylsulfonyl)benzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(4-(methylsulfonyl)benzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(1−phenylethyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(1-phenylethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(4−nitrobenzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>4−((4−(2−(4−Chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−yl)methyl)aniline,<annotation encoding="application / x-tex">4-((4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)aniline,< / annotation>< / semantics>< / com:Math> 2-Chloro-5-(1-(4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)ethyl)benzamide, 2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)pyridin-2-yl)amino)benzamide, 2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)pyridin-2-yl)oxy)benzamide, <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(4−(methylthio)benzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(4-(methylthio)benzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> 2-Chloro-5-<com:Math><semantics>((4−(2−(4−chlorophenyl)−8−fluoroimidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−<annotation encoding="application / x-tex">((4-(2-(4-chlorophenyl)-8-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-< / annotation>< / semantics>< / com:Math> yl)methyl)benzamide, 2-Chloro-5-((4-(2-(4-chlorophenyl)-7-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide, 2-Chloro-5-((4-(2-(4-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide, 2-Chloro-5-<com:Math><semantics>((4−(2−(4−chlorophenyl)−6,8−difluoroimidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−<annotation encoding="application / x-tex">((4-(2-(4-chlorophenyl)-6,8-difluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-< / annotation>< / semantics>< / com:Math> yl)methyl)benzamide, 2-Chloro-5-((4-(2-(4-cyclopropylphenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide, 2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzaldehyde, <com:Math><semantics>(E)<annotation encoding="application / x-tex">(E)< / annotation>< / semantics>< / com:Math>-2-chloro-5-<com:Math><semantics>((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1<math>H<annotation encoding="application / x-tex">((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H< / annotation>< / semantics>< / com:Math>-1,2,3-triazol-1- yl)methyl)benzaldehyde oxime, <com:Math><semantics>N−(4−((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−<annotation encoding="application / x-tex">N-(4-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-< / annotation>< / semantics>< / com:Math> yl)methyl)phenyl)acetamide, <com:Math><semantics>3−(1−(4−Chloro−3−nitrobenzyl)−1H−1,2,3−triazol−4−yl)−2−(4−chlorophenyl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">3-(1-(4-Chloro-3-nitrobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> 2-Chloro-5-<com:Math><semantics>((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−yl)methyl)aniline,<annotation encoding="application / x-tex">((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)aniline,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>N<annotation encoding="application / x-tex">N< / annotation>< / semantics>< / com:Math>-(2-chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1<com:Math><semantics>H<annotation encoding="application / x-tex">H< / annotation>< / semantics>< / com:Math>-1,2,3-triazol-1- yl)methyl)phenyl)acetamide, <com:Math><semantics>3−(4−Benzylphenyl)−2−(4−chlorophenyl)imidazo[1,2−a]pyridine,<annotation encoding="application / x-tex">3-(4-Benzylphenyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine,< / annotation>< / semantics>< / com:Math> 3-(6-Benzylpyridin-3-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine, 2-(4-Chlorophenyl)-3-(6-(1-phenylvinyl)pyridin-3-yl)imidazo[1,2-a]pyridine, 2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-5-iodo-1H-1,2,3-triazol-1- yl)methyl)benzamide, <com:Math><semantics>2−(4−Chlorophenyl)−3−(1H−1,2,3−triazol−4−yl)imidazo[1,2−a]<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1H-1,2,3-triazol-4-yl)imidazo[1,2-a]< / annotation>< / semantics>< / com:Math>pyridine, 3-(4-Benzylcyclohex-1-en-1-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine, 4-Benzyl-1-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)cyclohexan-1-ol, 1-(5-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)pyridin-2-yl)-1-phenylethane-1,2-diol, (5-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)pyridin-2-yl)(phenyl)methanone, 2-Chloro-5-((4-(2-(pyridine-4-yl)imidazo[1,2-a]pyridine-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzamide. One embodiment of the present invention is a compound of general formula I for use as a medicament. Another aspect of the present invention is a compound of general formula I for use in prevention or treatment of a condition which is mediated by the action, or by loss of action, of constitutive androstane receptor (CAR) receptor or its endogenous ligands, preferably in the liver or in other organs with CAR expression such as in the kidney, intestine, brain, thyroid, heart, ovary or prostate. One aspect of the present invention is a compound of the general formula I for use in prevention or treatment of metabolic disorders such as defects in glucose, cholesterol and lipid metabolism, including impaired glucose tolerance and insulin sensitivity, metabolic syndrome, type II diabetes, gestational diabetes as a risk factor for preeclampsia, obesity, obesity related atherosclerosis, cholesterol gallstone disease, dyslipidemia, cholelithiasis, cholangitis, lipid metabolic disorders, cholesterol or bilirubin gallstone disease, high cholesterol diseases, acute liver failure, cholelithiasis and choledocholithiasis, hyperbilirubinemia and jaundice, hyperthyreosis, inflammation of the gallbladder and pancreas, cholestasis diseases, liver steatosis, inflammatory liver diseases connected with metabolic diseases such as non-alcoholic steatohepatitits (NASH) or non-alcoholic fatty liver disease (NAFLD), in protection against liver stress, intoxication or liver infection such as viral infection or intracellular parasite infection, in the treatment of cancers or leukemia and as a cytostatic prodrugs activator. An aspect of the present invention is a compound of general formula I for use in a method of stimulation of liver regeneration after partial hepatectomy or in liver injuries connected with the need of fast liver regeneration and parenchymal cells proliferation. Another aspect of the present invention is a compound of general formula I, for use in human adjuvant treatment of a condition or disease connected with malignancy and in the metabolic activation of antineoplastic drugs. The medical uses of compounds of general formula I are relevant in particular for human subjects. This invention relates to compounds for treating or preventing the aforementioned disease or medical condition, wherein said compounds have high selectivity or affinity for human CAR receptor and / or its transcript variants (including variant 3), but does not significantly activate Pregnane X receptor (PXR) in comparison with CAR or other nuclear receptors involved in regulation of endogenous intermediary metabolism or hormonal regulation. More specifically, said compounds have direct agonistic, inverse agonistic or partial agonistic activity for human CAR and interact with the human CAR. Another embodiment of the present invention is a pharmaceutical composition comprising as an active ingredient a compound of general formula (I) and / or its pharmaceutically acceptable salt or solvates, and one or more pharmaceutically acceptable carriers, polymers, or excipients. Pharmaceutically acceptable salts may be salts derived from inorganic or organic acids. A person skilled in the art will be able to determine which are pharmaceutically acceptable salts; particularly they are salts having one or more desirable physical properties, such as enhanced pharmaceutical stability at different temperatures, the required higher solubility in water or oil, or they are non-toxic. Suitable pharmaceutically acceptable salts of substances according to the invention preferably comprise anions derived from inorganic acids such as hydrochloric, hydrobromic, hydrofluoric, boric, fluoboric, phosphoric, metaphosphoric, nitric, carbonic, sulphurous and sulfuric acids, and organic acids such as acetic acid, benzenesulfonic, benzoic, citric, ethanesulfonic, fumaric, gluconic, glycolic, isethionic, lactic, lactobionic, maleic, malonic, methanesulfonic, trifluoromethanesulfonic, succinic, toluenesulfonic, tartaric, and trifluoroacetic acids. Suitable organic acids generally include, for example, the following classes of organic acids: aliphatic, cycloaliphatic, aromatic, araliphatic, heterocyclic, carboxylic and sulfonic acids. Specific examples of suitable organic acids include acetate, trifluoroacetate, formate, propionate, succinate, glycolate, gluconate, digluconate, lactate, malate, tartrate, citrate, ascorbate, glucuronate, maleate, fumarate, pyruvate, aspartate, glutamate, benzoate, anthranilate, stearate, salicylate, p- hydroxybenzoate, phenylacetate, mandelate, pamoate, methanesulfonate, ethanesulfonate, benzenesulfonate, pantothenate, toluenesulfonate, 2-hydroxyethanesulfonate, sulfanilate, cyclohexylaminosulfonate, 13-hydroxybutyrate, galactarate, galacturonate, adipate, alginate, butyrate, camphorate, camphorsulfonate, cyclopentanepropionate, dodecylsulfate, glycoheptanoate, glycerophosphate, heptanoate, hexanoate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, 3-phenylpropionate, picrate, pivalate, thiocyanate, and undecanoate. The compounds of formula I may be prepared in a crystalline or an amorphous form, and may be optionally hydrated or solvated. The compounds of general formula I according to this invention can also be used in the form of a precursor (prodrug) or in another suitable form which releases the active substance in vivo. In the framework of the present invention, it was found that compounds of the invention activate human CAR receptor or its variant CAR3 in luciferase gene reporter assays (Table 1) or in the TR-FRET CAR Coactivator in vitro assay with recombinant human CAR LBD. The compounds of formula I are agonists for human CAR with higher activity or affinity to activate human CAR in comparison with human Pregnane X receptor (PXR) (see Table 1) In comparison with CITCO, the only known high-affinity human CAR ligand, the compounds of EXAMPLES 89, 93, 109, 110, 111 and 112 of the invention are highly selective and specific for human CAR. The compounds of formula I may be administered by any convenient method, for example by oral, parenteral (e.g. intravenous), buccal, sublingual, nasal, rectal, subcutaneous or transdermal administration and the pharmaceutical compositions adapted accordingly. For use in human medicine, the compounds of the present invention are usually administered as a standard pharmaceutical composition. The present invention therefore provides a pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically (i.e physiologically) acceptable salt thereof and a pharmaceutically acceptable carrier or excipient to form appropriate formulation, microformulation or nanoformulation. The pharmaceutical composition can be for use in the treatment of any of the conditions described herein. A composition in the form of a tablet can be prepared using any suitable pharmaceutical carrier(s) routinely used for preparing solid pharmaceutical formulations. Examples of such carriers include lactose, sucrose, cellulose magnesium stearate or starch. A composition in the form of a capsule can be prepared using routine encapsulation procedures. For example, pellets containing the active ingredient can be prepared using standard carriers and filled into a hard gelatin capsule. Alternatively, a dispersion or suspension can be prepared using any suitable pharmaceutical carrier(s) and then filled into a soft gelatin capsule. Brief Description of the Drawings To further clarify the invention and its features, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings in which: Fig. 1 shows the dose-response curves for selected compounds of the invention in TR-FRET CAR Coactivation assay. Data show relative activities of compounds of the invention to activate human CAR LBD with respect to increasing concentration tested. Data have been fitted using GraphPad software and EC<com:Sub>50< / com:Sub> (Half-maximum activating concentration) values are presented in Table 1. In addition, activation of human CAR receptor by selected compounds of the invention in CAR LBD assembly assay and in luciferase reporter gene assay with CAR variant 3 is presented in Fig. 1 and Table 1. Fig. 2 evidences no activation of PXR by selected compounds of the invention in human PXR-responsive luciferase reporter gene assay in HepG2 cells. The embodiment indicates fold activation of PXR- responsive luciferase construct in response to compounds of the invention treatment for 24 hours. Rifampicin has been used as the prototype PXR ligand. * denotes statistical significance at the level of p<0.05 compared to controls. Fig. 3 demonstrates that the compounds of EXAMPLES 110 and 93 show up-regulation of the major human CAR target gene CYP2B6 in HepaRG, but not in CAR-deficient HepaRG KO CAR cells as determined by RT-qPCR. Fold induction of the target gene mRNA versus vehicle-treated control samples are presented after 24 hours treatment. At the same time, activities of prototype CAR (CITCO) and common PXR / CAR activator (phenobarbital) are shown. *,** denotes statistical significance p<0.05 or p<0.01, respectively, compared to controls. Fig. 4 demonstrates that the compounds of EXAMPLES 110 and 93 up-regulates CYP2B6 mRNA in primary human hepatocytes after 48 hours of treatment with 1 and 5 µM / L. CITCO is a prototype CAR ligand. Fig. 5 shows that the compounds of EXAMPLES 169 (a hydrochloric salt of compound in EXAMPLE 110) and 93 up-regulate Cyp2b10, Cyp2c29and CYP3A4 mRNA, in the liver of humanized huPXR / huCAR / huCYP3A4 / huCYP3A7 mice after peroral (gavage) administration of 10 mg / kg of the invented compounds. Data show fold mRNA upregulation of CAR target genes in the liver of humanized mouse model analyzed after 24 hours after application using RT-qPCR with specific TaqMan<com:Sup>TM< / com:Sup> probes. * and *** denotes statistical significance at the level of p<0.05 or p<0.001 compared to vehicle controls (either 5% glycerol solution or olive oil). Figure 6 show pharmakokinetics (PK) in humanized huPXR / huCAR / huCYP3A4 / huCYP3A7 male mice after peroral, i.p. or i.v. application of compounds of EXAMPLES 169 and 93. Plasma as well as liver and bile concentrations have been analyzed over 1440 minutes (24 h) in at least three animals per time point. Figure 7 shows that the compound of EXAMPLE 93 alleviates insuline resistance and stimulates the effect of insuline in i.p. glucose tolerance test (IPGTT) and i.p. in insulin tolerance test (ITT), but does not stimuate significantly liver hypertrophy (inicated as live-to-body weight ratio, LW / BW) in humanized PXR-CAR-CYP3A4 / 3A7 mice (n=5) feeded with 60% high-fat died for 8 weeks and administed with 10 mg / kg of b.w of invented compound of EXAMPLE 93 by gavage for 4 weeks (3 times per week) in comparison with vehicle treated control animals. Figure 7 also shows that compound of EXAMPLE 93 reduces the body weight in the experiments, decreases plasma cholesterol and LDL levels, but does not display hepatotoxicity as indicated by no effects on ALT, AST, ALP or LDH biochemical markers. Figure 8 shows the effect of compound of EXAMPLE 93 and 110 on the panel of major cytochrome P450 enzymes. Both compounds are weak inhibitors of these enzymes with IC<com:Sub>50< / com:Sub> being higher than 10 <com:Math><semantics>μ<annotation encoding="application / x-tex">\mu< / annotation>< / semantics>< / com:Math>M. Examples Abbreviations [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] Scheme 1. [Image disponible dans le document PDF, Image available in the PDF document] General procedure I. Cyclization of heterocycle 2-Aminopyridine (or 2-aminothiazole) was dissolved in EtOH and substituted or unsubstituted bromoacetophenone derivative (1eq) was added followed by an addition of NaHCO3 (1eq). The reaction mixture was heated at 70 °C overnight. After the completion of the reaction (monitored by TLC or UPLC), the solvent was evaporated to a minimal volume, a residue was diluted with EtOAc and washed with water. Water phase was extracted twice more with EtOAc, combined organic phases were dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography (eluent petrolether / EtOAc or EtOAc / MeOH). EXAMPLE 1 6-(4-Chlorophenyl)imidazo[2,1-b]thiazole (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-60 %). Yield: 981 mg (82 %). 1H NMR (401 MHz, DMSO-d6) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.26 (s, 1H), 7.94 (d, J = 4.4 Hz, 1H), 7.90 – <com:Math><semantics>7.80 (m, 2H),7.48−7.39 (m, 2H),7.28 (d, J = 4.4 Hz, 1H).13CNMR(101)<annotation encoding="application / x-tex">7.80 \text{ (m, 2H)}, 7.48 - 7.39 \text{ (m, 2H)}, 7.28 \text{ (d, J = 4.4 Hz, 1H)}. 13C NMR (101)< / annotation>< / semantics>< / com:Math> MHz, DMSO) δ 149.88, 145.54, 133.64, 131.78, 129.09, 126.85, 120.52, 113.85, 110.30. EI MS: calcd for [M + H], 234.0018; found, 234.0020. EXAMPLE 2 2-(4-Chlorophenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-60 %). Yield: 1.49 g (88 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, Chloroform-d) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.12 (dt, <com:Math><semantics>J=1.2<annotation encoding="application / x-tex">J = 1.2< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.93−7.87<annotation encoding="application / x-tex">7.93 - 7.87< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.84<annotation encoding="application / x-tex">7.84< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> <com:Math><semantics>=0.7 Hz<annotation encoding="application / x-tex">= 0.7 \text{ Hz}< / annotation>< / semantics>< / com:Math>, 1H), 7.64 (dq, <com:Math><semantics>J=1.0 Hz<annotation encoding="application / x-tex">J = 1.0 \text{ Hz}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>J=9.2 Hz<annotation encoding="application / x-tex">J = 9.2 \text{ Hz}< / annotation>< / semantics>< / com:Math>, 1H), 7.44 <com:Math><semantics>−7.40 (m, 2H)<annotation encoding="application / x-tex">- 7.40 \text{ (m, 2H)}< / annotation>< / semantics>< / com:Math>, 7.20 (ddd, <com:Math><semantics>J=1.3 Hz<annotation encoding="application / x-tex">J = 1.3 \text{ Hz}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>J=6.8 Hz<annotation encoding="application / x-tex">J = 6.8 \text{ Hz}< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=9.2<annotation encoding="application / x-tex">J = 9.2< / annotation>< / semantics>< / com:Math> Hz, 1H), 6.80 (td, <com:Math><semantics>J=1.2<annotation encoding="application / x-tex">J = 1.2< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, CDCl<com:Sub>3< / com:Sub>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 145.86, 144.82, 133.79, 132.45, 129.02, 127.38, 125.73, 125.03, 117.69, 112.72, 108.31. EI MS: calcd for [M + H], 228.0454; found, 228.0456. EXAMPLE 3 6-Chloro-2-(4-chlorophenyl)imidazo[1,2-b]pyridazine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (10-30 %). Yield 152 mg (63 %). 'H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.94 (d, <com:Math><semantics>J=0.7<annotation encoding="application / x-tex">J = 0.7< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.22 (dd, <com:Math><semantics>J=9.5,0.7<annotation encoding="application / x-tex">J = 9.5, 0.7< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.09 – 8.01 (m, 2H), <com:Math><semantics>7.60−7.48<annotation encoding="application / x-tex">7.60 - 7.48< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.38<annotation encoding="application / x-tex">7.38< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=9.5<annotation encoding="application / x-tex">J = 9.5< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 146.48, 144.39, 138.00, 133.18, 132.01, 129.08, 127.55, 127.44, 119.70, 114.40. HRMS: calcd for [M + Na], 264.00898; found, 264.00901. 2-(3,4-Dichlorophenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 533 mg (87 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.54 – 8.49 (m, 2H), 8.18 (d, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 2.0 Hz, 1H), 7.93 (dd, <com:Math><semantics>J=8.4<annotation encoding="application / x-tex">J = 8.4< / annotation>< / semantics>< / com:Math>, 2.0 Hz, 1H), 7.68 (d, <com:Math><semantics>J=8.4<annotation encoding="application / x-tex">J = 8.4< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.58 (dq, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.0 Hz, 1H), 7.27 (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.7, 1.3 Hz, 1H), 6.91 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 145.10, 141.99, 134.88, 131.74, 131.13, 130.02, 127.25, 127.23, 125.73, 125.70, 116.94, 112.84, 110.47. HRMS: calcd for [M + H], 263.01373; found, 263.01393. 4-(Imidazo[1,2-a]pyridin-2-yl)benzonitrile (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 952 mg (82 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.56 (s, 1H), 8.54 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.18 – 8.12 (m, 2H), 7.91 – 7.85 (m, 2H), 7.60 (dq, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.0 Hz, 1H), 7.28 (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.7, 1.3 Hz, 1H), 6.92 (td, <com:Math><semantics>J=6.7<annotation encoding="application / x-tex">J = 6.7< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 145.40, 142.63, 138.68, 133.03, 127.44, 126.39, 126.10, 119.33, 117.14, 113.13, 111.41, 110.06. HRMS: calcd for [M + H], 220.08692; found, 220.08686. EXAMPLE 6 6-(3,4-Dichlorophenyl)imidazo[2,1-b]thiazole (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 878 mg (65 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.37 (s, 1H), 8.06 (d, <com:Math><semantics>J=2.0<annotation encoding="application / x-tex">J = 2.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.97 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.82 (dd, <com:Math><semantics>J=8.4<annotation encoding="application / x-tex">J = 8.4< / annotation>< / semantics>< / com:Math>, 2.1 Hz, 1H), 7.64 (d, <com:Math><semantics>J=8.4<annotation encoding="application / x-tex">J = 8.4< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.30 (d, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 4.5 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 149.83, 143.93, 135.18, 131.65, 131.04, 129.21, 126.38, 124.93, 120.26, 113.98, 110.90. HRMS: calcd for [M + Na], 268.97015; found, 268.97029. EXAMPLE 7 6-Phenylimidazo[2,1-b]thiazole (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 564 mg (55 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.22 (s, 1H), 7.93 (d, <com:Math><semantics>J=4.4<annotation encoding="application / x-tex">J = 4.4< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.86 – 7.80 (m, 2H), 7.39 (dd, <com:Math><semantics>J=8.4,7.0 Hz,2H),7.29−7.22 (m, 2H).<annotation encoding="application / x-tex">J = 8.4, 7.0 \text{ Hz}, 2\text{H}), 7.29 - 7.22 \text{ (m, 2H)}.< / annotation>< / semantics>< / com:Math> <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 149.66, 146.74, 134.71, 129.08, 127.47, 125.18, 120.49, 113.55, 109.85. HRMS: calcd for [M+H], 201.04810; found, 201.04796. EXAMPLE 8 2-Phenylimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 739 mg (77 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.51 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.39 (d, <com:Math><semantics>J=0.7<annotation encoding="application / x-tex">J = 0.7< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.02 – 7.93 (m, 2H), 7.59 (dq, <com:Math><semantics>J=9.1,1.0 Hz,1H,7.48−7.40 (m, 2H),7.31 (ddt,J=8.0,6.8,1.3 Hz,1H),7.24 (ddd,J=9.1,6.7,1.3)<annotation encoding="application / x-tex">J = 9.1, 1.0 \text{ Hz}, 1\text{H}, 7.48 - 7.40 \text{ (m, 2H)}, 7.31 \text{ (ddt}, J = 8.0, 6.8, 1.3 \text{ Hz}, 1\text{H}), 7.24 \text{ (ddd}, J = 9.1, 6.7, 1.3)< / annotation>< / semantics>< / com:Math> Hz, 1H), 6.88 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 145.30, 144.83, 134.38, 129.17, 128.16, 127.32, 126.03, 125.40, 117.10, 112.73, 109.56. HRMS: calcd for [M + H], 195.09167; found, 195.09161. EXAMPLE 9 2-(Pyridin-4-yl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (40-100 %). Yield 98 mg (48 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.64 – 8.59 (m, 3H), 8.56 (dt, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 6.8, 1.2 Hz, 1H), 7.94 – 7.86 (m, 2H), 7.62 (dq, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 9.1, 1.0 Hz, 1H), 7.30 (ddd, <com:Math><semantics>J=9.1,6.7,1.3<annotation encoding="application / x-tex">J = 9.1, 6.7, 1.3< / annotation>< / semantics>< / com:Math> Hz, 1H), 6.94 (td, <com:Math><semantics>J=6.8,1.2<annotation encoding="application / x-tex">J = 6.8, 1.2< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 150.33, 145.29, 141.82, 141.26, 127.41, 125.95, 120.08, 117.18, 113.03, 111.62. HRMS: calcd for [M + H], 196.08692; found, 196.08678. 2-(4-Nitrophenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 214 mg (77 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.64 (d, <com:Math><semantics>J=0.7<annotation encoding="application / x-tex">J = 0.7< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.57 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.33 – 8.27 <com:Math><semantics>(m,2H),8.24−8.19(m,2H),7.62(dq,J=9.1,1.1Hz,1H),7.31(ddd,J=9.1,6.7,1.3Hz,1H),6.95<annotation encoding="application / x-tex">(m, 2H), 8.24 - 8.19 (m, 2H), 7.62 (dq, J = 9.1, 1.1 Hz, 1H), 7.31 (ddd, J = 9.1, 6.7, 1.3 Hz, 1H), 6.95< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(td,J=6.7,1.2 Hz,1H)<annotation encoding="application / x-tex">(td, J = 6.7, 1.2 \text{ Hz}, 1H)< / annotation>< / semantics>< / com:Math>. <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 146.93, 145.71, 142.45, 140.97, 127.73, 126.76, 126.39, 124.65, 117.46, 113.39, 112.16. HRMS: calcd for [M + H], 240.07675; found, 240.07674. EXAMPLE 11 2-(4-Methoxyphenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 200 mg (84 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.49 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), <com:Math><semantics>7.92−7.87<annotation encoding="application / x-tex">7.92 - 7.87< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.54<annotation encoding="application / x-tex">7.54< / annotation>< / semantics>< / com:Math> (dq, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.0 Hz, 1H), 7.21 (ddd, <com:Math><semantics>J=9.1,6.7,1.3<annotation encoding="application / x-tex">J = 9.1, 6.7, 1.3< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.03−6.98<annotation encoding="application / x-tex">7.03 - 6.98< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>6.86<annotation encoding="application / x-tex">6.86< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=6.7,1.2<annotation encoding="application / x-tex">J = 6.7, 1.2< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 159.48, 145.19, 144.90, 127.33, 127.16, 127.00, 125.09, 116.86, 114.59, 112.51, 108.48, 55.60. HRMS: calcd for [M + H], 240.07675; found, 240.07674 EXAMPLE 12 2-(2,4-Dichlorophenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 634 mg (76 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.64 (d, <com:Math><semantics>J=0.7<annotation encoding="application / x-tex">J = 0.7< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.61 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.29 (d, <com:Math><semantics>J=8.5<annotation encoding="application / x-tex">J = 8.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.71 (d, <com:Math><semantics>J=2.2<annotation encoding="application / x-tex">J = 2.2< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.60 (dq, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.0 Hz, 1H), 7.54 (dd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>) 8.6, 2.2 Hz, 1H), 7.30 (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.7, 1.3 Hz, 1H), 6.94 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 144.26, 139.80, 132.92, 132.22, 131.75, 131.67, 130.15, 128.08, 127.69, 126.21, 117.15, 113.42, 113.01. HRMS: calcd for [M + H], 263.01373; found, 263.01390 EXAMPLE 13 2-(4-(Trifluoromethyl)phenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 1.07 g (77 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.57 – 8.53 (m, 1H), 8.21 – 8.15 (m, 1H), 7.82 – 7.77 (m, 1H), 7.61 (dq, <com:Math><semantics>J=9.1,1.0 Hz,0H<annotation encoding="application / x-tex">J = 9.1, 1.0 \text{ Hz}, 0\text{H}< / annotation>< / semantics>< / com:Math>), 7.29 (ddd, <com:Math><semantics>J=9.1,6.7,1.3 Hz,1H<annotation encoding="application / x-tex">J = 9.1, 6.7, 1.3 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 6.93 (td, <com:Math><semantics>J=6.8,1.2 Hz,1H<annotation encoding="application / x-tex">J = 6.8, 1.2 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 145.20, 142.84, 138.12, 128.06, 127.75, 127.30, 126.21, 125.89, 125.86, 125.82, 125.78, 125.71, 117.04, 112.84, 110.73. HRMS: calcd for [M + H], 263.07906; found, 263.07907 2-(4-Fluorophenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] tle compound was prepared according to the General Procedure I (Scheme . Mobile phase petrolether / EtOAc (20-70 %). Yield 988 mg (88 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.52 (dt, <com:Math><semantics>J=1.2,7.0<annotation encoding="application / x-tex">J = 1.2, 7.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.38 (s, 1H), 8.04 – 7.96 (m, 2H), 7.57 (d, <com:Math><semantics>J=9.1 Hz<annotation encoding="application / x-tex">J = 9.1 \text{ Hz}< / annotation>< / semantics>< / com:Math>, 1H), <com:Math><semantics>7.31−7.21 (m, 3H)<annotation encoding="application / x-tex">7.31 - 7.21 \text{ (m, 3H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>6.89 (td, J=1.3,6.8 Hz<annotation encoding="application / x-tex">6.89 \text{ (td, } J = 1.3, 6.8 \text{ Hz}< / annotation>< / semantics>< / com:Math>, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 145.30, 143.91, 130.93, 127.37, 125.51, 117.06, 112.80, 109.41. <com:Math><semantics>13<annotation encoding="application / x-tex">^{13}< / annotation>< / semantics>< / com:Math>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> <com:Math><semantics>162.29(d,J=244.2Hz),130.93,127.97(d,J=8.2Hz),116.05(d,J=21.5Hz).<annotation encoding="application / x-tex">162.29 (d, J = 244.2 Hz), 130.93, 127.97 (d, J = 8.2 Hz), 116.05 (d, J = 21.5 Hz).< / annotation>< / semantics>< / com:Math> HRMS: calcd for [M + H], 213.08225; found, 213.08226. EXAMPLE 15 2-(4-Ethylphenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 1.02 g (74 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.51 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.34 (d, <com:Math><semantics>J=0.7<annotation encoding="application / x-tex">J = 0.7< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.90 – 7.85 (m, 2H), 7.56 <com:Math><semantics>(dq,J=9.1,1.0Hz,1H),7.29−7.26(m,2H),7.23(ddd,J=9.1,6.7,1.3Hz,1H),6.88(td,J=6.7,1.2)<annotation encoding="application / x-tex">(dq, J = 9.1, 1.0 Hz, 1H), 7.29 - 7.26 (m, 2H), 7.23 (ddd, J = 9.1, 6.7, 1.3 Hz, 1H), 6.88 (td, J = 6.7, 1.2)< / annotation>< / semantics>< / com:Math> Hz, 1H), 2.63 (q, <com:Math><semantics>J=7.6<annotation encoding="application / x-tex">J = 7.6< / annotation>< / semantics>< / com:Math> Hz, 2H), 1.21 (t, <com:Math><semantics>J=7.6<annotation encoding="application / x-tex">J = 7.6< / annotation>< / semantics>< / com:Math> Hz, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 145.21, 144.97, 143.79, 131.88, 128.56, 127.25, 126.04, 125.24, 117.00, 112.63, 109.14, 28.44, 16.01. HRMS: calcd for [M + H], 223.12298; found, 223.12301. EXAMPLE 16 2-(4-Chlorophenyl)-8-fluoroimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 1.01 g (93 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.55 (d, <com:Math><semantics>J=3.1<annotation encoding="application / x-tex">J = 3.1< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.39 (dd, <com:Math><semantics>J=6.7,0.9<annotation encoding="application / x-tex">J = 6.7, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>8.02−7.94<annotation encoding="application / x-tex">8.02 - 7.94< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.54−7.45<annotation encoding="application / x-tex">7.54 - 7.45< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.15<annotation encoding="application / x-tex">7.15< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=11.4,7.7,0.9<annotation encoding="application / x-tex">J = 11.4, 7.7, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>6.87<annotation encoding="application / x-tex">6.87< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=11.4,7.7,0.9<annotation encoding="application / x-tex">J = 11.4, 7.7, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>6.87<annotation encoding="application / x-tex">6.87< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=11.4,7.7,0.9<annotation encoding="application / x-tex">J = 11.4, 7.7, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>6.87<annotation encoding="application / x-tex">6.87< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=11.4,7.7,0.9<annotation encoding="application / x-tex">J = 11.4, 7.7, 0.9< / annotation>< / semantics>< / com:Math> Hz, 7.7, 6.8, 4.7 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 150.88 (d, <com:Math><semantics>J=249.1<annotation encoding="application / x-tex">J = 249.1< / annotation>< / semantics>< / com:Math> Hz), 143.85, 137.77 (d, <com:Math><semantics>J=249.1<annotation encoding="application / x-tex">J = 249.1< / annotation>< / semantics>< / com:Math> Hz) 28.4 Hz), 132.93, 132.69, 129.27, 127.84, 124.17 (d, <com:Math><semantics>J=4.8<annotation encoding="application / x-tex">J = 4.8< / annotation>< / semantics>< / com:Math> Hz), 112.02 (d, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math> Hz), 111.77 – 111.62 (m), <com:Math><semantics>108.35<annotation encoding="application / x-tex">108.35< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=16.1<annotation encoding="application / x-tex">J = 16.1< / annotation>< / semantics>< / com:Math> Hz). HRMS: calcd for [M + H], <com:Math><semantics>247.0438<annotation encoding="application / x-tex">247.0438< / annotation>< / semantics>< / com:Math>; found, <com:Math><semantics>247.0439<annotation encoding="application / x-tex">247.0439< / annotation>< / semantics>< / com:Math>. EXAMPLE 17 2-(4-Chlorophenyl)-7-fluoroimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 510 mg (83 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.59 (ddd, <com:Math><semantics>J=7.5,5.9,0.8<annotation encoding="application / x-tex">J = 7.5, 5.9, 0.8< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.40 (d, <com:Math><semantics>J=0.7<annotation encoding="application / x-tex">J = 0.7< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>8.01−7.89<annotation encoding="application / x-tex">8.01 - 7.89< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.51−7.46<annotation encoding="application / x-tex">7.51 - 7.46< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.43<annotation encoding="application / x-tex">7.43< / annotation>< / semantics>< / com:Math> (ddt, <com:Math><semantics>J=10.1,2.7,0.8<annotation encoding="application / x-tex">J = 10.1, 2.7, 0.8< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>6.97<annotation encoding="application / x-tex">6.97< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=7.6,2.6<annotation encoding="application / x-tex">J = 7.6, 2.6< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 160.04 (d, <com:Math><semantics>J=248.4<annotation encoding="application / x-tex">J = 248.4< / annotation>< / semantics>< / com:Math> Hz), 145.15 (d, <com:Math><semantics>J=14.3<annotation encoding="application / x-tex">J = 14.3< / annotation>< / semantics>< / com:Math> Hz), 144.32 (d, <com:Math><semantics>J=14.3<annotation encoding="application / x-tex">J = 14.3< / annotation>< / semantics>< / com:Math> Hz) 1.5 Hz), 132.72, 132.41, 129.14 (d, <com:Math><semantics>J=11.1<annotation encoding="application / x-tex">J = 11.1< / annotation>< / semantics>< / com:Math> Hz), 128.94, 104.74 (d, <com:Math><semantics>J=29.4<annotation encoding="application / x-tex">J = 29.4< / annotation>< / semantics>< / com:Math> Hz), 100.36 (d, <com:Math><semantics>J=23.7<annotation encoding="application / x-tex">J = 23.7< / annotation>< / semantics>< / com:Math> Hz). HRMS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 247.0438; found, 247.0439. EXAMPLE 18 2-(4-Chlorophenyl)-6-fluoroimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 1.2 g (91 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.75 (ddd, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 4.6, 2.5, 0.8 Hz, 1H), 8.41 (d, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 0.7 Hz, 1H), 8.00 <com:Math><semantics>−7.94<annotation encoding="application / x-tex">-7.94< / annotation>< / semantics>< / com:Math> (m, 2H), 7.64 (ddt, <com:Math><semantics>J=9.9<annotation encoding="application / x-tex">J = 9.9< / annotation>< / semantics>< / com:Math>, 5.4, 0.8 Hz, 1H), <com:Math><semantics>7.52−7.45<annotation encoding="application / x-tex">7.52 - 7.45< / annotation>< / semantics>< / com:Math> (m, 2H), 7.34 (ddd, <com:Math><semantics>J=9.9<annotation encoding="application / x-tex">J = 9.9< / annotation>< / semantics>< / com:Math>, 8.4, 2.5 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 152.79 (d, <com:Math><semantics>J=232.7<annotation encoding="application / x-tex">J = 232.7< / annotation>< / semantics>< / com:Math> Hz), 144.61 (d, <com:Math><semantics>J=2.0<annotation encoding="application / x-tex">J = 2.0< / annotation>< / semantics>< / com:Math> Hz), 143.00, 132.73, 132.49, 128.97, 127.43, 117.57 (d, <com:Math><semantics>J=9.4<annotation encoding="application / x-tex">J = 9.4< / annotation>< / semantics>< / com:Math> Hz), 117.16 (d, <com:Math><semantics>J=25.9<annotation encoding="application / x-tex">J = 25.9< / annotation>< / semantics>< / com:Math> Hz), 113.84 (d, <com:Math><semantics>J=41.4<annotation encoding="application / x-tex">J = 41.4< / annotation>< / semantics>< / com:Math> Hz), 111.16 <com:Math><semantics>(d,J=2.3 Hz)<annotation encoding="application / x-tex">(d, J = 2.3 \text{ Hz})< / annotation>< / semantics>< / com:Math>. HRMS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 247.0438; found, 247.0439. EXAMPLE 19 2-(4-Chlorophenyl)-5-fluoroimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1) with modification. 2-Amino-6-fluoropyridine was combined with 1-(2- bromo-1,1-dimethoxyethyl)-4-chlorobenzene (1 eq) and CH<com:Sub>3< / com:Sub>CN was added followed by a catalytic amount of Sc(OTf)<com:Sub>3< / com:Sub>. The reaction mixture was stirred in the sealed tube at 120 °C overnight. Mobile phase petrolether / EtOAc (20-100 %). Yield 70 mg (18 %). H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.58 (s, 1H), 8.10 – 8.04 (m, 2H), 7.54 – 7.47 (m, 3H), 7.37 (dt, <com:Math><semantics>J=9.0,6.9<annotation encoding="application / x-tex">J = 9.0, 6.9< / annotation>< / semantics>< / com:Math> Hz, 1H), 6.83 (dd, <com:Math><semantics>J=7.4<annotation encoding="application / x-tex">J = 7.4< / annotation>< / semantics>< / com:Math>, 5.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 148.78 (d, <com:Math><semantics>J=265.0<annotation encoding="application / x-tex">J = 265.0< / annotation>< / semantics>< / com:Math> Hz), 146.93 (d, <com:Math><semantics>J=5.0<annotation encoding="application / x-tex">J = 5.0< / annotation>< / semantics>< / com:Math> Hz), 144.16, 132.78, 132.35, 128.94, 127.72, 126.53 (d, <com:Math><semantics>J=6.6<annotation encoding="application / x-tex">J = 6.6< / annotation>< / semantics>< / com:Math> Hz), 112.83 (d, <com:Math><semantics>J=4.7<annotation encoding="application / x-tex">J = 4.7< / annotation>< / semantics>< / com:Math> Hz), 104.54, 93.06 <com:Math><semantics>(d,J=15.7 Hz)<annotation encoding="application / x-tex">(d, J = 15.7 \text{ Hz})< / annotation>< / semantics>< / com:Math>. HRMS: calcd for [M + H], 247.0439; found, 247.0439. EXAMPLE 20 2-(4-Bromophenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 1.87 g (94 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.52 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.43 (d, <com:Math><semantics>J=0.7<annotation encoding="application / x-tex">J = 0.7< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.98 – 7.86 (m, 2H), <com:Math><semantics>7.65−7.60<annotation encoding="application / x-tex">7.65 - 7.60< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.58<annotation encoding="application / x-tex">7.58< / annotation>< / semantics>< / com:Math> (dq, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>1.0<annotation encoding="application / x-tex">1.0< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.25<annotation encoding="application / x-tex">7.25< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>6.7<annotation encoding="application / x-tex">6.7< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>1.3<annotation encoding="application / x-tex">1.3< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>6.90<annotation encoding="application / x-tex">6.90< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>), <com:Math><semantics>3.65−7.60<annotation encoding="application / x-tex">3.65 - 7.60< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>3.65−7.60<annotation encoding="application / x-tex">3.65 - 7.60< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>3.65−7.60<annotation encoding="application / x-tex">3.65 - 7.60< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>3.65−7.60<annotation encoding="application / x-tex">3.65 - 7.60< / annotation>< / semantics>< / com:Math> (m = 6.7, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 145.04, 143.33, 133.38, 131.81, 127.71, 127.13, 125.38, 120.85, 116.85, 112.61, 109.68. HRMS: calcd for [M + H], 273.0027; found, 273.0028. EXAMPLE 21 2-(4-Chlorophenyl)-6,8-difluoroimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure I (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 0.45 g (87 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.70 (ddd, <com:Math><semantics>J=4.3,2.1,0.9<annotation encoding="application / x-tex">J = 4.3, 2.1, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.55 (d, <com:Math><semantics>J=3.1<annotation encoding="application / x-tex">J = 3.1< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.01 – 7.96 (m, 2H), 7.57 – 7.48 (m, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 151.59 (dd, <com:Math><semantics>J=233.31<annotation encoding="application / x-tex">J = 233.31< / annotation>< / semantics>< / com:Math>, 11.12 Hz), 150.03 (dd, <com:Math><semantics>J=252.4<annotation encoding="application / x-tex">J = 252.4< / annotation>< / semantics>< / com:Math>, 14.9 Hz), 144.75 (d, <com:Math><semantics>J=1.7<annotation encoding="application / x-tex">J = 1.7< / annotation>< / semantics>< / com:Math> Hz), 135.76 (d, <com:Math><semantics>J=1.7<annotation encoding="application / x-tex">J = 1.7< / annotation>< / semantics>< / com:Math> Hz), 135.76 (d, <com:Math><semantics>J=1.7<annotation encoding="application / x-tex">J = 1.7< / annotation>< / semantics>< / com:Math> Hz) <com:Math><semantics>=27.8 Hz<annotation encoding="application / x-tex">= 27.8 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 133.11, 132.41, 129.31, 127.86, 113.25 (d, <com:Math><semantics>J=2.6 Hz<annotation encoding="application / x-tex">J = 2.6 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 111.38 (dd, <com:Math><semantics>J=41.5<annotation encoding="application / x-tex">J = 41.5< / annotation>< / semantics>< / com:Math>, 5.9 Hz), 102.38 <com:Math><semantics>(dd,J=30.3,20.3 Hz)<annotation encoding="application / x-tex">(dd, J = 30.3, 20.3 \text{ Hz})< / annotation>< / semantics>< / com:Math>. HRMS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 265.0344; found, 265.0343. EXAMPLE 22 2-(4-Cyclopropylphenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared from Example 20 (0.1 g, 0.36 mmol), which was dissolved in H<com:Sub>2< / com:Sub>O / CH<com:Sub>3< / com:Sub>CN (1:1) mixture and cyclopropylboronic acid (1.5 eq) was added. The reaction mixture was degassed and refilled with argon. Subsequently K<com:Sub>3< / com:Sub>PO<com:Sub>4< / com:Sub> (3.5 eq), Pd(OAc)<com:Sub>2< / com:Sub> (5 mol %) and Pcy<com:Sub>3< / com:Sub> (10 mol %) were added and the reaction mixture was stirred at 110 °C under argon. After completion of the reaction, the mixture was filtrated over celite<com:Sup>TM< / com:Sup>, extracted with EtOAc, the organic phase was dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography. Mobile phase petrolether / EtOAc (20-70 %). Yield 86 mg (73 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.50 (dt, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 6.8, 1.3 Hz, 1H), 8.33 (s, 1H), 7.85 – 7.80 (m, 2H), 7.55 (dq, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 9.1, 1.0 Hz, 1H), 7.22 (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.7, 1.3 Hz, 1H), 7.16 – 7.10 (m, 2H), 6.87 (td, <com:Math><semantics>J=6.7<annotation encoding="application / x-tex">J = 6.7< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 1.94 (tt, <com:Math><semantics>J=8.4<annotation encoding="application / x-tex">J = 8.4< / annotation>< / semantics>< / com:Math>, 5.1 Hz, 1H), 1.00 – 0.92 (m, 2H), 0.74 – 0.66 (m, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 144.88, 144.61, 143.51, 131.17, 126.93, 125.78, 125.71, 125.66, 124.93, 116.66, 112.31, 108.75, 15.17, 9.67. HRMS: calcd for [M + H], 235.1235; found, 235.1234. General procedure II. Iodination 2-Substituted imidazo[1,2-a]pyridines or imidazo[2,1-b]thiazoles were dissolved in CH<com:Sub>3< / com:Sub>CN (5ml / mmol) and NIS (1.05 eq) was added in one portion. The suspension was stirred at r.t. and the conversion was monitored by TLC. After the completion of the reaction (1-4 h), the reaction mixture was diluted with EtOAc and washed with saturated Na<com:Sub>2< / com:Sub>S<com:Sub>2< / com:Sub>O<com:Sub>3< / com:Sub> solution. Inorganic phase was extracted twice more with EtOAc, combined organic phases were dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography, mobile phase petrolether / EtOAc (10-50 %). EXAMPLE 23 2-(4-Chlorophenyl)-3-iodoimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 352 mg (98 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.42 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.11 – 8.06 (m, 2H), 7.63 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 7.60 – 7.55 (m, 2H), 7.38 (ddd, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 6.8, 1.3 Hz, 1H), 7.09 (td, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 7.63 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 6.8, 1.3 Hz, 1H), 7.09 (td, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 7.63 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 6.8, 1.3 Hz, 1H), 7 6.8, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, CDCl<com:Sub>3< / com:Sub>) δ 147.52, 145.52, 132.99, 132.85, 129.73, 128.67, 127.35, 126.47, 117.16, 113.93, 63.82. HRMS: calcd for [M + H], 354.94935; found, 354.94944. EXAMPLE 24 6-(4-Chlorophenyl)-5-iodoimidazo[2,1-b]thiazole (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 421 mg (89 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 7.98 (m, 2H), 7.87 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.52 (m, 2H), 7.42 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 149.88, 145.54, 133.64, 131.78, 129.09, 126.85, 120.52, 113.85, 110.30. HRMS: calcd for [M+H], 360.90577; found, 360.90586. EXAMPLE 25 6-Chloro-2-(4-chlorophenyl)-3-iodoimidazo[1,2-b]pyridazine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 150 mg (82 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.21 (d, <com:Math><semantics>J=9.4<annotation encoding="application / x-tex">J = 9.4< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.15 <com:Math><semantics>−8.10<annotation encoding="application / x-tex">-8.10< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.62−7.58<annotation encoding="application / x-tex">7.62 - 7.58< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.46<annotation encoding="application / x-tex">7.46< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=9.4<annotation encoding="application / x-tex">J = 9.4< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 147.51, 146.14, 140.77, 133.85, 132.40, 129.88, 129.11, 127.84, 121.02, 72.31. HRMS: calcd for [M + Na], 389.90562; found, 389.90582. EXAMPLE 26 2-(3,4-Dichlorophenyl)-3-iodoimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 638 mg (98 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, Chloroform-d) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.24 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 8.22 (d, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 2.1 Hz, 1H), 7.96 (dd, <com:Math><semantics>J=8.4<annotation encoding="application / x-tex">J = 8.4< / annotation>< / semantics>< / com:Math>, 2.1 Hz, 1H), 7.66 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 7.55 (d, <com:Math><semantics>J=8.4<annotation encoding="application / x-tex">J = 8.4< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.33 (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.8, 1.3 Hz, 1H), 6.99 (td, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 179.90, 147.82, 144.25, 134.93, 131.66, 131.24, 131.09, 129.70, 128.14, 127.74, 127.08, 117.55, 114.43, 64.93. HRMS: calcd for [M + H], 388.91037; found, 388.91052. EXAMPLE 27 6-(3,4-Dichlorophenyl)-5-iodoimidazo[2,1-b]thiazole (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme) 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 514 mg (96 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.17 (d, <com:Math><semantics>J=2.1<annotation encoding="application / x-tex">J = 2.1< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.99 (dd, <com:Math><semantics>J=8.5<annotation encoding="application / x-tex">J = 8.5< / annotation>< / semantics>< / com:Math>, 2.1 Hz, 1H), 7.90 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.75 (d, <com:Math><semantics>J=8.5<annotation encoding="application / x-tex">J = 8.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.46 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 150.98, 145.37, 134.98, 131.61, 131.21, 130.34, 128.53, 126.97, 120.67, 114.97, 60.96. HRMS: calcd for [M + H], 394.86679; found, 394.86699. EXAMPLE 28 3-Iodo-2-phenylimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 468 mg (95 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.43 (dt, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 6.9, 1.1 Hz, 1H), 8.11 – 8.01 (m, 2H), 7.63 (dt, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 9.0, 1.2 Hz, 1H), <com:Math><semantics>7.54−7.47<annotation encoding="application / x-tex">7.54 - 7.47< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.44−7.35<annotation encoding="application / x-tex">7.44 - 7.35< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.08<annotation encoding="application / x-tex">7.08< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 147.43, 146.70, 133.92, 128.54, 128.30, 128.27, 128.13, 127.25, 126.21, 117.08, 113.76, 63.44. HRMS: calcd for [M + H], 320.98832; found, 320.98819. EXAMPLE 29 5-Iodo-6-phenylimidazo[2,1-b]thiazole (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 425 mg (87 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 7.99 – 7.93 (m, 2H), 7.85 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.45 (m, 2H), 7.40 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.37−7.29<annotation encoding="application / x-tex">7.37 - 7.29< / annotation>< / semantics>< / com:Math> (m, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 150.27, 147.85, 134.02, 128.51, 127.71, 127.03, 120.30, 113.93, 59.05. HRMS: calcd for [M + H], 326.94474; found, 326.94476. EXAMPLE 30 3-Iodo-2-(p-tolyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 501 mg (94 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.41 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 7.98 – 7.92 (m, 2H), 7.61 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.36 (ddd, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 6.7, 1.3 Hz, 1H), 7.31 (d, <com:Math><semantics>J=8.0<annotation encoding="application / x-tex">J = 8.0< / annotation>< / semantics>< / com:Math> Hz, 2H), 7.06 (td, <com:Math><semantics>J=6.8,1.2 Hz,1H<annotation encoding="application / x-tex">J = 6.8, 1.2 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 2.36 (s, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 147.70, 147.12, 137.95, 131.41, 129.41, 128.32, 127.44, 126.35, 117.29, 113.92, 63.23, 21.36. HRMS: calcd for [M + H], 335.00397; found, 335.00397. 3-Iodo-2-(pyridin-4-yl)imidazo[1,2-a]pyridine (intermediate compound) Title compound was prepared according to the General Procedure II (Scheme 1). [Image disponible dans le document PDF, Image available in the PDF document] Mobile phase petrolether / EtOAc (10-50 %). Yield: 253 mg (87 %). H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.71 – 8.66 (m, 2H), 8.43 (dt, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 6.9, 1.2 Hz, 1H), 8.10 – 30 8.05 (m, 2H), 7.65 (dt, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.39 (ddd, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 6.7, 1.2 Hz, 1H), 7.09 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H).<com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 150.37, 147.91, 143.89, 141.53, 127.75, 127.17, 122.29, 117.73, 114.54, 65.91. HRMS: calcd for [M + H], 321.98357; found, 321.98367. EXAMPLE 32 [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme) 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 238 mg (89 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.39 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 8.05 – 7.96 (m, 2H), 7.60 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.35 (ddd, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 6.7, 1.2 Hz, 1H), 7.09 – 7.05 (m, 3H), 3.82 (s, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 159.68, 147.67, 146.99, 129.70, 127.38, 126.59, 126.27, 117.16, 114.27, 113.83, 62.62, 55.66. HRMS: calcd for [M + H], 350.99888; found, 350.99893. EXAMPLE 33 2-(2,4-Dichlorophenyl)-3-iodoimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 238 mg (89 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.40 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 7.79 (d, <com:Math><semantics>J=2.0<annotation encoding="application / x-tex">J = 2.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.64 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.59 – 7.51 (m, 2H), 7.40 (ddd, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 9.0, 6.8, 1.3 Hz, 1H), 7.12 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 147.39, 146.72, 134.57, 134.42, 134.34, 132.87, 129.62, 127.72, 127.46, 126.52, 117.62, 114.32, 67.98. HRMS: calcd for [M + H], 388.91037; found, 388.91071. EXAMPLE 34 4-(3-Iodoimidazo[1,2-a]pyridin-2-yl)benzonitrile (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II. Mobile phase petrolether / EtOAc (10-50 %). Yield: 245 mg (90 %). H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.46 (dt, <com:Math><semantics>J=7.0<annotation encoding="application / x-tex">J = 7.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 8.31 – 8.26 (m, 2H), 8.00 <com:Math><semantics>−7.95<annotation encoding="application / x-tex">-7.95< / annotation>< / semantics>< / com:Math> (m, 2H), 7.66 (dt, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.41 (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.8, 1.2 Hz, 1H), 7.11 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 147.64, 144.64, 138.54, 132.60, 128.49, 127.49, 126.85, 119.02, 117.37, 114.20, 110.54, 65.39. HRMS: calcd for [M + H], 345.98357; found, 345.98370. EXAMPLE 35 3-Iodo-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 1.25 g (92 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.46 (d, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.31 (d, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 8.0 Hz, 2H), 7.88 (d, <com:Math><semantics>J=8.1<annotation encoding="application / x-tex">J = 8.1< / annotation>< / semantics>< / com:Math> Hz, 2H), 7.67 (d, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.42 (dd, <com:Math><semantics>J=8.9<annotation encoding="application / x-tex">J = 8.9< / annotation>< / semantics>< / com:Math>, 6.9 Hz, 1H), 7.12 (t, <com:Math><semantics>J=8.0<annotation encoding="application / x-tex">J = 8.0< / annotation>< / semantics>< / com:Math> Hz, 2H), 7.88 (d, <com:Math><semantics>J=8.1<annotation encoding="application / x-tex">J = 8.1< / annotation>< / semantics>< / com:Math> Hz, 2H), 7.67 (d, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.42 (dd, <com:Math><semantics>J=8.9<annotation encoding="application / x-tex">J = 8.9< / annotation>< / semantics>< / com:Math>, 6.9 Hz, 1H), = 6.8 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 147.90, 145.35, 138.31, 128.87, 128.65 127.74, 126.96, 125.81 (<com:Math><semantics>J=3.78<annotation encoding="application / x-tex">J = 3.78< / annotation>< / semantics>< / com:Math> Hz), 124.77, 117.61, 114.38, 65.13. HRMS: calcd for [M + H], 388.97570; found, 388.97582. EXAMPLE 36 2-(4-Fluorophenyl)-3-iodoimidazo[1,2-a]pyridine (intermediate compound) 27 [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme) 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 1.42 g (97 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.40 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 8.12 – 8.06 (m, 2H), 7.62 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.40 – 7.30 (m, 3H), 7.07 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 162.15 (d, <com:Math><semantics>J=245.5<annotation encoding="application / x-tex">J = 245.5< / annotation>< / semantics>< / com:Math> Hz), 147.44, 145.88, 130.42 (d, <com:Math><semantics>J=3.0<annotation encoding="application / x-tex">J = 3.0< / annotation>< / semantics>< / com:Math> Hz), 130.15 (d, <com:Math><semantics>J=8.3<annotation encoding="application / x-tex">J = 8.3< / annotation>< / semantics>< / com:Math> Hz), 127.25, 126.28, 117.05, 115.48 (d, <com:Math><semantics>J=21.5 Hz<annotation encoding="application / x-tex">J = 21.5 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 113.78, 63.34. HRMS: calcd for [M + H], 338.97890; found, 338.97902. EXAMPLE 37 2-(4-Ethylphenyl)-3-iodoimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 1.23 g (86 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.41 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.00 – 7.95 (m, 2H), 7.62 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.39 – 7.36 (m, 3H), 7.35 – 7.31 (m, 2H), 7.07 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 2.66 (q, <com:Math><semantics>J=7.6<annotation encoding="application / x-tex">J = 7.6< / annotation>< / semantics>< / com:Math> Hz, 2H), 1.22 (t, <com:Math><semantics>J=7.6<annotation encoding="application / x-tex">J = 7.6< / annotation>< / semantics>< / com:Math> Hz, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 147.41, 146.83, 143.95, 131.35, 128.10, 127.93, 127.16, 126.08, 117.00, 113.65, 62.95, 28.15, 15.67. HRMS: calcd for [M + H], 349.01962; found, 349.01982. EXAMPLE 38 2-(4-Chlorophenyl)-8-fluoro-3-iodoimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 0.35 g (92 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.30 (dd, <com:Math><semantics>J=6.9,0.9<annotation encoding="application / x-tex">J = 6.9, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.11 – 8.04 (m, 2H), <com:Math><semantics>7.63−7.55<annotation encoding="application / x-tex">7.63 - 7.55< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.32<annotation encoding="application / x-tex">7.32< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=11.0,7.7,0.9<annotation encoding="application / x-tex">J = 11.0, 7.7, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.06<annotation encoding="application / x-tex">7.06< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=11.0,7.7,0.9<annotation encoding="application / x-tex">J = 11.0, 7.7, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.06<annotation encoding="application / x-tex">7.06< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=11.0,7.7,0.9<annotation encoding="application / x-tex">J = 11.0, 7.7, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.06<annotation encoding="application / x-tex">7.06< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=11.0,7.7,0.9<annotation encoding="application / x-tex">J = 11.0, 7.7, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.06<annotation encoding="application / x-tex">7.06< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=11.<annotation encoding="application / x-tex">J = 11.< / annotation>< / semantics>< / com:Math> = 7.6, 6.9, 4.8 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 150.29 (d, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 250.5 Hz), 145.73, 139.66 (d, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> <com:Math><semantics>=28.7 Hz<annotation encoding="application / x-tex">= 28.7 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 133.22, 132.30, 129.80, 128.69, 124.18 (d, <com:Math><semantics>J=4.8 Hz<annotation encoding="application / x-tex">J = 4.8 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 112.71 (d, <com:Math><semantics>J=7.1 Hz<annotation encoding="application / x-tex">J = 7.1 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 109.01 (d, <com:Math><semantics>J=7.1 Hz<annotation encoding="application / x-tex">J = 7.1 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 109.01 (d, <com:Math><semantics>J=7.1 Hz<annotation encoding="application / x-tex">J = 7.1 \text{ Hz}< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>=16.0 Hz<annotation encoding="application / x-tex">= 16.0 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 66.13. HRMS: calcd for [M + H], 372.9405; found, 372.9407. EXAMPLE 39 2-(4-Chlorophenyl)-7-fluoro-3-iodoimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 0.32 g (93 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.49 (t, <com:Math><semantics>J=6.6<annotation encoding="application / x-tex">J = 6.6< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.07 <com:Math><semantics>(d,J=8.2 Hz,2H),7.57 (dd,J=9.0,6.0 Hz,3H),7.12 (td,J=7.6,2.6 Hz,1H).<annotation encoding="application / x-tex">(d, J = 8.2 \text{ Hz}, 2H), 7.57 \text{ } (dd, J = 9.0, 6.0 \text{ Hz}, 3H), 7.12 \text{ } (td, J = 7.6, 2.6 \text{ Hz}, 1H).< / annotation>< / semantics>< / com:Math> <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 160.72 (d, <com:Math><semantics>J=249.8<annotation encoding="application / x-tex">J = 249.8< / annotation>< / semantics>< / com:Math> Hz), 147.16 (d, <com:Math><semantics>J=14.2<annotation encoding="application / x-tex">J = 14.2< / annotation>< / semantics>< / com:Math> Hz), 146.55, 133.05, 132.58, 129.57, 128.94, 128.68, 127.37, 105.83 (d, <com:Math><semantics>J=29.7<annotation encoding="application / x-tex">J = 29.7< / annotation>< / semantics>< / com:Math> Hz), 100.73 (d, <com:Math><semantics>J=23.8<annotation encoding="application / x-tex">J = 23.8< / annotation>< / semantics>< / com:Math> Hz), 63.43. HRMS: calcd for [M + H], 372.9405; found, 372.9407. EXAMPLE 40 2-(4-Chlorophenyl)-6-fluoro-3-iodoimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 0.29 g (92 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.57 (ddd, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 4.6, 2.4, 0.8 Hz, 1H), <com:Math><semantics>8.09−8.03<annotation encoding="application / x-tex">8.09 - 8.03< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.73<annotation encoding="application / x-tex">7.73< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=9.8<annotation encoding="application / x-tex">J = 9.8< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>5.3<annotation encoding="application / x-tex">5.3< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>0.8<annotation encoding="application / x-tex">0.8< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.60−7.55<annotation encoding="application / x-tex">7.60 - 7.55< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.47<annotation encoding="application / x-tex">7.47< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=9.8<annotation encoding="application / x-tex">J = 9.8< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>5.3<annotation encoding="application / x-tex">5.3< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>0.8<annotation encoding="application / x-tex">0.8< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.60−7.55<annotation encoding="application / x-tex">7.60 - 7.55< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.47<annotation encoding="application / x-tex">7.47< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=9.8<annotation encoding="application / x-tex">J = 9.8< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>5.3<annotation encoding="application / x-tex">5.3< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>0.8<annotation encoding="application / x-tex">0.8< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>1<annotation encoding="application / x-tex">1< / annotation>< / semantics>< / com:Math>H), <com:Math><semantics>1.<annotation encoding="application / x-tex">1.< / annotation>< / semantics>< / com:Math> 9.8, 8.3, 2.4 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 153.66 (d, <com:Math><semantics>J=235.2<annotation encoding="application / x-tex">J = 235.2< / annotation>< / semantics>< / com:Math> Hz), 146.82 (d, <com:Math><semantics>J=2.3<annotation encoding="application / x-tex">J = 2.3< / annotation>< / semantics>< / com:Math>) Hz), 145.33, 133.08, 132.63, 129.65, 128.68, 118.23 (d, <com:Math><semantics>J=13.6<annotation encoding="application / x-tex">J = 13.6< / annotation>< / semantics>< / com:Math> Hz), 118.05 (d, <com:Math><semantics>J=3.0<annotation encoding="application / x-tex">J = 3.0< / annotation>< / semantics>< / com:Math> Hz), 114.46 (d, <com:Math><semantics>J=42.7 Hz<annotation encoding="application / x-tex">J = 42.7 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 65.73. HRMS: calcd for [M + H], 372.9405; found, 372.9406. EXAMPLE 41 2-(4-Chlorophenyl)-5-fluoro-3-iodoimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 14 mg (75 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 7.98 – 7.92 (m, 2H), 7.60 – 7.55 (m, 2H), <com:Math><semantics>7.55−7.50<annotation encoding="application / x-tex">7.55 - 7.50< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>7.38<annotation encoding="application / x-tex">7.38< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>7.5<annotation encoding="application / x-tex">7.5< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>6.0<annotation encoding="application / x-tex">6.0< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>6.83<annotation encoding="application / x-tex">6.83< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=7.5<annotation encoding="application / x-tex">J = 7.5< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>1.0<annotation encoding="application / x-tex">1.0< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 149.83 (d, <com:Math><semantics>J=268.7<annotation encoding="application / x-tex">J = 268.7< / annotation>< / semantics>< / com:Math> Hz), 149.66 (d, <com:Math><semantics>J=4.6<annotation encoding="application / x-tex">J = 4.6< / annotation>< / semantics>< / com:Math> Hz), 148.00, 126.85 (d, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math> Hz), 113.62 (d, <com:Math><semantics>J=4.9<annotation encoding="application / x-tex">J = 4.9< / annotation>< / semantics>< / com:Math> Hz), 94.58 (d, <com:Math><semantics>J=17.4<annotation encoding="application / x-tex">J = 17.4< / annotation>< / semantics>< / com:Math> Hz), 54.45 (d, <com:Math><semantics>J=2.2<annotation encoding="application / x-tex">J = 2.2< / annotation>< / semantics>< / com:Math> Hz). HRMS: calcd for [M + H], 372.9405; found, 372.9407. EXAMPLE 42 2-(4-Chlorophenyl)-6,8-difluoro-3-iodoimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 0.345 g (94 %). H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.49 (ddd, <com:Math><semantics>J=4.4,2.1,0.9<annotation encoding="application / x-tex">J = 4.4, 2.1, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>8.07−8.01<annotation encoding="application / x-tex">8.07 - 8.01< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.67<annotation encoding="application / x-tex">7.67< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=11.1<annotation encoding="application / x-tex">J = 11.1< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>9.2<annotation encoding="application / x-tex">9.2< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>2.1<annotation encoding="application / x-tex">2.1< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.59−<annotation encoding="application / x-tex">7.59 -< / annotation>< / semantics>< / com:Math> 7.52 (m, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 151.95 (dd, <com:Math><semantics>J=235.62<annotation encoding="application / x-tex">J = 235.62< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=11.32<annotation encoding="application / x-tex">J = 11.32< / annotation>< / semantics>< / com:Math> Hz), 149.72 (dd, <com:Math><semantics>J=235.62<annotation encoding="application / x-tex">J = 235.62< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=11.32<annotation encoding="application / x-tex">J = 11.32< / annotation>< / semantics>< / com:Math> Hz), 149.72 (dd, <com:Math><semantics>J=235.62<annotation encoding="application / x-tex">J = 235.62< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=11.32<annotation encoding="application / x-tex">J = 11.32< / annotation>< / semantics>< / com:Math> Hz) <com:Math><semantics>=253.9,14.6 Hz),146.63 (d, J=1.9 Hz),137.70 (d, J=28.1 Hz),133.34,132.10,129.72,128.71,111.71<annotation encoding="application / x-tex">= 253.9, 14.6 \text{ Hz}), 146.63 \text{ (d, } J = 1.9 \text{ Hz)}, 137.70 \text{ (d, } J = 28.1 \text{ Hz)}, 133.34, 132.10, 129.72, 128.71, 111.71< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(dd,J=42.6,5.8 Hz),103.00(dd,J=30.2,20.3 Hz),68.18(d,J=2.5 Hz).<annotation encoding="application / x-tex">(dd, J = 42.6, 5.8 \text{ Hz}), 103.00 (dd, J = 30.2, 20.3 \text{ Hz}), 68.18 (d, J = 2.5 \text{ Hz}).< / annotation>< / semantics>< / com:Math> HRMS: calcd for [M + H], 390.9311; found, 390.9312. EXAMPLE 43 2-(4-Cyclopropylphenyl)-3-iodoimidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure II (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 0.287 g (99 %). H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.40 (d, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.95 (d, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 8.0 Hz, 2H), 7.61 (d, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.35 (t, <com:Math><semantics>J=7.9<annotation encoding="application / x-tex">J = 7.9< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.19 (d, <com:Math><semantics>J=7.9<annotation encoding="application / x-tex">J = 7.9< / annotation>< / semantics>< / com:Math> Hz, 2H), 7.06 (t, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math> Hz, 1H), 1.97 (td, <com:Math><semantics>J=8.5<annotation encoding="application / x-tex">J = 8.5< / annotation>< / semantics>< / com:Math>, 4.3 Hz, 1H), 0.98 (d, <com:Math><semantics>J=7.7<annotation encoding="application / x-tex">J = 7.7< / annotation>< / semantics>< / com:Math> Hz, 2H), 0.73 (d, <com:Math><semantics>J=5.4<annotation encoding="application / x-tex">J = 5.4< / annotation>< / semantics>< / com:Math> Hz, 2H). <com:Sup>13< / com:Sup>C NMR (101) MHz, DMSO) δ 147.37, 146.72, 144.04, 130.89, 127.98, 127.13, 126.06, 125.43, 116.95, 113.62, 62.86, 15.18, 9.83. HRMS: calcd for [M + H], 361.0202; found, 361.0206. General procedure III. Sonogashira coupling 3-Iodoimidazo[1,2-a]pyridines or 5-iodoimidazo[2,1-b]thiazoles were placed in dried round bottom flask, diluted with dry DMF and degassed at 0 °C and flushed with argon. CuI (10 mol%), Pd(PPh<com:Sub>3< / com:Sub>)<com:Sub>2< / com:Sub>Cl<com:Sub>2< / com:Sub> (5 mol%) were added and the mixture was properly degassed and dry TEA (3 eq) was added and the mixture degassed again. Finally TMS-acetylene (5 eq) was added in one portion. The reaction mixture was stirred at r.t. under the argon atmosphere. After the completion of the reaction (monitored by TLC), the mixture was if necessary diluted with CHCl<com:Sub>3< / com:Sub> and filtered over celite. Filtrate was washed with water, water phase was extracted twice more with CHCl<com:Sub>3< / com:Sub>, combined organic phases were dried over sodium sulfate and evaporated. A residue was purified by flash column chromatography (mobile phase petrolether / EtOAc). EXAMPLE 44 2-(4-Chlorophenyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 625 mg (56 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.41 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.28 – 8.21 (m, 2H), 7.70 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.59 – 7.53 (m, 2H), 7.46 (ddd, <com:Math><semantics>J=9.0,6.8,1.3 Hz,1H<annotation encoding="application / x-tex">J = 9.0, 6.8, 1.3 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 7.14 (td, <com:Math><semantics>J=6.8,1.2 Hz,1H<annotation encoding="application / x-tex">J = 6.8, 1.2 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 0.34 (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 146.17, 144.70, 133.43, 132.04, 128.88, 128.28, 127.82, 125.82, 117.30, 114.28, 108.95, 104.06, 93.27, -0.10. HRMS: calcd for [M + H], 325.09223; found, 325.09232. EXAMPLE 45 6-(4-Chlorophenyl)-5-((trimethylsilyl)ethynyl)imidazo[2,1-b]thiazole (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 458 mg (61 %). <com:Sup>1< / com:Sup>H NMR (500 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.10 (m, 2H), 7.92 (d, <com:Math><semantics>J=4.4<annotation encoding="application / x-tex">J = 4.4< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.51 – 7.54 (m, 2H), 7.44 (d, <com:Math><semantics>J=4.4<annotation encoding="application / x-tex">J = 4.4< / annotation>< / semantics>< / com:Math> Hz, 1H), 0.31. <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 149.86, 145.03, 133.72, 132.31, 128.81, 127.46, 119.32, 115.60, 106.93, 105.19, 93.51, -0.17. EI MS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 330.0414; found, 330.0416. 6-Chloro-2-(4-chlorophenyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-b]pyridazine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 165 mg (46 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, Chloroform-d) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 7.53 – 7.47 (m, 2H), 7.09 <com:Math><semantics>(d,J=9.4 Hz,1H),6.68−6.61 (m, 2H),6.33 (d, J=9.4 Hz,1H),−0.43<annotation encoding="application / x-tex">(d, J = 9.4 \text{ Hz}, 1\text{H}), 6.68 - 6.61 \text{ (m, 2H)}, 6.33 \text{ (d, } J = 9.4 \text{ Hz}, 1\text{H)}, -0.43< / annotation>< / semantics>< / com:Math> (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, CDCl<com:Sub>3< / com:Sub>) δ 147.66, 147.41, 137.38, 135.17, 131.02, 128.95, 128.78, 128.58, 128.47, 127.47, 126.23, 120.62, 109.89, 91.62, -0.26. HRMS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 360.04851; found, 360.04867. EXAMPLE 47 2-Phenyl-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) Title compound was prepared according to the General Procedure III (Scheme 1). [Image disponible dans le document PDF, Image available in the PDF document] Mobile phase petrolether / EtOAc (10-50 %). Yield: 78 mg (62 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.41 (dt, <com:Math><semantics>J=6.7,1.2<annotation encoding="application / x-tex">J = 6.7, 1.2< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>8.32−8.24<annotation encoding="application / x-tex">8.32 - 8.24< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.71<annotation encoding="application / x-tex">7.71< / annotation>< / semantics>< / com:Math> (dt, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 9.0, 1.2 Hz, 1H), <com:Math><semantics>7.53−7.38<annotation encoding="application / x-tex">7.53 - 7.38< / annotation>< / semantics>< / com:Math> (m, 4H), <com:Math><semantics>7.13<annotation encoding="application / x-tex">7.13< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), <com:Math><semantics>0.34<annotation encoding="application / x-tex">0.34< / annotation>< / semantics>< / com:Math> (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 147.48, 144.68, 133.17, 128.91, 128.81, 128.76, 127.57, 126.71, 125.73, 117.26, 114.11, 108.44, 103.86, 93.66, -0.08. HRMS: calcd for [M + H], 291.13120; found, 291.13125. EXAMPLE 48 6-Phenyl-5-((trimethylsilyl)ethynyl)imidazo[2,1-b]thiazole (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 82 mg (71 %). H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.16 – 8.10 (m, 2H), 7.88 (d, <com:Math><semantics>J=4.4<annotation encoding="application / x-tex">J = 4.4< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.46 – 7.39 (m, 3H), <com:Math><semantics>7.35−7.30<annotation encoding="application / x-tex">7.35 - 7.30< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>0.30<annotation encoding="application / x-tex">0.30< / annotation>< / semantics>< / com:Math> (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 149.93, 149.66, 133.78, 128.93, 128.53, 126.20, 119.51, 115.53, 106.59, 105.28, 94.25, 0.14. HRMS: calcd for [M + H], 297.08762; found, 297.08771. EXAMPLE 49 2-(p-Tolyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) Title compound was prepared according to the General Procedure III (Scheme) [Image disponible dans le document PDF, Image available in the PDF document] 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 117 mg (64 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.39 (d, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.16 (d, <com:Math><semantics>J=7.8<annotation encoding="application / x-tex">J = 7.8< / annotation>< / semantics>< / com:Math> Hz, 2H), 7.69 (d, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.43 (dd, <com:Math><semantics>J=8.9<annotation encoding="application / x-tex">J = 8.9< / annotation>< / semantics>< / com:Math>, 6.9 Hz, 1H), 7.30 (d, <com:Math><semantics>J=7.9<annotation encoding="application / x-tex">J = 7.9< / annotation>< / semantics>< / com:Math> Hz, 2H), 7.12 (t, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math> Hz, 1H), 2.36 (s, 3H), 0.34 (s, 9H). <com:Sup>13< / com:Sup>C NMR (101) MHz, DMSO) δ 147.99, 144.94, 138.80, 130.71, 129.64, 127.79, 126.95, 125.98, 117.43, 114.32, 108.68, 103.79, 94.13, 21.38, 0.24. HRMS: calcd for [M + H], 305.14685; found, 305.14690. 31 2-(4-Nitrophenyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 25 mg (11 %). H NMR (401 MHz, Chloroform-d) <com:Math><semantics>δ8.59−8.52<annotation encoding="application / x-tex">\delta 8.59 - 8.52< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>8.38−8.31<annotation encoding="application / x-tex">8.38 - 8.31< / annotation>< / semantics>< / com:Math> (m, 3H), 7.70 (dt, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.40 – 7.34 (m, 1H), 7.02 (td, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 6.8, 1.2 Hz, 1H), 0.41 (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, CDCl<com:Sub>3< / com:Sub>) δ 127.60, 127.21, 125.51, 123.82, 117.85, 113.65, 92.75, -0.12. HRMS: calcd for [M + H], 336.11628; found, 336.11584. EXAMPLE 51 2-(2,4-Dichlorophenyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 98 mg (64 %). H NMR (401 MHz, Chloroform-d) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.30 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 7.64 (m, 2H), 7.54 (d, <com:Math><semantics>J=2.1<annotation encoding="application / x-tex">J = 2.1< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.38 – 7.27 (m, 2H), 6.97 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2) Hz, 1H), 0.27 (s, 9H). <com:Math><semantics>13<annotation encoding="application / x-tex">^{13}< / annotation>< / semantics>< / com:Math>C NMR (101 MHz, CDCl<com:Sub>3< / com:Sub>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 146.79, 144.80, 135.05, 134.32, 133.22, 131.39, 130.12, 126.95, 126.52, 125.55, 117.98, 113.42, 108.14, 92.17, 0.04. HRMS: calcd for [M + H], 321.14177; found, 321.14179. EXAMPLE 52 2-(4-Methoxyphenyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 98 mg (64 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.38 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.26 – 8.18 (m, 2H), 7.67 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.42 (ddd, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 6.8, 1.3 Hz, 1H), 7.11 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), <com:Math><semantics>7.08−7.03<annotation encoding="application / x-tex">7.08 - 7.03< / annotation>< / semantics>< / com:Math> (m, 2H), 3.82 (s, 3H), 0.34 (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 159.83, 147.63, 144.60, 128.13, 127.19, 125.75, 125.49, 116.93, 114.07, 113.72, 108.09, 102.92, 94.03, 55.32, -0.04, -0.06, -0.08. HRMS: calcd for [M + H], 321.14177; found, 321.14179 EXAMPLE 53 4-(3-((Trimethylsilyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)benzonitrile (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 170 mg (65 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.44 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.42 – 8.38 (m, 2H), <com:Math><semantics>7.99−7.94<annotation encoding="application / x-tex">7.99 - 7.94< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.74<annotation encoding="application / x-tex">7.74< / annotation>< / semantics>< / com:Math> (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), <com:Math><semantics>7.49<annotation encoding="application / x-tex">7.49< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=9.1,6.8,1.3 Hz,1H<annotation encoding="application / x-tex">J = 9.1, 6.8, 1.3 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 7.17 (td, <com:Math><semantics>J=6.8,1.1 Hz,1H<annotation encoding="application / x-tex">J = 6.8, 1.1 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 145.16, 144.88, 137.51, 132.85, 128.24, 127.06, 125.97, 118.91, 117.56, 114.62, 110.97, 109.67, 105.24, 92.83, -0.14. HRMS: calcd for [M + H], 316.12645; found, 316.12656. EXAMPLE 54 2-(4-(Trifluoromethyl)phenyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 123 mg (54) %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.45 (tt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.0 Hz, 3H), 7.91 – 7.82 (m, 2H), 7.74 (dt, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.49 (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.8, 1.3 Hz, 1H), 7.17 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 0.37 (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 145.80, 145.12, 137.36, 137.35, 129.25, 128.93, 128.38, 127.42, 126.23, 126.08 (q, <com:Math><semantics>J=3.9<annotation encoding="application / x-tex">J = 3.9< / annotation>< / semantics>< / com:Math>) Hz), 117.80, 114.82, 109.61, 105.20, 93.24, 0.18. HRMS: calcd for [M + H], 359.11859; found, 359.11862. EXAMPLE 55 2-(4-Fluorophenyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 250 mg (69 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.41 (dd, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.4 Hz, 1H), 8.32 – 8.25 (m, 2H), 7.70 (dd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.4 Hz, 1H), 7.45 (ddt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 6.8, 1.3 Hz, 1H), 7.38 <com:Math><semantics>−7.31<annotation encoding="application / x-tex">-7.31< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.13<annotation encoding="application / x-tex">7.13< / annotation>< / semantics>< / com:Math> (tt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>1.3<annotation encoding="application / x-tex">1.3< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>0.36−0.31<annotation encoding="application / x-tex">0.36 - 0.31< / annotation>< / semantics>< / com:Math> (m, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 162.46 (d, <com:Math><semantics>J=246.2<annotation encoding="application / x-tex">J = 246.2< / annotation>< / semantics>< / com:Math> Hz), 146.53, 144.70, 129.74 (d, <com:Math><semantics>J=3.0<annotation encoding="application / x-tex">J = 3.0< / annotation>< / semantics>< / com:Math> Hz), 128.79 (d, <com:Math><semantics>J=3.0<annotation encoding="application / x-tex">J = 3.0< / annotation>< / semantics>< / com:Math> Hz) 8.4 Hz), 127.74, 125.81, 117.24, 117.24, 115.81 (d, <com:Math><semantics>J=21.6<annotation encoding="application / x-tex">J = 21.6< / annotation>< / semantics>< / com:Math> Hz), 114.21, 114.21, 108.58, 103.68, 93.46, -0.05. HRMS: calcd for [M + H], 309.12178; found, 309.12195. EXAMPLE 56 2-(4-Ethylphenyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 126 mg (63) %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.39 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.22 – 8.16 (m, 2H), 7.69 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.42 (ddd, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 6.8, 1.3 Hz, 1H), <com:Math><semantics>7.35−7.29<annotation encoding="application / x-tex">7.35 - 7.29< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.11<annotation encoding="application / x-tex">7.11< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>1.2<annotation encoding="application / x-tex">1.2< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>2.65<annotation encoding="application / x-tex">2.65< / annotation>< / semantics>< / com:Math> (q, <com:Math><semantics>J=7.6<annotation encoding="application / x-tex">J = 7.6< / annotation>< / semantics>< / com:Math> Hz, 2H), 1.20 (t, <com:Math><semantics>J=7.6<annotation encoding="application / x-tex">J = 7.6< / annotation>< / semantics>< / com:Math> Hz, 3H), 0.34 (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 147.66, 144.72, 144.65, 130.69, 128.12, 127.44, 126.73, 125.64, 117.14, 113.98, 108.33, 103.51, 93.84, 28.18, 15.57, -0.06. HRMS: calcd for [M + H], 319.16250; found, 319.16255. EXAMPLE 57 2-(4-Chlorophenyl)-8-fluoro-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine(intermediate compound) 33 [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 125 mg (76 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.28 – 8.21 (m, 3H), 7.59 – 7.54 (m, 2H), 7.36 (ddd, <com:Math><semantics>J=11.0<annotation encoding="application / x-tex">J = 11.0< / annotation>< / semantics>< / com:Math>, 7.8, 0.9 Hz, 1H), 7.09 (ddd, <com:Math><semantics>J=7.7<annotation encoding="application / x-tex">J = 7.7< / annotation>< / semantics>< / com:Math>, 6.7, 4.6 Hz, 1H), 0.35 (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 150.88 (d, <com:Math><semantics>J=250.2<annotation encoding="application / x-tex">J = 250.2< / annotation>< / semantics>< / com:Math> Hz), 146.41, 137.25 (d, <com:Math><semantics>J=28.8<annotation encoding="application / x-tex">J = 28.8< / annotation>< / semantics>< / com:Math> Hz), 134.04, 131.82, 129.27, 128.67, 122.87 <com:Math><semantics>(d,J=4.7 Hz),113.82(d,J=7.0 Hz),110.96(d,J=16.0 Hz),109.84,106.00,92.94.<annotation encoding="application / x-tex">(d, J = 4.7 \text{ Hz}), 113.82 (d, J = 7.0 \text{ Hz}), 110.96 (d, J = 16.0 \text{ Hz}), 109.84, 106.00, 92.94.< / annotation>< / semantics>< / com:Math> HRMS: calcd for [M + H], 343.0834; found, 343.0836. EXAMPLE 58 2-(4-Chlorophenyl)-7-fluoro-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 171 mg (58 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.44 (dd, <com:Math><semantics>J=7.5<annotation encoding="application / x-tex">J = 7.5< / annotation>< / semantics>< / com:Math>, 5.6 Hz, 1H), <com:Math><semantics>8.25−8.19<annotation encoding="application / x-tex">8.25 - 8.19< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.64−7.58<annotation encoding="application / x-tex">7.64 - 7.58< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>7.57−7.53<annotation encoding="application / x-tex">7.57 - 7.53< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.16<annotation encoding="application / x-tex">7.16< / annotation>< / semantics>< / com:Math> (td, J) = 7.6, 2.6 Hz, 1H), 0.34 (s, 9H). <com:Math><semantics>13<annotation encoding="application / x-tex">{}^{13}< / annotation>< / semantics>< / com:Math>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 161.38 <com:Math><semantics>(d,J=251.3 Hz),147.05,145.42,133.58,131.78,128.97,128.23,109.11,106.21(d,<math>J=29.3 Hz),101.39<annotation encoding="application / x-tex">(d, J = 251.3 \text{ Hz}), 147.05, 145.42, 133.58, 131.78, 128.97, 128.23, 109.11, 106.21 (d, J = 29.3 \text{ Hz}), 101.39< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(d,J=24.0 Hz),92.91,−0.12.HRMS:calcdfor[M+H],343.0834;found,343.0833.<annotation encoding="application / x-tex">(d, J = 24.0 \text{ Hz}), 92.91, -0.12. HRMS: calcd for [M + H], 343.0834; found, 343.0833.< / annotation>< / semantics>< / com:Math> EXAMPLE 59 2-(4-Chlorophenyl)-6-fluoro-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 74 mg (40 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.54 (ddd, <com:Math><semantics>J=4.0,2.5,0.8<annotation encoding="application / x-tex">J = 4.0, 2.5, 0.8< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>8.28−8.18<annotation encoding="application / x-tex">8.28 - 8.18< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.77<annotation encoding="application / x-tex">7.77< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=9.8<annotation encoding="application / x-tex">J = 9.8< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>5.1<annotation encoding="application / x-tex">5.1< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>0.8<annotation encoding="application / x-tex">0.8< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.61−7.50<annotation encoding="application / x-tex">7.61 - 7.50< / annotation>< / semantics>< / com:Math> (m, 3H), 0.35 (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 153.80 (d, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 236.5 Hz), 147.10, 142.48, 133.58, 131.85, 128.96, 128.24, 119.52 (d, <com:Math><semantics>J=25.6<annotation encoding="application / x-tex">J = 25.6< / annotation>< / semantics>< / com:Math> Hz), 118.26 (d, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math> Hz), 112.95 (d, <com:Math><semantics>J=41.3<annotation encoding="application / x-tex">J = 41.3< / annotation>< / semantics>< / com:Math> Hz), 109.91, 92.54, -0.15. HRMS: calcd for [M + H], 343.0834; found, 343.0835. EXAMPLE 60 2-(4-Chlorophenyl)-5-fluoro-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1) and used as crude for the next step without further purification. EXAMPLE 61 2-(4-Chlorophenyl)-6,8-difluoro-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1) and used as crude for the next step without further purification. EXAMPLE 62 <com:Math><semantics>2−(4−Cyclopropylphenyl)−3−((trimethylsilyl)ethynyl)imidazo[1,2−a]pyridine(intermediate<annotation encoding="application / x-tex">2-(4-Cyclopropylphenyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine (intermediate< / annotation>< / semantics>< / com:Math> compound) [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General Procedure III (Scheme 1). Mobile phase petrolether / EtOAc (10-50 %). Yield: 211 mg (93) %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.38 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.19 <com:Math><semantics>−8.11<annotation encoding="application / x-tex">-8.11< / annotation>< / semantics>< / com:Math> (m, 2H), 7.68 (dt, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.42 (ddd, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math>, 6.8, 1.3 Hz, 1H), <com:Math><semantics>7.22−7.14<annotation encoding="application / x-tex">7.22 - 7.14< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.11<annotation encoding="application / x-tex">7.11< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), <com:Math><semantics>1.99−1.89<annotation encoding="application / x-tex">1.99 - 1.89< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>1.02−0.90<annotation encoding="application / x-tex">1.02 - 0.90< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>0.77−0.68<annotation encoding="application / x-tex">0.77 - 0.68< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>0.34<annotation encoding="application / x-tex">0.34< / annotation>< / semantics>< / com:Math> (s, 9H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 147.62, 144.87, 144.64, 130.25, 127.43, 126.63, 125.61, 117.10, 113.95, 108.37, 103.39, 93.85, 15.25, 9.90, - <com:Math><semantics>0.04<annotation encoding="application / x-tex">0.04< / annotation>< / semantics>< / com:Math>. HRMS: calcd for [M + H], <com:Math><semantics>331.1631<annotation encoding="application / x-tex">331.1631< / annotation>< / semantics>< / com:Math>; found, <com:Math><semantics>331.1630<annotation encoding="application / x-tex">331.1630< / annotation>< / semantics>< / com:Math>. Generale procedure IV. Click reaction Trimethylsilyl(ethynyl)imidazo[2,1-b]thiazole or trimethylsilyl(ethynyl)imidazo[1,2-a]pyridine derivatives were dissolved in THF / H<com:Sub>2< / com:Sub>O mixture (1:1) and an appropriate azido intermediate (1 eq) was added. The reaction mixture was degassed at 0 °C, refilled with argon and CuSO<com:Sub>4< / com:Sub>.5H<com:Sub>2< / com:Sub>O (10 mol %), KF (1 eq), Na-ascorbate (1 eq) were added in one portion. The reaction mixture was stirred at r.t. and monitored by TLC. After the completion of the reaction, the mixture was diluted with EtOAc and washed with water. The water phase was extracted twice more with EtOAc, combined organic phases were dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography (eluent petrolether / EtOAc or EtOAc / MeOH). EXAMPLE 63 2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1<com:Math><semantics>H<annotation encoding="application / x-tex">H< / annotation>< / semantics>< / com:Math>-1,2,3-triazol-4-yl)imidazo[1,2-<com:Math><semantics>a<annotation encoding="application / x-tex">a< / annotation>< / semantics>< / com:Math>]pyridine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 130 mg (57) %). H NMR (500 MHz, DMSO-d6) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.53 (s, 1H), 8.48 (dt, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math> 6.9 Hz, 1H), 7.67-7.71 (m, 5H), <com:Math><semantics>7.41−7.44<annotation encoding="application / x-tex">7.41 - 7.44< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.39<annotation encoding="application / x-tex">7.39< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=1.2<annotation encoding="application / x-tex">J = 1.2< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=6.8 Hz,J=9.1 Hz,1H,7.35 (dd,J=2.1 Hz,J=8.4 Hz,1H,7.00 (td,J)<annotation encoding="application / x-tex">J = 6.8 \text{ Hz}, J = 9.1 \text{ Hz}, 1\text{H}, 7.35 \text{ (dd}, J = 2.1 \text{ Hz}, J = 8.4 \text{ Hz}, 1\text{H}, 7.00 \text{ (td}, J)< / annotation>< / semantics>< / com:Math> = 1.2 Hz, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math> Hz, 1H), 5.75 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, CDCl<com:Sub>3< / com:Sub>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 144.95, 142.52, 137.05, 136.40, 133.04, 132.86, 131.53, 131.28, 131.21, 130.34, 129.67, 128.71, 128.59, 126.30, 125.95, 125.45, 117.13, 113.38, 111.57, 51.94. HRMS: calcd for [M + H], 454.03876; found, 454.03886. EXAMPLE 64 <com:Math><semantics>6−(4−Chlorophenyl)−5−(1−(3,4−dichlorobenzyl)−1H−1,2,3−triazol−4−yl)imidazo[2,1−b]thiazole<annotation encoding="application / x-tex">6-(4-Chlorophenyl)-5-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[2,1-b]thiazole< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 268 mg (90 %). 'H NMR (500 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.49 (s, 1H), 8.04 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.67 – 7.70 (m, 4H), 7.42-7.45 (m, 2H), 7.39 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.34 (ddm, <com:Math><semantics>J=2.1<annotation encoding="application / x-tex">J = 2.1< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=8.3<annotation encoding="application / x-tex">J = 8.3< / annotation>< / semantics>< / com:Math> Hz, 1H), 5.69 (bs, 2H). <com:Math><semantics>13<annotation encoding="application / x-tex">^{13}< / annotation>< / semantics>< / com:Math>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 149. 63, 142.82, 137.13, 136.99, 133.30, 132.39, 131.49, 131.24, 131.19, 130.42, 129.30, 128.73, 128.66, 123.62, 120.02, 114.52, 113.92, 51.85. HRMS: calcd for [M + H], 459.99518; found, 459.99522. EXAMPLE 65 <com:Math><semantics>5−(1−(3,4−Dimethoxybenzyl)−1H−1,2,3−triazol−4−yl)−6−phenylimidazo[2,1−b]thiazole<annotation encoding="application / x-tex">5-(1-(3,4-Dimethoxybenzyl)-1H-1,2,3-triazol-4-yl)-6-phenylimidazo[2,1-b]thiazole< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 120 mg (86 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.40 (s, 1H), 8.01 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.71−7.64<annotation encoding="application / x-tex">7.71 - 7.64< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.45−7.40<annotation encoding="application / x-tex">7.45 - 7.40< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.38<annotation encoding="application / x-tex">7.38< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.05 (d, <com:Math><semantics>J=2.0<annotation encoding="application / x-tex">J = 2.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 6.95 (d, <com:Math><semantics>J=8.2<annotation encoding="application / x-tex">J = 8.2< / annotation>< / semantics>< / com:Math> Hz, 1H), 6.90 (dd, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 2.0, 8.2 Hz, 1H), 5.56 (s, 2H), 3.74 (s, 6H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 149.80, 149.24, 142.95, 137.18, 133.60, 132.60, 129.53, 128.95, 128.45, 123.44, 121.13, 120.20, 114.75, 114.35, 112.48, 112.30, 56.00, 55.97, 53.45. HRMS: calcd for [M + H], 452.09425; found, 452.09438. 6-(4-Chlorophenyl)-5-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)imidazo[2,1-b]thiazole [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 121 mg (86 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.40 (s, 1H), 8.02 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.76 – 7.61 (m, 3H), <com:Math><semantics>7.45−7.41<annotation encoding="application / x-tex">7.45 - 7.41< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.38<annotation encoding="application / x-tex">7.38< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.33<annotation encoding="application / x-tex">7.33< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=8.7<annotation encoding="application / x-tex">J = 8.7< / annotation>< / semantics>< / com:Math> Hz, 2H), <com:Math><semantics>7.01−6.88<annotation encoding="application / x-tex">7.01 - 6.88< / annotation>< / semantics>< / com:Math> (m, 3H), 5.59 (s, 2H), 3.75 (s, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 159.63, 149.81, 142.96, 137.20, 133.60, 132.60, 130.06, 129.52, 128.97, 128.22, 123.42, 120.23, 114.60, 114.34, 55.62, 53.06. HRMS: calcd for [M + H], 422.08369; found, 422.08372. EXAMPLE 67 2-(4-Chlorophenyl)-3-(1-(3,4-dimethoxybenzyl)-1<com:Math><semantics>H<annotation encoding="application / x-tex">H< / annotation>< / semantics>< / com:Math>-1,2,3-triazol-4-yl)imidazo[1,2-<com:Math><semantics>a<annotation encoding="application / x-tex">a< / annotation>< / semantics>< / com:Math>]pyridine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-60 %). Yield 111 mg (81 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.47 – 8.42 (m, 2H), 7.71 – 7.66 (m, 3H), <com:Math><semantics>7.43−7.36<annotation encoding="application / x-tex">7.43 - 7.36< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.05<annotation encoding="application / x-tex">7.05< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=1.9<annotation encoding="application / x-tex">J = 1.9< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.03−6.95<annotation encoding="application / x-tex">7.03 - 6.95< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>6.91<annotation encoding="application / x-tex">6.91< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(dd,J=2.0,8.2 Hz,1H),5.62 (s, 2H),3.75 (d, J=3.8 Hz, 6H).<annotation encoding="application / x-tex">(dd, J = 2.0, 8.2 \text{ Hz}, 1\text{H}), 5.62 \text{ (s, 2H)}, 3.75 \text{ (d, } J = 3.8 \text{ Hz, 6H)}.< / annotation>< / semantics>< / com:Math> <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 149.27, 149.24, 145.12, 142.55, 136.41, 133.26, 133.11, 129.92, 128.94, 128.51, 126.60, 125.78, 125.63, 121.03, 117.34, 113.67, 112.40, 112.33, 112.05, 56.00, 55.97, 53.53. HRMS: calcd for [M + Na], 446.13783; found, 446.13786. EXAMPLE 68 <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(4−methoxybenzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 96 mg (75 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.50 – 8.35 (m, 2H), 7.71 – 7.66 (m, 3H), <com:Math><semantics>7.44−7.31<annotation encoding="application / x-tex">7.44 - 7.31< / annotation>< / semantics>< / com:Math> (m, 5H), <com:Math><semantics>7.02−6.93<annotation encoding="application / x-tex">7.02 - 6.93< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>5.63<annotation encoding="application / x-tex">5.63< / annotation>< / semantics>< / com:Math> (s, 2H), <com:Math><semantics>3.76<annotation encoding="application / x-tex">3.76< / annotation>< / semantics>< / com:Math> (s, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 159.64, 145.18, 142.68, 136.46, 133.33, 133.07, 129.96, 129.90, 128.95, 128.27, 126.51, 125.76, 125.62, 117.40, 114.64, 113.63, 112.01, 55.63, 53.16. HRMS: calcd for [M + H], 416.12726; found, 416.12730. EXAMPLE 69 [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 139 mg (78 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.50 (s, 1H), 8.45 (dt, <com:Math><semantics>J=1.1<annotation encoding="application / x-tex">J = 1.1< / annotation>< / semantics>< / com:Math>, 6.9 Hz, 1H), 7.69 (m, 3H), 7.44 – 7.37 (m, 8H), 7.00 (td, <com:Math><semantics>J=1.2<annotation encoding="application / x-tex">J = 1.2< / annotation>< / semantics>< / com:Math>, 6.8 Hz, 2H), 5.73 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 145.20, 142.73, 136.53, 136.40, 133.32, 133.09, 129.92, 129.29, 128.95, 128.65, 128.24, 126.54, 126.12, 125.63, 117.40, 113.65, 111.95, 53.57. HRMS: calcd for [M + H], 386.11670; found, 386.11681. EXAMPLE 70 2-(4-Chlorophenyl)-3-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 147 mg (83 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.58 (dt, <com:Math><semantics>J=4.7<annotation encoding="application / x-tex">J = 4.7< / annotation>< / semantics>< / com:Math>, 1.4 Hz, 1H), 8.52 (s, 1H), 8.47 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 7.85 (td, <com:Math><semantics>J=7.7<annotation encoding="application / x-tex">J = 7.7< / annotation>< / semantics>< / com:Math>, 1.8 Hz, 1H), 7.77 – 7.71 (m, 2H), 7.68 (dt, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 7.44 – 7.39 (m, 2H), 7.39 – 7.33 (m, 3H), 6.99 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 5.87 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 155.00, 149.65, 144.91, 142.41, 137.55, 136.14, 133.05, 132.80, 129.64, 128.63, 126.55, 126.16, 125.31, 123.45, 122.21, 117.10, 113.29, 111.70, 54.75. HRMS: calcd for [M + H], 387.11195; found, 387.11198. EXAMPLE 71 <com:Math><semantics>5−(1−Benzyl−1H−1,2,3−triazol−4−yl)−6−(4−chlorophenyl)imidazo[2,1−b]thiazole<annotation encoding="application / x-tex">5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-6-(4-chlorophenyl)imidazo[2,1-b]thiazole< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 154 mg (87 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.45 (s, 1H), 8.03 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.75−7.65<annotation encoding="application / x-tex">7.75 - 7.65< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.45−7.41<annotation encoding="application / x-tex">7.45 - 7.41< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>7.40−7.32<annotation encoding="application / x-tex">7.40 - 7.32< / annotation>< / semantics>< / com:Math> (m, 8H), 5.68 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 149.84, 143.02, 137.27, 136.33, 133.59, 132.62, 129.54, 129.25, 128.97, 128.64, 128.34, 123.75, 120.24, 114.75, 114.29, 53.49. HRMS: calcd for <com:Math><semantics>[M+Na]<annotation encoding="application / x-tex">[M + Na]< / annotation>< / semantics>< / com:Math>, 392.07312; found, 392.07318. EXAMPLE 72 <com:Math><semantics>6−(4−Chlorophenyl)−5−(1−(pyridin−2−ylmethyl)−1H−1,2,3−triazol−4−yl)imidazo[2,1−b]thiazole<annotation encoding="application / x-tex">6-(4-Chlorophenyl)-5-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)imidazo[2,1-b]thiazole< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 143 mg (80 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.57 (ddd, <com:Math><semantics>J=4.8,1.9,1.0<annotation encoding="application / x-tex">J = 4.8, 1.9, 1.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.46 (s, 1H), 8.05 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.85 (td, <com:Math><semantics>J=7.7<annotation encoding="application / x-tex">J = 7.7< / annotation>< / semantics>< / com:Math>, 1.8 Hz, 1H), <com:Math><semantics>7.77−7.69<annotation encoding="application / x-tex">7.77 - 7.69< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.47−7.42<annotation encoding="application / x-tex">7.47 - 7.42< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.41−7.35<annotation encoding="application / x-tex">7.41 - 7.35< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.33<annotation encoding="application / x-tex">7.33< / annotation>< / semantics>< / com:Math> (dd, <com:Math><semantics>J=7.8,1.1 Hz,1H),5.81 (s, 2H).<annotation encoding="application / x-tex">J = 7.8, 1.1 \text{ Hz}, 1\text{H}), 5.81 \text{ (s, 2H)}.< / annotation>< / semantics>< / com:Math> <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 154.95, 149.61, 149.53, 142.69, 137.55, 136.85, 133.31, 132.31, 129.26, 128.67, 124.16, 123.44, 122.24, 119.94, 114.47, 114.02, 54.64. HRMS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 393.06837; found, 393.06845. EXAMPLE 73 <com:Math><semantics>3−(1−(4−Chlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(4−chlorophenyl)imidazo[1,2−a]pyridine<annotation encoding="application / x-tex">3-(1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-50 %). Yield 145 mg (92 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.49 (s, 1H), 8.45 (dt, <com:Math><semantics>J=7.0<annotation encoding="application / x-tex">J = 7.0< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), <com:Math><semantics>7.71−7.66<annotation encoding="application / x-tex">7.71 - 7.66< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.51−7.47<annotation encoding="application / x-tex">7.51 - 7.47< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.45−7.36<annotation encoding="application / x-tex">7.45 - 7.36< / annotation>< / semantics>< / com:Math> (m, 5H), <com:Math><semantics>7.00<annotation encoding="application / x-tex">7.00< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=6.8,1.2 Hz,1H<annotation encoding="application / x-tex">J = 6.8, 1.2 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 5.73 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 149.57, 142.75, 137.05, 135.01, 133.28, 133.07, 132.35, 130.04, 129.25, 128.95, 128.69, 123.45, 119.96, 114.46, 113.94, 52.40. HRMS: calcd for [M + H], 420.07773; found, 420.07765. EXAMPLE 74 5-(1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)-6-(4-chlorophenyl)imidazo[2,1-b]thiazole [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme) 1). Mobile phase petrolether / EtOAc (20-60 %). Yield 136 mg (88 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.45 (s, 1H), 8.03 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.75 – 7.64 (m, 2H), <com:Math><semantics>7.49−7.41<annotation encoding="application / x-tex">7.49 - 7.41< / annotation>< / semantics>< / com:Math> (m, 4H), <com:Math><semantics>7.40−7.36<annotation encoding="application / x-tex">7.40 - 7.36< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>5.68<annotation encoding="application / x-tex">5.68< / annotation>< / semantics>< / com:Math> (s, 2H). <com:Sup>13< / com:Sup>C NMR (101) MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 149.57, 142.75, 137.05, 135.01, 133.28, 133.07, 132.35, 130.04, 129.25, 128.95, 128.69, 123.45, 119.96, 114.46, 113.94, 52.40. HRMS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 426.03415; found, 426.03423. EXAMPLE 75 6-Chloro-2-(4-chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2- b]pyridazine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase EtOAc / MeOH (0-10 %). Yield 190 mg (89 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.78 (s, 1H), 8.33 (d, <com:Math><semantics>J=9.5<annotation encoding="application / x-tex">J = 9.5< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.94−7.82<annotation encoding="application / x-tex">7.94 - 7.82< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.73−7.66<annotation encoding="application / x-tex">7.73 - 7.66< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.53−7.44<annotation encoding="application / x-tex">7.53 - 7.44< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.38<annotation encoding="application / x-tex">7.38< / annotation>< / semantics>< / com:Math> (dd, <com:Math><semantics>J=8.4,2.1 Hz,1H),5.82 (s, 2H).<annotation encoding="application / x-tex">J = 8.4, 2.1 \text{ Hz}, 1\text{H}), 5.82 \text{ (s, 2H)}.< / annotation>< / semantics>< / com:Math> <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 147.12, 143.30, 138.19, 137.36, 135.24, 133.71, 132.67, 131.84, 131.57, 131.52, 130.60, 130.31, 128.90, 128.84, 128.14, 126.57, 120.71, 117.02, 52.16. HRMS: calcd for [M + H], 488.99503; found, 488.99520. 39 EXAMPLE 76 6-Chloro-3-(1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-chlorophenyl)imidazo[1,2-b]pyridazine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-60 %). Yield 63 mg (87 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.74 (s, 1H), 8.33 (d, <com:Math><semantics>J=9.4<annotation encoding="application / x-tex">J = 9.4< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.93−7.82<annotation encoding="application / x-tex">7.93 - 7.82< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.52−7.46<annotation encoding="application / x-tex">7.52 - 7.46< / annotation>< / semantics>< / com:Math> (m, 6H), <com:Math><semantics>7.44−7.40<annotation encoding="application / x-tex">7.44 - 7.40< / annotation>< / semantics>< / com:Math> (m, 2H), 5.80 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 146.81, 142.97, 137.87, 135.09, 134.87, 133.40, 133.15, 132.40, 130.08, 130.02, 129.02, 128.55, 127.84, 126.10, 120.38, 116.80, 52.44. HRMS: calcd for [M + H], 455.03400; found, 455.03402. EXAMPLE 77 <com:Math><semantics>3−(1−Benzyl−1H−1,2,3−triazol−4−yl)−6−chloro−2−(4−chlorophenyl)imidazo[1,2−b]pyridazine<annotation encoding="application / x-tex">3-(1-Benzyl-1H-1,2,3-triazol-4-yl)-6-chloro-2-(4-chlorophenyl)imidazo[1,2-b]pyridazine< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-80 %). Yield 36 mg (62 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.73 (s, 1H), 8.33 (d, <com:Math><semantics>J=9.5<annotation encoding="application / x-tex">J = 9.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.89 (d, <com:Math><semantics>J=6.6<annotation encoding="application / x-tex">J = 6.6< / annotation>< / semantics>< / com:Math> Hz, 2H), <com:Math><semantics>7.51−7.33<annotation encoding="application / x-tex">7.51 - 7.33< / annotation>< / semantics>< / com:Math> (m, 8H), <com:Math><semantics>5.79<annotation encoding="application / x-tex">5.79< / annotation>< / semantics>< / com:Math> (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 146.79, 142.95, 137.85, 136.10, 134.81, 133.39, 132.41, 130.00, 129.01, 128.53, 128.42, 128.07, 127.83, 126.10, 120.36, 116.86, 53.23. HRMS: calcd for [M + H], 421.07298; found, 421.07299. EXAMPLE 78 <span class="math inline">$2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1\\H-1,2,3-triazol-4-yl)imidazo[1,2-b]pyridazine$ [Image disponible dans le document PDF, Image available in the PDF document] Example 56 (36 mg, 0.07 mmol) was dissolved in MeOH / THF mixture (2) ml, 1:1) and TEA (0.02 ml, 2 eq) was added. The mixture was cooled in an ice bath, degassed and Pd(OH)<com:Sub>2< / com:Sub> (5 mg, 10 mol %) was added. The reaction mixture was stirred under the hydrogen atmosphere (balloon) overnight at r.t. After the completion the mixture was filtrated over celite, evaporated and the residue purified by flash column chromatography. Mobile phase petrolether / EtOAc (50-100 %). Yield 29 mg (90 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.73 (s, 1H), 8.57 (dd, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 4.4, 1.6 Hz, 1H), 8.25 (dd, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 9.2, 1.6 Hz, 1H), 7.89 – 7.84 (m, 2H), 7.44 – 7.32 (m, 8H), 5.77 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 144.17, 143.52, 138.93, 136.19, 135.61, 133.91, 131.17, 129.01, 128.39, 128.36, 128.28, 128.06, 125.98, 125.58, 118.51, 115.93, 53.18. HRMS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 353.15092; found, 353.15104. EXAMPLE 79 <com:Math><semantics>4−((4−(2−(4−Chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−yl)methyl)benzonitrile<annotation encoding="application / x-tex">4-((4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzonitrile< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-80 %). Yield 148 mg (82 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.53 (s, 1H), 8.48 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), <com:Math><semantics>7.94−7.88<annotation encoding="application / x-tex">7.94 - 7.88< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.72−7.67<annotation encoding="application / x-tex">7.72 - 7.67< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.53−7.48<annotation encoding="application / x-tex">7.53 - 7.48< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.47−<annotation encoding="application / x-tex">7.47 -< / annotation>< / semantics>< / com:Math> 7.42 (m, 2H), 7.39 (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.7, 1.3 Hz, 1H), 7.01 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 5.85 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 145.23, 142.82, 141.84, 136.69, 133.31, 133.27, 133.14, 129.94, 129.06, 129.00, 126.57, 126.42, 125.70, 119.02, 117.41, 113.65, 111.82, 111.44, 52.96. HRMS: calcd for [M + H], 411.11195; found, 411.11215. EXAMPLE 80 <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(2,4−dichlorophenyl)imidazo[1,2−a]pyridine<annotation encoding="application / x-tex">3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(2,4-dichlorophenyl)imidazo[1,2-a]pyridine< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-80 %). Yield 120 mg <com:Math><semantics>(74%)<annotation encoding="application / x-tex">(74\%)< / annotation>< / semantics>< / com:Math>. H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 9.11 (dt, <com:Math><semantics>J=7.0<annotation encoding="application / x-tex">J = 7.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 8.02 (s, 1H), 7.71 (dt, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 7.68 (d, <com:Math><semantics>J=2.1<annotation encoding="application / x-tex">J = 2.1< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.64 <com:Math><semantics>(d,J=8.3 Hz,1H),7.58(d,J=8.3 Hz,1H),7.54(d,J=2.1 Hz,1H),<annotation encoding="application / x-tex">(d, J = 8.3 \text{ Hz}, 1\text{H}), 7.58 (d, J = 8.3 \text{ Hz}, 1\text{H}), 7.54 (d, J = 2.1 \text{ Hz}, 1\text{H}),< / annotation>< / semantics>< / com:Math> 7.52 (dd, <com:Math><semantics>J=8.3,2.1 Hz,1H<annotation encoding="application / x-tex">J = 8.3, 2.1 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 7.42 (ddd, <com:Math><semantics>J=9.1,6.7,1.3 Hz,1H<annotation encoding="application / x-tex">J = 9.1, 6.7, 1.3 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 7.25 (dd, <com:Math><semantics>J=8.3,2.1 Hz,1H<annotation encoding="application / x-tex">J = 8.3, 2.1 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 7.11 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 5.67 (s, 2H). C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 144.69, 140.47, 137.27, 137.05, 134.19, 133.95, 133.64, 132.58, 131.46, 131.09, 130.00, 129.45, 128.30, 127.75, 126.19, 126.02, 123.26, 117.31, 113.72, 113.61, 51.61. HRMS: calcd for [M + H], 417.06837; found, 417.06839. <com:Math><semantics>5−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−6−(3,4−dichlorophenyl)imidazo[2,1−b]thiazole<annotation encoding="application / x-tex">5-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-6-(3,4-dichlorophenyl)imidazo[2,1-b]thiazole< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-60 %). Yield 51 mg (92 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.57 (s, 1H), 8.01 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.87 (d, <com:Math><semantics>J=2.0<annotation encoding="application / x-tex">J = 2.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.71 (d, <com:Math><semantics>J=2.1<annotation encoding="application / x-tex">J = 2.1< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.69 – 7.64 (m, 2H), 7.61 (d, <com:Math><semantics>J=8.4<annotation encoding="application / x-tex">J = 8.4< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.40 <com:Math><semantics>(d,J=4.5 Hz,1H),7.36(dd,J=8.3,2.1 Hz,1H),5.70(s,2H).<annotation encoding="application / x-tex">(d, J = 4.5 \text{ Hz}, 1\text{H}), 7.36 (dd, J = 8.3, 2.1 \text{ Hz}, 1\text{H}), 5.70 (s, 2\text{H}).< / annotation>< / semantics>< / com:Math> <com:Sup>13< / com:Sup>C NMR (101) MHz, DMSO) δ 149.77, 141.34, 136.86, 136.81, 135.00, 131.52, 131.39, 131.24, 131.21, 130.87, 130.44, 130.14, 128.90, 128.65, 127.44, 123.91, 119.85, 114.89, 114.40, 51.92. HRMS: calcd for [M + H], 493.95620; found, 493.95625. EXAMPLE 82 <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(p−tolyl)imidazo[1,2−a]<annotation encoding="application / x-tex">3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-2-(p-\text{tolyl})\text{imidazo}[1,2-a]< / annotation>< / semantics>< / com:Math>pyridine 41 [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme) 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 140 mg (84 %). H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.47 (dd, <com:Math><semantics>J=7.1<annotation encoding="application / x-tex">J = 7.1< / annotation>< / semantics>< / com:Math>, 1.5 Hz, 1H), 8.45 (d, <com:Math><semantics>J=1.5<annotation encoding="application / x-tex">J = 1.5< / annotation>< / semantics>< / com:Math> Hz, 0H), <com:Math><semantics>7.72−7.65<annotation encoding="application / x-tex">7.72 - 7.65< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>7.56−7.51<annotation encoding="application / x-tex">7.56 - 7.51< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>7.39−7.33<annotation encoding="application / x-tex">7.39 - 7.33< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>7.16<annotation encoding="application / x-tex">7.16< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=7.8<annotation encoding="application / x-tex">J = 7.8< / annotation>< / semantics>< / com:Math> Hz, 1H), 6.97 (td, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.7 Hz, 0H), 5.74 (s, 1H), 2.32 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 144.82, 143.87, 137.48, 137.11, 136.79, 131.51, 131.27, 131.23, 131.16, 130.25, 129.17, 128.54, 125.88, 125.74, 125.30, 116.96, 113.06, 110.91, 51.86, 21.01. HRMS: calcd for [M + H], 434.09338; found, 434.09355. EXAMPLE 83 <com:Math><semantics>4−((4−(6−(4−Chlorophenyl)imidazo[2,1−b]thiazol−5−yl)−1H−1,2,3−triazol−1−yl)methyl)−benzonitrile<annotation encoding="application / x-tex">4-((4-(6-(4-Chlorophenyl)imidazo[2,1-b]thiazol-5-yl)-1H-1,2,3-triazol-1-yl)methyl)-benzonitrile< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme) 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 87 mg (87 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.49 (s, 1H), 8.05 (d, <com:Math><semantics>J=4.5<annotation encoding="application / x-tex">J = 4.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.92 – 7.79 (m, 2H), <com:Math><semantics>7.73−7.66<annotation encoding="application / x-tex">7.73 - 7.66< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.52−7.47<annotation encoding="application / x-tex">7.52 - 7.47< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.47−7.42<annotation encoding="application / x-tex">7.47 - 7.42< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.39<annotation encoding="application / x-tex">7.39< / annotation>< / semantics>< / com:Math> (d, J) = 4.5 Hz, 1H), 5.80 (s, 2H). <com:Math><semantics>13<annotation encoding="application / x-tex">^{13}< / annotation>< / semantics>< / com:Math>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 149.61, 142.82, 141.48, 137.13, 133.27, 132.93, 132.37, 129.28, 128.83, 128.72, 123.76, 120.00, 118.72, 114.49, 113.87, 111.11, 52.56. HRMS: calcd for [M + H], 487.99978; found, 487.99993. EXAMPLE 84 <com:Math><semantics>4−(3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridin−2−yl)benzonitrile<annotation encoding="application / x-tex">4-(3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridin-2-yl)benzonitrile< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-80 %). Yield 189 mg (89 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.59 (s, 1H), 8.44 (dt, <com:Math><semantics>J=7.0<annotation encoding="application / x-tex">J = 7.0< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), <com:Math><semantics>7.89−7.81<annotation encoding="application / x-tex">7.89 - 7.81< / annotation>< / semantics>< / com:Math> (m, 4H), <com:Math><semantics>7.75−7.69<annotation encoding="application / x-tex">7.75 - 7.69< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.42<annotation encoding="application / x-tex">7.42< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.7, 1.3 Hz, 1H), 7.36 (dd, <com:Math><semantics>J=8.3<annotation encoding="application / x-tex">J = 8.3< / annotation>< / semantics>< / com:Math>, 2.1 Hz, 1H), 7.03 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 5.75 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 178.80, 132.59, 131.51, 131.28, 131.21, 130.39, 128.58, 128.51, 126.70, 126.27, 125.49, 117.31, 113.66, 52.00. HRMS: calcd for [M + H], 445.07298; found, 445.07299. EXAMPLE 85 <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(4−methoxyphenyl)imidazo[1,2−a]pyridine<annotation encoding="application / x-tex">3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyridine< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-80 %). Yield 385 mg (92 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.46 (d, <com:Math><semantics>J=6.5<annotation encoding="application / x-tex">J = 6.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.72 <com:Math><semantics>−7.64<annotation encoding="application / x-tex">-7.64< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>7.63−7.57<annotation encoding="application / x-tex">7.63 - 7.57< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>7.38−7.32<annotation encoding="application / x-tex">7.38 - 7.32< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>6.96<annotation encoding="application / x-tex">6.96< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 6.8, 1.2 Hz, 0H), 6.95 – 6.90 (m, 1H), 5.74 (s, 1H), 3.78 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 159.28, 144.78, 143.76, 137.11, 136.88, 131.49, 131.23, 131.14, 130.23, 129.21, 128.52, 126.50, 125.77, 125.70, 125.23, 116.84, 114.00, 112.96, 110.44, 55.28, 51.88. HRMS: calcd for [M + H], 450.08829; found, 450.08826. EXAMPLE 86 <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(4−(trifluoromethyl)phenyl)imidazo[1,2−1,2,3−triazol−4−yl)−2−(4−(trifluoromethyl)phenyl)imidazo[1,2−1,3−triazol−4−yl)−2−(4−(trifluoromethyl)phenyl)imidazo[1,2−1,3−triazo<annotation encoding="application / x-tex">3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-1,2,3-triazol-4-yl)-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-1,3-triazol-4-yl)-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-1,3-triazo< / annotation>< / semantics>< / com:Math> a]pyridine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-80 %). Yield 143 mg (86 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.52 (dt, <com:Math><semantics>J=7.0<annotation encoding="application / x-tex">J = 7.0< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 8.38 (s, 1H), <com:Math><semantics>8.04−7.96<annotation encoding="application / x-tex">8.04 - 7.96< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.57<annotation encoding="application / x-tex">7.57< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.31−7.21<annotation encoding="application / x-tex">7.31 - 7.21< / annotation>< / semantics>< / com:Math> (m, 3H), 6.89 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.3 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 162.01 (d, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> <com:Math><semantics>=244.2 Hz<annotation encoding="application / x-tex">= 244.2 \text{ Hz}< / annotation>< / semantics>< / com:Math>), <com:Math><semantics>145.01<annotation encoding="application / x-tex">145.01< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>143.63<annotation encoding="application / x-tex">143.63< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>130.65<annotation encoding="application / x-tex">130.65< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>127.68<annotation encoding="application / x-tex">127.68< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=8.2 Hz<annotation encoding="application / x-tex">J = 8.2 \text{ Hz}< / annotation>< / semantics>< / com:Math>), <com:Math><semantics>127.09<annotation encoding="application / x-tex">127.09< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>125.23<annotation encoding="application / x-tex">125.23< / annotation>< / semantics>< / com:Math>, 116.78, 115.77 (d, <com:Math><semantics>J=21.5 Hz<annotation encoding="application / x-tex">J = 21.5 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 112.51, 109.12. HRMS: calcd for [M + H], 488.06511; found, 488.06511. EXAMPLE 87 <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(4−fluorophenyl)imidazo[1,2−a]pyridine<annotation encoding="application / x-tex">3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-fluorophenyl)imidazo[1,2-a]pyridine< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-80 %). Yield 211 mg (74 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.50 (s, 1H), 8.48 (dt, <com:Math><semantics>J=7.0<annotation encoding="application / x-tex">J = 7.0< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), <com:Math><semantics>7.75−7.65<annotation encoding="application / x-tex">7.75 - 7.65< / annotation>< / semantics>< / com:Math> (m, 6H), <com:Math><semantics>7.41−7.32<annotation encoding="application / x-tex">7.41 - 7.32< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.24−7.15<annotation encoding="application / x-tex">7.24 - 7.15< / annotation>< / semantics>< / com:Math> (m, 2H), 6.99 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 5.74 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 162.40 (d, <com:Math><semantics>J=245.1 Hz<annotation encoding="application / x-tex">J = 245.1 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 145.14, 143.14, 137.30, 136.80, 131.80, 131.53, 131.47, 130.91 (d, <com:Math><semantics>J=3.1 Hz<annotation encoding="application / x-tex">J = 3.1 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 130.62, 130.31 (d, <com:Math><semantics>J=8.3 Hz<annotation encoding="application / x-tex">J = 8.3 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 128.81, 126.41, 126.10, 125.68, 117.33, 115.82 (d, <com:Math><semantics>J=21.5<annotation encoding="application / x-tex">J = 21.5< / annotation>< / semantics>< / com:Math> Hz), 113.53, 111.49, 52.21. HRMS: calcd for [M + H], 438.06831; found, 438.06851. EXAMPLE 88 <com:Math><semantics>3−(1−(3,4−Dichlorobenzyl)−1H−1,2,3−triazol−4−yl)−2−(4−ethylphenyl)imidazo[1,2−a]pyridine<annotation encoding="application / x-tex">3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-ethylphenyl)imidazo[1,2-a]pyridine< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (20-70 %). Yield 350 mg (70 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.48 – 8.43 (m, 2H), 7.72 – <com:Math><semantics>7.65<annotation encoding="application / x-tex">7.65< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.59−7.54<annotation encoding="application / x-tex">7.59 - 7.54< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.38−7.33<annotation encoding="application / x-tex">7.38 - 7.33< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.20−7.15<annotation encoding="application / x-tex">7.20 - 7.15< / annotation>< / semantics>< / com:Math> (m, 2H), 6.97 (td, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 5.74 (s, 2H), 2.61 (q, <com:Math><semantics>J=7.6<annotation encoding="application / x-tex">J = 7.6< / annotation>< / semantics>< / com:Math> Hz, 2H), 1.19 (t, <com:Math><semantics>J=7.6<annotation encoding="application / x-tex">J = 7.6< / annotation>< / semantics>< / com:Math> Hz, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 144.85, 143.88, 143.75, 137.12, 136.79, 131.52, 131.24, 131.19, 130.26, 128.56, 127.95, 127.90, 125.90, 125.86, 125.28, 116.98, 113.09, 110.92, 51.91, 28.10, 15.55. HRMS: calcd for [M + H], 448.10903; found, 448.10914. EXAMPLE 89 Methyl 2-chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)- methyl)benzoate [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (60-90 %). Yield 456 mg (84 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.54 (s, 1H), 8.46 (dt, <com:Math><semantics>J=7.0,1.1 Hz,1H,7.84−7.81 (m, 1H),7.72−7.67 (m, 3H),7.65<annotation encoding="application / x-tex">J = 7.0, 1.1 \text{ Hz}, 1\text{H}, 7.84 - 7.81 \text{ (m, 1H)}, 7.72 - 7.67 \text{ (m, 3H)}, 7.65< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(d,J=8.3 Hz,1H),7.56(dd,J=8.3,2.3 Hz,1H),7.44−7.40(m,J=8.3,2.3 Hz,1H)<annotation encoding="application / x-tex">(d, J = 8.3 \text{ Hz}, 1\text{H}), 7.56 (dd, J = 8.3, 2.3 \text{ Hz}, 1\text{H}), 7.44 - 7.40 (m, J = 8.3, 2.3 \text{ Hz}, 1\text{H})< / annotation>< / semantics>< / com:Math> 2H), <com:Math><semantics>7.40−7.36<annotation encoding="application / x-tex">7.40 - 7.36< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>7.00<annotation encoding="application / x-tex">7.00< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>1.2<annotation encoding="application / x-tex">1.2< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>5.79<annotation encoding="application / x-tex">5.79< / annotation>< / semantics>< / com:Math> (s, 2H), 3.87 (s, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 165.39, 144.95, 142.46, 136.39, 135.56, 133.01, 132.84, 132.82, 131.82, 131.52, 130.65, 130.46, 129.62, 128.68, 126.29, 125.94, 125.39, 117.12, 113.37, 111.55, 52.89, 52.07. HRMS: calcd for [M + H], 478.08328; found, 478.08321. EXAMPLE 90 <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(3,4−dichlorophenyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-100 %). Yield 225 mg (73 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 9.31 (s, 1H), 8.49 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 2H), 8.37 (d, <com:Math><semantics>J=2.5<annotation encoding="application / x-tex">J = 2.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 8.07 (dd, <com:Math><semantics>J=8.8<annotation encoding="application / x-tex">J = 8.8< / annotation>< / semantics>< / com:Math>, 2.5 Hz, 1H), 7.95 (d, <com:Math><semantics>J=8.8<annotation encoding="application / x-tex">J = 8.8< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.85−7.78<annotation encoding="application / x-tex">7.85 - 7.78< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.73<annotation encoding="application / x-tex">7.73< / annotation>< / semantics>< / com:Math> (dt, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.0 Hz, 2H), <com:Math><semantics>7.48−7.44<annotation encoding="application / x-tex">7.48 - 7.44< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.44−7.39<annotation encoding="application / x-tex">7.44 - 7.39< / annotation>< / semantics>< / com:Math> (m, 1H), <com:Math><semantics>7.02<annotation encoding="application / x-tex">7.02< / annotation>< / semantics>< / com:Math> (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>1.2<annotation encoding="application / x-tex">1.2< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 145.10, 142.84, 136.98, 136.19, 132.88, 132.84, 132.55, 132.06, 131.49, 129.65, 128.73, 126.53, 125.45, 124.34, 122.30, 120.57, 117.14, 113.39, 110.89. HRMS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 440.02311; found, 440.02321. EXAMPLE 91 <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(3,4−dichlorophenethyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(3,4-dichlorophenethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-100 %). Yield 138 mg (95 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.33 (s, 0H), 8.25 (d, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 6.9 Hz, 1H), 7.69 (d, <com:Math><semantics>J=9.0<annotation encoding="application / x-tex">J = 9.0< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.64 (d, <com:Math><semantics>J=8.5<annotation encoding="application / x-tex">J = 8.5< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.58 – 7.49 (m, 1H), 7.39 (d, <com:Math><semantics>J=8.5<annotation encoding="application / x-tex">J = 8.5< / annotation>< / semantics>< / com:Math> Hz, 2H), 7.21 – 7.13 (m, 1H), 6.99 (t, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 6.6 Hz, 1H), 4.78 (t, <com:Math><semantics>J=6.7<annotation encoding="application / x-tex">J = 6.7< / annotation>< / semantics>< / com:Math> Hz, 1H), 3.26 (t, <com:Math><semantics>J=6.7<annotation encoding="application / x-tex">J = 6.7< / annotation>< / semantics>< / com:Math> Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 144.84, 142.21, 139.06, 135.60, 132.98, 132.77, 131.08, 131.05, 130.64, 129.49, 129.46, 129.40, 128.61, 126.20, 125.77, 125.00, 117.13, 113.27, 111.64, 50.51, 34.70. HRMS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 468.05441; found, 468.05450. EXAMPLE 92 2-Chloro-5-((4-(2-(4-chlorophenyl)-8-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-100 %). Yield 105 mg (89 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.59 (s, 1H), 8.35 (dd, <com:Math><semantics>J=6.9,0.9 Hz,1H<annotation encoding="application / x-tex">J = 6.9, 0.9 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 7.93 (s, 1H), 7.74 – 7.69 (m, 2H), 7.69 – 7.67 (m, 1H), 7.54 (d, <com:Math><semantics>J=8.2<annotation encoding="application / x-tex">J = 8.2< / annotation>< / semantics>< / com:Math> Hz, 1H), 7.49 – 7.45 (m, 3H), 7.43 (dd, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 8.2, 2.3 Hz, 1H), 7.31 (ddd, <com:Math><semantics>J=11.0,7.7,0.9<annotation encoding="application / x-tex">J = 11.0, 7.7, 0.9< / annotation>< / semantics>< / com:Math> Hz, 1H), 6.98 (ddd, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 7.7, 6.9, 4.8 Hz, 1H), 5.76 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 168.25, 150.90 (d, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 249.7 Hz), 142.85, 137.98, 137.64 (d, <com:Math><semantics>J=28.8 Hz<annotation encoding="application / x-tex">J = 28.8 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 136.22 (d, <com:Math><semantics>J=1.3 Hz<annotation encoding="application / x-tex">J = 1.3 \text{ Hz}< / annotation>< / semantics>< / com:Math>), 135.31, 133.50, 132.72, 131.94 (d, <com:Math><semantics>J=1.3 Hz<annotation encoding="application / x-tex">J = 1.3 \text{ Hz}< / annotation>< / semantics>< / com:Math>) 9.8 Hz), 130.53, 129.99, 129.94, 129.12, 128.62, 126.38, 122.50 (d, <com:Math><semantics>J=4.9<annotation encoding="application / x-tex">J = 4.9< / annotation>< / semantics>< / com:Math> Hz), 113.70, 112.83 (d, <com:Math><semantics>J=4.9<annotation encoding="application / x-tex">J = 4.9< / annotation>< / semantics>< / com:Math> Hz) 6.9 Hz), 109.32 (d, <com:Math><semantics>J=15.9<annotation encoding="application / x-tex">J = 15.9< / annotation>< / semantics>< / com:Math> Hz), 52.54. HRMS: calcd for [M + H], 481.07412; found, 481.07324. EXAMPLE 93 2-Chloro-5-((4-(2-(4-chlorophenyl)-7-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-100 %). Yield 75 mg (83 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.58 – 8.51 (m, 2H), 7.92 (s, 1H), <com:Math><semantics>7.72−7.65<annotation encoding="application / x-tex">7.72 - 7.65< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.58<annotation encoding="application / x-tex">7.58< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 9.9, 2.7, 0.8 Hz, 1H), 7.53 (s, 1H), 7.49 – 7.38 (m, 4H), 7.05 (td, <com:Math><semantics>J=7.6,2.7 Hz,1H<annotation encoding="application / x-tex">J = 7.6, 2.7 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 5.75 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO- <com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 167.96, 160.47 (d, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 249.8 Hz), 145.15 (d, <com:Math><semantics>J<annotation encoding="application / x-tex">J< / annotation>< / semantics>< / com:Math> = 14.2 Hz), 143.16, 137.68, 136.07, 135.04, 133.02, 132.72, 131.66 (d, <com:Math><semantics>J=9.6<annotation encoding="application / x-tex">J = 9.6< / annotation>< / semantics>< / com:Math> Hz), 130.24, 129.63, 129.53, 128.80, 128.32, 127.69 (d, <com:Math><semantics>J=11.2<annotation encoding="application / x-tex">J = 11.2< / annotation>< / semantics>< / com:Math> Hz), 125.88, 111.61 (d, <com:Math><semantics>J=1.5<annotation encoding="application / x-tex">J = 1.5< / annotation>< / semantics>< / com:Math> Hz), 105.38 (d, <com:Math><semantics>J=29.4<annotation encoding="application / x-tex">J = 29.4< / annotation>< / semantics>< / com:Math> Hz), 100.73 (d, <com:Math><semantics>J=23.7<annotation encoding="application / x-tex">J = 23.7< / annotation>< / semantics>< / com:Math> Hz), 52.23. HRMS: calcd for [M + H], 481.07412; found, 481.07370. EXAMPLE 94 2-Chloro-5-((4-(2-(4-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (30-100 %). Yield 63 mg (84 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.65 (dd, <com:Math><semantics>J=4.8,2.4 Hz,1H<annotation encoding="application / x-tex">J = 4.8, 2.4 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 8.57 (s, 1H), 7.92 (s, 1H), 7.78 (dd, <com:Math><semantics>J=9.8<annotation encoding="application / x-tex">J = 9.8< / annotation>< / semantics>< / com:Math>, 5.2 Hz, 1H), 7.69 (dd, <com:Math><semantics>J=7.9<annotation encoding="application / x-tex">J = 7.9< / annotation>< / semantics>< / com:Math>, 5.8 Hz, 3H), 7.54 (d, <com:Math><semantics>J=8.2<annotation encoding="application / x-tex">J = 8.2< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.49−7.43<annotation encoding="application / x-tex">7.49 - 7.43< / annotation>< / semantics>< / com:Math> (m, 4H), <com:Math><semantics>5.75<annotation encoding="application / x-tex">5.75< / annotation>< / semantics>< / com:Math> (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 167.98, 153.23 (d, <com:Math><semantics>J=234.3<annotation encoding="application / x-tex">J = 234.3< / annotation>< / semantics>< / com:Math> Hz), 143.62 (d, <com:Math><semantics>J=2.2<annotation encoding="application / x-tex">J = 2.2< / annotation>< / semantics>< / com:Math> Hz), 142.77, 137.67, 135.98, 135.01, 133.06, 132.77, 131.66 (d, <com:Math><semantics>J=9.8<annotation encoding="application / x-tex">J = 9.8< / annotation>< / semantics>< / com:Math> Hz), 130.27 (d, <com:Math><semantics>J=8.0<annotation encoding="application / x-tex">J = 8.0< / annotation>< / semantics>< / com:Math> Hz), 129.63, 128.80, 128.38, 125.79, 118.09 <com:Math><semantics>(d,J=3.6 Hz),117.92(d,J=12.9 Hz),113.25(d,J=2.0 Hz),112.30(d,J=42.5 Hz),52.25HRMS:<annotation encoding="application / x-tex">(d, J = 3.6 \text{ Hz}), 117.92 (d, J = 12.9 \text{ Hz}), 113.25 (d, J = 2.0 \text{ Hz}), 112.30 (d, J = 42.5 \text{ Hz}), 52.25 HRMS:< / annotation>< / semantics>< / com:Math> calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 481.07412; found, 481.07346. EXAMPLE 95 2-Chloro-5-((4-(2-(4-chlorophenyl)-6,8-difluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)-benzamide [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-100 %). Yield 79 mg (88 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.60 (s, 1H), 8.59 (s, 1H), 7.91 (s, 1H), <com:Math><semantics>7.74−7.65<annotation encoding="application / x-tex">7.74 - 7.65< / annotation>< / semantics>< / com:Math> (m, 4H), <com:Math><semantics>7.54<annotation encoding="application / x-tex">7.54< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 8.2 Hz, 1H), <com:Math><semantics>7.51−7.40<annotation encoding="application / x-tex">7.51 - 7.40< / annotation>< / semantics>< / com:Math> (m, 4H), <com:Math><semantics>5.75<annotation encoding="application / x-tex">5.75< / annotation>< / semantics>< / com:Math> (s, 2H). <com:Sup>13< / com:Sup>C NMR (101) MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 167.95, 151.91 (dd, J = 234.7 Hz, J = 11.2 Hz), 149.90 (dd, <com:Math><semantics>J=253.3<annotation encoding="application / x-tex">J = 253.3< / annotation>< / semantics>< / com:Math> Hz, <com:Math><semantics>J=14.6<annotation encoding="application / x-tex">J = 14.6< / annotation>< / semantics>< / com:Math> Hz), 143.36 (d, <com:Math><semantics>J=2.0<annotation encoding="application / x-tex">J = 2.0< / annotation>< / semantics>< / com:Math> Hz), 137.67, 135.47, 135.16, 134.93, 133.35, 132.22, 130.32, 130.21, 129.68, 128.87, 128.39, 126.11, <com:Math><semantics>115.20−114.94<annotation encoding="application / x-tex">115.20 - 114.94< / annotation>< / semantics>< / com:Math> (m), <com:Math><semantics>109.62<annotation encoding="application / x-tex">109.62< / annotation>< / semantics>< / com:Math> (dd, <com:Math><semantics>J=114.94<annotation encoding="application / x-tex">J = 114.94< / annotation>< / semantics>< / com:Math> (m), 109.62 (dd, <com:Math><semantics>J=114.94<annotation encoding="application / x-tex">J = 114.94< / annotation>< / semantics>< / com:Math> (m), 109.62 (dd, <com:Math><semantics>J=114.94<annotation encoding="application / x-tex">J = 114.94< / annotation>< / semantics>< / com:Math> (m), 109.62 (dd, <com:Math><semantics>J=114.94<annotation encoding="application / x-tex">J = 114.94< / annotation>< / semantics>< / com:Math> (m), 109.62 (dd, 43.0, 6.1 Hz), 103.01 (dd, <com:Math><semantics>J=30.1<annotation encoding="application / x-tex">J = 30.1< / annotation>< / semantics>< / com:Math>, 20.3 Hz), 52.27. HRMS: calcd for [M + H], 499.06470; found, 499.06396. EXAMPLE 96 2-Chloro-5-((4-(2-(4-cyclopropylphenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-100 %). Yield 200 mg (92 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.50 (s, 1H), 8.47 (dt, <com:Math><semantics>J=7.0,1.2 Hz,1H<annotation encoding="application / x-tex">J = 7.0, 1.2 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), <com:Math><semantics>8.01−7.92 (m, 1H)<annotation encoding="application / x-tex">8.01 - 7.92 \text{ (m, 1H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>7.71 (s, 1H)<annotation encoding="application / x-tex">7.71 \text{ (s, 1H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>7.67 (dt, J=1.00 (s, 1H)<annotation encoding="application / x-tex">7.67 \text{ (dt, } J = 1.00 \text{ (s, 1H)}< / annotation>< / semantics>< / com:Math>) 9.1, 1.2 Hz, 1H), <com:Math><semantics>7.60−7.52<annotation encoding="application / x-tex">7.60 - 7.52< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.48<annotation encoding="application / x-tex">7.48< / annotation>< / semantics>< / com:Math> (d, <com:Math><semantics>J=2.2<annotation encoding="application / x-tex">J = 2.2< / annotation>< / semantics>< / com:Math> Hz, 1H), <com:Math><semantics>7.43<annotation encoding="application / x-tex">7.43< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(dd,J=8.3,2.3 Hz,1H),7.35(ddd,J=9.1,6.7,1.3 Hz,1H),7.10−<annotation encoding="application / x-tex">(dd, J = 8.3, 2.3 \text{ Hz}, 1\text{H}), 7.35 (ddd, J = 9.1, 6.7, 1.3 \text{ Hz}, 1\text{H}), 7.10 -< / annotation>< / semantics>< / com:Math> 7.05 (m, 2H), 6.97 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.3 Hz, 1H), 5.76 (s, 2H), 1.93 (tt, <com:Math><semantics>J=8.4<annotation encoding="application / x-tex">J = 8.4< / annotation>< / semantics>< / com:Math>, 5.1 Hz, 1H), 1.01 – 0.87 (m, 2H), <com:Math><semantics>0.74−0.66<annotation encoding="application / x-tex">0.74 - 0.66< / annotation>< / semantics>< / com:Math> (m, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 168.00, 144.86, 143.97, 143.81, 137.72, 136.79, 135.17, 131.08, 130.24, 130.19, 129.66, 128.27, 127.82, 125.84, 125.75, 125.53, 125.24, 116.96, 113.04, 110.88, 52.20, 15.18, 9.84. HRMS: calcd for [M + H], 469.15381; found, 469.15344. EXAMPLE 97 2-(4-Chlorophenyl)-3-(1-(4-(methylthio)benzyl)-1<com:Math><semantics>H<annotation encoding="application / x-tex">H< / annotation>< / semantics>< / com:Math>-1,2,3-triazol-4-yl)imidazo[1,2-<com:Math><semantics>a<annotation encoding="application / x-tex">a< / annotation>< / semantics>< / com:Math>]pyridine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-100 %). Yield 72 mg <com:Math><semantics>(80%)<annotation encoding="application / x-tex">(80\%)< / annotation>< / semantics>< / com:Math>. <com:Sup>1< / com:Sup>H NMR <com:Math><semantics>(401 MHz,DMSO-d6)δ8.46 (s, 1H),8.44 (dt, J=6.9,<annotation encoding="application / x-tex">(401 \text{ MHz}, \text{DMSO-}d_6) \delta 8.46 \text{ (s, 1H)}, 8.44 \text{ (dt, } J = 6.9,< / annotation>< / semantics>< / com:Math> <com:Math><semantics>1.2 Hz<annotation encoding="application / x-tex">1.2 \text{ Hz}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>1H<annotation encoding="application / x-tex">1\text{H}< / annotation>< / semantics>< / com:Math>), <com:Math><semantics>7.72−7.65 (m, 3H)<annotation encoding="application / x-tex">7.72 - 7.65 \text{ (m, 3H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>7.44−7.35 (m, 3H)<annotation encoding="application / x-tex">7.44 - 7.35 \text{ (m, 3H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>7.33−7.27 (m, 3H)<annotation encoding="application / x-tex">7.33 - 7.27 \text{ (m, 3H)}< / annotation>< / semantics>< / com:Math> 3H), 6.99 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 5.67 (s, 2H), 2.47 (s, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 144.91, 142.43, 138.60, 136.24, 133.02, 132.81, 132.52, 129.62, 128.76, 128.67, 126.28, 126.24, 125.67, 125.34, 117.10, 113.35, 111.67, 52.88. HRMS: calcd for [M + H], 431.09715; found, 431.09723. EXAMPLE 98 <com:Math><semantics>2−(4−Chlorophenyl)−3−(1−(4−(methylsulfonyl)benzyl)−1H−1,2,3−triazol−4−yl)imidazo[1,2−a]pyridine<annotation encoding="application / x-tex">2-(4-Chlorophenyl)-3-(1-(4-(methylsulfonyl)benzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-100 %). Yield 613 mg (92 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.52 (dt, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 8.07 (s, 1H), 7.98 (m, 2H), 7.72 (dt, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 7.69 (m, 2H), 7.60 (m, 2H), 7.45 (m, 2H), 7.42 (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.8, 1.1 Hz, 1H), 7.04 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.1 Hz, 1H), 5.97 (s, 2H), 3.23 (s, 3H). <com:Math><semantics>13<annotation encoding="application / x-tex">^{13}< / annotation>< / semantics>< / com:Math>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 145.13, 143.06, 141.54, 140.72, 137.61, 135.29, 133.03, 132.90, 129.83, 128.91, 128.72, 127.68, 126.50, 125.39, 117.20, 113.61, 111.13, 57.56, 43.65. HRMS: calcd for [M - H], 462.07970; found, 462.07935. EXAMPLE 99 2-(4-Chlorophenyl)-3-(1-(4-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2- a]pyridine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-100 %). Yield 144 mg (93 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.49 (d, <com:Math><semantics>J=6.6 Hz,1H,8.03 (s, 1H),7.85 (m, 2H),7.67−7.73 (m, 3H),<annotation encoding="application / x-tex">J = 6.6 \text{ Hz}, 1\text{H}, 8.03 \text{ (s, 1H)}, 7.85 \text{ (m, 2H)}, 7.67-7.73 \text{ (m, 3H)},< / annotation>< / semantics>< / com:Math> <com:Math><semantics>7.57 (m, 2H)<annotation encoding="application / x-tex">7.57 \text{ (m, 2H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>7.43 (m, 2H)<annotation encoding="application / x-tex">7.43 \text{ (m, 2H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>7.40 (m, 1H)<annotation encoding="application / x-tex">7.40 \text{ (m, 1H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>7.02 (t, J=6.6 Hz, 1H)<annotation encoding="application / x-tex">7.02 \text{ (t, J} = 6.6 \text{ Hz, 1H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>5.94 (s, 2H)<annotation encoding="application / x-tex">5.94 \text{ (s, 2H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>3.17 (m, 4H)<annotation encoding="application / x-tex">3.17 \text{ (m, 4H)}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>1.66 (m, 1H)<annotation encoding="application / x-tex">1.66 \text{ (m, 1H)}< / annotation>< / semantics>< / com:Math> 4H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 144.97, 142.99, 140.4, 137.50, 136.50, 134.97, 132-132.89 (m), 129.62, 128.55, 127.63, 126.13, 125.07, 116.98, 113.26, 110.97, 57.43, 47.71, 24.65. HRMS: calcd for [M - H], 517.12190; found, 517.12134. EXAMPLE 100 2-(4-Chlorophenyl)-3-(1-(1-phenylethyl)-1<com:Math><semantics>H<annotation encoding="application / x-tex">H< / annotation>< / semantics>< / com:Math>-1,2,3-triazol-4-yl)imidazo[1,2-<com:Math><semantics>a<annotation encoding="application / x-tex">a< / annotation>< / semantics>< / com:Math>]pyridine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-100 %). Yield 72 mg (80 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.58 (s, 1H), 8.41 (dt, <com:Math><semantics>J=6.9<annotation encoding="application / x-tex">J = 6.9< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 7.69 (dd, <com:Math><semantics>J=8.4<annotation encoding="application / x-tex">J = 8.4< / annotation>< / semantics>< / com:Math>, 1.7 Hz, 3H), 7.44 – 7.32 (m, 9H), 6.99 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 6.08 (q, <com:Math><semantics>J=7.1<annotation encoding="application / x-tex">J = 7.1< / annotation>< / semantics>< / com:Math> Hz, 1H), 1.96 (d, <com:Math><semantics>J=7.1<annotation encoding="application / x-tex">J = 7.1< / annotation>< / semantics>< / com:Math> Hz, 3H). <com:Sup>13< / com:Sup>C NMR (101) MHz, DMSO) δ 144.88, 142.41, 141.14, 136.02, 133.00, 132.75, 129.52, 128.95, 128.58, 128.24, 126.43, 126.20, 125.28, 124.60, 117.08, 113.30, 111.70, 59.89, 21.25. HRMS: calcd for [M + H], 400.13235; found, 400.13214. EXAMPLE 101 2-(4-Chlorophenyl)-3-(1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-100 %). Yield 253 mg (88 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.56 (s, 1H), 8.49 (dt, J <com:Math><semantics>=6.9,1.2 Hz,1H,8.31−8.21 (m, 2H),7.73−7.67 (m, 3H),7.62−<annotation encoding="application / x-tex">= 6.9, 1.2 \text{ Hz}, 1\text{H}, 8.31 - 8.21 \text{ (m, 2H)}, 7.73 - 7.67 \text{ (m, 3H)}, 7.62 -< / annotation>< / semantics>< / com:Math> <Formule mathématique disponible dans le document PDF, Math available in the PDF document>7.54 \text{ (m, 2H)}, 7.47 - 7.41 \text{ (m, 2H)}, 7.39 \text{ (ddd}, J = 9.0, 6.7, 1.3 Hz, 1H)}, 7.00 (td, <com:Math><semantics>J=6.8,1.3<annotation encoding="application / x-tex">J = 6.8, 1.3< / annotation>< / semantics>< / com:Math> Hz, 1H), 5.92 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 147.73, 145.24, 143.78, 142.85, 136.75, 133.30, 133.14, 129.95, 129.39, 129.00, 126.55, 126.44, 125.70, 124.43, 117.40, 113.64, 111.80, 52.70. HRMS: calcd for [M - H], 430.09; found, 429.555. EXAMPLE 102 3-(1-(4-Chloro-3-nitrobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-100 %). Yield 835 mg (83 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.58 (s, 1H), 8.50 (dt, J <com:Math><semantics>=6.9,1.2 Hz,1H<annotation encoding="application / x-tex">= 6.9, 1.2 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), <com:Math><semantics>8.15 (d, J=2.1 Hz,1H)<annotation encoding="application / x-tex">8.15 \text{ (d, } J = 2.1 \text{ Hz}, 1\text{H})< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>7.82 (d, J=8.4 Hz,1H)<annotation encoding="application / x-tex">7.82 \text{ (d, } J = 8.4 \text{ Hz}, 1\text{H})< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>7.73−7.65<annotation encoding="application / x-tex">7.73 - 7.65< / annotation>< / semantics>< / com:Math> (m, 4H), <com:Math><semantics>7.43−7.38<annotation encoding="application / x-tex">7.43 - 7.38< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.36<annotation encoding="application / x-tex">7.36< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=9.1,6.7,1.3<annotation encoding="application / x-tex">J = 9.1, 6.7, 1.3< / annotation>< / semantics>< / com:Math> Hz, 1H), 6.98 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 147.65, 144.93, 142.50, 136.94, 136.53, 133.62, 132.99, 132.85, 132.31, 129.63, 128.62, 126.15, 125.94, 125.41, 125.39, 125.10, 117.06, 113.23, 111.50, 51.70. HRMS: calcd for [M - H], 465.06281; found, 465.06250. EXAMPLE 103 2-Chloro-5-(1-(4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)ethyl)benzamide [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure IV (Scheme 1). Mobile phase petrolether / EtOAc (40-100 %). Yield 56 mg (81 %). H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.67 (s, 1H), 8.42 (dt, <com:Math><semantics>J=7.0<annotation encoding="application / x-tex">J = 7.0< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 7.96 (s, 1H), 7.74 – 7.67 (m, 4H), 7.54 (d, <com:Math><semantics>J=<annotation encoding="application / x-tex">J =< / annotation>< / semantics>< / com:Math> 8.3 Hz, 1H), 7.45 (ddt, <com:Math><semantics>J=9.2<annotation encoding="application / x-tex">J = 9.2< / annotation>< / semantics>< / com:Math>, 7.5, 2.4 Hz, 4H), 7.38 (ddd, <com:Math><semantics>J=9.1<annotation encoding="application / x-tex">J = 9.1< / annotation>< / semantics>< / com:Math>, 6.7, 1.3 Hz, 1H), 6.99 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), 6.15 (q, <com:Math><semantics>J=7.1<annotation encoding="application / x-tex">J = 7.1< / annotation>< / semantics>< / com:Math> Hz, 1H), 1.97 (d, <com:Math><semantics>J=7.1<annotation encoding="application / x-tex">J = 7.1< / annotation>< / semantics>< / com:Math> Hz, 3H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 168.06, 144.94, 142.43, 140.11, 137.69, 136.14, 132.97, 132.88, 130.24, 129.51, 128.71, 126.87, 126.27, 125.32, 124.66, 117.10, 113.32, 111.63, 59.04, 21.07. HRMS: calcd for [M + H], 477.09919; found, 477.09891. Scheme 2. [Image disponible dans le document PDF, Image available in the PDF document] General procedure V. Nitro group reduction Nitro derivative was dissolved in MeOH and AcOH (7 eq) and Fe (3.5 eq) was added (Scheme 2). The reaction mixture was stirred at reflux untill the completion of the reaction. After cooling to r.t., the mixture was extracted with EtOAc, washed with NaHCO<com:Sub>3< / com:Sub> solution and the organic phase was dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography. EXAMPLE 104 <com:Math><semantics>4−((4−(2−(4−Chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−yl)methyl)aniline<annotation encoding="application / x-tex">4-((4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)aniline< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure V (Scheme 2). Mobile phase cyclohexan / EtOAc (40-100 %). Yield 123 mg (78 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.41 (dt, <com:Math><semantics>J=7.0<annotation encoding="application / x-tex">J = 7.0< / annotation>< / semantics>< / com:Math>, 1.3 Hz, 1H), <com:Math><semantics>8.39<annotation encoding="application / x-tex">8.39< / annotation>< / semantics>< / com:Math> (s, 1H), <com:Math><semantics>7.72−7.65<annotation encoding="application / x-tex">7.72 - 7.65< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.43−7.32<annotation encoding="application / x-tex">7.43 - 7.32< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.10−7.04<annotation encoding="application / x-tex">7.10 - 7.04< / annotation>< / semantics>< / com:Math> (m, 2H), 6.98 (td, <com:Math><semantics>J=6.8<annotation encoding="application / x-tex">J = 6.8< / annotation>< / semantics>< / com:Math>, 1.3 Hz, 1H), 6.59 – 6.53 (m, 2H), 5.48 (s, 2H), 5.20 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 149.31, 145.14, 142.57, 136.35, 133.35, 133.06, 129.86, 129.63, 128.90, 126.44, 125.58, 125.47, 122.83, 117.37, 114.23, 113.57, 112.10, 53.72. HRMS: calcd for [M + H], 401.12760; found, 401.12735. EXAMPLE 105 2-Chloro-5-<com:Math><semantics>((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−yl)methyl)−1<annotation encoding="application / x-tex">((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-1< / annotation>< / semantics>< / com:Math> aniline [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure V (Scheme 2). Mobile phase cyclohexan / EtOAc (40-100 %). Yield 490 mg (79 %). <com:Sup>1< / com:Sup>H NMR (401 MHz, DMSO-<com:Math><semantics>d6<annotation encoding="application / x-tex">d_6< / annotation>< / semantics>< / com:Math>) <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> 8.46 (dt, <com:Math><semantics>J=7.0<annotation encoding="application / x-tex">J = 7.0< / annotation>< / semantics>< / com:Math>, 1.2 Hz, 1H), <com:Math><semantics>8.44<annotation encoding="application / x-tex">8.44< / annotation>< / semantics>< / com:Math> (s, 1H), <com:Math><semantics>7.73−7.66<annotation encoding="application / x-tex">7.73 - 7.66< / annotation>< / semantics>< / com:Math> (m, 3H), <com:Math><semantics>7.44−7.39<annotation encoding="application / x-tex">7.44 - 7.39< / annotation>< / semantics>< / com:Math> (m, 2H), <com:Math><semantics>7.37<annotation encoding="application / x-tex">7.37< / annotation>< / semantics>< / com:Math> (ddd, <com:Math><semantics>J=9.1,6.7,1.2 Hz,1H<annotation encoding="application / x-tex">J = 9.1, 6.7, 1.2 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 7.21 (d, <com:Math><semantics>J=8.2 Hz,1H<annotation encoding="application / x-tex">J = 8.2 \text{ Hz}, 1\text{H}< / annotation>< / semantics>< / com:Math>), 6.99 (td, <com:Math><semantics>J=6.8,1.2 Hz<annotation encoding="application / x-tex">J = 6.8, 1.2 \text{ Hz}< / annotation>< / semantics>< / com:Math>) Hz, 1H), 6.71 (d, <com:Math><semantics>J=2.1<annotation encoding="application / x-tex">J = 2.1< / annotation>< / semantics>< / com:Math> Hz, 1H), 6.52 – 6.47 (m, 1H), 5.59 (s, 2H), 5.50 (s, 2H). <com:Sup>13< / com:Sup>C NMR (101 MHz, DMSO) δ 145.11, 144.88, 142.37, 136.29, 135.75, 132.96, 132.81, 132.80, 129.65, 129.60, 129.49, 128.65, 128.61, 126.19, 126.14, 125.74, 125.33, 117.07, 116.94, 116.02, 114.31, 113.30, 111.65, 52.95. HRMS: calcd for <com:Math><semantics>[M+H]<annotation encoding="application / x-tex">[M + H]< / annotation>< / semantics>< / com:Math>, 435.08863; found, 435.08815. Genereal procedure VI. Acetylation of aniline moieties Compounds with aniline moiety was dissolved in dioxane and Ac<com:Sub>2< / com:Sub>O (1.5 eq) was added followed by pyridine (1.5 eq). The reaction mixture was stirred at r.t. overnight. After the completion of the reaction the mixture was evaporated, diluted with EtOAc and washed with water. Organic phase was dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography. EXAMPLE 106 <com:Math><semantics>N−(4−((4−(2−(4−chlorophenyl)imidazo[1,2−a]pyridin−3−yl)−1H−1,2,3−triazol−1−yl)methyl)phenyl)−1<annotation encoding="application / x-tex">N-(4-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1< / annotation>< / semantics>< / com:Math> acetamide [Image disponible dans le document PDF, Image available in the PDF document] Title compound was prepared according to the General procedure VI (Scheme 2). Mobile phase cyclohexan / EtOAc (40-100 %). Yield 63 mg (92 %). <com:Sup>1&...

Claims

1. A compound of general formula I [Image disponible dans le document PDF, Image available in the PDF document] (I) wherein L 1 L_1 is pyridine, thiazole, pyrimidine, pyridazine, or pyrazine; L 2 is a bivalent residue of pyridine, thiene, furane, oxazole, thiazole, isothiazole, isoxazole, oxadiazole, thiadiazole, triazole, tetrazole, imidazole, pyrrole, dihydropyrane, dihydrofurane, pyrimidine, triazine, tetrazine, cyclohexane, or cyclohexene; R 1 is independently halogen, pseudohalogen, amino, hydrocarbylamino, dihydrocarbylamino, nitro, C1- C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, acyl, alkylcarbamoyl, carbamoyl, alkylthiocarbamoyl, thiocarbamoyl, alkylsulfonyl, sulfonamido, N-alkylsulfonamido, N,N- dialkylsulfonamido, carboxyl, alkyloxycarbonyl, amide, N-alkylamide, N,N-dialkylamide, thioamide, N- alkylthioamide, N,N-dialkylthioamide, or oxime, wherein each of these substituents may optionally be further substituted by one or more substituents which is halogen, pseudohalogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, hydrocarbylamino, or dihydrocarbylamino; R 2 is independently halogen, pseudohalogen, amino, hydrocarbylamino, dihydrocarbylamino, nitro, C1- C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, acyl, alkylcarbamoyl, carbamoyl, alkylthiocarbamoyl, thiocarbamoyl, alkylsulfonyl, sulfonamido, N-alkylsulfonamido, N,N- dialkylsulfonamido, carboxyl, alkyloxycarbonyl, amide, N-alkylamide, N,N-dialkylamide, thioamide, N- alkylthioamide, N,N-dialkylthioamide, or oxime, wherein each of these substituents may optionally be further substituted by one or more substituents which is halogen, pseudohalogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, hydrocarbylamino, or dihydrocarbylamino; wherein at least one R 1 or R 2 is present, and wherein the said at least one R 1 or R 2 is independently halogen, pseudohalogen or alkoxy; each of R 3 and R 4 is independently H, OH, or C1-C6 alkyl, wherein each of these substituents may optionally be further substituted by one or more substituents OH; or R 3 and R 4 together form a C1-C4 alkylidene or =O; each R 5 is independently halogen, or pseudohalogen; each R 6 is independently 3 H, halogen, pseudohalogen, or OH; each X is independently CH or N; each Y is independently C, O, S, or N; wherein when Y is O or S, R 3 and R 4 are not present, and when Y is N, R 4 is not present; m is 1 or 2; n, o, q are independently 0, 1 or 2; and p is 1 and wherein the pseudohalogen R 1 , R 2 , R 5 or R 6 is cyanide, cyanate, thiocyanate, selenocyanate, trifluoromethyl, or azide.

2. A compound, which is: 2 − ( 4 − C h l o r o p h e n y l ) − 3 − ( 1 − ( 3 , 4 − d i c h l o r o b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine, 6 − ( 4 − Chlorophenyl ) − 5 − ( 1 − ( 3 , 4 − dichlorobenzyl ) − 1 H − 1 , 2 , 3 − triazol − 4 − yl ) imidazo [ 2 , 1 − b ] thiazole , 6-(4-\text{Chlorophenyl})-5-(1-(3,4-\text{dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})\text{imidazo}[2,1-b]\text{thiazole}, 5 − ( 1 − ( 3 , 4 − D i m e t h o x y b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) − 6 − p h e n y l i m i d a z o [ 2 , 1 − b ] t h i a z o l e , 5-(1-(3,4-Dimethoxybenzyl)-1H-1,2,3-triazol-4-yl)-6-phenylimidazo[2,1-b]thiazole, 6 − ( 4 − Chlorophenyl ) − 5 − ( 1 − ( 4 − methoxybenzyl ) − 1 H − 1 , 2 , 3 − triazol-4-yl ) imidazo [ 2 , 1 − b ] thiazole , 6-(4-\text{Chlorophenyl})-5-(1-(4-\text{methoxybenzyl})-1H-1,2,3-\text{triazol-4-yl})\text{imidazo}[2,1-b]\text{thiazole}, 2 − ( 4 − C h l o r o p h e n y l ) − 3 − ( 1 − ( 3 , 4 − d i m e t h o x y b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 2-(4-Chlorophenyl)-3-(1-(3,4-dimethoxybenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine, 2 − ( 4 − C h l o r o p h e n y l ) − 3 − ( 1 − ( 4 − m e t h o x y b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 2-(4-Chlorophenyl)-3-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine, 3 − ( 1 − Benzyl- 1 H − 1 , 2 , 3 − triazol- 4 − yl ) − 2 − ( 4 − chlorophenyl ) imidazo [ 1 , 2 − a ] pyridine , 3-(1-\text{Benzyl-}1H-1,2,3-\text{triazol-}4-\text{yl})-2-(4-\text{chlorophenyl})\text{imidazo}[1,2-a]\text{pyridine}, 2-(4-Chlorophenyl)-3-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine, 5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-6-(4-chlorophenyl)imidazo[2,1-b]thiazole, 6 − ( 4 − Chlorophenyl ) − 5 − ( 1 − ( pyridin- 2 − ylmethyl ) − 1 H − 1 , 2 , 3 − triazol- 4 − yl ) imidazo [ 2 , 1 − b ] thiazole , 6-(4-\text{Chlorophenyl})-5-(1-(\text{pyridin-}2-\text{ylmethyl})-1H-1,2,3-\text{triazol-}4-\text{yl})\text{imidazo}[2,1-b]\text{thiazole}, 3 − ( 1 − ( 4 − Chlorobenzyl ) − 1 H − 1 , 2 , 3 − triazol − 4 − yl ) − 2 − ( 4 − chlorophenyl ) imidazo [ 1 , 2 − a ] pyridine , 3-(1-(4-\text{Chlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-2-(4-\text{chlorophenyl})\text{imidazo}[1,2-a]\text{pyridine}, 5 − ( 1 − ( 4 − Chlorobenzyl ) − 1 H − 1 , 2 , 3 − triazol − 4 − yl ) − 6 − ( 4 − chlorophenyl ) imidazo [ 2 , 1 − b ] thiazole , 5-(1-(4-\text{Chlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-6-(4-\text{chlorophenyl})\text{imidazo}[2,1-b]\text{thiazole}, 3-Benzyl-5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)isoxazole, 4 − ( ( 4 − ( 2 − ( 4 − C h l o r o p h e n y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n − 3 − y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 1 − y l ) m e t h y l ) b e n z o n i t r i l e , 4-((4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzonitrile, 2 − ( 4 − C h l o r o p h e n y l ) − 3 − ( 1 − ( 3 , 4 − d i c h l o r o b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) i m i d a z o [ 1 , 2 − b ] p y r i d a z i n e , 2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-b]pyridazine, 3 − ( 1 − ( 3 , 4 − Dichlorobenzyl ) − 1 H − 1 , 2 , 3 − triazol − 4 − yl ) − 2 − ( 3 , 4 − dichlorophenyl ) imidazo [ 1 , 2 − a ] pyridine , 3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-2-(3,4-\text{dichlorophenyl})\text{imidazo}[1,2-a]\text{pyridine}, 5 − ( 1 − ( 3 , 4 − Dichlorobenzyl ) − 1 H − 1 , 2 , 3 − triazol − 4 − yl ) − 6 − ( 3 , 4 − dichlorophenyl ) imidazo [ 2 , 1 − b ] thiazole , 5-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-6-(3,4-\text{dichlorophenyl})\text{imidazo}[2,1-b]\text{thiazole}, 3-(1-Benzyl-1H-1,2,3-triazol-4-yl)-6-chloro-2-(4-chlorophenyl)imidazo[1,2-b]pyridazine, 5-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-3-(3,4-dichlorobenzyl)-1,2,4-oxadiazole, 2-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-5-(3,4-dichlorobenzyl)-1,3,4-oxadiazole, 5-(6-(4-Chlorophenyl)imidazo[2,1-b]thiazol-5-yl)-3-(3,4-dichlorobenzyl)-1,2,4-oxadiazole, 2 − ( 4 − Chlorophenyl ) − 3 − ( 5 − ( 3 , 4 − dichlorobenzyl ) − 1 H − 1 , 2 , 4 − triazol − 3 − yl ) imidazo [ 1 , 2 − a ] pyridine , 2-(4-\text{Chlorophenyl})-3-(5-(3,4-\text{dichlorobenzyl})-1H-1,2,4-\text{triazol}-3-\text{yl})\text{imidazo}[1,2-a]\text{pyridine}, 6-(4-Chlorophenyl)-5-(2-(3,4-dichlorobenzyl)thiazol-4-yl)imidazo[2,1-b]thiazole, 4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-2-(3,4-dichlorobenzyl)thiazole, 2-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-5-(3,4-dichlorobenzyl)-1,3,4-thiadiazole, 3 − ( 1 − ( 3 , 4 − D i c h l o r o b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) − 2 − ( p − t o l y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(p-tolyl)imidazo[1,2-a]pyridine, 3 − ( 1 − ( 3 , 4 − Dichlorobenzyl ) − 1 H − 1 , 2 , 3 − triazol − 4 − yl ) − 2 − ( 2 , 4 − dichlorophenyl ) imidazo [ 1 , 2 − a ] pyridine , 3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-2-(2,4-\text{dichlorophenyl})\text{imidazo}[1,2-a]\text{pyridine}, 4 − ( 3 − ( 1 − ( 3 , 4 − Dichlorobenzyl ) − 1 H − 1 , 2 , 3 − triazol − 4 − yl ) imidazo [ 1 , 2 − a ] pyridin − 2 − yl ) benzonitrile , 4-(3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})\text{imidazo}[1,2-a]\text{pyridin}-2-\text{yl})\text{benzonitrile}, 103 3 − ( 1 − ( 3 , 4 − D i c h l o r o b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) − 2 − ( 4 − m e t h o x y p h e n y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyridine, 3 − ( 1 − ( 3 , 4 − Dichlorobenzyl ) − 1 H − 1 , 2 , 3 − triazol − 4 − yl ) − 2 − ( 4 − ( trifluoromethyl ) phenyl ) imidazo [ 1 , 2 − a ] pyridine , 3-(1-(3,4-\text{Dichlorobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-2-(4-(\text{trifluoromethyl})\text{phenyl})\text{imidazo}[1,2-a]\text{pyridine}, 3 − ( 1 − ( 3 , 4 − D i c h l o r o b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) − 2 − ( 4 − f l u o r o p h e n y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-fluorophenyl)imidazo[1,2-a]pyridine, 3 − ( 1 − ( 3 , 4 − D i c h l o r o b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) − 2 − ( 4 − e t h y l p h e n y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 3-(1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)-2-(4-ethylphenyl)imidazo[1,2-a]pyridine, Methyl 2-chloro-5- ( ( 4 − ( 2 − ( 4 − c h l o r o p h e n y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n − 3 − y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 1 − ((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzoate, (2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)phenyl)methanol, 2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine, 2-(4-Chlorophenyl)-3-(1-(3,4-dichlorobenzyl)-1H-pyrrol-2-yl)imidazo[1,2-a]pyridine, 2 − ( 4 − C h l o r o p h e n y l ) − 3 − ( 1 − ( 3 , 4 − d i c h l o r o p h e n e t h y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 2-(4-Chlorophenyl)-3-(1-(3,4-dichlorophenethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine, 2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide, 2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-N,N- dimethylbenzamide, 2-Chloro-5- ( ( 4 − ( 2 − ( 4 − c h l o r o p h e n y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n − 3 − y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 1 − y l ) m e t h y l ) − N − ((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-N- methoxy-N-methylbenzamide, 1-(2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)phenyl)ethan-1-one, 2-Chloro-5- ( ( 4 − ( 2 − ( 4 − c h l o r o p h e n y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n − 3 − y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 1 − y l ) m e t h y l ) − N − ((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-N- methylbenzamide, 1-(2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)phenyl)propan-1-one, 2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)-N,N- dimethylbenzamide, 2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)-N,N- dimethylbenzothioamide, 2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-oxadiazol-2-yl)methyl)-N- methylbenzothioamide, 2-Chloro-5-((5-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1,3,4-oxadiazol-2-yl)methyl)-N- methylbenzamide, 2 − ( 4 − C h l o r o p h e n y l ) − 3 − ( 1 − ( 4 − ( m e t h y l s u l f o n y l ) b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 2-(4-Chlorophenyl)-3-(1-(4-(methylsulfonyl)benzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine, 2-(4-Chlorophenyl)-3-(1-(1-phenylethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine, 2 − ( 4 − C h l o r o p h e n y l ) − 3 − ( 1 − ( 4 − n i t r o b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 2-(4-Chlorophenyl)-3-(1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine, 4 − ( ( 4 − ( 2 − ( 4 − C h l o r o p h e n y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n − 3 − y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 1 − y l ) m e t h y l ) a n i l i n e , 4-((4-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)aniline, 2-Chloro-5-(1-(4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)ethyl)benzamide, 2 − ( 4 − C h l o r o p h e n y l ) − 3 − ( 1 − ( 4 − ( m e t h y l t h i o ) b e n z y l ) − 1 H − 1 , 2 , 3 − t r i a z o l − 4 − y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n e , 2-(4-Chlorophenyl)-3-(1-(4-(methylthio)benzyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine, 2-Chloro-5-((4-(2-(4-chlorophenyl)-8-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide, 2-Chloro-5-((4-(2-(4-chlorophenyl)-7-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide, 2-Chloro-5-((4-(2-(4-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide, 2-Chloro-5-((4-(2-(4-chlorophenyl)-6,8-difluoroimidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzamide, 2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H-1,2,3-triazol-1- yl)methyl)benzaldehyde, ( E ) (E) -2-chloro-5- ( ( 4 − ( 2 − ( 4 − c h l o r o p h e n y l ) i m i d a z o [ 1 , 2 − a ] p y r i d i n − 3 − y l ) − 1 < m a t h > H ((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1H -1,2,3-triazol-1- yl)methyl)benzaldehyde oxime, N − ( 4 − ( 4 − ( 4 − ( 4 − ( 4 − ( 4 − ( 4 − ( 4 − ( 4 − ( 4 − ( 4 − ( 4 − ( 4 − N-(4-(4-(4-(4-(4-(4-(4-(4-(4-(4-(4-(4-(4- yl)methyl)phenyl)acetamide, 3 − ( 1 − ( 4 − Chloro − 3 − nitrobenzyl ) − 1 H − 1 , 2 , 3 − triazol − 4 − yl ) − 2 − ( 4 − chlorophenyl ) imidazo [ 1 , 2 − a ] pyridine , 3-(1-(4-\text{Chloro}-3-\text{nitrobenzyl})-1H-1,2,3-\text{triazol}-4-\text{yl})-2-(4-\text{chlorophenyl})\text{imidazo}[1,2-a]\text{pyridine}, 2 2 -Chloro- 5 5 -(( 4 4 -( 2 2 -( 4 4 -chlorophenyl)imidazo[ 1 1 , 2 2 - a a ]pyridin- 3 3 -yl)- 1 1 H H - 1 1 , 2 2 , 3 3 -triazol- 1 1 -yl)methyl)aniline, 3-(4-Benzylphenyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine, 3-(6-Benzylpyridin-3-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine, 2-(4-Chlorophenyl)-3-(6-(1-phenylvinyl)pyridin-3-yl)imidazo[1,2-a]pyridine, 2-Chloro-5-((4-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-5-iodo-1H-1,2,3-triazol-1- yl)methyl)benzamide, 2-(4-Chlorophenyl)-3-(1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine, 3-(4-Benzylcyclohex-1-en-1-yl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine, 4-Benzyl-1-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)cyclohexan-1-ol, 1-(5-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)pyridin-2-yl)-1-phenylethane-1,2-diol, (5-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)pyridin-2-yl)(phenyl)methanone, or 2-Chloro-5-((4-(2-(pyridine-4-yl)imidazo[1,2-a]pyridine-3-yl)-1H-1,2,3-triazol-1-yl)methyl)benzamide.

3. The compound according to claim 1 or 2 for use as a medicament.

4. The compound according to claim 1 or 2 for use in the prevention or treatment of a condition which is mediated by the action, or by loss of action, of constitutive androstane receptor (CAR) or its endogenous ligands.

5. The compound according claim 1 or 2 for use in the prevention or treatment of a disorder which is: metabolic disorder, metabolic syndrome, type II diabetes, gestational diabetes, obesity, obesity related atherosclerosis, cholesterol gallstone disease, dyslipidemia, cholelithiasis, cholangitis, high cholesterol diseases, acute liver failure, lipid metabolic disorders, bilirubin gallstone disease, cholelithiasis, choledocholithiasis, inflammation of gallbladder, inflammation of pancreas, cholestasis diseases, liver steatosis, hyperbilirubinemia, jaundice, hyperthyreosis, or inflammatory liver disease connected with metabolic disease.

6. The compound for use according to claim 5, wherein the metabolic disorder is a defect in glucose, cholesterol or lipid metabolism.

7. The compound for use according to claim 5, wherein the metabolic disorder is impaired glucose tolerance or insulin sensitivity.

8. The compound for use according to claim 5, wherein the gestational diabetes is a risk factor for preeclampsia.

9. The compound for use according to claim 5, wherein the inflammatory liver disease connected with metabolic disease is a non-alcoholic steatohepatitits or non-alcoholic fatty liver disease.

10. The compound according to claim 1 or 2 for use in protection against liver stress, intoxication or liver infections.

11. The compound according to claim 1 or 2 for use in the treatment of cancers or leukemia.

12. The compound according to claim 1 or 2 for use as a cytostatic prodrug activator.

13. The compound according to claim 1 or 2 for use in the stimulation of liver regeneration after partial hepatectomy or liver injuries connected with the need of liver regeneration and parenchyma cells proliferation.

14. The compound according to claim 1 or 2 for use in human adjuvant treatment of a condition or disease connected with malignancy and / or in metabolic activation of antineoplastic drugs.

15. A pharmaceutical composition comprising as active ingredient the compound as defined in claim 1 or 2 or a pharmaceutically acceptable salt or solvate thereof, and one or more pharmaceutically acceptable carriers, polymers and / or excipients.