IMIDAZOPYRIDINYL COMPOUNDS AND THEIR USE FOR THE TREATMENT OF NEURODEGENERATIVE DISORDERS - Patent application

Abstract

The present disclosure provides compounds of formula (I) or pharmaceutically acceptable salts thereof, stereoisomers thereof, pharmaceutical compositions containing the compounds, and methods for treating or preventing neurodegenerative diseases using the compounds. TIFF2022521536000070.tif49169

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of and priority to US Ser. No. 62 / 809,230, filed Feb. 22, 2019. The entire disclosures of the applications identified in this paragraph are incorporated herein by reference.

[0002] Field FIELD OF THE DISCLOSURE This disclosure relates generally to compounds with enzyme inhibitor activity, pharmaceutical compositions containing such compounds, and methods of using such compounds to treat disease.

[0003] background Alpha-synuclein is part of a large family of proteins that includes beta- and gamma-synuclein and synoretin. Alpha-synuclein is expressed in normal conditions associated with synapses and is thought to play a role in neuroplasticity, learning and memory. Several studies have shown that Alpha-synuclein plays a central role in the pathogenesis of Parkinson's disease. Molecular changes in Alpha-synuclein protein that increase protein misfolding and aggregation play a direct role in the pathogenesis of the disease. Aggregation of Alpha-synuclein contributes to the formation of Lewy bodies and neurites, which are pathological hallmarks of Parkinson's disease and Alpha-synucleinopathies. Activation of the tyrosine kinase c-abl contributes to Alpha-synuclein-induced neurodegeneration.

[0004] The tyrosine kinase c-abl is a tightly regulated non-receptor protein tyrosine kinase involved in a wide range of cellular processes including growth, survival and stress response (Nat Rev Mol Cell Biol, 2004, 5:33-44), and c-abl is involved in the regulation of several cellular processes and is involved in the development of the central nervous system by controlling neurogenesis. Furthermore, in recent years, increasing evidence from various experimental model systems has revealed that c-abl is activated in neurodegenerative diseases, such as Alzheimer's disease, Parkinson's disease, Niemann-Pick C disease and tauopathy (Human Molecular Genetics, 2014, Vol. 23, No.11).

[0005] The stress-signaling non-receptor tyrosine kinase c-abl has been linked to sporadic Parkinson's disease through tyrosine phosphorylation. Tyrosine phosphorylation of parkin by c-abl is the major post-translational modification that leads to loss of parkin function and disease progression in sporadic Parkinson's disease. Inhibition of c-abl provides a new therapeutic opportunity to halt Parkinson's disease progression (The Journal of Neuroscience, 2011, 31(1):157-163). Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by progressive death of motor neurons. Knockdown of c-abl by small interfering RNA (siRNA) also rescued ALS motor neuron degeneration (Imamura et al., Sci. Transl. Med. 9, 2017). Multiple system atrophy (MSA) is a rare, rapidly progressive neurodegenerative disease for which no treatment is currently available. In MSA, accumulation of α-synuclein is observed in neurons and oligodendrocytes in the substantia nigra, striatum, olivopontocerebellar structures, and spinal cord (J Neural Trans Vienna Austria 1996. 2016;123(6)).

[0006] Administration of the tyrosine kinase inhibitor nilotinib reduces c-abl activity and improves autophagic clearance of α-synuclein in transgenic and lentiviral transgenic models. Activation of c-abl in the mouse forebrain induces neurodegeneration in the hippocampus and striatum. Thus, phosphorylation-mediated increase in c-abl activity may be related to α-synuclein pathology detected in Parkinson's disease and other neurodegenerative diseases (Hum Mol Genet. 2013 Aug 15).

[0007] C-abl is a promising therapeutic target for α-synucleinopathy, Parkinson's disease, Alzheimer's disease, ALS, dementia with Lewy bodies and MSA.

[0008] Mutations in the leucine-rich repeat kinase 2 (LRRK2) gene are the most common cause of familial Parkinson's disease with autosomal dominant inheritance. LRRK2 played a key role in neuronal death by directly phosphorylating apoptosis signal-regulating kinase 1 at the Thr832 site and activating its kinase activity. LRRK2 G2019S mutation impairs dopamine receptor D1 internalization, resulting in altered signal transduction. Parkinson's disease-associated LRRK2 mutations upregulate the expression of the mitochondrial calcium uniporter, a mitochondrial calcium transporter, which in turn promotes dendritic and mitochondrial calcium uptake in cortical neurons and familial Parkinson's disease patient fibroblasts (Frontiers in aging Neuroscience, 2018 April (10)). Thus, LRRK2 has emerged as a promising therapeutic target for disease modification in Parkinson's disease.

[0009] overview The present disclosure provides compounds having c-abl and LRRK2 kinase inhibitory activity, compositions comprising such compounds and methods useful for treating neurodegenerative diseases.

[0010] In an embodiment, the compound of formula (I) [ka] [In the formula, R 1 , R 2 , R 3 , R 4 and R 5 is defined as follows: and pharma- ceutically acceptable salts thereof.

[0011] In another embodiment, the disclosure provides a pharmaceutical composition comprising a therapeutically effective amount of a compound described herein and a pharma- ceutically acceptable carrier.

[0012] In yet another embodiment, the disclosure provides a method of inhibiting or treating a neurodegenerative disease, comprising administering to a subject in need thereof a therapeutically effective amount of one or more compounds described herein.

[0013] Detailed Description The following description is merely exemplary in nature and is in no way intended to limit the disclosure, its application, or uses.

[0014] definition Common terms used in this disclosure are defined herein for the sake of clarity.

[0015] The terms "substituent," "radical," "group," "moiety," and "fragment" are used interchangeably herein.

[0016] As used herein, the term "alkenyl" refers to a straight or branched chain hydrocarbon group having at least one site of unsaturation, i.e., a carbon-carbon sp2 double bond. In embodiments, an alkenyl has 2 to 12 carbon atoms. In some embodiments, an alkenyl has C2 to C6 10alkenyl group or a C2-C6 alkenyl group. Examples of alkenyl groups include, but are not limited to, ethylene or vinyl (-CH=CH2), allyl (-CH2CH=CH2), cyclopentenyl (-C5H7), and 5-hexenyl (-CH2CH2CH2CH2CH=CH2).

[0017] As used herein, the term "alkoxy" refers to RO-, where R is alkyl. Non-limiting examples of alkoxy groups include methoxy, ethoxy and propoxy.

[0018] As used herein, the term "alkoxyalkyl" refers to an alkyl moiety substituted with an alkoxy group. Examples of alkoxyalkyl groups include methoxymethyl, methoxyethyl, methoxypropyl, and ethoxyethyl.

[0019] As used herein, the term "alkoxycarbonyl" refers to ROC(O)-, where R is an alkyl group as defined herein. In various embodiments, R is a C1-C 10 It is an alkyl group or a C1 to C6 alkyl group.

[0020] As used herein, the term "alkyl" refers to a straight or branched chain hydrocarbon group. In embodiments, an alkyl has 1 to 12 carbon atoms. In some embodiments, an alkyl has C1 to C6. 10 An alkyl group or a C1-C6 alkyl group. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl. "Lower alkyl" means an alkyl group having 1 to 4 carbon atoms.

[0021] As used herein, the term "alkylamino" refers to an amino group substituted with one or more alkyl groups. "N-(alkyl)amino" is RNH- and "N,N-(alkyl)2amino" is R2N-, where the R groups are alkyl as defined herein and may be the same or different. In various embodiments, R is a C1-C 10 It is an alkyl group or a C1 to C6 alkyl group. Examples of the alkylamino group include methylamino, ethylamino, propylamino, butylamino, dimethylamino, diethylamino and methylethylamino.

[0022] As used herein, the term "alkylaminoalkyl" refers to an alkyl moiety substituted with an alkylamino group, where alkylamino is as defined herein. Examples of alkylaminoalkyl groups include methylaminomethyl and ethylaminomethyl.

[0023] As used herein, the term "alkynyl" refers to a straight or branched carbon chain group having at least one site of unsaturation, i.e., a carbon-carbon sp triple bond. In embodiments, alkynyl has 2 to 12 carbon atoms. In some embodiments, alkynyl has C2 to C6. 10 An alkynyl group or a C2-C6 alkynyl group. Examples of alkynyl groups include acetylene (-C≡CH) and propargyl (-CH2C≡CH).

[0024] As used herein, the term "aryl" refers to any monocyclic or bicyclic carbocyclic ring of up to 7 atoms in each ring, where at least one ring is an aromatic ring system of 5 to 14 carbon atoms that is aromatic or contains a carbocyclic aromatic group fused to a 5- or 6-membered cycloalkyl group. Representative examples of aryl groups include, but are not limited to, phenyl, tolyl, xylyl, naphthyl, tetrahydronaphthyl, anthracenyl, fluorenyl, indenyl, azulenyl, and indanyl. Carbocyclic aromatic groups can be unsubstituted or optionally substituted.

[0025] As used herein, the term "cycloalkyl" refers to Contains one saturated ring structure , a hydrocarbyl group attached via a ring carbon. In various embodiments, cycloalkyl is saturation C3~C 12 It refers to a ring moiety. Examples are cyclopropyl, cyclobutyl, cyclopentyl 、 Cyclohexyl 、 "Cycloalkyloxy" refers to RO--, where R is cycloalkyl.

[0026] As used herein, the terms "halogen" and "halo" refer to chloro (-Cl), bromo (-Br), fluoro (-F) or iodo (-I). "Haloalkoxy" refers to an alkoxy group substituted with one or more halo groups. Examples of haloalkoxy groups include, but are not limited to, -OCF3, -OCHF2 and -OCH2F. "Haloalkoxyalkyl" refers to an alkyl moiety substituted with a haloalkoxy group, where haloalkoxy is as defined herein. Examples of haloalkoxyalkyl groups include trifluoromethoxymethyl, trifluoroethoxymethyl and trifluoromethoxyethyl. "Haloalkyl" refers to an alkyl moiety substituted with one or more halo groups. Examples of haloalkyl groups include -CF3 and -CHF2.

[0027] As used herein, the term "heteroalkyl" refers to a straight- or branched-chain alkyl group having 2 to 14 carbons (and in some embodiments 2 to 10 carbons) in the chain, where one or more of the carbons is replaced by a heteroatom selected from S, O, P, and N. Exemplary heteroalkyls include alkyl ethers, secondary and tertiary alkyl amines, amides, alkyl sulfides, and the like.

[0028] As used herein, the term "heterocyclyl" includes heteroaryl, as defined below, and refers to a saturated or partially unsaturated monocyclic, bicyclic, or tricyclic group of 2 to 14 ring carbon atoms and, in addition to the ring carbon atoms, 1 to 4 heteroatoms selected from P, N, O, and S. In various embodiments, a heterocyclic group is attached to another moiety through a carbon or heteroatom and is optionally substituted at a carbon or heteroatom. Examples of heterocyclyl include azetidinyl, benzimidazolyl, benzofuranyl, benzofurazanyl, benzopyrazolyl, benzotriazolyl, benzothiophenyl, benzoxazolyl, carbazolyl, carbolinyl, cinnolinyl, furanyl, imidazolyl, indolinyl, indolyl, indolazinyl, indazolyl, isobenzofuranyl, isoindolyl, isoquinolyl, isothiazolyl, isoxazolyl, naphthapyridinyl, Oxadiazolyl, oxazolyl, oxazoline, isoxazoline, oxetanyl, pyranyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridopyridinyl, pyridazinyl, pyridyl, pyrimidyl, pyrrolyl, quinazolinyl, quinolyl, quinoxalinyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydroisoquinolinyl, tetrazolyl, tetrazolopyridyl, thiadiazolyl, thiazolyl, thienyl, triazolyl , azetidinyl, 1,4-dioxanyl, hexahydroazepinyl, piperazinyl, piperidinyl, pyridin-2-onyl, pyrrolidinyl, morpholinyl, thiomorpholinyl, dihydrobenzimidazolyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydrobenzoxazolyl, dihydrofuranyl, dihydroimidazolyl, dihydroindolyl, dihydroisoxazolyl, dihydroisothiazolyl, dihydrooxadiazolyl, dihydrooxazolyl, dihydropyrazinyl, dihydropyrazolyl, dihydropyridinyl, dihydropyrimidinyl, dihydropyrrolyl, dihydroquinolinyl, dihydrotetrazolyl, dihydrothiadiazolyl, dihydrothiazolyl, dihydrothienyl, dihydrotriazolyl, dihydroazetidinyl, methylenedioxybenzoyl, tetrahydrofuranyl and tetrahydrothienyl and their N-oxides. "Heterocyclyloxy" is RO-, where R is heterocyclyl."Heterocyclylthio" is RS-, where R is heterocyclyl.

[0029] As used herein, the term "3- or 4-membered heterocyclyl" refers to a monocyclic ring having 3 or 4 ring atoms, where at least one ring atom is a heteroatom selected from the group consisting of N, O, and S. Non-limiting examples of 3- or 4-membered heterocyclyls include aziridinyl, 2H-azirinyl, oxiranyl, thiiranyl, azetidinyl, 2,3-dihydroazetyl, azetyl, 1,3-diazetidinyl, oxetanyl, 2H-oxetyl, thietanyl, and 2H-thiethyl.

[0030] As used herein, the term "heteroaryl" refers to a monocyclic, bicyclic, or tricyclic ring having up to seven atoms in each ring, where at least one ring is aromatic and contains from 1 to 4 heteroatoms in the ring selected from the group consisting of N, O, and S. Non-limiting examples of heteroaryl include pyridyl, thienyl, furanyl, pyrimidyl, imidazolyl, pyranyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrrolyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzothienyl, indolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, isoindolyl, benzotriazolyl, purinyl, thianaphthenyl, and pyrazinyl. The attachment of the heteroaryl may occur through an aromatic ring or through a non-aromatic ring or a ring that does not contain a heteroatom if the heteroaryl is bicyclic or tricyclic and one of the rings is not aromatic or does not contain a heteroatom. "Heteroaryl" is also understood to include the N-oxide derivative of any nitrogen-containing heteroaryl. "Heteroaryloxy" is RO-, where R is a heteroaryl.

[0031] As used herein, the term "hydroxyalkoxy" refers to an alkoxy group substituted with a hydroxyl group (-OH), where alkoxy is as defined herein. An example of a hydroxyalkoxy is hydroxyethoxy.

[0032] As used herein, the term "hydroxyalkyl" refers to a linear or branched, monovalent C1-C alkyl group substituted with at least one hydroxy group. 10 refers to a hydrocarbon group. Examples of hydroxyalkyl groups include, but are not limited to, hydroxymethyl, hydroxyethyl, hydroxypropyl, and hydroxybutyl.

[0033] As used herein, the term "pharmaceutical acceptable" means suitable for use in pharmaceutical preparations that are generally considered safe for such use, officially approved for such use by a national or state government regulatory agency, or listed in the United States Pharmacopeia or other generally recognized pharmacopoeias for use in animals, especially humans.

[0034] As used herein, the term "pharmaceutically acceptable carrier" refers to a diluent, adjuvant, excipient or carrier or other ingredient that is pharma-ceutically acceptable and with which a compound of the invention is administered.

[0035] As used herein, the term "pharmaceutical acceptable salt" refers to a salt that can enhance the desired pharmacological activity. Examples of pharmaceutical acceptable salts include acid addition salts formed with inorganic or organic acids, metal salts, and amine salts. Examples of acid addition salts formed with inorganic acids include salts with hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid. Examples of acid addition salts formed with organic acids include, for example, salts with acetic acid, propionic acid, hexanoic acid, heptanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, o-(4-hydroxy-benzoyl)-benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, p- Examples of salts include salts with chlorobenzenesulfonic acid, 2-naphthalenesulfonic acid, p-toluenesulfonic acid, camphorsulfonic acid, 4-methyl-bicyclo[2.2.2]oct-2-ene-1-carboxylic acid, glucoheptonic acid, 4,4'-methylenebis(3-hydroxy-2-naphthoic) acid, 3-phenylpropionic acid, trimethyl-acetic acid, tertiary butylacetic acid, lauryl sulfate, gluconic acid, glutamic acid, hydroxy-naphthoic acid, salicylic acid, stearic acid and muconic acid. Examples of metal salts include salts with sodium, potassium, calcium, magnesium, aluminum, iron and zinc ions. Examples of amine salts include salts with ammonia and organic nitrogen bases strong enough to form salts with carboxylic acids.

[0036] As used herein, the term "therapeutically effective amount" when applied to a compound of the present invention is intended to mean an amount of compound sufficient to ameliorate, alleviate, stabilize, reverse, slow or retard the progression of a disorder or disease state or symptoms of a disorder or disease. In an embodiment, the method of the present invention provides for the administration of a combination of compounds. In such a case, the "therapeutically effective amount" is the amount of a compound of the present invention in the combination sufficient to cause the intended biological effect.

[0037] As used herein, the term "treatment" or "treating" means improving or reversing the progression or severity of a disease or disorder or improving or reversing one or more symptoms or side effects of such a disease or disorder. As used herein, "treatment" or "treating" also means inhibiting or arresting the progression of the general condition or state of a disease or disorder, such as delaying, halting, inhibiting, hindering, or blocking. For purposes of the present invention, "treatment" or "treating" further refers to an approach to obtain beneficial or desired clinical results. In this case, "beneficial or desired clinical results" include, but are not limited to, alleviation of symptoms, reduction in the extent of the disorder or disease, stabilized (i.e., not worsening) disease or disorder state, delay or slowing of the disease or disorder state, improvement or alleviation of the disease or disorder state, and remission of the disease or disorder, whether partial or total.

[0038] In another embodiment, the compounds of formula (I) are used to modulate the activity of the protein kinase, c-abl.

[0039] As used herein, the term "modulate" or "modulation" refers to a change in the catalytic activity of a protein kinase. In particular, modulate refers to the activation or inhibition of the catalytic activity of a protein kinase depending on the concentration of a compound or salt to which the protein kinase is exposed, or more preferably, the inhibition of the catalytic activity of the protein kinase. As used herein, the term "catalytic activity" refers to the rate of phosphorylation of tyrosine, serine, or threonine under the direct or indirect influence of a protein kinase.

[0040] Pharmacological inhibitors of kinase activity are classified into three major classes: (1) type I or "DFG-in" ATP-competitive inhibitors that directly compete with ATP at the ATP-binding site (i.e., the Src and Abl inhibitor dasatinib), (2) type II or "DFG-out" ATP-competitive inhibitors (i.e., imatinib, nilotinib), which in addition to binding to the ATP-binding site also engage an adjacent hydrophobic binding site that is accessible only when the kinase is in an inactivated configuration (i.e., the activation loop is oriented in a conformation that would prevent substrate binding), and (3) non-ATP-competitive inhibitors (i.e., GNF-2), which bind to a site outside the ATP-binding site affecting the activity of the kinase.

[0041] As used herein, the phrase "compounds of the present disclosure" includes any compound of formula (I) and clathrates, hydrates, solvates, or polymorphs thereof. Even if the term "compounds of the present disclosure" does not refer to a pharma- ceutically acceptable salt thereof, the term includes the salt. In one embodiment, the compounds of the present disclosure include stereochemically pure compounds, e.g., compounds that are substantially free of other stereoisomers (e.g., greater than 85% ee, greater than 90% ee, greater than 95% ee, greater than 97% ee, or greater than 99% ee). That is, when the compounds of formula (I) of the present disclosure or salts thereof are tautomers and / or stereoisomers (e.g., geometric and conformational isomers), such isolated isomers and mixtures thereof are also included within the scope of the present disclosure. When the compounds of the present disclosure or salts thereof have asymmetric carbons in their structure, their active optical isomers and racemic mixtures thereof are also included within the scope of the present disclosure.

[0042] As used herein, the term "polymorph" refers to a solid crystalline form of a compound of the present disclosure or a complex thereof. Different polymorphs of the same compound may exhibit different physical, chemical and / or spectroscopic properties. Different physical properties include, but are not limited to, stability (e.g., against heat or light), compressibility and density (important for formulation and product manufacturing) and dissolution rate (which may affect bioavailability). Differences in stability may result from changes in chemical reactivity (e.g., differences in oxidation, resulting in a dosage form discoloring more quickly when composed of one polymorph than when composed of another polymorph) or mechanical properties (e.g., a tablet that disintegrates on storage because a kinetically favored polymorph converts to a thermodynamically more stable polymorph) or both (e.g., a tablet of one polymorph is more susceptible to disintegration at high humidity). Different physical properties of polymorphs may affect their processing. For example, one polymorph may be more likely to form solvates or may be more difficult to filter or wash away impurities than another polymorph because of its particle shape or size distribution.

[0043] As used herein, the term "solvate" refers to a compound of the present disclosure or a salt thereof that further comprises a stoichiometric or non-stoichiometric amount of a solvent bound by non-covalent intermolecular forces. Preferred solvents are volatile, non-toxic and / or acceptable for administration to humans in trace amounts.

[0044] As used herein, the term "hydrate" means a compound of the present disclosure or a salt thereof that further includes a stoichiometric or non-stoichiometric amount of water bound by non-covalent intermolecular forces.

[0045] As used herein, the term "clathrate" means a compound or a salt thereof in the form of a crystal lattice that contains spaces (e.g., channels) having guest molecules (e.g., solvent or water) trapped within.

[0046] Compounds of the Disclosure The present disclosure provides a compound of formula (I): [ka] [In the formula, R 1 is cyclopropyl, cyclobutyl or 4-membered heterocyclyl, where R 1 is optionally substituted with one or more groups selected from the group consisting of halo, alkyl, hydroxyalkyl, haloalkyl, and monoalkylaminoalkyl; R 2 and R 3 are independently -H, halo, alkyl, alkoxy, -CF3, -CHF2, -CH2F, or -OCF3; R 4 is aryl, heteroaryl, cycloalkyl, heterocyclyl, or heteroalkyl, where R 4 is halo, hydroxyl, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, hydroxyalkyl, dialkylaminoalkyl, trimethylsilylethoxymethyl, -CH2NHC(O)CH3, -NO2, -NR a R b , -NR a C(=O)R b , -NR a C(=O)NR a R b , -NR a C(=O)OR b , -OR a , -CN, -C(=O)R a , -C(=O)OR a , -C(=O)NR a R b , -OC(=O)R a , -OC(=O)OR a , -OC(=O)NR a R b , -SR a, azetidinyl, oxetanyl, tetrahydrofuranyl, furanyl, pyrrolidinyl, pyrrolyl, pyrazolyl, thiophenyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, furazanyl, oxadiazolyl, thiadiazolyl, phenyl, tetrahydropyranyl, pyranyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, piperidinyl, piperazinyl, morpholinyl, and thiomorpholinyl; R a and R b are independently -H, halo, amino, alkyl, or haloalkyl; R 5 is H, halo or alkyl. or a pharma- ceutically acceptable salt thereof.

[0047] In some embodiments, R 1 is cyclopropyl or cyclobutyl, where R 1 is optionally substituted with one or more groups selected from the group consisting of halo, C1-C3 alkyl, C1-C3 hydroxyalkyl, and C1-C3 haloalkyl; R 2 and R 3 are independently -H, halo, C1-C3 alkyl, C1-C3 alkoxy, -CF3, -CHF2, -CH2F, or -OCF3; R 4 is aryl, heteroaryl, cycloalkyl, or heterocyclyl, where R 4 is halo, hydroxyl, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, mono-C1-C3 alkylamino, di-C1-C3 alkylamino, -NO2, -NR a R b , -NR a C(=O)R b , -NR a C(=O)NR a R b , -NR a C(=O)OR b , -OR a, -CN, -C(=O)R a , -C(=O)OR a , -C(=O)NR a R b , -OC(=O)R a , -OC(=O)OR a , -OC(=O)NR a R b , -SR a , azetidinyl, oxetanyl, tetrahydrofuranyl, furanyl, pyrrolidinyl, pyrrolyl, pyrazolyl, thiophenyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, furazanyl, oxadiazolyl, thiadiazolyl, phenyl, tetrahydropyranyl, pyranyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, piperidinyl, piperazinyl, morpholinyl, and thiomorpholinyl; a and R b are independently -H, halo, amino, C1-C3 alkyl or C1-C3 haloalkyl; R 5 is H, F-, Cl-, Br- or methyl.

[0048] In various embodiments, R 1 is cyclopropyl or cyclobutyl, where R 1 is optionally substituted with one or more groups selected from the group consisting of halo, C1-C3 alkyl, C1-C3 hydroxyalkyl, and C1-C3 haloalkyl. 1 is cyclopropyl, fluorocyclopropyl, hydroxycyclopropyl, hydroxymethylcyclopropyl, difluorocyclopropyl, methylaminomethylcyclopropyl, cyclobutyl, fluorocyclobutyl or difluorocyclobutyl. 1 is cyclopropyl, fluorocyclopropyl, cyclobutyl or fluorocyclobutyl.

[0049] In some other embodiments, R 1is a 4-membered heterocyclyl optionally substituted with one or more groups selected from the group consisting of halo, C1-C3 alkyl, C1-C3 hydroxyalkyl, and C1-C3 haloalkyl. In certain embodiments, the 4-membered heterocyclyl is selected from the group consisting of aziridinyl, 2H-azirinyl, oxiranyl, thiiranyl, azetidinyl, 2,3-dihydroazetyl, azetyl, 1,3-diazetidinyl, oxetanyl, 2H-oxetyl, thietanyl, and 2H-thiethyl.

[0050] In some embodiments, R 2 and R 3 is independently -H, methyl or fluoro.

[0051] In some embodiments, R 4 is phenyl, pyridinyl, pyrimidinyl, indolinyl, pyrazolyl, thiazolyl, oxoindolinyl, pyrrolopyridinyl, pyrazolyl, pyrazolopyridinyl, oxodihydropyrrolopyridinyl, oxodihydrobenzothiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, thiophenyl, pyrrolopyridinyl or isothiazolyl, where R 4 is optionally substituted with one or more groups selected from the group consisting of halo, alkyl, alkenyl, alkynyl, hydroxyalkyl, amino, cyano, acetyl, hydroxy, and haloalkyl. 4are fluoro-methylphenyl, fluoro-hydroxymethylphenyl, chloro-hydroxymethylphenyl, methyl-hydroxymethylphenyl, difluoro-hydroxymethylphenyl, chloro-hydroxymethylphenyl, chloro-methylphenyl, dimethylphenyl, acetamido-methylphenyl, hydroxy-methylphenyl, hydroxypropanyl-methylphenyl, methyl-propenylphenyl, methyl-pyridinylethynylphenyl, methyl-pyrrolylphenyl, methyl-thiazolylphenyl, imidazolyl-methylphenyl, cyano-methylphenyl, methyl-pyrazolylphenyl, ethynyl-methylphenyl, methylpyridinyl, fluoro-methyl-methylaminophenyl, dimethylpyridinyl, fluoro-methylpyridinyl, fluoromethyl-methylpyridinyl, cyanopyridinyl, trifluoromethyl In certain embodiments, R is selected from the group consisting of aryl-methylpyridinyl, hydroxymethylpyridinyl, hydroxymethyl-methylpyridinyl, hydroxyethyl-methylpyridinyl, chloro-methylpyridinyl, aminopyridinyl, acetyl-methylpyridinyl, amino-dimethylpyridinyl, hydroxyethyl-methylpyridinyl, methylindolyl, methyloxoindolyl, trimethylsilylethoxymethylindolyl, acetyl-methylindolinyl, methylpyrimidinyl, dimethylpyrimidinyl, trifluoromethylpyrimidinyl, pyrazolyl, methylthiazolyl, methyloxoindolinyl, pyrrolopyridinyl, methylpyrrolopyridinyl, methyl-tetrahydropyranyl, methylpyrazolyl, methyl-oxodihydrobibenzothiazolyl, pyrazolopyridinyl, oxodihydropyrrolopyridinyl, methylisothiazolyl, chloro-methylisothiazolyl, dimethylisothiazolyl, and fluoro-methylindolyl. 4are fluoro-methylphenyl, fluoro-hydroxymethylphenyl, chloro-hydroxymethylphenyl, methyl-hydroxymethylphenyl, difluoro-hydroxymethylphenyl, chloro-hydroxymethylphenyl, chloro-methylphenyl, dimethylphenyl, acetamido-methylphenyl, hydroxy-methylphenyl, methyl-propenylphenyl, ethynyl-methylphenyl, fluoro-methyl-methylaminophenyl, fluoro-hydroxy-methylphenyl, methyl-methylaminophenyl, methyl-propylphenyl, methyl-thiazolylphenyl, cyano-methylphenyl, imidazolyl-methylphenyl, methylpyridinyl, chloro-methylpyridinyl, fluoro-methyl-phenyl, methyl ...propylphenyl, methyl-thiazolylphenyl, cyano-methylphenyl, imidazolyl-methylphenyl, methylpyridinyl, In certain embodiments, R is selected from the group consisting of methylpyridinyl, methylpyridinyl, methylpyridinyl, methylpyridinyl, methylpyridinyl, methylpyridinyl, pyrazolyl, methylpyrazolyl, methylindolinyl, methyloxoindolinyl, pyrrolopyridinyl, methylpyrrolopyridinyl, methylpyrrolyl, pyrazolopyridinyl, dihydropyrrolopyridinyl, methylisothiazolyl, dimethylisothiazolyl, methylindazolyl, and methyl-benzothiazolyl. 4 is pyridinyl or phenyl having one or more substitutions selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, halo, hydroxy, hydroxyalkyl, haloalkyl, cyano, amino, alkoxy, alkoxyalkoxyalkyl, alkoxyalkyl, and haloalkoxy. 4 is below: [ka] TIFF0007609790000004.tif230169 TIFF0007609790000005.tif244169 TIFF0007609790000006.tif134169 is selected from the group consisting of:

[0052] In some embodiments, R 1 is cyclopropyl, fluorocyclopropyl, difluorocyclopropyl, cyclobutyl, fluorocyclobutyl or difluorocyclobutyl; R 2 and R 3 are independently -H, methyl or fluoro; R 4 are fluoro-methylphenyl, fluoro-hydroxymethylphenyl, chloro-methylphenyl, dimethylphenyl, acetamido-methylphenyl, hydroxy-methylphenyl, methyl-propenylphenyl, ethynyl-methylphenyl, fluoro-methyl-methylaminophenyl, methyl-pyrrolylphenyl, methyl-thiazolylphenyl, cyano-methylphenyl, imidazolyl-methylphenyl, methylpyridinyl, chloro-methylpyridinyl, fluoro-methylpyridinyl, fluoromethyl-methylpyridinyl, bimethylpyridinyl, aminopyridinyl, amino-dimethylpyridinyl, methoxypyridinyl, lysinyl, acetyl-methylpyridinyl, hydroxymethylpyridinyl, hydroxymethyl-methylpyridinyl, hydroxyethyl-methylpyridinyl, cyanopyridinyl, trifluoromethylpyridinyl, methylthiophenyl, methylindolinyl, methylpyrimidinyl, dimethylpyrimidinyl, pyrazolyl, methylpyrazolyl, methylindolinyl, methyloxoindolinyl, pyrrolopyridinyl, methylpyrrolopyridinyl, methylpyrrolyl, pyrazolopyridinyl, dihydropyrrolopyridinyl, methylisothiazolyl, dimethylisothiazolyl, methylindazolyl or methyl-bibenzothiazolyl.

[0053] The compounds described herein have c-abl inhibitory activity and selectivity for c-abl, making them effective in treating neurodegenerative diseases.

[0054] In an embodiment, R 1 is cyclopropyl, fluorocyclopropyl, cyclobutyl, fluorocyclobutyl or difluorocyclobutyl; R 2 and R 3 is -H, R 4 is phenyl, pyridinyl, pyrazolyl, pyrrolopyridinyl, indolinyl, oxoindolinyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, or thiophenyl, where R 4 is halo, hydroxyl, alkyl, haloalkyl, hydroxyalkyl, cycloalkyl, alkoxyalkyl, alkoxyalkoxy, alkylaminoalkyl, -NR a R b , -NR a C(=O)R b , -OR a , -SR a , -CN, -C(=O)R a , -C(=O)OR a , -C(=O)NR a R b , -OC(=O)R a , furanyl, or pyrrolyl; R a and R b are independently -H, halo, amino, alkyl, or haloalkyl; R 5 is -H, halo, or C1-C3 alkyl.

[0055] In various embodiments, R 1 is fluorocyclopropyl, and such compounds include the following compounds and salts thereof: 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-chloro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(3-chloro-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(3-methyl-6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-chloro-6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-fluoro-4-methylpyridin-3-yl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; Methyl 3-(2-(2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-4-methylbenzoate; 2-Fluoro-N-(6-(5-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-methyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-chloro-6-(5-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-cyano-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(1H-pyrazol-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(4-chloropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2,3-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-amino-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-methyl-5-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-acetamido-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-methyl-5-(1H-pyrazol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(4-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-(trifluoromethyl)pyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,4-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(3-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,5-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-oxoindolin-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(4-cyanopyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-fluoro-2,3-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-fluoro-2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-methyl-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-methylthiophen-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-fluoro-5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3,4-difluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3,6-difluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(4-chloro-3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-methoxypyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(6-amino-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-amino-3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-methyl-2-oxoindolin-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-chloro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-oxo-2,3-dihydrobenzo[d]thiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(6-aminopyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-methyl-5-(1H-pyrazol-1-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-bromo-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methoxyphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-cyano-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(2-chloro-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(2,3-difluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(3,5-dimethyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-(methoxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-(furan-2-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-(methylthio)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(6-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-acetyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(6-(dimethylamino)-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-(aminomethyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(2-(acetamidomethyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2,2-Difluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-((methylamino)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-((isopropylamino)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-((2-methoxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-((2-hydroxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-((dimethylamino)methyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(o-tolyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-hydroxyphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-amino-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(5-methyl-1H-indol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(6-methyl-1H-indol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-(dimethylamino)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(5-methyl-1H-benzo[d]imidazo l-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-ethyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-cyclopropyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-methylbenzo[d]oxazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-methyl-1H-benzo[d]imidazo l-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(6-methylbenzo[d]thiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-methylbenzo[d]oxazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-methylbenzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(7-methylbenzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-isopropylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-methyl-3-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-fluoro-2-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-fluoro-2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-ethyl-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide N-(6-(4-acetyl-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2-chloro-3,4-difluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2-chloro-3,6-difluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(furan-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(thiophen-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(thiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-methylisothiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-methylthiazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(8-(difluoromethyl)-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)-8-(fluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(8-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(7-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-fluoro-2-methylphenyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(8-(difluoromethyl)-6-(4-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-fluoro-2-methylphenyl)-8-(fluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(8-fluoro-6-(4-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(7-fluoro-6-(4-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-fluoro-2-methylphenyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(8-(difluoromethyl)-6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-fluoro-2-methylphenyl)-8-(fluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(8-fluoro-6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(7-fluoro-6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(8-(difluoromethyl)-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)-8-(fluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(8-fluoro-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(7-fluoro-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(4-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(4-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-fluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-fluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3-chloro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(3-chloro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(4-chloro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(4-chloro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-chloro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(5-chloro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2-chloro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-chloro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2-(hydroxymethyl)-3-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-(hydroxymethyl)-3-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-(hydroxymethyl)-4-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-(hydroxymethyl)-4-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-(hydroxymethyl)-5-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-(hydroxymethyl)-5-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-(hydroxymethyl)-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-(hydroxymethyl)-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3,4-difluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(3,4-difluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(4,5-difluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(4,5-difluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2,3-difluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2,3-difluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3,6-difluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(3,6-difluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3-chloro-4-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(3-chloro-4-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(4-chloro-5-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(4-chloro-5-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3-chloro-2-fluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(3-chloro-2-fluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(6-chloro-3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(6-chloro-3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(4-fluoro-2-(hydroxymethyl)-3-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(4-fluoro-2-(hydroxymethyl)-3-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-fluoro-2-(hydroxymethyl)-4-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-fluoro-2-(hydroxymethyl)-4-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-fluoro-6-(hydroxymethyl)-3-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-fluoro-6-(hydroxymethyl)-3-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3-fluoro-2-(hydroxymethyl)-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-(hydroxymethyl)-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(4-chloro-3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(4-chloro-3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3-fluoro-2-(hydroxymethyl)-4-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-(hydroxymethyl)-4-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3,5-difluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(3,5-difluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-chloro-3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(5-chloro-3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3-fluoro-2-(hydroxymethyl)-5-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-(hydroxymethyl)-5-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-chloro-4-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(5-chloro-4-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3,4-difluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(3,4-difluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2,4-difluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2,4-difluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2-chloro-4-fluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-chloro-4-fluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(4-fluoro-2-(hydroxymethyl)-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(4-fluoro-2-(hydroxymethyl)-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-chloro-3-fluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-chloro-3-fluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3,5-difluoro-2-(hydroxymethyl)-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(3,5-difluoro-2-(hydroxymethyl)-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3-chloro-5-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(3-chloro-5-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-fluoro-2-(hydroxymethyl)-3-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-fluoro-2-(hydroxymethyl)-3-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-fluoro-2-(hydroxymethyl)-4-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-fluoro-2-(hydroxymethyl)-4-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3-chloro-6-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(3-chloro-6-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(6-fluoro-2-(hydroxymethyl)-3-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(6-fluoro-2-(hydroxymethyl)-3-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(4-chloro-2-fluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(4-chloro-2-fluoro-6-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2-fluoro-6-(hydroxymethyl)-4-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-fluoro-6-(hydroxymethyl)-4-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-(hydroxymethyl)-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(4-(hydroxymethyl)-1H-pyrazol-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(4-(hydroxymethyl)-1H-pyrazol-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-(hydroxymethyl)-5-(1H-pyrazol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-(hydroxymethyl)-5-(1H-pyrazol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-(hydroxymethyl)-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-(hydroxymethyl)-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3-(hydroxymethyl)thiophen-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-(hydroxymethyl)thiophen-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)-2-oxoindolin-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-(hydroxymethyl)-2-oxoindolin-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-(hydroxymethyl)-5-(1H-pyrazol-1-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(2-(hydroxymethyl)-5-(1H-pyrazol-1-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)-3-methyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-(hydroxymethyl)-3-methyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(4-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(4-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)-1H-indol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-(hydroxymethyl)-1H-indol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(6-(hydroxymethyl)-1H-indol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(6-(hydroxymethyl)-1H-indol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)-1H-benzo[d]imidazo l-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-(hydroxymethyl)-1H-benzo[d]imidazo l-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)benzo[d]oxazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-(hydroxymethyl)benzo[d]oxazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)-1H-benzo[d]imidazo l-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-(hydroxymethyl)-1H-benzo[d]imidazo l-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)benzo[d]thiazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-(hydroxymethyl)benzo[d]thiazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)benzo[d]oxazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-(hydroxymethyl)benzo[d]oxazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)benzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-(hydroxymethyl)benzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(7-(hydroxymethyl)benzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(7-(hydroxymethyl)benzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-(hydroxymethyl)thiazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; and 2-Fluoro-N-(6-(5-(hydroxymethyl)thiazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide Including, but not limited to:

[0056] In an embodiment, R 1 is fluorocyclopropyl, R 2 and R3 is -H, R 4 is phenyl, indolinyl, oxoindolinyl or benzothiazolyl, where R 4 is optionally substituted with one or more groups selected from the group consisting of halo, hydroxyl, alkyl, alkylamino, and pyrrolyl; R 5 is -H, halo, or C1-C3 alkyl. In various embodiments, such compounds include the following compounds and salts thereof: 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-chloro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(3-chloro-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-methyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,3-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-methyl-5-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,4-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(3-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,5-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-oxoindolin-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-methyl-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-fluoro-5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-methyl-2-oxoindolin-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-bromo-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3,5-dimethyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(5-methyl-1H-indol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(6-methyl-1H-indol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; and 2-Fluoro-N-(6-(5-methylbenzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide Including, but not limited to:

[0057] In one embodiment, the compound of formula (I) has formula (II): [ka] [In the formula, R 6 is selected from the group consisting of halo, C1-C3 alkyl, C1-C3 hydroxyalkyl, and C1-C3 haloalkyl; R 2 , R 3 , R 4 and R 5 is as defined above] and pharma- ceutically acceptable salts thereof.

[0058] In one embodiment, the compound of formula (I) is1 is cyclopropyl. In an embodiment, the compound of Formula (I) is N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide or a salt thereof.

[0059] In another embodiment, the compound of formula (I) is 1 is cyclobutyl optionally substituted with one or more groups selected from the group consisting of halo, alkyl, hydroxyalkyl, haloalkyl, and monoalkylaminoalkyl; R 2 , R 3 , R 4 , and R 5 In various embodiments, the compound of formula (I) is the following compound and salts thereof: N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclobutanecarboxamide, 3-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclobutanecarboxamide; and 3,3-Difluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclobutanecarboxamide is selected from the group consisting of:

[0060] The compounds of the present disclosure include stereoisomers of the compounds described herein. In some embodiments, the compounds are stereochemically pure compounds, e.g., compounds that are substantially free of other stereoisomers (e.g., greater than 85% ee, greater than 90% ee, greater than 95% ee, greater than 97% ee, or greater than 99% ee). Examples of such stereoisomers include the following: [ka] [In the formula, R 2 , R 3 , R 4 , R 5 and R 6is as defined above] Including, but not limited to:

[0061] In one embodiment, the compound of formula (I) has formula (III): [ka] [In the formula, R 6 is selected from the group consisting of halo, C1-C3 alkyl, C1-C3 hydroxyalkyl, and C1-C3 haloalkyl; R 2 , R 3 , R 4 and R 5 is as defined above] and pharma- ceutically acceptable salts thereof. Exemplary compounds having the stereochemistry of formula (III) are shown in Table 1. Examples of compounds having formula (III) are the following compounds and salts thereof: (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(3-chloro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(3-chloro-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(3-methyl-6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(3-chloro-6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(5-fluoro-4-methylpyridin-3-yl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; Methyl 3-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-4-methylbenzoate; (1S,2S)-2-Fluoro-N-(6-(5-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(5-methyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(3-chloro-6-(5-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(5-cyano-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(1H-pyrazol-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(4-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(3-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(4-chloropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(2,3-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(5-amino-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(5-acetamido-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(5-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(1H-pyrazol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(4-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(3-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(4-(trifluoromethyl)pyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(2,4-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(3-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(2,5-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-oxoindolin-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(4-cyanopyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(4-fluoro-2,3-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(4-fluoro-2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(4-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(3-methylthiophen-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(4-fluoro-5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(3,4-difluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(3,6-difluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(4-chloro-3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(4-methoxypyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(6-amino-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(5-amino-3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(5-methyl-2-oxoindolin-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(2-chloro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-oxo-2,3-dihydrobenzo[d]thiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(6-aminopyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(1H-pyrazol-1-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(3-bromo-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-methoxyphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-cyano-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(2-chloro-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(2,3-difluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(3,5-dimethyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-(methoxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-(furan-2-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-(methylthio)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(6-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-acetyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(6-(dimethylamino)-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide (1S,2S)-N-(6-(2-(aminomethyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(2-(acetamidomethyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-((methylamino)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-((isopropylamino)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-((2-methoxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-((2-hydroxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-((dimethylamino)methyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(o-tolyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-hydroxyphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-amino-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(5-methyl-1H-indol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(6-methyl-1H-indol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-(dimethylamino)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(5-methyl-1H-benzo[d]imidazo-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-ethyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-cyclopropyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(5-methylbenzo[d]oxazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(5-methyl-1H-benzo[d]imidazo-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(6-methylbenzo[d]thiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(5-methylbenzo[d]oxazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(5-methylbenzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-Fluoro-N-(6-(7-methylbenzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; and (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-isopropylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide Including, but not limited to:

[0062] In certain embodiments, the compound according to formula (I) is the following compound and salts thereof: (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(5-methyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(2,5-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(4-fluoro-5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-Fluoro-N-(6-(6-methyl-1H-indol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; and (1S,2S)-2-Fluoro-N-(6-(5-methylbenzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide is selected from the group consisting of:

[0063] The present disclosure provides pharma- ceutically acceptable salts of the above-mentioned compounds. Pharmaceutically acceptable salts are as defined above in the definition section. In some embodiments, the salt is a hydrochloride, a tartrate, a phosphate or a maleate.

[0064] Treatment The present disclosure further provides a method for treating a neurodegenerative disease or disorder in a subject having or susceptible to having a neurodegenerative disease or disorder by administering to the subject a therapeutically effective amount of one or more of the compounds described above. In one embodiment, the treatment is a preventive treatment. In another embodiment, the treatment is a palliative treatment. In another embodiment, the treatment is a restorative treatment.

[0065] 1. Disease or condition The compounds of the present disclosure for inhibiting c-abl and / or LRRK2 activity are useful for treating or preventing neurodegenerative diseases or disorders. The compounds can be used to inhibit or interfere with c-abl and / or LRRK2 kinase activity and treat neurodegenerative diseases or disorders or prevent the worsening of such diseases. Thus, the present disclosure provides a method for inhibiting or interfering with c-abl and / or LRRK activity in a cell, contacting the cell with an effective amount of a compound of the present disclosure. In one embodiment, such a cell is present in a subject (e.g., an Alzheimer's patient). In another embodiment, a medical use is provided for treating or preventing a neurodegenerative disease or disorder in a subject using a compound of the present disclosure. The method of the present disclosure includes administering a pharmaceutical composition containing a therapeutically or prophylactically effective amount of a c-abl and / or LRRK2 inhibitor to a subject in need of treatment or prevention of a neurodegenerative disease or disorder. Neurodegenerative diseases or disorders include, but are not limited to, alpha-synucleinopathy, Parkinson's disease, dementia with Lewy bodies, multiple system atrophy (MSA), Alzheimer's disease or amyotrophic lateral sclerosis (ALS). Medical uses of the present disclosure also include inflammatory diseases, inflammatory bowel disease, Crohn's disease, ulcerative colitis, rheumatoid arthritis, psoriasis, contact dermatitis or delayed hypersensitivity reactions.

[0066] 2. Target Subjects suitable for treatment according to the present disclosure include mammalian subjects. Mammals of the present disclosure include, but are not limited to, humans, dogs, cats, cows, goats, horses, sheep, pigs, rodents, rabbits, primates, etc., including mammals in utero. Subjects may be of any gender and at any stage of development. In one embodiment, subjects suitable for treatment according to the present disclosure are humans.

[0067] 3. Administration and Dosage The compounds of the present disclosure are generally administered in a therapeutically effective amount. The compounds of the present disclosure can be administered by any suitable route, in the form of a pharmaceutical composition adapted to such route, and in a dose effective for the intended treatment. An effective dose is typically in the range of about 0.001 to about 100 mg / kg body weight / day, preferably about 0.01 to about 50 mg / kg / day, in single or divided doses. Depending on the age, species, and disease or condition being treated, dosage levels below the lower end of this range may be appropriate. In other cases, even higher doses may be used without adverse side effects. Also, larger doses may be administered in several small doses throughout the day. Methods for determining appropriate doses are well known in the art to which the present disclosure pertains. For example, Remington: The Science and Practice of Pharmacy, Mack Publishing Co., 20th ed., 2000 may be used.

[0068] Pharmaceutical compositions, dosage forms and routes of administration For the treatment of the above-mentioned diseases or conditions, the compounds described herein, or a pharma- ceutically acceptable salt thereof, can be administered as follows.

[0069] Oral route Compounds of the disclosure can be administered orally, including by swallowing, so that the compound enters the gastrointestinal tract or absorbed into the blood stream directly from the mouth (eg, buccal or sublingual administration).

[0070] Compositions suitable for oral administration include solid, liquid, gel or powder preparations, having dosage forms such as tablets, lozenges, capsules, granules or powders.

[0071] Compositions for oral administration may be formulated as immediate or modified release (including delayed or sustained release), optionally with an enteric coating.

[0072] Liquid formulations can include solutions, syrups and suspensions that can be used in soft or hard capsules. Such formulations can include pharma- ceutically acceptable carriers, such as water, ethanol, polyethylene glycol, cellulose or oil. The formulations can also include one or more emulsifiers and / or suspending agents.

[0073] In tablet dosage forms, the amount of drug present can be from about 0.05% to about 95% by weight of the dosage form, more typically from about 2% to about 50% by weight. In addition, tablets can contain a disintegrant comprising from about 0.5% to about 35% by weight of the dosage form, more typically from about 2% to about 25% by weight. Examples of disintegrants include, but are not limited to, lactose, starch, sodium starch glycolate, crospovidone, croscarmellose sodium, maltodextrin, or mixtures thereof.

[0074] Suitable lubricants for use in tablets may be present in amounts of about 0.1% to about 5% by weight and include, but are not limited to, talc, silicon dioxide, stearic acid, calcium, zinc or magnesium stearate, sodium stearyl fumarate, and the like.

[0075] Binders suitable for use in tablets include, but are not limited to, gelatin, polyethylene glycol, sugars, gums, starch, polyvinylpyrrolidone, hydroxypropyl cellulose, hydroxypropyl methylcellulose, etc. Diluents suitable for use in tablets include, but are not limited to, mannitol, xylitol, lactose, dextrose, sucrose, sorbitol, microcrystalline cellulose and starch.

[0076] Solubilizers suitable for use in tablets may be present in an amount of about 0.1% to about 3% by weight and include, but are not limited to, polysorbates, sodium lauryl sulfate, sodium dodecyl sulfate, propylene carbonate, diethylene glycol monoethyl ether, dimethyl isosorbide, polyethylene glycol (natural or hydrogenated) castor oil, HCOR™ (Nikkol), oleyl esters, Gelucire™, caprylic / caprylic acid mono / diglycerides, sorbitan fatty acid esters, and Solutol HS™.

[0077] Parenteral Administration The compounds of the present disclosure can be administered directly into the bloodstream, muscle, or an internal organ. Suitable means for parenteral administration include intravenous, intramuscular, subcutaneous, intraarterial, intraperitoneal, intrathecal, intracranial, etc. Suitable devices for parenteral administration include syringes (including needle and needle-free syringes) and infusion techniques.

[0078] Compositions for parenteral administration can be formulated as immediate release or modified release (including delayed release or sustained release). Most parenteral formulations are aqueous solutions containing excipients including salts, buffers and isotonicity agents. Parenteral formulations can also be prepared in dehydrated form (e.g., by lyophilization) or as sterile non-aqueous solutions. These formulations can be used with a suitable vehicle, e.g., sterile water. Solubility enhancers can also be used in the preparation of parenteral solutions.

[0079] Transdermal Administration The compounds of the present disclosure can be administered topically or transdermally to the skin. The formulations for topical administration can include lotions, liquids, creams, gels, hydrogels, ointments, foams, implants, patches, etc. Pharmaceutically acceptable carriers for topical administration formulations can include water, alcohol, mineral oil, glycerin, polyethylene glycol, etc. Topical or transdermal administration can also be performed by electroporation, iontophoresis, migration, etc.

[0080] Compositions for topical administration may be formulated to be immediate or modified release (including delayed or sustained release).

[0081] Combination therapy The pharmaceutical composition of the present disclosure may contain one or more additional therapeutic agents, for example, to improve efficacy or reduce side effects.Thus, in some embodiments, the pharmaceutical composition further contains one or more additional therapeutic agents selected from active ingredients useful for treating or inhibiting diseases directly or indirectly mediated by c-abl and / or LRRK2 kinase.Examples of such active ingredients are agents for treating neurodegenerative diseases or disorders, such as, but not limited to, DNL151 and DNL201.

[0082] References for preparing pharmaceutical compositions Methods for preparing pharmaceutical compositions for treating or preventing a disease or condition are well known in the art to which this disclosure pertains. th ed.), Remington: The Science and Practice of Pharmacy (20 th ed.), Encyclopedia of Pharmaceutical Technology (3 rdPharmaceutically acceptable excipients, carriers, additives, etc. can be selected based on the principles of the present invention, such as those described in US Pat. No. 6,399,411 and US Pat. No. 6,399,421, and Sustained and Controlled Release Drug Delivery Systems (1978), and then mixed with the compounds of the present disclosure to prepare pharmaceutical compositions.

[0083] The present disclosure provides compounds having various pharmacological effects by inhibiting c-abl and / or LRRK2 activity, pharmaceutical compositions having the compounds as effective drugs, in particular medical uses of the compounds for treating neurodegenerative diseases or disorders, and therapeutic or prophylactic methods comprising administering the compounds to subjects in need of such treatment or prevention. The compounds of the present disclosure and their pharma- ceutically acceptable salts have good safety and high selectivity for c-abl and / or LRRK2, and therefore exhibit excellent properties as drugs.

[0084] Working Example In the following, the present disclosure will be described in detail by examples to help those skilled in the art understand the present disclosure. However, the following examples are provided as illustrations and are not intended to limit the scope of the present invention. It is clear that various modifications can be made without departing from the spirit and scope of the present invention or sacrificing all of its important advantages.

[0085] Synthesis of compounds of formula (I) The following compounds were prepared using synthetic methods A to N. Below, exemplary synthetic examples of some compounds of the present disclosure are described, and other compounds can be prepared by methods similar to those described below using different starting materials or reactants.

[0086] Synthesis method A Example 1. (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide hydrochloride [ka] Step 1) 6-iodoimidazo[1,2-a]pyridin-2-amine A mixture of compound 1 (10.000 g, 28.164 mmol) and lithium hydroxide monohydrate (4.727 g, 112.657 mmol) in water (100 mL) / methanol (300 mL) was heated at reflux for 18 h, cooled to room temperature, concentrated under reduced pressure, and partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic layer was washed with saturated aqueous sodium chloride, separated, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was diluted with dichloromethane (30 mL) and hexanes (200 mL) and stirred at ambient temperature. The resulting precipitate was collected by filtration, washed with hexanes, and dried to give compound 2 as a brown solid (5.890 g, 80.7%).

[0087] Step 2) (1S,2S)-2-Fluoro-N-(6-iodoimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide A mixture of compound 2 (5.890 g, 22.737 mmol), (1S,2S)-2-fluorocyclopropane-1-carboxylic acid (3.076 g, 29.558 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl, 6.538 g, 34.105 mmol) in dichloromethane (100 mL) was treated with N,N-diisopropylethylamine (2.376 mL, 13.642 mmol) at room temperature and stirred at the same temperature for 40 h. The precipitate was collected by filtration, washed with dichloromethane and dried to give compound 3 as a beige solid (3.870 g, 49.3%). 1H NMR (400 MHz, DMSO-d6) δ 10.99 (s, 1H), 8.87 (s, 1H), 8.02 (s, 1H), 7.36 - 7.23 (m, 2H), 4.97 - 4.77 (m, 1H), 2.09 - 2.07 (m, 1H), 1.65 - 1.57 (m, 1H), 1.16 - 1.09 (m, 1H).

[0088] Step 3) (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide Compound 3 (1.000 g, 2.898 mmol), (3-fluoro-2-methylphenyl)boronic acid (0.535 g, 3.477 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2, 0.212 g, 0.290 mmol) and cesium carbonate (1.416 g, 4.346 mmol) in tetrahydrofuran (12 mL) / water (3 mL) were mixed at room temperature, then heated at 100°C for 30 min in a microwave, cooled to room temperature, filtered through a celite pad to remove solids and partitioned with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with saturated aqueous sodium chloride, separated, dried (anhydrous MgSO4), filtered and concentrated under reduced pressure. The residue was chromatographed (SiO2, 45 g cartridge; ethyl acetate / hexanes = 70% to 100%) to give the crude product, which was crystallized with diethyl ether (5 mL) at room temperature. The resulting precipitate was filtered, washed with diethyl ether, and dried to give compound 4 as a white solid (0.700 g, 73.8%).

[0089] Step 4) (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide hydrochloride A solution of compound 4 (0.600 g, 1.833 mmol) in ethyl acetate (100 mL) was mixed with hydrochloric acid (1.00 M solution in EtOAc, 1.925 mL, 1.925 mmol) at room temperature. The reaction mixture was stirred at the same temperature for 3 hours. The precipitate was collected by filtration, washed with diethyl ether and dried to give Example 1 as a white solid (0.665 g, 99.7%). 1H NMR (400 MHz, DMSO-d6) δ 11.67 (s, 1H), 8.74 (s, 1H), 8.13 (s, 1H), 7.69 (d, J = 9.2 Hz, 1H), 7.55 (d, J = 9.2 Hz, 1H), 7.35 - 7.30 (m, 1H), 7.23 (t, J = 9.2 Hz, 1H), 7.15 (d, J = 7.2 Hz, 1H), 5.05 - 4.85 (m, 1H), 7.21 - 7.14 (m, 4H), 1.69 - 1.63 (m, 1H), 1.21 - 1.18 (m, 1H).

[0090] Synthesis method B Example 3. (1S,2S)-N-(3-chloro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide [ka] Step 1) (1S,2S)-N-(3-chloro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide A solution of Example 1 (0.060 g, 0.183 mmol) in acetonitrile (8 mL) was mixed with 1-chloropyrrolidine-2,5-dione (NCS, 0.027 g, 0.202 mmol) at room temperature, stirred at the same temperature for 3 h, and partitioned with ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, separated, dried (anhydrous MgSO4), filtered, and concentrated under reduced pressure. The residue was chromatographed (SiO2, 12 g cartridge; ethyl acetate / hexane = 70% to 100%) to give the crude product, which was crystallized at room temperature with diethyl ether (5 mL). The resulting precipitate was filtered, washed with diethyl ether, and dried to give Example 3 as a white solid (0.015 g, 22.6%). 1H NMR (400 MHz, DMSO-d6) δ 10.44 (s, 1H), 8.21 (s, 1H), 7.62 (d, J = 9.6 Hz, 1H), 7.35 (dd, J = 9.2, 1.6 Hz, 1H), 7.30 (t, J = 7.0 Hz, 1H), 7.24 - 7.19 (m, 2H), 5.01 - 4.83 (m, 1H), 2.15 (d, J = 2.4 Hz, 3H), 2.06 - 2.03 (m, 1H), 1.64 - 1.56 (m, 1H), 1.15 - 1.08 (m, 1H).

[0091] Synthesis method C Example 5. (1S,2S)-2-Fluoro-N-(3-methyl-6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide [ka] Step 1) (E)-2-(5-iodo-2-(tosylimino)pyridin-1(2H)-yl)propanamide A mixture of compound 5 and 2-bromopropanamide (4.549 g, 29.931 mmol) in N,N-dimethylformamide (40 mL) was treated with N,N-diisopropylethylamine (5.213 mL, 29.931 mmol) at room temperature and stirred at the same temperature for 24 h. The reaction mixture was diluted with water (500 mL) and stirred at ambient temperature. The resulting precipitate was collected by filtration, washed with water and dried to give the crude product, which was redissolved in ethyl acetate (100 mL) and diethyl ether (300 mL) and stirred at ambient temperature. The resulting precipitate was collected by filtration, washed with diethyl ether and dried to give compound 6 as a slightly pink solid (4.220 g, 35.5%). 1H NMR (400 MHz, DMSO-d6) δ 8.15 (d, J = 1.6 Hz, 1H), 7.87 (dd, J = 9.6, 2.4 Hz, 1H), 7.75 (s, 1H), 7.62 (d, J = 8.0 Hz, 2H), 7.38 (s, 1H), 7.24 (d, J = 8.4 Hz, 2H), 7.16 (d, J = 9.6 Hz, 1H), 5.63 (m, 1H), 2.30 (s, 3H), 1.60 (d, J = 7.2 Hz, 3H).

[0092] Step 2) 2,2,2-trifluoro-N-(6-iodo-3-methylimidazo[1,2-a]pyridin-2-yl)acetamide A stirred slurry of compound 6 (4.220 g, 9.477 mmol) in dichloromethane (50 mL) was mixed with trifluoroacetic anhydride (8.032 mL, 56.863 mmol) at room temperature. The reaction mixture was heated at reflux for 4 h, cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with diethyl ether (300 mL) and stirred at ambient temperature. The resulting precipitate was collected by filtration, washed with diethyl ether, and dried to give the crude product, which was redissolved in water (300 mL) and stirred at ambient temperature. The resulting precipitate was collected by filtration, washed with water, and dried to give compound 7 as a beige solid (3.098 g, 88.6%).

[0093] Step 3) 6-iodo-3-methylimidazo[1,2-a]pyridin-2-amine Compound 7 (3.098 g, 8.394 mmol) and lithium hydroxide monohydrate (1.057 g, 25.181 mmol) in water (15 mL) / ethanol (30 mL) were mixed at room temperature, then heated at 140° C. for 30 min in a microwave, cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with saturated aqueous ammonium chloride solution (20 mL) and stirred at ambient temperature. The resulting precipitate was collected by filtration, washed with water, and dried to give compound 8 as a pale yellow solid (1.400 g, 61.1%).

[0094] Step 4) (1S,2S)-2-Fluoro-N-(6-iodo-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide A mixture of compound 8 (1.400 g, 5.127 mmol), (1S,2S)-2-fluorocyclopropane-1-carboxylic acid (0.640 g, 6.152 mmol) and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 2.924 g, 7.690 mmol) in N,N-dimethylformamide (20 mL) was treated with N,N-diisopropylethylamine (2.679 mL, 15.380 mmol) at room temperature, stirred at 60° C. for 48 hours, cooled to room temperature and concentrated under reduced pressure. The residue was diluted with water (100 mL) and stirred at ambient temperature. The resulting precipitate was collected by filtration, washed with water, and dried to give the crude product, which was redissolved in ethyl acetate (50 mL) and stirred at ambient temperature The resulting precipitate was collected by filtration, washed with ethyl acetate, and dried to give compound 9 as a white solid (1.070 g, 58.1%). 1H NMR (400 MHz, DMSO-d6) δ 10.24 (s, 1H), 8.51 (s, 1H), 7.36 (dd, J = 9.2, 1.6 Hz, 1H), 7.27 (d, J = 9.2 Hz, 1H), 4.97 - 4.80 (m, 1H), 2.25 (s, 3H), 2.03 (m, 1H), 1.60 - 1.53 (m, 1H), 1.11 - 1.06 (m, 1H).

[0095] Step 5) (1S,2S)-2-Fluoro-N-(3-methyl-6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide Compound 9 (0.200 g, 0.557 mmol), (4-methylpyridin-3-yl)boronic acid (0.099 g, 0.724 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2, 0.041 g, 0.056 mmol) and potassium carbonate (0.231 g, 1.671 mmol) in water (3 mL) / tetrahydrofuran (12 mL) were mixed at room temperature, then heated at 120°C for 1 h in a microwave, cooled to room temperature and partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, separated, dried (anhydrous MgSO4), filtered and concentrated under reduced pressure. The residue was chromatographed (SiO2, 10 g cartridge; tetrahydrofuran / ethyl acetate = 0% to 10%) to give the crude product, which was dissolved in diethyl ether (5 mL) and hexane (20 mL) and stirred at ambient temperature. The resulting precipitate was collected by filtration, washed with hexane, and dried to give Example 5 as a beige solid (0.100 g, 55.4%). 1H NMR (400 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.47 (s, 1H), 8.44 (d, J = 5.2 Hz, 1H), 8.26 (s, 1H), 7.51 (d, J = 9.2 Hz, 1H), 7.34 (d, J = 5.2 Hz, 1H), 7.24 (d, J = 9.2 Hz, 1H), 4.99 - 4.81 (m, 1H), 2.29 (s, 6H), 2.07 - 2.03 (m, 1H), 1.63 - 1.56 (m, 1H), 1.15 - 1.05 (m, 1H).

[0096] Synthesis method D Example 29. (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(1H-pyrazol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide [ka] Step 1) (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(1H-pyrazol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide Example 26 (0.100 g, 0.291 mmol), (1H-pyrazol-3-yl)boronic acid (0.042 g, 0.378 mmol), [1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II) dichloride (Pd(dtbpf)Cl2, 0.019 g, 0.029 mmol) and cesium carbonate (0.284 g, 0.873 mmol) in 1,4-dioxane (12 mL) / water (3 mL) were mixed at room temperature, then heated at 140°C for 1 h in a microwave, cooled to room temperature and partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, separated, dried (anhydrous MgSO4), filtered and concentrated under reduced pressure. The residue was chromatographed (SiO2, 10 g cartridge; tetrahydrofuran / ethyl acetate = 0% to 20%) to give the crude product, which was dissolved in dichloromethane (3 mL) and hexane (20 mL) and stirred at ambient temperature. The resulting precipitate was collected by filtration, washed with diethyl ether and dried to give Example 29 as a beige solid (0.005 g, 4.6%). 1H NMR (400 MHz, DMSO-d6) δ 12.82 (s, 1H), 10.99 (s, 1H), 8.58 (s, 1H), 8.08 (s, 1H), 7.73 - 7.69 (m, 2H), 7.46 - 7.23 (m, 4H), 6.70 (s, 1H), 4.97 - 4.80 (m, 1H), 2.25 (s, 3H), 2.14 - 2.09 (m, 1H), 1.66 - 1.59 (m, 1H), 1.13 - 1.08 (m, 1H).

[0097] Synthesis method E Example 34. (1S,2S)-2-fluoro-N-(3-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide [ka] Step 1) (1S,2S)-2-fluoro-N-(3-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide A solution of Example 1 (0.1 g, 0.3055 mmol) in tetrahydrofuran (4 mL) was mixed with 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate (Selectfluor®, 0.162 g, 0.4582 mmol) at 0° C., stirred at room temperature for 3 h, and partitioned with dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was washed with saturated aqueous sodium chloride, separated, dried (anhydrous Na2SO4), filtered, and concentrated under reduced pressure. The residue was chromatographed (SiO2, 12 g cartridge; ethyl acetate / hexane=0%-30%) to give Example 34 as a yellow solid (0.021 g, 15%). 1H NMR (400 MHz, DMSO-d6) δ 10.56 (s, 1H), 8.23 ​​(s, 1H), 7.49 (d, J = 9.6 Hz, 1H), 7.33 - 7.27 (m, 1H), 7.24 - 7.16 (m, 3H), 5.01 - 4.81 (m, 1H), 2.15 (s, 3H), 2.05 - 2.05 (m, 1H), 1.63 - 1.56 (m, 1H), 1.17 - 1.09 (m, 1H).

[0098] Synthesis method F Example 41. (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide [ka] Step 1) 3-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-4-methylphenyl trifluoromethanesulfonate A mixture of Example 12 (0.842 g, 2.588 mmol) and pyridine (0.313 mL, 3.882 mmol) in dichloromethane (100 mL) was treated with trifluoromethanesulfonic anhydride (0.479 mL, 2.847 mmol) at 0° C., stirred at the same temperature for 1 h, and partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, separated, dried (anhydrous MgSO4), filtered, and concentrated under reduced pressure. The residue was chromatographed (SiO2, 10 g cartridge; ethyl acetate / hexane=80%-100%) to give compound 10 as a purple solid (0.056 g, 4.7%).

[0099] Step 2) (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide Compound 10 (0.056 g, 0.122 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole (0.031 g, 0.159 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2, 0.009 g, 0.012 mmol) and potassium carbonate (0.051 g, 0.367 mmol) in water (3 mL) / tetrahydrofuran (12 mL) were mixed at room temperature, then heated at 120°C for 30 min in a microwave, cooled to room temperature and partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, separated, dried (anhydrous MgSO4), filtered and concentrated under reduced pressure. The residue was chromatographed (SiO2, 10 g cartridge; tetrahydrofuran / ethyl acetate = 0% to 10%) to give the crude product, which was dissolved in diethyl ether (5 mL) and hexane (5 mL) and stirred at ambient temperature. The resulting precipitate was collected by filtration, washed with diethyl ether, and dried to give Example 41 as a white solid (0.005 g, 10.9%). 1H NMR (400 MHz, DMSO-d6) δ 10.97 (s, 1H), 10.86 (bs, 1H), 8.54 (s, 1H), 8.07 (s, 1H), 7.44 - 7.40 (m, 3H), 7.23 - 7.19 (m, 3H), 6.74 (dd, J = 4.4, 2.8 Hz, 1H), 6.41 (dd, J = 4.4, 2.8 Hz, 1H), 4.97 - 4.79 (m, 1H), 2.20 (s, 3H), 2.11 (m, 1H), 1.66 - 1.59 (m, 1H), 1.15 - 1.10 (m, 1H).

[0100] Synthesis method G Example 44. (1S,2S)-2-Fluoro-N-(6-(4-fluoro-5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide [ka] Step 1) (1S,2S)-2-Fluoro-N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide Compound 3 (0.800 g, 2.318 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane, 1.177 g, 4.636 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2, 0.169 g, 0.231 mmol) and potassium acetate (0.796 g, 8.113 mmol) were mixed in DMSO (20 mL) at room temperature, then stirred at 90 °C for 24 h, cooled to room temperature, filtered through a celite pad to remove solids and partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, separated, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to chromatography (SiO2, 12 g cartridge; ethyl acetate / hexanes = 0% to 100%) to give compound 11 as a brown solid (0.560 g, 69.9%).

[0101] Step 2) (1S,2S)-2-Fluoro-N-(6-(4-fluoro-5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide Compound 11 (0.080 g, 0.231 mmol), 5-bromo-2-fluoro-4-methylphenol (0.056 g, 0.277 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2, 0.017 g, 0.023 mmol) and Na2CO3 (0.049 g, 0.462 mmol) in dioxane (2 mL) / water (0.5 mL) were mixed at room temperature, then the mixture was degassed and purged with N2 for 1 min, after which the mixture was stirred under N2 atmosphere at 80°C for 12 h. The reaction mixture was concentrated to give a residue. The residue was purified. The residue was chromatographed (SiO2, 12 g cartridge; ethyl acetate / hexanes=80% to 100%) to give Example 44 as a white solid (0.031 g, 39.8%). 1H NMR (400 MHz, DMSO-d6) δ 10.98 (s, 1H), 9.75 (bs, 1H), 8.47 (s, 1H), 8.05 (s, 1H), 7.40 (d, J = 9.2 Hz, 1H), 7.13 (dd, J = 9.2, 2.0 Hz, 1H), 7.06 (d, J = 12.4 Hz, 1H), 6.81 (d, J = 9.2 Hz, 1H), 4.98 - 4.78 (m, 1H), 2.14 - 2.07 (m, 4H), 1.65 - 1.58 (m, 1H), 1.16 - 1.07 (m, 1H).

[0102] Synthesis method H Example 66. (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-(methoxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide [ka] Step 1) 1-Bromo-3-fluoro-2-(methoxymethyl)benzene To a solution of compound 12 (500 mg, 2.44 mmol, 1 equiv) in THF (10 mL) was added NaH (146.31 mg, 3.66 mmol, 60% purity, 1.5 equiv) in portions at 0° C. under N2, the reaction mixture was stirred at 0° C. under N2 for 0.5 h, after which MeI (692.30 mg, 4.88 mmol, 303.64 μL, 2 equiv) was added dropwise, and then the mixture was stirred at 20° C. under N2 for another 1 h. Saturated aqueous NH4Cl solution (30 mL) was added to the reaction mixture, then the mixture was extracted with ethyl acetate (20 mL*2), the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a residue. Compound 13 (510 mg, crude) was obtained as a yellow oil. 1H NMR (400MHz, CDCl3) δ 7.41 (d, J=8.1 Hz, 1H), 7.18 (dt, J=5.9, 8.2 Hz, 1H), 7.10 - 7.00 (m, 1H), 4.64 (d, J=2.3 Hz, 2H), 3.42 (s, 3H).

[0103] Step 2) (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-(methoxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide To a solution of compound 13 (80 mg, 365.21 μmol, 1 eq.) and compound 11 (151.27 mg, 438.25 μmol, 1.2 eq.) in dioxane (2 mL) and H2O (0.4 mL), Pd(dppf)Cl2 (26.72 mg, 36.52 μmol, 0.1 eq.) and Na2CO3 (77.42 mg, 730.42 μmol, 2 eq.) were added, and then the mixture was stirred at 90 °C under N2 for 12 h. The reaction mixture was diluted with ethyl acetate (300 mL), then the mixture was filtered through silica gel, and the filtrate was concentrated to give a residue. The residue was purified by preparative HPLC (column: Phenomenex luna C18 150*40 mm*15 um; mobile phase: [water (0.1% TFA)-ACN]; B%: 17%-47%, 10 min). Example 66 (91.3 mg, 193.69 μmol, 53.03% yield, 100% purity, TFA) was obtained as a white solid. 1H NMR (400MHz, DMSO-d6) δ 11.25 (s, 1H), 8.68 (s, 1H), 8.14 (s, 1H), 7.60 (d, J=9.2 Hz, 1H), 7.52 (dt, J=6.0, 7.9 Hz, 1H), 7.44 (dd, J=1.6, 9.2 Hz, 1H), 7.33 (d, J=8.7 Hz, 1H), 7.30 - 7.25 (m, 1H), 5.11 - 4.76 (m, 1H), 4.30 (br d, J=1.3 Hz, 2H), 3.25 (s, 3H), 2.23 - 2.08 (m, 1H), 1.76 - 1.59 (m, 1H), 1.20 (tdd, J=6.3, 9.1, 12.4 Hz, 1H).

[0104] Synthesis method I Example 67. (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-(furan-2-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide [ka] Step 1) 2-(2-bromo-6-fluorophenyl)furan To a solution of compound 14 (511.74 mg, 1.70 mmol, 1.1 equiv) and 2-(furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (300 mg, 1.55 mmol, 1 equiv) in dioxane (3 mL) and H2O (0.6 mL), Pd(dppf)Cl2 (113.13 mg, 154.61 μmol, 0.1 equiv) and Na2CO3 (491.61 mg, 4.64 mmol, 3 equiv) were added, and then the reaction mixture was stirred at 80 °C under N2 for 3 h. The reaction mixture was poured into water (50 mL), then the mixture was extracted with ethyl acetate (50 mL * 2), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by preparative TLC (SiO2, petroleum ether: ethyl acetate = 3:1). The residue was purified by preparative TLC (SiO2, petroleum ether:ethyl acetate=1:0). Compound 15 (70 mg, 290.39 μmol, 18.78% yield) was obtained as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.61 (dd, J = 0.8, 1.8 Hz, 1H), 7.48 (td, J = 1.1, 8.0 Hz, 1H), 7.21 (dt, J = 5.8, 8.1 Hz, 1H), 7.15 - 7.08 (m, 1H), 6.70 (td, J = 0.9, 3.3 Hz, 1H), 6.56 (dd, J = 1.8, 3.3 Hz, 1H).

[0105] Step 2) (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-(furan-2-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide To a solution of compound 15 (70 mg, 290.39 μmol, 1 equiv.) and compound 11 (110.26 mg, 319.43 μmol, 1.1 equiv.) in dioxane (1 mL) and H2O (0.2 mL), Pd(dppf)Cl2 (21.25 mg, 29.04 μmol, 0.1 equiv.) and Na2CO3 (92.33 mg, 871.17 μmol, 3 equiv.) were added, and the reaction mixture was then stirred at 80° C. under N2 for 12 h. The reaction mixture was poured into brine (10 mL), and the mixture was then extracted with ethyl acetate (10 mL*2), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was dissolved in methanol:dichloromethane (1:10, 100 mL), and the mixture was then filtered through silica gel, and the filtrate was concentrated to give a residue. The residue was purified by preparative HPLC (column: Phenomenex Synergi C18 150*25*10um; mobile phase: [water (0.1% TFA)-ACN]; B%: 34%-54%, 9 min). Example 67 (38.3 mg, 77.63 μmol, yield 26.73%, purity 100%, TFA) was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.20 (s, 1H), 8.61 (s, 1H), 8.08 (s, 1H), 7.61 (dd, J = 0.9, 1.6 Hz, 1H), 7.60 - 7.54 (m, 1H), 7.45 - 7.41 (m, 1H), 7.40 - 7.36 (m, 2H), 6.93 (dd, J = 1.3, 9.3 Hz, 1H), 6.56 - 6.48 (m, 2H), 5.05 - 4.83 (m, 1H), 2.19 - 2.09 (m, 1H), 1.75 - 1.59 (m, 1H), 1.19 (tdd, J = 6.3, 9.1, 12.4 Hz, 1H).

[0106] Synthesis method J Example 72. N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide [ka] Step 1) 2,2,2-trifluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)acetamide To a solution of compound 1 (1 g, 2.82 mmol, 1 equiv.) in dioxane (10 mL) and H2O (1 mL), compound 2 (520.30 mg, 3.38 mmol, 1.2 equiv.), Pd(dppf)Cl2 (206.08 mg, 281.65 μmol, 0.1 equiv.) and Na2CO3 (298.52 mg, 2.82 mmol, 1 equiv.) were added. The mixture was stirred at 80 °C under N2 atmosphere for 16 h. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (30 mL*2). The combined organic layers were washed with brine (30 mL*2), dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=20:1 to 5:1). Compound 16 (500 mg, 1.48 mmol, 52.64% yield) was obtained as a white solid.

[0107] Step 2) 6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-amine To a solution of compound 16 (500 mg, 1.48 mmol, 1 equiv) in MeOH (10 mL) and H2O (10 mL) was added K2CO3 (1.02 g, 7.41 mmol, 5 equiv). The mixture was stirred at 75 °C for 2 h. Water (50 mL) was added to the reaction mixture and extracted with ethyl acetate (50 mL * 2). The combined organic layers were washed with brine (50 mL * 2), dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to give a residue. Compound 17 (300 mg, 1.24 mmol, 83.88% yield) was obtained as a yellow solid.

[0108] Step 3) N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide To a solution of compound 17 (100 mg, 414.49 μmol, 1 equiv) in EtOAc (2 mL) was added cyclopropanecarboxylic acid (53.52 mg, 621.73 μmol, 49.10 μL, 1.5 equiv) and DCC (85.52 mg, 414.49 μmol, 83.84 μL, 1 equiv). The mixture was stirred at 20° C. for 32 h. Then, DMAP (5.06 mg, 41.45 μmol, 0.1 equiv) was added to the mixture and stirred at 20° C. for 16 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (20 mL*2). The combined organic layers were washed with brine (20 mL*2), dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to give a residue. The residue was purified by preparative HPLC (column: Phenomenex Luna C18 150*25mm*10um; mobile phase: [water (0.1% TFA)-ACN]; B%: 22%-52%, 10min). Example 72 (45.9mg, 106.25μmol, yield 25.63%, purity 98%, TFA) was obtained as a pink solid. 1H NMR (400MHz, DMSO-d6) δ 11.22 (br s, 1H), 8.66 (s, 1H), 8.09 (s, 1H), 7.59 (d, J=9.2 Hz, 1H), 7.40 (br d, J=9.3 Hz, 1H), 7.38 - 7.30 (m, 1H), 7.28 - 7.21 (m, 1H), 7.17 (d, J=7.5 Hz, 1H), 2.18 (d, J=2.3 Hz, 3H), 1.94 (quin, J=6.2 Hz, 1H), 0.85 (d, J=6.1 Hz, 4H).

[0109] Synthesis method K Example 77. (1S,2S)-N-(6-(2-(acetamidomethyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide [ka] Step 1) N-(2-bromo-6-fluorobenzyl)acetamide To a solution of compound 18 (200 mg, 695.94 μmol, 1 equiv) in Py (5 mL) was added Ac2O (85.26 mg, 835.13 μmol, 78.22 μL, 1.2 equiv). The mixture was stirred at 25 °C for 3 h. The desired MS was detected by LC-MS. The mixture was concentrated under reduced pressure to give a residue. The residue was adjusted to pH = 6 with HCl and extracted with EA (30 mL * 3). The organic phase was concentrated under reduced pressure to give a residue. Compound 19 (130 mg, 412.07 μmol, yield 59.21%, purity 78%) was obtained as a pale yellow solid.

[0110] Step 2) (1S,2S)-N-(6-(2-(acetamidomethyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide A mixture of compound 19 (100 mg, 361.68 μmol, 1 equiv.), compound 11 (122.35 mg, 354.44 μmol, 0.98 equiv.), Pd(dppf)Cl2 (26.46 mg, 36.17 μmol, 0.1 equiv.) and Na2CO3 (76.67 mg, 723.35 μmol, 2 equiv.) in water (1 mL) and dioxane (4 mL) was degassed and purged with N2 three times, then the mixture was stirred under N2 atmosphere at 80° C. for 16 h. The desired MS was detected by LC-MS. The mixture was filtered and the filtrate was concentrated under reduced pressure to give a residue. The residue was purified by preparative HPLC (column: Phenomenex luna C18 250*50mm*10um; mobile phase: [water (0.1% TFA)-ACN]; B%: 10%-40%, 9 min). Example 77 (15.3 mg, 29.84 μmol, yield 8.25%, purity 97.2%, TFA) was obtained as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.67 (s, 1H), 7.81 - 7.71 (m, 2H), 7.49 - 7.47 (m, 1H), 7.31 - 7.22 (m, 2H), 5.04 - 5.01 (m, 0.5H), 4.87 - 4.85 (m, 0.5H), 4.38 (s, 2H), 2.16 - 2.12 (m, 1H), 1.90 - 1.84 (m, 1H), 1.31 - 1.28 (m, 1H).

[0111] Synthesis method L Example 84. (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-((2-methoxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. TFA salt [ka] Step 1) 1-Bromo-3-fluoro-2-((2-methoxyethoxy)methyl)benzene Compound 20 (445.00 mg, 2.17 mmol, 1 equiv) was dissolved in DMF (15 mL) and NaH (130.22 mg, 3.26 mmol, 60% purity, 1.5 equiv) was added in portions at 0° C. The resulting mixture was then stirred under N2 atmosphere for 30 min, after which 1-bromo-2-methoxy-ethane (362.01 mg, 2.60 mmol, 244.60 μL, 1.2 equiv) was added at 0° C. The mixture was then stirred under N2 atmosphere at 15° C. for another 11.5 h. The mixture was quenched with EtOH (5 mL), diluted with water (20 mL), and extracted with EA (20 mL×3). The combined organic layers were concentrated under reduced pressure. The residue was purified by silica gel chromatography (pure PE to PE / EA=4 / 1) to give compound 21 (178 mg, 676.54 μmol, 31.17% yield) as a pale yellow oil.

[0112] Step 2) (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-((2-methoxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide.TFA salt A mixture of compound 21 (178 mg, 676.54 μmol, 1 eq.) and compound 11 (210.17 mg, 608.89 μmol, 0.9 eq.) was dissolved in dioxane (10 mL) and H2O (2 mL), to which Pd(dppf)Cl2 (99.01 mg, 135.31 μmol, 0.2 eq.) and Na2CO3 (215.12 mg, 2.03 mmol, 3 eq.) were added in portions. The resulting mixture was then stirred at 80 °C under N2 atmosphere for 16 h. The desired m / z was detected by LC-MS. The mixture was filtered, the filtrate was diluted with water (20 mL), and extracted with EA (20 mL x 3). The combined organic layers were concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE / EA=10 / 1~1 / 1) then preparative HPLC (column: Phenomenex Gemini-NX C18 75*30mm*3um; mobile phase: [water (0.1% TFA)-ACN]; B%: 18%~48%, 7min) and lyophilized to give Example 84 (32.2mg, 62.10μmol, yield 9.18%, purity 99.4%, TFA) as an off-white solid. 1H NMR (400 MHz, DMSO) δ 11.23 - 11.19 (br s, 1H), 8.72 (s, 1H), 8.10 (s, 1H), 7.56 -7.50 (m, 3H), 7.32 - 7.28 (m, 2H), 5.04 - 4.84 (m, 1H), 4.35 (s, 2H), 3.47 - 3.44 (m, 4H), 3.25 (s, 3H), 2.16 - 2.11 (m, 1H), 1.70 - 1.64 (m, 1H), 1.21 - 1.16 (m, 1H).

[0113] Synthesis method M Example 85. (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-((2-hydroxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide [ka] Step 1) (2-((2-bromo-6-fluorobenzyl)oxy)ethoxy)(tert-butyl)dimethylsilane Compound 22 (1 g, 4.88 mmol, 1 equiv) was dissolved in DMF (50 mL) and NaH (292.65 mg, 7.32 mmol, 60% purity, 1.5 equiv) was added in portions at 0 °C. The resulting mixture was then stirred under N2 atmosphere for 30 min, after which 2-bromoethoxy-tert-butyl-dimethyl-silane (1.40 g, 5.85 mmol, 109.93 μL, 1.2 equiv) was added at 0 °C. The mixture was then stirred under N2 atmosphere at 15 °C for another 11.5 h. A new spot was formed according to the results of TLC (PE / EA=4 / 1). The mixture was quenched with EtOH (5 mL), diluted with water (20 mL), and extracted with EA (20 mL x 3). The combined organic layers were concentrated under reduced pressure. The residue was purified together with the previous batch by silica gel chromatography (pure PE to PE / EA=4 / 1) to give compound 23 (372 mg, 1.02 mmol, yield 20.99%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.52 - 7.50 (m, 1H), 7.37 - 7.36 (m, 1H), 7.34 - 7.30 (m, 1H), 4.61 - 4.60 (m, 2H), 3.90 - 3.80 (m, 2H), 3.58 - 3.47 (m, 2H), 0.835 (s, 9H), 0.02 (s, 6H).

[0114] Step 2) 2-((2-bromo-6-fluorobenzyl)oxy)ethanol Compound 23 (352 mg, 968.80 μmol, 1 equiv.) was dissolved in DMF (10 mL), and CsF (147.16 mg, 968.80 μmol, 35.72 μL, 1 equiv.) was added. The resulting mixture was then stirred at 80° C. for 12 h. The starting material was consumed according to the results of TLC (PE / EA=4 / 1). The mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE~PE / EA=5 / 1) to give compound 24 (120 mg, 481.78 μmol, 49.73% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.52 - 7.50 (m, 1H), 7.36 - 7.28 (m, 2H), 4.60 - 4.59 (m, 2H), 3.52 - 3.47 (m, 4H).

[0115] Step 3: (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-((2-hydroxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide A mixture of compound 24 (120 mg, 481.78 μmol, 1 eq.) and compound 11 (149.67 mg, 433.60 μmol, 0.9 eq.) was dissolved in a mixture of dioxane (10 mL) and H2O (2 mL), and Pd(dppf)Cl2 (35.25 mg, 48.18 μmol, 0.1 eq.) and Na2CO3 (153.19 mg, 1.45 mmol, 3 eq.) were added in portions. The resulting mixture was then stirred at 80 °C under N2 atmosphere for 12 h. The desired m / z was detected by LC-MS. The mixture was filtered, the filtrate was diluted with water (20 mL), and extracted with EA (20 mL x 3). The combined organic layers were concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE / EA=2 / 1~EA / MeOH=10 / 1) then by preparative HPLC (column: Phenomenex Gemini-NX C18 75*30mm*3um; mobile phase: [water (0.1% TFA)-ACN]; B%: 12%~42%, 9 min) and lyophilized to give Example 85 (74.1 mg, 143.65 μmol, yield 29.82%, purity 97.2%, TFA) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.21 (s, 1H), 8.78 (s, 1H), 8.14 (s, 1H), 7.58 - 7.47 (m, 3H), 7.33 - 7.29 (m, 2H), 5.05 - 4.85 (m, 1H), 4.36 (s, 2H), 3.55 - 3.52 (m, 2H), 3.47 - 3.45 (m, 2H), 2.16 - 2.13 (m, 1H), 1.71 - 1.69 (m, 1H), 1.65 - 1.64 (m, 1H).

[0116] Synthesis method N Example 105. (1S,2S)-2-Fluoro-N-(6-(2-methyl-5-(1H-pyrazol-1-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide [ka] Step 1) 3-Bromo-4-methyl-2-nitrophenol To a solution of compound 25 (5 g, 26.73 mmol, 1 equiv.) in CHCl3 (50 mL), HNO3 (2.85 g, 29.41 mmol, 2.04 mL, 1.1 equiv.) was added dropwise at -50 °C, then the reaction mixture was stirred at -50 °C for 1 h. The reaction mixture was slowly poured into ice water (200 mL), then the mixture was extracted with dichloromethane (100 mL*2), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether / ethyl acetate = 1 / 0 to 100 / 1). Compound 26 (550 mg, 2.37 mmol, 8.87% yield) was obtained as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.84 - 8.20 (m, 1H), 7.31 (d, J = 8.7 Hz, 1H), 7.00 (d, J = 8.6 Hz, 1H), 2.41 (s, 3H).

[0117] Step 2) 2-Amino-3-bromo-4-methylphenol To a solution of compound 26 (450 mg, 1.94 mmol, 1 equiv) in EtOH (5 mL) and H2O (5 mL) was added Fe (649.83 mg, 11.64 mmol, 6 equiv) and NH4Cl (622.44 mg, 11.64 mmol, 6 equiv). The suspension was purged with N2 three times. The reaction mixture was stirred under N2 at 80 °C for 2 h. The reaction mixture was filtered, the filter cake was washed with methanol (50 mL * 3), and the filtrate was concentrated under reduced pressure to give a residue. The residue was poured into water (50 mL), then the mixture was extracted with ethyl acetate (50 mL * 2), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by reverse flase (MeCN / H2O, CF3COOH), then the mixture was concentrated to remove MeCN, then the pH of the mixture was adjusted to pH=7 by using saturated aqueous sodium bicarbonate solution, then the mixture was extracted with ethyl acetate (100mL*2), the combined organic layers were dried over saturated sodium sulfate, filtered, and concentrated under reduced pressure to give the residue. Compound 27 (210mg, 1.02mmol, yield 52.52%, purity 98%) was obtained as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 6.64 - 6.59 (m, 1H), 6.54 - 6.50 (m, 1H), 2.30 (s, 3H).

[0118] Step 3) 4-Bromo-5-methylbenzo[d]oxazole To a solution of compound 27 (210 mg, 1.02 mmol, 1 equiv) and trimethoxymethane (162.14 mg, 1.53 mmol, 167.50 μL, 1.5 equiv) in EtOH (3 mL) was added tris(trifluoromethylsulfonyloxy)ytterbium (14.19 mg, 22.87 μmol, 2.25e-2 equiv), then the reaction mixture was stirred at 90° C. for 12 h. LCMS showed that 19% of compound 3 remained and 81% of the desired mass was detected. Trimethoxymethane (108.09 mg, 1.02 mmol, 111.66 μL, 1 equiv) was added to the reaction mixture, then the reaction mixture was stirred at 90° C. for an additional 2 h. The reaction mixture was concentrated under reduced pressure to remove the solvent. Saturated aqueous NaHCO3 solution (50 mL) was added to the residue, then the mixture was extracted with ethyl acetate (30 mL*3), the combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue.

[0119] Compound 28 (160 mg, crude) was obtained as a brown solid. 1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 7.43 (d, J = 8.3 Hz, 1H), 7.29 (d, J = 8.4 Hz, 1H), 2.54 (s, 3H).

[0120] Step 4) (1S,2S)-2-Fluoro-N-(6-(5-methylbenzo[d]oxazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide To a solution of compound 28 (130 mg, 613.08 μmol, 1 eq.) and compound 11 (253.95 mg, 735.70 μmol, 1.2 eq.) in dioxane (2 mL) and H2O (0.4 mL), Pd(dppf)Cl2 (44.86 mg, 61.31 μmol, 0.1 eq.) and Na2CO3 (194.94 mg, 1.84 mmol, 3 eq.) were added, and the reaction mixture was then stirred at 90° C. under N2 for 12 h. The reaction mixture was poured into brine (30 mL), and the mixture was then extracted with ethyl acetate (30 mL*2), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was dissolved in methanol:dichloromethane (1:10, 100 mL), and the mixture was then filtered through silica gel, and the filtrate was concentrated to give a residue. The residue was purified by preparative HPLC (column: Xtimate C18 150*40mm*10um; mobile phase: [water (0.05% ammonia hydroxide v / v)-ACN]; B%: 25%-55%, 10min). Example 105 (118.4mg, 333.33μmol, yield 54.37%, purity 98.633%) was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.07 (s, 1H), 8.70 (s, 1H), 8.65 (s, 1H), 8.13 (s, 1H), 7.71 (d, J = 8.3 Hz, 1H), 7.53 (d, J = 9.2 Hz, 1H), 7.43 (d, J = 8.4 Hz, 1H), 7.29 (dd, J = 1.6, 9.2 Hz, 1H), 5.05 - 4.81 (m, 1H), 2.38 (s, 3H), 2.20 - 2.10 (m, 1H), 1.73 - 1.59 (m, 1H), 1.17 (tdd, J = 6.2, 9.1, 12.2 Hz, 1H).

[0121] Table 1 below lists example compounds along with the general synthetic methods used to generate the compounds and characterization data. [Table 1] TIFF0007609790000025.tif215165 TIFF0007609790000026.tif215165 TIFF0007609790000027.tif220165 TIFF0007609790000028.tif230165 TIFF0007609790000029.tif209165 TIFF0007609790000030.tif221165 TIFF0007609790000031.tif218165 TIFF0007609790000032.tif220165 TIFF0007609790000033.tif217165 TIFF0007609790000034.tif209165 TIFF0007609790000035.tif219165 TIFF0007609790000036.tif219165 TIFF0007609790000037.tif213165 TIFF0007609790000038.tif227165 TIFF0007609790000039.tif235165 TIFF0007609790000040.tif226165 TIFF0007609790000041.tif247165 TIFF0007609790000042.tif226165 TIFF0007609790000043.tif218165 TIFF0007609790000044.tif228165 TIFF0007609790000045.tif239165 TIFF0007609790000046.tif230165 TIFF0007609790000047.tif224165 TIFF0007609790000048.tif242165 TIFF0007609790000049.tif241165 TIFF0007609790000050.tif229165 TIFF0007609790000051.tif178165 TIFF0007609790000052.tif238165 TIFF0007609790000053.tif218165 TIFF0007609790000054.tif234165 TIFF0007609790000055.tif230165 TIFF0007609790000056.tif238165 TIFF0007609790000057.tif232165 TIFF0007609790000058.tif223165 TIFF0007609790000059.tif86165

[0122] Compound evaluation c-abl kinase assay ADP-Glo ​​assay kit was purchased from Promega. Magnesium chloride (MgCl2), bovine serum albumin (BSA), ethylene glycol-bis(β-aminoethyl ether)-N,N,N',N'-tetraacetic acid (EGTA), triton X-100, 1,4-dithiothreitol (DTT) and dimethyl sulfoxide (DMSO) were purchased from Sigma-Aldrich. HEPES buffer was purchased from Gibco. ABL1 kinase and Abltide were purchased from Signalchem.

[0123] c-Abl kinase activity was measured by Promega's ADP-Glo™ assay. In this assay, His-tagged recombinant human ABL1 (0.25ng / μl) was incubated with 5μL of compound (0.5% DMSO), 5μL of Abltide (0.01μg / μl) and 5μL of ATP (25μM) in buffer (50mM HEPES, 7.5; 10mM MgCl2; 1mM EGTA; 0.05% BSA; 0.01% Triton X-100; 2mM DTT). The assay was initiated by incubating the reaction mixture in a 96-well plate at 30°C for 30 minutes. After incubation, 25μL of ADP-Glo ​​reagent was added and the reaction was incubated at room temperature for 40 minutes to stop the reaction and decompose residual ATP. The ADP product was then converted to ATP by adding 50 μL of detection reagent per well. Luminescence was detected after 30 min incubation at room temperature using a Molecular device I3X plate reader. IC 50 Values ​​were calculated from a series of % inhibition values ​​measured over a range of inhibitor concentrations using GraphPad Prism 7 software and software routines implemented in Sigma Plot 13.0.

[0124] LRRK2 and LRRK2 G2019S kinase assays LRRK2 and LRRK2 G2019S kinase assays were performed using ThermoFisher Scientific's Adapta™ technology. The experiments were performed according to the supplier's protocol. Briefly, the assay conditions were as follows: Substrate (LRRKtide) and each kinase mixture was prepared in 50 mM Tris pH 8.5, 0.01% BRIJ-35, 10 mM MgCl2, 1 mM EGTA, 0.02% NaN3. Assays were performed in the presence of 70 μM ATP and 100 μM ATP (KmATP) for LRRK2 and LRRK2 G2019S, respectively. Reactions were allowed to proceed for 1 hour at room temperature. Upon completion of the kinase reaction, 5 μL of Detection Mix was added and the 665 / 615 nm emission ratio was calculated after 60 minutes of incubation time.

[0125] Table 2 shows the IC of the compounds of the present invention, which is + for >1000 nM, ++ for 101 to 1000 nM, +++ for 10 to 100 nM, and ++++ for <10 nM. 50 Indicates the value.

[0126] [Table 2] TIFF0007609790000061.tif252165 TIFF0007609790000062.tif245165 TIFF0007609790000063.tif106165

Claims

1. Formula I 【Chemistry 1】 [In the formula, R １ is cyclopropyl substituted with one or more groups selected from the group consisting of halo, alkyl, hydroxyalkyl, haloalkyl, and monoalkylaminoalkyl; R ２ and R ３ are independently -H, halo, alkyl, alkoxy, -CF ３ , -CHF ２ , -CH ２ F or -OCF ３ and R ４ is a 6-membered aryl, pyridyl, pyrimidyl, pyranyl, pyridazinyl, pyrazinyl, 【Chemistry 2】 wherein said 6-membered aryl, said pyridyl, said pyrimidyl, said pyranyl, said pyridazinyl or said pyrazinyl is selected from the group consisting of: Halo, hydroxyl, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, hydroxyalkyl, dialkylaminoalkyl, trimethylsilylethoxymethyl, -CH ２ NHC(O)CH ３ , -NO ２ , -NR ａ R ｂ , -NR ａ C(=O)R ｂ , -NR ａ C(=O)NR ａ R ｂ , -NR ａ C(=O)OR ｂ , -OR ａ , -CN, -C(=O)R ａ , -C(=O)OR ａ , -C(=O)NR ａ R ｂ , -OC(=O)R ａ , -OC(=O)OR ａ , -OC(=O)NR ａ R ｂ , -SR ａ , azetidinyl, oxetanyl, tetrahydrofuranyl, furanyl, pyrrolidinyl, pyrrolyl, pyrazolyl, thiophenyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, furazanyl, oxadiazolyl, thiadiazolyl, phenyl, tetrahydropyranyl, pyranyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, piperidinyl, piperazinyl, morpholinyl, and thiomorpholinyl; R ａ and R ｂ is independently -H, halo, amino, alkyl, or haloalkyl; R ５ is H, halo or alkyl. or a pharma- ceutically acceptable salt thereof.

2. R １ But, Halo, C １ ~C ３ Alkyl, C １ ~C ３ Hydroxyalkyl and C １ ~C ３ cyclopropyl, substituted by one or more groups selected from the group consisting of haloalkyl; R ２ and R ３ are independently -H, halo, C １ ~C ３ Alkyl, C １ ~C ３ Alkoxy, -CF ３ , -CHF ２ , -CH ２ F or -OCF ３ and R ４ is a 6-membered aryl, pyridyl, pyrimidyl, pyranyl, pyridazinyl or pyrazinyl, wherein said 6-membered aryl, said pyridyl, said pyrimidyl, said pyranyl, said pyridazinyl or said pyrazinyl is Halo, Hydroxyl, C １ ~C ３ Alkyl, C ２ ~C ３ Alkenyl, C ２ ~C ３ Alkynyl, C ３ ~C ４ Cycloalkyl, C １ ~C ３ Haloalkyl, -CH ２ NHC(O)CH ３ , -NO ２ , -NR ａ R ｂ , -NR ａ C(=O)R ｂ , -NR ａ C(=O)NR ａ R ｂ , -NR ａ C(=O)OR ｂ , -OR ａ , -CN, -C(=O)R ａ , -C(=O)OR ａ , -C(=O)NR ａ R ｂ , -OC(=O)R ａ , -OC(=O)OR ａ , -OC(=O)NR ａ R ｂ , -SR ａ , azetidinyl, oxetanyl, tetrahydrofuranyl, furanyl, pyrrolidinyl, pyrrolyl, pyrazolyl, thiophenyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, furazanyl, oxadiazolyl, thiadiazolyl, phenyl, tetrahydropyranyl, pyranyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, piperidinyl, piperazinyl, morpholinyl, and thiomorpholinyl; R ａ and R ｂ are independently -H, halo, amino, C １ ~C ３ Alkyl or C １ ~C ３ is haloalkyl, and R ５ The compound according to claim 1, wherein is H, F-, Cl-, Br- or methyl, or a pharma- ceutically acceptable salt thereof.

3. R １ But Fluoro, C １ ~C ３ Alkyl, C １ ~C ３ Hydroxyalkyl and C １ ~C ３ cyclopropyl substituted with one or more selected from the group consisting of fluoroalkyl; R ２ and R ３ are independently -H, -F, -Br, -Cl, １ ~C ３ Alkyl or -CF ３ and R ４ is phenyl, pyridinyl, pyrimidinyl or pyrazinyl, wherein said phenyl, said pyridinyl, said pyrimidinyl or said pyrazinyl is halo, hydroxyl, C １ ~C ３ Alkyl, C １ ~C ３ Haloalkyl, -NR ａ R ｂ , -OR ａ , -CN, -C(=O)R ａ , -C(=O)OR ａ , -OC(=O)R ａ , -OC(=O)OR ａ , -SR ａ , furanyl, pyrazolyl, imidazolyl, isothiazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, and pyrrolyl, and R ａ and R ｂ are independently -H, halo, amino, C １ ~C ３ Alkyl or C １ ~C ３ 2. The compound of claim 1, or a pharma- ceutically acceptable salt thereof, which is haloalkyl.

4. R １ 2. The compound of claim 1, wherein is cyclopropyl substituted with one or more groups selected from the group consisting of fluoro, methyl, ethyl, hydroxymethyl, hydroxyethyl, and methylaminomethyl, or a pharma- ceutically acceptable salt thereof.

5. R １ is fluorocyclopropyl, hydroxymethylcyclopropyl, difluorocyclopropyl, or methylaminomethylcyclopropyl; R ２ and R ３ The compound of claim 1, wherein is independently -H, methyl or fluoro, or a pharma- ceutically acceptable salt thereof.

6. R ４ is fluoro-methylphenyl, fluoro-hydroxymethylphenyl, chloro-methylphenyl, dimethylphenyl, acetamido-methylphenyl, hydroxy-methylphenyl, hydroxypropanyl-methylphenyl, methyl-propenylphenyl, ethynyl-methyl-pyridinylphenyl, methyl-pyrrolylphenyl, methyl-thiazolylphenyl, imidazolyl-methylphenyl, cyano-methylphenyl, methyl-pyrazolylphenyl, ethynyl-methylphenyl, methylpyridinyl, fluoro-methyl-methylaminophenyl, dimethylpyridinyl, fluoro-methylpyridinyl, fluoromethyl-methylpyridinyl, cyanopyridinyl, trifluoromethyl-methylpyridinyl, hydroxymethylpyridinyl, hydroxymethyl-methylpyridinyl, hydroxyethyl-methylpyridinyl, chloro-methylpyridinyl, aminopyridinyl, acetyl-methylpyridinyl, amino-dimethylpyridinyl, hydroxyethyl-methylpyridinyl, methylpyrimidinyl, dimethylpyrimidinyl, or trifluoromethylpyrimidinyl, or a pharma- ceutically acceptable salt thereof.

7. R ４ is fluoro-methylphenyl, fluoro-hydroxymethylphenyl, chloro-methylphenyl, dimethylphenyl, acetamido-methylphenyl, hydroxy-methylphenyl, methyl-propenylphenyl, ethynyl-methylphenyl, fluoro-methyl-methylaminophenyl, fluoro-hydroxy-methylphenyl, methyl-methylaminophenyl, methyl-pyrrolylphenyl, methyl-thiazolylphenyl, cyano-methylphenyl, imidazolyl-methylphenyl, methylpyridinyl, chloro-methylpyridinyl, fluoro-methylpyridinyl, fluoromethyl-methylpyridinyl, dimethylpyridinyl, aminopyridinyl, amino-dimethylpyridinyl, methoxypyridinyl, acetyl-methylpyridinyl, hydroxymethylpyridinyl, hydroxymethyl-methylpyridinyl, hydroxyethyl-methylpyridinyl, cyanopyridinyl, trifluoromethylpyridinyl, methylpyrimidinyl or dimethylpyrimidinyl.

8. R ４ or a pharma- ceutically acceptable salt thereof, wherein said phenyl, said pyridinyl or said pyrimidinyl is optionally substituted with one or more groups selected from the group consisting of halo, alkyl, alkynyl, hydroxyalkyl, amino, cyano, acetyl, hydroxy and haloalkyl.

9. R ４ But the following: 【Chemistry 3】 【change】 2. The compound of claim 1, selected from the group consisting of:

10. R １ or a pharma- ceutically acceptable salt thereof.

2. The compound of claim 1, wherein: is fluorocyclopropyl; or a pharma- ceutically acceptable salt thereof.

11. R ２ and R ３ is -H, R ４ is phenyl or pyridinyl, wherein said phenyl or said pyridinyl is halo, hydroxyl, alkyl, haloalkyl, hydroxyalkyl, cycloalkyl, -NR ａ R ｂ , -NR ａ C(=O)R ｂ , -OR ａ , -SR ａ , -CN, -C(=O)R ａ , -C(=O)OR ａ , -C(=O)NR ａ R ｂ , -OC(=O)R ａ , furanyl, or pyrrolyl; R ａ and R ｂ is independently -H, halo, amino, alkyl, or haloalkyl, and R ５ The compound of claim 10, or a pharma- ceutically acceptable salt thereof, wherein is -H, halo, or methyl.

12. Formula II: 【Chemistry 4】 [In the formula, R ２ , R ３ , R ４ and R ５ is as defined in claim 1, and R ６ But, Halo, C １ ~C ３ Alkyl, C １ ~C ３ Hydroxyalkyl and C １ ~C ３ haloalkyl] 2. The compound according to claim 1, which is a compound represented by the formula: or a pharma- ceutically acceptable salt thereof.

13. R ２ and R ３ is -H, R ４ is phenyl or pyridinyl, wherein said phenyl or said pyridinyl is halo, hydroxyl, alkyl, haloalkyl, hydroxyalkyl, cycloalkyl, -NR ａ R ｂ , -NR ａ C(=O)R ｂ , -OR ａ , -SR ａ , -CN, -C(=O)R ａ , -C(=O)OR ａ , -C(=O)NR ａ R ｂ , -OC(=O)R ａ , furanyl, or pyrrolyl; R ａ and R ｂ is independently -H, halo, amino, alkyl, or haloalkyl, and R ５ The compound of claim 12, or a pharma- ceutically acceptable salt thereof, wherein is -H, halo, or alkyl.

14. the below described: 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-chloro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(3-chloro-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(3-methyl-6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-chloro-6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(3-fluoro-2-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(6-(2-fluoro-6-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-fluoro-4-methylpyridin-3-yl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; Methyl 3-(2-(2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-4-methylbenzoate; 2-Fluoro-N-(6-(5-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-chloro-6-(5-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-cyano-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(4-chloropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2,3-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-amino-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(2-methyl-5-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(5-acetamido-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(4-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-(trifluoromethyl)pyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,4-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(3-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,5-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(4-cyanopyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(4-fluoro-2,3-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-fluoro-2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(6-(4-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(6-(2-methyl-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(4-fluoro-5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3,4-difluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(3,6-difluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(4-chloro-3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-methoxypyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(6-amino-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(5-amino-3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2-chloro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(6-aminopyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(2-methyl-5-(1H-pyrazol-1-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(6-(3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-bromo-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(3-fluoro-2-methoxyphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-cyano-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(2-chloro-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(2,3-difluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-fluoro-N-(6-(3-fluoro-2-(methoxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(3-fluoro-2-(furan-2-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(3-fluoro-2-(methylthio)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(6-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-acetyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(6-(dimethylamino)-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-(aminomethyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(2-(acetamidomethyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2,2-difluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(3-fluoro-2-((methylamino)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(3-fluoro-2-((isopropylamino)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(3-fluoro-2-((2-methoxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(3-fluoro-2-((2-hydroxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-((dimethylamino)methyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(o-tolyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-hydroxyphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-amino-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(2-(dimethylamino)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(2-ethyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-fluoro-N-(6-(3-fluoro-2-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(2-cyclopropyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-fluoro-N-(6-(3-fluoro-2-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(3-fluoro-2-isopropylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(3-fluoro-2-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-fluoro-2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2-ethyl-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide N-(6-(4-acetyl-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2-chloro-3,4-difluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(6-(2-chloro-3,6-difluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(8-(difluoromethyl)-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(3-fluoro-2-methylphenyl)-8-(fluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(8-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(7-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(6-(4-fluoro-2-methylphenyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(8-(difluoromethyl)-6-(4-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(4-fluoro-2-methylphenyl)-8-(fluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(8-fluoro-6-(4-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(7-fluoro-6-(4-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-fluoro-2-methylphenyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(8-(difluoromethyl)-6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(5-fluoro-2-methylphenyl)-8-(fluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(8-fluoro-6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(7-fluoro-6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(8-(difluoromethyl)-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(2-fluoro-6-methylphenyl)-8-(fluoromethyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(8-fluoro-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; and 2-Fluoro-N-(7-fluoro-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide or a pharma- ceutically acceptable salt thereof, selected from the group consisting of:

15. the below described: 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-chloro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; N-(3-chloro-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(3-fluoro-2-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(6-(2-fluoro-6-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,3-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(2-methyl-5-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,4-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(3-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,5-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(2-methyl-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(4-fluoro-5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(3-bromo-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; and 2-Fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide or a pharma- ceutically acceptable salt thereof, selected from the group consisting of:

16. Formula III: 【Chemistry 5】 [In the formula, R ２ , R ３ , R ４ and R ５ is as defined in claim 1, and R ６ But, Halo, C １ ~C ３ Alkyl, C １ ~C ３ Hydroxyalkyl and C １ ~C ３ haloalkyl] 2. The compound according to claim 1, which is a compound represented by the formula: or a pharma- ceutically acceptable salt thereof.

17. R ２ and R ３ is -H, R ４ is phenyl or pyridinyl, wherein said phenyl or said pyridinyl is halo, hydroxyl, alkyl, haloalkyl, hydroxyalkyl, cycloalkyl, -NR ａ R ｂ , -NR ａ C(=O)R ｂ , -OR ａ , -SR ａ , -CN, -C(=O)R ａ , -C(=O)OR ａ , -C(=O)NR ａ R ｂ , -OC(=O)R ａ , furanyl, or pyrrolyl; R ａ and R ｂ is independently -H, halo, amino, alkyl, or haloalkyl; R ５ 17. The compound of claim 16, wherein is -H, halo, or alkyl, or a pharma- ceutically acceptable salt thereof.

18. the below described: (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(3-chloro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(3-chloro-6-(2-fluoro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(3-methyl-6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(3-chloro-6-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(2-fluoro-6-methylphenyl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(5-fluoro-4-methylpyridin-3-yl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; Methyl 3-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-4-methylbenzoate; (1S,2S)-2-fluoro-N-(6-(5-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(3-chloro-6-(5-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(5-cyano-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(3-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(4-chloropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(2,3-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(5-amino-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(2-methyl-5-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(5-acetamido-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(5-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(2-methyl-5-(1H-pyrazol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(4-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(3-chloro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(4-(trifluoromethyl)pyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(2,4-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(3-fluoro-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(2,5-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(4-cyanopyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(4-fluoro-2,3-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(4-fluoro-2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(4-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(2-methyl-5-(1H-pyrrol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(3-methylthiophen-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(2,6-dimethylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(4-fluoro-5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(3,4-difluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(3,6-difluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(4-chloro-3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(2-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(4-methoxypyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(6-amino-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(5-amino-3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(2-chloro-6-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-N-(6-(6-aminopyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(2-methyl-5-(1H-pyrazol-1-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-(hydroxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(3-bromo-6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-methoxyphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-cyano-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(2-chloro-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(2,3-difluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-(methoxymethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-(furan-2-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-(methylthio)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(6-fluoro-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-acetyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(6-(dimethylamino)-4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(2-(aminomethyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(2-(acetamidomethyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-((methylamino)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-((isopropylamino)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-((2-methoxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-((2-hydroxyethoxy)methyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-((dimethylamino)methyl)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(o-tolyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-hydroxyphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-amino-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(2-(dimethylamino)-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-N-(6-(2-ethyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-N-(6-(2-cyclopropyl-3-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; and (1S,2S)-2-Fluoro-N-(6-(3-fluoro-2-isopropylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide or a pharma- ceutically acceptable salt thereof, selected from the group consisting of:

19. the below described: (1S,2S)-2-fluoro-N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(5-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(4-chloropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(2-methyl-5-(methylamino)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(3-methylthiophen-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; and (1S,2S)-N-(6-(3,4-difluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide or a pharma- ceutically acceptable salt thereof, selected from the group consisting of:

20. 2. The compound of claim 1, wherein the salt is a hydrochloride, tartrate, phosphate or maleate salt.

21. the below described: 2-Fluoro-N-(6-(5-methyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(1H-pyrazol-3-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-Fluoro-N-(6-(4-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; 2-fluoro-N-(6-(2-methyl-5-(1H-pyrazol-3-yl)phenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-oxoindolin-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-methylthiophen-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-methyl-2-oxoindolin-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(6-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(2-oxo-2,3-dihydrobenzo[d]thiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; N-(6-(3,5-dimethyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; N-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-fluoro-N-(6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; N-(6-(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; 2-Fluoro-N-(6-(5-methyl-1H-indol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(6-methyl-1H-indol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(5-methyl-1H-benzo[d]imidazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(5-methylbenzo[d]oxazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(5-methyl-1H-benzo[d]imidazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-fluoro-N-(6-(6-methylbenzo[d]thiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(5-methylbenzo[d]oxazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(5-methylbenzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-fluoro-N-(6-(7-methylbenzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; 2-Fluoro-N-(6-(furan-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(thiophen-2-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(thiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(3-methylisothiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-methylthiazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; 2-Fluoro-N-(6-(5-methyl-2-oxoindolin-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; and N-(6-(3-fluoro-2-methylphenyl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide or a pharma- ceutically acceptable salt thereof.

22. the below described: (1S,2S)—N-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(2-oxoindolin-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(5-methyl-2-oxoindolin-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(2-oxo-2,3-dihydrobenzo[d]thiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-N-(6-(3,5-dimethyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)—N-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)—N-(6-(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(5-methyl-1H-indol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(6-methyl-1H-indol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(5-methyl-1H-benzo[d]imidazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(5-methylbenzo[d]oxazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(5-methyl-1H-benzo[d]imidazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide; (1S,2S)-2-fluoro-N-(6-(6-methylbenzo[d]thiazol-5-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(5-methylbenzo[d]oxazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(5-methylbenzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; (1S,2S)-2-fluoro-N-(6-(7-methylbenzo[d]thiazol-6-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide; and (1S,2S)-2-Fluoro-N-(6-(5-methyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide or a pharma- ceutically acceptable salt thereof.

23. A therapeutically effective amount of a compound according to any one of claims 1 to 22 or a pharma- ceutically acceptable salt thereof and at least one pharma- ceutically acceptable carrier. Pharmaceutical compositions.

24. 24. The pharmaceutical composition of claim 23, further comprising one or more active ingredients useful for treating a neurodegenerative disease.

25. The pharmaceutical composition according to any one of claims 1 to 22 for treating a neurodegenerative disease in a subject.

26. The pharmaceutical composition according to claim 25, wherein the neurodegenerative disease is selected from the group consisting of α-synucleinopathy, Parkinson's disease, dementia with Lewy bodies, multiple system atrophy (MSA), Alzheimer's disease and amyotrophic lateral sclerosis (ALS).

27. 27. The pharmaceutical composition of claim 26, wherein the subject is a human.

28. 23. Use of a compound according to any one of claims 1 to 22, or a pharma- ceutically acceptable salt thereof, in the preparation of a medicament for treating a neurodegenerative disease in a subject.

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