IMIDAZOPYRIDINE COMPOUNDS AND USES THEREOF

FIELD OF THE INVENTION

The present invention relates to imidazopyridine compounds (the compounds of formula 1 described herein), to processes for their preparation, pharmaceutical compositions containing them, and their use as inhibitors of pro-inflammatory cytokines selected from TNF-cc, IL-1 β, IL-6, IL-8, IL-12, IL-17 and IL-23 and further, use of the compounds in the treatment of diseases or disorders mediated by one or more of said pro-inflammatory cytokines.

BACKGROUND OF THE INVENTION

Tumor Necrosis Factor (TNF) - a, a potent cytokine is a soluble 17-Kd protein with three identical subunits. TNF is produced by the body and is involved in normal inflammatory and immune responses. (Indian J Critical Care Med, 2007, 1 1 , 3, 139- 148). It is both autocrine and paracrine inducer of other cytokines like IL (interleukin)-l , IL-6, IL-8, platelet derived growth factor-B, ecosanoids, platelet activating factors and granulocyte monocyte colony stimulating factor.

TNF-a alters the properties of endothelial cells and has various pro-coagulant activities, such as production of an increase in tissue factor procoagulant activity and suppression of the anticoagulant protein C pathway as well as down-regulating the expression of thrombomodulin (Sherry et.al., Jour. Cell. Biol., 1988, 107, 1269-1277). TNF-a has activities which, together with its early production (during the initial stages of a trauma or injury event), make it a mediator of response to tissue injury in several important disorders including, but not limited to myocardial infarction, stroke and circulatory shock. Noradrenaline, angiotensin, vasopressin, endothelin, and tumor- necrosis factor (TNF- alpha) play a major role in heart failure (N.E. J. Med., 1990, 323, 236-241 ).

TNF-a also plays a central role in the state of insulin resistance associated with obesity. One important mechanism by which TNF-a interferes with insulin signaling is through serine phosphorylation of insulin receptor substrate-1 (IRS-1 ), which can function as an inhibitor of the tyrosine kinase activity of the insulin receptor (IR) (The Journal of Biological Chemistry, 1996, 271 , 22, 13018-13022).

Multiple sclerosis (MS) plaques within the central nervous system (CNS) are infiltrated by peripheral blood mononuclear cells. In patients, TNF-a is overproduced by peripheral blood mononuclear cells during MS relapse. TNF-a is found at high levels in multiple sclerosis (MS) plaques and induces both apoptotic and necrotic death of oligodendrocytes (Neuroscience & Medicine, 201 1 , 2, 93-103). This aspect of TNF-a activity may contribute directly to myelin damage and/or the demyelination process observed in diseases such as multiple sclerosis (MS).

TNF-a is a potent factor that promotes renal cyst development, especially in the autosomal dominant polycystic kidney disease (ADPKD) genetic background. A relatively recent study found that TNF-a can also activate mTOR pathway through ΙΚΚβ (inhibitor of nuclear factor kappa-B kinase subunit beta), and inhibition of mTOR has been shown to revert cystogenesis in polycystic kidney disease (Nat Med. 2008, 14, 8, 863-868).

Several proinflammatory cytokines, especially TNF-a, IL-Ι β, IL-6, IL-8, IL-12, IL- 17 and IL-23 play an important role in the inflammatory process. Both IL-1 and TNF-a are derived from mononuclear cells and macrophages and in turn induce the expression of a variety of genes that contribute to the inflammatory process.

Inflammation occurs in response to tissue damage, either through injury or from infection. In the case of an infection, inflammation causes the activation of the immune response. Inflammation, the response of tissue to injury, is characterized by increased blood flow and vascular permeability along with the accumulation of fluid, leukocytes, and inflammatory mediators such as cytokines.

An increase in TNF-a synthesis/release is a common phenomenon during the inflammatory process. Another pro-inflammatory cytokine, namely IL-6, is involved in immune reaction regulation, hematopoiesis, acute phase response, and growth of certain types of tumor cells. Evidence has recently shown that overproduction of IL-6 is critically involved in the pathogenesis of RA. Therefore, modulation of this cytokine function may be potentially effective against RA and other chronic and refractory autoimmune/inflammatory diseases or disorders. Thus, reduction of these cytokine levels has become an attractive goal to discover disease modifying treatments for inflammatory diseases or disorders.

Thus, TNF-a and interleukins have been reported to play a crucial role in the pathogenesis of many diseases or disorders such as osteoporosis, rheumatoid arthritis, osteoarthritis, juvenile rheumatoid arthritis, psoriatic arthritis, osteoarthritis, refractory rheumatoid arthritis, chronic non-rheumatoid arthritis, adult respiratory distress syndrome, asthma, rheumatoid asthma, systemic lupus erythematosus (SLE), pulmonary fibrosis, chronic obstructive pulmonary disease, lung sarcoidosis, renal fibrosis, polycystic kidney disease (PKD), nephritis, diabetic nephropathy, glomerular nephritis, Alzheimer's disease, Parkinson's disease, multiple sclerosis, liver disorders, inflammatory bowel disease, Crohn's disease, ulcerative colitis, delayed-type hypersensitivity in skin, dermatitis, urticaria, psoriasis, scleroderma, coronary heart disease, myocardial infarction, stroke, circulatory shock, arterial sclerosis, atherosclerosis, varicose veins, vasculitis, septic shock syndrome, allergic rhinitis, allergic conjunctivitis, glioblastoma, myeloid leukemia, acute myeloid leukemia, ovarian cancer, Kaposi's sarcoma, graft versus host disease, diverticulitis, Type II diabetes, diabetic retinopathy, glaucoma and ankylosing spondylitis.

Currently a few treatment options are available for the treatment of diseases or disorders mediated by TNF-cc and interleukins. The first line of treatment for disorders such as systemic lupus erythematosus, Alzheimer's disease, arthritis, Crohn's disease, ulcerative colitis and inflammatory bowel disease involves the use of non-steroidal antiinflammatory drugs (NSAIDs) e.g. ibuprofen, naproxen to alleviate symptoms such as pain. However, despite the widespread use of NSAIDs, many individuals cannot tolerate the doses necessary to treat the disorders over a prolonged period of time as NSAIDs are known to cause gastric erosions. Moreover, NSAIDs merely treat the symptoms of disorder and not the cause. When patients fail to respond to NSAIDs, other drugs such as methotrexate, gold salts, D-penicillamine and corticosteroids are used. These drugs also have significant toxic effects.

Relatively recently certain drugs namely etanercept (Enbrel®, Amgen/Wyeth), infliximab (Remicade®, Centocor/Schering-Plough/Tanabe Sieyaku) and adalimumab (Humira®, Abbott), which functions as monoclonal antibodies to TNF-a or interfere with TNF-a receptors, are used in the treatment of disorders or diseases mediated by TNF- a. However, the monoclonal antibodies are associated with certain drawbacks such as the route of administration (only parenteral), high cost, allergy induction, activation of latent tuberculosis, increased risk of cancer and congestive heart disease. A review on infectious complications associated with monoclonal antibodies is provided in Clinical Microbiology Reviews, 2009, 22, 2, 274-290.

Cunningham et. al. (Science, 2005, 310, 1022-1025) provides a small-molecule inhibitor of tumor necrosis factor a (TNF-a) that inhibits TNF-a activity in biochemical and cell-based assays. The molecule displaces a subunit of the trimer to form a complex with a dimer of TNF-a subunits. US 7,098, 221 discloses amide substituted imidazopyridines for the inhibition of TNF-a and various interleukins.

Notwithstanding the availability of a number of therapies for the treatment of diseases or disorders mediated by one or more proinflammatory cytokines, there still exists a continuing need for improved and alternative medicaments for the treatment of said disorders.

SUMMARY OF THE INVENTION

The present invention relates to the compounds of formula 1 (as described herein), processes for their preparation and their use in the treatment of diseases or disorders mediated by one or more of the pro-inflammatory cytokines described herein.

According to one aspect of the present invention, there are provided compounds of formula 1 (as described herein), stereoisomers and tautomers thereof, pharmaceutically acceptable salts, solvates, prodrugs and polymorphs thereof.

According to another aspect of the present invention, there are provided processes for the preparation of the compounds of formula 1 .

According to another aspect of the present invention, there are provided pharmaceutical compositions comprising one or more compounds of formula 1 or pharmaceutically acceptable salts thereof and at least one pharmaceutically acceptable carrier or excipient.

According to yet another aspect of the present invention, there are provided compounds of formula 1 which inhibit one or more of pro-inflammatory cytokines selected from TNF-a, IL-1 β , IL-6, IL-8, IL-12, IL-17 or IL-23.

According to yet another aspect of the present invention, there is provided a use of the compounds of formula 1 in the treatment of diseases or disorders mediated by one or more of pro-inflammatory cytokines selected from TNF-a, I L-1 β , IL-6, IL-8, IL-12, IL-17 or IL-23.

According to a further aspect of the present invention, there is provided a method for the treatment of diseases or disorders mediated by one or more of pro-inflammatory cytokines selected from TNF-a, IL-1 β , IL-6, IL-8, IL-12, IL-17 or IL-23; comprising administering to a subject in need thereof a therapeutically effective amount of the compound of formula 1 .

According to a further aspect of the present invention, there is provided a method for inhibiting one or more pro-inflammatory cytokines selected from TNF-a, I L- 1 β , IL-6, IL-8, IL-12, IL-17 or IL-23, comprising administering to a subject in need thereof an amount of the compounds of formula 1 effective to inhibit said pro-inflammatory cytokines.

According to yet another aspect of the present invention, there is provided use of the compounds of formula 1 for the manufacture of medicaments for the treatment of diseases or disorders mediated by one or more of pro-inflammatory cytokines selected from TNF-a, IL-1 β , IL-6, IL-8, IL-12, IL-17 or IL-23.

One or more further aspects of the present inventions are discussed in detail herein below. These and other objectives and advantages of the present invention will be apparent to those skilled in the art from the following description.

DETAILED DESCRIPTION OF THE INVENTION

The present invention p ula 1 :

Formula 1 in all their stereoisomeric and tautomeric forms and mixtures thereof in all ratios, or pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable prodrugs, N-oxides or pharmaceutically acceptable polymorphs thereof;

wherein,

X, Y, P and Q are independently selected from CR, N and N-oxide such that ring A and ring B independent of each other is a phenyl, pyridyl or pyrimidinyl ring;

R, R-i, R ₂ , R3, R4, R5 and R ₇ are independently selected from hydrogen, halogen, hydroxy, amino, cyano, (CrC ₆ )-alkyl, (Ci-C ₆ )-alkoxy, aryloxy, aralkyl, aralkyloxy, (C ₃ - C ₁₂ )-cycloalkyl, heterocyclyl, haloalkyl, COOR _a , CONR _a R _b , S(O) _m (C ₁ -C ₆ )-alkyl, and S(O) ₂ NR _a R _b ;

m is an integer from 0 to 2;

R ₆ is selected from hydrogen, halogen, hydroxy, cyano, (Ci-C ₆ )-alkyl, aralkyl, haloalkyl, COORa or CONR _a R _b ; and

R ₈ is hydrogen or (C-i-C ₆ )-alkyl; wherein,

(CrC ₆ )-alkyl is unsubstituted or substituted with one or more groups selected from halogen, hydroxy, cyano, (Ci-C ₆ )-alkyl, (Ci-C ₆ )-alkoxy, aryl, heterocyclyl or COOR _a ; each of (C ₃ -Ci ₂ )-cycloalkyl, aryl, ar(Ci-C ₆ )-alkyl and heterocyclyl is unsubstituted or substituted with one or more groups selected from halogen, hydroxy, cyano, amino, (d- C ₆ )-alkyl, (C ₁ -C ₆ )-alkoxy, haloalkyl, aryl, heterocyclyl, COOR _a or C(0)NR _a R _b ;

R _a and R _b are independently selected from hydrogen, (C-i-C ₆ )-alkyl, aralkyl, aryl and heterocyclyl;

with a proviso that when R ₆ is hydrogen, ring A is not a phenyl ring.

Definitions

Unless otherwise indicated, the following definitions are set forth to illustrate and define the meaning and scope of the various terms used to describe the invention herein and the appended claims. These definitions should not be interpreted in the literal sense as they are not general definitions and are relevant only for this application.

It will be understood that "substitution," "substituted" or "substituted with" means that one or more hydrogens of the specified moiety are replaced with a suitable substituent and includes the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and results in a stable compound.

As used herein, the term "alkyl" whether used alone or as part of a substituent group, refers to the radical of saturated aliphatic groups, including straight or branched- chain alkyl groups. An alkyl group can have a straight chain or branched chain containing carbon atoms. A straight-chain or branched chain alkyl has six or fewer carbon atoms in its backbone, for instance, C-|-C ₆ for straight chain and C ₃ -C ₆ for branched chain. Suitable alkyl groups containing from one to six carbon atoms, for example, include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, iso-butyl, sec-butyl, n-pentyl, isopentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, isohexyl, 2-hexyl and 3- hexyl.

Furthermore, unless stated otherwise, the alkyl groups may be unsubstituted or substituted. A substituted alkyl refers to a (Ci-C ₆ )-alkyl substituted with one or more groups selected from halogen, hydroxy, cyano, nitro, (C-i-C ₆ )-alkoxy, aryl, heterocyclyl, COOR _a , SR _a , C(O)R _a and C(O)NR _a R _b ; wherein R _a and R _b are independently selected from (CrC ₆ ) alkyl, aralkyl, aryl and heterocyclyl. Examples of substituted alkyls include, but not limited to, benzyl, hydroxymethyl, hydroxyethyl, 2-hydroxyethyl, N- morpholinomethyl, N-indolomethyl, piperidinylmethyl, and aminoethyl. When the alkyl group is substituted with one or more halogens, it is specifically referred to as "haloalkyl". A monohaloalkyl radical, for example, may have a chlorine, bromine, iodine or fluorine atom. Dihalo and polyhaloalkyi radicals may have two or more of the same or different halogen atoms. Examples of haloalkyl include but are not limited to chloromethyl, dichloromethyl, trichloromethyl, dichloroethyl, dichloropropyl, fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, difluorochloromethyl, dichlorofluoromethyl, difluoroethyl, difluoropropyl or the like groups.

As used herein, the term "alkoxy" refers to a (C-|-C ₆ ) alkyl having an oxygen radical attached thereto. The terms alkoxy or 0(Ci-C ₆ )alkyl wherever used in this specification have the same meaning. Representative alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy and t-butoxy.

A substituted alkoxy refers to an alkoxy group in which the alkyl is substituted with one or more groups selected from halogen, hydroxy, cyano, nitro, aryl, heterocyclyl, COORa, SR _a , C(0)R _a , or C(0)NR _a R _b ; wherein R _a and R _b are independently selected from hydrogen, (CrC ₆ ) alkyl, aralkyl, aryl and heterocyclyl. Examples of substituted alkoxy are chloromethoxy, 2-cyanoethoxy, trifluoromethoxy and benzyloxy group. A benzyloxy group refers to a benzyl having an oxygen radical attached thereto.

The term "aryl" as used herein refers to monocyclic or bicyclic hydrocarbon groups having 6 to 14 ring carbon atoms, preferably 6 to 10 carbon atoms in which the carbocyclic ring(s) present have a conjugated pi electron system. Examples of (C ₆ - Ci ₄ )aryl residues are phenyl, naphthyl, fluorenyl or anthracenyl. Examples of (C ₆ - Cio)aryl residues are phenyl or naphthyl. Aryl groups can be unsubstituted or substituted by one or more, for example 1 , 2, 3, 4 or 5, identical or different substituents selected from halogen, hydroxy, cyano, amino, nitro, (CrC ₆ )alkyl, (Ci-C ₆ )alkoxy, haloalkyl, heterocyclyl, COOR _a , SR _a , C(0)R _a or C(0)NR _a R _b ; wherein R _a and R _b are independently selected from hydrogen, unsubstituted or substituted (C-|-C ₆ ) alkyl, unsubstituted or substituted aralkyl, unsubstituted or substituted aryl and unsubstituted or substituted heterocyclyl. In monosubstituted phenyl residues, the substituent can be located in the 2-position, the 3-position or the 4-position. If the phenyl carries two substituents, they can be located in 2, 3-position, 2, 4-position, 2, 5-position, 2, 6- position, 3, 4-position or 3, 5-position. Examples of monosubstituted phenyl groups are 3-trifluoromethylphenyl, 4-chlorophenyl and 4-cyanophenyl. Examples of disubstituted phenyl groups include, but not limited to, 3, 5-difluorophenyl, and 3, 4-dimethoxyphenyl.

As used herein, the term "aryloxyl" or "aryloxy" refers to an aryl group having an oxygen radical attached thereto. The aryl of aryloxy group may be unsubstituted or substituted as explained in the definition of substituted aryl herein above. Examples of aryloxy groups include, but not limited to, phenoxy, 4-chlorophenoxy, 3, 4-dimethoxy phenoxy, etc.

The term "aralkyl" refers to an aryl group bonded directly through an alkyl group, such as benzyl. The aryl of the aralkyl group may be unsubstituted or substituted as explained in the definition of substituted aryl herein above.

As used herein, the term "aralkyloxyl" or "aralkyloxy" refers to an aralkyl group having an oxygen radical attached thereto. The aryl of aralkyloxy group may be unsubstituted or substituted as explained in the definition of substituted aryl herein above.

The term "heteroatom" as used herein includes nitrogen, oxygen, and sulfur. Any heteroatom with unsatisfied valency is assumed to have a hydrogen atom to satisfy the valency.

As used herein, the term "heterocyclyl" or "heterocycle" includes saturated heterocyclic ring systems, which do not contain any double bonds within the rings, as well as unsaturated heterocyclic ring systems, which contain one or more double bonds, for example, 3 double bonds within a ring, provided that the resulting mono, bi or tricyclic ring system is stable. In monocyclic heterocyclyl groups, heterocyclyl preferably is a 4-membered, 5-membered, 6-membered or 7-membered ring, more preferably a 5- or 6-membered ring. The heterocyclyl group may, for example, have one to four identical or different hetero atoms selected from : a nitrogen (N), a sulphur (S) or an oxygen (O) atom. Heterocyclyl monocyclic or bicyclic ring systems having an aromatic ring containing hetero atom/s are herein referred to by the customary term "heteroaryl" for which all the definitions and explanations relating to heterocyclyl apply. Examples of heterocyclyls include, but not limited to, pyrrolyl, pyrrolidinyl, pyrazolyl, imidazolyl, pyrazinyl, piperazinyl, oxazolyl, isoxazolyl, thiazolyl, tetrazolyl, furyl, thienyl, pyridyl, pyrimidyl, piperidyl, benzothiazolyl, purinyl, benzimidazolyl, benzoxazolyl, indolyl, isoindolyl, isoquinolyl, isoquinolyl, morpholinyl, thiomorpholinyl, thiomorpholinyl-1 , 1 - dioxide, quinoxalinyl, and quinolyl. A substituted heterocyclyl refers to a heterocyclyl substituted with one or more groups selected from halogen, hydroxy, amino, cyano, nitro, amino, (C-i-C ₆ )-alkyl, (d- C ₆ )-alkoxy, aryl, COOR _a , SR _a , C(0)R _a , (Ci-Ci ₂ )-alkyl-NR _a R _b or C(0)NR _a R _b; wherein R _a and Rb are independently selected from hydrogen, unsubstituted or substituted (CrC ₆ ) alkyl, unsubstituted or substituted aralkyl, aryl and heterocyclyl. The substituents may be present on either the ring carbon or the ring nitrogen atom(s). The substituents can be present at one or more positions provided that a stable molecule results.

The term "halogen" refers to a fluorine, chlorine, bromine, or iodine atom.

The term "amino" refers to the group "NH ₂ " which may be optionally substituted by one or more substituents. Examples of substituents include, but not limited to, (C-i- C ₄ )alkyl, (C ₆ -C-| ₀ ) aryl or the like groups.

The term "pharmaceutically acceptable solvate" or "solvates" as used herein refers to a compound formed by the interaction of a solute (in the present invention, a compound of formula 1 or a pharmaceutically acceptable salt thereof) and a solvent. Such solvents for the purpose of the invention may not interfere with the biological activity of the solute. Preferably, the solvent used is a pharmaceutically acceptable solvent. Examples of suitable pharmaceutically acceptable solvents include, without limitation, water, ethanol and acetic acid. Most preferably, the solvent used is water and the solvates obtained are referred to as hydrates. Examples for suitable solvates are the mono- or di-hydrates or alcoholates of the compounds according to the invention.

Within the context of the present invention and as used herein, the term "stereoisomer" is a general term used for all isomers of individual compounds that differ only in the orientation of their atoms in space. The term stereoisomer includes mirror image isomers (enantiomers), mixtures of mirror image isomers (racemates, racemic mixtures), geometric (cis/trans or E/Z) isomers, and isomers of compounds with more than one chiral center that are not mirror images of one another (diastereoisomers).

The term "tautomer" refers to the coexistence of two (or more) compounds that differ from each other only in the position of one (or more) mobile atoms and in electron distribution, for example, keto-enol tautomers.

The term "pharmaceutically acceptable salts" as used herein includes salts of the active compounds, which are prepared with acids or bases, depending on the particular substituents found on the compounds described herein. Within the context of the present invention and as used herein the term "polymorph" or "polymorphic form" refers to crystals of the same compound that differs only in the arrangement and/or conformation of the molecule in the crystal lattice.

Within the context of the present invention and as used herein, "N-oxide" refers to the oxide of the nitrogen atom of a nitrogen-containing heteroaryl or heterocycle. N- oxide can be formed in the presence of an oxidizing agent such as m-chloro-perbenzoic acid or hydrogen peroxide. N-oxide refers to an amine oxide, also known as amine-N- oxide, and is a chemical compound that contains N->0 bond.

Within the context of the present invention and as used herein, prodrug derivatives of any compound are derivatives of said compounds, which following administration, release the parent compound in vivo via a chemical or physiological process, e.g., a prodrug on being brought to the physiological pH or through enzyme action is converted to the parent compound. In the context of the present invention, the term "compound(s) of formula 1 " or "imidazopyridine compounds" or "compounds of the present invention" are used interchangeably and includes all the stereoisomeric and tautomeric forms and mixtures thereof in all ratios, and pharmaceutically acceptable salts, pharmaceutically acceptable solvates, prodrugs, N-oxides and polymorphs.

The term, "therapeutically effective amount" as used herein means an amount of compound or composition comprising compound of formula 1 , effective in producing the desired therapeutic response in a particular patient suffering from cancer. The therapeutically effective amount of the compound or composition will vary with the particular condition being treated, the age and physical condition of the end user, the severity of the condition being treated, the duration of the treatment, the nature of concurrent therapy, the specific compound or composition employed, the particular pharmaceutically acceptable carrier utilized, and like factors.

The term "subject" as used herein refers to an animal, preferably a mammal, and most preferably a human.

The term "mammal" used herein refers to warm-blooded vertebrate animals of the class 'Mammalia', including humans, characterized by a covering of hair on the skin and, in the female, milk-producing mammary glands for nourishing the young. The term mammal includes animals such as cat, dog, rabbit, bear, fox, wolf, monkey, deer, mouse, pig as well as human.

As used herein, the terms "treatment" "treat" and "therapy" and the like refer to alleviate, slow the progression, attenuation or cure of existing diseases or condition (e.g. inflammation). Treatment also includes treating the symptoms of the diseases condition.

Embodiments of the invention

In one embodiment, the present invention provides compounds of formula 1 ;

Formula 1

wherein,

X, Y, P and Q are independently selected from CR, N and N-oxide such that ring A and ring B independent of each other is a phenyl, pyridyl or pyrimidinyl ring;

R, R-i , R ₂ , R3, R4, R5 and R ₇ are independently selected from hydrogen, halogen, hydroxy, amino, cyano, (CrC ₆ )-alkyl, (CrC ₆ )-alkoxy, aryloxy, ar(Ci-C ₆ )alkyl, ar(CrC ₆ ) alkyloxy, (C ₃ -C ₁₂ )-cycloalkyl, heterocyclyl, haloalkyl, COOR _a , CONR _a R _b , S(0) _m (CrC ₆ )- alkyl wherein m is an integer from 0 to 2, and S(0) ₂ NR _a R _b ;

R ₆ is selected from hydrogen, halogen, hydroxy, cyano, (CrC ₆ )-alkyl, aralkyl, haloalkyl,

COORa or CONR _a R _b ; and

R ₈ is selected from hydrogen or (C-i-C ₆ )-alkyl ;

wherein,

(CrC ₆ )-alkyl is unsubstituted or substituted with one or more groups selected from halogen, hydroxy, cyano, (Ci-C ₆ )-alkyl, (CrC ₆ )-alkoxy, aryl, heterocyclyl or COOR _a ; each of (C ₃ -Ci ₂ )-cycloalkyl, aryl, ar(C-i-C ₆ )-alkyl and heterocyclyl is unsubstituted or substituted with one or more groups selected from halogen, hydroxy, cyano, amino, (C-i- C ₆ )-alkyl, (CrC ₆ )-alkoxy, aryl, heterocyclyl, haloalkyl, COOR _a or C(O)NR _a R _b ;

R _a and R _b are independently selected from hydrogen, (CrC ₆ )-alkyl, ar(Ci-C ₆ )-alkyl, aryl and heterocyclyl;

with a proviso that when R ₆ is hydrogen, X and Y are not CR such that ring A is not a phenyl ring; or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof. In a second embodiment, the present invention provides compounds of formula

1 ; wherein X, Y, P and Q are independently selected from CR, N and N-oxide such that ring A and ring B independent of each other is a phenyl, pyridyl or pyrimidinyl ring;

R is selected from hydrogen, halogen, hydroxy, amino, cyano, (C-i-C ₆ )-alkyl, (C-|-C ₆ )- alkoxy, haloalkyl, COOR _a or CONR _a R _b ;

Ri is selected from hydrogen, cyano, amino, (CrC ₆ )alkyl, haloalkyl, hydroxy or (CrC ₆ ) alkoxy;

R ₂ is H or (CrC ₆ ) alkyl;

R ₃ is selected from hydrogen, cyano, amino, (Ci-C ₆ )alkyl, (CrC ₆ ) alkoxy, S(0) _m (Ci-C ₆ )- alkyl wherein m is an integer from 0 to 2, or unsubstituted or substituted heterocyclyl; R ₄ , R ₅ and R ₇ are independently selected from hydrogen, halogen, cyano, amino, (C-i- C ₆ )alkyl and (C-|-C ₆ ) alkoxy;

R ₆ is selected from hydrogen, halogen, cyano, (CrC ₆ ) alkyl, haloalkyl, COOR _a or CONR _a R _b ;

R ₈ is selected from hydrogen or (CrC ₆ )-alkyl; and

R _a and Rb are independently selected from hydrogen, (CrC ₆ )-alkyl, ar(CrC ₆ )alkyl, aryl and heterocyclyl;

with a proviso that when R ₆ is hydrogen, X and Y are not CR such that ring A is not a phenyl ring;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

In a third embodiment, the present invention provides compounds of formula 1 ; wherein X is N, and Y is N or N-oxide; P and Q are CR; such that ring A is a pyrimidinyl ring and ring B is a phenyl ring; and R, Ri to R ₈ are as defined in the second embodiment;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

In a fourth embodiment, the present invention provides compounds of formula 1 ; wherein X is N, Y is N or N-oxide; P is N and Q is CR or P is CR and Q is N; such that ring A is a pyrimidinyl ring and ring B is a pyridyl ring; and R, Ri to R ₈ are as defined in the second embodiment;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

In a fifth embodiment, the present invention provides compounds of formula 1 ; wherein X is N, Y is N or N-oxide; P and Q are N; such that each of ring A and ring B is a pyrimidinyl ring; and R, Ri to R ₈ are as defined in the second embodiment;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

In a sixth embodiment, the present invention provides compounds of formula 1 ; wherein X is N, Y is CR; P and Q are CR; such that ring A is a pyridyl ring and ring B is a phenyl ring; and R, Ri to R ₈ are as defined in the second embodiment;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof. In a seventh embodiment, the present invention provides compounds of formula

1 ; wherein X is N and Y is CR; P is N and Q is CR or P is CR and Q is N; such that each of ring A and ring B is a pyridyl ring; and R, Ri to R ₈ are as defined in the second embodiment;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

In an eighth embodiment, the present invention provides compounds of formula 1 ; wherein X is N and Y is CR; P and Q are N; such that ring A is a pyridyl ring and ring B is a pyrimidinyl ring; and R, Ri to R ₈ are as defined in the second embodiment;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

In a ninth embodiment, the present invention provides compounds of formula 1 ; wherein X is CR and Y is N or N-oxide; P and Q are CR; such that ring A is a pyridyl ring and ring B is a phenyl ring; and R, Ri to R ₈ are as defined in the second embodiment;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

In a tenth embodiment, the present invention provides compounds of formula 1 ; wherein X is CR and Y is N or N-oxide; P is N and Q is CR or P is CR and Q is N ; such that each of ring A and ring B is a pyridyl ring; and R, Ri to R ₈ are as defined in the second embodiment;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

In an eleventh embodiment, the present invention provides compounds of formula 1 ; wherein X is CR and Y is N or N-oxide; P and Q are N ; such that ring A is a pyridyl ring and ring B is a pyrimidinyl ring; and R, Ri to R ₈ are as defined in the second embodiment;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

In a twelfth embodiment, the present invention provides compounds of formula 1 ; wherein X and Y are CR; P and Q are N ; such that ring A is a phenyl ring and ring B is a pyrimidinyl ring; R, R-i , R ₂ , R3, R4, R5, R7 and R ₈ are as defined in the second embodiment; R ₆ is selected from halogen, cyano, (CrC ₆ ) alkyl, haloalkyl, COOR _a or CONR _a R _b ; and R _a and R _b are independently selected from hydrogen, (C-i-C ₆ )-alkyl, aralkyl, aryl and heterocyclyl;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof. In a thirteenth embodiment, the present invention provides compounds of formula

1 ; wherein X and Y are CR; P is N and Q is CR or P is CR and Q is N ; such that ring A is a phenyl ring and ring B is a pyridyl ring; R, R-i , R ₂ , R3, R4, R5, R7 and R ₈ are as defined in the second embodiment; R ₆ is selected from halogen, cyano, (Ci-C ₆ )-alkyl, haloalkyl, COOR _a or CONR _a R _b ; and R _a and R _b are independently selected from hydrogen, (Ci-C ₆ )-alkyl, ar(Ci-C ₆ )alkyl, aryl and heterocyclyl; or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof. In a fourteenth embodiment, the present invention provides compounds of formula 1 ; wherein X and Y are CR; P and Q are CR; such that each of ring A and ring B is a phenyl ring; R, R _; R ₂ , R3, R ₄ , R5, R7 and R ₈ are as defined in the second embodiment; R ₆ is selected from halogen, cyano, (C-|-C ₆ ) alkyl, haloalkyl, COOR _a or CON R _a R _b ; and R _a and Rb are independently selected from hydrogen, (Ci -C ₆ )-alkyl, ar(Ci -C ₆ )alkyl, aryl and heterocyclyl;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

In a fifteenth embodiment, the present invention provides compounds of formula 1 ; wherein R is a heterocyclyl, where the heterocyclyl is selected from piperazinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl sulfone or tetrazolyl or N-oxides thereof; or the heterocyclyl may be substituted with one or more groups selected from halogen, hydroxy, cyano, (d-C ₆ )-alkyl, (C C ₆ )-alkoxy, haloalkyl, COOR _a or C(0)N R _a R _b ; R _a and Rb are independently selected from hydrogen, (CrC ₆ )-alkyl, ar(CrC ₆ )alkyl, aryl and heterocyclyl; X, Y, P, Q, R, R ₂ , R3, R4, R5, R7 and R ₈ are as defined in any of the preceding embodiments;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof. In a sixteenth embodiment, the present invention provides compounds of formula

1 ; wherein R ₂ is a heterocyclyl where the heterocyclyl is selected from piperazinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl sulfone or tetrazolyl or N-oxides thereof; or the heterocyclyl may be substituted with one or more groups selected from halogen, hydroxy, cyano, (C ₁ -C ₆ )-alkyl, (CrC ₆ )-alkoxy, haloalkyl, COOR _a or C(0)N R _a R _b ; R _a and R _b are independently selected from hydrogen, (C-i-C ₆ )-alkyl, ar(C-i-C ₆ )alkyl, aryl and heterocyclyl; X, Y, P, Q, R, R-i , R ₃ , R ₄ , R5, R7 and R ₈ are as defined in any of the preceding embodiments;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof. In a seventeenth embodiment, the present invention provides compounds of formula 1 ; wherein R ₃ , is a heterocyclyl where the heterocyclyl is selected from piperazinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl sulfone or tetrazolyl or N- oxides thereof;

or the heterocyclyl may be substituted with one or more groups selected from halogen, hydroxy, cyano, (C ₁ -C ₆ )-alkyl, (Ci-C ₆ )-alkoxy, haloalkyl, COOR _a or C(0)NR _a R _b ; R _a and R _b are independently selected from hydrogen, (C-i-C ₆ )-alkyl, ar(C-i-C ₆ )alkyl, aryl and heterocyclyl; X, Y, P, Q, R, R-i , R ₂ , R ₄ , R5, R7 and R ₈ are as defined in any of the preceding embodiments;

or a stereoisomer, tautomer or a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph or N-oxide thereof.

Representative compounds of formula 1 encompassed in accordance with the present invention include:

3-(4-(lsopropylthio)phenyl)-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine;

3-(4-(lsopropylsulfinyl)phenyl)-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine;

t-Butyl 4-(5-(3-(4-(isopropylsulfonyl) phenyl) imidazo [1 , 2-a] pyridin-6-yl) pyridin-2-yl) piperazine-1 -carboxylate

3-(4-(lsopropylthio)phenyl)-6-(6-(piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a] pyridine;

3- (4-(lsopropylsulfinyl)phenyl)-6-(6-(piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a] pyridine;

4- (3-(3-(4-(lsopropylthio)phenyl)imidazo[1 ,2-a]pyridin-6-yl)pyridin-2-yl) morpholine;

3-(4-(lsopropylthio)phenyl)-6-(6-methylpyridin-3-yl)imida zo[1 ,2-a]pyridine;

3-(4-(lsopropylsulfonyl) phenyl)-6-(6-methylpyridin-3-yl)imidazo[1 , 2-a]pyridine;

3-(6-Methylpyridin-3-yl)-6-(pyridin-3-yl) imidazo[1 , 2-a]pyridine;

3-(4-(lsopropylthio)phenyl)-8-methyl-6-(pyridin-3-yl)imid azo[1 , 2-a]pyridine;

3-(4-(lsopropylsulfinyl) phenyl)-8-methyl-6-(pyridin-3-yl) imidazo [1 , 2-a] pyridine;

3-(4-(lsopropylsulfonyl) phenyl)-8-methyl-6-(pyridin-3-yl) imidazo [1 , 2-a] pyridine;

8-Methyl-6-(2-methylpyrimidin-5-yl)-3-(4-(methylsulfonyl) phenyl)imidazo[1 ,2-a] pyridine; 3-(6-Methoxypyridin-3-yl)-8-methyl-6-(2-methylpyrimidin-5-yl )imidazo[1 ,2-a] pyridine; 3-(4-(lsopropylthio)phenyl)-6-(6-methoxypyridin-3-yl)-8-meth ylimidazo[1 ,2-a] pyridine; 6-(6-Methoxypyridin-3-yl)-8-methyl-3-(4-(methylsulfonyl)phen yl)imidazo [1 , 2-a] pyridine;

3-(4-(lsopropylthio)phenyl)-8-methyl-6-(6-methylpyridin-3-yl )imidazo[1 ,2-a] pyridine; 3-(4-(lsopropylsulfonyl) phenyl)-8-methyl-6-(6-methyl pyridine-3-yl)imidazo [1 , 2- a]pyridine;

8-Methyl-6-(6-methylpyridin-3-yl)-3-(4-(trifluoromethoxy) phenyl)imidazo [1 ,2-a] pyridine; 3-(4-(lsopropylsulfinyl)phenyl)-6-(pyrimidin-5-yl)imidazo[1 ,2-a] pyridine;

3-(4-(lsopropylsulfonyl) phenyl)-6-(pyrimidin-5-yl) imidazo [1 , 2-a] pyridine;

3-(3-(4-(lsopropylsulfonyl) phenyl) imidazo [1 , 2-a] pyridin-6-yl) pyridine-1 -oxide;

3-(6-Methoxypyridin-3-yl)-6-(pyridin-3-yl) imidazo [1 , 2-a] pyridine;

3-(3-(6-Methoxypyridin-3-yl) imidazo [1 , 2-a] pyridin-6-yl) pyridine-1 -oxide;

3- t-Butyl 4-(5-(6-(2,6-dimethylpyridin-3-yl)-8-methylimidazo [1 ,2-a]pyridin-3-yl) pyridin-

2- yl)piperazine-1 -carboxylate;

6-(2, 6-Dimethylpyridin-3-yl)-8-methyl-3 -(6-(piperazin-1 -yl) pyridin-3-yl) imidazo [1 , 2- a] pyridine;

3- (4-lsobutylphenyl)-8-methyl-6-(6-methylpyridin-3-yl) imidazo [1 , 2-a] pyridine;

t-Butyl 4-(5-(6-(6-cyanopyridin-3-yl)-8-methylimidazo [1 , 2-a] pyridin-3-yl) pyridin-2-yl) piperazine-1 -carboxylate;

5-(8-Methyl-3-(6-(piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl) picolinonitrile; 3-(4-(Methylsulfonyl) phenyl)-6-(pyridin-3-yl)imidazo [1 , 2-a] pyridine;

3-(4-(lsopropylthio) phenyl)-6-(2-methylpyridin-3-yl)imidazo [1 , 2-a] pyridine;

5-(3-(4-Morpholinophenyl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl)pyridin-2-amine; t-Butyl 4-(5-(6-(6-amino-5-(trifluoromethyl) pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl) pyridin-2-yl)piperazine-1 -carboxylate;

5-(3-(6-(Piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl) pyridin-

2- amine;

3- (4-(lsopropylthio)phenyl)-6-(5-(trifluoromethyl)pyridin-3-yl )imidazo[1 ,2-a] pyridine; 3-(4-(lsopropylsulfinyl)phenyl)-6-(5-(trifluoromethyl)pyridi n-3-yl)imidazo[1 ,2-a] pyridine; 3-(6-(Piperazin-1 -yl)pyridin-3-yl)-6-(5-(trifluoromethyl)pyridin-3-yl)imidazo [1 ,2-a] pyridine;

5-(3-(4-(Methylsulfonyl)phenyl)imidazo[1 ,2-a]pyridin-6-yl)picolinonitrile;

t-Butyl-4-(5-(6-(6-cyanopyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl) piperazine-1 - carboxylate;

5-(3-(6-(Piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl) picolinonitrile;

5-(3-(4-(lsopropylthio)phenyl)imidazo[1 ,2-a]pyridin-6-yl) picolinonitrile;

5-(6-(6-(Trifluoromethyl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-amine;

3-(4-Morpholinophenyl)-6-phenylimidazo[1 ,2-a]pyridine-8-carbonitrile; 3-(4-(lsopropylsulfonyl)phenyl)-6-phenylimidazo[1 ,2-a] pyridine-8-carbonitrile;

3-(4-(lsopropylthio)phenyl)-6-(6-methylpyridin-3-yl)imida zo[1 ,2-a]pyridine-8-carbonitrile; 6-(6-Methylpyridin-3-yl)-3-(4-morpholinophenyl)imidazo[1 ,2-a]pyridine-8-carbonitrile; Ethyl 6-(2-hydroxypyrimidin-5-yl)-3-(4-morpholinophenyl)imidazo[1 ,2-a]pyridine-8- carboxylate;

6-(2-Hydroxypyrimidin-5-yl)-3-(4-morpholinophenyl)imidazo [1 ,2-a]pyridine-8-carboxylic acid;

Methyl 3-(6-(4-(t-butoxycarbonyl)piperazin-1 -yl)pyridin-3-yl)-6-(2-methoxypyrimidin-5- yl)imidazo[1 ,2-a]pyridine-8-carboxylate;

Methyl 6-(2-methoxypyrimidin-5-yl)-3-(6-(piperazin-1 -yl) pyridin-3-yl)imidazo[1 ,2- a]pyridine-8-carboxylate;

3-(4-(1 ,1 -Dioxidothiomorpholino)phenyl)-6-(2-methoxy pyrimidin-5-yl)imidazo[1 ,2- a]pyridine-8-carbonitrile;

3-(4-(1 ,1 -Dioxidothiomorpholino)phenyl)-6-(2-hydroxypyrimidin -5-yl)imidazo[1 ,2- a]pyridine-8-carboxylic acid;

3-(6-(lsopropylthio)pyridin-3-yl)-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine;

5-(3-(6-(lsopropylthio)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl) pyridin-

2- amine;

t-Butyl 4-(3-methyl-5-(6-(5-(trifluoromethyl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl) pyridin-2-yl)piperazine-1 -carboxylate;

3- (5-Methyl-6-(piperazin-1 -yl)pyridin-3-yl)-6-(5-(trifluoro methyl)pyridin-3-yl) imidazo 1 ,2- a]pyridine;

5-(3-(4-Morpholinophenyl)imidazo[1 ,2-a]pyridin-6-yl)picolinonitrile;

5-(3-(4-(Methylsulfonyl)phenyl)imidazo[1 ,2-a]pyridin-6-yl)picolinamide;

N,N-Dimethyl-4-(5-(6-(5-(trifluoromethyl)pyridin-3-yl)imi dazo[1 ,2-a]pyridin-3-yl) pyridin-2- yl)piperazine-1 -carboxamide;

5-(3-(4-Thiomorpholine 1 ,1 -dioxidephenyl)imidazo[1 ,2-a]pyridin-6-yl) picolinonitrile; 5-(3-(6-Aminopyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl)pyridin-2-amine; 5-(3-(4-Aminophenyl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl)pyridin-2-amine;

5-(3-(5-Fluoropyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl)pyridin-2-amine; 5-(3-(4-(Methylsulfonyl)phenyl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl) pyridin-2- amine;

5-(6-(6-Methoxypyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)-3-(trifluoromethyl)pyridin-2- amine; 3- (6-Methoxypyridin-3-yl)-6-(5-(trifluoromethyl)pyridin-3-yl)i midazo[1 ,2-a]pyridine;

4- (4-(5,7-Dimethyl-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)phenyl)morpholine;

3-(2-Fluoropyridin-3-yl)-5,7-dimethyl-6-(pyridin-3-yl) imidazo [1 ,2-a]pyridine;

57-Dimethyl-6-(6-methylpyridin-3-yl)-3-(4-(methylsulfonyl )phenyl)imidazo[1 ,2-a] pyridine;

5- (5,7-Dimethyl-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)picolinonitrile;

3-(2-Methoxypyridin-3-yl)-5,7-dimethyl-6-(pyridin-3-yl)im idazo[1 ,2-a]pyridine;

57-Dimethyl-3-(4-(methylsulfonyl)phenyl)-6-(pyridin-3-yl) imidazo[1 ,2-a]pyridine;

3- (2-Methoxypyridin-3-yl)-7-methyl-6-(pyridin-3-yl) imidazo [1 ,2-a]pyridine;

4- (4-(8-Fluoro-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)phenyl)morpholine;

4- (8-Fluoro-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)benzene sulfonamide;

8-Fluoro-3-(4-(isopropylthio)phenyl)-6-(pyridin-3-yl)imid azo [1 ,2-a]pyridine;

5- (8-Fluoro-3-(4-(methylsulfonyl)phenyl)imidazo[1 ,2-a] pyridin-6-yl)picolinonitrile;

6- (6-(1 H-tetrazol-5-yl)pyridin-3-yl)-8-fluoro-3-(4-(methyl sulfonyl) phenyl) imidazo [1 ,2-a] pyridine;

4-(5-(8-Fluoro-6-(2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl) morpholine;

4-(4-(8-Fluoro-6-(6-methoxypyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl) phenyl) morpholine; 8-Fluoro-6-(6-methoxypyridin-3-yl)-3-(4-(methylsulfonyl)phen yl)imidazo[1 ,2-a] pyridine; t-Butyl 4-(5-(8-fluoro-6-(6-methoxypyridin-3-yl)imidazo[1 ,2-a] pyridin-3-yl)pyridin-2-yl) piperazine-1 -carboxylate;

Methyl 3-(8-fluoro-6-(6-methoxypyridin-3-yl) imidazo[1 ,2-a] pyridin-3-yl) benzoate;

3-(8-Fluoro-6-(6-methoxypyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)benzoic acid;

3-(4-(Methylthio)phenyl)-6-(pyridin-3-yl)-8-(trifluoromet hyl)imidazo[1 ,2-a]pyridine;

3-(4-(Methylsulfonyl)phenyl)-6-(pyridin-3-yl)-8-(trifluor omethyl)imidazo[1 ,2-a] pyridine; 6-(6-Methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)-8-(tri fluoromethyl)imidazo [1 ,2-a] pyridine;

6-(6-Methylpyridin-3-yl)-3-(3-(methylsulfonyl)phenyl)-8-(tri fluoromethyl)imidazo [1 ,2-a] pyridine;

t-Butyl 4-(5-(6-(6-methylpyridin-3-yl)-8-(trifluoromethyl) imidazo[1 ,2-a]pyridin-3-yl) pyridin-2-yl)piperazine-1 -carboxylate;

6-(6-Methylpyridin-3-yl)-3-(6-(piperazin-1 -yl)pyridin-3-yl)-8-(trifluoromethyl) imidazo[1 ,2- a]pyridine; N,N-dimethyl-4-(5-(6-(6-methylpyridin-3-yl)-8-(trifluorometh yl)imidazo[1 ,2-a] pyridin-3-yl) pyridin-2-yl)piperazine-1 -carboxamide;

4-(4-(6-(6-Methylpyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-3-yl)phenyl) morpholine;

4-(4-(6-(6-Methylpyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-3-yl) phenyl) morpholine 4-oxide;

4-(4-(6-(6-Methylpyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-3-yl)phenyl) thiomorpholine-1 ,1 -dioxide;

3-(4-(lsopropylthio)phenyl)-6-(6-methylpyridin-3-yl)-8-(trif luoromethyl)imidazo[1 ,2-a] pyridine;

3- (4-(lsopropylsulfonyl)phenyl)-6-(6-methylpyridin-3-yl)-8-(tr ifluoromethyl) imidazo[1 ,2-a] pyridine;

4- (5-(6-(2-methylpyrimidin-5-yl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-3-yl) pyridin-2- yl)morpholine;

5- (3-(3-(Methylsulfonyl)phenyl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoro methyl)pyridin-2-amine;

4- (4-(6-(o-Tolyl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-3-yl)phenyl)morpholine;

5- (3-(4-(t-Butyl)phenyl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-6-yl)picolinonitrile;

5-(3-(6-(Piperazin-1 -yl)pyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-6-yl) picolinonitrile;

4-(4-(6-(6-Cyanopyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a] pyridin-3-yl)phenyl) thiomorpholine-1 ,1 -dioxide;

4-(4-(6-(4-t-Butylphenyl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-3-yl)phenyl)

morpholine;

4-(6-(4-(t-Butyl)phenyl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-3-yl)benzene

sulfonamide;

4-(4-(6-(2-Methoxypyrimidin-5-yl)-8-(trifluoromethyl)imidazo [1 ,2-a]pyridin-3-yl) phenyl) morpholine;

4-(4-(8-Chloro-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)phenyl) morpholine; 3-(4-(lsopropylthio)phenyl)-6-(6-methylpyridin-3-yl)-8-(trif luoromethyl)imidazo[1 ,2-a] pyridine;

8-Chloro-3-(4-(isopropylsulfinyl)phenyl)-6-(6-methylpyridin- 3-yl)imidazo[1 ,2-a]pyridine; 8-Chloro-3-(4-(isopropylsulfonyl)phenyl)-6-(6-methylpyridin- 3-yl)imidazo[1 ,2-a]pyridine; 4-(5-(8-Chloro-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl) morpholine;

4-(4-(8-Chloro-6-(2-methoxypyrimidin-5-yl)imidazo[1 ,2-a]pyridin-3-yl)phenyl)

morpholine;

8-Chloro-3-(4-(isopropylthio)phenyl)-6-(2-methoxypyrimidin-5 -yl)imidazo[1 ,2-a] pyridine; 8-Chloro-3-(4-(isopropylsulfonyl)phenyl)-6-(2-methoxy pyrimidin-5-yl)imidazo[1 ,2-a] pyridine;

t-Butyl-4-(5-(8-chloro-6-(2-methoxypyrimidin-5-yl)imidazo [1 ,2-a]pyridin-3-yl)pyridin-2-yl) piperazine-1 -carboxylate;

8-Chloro-6-(2-methoxypyrimidin-5-yl)-3-(6-(piperazin-1 -yl) pyridin-3-yl) imidazo [1 ,2- a]pyridine;

4- (4-(8-Chloro-6-(2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridin-3-yl)phenyl) morpholine; 3-(2-Methoxypyridin-3-yl)-7-methyl-6-(6-methylpyridin-3-yl)i midazo[1 ,2-a]pyridine;

3-(6-Methoxypyridin-3-yl)-7-methyl-6-(6-methylpyridin-3-y l)imidazo[1 ,2-a]pyridine;

t-Butyl 4-(5-(6-(pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl)piperazine-1 - carboxylate;

3-(6-(Piperazin-1 -yl)pyridin-3-yl)-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine;

3-(3-(6-(4-(t-Butoxycarbonyl)piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl) pyridine 1 -oxide;

3-(3-(6-(Piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)pyridine 1 -oxide;

t-Butyl 4-(5-(6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl)piperazine-1 - carboxylate;

6-(6-Methylpyridin-3-yl)-3-(6-(piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridine;

5- (3-(6-(4-(t-Butoxycarbonyl)piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)-2- methylpyridine 1 -oxide;

t-Butyl 4-(5-(8-chloro-6-(2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl) piperazine-1 -carboxylate;

8-Chloro-6-(2-methylpyrimidin-5-yl)-3-(6-(piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a] pyridine;

or a stereoisomer, tautomer, pharmaceutically acceptable salt, pharmaceutically acceptable solvate, pharmaceutically acceptable prodrug or pharmaceutically acceptable polymorph thereof. The compounds of the present invention also include all stereoisomeric and tautomeric forms and mixtures thereof in all ratios and their pharmaceutically acceptable salts, solvates, prodrugs, N-oxides and polymorphs.

According to another aspect of the present invention, the compound of formula 1 can be prepared by various methods including using methods well known to the person skilled in the art. Examples of processes for the preparation of the compounds of formula 1 are described below and illustrated in the scheme but are not limited thereto. It will be appreciated by persons skilled in the art that within certain of the processes described herein, the order of the synthetic steps employed may be varied and will depend inter alia on factors such as the nature of functional groups present in a particular substrate and the protecting group strategy (if any) to be adopted. Clearly, such factors will also influence the choice of reagent such as bases, solvents, coupling agents to be used in the reaction steps.

The reagents, reactants and intermediates used in the following processes are either commercially available or can be prepared according to standard procedures known in the art, for instance those reported in the literature references. In the following schemes and the description of the processes for the synthesis of the compounds of formula 1 , the starting compounds and the intermediates used for the synthesis of compounds of the present invention, are designated as compounds 2, 3, 4, 5, 5a, 6, 7, 8 and 8a for ease of reference. Throughout the process description, the corresponding substituent groups in the various formulae representing starting compounds and intermediates have the same meanings as that for the compound(s) of formula 1 unless stated otherwise.

The processes used in the scheme of the present invention, are referred to by using general symbols namely 1 a, 1 b, 1 c and 1 d.

Processes for the preparation of compounds of the present invention are depicted in the following scheme: Scheme:

The following scheme depicts a process for the preparation of the compounds of formula 1 . Unless otherwise stated, the variables in X, Y, P, Q, R-i , R ₂ , R3, R4, R5, Re, R ₇ and R ₈ in the starting compounds and intermediates, designated herein as the compounds of formulae 2, 3, 4, 5, 5a, 6, 7, 8 and 8a, are as defined for the compounds of Formula 1 in any one of the embodiments related to the said compounds of formula 1 .

Formula 1

Step 1

Preparation of compound of formula 4:

The compound of formula 2;

2

wherein R ₅ , R ₆ , and R ₇ are as defined above,

is reacted with compound of formula 3;

3

wherein R ₈ is as defined above;

optionally in the presence of a base such as sodium acetate or potassium acetate, followed by reflux with concentrated hydrochloric acid in 40-70 % aqueous alcohol as the solvent, wherein the alcohol is selected from methanol, ethanol or isopropanol, preferably 60 % ethanol in water, for 3-24 h, to obtain the compound of formula 4 (Reaction 1 a);

4

wherein R ₅ , R ₆ , R ₇ , and R ₈ are as above. Step 2

Preparation of compound of formula 6:

The compound of formula 4 (obtained in Step 1 ) is reacted with the compound of formula 5 or formula 5a, which compounds are commercially available or may be synthesized by procedures well-known in the art;

5 5a wherein X, Y, R and R ₂ are as defined above; in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane, dichlorobis(triphenylphosphine)palladium(ll) or tetrakis(triphenyl- phosphine)palladium(O), in the presence of an aqueous solution of a base selected from sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide in a solvent such as dry DMF, 1 ,4-dioxane or THF at a temperature range of 80-150 °C for about 1 -5 h to obtain the compound of formula 6 (Journal of organic chemistry, 2004, 69, 20, 6812-6820);

6

wherein X, Y, R _; R ₂ , R5, Re, R7, and R ₈ are as defined above; Step 3

Preparation of compound of formula 7:

The compound of formula 6 (as obtained in Step 2) is reacted with N-bromosuccinimide in a solvent selected from chloroform, dichloromethane or carbon tetrachloride at a temperature range of 0-30 °C for 15 min to 2 h, to obtain the compound of formula 7;

7

wherein X, Y, R-i , R ₂ , R5, Re, R7, and R ₈ are as defined above. Step 4

Preparation of compound of formula 1 :

The compound of formula 7 (as obtained in Step 3) is reacted with the compound of formula 8 or formula 8a; wherein P, Q, R ₃ and R ₄ are as defined above;

in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane, dichlorobis(triphenylphosphine)palladium(ll) or tetrakis(triphenyl- phosphine)palladium(O), in the presence of an aqueous solution of a suitable base selected from sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide in a suitable solvent such as dry DMF, 1 ,4-dioxane or THF at a temperature range of 80-150 °C for about 1 -5 h to obtain the compound of formula 1 (Journal of organic chemistry, 2004, 69, 20, 6812-6820).

Step 5

Preparation of pharmaceutically acceptable salt of compound of formula 1 :

The compound of formula 1 (obtained in step 4) may be converted into its pharmaceutically acceptable salt.

The present invention also includes within its scope pharmaceutically acceptable salts or solvates thereof.

The term "pharmaceutically acceptable salts" as used herein refers to organic and inorganic salts of a compound of the invention, depending on the particular group (acidic or basic group) present in the compounds of formula 1 described herein. When compounds of the present invention contain relatively acidic groups, base addition salts can be obtained by contacting the compounds of formula 1 with a sufficient amount of an appropriate base, either neat or in a suitable inert solvent. Examples of pharmaceutically acceptable base addition salts include sodium, potassium, calcium, magnesium, ammonium or organic base salt. Examples of pharmaceutically acceptable organic base addition salts include those derived from organic bases like lysine, arginine, guanidine, diethanolamine, choline, and tromethamine.

When compounds of the present invention contain relatively basic groups, acid addition salts can be obtained by contacting the compounds of formula 1 with a sufficient amount of an appropriate acid, either neat or in a suitable inert solvent. Examples of pharmaceutically acceptable acid addition salts include those derived from inorganic acids like hydrochloric, hydrobromic, nitric, carbonic, monohydrogencarbonic, phosphoric, monohydrogenphosphoric, dihydrogenphosphoric, sulfuric, mono- hydrogensulfuric or hydriodic acids and the like, as well as the salts derived from organic acids like acetic, propionic, isobutyric, oxalic, maleic, malonic, benzoic, succinic, suberic, fumaric, mandelic, phthalic, benzenesulfonic, p-tolylsulfonic, citric, tartaric, methanesulfonic, glucuronic or galacturonic acids and the like. Certain specific compounds of the present invention contain both basic and acidic functionalities that allow the compounds to be converted into either base or acid addition salts.

The compounds of formula 1 may be regenerated from their corresponding salts by contacting the salt with an appropriate base or acid depending on the type of salt and isolating the parent compound in the conventional manner. The compound differs from the various salt forms in certain physical properties. An example of physical properties that may differ is solubility in polar solvents.

Certain compounds of the present invention can exist in unsolvated forms as well as solvated forms, including hydrated forms. Certain compounds of the present invention may exist in multiple crystalline or amorphous forms. In general, all physical forms are suitable for the uses contemplated by the present invention and are intended to be within the scope of the present invention.

Various polymorphs of compounds of formula 1 can be prepared by crystallization of the compounds under different conditions. The different conditions are, for example, using different solvents or their mixtures for crystallization; crystallization at different temperatures; various modes of cooling, ranging from very fast to very slow cooling during crystallizations. Polymorphs can also be obtained by heating or melting the compound followed by gradual or fast cooling. The presence of polymorphs can be determined by IR (Infra-red) spectroscopy, solid probe NMR (Nuclear Magnetic Resonance) spectroscopy, differential scanning calorimetry, powder X-ray diffraction or such other techniques.

Those skilled in the art will recognize that stereocentres exist in compounds of formula 1 . Accordingly, the present invention includes all possible stereoisomers and geometric isomers of formula 1 and includes not only racemic compounds but also the optically active isomers as well. When a compound of formula 1 is desired as a single enantiomer, it may be obtained either by resolution of the final product or by stereospecific synthesis from either isomerically pure starting material or an appropriate intermediate. Resolution of the final product, an intermediate or a starting material may be effected by any suitable method known in the art, for example, Chiral reagents for Asymmetric Synthesis by Leo A. Paquette; John Wiley & Sons Ltd (2003).

Additionally, in situations wherein tautomers of the compounds of formula 1 are possible, the present invention is intended to include all tautomeric forms of the compounds.

The present invention also encompasses within its scope prodrugs of the compound of formula 1 . The preferable prodrugs are those that are converted intracellular^, more preferably, where the cellular converting location is the site of therapeutic action. For instance, preferred produgs are pharmaceutically acceptable ester derivatives convertible by solvolysis under physiological conditions to the parent carboxylic acid, e.g., lower alkyl esters, cycloalkyl esters, lower alkenyl esters, benzyl esters, mono- or di-substituted lower alkyl esters such as the pivaloyloxymethyl ester and the like conventionally used in the art (An introduction to Medicinal Chemistry, Graham. L. Patrick, Second Edition, Oxford University Press, pg 239-248; Prodrugs: Challenges and Rewards, Part 1 and Part 2, AAPS Press, Edited by Valentino J. Stella, Renald T. Borchardt, Michael J. Hagemon, Reza Oliyai, Hans Maag, Jefferson W. Tilley).

The present invention furthermore relates to pharmaceutical compositions that contain a therapeutically effective amount of at least one compound of formula 1 or its pharmaceutically acceptable salt in addition to a customary pharmaceutically acceptable carrier, and to a process for the production of a pharmaceutical composition, which includes bringing at least one compound of formula 1 , into a suitable administration form using a pharmaceutically acceptable and physiologically tolerable excipient and, if appropriate, further suitable active compounds, additives or auxiliaries.

The compositions can be administered orally, for example in the form of pills, tablets, coated tablets, capsules, granules or elixirs. Administration, however, can also be carried out rectally, for example in the form of suppositories, or parenterally, for example intravenously, intramuscularly or subcutaneously, in the form of injectable sterile solutions or suspensions, or topically, for example in the form of ointments or creams or transdermal^, in the form of patches, or in other ways, for example in the form of aerosols or nasal sprays.

As used herein, the term "pharmaceutically acceptable" means that the carrier, diluent, excipients, and/or salt must be compatible with the other ingredients of the formulation, and not deleterious to the recipient thereof.

The pharmaceutical preparations according to the invention are prepared in a manner known and familiar to one skilled in the art. Pharmaceutically acceptable inert inorganic and/or organic carriers and/or additives can be used in addition to the compound(s) of formula 1 , and/or its (their) physiologically tolerable salt(s). For the production of pills, tablets, coated tablets and hard gelatin capsules it is possible to use, for example, lactose, corn starch or derivatives thereof, gum arabica, magnesia or glucose, etc. Carriers for soft gelatin capsules and suppositories are, for example, fats, waxes, natural or hardened oils, etc. Suitable carriers for the production of solutions, for example injection solutions, or of emulsions or syrups are, for example, water, physiological sodium chloride solution or alcohols, for example, ethanol, propanol or glycerol, sugar solutions, such as glucose solutions or mannitol solutions, or a mixture of the various solvents which have been mentioned.

The pharmaceutical preparations normally contain about 1 to 99 %, for example, about 5 to 70 %, or from about 1 0 to about 30 % by weight of the compound of formula 1 or its physiologically tolerable salt. The amount of the compound of formula 1 or its physiologically tolerable salt in the pharmaceutical preparations normally is from about 5 to 500 mg. The dose of the compounds of this invention, which is to be administered, can cover a wide range. The dose to be administered daily is to be selected to suit the desired effect. A suitable dosage is about 0.01 to 1 00 mg/kg/day of the compound of formula 1 or their physiologically tolerable salt, for example, about 0.1 to 50 mg/kg/day of a compound of formula 1 or a pharmaceutically acceptable salt of the compound. If required, higher or lower daily doses can also be administered.

The selected dosage level will depend upon a variety of factors including the activity of a compound of the present invention employed, or the salt thereof, the route of administration, the time of administration, the rate of excretion of the particular compound being employed, the duration of the treatment, other drugs, compounds and/or materials used in combination with the particular compounds employed, the age, sex, weight, condition, general health and prior medical history of the patient being treated, and like factors well known in the medical arts.

In addition to the compound of the formula 1 or its physiologically acceptable salt and carrier substances, the pharmaceutical preparations can contain additives such as, for example, fillers, antioxidants, dispersants, emulsifiers, defoamers, flavors, preservatives, solubilizers or colorants. They can also contain two or more compounds of formula 1 or their physiologically tolerable salts. Furthermore, in addition to at least one compound of formula 1 or its physiologically tolerable salt, the pharmaceutical preparations can also contain one or more other therapeutically or prophylactically active ingredients.

As used herein, the term "pharmaceutically acceptable carrier" refers to a material that is non-toxic, inert, solid, semi-solid or liquid filler, diluent, encapsulating material or formulation auxiliary of any type which is compatible with a subject, preferably a mammal, more preferably a human, and is suitable for delivering an active agent to the target site without terminating the activity of the agent.

The present invention also encompasses within its scope the use of a compound of formula 1 or a pharmaceutically acceptable salt of the compound in combination with other pharmaceutically active compounds selected from monoclonal antibodies, nonsteroidal anti-inflammatory drugs (NSAI Ds) such as COX inhibitors or PDE4 inhibitors. Examples of monoclonal antibodies include, but not limited to, rituximab, etanercept, infliximab, adalimumab, natalizumab and vedolizumab. Examples of NSAI Ds include, but not limited to, diclofenac, indomethacin, sulindac, mefenamic acid, piroxicam, ibuprofen, naproxen, ketoprofen, phenylbutazone, aspirin, diflunisal, nimesulide, celecoxib, valdecoxib, etorcoxib and meloxicam. Examples of PDE4 inhibitors include, but not limited to, rolipram, ibudilast, luteolin and roflumilast. For instance, a pharmaceutical composition including a compound of formula 1 or a pharmaceutically acceptable salt can be administered to a mammal, in particular a human, with any other pharmaceutically active compounds, in mixtures with one another or in the form of pharmaceutical preparations.

In one aspect, the present invention relates to a method for inhibiting one or more pro-inflammatory cytokines selected from TNF-a, IL-1 β , IL-6, IL-8, IL-1 2, IL-17 or IL-23, comprising administering to a subject in need thereof an amount of the compounds of formula 1 effective to inhibit said pro-inflammatory cytokines.

In another aspect, the present invention relates to a method for the treatment of diseases or disorders mediated by one or more pro-inflammatory cytokines selected from TNF-a, I L- 1 β , IL-6, IL-8, IL-1 2, IL-1 7 or IL-23, comprising administering to a subject in need thereof a therapeutically effective amount of the compounds of formula 1 . In another aspect, the present invention provides use of a compound of formula 1 ; for the treatment of diseases or disorders mediated by one or more proinflammatory cytokines selected from TNF-a, IL-1 β , IL-6, IL-8, IL-1 2, IL-1 7 or IL-23.

In one aspect, the present invention provides use of a compound of formula 1 ; for the manufacture of a medicament for the treatment of diseases or disorders mediated by one or more proinflammatory cytokines selected from TNF-a, I L- 1 β , IL-6, IL-8, IL- 1 2, IL-1 7 or IL-23.

In an embodiment of the present invention, the disease or disorder is mediated by one or more pro-inflammatory cytokines selected from TNF-a, I L-1 β , IL-6, IL-8, IL-1 2, IL-1 7 or IL- 23, selected from the group consisting of : bone resorption disease (osteoporosis); arthritis selected from rheumatoid arthritis, osteoarthritis, juvenile rheumatoid arthritis, psoriatic arthritis, osteoarthritis, refractory rheumatoid arthritis or chronic non-rheumatoid arthritis; respiratory disorders selected from adult respiratory distress syndrome, asthma, rheumatoid asthma, systemic lupus erythematosus (SLE), pulmonary fibrosis, chronic obstructive pulmonary disease or lung sarcoidosis; kidney disorders selected from renal fibrosis, polycystic kidney disease (PKD), nephritis, diabetic nephropathy or glomerular nephritis; central nervous system (CNS) disorders selected from Alzheimer's disease, Parkinson's disease or multiple sclerosis; liver disorders; inflammatory bowel disease selected from Crohn's disease or ulcerative colitis; skin disorders selected from delayed-type hypersensitivity in skin, dermatitis, urticaria, psoriasis or scleroderma; vascular disorders selected from coronary heart disease, myocardial infarction, stroke, circulatory shock, arterial sclerosis, atherosclerosis, varicose veins, vasculitis or septic shock syndrome; allergies selected from allergic rhinitis or allergic conjunctivitis; cancer selected from glioblastoma, myeloid leukemia, acute myeloid leukemia, ovarian cancer or Kaposi's sarcoma; graft versus host disease; diverticulitis; Type I I diabetes; diabetic retinopathy; glaucoma and ankylosing spondylitis.

According to an embodiment of the present invention, the disease or disorder mediated by one or more pro-inflammatory cytokines selected from TNF-a, IL-1 β , IL-6, IL-8, IL-1 2, IL-17 or IL-23 is arthritis selected from rheumatoid arthritis, osteoarthritis, juvenile rheumatoid arthritis, psoriatic arthritis, osteoarthritis, refractory rheumatoid arthritis or chronic non-rheumatoid arthritis.

According to a second embodiment of the present invention, the disease or disorder mediated by one or more pro-inflammatory cytokines selected from TNF-a, IL- 1 β , IL-6, IL-8, IL-12, IL-17 or IL-23 is a respiratory disorder selected from adult respiratory distress syndrome, asthma, rheumatoid asthma, systemic lupus erythematosus (SLE), pulmonary fibrosis, chronic obstructive pulmonary disease or lung sarcoidosis.

According to a third embodiment of the present invention, the disease or disorder mediated by one or more pro-inflammatory cytokines selected from TNF-a, I L- 1 β , IL-6, IL-8, IL-12, IL-17 or IL-23 is a kidney disorder selected from renal fibrosis, polycystic kidney disease (PKD), nephritis, diabetic nephropathy or glomerular nephritis.

According to a fourth embodiment of the present invention, the disease or disorder mediated by one or more pro-inflammatory cytokines selected from TNF-a, IL- 1 β , IL-6, IL-8, IL-12, IL-17 or IL-23 is a central nervous system (CNS) disorder selected from Alzheimer's disease, Parkinson's disease or multiple sclerosis, liver disorders, inflammatory bowel disease selected from Crohn's disease or ulcerative colitis

According to a fifth embodiment of the present invention, the disease or disorder mediated by one or more pro-inflammatory cytokines selected from TNF-a, I L- 1 β , IL-6, IL-8, IL-12, IL-17 or IL-23 is a skin disorder selected from delayed-type hypersensitivity in skin, dermatitis, urticaria, psoriasis or scleroderma.

According to a sixth embodiment of the present invention, the disease or disorder mediated by one or more pro-inflammatory cytokines selected from TNF-a, I L- 1 β , IL-6, IL-8, IL-12, IL-17 or IL-23 is a vascular disorder selected from coronary heart disease, myocardial infarction, stroke, circulatory shock, arterial sclerosis, atherosclerosis, varicose veins, vasculitis or septic shock syndrome.

According to a seventh embodiment of the present invention, the disease or disorder mediated by one or more pro-inflammatory cytokines selected from TNF-a, IL- 1 β , IL-6, IL-8, IL-12, IL-17 or IL-23 is cancer selected from glioblastoma, myeloid leukemia, acute myeloid leukemia, ovarian cancer or Kaposi's sarcoma.

It is understood that modifications that do not substantially affect the activity of the various aspects of this invention are included. Accordingly, the following examples are intended to illustrate but not to limit the present invention.

The following abbreviations or terms are used herein

CHCIs Chloroform

CDCI ₃ Deuteriated chloroform

C0 ₂ Carbon dioxide N, N-dimethylformamide

Dimethylsulfoxide

Ethylene diamine tetra acetic acid

Gram

Hour

Hydrochloric acid

Kilogram

Milligram

Minute(s)

Millilitre

Microlitre

Micromolar

Millimolar

Mole

Sodium carbonate

Degree Centigrade

Roswell Park Memorial Institute, USA

Tetrahydrofuran

Example 1 :

6-Bromoimidazo [1 , 2-a] pyridine

To a stirred solution of 5-bromo-pyridin-2-amine (5 g, 28.9 mmol) and sodium acetate (4.0 g, 48.76 mmol) in 100 mL of 60 % ethanol in water, was added a refluxed solution of sodium acetate (2.0 g, 24.38 mmol) followed by 2-chloro-1 ,1 -dimethoxyethane (6.66 g, 53.5 mmol) in concentrated hydrochloric acid (1 .0 mL) in water (6 mL) and the reaction mass was refluxed for 2.5 h. The solvent was removed, residue obtained was diluted with cold water and pH adjusted to neutral (~7) with saturated sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate (2x100 mL), washed with water (2x100 mL) and brine (2x100 mL) and dried over anhydrous sodium sulphate. The crude material obtained was purified by trituration using 2 % ethyl acetate in petroleum ether. Yield: 3.6 g (64.28 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.33 (dd, 1 H, J=1 .8, 9.6 Hz, Ar), 7.55 (d, 1 H, J=9.6 Hz, Ar), 7.60 (s, 1 H, Ar), 7.92 (s, 1 H, Ar), 8.91 (s, 1 H, Ar); MS (ES+): m/e 198 (M+1 ). Example 2:

6-(Pyridin-3-yl) imidazo [1 , 2-a] pyridine

[1 ,1 '-Bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.057 g, 0.069 mmol) was added to a stirred solution of the compound of example 1 (1 .0 g, 5.08 mmol) and pyridin-3-ylboronic acid (0.8 g, 6.51 mmol) in dry dimethylformamide (15 mL) under nitrogen atmosphere at 120 °C, followed by addition of potassium carbonate (1 .0 g, 7.23 mmol) in water (5 mL). The reaction mixture was stirred for 2 h at 120 °C. The reaction mixture was cooled, diluted with water (250 mL) and extracted with chloroform (3x50 mL). The organic layers were combined and washed with water (75 mL), brine (75 mL) and dried over anhydrous sodium sulphate. The crude material obtained was purified using column chromatography (silica gel, methanol in chloroform) to afford the title compound. Yield: 0.81 g (81 .8 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.52 (q, 1 H, J=4.8 Hz, Ar), 7.64-7.71 (m, 3H, Ar), 7.98 (s, 1 H, Ar), 8.12-8.15 (m, 1 H, Ar), 8.61 (d, 1 H, J=6.0 Hz, Ar), 8.95 (d, 1 H, J=2.4 Hz, Ar), 9.03 (s, 1 H, Ar); MS (ES+): m/e 196 (M+1 ).

Example 3:

3-Bromo-6-(pyridin-3-yl) imidazo [1 , 2-a] pyridine

N-Bromosuccinimide (0.95 g, 5.33 mmol) was added to a stirred solution of compound of example 2 (1 .0 g, 5.12 mmol) in chloroform at 10 °C. The reaction mixture was stirred for 1 h. The reaction mixture was diluted with water (75 mL) and extracted with chloroform (50 mL χ 3). The organic layers were combined, washed with water (75 mL), brine (75 mL) and dried over anhydrous sodium sulphate. The crude material obtained was purified using column chromatography (silica gel, methanol in chloroform) to afford the title compound. Yield: 1 .2 g (85.71 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.54 (q, 1 H, J=4.8 Hz, Ar), 7.72-7.81 (m, 3H, Ar), 8.20-8.24 (m, 1 H, Ar), 8.60 (s, 1 H, Ar), 8.64 (dd, 1 H, J=1 .5, 4.8 Hz, Ar), 9.01 (d, 1 H, J=2.1 Hz, Ar); MS (ES+): m/e 275 (M+1 ). Example 4:

3-(4-(lsopropylthio)phenyl)-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 3 (5.0 g, 18.24 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (4.65 g, 23.71 mmol) in the presence of dichlorobis(triphenylphosphine)palladium(ll) (0.238 g, 0.339 mmol) and potassium carbonate (3.78 g, 27.4 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 4.0 g (63.5 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1.29 (d, 6H, J=6.9 Hz, 2CH ₃ ), 3.55- 3.64 (m, 1H, CH), 7.48-7.53 (m, 3H, Ar), 7.65-7.81 (m, 4H, Ar), 7.84 (s, 1H, Ar), 8.15 (d, 1H, J=9.0 Hz, Ar), 8.60 (d, 1H, J=6.0 Hz, Ar), 8.75 (s, 1H, Ar), 8.96 (d, 1H, J=1.8 Hz, Ar); MS (ES+): m/e 346 (M+1).

Example 5:

3-(4-(lsopropylsulfinyl)phenyl)-6-(pyridin-3-yl)imidazo[1,2- a]pyridine

Metachloroperbenzoic acid (0.064 g, 0.37 mmol) was added to a stirred solution of compound of example 4 (0.1 g, 0.28 mmol) in dry dichloromethane (10 mL) at 25 °C. The reaction mixture was stirred for 1 h. The reaction mixture was diluted with water (25 mL) and stirred with saturated sodium bicarbonate solution and extracted with chloroform (20 mL ^χ 3). The organic layers were combined, washed with water (25 mL), brine (25 mL) and dried over sodium sulphate. The crude material obtained was purified using column chromatography (silica gel, methanol in chloroform) to afford the title compound. Yield: 0.080 g (76.19 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1.02 (d, 3H, J=6.9 Hz, CH ₃ ), 1.25 (d, 3H, J=6.9 Hz, CH ₃ ), 3.01-3.06 (m, 1H, CH), 7.52 (q, 1H, J=4.8 Hz, Ar), 7.70-7.85 (m, 4H, Ar), 7.94-8.02 (m, 3H, Ar), 8.16-8.19 (m, 1H, Ar), 8.61-8.62 (m, 1H, Ar), 8.85 (s, 1H, Ar), 8.98 (d, 1H, J=2.1 Hz, Ar); MS (ES+): m/e 362 (M+1).

Example 6:

t-Butyl 4-(5-(imidazo [1, 2-a] pyridin-6-yl) pyridin-2-yl) piperazine-1-carboxylate

A mixture of the compound of example 1 (1.0 g, 5.08 mmol) and t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (1.97 g, 5.08 mmol) were treated with [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.124 g, 0.152 mmol) and sodium carbonate (2.15 g, 20.30 mmol) in dry dimethylformamide (100 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.05 g (54.68 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1.39 (s, 9H, 3CH ₃ ), 3.44 (s, 4H, 2CH ₂ ), 3.55 (s, 4H, 2CH ₂ ), 6.95 (d, 1H, J=8.7 Hz, Ar), 7.50-7.62 (m, 3H, Ar), 7.87 (d, 1H, J=2.4 Hz, Ar), 7.90 (s, 1H, Ar), 8.46 (d, 1H, J=2.4 Hz, Ar), 8.83 (s, 1H, Ar); MS (ES+): m/e 380 (M+1). Example 7:

t-Butyl 4-(5-(3-bromoimidazo [1 , 2-a] pyridin-6-yl) pyridin-2-yl) piperazine-1 - carboxylate

The compound of example 6 (1 .0 g, 2.64 mmol) was treated with N-bromosuccinimide (0.51 6 g, 2.90 mmol) in dry chloroform (20 mL) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 1 .1 g (91 .66 %); MS (ES+): m/e 459 (M+1 ). Example 8:

t-Butyl 4-(5-(3-(4-(isopropylthio) phenyl) imidazo [1 , 2-a] pyridin-6-yl) pyridin-2-yl) piperazine-1 -carboxylate

Dichlorobis(triphenylphosphine)palladium(l l) (0.026 g, 0.037 mmol) was added to a stirred solution of (4-(isopropylthio)phenyl)boronic acid (0.584 g, 2.98 mmol) and the compound of example 7 (1 .050 g, 2.29 mmol) in dry dimethylformamide (1 00 mL) under nitrogen atmosphere at 1 20 °C, followed by addition of potassium carbonate (0.475 g, 3.44 mmol) in water (5 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.850 g (70.83 %) ; ¹ H NMR (DMSO-de, 300 MHz): δ 1 .26 (d, 6H, J=6.6 Hz, 2CH ₃ ), 1 .41 (s, 9H, 3CH ₃ ), 3.42 (s, 4H, 2CH ₂ ), 3.58 (s, 4H, 2CH ₂ ), 3.54-3.59 (m, 1 H, CH), 6.92 (d, 1 H, J=9.0 Hz, Ar), 7.48-7.59 (m, 3H, Ar), 7.69-7.73 (m, 3H, Ar), 7.78 (s, 1 H, Ar), 7.91 (dd, 1 H, J=2.4, 9.0 Hz, Ar), 8.48 (d, 1 H, J=2.4 Hz, Ar), 8.58 (s, 1 H, Ar); MS (ES+): m/e 530 (M+1 ).

Example 9A:

t-Butyl 4-(5-(3-(4-(isopropylsulfinyl)phenyl)imidazo[1 ,2-a]pyridin-6-yl) pyridin-2- yl)piperazine-1 -carboxylate

The compound of example 8 (0.3 g, 0.566 mmol) was treated with metachloroperbenzoic acid (0.293 g, 1 .69 mmol) in dry dichloromethane (1 0 mL) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.1 85 g (58.1 7 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.98 (d, 3H, J=6.9, CH ₃ ), 1 .20 (d, 3H, J=6.9, CH ₃ ), 1 .40 (s, 9H, 3CH ₃ ), 2.96-3.05 (m, 1 H, CH), 3.41 (s, 4H, 2CH ₂ ), 3.53 (s, 4H, 2CH ₂ ), 6.93 (d, 1 H, J=9.0, Ar), 7.64 (d, 1 H, J=9.3, Ar), 7.73-7.97 (m, 7H, Ar), 8.50 (d, 1 H, J=2.4 Hz, Ar), 8.67 (s, 1 H, Ar) ; MS (ES+): m/e 546 (M+1 ). Example 9B:

t-Butyl 4-(5-(3-(4-(isopropylsulfonyl) phenyl) imidazo [1 , 2-a] pyridin-6-yl) pyridin-

2- yl) piperazine-1 -carboxylate

The compound of example 8 (0.3 g, 0.566 mmol) was treated with metachloroperbenzoic acid (0.293 g, 1 .69 mmol) in dry dichloromethane (1 0 mL) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.070 g (22 %); ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .20 (d, 6H, J=6.9 Hz, 2CH ₃ ), 1 .40 (s, 9H, 3CH ₃ ), 3.41 (s, 4H, 2CH ₂ ), 3.53 (s, 4H, 2CH ₂ ), 3.54-3.59 (m, 1 H, CH), 6.93 (d, 1 H, J=9.0, Ar), 7.64 (d, 1 H, J=9.3, Ar), 7.74 (d, 1 H, J=9.3, Ar), 7.94-8.07 (m, 6H, Ar), 8.52 (s, 1 H, Ar), 8.75 (s, 1 H, Ar) ; MS (ES+): m/e 562 (M+1 ).

Example 10:

3- (4-(lsopropylthio) phenyl)-6-(6-(piperazin-1 -yl) pyridin-3-yl) imidazo [1 , 2-a] pyridine

Dioxane-HCI (1 .0 mL) was added to a stirred solution of the compound of example 8 (0.45 g, 0.850 mmol) in dry dioxane (1 0 mL) at 25 °C. The reaction mixture was stirred for 1 h. The reaction mixture obtained was concentrated, diluted with water (25 mL) and neutralized by adding dilute sodium carbonate solution. The reaction mixture was extracted with chloroform (25 mLx3). The organic layers were combined, washed with water (25 mL), brine (25 mL) and dried over sodium sulphate. The crude material obtained was purified using column chromatography (silica gel, methanol in chloroform) Yield: 0.350 g (95.89 %); ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .26 (d, 6H, J=6.6 Hz, 2CH ₃ ), 2.78 (bs, 4H, 2CH ₂ ), 3.54 (bs 4H, 2CH ₂ ), 3.54-3.59 (m, 1 H, CH), 6.86 (d, 1 H, J=9.0 Hz, Ar), 7.48-7.58 (m, 3H, Ar), 7.68-7.71 (m, 3H, Ar), 7.77 (s, 1 H, Ar), 7.86 (dd, 1 H, J=2.1 , 9.0 Hz, Ar), 8.45 (d, 1 H, J=1 .8 Hz, Ar); 8.57 (s, 1 H, Ar) ; MS (ES+): m/e 430 (M+1 ).

Example 11 :

3-(4-(lsopropylsulfinyl) phenyl)-6-(6-(piperazin-1 -yl) pyridin-3-yl) imidazo [1 , 2-a] pyridine

The compound of example 1 0 (0.1 50 g, 0.350 mmol) was treated with metachloroperbenzoic acid (0.1 21 g, 0.698 mmol) in dry dichloromethane (1 0 mL) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.085 g (54.6 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 0.97 (d, 3H, J=6.6 Hz, CH ₃ ), 1.20 (d, 3H, J=6.9 Hz, CH ₃ ), 2.78 (s, 4H, 2CH ₂ ), 2.96-3.03 (m, 1H, CH), 3.46 (s, 4H, 2CH ₂ ), 6.88 (d, 1H, J=8.7 Hz, Ar), 7.59-7.62 (m, 1H, Ar), 7.73-7.76 (m, 3H, Ar), 7.88-7.97 (m, 4H, Ar), 8.48 (s, 1H, Ar), 8.66 (s, 1H, Ar); MS (ES+): m/e 446 (M+1).

Example 12:

3-(3-Bromoimidazo[1 ,2-a]pyridin-6-yl)pyridine 1 -oxide

The compound of example 3 (0.5 g, 1.82 mmol) was treated with meta- chloroperbenzoic acid (1.25 g, 7.30 mmol) in dichloromethane according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.445 g (60.24 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.52 (t, 1 H, J=8.1 Hz, Ar), 7.67-7.77 (m, 3H, Ar), 7.79 (s, 1H, Ar), 8.25 (d, 1H, J=6.3 Hz, Ar), 8.65 (s, 1H, Ar), 8.74 (s, 1H, Ar); MS (ES+): m/e 291 (M+1).

Example 13:

3-(3-(4-(lsopropylthio) phenyl) imidazo [1, 2-a] pyridin-6-yl) pyridine 1 -oxide

The compound of example 12 (0.2 g, 0.689 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.176 g, 0.896 mmol) in the presence of dichlorobis(triphenylphosphine)palladium(ll) (0.007 g, 0.011 mmol) and potassium carbonate (0.143 g, 1.034 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.150 g (60.24 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1.28 (d, 6H, J=6.6 Hz, 2CH ₃ ), 3.56-3.61 (m, 1H, CH), 7.46-7.51 (m, 3H, Ar), 7.61-7.78 (m, 5H, Ar), 7.83 (s, 1H, Ar), 8.22 (d, 1H, J=6.3 Hz, Ar), 8.72 (s, 1 H, Ar), 8.79 (s, 1 H, Ar); MS (ES+): m/e 362 (M+1 ).

Example 14:

3-(3-(4-(lsopropylsulfinyl) phenyl) imidazo [1, 2-a] pyridin-6-yl) pyridine 1 -oxide

The compound of example 13 (0.050 g, 0.138 mmol) was treated with metachloroperbenzoic acid (0.026 g, 0.152 mmol) in dry dichloromethane (5 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.040 g (77 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1.01 (d, 3H, J=6.6 Hz, CH ₃ ), 1.25 (d, 3H, J=6.9 Hz, CH ₃ ), 3.01-3.06 (m, 1H, CH), 7.52 (t, 1H, J=6.3 Hz, Ar), 7.66-7.83 (m, 5H, Ar), 7.96 (s, 1H, Ar), 8.00-8.03 (m, 2H, Ar), 8.24 (d, 1H, J=6.0 Hz, Ar), 8.76 (s, 1 H, Ar), 8.89 (s, 1 H, Ar); MS (ES+): m/e 378 (M+1 ). Example 15:

4-(3-(lmidazo [1 , 2-a] pyridin-6-yl)pyridin-2-yl)morpholine

The compound of example 1 (0.5 g, 2.54 mmol) was treated with (2-morpholinopyridin- 3-yl)boronic acid (0.686 g, 3.30 mmol) in the presence of dichlorobis(triphenylphosphine)palladium(l l) (0.028 g, 0.041 mmol) and potassium carbonate (0.526 g, 3.81 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.51 0 g (71 .83 %); MS (ES+) : m/e 281 (M+1 ).

Example 16:

4-(3-(3-Bromoimidazo [1 , 2-a] pyridin-6-yl)pyridin-2-yl)morpholine

The compound of example 1 5 (0.5 g, 1 .78 mmol) was treated with N-bromosuccinimide (0.350 g, 1 .96 mmol) in chloroform (1 5 ml_) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.520 g (81 .1 2 %); MS (ES+): m/e 360 (M+1 ).

Example 17:

4-(3-(3-(4-(lsopropylthio)phenyl)imidazo[1 ,2-a]pyridin-6-yl)pyridin-2-yl) morpholine The compound of example 1 6 (0.51 0 g, 1 .42 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.362 g, 1 .84 mmol) in the presence of dichlorobis(triphenylphosphine)palladium(l l) (0.01 6 g, 0.023 mmol) and potassium carbonate (0.294 g, 2.1 3 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.525 g (85.92 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .31 (d, 6H, J=6.9 Hz, 2CH ₃ ), 2.99 (s, 4H, 2CH ₂ ), 3.51 (s, 4H, 2CH ₂ ), 3.53-3.61 (m, 1 H, CH), 6.86 (d, 1 H, J=9.0, Ar), 7.48- 7.58 (m, 3H, Ar), 7.68-7.88 (m, 5H, Ar), 8.45 (s, 1 H, Ar), 8.57 (s, 1 H, Ar) ; MS (ES+): m/e 431 (M+1 ). Example 18:

6-(6-Methylpyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 1 (1 .0 g, 5.08 mmol) was treated with (6-methylpyridin-3- yl)boronic acid (0.695 g, 5.08 mmol) in the presence of dichlorobis(triphenylphosphine)palladium(l l) (0.286 g, 0.407 mmol) and potassium carbonate (0.701 g, 5.08 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.950 g (89 %) ; MS (ES+) : m/e 21 0 (M+1 ). Example 19:

3-Bromo-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 1 8 (0.920 g, 4.40 mmol) was treated with N- bromosuccinimide (0.861 g, 4.84 mmol) in chloroform (1 5 ml_) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.800 g (63 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.59 (s, 3H, CH ₃ ), 7.47 (d, 1 H, J=4.8 Hz, Ar), 7.74-7.82 (m, 3H, Ar), 8.20 (d, 1 H, J=4.8 Hz, Ar), 8.59 (s, 1 H, Ar), 8.91 (s, 1 H, Ar) ; MS (ES+): m/e 289 (M+1 ).

Example 20:

3-(4-(lsopropylthio)phenyl)-6-(6-methylpyridin-3-yl)imida zo[1 ,2-a]pyridine

The compound of example 19 (0.550 g, 1 .91 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.41 2 g, 2.1 0 mmol) in the presence of [1 , 1 '-bis (diphenylphosphino) -ferrocene] dichloropalladium(l l) complex with dichloromethane (0.047 g, 0.057 mmol) and sodium carbonate (0.405 g, 3.82 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.7 g (94 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .29 (d, 6H, J=3.90 Hz, 2CH ₃ ), 2.54 (s, 3H, CH ₃ ), 3.58-3.61 (m, 1 H, CH), 7.35 (d, 1 H, J=4.8 Hz, Ar), 7.51 -7.53 (m, 2H, Ar), 7.64 (d, 1 H, J=5.7 Hz, Ar), 7.72-7.74 (m, 2H, Ar), 7.78 (d, 1 H, J=4.8 Hz, Ar), 783 (s, 1 H, Ar), 8.03 (d, 1 H, J=4.8 Hz, Ar), 8.70 (s, 1 H, Ar), 8.81 (s, 1 H, Ar); MS (ES+): m/e 360 (M+1 ).

Example 21 :

3-(4-(lsopropylsulfonyl)phenyl)-6-(6-methylpyridin-3-yl)imid azo[1 ,2-a] pyridine

The compound of example 20 (0.2 g, 0.556 mmol) was treated with metachloroperbenzoic acid (0.288 g, 1 .66 mmol) in dry dichloromethane (1 0 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.1 g (46 %); ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .22 (d, 6H, J=4.2, 2CH ₃ ), 2.50 (s, 3H, CH ₃ ), 3.48-3.51 (m, 1 H, CH), 7.37 (d, 1 H, J=5.1 , Ar), 7.73 (d, 1 H, J=5.7, Ar), 7.83 (d, 1 H, J=5.7, Ar), 7.97-8.1 0 (m, 6H, Ar), 8.85 (s, 1 H, Ar), 8.88 (s, 1 H, Ar) ; MS (ES+) : m/e 392 (M+1 ). Example 22:

3-(6-Methylpyridin-3-yl)-6-(pyridin-3-yl) imidazo [1 , 2-a] pyridine

The compound of example 3 (0.2 g, 0.730 mmol) was treated with 2-methylpyridine-5- boronic acid (0.1 g, 0.730 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.018 g, 0.022 mmol) and sodium carbonate (0.155 g, 1 .42 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.160 g (77 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.56 (s, 3H, CH ₃ ), 7.34 (d, 1 H, J=8.1 , Ar), 7.45-7.52 (m, 1 H, Ar), 7.69 (d, 1 H, J=9.3, Ar), 7.78-7.88 (m, 2H, Ar), 8.1 -8.18 (m, 2H, Ar), 8.59 (d, 1 H, J=4.8, Ar); 8.73 (s, 1 H, Ar), 8.81 (s, 1 H, Ar), 8.96 (s, 1 H, Ar), MS (ES+): m/e 287 (M+1 ).

Example 23:

6-Bromoimidazo[1 ,2-a]pyridine-8-carboxylic acid

To a stirred solution of 2-amino-5-bromonicotinic acid (5.0 g, 23.04 mmol) and sodium acetate (3.78 g, 46.1 mmol) in 100 ml_ of 60 % ethanol in water, were added a refluxed solution of sodium acetate (3.78 g, 46.1 mmol) followed by 2-chloro-1 ,1 - dimethoxyethane (5.74 g, 46.1 mmol) in concentrated hydrochloric acid (1 .0 ml_) in water (6 ml_) and the reaction mass was refluxed for 2.5 h. The solvent was removed, residue obtained was diluted with cold water and pH adjusted to neutral (~7) with saturated sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate (2x100 ml_), washed with water (2x100 ml_) and brine (2x100 ml_) and dried over anhydrous sodium sulphate. The crude material obtained was purified by trituration using 2 % ethyl acetate in petroleum ether. Yield: 4.8 g (86 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.66 (d, 1 H, J=1 .2 Hz, Ar), 7.79 (d, 1 H, J=1 .5 Hz, Ar), 8.04 (s, 1 H, Ar), 8.96 (d, 1 H, J=1 .5 Hz, Ar); MS (ES+): m/e 242 (M+1 ).

Example 24:

6-(Pyridin-3-yl) imidazo [1 , 2-a] pyridine-8-carboxylic acid

The compound of example 23 (1 .0 g, 4.15 mmol) was treated with pyridin-3-ylboronic acid (0.510 g, 4.15 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.102 g, 0.124 mmol) and sodium carbonate(0.829 g, 8.30 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.4 g (40.3 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.54 (q, 1 H, J=4.8 Hz, Ar), 7.68-7.72 (m, 2H, Ar), 8.04 (s, 1H, Ar), 8.53-8.65 (m, 2H, Ar), 8.99 (d, 1H, J=1.8 Hz, Ar); 9.29 (d, 1H, J=1.8 Hz, Ar); MS (ES+): m/e 240 (M+1).

Example 25:

3-Bromo-6-(pyridin-3-yl) imidazo [1, 2-a] pyridine-8-carboxylic acid

The compound of example 24 (0.350 g, 1.46 mmol) was treated with N- bromosuccinimide (0.312 g, 1.75 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.3 g (64.5 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.55-7.61 (m, 1H, Ar), 7.85-7.87 (m, 2H, Ar), 8.52-8.55 (m, 1H, Ar), 8.62-8.68 (m, 2H, Ar), 9.27 (d, 1H, J=1.8, Ar), 11.06 (s, 1H, COOH); MS (ES+): m/e 319 (M+1). Example 26:

3-(4-(lsopropylthio) phenyl)-6-(pyridin-3-yl) imidazo [1, 2-a] pyridine-8-carboxylic acid

The compound of example 25 (0.3 g, 0.943 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.22 g, 1.13 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.023 g, 0.028 mmol) and sodium carbonate(0.2 g, 1.88 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.050 g (14 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1.30 (d, 6H, J=6.0 Hz, 2CH ₃ ), 3.62-3.63 (m, 1H, CH), 7.50-7.52 (m, 1H, Ar), 7.75-7.78 (m, 2H, Ar), 7.87-7.88 (m, 2H, Ar), 8.23-8.26 (m, 3H, Ar), 8.61-8.62 (m, 1H, Ar); 8.73 (d, 1H, J=1.8 Hz, Ar), 9.05 (d, 1H, J=1.8 Hz, Ar), MS (ES+): m/e 390 (M+1).

Example 27:

6-(6-Methoxypyridin-3-yl)imidazo[1,2-a]pyridine-8-carboxylic acid

The compound of example 23 (1.0 g, 4.15 mmol) was treated with (6-methoxypyridin-3- yl)boronic acid (0.761 g, 4.98 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.102 g, 0.124 mmol) and sodium carbonate(0.879 g, 8.30 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.3 g (27 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.92 (s, 3H, OCH ₃ ), 6.98 (s, 1 H, Ar), 7.61 (s, 1 H, Ar), 8.04 (s, 1 H, Ar), 8.1 6 (dd, 1 H, J=2.4, 8.4Hz, Ar), 8.62 (d, 1 H, J=2.4 Hz, Ar); 8.92 (d, 1 H, J=1 .8 Hz, Ar), 9.06 (d, 1 H, J=2.4 Hz, Ar); MS (ES+): m/e 270 (M+1 ). Example 28:

3-Bromo-6-(6-methoxypyridin-3-yl)imidazo[1 ,2-a]pyridine-8-carboxylic acid

The compound of example 27 (0.300 g, 1 .1 1 mmol) was treated with N- bromosuccinimide (0.238 g, 1 .34 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.3 g (77 %); MS (ES+): m/e 349 (M+1 ).

Example 29:

3-(4-lsobutylphenyl)-6-(6-methoxypyridin-3-yl) imidazo [1 , 2-a] pyridine-8- carboxylic acid

The compound of example 28 (0.300 g, 0.862 mmol) was treated with (4- isobutylphenyl)boronic acid (0.1 84 g, 1 .03 mmol) in the presence of [1 , 1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.021 g, 0.026 mmol) and sodium carbonate (0.274 g, 2.59 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.1 g (29 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.92 (d, 6H, J=6.0 Hz, 2CH ₃ ), 1 .90-1 .93 (m, 1 H, CH), 2.53-2.55 (d, 2H, J=7.2 Hz, CH ₂ ), 3.91 (s, 3H, OCH ₃ ), 6.97 (d, 1 H, J=9.0 Hz, Ar), 7.05 (t, 1 H, J=6.0 Hz, Ar), 7.73-7.37 (m, 2H, Ar), 7.54-7.60 (m, 3H, Ar); 7.78 (s, 1 H, Ar), 8.47-8.53 (m, 1 H, Ar), 8.94 (d, 1 H, J=2.1 Hz, Ar), MS (ES+): m/e 402 (M+1 ).

Example 30:

6-Bromo-8-methylimidazo [1 ,2-a]pyridine

A mixture of 2-amino-3-methyl-5-bromopyridine (5 g, 26.7 mmol), 2-chloro-1 ,1 - dimethoxyethane (6.66 g, 53.5 mmol) and sodium acetate (4.39 g, 53.5 mmol) was treated with concentrated hydrochloric acid (1 .62 mL) in 60 % ethanol according to the procedure for the preparation of the compound of example 1 to afford the title compound. Yield: 4.5 g (79.8 %); ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 2.49 (s, 3H, CH ₃ ), 7.1 9 (s, 1 H, Ar), 7.55 (s, 1 H, Ar), 7.90 (s, 1 H, Ar), 8.75 (s, 1 H, Ar) ; MS (ES+): m/e 21 2 (M+1 ). Example 31 :

8-Methyl-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 30 (1 .0 g, 4.74 mmol) was treated with pyridin-3-ylboronic acid (0.699 g, 5.69 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.1 16 g, 0.142 mmol) and sodium carbonate (1 .00 g, 9.48 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.67 g (68 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.56 (s, 3H, CH ₃ ), 7.47-7.53 (m, 2H, Ar), 7.59 (s, 1 H, Ar), 7.95 (s, 1 H, Ar), 8.10-8.13 (m, 1 H, Ar), 8.59(dd, 1 H, J=1 .5, 8.4 Hz, Ar), 8.87 (s, 1 H, Ar), 8.93(d, 1 H, J=1 .8 Hz, Ar), ; MS (ES+): m/e 210 (M+1 ).

Example 32:

3-Bromo-8-methyl-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 31 (0.67 g, 3.20 mmol) was treated with N- bromosuccinimide (0.684 g, 3.84 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.6 g (65 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.67 (s, 3H, CH ₃ ), 7.52-7.56 (m, 1 H, Ar), 7.61 (s, 1 H, Ar), 7.77 (s, 1 H, Ar), 8.19-8.23 (m, 1 H, Ar), 8.46 (s, 1 H, Ar), 8.62(dd, 1 H, J=1 .5, 4.8 Hz, Ar), 9.00 (d, 1 H, J=2.1 Hz, Ar); MS (ES+): m/e 289 (M+1 ).

Example 33:

3-(4-(lsopropylthio)phenyl)-8-methyl-6-(pyridin-3-yl)imidazo [1 ,2-a]pyridine

The compound of example 32 (0.300 g, 0.862 mmol) was treated with 4- (isopropylthio)phenylboronic acid (0.184 g, 1 .03 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.021 g, 0.026 mmol) and sodium carbonate (0.274 g, 2.59 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.65 g (65.1 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .26 (d, 6H, J=6.9 Hz, 2CH ₃ ), 2.61 (s, 3H, CH ₃ ), 3.57-3.61 (m, 1 H, CH), 7.47-7.52 (m, 4H, Ar), 7.70-7.730 (m, 2H, Ar), 7.79 (s, 1 H, Ar), 8.12-8.16 (m, 1 H, Ar), 8.58-8.60 (m, 2H, Ar), 8.95 (d, 1 H, J=1 .8 Hz, Ar); MS (ES+): m/e 360 (M+1 ).

Example 34A:

3-(4-(lsopropylsulfinyl) phenyl)-8-methyl-6-(pyridin-3-yl) imidazo [1 , 2-a] pyridine The compound of example 33 (0.44 g, 1.24 mmol) was treated with metachloroperbenzoic acid (0.528 g, 3.06 mmol) in dry dichloromethane (10 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.225 g (49 %); (DMSO-d ₆ , 300 MHz): δ 1.01 (d, 3H, J=6.0 Hz, CH ₃ ), 1.24 (d, 3H, J=6.0 Hz, CH ₃ ), 2.62 (s, 3H, CH ₃ ), 2.98-3.02 (m, 1H, CH), 7.50 (q, 1H, J=4.8 Hz, Ar), 7.57 (s, 1H, Ar), 7.75-7.78 (m, 2H, Ar), 7.91 (s, 1H, Ar), 7.97-8.00 (m, 2H, Ar), 8.14-8.18 (m, 1H, Ar), 8.59-8.61 (dd, 1H, J=1.5, 4.8 Hz, Ar), 8.70 (s, 1H, Ar), 8.97 (d, 1H, J=2.1 Hz, Ar); MS (ES+): m/e 376 (M+1).

Example 34B:

3-(4-(lsopropylsulfonyl) phenyl)-8-methyl-6-(pyridin-3-yl) imidazo [1, 2-a] pyridine

The compound of example 33 (0.44 g, 1.24 mmol) was treated with metachloroperbenzoic acid (0.528 g, 3.06 mmol) in dry dichloromethane (10 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.115 g (24 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1.22 (s, 6H, 2CH ₃ ), 2.63 (s, 3H, CH ₃ ), 3.47-3.51 (m, 1H, CH), 7.49-7.53 (m, 1H, Ar), 7.61 (s, 1H, Ar), 7.96-7.99 (m, 3H, Ar), 8.06-8.09 (m, 2H, Ar), 8.16-8.20 (m, 1H, Ar), 8.60-8.62 (dd, 1H, J=1.5, 4.5 Hz, Ar), 8.79 (s, 1H, Ar), 8.99 (d, 1H, J=1.8 Hz, Ar),; MS (ES+): m/e 392 (M+1).

Example 35:

8-Methyl-6-(2-methylpyrimidin-5-yl)imidazo[1,2-a]pyridine

The compound of example 30 (2.0 g, 9.48 mmol) was treated with 2-methyl-5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidine (2.085 g, 9.48 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll)comp lex with dichloromethane (0.124 g, 0.152 mmol) and sodium carbonate (1.50 g, 14.21 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.5 g (70.6 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.58 (s, 3H, CH ₃ ), 2.68 (s, 3H, CH ₃ ), 7.69 (s, 1 H, Ar), 7.77 (s, 1 H, Ar), 8.05 (s, 1 H, Ar), 9.02 (s, 1 H, Ar), 9.07 (s, 2H, Ar); MS (ES+): m/e 225 (M+1 ).

Example 36:

3-Bromo-8-methyl-6-(2-methylpyrimidin-5-yl)imidazo[1,2-a]pyr idine The compound of example 35 (1 .50 g, 6.69 mmol) was treated with N- bromosuccinimide (1 .19 g, 6.69 mmol) in chloroform (1 5 ml_) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 1 .5 g (74 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 2.57 (s, 3H, CH ₃ ), 2.68 (s, 3H, CH ₃ ), 7.62 (s, 1 H, Ar), 7.76 (s, 1 H, Ar), 8.56 (s, 1 H, Ar), 9.1 1 (s, 2H, Ar) ; MS (ES+) : m/e 304 (M+1 ).

Example 37:

8-Methyl-6-(2-methylpyrimidin-5-yl)-3-(4-(methylsulfonyl) phenyl)imidazo [1 ,2-a] pyridine

The compound of example 36 (0.2 g, 0.660 mmol) was treated with (4- (methylsulfonyl)phenyl)boronic acid (0.1 32 g, 0.660 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l)complex with dichloromethane (0.01 6 g, 0.020 mmol) and sodium carbonate (0.140 g, 1 .31 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.1 55g (62.1 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.62 (s, 3H, CH ₃ ), 2.67 (s, 3H, CH ₃ ), 3.29 (s, 3H, CH ₃ ), 7.63 (s, 1 H, Ar), 7.98 (s, 1 H, Ar), 8.06 (s, 4H, Ar), 8.84 (s, 1 H, Ar), 9.09 (s, 2H, Ar); MS (ES+) : m/e 379 (M+1 ).

Example 38:

3-(6-Methoxypyridin-3-yl)-8-methyl-6-(2-methylpyrimidin-5-yl )imidazo[1 ,2-a] pyridine

The compound of example 36 (0.1 g, 0.330 mmol) was treated with (6-methoxypyridin- 3-yl)boronic acid (0.050 g, 0.330 mmol) in the presence of [1 , 1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(l l)complex with dichloromethane (0.004 g, 0.01 6 mmol) and sodium carbonate (0.052 g, 0.495 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.085g (75 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 2.60 (s, 3H, CH ₃ ), 2.66 (s, 3H, CH ₃ ), 3.93 (s, 3H, OCH ₃ ), 7.01 (d, 1 H, J= 8.4 Hz, Ar), 7.55 (s, 1 H, Ar), 7.76 (s, 1 H, Ar), 8.09 (d, 1 H, J= 8.4 Hz, Ar), 8.52 (s, 1 H, Ar), 8.62 (s, 1 H, Ar), 9.06 (s, 2H, Ar); MS (ES+) : m/e 332 (M+1 ).

Example 39:

6-(6-Methoxypyridin-3-yl)-8-methylimidazo[1 ,2-a]pyridine The compound of example 30 (1 .5 g, 7.1 1 mmol) was treated with (6-methoxypyridin-3- yl)boronic acid (1 .3 g, 8.53 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(l l) complex with dichloromethane (0.1 74 g, 0.21 3 mmol) and sodium carbonate (1 .5 g, 14.21 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1 .40 g (82 %) ; MS (ES+) : m/e 240 (M+1 ).

Example 40:

3-Bromo-6-(6-methoxypyridin-3-yl)-8-methylimidazo[1 ,2-a]pyridine

The compound of example 39 (1 .4 g, 5.85 mmol) was treated with N-bromosuccinimide (1 .25 g, 7.02 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 1 .3 g (70 %); MS (ES+) : m/e 31 9 (M+1 ).

Example 41 :

3-(4-(lsopropylthio)phenyl)-6-(6-methoxypyridin-3-yl)-8-meth ylimidazo[1 ,2-a] pyridine

The compound of example 40 (0.85 g, 2.67 mmol) was treated with 4- (isopropylthio)phenylboronic acid (0.629 g, 3.21 mmol) in the presence of [1 , 1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.065 g, 0.085 mmol) and sodium carbonate (0.566 g, 5.34 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.65 g (62 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .30 (d, 6H, J=8.4 Hz, 2CH ₃ ), 2.59 (s, 3H, CH ₃ ), 3.54-3.63 (m, 1 H, CH), 3.89 (s, 3H, OCH ₃ ), 6.91 (d, 1 H, J=8.7 Hz, Ar), 7.46-7.52 (m, 3H, Ar), 7.69-7.72 (m, 2H, Ar), 7.77 (s, 1 H, Ar), 8.05 (dd, 1 H, J=8.7, 2.7 Hz, Ar), 8.52-8.53 (m, 2H, Ar) ; MS (ES+) : m/e 390 (M+1 ).

Example 42:

3-(4-(lsopropylsulfinyl) phenyl)-6-(6-methoxypyridin-3-yl)-8-methylimidazo [1 , 2-a] pyridine

The compound of example 41 (0.4 g, 1 .027 mmol) was treated with metachloroperbenzoic acid (0.443 g, 2.57 mmol) in dry dichloromethane (1 0 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.150 g (36 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.99 (d, 3H, J=6.0 Hz, CH ₃ ), 1 .23 (d, 3H, J=6.0 Hz, CH ₃ ), 2.61 (s, 3H, CH ₃ ), 3.00-3.05 (m, 1 H, CH), 3.90 (s, 3H, CH ₃ ), 6.92 (d, 1 H, J=9.0 Hz, Ar), 7.51 (s, 1 H, Ar), 7.75-7.78 (m, 2H, Ar), 7.89 (s, 1 H, Ar), 7.96-7.98 (m, 2H, Ar), 8.07-8.10 (m, 1 H, Ar), 8.55 (d, 1 H, J=2.4 Hz, Ar), 8.61 (s, 1 H, Ar); MS (ES+): m/e 406 (M+1 ).

Example 43:

6-(6-Methoxypyridin-3-yl)-8-methyl-3-(4-(methylsulfonyl)p henyl)imidazo[1 ,2-a] pyridine

The compound of example 40 (0.250 g, 0.78 mmol) was treated with (4- (methylsulfonyl)phenyl)boronic acid (0.157 g, 0.78 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.019 g, 0.024 mmol) and sodium carbonate (0.167 g, 1 .57 mmol) in dry dimethylformamide (10 ml_) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.240 g (78 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.61 (s, 3H, CH ₃ ), 3.28 (s, 3H, CH ₃ ), 3.90 (s, 3H, OCH ₃ ), 6.93 (d, 1 H, J=8.7 Hz, Ar), 7.54 (s, 1 H, Ar), 7.95 (s, 1 H, Ar), 8.06-8.08 (m, 3H, Ar), 8.09 (d, 1 H, J=2.4 Hz, Ar), 8.1 1 (d, 1 H, J=2.4 Hz, Ar), 8.56 (d, 1 H, J=2.4 Hz, Ar), 8.66 (s, 1 H, Ar); MS (ES+): m/e 394 (M+1 ).

Example 44:

8-Methyl-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 30 (3.0 g, 14.21 mmol) was treated with (6-methylpyridin-3- yl)boronic acid (2.33 g, 17.06 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.348 g, 0.426 mmol) and sodium carbonate (3.0 g, 28.4 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.25 g (71 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.50 (s, 3H, CH ₃ ), 2.54 (s, 3H, CH ₃ ), 7.35 (d, 1 H, J=8.1 Hz, Ar), 7.43 (s, 1 H Ar), 7.56 (s, 1 H, Ar), 7.93 (s, 1 H, Ar), 7.99 (d, 1 H, J=8.1 Hz, Ar), 8.78-8.81 (m, 2H, Ar) ; MS (ES+): m/e 224 (M+1 ).

Example 45:

3-Bromo-8-methyl-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridine The compound of example 44 (2.1 g, 9.41 mmol) was treated with N-bromosuccinimide (2.0 g, 1 1 .29 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 2.0 g (70.4 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.49 (s, 3H, CH ₃ ), 2.57 (s, 3H, CH ₃ ), 7.37 (d, 1 H, J=8.1 Hz, Ar), 7.56 (s, 1 H Ar), 7.73 (s, 1 H, Ar), 8.07 (dd, 1 H, J=8.1 , 2.4 Hz, Ar), 8.38 (s, 1 H, Ar), 8.84 (d, 1 H, J=2.1 Hz, Ar) ; MS (ES+): m/e 303 (M+1 ).

Example 46:

3-(4-(lsopropylthio)phenyl)-8-methyl-6-(6-methylpyridin-3 -yl)imidazo[1 ,2-a] pyridine

The compound of example 45 (0.400 g, 1 .32 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.31 1 g, 1 .58 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.032 g, 0.040 mmol) and sodium carbonate (0.281 g, 2.65 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.310 g (63 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .30 (d, 6H, J=6.6 Hz, 2CH ₃ ), 2.48 (s, 3H, CH ₃ ), 2.59 (s, 3H, CH ₃ ), 3.54-3.63 (m, 1 H, CH), 7.33 (d, 1 H, J=7.8 Hz, Ar), 7.49-7.52 (m, 3H, Ar), 7.69-7.72 (m, 2H, Ar), 7.78 (s, 1 H, Ar), 8.01 (dd, 1 H, J=8.1 , 2.4 Hz, Ar), 8.55 (s, 1 H, Ar), 8.79 (d, 1 H, J=2.1 Hz, Ar) ; MS (ES+): m/e 374 (M+1 ).

Example 47A:

3-(4-(lsopropylsulfinyl) phenyl)-8-methyl-6-(6-methylpyridin-3-yl) imidazo [1 , 2-a] pyridine

The compound of example 46 (0.2 g, 0.535 mmol) was treated with metachloroperbenzoic acid (0.231 g, 1 .33 mmol) in dry dichloromethane (10 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound.Yield: 0.140 g (67 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.99 (d, 3H, J=6.0, CH ₃ ), 1 .22 (d, 3H, J=6.0, CH ₃ ), 2.49 (s, 3H, CH ₃ ), 2.60 (s, 3H, CH ₃ ), 2,97-3.06 (m, 1 H, CH), 7.33 (d, 1 H, J=8.1 Hz, Ar), 7.53 (s, 1 H, Ar), 7.74-7.76 (m, 2H, Ar), 7.88 (s, 1 H, Ar), 7.95-7.97 (m, 2H, Ar), 8.03 (dd, 1 H, J=8.1 , 2.4 Hz, Ar), 8.64 (s, 1 H, Ar), 8.80 (d, 1 H, J=2.1 Hz, Ar); MS (ES+): m/e 390 (M+1 ). Example 47B:

3-(4-(lsopropylsulfonyl) phenyl)-8-methyl-6-(6-methyl pyridine-3-yl)imidazo [1 , 2- a] pyridine

The compound of example 46 (0.2 g, 0.535 mmol) was treated with metachloroperbenzoic acid (0.231 g, 1 .33 mmol) in dry dichloromethane (1 0 mL) according to the procedure for the preparation of the compound of example 5 to afford the title compound.Yield: 0.050 g (23 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .21 (d, 6H, J=6.9 Hz, 2CH ₃ ), 2.49 (s, 3H, CH ₃ ), 2.61 (s, 3H, CH ₃ ), 2.97-3.06 (m, 1 H, CH), 7.35 (d, 1 H, J=8.1 Hz, Ar), 7.57 (s, 1 H, Ar), 7.95-8.07 (m, 6H, Ar), 8.72 (s, 1 H, Ar), 8.83 (d, 1 H, J=2.4 Hz, Ar); MS (ES+) : m/e 406 (M+1 ).

Example 48:

5-(3-(4-(lsopropylsulfonyl) phenyl)-8-methylimidazo [1 , 2-a] pyridin-6-yl)-2- methylpyridine-1 -oxide

The compound of example 47B (0.5 g, 1 .33 mmol) was treated with metachloroperbenzoic acid (0.508 g, 2.95 mmol) in dry dichloromethane (25 mL) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.370 g (66 %); ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .21 (d, 6H, J=6.6 Hz, 2CH ₃ ), 2.40 (s, 3H, CH ₃ ), 2.61 (s, 3H, CH ₃ ), 3.49-3.52 (m, 1 H, CH), 7.56-7.65 (m, 3H, Ar), 7.96-7.99 (m, 3H, Ar), 8.07-8.09 (m, 2H, Ar), 8.80 (s, 2H, Ar); MS (ES+): m/e 422 (M+1 ).

Example 49:

8-Methyl-6-(6-methylpyridin-3-yl)-3-(4-(trifluoromethoxy) phenyl)imidazo[1 , 2-a] pyridine

The compound of example 45 (0.21 0 g, 0.695 mmol) was treated with (4- (trifluoromethoxy)phenyl)boronic acid (0.143 g, 0.695 mmol) in the presence of [1 , 1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.01 7 g, 0.021 mmol) and sodium carbonate (0.147 g, 1 .39 mmol) in dry dimethylformamide (1 0 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.1 80 g (68 %); ¹ H NMR (DMSO-de, 300 MHz) : δ 2.51 (s, 3H, CH ₃ ), 2.61 (s, 3H, CH ₃ ), 7.34 (d, 1 H, J=8.1 Hz, Ar), 7.53-7.55 (m, 3H, Ar), 7.83 (s, 1 H, Ar), 7.88-7.51 (m, 2H, Ar), 8.04 (dd, 1 H, J=8.1 , 2.4 Hz, Ar), 8.59 (s, 1 H, Ar), 8.81 (d, 1 H, J=2.1 Hz, Ar); MS (ES+): m/e 384 (M+1 ). Example 50:

3-(2-Methoxypyrimidin-5-yl)-8-methyl-6-(6-methylpyridin-3-yl )imidazo[1, 2-a] pyridine

The compound of example 45 (0.350 g, 1.15 mmol) was treated with (2- methoxypyrimidin-5-yl)boronic acid (0.178 g, 1.15 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.028 g, 0.035 mmol) and sodium carbonate (0.246 g, 2.31 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.210 g (55 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.51 (s, 3H, CH ₃ ), 2.60 (s, 3H, CH ₃ ), 4.00 (s, 3H, OCH ₃ ), 7.32 (d, 1H, J=8.1 Hz, Ar), 7.54 (s, 1H, Ar), 7.81 (s, 1H, Ar), 8.06 (dd, 1H, J=8.1, 2.4 Hz, Ar), 8.51 (s, 1H, Ar), 8.83 (d, 1H, J=2.1 Hz, Ar), 8.96 (s, 2H, Ar); MS (ES+): m/e 332 (M+1). Example 51 :

6-(Pyrimidin-5-yl)imidazo[1,2-a]pyridine

The compound of example 1 (2.0 g, 10.15 mmol) was treated with pyrimidin-5-ylboronic acid (1.51 g, 12.18 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll)complex with dichloromethane (0.249 g, 0.305 mmol) and sodium carbonate (2.15 g, 20.30 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.8 g (90 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.66-7.72 (m, 3H, Ar), 7.99 (s, 1H, Ar), 9.12-9.13 (m, 1H, Ar), 9.20 (s, 2H, Ar), 9.21 (s, 1H, Ar); MS (ES+): m/e 197 (M+1).

Example 52:

3-Bromo-6-(pyrimidin-5-yl)imidazo[1,2-a]pyridine

The compound of example 51 (2.0 g, 10.19 mmol) was treated with N- bromosuccinimide (1.99 g, 11.21 mmol) in chloroform (15 ml_) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 2.7 g (96 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.80-7.84 (m, 3H, Ar), 8.77-8.78 (m, 1H, Ar), 9.24 (s, 1H, Ar), 9.26 (s, 2H, Ar); MS (ES+): m/e 276 (M+1). Example 53:

3-(4-(lsopropylthio)phenyl)-6-(pyrimidin-5-yl)imidazo[1 ,2-a] pyridine

The compound of example 52 (0.550 g, 1 .91 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.41 2 g, 2.1 0 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l)complex with dichloromethane (0.047 g, 0.057 mmol) and sodium carbonate (0.405 g, 3.82 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.4 g (79 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .29 (d, 6H, J=6.60 Hz, 2CH ₃ ), 3.58-3.63 (m, 1 H, CH), 7.50-7.53 (m, 2H, Ar), 7.71 -7.74 (m, 3H, Ar), 7.82-7.87 (m, 3H, Ar), 8.91 (s, 1 H, Ar), 9.22 (s, 2H, Ar); MS (ES+): m/e 347(M+1 ).

Example 54A:

3-(4-(lsopropylsulfinyl)phenyl)-6-(pyrimidin-5-yl)imidazo [1 ,2-a] pyridine

The compound of example 53 (0.3 g, 0.866 mmol) was treated with metachloroperbenzoic acid (0.374 g, 2.1 6 mmol) in dry dichloromethane (1 5 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.1 31 g (41 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.99 (d, 3H, J=6.9 Hz, CH ₃ ), 1 .25 (d, 3H, J=6.9 Hz, CH ₃ ), 2.99-3.08 (m, 1 H, CH), 7.75-7.78 (m, 3H, Ar), 9.22-9.23 (m, 2H, Ar), 7.857.89 (m, 1 H, Ar), 8.03 (s, 1 H, Ar), 8.99 (s, 1 H, Ar), 9.22-9.23 (m, 3H, Ar); MS (ES+) : m/e 363 (M+1 ).

Example 54B:

3-(4-(lsopropylsulfonyl) phenyl)-6-(pyrimidin-5-yl) imidazo [1 , 2-a] pyridine

The compound of example 53 (0.3 g, 0.866 mmol) was treated with metachloroperbenzoic acid (0.374 g, 2.1 6 mmol) in dry dichloromethane (1 5 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.1 1 5 g (35 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .21 (d, 6H, J=6.0 Hz, 2CH ₃ ), 3.46-3.52 (m, 1 H, CH), 7.92-8.01 (m, 4H, Ar), 8.10-8.13 (m, 2H, Ar), 8.1 6 (s, 1 H, Ar), 9.1 0 (s, 1 H, Ar), 9.24-9.26 (m, 3H, Ar); MS (ES+): m/e 379 (M+1 ).

Example 55:

3-(3-(4-(lsopropylsulfonyl) phenyl) imidazo [1 , 2-a] pyridin-6-yl) pyridine-1 -oxide The compound of example 4 (5.0 g, 14.47 mmol) was treated with metachloroperbenzoic acid (14.99 g, 87.0 mmol) in dry dichloromethane (1 50 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 2.6 g (46 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .21 (d, 6H, J=6.6 Hz, 2CH ₃ ), 3.48-3.53 (m, 1 H, CH), 7.53 (t, 1 H, J=7.8 Hz, Ar), 7.70-7.75 (m, 2H, Ar), 7.82-7.85 (m, 1 H, Ar), 7.97-8.00 (m, 2H, Ar), 8.04 (s, 1 H, Ar), 8.09-8.12 (m, 2H, Ar), 8.25 (d, 1 H, J=6.9 Hz, Ar), 8.78 (s, 1 H, Ar), 8.98 (s, 1 H, Ar); MS (ES+): m/e 394 (M+1 ). Example 56:

3-(6-Methoxypyridin-3-yl)-6-(pyridin-3-yl) imidazo [1 , 2-a] pyridine

The compound of example 3 (2.0 g, 7.30 mmol) was treated with (6-methoxypyridin-3- yl)boronic acid (1 .33 g, 8.76 mmol) in the presence of [1 , 1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(l l) complex with dichloromethane (0.095 g, 0.1 1 7 mmol) and sodium carbonate (1 .1 6 g, 1 0.94 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1 .8 g (82 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.93 (s, 3H, OCH ₃ ), 7.02 (d, 1 H, J=8.7 Hz, Ar), 7.51 (q, 1 H, J=4.8 Hz, Ar), 7.66-7.70 (m, 1 H, Ar), 7.78-7.81 (m, 2H, Ar), 8.1 0-8.1 7 (m, 2H, Ar), 8.54 (d, 1 H, J=2.4 Hz, Ar), 8.59 (d, 1 H, J=4.8 Hz, Ar), 8.67 (s, 1 H, Ar), 8.97 (d, 1 H, J=2.1 Hz, Ar); MS (ES+): m/e 303 (M+1 ).

Example 57:

3-(3-(6-Methoxypyridin-3-yl) imidazo [1 , 2-a] pyridin-6-yl) pyridine 1 -oxide

The compound of example 56 (0.5 g, 1 .65 mmol) was treated with metachloroperbenzoic acid (0.628 g, 3.64 mmol) in dry dichloromethane (25 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.260 g (49 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.94 (s, 3H, OCH ₃ ), 7.02 (d, 1 H, J=8.7 Hz, Ar), 7.50 (t, 1 H, J=7.5 Hz, Ar), 7.63-7.81 (m, 4H, Ar), 8.09-8.1 3 (m, 1 H, Ar), 8.22 (d, 1 H, J=6.3 Hz, Ar), 8.56 (s, 1 H, Ar), 8.74 (s, 2H, Ar) ; MS (ES+): m/e 319 (M+1 ).

Example 58:

6-(2,6-Dimethylpyridin-3-yl)-8-methylimidazo[1 ,2-a]pyridine

The compound of example 30 (1 .0 g, 4.74 mmol) was treated with 2,6-dimethyl-3- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (1 .1 0 g, 4.74 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.077 g, 0.095 mmol) and sodium carbonate (1 .0 g, 9.48 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.8 g (71 .2 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.43 (s, 3H, CH ₃ ), 2.47 (s, 3H, CH ₃ ), 2.52 (s, 3H, CH ₃ ), 7.08 (s, 1 H, Ar), 7.1 6 (d, 1 H, J=7.8 Hz, Ar), 7.55-7.57 (m, 2H Ar), 7.93 (s, 1 H, Ar), 8.43 (s, 1 H, Ar) ; MS (ES+) : m/e 238 (M+1 ).

Example 59:

3-Bromo-6-(2,6-dimethylpyridin-3-yl)-8-methylimidazo[1 ,2-a]pyridine

The compound of example 58 (0.8 g, 3.37 mmol) was treated with N-bromosuccinimide (0.660 g, 3.71 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.9 g (84 %); MS (ES+) : m/e 317 (M+1 ).

Example 60:

3- t-Butyl 4-(5-(6-(2,6-dimethylpyridin-3-yl)-8-methylimidazo [1 ,2-a]pyridin-3-yl) pyridin-2-yl)piperazine-1 -carboxylate

The compound of example 59 (0.7 g, 2.21 mmol) was treated with (6-(4-(t- butoxycarbonyl)piperazin-1 -yl)pyridin-3-yl)boronic acid (0.748 g, 2.43 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.029 g, 0.035 mmol) and sodium carbonate (0.35 g, 3.32 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.375 g (34 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .42 (s, 9H, 3CH ₃ ), 2.42 (s, 3H, CH ₃ ), 2.48 (s, 3H, CH ₃ ), 2.56 (s, 3H, CH ₃ ), 3.42 (s, 4H, 2CH ₂ ), 3.56 (s, 4H, 2CH ₂ ), 6.97 (d, 1 H, J=9.0 Hz, Ar), 7.1 2-7.1 5 (m, 2H, Ar), 7.58-7.61 (m, 1 H, Ar), 7.68 (s, 1 H, Ar), 7.83-8.87 (dd, 1 H, J=8.7, 2.1 Hz, Ar), 8.1 0 (s, 1 H, Ar), 8.38 (d, 1 H, J=2.1 Hz, Ar); MS (ES+) : m/e 499 (M+1 ). Example 61 :

6-(2,6-Dimethylpyridin-3-yl)-8-methyl-3-(6-(piperazin-1 -yl)pyridin-3-yl) imidazo [1 , 2-a] pyridine

The compound of example 60 (0.050 g, 0.1 00 mmol) was treated with dioxane- hydrochloride (1 .0 ml_) in dry 1 ,4-dioxane (2 ml_) according to the procedure for the preparation of the compound of example 1 0 to afford the title compound. Yield: 0.020 g (67 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.42 (s, 3H, CH ₃ ), 2.46 (s, 3H, CH ₃ ), 2.56 (s, 3H, CH ₃ ), 2.79 (s, 4H, 2CH ₂ ), 3.48 (s, 4H, 2CH ₂ ), 6.92 (d, 1H, J=9.0 Hz, Ar), 7.12-7.15 (m, 2H, Ar), 7.61 (d, 1H, J=7.8 Hz, Ar), 7.67 (s, 1H, Ar), 7.80 (d, 1H, J=8.7 Hz, Ar), 8.10 (s, 1H, Ar), 8.36 (d, 1H, J=2.1 Hz, Ar); MS (ES+): m/e 399 (M+1).

Example 62:

3-(4-lsobutylphenyl)-8-methyl-6-(6-methylpyridin-3-yl)imidaz o[1,2-a] pyridine

The compound of example 45 was treated with (4-isobutylphenyl)boronic acid (0.118 g, 0.662 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.016 g, 0.020 mmol) and sodium carbonate (0.140 g, 1.32 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound . Yield: 0.165 g (70 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.91 (d, 6H, J=6.6 Hz, 2CH ₃ ), 1.85-1.94 (m, 1H, CH), 2.53 (s, 3H, CH ₃ ), 2.60 (s, 3H, CH ₃ ), 2.89 (s, 2H, CH ₂ ), 7.34 (m, 3H, 3Ar), 7.48 (s, 1H, Ar), 7.64-7.66 (m, 2H, Ar), 7.74 (s, 1H, Ar), 8.01 (dd, 1H, J=8.1, 2.1 Hz, Ar), 8.52 (s, 1H, Ar), 8.78 (d, 1H, J=2.1 Hz, Ar); MS (ES+): m/e 356 (M+1). Example 63:

5-(8-Methylimidazo[1,2-a]pyridin-6-yl)picolinonitrile

The compound of example 30 (5.0 g, 23.69 mmol) was treated with 5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)picolinonitrile (5.45 g, 23.69 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.310 g, 0.379 mmol) and sodium carbonate (3.77 g, 35.5 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 3.8 g (68.5 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.56 (s, 3H, CH ₃ ), 7.56 (s, 1H, Ar), 7.62 (s, 1H, Ar), 7.97 (s, 1H, Ar), 7.16 (d, 1H, J=8.1 Hz, Ar), 8.38 (dd, 1H, J=8.1, 2.1 Hz, Ar), 9.04 (s, 1H, Ar), 9.14 (d, 1H, J=1.81 Hz, Ar) ; MS (ES+): m/e 235 (M+1).

Example 64:

5-(3-Bromo-8-methylimidazo[1,2-a]pyridin-6-yl)picolinonitril e

The compound of example 63 (0.8 g, 3.37 mmol) was treated with N-bromosuccinimide (0.660 g, 3.71 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 3.5 g (73 %); MS (ES+) : m/e 314 (M+1 ). Example 65:

t-Butyl 4-(5-(6-(6-cyanopyridin-3-yl)-8-methylimidazo [1 ,2-a] pyridin-3-yl) pyridin-2- yl) piperazine-1 -carboxylate

The compound of example 64 (2.0 g, 6.39 mmol) was treated with t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (2.73 g, 7.03 mmol) in the presence of [1 , 1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.083 g, 0.102 mmol) and sodium carbonate (1 .01 5 g, 9.58 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound Yield: 1 .4 g (44 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .43 (s, 9H, 3CH ₃ ), 2.60 (s, 3H, CH ₃ ), 3.47 (s, 4H, 2CH ₂ ), 3.58 (s, 4H, 2CH ₂ ), 7.01 (d, 1 H, J=9.0 Hz, Ar), 7.58 (s, 1 H, Ar), 7.71 (s, 1 H, Ar), 7.92 (dd, 1 H, J=8.7, 2.4 Hz, Ar), 8.1 3 (d, 1 H, J=8.4 Hz, Ar), 8.40-8.46 (m, 2H, Ar), 8.64 ( s, 1 H Ar), 9.1 6 ( d, 1 H, J=1 .5 Hz, Ar); MS (ES+): m/e 496 (M+1 )

Example 66:

5-(8-Methyl-3-(6-(piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)

picolinonitrile

The compound of example 65 (1 .0 g, 2.01 8 mmol) was treated with dioxane-HCI in dry dioxane (1 0 mL) according to the procedure for the preparation of the compound of example 1 0 to afford the title compound. Yield: 0.55 g (69 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.65 (s, 3H, CH ₃ ), 3.24 (s, 4H, 2CH ₂ ), 3.83 (s, 4H, 2CH ₂ ), 7.1 2 (d, 1 H, J=9.0 Hz, Ar), 7.83 (s, 1 H, Ar), 7.98 (s, 1 H, Ar), 8.03 (d, 1 H, J=9.0 Hz, Ar), 8.1 6 (d, 1 H, J=9.0 Hz, Ar), 8.44 (d, 1 H, J=9.0 Hz, Ar), 8.52 (s, 1 H, Ar), 8.73 (s, 1 H, Ar), 8.96 (bs, 1 H, NH), 9.18 (s, 1 H, Ar); MS (ES+) : m/e 396 (M+1 ). Example 67:

6-(6-(Trifluoromethyl)pyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 1 (20.0 g, 1 02.0 mmol) was treated with 6- (trifluoromethyl)pyridin-3-ylboronic acid (21 .32 g, 1 1 2.0 mmol) in the presence of [1 , 1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (1 .65 g, 2.03 mmol) and sodium carbonate (21 .52 g, 203 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 20.0 g (74.9 %);; MS (ES+): m/e 264 (M+1). Example 68:

3-Bromo-6-(6-(trifluoromethyl)pyridin-3-yl)imidazo[1,2-a] pyridine

N-Bromosuccinimide (14.88 g, 84.0 mmol) was added to a stirred solution of the compound of example 67 (20.0 g, 76.0 mmol) in chloroform at 10 °C. The reaction mixture was stirred for 1 h. The reaction mixture was diluted with water (175 mL) and extracted with chloroform (150 mL ^χ 3). The organic layers were combined, washed with water (175 mL), brine (175 mL) and dried over anhydrous sodium sulphate. The crude material obtained was purified using column chromatography (silica gel, methanol in chloroform) to afford the title compound. Yield: 21.0 g (81.0 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.79-7.86 (m, 3H, Ar), 8.04 (d, 1H, J=8.1 Hz, Ar), 8.53 (d, 1H, J=1.8 Hz, Ar), 8.75 (s, 1H, Ar), 9.22 (s, 1H, Ar); MS (ES+): m/e 343 (M+1).

Example 69:

3-(6-Methoxypyridin-3-yl)-6-(6-(trifluoromethyl)pyridin-3-yl ) imidazo [1, 2-a] pyridine

The compound of example 68 (0.4 g, 1.17 mmol) was treated with (6-methoxypyridin-3- yl)boronic acid (0.197 g, 1.28 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.019 g, 0.023 mmol) and sodium carbonate (0.248 g, 2.34 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.350 g (81 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.94 (s, 3H, OCH ₃ ), 7.01 (d, 1H, J=8.4 Hz, Ar), 7.75-7.76 (m, 1H, Ar), 7.82-7.85 (m, 2H, Ar), 8.02 (d, 1H, J=8.1 Hz, Ar), 8.13 (dd, 1H, J=8.7, 2.4 Hz, Ar), 8.50-8.60 (m, 1H, Ar), 8.55 ( d, 1H, J=2.1 Hz, Ar), 8.82 (s, 1H, Ar), 9.16 (s, 1H, Ar); MS (ES+): m/e 371 (M+1). Example 70:

3-(4-(Methylsulfonyl) phenyl)-6-(pyridin-3-yl) imidazo [1, 2-a] pyridine

The compound of example 3 (0.2 g, 0.73 mmol) was treated with (4- (methylsulfonyl)phenyl)boronic acid (0.19 g, 0.949 mmol) in the presence of [1,1'- bis(diphenylphosphino) ferrocene]dichloropalladium(ll) complex with dichloromethane (0.08 g, 0.012 mmol) and sodium carbonate (0.15 g, 1.44 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.120 g (48 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.29 (s, 3H, CH ₃ ), 7.50-7.54 (q, 1H, J=4.2 Hz, Ar), 7.74-7.87 (m, 2H, Ar), 8.02 (s, 1H, Ar), 8.05-8.11 (m, 4H, Ar), 8.17-8.21 (m, 1H, Ar), 8.62 (dd, 1H, J=4.8, 1.8 Hz, Ar), 8.90 (s, 1H, Ar), 9.00 (d, 1H, J=2.1 Hz, Ar); MS (ES+): m/e 350 (M+1).

Example 71 :

6-(2-Methylpyridin-3-yl) imidazo [1, 2-a] pyridine

The compound of example 1 (0.195 g, 0.990 mmol) was treated with (2-methylpyridin-3- yl)boronic acid (0.176 g, 1.28 mmol) in the presence of dichlorobis(triphenylphosphine)palladium(ll) (0.011 g, 0.016 mmol) and potassium carbonate (0.205 g, 1.48 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.2 g (95 %); MS (ES+): m/e 210 (M+1).

Example 72:

3-Bromo-6-(2-methylpyridin-3-yl) imidazo [1, 2-a] pyridine

The compound of example 71 (0.2 g, 0.956 mmol) was treated with N- bromosuccinimide in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.210 g (75 %), MS (ES+): m/e 289 (M+1).

Example 73:

3-(4-(lsopropylthio) phenyl)-6-(2-methylpyridin-3-yl)imidazo[1, 2-a] pyridine

The compound of example 72 (0.4 g, 1.38 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.350 g, 1.80 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.016 g, 0.019 mmol) and potassium carbonate (0.288 g, 2.08 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.350 g (70 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1.25 (d, 6H, J=6.6 Hz, 2CH ₃ ), 2.45 (s, 3H, CH ₃ ), 3.52-3.56 (m, 1H, CH), 7.28 (q, 1H, J=4.8 Hz, Ar), 7.36 (d, 1H, J=9.0 Hz, Ar), 7.44-7.47 (m, 2H, Ar), 7.63-7.66 (m, 2H, Ar), 7.70-7.75 (m, 2H, Ar), 7.82 (s, 1H, Ar), 8.43 (s, 1H, Ar), 8.47 (d, 1H, J=4.5 Hz, Ar); MS (ES+): m/e 360 (M+1). Example 74:

5-(lmidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl)pyridin-2-amine

The compound of example 1 (0.1 0 g, 0.5 mmol) was treated with 5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amine (0.201 g, 0.7 mmol) in dry 1 ,4-dioxane (1 0 mL ) in presence of sodium carbonate (0.424 g, 4.0 mmol) in water (2 mL) and dichlorobis(triphenylphosphine)palladium(l l) (0.041 g, 0.05 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.1 30 g (92.1 2 %); ¹ H NMR (CDCI3, 300 MHz): δ 5.1 5 (s, 2H, NH2), 7.39 (dd, 1 H, J= 9.3 Hz,1 .8 Hz , Ar), 7.71 (d, 2H, J = 9.3 Hz Ar), 7.93 (d, 1 H, J = 2.1 Hz, Ar), 8.22 (s, 1 H, Ar), 8.50 (d, 2H, J = 1 .8 Hz, Ar) ; MS (ES+) : m/e 254.0 (M+1 ).

Example 75:

5-(3-Bromoimidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl) pyridin-2-amine

The compound of example 74 (0.1 2 g, 0.431 mmol) was treated with N- bromosuccinimide (0.08 g, 0.44 mmol) in chloroform (1 0 mL) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.1 2 g (84.59 %) ; ¹ H NMR (CDCIs, 300 MHz) : δ 5.1 5 (s, 2H, NH ₂ ), 7.41 (dd, 1 H, J= 9.3 Hz, 1 .8 Hz , Ar), 7.69(s, 1 H, Ar), 7.73 (d, 1 H, J = 9.3 Hz, Ar), 7.93 (d, 1 H, J = 2.1 Hz, Ar), 8.22 (s, 1 H, Ar), 8.50 (d, 1 H, J = 1 .8 Hz, Ar) ; MS (ES+) : m/e 357.0 (M+1 ).

Example 76:

5-(3-(4-Morpholinophenyl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl) pyridine- amine

[1 ,1 '-Bis(diphenylphosphino)ferrocene]dichloro palladium(l l) complex with dichloromethane (0.01 37 g, 0.01 7 mmol) was added to a solution of the compound of example 75 (0.2 g, 0.560 mmol), 4-morpholinophenylboronic acid (0.145 g, 0.700 mmol), in DMF (2 mL) in a microwave tube followed by addition of sodium carbonate (0.1 1 9 g, 1 .120 mmol) solution in 0.4 mL of water. The tube was sealed and heated on microwave at 140 °C for 40 min. The reaction mixture was quenched in cold water (20 mL) and extracted with ethyl acetate (2 ^χ 25mL). The organic layer was washed with water (2x50 mL) and brine (50 mL) and dried over anhydrous sodium sulphate The solvent was evaporated to obtain the crude material, which was purified by column chromatography (silica gel, 3 % methanol in chloroform). Yield: 0.1 1 g (44.50 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 3.1 8 (t, 4H, 2CH ₂ ), 3.74 (t, 4H, 2CH ₂ ), 6.62 (s, 2H, NH ₂ , exchangeable with D ₂ 0), 7.09 (d, 2H, J = 8.7 Hz, Ar), 7.52 - 7.59 (m, 3H, Ar), 7.64 - 7.69 (m, 2H, Ar), 8.01 (s, 1 H, Ar), 8.52 (d, 2H, d, J = 4.5 Hz, Ar); MS (ES+): m/e 440.2 (M+1 ).

Example 77:

t-Butyl 4-(5-(6-(6-amino-5-(trifluoromethyl)pyridin-3-yl)imidazo[1 ,2-a] pyridin-3- yl)pyridin-2-yl)piperazine-1-carboxylate

Bis(triphenylphosphin)-palladium(ll)-dichloride (6.29 mg, 8.96 μιηοΙ was added to a solution of the compound of example 75 (0.2 g, 0.560 mmol) and t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (262 mg, 0.672 mmol), in DMF (5 mL) in a microwave tube followed by addition of potassium carbonate (1 16 mg, 0.840 mmol) solution in 1 mL of water. The tube was sealed and heated on microwave at 140°C for 40 min. The reaction mixture was quenched in cold water (20 mL) and extracted with ethyl acetate (2x25 mL). The organic layer was washed with water (2x50 mL) and brine (50 mL) and dried over anhydrous sodium sulphate The solvent was evaporated to obtain the crude material, which was purified by column chromatography (silica gel, 3 % methanol in chloroform). Yield: 0.125 g (41 .40 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 1 .41 (s, 9H, 3CH3), 3.44 (d, 4H, J = 8.7 Hz, 5.1 Hz, 2CH ₂ ), 3.56 (d, 4H, J = 5.7 Hz, 2CH ₂ ), 6.61 (s, 2H, NH ₂ , Exchangeable with D ₂ 0), 6.99 (d, 1 H, J = 9.0 Hz, Ar), 7.55 (d, 1 H, J = 9.3 Hz, Ar), 7.66-7.69 (m, 2H, Ar), 7.91 (dd, 1 H, J = 8.7 Hz, J = 2.1 Hz, Ar), 8.04 (s, 1 H, Ar), 8.44(d, 1 H, Ar), 8.51 (d, 2H, d, J= 5.7 Hz, Ar); MS (ES+): m/e 540.0 (M+1 ). Example 78:

5-(3-(6-(Piperazin-1-yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl) pyridin-2-amine

The compound of example 77 (0.08 g, 0.148 mmol) was treated with dioxane-HCI (10 mL, 3.29 mmol) in dioxane (5 mL) according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 0.06 g (92.00 %); ¹ H NMR (300 MHz, DMSO-de): δ 2.78 (s, 4H, 2CH ₂ ), 3.47 (s, 4H, 2CH ₂ ), 6.61 (s, 2H, NH ₂ , Exchangeable with D ₂ 0), 6.92 (d, 1 H, J = 9.0 Hz, Ar), 7.55 (d, 1 H, J = 9.3 Hz, Ar), 7.68 (d, 2H, J = 9.3 Hz, Ar), 7.86 (dd, 1 H, J = 8.7 Hz, J = 2.1 Hz, Ar), 8.03 (s, 1 H, Ar), 8.40 (d, 1 H, J = 2.1 Hz, Ar), 8.50 (d, 2H, J = 6.0 Hz, Ar); MS (ES+): m/e 440.2 (M+1 ). Example 79:

6-(5-(Trifluoromethyl)pyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 1 (2.0 g, 10.15 mmol) was treated with 5- (trifluoromethyl)pyridin-3-ylboronic acid (2.422 g, 12.69 mmol) in DMF (25 mL) in presence of sodium carbonate (2.152 g, 20.30 mmol) solution in 5 mL of water and [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.249 g, 0.305 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound Yield: 2.15 g (80.00 %). ¹ H NMR (CDCI3, 300 MHz): δ 7.39 - 7.42 (m, 1 H, Ar), 7.72 - 7.79 (m, 3H, Ar), 8.09 (s, 1 H, Ar), 8.41 (s, 1 H, Ar), 8.92 (s, 1 H, Ar), 9.02 (d, 1 H, J = 1 .5 Hz, Ar); MS (ES+): m/e 264.1 (M+1 ).

Example 80:

3-Bromo-6-(5-(trifluoromethyl)pyridin-3-yl)imidazo[1 ,2-a] pyridine

The compound of example 79 (2.100 g, 7.98 mmol) was treated with N- bromosuccinimide (1 .562 g, 8.78 mmol) in chloroform (25 mL), at 10-15°C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 2.23 g (82.00 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.46 - 7.49 (dd, 1 H, J = 9.3 Hz, J = 1 .5 Hz, Ar), 7.72 (s, 1 H, Ar), 7.77 (d, 1 H, J = 9.3 Hz, Ar), 8.13 (s, 1 H, Ar), 8.34 (s, 1 H, Ar), 8.95 (s, 1 H, Ar), 9.06 (d, 1 H, J = 1 .5 Hz, Ar); MS (ES+): m/e 344.0 (M+2).

Example 81 :

3-(4-(lsopropylthio)phenyl)-6-(5-(trifluoromethyl) pyridin-3-yl)imidazo[1 ,2-a] pyridine

The compound of example 80 (600 mg, 1 .754 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (430 mg, 2.192 mmol), in DMF (10 mL) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (43.0 mg, 0.053 mmol) and sodium carbonate 372 mg, 3.51 mmol) solution in 2 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.463 g (63.90 %); ¹ H NMR (300 MHz, DMSO-de): δ 1 .28 (d, 6H, J = 6.6 Hz, 2CH ₃ ), 3.59 (m, 1 H, CH), 7.50(d, 2H, J =8.1 Hz, Ar), 7.72 - 7.84 (m, 5H, Ar), 8.58 (s, 1 H, Ar), 8.90 (s, 1 H, Ar), 8.98 (s, 1 H, Ar), 9.25 (s, 1 H, Ar); MS (ES+): m/e 414.1 (M+1 ). Example 82:

3-(4-(lsopropylsulfinyl)phenyl)-6-(5-(trifluoromethyl)pyridi n-3-yl)imidazo[1 ,2-a] pyridine

The compound of example 81 (0.240 g, 0.580 mmol) was treated with metachloroperbenzoic acid (0.15 g, 0.871 mmol) in dichloromethane (20 mL) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 145 mg (58.20 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 0.97 (d, 3H, J = 6.6 Hz, CH ₃ ), 1 .21 (d, 3H, J = 6.9 Hz, CH ₃ ), 3.01 (m, 1 H, CH), 7.74 - 7.85 (m, 4H, Ar), 7.95 (s, 1 H, Ar), 7.98 (d, 2H, J = 8.1 Hz, Ar), 8.59 (s, 1 H, Ar), 8.98 (s, 2H, Ar), 9.26 (d, 1 H, J= 1 .5 Hz, Ar); MS (ES+): m/e 430.1 (M+1 ).

Example 83:

t-Butyl 4-(5-(6-(5-(trifluoromethyl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl) pyridin-2- yl)piperazine-1 -carboxylate

The compound of example 80 (250 mg, 0.733 mmol) was treated with t-butyl 4-(5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (342 mg, 0.879 mmol), in DMF (5 mL) in presence of bis(triphenylphosphin)-palladium(ll)- dichloride (15.43 mg, 0.022 mmol) and potassium carbonate (152 mg, 1 .099 mmol) solution in 1 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.35 g (91 .00 %); ¹ H NMR (300 MHz, DMSO-de): δ 1 .41 (s, 9H, 3CH ₃ ), 3.44 (t, 4H, 2CH ₂ ), 3.58 (t, 4H, 2CH ₂ ), 7.01 (d, 1 H, J = 8.7 Hz, Ar), 7.70 - 7.79 (m, 3H, Ar), 7.94 (dd, 1 H, J = 9.0 Hz, J = 2.4, Ar ), 8.47 (d, 1 H, J = 2.1 Hz, Ar), 8.58 (s, 1 H, Ar), 8.78 (s, 1 H, Ar), 8.97 (s, 1 H, Ar), 9.24 (d, 1 H, J = 1 .5 Hz, Ar); MS (ES+): m/e 525.2 (M+1 ).

Example 84:

3-(6-(Piperazin-1 -yl)pyridin-3-yl)-6-(5-(trifluoromethyl)pyridin-3-yl)imidazo [1 ,2- a] pyridine

The compound of example 83 (0.15 g, 0.286 mmol) was treated with dioxane-HCI (1 mL, 0.286 mmol) in dioxane (2 mL) according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 0.12 g (96.00 %); ¹ H NMR (300 MHz, DMSO-de): δ 2.78 (t, 4H, J = 5.1 Hz, 2CH ₂ ), 3.48 (t, 4H, J = 5.1 Hz, 2CH ₂ ), 6.93 (d, 1 H, J = 9.0 Hz, Ar), 7.68 - 7.78 (m, 3H, Ar), 7.87 (dd, 1 H, J = 9.0 Hz, J = 2.4, Ar), 8.44 (d, 1H, J= 2.1 Hz, Ar), 8.58 (s, 1H, Ar), 8.77 (s, 1H, Ar), 8.96 (s, 1H, Ar), 9.24 (d, 1 H, J = 1.5 Hz, Ar); MS (ES+): m/e 425.2 (M+1 ). Example 85:

5-(lmidazo[1,2-a]pyridin-6-yl)picolinonitrile

The compound of example 1 (2.0 g, 10.15 mmol) was treated with 5-(4, 4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (2.80 g, 12.18 mmol) in DMF (25 mL) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.249 g, 0.305 mmol) sodium carbonate (2.152 g, 20.30 mmol) solution in 5 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.91 g (85.00 %) ¹ H NMR (DMSO-de, 300 MHz): δ 7.65 (s, 1H, Ar), 7.70 (s, 2H, Ar), 7.98 (s, 1H, Ar), 8.14 (d, 1H, J= 8.1 Hz, Ar), 8.37 (dd, 1H, J= 8.4 Hz, J= 2.4 Hz, Ar), 9.14 - 9.17 (m, 2H, Ar); MS (ES+): m/e 221.1 (M+1H).

Example 86:

5-(3-Bromoimidazo[1,2-a]pyridin-6-yl)picolinonitrile

The compound of example 85 (1.7 g, 7.72 mmol) was treated with N-bromosuccinimide (1.562 g, 8.78 mmol) in chloroform (20 mL) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 1.9 g (82.00 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.80-7.81 (m, 3H, Ar), 8.15-8.18 (d, 1H, J=8.1 Hz, Ar), 8.47-8.50 (dd, 1H, J=8.4 Hz, J=2.1 Hz, Ar), 8.75 (s, 1H, Ar), 9.210- 9.216 (d, 1H, J= 1.8 Hz, Ar); MS (ES+): m/e 299.0 (M+1).

Example 87:

5-(3-(4-(Methylsulfonyl)phenyl)imidazo[1,2-a]pyridin-6-yl)pi colinonitrile

The compound of example 86 (0.200 g, 0.669 mmol) was treated with (4- (methylsulfonyl)phenyl)boronic acid (0.167 g, 0.836 mmol) in DMF (5 mL) in presence of [1,1'-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.01638 g, 0.020 mmol) and sodium carbonate (0.142 g, 1.337 mmol) solution in 1 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.11 g (42.90 %); ¹ H NMR (300 MHz, DMSO-de): δ 3.27 (s, 3H, SO ₂ CH ₃ ), 7.78 - 7.88 (m, 2H, Ar), 8.02 (s, 1 H, Ar), 8.03 - 8.09 (m, 4H, Ar), 8.14 (d, 1H, J= 8.1 Hz, Ar), 8.44 (dd, 1H, J= 8.1 Hz, J = 2.4 Hz, Ar), 9.03 (s, 1H, Ar), 9.19 ( d, 1H, J= 2.1 Hz, Ar); MS (ES+): m/e 375.1 (M+1). Example 88:

t-Butyl-4-(5-(6-(6-cyanopyridin-3-yl)imidazo

piperazine-1 -carboxylate

The compound of example 86 (0.25 g, 0.836 mmol) was treated with t-butyl 4-(5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (0.407 g, 1.045 mmol) in DMF (20 mL) in presence of [1,1'- bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.02048 mg, 0.025 mmol) and sodium carbonate (0.177 g, 1.672 mmol) solution in 4 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.25 g (61.40 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 1.41 (s, 9H, 3CH ₃ ), 3.45 (s, 4H, 2CH ₂ ), 3.58 (s, 4H, 2CH ₂ ), 6.98 (d, 1 H, J= 9.0 Hz, Ar), 7.71 (d, 1 H, J = 1.5 Hz, Ar), 7.74 (d, 1 H, J = 9 Hz, Ar), 7.80 (s, 1 H, Ar), 7.92 (dd, 1 H, J = 9.0 Hz, J= 2.4 Hz, Ar), 8.11 (d, 1H, J= 8.1 Hz, Ar), 8.40 (dd, 1H, J= 8.1 Hz, J = 2.4 Hz, Ar), 8.45 (d, 1H, J = 2.1 Hz, Ar), 8.76 (s, 1H, Ar), 9.15 (d, 1H, J= 2.1 Hz, Ar) ; MS (ES+): m/e 482.2 (M+1).

Example 89:

5-(3-(6-(Piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl) picolinonitrile

The compound of example 88 (0.150 g, 0.311 mmol) was treated with dioxane-HCI (0.11 g, 0.311 mmol) in 1,4-dioxane (2 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.087 g (73.00 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 2.80 (t, 4H, 2CH ₂ ), 3.51 (t, 4H, 2CH ₂ ), 6.96 (d, 1H, J= 8.7 Hz, Ar), 7.70 (dd, 1H, J= 5.4 Hz, J= 1.2 Hz, Ar), 7.75 (s, 1H, Ar), 7.79 (d, 1H, J= 5.7 Hz, Ar), 7.90 (dd, 1H, J= 5.1 Hz, J= 1.2 Hz, Ar), 8.13 (d, 1H, J=5.1 Hz, Ar), 8.43-8.45 (m, 2H, Ar), 8.78 (s, 1H, Ar), 9.17 (d, 1H, J = 1.2Hz, Ar); MS (ES+): m/e 382.2 (M+1).

Example 90:

5-(3-(4-(lsopropylthio)phenyl)imidazo[1,2-a]pyridin-6-yl) picolinonitrile

The compound of example 86 (0.3 mg, 1.003 mmol) was treated with 4- (isopropylthio)phenylboronic acid (0.236 g, 1.204 mmol) in DMF (5 mL) in presence of [1 ,1 '-bis(diphenylphosphino) ferrocene] dichloro palladium(ll) complex with dichloromethane (0.02457 g, 0.030 mmol) and sodium carbonate (0.213 g, 2.006 mmol) solution in 1 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.328 g (87.00 %); ¹ H NMR (300 MHz, DMSO-de): δ 1 .27 (d, 6H, J = 6.6 Hz, 2CH ₃ ), 3.59 (m, 1 H, CH ), 7.48 (d, 2H, J = 8.1 Hz, Ar), 7.71 (d, 3H, J = 7.8 Hz, Ar), 7.79 (s, 1 H, Ar), 7.83 (d, 1 H, Ar), 8.12 (d, 1 H, J = 8.1 Hz, Ar), 8.41 (dd, 1 H, J = 8.1 Hz, J = 2.4 Hz, Ar), 8.89 (s, 1 H, Ar), 9.15( d, 1 H, J = 2.1 Hz, Ar); MS (ES+): m/e 371 .2 (M+1 ).

Example 91 :

5- (6-(6-(Trifluoromethyl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-amine

The compound of example 68 (2 g, 5.85 mmol) was treated with 5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)pyridin-2-amine (1 .544 g, 7.02 mmol) in DMF (10 mL) in presence of [1 ,1 '-bis(diphenylphosphino) ferrocene] dichloro palladium(ll) complex with dichloromethane (0.143 g, 0.175 mmol) and sodium carbonate (1 .239 g, 1 1 .69 mmol) solution in 2 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1 .585 g (76.00 %); ¹ H NMR (300 MHz, DMSO-de): δ 6.27 { s, 2H, exchangeable with D ₂ O, NH ₂ ), 6.61 ( d, 1 H, J = 8.7Hz, Ar), 7.67-7.81 (m, 4H, Ar), 7.99 (d, 1 H, J = 8.4Hz, Ar), 8.23(d, 1 H, J= 2.4Hz), 8.44 (dd, 1 H, J = 8.1 Hz, J = 1 .8 Hz, Ar), 8.71 (s, 1 H, Ar), 9.15 ( d, 1 H, J = 1 .8Hz, Ar); MS (ES+): m/e 356.1 (M+1 ).

Example 92:

2-Amino-5-bromonicotinonitrile

2-Aminonicotinonitrile (0.5 g, 4.20 mmol) was treated with N-bromosuccinimide (0.777 g, 4.37 mmol) in chloroform (10 mL) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.467 g (56.20 %) ¹ H NMR (DMSO-de, 300 MHz): δ 7.14 (s, 2H, NH ₂ ), 8.15 (d, 1 H, J = 2.7 Hz, Ar), 8.27 (d, 1 H, J = 2.4 Hz, Ar); MS (ES+): m/e 200 (M+1 ).

Example 93:

6- Bromoimidazo[1 ,2-a]pyridine-8-carbonitrile

The compound of example 92 (30.0 g, 151 mmol) was treated with 2-chloro-1 ,1 - dimethoxyethane (42.5 g, 341 mmol) in 60 % ethanol (300 mL) in presence of sodium acetate (28.0 g, 341 mmol), and concentrated HCI (12.43 g, 341 mmol) according to the procedure for the preparation of the compound of example 1 to afford the title compound. Yield: 30.0 g (89.00 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.75 (d, 1H, J = 0.9 Hz, Ar), 8.083 (d, 1 H, J = 1.2 Hz, Ar), 8.23 (d, 1 H, J = 1.8 Hz, Ar), 9.24 (d, 1 H, J = 1.8 Hz, Ar); MS (ES+): m/e 223.9 (M+1 ).

Example 94:

6-Phenylimidazo[1,2-a]pyridine-8-carbonitrile

The compound of example 93 (3.0 g, 13.51 mmol) was treated with phenylboronic acid (1.977 g, 16.21 mmol) in DMF (20 ml_) in presence of [1,1'- bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.331 g, 0.405 mmol) and sodium carbonate (2.86 g, 27.0 mmol) solution in 4 ml_ of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.5 g (84.47 %) ¹ H NMR (CDCI ₃ , 300 MHz): δ 7.44 (t, 1H, J =7.2 Hz, Ar), 7.53 (t, 2H, J =7.2 Hz, Ar), 7.76-7.79 (m, 3H, Ar), 8.14 (d, 1H, J = 1.2 Hz, Ar), 8.38 (d, 1H, J= 1.5 Hz, Ar), 9.27 (d, 1H, J= 1.5 Hz, Ar); MS (ES+): m/e 220.1 (M+1). Example 95:

3-Bromo-6-phenylimidazo[1,2-a]pyridine-8-carbonitrile

The compound of example 94 (0.8 g, 3.42 mmol) was treated with N-bromosuccinimide (0.632 g, 3.55 mmol) in chloroform (20 ml_) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.924 g (85.55 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.47-7.56 (m, 3H, Ar), 7.83 (s, 1 H, Ar), 7.85 (s, 1H, Ar), 7.94 (s, 1H, Ar), 8.50 (s, 1H, Ar), 8.73 (s, 1H, Ar); MS (ES+): m/e 299.1 (M+1).

Example 96:

3-(4-Morpholinophenyl)-6-phenylimidazo[1,2-a]pyridine-8-c arbonitrile

The compound of example 95 (0.2 g, 0.671 mmol) was treated with 4- morpholinophenylboronic acid (0.167 g, 0.805 mmol) in DMF (5 ml_) in presence of [1,1'-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.02457 g, 0.030 mmol) and sodium carbonate (0.142 g, 1.342 mmol) solution in 1 ml_ of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.038 g (14.75 %); ¹ H NMR (300 MHz, DMSO-de): δ 3.21 (t, 4H, J = 4.8Hz, 2CH ₂ ), 3.76 (t, 4H, J= 4.8 Hz, 2CH ₂ ), 7.11 (d, 2H, J = 8.7 Hz, Ar), 7.40 - 7.52 (m, 3H, Ar), 7.60 (d, 2H, J = 8.7 Hz, Ar), 7.74 (d, 2H, J = 6.9 Hz), 7.84 (s, 1 H, Ar), 8.373 (d, 1 H, J = 1.5 Hz, Ar), 8.75 (d, 1 H, J = 1.5 Hz, Ar); MS (ES+): m/e 381.1 (M+1).

Example 97:

3-(4-(lsopropylthio)phenyl)-6-phenylimidazo[1,2-a]pyridine-8 -carbonitrile

The compound of example 95 (400 mg, 1.342 mmol) was treated 4- (isopropylthio)phenylboronic acid (316 mg, 1.610 mmol) in DMF (5 mL) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (32.9 mg, 0.040 mmol) and sodium carbonate (284 mg, 2.68 mmol) solution in 1 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.417 g (84.00 %); ¹ H NMR (300 MHz, DMSO-de): δ 1.30 (d, 6H, J= 6.6 Hz, 2CH ₃ ), 3.62 (m, 1H, CH), 7.40 - 7.54 (m, 5H, Ar), 7.72 -7.79 (m, 4H, Ar), 7.96 (s, 1H, Ar), 8.41 (d, 1H, J= 1.5 Hz, Ar), 8.85 (d, 1H, J= 1.5 Hz ,Ar); MS (ES+): m/e 370.1 (M+1). Example 98:

3-(4-(lsopropylsulfonyl)phenyl)-6-phenylimidazo[1,2-a] pyridine-8-carbonitrile

The compound of example 97 (0.3 g, 0.812 mmol) was treated with metachloroperbenzoic acid (0.26 g, 1.507 mmol) in chloroform (10 mL) according to the procedure for the preparation of the compound of example 5 to afford the title compound .Yield: 0.07 mg (24.52 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 1.20 (d, 6H, J = 6.9 Hz, 2CH ₃ ), 3.50 (m, 1 H, CH), 7.44 - 7.54 (m, 3H, Ar), 7.80 (d, 2H, J= 7.2 Hz, Ar), 7.99 (d, 2H, J =8.4 Hz, Ar), 8.08 (d, 2H, J =8.4 Hz, Ar), 8.14 (s, 1H, Ar), 8.48 (d, 1H, J = 1.2 Hz, Ar), 9.020 (d, 1H, J= 1.5 Hz, Ar); MS (ES+): m/e 402.1 (M+1). Example 99:

6-(6-Methylpyridin-3-yl)imidazo[1,2-a]pyridine-8-carbonitril e

The compound of example 93 (2.0 g, 9.01 mmol) was treated with 6-methylpyridin-3- ylboronic acid (1.480 g, 10.81 mmol) in DMF (10 mL) in presence of [1,1'- bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.221 g, 0.270 mmol) and sodium carbonate (1.909 g, 18.01 mmol) solution in 2 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1 .0 g (46.90 %) ¹ H NMR (DMSO, 300 MHz): δ 2.53 (s, 3H, CH ₃ ), 7.40 (d, 1 H, J = 8.4 Hz, Ar), 7.78 (d, 1 H, J = 1 .2 Hz, Ar), 8.06 (dd, 1 H, J = 8.1 Hz, J = 2.4 Hz, Ar), 8.143 (d, 1 H, J = 1 .2 Hz, Ar), 8.43 (d, 1 H, J = 1 .8 Hz, Ar), 8.85 (d, 1 H, J = 1 .8 Hz, Ar), 9.32 (d, 1 H, J = 1 .8 Hz, Ar); MS (ES+): m/e 235.1 (M+2H).

Example 100:

3-Bromo-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridine-8-carbonitrile

The compound of example 99 (0.8 g, 3.42 mmol) was treated with N-bromosuccinimide (0.632 g, 3.55 mmol) in chloroform (20 ml_) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.924 g (86.00 %) ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.50 (s, 3H, CH ₃ ), 7.40 (d, 1 H, J = 8.1 Hz, Ar), 7.95 (s, 1 H, Ar), 8.14 (dd, 1 H, J = 8.1 Hz, J = 2.4 Hz, Ar), 8.53 (d, 1 H, J = 1 .8 Hz, Ar), 8.48 - 8.91 (m, 2H, Ar); MS (ES+): m/e 315.1 (M+1 ).

Example 101 :

3-(4-(lsopropylthio)phenyl)-6-(6-methylpyridin-3-yl)imidazo [1 ,2-a] pyridine-8- carbonitrile

The compound of example 100 (0.35 g, 1 .1 18 mmol) was treated with 4- (isopropylthio)phenylboronic acid (0.263 g, 1 .341 mmol) in DMF (10 ml_) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.0274 g, 0.034 mmol) and sodium carbonate (0.237 g, 2.235 mmol) solution in 2 ml_ according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.425 g (98.00 %); ¹ H NMR (300 MHz, DMSO-de) : δ 1 .38 (d, 6H, J = 6.6 Hz, 2CH ₃ ), 2.65 (s, 3H, CH ₃ ), 3.49 - 3.58 (m, 1 H, CH), 7.32 (d, 1 H, J = 9.0 Hz, Ar), 7.48 - 7.57 (m, 4H, Ar), 7.74 (dd, 1 H, J = 8.1 Hz, J = 2.4 Hz, Ar), 7.86 (d, 1 H, J = 1 .5 Hz, Ar), 7.87 (s, 1 H, Ar), 8.60 (d, 1 H, J = 1 .8 Hz, Ar), 8.68 (d, 1 H, J = 2.1 Hz, Ar); MS (ES+): m/e 385.2 (M+1 ).

Example 102A:

3-(4-(lsopropylsulfinyl)phenyl)-6-(6-methylpyridin-3-yl)imid azo[1 ,2-a] pyridine-8- carbonitrile

The compound of example 101 (0.26 g, 0.676 mmol) was treated with metachloroperbenzoic acid (0.21 g, 1 .217 mmol) in CHCI ₃ (20 ml_) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.15 g (52.2 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 0.99 (d, 3H, J= 6.9 Hz, CH ₃ ), 1.23 (d, 3H, J= 6.9 Hz, CH ₃ ), 2.51 (s, 3H, CH ₃ ), 3.04 (m, 1H, CH), 7.38 (d, 1H, J= 8.1 Hz, Ar), 7.78 (d, 2H, J= 8.7 Hz, Ar), 8.00 (d, 2H, J= 8.4 Hz, Ar), 8.08 (s, 1H, Ar), 8.09 (dd, 1H, J =8.1 Hz, J =2.4 Hz, Ar), 8.493 (d, 1H, J= 1.5 Hz, Ar), 8.87 (d, 1H, J=2.1 Hz, Ar), 9.03 (d, 1H, 1.5 Hz, Ar); MS (ES+): m/e 401.1 (M+1).

Example 102B:

3-(4-(lsopropylsulfonyl)phenyl)-6-(6-methylpyridin-3-yl) imidazo[1 ,2-a]pyridine-8- carbonitrile

The compound of example 101 (0.26 g, 0.676 mmol) was treated with metachloroperbenzoic acid (0.21 g, 1.217 mmol) in CHCI ₃ (20 mL) according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.07 g (24.52 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 1.21 (d, 6H, J = 6.6 Hz, 2CH ₃ ), 2.51 (s, 3H, CH ₃ ), 3.51 (m, 1 H, CH), 7.39 (d, 1 H, J= 8.1 Hz, Ar), 8.00 (d, 2H, J= 8.4 Hz, Ar), 8.10 (s, 1H, Ar), 8.13 - 8.16 (m, 3H, Ar), 8.53 (s, 1H, Ar), 8.89 (d, 1H, J=2.1 Hz, Ar), 9.12 (s, 1H, Ar); MS (ES+): m/e 417.1 (M+1). Example 103:

6-(6-Methylpyridin-3-yl)-3-(4-morpholinophenyl)imidazo[1,2-a ]pyridine-8- carbonitrile

The compound of example 100 (0.2 g, 0.639 mmol) was treated with 4- morpholinophenylboronic acid (0.159 g, 0.766 mmol) in DMF (5 mL) in presence of [1,1'-bis(diphenylphosphino) ferrocene]dichloro palladium(ll) complex with dichloromethane (0.01565 g, 0.019 mmol) and sodium carbonate (0.135 g, 1.277 mmol) solution in 1 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.182 g (71.9 %); ¹ H NMR (300 MHz, DMSO-de): δ 2.65 (s, 3H, CH ₃ ), 3.22 (t, 4H, 2CH ₂ ), 3.77 (t, 4H, 2CH ₂ ), 7.11 (d, 2H, J= 8.7 Hz, Ar), 7.36 (d, 1H, J= 8.1 Hz, Ar), 7.62 (d, 2H, J= 8.7 Hz, Ar), 7.86 (s, 1H, Ar), 8.06 (dd, 1H, J= 8.1 Hz, J= 2.4 Hz, Ar), 8.41 (d, 1H, J= 1.5Hz, Ar), 8.84 (d, 2H, J= 1.5 Hz, Ar); MS (ES+): m/e 396.2 (M+1). Example 104:

t-Butyl 4-(5-(8-cyano-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a] pyridin-3-yl) pyridin-2- yl)piperazine-1 -carboxylate

The compound of example 1 00 (0.2 g, 0.639 mmol) was treated with 6-(4-(t- butoxycarbonyl)piperazin-1 -yl)pyridin-3-ylboronic acid (0.235 g, 0.766 mmol) in DMF (5 ml_) in presence of [1 , 1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(l l) complex with dichloromethane (0.01 565 g, 0.01 9 mmol) and sodium carbonate (0.1 35 g, 1 .277 mmol) solution in 1 ml_ of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.1 73 g (54.6 %) ; ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 1 .43 (s, 9H, 3CH ₃ ), 2.50 (s, 3H, CH ₃ ), 3.45 (s, 4H, 2CH ₂ ), 3.61 (s, 4H, 2CH ₂ ), 7.01 (d, 1 H, J = 8.7 Hz, Ar), 7.36 (d, 1 H, J = 8.1 Hz, Ar), 7.88 (s, 1 H, Ar), 7.95 (d, 1 H, J = 9.0 Hz, Ar), 8.08 (d, 1 H, J = 8.1 Hz, Ar), 8.43 - 8.47 (m, 2H, Ar), 8.84 (s, 2H, Ar) ; MS (ES+) : m/e 496.2 (M+1 ).

Example 105:

6-(6-Methylpyridin-3-yl)-3-(6-(piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a] pyridine-8- carbonitrile

The compound of example 1 04 (0.1 g, 0.202 mmol) was treated with dioxane HCI (0.031 ml_, 1 .009 mmol) in 1 ,4-dioxane (2 ml_) according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 0.08 g (99.00 %); ¹ H NMR (300 MHz, DMSO-d ₆ ) : δ 2.50 (s, 3H, CH ₃ ), 3.20 (s, 4H, 2CH ₂ ), 3.85 (s, 4H, 2CH ₂ ), 7.1 0 (d, 1 H, J = 9.0 Hz, Ar), 7.36 (d, 1 H, J = 8.1 Hz, Ar), 7.90 (s, 1 H, Ar ), 8.02 - 8.1 1 (m, 2H, Ar), 8.44 - 8.52 (m, 2H, Ar), 8.83 - 8.85 (m, 2H, Ar), 9.1 5 (s, 1 H, exchangeable with D ₂ 0, NH) ; MS (ES+) : m/e 396.2 (M+1 ).

Example 106:

6-(2-Methoxypyrimidin-5-yl)imidazo[1 ,2-a]pyridine-8-carbonitrile

The compound of example 93 (5.0 g, 22.52 mmol) was treated with 2-methoxypyrimidin- 5-ylboronic acid (4.1 6 g, 27.0mmol) in DMF (25 ml) in presence of [1 , 1 '- bis(diphenylphosphino)ferrocene]dichloro palladium(l l) complex with dichloromethane (0.552 g, 0.676 mmol) and sodium carbonate (4.77 g, 45.0 mmol) solution in 5 ml_ of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 4.61 g (81 .00 %) ¹ H NMR (DMSO-d6, 300 MHz): δ 3.98 (s, 3H, OCH ₃ ), 7.99 (s, 1 H, Ar), 8.15 (s, 1 H, Ar), 8.45 (s, 1 H, Ar), 9.01 (s, 2H, Ar), 9.32 (d, 1 H, J = 1 .5 Hz, Ar); MS (ES+): m/e 252.1 (M+1 ). Example 107:

3-Bromo-6-(2-methoxypyrimidin-5-yl)imidazo[1 ,2-a]pyridine-8-carbonitrile

The compound of example 106 (4.6 g, 18.31 mmol) was treated with N- bromosuccinimide (3.42 g, 19.22 mmol) in chloroform (50 mL) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 6.0g (92..53%). ¹ H NMR (DMSO-d6, 300 MHz): δ 3.99 (s, 3H, OCH ₃ ), 7.96 (s, 1 H, Ar), 8.53 (d, J = 1 .5Hz, 1 H, Ar), 8.97 (d, 1 H, J = 1 .2 Hz, Ar), 9.07 (s, 2H, Ar); MS (ES+): MS (ES+): m/e 331 .1 (M+1 ).

Example 108:

6-(2-Methoxypyrimidin-5-yl)-3-(4-morpholinophenyl) imidazo [1 ,2-a] pyridine-8- carbonitrile

The compound of example 107 (0.5 g, 1 .515 mmol) was treated with (4- morpholinophenyl)boronic acid (0.376 g, 1 .817 mmol) in DMF (10 mL) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.037 g, 0.045 mmol) and sodium carbonate (0.321 g, 3.03 mmol) solution in 2 mL according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.36 g (57.4 %); ¹ H NMR (300 MHz, DMSO-de) : δ 3.21 (t, 4H, J = 3.0 Hz, 2CH ₂ ), 3.77 (t, 4H, J = 3.0 Hz, 2CH ₂ ), 3.97 (s, 3H, OCHs ), 7.12 (d, 2H, J = 5.4 Hz, Ar), 7.64 (d, 2H, J = 5.1 Hz Ar), 7.87 (s, 1 H, Ar), 8.41 (s, 1 H, Ar), 8.96 (s, 1 H, Ar), 9.00 (s, 2H, Ar); MS (ES+): m/e 413.2 (M+1 ).

Example 109:

Ethyl 6-(2-hydroxypyrimidin-5-yl)-3-(4-morpholinophenyl) imidazo[1 ,2-a] pyridine- 8-carboxylate

The compound of example 108 was treated with sodium hydroxide (0.291 g, 7.27 mmol) in ethanol (10 ml) at 50°C for 3 h. The solvent was removed, residue obtained was diluted with cold water and pH adjusted to neutral with dilute hydrochloric acid. The reaction mixture was extracted with ethyl acetate (2x25 mL), washed with water (2x50 mL) and brine (50 mL) and dried over anhydrous sodium sulphate. The crude material obtained was purified using column chromatography (silica gel, 10 % methanol in chloroform) to afford the title compound. Yield: 0.203 g (62.5 %); %); ¹ H NMR (300 MHz, DMSO-de) : δ 1 .36 (t, 3H, J = 6.9 Hz, CH ₃ ), 3.21 (s, 4H, 2CH ₂ ), 3.77 (s, 4H, 2CH ₂ ), 4.21 (q, 2H, OCH ₂ ), 7.12 (d, 2H, J = 8.7 Hz, Ar), 7.64 (d, 2H, J = 8.4 Hz Ar), 7.83 (s, 1 H, Ar), 8.24 (s, 1 H, Ar), 8.84(s, 1 H, Ar), 8.97 (s, 2H, Ar), 9.58(s, 1 H, OH, Exchangeable with D ₂ O); MS (ES+): m/e 413.2 (M+1 ).

Example 110:

6-(2-Hydroxypyrimidin-5-yl)-3-(4-morpholinophenyl)imidazo[1 ,2-a]pyridine-8- carboxylic acid

The compound of example 109 was treated with sodium hydroxide (0.291 g, 7.27 mmol) in ethanol (10 mL) according to the procedure for preparation of compound of example 109, to afford the title compound. Yield: 0.024 g (7.74 %); δ 3.21 (s, 4H, 2CH ₂ ), 3.77 (s, 4H, 2CH ₂ ), 7.12 (d, 2H, J = 8.4 Hz, Ar), 7.62 (d, 2H, J = 8.4 Hz Ar), 7.80 (s, 1 H, Ar), 8.1 1 (s, 1 H, Ar), 8.16 (s, 1 H, Ar), 8.66 (s, 1 H, Ar), 8.76 (s, 1 H, Ar), 9.57 (s, 1 H, OH, Exchangeable with D ₂ O), 12.29 (s, 1 H, COOH, Exchangeable with D ₂ O); MS (ES+): m/e 417.2 (M+1 ).

Example 111 :

t-Butyl 4-(5-(8-cyano-6-(2-methoxypyrimidin-5-yl)imidazo[1 ,2-a]pyridin-3-yl) pyridin-2-yl)piperazine-1-carboxylate

The compound of example 107 (1 .0 g, 3.03 mmol) was treated with t-butyl 4-(5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (1 .415 g, 3.63 mmol) in DMF (20 ml) in presence of [1 ,1 '- bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.074 g, 0.091 mmol) and sodium carbonate (0.642 g, 6.06 mmol) solution in 4 mL according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.945 g (60.7 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 1 .43 (s, 9H, 3CH ₃ ), 3.45 (s, 4H, 2CH ₂ ), 3.61 (s, 4H, 2CH ₂ ), 3.97(s, 3H, OCH ₃ ), 7.02 (d, 1 H, J = 5.4 Hz, Ar), 7.89 (s, 1 H, Ar), 7.95 (dd, 1 H, J = 5.4 Hz, J = 1 .2 Hz, Ar), 8.43(s, 1 H, Ar), 8.48 (d, 1 H, J = 1 .2 Hz, Ar), 8.97 (s, 1 H, Ar), 9.01 (s, 2H, Ar); MS (ES+): m/e 513.3 (M+1 ). Example 112:

Methyl 3-(6-(4-t -butoxycarbonyl)piperazin-1 -yl)pyridin-3-yl)-6-(2-methoxy pyrimidin-5-yl)imidazo[1 ,2-a]pyridine-8-carboxylate

The compound of example 1 1 1 (0.400 g, 0.780 mmol) was treated with sodium hydroxide (0.312 g, 7.80 mmol) in methanol (20 mL) at reflux for 6 h. The solvent was removed, residue obtained was diluted with cold water and pH adjusted to neutral (~7) with dil HCI. The reaction mixture was extracted with ethyl acetate (2x25 mL), washed with water (2x50 mL) and brine (50 mL) and dried over anhydrous sodium sulphate. The crude material obtained was purified using column chromatography (silica gel, 10 % methanol in chloroform) to afford the title compound. Yield: 0.290 g (66.9 %); ¹ H NMR (300 MHz, CDCI ₃ ): δ 1 .66 (s, 9H, 3CH ₃ ), 3.61 (s, 4H, 2CH ₂ ), 3.66 (s, 4H, 2CH ₂ ), 4.09(s, 3H, OCHs), 4.13(s, 3H, OCH ₃ ), 6.81 (d, 1 H, J = 8.7 Hz, Ar), 7.65 (d, 1 H, J = 6.9 Hz, Ar), 7.83 (s, 1 H, Ar), 8.17(s, 1 H, Ar), 8.38(s, 1 H, Ar), 8.43 (s, 1 H, Ar), 8.72 (s, 2H, Ar); MS (ES+): m/e 546.3 (M+1 ).

Example 113:

Methyl 6-(2-methoxypyrimidin-5-yl)-3-(6-(piperazin-1 -yl)pyridin-3-yl)imidazo [1 ,2- a]pyrid i ne-8-car boxylate

The compound of example 1 12 (0.2 g, 0.367 mmol) was treated with trifluoroacetic acid (0.282 ml, 3.67 mmol) according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 0.128 g (77 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.23 (s, 4H, 2CH ₂ ), 3.84 (s, 4H, 2CH ₂ ), 3.98(s, 3H, OCH ₃ ), 3.99(s, 3H, OCH3), 7.13 (d, 1 H, J = 8.7 Hz, Ar), 8.02 (s, 2H, Ar), 8.37 (s, 1 H, Ar), 8.52(s, 1 H, Ar), 8.96(s, 1 H, Ar), 9.02 (s, 2H, Ar); MS (ES+): m/e 546.3 (M+1 ).

Example 114:

3-(4-(1 ,1 -Dioxidothiomorpholino)phenyl)-6-(2-methoxy pyrimidin-5-yl) imidazo[1 ,2- a]pyridine-8-carbonitrile

The compound of example 107 (0.6 g, 1 .817 mmol) was treated with 4-(4-(4, 4,5,5- tetramethyl-1 ,3, 2-dioxaborolan-2-yl)phenyl)thiomorpholine-1 ,1 -dioxide (0.797 g, 2.363 mmol) in DMF (10 mL) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.045 g, 0.055 mmol) and sodium carbonate (0.385 g, 3.63 mmol) solution in 2 mL according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.59 g (69.7 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.15 (s, 4H, 2CH ₂ ), 3.90 (s, 4H, 2CH ₂ ), 3.97(s, 3H, OCH ₃ ), 7.21 (d, 2H, J = 8.7 Hz, Ar), 7.66(d, 2H, J = 8.4 Hz), 7.89 (s, 1 H, Ar), 8.42 (s, 1 H, Ar), 8.97(s, 1 H, Ar), 9.01 (s, 2H, Ar) ; MS (ES+): m/e 461 .1 (M+1 ).

Example 115:

3-(4-(1 ,1 -Dioxidothiomorpholino)phenyl)-6-(2-hydroxypyrimidin-5-yl) imidazo[1 ,2- a]pyridine-8-carboxylic acid

The compound of example 1 14 (0.3 g, 0.651 mmol) was treated with sodium hydroxide (0.130 g, 3.26 mmol) in ethanol (10 mL) at reflux for 4 h. The solvent was removed, residue obtained was diluted with cold water and pH adjusted to neutral (~7) with dil HCI. The reaction mixture was extracted with ethyl acetate (2x25 mL), washed with water (2x50 mL) and brine (50 mL) and dried over anhydrous sodium sulphate. The crude material obtained was purified by using column chromatography (silica gel, 10 % methanol in chloroform) to afford the title compound. Yield: 0.05 g (15.45 %); ¹ H NMR (DMSO-de, 300 MHz): δ 3.16 (s, 4H, 2CH ₂ ), 3.90 (s, 4H, 2CH ₂ ), 7.21 (d, 2H, J = 8.4 Hz, Ar), 7.65 (d, 2H, J = 8.1 Hz), 7.82 (s, 1 H, Ar), 812 (s, 1 H, Ar), 8.17(s, 1 H, Ar), 8.64 (s, 1 H, Ar), 8.78 (s, 1 H, Ar), 9.57 (s, 1 H, OH, Exchangeable with D ₂ O), 12.30 (s, 1 H, OH, Exchangeable with D ₂ O); MS (ES+): m/e 465.1 (M+1 ).

Example 116:

6-(6-(1 H-tetrazol-5-yl)pyridin-3-yl)-3-(4-(methylsulfonyl) phenyl)imidazo [1 ,2-a] pyridine

The compound of example 87 (200 mg, 0.534 mmol) was treated with sodium azide (69.5 mg, 1 .068 mmol) and ammonium chloride (57.1 mg, 1 .068 mmol) in DMF (5 mL) at 120 °C for 1 h. The solvent was evaporated to yield a residue which was purified by combiflash chromatography in 20 % methanol in chloroform to afford the title compound. Yield: 0.070 g (30.9 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 3.29 (s, 3H, SO ₂ CH ₃ ), 7.79-7.88 (m, 2H, Ar), 8.02 (s, 1 H, Ar), 8.06 - 8.15 (m, 5H, Ar), 8.26 (d, 1 H, J = 6.0 Hz, Ar), 8.95 (s, 1 H, Ar), 9.02 (s, 1 H, Ar); MS (ES+): m/e 418.1 (M+1 ).

Example 117:

3-(6-(lsopropylthio)pyridin-3-yl)-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 3 (0.3 g, 1 .094 mmol) was treated with 2-(isopropylthio)-5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (0.367 g, 1 .313 mmol) in DMF (5 mL) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.0268 g, 0.033 mmol) and sodium carbonate (0.232 g, 2.189 mmol) solution in 1 mL of water according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 425 mg (98.00 %); ¹ H NMR (300 MHz, DMSO-de): δ 1 .37 (d, 6H, J = 6.9 Hz, 2CH ₃ ), 4.01 (m, 1 H, CH), 7.40 (d, 1 H, J = 8.4 Hz, Ar), 7.48 (q, 1 H, Ar), 7.68 (dd, 1 H, J = 9.3 Hz, J = 1 .5 Hz, Ar), 7.79 (d, 1 H, J = 9.3 Hz, Ar), 7.88 (s, 1 H, Ar), 8.05 (dd, 1 H, J = 8.4 Hz, J = 2.4 Hz, Ar), 8.16 (d, 1 H, J = 8.1 Hz, Ar),8.59 (d, 1 H, J = 3.3 Hz, Ar), 8.76 (s, 1 H, Ar), 8.81 (d, 1 H, J =2.1 Hz, Ar), 8.97 (d, 1 H, J = 2.1 Hz, Ar); MS (ES+): m/e 347.1 (M+1 ).

Example 118:

5-(3-(6-(lsopropylthio)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoro

methyl)pyridin-2-amine

The compound of example 75 (0.5 g, 1 .400 mmol) was treated with 2-(isopropylthio)-5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (0.586 g, 2.100 mmol) in DMF (5 mL) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.0343 g, 0.042 mmol) and sodium carbonate (0.297 g, 2.80 mmol) solution in 1 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 425 mg (98.00 %); ¹ H NMR (300 MHz, DMSO-de): δ 1 .38 - 1 .40 (d, 6H, J = 6.9Hz, 2CH ₃ ), 4.01 (m, 1 H, CH), 6.64 (s, 2H, exchangeable with D ₂ O, NH ₂ ), 7.40 - 7.42 (d, 1 H, J = 8.1 Hz, Ar), 7.61 (dd, 1 H, J = 9.3 Hz, J = 1 .5 Hz, Ar), 7.72 (d, 1 H, J = 9.3 Hz, Ar), 7.84 (s, 1 H, Ar), 8.03 - 8.09 (m, 2H, Ar), 8.57 (d, 1 H, J = 2.1 Hz, Ar), 8.68 (s, 1 H, Ar), 8.81 (d, 1 H, J = 2.1 Hz, Ar); MS (ES+): m/e 430.1 (M+1 ).

Example 119:

t-Butyl 4-(3-methyl-5-(6-(5-(trifluoromethyl)pyridin-3-yl) imidazo[1 ,2-a] pyridin-3- yl)pyridin-2-yl)piperazine-1-carboxylate

The compound of example 80 (400 mg, 1 .169 mmol) was treated with tert-butyl 4-(3- methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl) piperazine-1 - carboxylate (613 mg, 1 .520 mmol), in DMF (10 mL) in presence of [1 ,1 '- bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (28.6 mg, 0.035 mmol) and sodium carbonate (248 mg, 2.338 mmol) solution in 2 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.487 g (76.00 %) ; ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 1 .43(s, 9H, 3CH ₃ ), 2.35(s, 3H, CH ₃ ), 3.1 2 (s, 4H, 2CH ₂ ), 3.50 (s, 4H, 2CH ₂ ), 7.74 - 7.81 (m, 3H, Ar), 7.94 (s, 1 H, Ar), 8.52 (d, 1 H, J = 2.1 , Ar ), 8.61 (s, 1 H, Ar), 8.89 (s, 1 H, Ar ), 8.99 (s 1 H, Ar), 9.27 (s, 1 H, Ar) ; MS (ES+): m/e 539.2 (M+1 ).

Example 120:

3-(5-Methyl-6-(piperazin-1-yl)pyridin-3-yl)-6-(5-(trifluoro methyl)pyridin-3-yl) imidazo[1 ,2-a]pyridine

The compound of example 1 1 9 (0.3 g, 0.557 mmol) was treated with trifluoroacetic acid (0.31 8 g, 2.79 mmol) in dichloromethane (1 0 mL) according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 80 mg (99.00 %); ¹ H NMR (300 MHz, DMSO-d ₆ ) : δ 2.33 (s, 3H, CH ₃ ), 2.87 (s, 4H, 2CH ₂ ), 3.09 (s, 4H, 2CH ₂ ), 7.76 - 7.90 (m, 4H, Ar), 8.50 (d, 1 H, J = 1 .8 Hz, Ar), 8.61 (s, 1 H, Ar ), 8.88 (s, 1 H, Ar), 8.99 (s, 1 H, Ar), 9.27 (s, 1 H, Ar) ; MS (ES+) : m/e 439.2 (M+1 ).

Example 121 :

5-(3-(4-Morpholinophenyl)imidazo[1 ,2-a]pyridin-6-yl)picolino nitrile

The compound of example 86 (1 .0 g, 3.34 mmol) was treated with 4-(4-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl) morpholine (1 .1 60 g, 4.01 mmol) in DMF (25 mL) in presence of [1 , 1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(l l) complex with dichloromethane (0.082 g, 0.100 mmol) and sodium carbonate (0.709 g, 6.69 mmol) solution in 5 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.1 82 g (71 .9 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 3.55 (t, 4H, 2CH ₂ ), 3.73 (t, 4H, 2CH ₂ ), 7.00 (d, 1 H, J = 8.7 Hz, Ar), 7.73 (d, 1 H, J = 1 .5 Hz, Ar), 7.77 (s, 1 H, Ar), 7.79 (d, 1 H, J = 9.6 Hz, Ar), 7.82 (s, 1 H, Ar) 7.94 (dd, 1 H, J = 8.7 Hz, J = 2.4 Hz, Ar), 8.1 3 (d, 1 H, J = 8.1 Hz, Ar), 8.42 (dd, 1 H, J = 8.4 Hz, J = 2.4 Hz, Ar), 8.48 (d, 1 H, J = 2.1 Hz, Ar), 8.79 (s, 1 H, Ar), 9.1 7 (d, 1 H, J = 1 .8 Hz, Ar); MS (ES+): m/e 383.1 (M+2).

Example 122:

5-(3-(4-(Methylsulfonyl)phenyl)imidazo[1 ,2-a]pyridin-6-yl) picolinamide

The compound of example 87 (0.3 g, 0.801 mmol) were suspended in ethanol (20 mL). Sodium hydroxide (0.1 28 g, 3.20 mmol) was dissolved in 4mL of water and half of the volume of sodium hydroxide was added to the reaction mixture with further addition of hydrogen peroxide (0.270 mL, 8.81 mmol) (30 percent). After stirring the reaction mixture for 30 minutes, remaining sodium hydroxide solution was added. The reaction mixture was stirred at 25 - 30 °C for 3 h. The reaction mixture was diluted with water and the pH was adjusted to 7.0 with 2N HCI. The precipitate obtained was isolated by filtration. The crude material obtained was purified by column chromatography (silica gel, 7 % methanol in chloroform). Yield: 0.177 g (52.90 %); ¹ H NMR (300 MHz, DMSO- d ₆ ): δ 3.29 (s, 3H, S0 ₂ CH ₃ ), 7.72 (s, 1 H, NH2), 7.79 - 7.89 (m, 2H, Ar), 8.03 - 8.15 (m, 6H, Ar), 8.37 - 8.39 (d, 1 H, J = 8.1 Hz, Ar), 8.99 - 9.03 (m, 2H, Ar); MS (ES+): m/e 393.1 (M+1 ).

Example 123:

N,N-Dimethyl-4-(5-(6-(5-(trifluoromethyl)pyridin-3-yl)imidaz o [1 ,2-a]pyridin-3- yl)pyridin-2-yl)piperazine-1 -carboxamide

To a stirred solution of compound of example 84 (0.2 g, 0.471 mmol) in dichloromethane (10 mL) pyridine was added (0.057 mL, 0.707 mmol). The reaction mixture was cooled to 0 - 5 °C, dimethylcarbamic chloride was added at the same temperature (0.052 mL, 0.565 mmol) and the reaction mixture was stirred for 2 h keeping the temperature constant. The reaction mixture was diluted with dichloromethane and washed with water (2x25 mL) and brine (25 mL). The reaction mixture was dried over anhydrous sodium sulphate and the solvent was evaporated to obtain the crude material. The crude material obtained was purified by column chromatography (silica gel, 5 % methanol in chloroform). Yield: 0.07 g (29.7 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 2.79 (s, 6H, 2CH ₃ ), 3.23 (s, 4H, 2CH ₂ ), 3.59 (s, 4H, 2CH ₂ ), 7.00 - 7.03 (d, 1 H, J = 9.0 Hz, Ar), 7.76 - 7.77 (m, 3H, Ar), 7.94 (dd, 1 H, J = 9.0, 2.4 Hz, Ar), 8.491 (d, 1 H, J = 2.1 Hz, Ar), 8.60 (s, 1 H, Ar), 8.80 (s, 1 H, Ar), 8.98 (s, 1 H, Ar), 9.25 (s, 1 H, Ar); MS (ES+): m/e 496.2 (M+1 ).

Example 124:

5-(3-(4-Thiomorpholine 1 ,1 -dioxidephenyl)imidazo[1 ,2-a] pyridin-6-yl)

picolinonitrile

The compound of example 86 (0.3 g, 1 .003 mmol) was treated with 4-(4-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl) phenyl) thiomorpholine 1 ,1 -dioxide (0.44 g, 1 .304 mmol) in DMF (10 mL) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.02457 g, 0.030 mmol) and sodium carbonate (0.213 g, 2.006 mmol) solution in 2 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.043 g (9.05 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 3.16 (s, 4H, 2CH ₂ ), 3.88 (s, 4H, 2CH ₂ ), 7.18 (d, 2H, J= 8.7 Hz, Ar), 7.62 (d, 2H, J= 8.7 Hz, Ar), 7.68 - 7.80 (m, 3H, Ar), 8.09 (d, 1H, J= 8.1 Hz, Ar), 8.36 (dd, 1H, J= 8.1 Hz, J= 2.1 Hz, Ar), 8.79 (s, 1H, Ar), 9.122 (d, 1H, J= 1.8 Hz, Ar); MS (ES+): m/e 430.1 (M+1).

Example 125:

5-(3-(6-Methoxypyridin-3-yl)imidazo[1,2-a]py

The compound of example 86 (0.5 g, 1.672 mmol) was treated with (6-methoxypyridin- 3-yl)boronic acid (0.307 g, 2.006 mmol) in DMF (10 mL) in presence of [1,1'- bis(diphenylphosphino)ferrocene] dichloro palladium(ll) complex with dichloromethane (0.041 g, 0.050 mmol) and sodium carbonate (0.354 g, 3.34 mmol) solution in 2 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.47 g (86.0 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 3.94 (s, 3H, OCH ₃ ), 7.00 (d, 1H, J= 8.7 Hz, Ar), 7.73 (dd, 1H, J= 9.6 Hz, J= 1.5 Hz, Ar), 7.82 - 7.85 (m, 2H, Ar), 8.10 - 8.17 (m, 2H, Ar), 8.44 (dd, 1 H, J = 8.1 Hz, J = 2.1 Hz, Ar), 8.55 (d, 1H, J= 2.4 Hz, Ar), 8.84 (s, 1H, Ar), 9.18 (d, 1H, J= 1.8 Hz, Ar); MS (ES+): m/e 328.1 (M+1).

Example 126:

5-(3-(6-Aminopyridin-3-yl)imidazo[1,2-a]pyridin-6-yl)-3-(tri fluoromethyl) pyridine- amine

The compound of example 75 (0.200 g, 0.56 mmol) was treated with 5-(4, 4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.186 g, 0.84 mmol) in DMF (20 mL) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (45.8 mg, 0.056 mmol) and sodium carbonate (0.474 g, 4.48 mmol) solution in 4 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.11 g (53.02 %) ¹ H NMR (CDCI ₃ , 300 MHz): 56.24 (s, 2H, NH2), 6.59 (s, 1H, Ar), 6.62 (s, 2H, NH2), 7.53 - 7.75 (m, 4H Ar), 8.04 (d, 1 H, J = 2.1 Hz, Ar), 8.21 (d, 1 H, J = 2.1 Hz, Ar), 8.21 - 8.54 (m, 2H, Ar),; MS (ES+): m/e 409.1 (M+1). Example 127:

5-(3-(4-Aminophenyl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl)pyridin-2-ami

The compound of example 75 (0.2 g, 0.56 mmol) was treated with 4-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (0.1 86 g, 0.84 mmol) in dry DMF (20 mL) in presence of dichlorobis(triphenylphosphine)palladium(l l) (0.0063 g, 0.009 mmol) and potassium carbonate (0.1 1 6 g, 0.84 mmol) in water (1 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.085 g (41 .56 %) ; ¹ H NMR (CDCI ₃ , 300 MHz) : δ 5.40 (s, 2H, NH ₂ ), 6.63 (s, 2H, NH ₂ ), 6.71 (d, 2H, J =8.4 Hz, Ar), 7.35 (d, J = 8.4 Hz, 2H, Ar), 7.50 (dd, J = 9.3 Hz, J = 1 .5 Hz, 1 H, Ar), 7.59 (s, 1 H, Ar), 7.65 (d, J = 9.3 Hz, 1 H, Ar), 8.01 3 (d, J = 1 .8 Hz, 1 H, Ar), 8.48 - 8.53 (m, 2H, Ar); MS (ES+) : m/e 370.1 (M+1 ).

Example 128:

5-(3-(5-Fluoropyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl) pyridine- amine

The compound of example 75 (0.1 50 g, 0.42 mmol) was treated with 5-fluoropyridin-3- ylboronic acid (0.077 g, 0.54 mmol) in DMF (20 mL) in presence of [1 ,1 '- bis(diphenylphosphino)ferrocene]dichloro palladium(l l) complex with dichloromethane (0.0343 g, 0.042 mmol) and sodium carbonate (0.356 g, 3.36 mmol) solution in 4 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound Yield: 0.1 1 0 g (47.94 %) ¹ H NMR (CDCI ₃ , 300 MHz): δ 5.1 6 (s, 2H, NH ₂ ), 7.42 (dd, 1 H, J = 9.3 Hz, J = 1 .5 Hz, Ar), 7.63 - 7.67 (m, 1 H, Ar), 7.81 - 7.85 (m, 3H, Ar), 8.36 - 8.42 (m, 2H, Ar), 8.57 (d, 1 H, J = 2.7 Hz), 8.74 (s, 1 H, Ar) ; MS (ES+): m/e 371 .1 (M+1 ).

Example 129:

5-(3-(4-(Methylsulfonyl)phenyl)imidazo[1 ,2-a]pyridin-6-yl)-3-(trifluoromethyl) pyridin-2-amine

The compound of example 75 (1 00 g, 0.28 mmol) was treated with 4- (methylsulfonyl)phenylboronic acid (72.8 g, 0.84 mmol) in DMF (5 mL) in a microwave tube in presence of [1 , 1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(l l) complex with dichloromethane (0.020 g, 0.028 mmol) and sodium carbonate (0.237 g, 2.24 mmol) solution in 1 mL of water. The reaction mixture was heated to 1 20 °C on microwave for 10 min. The reaction mixture was quenched in cold water (25 mL) and extracted with ethyl acetate (2x25ml_) The organic layer was washed with water (2x50 ml_) and brine (50 ml_) and dried over anhydrous sodium sulphate The solvent was evaporated to obtain the crude material which was purified by column chromatography (silica gel, 3 % methanol in chloroform). Yield: 0.0875 g (59.70 %); ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 3.1 6 (s, 3H, S0 ₂ CH ₃ ), 5.14 (s, 2H, NH ₂ ), 7.43(d, 1 H, J =9.0Hz), 7.82-7.86 (m, 5H), 8.12 (d, 2H, J = 7.5 Hz, Ar ), 8.44 (s, 2H, Ar) ; MS (ES+) : m/e 432.9 (M+1 ).

Example 130:

6-(6-Methoxypyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 1 (1 .0 g, 5.07 mmol) was treated with (6-methoxypyridin-3- yl)boronic acid (0.97 g, 6.34 mmol) in the presence of dichlorobis(triphenylphosphine)palladium(l l) (0.057 g, 0.0812 mmol) and potassium carbonate (1 .051 g, 7.605 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1 .0 g (87.71 %); ¹ H NMR (DMSO-d ₆ , 300 MHz) : 5 4.01 (s, 3H, OCH ₃ ), 6.87 (d, 1 H, J = 8.4Hz, Ar), 7.36 (d, 1 H, J = 9.0 Hz, Ar), 7.66 - 7.78 (m, 4H, Ar ), 8.27 (s, 1 H, Ar), 8.37 (s, 1 H, Ar) ; MS (ES+) : m/e 226 (M+1 ). Example 131 :

3-Bromo-6-(6-methoxypyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 1 30 (0.875 g, 3.88 mmol) was treated with N- bromosuccinimide (0.71 9 g, 4.04 mmol) in chloroform (20 ml_) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 1 .17 g ( 99.51 %); ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 4.01 (s, 3H, OCHs), 6.89 (d, 1 H, J = 8.4Hz, Ar), 7.43 (d, 1 H, J = 8.7 Hz, Ar), 7.67 - 7.72 (m, 2H, Ar ), 7.81 (d, 1 H, J = 7.8Hz, Ar), 8.23 (s, 1 H, Ar), 8.41 (s, 1 H, Ar); MS (ES+): m/e 304 (M+1 ).

Example 132:

5-(6-(6-Methoxypyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)-3-(trifluoromethyl) pyridin- 2-amine

The compound of example 1 31 (0.4 g, 1 .31 mmol) was treated with 5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amine (0.491 g, 1 .70 mmol) in DMF (20 ml_) in presence of [1 , 1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(l l) complex with dichloromethane (0.1 00 g, 0.1 31 mmol) and sodium carbonate (1 .1 1 g, 1 0.48 mmol) solution in 4 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.36 g (71 .22 %); ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 3.89 (s, 3H, OCH ₃ ), 6.76 (s, 2H, NH ₂ ), 6.91 (d, 1 H, J = 8.4 Hz, Ar), 7.58 (d, 1 H, J = 8.7 Hz, Ar ), 7.73 (s, 2H, Ar), 8.03 (s, 2H, Ar), 8.52 (s, 3H, Ar) ; MS (ES+) : m/e 385.8 (M+1 ).

Example 133:

3-(6-Methoxypyridin-3-yl)-6-(5-(trifluoromethyl)pyridin-3-yl )imidazo[1 ,2-a] pyridine The compound of example 80 (0.3 g, 0.87 mmol) was treated with 6-methoxypyridin-3- ylboronic acid (0.1 65 g, 1 .08 mmol) in DMF (20 mL) in presence of [1 ,1 '- bis(diphenylphosphino)ferrocene]dichloro palladium(l l) complex with dichloromethane (0.071 g, 0.08 mmol) and sodium carbonate (0.738 g, 6.09 mmol) solution in 4 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.28 g (86.1 9 %) ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 4.02 (s, 3H, OCH ₃ ), 6.93 (d, 1 H, J = 8.7 Hz, Ar), 7.41 (dd, 1 H, J = 9.3 Hz, J = 1 .8 Hz, Ar), 7.74 - 7.85 (m, 3H, Ar ), 8.04 (s, 1 H, Ar), 8.35 (s, 1 H, Ar), 8.39 (d, 1 H, J = 2.1 Hz, Ar), 8.91 - 8.98 (m, 2H, Ar); MS (ES+) : m/e 371 (M+1 ). Example 134:

6-Bromo-5,7-dimethylimidazo[1 ,2-a]pyridine

(Commercially available) 5-Bromo-4,6-dimethylpyridin-2-amine (1 0 g, 49.7 mmol) and 2- bromo-1 , 1 -dimethoxyethane [42 g (d=1 .43 g/mL), 249 mmol] were treated with concentrated hydrochloric acid (7.68 mL (d=1 .1 8 g/mL), 249 mmol) in 60 % ethanol according to the procedure for the preparation of the compound of example 1 to afford the title compound. Yield: 1 0 g (89 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.41 (s, 3H, CH ₃ ), 2.76 (s, 3H, CH ₃ ), 7.49 (s, 1 H, Ar), 7.59 (d, 1 H, J=1 .2 Hz Ar), 7.78 (s, 1 H, Ar); MS (ES+): m/e 225 (M +1 ). Example 135:

5,7-Dimethyl-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 134 (2.5 g, 1 1 .1 1 mmol) was treated with pyridin-3-ylboronic acid (1 .77 g, 5.08 mmol) in the presence of tetrakis(triphenyl-phosphine)palladium(0) (0.205 g, 0.178 mmol) and potassium carbonate (1 .76 g, 1 6.66 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1 .2 g (48.4 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.02 (s, 3H, CH ₃ ), 2.31 (s, 3H, CH ₃ ), 7.45 (s, 1 H, Ar), 7.51 -7.55 (dd, 1 H, J=4.8 & J=7.5 Hz, Ar), 7.61 (d, 1 H, J=0.6 Hz Ar), 7.75-7.78 (m, 1 H, Ar), 7.82 (s, 1 H, Ar), 8.51 (d, 1 H, J=1 .5 Hz, Ar), 8.64-8.66 (dd, 1 H, J=1 .2 & J=4.5 Hz, Ar); MS (ES+): m/e 224.1 (M+1 ).

Example 136:

3- Bromo-5,7-dimethyl-6-(pyridin-3-yl)imidazo[1 ,2-a] pyridine

The compound of example 135 (0.950 g, 4.25 mmol) was treated with N- bromosuccinimide (0.788 g, 4.43 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.502 g (39.0 %); NMR (DMSO-d ₆ , 300 MHz): δ 1 .95 (s, 3H, CH ₃ ), 2.69 (s, 3H, CH ₃ ), 7.47 (s, 1 H, Ar), 7.52-7.56 (dd, 1 H, J=4.8 Hz, J=7.8 Hz, Ar), 7.60 (s, 1 H, Ar), 7.73-7.77 (m, 1 H, Ar), 8.49 (d, 1 H, J=1 .5 Hz, Ar), 8.64-8.66 (dd, 1 H, J=1 .8 Hz & J=4.8 Hz, Ar); MS (ES+): m/e 302 (M+1 ).

Example 137:

4- (4-(5,7-Dimethyl-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)phenyl) morpholine

The compound of example 136 (0.200 g, 0.662 mmol) was treated with (4- morpholinophenyl)boronic acid (0.151 g, 0.728 mmol) in the presence of dichlorobis(triphenylphosphine) palladium(ll) (0.0074 g, 0.016 mmol) and potassium carbonate (0.137 g, 0.993 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield : 0.050 g (18.74 %);

¹ H NMR (DMSO-de, 300 MHz): δ 1 .90 (s, 3H, CH ₃ ), 1 .98 (s, 3H, CH ₃ ), 3.15 (t, 4H, 2CH ₂ ), 3.74 (t, 4H, 2CH ₂ ), 6.9 (d, 1 H, J=8.7 Hz, Ar), 7.33 (d, 2H, J=8.7 Hz, Ar), 7.39 (s,

1 H, Ar), 7.47-7.51 (m, 2H, Ar), 7.73 (d, 1 H, J=7.8 Hz, Ar), 8.47 (s, 1 H, Ar), 8.61 (d, 1 H,

J=4.8 Hz, Ar); MS (ES+): m/e 385.2 (M+1 ).

Example 138:

3-(4-(lsopropylthio)phenyl)-5,7-dimethyl-6-(pyridin-3-yl) imidazo[1 ,2-a] pyridine

The compound of example 136 (0.200 g, 0.662 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.156 g, 0.794 mmol) in the presence of dichlorobis(triphenylphosphine)palladium(ll) (0.0074 g, 0.016 mmol) and potassium carbonate (0.137 g, 0.993 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield : 0.070 g (28.3 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .2 (s, 6H, 2CH ₃ ), 1 .88 (s, 3H, CH ₃ ), 2.00 (s, 3H, CH ₃ ), 3.54-3.58 (m, 1 H, CH), 7.36-7.39 (d, 2H, J=8.4 Hz, Ar), 7.46-7.43 (d, 2H, J=8.4 Hz, Ar), 7.48-7.52 (m, 3H, Ar), 7.71 -7.74 (m, 1 H, Ar), 8.48 (d, 1 H, J=1 .8 Hz, Ar), 8.60-8.62 (dd, 1 H, J=1 .8 Hz & J=4.8 Hz, Ar); MS (ES+): m/e 374.2 (M+1 ).

Example 139:

3-(2-Fluoropyridin-3-yl)-5,7-dimethyl-6-(pyridin-3-yl) imidazo[1 ,2-a]pyridine

The compound of example 136 (0.200 g, 0.662 mmol) was treated with (2-fluoropyridin- 3-yl)boronic acid (0.1 12 g, 0.794 mmol) in the presence of dichlorobis(triphenylphosphine) palladium(ll) (0.0074 g, 0.016 mmol) and potassium carbonate (0.137 g, 0.993 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.040 g (18.98 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .90 (s, 3H, CH ₃ ), 2.0 (s, 3H, CH ₃ ), 7.47-7.53 (m, 2H, Ar), 7.58 (s, 1 H, Ar), 7.65 (s, 1 H, Ar), 7.69 (m, 1 H, Ar), 8.1 (t, 1 H, J=8.4 Hz, Ar), 8.3 (m, 1 H, Ar), 8.5 (m, 1 H, Ar), 8.62 (d, 1 H, J=3.9Hz, Ar); MS (ES+): m/e 319.1 (M+1 ).

Example 140:

5,7-Dimethyl-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 134 (5.0 g, 22.21 mmol) was treated with (6-methylpyridin-3- yl)boronic acid (3.35 g, 24.44 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (0.54 g, 0.66 mmol) and potassium carbonate (3.53 g, 33.3 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.7 g (51 .2 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.02 (s, 3H, CH ₃ ), 2.30 (s, 3H, CH ₃ ), 2.55 (s, 3H, CH ₃ ), 7.38 (d, 1 H, J=7.8 Ar), 7.43 (s, 1 H, Ar), 7.60-6.64 (m, 2H, Ar), 7.8 (s, 1 H, Ar), 8.35 (d, 1 H, J=1.8 z Ar); MS (ES+): m/e 238.1 (M+1 ).

Example 141 :

3-Bromo-5,7-dimethyl-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 140 (2.6 g, 10.96 mmol) was treated with N- bromosuccinimide (2.03 g, 1 1 .39 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 1 .2 g (34.6 %); NMR (DMSO-d ₆ , 300 MHz): δ 1 .94 (s, 3H, CH ₃ ), 2.54 (s, 3H, CH ₃ ), 2.68 (s, 3H, CH ₃ ), 7.41 (d, 2H, J=7.8 Hz, Ar), 7.45 (s, 1 H, Ar), 7.6 (dd, 1 H, J=2.4 Hz & J=7.8 Hz, Ar), 8.3 (d, 1 H, J=1 .8 Hz, Ar), MS (ES+): m/e 316.0 (M+1 ). Example 142:

5,7-Dimethyl-6-(6-methylpyridin-3-yl)-3-(4-(methyl sulfonyl)phenyl)imidazo [1 ,2- a]pyridine

The compound of example 141 (0.200 g, 0.633 mmol) was treated with (4- (methylsulfonyl)phenyl)boronic acid (0.139 g, 0.696 mmol) in the presence of dichlorobis(triphenylphosphine)palladium(ll) (0.0071 g, 0.001 mmol) and potassium carbonate (0.131 g, 0.949 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield : 0.120 g (48.5 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .9 (s, 3H, CH ₃ ), 2.09 (s, 3H, CH ₃ ), 2.55 (s, 3H, CH ₃ ), 3.2 (s, 3H, CH ₃ ), 7.37 (d, 1 H, J=7.8 Hz, Ar), 7.5 (s, 1 H, Ar), 7.63-7.65 (m, 2H, Ar), 7.78 (d, 2H, J=8.4 Hz, Ar), 7.9 (d, 2H, J=8.1 Hz, Ar), 8.3 (d, 1 H, J=1 .8 Hz, Ar); MS (ES+): m/e 392 (M+1 ).

Example 143:

5-(5 -Dimethyl-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)picolinonitrile

The compound of example 136 (0.250 g, 0.827 mmol) was treated with (6-cyanopyridin- 3-yl)boronic acid (0.135 g, 0.910 mmol) in the presence of dichlorobis(triphenylphosphine) palladium(ll) (0.0093 g, 0.013 mmol) and potassium carbonate (0.172 g, 1 .241 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield : 0.1 15 g (42.7 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .9 (s, 3H, CH ₃ ), 2.00 (s, 3H, CH ₃ ), 7.2 (d, 2H, J=8.4 Hz, Ar), 7.42-7.52 (m, 5H, Ar), 7.75 (m, 1 H, Ar), 8.49 (d, 1 H, J=1 .5 Hz, Ar), 8.60-8.62 (dd, 1 H, J=4.8 Hz & J=1 .5 Hz, Ar); MS (ES+): m/e 346.1 (M+Na).

Example 144:

3-(2-Methoxypyridin-3-yl)-5,7-dimethyl-6-(pyridin-3-yl)im idazo[1 ,2-a]pyridine

The compound of example 136 (0.250 g, 0.827 mmol) was treated with (2- methoxypyridin-3-yl)boronic acid (0.139 g, 0.910 mmol) in the presence of dichlorobis(triphenylphosphine) palladium(ll) (0.0093 g, 0.013 mmol) and potassium carbonate (0.172 g, 1 .241 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.100 g (36.6 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .87 (s, 3H, CH ₃ ), 1 .99 (s, 3H, CH ₃ ), 3.8 (s, 3H, OCH ₃ ), 7.07-7.1 1 (m, 1 H, Ar), 7.46-7.50 (m, 3H, Ar), 7.6-7.7 (m, 1 H, Ar), 7.80-7.83 (m, 1 H, Ar), 8.24 (dd, 1 H, J=4.8 Hz & J=1 .8 Hz, Ar), 8.42 (d, 1 H, J=19.2 Hz Ar); 8.6 (m, 1 H, Ar), MS (ES+): m/e 331 .2 (M+1 ).

Example 145:

5 -Dimethyl-3-(4-(methylsulfonyl)phenyl)-6-(pyridin-3-yl)imida zo[1 ,2-a] pyridine

The compound of example 136 (0.250 g, 0.827 mmol) was treated with (4- (methylsulfonyl)phenyl)boronic acid (0.182 g, 0.910 mmol) in the presence of dichlorobis(triphenylphosphine) palladium(ll) (0.0093 g, 0.013 mmol) and potassium carbonate (0.172 g, 1 .241 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.050 g (16.01 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .9 (s, 3H, CH ₃ ), 2.04 (s, 3H, CH ₃ ), 3.26 (s, 3H, CH ₃ ), 7.49 (dd, 1 H, J=4.8 Hz & J=5.1 Hz, Ar), 7.58 (s, 1 H, Ar), 7.6 (s, 1 H, Ar), 7.75-7.78 (m, 3H, Ar), 7.94-7.97 (d, 2H, J=8.1 Hz Ar), 8.52 (d, 1 H, J=1 .5 Hz, Ar), 8.61 -8.63 (m, 1 H, Ar); MS (ES+): m/e 378.1 (M+1 ).

Example 146:

6-Bromo-7-methylimidazo[1 ,2-a]pyridine

5-Bromo-4-methylpyridin-2-amine (10 g, 53.5 mmol) and 2-chloro-1 ,1 -dimethoxyethane (14.98 g, 120 mmol) was treated with sodium acetate (9.78 g, 120 mmol) and concentrated hydrochloric acid (3.66 ml_, 120 mmol) in 60 % ethanol according to the procedure for the preparation of the compound of example 1 to afford the title compound. Yield: 4.5 g (80 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.32 (s, 3H, CH ₃ ), 7.53-7.54 (m, 2H, Ar), 7.83 (s, 1 H, Ar), 8.9 (s, 1 H, Ar); MS (ES+): m/e 21 1 (M ⁺ ).

Example 147:

7-Methyl-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 146 (10 g, 47.4 mmol) was treated with pyridin-3-ylboronic acid (6.41 g, 52.1 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.77 g, 0.948 mmol) and sodium carbonate (7.53 g, 71 .1 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 8.2 g (83 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.2 (s, 3H, CH ₃ ), 7.49-7.57 (m, 3H, Ar), 7.70-7.84 (d, 1 H, J=8.1 Hz Ar), 7.90-7.92 (d, 1 H, J=7.5 Hz, Ar), 8.5 (s, 1 H, Ar), 8.6 (s, 1 H, Ar), 8.9 (s, 1 H, Ar); MS (ES+): m/e 210.1 (M+1 ). Example 148:

3-Bromo-7-methyl-6-(pyridin-3-yl)imidazo[1 ,2-a] pyridine

The compound of example 147 (7.0 g, 33.5 mmol) was treated with N- bromosuccinimide (6.19 g, 34.8 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 6.6 g (68.5.0 %); NMR (DMSO-d ₆ , 300 MHz): δ 2.25 (s, 3H, CH ₃ ), 7.50-7.55 (dd, 1 H, J=4.8 Hz & J=7.8 Hz, Ar), 7.62 (s, 1 H, Ar), 7.67-7.69 (d, 1 H, J=5.4 Hz, Ar), 7.70 (s, 1 H, Ar), 7.93-7.97 (m, 1 H, Ar) 8.15 (s, 1 H, Ar), 8.65-8.69 (m, 1 H, Ar); MS (ES+): m/e 288 (M+1 ).

Example 149:

3-(2-Methoxypyridin-3-yl)-7-methyl-6-(pyridin-3-yl) imidazo [1 ,2-a] pyridine

The compound of example 148 (0.250 g, 0.868 mmol) was treated with (2- methoxypyridin-3-yl)boronic acid (0.146 g, 0.954 mmol) in the presence of dichlorobis(triphenylphosphine) palladium(ll) (0.0097 g, 0.014 mmol) and potassium carbonate (0.180 g, 1 .301 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield : 0.150 g (54.6 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.29 (s, 3H, CH ₃ ), 3.90 (s, 3H, OCH ₃ ), 7.13-7.17 (dd, 1 H, J=5.1 Hz & J=7.2 Hz, Ar), 7.47-7.54 (dd, 1 H, J=4.8 Hz & J=7.8 Hz, Ar), 7.68 (s, 1 H, Ar), 7.78 (s, 1 H, Ar), 7.88-7.93 (m, 2H, Ar), 8.03 (s, 1 H, Ar), 8.28-8.304 (dd, 1 H, J=1 .5 Hz & J=5.1 Hz, Ar), 8.6 (m, 2H, Ar); MS (ES+): m/e 317.1 (M+1 ).

Example 150:

6-Chloro-8-fluoroimidazo [1 , 2-a] pyridine

5-Chloro-3-fluoropyridin-2-amine (15 g, 102 mmol), 2-chloro-1 ,1 -dimethoxyethane (86 g, 512 mmol) and sodium acetate (4.39 g, 53.5 mmol) was treated with concentrated hydrochloric acid (15.55 ml_) in 60 % ethanol in water (120 ml_) according to the procedure for the preparation of the compound of example 1 to afford the title compound. Yield: 16.8 g (96 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.42 (d, 1 H, J=6.6 Hz, Ar), 7.67 (s, 1 H, Ar), 8.06 (d, 1 H, J=1 .2 Hz, Ar), 8.76 (d, 1 H, J=0.9 Hz, Ar); MS (ES+): m/e 171 (M+1 ). Example 151 :

8-Fluoro-6-(pyridin-3-yl) imidazo [1, 2-a] pyridine

A stirred solution of compound of example 150 (5 g, 23.25 mmol) and pyridin-3- ylboronic acid (3.14 g, 25.6 mmol) was reacted with [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane) (0.20 g, 0.26 mmol) and sodium carbonate (3.70 g, 34.9 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.2 g (24.20 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.52 (q, 1H, J=3.0 Hz., Ar), 7.65 (d, 1H, J=7.5 Hz, Ar), 7.68 (s, 1H, Ar), 8.10 (d, 1H, J=1.5 Hz, Ar), 8.61 (d, 1H, , J=2.7 Hz, Ar), 8.94-8.9 (m, 3H, Ar); MS (ES+): m/e 214 (M+1).

Example 152:

3- Bromo-8-fluoro-6-(pyridin-3-yl) imidazo [1, 2-a] pyridine

The compound of example 151 (1.2 g, 5.63 mmol) was treated with N- bromosuccinimide (1.50 g, 8.44 mmol) in dry chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 1.1 g (64.2 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 6.95 (d, 1H, J=8.7 Hz, Ar), 7.74 (dd, 1H, J=12.5, 2.4 Hz, Ar), 7.82 (s, 2H, Ar),8.16 (dd, 1H, J=8.7, 2.4 Hz, Ar), 8.40 (d, 1H, J=1.2 Hz, Ar), 8.60 (d, 1H, J=2.1 Hz, Ar); MS (ES+): m/e 293 (M+1).

Example 153:

4- (4-(8-Fluoro-6-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)phen yl)morpholine.

The compound of example 152 (0.250 g, 0.856 mmol) was treated with (4- morpholinophenyl)boronic acid (0.213 g, 1.027 mmol) in the presence of [1,1'- Bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane) (0.020 g, 0.026 mmol) and sodium carbonate (0.23 g, 2.17 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.060 g (17.4 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.20 (t, 4H, J=4.8 Hz, 2CH ₂ ), 3.76 (t, 4H, J=4.5 Hz, 2CH ₂ ), 7.10-7.13 (m, 2H, Ar), 7.50 (q, 1H, J=4.8 Hz, Ar), 7.60-7.63 (m, 2H, Ar), 7.64 (s, 1H, Ar), 7.74 (s, 1H, Ar), 8.12-8.16 (m, 1H, Ar), 8.51 (d, 1H, J=1.2 Hz, Ar), 8.61 (d, 1H, J=4.8 Hz, Ar), 8.95 ( d, 1H, J=2.1 Hz, Ar); MS (ES+): m/e 375 (M+1). Example 154:

4- (8-Fluoro-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)benzene sulfonamide

The compound of example 152 (0.3 g, 1 .027 mmol) was treated with 4-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzene sulfonamide (0.436 g, 1 .54 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.025 g, 0.031 mmol) and sodium carbonate (0.218 g, 2.054 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.050 g (13.22 %); ¹ H NMR (DMSO-de, 300 MHz): δ 7.45-7.55 (m, 3H, Ar), 7.64-7.68 (m, 2H, Ar), 7.93-7.95 (m, 3H, Ar), 8.14-8.16 (m, 1 H, Ar), 8.60-8.62 (m, 1 H, Ar), 8.95-8.96 (m, 1 H, Ar); MS (ES+): m/e 369 (M+1 ).

Example 155:

8-Fluoro-3-(4-(isopropylthio)phenyl)-6-(pyridin-3-yl)imid azo[1 ,2-a]pyridine

The compound of example 152 (0.165 g, 0.565 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.133 g, 0.678 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.017 g, 0.030 mmol) and potassium carbonate (0.156 g, 1 .13 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.01 1 g (5.36 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .31 (d, 6H, J=6.6 Hz, 2CH ₃ ), 3.60-3.65 (m, 1 H, CH), 7.49-7.55 (m, 3H, Ar), 7.70-7.76 (m, 3H, Ar), 7.79 (s, 1 H, Ar), 8.16-8.20 (m, 1 H, Ar), 8.61 -8.63 (m, 2H, Ar), 8.99 (d, 1 H, J=1 .8 Hz, Ar); MS (ES+): m/e 364 (M+1 ).

Example 156:

5- (8-Fluoroimidazo[1 ,2-a]pyridin-6-yl)picolinonitrile

The compound of example 150 (4.0 g, 23.45 mmol) was treated with 5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)picolinonitrile (6.47 g, 28.1 mmol) in DMF (60 mL) in presence of palladiumtetrakis (0.813 g, 0.704 mmol) and sodium carbonate (4.97 g, 46.9 mmol) solution in 12 mL of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.5 g (8.69 %); ¹ H NMR (DMSO, 300 MHz): δ 7.70 (s, 1 H, Ar), 7.76 (d, 1 H, J = 12.6 Hz, Ar), 8.1 1 (d, 1 H, J = 2.7 Hz, Ar), 8.18( d, 1 H, J = 8.4 Hz, Ar), 8.42 (dd, 1 H, J = 8.1 Hz, J = 2.1 Hz, Ar), 9.10 (s, 1 H, Ar), 9.16 (s, 1 H, Ar); MS (ES+): m/e 239 (M+1 ). Example 157:

5-(3-Bromo-8-fluoroimidazo[1 ,2-a]pyridin-6-yl)picolinonitrile

The compound of example 156 (460 mg, 1 .931 mmol) was treated with N- bromosuccinimide (357 mg, 2.008 mmol) in chloroform (10 mL) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.5g (78%). %); ¹ H NMR (DMSO, 300 MHz): δ 7.90 (d, 2H, J = 9.9 Hz, Ar), 8.20 (d, 1 H, J = 8.4 Hz, Ar), 8.53 (dd, 1 H, J = 8.1 Hz, J = 2.4 Hz, Ar), 8.70 (s, 1 H, Ar), 9.24 (d, 1 H, J= 1 .5 Hz, Ar); MS (ES+): m/e 317 (M+1 ).

Example 158:

5- (8-Fluoro-3-(4-(methylsulfonyl)phenyl)imidazo[1 ,2-a] pyridin-6-yl) picolinonitrile

The compound of example 157 (300 mg, 0.946 mmol) was treated with (4- (methylsulfonyl)phenyl)boronic acid (227 mg, 1 .135 mmol) in DMF (10 mL) in presence of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(ll) complex with dichloromethane (23.18 mg, 0.028 mmol) and sodium carbonate (201 mg, 1 .892 mmol) solution in 2 mL according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.243 g (61 .8 %); ¹ H NMR (300 MHz, DMSO-de) : δ 3.30 (s, 3H, S0 ₂ CH ₃ ), 7.89 (d, 1 H, J = 12.3 Hz, Ar), 8.07 (s, 1 H, Ar), 8.10 (s, 4H, Ar), 8.19 (d, 1 H, J = 8.1 Hz, Ar), 8.50 (d, 1 H, J = 8.1 Hz, Ar), 8.92 (s, 1 H, Ar), 9.22 (s, 1 H, Ar); MS (ES+): m/e 393.1 (M+1 ).

Example 159:

6- (6-(1 H-Tetrazol-5-yl)pyridin-3-yl)-8-fluoro-3-(4-(methyl sulfonyl)phenyl)

imidazo[1 ,2-a]pyridine

The compound of example 158 (150 mg, 0.382 mmol) was treated with sodium azide (99 mg, 1 .529 mmol) and ammonium chloride (82 mg, 1 .529 mmol) in DMF (2 ml) at 120°C for about 16 h. The solvent was evaporated to yield a residue, which was purified using column chromatography (silica gel, 20% methanol in chloroform) to afford the title compound Yield: 0.058 g (33.6 %); ¹ H NMR (300 MHz, DMSO-d ₆ ): δ 3.35 (s, 3H, SO ₂ CH ₃ ), 5.76 (s, 1 H, NH, Exchangeable with D ₂ 0), 7.92 (d, 1 H, J = 12.0 Hz, Ar), 8.07 (s, 1 H, Ar), 8.1 1 (s, 4H, Ar), 8.30 (d, 1 H, J = 8.1 Hz, Ar), 8.50 (d, 1 H, J = 6.6 Hz, Ar), 8.91 (s, 1 H, Ar), 9.21 (s, 1 H, Ar); MS (ES+): m/e 436.1 (M+1 ). Example 160:

8-Fluoro-6-(2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridine

The compound of example 1 50 (5.0 g, 29.3 mmol)was treated with 2-methyl-5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidine (9.68 g, 44.0 mmol) in DMF (50 ml) in presence of tetrakis(triphenylphosphine)palladium(0) (1 .01 6 g, 0.879 mmol) and sodium carbonate (6.21 g, 58.6 mmol) solution (in 10 mLwater) at 1 20 °C for 4 hr according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1 .2 g (1 7.28 %). ¹ H NMR (DMSO-d6, 300 MHz): δ 2.68 (s, 3H, CH ₃ ), 7.71 (d, 2H, J = 1 3.5 Hz, Ar), 8.1 0 (s, 1 H, Ar), 8.99 (s, 1 H, Ar), 9.08 (s, 2H, Ar); MS (ES+): m/e 229.1 (M+1 ).

Example 161 :

3- Bromo-8-fluoro-6-(2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridine

The compound of example 1 60 (1 .2 g, 5.26 mmol) was treated with N- bromosuccinimide (0.973 g, 5.47 mmol) in chloroform (20 ml_) according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 1 .3 g (81 .00%). ¹ H NMR (DMSO-d6, 300 MHz) : δ 2.69 (s, 3H, CH ₃ ), 7.85 (d, 2H, J = 1 1 .1 Hz, Ar), 8.63 (s, 1 H, Ar), 9.14 (s, 2H, Ar) ; MS (ES+): m/e 307.2 (M+1 ).

Example 162:

4- (5-(8-Fluoro-6-(2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl) morpholine

The compound of example 161 (0.2 g, 0.651 mmol) was treated with 4-(5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (0.227 g, 0.781 mmol) in DMF (5 ml) in presence of [1 , 1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(l l) complex with dichloromethane (0.01 6 g, 0.020 mmol) and sodium carbonate (0.1 38 g, 1 .302 mmol) solution in 1 ml_ of water according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.06 g (23.6 %) ; ¹ H NMR (300 MHz, DMSO-d ₆ ) : δ 2.67 (s, 3H, CH ₃ ), 3.56 (s, 4H, 2CH ₂ ), 3.72 (s, 4H, 2CH ₂ ), 7.01 (d, 1 H, J = 9.0 Hz, Ar), 7.72 (d, 1 H, J = 1 2.3 Hz, Ar), 7.79 (s, 1 H, Ar), 7.95 (d, 1 H, J = 8.7 Hz, Ar), 8.48 (s, 1 H, Ar), 8.62 (s, 1 H, Ar), 9.08(s, 2H, Ar) ; MS (ES+) : m/e 391 .2 (M+1 ). Example 163:

8-Fluoro-6-(6-methoxypyridin-3-yl)imidazo[1,2-a]pyridine

A stirred solution of the compound of example 150 (0.5 g, 2.93 mmol) and (6- methoxypyridin-3-yl)boronic acid (0.493 g, 3.22 mmol) was reacted with palladiumtetrakis (0.20 g, 0.26 mmol) and sodium carbonate (0.466 g, 4.40 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.060 g (8.42 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.90 (s, 3H, OCH ₃ ), 7.53-7.56 (m, 2H, Ar), 5.59-7.65 (m, 4H, Ar), 8.05- 8.07 (m, 1H, Ar); MS (ES+): m/e 244 (M+1).

Example 164:

3- Bromo-8-fluoro-6-(6-methoxypyridin-3-yl)imidazo[1,2-a]pyridi ne

The compound of example 163 (0.270 g, 1.1150 mmol) was treated with N- bromosuccinimide (0.296 g, 1.66 mmol) in dry chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.062 g (17.34 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.91 (s, 3H, OCH ₃ ), 6.95 (d, 1H, J=8.7 Hz, Ar), 7.72 (dd, 1H, J=12.3, 2.4 Hz, Ar), 7.82 (s, 1H, Ar), 8.15 (dd, 1H, J=8.7, 2.4 Hz, Ar), 8.40 (d, 1H, J=1.2 Hz, Ar), 8.60 (d, 1H, J=2.1 Hz, Ar); MS (ES+): m/e 323 (M+1).

Example 165:

4- (4-(8-Fluoro-6-(6-methoxypyridin-3-yl)imidazo[1,2-a]pyridin- 3-yl)phenyl) morpholine

The compound of example 164 (0.5 g, 1.55 mmol) was treated with (4- morpholinophenyl)boronic acid (0.386 g, 1.86 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane) (0.038 g, 0.047 mmol) and sodium carbonate (0.230 g, 2.17 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.060 g (9.38 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.21 (t, 4H, J=4.8 Hz, 2CH ₂ ), 3.77 (t, 4H, J=4.5 Hz, 2CH ₂ ), 3.90 (s, 3H, OCH ₃ ), 6.93 (d, 1H, J=8.7 Hz, Ar), 7.14 (m, 2H, Ar), 7.58-7.62 (m, 3H, Ar), 7.73 (s, 1H, Ar), 8.07 (dd, 1H, J=8.7 Hz and 2.4 Hz, Ar), 8.42 (d, 1H, J=1.2 Hz, Ar), 8.53 (d, 1H, J=2.4 Hz, Ar); MS (ES+): m/e 405 (M+1). Example 166:

8-Fluoro-6-(6-methoxypyridin-3-yl)-3-(4-(methylsulfonyl)phen yl)imidazo[1,2-a] pyridine

The compound of example 164 (0.3 g, 0.931 mmol) was treated with (4- (methylsulfonyl)phenyl)boronic acid (0.224 g, 1.12 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane) (0.022 g, 0.028 mmol) and sodium carbonate (0.197 g, 1.87 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.145 g (38.4 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.29 (s, 3H, CH ₃ ), 3.90 (s, 3H, OCH ₃ ), 6.94 (d, 1H, J=8.7 Hz, Ar), 7.71-7.75 (m, 1H, Ar), 8.02 (s, 1H, Ar), 8.08 (s, 4H, Ar), 8.13(dd, 1H, J=8.7, 2.7 Hz, Ar), 8.59 (d, 1H, J=2.1 Hz, Ar), 8.66 (s, 1H, Ar); MS (ES+): m/e 398 (M+1). Example 167:

8-Fluoro-3-(4-(isopropylthio)phenyl)-6-(6-methoxypyridin-3-y l)imidazo[1,2-a] pyridine

The compound of example 164 (0.5 g, 1.55 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.412 g, 1.86 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane) (0.040 g, 0.049 mmol) and sodium carbonate (0.329 g, 3.10 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.215 g (34.9 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.29 (d, 6H, J=6.6 Hz, 2CH ₃ ), 3.58-3.66 (m, 1H, CH), 3.90 (s, 3H, OCH ₃ ), 6.94 (d, 1H, J=8.7 Hz, Ar), 7.51-7.54 (m, 2H, Ar), 7.63-7.67 (m, 1H, Ar), 7.72-7.75 (m, 2H, Ar), 7.86 (s, 1H, Ar), 8.10 (dd, 1H, J=8.7 Hz and 2.4 Hz, Ar), 8.54 (s, 1H, Ar), 8.57 (d, 1H, J=2.4 Hz, Ar); MS: m/e (ES+) 394 (M+1).

Example 168:

t-Butyl-4-(5-(8-fluoro-6-(6-methoxypyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl) pyridin- 2-yl)piperazine-1 -carboxylate

The compound of example 164 (0.5 g, 1.55 mmol) was treated with t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3, 2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (0.725 g, 1.86 mmol) in the presence of [1 ,1 '-bis(diphenyl phosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane) (0.038 g, 0.047 mmol) and sodium carbonate (0.329 g, 3.10 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.430 g (51 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .43 (s, 9H, 3CH ₃ ), 3.45-3.51 (m, 4H, 2CH ₂ ), 3.59-3.60 (m, 4H, 2CH ₂ ), 3.89 (s, 3H, OCH ₃ ), 6.90.6.93 (m, 1 H, Ar), 7.02 (d, 1 H, J=9.0 Hz, Ar), 7.60- 7.64 (m, 1 H, Ar), 7.75 (s, 1 H, Ar), 7.94 (dd, 1 H, J=8.7, 2.4 Hz, Ar), 8.09 (dd, 1 H, J=8.7, 2.4 Hz, Ar), 8.39 (s, 1 H, Ar), 8.45 (d, 1 H, J=2.1 Hz, Ar), 8.52 (d, 1 H, J=2.1 Hz, Ar); MS (ES+): m/e 505 (M+1 ). Example 169:

3-(4-(t-Butyl)phenyl)-8-fluoro-6-(6-methoxypyridin-3-yl) imidazo[1 ,2-a] pyridine

The compound of example 164 (0.3 g, 0.931 mmol) was treated with (4-(t- butyl)phenyl)boronic acid (0.199 g, 1 .12 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane) (0.022 g, 0.028 mmol) and sodium carbonate (0.197 g, 1 .86 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.21 1 g (60.1 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .34 (s, 9H, 3CH ₃ ), 3.89 (s, 3H, OCH ₃ ), 6.93 (d, 1 H, J=8.4 Hz, Ar), 7.57- 7.72 (m, 5H, Ar), 7.81 (s, 1 H, Ar), 8.10 (dd, 1 H, J=8.7, 2.7 Hz, Ar), 8.51 (s, 1 H, Ar), 8.56 (d, 1 H, J=2.1 Hz, Ar); MS (ES+): m/e 376 (M+1 ).

Example 170:

Methyl 3-(8-fluoro-6-(6-methoxypyridin-3-yl) imidazo [1 , 2-a] pyridin-3-yl) benzoate

The compound of example 164 (0.3 g, 0.931 mmol) was treated with (3- (methoxycarbonyl)phenyl)boronic acid (0.201 g, 1 .12 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.022 g, 0.028 mmol) and pottasium carbonate (0.257 g, 1 .86 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.155 g (44.1 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.89 (s, 6H, 20CH ₃ ), 6.93 (d, 1 H, J=8.7 Hz, Ar), 7.66-7.76 (m, 2H, Ar), 7.92 (s, 1 H, Ar), 8.03-8.10 (m, 3H, Ar), 8.21 (s, 1 H, Ar), 8.54-8.566 (m, 2H, Ar); MS (ES+): m/e 378 (M+1 ).

Example 171 :

3-(8-Fluoro-6-(6-methoxypyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)benzoic acid The compound of example 170 (0.1 g, 0.265 mmol) was treated with sodium hydroxide (0.106 g, 2.65 mmol) in methanol (20 ml_) and heated at reflux for 2 h. The solvent was distilled and dilute hydrochloric acid was added drop wise to make the pH neutral. The crude product was filtered and washed with water till pH was neutral and dried to afford the title compound. Yield: 0.030 g (30.8 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.89 (s, 3H, OCH ₃ ), 6.93 (d, 1 H, J=8.4 Hz, Ar), 7.46-7.51 (m, 1 H, Ar), 7.62-7.70 (m, 2H, Ar), 7.81 (s, 1 H, Ar), 7.95 (d, 1 H, J=6.6 Hz, Ar), 8.06 (d, 1 H, J=8.4 Hz, Ar), 8.15 (s, 1 H, Ar), 8.47-8.52 (m, 2H, Ar); MS (ES+): m/e 364 (M+1 ).

Example 172:

6-Bromo-8-(trifluoromethyl)imidazo[1 ,2-a]pyridine

To a stirred solution of 5-bromo-3-(trifluoromethyl)pyridin-2-amine (1 g, 4.15 mmol) and sodium acetate (0.681 g, 8.30 mmol) in 100 ml_ of 60 % ethanol-water, were added separately refluxed solution of sodium acetate (0.681 g, 8.30 mmol), 2-chloro-1 ,1 - dimethoxyethane (1 .034 g, 8.30 mmol) in concentrated hydrochloric acid (0.252 ml_, 8.30 mmol) (1 :6- HCI/water) according to the procedure for the preparation of the compound of example 1 to afford the title compound. Yield: 0.79 g (71 .8 %); ¹ H NMR (DMSO-de, 300 MHz): δ 7.71 (s, 1 H, Ar), 7.83 (s, 1 H, Ar), 8.07 (s, 1 H, Ar), 9.20 (s, 1 H, Ar) ; MS (ES+) : m/e 267 (M+1 ).

Example 173:

6-(Pyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridine

The compound of example 172 (1 .5 g, 5.66 mmol) was treated with pyridine-3-boronic acid (0.835 g, 6.79 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.079 g, 0.1 13 mmol) and sodium carbonate (1 .173 g, 8.49 mmol) in dry dimethylformamide (10 ml_) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.680 g (44.5 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.51 -7.55 (m, 1 H, Ar), 7.74 (s, 1 H, Ar), 8.04 (s, 1 H, Ar), 8.13 (s, 1 H, Ar), 8.17-8.21 (m, 1 H, Ar), 8.62 (dd, J =3.0 Hz, J =4.8 Hz, 1 H, Ar), 8.98 (d, 1 H, J=3.0 Hz, Ar), 9.28 (s, 1 H, Ar); MS (ES+): m/e 264 (M+1 ).

Example 174:

3-Bromo-6-(pyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridine The compound of example 173 (0.650 g, 2.47 mmol) in dry CHCI ₃ (50 mL) was reacted with dried N-bromosuccinimide (457 mg, 2.57 mmol) at 10 °C acccording to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.750 g (89 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.51 -7.56 (m, 1 H, Ar), 7.91 (s, 1 H, Ar), 8.14 (s, 1 H, Ar), 8.24-8.28 (m, 1 H, Ar), 8.64 (dd, 1 H, J =3.0 Hz, J =4.8 Hz, Ar), 8.82 (s, 1 H, Ar), 9.04 (d, 1 H, J =3.0 Hz, Ar); MS (ES+): m/e 342 (M+1 ).

Example 175:

3-(4-(Methylthio)phenyl)-6-(pyridin-3-yl)-8-(trifluoromet hyl) imidazo[1 ,2-a] pyridine

The compound of example 174 (0.250 g, 0.731 mmol) was treated with 4- (methylthio)phenylboronic acid (0.147 g, 0.877 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.0102 g, 0.015 mmol) and sodium carbonate (0.151 g, 1 .096 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield 0.1 12 g (39.3 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.48 (s, 3H, CH ₃ ), 7.43 (d, 2H, J =9.0 Hz, Ar), 7.48-7.52 (m, 1 H, Ar), 7.73 (d, 2H, J=9.0 Hz, Ar), 7.90 (s, 1 H, Ar), 8.07 (s, 1 H, Ar), 8.19-8.22 (m, 1 H, Ar), 8.61 (dd, 1 H, J =3.0 Hz, J =4.8 Hz, Ar), 8.88 (s, 1 H, Ar), 8.99 (d, 1 H, J =3.0 Hz, Ar); MS (ES+): m/e 386 (M+1 ).

Example 176:

3-(4-(Methylsulfonyl)phenyl)-6-(pyridin-3-yl)-8-(trifluorome thyl)imidazo [1 ,2-a] pyridine

The compound of example 174 (150 mg, 0.438 mmol) was treated with 4- (methylsulfonyl)phenylboronic acid (105 mg, 0.526 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (17.90 mg, 0.022 mmol) and sodium carbonate (91 mg, 0.658 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield 0.56 g (30.0 %); ¹ H NMR (DMSO-de, 300 MHz): δ 3.28 (s, 3H, SO ₂ CH ₃ ), 7.49-7.54 (m, 1 H, Ar), 8.08-8.1 1 (m, 5H, Ar), 8.15 (s, 1 H, Ar), 8.23-8.26 (m, 1 H, Ar), 8.63 (dd, J =1 .2 Hz, J =4.5 Hz, 1 H, Ar), 9.03 (d, 1 H, J=3.0 Hz, Ar), 9.06 (s, 1 H, Ar); MS (ES+): m/e 418 (M+1 ). Example 177:

6-(Pyridin-3-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyridine

The compound of example 172 (1 g, 3.77 mmol) was treated with 5- (trifluoromethyl)pyridin-3-ylboronic acid (0.864 g, 4.53 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.053 g, 0.075 mmol) and sodium carbonate (0.782 g, 5.66 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield, 0.530 g (41.3 %); ¹ H NMR (DMSO-de, 300 MHz): δ 7.76 (s, 1 H, Ar), 8.14 (s, 1 H, Ar), 8.20 (s, 1 H, Ar), 8.65 (s, 1 H, Ar), 9.01 (s, 1H, Ar), 9.30 (d, 1H, J =3.0 Hz, Ar), 9.40 (s, 1H, Ar); MS (ES+): m/e 332 (M+1).

Example 178:

3-Bromo-8-(trifluoromethyl)-6-(5-(trifluoromethyl)pyridin -3-yl) imidazo[1 ,2-a] pyridine

N-bromosuccinimide (0.279 g, 1.570 mmol) was added to a stirred solution of the compound of example 177 (0.500 g, 1.510 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.504 g (81 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.93 (s, 1 H, Ar), 8.27 (s, 1H, Ar), 8.73 (s, 1H, Ar),9.02 (d, J =6.0 Hz, 2H, Ar), 9.33 (d, J =3.0 Hz, 1H, Ar); MS (ES+): m/e 411 (M+1).

Example 179:

3-(4-(Methylsulfonyl)phenyl)-8-(trifluoromethyl)-6-(5-(tr ifluoromethyl) pyridin-3- yl)imidazo[1 ,2-a]pyridine

The compound of example 178 (0.150 g, 0.366 mmol) was treated with 4- (methylsulfonyl)phenylboronic acid (88 mg, 0.439 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.0149 g, 0.018 mmol) and sodium carbonate (0.076 g, 0.549 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.79 g (44.1 %); ¹ H NMR (DMSO-de, 300 MHz): δ 3.24 (s, 3H, SO ₂ CH ₃ ), 7.86 (d, 1H, J =3.0 Hz, Ar), 7.99 (d, 2H, J =8.4 Hz, Ar), 8.27 (d, 2H, J =8.4 Hz, Ar), 8.64 (d, 2H, J =9.0 Hz, Ar), 9.00 (s, 1H, Ar), 9.24 (d, 1H, J =3.0 Hz, Ar), 9.31 (d, J =3.0 Hz, 1H, Ar); MS (ES+): m/e 486 (M+1). Example 180:

6-(6-Methylpyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a] pyridine

The compound of example 172 (3 g, 1 1 .32 mmol) was treated with 2-methylpyridine-5- boronic acid (2.015 g, 14.72 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.159 g, 0.226 mmol) and sodium carbonate (2.347 g, 16.98 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 3.0 g (91 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.51 (s, 3H, CH ₃ ), 7.40 (d, 1 H, J =8.1 Hz, Ar), 7.75 (s, 1 H, Ar), 8.026 (s, 1 H, Ar), 8.10 (dd, 1 H, J =3.0 Hz, J=8.1 Hz, Ar), 8.14 (s, 1 H, Ar), 8.86 (d, 1 H, J =3.0 Hz, Ar), 9.26 (s, 1 H, Ar); MS (ES+): m/e 278 (M+1 ).

Example 181 :

3-Bromo-6-(6-methylpyridin-3-yl)-8-(trifluoromethyl)imida zo [1 ,2-a]pyridine

N-bromosuccinimide (2.03 g, 1 1 .25 mmol) was added to a stirred solution of compound of example 180 (3 g, 10.82 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 3.25 g (84 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.51 (s, 3H, CH ₃ ), 7.42 (d, 1 H, J =8.1 Hz, Ar), 7.92 (s, 1 H, Ar), 8.14 (s, 1 H, Ar), 8.19 (dd, 1 H, J =2.4 Hz, J =8.1 Hz, Ar), 8.81 (s, 1 H, Ar), 8.93 (d, 1 H, J =3.0 Hz, Ar); MS (ES+): m/e 357.1 (M+1 ).

Example 182:

6-(6-Methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)-8-(tri fluoromethyl) imidazo

[1 ,2-a]pyridine

The compound of example 181 (0.150 g, 0.421 mmol) was treated with 4- (methylsulfonyl)phenylboronic acid (0.101 g, 0.505 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.0172 g, 0.021 mmol), and sodium carbonate (0.087 g, 0.632 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.50 g (26.2 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.51 (s, 3H, CH ₃ ), 3.28 (s, 3H, S0 ₂ CH ₃ ), 7.37 (d, 1 H, J =8.1 Hz, Ar), 7.67 (d, 1 H, J =1 .5 Hz, Ar), 7.98 (d, 2H, J =8.4 Hz, Ar), 8.07 (s, 1 H, Ar), 8.23 (d, 2H, J =8.1 Hz, Ar), 8.64 (s, 1 H, Ar), 8.84 (d, 1 H, J =2.1 Hz, Ar), 9.03 (d, 1 H, J =1 .5 Hz, Ar); MS (ES+): m/e 432 (M+1 ). Example 183:

6-(6-Methylpyridin-3-yl)-3-(3-(methylsulfonyl)phenyl)-8-(tri fluoromethyl) imidazo

[1 ,2-a]pyridine

The compound of example 181 (0.150 g, 0.421 mmol) was treated with (3- (methylsulfonyl)phenyl)boronic acid (0.101 g, 0.505 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.0172 g, 0.021 mmol) and sodium carbonate (0.087 mg, 0.632 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.30 g (15.68 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.47 (s, 3H, CH ₃ ), 3.29 (s, 3H, S0 ₂ CH ₃ ), 7.37 (d, 1 H, J =8.1 Hz, Ar),7.66 (d, 1 H, J =1 .5 Hz, Ar), 7.73 (t, 1 H, J =7.8 Hz, Ar), 7.88 (d, 1 H, J =7.8 Hz, Ar), 8.06 (dd, 1 H, J =2.4 Hz, J =8.1 Hz, Ar), 8.31 (d, 1 H, J =7.8 Hz, Ar), 8.47 (s, 1 H, Ar), 8.63 (s, 1 H, Ar), 8.84 (d, J =2.1 Hz, 1 H, Ar), 9.03 (d, J =1 .5 Hz, 1 H, Ar); MS (ES+): m/e 432 (M+1 ).

Example 184:

t-Butyl 4-(5-(6-(6-methylpyridin-3-yl)-8-(trifluoromethyl) imidazo[1 ,2-a] pyridin-3-yl) pyridin-2-yl)piperazine-1-carboxylate

The compound of example 181 (2 g, 5.62 mmol) was treated with t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (2.186 g, 5.62 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.229 g, 0.281 mmol) and sodium carbonate (1 .164 g, 8.42 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1 .6 g (52.3 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .39 (s, 9H, 3CH ₃ ), 2.52 (d, 3H, J =1 .8 Hz, CH ₃ ), 3.46 (d, 4H, J =5.4 Hz, 2CH ₂ ), 3.60 (d, 4H, J =5.4 Hz, 2CH ₂ ), 7.03 (d, 1 H, J =9.0 Hz, Ar), 7.36 (d, 1 H, J =8.1 Hz, Ar), 7.84 (s, 1 H, Ar), 7.97 (dd, 1 H, J =2.4 Hz, J =8.7 Hz, Ar), 8.04 (s, 1 H, Ar), 8.09 (dd, 1 H, J =2.4 Hz, J =8.1 Hz, Ar), 8.47 (d, 1 H, J =2.4 Hz, Ar), 8.77 (s, 1 H, Ar), 8.85 (d, J =2.1 Hz, 1 H, Ar); MS (ES+): m/e 539.2 (M+1 ).

Example 185:

6-(6-Methylpyridin-3-yl)-3-(6-(piperazin-1-yl)pyridin-3-yl)- 8-(trifluoromethyl) imidazo[1 ,2-a]pyridine The compound of example 184 (1.5 g, 2.79 mmol) was added to a stirred solution of HCI (0.085 mL, 2.79 mmol) solution in dioxane (10 mL) according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 0.48 g (20.23 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.49 (s, 3H, CH ₃ ), 2.78 (d, 4H, J =5.1 Hz, 2CH ₂ ), 3.50 (d, 4H, J =5.1 Hz, 2CH ₂ ), 6.98 (d, 1H, J =8.7 Hz, Ar), 7.36 (d, 1H, J =8.1 Hz, Ar), 7.83 (s, 1H, Ar), 7.92 (dd, 1H, J =2.4 Hz, J =8.7 Hz, Ar), 8.03 (s, 1H, Ar), 8.10 (dd, 1H, J =2.4 Hz, J =8.1 Hz, Ar), 8.45 (d, 1H, J =2.4 Hz, Ar), 8.77 (s, 1H, Ar), 8.86 (d, J =2.1 Hz, 1H, Ar); MS (ES+): m/e 439.2 (M+1).

Example 186:

N,N-dimethyl-4-(5-(6-(6-methylpyridin-3-yl)-8-(trifluorometh yl) imidazo[1 ,2-a] pyridin-3-yl)pyridin-2-yl)piperazine-1-carboxamide

Pyridine (0.055 mL, 0.684 mmol) was added to a stirred solution of the compound of example 185 (0.200 g, 0.456 mmol) and dimethylcarbamic chloride (0.058 g, 0.547 mmol) in dichloromethane (5 mL) according to the procedure for the preparation of the compound of example 100 to afford the title compound. Yield: 0.970 g (79 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.50 (s, 3H, CH ₃ ), 2.79 (s, 6H, 2CH ₃ ), 3.23 (s, 4H, 2CH ₂ ) 3.62 (s, 4H, 2CH ₂ ), 7.02 (d, 1H, J =9.0 Hz, Ar), 7.36 (d, 1H, J =9.0 Hz, Ar), 7.84 (s, 1H, Ar), 7.97 (d, 1H, J =9.0 Hz, Ar), 8.03 (s, 1H, Ar), 8.10 (d, 1H, J =9.0 Hz, Ar), 8.46 (d, 1H, J =3.0 Hz, Ar), 8.77 (s, 1H, Ar), 8.85 (d, 1H, J =3.0 Hz, Ar), MS (ES+): m/e 510.1 (M+1).

Example 187:

4-(4-(6-(6-Methylpyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a] pyridin-3-yl) phenyl) morpholine

The compound of example 181 (0.200 g, 0.562 mmol) was treated with (4- morpholinophenyl)boronic acid (0.145 g, 0.702 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.013 g, 0.017 mmol) and sodium carbonate (0.119 g, 1.123 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.150 g (60.8 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.48 (s, 3H, CH ₃ ), 3.19 (d, 4H, J =4.8 Hz, 2CH ₂ ), 3.74 (d, 4H, J =5.4 Hz, 2CH ₂ ), 7.10 (d, 2H, J =9.0 Hz, Ar), 7.36 (d, 1H, J =9.9 Hz, Ar), 7.60 (d, 2H, J =8.7 Hz, Ar), 7.79 (s, 1H, Ar), 7.99 (s, 1H, Ar), 8.06 (dd, 1H, J =2.1 Hz, J =8.1 Hz, Ar), 8.76 (s, 1 H, Ar), 8.81 (d, 1 H, J =2.1 Hz, Ar); MS (ES+): m/e 439.2 (M+1 ). Example 188:

4-(4-(6-(6-Methylpyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin phenyl) morpholine 4-oxide

Metachloroperbenzoic acid (0.039 g, 0.228 mmol) was added to a stirred solution of the compound of example 1 87 (0.100 g, 0.228 mmol) in dichloromethane (1 0 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound.Yield: 0.55 g (52.6 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.49 (s, 3H, CH ₃ ), 2.86 (d, 2H, J =1 0.8 Hz, CH ₂ ), 3.79-3.83 (m, 2H), 4.07-4.1 3 (m, 2H), 4.43-4.51 (m, 2H), 7.38 (d, 1 H, J =8.1 Hz, Ar), 7.94 (d, 2H, J =8.7 Hz, Ar), 8.01 (s, 1 H, Ar), 8.09 (s, 1 H, Ar), 8.1 2 (dd, 1 H, J =2.4 Hz, J =8.1 Hz, Ar), 8.32 (s, 1 H, Ar), 8.37 (d, 1 H, J =8.7 Hz, Ar), 8.87 (d, 1 H, J =2.1 Hz, Ar), 8.95 (s, 1 H, Ar); MS (ES+): m/e 455.5 (M+1 ).

Example 189:

4-(4-(6-(6-Methylpyridin-3-yl)-8-(trifluoromethyl)imidazo [1 ,2-a]pyridin-3-yl) phenyl) thiomorpholine-1 ,1 -dioxide

The compound of example 181 (0.500 g, 1 .404 mmol) was treated with 4-(4-(4, 4,5,5- tetramethyl-1 ,3, 2-dioxaborolan-2-yl)phenyl)thiomorpholine-1 , 1 -dioxide (0.521 g, 1 .544 mmol) in the presence of [1 , 1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.057 g, 0.070 mmol) and sodium carbonate (0.291 g, 2.1 06 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.389 g (56 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.50 (s, 3H, CH ₃ ), 3.1 5 (s, 4H, 2CH ₂ ), 3.90 (s, 4H, 2CH ₂ ), 7.22 (d, 2H, J =9.0 Hz, Ar), 7.37 (d, 1 H, J=9.0 Hz, Ar), 7.65 (d, 2H, J =9.0 Hz, Ar), 7.83 (s, 1 H, Ar), 8.02 (s, 1 H, Ar), 8.08 (dd, 1 H, J =3.0 Hz, J =8.1 Hz, Ar), 8.80- 8.84 (m, 2H, Ar); MS (ES+) : m/e 487.5 (M+1 ).

Example 190:

3-(4-lsobutylphenyl)-6-(6-methylpyridin-3-yl)-8-(trifluoro methyl)imidazo[1 ,2-a] pyridine

The compound of example 1 81 (0.200 g, 0.562 mmol) was treated with 4- isobutylphenylboronic acid (0.1 20 mg, 0.674 mmol) in the presence of [1 , 1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.022 g, 0.028 mmol) and sodium carbonate (0.1 16 g, 0.842 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.50 g (20.98 %); ¹ H NMR (DMSO-de, 300 MHz): δ 0.87 (d, 3H, J =6.3 Hz, CH3), 0.89 (d, 3H, J =6.3 Hz, CH3), 1 .76-1 .86 (m, 1 H, CH), 2.40 (d, 2H, J =7.2 Hz, CH ₂ ), 2.53 (s, 3H, CH ₃ ), 7.07 (d, 1 H, J =7.8 Hz, Ar), 7.34 (dd, 2H, J =2.4 Hz, J =8.1 Hz, Ar), 7.65 (dd, 3H, J =1 .8 Hz, J =8.1 Hz, Ar), 7.86 (s, 1 H, Ar), 8.00 (s, 1 H, Ar), 8.04 (dd, 1 H, J =2.4 Hz, J =8.1 Hz, Ar), 8.79 (s, 1 H, Ar); MS (ES+): m/e 410.2 (M+1 ).

Example 191 :

3-(4-(lsopropylthio)phenyl)-6-(6-methylpyridin-3-yl)-8-(t rifluoromethyl) imidazo

[1 ,2-a]pyridine

The compound of example 181 (0.500 g, 1 .404 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.330 g, 1 .685 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.057 g, 0.070 mmol) and sodium carbonate (0.291 g, 2.106 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.280 g (46.3 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .28 (d, 6H, J =6.0 Hz, 2CH ₃ ), 2.48 (s, 3H, CH ₃ ), 3.56-3.63 (m, 1 H, CH), 7.35 (d, 1 H, J =9.0 Hz, Ar), 7.52 (d, 2H, J =9.0 Hz, Ar), 7.72 (d, 2H, J =9.0 Hz, Ar), 7.91 (s, 1 H, Ar), 8.04 (s, 1 H, Ar), 8.08 (dd, 1 H, J =3.0 Hz , J =8.1 Hz, Ar), 8.83 (d, 1 H, J =3.0 Hz, Ar), 8.87 (s, 1 H, Ar); MS (ES+): m/e 428.1 (M+1 ).

Example 192A:

3-(4-(lsopropylsulfinyl)phenyl)-6-(6-methylpyridin-3-yl)-8-( trifluoromethyl) imidazo

[1 ,2-a]pyridine

Metachloroperbenzoic acid (0.121 g, 0.702 mmol) was added to a stirred solution of the compound of example 191 (0.150 g, 0.351 mmol) in dichloromethane (10 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.94 g (59.9 %); ¹ H NMR (DMSO-d ₆ , 300 MHz: δ 0.96 (d, 3H, J =6.0 Hz, CH ₃ ), 1 .22 (d, 3H, J =6.0 Hz, CH ₃ ), 2.48 (s, 3H, CH ₃ ), 3.00-3.04 (m, 1 H, CH), 7.36 (d, 1 H, J =9.0 Hz, Ar), 7.76 (d, 2H, J =9.0 Hz, Ar), 7.99 (d, 2H, J =9.0 Hz, Ar), 8.02 (s, 1 H, Ar), 8.07 (s, 1 H, Ar), 8.1 1 (dd, 1 H, J =3.0 Hz, J =5.7 Hz, Ar), 8.86 (d, 1 H, J =3.0 Hz, Ar), 8.95 (s, 1 H, Ar); MS (ES+): m/e 444.1 (M+1 ). Example 192B:

3- (4-(lsopropylsulfonyl)phenyl)-6-(6-methylpyridin-3-yl)-8-(tr ifluoromethyl) imidazo[1 ,2-a]pyridine

Metachloroperbenzoic acid (0.1 21 g, 0.702 mmol) was added to a stirred solution of the compound of example 1 91 (0.150 g, 0.351 mmol) in dichloromethane (1 0 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.22 g (1 3.51 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .1 9 (d, 6H, J=6.0 Hz, 2CH ₃ ), 2.51 (s, 3H, CH ₃ ), 3.46-3.51 (m, 1 H, CH), 7.36 (d, 1 H, J =9.0 Hz, Ar), 7.99 (d, 2H, J =9.0 Hz, Ar), 8.08 (s, 1 H, Ar), 8.09 (d, 2H, J =9.0 Hz, Ar), 8.14 (d, 2H, J =3.0 Hz,Ar), 8.88 (d, 1 H, J =3.0 Hz, Ar), 9.03 (s, 1 H, Ar); MS (ES+) : m/e 460.4 (M+1 ).

Example 193:

6-(2-Methylpyrimidin-5-yl)-8-(trifluoromethyl)imidazo[1 ,2-a] pyridine

The compound of example 1 72 (5 g, 1 8.87 mmol) was treated with 2-methyl-5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidine (6.23 g, 28.3 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.308 g, 0.377 mmol) and sodium carbonate (3.00 g, 28.3 mmol) in dry dimethylformamide (25 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.65 g (49.5 %) ; ¹ H NMR (DMSO-de, 300 MHz) : δ 2.69 (s, 3H, CH ₃ ), 7.77 (s, 1 H, Ar), 8.14 (d, 2H, J =6.0 Hz, Ar), 9.1 3 (s, 2H, Ar), 9.34 (s, 1 H, Ar); MS (ES+) : m/e 279.5 (M+1 ).

Example 194:

3-Bromo-6-(2-methylpyrimidin-5-yl)-8-(trifluoromethyl) imidazo[1 ,2-a] pyridine

N-Bromosuccinimide (1 .730 g, 9.72 mmol) was added to a stirred solution of the compound of example 1 93 (2.6 g, 9.34 mmol) in dry CHCI ₃ (50 mL) at 1 0 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 2.97 g (87 %); ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 2.70 (s, 3H, CH ₃ ), 7.94 (s, 1 H, Ar), 8.22 (s, 1 H, Ar), 8.96 (s, 1 H, Ar), 9.1 8 (s, 2H, Ar); MS (ES+) : m/e 356 (M+1 ).

Example 195:

4- (5-(6-(2-methylpyrimidin-5-yl)-8-(trifluoromethyl) imidazo [1 ,2-a]pyridin-3-yl) pyridin-2-yl)morpholine The compound of example 194 (0.250 g, 0.700 mmol) was treated with 6- morpholinopyridin-3-ylboronic acid (0.175 g, 0.840 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.011 g, 0.014 mmol) and sodium carbonate (0.111 g, 1.050 mmol) in dry dimethylformamide (15 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.028 g (8.86 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.68 (s, 3H, CH ₃ ), 3.56 (s, 4H, 2CH ₂ ), 3.73 (s, 4H, 2CH ₂ ), 7.02 (d, 1H, J =6.0 Hz, Ar), 7.86 (s, 1H, Ar), 7.96 (d, 1H, J =6.0 Hz, Ar), 8.12 (s, 1H, Ar), 8.49 (s, 1H, Ar), 8.95 (s, 1H, Ar), 9.12 (s, 2H, Ar); MS (ES+): m/e441.2 (M+1).

Example 196:

3-(Trifluoromethyl)-5-(8-(trifluoromethyl)imidazo[1,2-a] pyridin-6-yl)pyridin-2- amine

The compound of example 172 (2 g, 7.55 mmol) was treated with 6-amino-5- (trifluoromethyl)pyridin-3-ylboronic acid (1.865 g, 9.06 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.106 g, 0.151 mmol) and sodium carbonate (2.000 g, 18.87 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.3 g (49.8 %); ¹ H NMR (DMSO-de, 300 MHz): δ 6.69 (s, 2H, Ar-NH ₂ ), 7.69 (s, 1H, Ar), 7.99 (s, 1H, Ar), 8.06 (s, 1H, Ar), 8.13 (d, 1H, J =1.2 Hz, Ar), 8.59 (d, 1H, J =3.0 Hz, Ar), 9.15 (s, 1H, Ar); MS (ES+): m/e 347.1 (M+1). Example 197:

5-(3-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl)-3- (trifluoromethyl) pyridin-2-amine

N-bromosuccinimide (4.01 g, 22.53 mmol) was added to a stirred solution of compound of example 196 (6 g, 17.33 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 1.6 g (21.72 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 6.74 (s, 2H, Ar- NH ₂ ), 7.86 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.20 (d, 1H, J =3.0 Hz, Ar), 8.64 (d, 1H, J =3.0 Hz, Ar), 8.74 (s, 1H, Ar); MS (ES+): m/e 426.1 (M+1). Example 198:

5-(3-(3-(Methylsulfonyl)phenyl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-6-yl) -3- (trifluoromethyl)pyridin-2-amine

The compound of example 197 (0.150 g, 0.353 mmol) was treated with (3- (methylsulfonyl)phenyl)boronic acid (85 mg, 0.423 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.014 g, 0.018 mmol) and sodium carbonate (0.073 g, 0.529 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.80 g (43.6 %); ¹ H NMR (DMSO-de, 300 MHz): δ 3.28 (s, 3H, CH ₃ ), 6.69 (s, 2H, Ar-NH2), 7.83 (t, 1 H,Ar), 7.98 (d, 1 H, J =9.0 Hz, Ar), 8.02 (s, 1 H, Ar), 8.1 1 (s, 1 H, Ar), 8.14 (d, 2H, J =9.0 Hz, Ar), 8.28 (s, 1 H, Ar), 8.59 (s, 1 H, Ar), 8.91 (s, 1 H, Ar); MS (ES+): m/e 501 (M+1 ). Example 199:

5-(3-(4-(lsopropylthio)phenyl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-6-yl)-3- (trifluoromethyl)pyridin-2-amine

The compound of example 197 (0.400 g, 0.941 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.221 g, 1 .129 mmol in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.038 mg, 0.047 mmol) and sodium carbonate (0.195 g, 1 .41 1 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.350 g (74.3 %); ¹ H NMR (DMSO-de, 300 ΜΗζ) :δ 1 .28 (d, 6H, J =6.6 Hz, 2CH ₃ ), 3.56-3.65 (m, 1 H, CH), 6.68 (s, 2H, Ar-NH ₂ ), 7.51 (d, 2H, J =8.1 Hz, Ar), 7.72 (d, 2H, J =8.1 Hz, Ar), 7.88 (s, 1 H, Ar), 8.03 (s, 1 H, Ar), 8.14 (d, 1 H, J =1 .5 Hz , J =8.1 Hz, Ar), 8.57 (s, 1 H, Ar), 8.83 (s, 1 H, Ar); MS (ES+): m/e 497.1 (M+1 ).

Example 200:

5-(3-(4-(lsopropylsulfinyl)phenyl)-8-(trifluoromethyl)imi dazo[1 ,2-a]pyridin-6-yl)-3- (trifluoromethyl)pyridin-2-amine

Metachloroperbenzoic acid (0.188 g, 1 .088 mmol) was added to a stirred solution of the compound of example 199 (0.270 g, 0.544 mmol) in dichloromethane (10 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.67 g (22.89 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.97 (d, 3H, J=6.0 Hz, CH ₃ ), 1.22 (d, 3H, J =6.0 Hz, CH ₃ ), 3.00-3.04 (m, 1H, CH), 6.69 (s, 2H, Ar-NH2), 7.76 (d, 2H, J =9.0 Hz, Ar), 7.98 (d, 2H, J =6.0 Hz, Ar), 8.00 (s, 1H, Ar), 8.07 (s, 1H, Ar), 8.16 (s, 1H, Ar), 8.59 (d, 1H, J =3.0 Hz, Ar), 8.91 (s, 1H, Ar); MS (ES+): m/e 513.1 (M+1).

Example 201 :

5- (3-(4-(lsopropylsulfinyl)phenyl)-8-(trifluoromethyl)imidazo [1,2-a]pyridin-6-yl)-3- (trifluoromethyl)pyridin-2-amine

Metachloroperbenzoic acid (0.188 g, 1.088 mmol) was added to a stirred solution of compound of example 199 (0.270 g, 0.544 mmol) in dichloromethane (10 ml_), according to the procedure for the preparation of the compound of example 5 to afford the title compound.Yield: 0.56 g (19.25 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1.10 (d, 6H, J =6.0 Hz, 2CH ₃ ), 3.44-3.53 (m, 1H,CH), 6.70 (s, 2H, Ar-NH ₂ ), 7.97 (d, 2H, J =9.0 Hz, Ar), 8.07 (d, 4H, J =6.0 Hz, Ar), 8.17 (d, 1H, J =3.0 Hz, Ar), 8.61 (d, 1H, J =3.0 Hz, Ar), 8.99 (s, 1H,Ar); MS (ES+): m/e 529.1 (M+1).

Example 202:

6- (6-Methoxypyridin-3-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyr idine

The compound of example 172 (3 g, 11.32 mmol) was treated with (6-methoxypyridin-3- yl)boronic acid (1.731 g, 11.32 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.159 g, 0.226 mmol) and sodium carbonate (2.347 g, 16.98 mmol) in dry dimethylformamide (10 ml_) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.3 g (39 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.89 (s, 3H, CH ₃ ), 6.94 (d, 1H, J =9.0 Hz, Ar), 7.71 (s, 1H, Ar), 7.96 (s, 1H, Ar), 8.10 (m, 2H, Ar), 8.55 (d, 1H, J =3.0 Hz, Ar), 9.16 (s, 1H, Ar); MS(ES+): m/e 294 (M+1).

Example 203:

3-Bromo-6-(6-methoxypyridin-3-yl)-8-(trifluoromethyl)imid azo[1 ,2-a] pyridine

N-bromosuccinimide (1.736 g, 9.75 mmol) was added to a stirred solution of the compound of example 202 (2.2 g, 7.50 mmol) in dry CHCI ₃ (50 ml_) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 2.1 g (75 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.89 (s, 3H, CH ₃ ), 6.94 (d, 1 H, J =9.0 Hz, Ar), 7.88 (s, 1 H, Ar), 8.07 (s, 1 H, Ar), 8.18 (dd, 1 H, J =3.0 Hz, J =8.7 Hz, Ar), 8.62 (d, 1 H, J =3.0 Hz, Ar), 8.71 (s, 1 H, Ar); MS (ES+): m/e 374.1 (M+1 ). Example 204:

3-(4-(lsopropylthio)phenyl)-6-(6-methoxypyridin-3-yl)-8-(tri fluoromethyl) imidazo

[1 ,2-a]pyridine

The compound of example 203 (0.500 g, 1 .344 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.316 g, 1 .612 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.054 g, 0.067 mmol) and sodium carbonate (0.279 g, 2.015 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.335 g (56 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .28 (d, 6H, J =9.0 Hz, 2CH ₃ ), 3.58-3.62 (m, 1 H, Ar), 3.88 (s, 3H, OCH ₃ ), 6.92 (d, 1 H, J =8.7, Ar), 7.51 (d, 2H, J =8.1 , Ar), 7.73 (d, 2H, J =8.1 Hz, Ar), 7.91 (s, 1 H, Ar), 8.01 (s, 1 H, Ar), 8.13 (dd, 1 H, J =2.4 Hz, J =8.7 Hz, Ar), 8.58 (d, 1 H, J =2.4 Hz, Ar), 8.83 (s, 1 H, Ar); MS (ES+): m/e 444.1 (M+1 ).

Example 205:

5-(3-(4-(lsopropylsulfinyl)phenyl)-8-(trifluoromethyl)imi dazo [1 ,2-a]pyridin-6 -yl)-3- (trifluoromethyl)pyridin-2-amine

Metachloroperbenzoic acid (0.140 g, 0.812 mmol) was added to a stirred solution of the compound of example 204 (0.180 g, 0.406 mmol) in dichloromethane (10 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.80 g (42.7 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.98 (d, 3H, J=6.0 Hz, CH ₃ ), 1 .22 (d, 3H, J =6.0 Hz, CH ₃ ), 3.00-3.04 (m, 1 H, CH), 3.88 (s, 3H, OCH ₃ ), 6.93 (d, 2H, J =9.0 Hz, Ar), 7.77 (d, 2H, J =9.0 Hz, Ar), 7.99 (d, 2H, J =9.0 Hz, Ar), 8.04 (s, 1 H, Ar), 8.14 (dd, 1 H, J =3.0 Hz, J =8.4 Hz, Ar), 8.59 (d, 1 H, J =3.0 Hz, Ar), 8.91 (s, 1 H, Ar); MS (ES+): m/e 460.1 (M+1 ).

Example 206:

3-(4-(lsopropylsulfonyl)phenyl)-6-(6-methoxypyridin-3-yl)-8- (trifluoromethyl) imidazo[1 ,2-a]pyridine

Metachloroperbenzoic acid (0.140 g, 0.812 mmol) was added to a stirred solution of the compound of example 204 (0.180 g, 0.406 mmol) in dichloromethane (10 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound.Yield: 0.57 g (29.3 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): 51.19 (d, 6H, J =6.0 Hz, 2CH ₃ ), 3.41-3.53 (m, 1H, CH), 3.88 (s, 3H, OCH ₃ ), 6.94 (d, 1H, J =9.0 Hz, Ar), 7.97 (d, 2H, J =9.0 Hz, Ar), 8.07-8.10 (m, 4H, Ar), 8.16 (dd, 1H, J =3.0 Hz, J =8.7 Hz, Ar), 8.61 (d, 1 H, J =3.0 Hz, Ar), 8.99 (s, 1 H, Ar); MS (ES+): m/e 476.1 (M+1).

Example 207:

3-(4-(t-Butyl)phenyl)-6-(6-methoxypyridin-3-yl)-8-(trifluoro methyl)imidazo [1,2-a] pyridine

The compound of example 203 (0.200 g, 0.537 mmol) was treated with (4-(t- butyl)phenyl)boronic acid (0.115 g, 0.645 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.021 g, 0.027 mmol) and sodium carbonate (0.111 g, 0.806 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.107 g (46.6 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1.35 (s, 9H, 3CH ₃ ), 3.90 (s, 3H, OCH ₃ ), 6.94 (d, 1H, J =6.0 Hz, Ar), 7.60 (d, 2H, J =6.0 Hz, Ar), 7.72 (d, 2H, J =6.0 Hz, Ar), 7.89 (s, 1H, Ar), 8.02 (s, 1H, Ar), 8.14 (d, 1H, J =6.0 Hz, Ar), 8.59 (s, 1H, Ar), 8.84 (s, 1H, Ar); MS (ES+): m/e 426.1 (M+1).

Example 208:

6-(6-Methoxypyridin-3-yl)-3-(4-propylphenyl)-8-(trifluoro methyl)imidazo[1,2-a] pyridine

The compound of example 203 (0.200 g, 0.537 mmol) was treated with 4- propylphenylboronic acid (0.106 g, 0.645 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.021 g, 0.027 mmol) and sodium carbonate (0.111 g, 0.806 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.102 g (46.1 %); ¹ H NMR (DMSO-de, 300 MHz): δ 0.94 (t, 3H, J =3.0 Hz, CH ₃ ), 1.64-1.66 (m, 2H, J =6.0 Hz, CH ₂ ), 2.65 (d, 2H, J =3.0 Hz, CH ₂ ), 3.90 (s, 3H, OCH ₃ ), 6.93 (d, 1H, J =6.0 Hz, Ar), 7.40 (d, 2H, J =3.0 Hz, Ar), 7.70 (d, 2H, J =3.0 Hz, Ar), 7.88 (s, 1H, Ar), 8.01 (s, 1H, Ar), 8.13 (d, 1H, J =6.0 Hz, Ar), 8.58 (s, 1H, Ar), 8.81 (s, 1H, Ar); MS (ES+): m/e 412.1 (M+1). Example 209:

3-(4-(Ethylthio)phenyl)-6-(6-methoxypyridin-3-yl)-8-(trifluo romethyl)imida [1,2-a] pyridine

The compound of example 203 (0.200 g, 0.537 mmol) was treated with 4- (ethylthio)phenylboronic acid (0.117 g, 0.645 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.021 g, 0.027 mmol) and sodium carbonate (0.111 g, 0.806 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.100 g (42.4 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1.30 (t, 3H, J =6.0 Hz, CH ₃ ), 3.06 (q, 2H, J =6.0 Hz, CH ₂ ), 3.91 (s, 3H, OCHs), 6.94 (d, 1H, J =6.0 Hz, Ar), 7.49 (d, 2H, J =3.0 Hz, Ar), 7.73 (d, 2H, J =3.0 Hz, Ar), 7.91 (s, 1H, Ar), 8.03 (s, 1H, Ar), 8.15 (dd, 1H, J =1.2 Hz, J =5.1 Hz, Ar), 8.59 (d, 1H, J =3.0 Hz, Ar), 8.83 (s, 1H, Ar); MS (ES+): m/e 430.6 (M+1).

Example 210:

6-(2-Methoxypyridin-3-yl)-8-(trifluoromethyl)imidazo[1,2-a] pyridine

The compound of example 172 (3 g, 11.32 mmol) was treated with (2-methoxypyridin-3- yl)boronic acid (2.077 g, 13.58 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.159 g, 0.226 mmol) and sodium carbonate (2.347 g, 16.98 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.7 g (79 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.93 (s, 3H, OCH3), 7.14 (dd, 1H, J =6.0 Hz, J =7.5 Hz, Ar), 7.73 (d, 1H, J =1.2 Hz, Ar), 7.87 (s, 1H, Ar), 7.94 (dd, 1 H, J =3.0 Hz, J =7.2 Hz, Ar), 8.16 (d, 1 H, J =1.2 Hz, Ar), 8.24 (dd, 1 H, J =2.0 Hz, J =4.8 Hz, Ar), 9.07 (s, 1H, Ar); MS (ES+): m/e 294 (M+1).

Example 211 :

3-Bromo-6-(2-methoxypyridin-3-yl)-8-(trifluoromethyl) imidazo[1 ,2-a] pyridine

N-Bromosuccinimide (2.130 g, 11.97 mmol) was added to a stirred solution of the compound of example 210 (2.7 g, 9.21 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 3.1 g (90 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.93 (s, 3H, OCH ₃ ), 7.14 (dd, 1H, J =3.0 Hz, J =4.5 Hz, Ar), 7.90 (s, 1H, Ar), 8.00 (s, 1H, Ar), 8.02 (d, 1H, J =0.9 Hz, Ar), 8.25-8.26 (m, 1 H, Ar), 8.71 (s, 1 H, Ar); MS (ES+): m/e 373.1 (M+1 ). Example 212:

3-(4-lsobutylphenyl)-6-(2-methoxypyridin-3-yl)-8-(trifluorom ethyl)imidazo [1,2-a] pyridine

The compound of example 211 (0.200 g, 0.537 mmol) was treated with (4- isobutylphenyl)boronic acid (0.115 g, 0.645 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.021 g, 0.027 mmol) and sodium carbonate (0.111 mg, 0.806 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.152 g (65.5 %); ¹ H NMR (DMSO-de, 300 MHz): δ 0.91 (d, 6H, J =3.0 Hz, 2CH ₃ ), 1.88-1.92 (m, 1H, CH), 2.50- 2.53 (m, 2H, CH ₂ ), 3.92 (s, 1H, OCH ₃ ), 7.13 (dd, 1H, J =3.0 Hz, J =4.2 Hz, Ar), 7.37 (d, 2H, J =6.0 Hz, Ar), 7.65 (d, 2H, J =6.0 Hz, Ar), 7.89 (s, 1H, Ar), 7.95 (s, 1H, Ar), 8.02 (d, 1H, J =4.2 Hz, Ar), 8.24 (d, 1H, J =2.7 Hz, Ar), 8.87 (s, 1H, Ar); MS (ES+): m/e 426.2 (M+1).

Example 213:

6-Phenyl-8-(trifluoromethyl)imidazo[1,2-a]pyridine

The compound of example 172 (3 g, 11.32 mmol) was treated with phenylboronic acid (1.656 g, 13.58 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.159 g, 0.226 mmol) and sodium carbonate (2.347 g, 16.98 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.6 g (87 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.39-7.45 (m, 1H, Ar), 7.52 (t, 2H, J =4.5 Hz, Ar), 7.74 (s, 1H, Ar), 7.77 (d, 2H, J =6.0 Hz, Ar), 7.96 (s, 1H, Ar), 8.14 (s, 1H, Ar), 9.20 (s, 1H, Ar); MS (ES+): m/e 263 (M+1).

Example 214:

3-Bromo-6-phenyl-8-(trifluoromethyl)imidazo[1,2-a]pyridine

N-bromosuccinimide (2.294 g, 12.89 mmol) was added to a stirred solution of the compound of example 213 (2.6 g, 9.91 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 3.1 g (91 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.45-7.48 (m, 1H, Ar), 7.52 (t, 2H, Ar), 7.84 (d, 2H, J =6.0 Hz, Ar), 7.91 (s, 1H, Ar), 8.07 (s, 1H, Ar), 8.68 (s, 1H, Ar); MS (ES+): m/e 342.1 (M+1). Example 215:

3- (4-(lsopropylthio)phenyl)-6-phenyl-8-(trifluoromethyl) imidazo[1 ,2-a] pyridine

The compound of example 214 (0.500 g, 1.466 mmol) was treated with 4- (isopropylthio)phenylboronic acid (0.345 g, 1.759 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.059 g, 0.073 mmol) and sodium carbonate (0.304 g, 2.199 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.110 g (17.71 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1.29 (d, 6H, J =6.0 Hz, 2CH ₃ ), 3.58-3.67 (m, 1 H, CH), 7.42 (dd, 1H, J =3.0 Hz, J =7.2 Hz, Ar), 7.47 (d, 2H, J =6.0 Hz, Ar), 7.51-7.55 (m, 2H, Ar), 7.73 (s, 2H, Ar), 7.77 (d, 1H, J =6.0 Hz, Ar), 7.80 (d, 1H, J =1.2 Hz, Ar), 7.93 (s, 1H, Ar), 8.02 (s, 1 H, Ar), 8.81 (s, 1 H, Ar); MS (ES+): m/e 413.4 (M+1 ). Example 216:

4- (4-(6-Phenyl-8-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)p henyl) morpholine

The compound of example 214 (0.200 g, 0.586 mmol) was treated with (4- morpholinophenyl)boronic acid (0.146 g, 0.704 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.023 g, 0.029 mmol) and sodium carbonate (0.122 g, 0.879 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.138 g (54.8 %); ¹ H NMR (DMSO-de, 300 MHz): δ 3.21 (d, 4H, J =9.0 Hz, 2CH ₂ ), 3.76 (d, 4H, J =9.0 Hz, 2CH ₂ ), 7.14 (d, 2H, J =9.0 Hz, Ar), 7.43-7.53 (m, 3H, Ar), 7.63 (d, 2H, J =9.0 Hz, Ar), 7.77 (d, 2H, J =9.0 Hz, Ar), 7.80 (s, 1H, Ar), 7.98 (s, 1H, Ar), 8.71 (s, 1H, Ar) ; MS (ES+): m/e 424.2 (M+1).

Example 217:

6-(o-Tolyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridine

The compound of example 172 (2 g, 7.55 mmol) was treated with o-tolylboronic acid (1.231 g, 9.06 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.106 g, 0.151 mmol) and sodium carbonate (1.564 g, 11.32 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.56 g (74.7 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.29 (s, 3H, CH ₃ ), 7.30 (d, 1H, J =3.0 Hz, Ar), 7.31-7.37 (m, 3H, Ar), 7.68 (s, 1H, Ar), 7.74 (d, 1H, J =1.2 Hz, Ar), 8.13 (d, 1H, J =1.2 Hz, Ar), 8.87 (s, 1H, Ar); MS (ES+): m/e 277 (M+1).

Example 218:

3-Bromo-6-(o-tolyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin e

N-bromosuccinimide (1.307 g, 7.34 mmol) was added to a stirred solution of the compound of example 217 (1.56 g, 5.65 mmol) in dry CHCI ₃ (50 mL) at 10 °C and stirred for 1 h under nitrogen atmosphere. The reaction mixture was diluted with water (10 mL), extracted with chloroform (2x25 mL) and washed with water (25 mL), brine (25 mL) and dried over sodium sulphate. The crude material obtained was purified by column chromatography (silica gel, methanol in chloroform) to afford the title compound. Yield: 1.76 g (86 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.29 (s, 3H, CH ₃ ), 7.33 (d, 2H, J =3.0 Hz, Ar), 7.38-7.43 (m, 2H, Ar), 7.83 (s, 1H, Ar), 7.92 (s, 1H, Ar),8.47 (s, 1H, Ar); MS (ES+): m/e 356.1 (M+1).

Example 219:

3-(4-(lsopropylthio) phenyl)-6-phenyl-8-(trifluoromethyl) imidazo[1,2-a] pyridine The compound of example 218 (0.500 g, 1.408 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.331 g, 1.689 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.057 g, 0.070 mmol) and sodium carbonate (0.292 g, 2.112 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.420 g (69.4 %); ¹ H NMR (DMSO-de, 300 MHz): δ 0.90 (d, 6H, J=6.0 Hz, 2CH ₃ ), 1.86-1.90 (m, 1H, CH), 2.28 (s, 3H, CH ₃ ), 7.27 (d, 1H, J =6.0 Hz, Ar), 7.29-7.36 (m, 4H, Ar), 7.39 (d, 1H, J =6.0 Hz, Ar), 7.63 (d, 2H, J =9.0 Hz, Ar), 7.75 (s, 1H, Ar), 7.90 (s, 1H, Ar), 8.51 (s, 1H, Ar); MS (ES+): m/e 427.5 (M+1).

Example 220:

3-Bromo-6-(o-tolyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin e

Metachloroperbenzoic acid (0.283 g, 1.641 mmol) was added to a stirred solution of the compound of example 219 (0.350 g, 0.821 mmol) in dichloromethane (10 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.140 g (38.2 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.97 (d, 3H, J =6.0 Hz, CH ₃ ), 1 .22 (d, 3H, J =6.0 Hz, CH ₃ ), 2.30 (s, 3H, CH ₃ ), 2.99-3.03 (m, 1 H, CH), 7.28-7.42(m, 4H, Ar), 7.78 (t, 3H, Ar), 7.95 (d, 2H, J =6.0 Hz, Ar), 8.04 (s, 1 H, Ar), 8.65 (s, 1 H, Ar); MS (ES+): m/e 443.1 (M+1 ).

Example 221 :

3-(4-(lsopropylsulfonyl)phenyl)-6-(o-tolyl)-8-(trifluorometh yl) imidazo[1 ,2-a] pyridine

Metachloroperbenzoic acid (0.283 g, 1 .641 mmol) was added to a stirred solution of the compound of example 219 (0.350 g, 0.821 mmol) in dichloromethane (10 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.40 g (10.32 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .21 (d, 6H, J =9.0 Hz, 2CH ₃ ), 2.30 (s, 3H, CH ₃ ), 3.43-3.52 (m, 1 H, J =6.0 Hz, CH), 7.27-7.43 (m, 4H, Ar), 7.84 (s, 1 H, Ar), 7.97-8.03 (m, 4H, Ar), 8.12 (s, 1 H, Ar), 8.74 (s, 1 H, Ar); MS (ES+): m/e 459.1 (M+1 ).

Example 222:

4-(4-(6-(o-Tolyl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-3-yl)phenyl) morpholine

The compound of example 218 (0.200 g, 0.563 mmol) was treated with (4- morpholinophenyl)boronic acid (0.140 g, 0.676 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.022 g, 0.028 mmol) and sodium carbonate (0.1 17 g, 0.845 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.127 g (49.5 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.29 (s, 3H, CH ₃ ), 3.19 (d, 4H, J =6.0 Hz, 2CH ₂ ), 3.74 (d, 4H, J =6.0 Hz, 2CH ₂ ), 7.10 (d, 2H, J =9.0 Hz, Ar), 7.27-7.39 (m, 4H, Ar), 7.57 (d, 2H, J =9.0 Hz, Ar), 7.73 (s, 1 H, Ar), 7.82 (s, 1 H, Ar), 8.43 (s, 1 H, Ar); MS (ES+): m/e 438.2 (M+1 ).

Example 223:

3-(4-(Methylsulfonyl)phenyl)-6-(o-tolyl)-8-(trifluoromethyl) imidazo[1 ,2-a] pyridine

The compound of example 218 (0.200 g, 0.563 mmol) was treated with (4- (methylsulfonyl)phenyl)boronic acid (0.135 g, 0.676 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.022 g, 0.028 mmol),and sodium carbonate (0.1 17 g, 0.845 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.178 g (68.3 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .99 (s, 3H, CH ₃ ), 3.33 (s, 3H, CH ₃ ), 7.27-7.37 (m, 3H, Ar), 7.42 (d, 1 H, J =6.0 Hz, Ar), 7.84 (s, 1 H, Ar), 8.02-8.09 (m, 4H, Ar), 8.10 (s, 1 H, Ar), 8.69 (s, 1 H, Ar); MS (ES+): m/e 431 .4 (M+1 ).

Example 224:

5-(8-(Trifluoromethyl)imidazo[1 ,2-a]pyridin-6-yl)picolinonitrile

The compound of example 172 (2.5 g, 9.43 mmol) was treated with 4-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)picolinonitrile (2.170 g, 9.43 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.132 g, 0.189 mmol) and sodium carbonate (1 .956 g, 14.15 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.0 g (67.8 %); ¹ H NMR (DMSO-de, 300 MHz): δ 7.79 (d, 1 H, J =1 .2 Hz, Ar), 8.17 (d, 2H, J =1 .2 Hz, Ar), 8.21 (d, 1 H, J =9.0 Hz, Ar), 8.50 (dd, 1 H, J =3.0 Hz, J =8.1 Hz, Ar), 9.21 (t, 1 H, Ar), 9.43 (s, 1 H, Ar); MS (ES+): m/e 289 (M+1 ).

Example 225:

5-3-Bromo-6-(o-tolyl)-8-(trifluoromethyl)imidazo[1 ,2-a] pyridine

N-bromosuccinimide (2.007 g, 1 1 .28 mmol) was added to a stirred solution of the compound of example 224 (2.5 g, 8.67 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 1 .76 g (46.4 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.94 (s, 1 H, Ar), 8.20-8.25 (m, 2H, Ar), 8.58 (d, 1 H, J =3.0 Hz, J =8.1 Ar), 9.01 (s, 1 H, Ar), 9.28 (d, 1 H, J =3.0 Hz, Ar); MS (ES+): m/e 368.1 (M+1 ). Example 226:

5-(3-(4-lsobutylphenyl)-8-(trifluoromethyl)imidazo[1 ,2-a] pyridin-6-yl)

picolinonitrile

The compound of example 225 (0.200 g, 0.545 mmol) was treated with (4- isobutylphenyl)boronic acid (0.1 16 g, 0.654 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.022 g, 0.027 mmol) and sodium carbonate (0.113 g, 0.817 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.70 g (30.3 %); ¹ H NMR (DMSO-de, 300 MHz): δ 0.93 (d, 6H, J =3.0 Hz, 2CH ₃ ), 1.86-1.97 (m, 1H, CH), 2.50- 2.56 (m, 2H, CH ₂ ), 7.38 (d, 2H, J =9.0 Hz, Ar), 7.72 (d, 2H, J =9.0 Hz, Ar), 7.94 (s, 1H, Ar), 8.18 (d, 2H, J =9.0 Hz, Ar), 8.52 (dd, 1H, J =3.0 Hz, J=8.1 Hz, Ar), 9.06 (s, 1H, Ar), 9.22 (d, 1 H, J =3.0 Hz, Ar); MS (ES+): m/e 421.4 (M+1 ).

Example 227:

5-(3-(4-(t-Butyl)phenyl)-8-(trifluoromethyl)imidazo[1,2-a] pyridin-6-yl)

picolinonitrile

The compound of example 225 (0.200 g, 0.545 mmol) was treated with (4-(t- butyl)phenyl)boronic acid (0.116 g, 0.654 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.022 g, 0.027 mmol) and sodium carbonate (0.113 g, 0.817 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.77 g (33.4 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1.35 (s, 9H, 3CH3), 7.60 (d, 2H, J =9.0 Hz, Ar), 7.75 (d, 2H, J =9.0 Hz, Ar), 7.94 (s, 1H, Ar), 8.18 (d, 2H, J =9.0 Hz, Ar), 8.53 (dd, 1H, J =3.0 Hz, J=8.1 Hz, Ar), 9.10 (s, 1H, Ar), 9.25 (d, 1H, J =3.0 Hz, Ar); MS (ES+): m/e 421.4 (M+1).

Example 228:

t-Butyl 4-(5-(6-(6-cyanopyridin-3-yl)-8-(trifluoromethyl) imidazo[1,2-a] pyridin-3-yl) pyridin-2-yl)piperazine-1-carboxylate

The compound of example 225 (0.300 g, 0.817 mmol) was treated with t-butyl 4-(5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (0.382 g, 0.981 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.033 g, 0.041 mmol) and sodium carbonate (0.169 g, 1.226 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.140 g (30.0 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1.43 (d, 9H, 3CH3), 3.45 (s, 4H, 2CH ₂ ), 3.62 (d, 4H, J =6.0 Hz, 2CH ₂ ), 7.03 (d, 1H, J =9.0 Hz, Ar), 7.88 (s, 1H, Ar), 7.97 (dd, 1H, J =3.0 Hz, J =9.0 Hz, Ar), 8.18 (d, 2H, J =9.0 Hz, Ar), 8.49-8.54 (m, 2H, Ar), 9.00 (s, 1H, Ar), 9.24 (d, 1H, J =3.0 Hz, Ar); MS (ES+): m/e 550.1 (M+1). Example 229:

5- (3-(6-(Piperazin-1-yl)pyridin-3-yl)-8-(trifluoromethyl) imidazo [1,2-a] pyridin-6-yl) picolinonitrile

The compound of example 228 (0.100 g, 0.182 mmol) was added to a stirred solution of HCI (5.53 μΙ_, 0.182 mmol) solution in dioxane (10 mL) according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 0.70 g (79 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.80 (d, 4H, J =6.0 Hz, 2CH ₂ ), 3.52 (s, 4H, 2CH ₂ ), 6.98 (d, 1H, J =9.0 Hz, Ar), 7.86 (s, 1H, Ar), 7.91-7.94 (m, 1H, Ar), 8.16 (t, 3H, Ar), 8.46 (d, 1H, J =3.0 Hz, Ar), 8.52 (d, 1H, J =9.0 Hz, Ar), 9.00 (s, 1H, Ar), 9.23 (s, 1H, Ar); MS (ES+): m/e 450.5 (M+1).

Example 230:

4-(4-(6-(6-Cyanopyridin-3-yl)-8-(trifluoromethyl)imidazo[1 ,2-a] pyridin-3-yl) phenyl) thiomorpholine 1,1 -dioxide

The compound of example 225 (0.500 g, 1.404 mmol) was treated with 4-(4-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)thiomorpholine 1,1 -dioxide (0.521 g, 1.544 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.057 g, 0.070 mmol) and sodium carbonate (0.291 g, 2.106 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.219 g (38.5 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.16 (s, 4H, 2CH ₂ ), 3.90 (s, 4H, 2CH ₂ ), 7.23 (d, 2H, J =9.0 Hz, Ar), 7.68 (d, 2H, J =9.0 Hz, Ar), 7.87 (s, 1H, Ar), 8.15-8.19 (m, 2H, Ar), 8.50 (dd, 1H, J =3.0 Hz, J =8.1 Hz, Ar), 9.01 (s, 1H, Ar), 9.23 (d, 1H, J =3.0 Hz, Ar); MS (ES+): m/e 498.4 (M+1). Example 231 :

6- (4-(t-Butyl)phenyl)-8-(trifluoromethyl)imidazo[1,2-a] pyridine

The compound of example 172 (2.5 g, 9.43 mmol) was treated with (4-(t- butyl)phenyl)boronic acid (2.015 g, 11.32 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.132 g, 0.189 mmol) and sodium carbonate (1.956 g, 14.15 mmol) in dry dimethylformamide (1 0 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.6 g (86 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .32 (s, 9H, 3CH ₃ ), 7.53 (d, 2H, J =9.0 Hz, Ar), 7.69 (d, 2H, J =9.0 Hz, Ar), 7.73 (d, 1 H, J =1 .2 Hz, Ar), 7.95 (s, 1 H, Ar), 8.1 3 (d, 1 H, J =1 .2 Hz, Ar), 9.1 7 (d, 1 H, J =0.6 Hz, Ar); MS (ES+): m/e 31 9 (M+1 ).

Example 232:

3-Bromo-6-(4-(t-butyl)phenyl)-8-(trifluoromethyl) imidazo[1 ,2-a]pyridine

N-bromosuccinimide (1 .672 g, 9.39 mmol) was added to a stirred solution of the compound of example 231 (2.3 g, 7.23 mmol) in dry CHCI ₃ (50 mL) at 1 0 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 2.6 g (86 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .33 (s, 9H, 3CH ₃ ), 7.54 (d, 2H, J =9.0 Hz, Ar), 7.75 (d, 2H, J =9.0 Hz, Ar), 7.90 (s, 1 H, Ar), 8.05 (s, 1 H, Ar), 8.66 (s, 1 H, Ar); MS (ES+) : m/e 398.2 (M+1 ).

Example 233:

6-(4-(t-Butyl)phenyl)-3-(4-(isopropylthio)phenyl)-8-(trifluo romethyl)imidazo [1 ,2-a] pyridine

The compound of example 232 (0.500 g, 1 .259 mmol) was treated with (4- (isopropylthio)phenyl)boronic acid (0.296 g, 1 .51 0 mmol) in the presence of [1 , 1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.051 g, 0.063 mmol) and sodium carbonate (0.261 g, 1 .888 mmol) in dry dimethylformamide (1 0 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.325 g (52 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .22-1 .31 (s, 1 5H, 5CH ₃ ), 3.61 -3.64 (m, 1 H, CH), 7.50-7.55 (m, 4H, Ar), 7.69 (d, 2H, J =9.0 Hz, Ar), 7.74 (d, 2H, J =9.0 Hz, Ar), 7.92 (s, 1 H, Ar), 8.01 (s, 1 H, Ar), 8.78 (s, 1 H, Ar); MS (ES+): m/e 469.2 (M+1 ). Example 234:

6-(4-t-Butylphenyl)-3-(4-(isopropylsulfinyl)phenyl)-8-(trifl uoromethyl) imidazo [1 ,2- a] pyridine

Metachloroperbenzoic acid (0.21 7 g, 1 .259 mmol) was added to a stirred solution of the compound of example 233 (0.250 g, 0.629 mmol) in dichloromethane (1 0 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.1 08 g (34.0 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .24 (d, 6H, J =6.0 Hz, 2CH ₃ ), 1 .32 (s, 9H, 3CH3), 3.00-3.05 (m, 1 H, CH), 7.52 (d, 2H, J =9.0 Hz, Ar), 7.71 (d, 2H, J =9.0 Hz, Ar), 7.80 (d, 2H, J =9.0 Hz, Ar), 8.00 (s, 1 H, Ar), 8.03 (s, 2H, Ar), 8.32 (s, 1 H, Ar), 8.87 (s, 1 H, Ar); MS (ES+) : m/e 485.1 (M+1 ).

Example 235:

4-(4-(6-(4-t-Butylphenyl)-8-(trifluoromethyl)imidazo[1 ,2-a] pyridin-3-yl) phenyl) morpholine

The compound of example 232 (0.200 g, 0.503 mmol) was treated with (4- morpholinophenyl)boronic acid (0.130 g, 0.629 mmol) in the presence of [1 , 1 '- Bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.01 2 g, 0.01 5 mmol) and sodium carbonate (0.1 07 g, 1 .007 mmol) in dry dimethylformamide (1 0 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.145 g (55.4 %) ; ¹ H NMR (DMSO-de, 300 MHz) : δ 1 .32 (s, 9H, 3CH3), 3.22 (d, 4H, J =2.4 Hz, 2CH ₂ ), 3.69 (d, 4H, J =2.4 Hz, 2CH ₂ ), 7.1 3 (d, 2H, J =9.0 Hz, Ar), 7.50 (d, 2H, J =9.0 Hz, Ar), 7.60-7.68 (m, 4H, Ar), 7.80 (s, 1 H, Ar), 7.95 (s, 1 H, Ar), 8.68 (s, 1 H, Ar); MS (ES+) : m/e 480.5 (M+1 ). Example 236:

4-(6-(4-(t-Butyl)phenyl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-3-yl) benzene sulfonamide

The compound of example 232 (2 g, 5.03 mmol) was treated with 4-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzenesulfonamide (1 .426 g, 5.03 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.206 g, 0.252 mmol) and sodium carbonate (1 .044 g, 7.55 mmol) in dry dimethylformamide (1 0 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1 .05 g (43.2 %) ; ¹ H NMR (DMSO-de, 300 MHz): δ 1 .32 (s, 9H, 3CH ₃ ), 7.49 (s, 2H, Ar), 7.52 (d, 2H, J =9.0 Hz, Ar), 7.73 (d, 2H, J =9.0 Hz, Ar), 8.00 (s, 4H, Ar), 8.04 (d, 2H, J =9.0 Hz, Ar), 8.88 (s, 1 H, Ar) ; MS (ES+) : m/e 474.5 (M+1 ).

Example 237:

6-(2-Methoxypyrimidin-5-yl)-8-(trifluoromethyl)imidazo[1 ,2-a] pyridine The compound of example 172 (3 g, 11.32 mmol) was treated with (2- methoxypyrimidin-5-yl)boronic acid (2.091 g, 13.58 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene] dichloropalladium(ll) complex with dichloromethane (0.159 g, 0.226 mmol) and sodium carbonate (2.347 g, 16.98 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.23 g (66.2 %); ¹ H NMR (DMSO-de, 300 MHz): δ 3.98 (s, 3H, OCH ₃ ), 7.76 (d, 1H, J =0.9 Hz, Ar), 8.07 (s, 1H, Ar), 8.14 (d, 1H, J =0.9 Hz, Ar), 9.02 (s, 2H, Ar), 9.25 (s, 1H, Ar); MS (ES+): m/e 295.4 (M+1).

Example 238:

3- Bromo-6-(2-methoxypyrimidin-5-yl)-8-(trifluoromethyl) imidazo[1 ,2-a] pyridine

N-Bromosuccinimide (1.730 g, 9.72 mmol) was added to a stirred solution of the compound of example 237 (2.2 g, 7.48 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 2.2 g (79 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.99 (s, 3H, OCH ₃ ), 7.93 (s, 1H, Ar), 8.18 (s, 1H, Ar), 8.90 (s, 1H, Ar), 9.07 (s, 2H, Ar); MS (ES+): m/e 374.1 (M+1).

Example 239:

4- (4-(6-(2-Methoxypyrimidin-5-yl)-8-(trifluoromethyl)imidazo[1 ,2-a]pyridin-3-yl) phenyl)morpholine

The compound of example 238 (0.300 g, 0.804 mmol) was treated with (4- morpholinophenyl)boronic acid (0.208 g, 1.005 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.19 g, 0.024 mmol) and sodium carbonate (0.170 g, 1.608 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.156 g (42.1 %); ¹ H NMR (DMSO-de, 300 MHz): δ 3.21 (t, 4H, 2CH ₂ ), 3.75 (t, 4H, 2CH ₂ ), 3.97 (s, 3H, OCH ₃ ), 7.13 (d, 2H, J =8.7 Hz, Ar), 7.64 (d, 2H, J =8.7 Hz, Ar), 7.83 (s, 1H, Ar), 8.06 (s, 1H, Ar), 8.89 (s, 1H, Ar), 9.01 (s, 2H, Ar); MS (ES+): m/e 456.2 (M+1). Example 240:

3-(2-Methoxypyridin-4-yl)-6-(2-methoxypyrimidin-5-yl)-8-(tri fluoromethyl) imidazo

[1 ,2-a]pyridine

The compound of example 238 (0.300 g, 0.804 mmol) was treated with 2- methoxypyridin-4-ylboronic acid (0.154 g, 1 .005 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.019 g, 0.024 mmol) and sodium carbonate (0.170 g, 1 .608 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.102 g (31 .4 %); ¹ H NMR (DMSO-de, 300 MHz): δ 3.95 (d, 6H, J =8.7 Hz, 20CH ₃ ), 7.02 (d, 1 H, J =8.4 Hz, Ar), 7.91 (s, 1 H, Ar), 8.1 1 (d, 1 H, J =2.4 Hz, Ar), 8.13 (d, 1 H, J =2.4 Hz, Ar), 8.56 (d, 1 H, J =2.1 Hz, Ar), 8.94 (s, 1 H, Ar), 9.03 (s, 2H, Ar); MS (ES+): m/e 402.3 (M+1 ). Example 241 :

5-(lmidazo[1 ,2-a]pyridin-6-yl)-2-(trif luoromethyl)pyridine 1 -oxide

The compound of example 67 (5 g, 19 mmol) in acetonitrile (5 mL) was added to a mixture of Na ₂ C0 ₃ (2.013 g, 19.00 mmol), H ₂ 0 ₂ (1 .746 mL, 28.5 mmol) and cooled to 0 °C. To this cooled suspension was added triflic anhydride (6.42 mL, 38 mmol) dropwise. The mixture was cooled to 0 °C for 1 hour, then at room temperature for 24 h. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was added to crushed ice and quenched with saturated sodium bicarbonate solution, extracted using ethylacetate and dried over sodium sulphate. The solvent was removed and the solid obtained was triturated to afford the title compound. Yield: 0.500 g (9.36 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.67-7.70 (m, 3H, Ar), 7.86 (d, 1 H, J =9.0 Hz, Ar), 7.98 (s, 1 H, Ar), 8.06 (d, 1 H, J =9.0 Hz, Ar),8.93 (s, 1 H, Ar), 9.20 (s, 1 H, Ar); MS (ES+): m/e 280.1 (M+1 ).

Example 242:

5-(3-Bromoimidazo[1 ,2-a]pyridin-6-yl)-2-(trifluoromethyl) pyridine 1 -oxide

N-bromosuccinimide (0.331 g, 1 .862 mmol) was added to a stirred solution of the compound of example 241 (0.500 g, 1 .791 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 0.50 g (77 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.73-7.79 (m, 2H, Ar), 7.83 (s, 1 H, Ar), 7.93 (d, 1 H, J =9.0 Hz, Ar), 8.05 (d, 1 H, J =9.0 Hz, Ar),8.78 (s, 1 H, Ar), 9.04 (s, 1 H, Ar); MS (ES+): m/e 359.1 (M+1 ). Example 243:

5-(3-(4-(lsopropylthio)phenyl)imidazo[1 ,2-a]pyridin-6-yl)-2-(trifluoromethyl) pyridine-1 -oxide

The compound of example 242 (0.450 g, 1 .257 mmol) was treated with 4- (isopropylthio)phenylboronic acid (0.296 g, 1 .508 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.017 g, 0.025 mmol) and sodium carbonate (0.261 g, 1 .885 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.325 g (60 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1 .30 (d, 6H, J =6.6 Hz, 2CH ₃ ), 3.59-3.63 (m, 1 H, CH), 7.53 (d, 2H, J=9.0 Hz, Ar), 7.69 (dd, 1 H, J =3.0 Hz, J =9.6 Hz, Ar), 7.74-7.80 (m, 3H, Ar), 7.83 (s, 1 H, Ar), 7.87 (s, 1 H, Ar), 8.04 (d, 1 H, J =9.0 Hz, Ar), 8.92 (s, 1 H, Ar), 9.01 (s, 1 H, Ar); MS (ES+): m/e 430.4 (M+1 ).

Example 244A:

5-(3-(4-(lsopropylsulfinyl)phenyl)imidazo[1 ,2-a]pyridin-6-yl)-2-(trifluoromethyl) pyridine-1 -oxide

Metachloroperbenzoic acid (0.171 g, 0.990 mmol) was added to a stirred solution of the compound of example 243 (0.250 g, 0.582 mmol) in dichloromethane (10 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.55 g (20.9 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.10 (d, 3H, J=6.0 Hz, CH ₃ ), 1 .24 (d, 3H, J =6.0 Hz, CH ₃ ), 3.01 -3.06 (m, 1 H, CH), 7.70-7.79 (m, 3H, Ar), 7.83 (s, 1 H, Ar), 7.86-7.90 (m, 1 H, Ar), 7.98-8.06 (m, 4H, Ar), 9.02 (d, 2H, J =12.0 Hz, Ar); MS (ES+): m/e 446.1 (M+1 ). Example 244B:

5-(3-(4-(lsopropylsulfonyl)phenyl)imidazo[1 ,2-a]pyridin-6-yl)-2-(trifluoromethyl) pyridine-1 -oxide

Metachloroperbenzoic acid (0.171 g, 0.990 mmol) was added to a stirred solution of the compound of example 243 (0.250 g, 0.582 mmol) in dichloromethane (10 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.65 g (23.83 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1.22 (d, 6H, J =6.0 Hz, 2CH ₃ ), 3.46-3.55 (m, 1H, CH), 7.76 (dd, 1H, J =3.0 Hz, J =9.6 Hz, Ar), 7.85-7.92 (m, 2H, Ar), 7.98 (d, 2H, J =9.0 Hz, Ar), 8.05 (d, 2H, J =9.0 Hz, Ar), 8.12 (d, 2H, J =9.0 Hz, Ar), 9.06 (d, 2H, J =9.0 Hz, Ar); MS (ES+): m/e 462.1 (M+1).

Example 245:

6-Bromo-8-chloroimidazo[1,2-a]pyridine

To a stirred solution of 5-bromo-3-chloropyridin-2-amine (20 g, 96 mmol) and sodium acetate (0.681 g, 8.30 mmol) in 100 mL of 60 % ethanol in water were added choloroacetaldehyde dimethylacetal (33.1 mL, 289 mmol) in concentrated hydrochloric acid (14.65 mL, 482 mmol) (1:6- HCI/water) according to the procedure for the preparation of the compound of example 1 to afford the title compound. Yield: 20.3 g (71.3 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 7.66 (d, 1H, J =0.9 Hz, Ar), 7.67 (d, 1H, J =1.5 Hz, Ar), 8.02 (d, 1H, J =0.9 Hz, Ar), 8.92 (d, 1H, J =1.5 Hz, Ar); MS (ES+): m/e 232 (M+1).

Example 246:

8-Chloro-6-(6-methylpyridin-3-yl)imidazo[1,2-a]pyridine

The compound of example 245 (3 g, 12.96 mmol) was treated with 6-methylpyridin-3- ylboronic acid (2.130 g, 15.55 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.182 g, 0.259 mmol) and sodium carbonate (2.69 g, 19.44 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.1 g (61.7 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.51 (s, 3H, CH ₃ ), 7.37 (d, 1H, J =9.0 Hz, Ar), 7.67 (s, 1H, Ar), 7.86 (d, 1H, J =1.2 Hz, Ar), 8.04 (dd, J =3.0 Hz, J =8.1 Hz, 1H, Ar), 8.07 (d, 1H, J =0.9 Hz, Ar), 8.81 (d, 1H, J =2.4 Hz, Ar), 9.01 (d, 1 H, J =1.5 Hz, Ar); MS (ES+): m/e 244.6 (M+1 ). Example 247:

3-Bromo-8-chloro-6-(6-methylpyridin-3-yl)imidazo[1,2-a] pyridine

N-bromosuccinimide (1.899g, 10.67mmol) was added to a stirred solution of the compound of example 246 (2 g, 8.21 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 2.3 g (87 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.53 (s, 3H, CH ₃ ), 7.38 (d, 1H, J =8.1 Hz, Ar), 7.85 (s, 1H, Ar), 7.98 (s, 1H, Ar), 8.13 (dd, 1H, J =2.4 Hz, J =8.1 Hz, Ar), 8.54 (s, 1H, Ar), 8.87 (d, 1H, J =2.1 Hz, Ar); MS (ES+): m/e 323.9 (M+1). Example 248:

4-(4-(8-Chloro-6-(6-methylpyridin-3-yl)imidazo[1,2-a]pyridin -3-yl)phenyl)

morpholine

The compound of example 247 (0.200 g, 0.620 mmol) was treated with (4- morpholinophenyl)boronic acid (0.160 g, 0.775 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.015 g, 0.019 mmol) and sodium carbonate (0.131 g, 1.240 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.012 g (4.54 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.50 (d, 3H, J =3.0 Hz, CH ₃ ), 3.21 (d, 4H, J =6.0 Hz, 2CH ₂ ), 3.75 (d, 4H, J =6.0 Hz, 2CH ₂ ), 7.12 (d, 2H, J =9.0 Hz, Ar), 7.35 (d, 1H, J =9.9 Hz, Ar), 7.61 (d, 2H, J =8.7 Hz, Ar), 7.75 (s, 1H, Ar), 7.87 (s, 1H, Ar), 8.04 (d, 1H, J =8.1 Hz, Ar), 8.57 (s, 1H, Ar), 8.80 (d, 1H, J=1.2 Hz, Ar) ; MS (ES+): m/e 405.2 (M+1).

Example 249:

3-(4-(lsopropylthio)phenyl)-6-(6-methylpyridin-3-yl)-8-(t rifluoromethyl) imidazo

[1,2-a]pyridine

(4-(lsopropylthio)phenyl)boronic acid (0.304 g, 1.550 mmol) was treated with the compound of example 247 (0.500 g, 1.550 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (38.0 g, 0.046 mmol) and sodium carbonate (0.329 g, 3.10 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.520 g (82 %); ¹ H NMR (DMSO-de, 300 MHz): δ 1.30 (d, 6H, J =6.0 Hz, 2CH ₃ ), 3.90 (s, 3H, CH ₃ ), 3.60-3.64 (m, 1H, CH), 7.36 (d, 1H, J =9.0 Hz, Ar), 7.52 (d, 2H, J =9.0 Hz, Ar), 7.74 (d, 2H, J =9.0 Hz, Ar), 7.89 (s, 1H, Ar), 7.92 (d, 1H, J =1.8 Hz, Ar), 8.07 (dd, 1H, J =2.4 Hz, J =8.1 Hz, Ar), 8.67 (d, 1 H, J =1.2 Hz, Ar), 8.83 (d, 1 H, J =2.1 Hz, Ar); MS (ES+): m/e 394.8 (M+1 ).

Example 250A:

8-Chloro-3-(4-(isopropylsulfinyl)phenyl)-6-(6-methylpyridin- 3-yl)imidazo[1,2-a] pyridine Metachloroperbenzoic acid (0.274 g, 1 .587 mmol) was added to a stirred solution of the compound of example 249 (0.250 g, 0.635 mmol) in dichloromethane (10 ml_), according to the procedure for the preparation of the compound of example 5 to afford the title compound.Yield: 0.45 g (16.47 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 0.99 (d, 3H, J =6.0 Hz, CH ₃ ), 1 .24 (d, 3H, J =6.0 Hz, CH ₃ ), 2.50 (s, 3H, CH ₃ ), 3.01 -3.08 (m, 1 H,CH), 7.37 (d, 1 H, J =9.0 Hz, Ar), 7.78 (d, 2H, J =9.0 Hz, Ar), 7.95-8.01 (m, 4H, Ar), 8.08 (dd, 1 H, J =3.0 Hz, J =8.1 Hz, Ar), 8.76 (s, 1 H, Ar), 8.85 (d, 1 H, J =3.0 Hz, Ar); MS (ES+): m/e 410.1 (M+1 ).

Example 250B:

8-Chloro-3-(4-(isopropylsulfonyl)phenyl)-6-(6-methylpyridin- 3-yl)imidazo [1 ,2-a] pyridine

Metachloroperbenzoic acid (0.274 g, 1 .587 mmol) was added to a stirred solution of the compound of example 249 (0.250 g, 0.635 mmol) in dichloromethane (10 ml_), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.52 g (18.8 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .21 (d, 6H, J =6.0 Hz, 2CH ₃ ), 2.50 (s, 3H, CH ₃ ), 3.49-3.51 (m,1 H,CH), 7.37 (d, 1 H, J =9.0 Hz, Ar), 7.99 (m, 3H, Ar), 8.06-8.10 (m, 4H, Ar), 8.86 (dd, 2H, J =1 .8 Hz, J =7.2 Hz, Ar); MS (ES+): m/e 426.9 (M+1 ).

Example 251 :

4-(5-(8-Chloro-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl) morpholine

Compound of example 247 (0.200 g, 0.620 mmol) was treated with 6-morpholinopyridin- 3-ylboronic acid (0.155 g, 0.744 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloro methane (0.087 g, 0.012 mmol) and sodium carbonate (0.129 g, 0.930 mmol) in dry dimethylformamide (10 ml_) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.95 g (35.6 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.50-2.51 (d, 3H, J =3.0 Hz, CH ₃ ), 3.55 (t, 4H, 2CH ₂ ), 3.73 (t, 4H, 2CH ₂ ), 7.02 (d, 1 H, J =9.0 Hz, Ar), 7.35 (d, 1 H, J =9.0 Hz, Ar), 7.78 (s, 1 H, Ar), 7.89 (d, 1 H, J =1 .2 Hz, Ar), 7.95 (dd, 1 H, J =3.0 Hz, J =9.0 Hz, Ar), 8.06 (dd, 1 H, J =3.0 Hz, J =8.1 Hz, Ar), 8.46 (d, 1 H, J =39.0 Hz, Ar), 8.55 (d, 1 H, J =3.0 Hz, Ar), 8.82 (d, 1 H, J =3.0 Hz, Ar); MS (ES+): m/e 406.8 (M+1 ). Example 252:

8-Chloro-6-(2-methoxypyrimidin-5-yl)imidazo[1 ,2-a]pyridine

The compound of example 245 (3 g, 12.96 mmol) was treated with (2- methoxypyrimidin-5-yl)boronic acid (2.394 g, 15.55 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloro methane (0.182 g, 0.259 mmol) and sodium carbonate (2.69 g, 19.44 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.7 g (80 %); ¹ H NMR (DMSO-de, 300 MHz): δ 3.99 (s, 3H, OCH ₃ ), 7.69 (d, 1 H, J =0.9 Hz, Ar), 7.90 (d, 1 H, J =1 .5 Hz, Ar), 8.07 (d, 1 H, J =1 .2 Hz, Ar), 8.98 (s, 2H, Ar), 9.01 (d, 1 H, J =1 .5 Hz, Ar); MS (ES+): m/e 261 .1 (M+1 ).

Example 253:

3-Bromo-8-chloro-6-(2-methoxypyrimidin-5-yl)imidazo[1 ,2-a]pyridine

Dried N-bromosuccinimide (2.308 g, 12.97 mmol) was added to a stirred solution of the compound of example 252 (2.6 g, 9.97 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 3.2 g (94 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 3.99 (s, 3H, OCH ₃ ), 7.85 (s, 1 H, Ar), 8.00 (d, 1 H, J =1 .2 Hz, Ar), 8.65 (d, 1 H, J =1 .5 Hz, Ar), 9.03 (s, 2H, Ar); MS (ES+): m/e 340.1 (M+1 ).

Example 254:

4-(4-(8-Chloro-6-(2-methoxypyrimidin-5-yl)imidazo[1 ,2-a] pyridin-3-yl) phenyl) morpholine

The compound of example 253 (0.300 g, 0.883 mmol) was treated with (4- morpholinophenyl)boronic acid (0.229 g, 1 .104 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloro methane (0.021 g, 0.027 mmol) and sodium carbonate (0.187 g, 1 .767 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.153 g (40.9 %); ¹ H NMR (DMSO-de, 300 MHz): δ 3.21 (t, 4H, 2CH ₂ ), 3.77 (t, 4H, 2CH ₂ ), 3.96 (s, 3H, OCH ₃ ), 7.1 1 (d, 2H, J =9.0 Hz, Ar), 7.62 (d, 2H, J =9.0 Hz, Ar), 7.77 (s, 1 H, Ar), 7.89 (d, 1 H, J =1 .5 Hz, Ar), 8.67 (d, 1 H, J =1 .5 Hz, Ar), 8.98 (s, 2H, Ar) ; MS (ES+): m/e 422.8 (M+1 ). Example 255:

8-Chloro-3-(4-(isopropylthio)phenyl)-6-(2-methoxypyrimidin-5 -yl)imidazo[1 ,2-a] pyridine

The compound of example 253 (0.400 g, 1 .1 78 mmol) was treated with 4- (isopropylthio)phenylboronic acid (0.289 g, 1 .472 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.028 g, 0.035 mmol) and sodium carbonate (250 mg, 2.356 mmol) in dry dimethylformamide (1 0 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.27 g (54.7 %) ; ¹ H NMR (DMSO-de, 300 MHz) : δ 1 .30 (d, 6H, J =6.0 Hz, 2xCH ₃ ), 3.55-3.66 (m, 1 H, CH), 3.97 (s, 3H, OCHs), 7.52 (d, 2H, J =9.0 Hz, Ar), 7.74 (d, 2H, J =9.0 Hz, Ar), 7.90 (s, 1 H, Ar), 7.94 (d, 1 H, J =1 .5 Hz, Ar), 8.78 (d, 1 H, J =3.0 Hz, Ar), 9.00 (s, 2H, Ar) ; MS (ES+) : m/e 41 1 .9 (M+1 ).

Example 256:

8-Chloro-3-(4-(isopropylsulfonyl)phenyl)-6-(2-methoxy pyrimidin-5-yl) imidazo

[1 ,2-a]pyridine

Metachloroperbenzoic acid (0.21 0 g, 1 .21 7 mmol) was added to a stirred solution of the compound of example 255 (0.200 g, 0.487 mmol) in dichloromethane (1 0 mL), according to the procedure for the preparation of the compound of example 5 to afford the title compound. Yield: 0.45 g (20.6 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .21 (d, 6H, J =6.0 Hz, 2CH ₃ ), 3.46-3.55 (m, 1 H, CH), 3.97 (s, 3H, OCH ₃ ), 7.98 (s, 1 H, Ar), 8.01 (s, 1 H, Ar), 8.03 (d, 1 H, J =1 .2 Hz, Ar), 8.08-8.1 1 (m, 3H, Ar), 8.93 (d, 1 H, J =1 .5 Hz, Ar), 9.04 (s, 2H, Ar); MS (ES+) : m/e 443.9 (M+1 ).

Example 257:

t-Butyl 4-(5-(8-chloro-6-(2-methoxypyrimidin-5-yl)imidazo [1 ,2-a]pyridin-3-yl) pyridin-2-yl)piperazine-1-carboxylate

The compound of example 253 (0.300 g, 0.883 mmol) was treated with t-butyl 4-(5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (0.41 3 g, 1 .060 mmol) in the presence of [1 , 1 '-bis(diphenyl phosphino)- ferrocene]dichloropalladium(l l) complex with dichloromethane (0.036 g, 0.044 mmol) and sodium carbonate (0.1 83 g, 1 .325 mmol) in dry dimethylformamide (1 0 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.160 g (34.2 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .43 (d, 9H, 3xCH3), 3.46 (d, 4H, J =6.0 Hz, 2xCH ₂ ), 3.61 (d, 4H, J =6.0 Hz, 2xCH ₂ ), 3.96 (s, 3H, OCHs), 7.00 (d, 1 H, J =9.0 Hz, Ar), 7.79 (s, 1 H, Ar), 7.90 (d, 1 H, J =1 .2 Hz, Ar), 7.93 (dd, 1 H, J =3.0 Hz, J =9.0 Hz, Ar), 8.46 (d, 1 H, J =3.0Hz, Ar), 8.66 (d, 1 H, J =1 .2 Hz, Ar), 8.99 (s, 2H, Ar); MS (ES+): m/e 523.2 (M+1 ).

Example 258:

8-Chloro-6-(2-methoxypyrimidin-5-yl)-3-(6-(piperazin-1-yl)py ridin-3-yl) imidazo

[1 ,2-a]pyridine

Dioxane-HCI (1 .2 mL, excess) was added to a stirred solution of the compound of example 257 (0.100 g, 0.192 mmol) in dichloromethane (5 mL) according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 0.045 g (55.4 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.80 (t, 4H, J =1 .8 Hz, 2CH ₂ ), 3.51 (t, 4H, J =1 .8 Hz, 2CH ₂ ), 3.96 (s, 3H, OCH ₃ ), 6.97 (d, 1 H, J =9.0 Hz, Ar), 7.78 (s, 1 H, Ar), 7.87 (d, 1 H, J =3.0 Hz, Ar), 7.90 (d, 1 H, J =0.9 Hz, Ar), 8.43 (d, 1 H, J =2.1 Hz , Ar), 8.67 (d, 1 H, J =1 .5 Hz, Ar), 8.99 (s, 2H, Ar); MS (ES+): m/e 423.2 (M+1 ). Example 259:

8-Chloro-6-(2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridine

The compound of example 245 (4 g, 17.28 mmol) was treated with 2-methyl-5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidine (5.70 g, 25.9 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.282 g, 0.346 mmol) and sodium carbonate (2.75 g, 25.9 mmol)in dry dimethylformamide (25 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 2.05 g (48.5 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.68 (s, 3H, CH ₃ ), 7.69 (s, 1 H, Ar), 7.93 (s, 1 H, Ar), 8.09 (s, 1 H, Ar), 9.06 (s, 3H, Ar); MS (ES+): m/e 245.1 (M+1 ).

Example 260:

3-Bromo-8-chloro-6-(2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridine

N-bromosuccinimide (1 .513 g, 8.50 mmol)was added to a stirred solution of the compound of example 259 (2 g, 8.17 mmol) in dry CHCI ₃ (50 mL) at 10 °C according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 2.33 g (88 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.29 (s, 3H, CH ₃ ), 7.87 (s, 1 H, Ar), 8.06 (s, 1 H, Ar), 8.71 (s, 1 H, Ar), 9.14 (s, 2H, Ar); MS (ES+): m/e 325 (M+1 ).

Example 261 :

4-(4-(8-Chloro-6-(2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridin-3-yl)phenyl) morpholine

The compound of example 260 (0.500 g, 1 .545 mmol) was treated with 4- morpholinophenylboronic acid (0.384 g, 1 .854 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (25.2 mg, 0.031 mmol) and sodium carbonate (246 mg, 2.318 mmol) in dry dimethylformamide (15 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.342 g (52.2 %); ¹ H NMR (DMSO-de, 300 MHz): δ 2.67 (s, 3H, CH ₃ ), 3.21 (t, 4H, J =3.0 Hz, 2CH ₂ ), 3.77 (t, 4H, J =3.0 Hz, 2CH ₂ ), 7.12 (d, 2H, J =6.0 Hz, Ar), 7.62 (d, 2H, J =6.0 Hz, Ar), 7.78 (s, 1 H, Ar), 7.94(s, 1 H, Ar), 8.72 (s, 1 H, Ar), 9.08 (s, 2H, Ar); MS (ES+): m/e 406.3 (M+1 ).

Example 262:

7-Methyl-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 146 (8 g, 37.9 mmol) was treated with 6-methylpyridin-3- ylboronic acid (5.71 g, 41 .7 mmol) in the presence of [1 ,1 '-Bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.495 g, 0.606 mmol) and sodium carbonate (6.03 g, 56.9 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 8.0 g (95 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.2 (s, 3H, CH ₃ ), 2.54 (s, 3H, CH ₃ ), 7.35-7.37 (d, 1 H, J=8.1 Hz, Ar), 7.50-7.53 (d, 1 H, J=8.7 Hz Ar), 7.53 (s, 1 H, Ar), 7.76-7.80 (dd, 1 H, J=2.4 Hz & J=5.7 Hz, Ar Ar), 7.8 (s, 1 H, Ar), 8.4 (s, 1 H, Ar), 8.49-8.50 (d, 1 H, J=1 .8 Hz, Ar); MS (ES+): m/e 224.1 (M+1 ).

Example 263:

3-Bromo-7-methyl-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 262 (3.0 g, 13.44 mmol) was treated with N- bromosuccinimide (2.48 g, 13.97 mmol) in chloroform according to the procedure for the preparation of the compound of example 3 to afford the title compound. Yield: 2.0 g (49.3 %); NMR (DMSO-d ₆ , 300 MHz): δ 2.29 (s, 3H, CH ₃ ), 2.66 (s, 3H, CH ₃ ), 7.28-7.30 (d, 1 H, J=7.5 Hz, Ar), 7.52 (s, 1 H, Ar), 7.56 (s, 1 H, Ar), 7.60-7.63 (d,d 1 H, J=2.1 & J=7.5 Hz, Ar), 7.95 (s, 1 H, Ar), 8.52-8.53 (d, 1 H, J=2.1 Hz, Ar); MS (ES+): m/e 302 (M+).

Example 264:

3-(2-Methoxypyridin-3-yl)-7-methyl-6-(6-methylpyridin-3-yl) imidazo[1 ,2-a] pyridine.

The compound of example 263 (0.300 g, 0.993 mmol) was treated with (2- methoxypyridin-3-yl)boronic acid (0.167 g, 1 .092 mmol) in the presence of dichlorobis(triphenylphosphine) palladium(ll) (0.012 g, 0.016 mmol) and potassium carbonate (0.206 g, 1 .489 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield : 0.1 10 g (33.1 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.26 (s, 3H, CH ₃ ), 2.5 (s, 3H, CH ₃ ), 3.9 (s, 3H, OCH ₃ ), 7.1 1 -7.15 (dd, 1 H, J=5.1 Hz & J=7.2 Hz, Ar), 7.32-7.35 (d, 1 H, J=7.8 Hz, Ar), 7.61 (s, 1 H, Ar), 7.68 (s, 1 H, Ar), 7.75-7.78 (dd, 1 H, J=1 .5 Hz & J=7.8 Hz, Ar), 7.89-7.90 (m, 2H, Ar), 8.2 (d, 1 H, J=3.3 Hz, Ar), 8.4 (d, 1 H, J=1 .5 Hz, Ar); MS (ES+): m/e 331 .2 (M+1 ).

Example 265:

3-(6-Methoxypyridin-3-yl)-7-methyl-6-(6-methylpyridin-3-y l)imidazo[1 ,2-a] pyridine

The compound of example 263 (0.300 g, 0.993 mmol) was treated with (6- methoxypyridin-3-yl)boronic acid (0.167 g, 1 .092 mmol) in the presence of dichlorobis(triphenylphosphine) palladium(ll) (0.012 g, 0.016 mmol) and potassium carbonate (0.206 g, 1 .489 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield : 0.050 g (15.05 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.25 (s, 3H, CH ₃ ), 2.52 (s, 3H, CH ₃ ), 3.89 (s, 3H, OCH ₃ ), 6.97-6.97 (d, 1 H, J=8.7 Hz, Ar), 7.32-7.35 (d, 1 H, J=8.1 Hz, Ar), 7.61 (s, 1 H, Ar), 7.72 (s, 1 H, Ar), 7.79-7.81 (dd, 1 H, J=2.4 Hz & J=5.7 Hz Ar), 8.02-8.05 (dd, 1 H, J=2.4 Hz & J=6.0 Hz, Ar), 8.21 (s, 1 H, Ar), 8.47-8.52 (d, 2H, J=16.8 Hz, Ar); MS (ES+): m/e 331 .2 (M+1 ).

Example 266:

3-(2-Methoxypyrimidin-5-yl)-7-methyl-6-(6-methylpyridin-3-yl )imidazo[1 ,2-a] pyridine The compound of example 263 (0.330 g, 1 .092 mmol) was treated with (2- methoxypyrimidin-5-yl)boronic acid (0.1 68 g, 1 .092 mmol) in the presence of dichlorobis(triphenylphosphine) palladium(ll) (0.01 2 g, 0.01 7 mmol) and potassium carbonate (0.226 g, 1 .638 mmol) in DMF according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.1 82 g (50.3 %) ; ¹ H NMR (DMSO-de, 300 MHz): δ 2.27 (s, 3H, CH ₃ ), 2.50 (s, 3H, CH ₃ ), 3.97 (s, 3H, OCH ₃ ), 7.33-7.35 (d, 1 H, J=7.8 Hz, Ar), 7.62 (s, 1 H, Ar), 7.79-7.81 (m, 2H, Ar), 8.34 (s, 1 H, Ar), 8.54 (d, 1 H, J=1 .5 Hz, Ar), 8.92 (s, 2H, Ar); MS (ES+): m/e 332.2 (M+1 ).

Example 267:

t-Butyl 4-(5-(6-(pyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl)piperazine-1 - carboxylate

The compound of example 3 (1 .0 g, 3.65 mmol) was treated with t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3, 2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (1 .56 g, 4.01 mmol) in the presence of [1 , 1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.089 g, 0.109 mmol) and sodiumcarbonate (0.773 g, 7.30 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.31 0 g (1 8.61 %); ¹ H NMR (DMSO-de, 300 MHz) : δ 1 .43 (s, 9H, 3CH ₃ ), 3.44 (s, 4H, 2CH ₂ ), 3.59 (s, 4H, 2CH ₂ ), 7.01 (d, 1 H, J=8.7 Hz, Ar), 7.47-7.51 (m, 1 H, Ar), 7.62-7.78 (m, 3H, Ar), 7.96 (d, 1 H, J=7.2 Hz, Ar), 8.14 (d, 1 H, J=7.8 Hz, Ar), 8.45 (s, 1 H, Ar), 8.58-8.60 (m, 2H, Ar),

8.94 (s, 1 H, Ar); MS (ES+) : m/e 457 (M+1 ). Example 268:

3-(6-(piperazin-1 -yl)pyridin-3-yl)-6-(pyridin-3-yl)imidazo[1 ,2-a]pyridine

The compound of example 3 (0.250 g, 0.548 mmol) was treated with dioxane- hydrochloride (1 .0 mL) in dry 1 ,4-dioxane (2 mL) according to the procedure for the preparation of the compound of example 1 0 to afford the title compound. Yield: 0.2 g (85.0 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .98 (s, 1 H, NH), 2.81 (s, 4H, 2CH ₂ ), 3.51 (s, 4H, 2CH ₂ ), 6.96 (d, 1 H, J=8.7 Hz, Ar), 7.47-7.51 (m, 1 H, Ar), 7.62-7.92 (m, 3H, Ar), 7.91 (d, 1 H, J=7.5 Hz, Ar), 8.14 (d, 1 H, J=7.8 Hz, Ar), 8.43 (s, 1 H, Ar), 8.58-8.60 (m, 2H, Ar),

8.95 (s, 1 H, Ar); MS (ES+) : m/e 357 (M+1 ). Example 269:

3-(3-(6-(4-(t-Butoxycarbonyl)piperazin-1 -yl)pyri^

pyridine 1 -oxide

The compound of example 1 2 (0.250 g, 0.862 mmol) was treated with t-butyl 4-(5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (0.369 g, 0.948 mmol) in the presence of [1 , 1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(l l) complex (0.021 g, 0.026 mmol) and sodium carbonate (0.1 83 g, 1 .73 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.31 0 g (76 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .43 (s, 9H, 3CH ₃ ), 3.45 (s, 4H, 2CH ₂ ), 3.60 (s, 4H, 2CH ₂ ), 7.02 (d, 1 H, J=9.0 Hz, Ar), 7.47-7.52 (m, 1 H, Ar), 7.61 -7.77 (m, 4H, Ar), 7.95 (d, 1 H, J=6.9 Hz, Ar), 8.22 (d, 1 H, J=6.3 Hz, Ar), 8.47 (s, 1 H, Ar), 8.68-8.73 (m, 2H, Ar) ; MS (ES+) : m/e 457 (M+1 ). Example 270:

3-(3-(6-(Piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)pyridine 1 -oxide

The compound of example 1 2 (0.250 g, 0.529 mmol) was treated with dioxane- hydrochloride (1 .0 ml_) in dry 1 ,4-dioxane (2 ml_) according to the procedure for the preparation of the compound of example 1 0 to afford the title compound. Yield: 0.2 g (92.0 %) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 1 .95 (s, 1 H, NH), 2.84 (s, 4H, 2CH ₂ ), 3.54 (s, 4H, 2CH ₂ ), 6.98 (d, 1 H, J=8.7 Hz, Ar), 7.47-7.52 (m, 1 H, Ar), 7.59-7.76 (m, 4H, Ar), 7.92 (d, 1 H, J=6.9 Hz, Ar), 8.22 (d, 1 H, J=6.0 Hz, Ar), 8.45 (s, 1 H, Ar), 8.67-8.73 (m, 2H, Ar) ; MS (ES+): m/e 373 (M+1 ). Example 271 :

t-Butyl 4-(5-(6-(6-methylpyridin-3-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl) piperazine-1 -carboxylate

The compound of example 19 (2.0g, 6.94 mmol) was treated with t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3, 2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (2.97 g, 7.64 mmol) in the presence of [1 , 1 '-Bis(diphenylphosphino)- ferrocene]dichloropalladium(l l)complex with dichloromethane (0.1 70 g, 0.208 mmol) and sodium carbonate (0.736 g, 6.94 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.620 g (1 9 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .43 (s, 9H, 3CH ₃ ), 2.51 (s, 3H, CH ₃ ), 3.44 (s, 4H, 2CH ₂ ), 3.59 (s, 4H, 2CH ₂ ), 7.01 (d, 1 H, J=9.0 Hz, Ar), 7.35 (d, 1 H, J=8.1 Hz, Ar) 7.60-7.76 (m, 3H, Ar), 7.95 (d, 1 H, J=7.2 Hz, Ar), 8.02 (d, 1 H, J=6.0 Hz, Ar), 8.45 (s, 1 H, Ar), 8.56 (s, 1 H, Ar), 8.79 (s, 1 H, Ar); MS (ES+): m/e 471 (M+1 ).

Example 272:

6-(6-Methylpyridin-3-yl)-3-(6-(piperazin-1-yl)pyridin-3-yl)i midazo[1 ,2-a]pyri^

The compound of example 19 (0.250 g, 0.531 mmol) was treated with dioxane- hydrochloride (1 .0 ml_) in dry 1 ,4-dioxane (2 ml_) according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 0.2 g (93.0%); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 2.51 (s, 3H, CH ₃ ), 2.80 (s, 4H, 2CH ₂ ), 3.50 (s, 4H, 2CH ₂ ), 6.95 (d, 1 H, J=9.0 Hz, Ar), 7.34 (d, 1 H, J=8.1 Hz, Ar) 7..59-7.62 (m, 1 H, Ar), 7.71 -7.76 (m, 2H, Ar), 7.90 (d, 1 H, J=9.0 Hz, Ar), 8.02 (d, 1 H, J=8.1 Hz, Ar), 8.42 (m, 1 H, J=2.4 Hz, Ar), 8.55 (s, 1 H, Ar), 8.80 (m, 1 H, J=2.1 Hz, Ar); MS (ES+): m/e 371 (M+1 ).

Example 273:

5-(3-(6-(4-(t-Butoxycarbonyl)piperazin-1-yl)pyridin-3-yl)imi dazo[1 ,2-a]pyridin-6-yl)- 2-methylpyridine 1 -oxide

The compound of example 19 (0.250 gm, 0.822 mmol) was treated with t-butyl 4-(5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (0.352 g, 0.904 mmol) in the presence of [1 ,1 '-Bis(diphenylphosphino)- ferrocene]dichloropalladium(ll)complex with dichloromethane (0.020 g, 0.025 mmol) and sodium carbonate (0.174 g, 1 .64 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.310 g (78 %); ¹ H NMR (DMSO-d ₆ , 300 MHz): δ 1 .43 (s, 9H, 3CH ₃ ), 2.39 (s, 3H, CH ₃ ), 3.45 (s, 4H, 2CH ₂ ), 3.59 (s, 4H, 2CH ₂ ), 7.02 (d, 1 H, J=9.0 Hz, Ar), 7.54-7.76 (m, 5H, Ar), 7.95 (d, 1 H, J=8.7 Hz, Ar), 8.47 (s, 1 H, Ar), 8.64 (s, 1 H, Ar), 8.78 (s, 1 H, Ar); MS (ES+): m/e 487 (M+1 ).

Example 274:

2-Methyl-5-(3-(6-(piperazin-1 -yl)pyridin-3-yl)imidazo[1 ,2-a]pyridin-6-yl)pyridine 1 - oxide

The compound of example 19 (0.250 g, 0.514 mmol) was treated with dioxane- hydrochloride (1 .0 ml_) in dry 1 ,4-dioxane (2 ml_) according to the procedure for the preparation of the compound of example 10 to afford the title compound. Yield: 0.1 50 g (69.0%) ; ¹ H NMR (DMSO-d ₆ , 300 MHz) : δ 2.38 (s, 3H, CH ₃ ), 2.81 (s, 4H, 2CH ₂ ), 3.51 (s, 4H, 2CH ₂ ), 6.96 (d, 1 H, J=8.7 Hz, Ar), 7..54-7.75 (m, 5H, Ar), 7.91 (d, 1 H, J=8.7 Hz, Ar), 8.44 (s, 1 H, Ar), 8.64 (s, 1 H, Ar), 8.77 (s, 1 H, Ar) ; MS (ES+) : m/e 387 (M+1 ).

Example 275:

t-Butyl 4-(5-(8-chloro-6-(2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridin-3-yl) pyridin- 2-yl)piperazine-1 -carboxylate

The compound of example 260 (0.5 g, 1 .545 mmol) was treated with t-butyl 4-(5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1 -carboxylate (0.722 g, 1 .854 mmol) in the presence of [1 , 1 '-Bis(diphenylphosphino)- ferrocene]dichloropalladium(l l) complex with dichloromethane (0.025 g, 0.031 mmol) and sodium carbonate (0.246 g, 2.318 mmol) in dry dimethylformamide (1 0ml) according to the preparation of compound of example 1 to give t-butyl 4-(5-(8-chloro-6- (2-methylpyrimidin-5-yl)imidazo[1 ,2-a]pyridin-3-yl)pyridin-2-yl)piperazine-1 -carboxylate. Yield: 0.351 g(42.7%) ; 1 H NMR (DMSO-d6, 300 MHz): δ 1 .43 (s, 9H, 3xCH3), 2.67(s, 3H, CH3), 3.45 (t, 4H, J =3.0 Hz, 2CH ₂ ), 3.61 (t, 4H, J =3.0 Hz, 2CH ₂ ), 7.02 (d, 2H, J =6.0 Hz, Ar), 7.81 (s, 2H, Ar), 8.47(s, 1 H, Ar), 8.72 (s, 1 H, Ar), 9.08 (s, 2H, Ar) ; MS (ES+): m/e 507.3 (M+1 ).

Example 276:

8-Chloro-6-(2-methylpyrimidin-5-yl)-3-(6-(piperazin-1 -yl)pyridin-3-yl) imidazo [1 ,2- a]pyridine

Dioxane-HCI (1 .2 mL, excess) was added to a stirred solution of the compound of example 276 (0.1 75 g, 0.346 mmol) in dichloromethane (5 mL) according to the procedure for the preparation of the compound of example 1 0 to afford the title compound. Yield: 0.1 22 g (86 %);1 H NMR (DMSO-d6, 300 MHz) : δ 2.51 (s, 3H, CH3), 3.23 (t, 4H, J =3.0 Hz, 2CH ₂ ), 3.83 (t, 4H, J =3.0 Hz, 2CH ₂ ), 7.1 (d, 1 H, J =6.0 Hz, Ar), 7.83 (s, 1 H, Ar), 7.98 (s, 1 H, Ar), 8.02(d, 1 H, J =7.5 Hz, Ar), 8.52 (s, 1 H, Ar), 8.71 (s, 1 H, Ar), 8.92 (s, 1 H, NH-Ar), 9.08 (s, 2H, Ar); MS (ES+) : m/e 407 (M+1 ). BIOLOGICAL EVALUATION OF THE COMPOUNDS

Example 277:

LPS-induced cytokine production by Peripheral blood mononuclear cells (PBMCs):

TNF-a production by LPS in peripheral blood mononuclear cells (PBMC) was measured according to the method described by Henry et al (J. Bioorg. Med. Chem. Lett., 8: 3335- 3340, 1998).

Blood was collected from healthy donors into Potassium EDTA vacutainer tubes (Vacutest Plast/Becton Dickinson). PBMC were isolated using gradient centrifugation in Ficoll-Paque solution (Pharmacia). Isolated PBMC were suspended in RPMI 1640 culture medium (Gibco BRL, Pasley, UK) containing 10 % fetal bovine serum (FBS) (Hyclone, Utah, USA), 100 U/mL penicillin (Sigma Chemical Co. St Louis, MO) and 100 g/mL streptomycin (Sigma Chemical Co. St Louis, MO). The cell concentration was adjusted to 1 x10 ⁶ cells/mL. The viability as determined by trypan blue dye exclusion was uniformly >98 %. The cell suspension (100 L) was added to the wells of a 96-well culture plate. Following cell plating, 79 L of the culture medium and 1 L of eight different concentrations of the test compounds (final concentration 0.03, 0.1 , 0.3, 1 ,3, 10, 30, 100 μΜ) dissolved in DMSO (dimethylsulfoxide, Sigma, MO, USA) were added to the cells. The final concentration of DMSO was adjusted to 0.5 %. The appropriate DMSO concentration was used as control. Rolipram (30 μΜ) was used as a standard compound. The plates were incubated for 30 min at 37 °C in an atmosphere of 5 % CO ₂ . Finally, 20 pL (10 pg/mL) per well of LPS, (Escherchia coli 0127:B8, Sigma Chemical Co., St. Louis, MO) was added, for a final concentration of 1 g/mL. The plates were incubated at 37 °C for 4.5 h in an atmosphere of 5 % CO ₂ . To determine the cytotoxicity of the test compounds, the cell viability was assessed using MTS (3-(4, 5- dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfon yl)-2H-tetrazolium) reagent (Promega) after 4.5 h of incubation. Supernatants were harvested and assayed for TNF-a by ELISA as described by the manufacturer (R&D Systems, MN, BD Biosciences Pharmingen) or by cytotoxicity bioassay in L929 cells. The 50 % inhibitory concentration (IC ₅ o) values were calculated by a nonlinear regression method using GraphPad software (Prism 3.03).

Results presented in table 1 below are representative (average value) of three separate experiments. The symbols used to indicate different IC ₅ o range class are depicted below.

Table 1 :

145 + 222 +

149 + 227 +

153 ++ 229 +

155 + 230 ++

158 + 235 +

159 + 236 +

165 ++ 248 +++

166 + 249 +

175 ++ 250A +++

176 + 250B ++

182 ++ 254 +++

183 +++ 256 ++

184 ++ 257 +++

185 ++ 258 +

186 ++ 264 ++

187 +++ 265 ++

188 +++ 268 +++

189 +++ 270 +++

191 ++ 272 +++

192B ++ 276 ++

198 +